I posted this story like 6 months ago and deleted it but found it again in my notes and figured I'd post it again.

I was living in Hawaii at the time amd would go down to Waikiki most weekends with my friends, we would go bar hopping and most nights I'd end up going back to some girls place and hooking up. One night we were out in a bar. It was the usual friday night crowd, packed with tourists and locals. Nice dance floor and big horseshoe shaped bar. I was dancing and saw a girl on the edge of the crowd with dirty blonde hair in a tight orange dress nursing a drink. She had amazing tits and from the look of it a great ass.

She caught me staring at her and smiled, I smiled back and walked over. I said I couldn't help but notice how amazing she looked and asked if I could buy her a drink (my classic pick-up line). Unfortunately for me her drink was basically full and she declined so I offered to buy us shots which she agreed to. She grabbed my hand and we worked our way to the bar and took a shot. I complemented her on her dress and she said thanks but that she wished it had pockets as her cigarettes didnt fit in her purse so she couldn't bring them. I offred to let her bum one of mine and we went outside and smoked. It was much quieter out on the sidewalk and we were able to have more of a conversation, names, work, hobbies, typical stuff. We finished and went back into the bar and danced. We started dancing with some room in between us but very quickly I was holding her hips while she grinded her ass aginst me.

I was wearing shorts and I'm sure she must've felt my cock hardening aginst her ass. While we danced she would look back and smile a very seductive smile at me and I would smile back or kiss her neck and she would look up and lean into me. I would try and turn her around so we could grind face to face but she would just turn back around and push her ass into my crotch which was fine by me. After a few songs she said it was getting late and she needed to go home. I walked her out and we lit a couple more of my smokes and I asked if she wanted to take me back to her place, she smiled and said no she barely knew me. We had some flirty banter while we finished our cigarettes, and she put her number in my phone. She kinda looked at me, I think contemplating if she should take me home, so I leaned in and she lunged forward kissing me. Letting our tounges touch and slip in and out of each others mouths. I pulled her close and felt her push her tits against me. She broke off the kiss, a little out of breath and said to text her tomorrow. I had major blue balls at this point and called a taxi to go home.

The next day I woke up and texted her, we talked and joked and eventually made plans to go get some food and watch a movie. I picked her up, she was wearing short jean shorts that shaped her ass nicely and a nice shirt. We ate then went to the movies. We picked a movie that had been out for awhile and sat in the back row. The theater was basically empty. We spent most of the movie making out. She would rub my cock through my shorts and I would cup and squeeze her tits. Every time I would reach down between her legs she would grab my hand and put it back on her tit. No big deal just not wanting to go crazy in a public place, I get it. After proably 45 minutes of making out I said we should ditch the movie and go back to her place. She hesitated but finally said ok as I was kissing her neck and squeezing her tits. We walked back to my car groping each others asses in the parking garage as we walked around looking for where I parked.

We got back to her place and parked. She said maybe we should go to the backseat first. We climbed into the back seat, she got on top of me and we started making out again. When I tried to grab her hips and pull her into me she pushed me back so I was on my back with her on top of me grabbing her ass and trying to press her aginst me. She eventually gave in and strted to press her hips against mine grinding our pelvises together. I thought I felt somthing hard press against my cock. After a couple seconds of hard grinding feeling somthing hard pressed against my hard cock she sat up and said she had to tell me somthing. I was kinda caught off guard as she told me she's not like most girls. It took a couple seconds for it to register, but to my surprise once I knew, I loved the idea. I'd never been with or even thought about being with a transwoman, but the thought of it made me so horny. I told her thats fine by me but I've never been with a transwoman and I could see the immediate releif on her face. She said good, squeezed my hard cock through my shorts and said to follow her.

We got into her apartment and went straight for the couch. Immediately our mouths were locked together kissing each other hard, lettting our tounge mingle. I was holding her face as she grabbed the back of my head and pushed her hips into mine slowly gyrating her hips on me. I could feel both our cocks grinding against each other and she reached down and pulled my cock out and started stroking me while we made out. She pushed me onto my back, took off my shorts and underwear then took hers off too. She climbed back on top of me sitting on my legs and kept stroking me. I could feel our tips brushing aginst each other. She spit on her hand and struggled to hold them both together and stroke them so I grabbed them and stroked our throbbing cocks together while she grinded her ass on me. She got off and took me in her mouth and started sucking me and playing with her clit until I was leaking pre cum. She wiped the drop off and turned around and showed me as she rubbed it on her hole. I sat up and I grabbed her by her hips and started eating her ass until she was moaning. I reached forward and played with her clit and let my tounge explore down to the back of her balls along to the tip then back up to her hole. She was moaning and leaking, letting my palm slip down to the tip getting her pre-cum on my hand. I'd never done that before and wondered what it taste like so I slowly tasted her as she looked back at me.

She said she wanted to feel me inside of her so I layed her on her back and slowly pushed inside of her a little bit at a time. She had some coconut oil and I used that to oil up both our cocks and her hole then put myself back inside of her. With every thrust I went deeper and faster until I felt every inch of my shaft streching her hole as I pushed my cock all the way in. I slowly pulled myself out letting her savor the feeling. I kept fucking her while she played with her nipples and moaned. It was such a turn on that I started stroking her clit. I was getting close so I pulled out and she said she wanted more, I didn't want to cum so I got down between her legs and took her in my mouth while I played with her balls, she was moaning and spasming I reached up and choked her and she said, "please daddy put it back inside of me", I layed down and she got on top and lowered herslef on my oiled up cock until I could feel her lowerd all the way. She rode my cock slowly then faster and faster while I watched her clittly bounce and leak, dripping onto my stomach She stopped and I could tell she was close so I grabbed her ass lifting her up and kept pumping my hips up thrusting my cock inside of her and she exploded while she was stroking her clit, cumming all over both of us. I was like am animal at this point knowing all I wanted in the world at that moment was to release my seed inside of her. I got up, pushed her face down and fucked her from behind until I came, which didn't take too much longer in her oiled hot hole. I watched my seed leak out of her pussy, while her hot cum was still on my chest and stomach. We both layed back on her couch panting, smoked cigarettes and she said its time to clean me up. She pushed me back so i was laying down, she climbed on top of me with her back turned and started to lick the cum that was on my stomach and my cock, still wet with her juices and coconut oil. I was starting to get hard again and pushed on her back so she was all the way down and I had an amazing view of her pussy still leaking my cum and running down the back of her clitty. I grabbed her hips and began to eat her ass again. We fucked and played eating each others asses and sloppy 69'ing proably 2 or 3 more times that day, and would continue to hookup trying new things and pleasuring each other for a few months until I had to leave the island for work.

Hooking up with her was the start of me finding out I love being with transwomen, and it opened the door for me to be with other transwomen, CD's and sissies.