Beginnings: My First Time As A Crossdresser (PT 1) free porn video

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( Hi I am repostng because I want to string everything together for continuity ) Everything is connected so you should start at the beginning.) (This is a true story, the conversations in it are only as accurate as my memory can supply, as this happened Thirty years ago)
When I was 17 I was dating a girl from the local college. I lived in a medium sized college town in a western state and it was 1983. It was Halloween weekend and we were both drinking some wine coolers she’d bought, the drinking age was eighteen at the time and she was nineteen, and smoking some pot I had brought over. We had planned on going to a party at a local frat house but it had gotten cancelled because the police had raided it the night before and busted them for u******e drinking at the frat.. So we had no specific plans and were bored, figuring out what to do with our Saturday night. Like I mentioned earlier it was Halloween so we absolutely had to go somewhere and party. She brought up Doctor Feelgoods which was a bar near campus, favored by college students and locals alike. I reminded her that my fake ID had been confis**ted a couple weeks earlier.
“That’s okay. My roommate left her purse here and her ID is in it” Michelle said with a wicked glint in her eyes. I was confused, not seeing how it was relevant. “I’m sure if we dressed you up right you could pass for her. You’re both about the same height and have brown hair with green eyes. With your skinny frame all we’d have to do is put some of her clothes on you, style your hair right, and put some makeup on you and you would look like her. You two look practically like brother and sister anyways.”
I realized that she was right, I was fairly slender. I was a competitive bicycle racer and swimmer which kept me very lean, and I kept my body hairless like the other swimmers on my team (although it was as much a hairless fetish as anything else, I couldn’t stand body hair on me). I was 5’7” and 135#, smooth and hairless from the eyebrows down and my features weren’t particularly masculine, girls always thought of me as “cute” which was fine by me as long as it got me dates. My long brown hair (it was the eighties after all) was about the same length as Kayla’s. Other people had remarked upon the supposed family resemblance before so maybe we could pull it off.
I had dabbled in crossdressing a few years before, sometimes stealing my mother’s panty hose and bras, putting them on and jerking off, while I pretended I was a hot teenage girl. Once I even dressed in her bra and panties while I sucked off my best friend and neighbor, who I experimented with a few times when we were younger. So the idea wasn’t completely out of the question. But by this time I was no longer a virgin with girls and I was quite sure I was straight, so the prospect of dressing up as a girl and going out in public did make me a bit nervous. But I was a bit buzzed and stoned so it didn’t take long for Michelle to convince me, especially when she threatened to go out to the bar without me if I didn’t play along.
Soon Michelle had me dressed up Madonna style in a Fishnet crotchless bodysuit, black satin panties. a ruffled denim miniskirt, and a black leather and lace corset with rhinestones which she pulled really tight in the middle. This pushed up my pecs and squeezed them together, giving me small but respectable cleavage, and made my hips flare out a bit. Next she had me put on Kayla’s leather “biker” ¾ jacket and blood red stiletto heels . When I saw myself in the mirror I was surprised at how girly I already looked and we hadn’t done my hair or makeup yet.
Next Michelle curled my hair with a curling iron and used a brush to tease it into a big hair style that was very popular back then, finishing it with a red ribbon hairband with a cute bow. She had some dangly red clip on earrings (they were a lot easier to find back then) and several necklaces and bracelets that she had me put on. Next came a couple belts with studs she wrapped around my waist, completing the Madonna look that was so en’ vogue at the time.
After this she glued fake nails on me saying it would help my hands look more feminine.( I didn’t realize at the time how hard it would be to get them off!) These she painted the same red as my heels calling it CFM red with a smirk. After this she did my makeup, applying it rather heavy with lots of eyeliner and mascara, making envious comments about the length of my lashes, which women have always remarked upon. The blush really made my cheekbones stand out, giving my face a more feminine exotic appearance. She even used some on my cleavage ,after putting pads in the corset , making it look deeper and giving me the appearance of decent B cup size breasts. Lastly she applied lipstick and lipliner to my lips with a heavy dose of gloss atop the bloodred lipstick which made my lips look sexy and pouty. “There you go, perfect little cocksucker lips! The guys at the bar are gonna go crazy over you” she said laughing, as she finished this.
“Hang on there MikkiI!” I protested “I’m not gay!”
I never said that, but you sure do make a hot girl with my help! I’m rather proud of my work if I do say so myself” She replied with a wink. “Take a look for yourself!” as she led me over to the full length mirror on her dorm room door. I stumbled a bit in the high heels but not too much as I had some practice from borrowing my mom’s from time to time. When we got over to the mirror I took my first real look and was shocked at what I saw in the mirror. I didn’t recognize myself , there was a hot, sexy, slightly slutty, young woman looking back at me. The corset had given me a curvier figure, and my legs looked fantastic in the high heels and fishnet body stocking. My nagging worries that I would be recognized by someone I knew vanished in an instant. I realized there was going to be at least one problem as I felt my erection spring to life. “Oh my, we can’t have that now, can we?” Mikki exclaimed. “Well I know how to deal with that little problem “then dropped to her knees, pulled down my black satin panties and started sucking me off. I came in seconds, nearly falling down as my legs went jelly on me and I had a hard time staying up in those heels. Mikki wiped off her lips and smirked at me, ”You may not think your gay but you sure seem to like being dressed like a girl. Now pull up your panties miss Bobbi (little did I know at that moment that would become my Gurl name) and practice walking around in those heels a bit while I get ready. It’s a couple blocks to the bar and I don’t want you spraining an ankle on the way there.”
Feeling a little nervous and excited I downed a wine cooler and couple shots of tequila, admiring myself in the mirror, while walking around the room. I smoked another bowl and felt my nerves calm a lot. Realizing that there wasn’t much room to walk around in the cramped dorm room I told Mikki I was going out to walk the hallways. “Fine” she said ”I’m not going to be ready for about 20 minutes. Just don’t get picked up by some guy before we get to the bar.” “HaHa, you’re soooo funny!” I retorted and slipped out into the hallway. There was a girl letting herself into her dorm room who glanced up “Kayla, you’re looking good! Hot date tonight?” I was startled and blurted out in a breathless high pitched voice “Oh I’m not Kayla. I’m umm… her cousin Bobbi” The girl took a closer look at me and said “Oh, wow you could be sisters. Well you look great anyways, are you going out with Michelle tonight?” I nodded “Well don’t let her get you in trouble. She can be a wild one at times. Have fun!” I mumbled thanks and walked away down the hallway. Not trusting my ability to deal with stairs in those heels yet I crossed over to the next wing of the dorm which was the guys’ side as it was a coed dorm. There were a few guys in the hall talking and they definitely took notice as I walked by whistling and making lewd comments. I didn’t say anything and walked by them without looking at them. “Stuck up Slut” one of them commented as I walked by. “Ha! If only they knew” I thought to myself. I walked around the dorm for about 10 minutes to get used to the Come Fuck Me Pumps Mikki had put me in and made my way back to her room, earning more admiring looks from the guys and a few jealous glares from some of the girls.
When I got to her room she wasn’t quite ready so I loaded us another bowl and handed it to her.”So I heard some whistles out there. I told you the boys would love you” She teased. I didn’t say anything but blushed a deep red. “Oh don’t worry, we’ll have fun tonight and it will be our little secret. Come on let’s go I’m ready.” With that she threw on a jacket, grabbed her little purse and handed me Kayla’s. “Open it up and memorize Kayla’s info in case they ask you at the door.” I did this, noting that she had put the red lipstick I was wearing along with a powder compact and some blush in the purse. I also noticed there were some condoms in there. “What’s this?” I asked, rolling my eyes at her. “Oh those are Kayla’s, put them back!” she said, then winked “Besides a girl can never be too careful.” I put them back and took another hit off the pipe for courage and we left the dorm.
It was pretty chilly that night and the fishnet stockings did nothing to cut the cold. My legs had goosebumps and I was shivering by the time we got to the bar “This will be good for you” Mikki said, “Now you’ll understand what we go through for you guys.” What I understood was that my feet were killing me after the long two block walk to the bar and I couldn’t wait to get into the bar. Fortunately the bouncer barely glanced at Kayla’s license before waiving us in. The bar was very crowded and noisy with about ½ of the patrons dressed in costume. A lot of the girls there were dressed in similar fashion to me and Mikki, ala’ trashy Madonna style, although the phrase New Wave Hooker comes to mind also.
It was definitely an eye-opening experience as we made our way through the crowded bar. I lost count of the number of times I was propositioned or groped by the time we got over to a booth that Mikki led us to, saying she knew someone at the table. There were a couple of girls from Michelle’s dorm sitting at the table and they invited us to join them. “Where’s your little boyfriend Mikki?” one asked.
“Oh, he lost his Fake and I wasn’t about to miss out on Halloween at Dr Feelgoods. It’s the best party of the year! “ She exclaimed “This is Kayla’s cousin Bobbi. She’s in town visiting for the weekend checking out the campus to see if she wants to go to college here next year. “
The two girls introduced themselves, Cindy was a tallish blonde with big permed hair, Danni was a petite asian girl with a cute pixie cut. Both were dressed in classic eighties slutwear with heavy makeup
“Where’s Kayla” asked Cindy
“Oh, she had a sorority rush function she had to attend so she asked me to show Bobbi around, and keep her company tonight. “
“She trusted you with her cousin? That’s fresh!”
They all laughed and I wondered what I had gotten myself into. One of the bartenders stopped by our table and said “Hi ladies, Mikki, good to see you again. Haven’t seen you in a couple weeks since we took your little boyfriends ID. I still cant see what you see in him. He’s just a pretty boy that cant even get into bar now.” I was glaring at him because he was the one who had taken it but he didn’t seem to notice ”Who’s the fresh meat?” he asked looking me over with apparent admiration. I blushed and was about to say something rude when Mikki put her arm protectively around me.
“Don’t get any ideas Derek, she’s Kayla’s cousin and she’ll roast your balls over an open fire if you even try to hookup with her. And as for my boyfriend if you could eat pussy half as good as he can maybe I wouldn’t have dumped you.”
The girls laughed while I turned a deep red, and Derek took our order and huffed off to the bar. I couldn’t believe he looked me over like I was a piece of ass ripe for the plucking and didn’t recognize me. I was going to get a beer but Mikki insisted I have a Long Island Ice Tea. “You need something with a straw so you don’t mess up your pretty little lipstick.”
Derek brought back our drinks, warning me that he’d made my LIT extra strong so be careful . Well it tasted fine and went down smooth and before I knew it he’d brought me another “On the House “, He said with a wink. That one didn’t last long either and soon I was feeling no pain. Guys kept coming over asking us to dance, buying us drinks and flirting with us. I let the other girls do most of the talking. Eventually some guys asked us to dance that the other girls liked, I tried to demur but Mikki insisted. “It’s just one little dance, don’t be such a prude” I relented and let my escort lead me to the dance floor. It was I little tough in heels but I’m a great dancer and picked up a decent rhythm pretty quickly, I looked at the other girls for inspiration and soon had my hips gyrating like them and then James moved behind me grinding up against me. He had his hands all over me, my hips, my shoulders, my ass. I could feel his erection pressing against my backside. I was a little freaked out by how aroused I was getting by it and was glad when the song ended. The next song was a slow song and I made to leave the floor but he grabbed me by the hand and pulled me back. I was pretty drunk and didn’t resist much. The next thing I know we’re dancing slow and sensually, our bodies pressed tight together, his hands cupping my asscheeks squeezing them in time with the music. He nuzzled my neck kissing it softly whispering how sexy I was into my ear, sending delicious waves of pleasure rippling through my body. When the song ended I fairly bolted from the dance floor back to the safety of our table.
When I got there I saw Mikki making out with some guy and I turned away from the table before she saw me. I was pissed off, very drunk and stoned, and decided I needed some fresh air. Not wanting to fight the crowd at the front entrance I went out the back and stood by the dumpsters smoking a cigarette, waiting for my head to clear a bit. Of course who should show up a minute later but Derek with a load of beer bottles for the dumpster. I had my back turned and didn’t see him until he dumped them in, the crashing noise of all those bottles startled me and I must have jumped about a foot.
When I turned around there was Derek laughing so hard he had tear in his eyes. “Oh you should have seen yourself!” he chortled “ You just about jumped out of your panties. It was classic!” I called him an asshole and bent over to pick up my cigarette which I had dropped. It had gone out so I fumbled in Kayla’s purse for a lighter. Naturally one of the condoms fell out onto the ground. Derek picked it up quickly, “Planning on using this tonight you little slut? I saw how hot and bothered you were getting with that guy on the dance floor. Were you planning on sucking his dick? Those lips of yours just scream cocksucker! Maybe you were planning on getting a hard cock in your tight little twat? After all if you’re just visiting who’s to know what a horny little slut you are? ”
I was so pissed I couldn’t say a word, but he had to feel the anger and contempt blazing from my heavily mascara’d eyes. It only goaded him on more. I took a deep drag from my cigarette which was mostly weed with a little bit of clove and tobacco. Derek sniffed the air snatched the cigarette from my fingers and took a puff. He grabbed me by the arm and pulled me to him.
“This shit can get you in some real trouble around here Bobbi. The local cops love busting liitle out of towners like you. And it could get the bars license suspended as well. There’s a squad car out in the front parking lot. What are we going to do about this? I’m sure your parents would be pretty pissed if you got arrested while visiting our fine college here, wouldn’t they? It also wouldn’t do much for your chances of admission either!”
Obviously, he still had no idea who I really was and none of the crap he was talking about really applied but I had to play along or face even worse consequences! Namely getting caught all dressed up as a slut! I’d never be able to explain it away and our town isn’t all that big. Everybody would know ! I’d be humiliated and my parents would freak out. All of my friends would know and I just couldn’t have that!
I looked at him through my lashes, “Please, Derek, I can’t get busted! My family would go ballistic. ” I took a deep breath knowing my next words would doom me. “Can’t we come to some sort of arrangement? Please?”
Derek smirked, grabbing my wrist and led me back into the bar and into a storage room near the back of the bar. There were shelves of liquor and kegs of beer stacked up all over the room. He led me behind one of the shelves where I was out of sight from the door. I was a little scared but also getting turned on. He grabbed me by the hair and pulled my mouth to his French kissing me roughly, his five o’clock shadow scr****g my soft skin (I didn’t have facial hair yet). At first I was repulsed, I had never kissed a guy before, but the weed and the alcohol lowered my resistance and I started kissing him back moaning softly. I was getting very aroused but was grateful that I wasn’t getting an erection. Maybe it was all the alcohol? After a couple minutes he broke it off, looking deep into my eyes. “God you’re a hot little bitch. I sure hope you come to school here next fall. But it’s time to pay the Piper Bobbi.” With that he started pushing down on my shoulders, forcing me to my knees. He undid his belt buckle and told me to do the rest so he could watch. I undid the buttons on the crotch of his Levis 501’s, his cock sprang out immediately and I discovered he was going commando. His dick was thick and veiny maybe about 7 inches long. It wasn’t as big as my best friends cock that I had sucked years earlier who was about 8 1/2 inches long and a lot thicker, so I figured I could handle it.
I took it in my mouth and started to suck it tentatively, working my way up and down the shaft. This wasn’t my first rodeo so soon I was sucking like a pro, stopping to lick his balls now and then. He loved this and was calling me names like dirty lil slut, whore, and bitch. I was really starting to get into it, the thought of sucking Dereks cock in the store room while dressed as a girl was getting me really hot. In my mind I wasn’t gay at all, I was a sexy girl making love to his cock with my mouth. He fumbled in his jeans pocked and pulled out a little brown bottle held it to my nose and told me to inhale. I didn’t know what it was but did it. Almost immediately I felt a huge rush of warmth go through my body and my pulse went way up. My head began buzzing very pleasantly yet intensely and my whole world became focused on the cock he was now forcing down my throat, both hands holding my head, fucking my face like a piston driving in and out past my pretty red lips. I gagged a couple times but that only made him thrust harder., Eventually he cried out and brutally rammed his cock to the hilt, my face pressed flat against his crotch, his hands holding my head in place, tears streaming down my face, while his cocked spasmed in my throat, shooting what seemed like a huge load down my gullet. I don’t know if it was a big load because there was no option of spit or swallow. After a bit I felt him soften in my mouth and he released my head, sliding his semi erect cock out of my mouth. He squeezed his cock from the base to the tip leaving a huge drop at the tip.” Lick it off!” he commanded. I complied eagerly reveling in the salty taste and texture. Suddenly the door opened and I froze, terrified we were discovered!
“Derek, you in here?” somebody asked, unable to see us behind the shelving.
“Yeah, I was changing out a keg. It was a little bitch but once I got the tap in right it fit fine” he said, smirking down at me his cock resting on my lips.
“Well get your ass out here, we need you at the bar!”
“Be right there” he shouted. Tucking his cock back into his Levis, he buttoned up and told me to wait a couple minutes before I left the storeroom. Before he left he told me he was looking forward to seeing me as a freshman next year and that I sucked dick even better than his old girlfriend Mikki. “Maybe I can tap that hot little ass of yours next fall!” and walked out.
I was woozy from the booze, the pot, and the forceful face fucking I had just received, and giddy with the thought of what I had just done. Secretly pleased that Derek thought I was a better cocksucker than my girlfriend. I lay there on the floor for what seemed like a few minutes but must have passed out for a bit as it was near closing time when I gathered myself up and staggered out of the storeroom. I went into the girls’ bathroom and straightened out my makeup as best I could. I looked quite the sight, my mascara was running down my face, my lipstick was smeared and my lips were red raw and puffy from the brutal treatment they had received from Derek. I don’t think anyone could have looked at me and not known what I had been doing. It took about ten minutes but finally I Iooked presentable. Walking out to the main area of the bar I realized Mikki was nowhere in sight. Danni was still there and I asked her where Mikki was. “She thought you left the bar without telling her so she left with that guy. What happened to you? You look like you’ve been rode hard and put away wet!” Feeling a bit naughty I replied “I was.” Then winked and walked out of the bar.
I froze my legs off walking back to Mikki’s dorm, when I got there her door was locked and I couldn’t hear any noise coming from inside. I knocked but there was no answer. I was totally screwed. I couldn’t hang out in the hallway and I couldn’t walk home in those heels, especially dressed up the way I was. My clothes were in Mikki’s room and I had no idea where she was. I thought about it for a bit and realized that I did have one option open to me. One I felt oddly appealing, I played Dungeons and Dragons back then and one of the guys I played with, Tracey, lived in an apartment a few blocks away. Tracey was older, maybe around 30 and was gay. I also knew he had a bit of a crush on me. I had turned him down months before but now seemed like a good opportunity to have some more fun while I was dressed up and I knew he wouldn’t out me to everybody as he had told me it would be our little secret if I ever changed my mind.
I walked the five blocks to his apartment and was chilled to the bone by the time I got there. Praying that he was home, I rang his doorbell. It was about 2 am. After another minute I rang it again. I saw a light flick on, Thank God! After a couple minutes Tracey answered the door in his bathrobe. Blinking, he looked at me in confusion “Excuse me miss can I help you?”
“Tracey , it’s me Rob. Can I come in?”
Now he looked even more confused for a moment until I saw realization blossom in his eyes, grinning broadly he stepped back and motioned for me to come in. “And to what honor does bring the warrior maiden Leighanne to my humble abode?” (He always talked that way and Leighanne was the name of one of the characters I played sometimes, an elven warrior princess.) Looking at me he could tell I was freezing so he took me over by the fireplace and got a fire going while I huddled under a blanket he had put around my shoulders. Then he grabbed us a couple glasses of Brandy, waited a few minutes until I had stopped shivering and said “So this is a story I’ve got to hear, Out with it. And I want ALL the details!”
First I needed some more weed, so I had him load us a fat bowl, and then I told him everything between deep pulls on the pipe and sips of Brandy. It was a very good brand, smooth and mellow and also quite strong. By the time my story was finished I was feeling quite mellow and very aroused.”…. And so since I just sucked my first cock as a girl I was hoping maybe you would take my cherry tonite?”
’ Tracey had a grin on about as big as the Cheshire Cat, he leaned forward and took my rednailed hands in has and asked if I was sure, if I wanted I could just crash at his place and he’d go get my stuff in the morning and nobody had to know . I’d had a long time to think about it on the walk over, even though I was freezing the thought of having a man fuck me as a girl got me hotter and hotter the closer I got to Tracey’s apt. But the thought of doing it with Tracey as a guy still repelled me. I didn’t understand the difference and told Tracey this.
“That my dear is because you’re a true Sissy” he explained. “Tell me, when Derek was fucking your mouth, did you get an erection?”
“No” I replied “But I was totally turned on by it. Getting used and dominated like that. It made me feel like a submissive girly slut. But the thought of doing that as a guy grosses me out. So what gives?”
While Tracey worked in the burgeoning field of IT as a systems administrator I also knew he had a Masters in Psychology. “ There isn’t a lot of research in this area,” (It WAS the early eighties)” but I think you have a situational based form of Gender Dysphoria . Basically, put you in the right situation, as in dressed like a girl, and in your mind you become a girl, with all that that implies. In essence, in your mind, you become whatever the clothes you are wearing dictate according to your expectations based upon societal perceptions. “
It was a bit deep for my 17 year old mind but I got the gist of it. If I was dressed like a slut I would act like a slut. If I was dressed like a guy I would act like a guy.
“So I’m not gay then?” I asked with a little too much relief for my comfort. I blushed a bit, my face reddening as I realized the unintended slight to Tracey’s sexuality .
“Do you get Hard with women? “ he asked
“Hell yeah! Mikki and I have been dating for a few months now!” We had met at one of the Universities home games . I had worked the stadiums concession stands for the last few years. Moving my way up as a “Coke” hawker making 10 cents per Coke to a concession stand Mgr by the time I met Mikki. I was serving up some Nachos When this hot lil blonde girl shows up in front of me and asks for no jalapeños, Really? I give her some skin about it and she responds by giving me a challenge. “Fine, if you can eat a beer cup full of these “lightweight” jalapeños. We’ll go out next weekend.” Well, that was a definite ‘no balls” so I had to take the challenge . I wound up shitting fire for three days but I won the challenge. Mikki and had been dating ever since. Sex with her was incredible and I loved eating her pussy til she came. She was VERY responsive and loved having her pussy licked. She even told me I did as good as her old roommate from last year. Who I eventually figured out was Danni, the petite asian girl. I knew Mikki was bisexual and a bit of a self confessed slut, so I had no illusions about her faithfulness. But hell, I was 17 and NOT about to look a gift horse in the mouth. Sex with her was great and I was willing to put up with a lot to keep that going.
“Well then that’s your primary identity and how you feel dressed as a girl is like an alternate personality” he explained.
Which was all well and good but I was realizing that I was currently dressed as a hot slutty girl, and getting more aroused by the moment. Also that there was an attractive man sitting in front of me with nothing but a silk robe on. One who I knew wanted me and that only made things worse! “Ok, I think I get it but it’s getting really late and I want to feel you inside me”
Smiling, he took the glass from my hand and pulled me to him. He turned me around and took the blanket from my shoulders and then helped me out of my cropped leather biker jacket. He started to massage my neck and shoulders, kissing my neck gently as he did so. His touch was like heaven. He knew all of the right spots to hit and his tongue on my neck was doing very naughty things to my brains pleasure centers. He continued to massage my back shoulders and neck, making me melt with desire. I turned on his lap straddling him and started to kiss him. He responded in kind and I felt his tongue darting in my mouth like an asp, gentle and delicate. His hands rubbed over my body, cupping my ass, feeling my legs and thighs. I got a special thrill when he ran his hands over my ersatz titties as they were feeling especially sensitive. I kissed my way down his neck and chest, opening his robe as I did so. Working my way down to his cock, I had an insatiable need to feel it between my lips. I was gratified to see that he wasn’t as large as Derek or Jon my best friend. I was determined to feel him inside me but was a bit worried about how I would handle it. I had played with some makeshift toys before( a handle from a large screwdriver, a small vibrator I stole from my sister, the handle of a brush, etc.) but had never had a cock in me before and was unsure how I’d handle a real cock. He was about 6 ½ inches long and thick but not too thick. I started to make love to his dick with my mouth, attempting to emulate the porn stars I’d watched on vhs ,when I would babysit for our neighbors, after the k**s were asleep. They had a nice collection and my favorite at the time was a star named Ginger Lynn. He was gentle and totally different from Derek and I loved it. I swirled my tongue around the head of his dick and licked up and down his shaft with my lips caressing his balls. Soon he was moaning in pleasure and lifted my head up from his lap. He looked into my eyes for a moment and then kissed me deeply. I knew he was ready to fuck me so I fumbled on the coffee table for Kayla’s purse and the condom’s in it. Pulling one out I tore the wrapper open with my teeth and slipped the condom in my mouth so I could apply it over his dick just like Michelle had done with me so many times before. I tried to roll it down over his cock but it wouldn’t roll down. Eventually I figured out the condom was facing the wrong way and took it out of my mouth and just rolled it on with my hands. So much for my ultra smooth seduction moment!
After I got the condom on him I climbed up on his lap and straddled him, I spit into my hand and lubed up my ass with my saliva and lowered myself upon him. There was a lot of resistance at first but finally the head of his cock slipped inside me. My eyes flew wide open as the pain was pretty intense at first! I held myself there with just the head of him in me and waited until the pain gradually subsided. Slowly I lowered myself down on him pulling back up only to slide back down a little deeper each time, eventually I had all of him inside me and loved the feeling. It was hard but not rigid and unyielding like the toys I had played with before, plus it was warm and velvety. It only took a few moments to decide I loved it. I slid up and down on his cock loving the way he felt in me increasing the speed of my gyrations. After awhile he grabbed my ass and stood up leaving me impaled upon his awesome dick. He gently lowered me down on my back on the carpet next to the fireplace. Putting my legs over his shoulders he started thrusting into me, slowly at first. Soon his tempo increased and he was fucking my ass like a jackhammer. The feeling was incredible! I felt a slow burn starting deep inside me building to a raging bonfire. I knew then that I loved being a girl and taking a man’s cock deep inside me. In that moment I felt completely like I was a female and born for this glory. After what seemed like hours but was entirely too short of a time Tracey cried out thrusting hard into me and collapsed on top of me. After a few minutes he straightened up, sliding his limp cock out of my sensitive ass.
“That was great Baby” he whispered “Was it worth the walk?”
“Definitely” I replied knowing I would find a way to do this again and the sooner the better!




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Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

3 years ago
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Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

2 years ago
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my life as a sissy crossdresser

it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

2 years ago
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Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

Crossdressing
1 year ago
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Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

4 years ago
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First Time With Crossdressers

For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...

3 years ago
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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

2 years ago
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First Time With A Hot Crossdresser

My email id is Please contact me for any queries, doubts or proposals. I usually work late nights, and leave home by 1 am. I take a rickshaw for home, which happens to cross this one spot where post-midnight you usually find young crossdressers here on business at the side of the road. They are dressed mostly in skimpy western outfits, some of them are really attractive. That’s saying a lot coming from me, for a 26-year-old straight guy. I’ve never been bi-curious either. It’s been months I’ve...

Gay Male
1 year ago
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Chronicles With Sexy Crossdressers

My email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...

Gay Male
1 year ago
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Experiences Of A Crossdresser

This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also. I usually...

2 years ago
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Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Crossdressing
2 years ago
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My first time as a Crossdresser

Its 18 months ago. I had now become comfortable wearing womens clothes. I had been experimenting for around 3 months. I gradually started to get more confident in both my clothes ......and without. I started to dress more like a slut. Short skits. Suspenders. Corsets. I had also become more comfortable with my body as well. My hole was tight as could be. Like everyone, i started with fingers, one, two .....before moving on to small toys. After a few months, i had graduated to a 9 inch...

3 years ago
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Mortimer and Myrtle A Love Story

Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry.Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...

Love Stories
1 year ago
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Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5’10’ in height. She is also a fairly busty woman with a 30DD chest with about 35′ hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

1 year ago
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The start of my life as a submissive crossdresser

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines.We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and when he removed his hand I curled my fingers around his erect shaft and began to slowly wank him.I just...

Crossdressing
3 years ago
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Craigslist crossdresser

It finally happened. I got a response! I’d been corresponding with him on Craigslist, but then suddenly Craigslist personals were banned. I tried to reply to the Craigslist generated email that I thought was his, but I’d deleted all of his email’s in a moment of weakness. Now I had no way to get in touch with him. He’d posted about hosting crossdressers and providing a safe, relaxed place for us to fulfill our fantasies. He said he would be gentle. I’d told him who I was, that I liked to wear...

1 year ago
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Motel Fun for College Crossdresser

Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...

Crossdressing
2 years ago
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A Tale Of Crossdresser

Hey, this is my first story that I am writing but not definite new to the glorious crossdressing field, Kindly forgive me if there are any mistakes, suggestions are welcomed people who are moving to Bangalore or in Bangalore if they want to my friends or a hook up we a cross dresser can contact me at m First, I don’t have a perfect girl figure but I wanted to be dressed as a girl, do a girl activity from a long time but it didn’t come true. I always used to wear my mom’s clothes like bra &...

Gay Male
3 years ago
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indian crossdresser

hiiiiiiiiii every one here's kiran from india ,punjab first of all its not a fictitous story ,it is  a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs............................... me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when our holidays were going on my parents were with at home ,i asked them about there relationship .they bit were not happy...

Crossdressing
4 years ago
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A great experience as a crossdresser

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie.One of my early experiences was when I was 18 going on 19. I had been to a thrift store and purchased several items of ladies...

Crossdressing
1 year ago
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Party Surprise First sex as a Crossdresser

This is a work of Fantasy. I hope you enjoy.Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.I didn’t consider myself bisexual,...

2 years ago
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First taste of cum for a Crossdresser

I had never really been with another man before and I had always thought about it as I dressed up as a slutty girl and played with my little toys to orgasm. I'm a little tall at 5, 9 and with heels a monster! I have an average body, nothing feminine, but not out of shape and a nice big bubble ass.Until that night. I had been sent to Dallas for a business trip and was super excited to dress up in my hotel room and play around! I played around a couple days in my room and just got dressed did...

3 years ago
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The Liberation Of Father Mortimer

When Father Mortimer checked into the hotel it was eight in the evening.The room was a basic no frills double with a small bathroom. He would never stay in such a hotel if he was attending one of his ecclesiastical conferences but for what he had planned it was just perfect.He got down on his knees and bent his balding aged head over a black gilt leaf Bible he had respectfully placed on the edge of the bed.“Blessed Lord Jesus forgive me for my sins,” he muttered and crossed himself three...

Spanking
1 year ago
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My First Crossdresser

Only a few years back in my young 20's i discovered Craigslist. I had no idea something like that existed and was immediately drawn to it. After building up the courage to meet up with a few guys a couple times i found an add in the T4M section. I got instantly hard when i seen this girls pictures. A slim sexy girl with an ass to die for and a desire for Cock. After some back and forth emailing for a few days we agreed to meet in her place.I went around to her place late that night when the...

3 years ago
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Cock sucking Crossdresser

When I was out on my own I started to buy a few things' mostly panties and thigh high stockings then a skirt and a blouse things that where ease to get to fit me. From there I learned to find my size in dresses and shoes this started to put my wardrobe to gather, but I still needed a wig and makeup so it was back online for more shopping, With lots of practice I became pretty good at putting on my makeup, plus doing my wig hair and a waste cincher I looked pretty darn good if I say so my...

2 years ago
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The feminine crossdresser

Chucky open’s his eyes as he awakes, looking around at his familiar surroundings in his bedroom. Band posters, comic books and video games all over the floor. His parents always gave him crap about the things he liked and tell him the typical “you’re too old to be into thoses kinda things!” He didn’t care though. He stepped out of his bed in his black t-shirt and grey track pant’s that he wear’s to bed and walks over to the window to look out as he...

4 years ago
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Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts. This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started...

3 years ago
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indian crossdresser

hiiiiiiiiii every one here’s kiran from india ,punjab first of all its not a fictitous story ,it is  a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs…………………………. me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when our holidays were going on my parents were with at home ,i asked them about there relationship .they bit were not happy with each other...

1 year ago
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  • 7
  • 0

Motel Fun for College Crossdresser

Before I start the story I want to describe the setting so you get a better idea: it’s a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that’s for sure. The layout of the motel is a rectangle. The rooms surround the rectangle’s perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...

3 years ago
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My Night with a Crossdresser

I am not a good writer but this was the hottest night of my life.I was out of town on a Business trip, staying alone at a nice hotel. After a long day of meetings, I was sitting at the Hotel bar drinking a glass of Scotch.The bar wasn’t crowded but wasn’t empty either. The seat next to me was open. Wasn’t long before what I initially thought was a woman came in and sat next to me. She said hello and ordered a glass of white wine. I realized then that she was a Cross Dresser. she looked to be...

3 years ago
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Halloween cd crossdresser

TinkerbelleMy sister , Candy, and I were fraternal twins, but looked nearlyidentical. Pretty much the same height weight and build. In high school,she was always teased about having small tits and I was always teasedbecause I was small, thin and had a big ass for a guy. Because of this wewere extremely close. Best friends really. We spent nearly all our timetogether.After college she became a consultant and I became a math teacher. Becausewe were so close, I spent lots of time at her house...

3 years ago
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Uber driver fuckes teen Crossdresser

Hi guys im a cd from Orange County and i had the sex ever last night with someone I never expected. So it was around 1 and i had just soent the night with my “friend” well I had just blew him and watched a movie and he got me an uber so i kissed him and left when tge uber came and I went on my night. He told me it was a white truck and espanic i went in and told me my “friends” name and we drove off. It wasnt even 10 seconds and he said what was my name i told him i was “. “ and he said nice to...

1 year ago
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Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts.This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started joining...

2 years ago
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How I became Jayne The Crossdresser

It started in 1976,around August,I had just met John a guy my around my age,who lived alone near me. He wasn't shy to admit he was gay,and I was curious,and I told him one Friday after we got back from the pub about my interest. Before I knew it John & I had undressed & I had Johns cock in my mouth,sucking him off,& he soon quaked into an orgasm,cumming in my mouth so fast I gagged slightly before I managed to swallow most of it.John was keen to make it a pleasure for me &...

3 years ago
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Natural Ingredients for a crossdresser

It was still snowing outside and I wasn't going to be recieving any visitors today so I decided to treat myself and while the day dressed how I wanted.... I had set the heating up high at my place, so I could wear one of my sexy side tie bikinis which show off my sweet little ass so well. Having enjoyed the view in a full length mirror and got some self shot snaps, I found myself sitting at my dressing table wondering how to amuse myself next.... Looking at my face in the mirror I noted a...

2 years ago
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Patni Patni A Crossdresser

“Oh Ramesh! I am so happy that you came today.”, I pressed my boobs against his chest and wrapped my arms around him, as soon as Ramesh entered in my flat. And he grabbed be in his arms too like a real man. He began to touch my body and moved his hands all over my back and lower waist. I was titillated by his sensual touch. “Where else I could be, my darling.”, he said and slowly slipped one of his fingers from the back of my saree blouse. He was feeling my bra strap with his finger. We two...

2 years ago
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transforming into ashley crossdresser

durring the day,i'm working i'm dressed in my work clothes,but when I come home I take a hot bath washing all over my body,then shave my legs,arms chest,and face.I even add babyoil in the water so that my skin becomes soft.then I will clean myself ass inside/out.then as i'm drying off i'll start ptting on my makeup,this takes me about an hour,I like taking my time so that my makeup looks perfect,so that when I put my wig on I'll have that female look.then go in the bedroom pick out something to...

2 years ago
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Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts. This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started...

Gay Male
2 years ago
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A great experience as a crossdresser

Note: ——I am NOT the author!so plz Don't ask me about part two,am simply sharing this lovely story with all of you because I have not seen it on hereI was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and...

1 year ago
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  • 7
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A great experience as a crossdresser

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie.One of my early experiences was when I was 18 going on 19. I had been to a thrift store and purchased several items of ladies...

1 year ago
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Beauty And A Crossdresser

Hi this is hotslutaddy back with my friend ishika’s story. Hi this is ishika. Those who have read my first story “lost virginity from behind” in virgin archive should know that I am a cross-dressing bottom gay.It had been 8 months till that incident and I had completed my schooling. Kartik had become my boyfriend and I love him more than my life. Now I was in a college in a nearby town and I lived at a house on rent. I lived alone there so I had an almira full of female clothes and make up.Most...

Lesbian
1 year ago
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The 2nd Halloween for a Boy Dressed as a GirlPart 1 A Blissful Young Crossdresser

5th Grade. 11 years old. Dressed as a girl again on Halloween. As a cheerleader. My next old sister's cheer uniform. Her idea. Her bra and panty too. My special "Boob" socks to give the appearance of breast. A discussion I had with my next 2 older sisters. How ample were my false breast to be? Normal size for girls my age? Bigger for my ego as a girl, for all the times I have dressed up with them through the years? Dolly Parton size? Because my 2nd oldest sis Joan, made...

2 years ago
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SALLYS RELUCTANT CROSSDRESSER

CHAPTER ONE                Sally and Dave had been dating since high school, it was a turbulent relationship, and at this moment in time they were having a few arguments, Sally called them dicusions. They were both nineteen and in love with each other, and both were jealous and possessive of each other. Sally was the one with the ideas, and Dave let things fall into place as he could never emulate her suggestions. They were sitting in the lounge of the flat they rented, they were not married...

1 year ago
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The hottest crossdresser

I was drinking with my friend Curtis one night as his girlfriend Jane was out with her friends having some drinks. The topic turned to cross dressers, as I had had let it slip, that one time I mentioned to him, I had dressed as a girl a few times when I younger in my moms clothes, and it felt great. He asked if I had any girl’s clothes at home that I wear from time to time, which I reluctantly said yes. With that Curtis asked if I would wear some of Jane’s clothes to see how I looked. “Sure,...

Bisexual
3 years ago
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Wifes FirstTime With Another Man

My wife Karen and I have been married for 9 years, and have three k**s. Karen is a short 5'1; slim, has an attractive face, short brunette hair, and smallish tits with magnificent large, puffy nipples. She’s fairly reserved, especially about sex. It’s not that Karen doesn’t enjoy it, she does, she’s just not comfortable talking about it. She claims to have no sexual fantasies, and outside of breathing heavily, makes little sound while we’re having sex, which is maybe once or twice a month since...

2 years ago
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Beginnings Chapter 4 Room For Change

Later that evening I chased like a child through the wide-open meadows of my mind, carefully sweeping as many of my butterfly thoughts into a delicate net as I could. The beach was now empty and only the sleepy ghosts of happy days remained. A tired sun, its dwindling energy spreading like a worn, burnished cape around it, was balancing uneasily on the far horizon. The darkening sea was giving up cool hints of her salt-scented breath, which every so often lifted wisps of hair from my face and...

Lesbian
2 years ago
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Beginnings

Beginnings Larry was hard at work on a new accounting cost model project. As the newest member of the firm and a recent university graduate, he was fortunate to draw this assignment. Stan stopped by to offer his congratulations. Stan was a long time member of the firm; and, had taken Larry under his tutelage at the firm. Larry was grateful as he was new to the area and did not have family or friends in the town since moving here from college. “Congratulations on your new project assignment....

Wife Lovers
3 years ago
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Beginnings

Beginnings It started out in such a simple and harmless way. Some friends were having a Halloween party for a Girl Scout Troup and I agreed to provide some entertainment by telling fortunes. For fun, we decided it would be best if I wore a costume so I agreed to become Caroline the fortune teller for the night. I had never worn women's clothing before so it seemed like quite the lark. I did some exploring on eBay and found I could shop anonymously as long as I knew what size to...

3 years ago
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Beginnings Day 5 Harrys Job Offer

BEGINNINGS - DAY 5 - HARRY'S JOB OFFER When I got out of my bath I checked the time. I had a few hours before Harry was due to pick me up. I decided to just relax and play through the last few days. It had been quite an experience. I had gone through a series of steps in adopting a female persona, each of which had a part, large or small, in placing me in my current situation. After liberal lotion, I had simply thrown on a bra and my robe and was sitting quietly in my television...

4 years ago
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Beginnings Day 7 A New Friend

BEGINNINGS - DAY 7 - A NEW FRIEND Driving to Harry's club for my 10:00 appointment, I thought about the days ahead and the enormity of the job I had accepted. So far, living as a woman full time had been nothing short of a spectacular experience for me. I simply adored the sensuous feel of my clothing and felt tingly just thinking about my new found sex life. My goodness, Suzy was an amazing lover! When I arrived at the club I had to focus. I had fallen into the trap...

1 year ago
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Beginnings and Endings

Beginnings and Endings By Ray Kitten Peter shifted the heavy garbage bag to the center of his back as it had once again managed to slip down towards his armpit. Once the traffic signal changed he trudged again onward, still deep in thought as he plodded right in front of a car that was trying to navigate a sharp left turn. The driver forced his brakes and narrowly avoided running Peter down, as he quick dashed to the sidewalk the driver leaned out the window to holler words which...

2 years ago
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Beginnings Day 2 Shopping

BEGINNINGS - DAY 2 - SHOPPING! I awoke slowly the following morning. When I had arrived home I was tired but exhilarated. What a wonderful night. From having never dressed as a woman before to coming home from my first kiss from a man, it certainly had been an eventful day. I remember coming into my house and thinking about going directly to bed. I took off my coat and looked into the mirror in the hallway. There stood a 50ish woman looking back at me. I smiled to myself and...

2 years ago
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Beginnings Day 3 Preparation

BEGINNINGS - DAY 3 - PREPARATION I slept quite late the next morning, spent from a night of sex with Suzy and generally basking in the memory of a quite fulfilling experience. When I finally stretched and stood up, I realized that it was Tuesday and I had one more day before my date with Harry. Harry. Hmmm. Last night Suzy and I had spent hours making love woman to woman. Of course, at times my manhood was welcomed but for the most part we just snuggled, nibbled and licked. I...

3 years ago
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Beginnings Day 6 Offer Accepted

BEGINNINGS - DAY 6 - OFFER ACCEPTED I arrived home entirely energized from the day, both what I had done and what lay ahead. I decided to take a quick shower before dressing to meet Harry and review his offer. I just used a scented body wash and toweled off rapidly. I decided to shave but first put on my bra. These wonderful breasts feel so much better with support! After a close shave I went to work on my hair. I massaged just a tad of product into it and used my blow dryer and...

4 years ago
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Beginnings Day 6 A Mary Kay Meeting

BEGINNINGS - DAY 6 - A MARY KAY MEETING After a full day, the thought of a relaxing party with Suzy's friends sounded wonderful. As I walked to her door I felt the breeze in my hair and on my legs. My heels clicked on the pavement and I licked my lipstick clad lips in anticipation of a fun night. Suzy was waiting at the door for me. As was her custom, she was very professionally dressed for her Mary Kay meeting and her makeup was beautiful. Of course I wanted to kiss her on the...

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Beginnings Day 8 Saturday Fun

BEGINNINGS - DAY 8 - SATURDAY FUN After Felicia left I had climbed into bed and pondered our time together and the events of my life since I had decided to live as a woman full time. Aside from the sex, which had been glorious beyond words, the sensations I felt throughout each day had been entirely titillating. I adored my clothing, especially hose and shoes, loved my breasts and wass entirely enamored with makeup and polished nails. With these delicious thoughts in my mind, I...

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