Chapter 5

That night, Teri had work and I really didn’t care to see her anyway. I drove home and showered. Clean and in fresh clothes, I decided to go on the prowl. I lived close to the downtown core and didn’t need to drive so I walked, the warm evening air felt good as I walked down the great hill that brought me to what I called choice Ville. Turn right and you were deep into the straight nightlife. Turn left and you were deep into the gay lifestyle, there was always overlap and tranny’s always made their way into the straight area but that was a matter of choice. I turned right and stepped into a small bar and ordered a draft. I got to talking to an older guy, he seemed very familiar, but I couldn’t place him. It seemed as if he knew me and quite well by the wasy he was talking to me. He was friendly and affable he have me a ton of places to look for girls, how to drink at top shelf clubs for half price and tricks on how to talk to women to get some sense of what dangle they may be playing. No joke, a man alone cruising strange women can be in danger, some women are violent others mentally or emotionally scared, others yet reeking with disease and getting revenge by infecting every guy she comes across, I’ve run into all kinds, had to jump out of second story windows, been held at knife point, scissor point I was lucky not to have been hung by my gizzard so be careful, women are not as helpless or harmless as we’d like to believe. I was really happy for the insight and bought him one for the road. I never did figure out who he was or where I knew him from.

I ran into this gal later on she had long, mousy brown hair, a forgettable face and looked like a soccer mom. I wasn’t horny but I decided to use some of my newfound knowledge on her. I asked if she was alone. It must have been my tone because at first she looked like she was going to show me the door but warmed up and said yes. I asked if she would like me to go or stay and buy her a drink.  Stay, she said smiling, I have a drink going so you don’t need to buy me one. I really don’t remember the chat except that it wasn’t long before she invited me to her place. Once in her bedroom she became very aggressive. She all but tore my clothes off as I pulled at hers. When we got in bed, I decided to treat her to the best fuck she ever had. Remembering my training in Japanese pillow technique I lay her on her back touching her here, stroking her there then I lifted her legs spreading her thickish thighs and entered her beginning the first of three hundred strokes. The first hundred light and not too deep in, the second medium and almost fully inserted, this is where she started to ask me how I got to be so horny. The third is full force thrust, slamming my organ balls deep into her pussy, this drove her nuts! She began to scream you horny bastard, horny fucker, ohh you bastard. Her body became stiff, her pale face red her eyes mere slits and her body became as stiff as a board “Ohhh, fuck, fuck you!” she screamed and collapsed in a heap. This is why this is my least favorite skill, the woman is usually turned into a hot, sweaty puddle of mush and the sex ends then and there. I wasn’t horny anyway, so it didn’t matter. She got out of bed carefully as her balance was still out of whack and braced herself against the vanity. I could tell by the gross folds on her bare ass where two sexy little eggs should be that she had squeezed out her share of rugrats. “Do you want to get married?” She asked as casually as she would ask the time. “I’m not planning on it” I said not taking the bait. That was her angle, she’s looking for a guy to take her and her kids. She asked me if I was sure several times before I left assuring me that she was quite the catch. What kind of catch was she, picked me up in a club, went to bed with me and didn’t care that I didn’t finish. I went in search of someone worthwhile fucking. I headed west until I came to a wide spot in the road that led into a small side street which led to the smallest street. There was a tall brunet looking at me from around the corner. She was slender. dressed expensively and cut quite a figure. I smiled and approached her, and she walked towards me clicking on stiletto heels. “Hi, beautiful night isn’t it?” I asked friendly but not pushy. “Only the night?” She asked jokingly, I hoped she wasn’t ill her voice had a raspiness to it. I didn’t need to catch the flu and asked her directly if she had flu. She laughed, “my voice is masculine because I’m a man.” It was so unexpected that I was struck dumb, all kinds of feelings ran through me at that moment including revulsion, but the overriding feeling dismay by this shemale, I was turned on, I felt like a horny teen. “We can go to a hotel, or we can go to my place its cleaner.” He/she asked her tone was hopeful but clearly expected to be rejected. To both of our surprise I said, “your place.” I hailed a cab, and my companion gave him the address. The drivers distaste for us was palpable almost tangible. When we arrived, the cabbie told me to drop the fare on the passenger seat he didn’t want to touch it. This actually brought the reality of what I was doing in full context and the reality of it turned me on even more. We got into her place, it was plain but bright and clean. She wanted to kiss me on the mouth, but I couldn’t, so we got undressed. He was very well done up, long dark hair well made-up eyes and quite effeminate. His cock was another matter, her organ was 8 or 9” and a little over an inch thick. No way was he sticking that up my ass, I’d never done that before and didn’t think I’d love being split in two. Before I realized what I was doing, I leaned over and for the first time in my life I was sucking cock and I liked it! She was leaning against the wall moaning deeply, I got the idea that she was liking this as much as I was. In no time she/he was on the bed on hands and knees, offering me their ass. As asses went this one wasn’t bad at all. Small, round with a short crack, I got between her spread legs and settled my pelvis over his rectum and as my cock head spread her crack open, I breathed into her ear, “whore.” “Ah.” She/he responded, and I started to push. She/he moaned. Dry as he was I was surprised that he wasn’t begging me for mercy, but she loved it. In no time my prick pushed past her anal sphincter, she gasped deeply, and we fucked like two animals. Screaming, groping, swearing and soon my lovers cock exploded blowing cum all over her sheets. I had no such plans, I kept pumping my cock up his ass until, over his protests, I came up his ass as deep as I could. She clearly was not happy about it but handled it, and my throbbing prick, very well. When I left her, I felt great, I couldn’t believe that I felt no shame or remorse for what I’d just done. This was a new facet of my life that I planned to explore deeply and soon.

The next afternoon Teri called and asked if I wanted to come over, I had nothing else going on, so I decided to go when I got there she was in a bubbly mood. Wow you look happy, did you get laid last night? I asked her smiling. No, she replied “guess what?” With that she dragged me into the house, although I told her all about what I did the night before, I left out the part about my sex partner having a cock and balls. As usual, Teri moaned and came her brains out leaving a Hugh wet spot on her sheets. I didn’t cum, my orgasm from the night before was so intense that I still felt empty. “If you give me anything from this, I’ll kill you.” She said laughing at the recklessness of her behavior. I was reckless and made no excuses for it but I didn’t hold anyone else responsible for my behavior. “Hey kid, “I replied. “If you get anything, you can take penicillin like the rest of us, its called expanding your horizons.” With that what else, Teri brewed a pot of coffee and we sat at the table.  As usual she talked about her friends dysfunctional relationships, the ideocracy of her coworkers and a bunch of other stuff that I didn’t give a shit about. Then it happened, she turned my life on its head and neither of us knew it. She began” My parents invited me to go to Florida for two weeks. How do you feel about it?” Now, I really didn’t care. After she pulled the stunt on me that she did, I no longer held a position in her life where it made any difference to me but I did not want to be insensitive or mean so I replied. “It’s your life, don’t worry about me.” Honestly, it seeing Teri was becoming more and more of a chore every week and I was relieved. “Oh.” She said obviously expecting more resistance. ”Ok, I leave next Tuesday.” She said fishing for a reaction. “Good, enjoy yourself, I guess I won’t see you before you leave.” With that I kissed her and took her for a drive, her mood was more somber than when I first showed up as we drove she said. “I really don’t have to go if it bothers you.” She quipped. “I wouldn’t dream of it.” I replied a tight grin crossing my mouth. After the drive, I dropped her off at home. She stuck her head into my passenger side window and said, “when I get back, be ready tp have a serious talk about our future.” “Until next we meet.” I said lightly and said my goodbyes. Little did either of us know that it would be the last time we would see each other romantically.