I had a secret, I wanted to be with a tranny. A shemale. A ladyboy. A chick with a dick. I don't know why, but it's something I wanted to try. Don't get me wrong, I'm not gay and I didn't want some guy wearing lingerie. I wanted someone I could believe was a legitimate woman, who just happened to have a dick. So here's the story of my exploration.
(I had a membership with an adult "dating" site. I wasn't too serious about it, mainly just used it to watch videos and look at pictures that I could believe came from a real person. I had traded emails with one person on there, she was a very large black woman. She also had huge tits. I never met her but we traded lots of text messages, mostly sexual in nature. We talked a lot about how she would love to be the first to make me fall in love with the so-called chocolate pussy, and how much she wanted my white chocolate cock in her ass. We even explored the idea of buying her a strapon and having some deviant fun but the time was never right. One night she texted me, she was horny, and wanted to cum but couldn't go anywhere. I asked her what I could do, expecting some sexting and pics of her masturbating that would get us both off. Instead she sent me a message telling me to jack off thinking about her and send a picture of me cumming. This was a new level for me, and I wasn't sure how to get the pic at first, but I finally figured it out. So I sent her the pic as soon as I had it, soft dick in my hand, and cum all over me. By the time I was cleaned up with my shorts back on I had a reply. She said I was a good boy, and she came really hard seeing my cum shooting up out of my hard dick like that, imagining I was shooting on her tits. She attached a pic of her licking her huge glistening dildo, I jacked off to that later. Maybe we would have to make the time right some day. But that's a different story, and I need to stop rambling and get back on track.)
So, I had finally decided I was going to start looking at the *tranny* section, and when I did the results covered the spectrum. From gay guys who figured they had a better shot advertising there, to "women" wanting relationships with straight men, only 1 dick in that relationship. I clicked around for a while, exploring what was out there, and finally started sending emails. I would tell them that I was a straight man looking to experience a shemale. I got a few "thanks but no thanks" replies, and more than a few of my emails were never returned. However, I did get some positive replies, mostly from crossdressers, but a few from the "gifted" women I sought. I did trade some emails with a few of the crossdressers, their talk of being balls deep in a straight ass did turn me on a bit, but mostly we chatted and they jacked off to me.
One day I logged in and saw I had a message from a member with private settings, I never emailed then. But when I clicked on the message I saw she had attached pictures along with a message expressing interest in being my first experience. She was stunning, blonde, nice big tits, and an ass that would take your breath away, exactly what I was looking for. She was wearing panties in all of the pics and seemed to enjoy hiding her secret from me.
We chatted for a few weeks, trading some more pics, but I never did see her take the panties off. And from the frontal shots I was starting to doubt her credentials, but either way I couldn't stop now. Within a couple days of the first text we were texting each other all day, talking about all sorts of things, sex talk fell by the wayside for a while.
A few weeks later I had a unexpected day off, on a Friday even. This was unprecedented for me. I texted her in my excitement, and without thinking accepted her offer to come over that evening. I even went out and bought a gallon of juice, supposedly the pineapple made cum taste better, I wondered if she was doing the same. As the hour grew nearer I started to realize what I was getting myself into, and it showed in my texts. She asked if I was freaking out, and when I replied that I didn't think I could touch a cock or ass, much less return any pleasure she reassured me we would take it very slow, and no reciprocation was necessary. So I packed an overnight bag, including extra condoms and a small bottle of lube, just in case, and started getting ready.
I knew she liked hair on a man, just not a hairy dick and balls, she didn't like hair in her mouth, so I trimmed back the undergrowth before hopping in the shower. She had gently asked me to make sure my asshole was clean, out of politeness, and I understood and hoped she did the same. Squeaky clean I got out and dried off, then pulled on the clothes I had picked to make a good impression. Boxer briefs to show off my package and ass when the jeans that did the same came off. Leather belt to add to the suspense when she sarted undressing me, and a semi-tight t-shirt/A-shirt combo to accentuate my upper body. All on top of my cleanest pair of boots and topped off with a light spritz of cologne and my Mossy Oak hat.
I pulled into her driveway with just enough time to take a deep breath before grabbing my bag and going to the door. She opened it just as I got there, and she was simply gorgeous, she obviously put even more effort into the first impression than I did. I stepped inside, saw the shoes lined up and took off my boots as she took my bag and set it aside. With the boots off she was a bit taller than me, and I stood there unsure what to do until she took my hand, spun me around, sighed deeply and then led me to the couch. She explained that she hadn't planned dinner for another 45 minutes so that we would have time to talk and get me comfortable with her. She complimented me on looking nice, and I did the same, blushing a bit the whole time.
We sat on the couch quietly for a few minutes, me fidgeting nervously and her running her eyes up and down me. Finally she turned on the tv, a good sitcom was showing, and snuggled into my chest. I was frozen until she pulled my arm around her shoulders, putting my hand on her breast. It was firm, the nipple was hard, and through the T-shirt I could tell it was very soft, I started to get hard, and my jeans started getting a little tight. She must have been waiting for it because she started stroking my cock through my jeans, running her fingers from bases to head and back, feeling the girth, and playing with my balls a bit. We sat there like that until the show ended, and all through the next, I was still too nervous explore the rest of her body, and she didn’t want to rush anything. As soon as the credits rolled on the 2nd episode she squeezed my cock and bounced up, exclaiming that it was time for dinner. She swayed over to the fridge, and offered me a beer which I gladly accepted, but before she handed it to me she explained her rule about drinks: Before each drink you had to remove an article of clothing. I agreed to her rules and, feeling bold, pulled off my T-shirt leaving me with my undershirt still on. With a nod of approval she handed me my beer and grabbed one for herself. She popped the top and moved to drink but I stopped her and reminded her of the rule. She giggled and winked, saying she was just testing me, and did a little dance as she pulled off her socks then took a swig of the beer. She set her beer down and handed me 2 steaks from the fridge, corn on the cob in foil, along with salt and pepper, she took the spatula and a large plate as she led me out on the porch to a charcoal grill. She started the coals as I opened the steaks and sprinkled a dash of salt and pepper across the tops. While we waited for the coals to finish we both finished our drinks, she went in and got 2 more before reminding me of the rule. Not wanting to completely reveal the major erection I had I pulled off my undershirt, with a wink she followed with her shirt giving me an amazing view of her D cup tits sitting in a half cup bra. My jeans were suddenly getting very tight.
The coals were ready by now, so I stepped up and laid the steaks and corn out with a sizzle, as she moved behind me and started caressing my body. Her hands roamed up my arms, over my shoulders, down my back and back up, around to my chest and down to the bulge in my pants. She gave my hard cock a squeeze while whispering in my ear that she couldn't wait to taste it and my cum after she felt it deep in her ass. I had to concentrate very hard on the steaks to keep from ruining dinner. Then her hands moved around, grabbed my ass, and she whispered that she would love to be inside my tight firm ass if I would let her, strangely my dick jumped a little at this. She only stopped exploring my half-nude body long enough to drink her beer. We both finished our drinks just before the steaks were done, and carried in the food and trash, she set the table while I unwrappd the corn and washed up.
When I came back from using the bathroom she was drinking another beer and holding one for me, but she hadn't removed any more clothing. I mentioned this and said that I shouldn't have to strip as a penalty, she countered that I agreed to the rule but she would give me a lap dance after dinner. I could tell she wouldn't budge so I pulled off my jeans and sat down beginning to serve the food, she had put our plates beside each other on the table. She set down her beer, reached around behind her and her bra dropped to the floor. I stared as they bounced, sagged slightly, and settled on her chest. I could tell they were fake but they were just the right amount o firm and perky with a real looking sag and bounce. Amazing. She laughed at my expression and sat down, crossed her legs and relaxed as she said it was my turn. I sudenly realized I only had two more articles of clothing before I would be nude, I grinned as I had an idea. I went back to the bathroom, and took off my boxers, walking back in just my jeans I tossed them to her. She laughed and said we should eat before it got cold.
We ate fairly quietly, our mouths were busy chewing, but we stared at each others bodies the entire time. I was captivated by the slow rise and fall of her tits, and how her nipples were hard from the attention. She split her attention between my shirtless torso, and my still, for now, clothed groin. By the time we finished our meal we both realized how silly we looked and laughed for a good 5 minutes. We cleaned up the table, and she grabbed another beer, I held out my hand for one but she said none for me, if I had anymore I would have a hard time getting hard enough to fuck her face and ass. I nodded, and asked if that was the case should she be drinking, she asked if I really wanted her to be hard, I nodded and said I wanted it all. She smiled and said that a big hard dick being shoved down her throat and up her ass always got her hard. I smiled and asked which piece of clothing she would be taking off, she told me to go wait on the couch and I'd find out.
Once I sat down I heard her voice frm the kitchen telling me to find something on tv, and once the tv was on she turned off the lights. I surfed around and saw that she had some porno channels, I found a good one with two hot trannys fucking a chick. She must have seen what I was watching because she laughed and told me not to jerk at all, she didn't want me cumming without her. I sat there for a few minutes watching the chick getting railed hard by two dicks, when I heard a noise and looked over to see Teri crawling towards me wearing nothing but some black lace boy shorts. She crawled between my knees, and started licking my nipples, working her way down my body and opening my jeans until she wrapped her lips around the head of my cock. I groaned in pleasure, after all the build up the warmth and wetness of her mouth was amazing. As she started taking me deeper she pulled my pants all the way off, when they came off she deepthroated my dick, her tight throat almost made me cum but I pulled her head off and sat there panting. She looked hurt and asked what she did wrong, so I told her that I had to stop her or I would have came, and I didn't want to yet. She giggled and said that if I was going to enjoy tonight I had to let her be in charge, then she swallowed my cock again. As I watched her bobbing up and down, twisting and pulling her nipples, I came, she swallowed all of it but the last squirt, which she held in her mouth. When I was done and she had sucked the last drops out of me she stood and turned around, pushed her panties down, and sat next to me. I looked over and smiled, her cock was just above average in size, completely shaven, and somehow looked very feminine. While I was staring she spit my cum into her hand and started jerking her cock with it, I was speechless. She saw my expression and laughed, then said that any minute now I should be ready to go again, this time deep in her tight ass, the beers were a special brand that reduced the time between orgasms, and increased semen production. She sighed and said that now I could give her hard cock and big creamy loads all night long, and sure enough as I sat there watching her stroke her cock mine grew hard again, she fondled my balls and told me they were just as big as last time. I asked her what would happen if I had another beer, and she said that my cock probably would stay hard and my loads would get bigger. Her voice trailed off as she scampered into the kitchen, returning with an open beer, while I chugged it she led me up to her bedroom and bent over the bed wiggling her delectable ass.
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