My first trans surprise

I had just flown in to town for a meeting and was going to be here for a few days.

After settling in to my hotel room I was looking for a stiff drink and a nice burger. The desk clerk said I should try the new sports bar that just opened across the street. So off I went to grab some food and see how skilled the bartender is, my favorite drink being a bourbon old fashioned. Entering the bar I chose to sit at the bar so I could at least converse with the bar staff Ordered my drink and perused the menu as the bartender placed my old fashioned I asked her for her recommendation of a burger. As she stood next to me showing her favorite items on the menu, I couldn’t help but check her out she was a petite redhead wearing a tshirt with the bar logo that fit her nice perky breasts (i’m a more than a mouthful is a waste guy) and her firm ass fit nicely in the her cutoff jean shorts. I ordered the bacon blue cheese burger and a side salad she said was awesome. After eating and on my second drink the bar kind of died after about an hour I was the only customer left.

So I got to flirt with the bartender we chatted as she cleaned and prepped for closing. She asked if I wanted another drink and I being emboldened by the drinks and my flirting said yes but only if I could buy her a drink and she join me. She said she would like that but the owner wouldn’t let staff drink where they worked. But if I wanted to purchase a bottle, she would bring the ingredients and we could have a drink in my room. Well that’s a no brainer I jumped at the chance to get to know her. She closed up the bar and we headed to my room. So I found out her name was Christy and she was new to town. We got back to my room and she made us drinks as I went and changed into gym shorts and a t-shirt. We chatted and really hit it off, I was definitely attracted to her and started to come on to her, she was quite responsive to my advances.

I leaned in and kissed her she passionately returned my kiss and after a bit i reached for her breast and fondled them . She responded to my advances and I pulled her shirt over her head exposing her tits they were just my size with puffy nipples my fingers caressing them and pinching them, they hardened as I leaned down and suckled them hearing her moan. She grasped for my cock rubbing it as it hardened in her hand. She reached in and took my cock out getting on her knees she took me in her mouth sucking me in as her tongue worked magic on my stiffening rod. She was giving me the best blow job I have ever had, I stood up and lifted Christy up carrying her to the bed lying her down as I stripped out of my clothes. Climbing on the bed reaching out to pull her shorts off she stopped me and said she wanted to finish sucking me off.

I lay back and she just swallowed my cock taking my whole length down her throat and she sucked me off as her head bounced on my shaft driving me crazy. Her legs spread as she shifted on the bed I reached out to rub her pussy, my fingers found a half hard cock tucked in her shorts. She froze at my touch and looked up into my eyes. Well this was a new experience that I wasn’t expecting but I never let an opportunity slip away. I continued to stroke her cock as it hardens in my hand her eyes lit up and she continued sucking me off. I shifted my position and pulled her shorts off revealing a sexy pair of black lace panties with a cute little penis sticking out. Reaching for her cock I stroked it gently and pulled the panties off , wrapping my hand around it I jerked her off as she sucked me. I have always been bi-curious and now or never was my decision. I lifted Christy up and spun her around with her cock in front of my face in a 69.

I opened my mouth and took it in my mouth sucking on it as it hardened I know what I like having my dick sucked so I did just that. Christy moaned around my cock and sucked me even harder as I felt my orgasm building and my cock swelled in her mouth as I grunted that I was going to cum her reaction was to suck harder and take my cock deep in her throat as blew a huge load down her throat which she swallowed every drop. I sucked Christy harder as she thrust into my mouth enjoying the feeling of being sucked off I kept going as she moaned with pleasure Waiting to get a mouthful of cum but all I got was a few drops of pre cum. As Christy sat up and kissed me passionately she informed me that due to her hormone therapy she can’t really cum from oral. We had another drink and talked about her being a trans woman and her sexuality.

After about 45 minutes she asked me if I would like to fuck her, I looked at her tight ass and reached over and grabbed her shoving my cock into her mouth telling her to get me hard again, she reached into her purse and pulled out a small bottle of Astro glide lubricant as she let me face fuck her my cock growing harder in her mouth. Christy took the lube and spread it on her ass preparing to take my cock. As she released me from her mouth she smeared my cock with lube. Climbing on the bed she got in position and told me to fuck her I stepped up and placed my cock against her ass pushing the head in as she pushed back taking more and more of my meat in her ass until I was buried balls deep, I started thrusting in and out of her tight ass. She was moaning with each thrust and telling me to fuck her harder so I started ramming my cock in her pulling out and driving back in as Christy slammed back on my cock .

I pushed her face down on the bed with her ass up as I pounded my cock in her ass hard and fast listening to her talk dirty and beg for my cock. Her muscles squeezing my cock so tightly that I knew that I was going to cum soon. Leaning over Christy i asked her if she wanted me to come in her ass. Yes she moaned come in my ass give me your hot cream pie in my ass. I ted deep in her ass as I saw her cock spewing cum all over the bed as she came with me. My cock soften and slipped out of Christy’s ass as her anal cream pie flooded out of her gaped ass. We cuddled on the bed and I fell asleep When I awoke the room was empty and as I got up to take a piss I saw the note

Thank you for treating me like the woman I am. Today you made me feel so special Would love to see you again Please call me She left me her phone number…