A Night with a Craigslist tranny

Over the past few years, I had had several girlfriends but currently I wasn’t in a relationship, but my last one had let me fuck her anally, but she only let me do it if she was fucked up on cocaine. It didn’t last long but this experience had me thinking about gay sex, and since I wasn’t in a relationship, I started watching porn and some of it was gay sex and even trannies.

With that said, I had started to look to the internet for possible no strings attached sex partners, and as I said earlier, it all started when I was searching for porn to watch and masturbating but I wanted more.

Not heeding my own warning that it could have deadly consequences, I thought about maybe trying to hook up with someone off Craigslist and so I started searching through the casual encounters postings, I tried contacting a few girls, but nothing happened and even though I fantasized about anal sex again, I wasn’t comfortable contacting other guys. However, when I ended up looking at posting by transsexuals and cross dresser, I fantasized about being with a tranny. They were attractive and I even started to realize that I could have anal sex and still felt I could experience the same thing that I could with a girl.

I wanted to try it and as I started to contact a few transsexuals through Craigslist, many respond and were open to meeting, but I never had the guts to pursue it. I continued to try to contact transsexual on Craigslist and got responds to meet up, but after only few messages, I usually became overly nervous and never went through with it.

However, there was one Craigslist ad that simply said, “Satisfaction Guaranteed.”

The photos she posted were great and she even had her own web site. She looked to have a pretty face, a nice body, and great boobs, and so, I decided to try to contact her. Just like all the other, I became nervous after hitting the send button, but when she finally responded back, she seemed to be personable in her message back.

In my email back, I tried to start with small talk but she was not into any small talk, instead she referred me to her website where she had contact information. 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 reviews.

Her name was Victoria, she was listed as 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; she looked nothing like a guy. Her website also 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 looked 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 lived and it happened to be very close. She also gave me a phone number and told me to give her a call when I was ready to meet.

I continued to be very nervous about meeting her, but I wanted to do it and I felt if I was ever going to do it, now would be the time. I finally got up the nerve one afternoon to telephone her, but I did not know what to expect as the phone rang and rang. Finally her answering machine picked up, I had to leave a message. I was somewhat disappointed, but in a way relieved and so I hung up. Ut no sooner I hung up, my phone was ringing; she had called me back and when I answered she introduced herself and we talk for a short while.

I explained that I had never done this before and 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 and I said, ‘ Okay,” and she immediately 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, which I felt would be nice with the weekend and all. The next day, when I called to set up something, I again 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 had never done this, right.”

I told her, yea and I 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, explained it was an apartment building, told me where I should park, and gave me the apartment number, saying she would have to buzz me in. Victoria also asked me to call when I was on my way, and I told her okay expressing my excitement to meet her. She paused briefly and replied, “Me too, see you Friday,” and told me to be sure to call.

I said, “Okay,” and we hung up.

When Friday came around, I was nervous but excited too, and as I headed out, I gave her a called. I again had to leave a message, but she again called right back, and when I answered, I told her I was on my way and she quickly replied, “Okay, I’ll be here.”

It did not take long before I was at her apartment building, parking my car and as she buzzed me into the building, I took a deep breath and headed up to her apartment and knocked on the door. When Victoria answered, she was dressed in a low cut, lace negligee and said hi about the same time I did. We smiled at one another and she asked me in, telling me to go ahead and have a seat.

As I went over to the couch, Victoria closed the door as I sat down and waited for her. It was hard to believe but she was more attractive than her photos and as she sat next to me she asked if I had the donation. I replied yes, and as I started to take out the envelope with the cash, she stood up and told me to go ahead and leave it on the coffee table. She then said, “Come on,” and motioned me to follow her into the bedroom.

I quickly tossed the envelope on the table and followed her toward the bedroom. She waited in the doorway for me and then closed the door behind us. She was so hot; sexy in her negligee and as she approached me, she asked if I liked her and told me not to be nervous. She kissed me on the cheek a couple of times and then moved my head kissing me on the lips, eventually French kissing as she started to feel on me.

Victoria now tried to take off my shirt as she gradually moved us over to the bed. After slipping my shirt off, she gently pinched and leaned down sucking my nipples. Victoria then had me sit down on the edge of the bed and then as she backed away, she did a strip tease of sorts, taking off her negligee and feeling on her boobs as I watched.

She had great boobs and they looked so firm with nice little nipples. Her body was tight and she did have a great ass. She kept her panties on but her cock was bulging, wanting to get out. Victoria now moved closer to me and pushing me back onto the bed, telling me to lie back.

She started to rub my cock through my jeans and then proceed to undo my jeans, pulling them off. As she did, my boxer slid down and before I could grab them, Victoria grabbed them too, pulling them both off and casting my pants and boxers aside. My cock was kind of hard, so she quickly started by fondling it and eventually she put a condom on me and tried sucking it.

It felt good as she sucked my cock, and I slowly got hard in her mouth. Victoria then 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 to suck it and eventually asked me if I wanted to suck it. I did, but I was nervous to try it, and after short pause to see if I would, she continued to put her cock in my face, even touching it to my lips.

She soon realized it was too soon, and stopped, moving down to suck my cock again. It felt great, but after only a little bit, she stopped again and looking up at me, asked what I wanted to do. I again paused to think and as I did, she moved back up, straddling my chest, wanting me to suck her cock. Victoria’s cock was big and as I watched her put a condom on her cock, she again pushed her cock in my face. I finally took it in my mouth and Victoria gradually leaned forward moving her cock in and out of my mouth.

I could feel it growing harder and harder in my mouth, and I wanted to feel her cum and I think she wanted to cum too. She had me stop, and taking her cock out of my mouth, she told how good it felt. I nodded my head and she climbed off me and told me she wanted to feel me in her. I again simply nodded my head and told her I wanted her to fuck me too. Victoria smiled and had me stand up and as I did, she climbed on the bed, and got on all fours in the middle of the bed. Victoria now patted the bed and said, “Come on.”

As I positioned myself behind her, she spread her legs. I wanted to be in her, and as she spread her one ass cheek, her butt hole looked so inviting. Victoria reached over to the nightstand, grabbing a tube of KY, and handing it to me, she told me to put some on my cock and to put some on her ass too. As I applied some to her ass, she spread her ass cheeks and fingered herself.

Victoria moaned and said, “Oh yea, put it in me,” grabbing for my cock.

She spread her legs a little further apart, as I inched closer, allowing me to get right up next to her. Her ass was so nice and as I started to push my cock in her ass, she pushed back letting my cock slowly slip in. As My cock entered her ass it seemed to suck me in

I was all the way in her now. It was wet and warm in her and as I started to fuck her, she said, “Oh yea, that feels so good, I want you to cum in me.”

She moved back and forth, helping me as I pumped her ass and soon I found myself slapping hard against her ass, wanting to cum in her. I could feel it, I was going to cum and as I got close, I tried to hold her close, eventually telling her to stop. My cock started to throb inside her and I think she could feel it too. Victoria then tried to move back and forth again, but I told her to wait.

We were both out of breath, and as I leaned forward, I kissed her on the back and reached around feeling on her boobs as I gradually took my cock out of her ass. As my cock slipped out, Victoria rolled onto her side and as she did, she took hold of my cock and took off the condom. I watched as she inspected it even smelling it before dropping it to the floor. She rolled onto her back now and pulled me down to kiss me.

As we kissed, she remarked how nice it felt and pausing asked what I thought. I told her it was great, but before I could finish she slid off the bed and motioning, told me to lay on my side. I said, “Okay,” and as I laid on my side, she told me that she wanted to be in me now. I did not know what to do, but I watched as she slid a condom on her hard cock, and then helped to position me in the middle of the bed.

She came around behind me now and spreading my ass cheeks she said, “Yea, that’s nice,” and asked, “Now you’ve done this before, right.”

I wasn’t sure how to answer but when she fingered my ass, she remarked,”I think you have, haven’t you.”

I was a little embarrassed but nodded my head and said, “Yea, I’ve done it before.”

Victoria slapped my ass slightly saying, “You bad boy,” as she climbed on the bed behind me.

I did want to feel her in me and as she inched closer, she told me to relax. I nodded and as she positioned herself, I heard her opening a tube of KY. Victoria then told me to spread my ass, and as I did, she smeared lube on my hole, and then slowly pushed her finger me. It felt good and I anticipated feeling her pushing her cock in me as she now moved to use two fingers, to help me relax.

It really felt good and as she withdrew her fingers, she repositioned herself behind me and tried to put her cock in me. As she tried to push her cock in me, she remarked, “You’re really tight.” She moved even closer, and I could feel her starting to push her cock in me. It hurt and when I tried to pull away. she asked what was wrong, and when I told her it hurt, she replied, “Okay,” and told me to try to relax.

I nodding my head, as she tried again, but this time as she pushed her cock in me, she simply started to wiggle her cock as she slowly pushed it in me. It still hurt but not as bad, and I wanted her in me, so I tried to relax. As Victoria continued to move her cock in and out of me the hurting subsided and soon she was deep inside me. Victoria immediately started to fuck me, and it did continue to hurt a little, but I wanted to feel her cum in me.

Her cock felt so big in me, especially when she would thrust deep in, it hurt, which caused me to pull away. She continually held me close as shE fucked me and eventually I could her she was breathing hard. Suddenly, she pushed deep in me a couple time, which made me again pull away in pain, but then she held me and said, “I’m cumming.”

She held me tight and I could feel her cock jerking inside me as she slowly started to fuck me again. I knew she had cum in me. She then leaned forward, forcing me flat on my stomach. Out of breath Victoria whispered, “That was great.”

She now slowly took her cock out my ass and then rolling off the bed, she moved around and stood in front of me. The tip of the condom drooped, full of cum and I watched as she take the condom off. She showed me how much cum there was and leaning down, she kissed me.

As she stood back up, she dropped it on the floor, and gently turned me on to my stomach, and rubbed my ass. It did feel good, and I wanted to do it again, but we eventually got out of bed, and I got dressed. As I got dressed, she put on a shear robe, waiting for me to leave. As I left, we kissed at the door and Victoria said, “Anytime you want to play, let me know.” We kissed again and I felt on her tits one last time. It was all I had hoped for but at the same time, I have not had the opportunity to be with her again. I have thought about trying it again, but again I haven’t had the chance.