Transsexual Encounter

Author: MM

I had always fantasized about being with a transsexual, but never had the guts to pursue it. I had responded to several Craigslist ads to meet trannys, but after only few messages, I usually became overly nervous and I never went through with it. However, there was one Craigslist ad that simply said, ”Satisfaction Guaranteed.” The photos she posted were great. She looked to have a pretty face, nice boobs, and a great body. So, I decided to respond like all the other, but in her message back, she seemed to be personable.

In my email back, I tried to start with small talk but she wasn’t into any small talk, instead she referred me to her website. I was attracted to her and when I went to her website she had a photo gallery, a bio page, and even a page with rates and reviews.

Her name was Victoria, she was 5’6” tall and it said she weighed about 130 pounds. She looked to be Latina, with long wavy brown hair, and a great shape. Her website listed her rates and she ensured that there would be no time constraints, because she wanted to make sure customers where fully satisfied. I continued to want to meet her, fantasizing about being with her, and looking at her photos often.

I tried to contact her again through email to find out where she lived and what her schedule was like and in her reply, she told me where she live, which happened to be close to where I worked, and she gave me a phone number to call when I was ready to meet. I was nervous; I wanted to meet her, but I was scared to call. I finally got up the nerve to telephone her, but what should I expect. The phone rang and rang and when she didn’t answer, I had to leave a message. I immediately felt disappointed, but soon my phone was ringing; she had called me back and introduced herself. We talk for a short while and I explained that I had never done this before. She tried to reassure me that she would be patient and she guaranteed I would enjoy it. She finished by again suggesting that I call when I am ready to meet.
I said, ‘ Okay,” and she told me, “Hope to see you soon.”

When we hung up, I was ready to meet her and I considered what would be a good day and a time to get together. I decided to try to schedule something for that Friday afternoon, after work. It would be easy to head over there after work and it was the weekend. The next day I called to set up something and again I had to leave a message, in which she returned my call almost immediately. I told her who I was and Victoria said, “Oh yea, I remember, you’re the one that wasn’t ever done this, right.” I told her, yea and express when I wanted to come by. She paused and then said, “I think that’ll work, sure.” She then asked if I knew how much the donation was and I replied, “Oh yea,” and she followed by telling me the address, which was an apartment building and she told me the apartment number too. Victoria also told me where I should park and told me to call when I was on my way. I told her okay and expressed my excitement to finally be meeting her. She paused briefly and replied, “Me too, see you Friday, be sure to call me.” I said, “Okay,” and we hung up. When Friday came around, I was nervous but excited too, and when my day was over, I called her as I headed out. I again had to leave a message, but she called right back. I answered and told her I was on my way. She said, “Okay, I’ll be here.” It didn’t take long before I was at her apartment building, parking my car, and heading up to her apartment. I took a deep breath and knocked. Victoria answered in a low cut, lacey negligee and I said, “Hi,” about the same time she did. We smiled at one another and she asked me in. Victoria closed the door behind and told me to go ahead and have a seat. I went over to the couch, sat down and waited for her. It was hard to believe but she was more attractive than her photos. She sat next to me and asked if I had the donation. I replied yes, and as I started to take out the envelope with the cash, she stood up. Victoria told me to go ahead and leave it on the coffee table and motioned for me to follow her into the bedroom. I quickly threw the envelope on the table and followed. She held the door waiting for me and then closed the door once I was in. She was so hot, sexy in her negligee and as she approached me, she asked if I liked her and told me to not be nervous. She kissed me on the cheek and then we kissed each other on the lips, eventually french kissing and feeling on each other. Victoria now started to take off my shirt and gradually moved us over to the bed. She pinched and sucked my nipples and then had me sit down on the edge of the bed. Victoria now backed up and did a strip tease, taking off her negligee and feeling on her boobs. She had great boobs. They looked so firm and she had nice little nipples too. Her body was tight and she did have a great ass too. She kept her panties on but her cock bulged forward, wanting to get out. Victoria told me to lie back on the bed and she started to rub my cock through my jeans and then proceed to undo my jeans, pulling them off. As she did my boxer practically came off too, but I quickly grabbed them, not letting them come down. Victoria cast my pants aside and then took off my boxers, casting them aside too. My cock wasn’t hard, but she quickly started by fondling it and eventually sucking it. It felt so good as she sucked my cock, which immediately got hard in her mouth. Victoria now stopped and climbed up on the bed so she was right next to my face. She pulled her panties to the side letting her cock hang right in my face. As she inched closer, she took hold of it trying to entice me and asking me if I wanted to suck it. I did, but I was nervous to try it. She continued to push her cock in my face and on my lips, until I finally took her cock in my mouth. Her cock was big and as she pushed her cock in and out of my mouth it grew harder and harder. I wanted to taste her cum and I think she wanted to cum too, but she suddenly stopped, taking her cock out of my mouth and moving down to suck my cock. After only a little bit, she stopped sucking my cock and as she looked at me, she asked what I wanted to do. I paused to think and told her I wanted to fuck her. She said ok and before she could finish I told her I also wanted her to fuck me. Victoria smiled, then reached over grabbing a condom off the nightstand, handing me it and proceeded to get on all fours in the middle of her bed. As I positioned myself behind her and put the condom on she handed me some KY. Her butt hole looked so tight and after applying KY to my cock, I fingered her little hole with it too. Victoria moaned and said, ”Oh yea, put it in me.” I inched closer and she spread her legs apart allowing me better access. Her ass was so nice and as I started to push my cock in her ass, she pushed back too. My cock slipped in fairly easy and as I started to fuck her, she remarked, “Oh yea, that feels so good, cum in me.” We moved back and forth in unison, my cock pumping her ass and we started slapping against each other. I was soon going to cum and as I got close to cumming, I tried to hold her close and told her to stop. My cock started to throb inside her and she could feel it too. Victoria kept moving back and forth as I came and being out of breath, I leaned forward, kissing her on the back and reaching around feeling on her boobs. As I took my cock out of her ass, she took hold of my cock and took off the condom and dropped it on the floor. We kissed and she remarked how nice it felt and asked what I thought. I told her it was great, but before I could finish she motioned for me to get on all fours now. I moved to the middle of the bed and I watched her put a condom on her cock and move around behind me, right between my legs. I wanted to feel her in me and as she inched closer she told me to relax. I nodded and she smeared KY on my hole, and started to finger my ass. Victoria gently fingered my ass at first and then gradually wiggled her finger in my ass to relax my hole before she tried to put her cock in me. She remarked, “You are so tight, I want to be in you.” She stopped finger my ass and as she moved closer, I could feel her starting to push her cock in me. It hurt and hen I told her she simply started to wiggle her cock while she tried to push it in me. It felt good, but hurt all the same; I wanted her in me, so I tried to relax. Victoria continued to move her cock in and out, stopping to wiggle it around from time to time. She soon was deep inside me and as she started to fuck me, it continued to hurt, but I wanted to feel her cum in me. Her cock felt big in me, especially when she pushed deep in me, it hurt causing me to rise up from time to time. Eventually I could her she was breathing hard and suddenly she stopped pumping my ass and said, “I’m cumming.” I could feel her cock jerking inside me and as she started to slowly fuck me again. I knew she had cum in me and as she leaned forward, she forced me flat on my stomach. Victoria kissed me on the side of my neck and whispered, “That was great.” She then slowly withdrew her cock from my ass and I watched her take the condom off. She showed me how much cum there was and kissed me, dropping it on the floor and laying next to me rubbing my ass and kissing me. It did feel really good, but eventually we got out of bed, got dressed and I left. We kissed at the door and Victoria said, “Anytime you want to play, let me know.” We kissed again and I groped her tits once last time as I left. I haven’t been back, but continue to look for the opportunity to be with someone like her, without spending the money.