So for the most part, having sex while crossdressing is a bit of a fetish and once people know you are into it they are now free to share their own fetishes with you. Thats were my next life lesson comes in and I have a couple of stories about people doing some surprising near me or to me. Around 26 years old, I was now going by the name Amanda and I met another crossdresser named Missy who I liked to hang out with and dress. Missy and I generally hung around either at her house or mine. Usually we dressed up casually, did our makeup, and just watched TV or played video games, no big show of it. On two occasions we hooked up and this is about one of those times. We were at Missys house and it was past midnight. Missy lived in the basement of her parents house; but entry to the basement was separated from the main house so the only ways in or out were through a door to the outside and through a door connected to a garage. The garage door was always locked and Missys parents never came into the basement at all. After all, Missy was paying rent and this was her place. We had been drinking rum, smoking weed, and playing PlayStation for most of the evening and were winding down. I always brought an overnight bag full of my makeup and some clothes even though I normally didnt stay the night. Missy would tease me about my bag a lot because I always had lube and some sort of toy in it a dildo, a butt plug, whatever. Missy started going through my overnight bag and teasing me about what she would find and lo and behold, she stumbled across a glittery purple, 10 inch double headed jelly dildo! It was new in the package and I had sheepishly purchased it a day ago from a sex shop downtown and then quickly stuffed it in my bag to make my getaway. Missy was histerical about it and was not going to let me live this down. She opened it up and waved it around in the air laughing her ass off. Then she suddenly got a grin on her face, and said Wanna try it! In no time Missy and I were on the floor. I was down to my underwear a basic set of white cotton string bikini panties and a white lace bra. Missy somehow was only in a satin camisole and white knee socks with no panties at all! Missy got on all fours with her ass in the air and I squirted lube on one end of the dildo. I slowly inserted the dildo into Missys ass and gradually worked it in and out until it could go at least a third of the way in. I squirted lube on my fingers and pushed them into my ass as far as I could reach to get the lube as far in as I could. I got on all fours with my ass pointing toward Missys and inched backward until my ass could just touch Missys ass. I pulled the back of my panties down, leaned forward, and placed the top of the dildo in my ass. I slowly leaned back against Missys ass and she let out a stream of curse words Holy Fucking , Stop! Apparently, I was not lubed enough and was driving the other end of the dildo deep into Missys ass. We reset and this time Missy held the dildo right where it entered her ass and I rocked back and forth driving the dildo in and out of my ass until I was nice and slick. We got a nice little rhythm going, rocking back and forth with our butts pressing together on every back stroke. We were both massaging our own cocks and I could feel the pressure of the dildo against my prostate. Just as I was really getting into it, Missy shouted What the fuck, Caleb! and I looked up to see Missys 18 year old brother standing over me with his cock in his hand masturbating like crazy. He crouched over me like he was going to sit on me and I felt his warm cum hit my back. Missy and I both got up from all fours and Missy chased Her brother out of the room shouting and cursing all the way. I toweled off to go home and there was more cum on me than I could ever imagine. Basically Missys brother had snuck into the basement and had been watching us for a little while. He knew we dressed up and must have liked to watch; but this time he just couldnt take it anymore. He left a huge pool of cum on my back and some in my hair. The next experience I want to share is the time I called a female escort to my apartment. I was going through a bit of an identity crisis and had packed up all of Amandas clothes, shoes, and makeup to drop off at a donation box somewhere. I suppose I thought if I fucked a real girl I could get everything out of my system, so I found an ad for an escort. When she showed up she was ice blonde, thin, and tiny, with elven facial features. She had large grey eyes and a slender face. She was very pretty; but her face was slightly wrinkled and worn and did not match the almost proportions of her body. In hindsight, she was likely much older than I was and also may have been a bit on coccaine, or had an eating disorder, or both; but who really knows. I remember she seemed confident and in control and I wasnt worried about her welfare. As soon as she arrived, we said a quick hello, she asked for the bathroom, and she went straight in to clean up and get changed. When she returned she was wearing a white gauzelike nightie and no panties. I vividly remember she had no pubic hair at all and very prominent hip bones. She asked where the bedroom was and I led her there. Once in my room she almost immediately noticed my large dildo and a bottle of lube laying on the nightstand and asked if that was for her. I blushed a bit and , then quickly raked the dildo and lube off into the nightstand drawer. She moved around my room looking at all of the things in boxes along the floor and stopped at a box of high heel shoes. She stared at me for what seemed like forever and finally asked if I liked to dress up. I replied that I did at one time but not anymore. She pulled a ziplock bag of makeup from one of the boxes and told me to sit down. She dumped the bag of makeup on the bed and picked up a bottle of foundation and some brushes. She grabbed my chin and demanded, Look up and started smearing foundation on my face with her fingers. The escort applied foundation, eye makeup, and lipstick to me, then stepped away and started rummaging through a box of dresses. I could see my face in the mirror and I had deep red lips and nice dark eyes; but overall the makeup was a bit rough. The escort pulled out two dresses: a semiformal, red cocktail dress and a silver, form fitting, spandex, sequined mini dress. She stepped into the cocktail dress and spun around, zip me. I zipped her up, but the dress swallowed her and hung slightly off one shoulder. She handed me the silver sequined mini dress and I pulled it on over my head and smoothed the sequins over my body. I had found my favorite auburn wig and put it on as well; but the escort pulled it back off and handed me a cheap blonde party wig with malt pink highlights instead. She next went through a box of shoes and pulled out a pair of sky high, black patent leather platform heels, handed them to me, and said find some panties. While I looked through the various boxes for panties, she was looking through the dresser drawers of my regular clothes. I was about to tell her to stop when she pulled a pair of denim shorts and a belt from the drawers. I watched as she lifted the cocktail dress and pulled on the shorts underneath and threaded the belt through the loops. She then took the large dildo from the nightstand drawer, unbuttoned and unzipped the shorts, shoved the dildo into the shorts, and finally buttoned and partially zipped up around it so it was jutting out like a strapon. She then cinched the belt tight around her small waist and gave me a long expressionless stare, turn around. I turned around and the escort guided me down onto all fours on the edge the bed and then she lifted my dress from the back. She pulled my panties down, fidgeted with something, and then wiped a well lubricated set of fingers across my asshole. She then leaned in closer and I felt the large dildo slide into my ass halfway, giving me a filling sensation. She shifted her feet forward to get closer and pushed the dildo even further. I felt an immense pressure inside and the dildo felt like it was hitting my pelvis when she placed her hand on my shoulder and lightly pushed me down until I was lying on my face with my ass high in the air. I could feel her shift behind me and push a little more, working the dildo deeper inside. I felt what I can only describe as a pop deep inside and the dildo immediately slipped even further in. I could feel the fabric of her cocktail dress pressing against my ass and her finger nails slightly digging into my hips and buttocks. She began moving the dildo in and out with her hips and I could see my stomach heaving out each time her hips thrust. She pushed faster and faster and all I could hear were the sucking and squishing sounds of my asshole expanding and contracting to accommodate the dildo. She fucked me for a good 15 minutes before finally backing away and pulling the dildo out. She removed the shorts and dildo contraption and tossed it to the corner of the room. The next sensation I felt were her fingers tracing around my asshole and one by one inserting them inside. I felt her fingers push forward into me, then a pause, and more fingers pushing in, followed by a sensation of fullness. I pulled my long hair to one side and glanced back over my shoulder to realize the escort now had her entire hand in my ass almost to her forearm! The escort began to move her arm slightly in and out of my ass; but never removed her hand. I could feel her moving her fingers around inside of me, like she was slowly making a fist and releasing it again, over and over. Waves of pleasure ran through my body like I was about to come; but I never did. I was perched on all fours on the edge of the bed and my knees and thighs would shake uncontrollably when the most intense waves would hit. I began to rock back and forth on her arm, pushing her hand and fingers deeper and pulling them back again. The escort pushed my dress further up my back, almost around my neck now, and ran the finger nails of her free hand up my spine and back down to the small of my back. I was fully in the moment now and gyrated my hips like a stripper giving a lap dance, rocking back and forth on the arm in my ass. The escort pulled my panties down to my knees and instructed me to lift my knees, so she could take them off. While I was shifting from one leg to the other, I looked down and noticed a large puddle of semen on the bed below my cock and a long, thin, glistening string of semen running from the tip of my cock down into the puddle. The escort took my panties and, with her free hand, wrapped them loosely around my cock and started to stroke, running the panties up and down my cock. At almost the same time, she began pushing her fingers against my stomach from the inside of my ass. I could feel the pleasure waves coming back again and began rocking and gyrating on her arm. I could feel the waves getting stronger and stronger until a huge wave ran up my legs and into my back as I pumped cum into the escorts hand and into the panties wrapped around my cock. The muscle spasms from my orgasm were so strong that my hips joints and back popped sending shivers down my spine. After a few minutes the escort slid her hand and arm out of my ass and I heard her take a step back. My asshole was still tightening and loosening in rhythm with each smaller wave that passed through my body. The panties were still loosely wrapped and clinging to my cock, soaked in my cum. I heard the clicking of heels as the escort walked down the hallway to the bathroom. I heard the sink water run and, shortly after, the sound of heels clicking through the living room, followed by the sound of the front door opening and closing. I composed myself and hobbled into the living room, on weak legs, wearing only the silver sequined mini dress and pink and blond wig. I had decided that night, being a boy/girl had its benefits and I began unpacking my clothes back into my closets. On later inventory, I found the escort had left behind her tshirt and shorts, a pair of cotton panties, the seethrough nightie, and fingernail scratches up and down my back, hips, and butt. She upgraded though, as she left that night wearing the red cocktail dress, a nice pair of heels, Victoria panties, real pearls, and holding a satin clutch purse and my iPod 🙂

I was 24 and living on my own in a different town from where I grew up. It was far enough away that I could be anyone I wanted to be and so I got deeper into dressing up. I had a good job now, so I could afford some nicer clothes, and now that I had my own place, I could order things through the mail without worrying about prying roommates or parents.
In the city where I lived, curious men placed personal ads asking for guys to meet them in a coffee shop, park, or something. It wasn’t to meet for sex in public, it was just to meet, sort of a way to determine if someone was gay before you make your move I guess. One day I followed up on an ad asking to meet in the back corner of a bookstore. The ad said to pick out a specific book (I don’t remember the book) and thumb through it so the guy would know you were there answering the ad. It sounded interesting, so I went to the book store, in guy clothes of course, found the book and sat down on a nearby chair. After a few people cleared out of the section, an older guy sat down in the chair next to me - and by older I mean around 55. He asked if I had ever read that book before and I but a friend I was meeting here had recommended it. He took the hint and introduced himself and we made small talk for a bit, then he asked if I would be interested in continuing our conversation over lunch. I went along with it for now, not quite sure where this was going, but we DID actually have lunch and we got to know each other with some pretty interesting conversation. We will call him Jones for this story. Jones was basically just a bit lonely and bi-curious and also seemed to be into the fact that I dressed. We met up again a few more times in public for lunch and conversation and eventually I gave Jones the address to my apartment.
After a few missed connections, Jones found his way to my apartment one night and I could tell he was excited and had finally built up his nerve. I let him in and excused myself to my bedroom to get dressed. At this point I was basically keeping myself smooth from the neck down on a full time basis, so all I needed to do was apply my makeup, shake out my wig, and get a dress on. I douched quickly before starting my makeup. The makeup was (and is still) the hardest part of my routine, so I didn’t present very well that night. For my outfit, I chose light pink panties with lace strappy sides and a matching bra. I had pads safety pinned inside the bra cups to fill out my top. I squirted a bit of lubricant deep into my ass using a syringe applicator I kept around just in case. I chose a form fitting black cocktail dress with a white collar, what I called my Audrey Hepburn dress, and a pair of black 5 inch heels. My legs were freshly shaven just before Jones showed up, so I skipped the stockings and went with bare legs. At the time my go to wig was a straight, auburn color with bangs that swept to one side (very 90s) and length down to the center of my back.
I walked into the living room and found Jones sitting on the couch. As soon as he saw me his eyes narrowed and a sly smile crossed his face. I’d never been on the receiving end of a look like that from a man; but I liked it. I turned off the living room light, leaving only the glow from the hallway light and television. I figured the low light would help cover my half-assed makeup situation. I sat down on the couch next to Jones and we talked a bit. He complemented my hair and my dress as I did my best to keep a feminine voice through the conversation. I wasn’t perfect by any means; but I could tell Jones was down to play pretend with me anyway.
Jones leaned in to kiss me and I guess because of the age difference or something, I was startled a bit; but let it happen. He moved to my neck and then my ear lobes, when one of my clip on earrings popped off and fell in between the couch cushion. He didn’t stop when the earring fell and I could feel his hand rest on my knee, then slowly slide up the top of my thigh.
Just as his hand almost reached the cock in my panties, he swerved over to my hip and slowly crept up inside my dress until his hand rested partly on my stomach with his fingers around my waist. He kissed me deeper and at this point I realized I very much liked the feel of a mans hands on my body. I started to get hard, so I pressed my thighs together to keep my cock from popping loose from where it was tucked into my panties.
Jones stood up in front of me and I could tell through his dress slacks that he was hard. Jones unzipped his slacks and reached down to hold both of my hands in his. He moved my right hand into his unzipped pants, so I reached in, pulled his underwear below his cock, and pulled it out of his pants. His cock was average to short in length but he was pretty thick and he wasn’t even fully hard yet. I was slightly afraid he was about to put this thick thing in my mouth; but instead he guided my hand over his shaft and started to move it up and down. Through later dates with Jones, I found that he has a fetish for handjobs from girls with large hands - so I was right up his alley. Honestly I’m not experienced with blowjobs anyway; but this I know!
My right hand slowly slid up and down his shaft, squeezing slightly at the base each time and turning as I worked toward the head. Every third stroke or so, I cupped my palm over the head of his cock and turned it slightly before going back down the shaft. With my left hand, I worked his pants and underwear down a bit so I could wrap my left hand around his balls. I cupped and lightly squeezed his balls each time I worked my other hand up to the head of his cock. I could feel his balls draw in a bit and knew he was getting very close to cumming.
I stood up and took Jones’s hand and led him down the hall to my bedroom. We left his pants and underwear in the living room and he pulled off his shirt as we walked. When we got to my room I was so hard at this point that I immediately sat down on the edge of the bed, rather than stand there pitching a tent in my little black dress. I reached over to the night stand for a condom and rolled it over Jones’s hard cock and then placed a strip of lubricant along the shaft and stroked his cock with in hands. He let out a deep breath and I thought he would come right there, so I backed off. Jones leaned toward me and laid me back onto the bed. His hands ran up the outside of my legs and pulled my dress up into a bunch just above my belly button. Jones grabbed the back of my panties and pulled them slightly down my thighs as I raised my knees as high as I could toward my chest. I could feel the lace band of my panties stretch tight and dig into my thighs as I wrapped my legs around Jones’s back. Jones leaned toward me and gave me a very light kiss as I felt his cock push into my ass. Jones was about as thick as my largest dildo, so I could feel the slight sting and stretching of my asshole as he entered. He pushed hard against me to go in as deep as he could and then, feeling the tightness I guess, he pulled all the way back out. His next thrust was a bit slower, as if he was trying to be more gentle, but his cock had already dipped into the lube I had put in my ass earlier, so there was almost no resistance this time. I could still feel the stretch, but no sting this time, and the fullness was exciting to say the least.
Jones laid on top of me with his head in my hair, breathing deep into my neck, and pushed in and out of me in a steady rhythm. The entire time his hands slid smoothly from my thighs to my butt and to my waist. Each time his hands moved to a new part of my body he would squeeze slightly and slide them to the next, I was in heaven! At one point my cock jumped a bit like I might cum and I instinctively tightened by sphincter around Jones’s cock as a reflex. Jones bucked slightly and let out a short groan and pushed his hips hard against my ass. I could feel his cock swell slightly inside of me and I was pretty certain he had come.
Jones slipped out of me and laid across the bed. I laid there with my dress pulled up and my panties at my knees as he traced my legs with his fingers. Jones took off one of my high heels and slowly massaged the arch of my foot and my toes. I had painted them bright red a few days earlier so they were still very pretty. We talked and laughed just like we had done weeks before during our lunches. Jones finally had to go, so I followed him to the front door as he collected his clothes and got dressed. I had gotten my dress and panties back into position and still had my heels on. At the door he wrapped his whole arm around my waist and pulled me in close to give me a deep kiss. It was sort of an awkward, old guy kiss, like from an old movie, but it still felt very nice.

By my first year of college, I had been dressing secretly almost every night for close to . I had stopped, purged, and restarted a few times - usually I stopped dressing whenever I had a girlfriend I was fucking. Ever since I began dressing, my late nights in my room would be consumed with dressing in my collection of lingerie and working myself into a frenzy with a dildo until I came. I would repeat over and over u til I was spent and . Sometimes I wouldnt get out of my nightie before falling asleep and I would wake up with a start, wearing lingerie with my ass gaping and sore and late for school or work. On occasion, my friends would get me to go out to a bar or just to go somewhere outside of the city to drink and smoking weed on the tailgate of a pickup truck somewhere, just being guys. I could play that side of my life just as well. One night we all went to a popular club in town and drank our share of nickel beers. We were pretty when we ran into a guy who asked if we wanted to go to a party he and his roommates were having. This guy was a real country boy, he had the hat, the boots, and everything. All night he was drinking Jack and Coke, so we kept calling him Jack. After a bit of cruising the club, we figured what the hell, should be some girls at Jacks party and they had more beer. We got in our cars and followed Jack way out of town to a townhouse in the burbs. As soon as we arrived we could tell this party was not happening. They did have more to drink but the only people there where Jack, his two guy roommates, and one of the roommates sister. The guys all took their chances trying to hook up with the sister; but it just wasnt happening. Meanwhile, I was at the kitchen table playing quarters with Jack and one of his roommates when an unexpected bet got thrown down. If the roommate made the next shot I had to kiss the Jack. The roommate sinks the shot, I look around for my buddies, and then I lean over the table and kiss Jack. Nothing much just a regular kiss. After a few more rounds at quarters, I hit the restroom and then head over to a table in the corner of the kitchen where the whiskey and mixers were. Im mixing a drink when Jack comes up behind me and starts kissing me on the neck. He reaches around and starts rubbing my cock through my jeans, then leans around and gives me a good deep French kiss. Just then one of my buddies rounds the corner as says its time to go. I could tell he thought he might have seen something strange going on; but just wasnt sure what. Jack tried to get us all to stay and then tried to get me to stay behind; but it wasnt happening. My friends dropped me off at my house and everyone went their separate ways heading home for the night. Honestly, that was my first kiss with a man and my head was spinning. I couldnt stop thinking about it.on the ride home I had made up my mind. As soon as I got inside the house I grabbed a duffel bag and threw some of my clothes in it. I went to the bathroom and cleaned up my downstairs and grabbed my car keys. I memorized every turn on the way back, so I knew exactly where to go. I showed up at the door to the townhouse and the roommate from the quarters game (Kyle) yelled back, Hey Jack, look who showed up. I came inside and Jack came up to me and gave me another deep kiss. I told him I needed to get changed then I pulled out the first thing in my bag - a black satin teddy - and said simply I dress. Jack and the Kyle looked slightly disappointed; but shrugged and said well, bathrooms over there. I went into the bathroom and pulled on the satin teddy but I had forgotten stockings or garters. My legs were hairy from the upper thigh down but I generally kept my face, chest, balls, and asshole cleanly shaven. I grabbed one of the guys razor and went to work on my legs and underarms (I was desperate). I had remembered to bring shoes, a little makeup, and a cheap blonde party wig. After I was as smooth as I could get, I put on a little lipstick and the party wig then slipped on a pair of red heels from my