Down and Out


Our divorce had been final for three months. I was devastated, my wife had been sleeping with her boss for a year before she finally got the courage to admit it and ask me for a divorce. I felt horrible. I stopped exercising and started eating poorly, gaining more than twenty pounds. I felt like a loser.

Finally I decided to go to a bar for the simple purpose of picking someone up for sex. I picked an out of the way place, not to seedy, but certainly not upscale. I had been drinking for two hours before I got the courage to talk to anyone. Finally I got up the courage to talk to a fairly sexy Latina girl sitting at the bar. I bought her a drink and we started chatting. We had nothing in common, but I found her attractive. The bar was about to close when I finally asked, "Do you want to come over to my place?"

She smiled and said, "No, but you can spend the night at my apartment if you want." Her name was Helena and she was dark completed with long brown hair. She was much to young for me, but for tonight she would be perfect. I followed her home, we both drove slowly to avoid getting pulled over as we both would blow over the legal limit if forced.

I pulled in next to her at the complex. I walked to the driver side door of her car and helped her out. We kissed for the first time. Her young body was tight and muscular, a little different than my ex-wife's 40-something soft-body. She took my hand and led me to her apartment. She offered me a drink and we sat on her couch and made out for a while. I was a little rusty at this sort of thing, having been out of the game for years. Her tits were fake, but they were perfect in size and shape. I had to get my lips around them. My ex-wife could have used a boob job like Helena.

Helena then got on her knees and pulled my pants down. She went down on me like a pro, despite the fact that I had never been with a pro and that my ex-wife would NEVER give me a blowjob. Her hair was so soft, I ran it through my fingers as her head bobbed up and down over my cock. She squeezed my balls and semen erupted from my cock filing her throat. She gagged a little, but swallowed every last bit of cum. Her top was off and my pants were off, she took my hand and let me to the bedroom. She had a four poster bed. I climbed in and she pulled out padded wrist and ankle cuffs and asked if she could tie me down. Reluctantly I agreed, again I wasn't used to this sort of thing, but I was horny as hell.

When Helena had me secure she blindfolded me. Then she began rubbing lubricant over my penis, which by this point was hard again. Helena positioned my cock under her and with a bit of work she managed to slide my cock inside of her. She was tight, far tighter than I recall anyone I had ever been with. She asked me how it felt, her Hispanic accent thick and seductive. I told her it was amazing, it was.

I asked her to take the blind fold off and when she did my eyes adjusted to the dim light and I saw her amazing tits bouncing up and down over me. Her hair flowed over her shoulders as she leaned over to kiss me. We kissed until I was getting close to cumming. I told her, "I am not wearing a condom, do I need to pull out." She laughed telling me it wasn't going to be a problem.

I wanted to hold her breasts, but my hands were restrained. Then she said, "I am about to cum as well." Just then I felt something hot hit my chin and then again on my chest. I looked down and saw than Helena had a PENIS! Helena was a man? She was so petite and beautiful. I realized my cock was in her, I mean his asshole. I immediately lost my erection as my penis shrunk to nothing. I begged him to let out, I just wanted to leave.

Helena smiled and said, "Almost baby, just a little longer and you can go, if you want to." Helena got up and got more lubricant. This time she began rubbing it all over her breasts, belly and then her cock. Then she began rubbing her body against mine. I was getting aroused again, I couldn't help it. Helena laughed, "You are still attracted to me, aren't you?" Her body was slithering all over mine. Then her finger slid inside of my anus, then another. She got more lubricant and put it in and around my anus and then on her penis. Carefully she slid it inside of me. It hurt at first, then I could feel the pressure on the base of my cock. It was like she was rubbing my cock from the inside. My erection grew as she fucked me.

Then she leaned forward and kissed me. I didn't kiss her back. She lifted up her body and asked if I wanted to feel her tits. I looked down and saw them swaying over me. I felt so helpless. She was violating me, but it felt good. She was a man, but looked like a woman. I was so confused. She leaned forward again and kissed me again, her tongue slipping in my mouth I kissed her back. As I kissed her she unbuckled my left hand, freeing she said, "Hold me." I thought about hitting her as hard as I could to free myself, but it didn't seem right.

She leaned up on her legs and lifted my butt so she could continue to fuck me from a seated position. She said, "Go ahead, touch them." I reached for her breast and squeezed it. Then she took my penis in her hand, it was erect, and began stroking it. I was close to ejaculation when she unbuckled my other hand. I was free, I could get away if I released my ankles, but Helena leaned forward to kiss me again I kissed her back and held her waist. Her waist was so small, like a young girl. My hands moved down to her ass and I felt her cum inside of me as I squeezed her ass.

Helena lifted up and released my legs and said, "You must be ready to explode" noting that I had not cum all evening. It was true. She laid on her back and said, "Take me." I thought about leaving right then, but instead I grabbed the KY and slid my cock in her asshole until I came. I could feel her penis against my stomach as I fucked her ass, and when I was done I reached down and began jerking her off until she came. When it was over I dressed and got the hell out of there. I never told anyone about that night, until now.

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