My first time dressed as a girl (A True Story) The

My first time dressed as a girl (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 s*******n 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 b*****r and s****r 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 f****y 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 bl**d 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 bl**dred 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 s****rs. 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 e****t 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 d***k 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 d***k 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 f****y 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 f***eful 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 jist 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 s*******n 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 s****r, 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 asl**p. 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!







..

100% (59/0)
 
Categories: Lesbian SexSex Humor
Posted by sbobbi66
1 year ago    Views: 3,792
Comments (5)
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5 months ago
A great story, with plenty of sex, and a thing or two to think about too!
5 months ago
What happened with Mikki?
7 months ago
What a great story. And for a couple of reasons. First, it sounds like you and I got our start in dressing up in the same manner. I to wore my Mom's and sister's sexist lingerie around the house whenever I could. I also experimented with my friend. Those where fun days. And while I have never been outside dressed up, I sure love fantising about it! Finally, you have shed some light on how i feel all dressed up. I am a total man in man clothes and a total slut when dressed. I had never really thought about it before in those terms so thank you. And again great story!
11 months ago
Damn good story! I have sex like this with men and I'm addicted to dressing like a woman and pleasing a man!
td2
retired
1 year ago
fantastic tale... i'm so anxious to have the experience when i'm dressed. I love feeling the "slut" role.