Shemale Surprise

by Tony (New York)

I work at a large financial company in the city, our company uses five floors in a large building, the worker bees working in the bottom two floors, middle management (which I am) has the third floor and the upper management, CEOs, CFOs and partners take the remaking two upper floors.

The higher up in the company you are the higher floor you have. Seldom does anyone from the top two floors have anything to do with us. Anyway the company was invited to a large company party given by the uppers (that’s what we call the top two floors). This was a surprise to us all.

It was being held on a Saturday night and I felt I should go. I got dressed in a suit with a collared shirt but no tie. We have to wear ties all week and I didn’t want to wear one on a weekend. When I got there one of the “uppers” assistants was checking people in. I never talked to this girl before, she was tall and skinny and had an unusual accent. Sounded like eastern block to me but what do I know.

When I checked in she said hello Anthony, everyone I mean everyone calls me Tony and I figured she had no idea who I am. I hung around about thirty minutes and was thinking about leaving, having said my politically correct hellos. All of a sudden the check in girl Anna walked over and said hello. I was a little surprised she said anything to me.

She asked if I was having a good time. I replied by asking if she wanted the “correct” answer or the truth. She said she only wants the truth always. So I answered honestly and told her I was bored and was thinking about leaving. I was surprised to hear that she was too but had to stay to the end. She asked if I could stick around a little longer and I thought what the fuck, I had nothing really to do so why not.

After another hour she said she could leave and asked if I wanted to go somewhere for a drink. Naturally I accepted, both out of curiosity and thinking maybe I will get lucky. We took the train to her neighborhood and had a drink at a hole in the wall place that she said was near her apartment.

This was a night of surprises because I would never expect one of the “uppers” assistants to ever walk into a place like this. We both had a couple of drinks and talked about everything BUT work, another surprise. I walked her to her place and she invited me in but said I had to take off my shoes. Glad I wore a good pair of socks. It was a great place, very small but very cool and eclectic.

She offered a nightcap before I go then realized she only had white wine, we sat on the couch. We started talking about relationships and discovered that we were both single. Once we finished the wine the conversation turned to sex. Between the drinks, her hot body, my testosterone and me always being horny I wanted to fuck her.

I stood up and so did she and stood close to me. I stepped toward her and we began kissing and taking each other’s outer layer of clothes off. She was a good kisser. She reached down and grabbed my cock which was erect and said hmmmmm. She led me onto her bed and laid on top of me. Now we were really trying to get each other undressed. She rolled off me and pulled off my pants and underwear and took my cock into her mouth.

She gave really good head and I just laid back enjoying this amazing blow job. We rolled over and she had taken off her panties and bra and was completely naked and to my surprise there was an erect penis staring at me. I had been with Shemales before but it had been a long time. I really was shocked to learn Anna was transgender. I took her cock in my hands and gently stroked her a few times before bringing my mouth to her cock.

She had a good sized cock. I liked the head of her cock and then began swallowing her cock, stroking her as I sucked her, my saliva acting like a lubricant on her cock. I sucked and stroked her. I couldn’t help but notice that she tasted amazing. Her cock tasted like jasmine or something. She must put something on her cock that lasts a long time. I looked up at her and she had her eyes closed so I know she liked what I was doing.

We found ourselves in the 69 position each of us on our sides sucking each other’s cocks. I began thinking while I am 69ing with a beautiful t-girl that I missed sucking cock. I asked Anna to sit up on the edge of her bed while I sucked her cock. I sucked her cock using my tongue, man I liked running my tongue over the head of her cock and licking up and down her shaft.

Her cock skin was so soft and felt so good in my mouth. I told her I wanted to fuck her, she asked when the last time I was with a t-girl and I thought it was about 3 years, she said she hadn’t been fucked in a while. I think I got even harder after that comment. She put this amazing lubricant on my cock, making it tingle a little. She got on her knees and spread her ass cheeks so I could enter her. Her ass was so tight it took a long time for me to fit all the way into her ass.

She was tight and felt so good. We fucked for a bit then I rolled her to her back, added some more lubricant to my cock, sucked her cock for a minute and re-entered her. We fucked slowly at first, I was stroking her cock as I was fucking her and felt some pre-cum on her cock. I put some lubricant on her cock and began stroking her faster and faster.

She said she was getting close, I couldn’t help myself and I started humping her faster and harder while she began to moan saying “oh fuck oh fuck I am going to cum” and she shot a load straight into the air. As soon as she stopped cumming I was about to cum and I never asked but I creampied her ass big time. My knees buckled a bit but hung on.

After I came I bent down and took her semi erect penis into my mouth so I could taste her cum, I used my tongue to lick out all the remaining cum in her shaft and began sucking her again until she got hard. I kept sucking her, deep throating her and having her cock gag me, tasting that lubricant and her cum was driving me crazy. I sucked and stroked her and she came again into mouth, I swallowed her entire load and loved it.

I never miss an office party now.