Melony reborn.
Reading so many of your stories Iâve decided to share some of mine. Iâm sorry, Iâm not much of a writer but I will try. A little about myself. If there was ever a guy made to be a crossdresser it was me. I pass as a girl.
Well, I used to, age came around and it just became too much work to try and keep a girlish figure. Iâm not a big guy by any means, 5â 7 at best, 5â8 Ish in heels. Iâm not a hairy guy, even at 58 my body is pretty much hair less. Even my Adamâs apple is not very pronounced. I have small feet small hands my butt even has a twitch when I walk. Drove my dad nuts. My stepsister used to tell me I had a body like a girl and dressed me up like a girl and would drag me out into public. I became a total sissy little fag slut way back in the day. Iâm sure youâve seen them on websites, the cross dressers that you wouldnât know it was a dude unless naked. I was one of those. I was also very lucky, that those that knew my secret. Kept it to themselves. I was only caught once. And it was a heart break.
In this story both of us were 19 years of age, at the beginning, this story took about 3 years.
I met Andy in high school around 1982. After graduation we just fucked off all summer and became best friends. BTW, Andy was a spoiled little rich grandson. His grandparents made sure he always had a car and always had money with him. They paid for us to go on trips pro sports games and what not. Spoiled little rich kid.
After the heart break I spoke about I stopped dressing, I stopped having sex I didnât care about much until Andy got me to start going out and doing things again.
One day, we were sitting at a red light and Andy started asking me about guy-to-guy sex, if I had ever done it, no. Was my reply, (I lied) and asked if I had ever thought about it. And if I ever would. My reply was, oh I donât know, it would just have to be all planned out I guess, or something. Never really thought about it. (I was still lying), Andy knew nothing of my past) He kept asking questions like, what do you think would have to happen? Pretty sure he was getting excited talking about it. I said, well. I would have to be drinking, it would have to be someone I knew wouldnât talk about it to people, and I would need a gay porn video because I wouldnât know what Iâm doing.
Sometime after his 19th birthday, which was October, after Christmas and before my 19th which was February, so it had to be in January, snow on the ground Andy called me and told me to pack a bag, his mom and grandmother had left and gone to their house in Florida. (I did say they were rich.) I was still living with my dad and Shirly. So, any chance to have a house to ourselves for a few days sounded awesome. I told mom Iâd be back in a few days, told her what was going on and was out the door when Andy pulled up to pick me up.
Andy had some other people over that night, we must have been boring, so they all had left around 10pm or so. We had been drinking a bit, after they left Andy brought out some porn movies that he had in his bed room, I said I need a shower first, going upstairs I found an enema bottle in the closet that held the towels. So, for my shower I got clean inside and out.
Once back downstairs Andy showed me the vhs vids, Debbie does Dallas , inside misty something and a guy one, back pack campers or something like that.
I said letâs watch that one first, we grabbed a couple blankets and laid at each end of the couch.
The movie started with guys packing their back packs and hiking through some woods, pitching camp and be for you know they were sucking cock. Watching the cock sucking made me hard, I stared wiggling around under my blanket and Andy asking what I was doing. I said Iâm taking off my sweatpants. He asked me why. I told him it just feels right watching something like this. I think you should too, it just feels right, I saw Andy wiggling under his blanket removing his sweatpants. Yeah, that feels right he said.
Thatâs when I made a move.
I could see Adny was hard, I rolled toward him and asked, âare you hard?â I reached out and put my hand on top of his dick head, I leaned in more and whispered, âI want to see itâ I was already pulling his blanket down past his waste. His dick popped up, and it was nice, prolyl 7 inches about as big around as a half dollar coin.
Once it popped up, I put my hands on his thighs and looked at it, briefly, then I just swallowed it, I took it all into the back of my throat, full strokes with my mouth. It felt so good to suck a cock again, I played with it a bit, I looked at the vid and they were kissing, I pointed to the tv and said we might as well get that out of the way. I sat up and put our dicks together and leaned in and kissed him opening up for his tongue, as I was grinding our cocks together, I started sucking his tongue instead of just Frenching when I started running his cock up and down the length of my butt crack. It felt wonderful. Andy wanted to sixty-nine, it felt great to have someone sucking my dick again. Again, I looked at the video to guys in a tent sixty-nine with one guy licking the other ones boi-pussy. I got up so Andy could see and told him âlookâ. He pulled me back down, with my knees in front of his arms an tried to sink his tongue in me. It was a wonderful feeling. I started humping his face with my ass. He responded well. With long licks an slipped a finger inside me, adding saliva to my inside, adding some lube to myself and his dick I sat across his waist legs spread across him, I raising up and placed his cock head at the entrance of my man pussy , I slowly slid down around his cock. It had been so long since I had cock in me I could feel the stretching and the pleasure of a cock inside me again.
Slowly, it took a little time, but I got all of him in me. I started to grind it in, his hands on my naked hips he started to meet my thrusts, But I wanted Andy between my legs fucking me like a little slut.
While slowly riding Andyâs cock, I looked at the tv, the guy had his legs back while they were being held back by the other guys arm, his legs were over his arms while he was getting fucked. I told Andy, âlookâ, I want to fuck like that. After I put a cushion in the corner of the couch I laid back and playfully lifted my legs for Andy,
As Andy got into place I guided him into me, My legs draped over his arms I was ready to take a good fucking, and I told him so, once he was all the way into me I told him, now fuck me, fuck my ass and donât stop until you cum. He started slowly to slow to suit me, I said fuck me, I told him, and thatâs what he did he started pounding my ass really good, I told him I could feel his balls slapping my ass, his strokes where long and deep and fast, he was grunting with the effort, sounds started to involuntarily come from me, I was feeling the fucking, each stroke brought a sound from me. With each trust came a âAhhhâ or an âuhhhhâ Andy asked if I was ok, my only words were âdonât stopâ I pulled his face down to me and sucked his tongue some more, I wanted that in me as well, I grabbed his ass and started pulling him into me. After maybe 15 minutes of this fucking I felt Andy speed up and started thrusting even harder, finally he says âIâm going to cumâ it came out in grunted words. I could feel the prostate orgasm building up in me, with those words it hit me I was trembling with extasy. Andy said he was going to cum, all I was able to say was âyeahâ it was barely a whisper. He began to breath even harder and started making an AhhhhâŚ.. Ahhh grr⌠sound, I pulled him even farther in, with a gasp he started to release his load into me, I could feel his cock pulse as he pumped he cum deep in me, this was happening as I was having my orgasm, for the third time in my life I was having a hands free orgasm. I made some kind of big mess. Andy practically collapsed on top of me, I wrapped my arms and legs around him while we tried to catch our breath, he kissed me deep tonguing me. After a few minutes he got up and went to get us a towel, when he came back and sat down, I took him back in my mouth to clean him up.
We had another brew and finally he said âI think thatâs the best pussy Iâve ever hadâ So I leaned forward and kissed him on the lips. Just a quick peck, but I said thereâs plenty more of that if you want.
He playfully called me a liar, youâve done this before havenât you? So, I confessed. I didnât tell him about the cross dressing though. Or the heart break, I wanted to keep that to myself.
This type of sex went on from then and all through summer, one day Andy gets us a room, and dinner, to tell me he would be leaving at the end of the month to move to Florida and start collage. I knew this day was going to come but I still wasnât ready for it.
He said he would come home on every break, every holiday. But he never did. It took almost two years for him to come home.
In the meantime, I had gotten a job as a dishwasher in the only fine dining restaurant in our area. I wanted to be a chief; I couldnât afford culinary school so the only way I could make it was to learn it first-hand. I wasnât by any means getting rich, but I was making enough money to move out of moms and get myself a very cool studio apartment. It was cool, not because it was my first place, but the front had a window all along the top in front, kind of like a sky light. My furniture was used but I had the comforts of home.
My job was going well, one day the chiefâs assistant called off work. I was training a new guy at the dish tank, and I was out on the floor cleaning tables. And did we ever get slammed. The cook, Chief Rick, started bitching he was beyond able to keep up. The boss (Terry) came out and told me to go help Rick.
I did my best once I figured out where the things were that Rick was asking for, I was actually helping out. We got caught up and at the end of service Rick told me for a guy just getting thrown in there I did an outstanding job. I was so fucking proud of myself.
Ricks back up chief just one day up and quit. Terry told him he would hire him some help. Rick said to Terry, get someone for the kitchen, I want Mel to back me up. He would do fine and do a good job and he has what it takes.
The thing was by this time I could do everything in the kitchen but run it. I could run it, and I had when we were short handed, and Terry didnât want to lose that. But he finally gave in, I got a good raise and moved up.
This took about a year and a half to get to this point. With the extra money I was able to get a dependable car, it wasnât pretty but it ran good. You know, a beater.
My first apartment and my first car. I was doing ok.
I think it was the month of November, I got a call,â heyâ was all he said, Andy?
He apologized.
He told me he was coming back to town in January. I need to know the date so I can plan something. I told him about my apartment and the job and that I was doing ok.
I got the date and wanted to make plans for something special.
Almost two months from then.
After a few days after getting this information, my sister Jess and bestie Sara stopped over with some wine, we sat around getting a buzz on and were talking. Andy came up, the girls and I had never talked about Andy, so I told them all about it. Jess was the one that got me to start dressing. I wanted to do something special and also explained that I was pissed about how he had not contacted me since he had left.
Sara said, âYou want to blow his mind?
Her idea was to bring back Melony. My cross-dressing alter ego.
Totally catch him off guard and dress. And fuck or suck off some other guy, and make sure he knows about it. Oh fuck, thatâs a great idea.
Jessica was all for it, she told me âYou have no idea how much I miss my little sisterâ.
So, we made a shopping date. I hadnât dressed in about 4 or 5 years. Jess and Sara brought over some of their clothes. Some makeup and other things a girl needs, they helped me with my make up and picking out an outfit from what they had brought with them. We went shopping, I went dressed for the first time in years.
Melony was reborn.
Our shopping date was sometime in December.
Andy wasnât coming back until January, I needed two winter outfits . Both slutty. I settled for two, one piece woven turtleneck sweater skirt that was charcoal gray and a black one. This would hide what Adams apple I did have, which wasnât pronounced at all. I was planning on knee high boots with heels. But, Sara found these little ankle boots that had a fur cuff at the top. They were so sexy. The whole idea was to look like a total sexy little slut. The skirts came down to be just above the middle of my thighs. The plan was, no stockings.
Then we started looking at wigs. I canât tell you how much fun it was to be out shopping with the girls dressed as Melony. I didnât realize how much I had been missing this.
This is when Jess grabbed me by the back of the head, by my hair, and said âI donât think you need a wigâ I didnât realize how long my hair had gotten. Mom had always gotten after me about my hair and to keep it cut. Now that I was out on my own, I thought back, I hadnât had a cut since I moved out of moms, I was putting my hair back in a tail to cook, but didnât really think about how long it was, My hair is curly anyway so.. Sorry old habits I apologized.
Sara suggested I dye it black. Add some product and stretch out the curls, she had found the cutest chauffeurs caps, I picked out a black one, it would go perfect with the outfit.
We took everything back to my place and the girls reminded me how to put-on makeup. We practiced walking, i which isnât hard you just have to walk in a straight line, kind of heel to toe, but with a stride. A straight line like walking on a rail. I practiced walking in heels which I hadnât done in what seemed like forever. They remined me of the exerciseâs girls do to keep their girly figure, which I hadnât forgotten and still did many of them. I couldnât get my girly voice back though; it just wasnât quite right. We came up with a plan for that as well.
The big night, Andy had been back in town for close to two days, I wouldnât let him see me. I wouldnât go see him; I wouldnât give him my address.
A new hotel had gone up since Andy had left. The rooms were set up to over look the dinning area and the pool, each floor had itâs own landing floor and balcony. Sort of a dome.
I had reserved a room for three days and used vacations days from work. I didnât want any of my neighbors to see Melony. So, I thought this was the best way to go. The idea was for Melony to have her fun at night on second shift, and Melven to go about his business on first shift so no one would know, in case anyone knew me.
I was a nervous wreck. I wasnât sure I could pull of the look any more even though the practice run went well. I was still a wreak.
Jess and Sara showed up that night to help me shave the hair I couldnât reach or see, my legs were shaven, my nether regions were shaved, I was pretty much completely hairless, except the hair on my head, they helped me with my makeup and the dress. Everything was dark, Dark sweater skirt, dark eye liner, the eye shadow was two tone, dark gray and lite gray in a cat eye shape, my lip stick was a very dark burgundy, bloodberry I think it was called, dark nail polish. Also bloodberry if I remember right. I was fully dressed and ready, I checked the mirror, and was happy with what I saw, Melony was back, my confidence had returned. I was one sexy hot fucking slut. Smelling of soft musk, it was my perfume of choice, And I was happy with it. I was ten minutes early. I was able to look down from my room and could see Andy was already there. The first thing that went through my mind was, Heâs lost weight. He looked good. I grabbed a small piece of paper from the little note pads they give you in a hotel, and wrote something for Andy.
The girls were practically pushing me out of the room. âheâs here, get down thereâ Sara said scoldingly.
Lock up the room, please, I said as I walked out of the room. Jess gave me a quick peck on the lips Sara smacked my ass and told me to go get him slut with a little laugh in her voice.
As I stepped out and started âthe walkâ I felt sexy as fuck, it was all I could do to keep from getting hard.
Did I say I could pass? The looks I got proved I still could.
I could hear my heels clicking as I walked on the marble walkway, heading towards the elevator,so could others, as I saw people looking up to see were the sound was coming from. I could feel my ass with its natural little twitch and the way I was walking I could feel my ass swaying, I was catching a slight breeze up my skirt, And it felt so fucking hot. All I can tell you, is, I felt so fucking hot I was starting to drip precum. If I had a vagina, it would be soaking wet.
My skirt had ridding up to just above mid-thigh, and I wasnât going to pull it down, let them look, I had worked hard and spent some money to look like this. I could feel the guys turn around to check out my ass as I walked by, and I loved it.
I walked right in, the host asked if he could help, I shook my head and pointed, I was in full Melony mode now, I was in the role.
I walked right up the Andyâs table and sat down.
He looked at me, and I could see wonder and a flash of lust in his eyes.
âIâm sorry miss Iâm waiting on a friend.â Andy said to me.
As I sat down, I let my skirt ride up to show the bottom of my ass, I acted shocked and reached down to smooth it out and pull it back down, I looked shocked, and looked around, I caught this older gentleman looking a little embarrassed that I had caught him, as I just smiled and looked away, as I had intended, I also saw a wife swat her husbands shoulder. It felt good.
Andy has said, Iâm waiting on a friend, He didnât know it was me.
I pulled out this little piece of paper and slid it across the table to him.
I leaned forward and whispered , âI know.â
He just looked at me and shifted his eyes to the paper.
It said.
You will call me Melony.
If anyone asks, Iâm just getting over strep throat and my voice isnât returning the way it should,
My doctors have told me to whisper if I had to speak and try to not even do that if it can be helped.
He had a confused look in his eyes, I leaned forward again and whispered,: âhi Andyâ
It still took a few seconds, then his mouth dropped, he whispered, oh my gawd. Then it got louder, Oh my gawd! I stuck my fingers to my lips and went shhhhâŚâŚ.
While still whispering, I said reread the paper.
He was still at a loss, I leaned forward and gave him a peck on the lips, he still wasnât sure and whispered . Melvin? ShhhhâŚ.. I whispered, âMelony.â
Then I whispered âclose your mouth. You look ridiculous. â He shook his head in disbelieve and said, you look great, he was getting his head straight after I had just rocked his world.
Dinner went well, Andy did well as we ordered, he explained I couldnât talk. I pointed to what I wanted Andy had a bottle of wine for us, as we caught up. I let him know I wasnât happy with him, and you better make it up to me. The waiter was someone I had gone to high school with. He was a real dick to me, so Andy explained to him I couldnât talk he asked if I was still sick, Adny did great, âno her voice is just taking it time to recover, he leaned over and told me how sorry he was to hear it, I mouthed the words Iâm sorry, thank you, as I touched the back of his leg, I decided if he was here tomorrow I was going to suck him off. After all, this weekend was all about getting dick, and I didnât care where it came from. During dinner I ask Andy if he remembered that guy, he did, Andy said something about him being a dick in high school. I told Andy, if he works tomorrow night Iâm going to suck his Dick He wanted to know why, I whispered my own little type of pay back. The pay back? Getting sucked off by a guy. Lol.
After dinner we went to the room, so I could check my makeup. After a little heavy petting, we went down to the club and danced, I had my hand in his pants on the floor, I was trying to get him off on the floor. But he wouldnât let me. I was still pissed at him though. This guy comes up and askes me to dance, out on the floor he asked me if he could get a dance like my friend was getting, I asked, did you see that?(still whispering) Yeah was his answer. Is that all you want? Sure, was all he said. I grabbed him by the belt and told him to follow me, I took him to restroom into a stall and sucked him off, I took his above average cock in my mouth and he put his hand on the back of my head, fucking my face and told me how good I was at it. He at least let me know when he was going to cum. He had a lot but I managed to get it down without getting my sweater messy.
I got back to the table and Andy asked what had happened, so I told him. He wasnât to pleased about it, but I didnât care. He must understand Melony is a slut. It just happened. And Iâm not sorry about it.
I reached under the table and rubbed his cock through his pants, I told him thereâs plenty more of where that came from, and you could have at least called me once in two years, and how Melony is a total slut, whispering I told him some more about my past. How all this started and the first time I sucked a cock. I swear he was blushing
I stroked him under the table. If the tablecloth had been longer, I would have blown him then and there. After toying with him some more I told him I was ready to go to the room, I had some wine sent up, I wanted to drink and get fucked.
Once we got to the room I poured us both a glass of wine and decided this wasnât going to be enough, so I ordered two more bottles of red to be brought to the room, Andy was eager to go but I wouldnât let him touch me just yet, âwe are waiting on room service, I told him. The guy that had been such an ass in high school brought the wine to the room, I answered the door and whispered a thank you and gave him a slow slutty wink slipping him a five and making sure my nails ever so slightly scratched the palm of his hand, I knew it had the effect I wanted by the way his hand twitched and the blush that filled his cheeks. I asked if he worked tomorrow night, he looked down at his feet saying yed, I gave him another sultry wink and whispered Iâll see you then. He walked away with a bright red face, I just laughed to myself.
I downed my wine and poured another, Andy so because of the flirting, Andy called me a whore, I was really feeling my buzz by now, I told him to put his money on the night stand as I crawled across the king sized bed like a cat, he told me ânoâ ok âwell you see lover, Iâm not a whore, Iâm a slut, and your going to fuck me like a slut.â He kept backing away from my lips until he couldnât retreat any more. In one swift move he flipped me over and shoved his tongue down my throat while pulling my panties off from under my skirt, it surprised me, he went down on me taking all of it, (just a little over 7 inches a little more then a 50 cent coin) and just held it in his mouth at the base making small sucking motions, it felt so good, my eyes rolled back and I just let out a moan. He slowly started sucking up and down, making me shiver each time he reached the base. âyour going to make me cum, you have to stop.â I told him, Iâm not ready yet.
I retreaded into the pillows at the head of the bed.
I asked him how he liked his home coming? âTotal shockâ he wanted to know why he hadnât seen this before, I wanted to keep it to myself I answered as I pulled my fake breasts out of my sweater. He told how good I looked, I kept saying ok, as I was taking his pants off of him, âyour fucking Melony tonightâ I told him tonight and you better be up to itâ. I went down on him, just the head, with a little nip, he jerked from it, then I took it all, five minutes of long deep sucking and I raised up, grinding our dicks together like we used to, kissing deeply he opened his mouth and I sucked his tongue as I tried to squeeze his cock with the cheeks of my ass. Squeezing his cock with my legs. I reached the night stand an got out a bottle of lube, slipping a finger in me lubing myself up, I lubed him up. Raising up, I guided him into me, in and out working the lube in till I could get all of him in me. I was grinding him, keeping it deep at the base, it just felt good having him in me again. This wasnât good enough for Andy.
He started saying things, I want to fuck you slut, Melony I want to fuck your slutty little ass, he pulled me off him and rolled me over, I stuck my ass in the air, laying facing sideways on a pillow, I told to fuck his little slut, fuck her good, and fuck me hard! He went all the way in me, making me arch my back, the sudden stretching was intense, almost painful but with a sense of pleasure Andy started his assault on my ass, all the way in sometimes staying in with short hard strokes, sometimes pulling all the way out, slamming it back home. He fucked the little slut good and hard for about an hour, calling me slut, you like that slut? Take it you fucking slut, I could hear him banging my ass the whole hotel could probably hear it, I could feel his balls slapping my ass, even with a assgasam, when you tighten up he was still punching it through, bringing animal grunts from me, I tried to keep it quit. He finally garbed my hips and just said, âCummingâ and did he ever, I could feel it dripping down my legs before he was even done. Then he just leaned over, reached in and started stroking me with his hand. I told him to stop, I needed to catch my breath, I had such a assgasam, not only was I visibly shaking, I donât know how or why I didnât have a hands free orgasm.
We just laid there for a few minutes, I started licking his cock and sucking it slightly just to clean him up an milked it to get it all out, I went and got us towels to clean up. After another glass of wine I started playing with him again, and told the job isnât finished, I started sucking him again, taking him deep and just sucking at the base until he came in my mouth. I gave him a few minutes and cross legged walked my dick up to his face, which he readily opened his mouth for me, I slowly fucked his face as his suction was hard as I fucked his mouth until I came, he made a point to see that he swallowed it. We lay down and turned the tv on. It was 2 am, we had fucked for two and a half hours.
I woke up to hear Andy in the shower, I staggered in and checked the mirror, my makeup was a mess. Lol eye liner smutched, hair a mess. I got in the shower with Andy and asked him what he was doing, he had to check in with his grandparents, (get more money) and other things he had to do. So, Iâll see ya tonight?
He asked if I was still going to suck that guy off and I said yes. His answer was then he wonât be back. I told him thatâs fine, if you donât show up Melony is going down to the bar and will find some one else to fuck her ass. He didnât like that and just left. I told, this weekend is about getting dick.
I get in the shower and clean up, I was surprised that I was not sorer then I was, the moths before meeting Andy I started using dildos and plugs to open it up. I got my make up cleaned off and went down to breakfast. There was this big guy said good morning to me, and just walked by, and sat at the table next to mine
Now keep in mind, this is and actual weekend, well not a weekend, but Thursday, Friday, Saturday, and part of Sunday. Today was Friday. Iâm having breakfast and he strikes up a conversation. About what time of day it was and how few people were in the dining area. Well, it was almost 11 oâclock. After you eat, want to hit the pool? I said yeah, I guess I could, Iâve got shorts in my room. Cool then he said see you there.
I went and changed cleaned everything out, it was just going to be that kind of weekend, I hit the pool. I had on my out in the back yard swimming shorts with the lobster print
When he showed up he said that will never do. He went to the swimming shop and bought me a speedo. Then ask me to go to my room and change. Looking at them I thought why not, my body isnât bad to look at. So, I changed. Wearing my robe and new speedo I Went back to the pool and he said thatâs better. We swam a couple laps, got up in our lounge chairs, I ordered a bloody Mary. He said something about I must of had some party.
We did a few more laps, kept the banter up. When we got back in our seats by the pool, we each ordered another bloody Mary to be brought to our seats. Then he floored me.
He said, âyou looked pretty good in here last night.â
I asked him what he was talking about.
I have a scar on my left leg just above my knee itâs the shape of a J.
Iâm not sure what your talking about, what are you talking about? I wasnât here. He said yes you were, then he touched my scar. And you were smoking hot.
I tried to deny it, but just wasnât getting anywhere with it.
He had me. I was busted. âŚâŚâŚâŚâŚâŚâŚâŚâŚâŚâŚ
He asked if I lived the live style, so I told him about my past, explaining that this was just for the weekend. He said you could pull it off, I would never expected it if I hadnât seen you here this morning.
I explained that this weekend was all about getting some dick, ( I was hoping). He told about other cross dressers he had met and how he like the idea that if some one was brave enough to offer, how we were almost a sure thing for sex, which was true in my case anyway. So I asked him, is that an offer?
Continued.
Well, I used to, age came around and it just became too much work to try and keep a girlish figure. Iâm not a big guy by any means, 5â 7 at best, 5â8 Ish in heels. Iâm not a hairy guy, even at 58 my body is pretty much hair less. Even my Adamâs apple is not very pronounced. I have small feet small hands my butt even has a twitch when I walk. Drove my dad nuts. My stepsister used to tell me I had a body like a girl and dressed me up like a girl and would drag me out into public. I became a total sissy little fag slut way back in the day. Iâm sure youâve seen them on websites, the cross dressers that you wouldnât know it was a dude unless naked. I was one of those. I was also very lucky, that those that knew my secret. Kept it to themselves. I was only caught once. And it was a heart break.
In this story both of us were 19 years of age, at the beginning, this story took about 3 years.
I met Andy in high school around 1982. After graduation we just fucked off all summer and became best friends. BTW, Andy was a spoiled little rich grandson. His grandparents made sure he always had a car and always had money with him. They paid for us to go on trips pro sports games and what not. Spoiled little rich kid.
After the heart break I spoke about I stopped dressing, I stopped having sex I didnât care about much until Andy got me to start going out and doing things again.
One day, we were sitting at a red light and Andy started asking me about guy-to-guy sex, if I had ever done it, no. Was my reply, (I lied) and asked if I had ever thought about it. And if I ever would. My reply was, oh I donât know, it would just have to be all planned out I guess, or something. Never really thought about it. (I was still lying), Andy knew nothing of my past) He kept asking questions like, what do you think would have to happen? Pretty sure he was getting excited talking about it. I said, well. I would have to be drinking, it would have to be someone I knew wouldnât talk about it to people, and I would need a gay porn video because I wouldnât know what Iâm doing.
Sometime after his 19th birthday, which was October, after Christmas and before my 19th which was February, so it had to be in January, snow on the ground Andy called me and told me to pack a bag, his mom and grandmother had left and gone to their house in Florida. (I did say they were rich.) I was still living with my dad and Shirly. So, any chance to have a house to ourselves for a few days sounded awesome. I told mom Iâd be back in a few days, told her what was going on and was out the door when Andy pulled up to pick me up.
Andy had some other people over that night, we must have been boring, so they all had left around 10pm or so. We had been drinking a bit, after they left Andy brought out some porn movies that he had in his bed room, I said I need a shower first, going upstairs I found an enema bottle in the closet that held the towels. So, for my shower I got clean inside and out.
Once back downstairs Andy showed me the vhs vids, Debbie does Dallas , inside misty something and a guy one, back pack campers or something like that.
I said letâs watch that one first, we grabbed a couple blankets and laid at each end of the couch.
The movie started with guys packing their back packs and hiking through some woods, pitching camp and be for you know they were sucking cock. Watching the cock sucking made me hard, I stared wiggling around under my blanket and Andy asking what I was doing. I said Iâm taking off my sweatpants. He asked me why. I told him it just feels right watching something like this. I think you should too, it just feels right, I saw Andy wiggling under his blanket removing his sweatpants. Yeah, that feels right he said.
Thatâs when I made a move.
I could see Adny was hard, I rolled toward him and asked, âare you hard?â I reached out and put my hand on top of his dick head, I leaned in more and whispered, âI want to see itâ I was already pulling his blanket down past his waste. His dick popped up, and it was nice, prolyl 7 inches about as big around as a half dollar coin.
Once it popped up, I put my hands on his thighs and looked at it, briefly, then I just swallowed it, I took it all into the back of my throat, full strokes with my mouth. It felt so good to suck a cock again, I played with it a bit, I looked at the vid and they were kissing, I pointed to the tv and said we might as well get that out of the way. I sat up and put our dicks together and leaned in and kissed him opening up for his tongue, as I was grinding our cocks together, I started sucking his tongue instead of just Frenching when I started running his cock up and down the length of my butt crack. It felt wonderful. Andy wanted to sixty-nine, it felt great to have someone sucking my dick again. Again, I looked at the video to guys in a tent sixty-nine with one guy licking the other ones boi-pussy. I got up so Andy could see and told him âlookâ. He pulled me back down, with my knees in front of his arms an tried to sink his tongue in me. It was a wonderful feeling. I started humping his face with my ass. He responded well. With long licks an slipped a finger inside me, adding saliva to my inside, adding some lube to myself and his dick I sat across his waist legs spread across him, I raising up and placed his cock head at the entrance of my man pussy , I slowly slid down around his cock. It had been so long since I had cock in me I could feel the stretching and the pleasure of a cock inside me again.
Slowly, it took a little time, but I got all of him in me. I started to grind it in, his hands on my naked hips he started to meet my thrusts, But I wanted Andy between my legs fucking me like a little slut.
While slowly riding Andyâs cock, I looked at the tv, the guy had his legs back while they were being held back by the other guys arm, his legs were over his arms while he was getting fucked. I told Andy, âlookâ, I want to fuck like that. After I put a cushion in the corner of the couch I laid back and playfully lifted my legs for Andy,
As Andy got into place I guided him into me, My legs draped over his arms I was ready to take a good fucking, and I told him so, once he was all the way into me I told him, now fuck me, fuck my ass and donât stop until you cum. He started slowly to slow to suit me, I said fuck me, I told him, and thatâs what he did he started pounding my ass really good, I told him I could feel his balls slapping my ass, his strokes where long and deep and fast, he was grunting with the effort, sounds started to involuntarily come from me, I was feeling the fucking, each stroke brought a sound from me. With each trust came a âAhhhâ or an âuhhhhâ Andy asked if I was ok, my only words were âdonât stopâ I pulled his face down to me and sucked his tongue some more, I wanted that in me as well, I grabbed his ass and started pulling him into me. After maybe 15 minutes of this fucking I felt Andy speed up and started thrusting even harder, finally he says âIâm going to cumâ it came out in grunted words. I could feel the prostate orgasm building up in me, with those words it hit me I was trembling with extasy. Andy said he was going to cum, all I was able to say was âyeahâ it was barely a whisper. He began to breath even harder and started making an AhhhhâŚ.. Ahhh grr⌠sound, I pulled him even farther in, with a gasp he started to release his load into me, I could feel his cock pulse as he pumped he cum deep in me, this was happening as I was having my orgasm, for the third time in my life I was having a hands free orgasm. I made some kind of big mess. Andy practically collapsed on top of me, I wrapped my arms and legs around him while we tried to catch our breath, he kissed me deep tonguing me. After a few minutes he got up and went to get us a towel, when he came back and sat down, I took him back in my mouth to clean him up.
We had another brew and finally he said âI think thatâs the best pussy Iâve ever hadâ So I leaned forward and kissed him on the lips. Just a quick peck, but I said thereâs plenty more of that if you want.
He playfully called me a liar, youâve done this before havenât you? So, I confessed. I didnât tell him about the cross dressing though. Or the heart break, I wanted to keep that to myself.
This type of sex went on from then and all through summer, one day Andy gets us a room, and dinner, to tell me he would be leaving at the end of the month to move to Florida and start collage. I knew this day was going to come but I still wasnât ready for it.
He said he would come home on every break, every holiday. But he never did. It took almost two years for him to come home.
In the meantime, I had gotten a job as a dishwasher in the only fine dining restaurant in our area. I wanted to be a chief; I couldnât afford culinary school so the only way I could make it was to learn it first-hand. I wasnât by any means getting rich, but I was making enough money to move out of moms and get myself a very cool studio apartment. It was cool, not because it was my first place, but the front had a window all along the top in front, kind of like a sky light. My furniture was used but I had the comforts of home.
My job was going well, one day the chiefâs assistant called off work. I was training a new guy at the dish tank, and I was out on the floor cleaning tables. And did we ever get slammed. The cook, Chief Rick, started bitching he was beyond able to keep up. The boss (Terry) came out and told me to go help Rick.
I did my best once I figured out where the things were that Rick was asking for, I was actually helping out. We got caught up and at the end of service Rick told me for a guy just getting thrown in there I did an outstanding job. I was so fucking proud of myself.
Ricks back up chief just one day up and quit. Terry told him he would hire him some help. Rick said to Terry, get someone for the kitchen, I want Mel to back me up. He would do fine and do a good job and he has what it takes.
The thing was by this time I could do everything in the kitchen but run it. I could run it, and I had when we were short handed, and Terry didnât want to lose that. But he finally gave in, I got a good raise and moved up.
This took about a year and a half to get to this point. With the extra money I was able to get a dependable car, it wasnât pretty but it ran good. You know, a beater.
My first apartment and my first car. I was doing ok.
I think it was the month of November, I got a call,â heyâ was all he said, Andy?
He apologized.
He told me he was coming back to town in January. I need to know the date so I can plan something. I told him about my apartment and the job and that I was doing ok.
I got the date and wanted to make plans for something special.
Almost two months from then.
After a few days after getting this information, my sister Jess and bestie Sara stopped over with some wine, we sat around getting a buzz on and were talking. Andy came up, the girls and I had never talked about Andy, so I told them all about it. Jess was the one that got me to start dressing. I wanted to do something special and also explained that I was pissed about how he had not contacted me since he had left.
Sara said, âYou want to blow his mind?
Her idea was to bring back Melony. My cross-dressing alter ego.
Totally catch him off guard and dress. And fuck or suck off some other guy, and make sure he knows about it. Oh fuck, thatâs a great idea.
Jessica was all for it, she told me âYou have no idea how much I miss my little sisterâ.
So, we made a shopping date. I hadnât dressed in about 4 or 5 years. Jess and Sara brought over some of their clothes. Some makeup and other things a girl needs, they helped me with my make up and picking out an outfit from what they had brought with them. We went shopping, I went dressed for the first time in years.
Melony was reborn.
Our shopping date was sometime in December.
Andy wasnât coming back until January, I needed two winter outfits . Both slutty. I settled for two, one piece woven turtleneck sweater skirt that was charcoal gray and a black one. This would hide what Adams apple I did have, which wasnât pronounced at all. I was planning on knee high boots with heels. But, Sara found these little ankle boots that had a fur cuff at the top. They were so sexy. The whole idea was to look like a total sexy little slut. The skirts came down to be just above the middle of my thighs. The plan was, no stockings.
Then we started looking at wigs. I canât tell you how much fun it was to be out shopping with the girls dressed as Melony. I didnât realize how much I had been missing this.
This is when Jess grabbed me by the back of the head, by my hair, and said âI donât think you need a wigâ I didnât realize how long my hair had gotten. Mom had always gotten after me about my hair and to keep it cut. Now that I was out on my own, I thought back, I hadnât had a cut since I moved out of moms, I was putting my hair back in a tail to cook, but didnât really think about how long it was, My hair is curly anyway so.. Sorry old habits I apologized.
Sara suggested I dye it black. Add some product and stretch out the curls, she had found the cutest chauffeurs caps, I picked out a black one, it would go perfect with the outfit.
We took everything back to my place and the girls reminded me how to put-on makeup. We practiced walking, i which isnât hard you just have to walk in a straight line, kind of heel to toe, but with a stride. A straight line like walking on a rail. I practiced walking in heels which I hadnât done in what seemed like forever. They remined me of the exerciseâs girls do to keep their girly figure, which I hadnât forgotten and still did many of them. I couldnât get my girly voice back though; it just wasnât quite right. We came up with a plan for that as well.
The big night, Andy had been back in town for close to two days, I wouldnât let him see me. I wouldnât go see him; I wouldnât give him my address.
A new hotel had gone up since Andy had left. The rooms were set up to over look the dinning area and the pool, each floor had itâs own landing floor and balcony. Sort of a dome.
I had reserved a room for three days and used vacations days from work. I didnât want any of my neighbors to see Melony. So, I thought this was the best way to go. The idea was for Melony to have her fun at night on second shift, and Melven to go about his business on first shift so no one would know, in case anyone knew me.
I was a nervous wreck. I wasnât sure I could pull of the look any more even though the practice run went well. I was still a wreak.
Jess and Sara showed up that night to help me shave the hair I couldnât reach or see, my legs were shaven, my nether regions were shaved, I was pretty much completely hairless, except the hair on my head, they helped me with my makeup and the dress. Everything was dark, Dark sweater skirt, dark eye liner, the eye shadow was two tone, dark gray and lite gray in a cat eye shape, my lip stick was a very dark burgundy, bloodberry I think it was called, dark nail polish. Also bloodberry if I remember right. I was fully dressed and ready, I checked the mirror, and was happy with what I saw, Melony was back, my confidence had returned. I was one sexy hot fucking slut. Smelling of soft musk, it was my perfume of choice, And I was happy with it. I was ten minutes early. I was able to look down from my room and could see Andy was already there. The first thing that went through my mind was, Heâs lost weight. He looked good. I grabbed a small piece of paper from the little note pads they give you in a hotel, and wrote something for Andy.
The girls were practically pushing me out of the room. âheâs here, get down thereâ Sara said scoldingly.
Lock up the room, please, I said as I walked out of the room. Jess gave me a quick peck on the lips Sara smacked my ass and told me to go get him slut with a little laugh in her voice.
As I stepped out and started âthe walkâ I felt sexy as fuck, it was all I could do to keep from getting hard.
Did I say I could pass? The looks I got proved I still could.
I could hear my heels clicking as I walked on the marble walkway, heading towards the elevator,so could others, as I saw people looking up to see were the sound was coming from. I could feel my ass with its natural little twitch and the way I was walking I could feel my ass swaying, I was catching a slight breeze up my skirt, And it felt so fucking hot. All I can tell you, is, I felt so fucking hot I was starting to drip precum. If I had a vagina, it would be soaking wet.
My skirt had ridding up to just above mid-thigh, and I wasnât going to pull it down, let them look, I had worked hard and spent some money to look like this. I could feel the guys turn around to check out my ass as I walked by, and I loved it.
I walked right in, the host asked if he could help, I shook my head and pointed, I was in full Melony mode now, I was in the role.
I walked right up the Andyâs table and sat down.
He looked at me, and I could see wonder and a flash of lust in his eyes.
âIâm sorry miss Iâm waiting on a friend.â Andy said to me.
As I sat down, I let my skirt ride up to show the bottom of my ass, I acted shocked and reached down to smooth it out and pull it back down, I looked shocked, and looked around, I caught this older gentleman looking a little embarrassed that I had caught him, as I just smiled and looked away, as I had intended, I also saw a wife swat her husbands shoulder. It felt good.
Andy has said, Iâm waiting on a friend, He didnât know it was me.
I pulled out this little piece of paper and slid it across the table to him.
I leaned forward and whispered , âI know.â
He just looked at me and shifted his eyes to the paper.
It said.
You will call me Melony.
If anyone asks, Iâm just getting over strep throat and my voice isnât returning the way it should,
My doctors have told me to whisper if I had to speak and try to not even do that if it can be helped.
He had a confused look in his eyes, I leaned forward again and whispered,: âhi Andyâ
It still took a few seconds, then his mouth dropped, he whispered, oh my gawd. Then it got louder, Oh my gawd! I stuck my fingers to my lips and went shhhhâŚâŚ.
While still whispering, I said reread the paper.
He was still at a loss, I leaned forward and gave him a peck on the lips, he still wasnât sure and whispered . Melvin? ShhhhâŚ.. I whispered, âMelony.â
Then I whispered âclose your mouth. You look ridiculous. â He shook his head in disbelieve and said, you look great, he was getting his head straight after I had just rocked his world.
Dinner went well, Andy did well as we ordered, he explained I couldnât talk. I pointed to what I wanted Andy had a bottle of wine for us, as we caught up. I let him know I wasnât happy with him, and you better make it up to me. The waiter was someone I had gone to high school with. He was a real dick to me, so Andy explained to him I couldnât talk he asked if I was still sick, Adny did great, âno her voice is just taking it time to recover, he leaned over and told me how sorry he was to hear it, I mouthed the words Iâm sorry, thank you, as I touched the back of his leg, I decided if he was here tomorrow I was going to suck him off. After all, this weekend was all about getting dick, and I didnât care where it came from. During dinner I ask Andy if he remembered that guy, he did, Andy said something about him being a dick in high school. I told Andy, if he works tomorrow night Iâm going to suck his Dick He wanted to know why, I whispered my own little type of pay back. The pay back? Getting sucked off by a guy. Lol.
After dinner we went to the room, so I could check my makeup. After a little heavy petting, we went down to the club and danced, I had my hand in his pants on the floor, I was trying to get him off on the floor. But he wouldnât let me. I was still pissed at him though. This guy comes up and askes me to dance, out on the floor he asked me if he could get a dance like my friend was getting, I asked, did you see that?(still whispering) Yeah was his answer. Is that all you want? Sure, was all he said. I grabbed him by the belt and told him to follow me, I took him to restroom into a stall and sucked him off, I took his above average cock in my mouth and he put his hand on the back of my head, fucking my face and told me how good I was at it. He at least let me know when he was going to cum. He had a lot but I managed to get it down without getting my sweater messy.
I got back to the table and Andy asked what had happened, so I told him. He wasnât to pleased about it, but I didnât care. He must understand Melony is a slut. It just happened. And Iâm not sorry about it.
I reached under the table and rubbed his cock through his pants, I told him thereâs plenty more of where that came from, and you could have at least called me once in two years, and how Melony is a total slut, whispering I told him some more about my past. How all this started and the first time I sucked a cock. I swear he was blushing
I stroked him under the table. If the tablecloth had been longer, I would have blown him then and there. After toying with him some more I told him I was ready to go to the room, I had some wine sent up, I wanted to drink and get fucked.
Once we got to the room I poured us both a glass of wine and decided this wasnât going to be enough, so I ordered two more bottles of red to be brought to the room, Andy was eager to go but I wouldnât let him touch me just yet, âwe are waiting on room service, I told him. The guy that had been such an ass in high school brought the wine to the room, I answered the door and whispered a thank you and gave him a slow slutty wink slipping him a five and making sure my nails ever so slightly scratched the palm of his hand, I knew it had the effect I wanted by the way his hand twitched and the blush that filled his cheeks. I asked if he worked tomorrow night, he looked down at his feet saying yed, I gave him another sultry wink and whispered Iâll see you then. He walked away with a bright red face, I just laughed to myself.
I downed my wine and poured another, Andy so because of the flirting, Andy called me a whore, I was really feeling my buzz by now, I told him to put his money on the night stand as I crawled across the king sized bed like a cat, he told me ânoâ ok âwell you see lover, Iâm not a whore, Iâm a slut, and your going to fuck me like a slut.â He kept backing away from my lips until he couldnât retreat any more. In one swift move he flipped me over and shoved his tongue down my throat while pulling my panties off from under my skirt, it surprised me, he went down on me taking all of it, (just a little over 7 inches a little more then a 50 cent coin) and just held it in his mouth at the base making small sucking motions, it felt so good, my eyes rolled back and I just let out a moan. He slowly started sucking up and down, making me shiver each time he reached the base. âyour going to make me cum, you have to stop.â I told him, Iâm not ready yet.
I retreaded into the pillows at the head of the bed.
I asked him how he liked his home coming? âTotal shockâ he wanted to know why he hadnât seen this before, I wanted to keep it to myself I answered as I pulled my fake breasts out of my sweater. He told how good I looked, I kept saying ok, as I was taking his pants off of him, âyour fucking Melony tonightâ I told him tonight and you better be up to itâ. I went down on him, just the head, with a little nip, he jerked from it, then I took it all, five minutes of long deep sucking and I raised up, grinding our dicks together like we used to, kissing deeply he opened his mouth and I sucked his tongue as I tried to squeeze his cock with the cheeks of my ass. Squeezing his cock with my legs. I reached the night stand an got out a bottle of lube, slipping a finger in me lubing myself up, I lubed him up. Raising up, I guided him into me, in and out working the lube in till I could get all of him in me. I was grinding him, keeping it deep at the base, it just felt good having him in me again. This wasnât good enough for Andy.
He started saying things, I want to fuck you slut, Melony I want to fuck your slutty little ass, he pulled me off him and rolled me over, I stuck my ass in the air, laying facing sideways on a pillow, I told to fuck his little slut, fuck her good, and fuck me hard! He went all the way in me, making me arch my back, the sudden stretching was intense, almost painful but with a sense of pleasure Andy started his assault on my ass, all the way in sometimes staying in with short hard strokes, sometimes pulling all the way out, slamming it back home. He fucked the little slut good and hard for about an hour, calling me slut, you like that slut? Take it you fucking slut, I could hear him banging my ass the whole hotel could probably hear it, I could feel his balls slapping my ass, even with a assgasam, when you tighten up he was still punching it through, bringing animal grunts from me, I tried to keep it quit. He finally garbed my hips and just said, âCummingâ and did he ever, I could feel it dripping down my legs before he was even done. Then he just leaned over, reached in and started stroking me with his hand. I told him to stop, I needed to catch my breath, I had such a assgasam, not only was I visibly shaking, I donât know how or why I didnât have a hands free orgasm.
We just laid there for a few minutes, I started licking his cock and sucking it slightly just to clean him up an milked it to get it all out, I went and got us towels to clean up. After another glass of wine I started playing with him again, and told the job isnât finished, I started sucking him again, taking him deep and just sucking at the base until he came in my mouth. I gave him a few minutes and cross legged walked my dick up to his face, which he readily opened his mouth for me, I slowly fucked his face as his suction was hard as I fucked his mouth until I came, he made a point to see that he swallowed it. We lay down and turned the tv on. It was 2 am, we had fucked for two and a half hours.
I woke up to hear Andy in the shower, I staggered in and checked the mirror, my makeup was a mess. Lol eye liner smutched, hair a mess. I got in the shower with Andy and asked him what he was doing, he had to check in with his grandparents, (get more money) and other things he had to do. So, Iâll see ya tonight?
He asked if I was still going to suck that guy off and I said yes. His answer was then he wonât be back. I told him thatâs fine, if you donât show up Melony is going down to the bar and will find some one else to fuck her ass. He didnât like that and just left. I told, this weekend is about getting dick.
I get in the shower and clean up, I was surprised that I was not sorer then I was, the moths before meeting Andy I started using dildos and plugs to open it up. I got my make up cleaned off and went down to breakfast. There was this big guy said good morning to me, and just walked by, and sat at the table next to mine
Now keep in mind, this is and actual weekend, well not a weekend, but Thursday, Friday, Saturday, and part of Sunday. Today was Friday. Iâm having breakfast and he strikes up a conversation. About what time of day it was and how few people were in the dining area. Well, it was almost 11 oâclock. After you eat, want to hit the pool? I said yeah, I guess I could, Iâve got shorts in my room. Cool then he said see you there.
I went and changed cleaned everything out, it was just going to be that kind of weekend, I hit the pool. I had on my out in the back yard swimming shorts with the lobster print
When he showed up he said that will never do. He went to the swimming shop and bought me a speedo. Then ask me to go to my room and change. Looking at them I thought why not, my body isnât bad to look at. So, I changed. Wearing my robe and new speedo I Went back to the pool and he said thatâs better. We swam a couple laps, got up in our lounge chairs, I ordered a bloody Mary. He said something about I must of had some party.
We did a few more laps, kept the banter up. When we got back in our seats by the pool, we each ordered another bloody Mary to be brought to our seats. Then he floored me.
He said, âyou looked pretty good in here last night.â
I asked him what he was talking about.
I have a scar on my left leg just above my knee itâs the shape of a J.
Iâm not sure what your talking about, what are you talking about? I wasnât here. He said yes you were, then he touched my scar. And you were smoking hot.
I tried to deny it, but just wasnât getting anywhere with it.
He had me. I was busted. âŚâŚâŚâŚâŚâŚâŚâŚâŚâŚâŚ
He asked if I lived the live style, so I told him about my past, explaining that this was just for the weekend. He said you could pull it off, I would never expected it if I hadnât seen you here this morning.
I explained that this weekend was all about getting some dick, ( I was hoping). He told about other cross dressers he had met and how he like the idea that if some one was brave enough to offer, how we were almost a sure thing for sex, which was true in my case anyway. So I asked him, is that an offer?
Continued.
11 months ago