Busted by step daughter in her panties
I went through forty-five years of my life as a single man, no one to answer to but myself. I watched my friends marry, have c***dren, and get divorced. I kept hearing the same old stories, 'money problems', 'she wasn't the same in bed after the k**s came', 'we are too tired because of the k**s', and the best of all 'we fight too much over money and the k**s'. I would just listen and laugh in my head at them. Then I met Emily. Emily was just your average sized woman on the outside, size 12 full figured, but she carried it well. It was her big boned body frame rather than just added weight. She had beautiful soft red hair that cascaded over her milky white skin. She had just enough freckles on her face to be attractive and not over powering. Her eyes were emerald green. Her breasts are the softest I have ever felt, white with the pinkest nipples that stick out a half inch when aroused. My heart would skip a beat when she laughed. I was hooked. I finally realized what my friends felt when they decided they found a woman that changed their life.
At my age I gave up on having c***dren of my own, with Emily came and instant family. Emily has a twenty-two year old daughter that is smoking hot. She lives at home and finishing her last year of college. Emily had Jessica when she was just twenty. Jessica has her father's features, tall, thin, brown hair with obvious natural red highlights, small petite breasts, and she is very athletic. When I moved in Jessica turned into an iceberg. Her father passed away in some traffic accident when Jessica was a small c***d so it's not like her parents will ever get back together. I never had c***dren so I was not looking to be this person of authority, besides the fact that she is an adult.
I work fifty percent out of my home and the other fifty percent I travel for my company. I moved into Emily's home because it was much bigger than my two bedroom condo, which I rent now. Emily has a large four bedroom home, pool, private large lot. She used the money from her husband's life insurance to invest in a home which is now bought and paid for. She was one smart woman.
Emily is an emergency room physician so she is at the hospital often and on call every other weekend. Our schedules allow for a lot of freedom, but it also means that we do not cross paths on a daily basis. We have to schedule sex in order to have it as regularly as possible.
Jessica does work hard at school and homework. The ice princess does have good study habits and good grades. She will go for her MBA and/or Phd in clinical psychology.
I asked Jessica why she was so hard on me and her response was that she didn't want to get too close in case it didn't work out with her mother. She said that men didn't stay too long because of her mom's work schedule. At least it wasn't me personally that she hated, she just doesn't want her feelings hurt. I could appreciate that.
I was working in my office at home, bored. What else do you do when you're bored? Surf porn. I started to surf porn and went to a few BDSM sites. I find dominant women to be very sexy. Some of the sites had men tied up and others had them dressed in women's clothes. I found some of the men looked pretty good wearing nylons and panties. I was almost hairless and still had a flat stomach so I figured I would look pretty good in some sexy clothes. I was alone at home so I thought I would play a little. I went to our bedroom and started to open the drawers pulling out some panties and bras. The panties were too big. Emily was a size 12 and I was thinner with a 30 inch waist, so they didn't look good. I was 5'10" tall, one hundred and sixty pounds. The bra barely stayed up on me. I was getting frustrated.
I started to walk around the house and found myself going into Jessica's room. Jessica's room was in perfect order. I opened her nightstand drawer, condoms, vibrator, lube, and nipple clamps, very naughty girl. I was careful not to touch or move anything. I moved to her dresser and opened the top drawer. Eureka, panties, bras, slips, and nighties. It was a veritable silk and lace bonanza.
I was standing in my step-daughter's room naked, running my hands through her silky lingerie. I felt so naughty and horny. My cock was hard as a rock. I reached down and gave it a couple of strokes. Crap that felt good. I was now super horny. I had to try on some clothes. I pulled a pink pair of panties out, with red bow ties on the sides. I bent over and slipped my left foot through the opening, and then the right. I slowly pulled them over my calves and up my thighs. I took a deep breath as the silk glided up my legs. My body shuddered as I pulled the panties over my hard cock.
I had to have more. I searched her drawers and pulled out a black slip. I pulled it over my head and let it cascade down my body. I ran my hands up and down my sides feeling the cool soft feel of the silk. I walked over to the closet door mirror to look at myself. The slip rubbed against my nipples and made them stick out. I was getting so excited.
I couldn't take it anymore, I threw myself on Jessica's bed, pulled out my hard cock, and started to jackoff. I was rubbing my nipple through the slip and pretending I was a girl, "Oh you like your tits played with don't you slut? You look so sexy in your slutty panties." I was wiggling my ass in the panties and dripping precum like crazy.
"WHAT THE HELL ARE YOU DOING?" Jessica was standing in her doorway screaming at me.
I heard the volume of the scream more than I heard the words. I knew I was busted and a million thoughts ran through my head as my cock shriveled down and popped back in the confines of the silky panties. "OH SHIT!" I rolled off the bed, away from the doorway, in a feeble attempt to hide behind the side of the bed.
"OH SHIT! IS RIGHT! What are you doing in my room James? Or do I need to call you Jamie now, you sick perverted fuck? My mother is going to kick your ass out of this house so fast. I knew not to trust you." Jessica's face was beet red.
"Please Jessica don't tell Emily. This was the first and only time this happened, I swear." I was pleading my best case standing in a slip and panties. I stood up, without thinking, and walked towards Jessica as I apologized.
Jessica stared me down, fire burned through her eyes, "Get out of my things. NO wait; keep them I never want to see them again. Look at you all dressed like a little sissy. Is that why you're with my mother, so she can dominate your sorry ass? I find it pathetic that a man can be so submissive."
I was now standing in front of her begging for the slightest bit of sympathy and praying that I can convince her not tell Emily. "Please Jessica I'll do anything you want just to keep this between the two of us. Please don't tell Emily, it will destroy her knowing about this. Please, please." I even sounded pathetic to myself but at the same time I was getting aroused at being in silky panties and being scolded by a woman. I felt my cock growing against the panties. When I moved my nipples were super charged as they rubbed against the satin slip.
My growing cock didn't go unnoticed, "Oh my god, you're getting a hardon from me yelling at you. You are one sick fucker."
Jessica crossed her arms and held her stance, "If my mother wasn't so damn happy with you I would call her right now. I do not know what she sees in you that she would want to stay with you. I will be damned if I am going to be the one that breaks her heart. I need some time to think about this."
Jessica turned and stormed out of her room, leaving me standing there in panties and a slip. I went to go after her, but I heard the front door slam and knew I was through. I ran to my room and pulled off the panties and kicked them aside. I went to take off the slip and as I moved the long flowing slip softly gliding over my bare ass and cock I was getting hard again. I was mad at myself for enjoying the feel of the silk against my naked skin. I kept the slip on as I went and gathered my man clothes. The feeling of walking around was turning me on more.
"Ah, fuck it!" I said to myself. "My life is over anyway" so I grabbed my hard cock through the slip and began to beat my cock with one hand and started to tweak my nipple with the other. The silky sensation pushed me over the edge and I was shooting my cum through the slip. The slip kept my cum from shooting out so my cum just oozed through the silky material. I wasn't prepared to catch my cum so on impulse I brought the puddle of cum up to my face and sucked it off the slip. I was so turned on that even when my lips made contact with the soft fabric by cock twitched. I swallowed my entire load down. I actually enjoyed the thick milky substance. I closed my eyes and swirled the concoction around in my mouth. It was smooth and thick. I thought it would be hotter than it was. I was expecting a sharp bitter taste, rather it was smooth going down my throat, with a hint of bitter and tang together. It wasn't unpleasant at all.
I pulled off the slip and made sure I had sucked all of the cum from it. I grabbed the panties as well and tossed them into the hamper. I reluctantly pulled on my 'man' clothes and returned to my home office to think. The hours felt like days as I waited for Jessica to return and find out my fate.
Four long hours went by. It wasn't until five thirty before I finally heard the front door open and then close. I assumed Jessica was going to tell me to pack my things and be gone before Emily got home. I was shocked and scared shitless when in runs Emily. I thought her haste was to chew me a new asshole and kick me out, until she rushed past me, gave me a peck on the cheek, and continued to our bedroom.
"I gotta go back to the hospital. I just received a call when I was pulling up to the driveway, big building on fire and we are going to get hit hard. I'll probably be there all night." Emily grabbed some clean clothes, changed, and was out the door in five minutes. It was obvious that she hadn't spoken with Jessica.
Another three hours passed and it was almost nine o'clock. I hadn't eaten dinner, my appetite was gone, and so I called it a night. I jumped in the shower before getting ready for bed. I let the hot water roll off my back as the tension floated down the drain with the water. My body is pretty hairless except for the usual head, pits, crotch, and ass. I have never had hairy legs side from a little patch along my shins. Having blonde hair and light skin, even the pit hair seemed sparse.
I was still horny from walking around wearing silky clothes so I grabbed Emily's shaver, poured some liquid soap in my hand, bent over, and began to lather and shave my legs. Once I felt how soft my skin felt I couldn't stop myself. Before I knew it I had my arm pits shaved, my cock and balls were now hairless, and even the hair in the crack of my ass was now void from my body. Even the water felt different. My cock was rock solid and I couldn't wait to put on a slip or nighty and go to bed.
I shut the water off and dried myself off with a towel. My skin was on sensory overload. Anything and everything that touched me right now brought me that much closer to cumming. Emily's granny panties were not going to do it for me. I didn't dare go back into Jessica's room and the slip and panties have dried cum stains on them. I fished around Emily's drawers until I found lodged way in the back of her drawer a matching red baby doll top and panty set. I pulled it out and held it up to my body.
The top was sheer red with a red satin ribbon outlining the entire top. It was open in the front like a short robe, a red silk thin belt with two red fluffy balls at the ends, and matching red sheer panties that were also outlined with red silk. They looked smaller than her usual things, this must have been a gift that she has had tucked away for long time.
I put my arms through the top and pulled it on, leaving it untied. I bent over and pulled on the panties. My shaved body was on fire. I looked hot in this outfit. I stood in front of the mirror and spun around. The top floated away from my body and as I stopped it fell lightly back against my body. My cock was bending in the confines of the panties.
Then I heard the front door slam. I began to panic. How would I explain my shaved body to Emily? I need to change and put her things away. She will be up the stairs and in our room in no time. Then I heard Jessica calling "James, are you home?"
I was still in panic mode as I threw the top back in the drawer and as I heard Jessica coming up the stairs I grabbed a pair of sweat pants and a t-shirt and slipped them on over my red panties, just in time to hear her knocking at the bedroom door.
"James, are you in hear?" Jessica called as she softly knocked on the bedroom door.
I was sitting on the edge of the bed, my heart was racing. In a low solemn tone I managed to say "Yes Jessica, I'm still here."
The door opened slowly and I sat awaiting my fate. Jessica walked in carrying a small pink bag. "I want to apologize for yelling at you this afternoon. I had every right to yell for being in my room and violating my things, but for someone that is working on a degree in psychology I didn't stop to recognize what you were doing and I just attacked you."
Was I dreaming? I thought this bitch of a girl was going to rip me to shreds and now she was apologizing to me? I don't get it. I sat there with my mouth open. "I am so sorry Jessica. I should have never gone in your room or touched your things. I was caught up in the moment and I wasn't thinking either."
Jessica walked over to me and gave me a hug. That was the first hug she has ever given me, let alone any ounce of sincerity. "I spent some time in the library and found that men wanting to wear women's clothes are more common then I realized. But if you have latent homosexual feelings I want you to be honest with my mother before she gets hurt."
I jumped off the bed, "Whoa! NO I don't have latent homosexual feelings. I just liked the feeling of the material against my body. I love your mother and LOVE having sex with her. I got caught up in the moment because I was surfing porn and was sexually frustrated, that's all."
"Surfing porn is very common as well, for both sexes. So you're just getting in touch with your feminine side, is that it? Tired of being the macho man and wanting to feel less pressure to please, you want to be pleased, pampered, feel special, like you treat mom? I understand mom works long hours and doesn't have time for you or me, I get that. You're not looking for a man to treat you like a lady? You just want to be put on a pedal stool for once, shown some real effection?"
I looked down at my hands, "I guess, something like that."
Jessica continued to taunt the truth out of me without me even realizing it, "Putting on women's clothes makes you feel sexy, attractive, desirable, don't they?"
My eyes were glazed over she nailed me, "Yes. They make me feel sexy."
Jessica handed me the bag, "Here I went out shopping and bought you a little apology gift. Go on, open it."
I opened the bag, reached my hand in, and pulled out a tissue wrapped bundle. I could tell it was clothing of some sort. I looked up at Jessica. She was staring at me with anticipation. I slowly removed the tissue paper to uncover soft silky pink garments. My first thought was that Jessica was making fun of me.
Jessica grabbed my hand before I could object, "Look James, I want to be friends. This will be our little secret. After thinking about things I realized that it would be better that you express yourself here at home than elsewhere. If you promise to keep your dressing up to this house then I will support you 100% and let you walk around in any outfit you like. I won't tell mom unless you want me to or when you want to. But if you're going to dress in pretty clothes than I want you to have your own and not wear my things, deal?"
My mouth was gaping open. Did I dare trust her? Was she really being sincere? Would I enjoy the feeling of silk against my body if the taboo was taken away? "I'm not sure Jessica. I did it once because I was horny and lonely. I'm not so sure I want to pursue this anymore. I appreciate you wanting to help me. I don't know if I would be comfortable walking around in lingerie with you here."
Jessica grabbed one of the items in my hand and rubbed it against my face, "Tell me this doesn't feel real nice against your skin Jamie? I have a nice pink slip, pink silk panties, and pink nylons with garter belts. You will look so sexy in this outfit and you can put them in my closet when mom is home. Let it go Jamie do what makes you feel good. Besides, I think you'll look sexy in this outfit that's why I picked it out with you in mind."
Jessica continued to rub the silky slip all over my face and arms. I closed my eyes and felt my cock getting hard. I soft moan escaped my lips giving me away to my desires. "That's it baby feel the soft material against your skin. Wait until you feel the nylons being pulled up your legs. Don't deny yourself Jamie."
I was ready to shoot my load when I opened my eyes and I could see the same lust that I was feeling reflected in Jessica's eyes. She was getting off on me dressing up. I grabbed the package and went into the bathroom to try it all on.
I raised my arms and let the slip slide down over my body. The cool material against my freshly shaven body was pure bliss. I then sat on the edge of the bathtub and started to put on one of the nylons. I wasn't sure how the garter belt would work so I grabbed the pink silk panties and pulled them up and over my hard cock. The head of my cock was sticking out the top of the panties. A clear drop of precum was leaking out already. I used my finger to clean the drop of precum, brought it up to my mouth and rubbed it on my lips like lipstick. I ran my tongue over my lips feeling the smooth feel of my cum on my lips.
I stepped out of the bathroom holding the nylons and garter belt, "Um Jessica I'm not sure how these work."
Jessica jumped off the bed and came to my assistance, "You look nice Jamie. First let's have you lip the garter belt on." Jessica held the belt open at my feet waiting for me to step inside the circle.
I pointed my toe and stepped into the circle one foot at a time. Jessica slowly pulled up the garter belt, "Jamie your legs are sooooo smooth. You're going to love the feeling of nylon against them."
When she got up to my crotch she pulled on the garter belt to stretch it over my hard cock. "Looks like someone is enjoying this?"
Jessica instructed me to sit on the edge of the bed as she rolled and bunched one of the nylons down in her hand. She told me to point my toe as she slipped it on my foot. She pulled up the nylon over my heel and up my calf. I could feel my eyes roll back in my head as I threw my head back. "Feels good, huh Jamie? Your skin is so soft. You really do have feminine features. I find that really sexy."
Jessica ran her hands up and down my nylon covered leg before she repeated her efforts on my other leg. They nylon against my smooth skin was causing my cock to leak forming a big wet spot on my new panties. I could feel Jessica's hands running along my legs. She attached the nylon tops to the garter clips that dangled from the belt.
Jessica stood up and took a step back, "Simply lovely Jamie," is all she said that caused my face to flush.
Jessica quickly grabbed my hand and pulled me into the bathroom. Jessica stood behind me and turned me to face the full length mirror. "Look at how nice you look in your pretty outfit. Does this make you feel sexy?"
As Jessica asked me how I looked she was running her hands up and down the silky slip. This was the attention I was craving. I wanted to be the center of someone's affection, to be wanted.
I fell back against Jessica and let my head fall back against her shoulder as I felt her breasts press against my back. Jessica reached around to my front and placed a hand over each of my nipples and began to knead my breasts through the silk slip. I began to moan in ecstasy, like a woman.
I could feel Jessica's hot breath in my ear, "That's it Jamie let it go baby. This is what you wanted all along isn't it? You want to be sexually attractive? Well I think you are the hottest thing I have ever seen."
I could feel Jessica's hard nipples pressing into my back. She was just as excited as I was. My knees began to shake as my orgasm built. Jessica grabbed my ear lobe with her mouth and I felt her hot tongue caress it. At the same time she grabbed both my nipples and lightly pinched and pulled on them through the silky material. My body went weak as I felt my cum shoot into my panties. "AAAGGGHHHH!!!" I screamed out with pure lust and guilt.
"Shhhhhh!!! It's ok Jamie. Enjoy the feeling." I felt Jessica's hand move down to my cum filled panties and push her hand past the waist line and grab my cum drenched cock. Jessica pulled out her hand and brought her cum covered hand to my mouth. "Lick it up baby. Taste your pleasure."
I was starving for this attention as I greedily licked my thick sperm off her hand. Jessica reached her hand into my panties again but this time she brought it up to her mouth and licked it, "MMMMM, yes that is nice."
Jessica then pushed me lightly away and patted me on the ass, "Now go get cleaned up before mom gets home. You can bring me your outfit when you change. I will wash it and put it away in my closet. When mom is out of the house you can come and dress in your little outfit."
This wasn't the special bond I was expecting between us. I hurried into the shower again and rinsed the cum off my cock and balls. I rinsed the panties off and put on a pair of sweats and t-shirt. I brought Jessica my clothes and as I knocked on her bedroom door I became guilt ridden.
Jessica noticed the change in my attitude as I could not look her in the eye. She stood up and took my clothes and placed them on her bed then gave me a hug. "Oh James don't worry we will work through this. It's just sexual release, that's all. Better that you release your sexual tension here at home than let it build up between you and mom, that will cause fights or you will go out and get it somewhere else. Nobody is hurt here and you look so damn sexy in your outfit. I love seeing you dressed up and you enjoy dressing up so who cares?"
We held each other for what seemed like an hour but really was only about a minute. I pulled away and Jessica gave me a friendly peck on the cheek. She did not make me feel like we were going to become an item or that she wanted any more than to be friends. I turned and went to bed.
I traveled for work for the next three days and kept myself busy. When I arrived back home on Friday night the house was empty. I dropped my luggage off at the front door and headed for the kitchen. As I flipped the light on I noticed the note on the kitchen counter, it was from Emily.
"Dearest James, I am so sorry I wasn't home to give you that well deserved welcome home evening but mother took a fall and I had to drive to Los Angeles for the weekend. I so wish we were together tonight I REALLY need you. This all happened when you were in the air so I couldn't contact you. Call me when you get the note. Love you M."
I grabbed my cell phone and called Emily. I thanked her for the note and getting me all horny sitting here by myself. We laughed and she assured me that she would make it up to me. I told her that I would take her up on that offer and we said goodnight.
I was dog ass tired so I grabbed a beer and headed for my room to shower the trip off. I was standing in the shower when my cock reminded me I needed to pay him some attention. I thought I better shave myself all over first. It felt so exhilarating to run the shaver up and down my legs, over my balls, and finish with my pits.
I got out of the shower and dried off. I was about to slip on my shorts when I remembered by outfit in Jessica's room. I went down the hall, still naked, and entered Jessica's room. We had an agreement that she would hide my clothes for me so I didn't think twice about going in her room. What I did find surprising was a magazine on Jessica's bed that had a picture on the front of a woman with a strap-on dildo fucking a man dressed in women's clothes.
I scooped up the magazine and plopped my naked ass down on her bed. I started to flip through the pages. Pictures and stories of women fucking guys dressed up as women. Is this what Jessica is into? I thought to myself. Does she expect this of me? Is this something I want? I had never thought that way. But I looked down and my cock was dripping and hard. I got up and went back to my room without getting my clothes. I went to bed and fell asleep. I dreamed of Jessica fucking me with a strapon and I was so turned on that I woke myself up covered in cum.
Saturday morning I woke up, stripped the bed, put on my bathrobe, and took the linens to the laundry room. I put the sheets in the washer and turned it on. I went to the kitchen to put on some coffee to start my day. As I rounded the corner I could smell coffee already brewing. Jessica was sitting at the table with a cup of coffee waiting for me. "Good morning James. I poured you a cup of coffee. Did mom get a hold of you?"
"Good morning. Thanks for the coffee I could really use it this morning. Ya, your mom and I talked last night." I sipped my coffee and grabbed a section of the newspaper.
Jessica put her cup down, "Chris and I are going to the beach today he should be here anytime to pick me up. What do you have on your agenda?"
"I'm wiped from my trip thought I would take it easy today. I'm going to mow the lawns and then sit out by the pool and veg." I told her. I was really enjoying this new relationship with Jessica. "Can I just say that this is the nicest feeling having such a casual conversation with you? Thank you"
"I know James I am sorry I was such a bitch it was very immature of me. Well I told you I was going to be gone all day in case you wanted to dress up. I laid some things out on my bed in case you get the urge. Chris and I will be home around 4 or 5 so we don't have an embarrassing moment. I don't think Chris would understand, unfortunately." Jessica sounded disappointed.
"Thanks but I'm not sure I am in the mood. What do you mean 'unfortunately'?" I asked.
"Chris isn't as open minded as I would like. I wish he would be comfortable wearing sexy clothes like you. Sometimes I think he is too macho for my taste."
"Thanks a lot." I retorted, kind of pissed that she doesn't look at me as being manly.
"No, no James you got me wrong. I believe you can be both. Look at you, all manly now but when you want to be relaxed you can put on a nice slip and panties and are just as comfortable showing your feminine side. I admire that in you. I also think that you are sexy in your clothes. I would love to see Chris dressed up in nylons, slip, and panties." Jessica looked at me and patted the back of my hand, which was resting on the top of the table.
"Nice back pedaling Jessica." I said sarcastically and gave her a wink at the same time.
"You know James it's no different than when you see us women dressed up for a night on the town. We see the glint in a man's eyes as we make our grand entrance. It's just outerwear that makes us look and feel sexy and desirable. Isn't that how you feel when you get dressed up? When you go that extra mile don't you want someone to seduce you with hot passion?" Jessica had that glazed look again.
"I would love Chris to be dressed up so I can seduce him. Make love to him the way I want to be made love to. He is always in charge in the bedroom and sometimes I want to be the aggressor, the one calling the shots. Men can be such controlling assholes when it comes to sex." Jessica sat back in her chair and grabbed her coffee.
"Well speaking as one of the assholes, we do that because we are focusing on bringing you to an orgasm which for us is the ultimate goal to stroke our ego. We need to hear you scream out so that we know we are good lovers. It's just too bad that we usually get caught up in the act and we cum first." We both broke out into laughter.
"Aint that the truth!" Jessica held up her hand for a high five. I quickly responded as our hands slapped in mid-air.
There was a horn honking from outside and Jessica got up from the table, "Speaking of assholes, mine is honking." Jessica gave me a peck on the cheek, "Have a good day James. I really do enjoy our talks."
Jessica grabbed a beach bag, which was on the counter, and headed out the door. I finished the paper and another cup of coffee. I cleaned the kitchen and went to my room to put some clothes on. I passed Jessica's room and noticed several things on her bed. I walked in the room and looked at the outfits displayed for me. There was a white string bikini, a light blue baby doll, a black corset with matching leather panties and black fishnet stockings. An envelope with "Jamie" written across it was propped up against her pillows.
I opened the envelope and read the note;
'Dear Jamie, I am glad you chose to come in my room and check out your new outfits. I hope you enjoy wearing them as much as I enjoyed buying them for you. It was such a nice day I thought you might like to lay by the pool in a bikini. Chris should be dropping me off round 5 tonight and I will get rid of him so maybe you can model your other outfits for me? I hope you say yes. Hugs Jess'
My robe just dropped to the floor and I was standing naked in front of these outfits. I grabbed the bikini and slipped on the bottoms, or more like the small triangle with dental floss. My balls hung out on either side and my cockhead was poking out the top. The g-string ran up my ass crack. I put the top on and felt the small triangles resting against my hardening nipples. Why are women's clothes so soft against the skin and men's clothes are just there?
I went out of the room and told myself that I had to do all my chores dressed in my bikini. I went to the back and mowed the lawn and trimmed a few bushes. Then I cleaned the pool and straightened out the house. I took the sheets out of the dryer and made the bed. It was noon and I was ready to relax. I grabbed a cold beer from the house and went out to the pool. I set my drink down on the table and dove into the pool. It felt so good and refreshing. I was nearly skinny dipping. The water against my smooth ass was making me hornier, if that was possible.
I went back in the house and headed for Jessica's room. The magazine was no longer sitting on her bed. I didn't want to snoop, but I just had to look at it again. I opened just one drawer by her nightstand and there is was. I pulled it out and threw myself on her bed. I looked at the pictures of dominating women controlling a man in various types of dress. I read a couple of the stories about how the men liked being submissive as a complete opposite of their "normal" lifestyle. Being a boss at work, the man of the house, the breadwinner, the rock that holds the family together, sometimes you just want to let someone make the decisions for you, to make love to YOU. It was like the story was written for me.
I went to put the magazine back the way I found it and I found myself picking up one of the cock shaped vibrators. I held it in my hand and gently stroked it as if I was jacking it off. The outside felt so much like real flesh. It even had veins running along the sides, much like mine does. The cock head flared out away from the shaft and came to a point. It was much longer than my average six inch cock this had at least a couple of inches on me. Only one way to find out, I dropped my bikini bottoms and stood naked again in Jessica's room. I placed the fake cock right next to mine to compare. I rubbed the cock heads together causing my cock to harden. I put the base of the cock against my groin and the fake cock beat me by a head, the cock head. I placed the fake cock under my cock and could see that the fake cock was thicker on either side.
I started to stroke the cocks together until a clear bead of precum seeped out of my cock head. I took the tip of the dildo and scooped up the droplet. I brought the cock to my mouth and licked it off. I felt so naughty and so horny. My mind flashed to Jessica pushing her strapon cock to my lips and making me suck it. My eyes closed and my mouth opened. I pushed a couple of inches of the cock into my mouth. I slowly began to fuck my mouth with the fake cock. My saliva built up and the cock easily slid back and forth until the tip hit the back of my throat.
I lay on the bed pretending to give head to my step daughter's dildo, dreaming it was strapped around her waist as she held my head. I felt a drop of my precum land on my stomach. I looked down at my cock to see it was dripping. I took the dildo from my mouth and used it to scoop up the couple of drops that formed on my stomach. Instead of bringing it back to my mouth I brought the tip of the dildo down between my legs and used it to smear the cum on my hole. My clean shaven ass was really sensitive. I didn't realize that the puckered hole would react as it did or that I would react the way I did.
I began to slowly swirl the cockhead around my tightly puckered hole. The cum made is slide around and made it even more sensitive. Instinctively as the tip of the cockhead centered onto my hole my body lurched forward against the dildo. I held the dildo firmly and let my body rotate against it. I wanted it inside. I continued to rotate my hips against the tip massaging my hole open. I was getting so turned on I pushed harder. The tip spread my hole open just enough to expose some of the inner flesh. The pressure and massage I was getting was pushing me over the edge. Before I could push anymore of the dildo inside my balls tightened up and my cock shot streams of cum across my stomach and chest. I quickly scooped up my cum with the dildo and shoved it in my mouth before I lost my nerve.
I came down from my orgasm and the usual wave of guilt rushed over my body. I crossed the line into an area I never thought to explore before. I wanted to be fucked with a strapon. I needed someone to complete the job that I couldn't. I wanted Jessica to fuck me or possibly Emily. I knew Emily would never be into this. I didn't know I would ever be into this.
I cleaned myself up and straightened out Jessica's room. I left the two outfits on the bed and went back to my room. I slipped on a pair of gym shorts and a tank top and camped out in front of the tv for the next few hours. The phone rang and woke me up. I groggily answered the phone to hear Emily on the other end.
"Hello? James?" Emily sounded concerned.
"Umm, Hi M. Sorry I must have dozed off in front of the tv." I shook the cobwebs out of my head and focused. "How's your mom?"
"I'm sorry I woke you. Mom is doing fine but they are going to have to do surgery on her hip. I am going to stay all week here. I hope you don't mind? I have clothes here and if I need to I can run to the store for a couple of outfits. I'll be home on Saturday. I love you and miss you."
"No, don't feel bad, do what you have to do. I'm sure your mom will feel better knowing that a doctor will be nursing her back to health. Jessica and I will get by."
"I hope she isn't going to be a big pain in your ass, you two don't have the best relationship."
"Actually, we had a nice conversation this morning. I think we broke down a couple of walls. We will be fine. I love and miss you too."
"That makes me so happy that you two are getting along. I can't wait to come home. I'll call tomorrow night after the surgery. Love you."
"Love you too, talk to you tomorrow."
Just my luck, horny as hell and now it will be a whole week with no sex. I have no business trips this week so I am going to go crazy. I heard the front door open and slam shut. Jessica stormed through the house "That little prick, he can be such a prick sometimes."
I felt a smirk cross my face "Trouble in paradise Jess?"
Jessica walked past me, plopped down next to me on the couch, and put her head on my shoulder. "Chris is being such an asshole. We had a great day at the beach so on the way home we pulled off the road and found a nice secluded spot to fool around. We were both horny and needed relief so I started giving him a blow job. He came really fast and when I went up to kiss him he backed away. I looked at him and asked what the problem was, and do you know what he said?"
I was sitting frozen not know what to do. Did I really want to hear this about my step-daughter? What advice was she expecting of me? "I can't imagine," was the only thing I could think to say.
"He said that he didn't want to kiss me with his cum in my mouth. Can you believe that? I told him that I kiss him after he eats my pussy and I don't complain. Actually I like the taste of my pussy on his lips, but that's beside the point. Sex is a two way street. He should at least be willing to do what pleases me as well. I gave him a few things to think about before we continue our relationship." Jessica was cuddled into me now and lightly rubbing my exposed chest at the top of my tank top.
I could feel her light touch drawing imaginary circles on my skin. I just had a pair of gym shorts on so my rising cock was impossible to hide.
Jessica continued on, "I just wish he were more like you, willing to go outside the macho comfort zone and try new things. I'm not saying that he has to like it, just at least be open to try new things. I don't want some guy that lives for the missionary position or just wants to get HIS rocks off. Sex should be fun, new, fresh, exciting, that's what keeps the spark. Who wants to eat the same meal every day?"
It was time for me to interject before my cock pops out of my shorts, "Jess, your psychology classes are getting to your head. Stop analyzing him. If he isn't into it you can't and shouldn't force him, unless he IS into that?" I laughed, but I was really thinking of Jessica's magazine and how she wants to dominate a guy.
"I am still not totally comfortable being outside my comfort zone yet. Slow little steps. Chris needs that too, slow little steps." I sounded so fatherly, I felt my chest puff up a bit.
"I know you're right James. I guess I just wish he was at least as far along as you. Why aren't you wearing one of your outfits, didn't you like them?" Jessica said as she lifted her head to look me in the eye.
"I loved them. I wasn't sure if Chris was coming into the house so I didn't put them on yet. I did wear the bikini today, thank you." I could feel my heart begin to race and my cock automatically flinched.
Jessica pushed herself up, "Please put on the black outfit for me. I really need to see you in it."
How could I refuse her and her pleading eyes? I leaned forward and Jessica placed her hand on my inner thigh to brace herself as she got up. In doing so the back of her hand grazed the side of my hard cock and sent a thrill through my body. She squeezed my thigh as she pushed herself off the couch and held out her hand for me to take. I grabbed her hand and she pulled me up off the couch. No mention was made that my cock was hard as a rock and pointing my shorts straight out. We went to her room like a couple of teenage girls.
Jessica picked up the black corset and held it up to me, "You will look so hot in this, quick, put it on."
I grabbed the garment and turned to leave the room, "Where are you going Jamie?"
"I was going to my room to change." I answered back.
"Really? Come on its just the two of us here you can change here. Now come on and strip those manly clothes off and step into your fun world." Jessica was upon me before I knew what hit me grabbing the bottom of my shirt and lifting up and over my head before I could baulk. Before I knew it she had grabbed the hem on my shorts and pulled them down to my ankles. My hard cock sprang out and slapped my stomach making a loud skin to bare skin noise.
Jessica stood up and looked me in the eye, "Need more help putting your clothes on?"
I quickly started to dress, more to cover up in front of her than to put on my new clothes. As soon as I lifted my arms and shimmied into the corset all inhibitions were gone. "MMMMM, that feels nice." I purred.
"You like your new clothes Jamie?" Jessica's voice was shaky and her breathing was fast. I could tell she was getting turned on by watching me change in front of her.
Jessica grabbed the black leather panties and held them open and ready for me to step into, "Put your feet in Jamie." She instructed.
I stepped into the shorts and she began to pull them up. The leather was tight and dragged against the skin on my legs and she pulled them up. She stood behind me to finish pulling up the short panties. She pulled the front of the short forward pulling the shorts over my throbbing hard cock. When she finished she patted my hard cock through the shorts, "Perfect fit don't you think Jamie?"
I was in a pure lust fog feeling the leather and satin against my skin. Jamie leaned into my back again and as she whispered in my ear she grabbed the cheeks of my ass and gave them a hard squeeze, "Your ass is so tight in these. You like the feel of your tight ass in these panties Jamie?"
Her hands continued to knead my ass as I tried to respond, "Oh god yes."
Jessica's hands move to the front of the leather corset and dragged across my nipples, "MMMMM." I moaned as my legs began to weaken.
Jessica licked my earlobe again. Damn her, she knows my weak spots. "Ya this is what you need Jamie. Doesn't this leather feel nice against your skin? You look and smell so good." Jessica's hot breath was in my ear. She continued to rub circles on my nipples.
"Oh god yes. Feels sooooo gooodddd." I felt my ass grinding back against Jessica's pussy. My head was spinning. I wanted to push back against her strapon. I wanted to be one of those guys in the magazine.
"Ya that's it baby grind that ass against me. Your ass is on fire isn't it?" I felt Jessica's hand on my ass. Then I felt her finger slip under the leg opening on my panties.
Jessica's finger started to massage my hole, my pussy. I pushed back against her finger and started to rotate my hips along with her finger. Jessica continued to work my nipple through the leather corset and the tip of her finger pushed into my ass. "That's it isn't it Jamie? This is what you want, what you need?"
Her voice, her hot breath, the pressure on my pussy, "Yes" I could barely breathe it out. I was lost in lust. I wanted her finger inside me. I wanted her cock inside me. I wanted to be fucked. I wanted to be made love to. I needed to be made love to.
Jessica guided me to her bed and we effortlessly fell together on top. I landed on my stomach and Jessica was on my back. The force of the fall and the reaction of the bed bouncing back forced Jessica's entire finger to embed itself into my ass. The tip of her finger pressed firmly against my prostate. I moaned with a pleasure I have never felt before, "Oh yes, mmmmmm, god, oh shit."
"You like that do you Jamie? You like to be fucked baby? Want more, want something bigger baby?" Jamie was biting and licking my earlobe as she finger fucked my pussy.
"Yes, please yes. Fuck me Jess." I was horny beyond any and every sensation I ever felt before.
Jessica reached under her pillows with her left hand and I saw the dildo that I played with earlier. Her finger slipped out of my ass, my pants were pulled down exposing my ass and freeing my cock. I felt Jess's hot tongue slide between my cheeks. Her hot tongue was wiggling its way into my man pussy. She was pushing her spit into my pussy. She pulled her face back and I quickly felt the pressure of something big being pushed into me.
"Push out baby. Relax and push out." Jess said seductively as she held by cheeks open with one hand and pushed the head of the dildo into me with the other.
My head dropped down onto the bed causing my ass to rise up. I relaxed my body and pushed out slowly. I felt my ass give and open to allow the intrusion. The dildo's cockhead spread my hole farther then I thought possible. There was a sharp pain as my muscles lost the fight to hold the intruder out. My pussy lost and the dildo slipped past the sphincter muscle. I felt my body go limp as I stopped pushing out. That relaxed my body more and Jess pushed more of the dildo into me.
There was that point between pain and pleasure that I crossed. The pain left and was instantly replaced by pleasure. "That's it Jamie, relax now. You want this I can feel it. This is so fucking hot watching this cock disappear inside you. That's it baby take it all." Jess continued to talk me through it and was now rubbing my lower back.
"Oh fuck, this is so fucking hot. I feel so full." I was slowly rotating my hips against the dildo as she fed more of its length inside me. The feeling was incredible. Jess pushed more of the dildo in until I felt pressure against my prostate.
Jess must have felt the dildo reach my prostate because she slowly began to massage my prostate with the tip of the dildo. "There's your little love button. Does that feel good Jamie?"
I all but cried, "UGH! Oh shit, what are you doing to me? MMMMMM, I never thought this would be so good." I wiggled my ass and pushed back, I wanted more. I wanted to be fucked.
Jess began to slowly pull out the dildo and push it back in, "That's it baby enjoy the ride. I'm going to give you the fucking of your life. Feel the big cock going in and out of your tight pussy. You like this don't you Jamie? Tell me you want it. Tell me you want to be fucked."
"Yes, god YES, fuck me Jess. Take that big cock and fuck me good and hard. OOOOHHH!" I was begging for it. I didn't care about anything but that cock fucking my ass.
Jessica fucked me for what I wished to be hours but was probably just a few minutes when the pressure on my prostate was too much, "Oh god I'm cumming, uuggggg!!! Fuck me harder, oh god yes fuck me harder." Jessica starting to pull the dildo almost all the way out and shoved it back in hard. When the dick head hit my prostate my cock shot out streams of cum. My body tensed and shook with the most powerful orgasm I ever had.
I fell forward onto the bed, feeling the puddle of cum against my stomach. Jessica left the dildo sticking out of my ass as she lay next to me. I was sweating and panting so hard I could barely catch my breath.
I felt Jessica's hand rub the sweat from my brow, "That was so hot Jamie, thank you. I have always wanted to do that. You made me cum as well."
"I should be thanking you. I never came so hard in my life. I think I need to wash your bedding."
"You go jump in the shower and clean up, I'll take care of everything else." With that she leaned in and kissed me on the cheek. It was such a nice kiss, the kind that really said 'thank you'.
At my age I gave up on having c***dren of my own, with Emily came and instant family. Emily has a twenty-two year old daughter that is smoking hot. She lives at home and finishing her last year of college. Emily had Jessica when she was just twenty. Jessica has her father's features, tall, thin, brown hair with obvious natural red highlights, small petite breasts, and she is very athletic. When I moved in Jessica turned into an iceberg. Her father passed away in some traffic accident when Jessica was a small c***d so it's not like her parents will ever get back together. I never had c***dren so I was not looking to be this person of authority, besides the fact that she is an adult.
I work fifty percent out of my home and the other fifty percent I travel for my company. I moved into Emily's home because it was much bigger than my two bedroom condo, which I rent now. Emily has a large four bedroom home, pool, private large lot. She used the money from her husband's life insurance to invest in a home which is now bought and paid for. She was one smart woman.
Emily is an emergency room physician so she is at the hospital often and on call every other weekend. Our schedules allow for a lot of freedom, but it also means that we do not cross paths on a daily basis. We have to schedule sex in order to have it as regularly as possible.
Jessica does work hard at school and homework. The ice princess does have good study habits and good grades. She will go for her MBA and/or Phd in clinical psychology.
I asked Jessica why she was so hard on me and her response was that she didn't want to get too close in case it didn't work out with her mother. She said that men didn't stay too long because of her mom's work schedule. At least it wasn't me personally that she hated, she just doesn't want her feelings hurt. I could appreciate that.
I was working in my office at home, bored. What else do you do when you're bored? Surf porn. I started to surf porn and went to a few BDSM sites. I find dominant women to be very sexy. Some of the sites had men tied up and others had them dressed in women's clothes. I found some of the men looked pretty good wearing nylons and panties. I was almost hairless and still had a flat stomach so I figured I would look pretty good in some sexy clothes. I was alone at home so I thought I would play a little. I went to our bedroom and started to open the drawers pulling out some panties and bras. The panties were too big. Emily was a size 12 and I was thinner with a 30 inch waist, so they didn't look good. I was 5'10" tall, one hundred and sixty pounds. The bra barely stayed up on me. I was getting frustrated.
I started to walk around the house and found myself going into Jessica's room. Jessica's room was in perfect order. I opened her nightstand drawer, condoms, vibrator, lube, and nipple clamps, very naughty girl. I was careful not to touch or move anything. I moved to her dresser and opened the top drawer. Eureka, panties, bras, slips, and nighties. It was a veritable silk and lace bonanza.
I was standing in my step-daughter's room naked, running my hands through her silky lingerie. I felt so naughty and horny. My cock was hard as a rock. I reached down and gave it a couple of strokes. Crap that felt good. I was now super horny. I had to try on some clothes. I pulled a pink pair of panties out, with red bow ties on the sides. I bent over and slipped my left foot through the opening, and then the right. I slowly pulled them over my calves and up my thighs. I took a deep breath as the silk glided up my legs. My body shuddered as I pulled the panties over my hard cock.
I had to have more. I searched her drawers and pulled out a black slip. I pulled it over my head and let it cascade down my body. I ran my hands up and down my sides feeling the cool soft feel of the silk. I walked over to the closet door mirror to look at myself. The slip rubbed against my nipples and made them stick out. I was getting so excited.
I couldn't take it anymore, I threw myself on Jessica's bed, pulled out my hard cock, and started to jackoff. I was rubbing my nipple through the slip and pretending I was a girl, "Oh you like your tits played with don't you slut? You look so sexy in your slutty panties." I was wiggling my ass in the panties and dripping precum like crazy.
"WHAT THE HELL ARE YOU DOING?" Jessica was standing in her doorway screaming at me.
I heard the volume of the scream more than I heard the words. I knew I was busted and a million thoughts ran through my head as my cock shriveled down and popped back in the confines of the silky panties. "OH SHIT!" I rolled off the bed, away from the doorway, in a feeble attempt to hide behind the side of the bed.
"OH SHIT! IS RIGHT! What are you doing in my room James? Or do I need to call you Jamie now, you sick perverted fuck? My mother is going to kick your ass out of this house so fast. I knew not to trust you." Jessica's face was beet red.
"Please Jessica don't tell Emily. This was the first and only time this happened, I swear." I was pleading my best case standing in a slip and panties. I stood up, without thinking, and walked towards Jessica as I apologized.
Jessica stared me down, fire burned through her eyes, "Get out of my things. NO wait; keep them I never want to see them again. Look at you all dressed like a little sissy. Is that why you're with my mother, so she can dominate your sorry ass? I find it pathetic that a man can be so submissive."
I was now standing in front of her begging for the slightest bit of sympathy and praying that I can convince her not tell Emily. "Please Jessica I'll do anything you want just to keep this between the two of us. Please don't tell Emily, it will destroy her knowing about this. Please, please." I even sounded pathetic to myself but at the same time I was getting aroused at being in silky panties and being scolded by a woman. I felt my cock growing against the panties. When I moved my nipples were super charged as they rubbed against the satin slip.
My growing cock didn't go unnoticed, "Oh my god, you're getting a hardon from me yelling at you. You are one sick fucker."
Jessica crossed her arms and held her stance, "If my mother wasn't so damn happy with you I would call her right now. I do not know what she sees in you that she would want to stay with you. I will be damned if I am going to be the one that breaks her heart. I need some time to think about this."
Jessica turned and stormed out of her room, leaving me standing there in panties and a slip. I went to go after her, but I heard the front door slam and knew I was through. I ran to my room and pulled off the panties and kicked them aside. I went to take off the slip and as I moved the long flowing slip softly gliding over my bare ass and cock I was getting hard again. I was mad at myself for enjoying the feel of the silk against my naked skin. I kept the slip on as I went and gathered my man clothes. The feeling of walking around was turning me on more.
"Ah, fuck it!" I said to myself. "My life is over anyway" so I grabbed my hard cock through the slip and began to beat my cock with one hand and started to tweak my nipple with the other. The silky sensation pushed me over the edge and I was shooting my cum through the slip. The slip kept my cum from shooting out so my cum just oozed through the silky material. I wasn't prepared to catch my cum so on impulse I brought the puddle of cum up to my face and sucked it off the slip. I was so turned on that even when my lips made contact with the soft fabric by cock twitched. I swallowed my entire load down. I actually enjoyed the thick milky substance. I closed my eyes and swirled the concoction around in my mouth. It was smooth and thick. I thought it would be hotter than it was. I was expecting a sharp bitter taste, rather it was smooth going down my throat, with a hint of bitter and tang together. It wasn't unpleasant at all.
I pulled off the slip and made sure I had sucked all of the cum from it. I grabbed the panties as well and tossed them into the hamper. I reluctantly pulled on my 'man' clothes and returned to my home office to think. The hours felt like days as I waited for Jessica to return and find out my fate.
Four long hours went by. It wasn't until five thirty before I finally heard the front door open and then close. I assumed Jessica was going to tell me to pack my things and be gone before Emily got home. I was shocked and scared shitless when in runs Emily. I thought her haste was to chew me a new asshole and kick me out, until she rushed past me, gave me a peck on the cheek, and continued to our bedroom.
"I gotta go back to the hospital. I just received a call when I was pulling up to the driveway, big building on fire and we are going to get hit hard. I'll probably be there all night." Emily grabbed some clean clothes, changed, and was out the door in five minutes. It was obvious that she hadn't spoken with Jessica.
Another three hours passed and it was almost nine o'clock. I hadn't eaten dinner, my appetite was gone, and so I called it a night. I jumped in the shower before getting ready for bed. I let the hot water roll off my back as the tension floated down the drain with the water. My body is pretty hairless except for the usual head, pits, crotch, and ass. I have never had hairy legs side from a little patch along my shins. Having blonde hair and light skin, even the pit hair seemed sparse.
I was still horny from walking around wearing silky clothes so I grabbed Emily's shaver, poured some liquid soap in my hand, bent over, and began to lather and shave my legs. Once I felt how soft my skin felt I couldn't stop myself. Before I knew it I had my arm pits shaved, my cock and balls were now hairless, and even the hair in the crack of my ass was now void from my body. Even the water felt different. My cock was rock solid and I couldn't wait to put on a slip or nighty and go to bed.
I shut the water off and dried myself off with a towel. My skin was on sensory overload. Anything and everything that touched me right now brought me that much closer to cumming. Emily's granny panties were not going to do it for me. I didn't dare go back into Jessica's room and the slip and panties have dried cum stains on them. I fished around Emily's drawers until I found lodged way in the back of her drawer a matching red baby doll top and panty set. I pulled it out and held it up to my body.
The top was sheer red with a red satin ribbon outlining the entire top. It was open in the front like a short robe, a red silk thin belt with two red fluffy balls at the ends, and matching red sheer panties that were also outlined with red silk. They looked smaller than her usual things, this must have been a gift that she has had tucked away for long time.
I put my arms through the top and pulled it on, leaving it untied. I bent over and pulled on the panties. My shaved body was on fire. I looked hot in this outfit. I stood in front of the mirror and spun around. The top floated away from my body and as I stopped it fell lightly back against my body. My cock was bending in the confines of the panties.
Then I heard the front door slam. I began to panic. How would I explain my shaved body to Emily? I need to change and put her things away. She will be up the stairs and in our room in no time. Then I heard Jessica calling "James, are you home?"
I was still in panic mode as I threw the top back in the drawer and as I heard Jessica coming up the stairs I grabbed a pair of sweat pants and a t-shirt and slipped them on over my red panties, just in time to hear her knocking at the bedroom door.
"James, are you in hear?" Jessica called as she softly knocked on the bedroom door.
I was sitting on the edge of the bed, my heart was racing. In a low solemn tone I managed to say "Yes Jessica, I'm still here."
The door opened slowly and I sat awaiting my fate. Jessica walked in carrying a small pink bag. "I want to apologize for yelling at you this afternoon. I had every right to yell for being in my room and violating my things, but for someone that is working on a degree in psychology I didn't stop to recognize what you were doing and I just attacked you."
Was I dreaming? I thought this bitch of a girl was going to rip me to shreds and now she was apologizing to me? I don't get it. I sat there with my mouth open. "I am so sorry Jessica. I should have never gone in your room or touched your things. I was caught up in the moment and I wasn't thinking either."
Jessica walked over to me and gave me a hug. That was the first hug she has ever given me, let alone any ounce of sincerity. "I spent some time in the library and found that men wanting to wear women's clothes are more common then I realized. But if you have latent homosexual feelings I want you to be honest with my mother before she gets hurt."
I jumped off the bed, "Whoa! NO I don't have latent homosexual feelings. I just liked the feeling of the material against my body. I love your mother and LOVE having sex with her. I got caught up in the moment because I was surfing porn and was sexually frustrated, that's all."
"Surfing porn is very common as well, for both sexes. So you're just getting in touch with your feminine side, is that it? Tired of being the macho man and wanting to feel less pressure to please, you want to be pleased, pampered, feel special, like you treat mom? I understand mom works long hours and doesn't have time for you or me, I get that. You're not looking for a man to treat you like a lady? You just want to be put on a pedal stool for once, shown some real effection?"
I looked down at my hands, "I guess, something like that."
Jessica continued to taunt the truth out of me without me even realizing it, "Putting on women's clothes makes you feel sexy, attractive, desirable, don't they?"
My eyes were glazed over she nailed me, "Yes. They make me feel sexy."
Jessica handed me the bag, "Here I went out shopping and bought you a little apology gift. Go on, open it."
I opened the bag, reached my hand in, and pulled out a tissue wrapped bundle. I could tell it was clothing of some sort. I looked up at Jessica. She was staring at me with anticipation. I slowly removed the tissue paper to uncover soft silky pink garments. My first thought was that Jessica was making fun of me.
Jessica grabbed my hand before I could object, "Look James, I want to be friends. This will be our little secret. After thinking about things I realized that it would be better that you express yourself here at home than elsewhere. If you promise to keep your dressing up to this house then I will support you 100% and let you walk around in any outfit you like. I won't tell mom unless you want me to or when you want to. But if you're going to dress in pretty clothes than I want you to have your own and not wear my things, deal?"
My mouth was gaping open. Did I dare trust her? Was she really being sincere? Would I enjoy the feeling of silk against my body if the taboo was taken away? "I'm not sure Jessica. I did it once because I was horny and lonely. I'm not so sure I want to pursue this anymore. I appreciate you wanting to help me. I don't know if I would be comfortable walking around in lingerie with you here."
Jessica grabbed one of the items in my hand and rubbed it against my face, "Tell me this doesn't feel real nice against your skin Jamie? I have a nice pink slip, pink silk panties, and pink nylons with garter belts. You will look so sexy in this outfit and you can put them in my closet when mom is home. Let it go Jamie do what makes you feel good. Besides, I think you'll look sexy in this outfit that's why I picked it out with you in mind."
Jessica continued to rub the silky slip all over my face and arms. I closed my eyes and felt my cock getting hard. I soft moan escaped my lips giving me away to my desires. "That's it baby feel the soft material against your skin. Wait until you feel the nylons being pulled up your legs. Don't deny yourself Jamie."
I was ready to shoot my load when I opened my eyes and I could see the same lust that I was feeling reflected in Jessica's eyes. She was getting off on me dressing up. I grabbed the package and went into the bathroom to try it all on.
I raised my arms and let the slip slide down over my body. The cool material against my freshly shaven body was pure bliss. I then sat on the edge of the bathtub and started to put on one of the nylons. I wasn't sure how the garter belt would work so I grabbed the pink silk panties and pulled them up and over my hard cock. The head of my cock was sticking out the top of the panties. A clear drop of precum was leaking out already. I used my finger to clean the drop of precum, brought it up to my mouth and rubbed it on my lips like lipstick. I ran my tongue over my lips feeling the smooth feel of my cum on my lips.
I stepped out of the bathroom holding the nylons and garter belt, "Um Jessica I'm not sure how these work."
Jessica jumped off the bed and came to my assistance, "You look nice Jamie. First let's have you lip the garter belt on." Jessica held the belt open at my feet waiting for me to step inside the circle.
I pointed my toe and stepped into the circle one foot at a time. Jessica slowly pulled up the garter belt, "Jamie your legs are sooooo smooth. You're going to love the feeling of nylon against them."
When she got up to my crotch she pulled on the garter belt to stretch it over my hard cock. "Looks like someone is enjoying this?"
Jessica instructed me to sit on the edge of the bed as she rolled and bunched one of the nylons down in her hand. She told me to point my toe as she slipped it on my foot. She pulled up the nylon over my heel and up my calf. I could feel my eyes roll back in my head as I threw my head back. "Feels good, huh Jamie? Your skin is so soft. You really do have feminine features. I find that really sexy."
Jessica ran her hands up and down my nylon covered leg before she repeated her efforts on my other leg. They nylon against my smooth skin was causing my cock to leak forming a big wet spot on my new panties. I could feel Jessica's hands running along my legs. She attached the nylon tops to the garter clips that dangled from the belt.
Jessica stood up and took a step back, "Simply lovely Jamie," is all she said that caused my face to flush.
Jessica quickly grabbed my hand and pulled me into the bathroom. Jessica stood behind me and turned me to face the full length mirror. "Look at how nice you look in your pretty outfit. Does this make you feel sexy?"
As Jessica asked me how I looked she was running her hands up and down the silky slip. This was the attention I was craving. I wanted to be the center of someone's affection, to be wanted.
I fell back against Jessica and let my head fall back against her shoulder as I felt her breasts press against my back. Jessica reached around to my front and placed a hand over each of my nipples and began to knead my breasts through the silk slip. I began to moan in ecstasy, like a woman.
I could feel Jessica's hot breath in my ear, "That's it Jamie let it go baby. This is what you wanted all along isn't it? You want to be sexually attractive? Well I think you are the hottest thing I have ever seen."
I could feel Jessica's hard nipples pressing into my back. She was just as excited as I was. My knees began to shake as my orgasm built. Jessica grabbed my ear lobe with her mouth and I felt her hot tongue caress it. At the same time she grabbed both my nipples and lightly pinched and pulled on them through the silky material. My body went weak as I felt my cum shoot into my panties. "AAAGGGHHHH!!!" I screamed out with pure lust and guilt.
"Shhhhhh!!! It's ok Jamie. Enjoy the feeling." I felt Jessica's hand move down to my cum filled panties and push her hand past the waist line and grab my cum drenched cock. Jessica pulled out her hand and brought her cum covered hand to my mouth. "Lick it up baby. Taste your pleasure."
I was starving for this attention as I greedily licked my thick sperm off her hand. Jessica reached her hand into my panties again but this time she brought it up to her mouth and licked it, "MMMMM, yes that is nice."
Jessica then pushed me lightly away and patted me on the ass, "Now go get cleaned up before mom gets home. You can bring me your outfit when you change. I will wash it and put it away in my closet. When mom is out of the house you can come and dress in your little outfit."
This wasn't the special bond I was expecting between us. I hurried into the shower again and rinsed the cum off my cock and balls. I rinsed the panties off and put on a pair of sweats and t-shirt. I brought Jessica my clothes and as I knocked on her bedroom door I became guilt ridden.
Jessica noticed the change in my attitude as I could not look her in the eye. She stood up and took my clothes and placed them on her bed then gave me a hug. "Oh James don't worry we will work through this. It's just sexual release, that's all. Better that you release your sexual tension here at home than let it build up between you and mom, that will cause fights or you will go out and get it somewhere else. Nobody is hurt here and you look so damn sexy in your outfit. I love seeing you dressed up and you enjoy dressing up so who cares?"
We held each other for what seemed like an hour but really was only about a minute. I pulled away and Jessica gave me a friendly peck on the cheek. She did not make me feel like we were going to become an item or that she wanted any more than to be friends. I turned and went to bed.
I traveled for work for the next three days and kept myself busy. When I arrived back home on Friday night the house was empty. I dropped my luggage off at the front door and headed for the kitchen. As I flipped the light on I noticed the note on the kitchen counter, it was from Emily.
"Dearest James, I am so sorry I wasn't home to give you that well deserved welcome home evening but mother took a fall and I had to drive to Los Angeles for the weekend. I so wish we were together tonight I REALLY need you. This all happened when you were in the air so I couldn't contact you. Call me when you get the note. Love you M."
I grabbed my cell phone and called Emily. I thanked her for the note and getting me all horny sitting here by myself. We laughed and she assured me that she would make it up to me. I told her that I would take her up on that offer and we said goodnight.
I was dog ass tired so I grabbed a beer and headed for my room to shower the trip off. I was standing in the shower when my cock reminded me I needed to pay him some attention. I thought I better shave myself all over first. It felt so exhilarating to run the shaver up and down my legs, over my balls, and finish with my pits.
I got out of the shower and dried off. I was about to slip on my shorts when I remembered by outfit in Jessica's room. I went down the hall, still naked, and entered Jessica's room. We had an agreement that she would hide my clothes for me so I didn't think twice about going in her room. What I did find surprising was a magazine on Jessica's bed that had a picture on the front of a woman with a strap-on dildo fucking a man dressed in women's clothes.
I scooped up the magazine and plopped my naked ass down on her bed. I started to flip through the pages. Pictures and stories of women fucking guys dressed up as women. Is this what Jessica is into? I thought to myself. Does she expect this of me? Is this something I want? I had never thought that way. But I looked down and my cock was dripping and hard. I got up and went back to my room without getting my clothes. I went to bed and fell asleep. I dreamed of Jessica fucking me with a strapon and I was so turned on that I woke myself up covered in cum.
Saturday morning I woke up, stripped the bed, put on my bathrobe, and took the linens to the laundry room. I put the sheets in the washer and turned it on. I went to the kitchen to put on some coffee to start my day. As I rounded the corner I could smell coffee already brewing. Jessica was sitting at the table with a cup of coffee waiting for me. "Good morning James. I poured you a cup of coffee. Did mom get a hold of you?"
"Good morning. Thanks for the coffee I could really use it this morning. Ya, your mom and I talked last night." I sipped my coffee and grabbed a section of the newspaper.
Jessica put her cup down, "Chris and I are going to the beach today he should be here anytime to pick me up. What do you have on your agenda?"
"I'm wiped from my trip thought I would take it easy today. I'm going to mow the lawns and then sit out by the pool and veg." I told her. I was really enjoying this new relationship with Jessica. "Can I just say that this is the nicest feeling having such a casual conversation with you? Thank you"
"I know James I am sorry I was such a bitch it was very immature of me. Well I told you I was going to be gone all day in case you wanted to dress up. I laid some things out on my bed in case you get the urge. Chris and I will be home around 4 or 5 so we don't have an embarrassing moment. I don't think Chris would understand, unfortunately." Jessica sounded disappointed.
"Thanks but I'm not sure I am in the mood. What do you mean 'unfortunately'?" I asked.
"Chris isn't as open minded as I would like. I wish he would be comfortable wearing sexy clothes like you. Sometimes I think he is too macho for my taste."
"Thanks a lot." I retorted, kind of pissed that she doesn't look at me as being manly.
"No, no James you got me wrong. I believe you can be both. Look at you, all manly now but when you want to be relaxed you can put on a nice slip and panties and are just as comfortable showing your feminine side. I admire that in you. I also think that you are sexy in your clothes. I would love to see Chris dressed up in nylons, slip, and panties." Jessica looked at me and patted the back of my hand, which was resting on the top of the table.
"Nice back pedaling Jessica." I said sarcastically and gave her a wink at the same time.
"You know James it's no different than when you see us women dressed up for a night on the town. We see the glint in a man's eyes as we make our grand entrance. It's just outerwear that makes us look and feel sexy and desirable. Isn't that how you feel when you get dressed up? When you go that extra mile don't you want someone to seduce you with hot passion?" Jessica had that glazed look again.
"I would love Chris to be dressed up so I can seduce him. Make love to him the way I want to be made love to. He is always in charge in the bedroom and sometimes I want to be the aggressor, the one calling the shots. Men can be such controlling assholes when it comes to sex." Jessica sat back in her chair and grabbed her coffee.
"Well speaking as one of the assholes, we do that because we are focusing on bringing you to an orgasm which for us is the ultimate goal to stroke our ego. We need to hear you scream out so that we know we are good lovers. It's just too bad that we usually get caught up in the act and we cum first." We both broke out into laughter.
"Aint that the truth!" Jessica held up her hand for a high five. I quickly responded as our hands slapped in mid-air.
There was a horn honking from outside and Jessica got up from the table, "Speaking of assholes, mine is honking." Jessica gave me a peck on the cheek, "Have a good day James. I really do enjoy our talks."
Jessica grabbed a beach bag, which was on the counter, and headed out the door. I finished the paper and another cup of coffee. I cleaned the kitchen and went to my room to put some clothes on. I passed Jessica's room and noticed several things on her bed. I walked in the room and looked at the outfits displayed for me. There was a white string bikini, a light blue baby doll, a black corset with matching leather panties and black fishnet stockings. An envelope with "Jamie" written across it was propped up against her pillows.
I opened the envelope and read the note;
'Dear Jamie, I am glad you chose to come in my room and check out your new outfits. I hope you enjoy wearing them as much as I enjoyed buying them for you. It was such a nice day I thought you might like to lay by the pool in a bikini. Chris should be dropping me off round 5 tonight and I will get rid of him so maybe you can model your other outfits for me? I hope you say yes. Hugs Jess'
My robe just dropped to the floor and I was standing naked in front of these outfits. I grabbed the bikini and slipped on the bottoms, or more like the small triangle with dental floss. My balls hung out on either side and my cockhead was poking out the top. The g-string ran up my ass crack. I put the top on and felt the small triangles resting against my hardening nipples. Why are women's clothes so soft against the skin and men's clothes are just there?
I went out of the room and told myself that I had to do all my chores dressed in my bikini. I went to the back and mowed the lawn and trimmed a few bushes. Then I cleaned the pool and straightened out the house. I took the sheets out of the dryer and made the bed. It was noon and I was ready to relax. I grabbed a cold beer from the house and went out to the pool. I set my drink down on the table and dove into the pool. It felt so good and refreshing. I was nearly skinny dipping. The water against my smooth ass was making me hornier, if that was possible.
I went back in the house and headed for Jessica's room. The magazine was no longer sitting on her bed. I didn't want to snoop, but I just had to look at it again. I opened just one drawer by her nightstand and there is was. I pulled it out and threw myself on her bed. I looked at the pictures of dominating women controlling a man in various types of dress. I read a couple of the stories about how the men liked being submissive as a complete opposite of their "normal" lifestyle. Being a boss at work, the man of the house, the breadwinner, the rock that holds the family together, sometimes you just want to let someone make the decisions for you, to make love to YOU. It was like the story was written for me.
I went to put the magazine back the way I found it and I found myself picking up one of the cock shaped vibrators. I held it in my hand and gently stroked it as if I was jacking it off. The outside felt so much like real flesh. It even had veins running along the sides, much like mine does. The cock head flared out away from the shaft and came to a point. It was much longer than my average six inch cock this had at least a couple of inches on me. Only one way to find out, I dropped my bikini bottoms and stood naked again in Jessica's room. I placed the fake cock right next to mine to compare. I rubbed the cock heads together causing my cock to harden. I put the base of the cock against my groin and the fake cock beat me by a head, the cock head. I placed the fake cock under my cock and could see that the fake cock was thicker on either side.
I started to stroke the cocks together until a clear bead of precum seeped out of my cock head. I took the tip of the dildo and scooped up the droplet. I brought the cock to my mouth and licked it off. I felt so naughty and so horny. My mind flashed to Jessica pushing her strapon cock to my lips and making me suck it. My eyes closed and my mouth opened. I pushed a couple of inches of the cock into my mouth. I slowly began to fuck my mouth with the fake cock. My saliva built up and the cock easily slid back and forth until the tip hit the back of my throat.
I lay on the bed pretending to give head to my step daughter's dildo, dreaming it was strapped around her waist as she held my head. I felt a drop of my precum land on my stomach. I looked down at my cock to see it was dripping. I took the dildo from my mouth and used it to scoop up the couple of drops that formed on my stomach. Instead of bringing it back to my mouth I brought the tip of the dildo down between my legs and used it to smear the cum on my hole. My clean shaven ass was really sensitive. I didn't realize that the puckered hole would react as it did or that I would react the way I did.
I began to slowly swirl the cockhead around my tightly puckered hole. The cum made is slide around and made it even more sensitive. Instinctively as the tip of the cockhead centered onto my hole my body lurched forward against the dildo. I held the dildo firmly and let my body rotate against it. I wanted it inside. I continued to rotate my hips against the tip massaging my hole open. I was getting so turned on I pushed harder. The tip spread my hole open just enough to expose some of the inner flesh. The pressure and massage I was getting was pushing me over the edge. Before I could push anymore of the dildo inside my balls tightened up and my cock shot streams of cum across my stomach and chest. I quickly scooped up my cum with the dildo and shoved it in my mouth before I lost my nerve.
I came down from my orgasm and the usual wave of guilt rushed over my body. I crossed the line into an area I never thought to explore before. I wanted to be fucked with a strapon. I needed someone to complete the job that I couldn't. I wanted Jessica to fuck me or possibly Emily. I knew Emily would never be into this. I didn't know I would ever be into this.
I cleaned myself up and straightened out Jessica's room. I left the two outfits on the bed and went back to my room. I slipped on a pair of gym shorts and a tank top and camped out in front of the tv for the next few hours. The phone rang and woke me up. I groggily answered the phone to hear Emily on the other end.
"Hello? James?" Emily sounded concerned.
"Umm, Hi M. Sorry I must have dozed off in front of the tv." I shook the cobwebs out of my head and focused. "How's your mom?"
"I'm sorry I woke you. Mom is doing fine but they are going to have to do surgery on her hip. I am going to stay all week here. I hope you don't mind? I have clothes here and if I need to I can run to the store for a couple of outfits. I'll be home on Saturday. I love you and miss you."
"No, don't feel bad, do what you have to do. I'm sure your mom will feel better knowing that a doctor will be nursing her back to health. Jessica and I will get by."
"I hope she isn't going to be a big pain in your ass, you two don't have the best relationship."
"Actually, we had a nice conversation this morning. I think we broke down a couple of walls. We will be fine. I love and miss you too."
"That makes me so happy that you two are getting along. I can't wait to come home. I'll call tomorrow night after the surgery. Love you."
"Love you too, talk to you tomorrow."
Just my luck, horny as hell and now it will be a whole week with no sex. I have no business trips this week so I am going to go crazy. I heard the front door open and slam shut. Jessica stormed through the house "That little prick, he can be such a prick sometimes."
I felt a smirk cross my face "Trouble in paradise Jess?"
Jessica walked past me, plopped down next to me on the couch, and put her head on my shoulder. "Chris is being such an asshole. We had a great day at the beach so on the way home we pulled off the road and found a nice secluded spot to fool around. We were both horny and needed relief so I started giving him a blow job. He came really fast and when I went up to kiss him he backed away. I looked at him and asked what the problem was, and do you know what he said?"
I was sitting frozen not know what to do. Did I really want to hear this about my step-daughter? What advice was she expecting of me? "I can't imagine," was the only thing I could think to say.
"He said that he didn't want to kiss me with his cum in my mouth. Can you believe that? I told him that I kiss him after he eats my pussy and I don't complain. Actually I like the taste of my pussy on his lips, but that's beside the point. Sex is a two way street. He should at least be willing to do what pleases me as well. I gave him a few things to think about before we continue our relationship." Jessica was cuddled into me now and lightly rubbing my exposed chest at the top of my tank top.
I could feel her light touch drawing imaginary circles on my skin. I just had a pair of gym shorts on so my rising cock was impossible to hide.
Jessica continued on, "I just wish he were more like you, willing to go outside the macho comfort zone and try new things. I'm not saying that he has to like it, just at least be open to try new things. I don't want some guy that lives for the missionary position or just wants to get HIS rocks off. Sex should be fun, new, fresh, exciting, that's what keeps the spark. Who wants to eat the same meal every day?"
It was time for me to interject before my cock pops out of my shorts, "Jess, your psychology classes are getting to your head. Stop analyzing him. If he isn't into it you can't and shouldn't force him, unless he IS into that?" I laughed, but I was really thinking of Jessica's magazine and how she wants to dominate a guy.
"I am still not totally comfortable being outside my comfort zone yet. Slow little steps. Chris needs that too, slow little steps." I sounded so fatherly, I felt my chest puff up a bit.
"I know you're right James. I guess I just wish he was at least as far along as you. Why aren't you wearing one of your outfits, didn't you like them?" Jessica said as she lifted her head to look me in the eye.
"I loved them. I wasn't sure if Chris was coming into the house so I didn't put them on yet. I did wear the bikini today, thank you." I could feel my heart begin to race and my cock automatically flinched.
Jessica pushed herself up, "Please put on the black outfit for me. I really need to see you in it."
How could I refuse her and her pleading eyes? I leaned forward and Jessica placed her hand on my inner thigh to brace herself as she got up. In doing so the back of her hand grazed the side of my hard cock and sent a thrill through my body. She squeezed my thigh as she pushed herself off the couch and held out her hand for me to take. I grabbed her hand and she pulled me up off the couch. No mention was made that my cock was hard as a rock and pointing my shorts straight out. We went to her room like a couple of teenage girls.
Jessica picked up the black corset and held it up to me, "You will look so hot in this, quick, put it on."
I grabbed the garment and turned to leave the room, "Where are you going Jamie?"
"I was going to my room to change." I answered back.
"Really? Come on its just the two of us here you can change here. Now come on and strip those manly clothes off and step into your fun world." Jessica was upon me before I knew what hit me grabbing the bottom of my shirt and lifting up and over my head before I could baulk. Before I knew it she had grabbed the hem on my shorts and pulled them down to my ankles. My hard cock sprang out and slapped my stomach making a loud skin to bare skin noise.
Jessica stood up and looked me in the eye, "Need more help putting your clothes on?"
I quickly started to dress, more to cover up in front of her than to put on my new clothes. As soon as I lifted my arms and shimmied into the corset all inhibitions were gone. "MMMMM, that feels nice." I purred.
"You like your new clothes Jamie?" Jessica's voice was shaky and her breathing was fast. I could tell she was getting turned on by watching me change in front of her.
Jessica grabbed the black leather panties and held them open and ready for me to step into, "Put your feet in Jamie." She instructed.
I stepped into the shorts and she began to pull them up. The leather was tight and dragged against the skin on my legs and she pulled them up. She stood behind me to finish pulling up the short panties. She pulled the front of the short forward pulling the shorts over my throbbing hard cock. When she finished she patted my hard cock through the shorts, "Perfect fit don't you think Jamie?"
I was in a pure lust fog feeling the leather and satin against my skin. Jamie leaned into my back again and as she whispered in my ear she grabbed the cheeks of my ass and gave them a hard squeeze, "Your ass is so tight in these. You like the feel of your tight ass in these panties Jamie?"
Her hands continued to knead my ass as I tried to respond, "Oh god yes."
Jessica's hands move to the front of the leather corset and dragged across my nipples, "MMMMM." I moaned as my legs began to weaken.
Jessica licked my earlobe again. Damn her, she knows my weak spots. "Ya this is what you need Jamie. Doesn't this leather feel nice against your skin? You look and smell so good." Jessica's hot breath was in my ear. She continued to rub circles on my nipples.
"Oh god yes. Feels sooooo gooodddd." I felt my ass grinding back against Jessica's pussy. My head was spinning. I wanted to push back against her strapon. I wanted to be one of those guys in the magazine.
"Ya that's it baby grind that ass against me. Your ass is on fire isn't it?" I felt Jessica's hand on my ass. Then I felt her finger slip under the leg opening on my panties.
Jessica's finger started to massage my hole, my pussy. I pushed back against her finger and started to rotate my hips along with her finger. Jessica continued to work my nipple through the leather corset and the tip of her finger pushed into my ass. "That's it isn't it Jamie? This is what you want, what you need?"
Her voice, her hot breath, the pressure on my pussy, "Yes" I could barely breathe it out. I was lost in lust. I wanted her finger inside me. I wanted her cock inside me. I wanted to be fucked. I wanted to be made love to. I needed to be made love to.
Jessica guided me to her bed and we effortlessly fell together on top. I landed on my stomach and Jessica was on my back. The force of the fall and the reaction of the bed bouncing back forced Jessica's entire finger to embed itself into my ass. The tip of her finger pressed firmly against my prostate. I moaned with a pleasure I have never felt before, "Oh yes, mmmmmm, god, oh shit."
"You like that do you Jamie? You like to be fucked baby? Want more, want something bigger baby?" Jamie was biting and licking my earlobe as she finger fucked my pussy.
"Yes, please yes. Fuck me Jess." I was horny beyond any and every sensation I ever felt before.
Jessica reached under her pillows with her left hand and I saw the dildo that I played with earlier. Her finger slipped out of my ass, my pants were pulled down exposing my ass and freeing my cock. I felt Jess's hot tongue slide between my cheeks. Her hot tongue was wiggling its way into my man pussy. She was pushing her spit into my pussy. She pulled her face back and I quickly felt the pressure of something big being pushed into me.
"Push out baby. Relax and push out." Jess said seductively as she held by cheeks open with one hand and pushed the head of the dildo into me with the other.
My head dropped down onto the bed causing my ass to rise up. I relaxed my body and pushed out slowly. I felt my ass give and open to allow the intrusion. The dildo's cockhead spread my hole farther then I thought possible. There was a sharp pain as my muscles lost the fight to hold the intruder out. My pussy lost and the dildo slipped past the sphincter muscle. I felt my body go limp as I stopped pushing out. That relaxed my body more and Jess pushed more of the dildo into me.
There was that point between pain and pleasure that I crossed. The pain left and was instantly replaced by pleasure. "That's it Jamie, relax now. You want this I can feel it. This is so fucking hot watching this cock disappear inside you. That's it baby take it all." Jess continued to talk me through it and was now rubbing my lower back.
"Oh fuck, this is so fucking hot. I feel so full." I was slowly rotating my hips against the dildo as she fed more of its length inside me. The feeling was incredible. Jess pushed more of the dildo in until I felt pressure against my prostate.
Jess must have felt the dildo reach my prostate because she slowly began to massage my prostate with the tip of the dildo. "There's your little love button. Does that feel good Jamie?"
I all but cried, "UGH! Oh shit, what are you doing to me? MMMMMM, I never thought this would be so good." I wiggled my ass and pushed back, I wanted more. I wanted to be fucked.
Jess began to slowly pull out the dildo and push it back in, "That's it baby enjoy the ride. I'm going to give you the fucking of your life. Feel the big cock going in and out of your tight pussy. You like this don't you Jamie? Tell me you want it. Tell me you want to be fucked."
"Yes, god YES, fuck me Jess. Take that big cock and fuck me good and hard. OOOOHHH!" I was begging for it. I didn't care about anything but that cock fucking my ass.
Jessica fucked me for what I wished to be hours but was probably just a few minutes when the pressure on my prostate was too much, "Oh god I'm cumming, uuggggg!!! Fuck me harder, oh god yes fuck me harder." Jessica starting to pull the dildo almost all the way out and shoved it back in hard. When the dick head hit my prostate my cock shot out streams of cum. My body tensed and shook with the most powerful orgasm I ever had.
I fell forward onto the bed, feeling the puddle of cum against my stomach. Jessica left the dildo sticking out of my ass as she lay next to me. I was sweating and panting so hard I could barely catch my breath.
I felt Jessica's hand rub the sweat from my brow, "That was so hot Jamie, thank you. I have always wanted to do that. You made me cum as well."
"I should be thanking you. I never came so hard in my life. I think I need to wash your bedding."
"You go jump in the shower and clean up, I'll take care of everything else." With that she leaned in and kissed me on the cheek. It was such a nice kiss, the kind that really said 'thank you'.
1 year ago
Would love Jessica to buy me some beautiful lingerie to wear too!