The following is a totally true story about the first date I ever had with a transsexual back in October of 1998. Only the names have been changed in case it ever got back to anybody either of us knew. If you are like I once was, a passive admirer of t-girls, I highly encourage you to pursue your desires, because you may wind up with an experience you will treasure for the rest of your life, or even better a relationship with a fantastic woman.
I was pretty nervous about my first social encounter with a transsexual. I'd paid for sex with a tranny once before, but never actually put myself in a position where I had to pick up a t-girl for a date. Sure, I've been on plenty of dates with genetic girls, and there's always a little nervousness on any first date, but the tension was especially high as I drove my Jeep Cherokee to Jenna's apartment.
We'd met on an adult phone service here in Dallas, one of those where you record an ad and listen to ads from other people. Most of the ads I heard on the service were chaff, but when I heard Jenna's ad I knew I had to give it a shot. Most of the time if I left a recording for someone, I would never hear anything back. Other times I got messages from gay guys or black chicks, neither of which I was terribly interested in. I was on that phone line for one reason only - to meet an exciting t-girl. Anyway, after a few days of phone calls back and forth I got up the nerve to ask her out on a date - she accepted, and we made plans for the coming Friday.
Turns out, she lived about 5 miles away from my place, which totally surprised me as I didn't really imagine there were too many t-girls out in the 'burbs. I lived in an apartment near the international airport here in Dallas at the time, and she had an apartment of her own just a few miles down highway 183. So, on that fateful day, I could barely sit in my seat at work as I was so looking forward to the date. When I got home I walked my dog, tried to relax a little, took a shower and wore my favorite pair of jeans, and a dark blue button down shirt that I thought looked pretty good on me, as well as my trusty pair of Doc Martens boots.
I am an above-average looking guy, though I could stand to lose a couple of pounds. At the time I was in better shape than I am now, 6'4" and about 245, with brown hair and green eyes. I never have trouble meeting girls, but my shyness does keep me from closing the deal as often as I might be able to. I've just always been so scared of rejection its kept me from really experiencing some things. Maybe that's why I chose the anonymity of a phone chat line to meet someone.
As I pulled into a parking spot at Jenna's apartment, my stomach was filled with apprehension. What if she thought me unattractive? What if she was scary looking (I've seen plenty of pictures of guys in dresses on the internet and they do not do a hell of a lot for me)? What if she was some kind of psycho? Jenna seemed to have a likeable personality and had her head on pretty straight from what I could tell (she worked as a nurse of some kind in a nearby hospital), but you never really know what to expect on a first date, and even less when you've met over an adult chat line.
Jenna described herself as about 5'4", 115 pounds with brown hair and brown eyes. She sounded nice but I didn't get my hopes up too high on her looks - I tried to temper my optimism a little bit.
Putting my hesitation aside, I climbed out of my car, and walked the few short steps to her front door. I had brought a bouquet of mixed roses (none red of course, didn't want to give the wrong idea) for her, and I held them in front of me as I knocked on the door. From inside I heard the yelping of some small dog (I am not a big fan of those yappy little dogs), so I knew I had the right place - Jenna had told me about her darling pooch during our phone conversations.
When the door opened, I was almost shocked, but in a good way. Jenna was incredibly cute! She was wearing a white blouse, tucked into a pair of fairly form-fitting jeans, with black platform boots. Her hair was brown and down to her shoulders, arrayed around her head so that it framed her cute face. She had brown eyes, a cute button nose, and lips so full I wondered if she had silicone injections into them. Additionally, her blouse highlighted her small but firm breasts.
"Rick?" she said.
"Hi," I grinned sheepishly, holding the flowers out in front of me like a shield. I could feel my cock stirring in my pants, so I tried to shift my weight to keep it from being obvious. While I did have hopes that I might bed this woman at some point in the future, I had no illusions that I'd be bagging her tonight. She seemed like a nice person over the phone and I've always been more of a relationship-oriented guy, so I wasn't looking for a wham-bam-thank-you-ma'am type of scenario to unfold.
"These are so pretty!" Jenna exclaimed as she took the flowers. "Just give me a minute to put these in water and we can get going," she said, closing the door to keep her dog from getting out into the parking lot. I got a wink of her ass as she turned around, and if the front of her wasn't enough to give me a raging hard-on, the back view certainly was. While a little small for my taste it was perfectly shaped. I wanted to reach out and grab it but I restrained myself.
Waiting patiently, I couldn't believe my luck. Not only had I met this nice t-girl over the phone, instead of just the average looking girl I had steeled myself for, here was a sexy cutie that wanted to go out with me! While she was inside, I managed to stifle my hard-on a little bit, so that when she came back outside, I didn't look like the total pervert I knew myself to be.
"Okay, ready to go!" Jenna exclaimed as she locked the door behind her. "First let me give you a hug!" she said, and reached her arms around me in a warm embrace. I could only return the hug, and as I pulled her into me, I felt those soft breasts that I had admired earlier squeezed against my own chest.
"Which car is yours?" Jenna asked as we started to walk to the parking lot. I motioned to the two door black 1998 Jeep Cherokee, and walked her to the passenger side. I had to help her in after opening the door, because the car is a little high off the ground for someone that size. After climbing in she just smiled at me, so I closed the door and walked around, getting into the car myself.
"So, where are we going to have dinner?" she asked.
"Well, there's a place that I think would be perfect on a night with weather like this. Have you ever had Tapas?" I replied.
"Tapas, what is that?"
"Tapas restaurants are basically big wine bars, that serve a large selection of appetizer sized items. Basically, what you do is order a few things each, and then share everything together as you have a few bottles of wine," I replied, pulling the Jeep onto 183 eastbound, heading into the heart of Dallas.
On the way we continued to make small talk, and it was obvious that we were really hitting it off. I was still very nervous but Jenna seemed totally at ease, and frequently would reach over and touch me warmly, though we hadn't kissed or anything like that yet. It just seemed like a totally natural first date between two people who enjoy each other's company - for me there was electricity in the air, though.
When we got to the restaurant off of Knox in Uptown Dallas, I had to drive around for 10 minutes before I found a parking space in an adjacent neighborhood. I was a little worried that I'd get a ticket where I was parked, but I was tired of driving around so I figured the hell with it, and parked there anyway. Jenna got out of the car and walked around to the front to meet me. I let her walk a couple of steps ahead of me so I could check out that fine ass once again, before joining her, as she clasped my hand and we chatted while walking a few steps to the restaurant.
Cafe Madrid is a fairly popular place on weekends, and this Friday night was no exception. Fortunately, while the place was pretty packed, a group left right before we got there, so we got a nice table inside of the restaurant. I had hoped to sit outside and enjoy the cool October air, but was happy just to get a seat, really.
"This is a nice place," Jenna murmured to me from across the table. "So, what do you want to drink?" she asked.
"I thought I'd start us off with a pitcher of Sangria," I mused. "They make the best Sangria here, I think you'll really like it," I said, knowing that a few glasses would serve well to put me at ease, too.
"What's Sangria?" Jenna responded.
"I'm surprised you don't know, seeing as you are Hispanic yourself," I said, "but Sangria is basically some cheap red table wine mixed in a big pitcher with chopped fresh fruit like oranges and apples, and some liquor to sweeten it up some more, and then the whole thing is iced. Its a very refreshing drink," I went on.
"Sounds lovely," Jenna said, beaming at me from across the table.
We chatted a little more, and our Sangria arrived quickly, so I poured us each a tall glass, and then we toasted to new friendships. Jenna really seemed to enjoy her Sangria and I quickly had to refill both of our glasses.
We drained the first pitcher quickly, and by then our food orders had arrived. Its been a while so I can't recall precisely what we ordered, but I do remember that Jenna so enjoyed the marinated, grilled Portobello mushroom that we ordered another one later on. The night went by quickly, and before I knew it we'd been laughing the whole evening away while drinking three pitchers of Sangria between the two of us, and I was quite tipsy.
Jenna was tipsy too, a fact brought home when I felt her stockinged foot between my legs, at crotch level. Out of reflex, I grabbed her leg, and she giggled.
"You better watch out where you put that leg .. I might not let go!" I exclaimed, laughing.
"Oh baby .. I hope you don't!" Jenna replied, sliding down in her seat as I felt her other foot creep between my legs. I grabbed it too. I knew she could feel my cock getting hard with her feet, and she smiled slyly. I was getting nervous again, because I didn't want to blow my chance with this great girl by acting like a dog in heat, but she was really turning me on.
"Lets get out of here," Jenna said, withdrawing her feet. She was right; it was getting late and the restaurant had really emptied out. I knew I'd had too much to drink, and its a pretty long drive from Uptown Dallas to the Mid-Cities area where we lived, and I still had to drive home after all that, too. I still wasn't planning on anything else happening tonight, except maybe a nice goodnight kiss which I was really hoping for.
We stumbled back to my car, and fortunately, there was no ticket, which pleased me to no end. We were both a little playful at this point, so on the way back I took the opportunity to slap her on the ass once or twice, leaving her giggling each time. I couldn't help but marvel at her sexy, petite frame and wonder what she would look like naked. I felt like the evening had gone well and that I could probably plan on seeing her again, and eventually getting those tight jeans off of her.
We started to drive back home, but I made a couple of wrong turns due to my inebriated state, so for a little while we wound up on I45 headed towards Houston, until I got us facing the right direction. Jenna didn't really help me much, she was distracting me the whole time with singing, rubbing her hands on my right arm and leg, and in general getting me all hot and bothered. Then, to my shock, Jenna pulled her tiny frame over the console, and sat right on my lap, kissing me passionately and deeply. I almost drove off the road!
"Hey baby I would love to kiss you but this is kind of a bad time, I'm driving and with you on my lap I can't see a damn thing, you better move back over to your seat," I said, as I lifted her off of me. I was terrified not only of getting into an accident, but of getting pulled over by a cop and getting a DWI. It was well after midnight by this time and there weren't many people on the road, so a car weaving around in a lane kind of sticks out.
Settling back into her seat, Jenna spoke. "Do you want to have sex with me tonight?" she asked. I was flabbergasted. Of course I wanted to have sex with her! I just didn't expect this to happen at all.
"Oh my God, of course I do," I responded, dumbfounded. To be honest I wasn't sure if she was serious or not.
A simple "OK" was her only reply.
"Wait, are you serious?" I asked. "I mean, I would love love love love to have sex with you but you are just kidding, right?"
"No way, lets go to your house, and I will show you that I'm not joking," Jenna replied.
At this point I wasn't that worried anymore about getting a ticket. I drove home in record time, and when I parked my car and Jenna climbed out, I kissed her deeply while holding her delicate frame in my arms. We climbed the stairs to my apartment, and when I opened the door my dog almost mobbed her. He's very friendly, but I could tell that Jenna was a little taken aback, as he's about 60 pounds and was jumping all over her. He had to take one for the team and get locked in a crate - I wasn't letting my best friend ruin this for me!
I closed the door, and we continued to kiss passionately. Now that we were in private, I reached down and squeezed that sexy ass while we kissed. God, it felt so great, and I could feel her getting hotter as her hands rubbed up and down my back.
"Lets go to the bedroom," Jenna said, and I was happy to oblige. We moved into the bedroom and she laid down on my bed, with me on top of her, as I continued to kiss her beautiful, sexy lips.
I reached back and helped her pull of her shirt, and opened her bra, releasing her perfect B cup tits. She'd obviously not had any implants and the breasts were soft and natural, just from hormone therapy. I started to lick and suck and nibble on her tits while she helped me get out of my shirt. I'd alternate between sucking her tits, licking her neck, and kissing her, but it quickly became obvious that she wanted to get the show on the road, as she reached down and rubbed my prick through my pants.
Quickly unbuttoning her pants, I pulled them down and saw her hardness through a sexy pair of silken panties. I pulled them down in one stroke, releasing her penis. It was almost as long as mine, but slimmer, and totally shaved save a small patch of dark hair at the base. A clear drop of precum oozed out of the hole. I just had to taste it.
I reached around the base of her cock with my hand, and squeezed her balls gently, taking the shaft into my mouth. For the next ten minutes I worshipped her cock, licking it up and down, sucking it, bobbing my head up and down on it, while Jenna moaned and rubbed her hands through my hair. It was slick with a mixture of her precum and my saliva and I loved every inch of it.
After a while, Jenna stopped me from sucking her cock and opened my pants, unleashing my thick 8 inch dick. I never thought of myself as extraordinarily gifted, but after seeing her penis next to mine I realized just how thick I really was. "Oh babe, your cock is so big," Jenna said as she slowly stroked my cock. "I want you now, Rick," Jenna said, looking in my eyes and kissing me deeply before laying back on the bed and raising her legs, exposing her totally shaved, luscious love hole.
"Babe, put it in," Jenna moaned. I guess she really wanted to be fucked. The problem was, I really hadn't planned on this happening - even when she invited herself over for sex I thought the most we would do was a little fooling around, maybe some oral sex - I never imagined she would want me inside her that night. Because of this, I really didn't have any preparation, nothing to lubricate the entry with. So I tried to wet her asshole with my tongue, and licked deeply of it.
"Don't do that, it embarrasses me," Jenna said, although it was obvious that she loved the feeling of my tongue lapping at her tight hole. Her asshole was so cute and small, with a ring of pink skin surrounding it. I was a little surprised that I enjoyed licking her so much, I really had only done it in the heat of the moment, but as I licked in and around her hole, I found myself getting more and more turned on. There was just something incredibly sexy about her legs over my shoulders, pulling her cheeks apart and burying my tongue in that hot ... pussy'.
Finally I couldn't take anymore foreplay, and when I thought her asshole was wet enough, I spit on my cock and started to line it up for entry inside of her. She was tight and as I pushed into her, she squealed in pain. "Use some lotion, its too tight," Jenna urged.
"I ... er ... don't have anything like that," I hemmed and hawed.
"You are supposed to have lotion! I guess you don't want to have sex with me after all," Jenna kidded. Not one to pass up an opportunity like this one, I quickly decided on a solution, jumping out of bed and rapidly throwing clothes on.
"Wait right here - I am going to the store and I will be right back, I promise," I said. True to my word I raced to the convenience store and bought the biggest tube of K-Y jelly they had. The clerk eyed me a little funny as I bought it, but I really didn't care - I was going home to the sexiest woman I'd ever been with.
When I walked into the bedroom, I again realized just how lucky I was. Jenna was laying on her side and stomach on my bed, her head on a pillow, eyes closed, breathing level. Only the bathroom light provided illumination for her beautiful body. I admired her for a moment as I undressed, watching the rise and fall of her body with her breathing. Her ass was slightly parted because of how her legs were positioned, so I could just see a glimpse of her love hole.
I laid down next to Jenna, putting my left arm around her waist. I guess she wasn't asleep after all, because she quickly turned her head and put her tongue in my mouth, getting my rod to full attention once again. I reached down between her legs, lovingly cupping an ass cheek, as I felt the heat from her opening on the side of my hand.
"Baby, fuck me now, I want you so bad," she whispered as she withdrew from our kiss. I leaned back as Jenna turned onto her back, once again raising her legs in beckoning fashion. Opening the K-Y, I smeared a healthy glob of it on my cock, and then proceeded to work my slippery fingers into her hole. "Stop, I want to feel your cock opening me up," she commanded. Who was I to disobey? I withdrew my fingers, and pulled her legs apart, marveling at how her love hole glistened from the K-Y I had applied to it. All of the veins in my cock were bulging - there was no question that I had never been this hard in my entire life - my cock was like concrete, totally engorged with blood.
Moving forward, I positioned the head of my cock at the center of her opening. I could feel how hot she was - I was just as hot. "Oh babe, put it inside me," Jenna moaned. Obliging, I began to push my penis into her asshole. Slowly but surely I could feel the head of my cock forcing itself inside of her.
"Ugh ... Oh!" Jenna grunted, throwing out her hand to indicate that I should stop, her eyes bulging, mouth open. "Oh my God .. Babe .. you're so big ... oh my god ... oh my god ..." Alarmed, I immediately stopped my progress. "Don't stop baby ... put it in," Jenna continued. With her words of encouragement I could feel myself getting even harder, and I renewed my assault on her asshole. After a minute or two of slowly pushing, the first inch of my cock finally disappeared into her ass.
I marveled at the sight. It was fucking beautiful. Jenna had her head back and was moaning softly. I had my hands on her ankles, and her legs pulled back, exposing her ass to me. Her penis was rock hard and pointing almost sideways from how I had her legs bent, precum dripping steadily onto her belly, and finally the piece de la resistance - my thick cock slowly disappearing into her tight asshole. Jenna stopped me a couple more times as I continued to push into her, but after about two or three minutes any pain that she was feeling must have subsided, because she now really encouraged me to put my dick all the way inside.
"Oh babe, it feels so fucking good, your cock is huge, fuck me babe!" Jenna moaned as I continued to push my way into her. Her asshole was so hot, hotter than any pussy I had ever fucked. And it was tight! Oh, was it ever tight. Jenna's ass felt like a wet velvet vise, gripping my cock mercilessly. Finally I hit bottom .. my cock was all the way up her ass, her balls resting comfortably against my pelvis. "Baby you are fucking beautiful, from the moment I saw you I wanted you, oh my god you are amazing and you feel incredible," it was my turn to moan. This moment was better than anything I had ever experienced in my entire life. I never wanted it to end.
"Babe, fuck me! Give me that cock," Jenna moaned, urging me to use my length to maximum advantage. After a moment had gone by and I had fully appreciated the feeling her tight love hole was giving me, I withdrew a few inches, then slid it back in. I repeated this process, and Jenna writhed and moaned, begging for more. Within a few minutes I was sliding almost the whole length in and out of her secret garden, as I admired the view of her jiggling breasts and leaking cock. I tried to jerk her off while I butt fucked her, but had a hard time concentrating on both things at once.
"Where's the K-Y," Jenna moaned, and I squirted a little onto her outstretched palm. She began stroking her penis in time with my thrusts. "Fuck me babe, come inside my ass, it feels so good babe," Jenna moaned as she writhed in pleasure. I leaned forward and forced my tongue into her mouth while my hard cock slid in and out of her ass. This was fucking incredible and in fact I was going to come very soon if I didn't hold back. I started to slow down, but Jenna would have none of it, "Babe, fuck me! Shoot your come inside of me, I want to feel it," Jenna moaned. The pace of her stroking was quickening, and I too was about to blow my load.
"Oh my God Jenna .. oh my God .. I'm going to come .. your ass is fucking incredible .. I am going to come baby .. oh God, oh God, here I go, I'm coming!!!" I screamed as I arched my back for maximum penetration, blasting off a huge load into her ass. I guess Jenna could feel my hot seed flowing into her, because she responded "Yes baby, oh yes, oh god, fuck me, oh god," Jenna said as she began her own orgasm. I was too busy focusing on my own orgasm to realize it, but later on I would discover that she had shot come all over my stomach and it had dripped down her cock onto her belly. I fucked her ass until my dick became too sensitive to continue, and then pulled out of her steaming hole.
Laying down beside Jenna, I cought my breath. "Jenna, that was fucking incredible - I have never had sex like this before in my life - you are the best I have ever had," I said. "Babe, your cock feels so good .. oh my god, this was the best ever for me, too," Jenna said. I wasn't sure if she was patronizing me or not, but really, I didn't care. Reaching my hand onto her stomach to fondle her shrinking penis, I felt the warm load she had shot off earlier, and rubbed my hands in it. I leaned over and kissed Jenna, this had been an incredible experience, and based on how well we hit it off, I imagined a relationship might form here. We both drifted off to sleep, satisfied, at least for the moment.
It didn't take me long to wake up to a raging hard-on! It couldn't have been more than twenty or thirty minutes since my orgasm, but I was ready to fuck Jenna again, and I nudged her awake.
"Oh my God," Jenna said, "Are you already ready to go again!?" she laughed as she wrapped her small hand around my fat prick.
"Baby, I have to have you again ... you are beautiful and I want you now," I responded, kissing her passionately.
"How do you want me," Jenna asked suggestively.
"I want you on top, so I can see your beautiful face while we make love," I responded, thinking of the scenes I had seen in shemale porn, with the t-girl riding a cock in her ass cowgirl style, head thrown back in pleasure, hard penis jutting out as her titties bounce up and down.
Jenna turned around and had me lay on my back, then she put one leg over my hips, smiled at me, and reached back to my hard cock, which was still slippery from our earlier session. Slowly, she lowered herself to my penis, and I felt the head touching her hot hole once again. Finally she leaned back and I could feel her ass engulfing my cock. It was easier this time since she had been stretched out earlier, and I don't think there was any pain for her.
"Ooooh babe, you feel so good inside of me," Jenna murmured as she totally impaled herself on my cock. For my part I could only moan my approval at the sight of this beautiful creature slowly gliding up and down my penis.
For the next two hours we fucked in every conceivable position - her on top cowgirl style, then reverse cowgirl, then her on top leaning over me as I thrust my hips, pushing my cock into her over and over again until I came in her ass again, then we did it doggy style, then standing up with her holding the doorjamb, we fucked until we were both totally satisfied. Finally we both drifted off to sleep, and at around 5 AM I took her home. My cock was sore and she said she wouldn't be able to sit down all weekend, but that it was worth it, and we departed with a warm kiss and hug at her front door.
For the next five years, Jenna and I met off and on for the hottest lovemaking I've ever experienced. Some times were better than others, but nothing ever matched up to that first time we made love on our first date. I told you earlier I had hoped for a relationship; Jenna had just gotten out of one, and still had contact with her old boyfriend, off and on, and by the time she was ready for a relationship I wasn't ready for one anymore. We still met often to rekindle our passion, but it really never grew beyond a friendship with benefits kind of thing. Every time I'd break up with a girlfriend, Jenna was one of the first people I would call, sometimes we would get together for a drink, but often for more. A few years after I met her, Jenna got some D breast implants, and has continued to take hormones so she looked more and more feminine. I think I liked her better without the implants, though.
So, that's it, that's the whole story, or at least as much as I can remember. Today I regularly date transsexuals, in fact almost to the exclusion of genetic girls. Sex with a genetic girl is fine, but sex with a t-girl is unbelievably intimate and intense. There's nothing like feeling a girl's hard penis rubbing your stomach while her ass has totally engulfed your cock, sitting on your lap and frenching you, with her breasts rubbing your chest. Just thinking about it is enough to make me come. T-girls are so much better at pleasing a man than a genetic girl, and so much more interested in being beautiful, feminine creatures, that I'm not sure if I will ever go back to a genetic girl again. I wish things had worked out long-term with Jenna, but even though they didn't, I still have her to thank for opening my eyes to the most wonderful women in the world -- transsexuals.