First Time Tranny Loving

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A young man pursues his transgender affection.
2.9k words
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It was a Friday night. I told my friends that I was going to stay in; but I really had other plans. It had been a year since I dreamt of being with a transgender woman. I had explored my growing fascination by visiting the tranny theater and peep booths at Show World. I talked and masturbated with the girls through the glass. In the theater, I would offer a tip to play with their clitty and they would play with my cock. A couple of girls even let me sneak in their booth for some very satisfying and mutual oral sex. But I needed more. My fascination had become obsession and now my obsession was yearning for more meaningful engagement.

I had been living with a beautiful genetic woman when I first had the dream. There was no indication that she had caught on to my growing obsession with transgender women, but I'm pretty sure it affected my growing indifference for her. And she left me. Now free to more deeply explore my new found love, I resolved to meet and engage with a transgender woman. So I did some more research and read about a bar for trannies in the east 30s of Manhattan, I believe it was. It was an early location of a well known club that would later have locations in Hell's Kitchen and then in Chelsea before being shut down for good.

I was nervous as hell, not knowing what to expect. I walked past the club several times trying to get a feel for what I would find. Trying to see who would go in. Finally, I got up my nerve and walked up to the door. I paid my cover and stepped inside. It was a small space back then. There was a bar to the left, I recall, and tables in front of a dance floor. the crowd was sparse, but I guess it was still early. So I walked to the bar, took a seat and ordered a beer.

It wasn't long before a women strolled over and sat next to me at the bar. She was attractive, feminine and wore a warm inviting smile. After introductions, she asked me if I would like to dance. I had barely had time to acclimate and was still a bit nervous, so politely declined, but offered to buy her a drink instead. She recognized that I was new to all of this and while I don't recall what we talked about over our drink, I do remember I was grateful that she gave me the lay of the land. After our drink she moved on. The place was starting to fill up and I noticed some attractive women on the dance floor, so I ordered another beer and moved to a table by the dance floor.

One girl in particular caught my eye. She was a slender latina girl in a short skirt and a tight camisole. She had straight brown hair to her shoulders and wore just the right amount of makeup to accentuate her very pretty face. Her dancing was mesmerizing; the way she moved had me in a trance. I guess I must have been staring, because eventually her girlfriend pointed over to me and said something to her. They continued dancing so I turned my attention to finding a waitress to order another beer.

Once I had flagged the waitress and gave her my order, I turned back and saw that the girl I had been staring at before was now standing at my table. She said hello and asked if she could sit down. She moved her chair close to mine and she introduced herself. She was adorable. My heart was racing. I asked if I could buy her a drink. We smiled at each other and talked. Her leg was rubbing against mine. My stomach was tingling from butterflies. The conversation became easier and she asked me if I would dance with her. I'm not much of a dancer, but wasn't going to pass up a second chance to dance with a pretty girl that night. We danced for several songs, smiling and laughing. She was a very good dancer and clearly enjoyed it. Each time we touched on the dance floor my heart skipped a beat.

When we sat down again, we ordered another drink. My confidence was back and I was feeling very comfortable with her, but still she took the lead. She took my hand in hers as we continued to talk. her hands were soft but thicker than the girls I had been used to dating. This was when she said to me, "you know I'm different than other girls, right?"

I was relieved to get that out of the way and answered that yes, I did and that I was very attracted to her. With that, she began to rub my leg as we talked. She leaned in and kissed me as her hand now found her way to my crotch as she began to rub the growing bulge in my pants. I began to wonder now if she was a pro and if this was going to cost me, but by the time the night was over, she never asked for a dime from me.

We began to kiss deeply there at the table and she unzipped my pants, reached her hand inside and began to stroke my stiff shaft in my pants. After a few moments, she suggested we find somewhere more private. So we got up and she led me downstairs to a door. It was a large supply closet of some sort, but at that point I was so fucking worked up, I didn't care where we were. I held her close to me as our tongues danced together in a deep passionate kiss. She was a fabulous kisser with soft lips, but again, I noticed her tongue was a little thicker than the girls I had been with up to then, but I liked it.

My fly came down again and this time she pulled my cock out into the fresh air. After a few strokes, she slid down my body to her knees, and took my cock into her warm, wet mouth. With her hand still on my shaft, she sucked gently on my big mushroom head, swirling her tongue around it before slowly taking my stiff length down her throat. I leaned back and groaned as I gently thrust my hips to her face. Her head began bobbing up and down as she furiously began to suck my cock. She took my cock out of her mouth for a moment and looked up at me with her dark brown eyes and smiled while she stroked my cock drenched from her saliva. At that moment, however, before she could put her magical mouth back on my cock, the door opened. She scrambled to her feet and I quickly put myself back into my pants. Clearly, this wasn't the place for privacy.

Back at the table she told me to wait a minute, she was going to try to find out where we could go for some privacy. When she returned, she placed her hands on my thighs and leaned in to me for another deep kiss. She then told me there was no place there at the club we could go. I offered to take her back to my apartment. It was a door man building I assured her, it would be fine, but she was uncomfortable with that. She sat down and began rubbing my thighs again as she explained that she wouldn't be able to take me to her place either, but her friend told her about a short stay hotel a short cab ride away. For some reason, that made her comfortable, so I agreed.

I escorted her outside and hailed a cab. Once in the cab, she was all over me, making out with our tongues down each others throats. Our hands were everywhere. I'm certain the cab driver enjoyed the show in his rear view mirror. She was very passionate and had her hands back in my pants stroking my cock again. I ran my hands under her top and up her slender body and began to massage her soft bumps. She started to nibble on my neck and gave me a nice big hickey - by the end of the night, she had left several marks on my neck that I found hard to explain to my friends who thought I had stayed in for the night.

After a stop at an ATM to get money to pay for the room, we arrived at the hotel. I paid for the room and we went upstairs to the small, dingy room. We sat on the bed and picked up where we left off in the cab. I wrapped my arms around her in a tight embrace, my hands exploring her tight sexy body; massaging her soft little breasts, feeling her nipples harden as I pinched them through the soft fabric of her top. She responded with soft moans as she kissed me deeper, her warm mouth on my mouth, feeling the texture of her tongue on mine. She rubbed my growing cock through my pants, massaging my balls, squeezing them just a little.

She began to unbuckle my belt, unbuttoned and unzipped my pants, and pushed them to the floor. She cupped my balls and softly ran her nails over them, gently scratching them as she continued up the shaft of my now rock hard cock with her nails. She unbuttoned my shirt slowly, and helped me out of my shirt as it dropped to the floor. She then placed her warm mouth on my nipple and gently bit and licked it while pinching the other between her thumb and forefinger. I gasped for air as she ran her tongue up my neck, nibbling and biting as her nails teased my nipples.

She stood up and stepped back as I sat naked on the edge of the bed. She began a sexy striptease for me. Grabbing the bottom of her camisole she slowly pulled it over her head and let it drop to the floor. Reaching both hands behind her back, pushing her chest out she unhooked her bra and covered her breasts with one arm as she teasingly tossed her bra on my lap. Running her hands down her stomach to the waist of her skirt she now revealed a lovely pair of small but perky breasts with big erect nipples. Wiggling her hips she slid out of her skirt letting it fall to the floor and did a quick little pirouette before pulling her pretty lace panties over her hips and down her long olive legs to reveal her big, delectable clitty.

I instinctively reached for her clitty taking it in my hand and began to stroke her, feeling it get harder with each stroke. Her cock was thick, long and uncut. As her cock grew in my hand I tightened my grip to peeled back her foreskin stroking the skin on and off the head. Now her breathing became heavy as she ran her fingers through my hair and then tightly taking two fistfuls of my hair she pulled me back onto the bed and climbed on top of me. Again our lips locked and our tongues danced she took my cock in her hand, gently stroking, using her thumb to tease the head of my cock. She then began to work her way down again, kissing and nibbling my neck, down to my chest, licking and nibbling my nipples. With soft kisses she slowly worked her way down my stomach to my raging hard cock.

She teased me at first, licking gently, alternating between licking my balls and licking just the head of my cock. My cock responded, growing harder with each lick. Finally, she wrapped her lips around me, swirling her tongue around. I began to moan and the anticipation was killing me. She continued to suck just on the tip for a while, before finally taking all of it in her mouth, picking up where we left off in the closet at the club. Oh god, did she know how to use her mouth on a man's cock!

I don't recall how long she sucked my cock, but I know I had to hold myself back from cumming several times, but she was relentless. It was clear she wanted me to cum. She ran her hand under my balls, pressing her fingers against that sensitive spot just above my ass. Then, sucking harder and harder, faster and faster, her tongue swirled and I couldn't hold back any longer. I grabbed the back of her head and thrust my hips forward exploding down her throat, filling her mouth with my hot cum. And she didn't spill a drop. When I was done, she opened her mouth wide, showing me my white creamy load, before swallowing it all in a big, erotic gulp.

She then fell back on the bed, pointed to her hard cock and commanded me to return the favor. I eagerly went to work. She laid on her back with her head on the pillow and I went down on her. I had some experience sucking a couple of the girls at the peep booth, but this was relatively new territory for me, so I did my best to mimic what she had so expertly done for me. I ran my tongue around the head under the foreskin, and she gasped ever so slightly. I loved the way she tasted and paused a moment to taste her delicious precum that oozed from her cock. I began working my hands, rubbing her balls, squeezing ever so slightly. I then plunge my head down all the way on her full length. She grabbed my head and pushed it further down on her making me gag slightly and drool all over her shaft. I began to bob up and down on her shaft, fucking her with my mouth. I wanted to make her explode in my mouth like she had done to me, but she had a different idea. Pulling my head off her cock, she asked, "baby, will you let me fuck you?"

My ass was virgin at the time and I hadn't progressed to the point where i was even considering it. I paused, but in the heat of the moment told her yes, before realizing that I hadn't anticipated needing lube for the night. After checking her purse, she didn't have any either and returned with only a lubed condom which would have to suffice.

We repositioned ourselves on the bed as she slipped the condom on her hard cock. She was bigger than average, probably about 7 inches and somewhat thick. Now with her hard cock wrapped, she began to poke the tip at my asshole. My cock was growing hard again as she ground her big cock against my ass, slowly she pushed harder, stretching my ass beyond what I thought possible before again meeting significant resistance. She tried pushing again and pushed harder, my ass burned in pain as she stretched it even more, yet I still hungered for her to enter. Nevertheless, the resistance was too much. I tried to relax, but after a short while of this, it became clear that my virgin ass was just not going to open up for her on this night.

I rolled on my back and she gently slid over on top of me and I wrapped my arms around her. We kissed some more before she rolled off me, took off her condom and reach for a new one. This time, she rolled the condom onto my hard cock and positioned herself with her knees on either side of me. She hovered over my cock for a minute, smiling before softly, gradually sliding down my shaft until my cock filled her. Once she settled herself on my cock she began to slowly ride me. Her pace was measured and deliberate at first as though she would do this all night. She began rocking back and forth, with her full weight on me, leaning back, she began stroking her hard clit, as I began to massage her small breasts while pinching her hard nipples. The image of her riding me is burned in my mind to this day.

She continued to fuck me slow, riding up and down on my cock. Her breathing grew faster and moaning grew louder. She began to ride me harder and stroke herself faster. I grabbed her hips and thrust my cock hard and deep inside her. She closed her eyes, leaned back and let loose - spraying her hot load all over my chest and stomach. Her ass clutching my cock, causing me to give in as well. My body stiffened, I groaned loudly, and exploded into the rubber deep inside her ass. she collapsed on top of me and we lay there exhausted in each others arms.

After a short while we got up, fondling and kissing and nibbling as we helped each other dress. Walking out the hotel into late city night, I hailed her a cab and we shared a long embrace with one last deep passionate kiss before I helped her in the cab and she drove off. I never saw her again, but every time I close my eyes and think of her, I see her riding on top of me stroking her beautiful hard clitty.

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AnonymousAnonymous19 days ago

Very good story and so hot. Please write a ch 2 & 3. I'd like more.

AnonymousAnonymousabout 6 years ago
Memories

Know the bar. Spent many weekends there at Edlewiess. When it was in the 30's, not many working girls till the end. Next two places lots of working girls as Dino preferred it that way. And then the Swan after Dino got shut down for good. Met my wife there.

WhiskeyIsGoodWhiskeyIsGoodabout 6 years ago
Really good

Would love to see more, for sure

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