I travel often for work, but this was my first time to Nebraska. After checking into my hotel, I decided to hit the local bar for a few drinks and unwind, it was Friday and my business meetings weren't till Monday morning. The first bar I came across had a happy hour going on, so why not. I noticed they had an advertisement for a drag show that evening, but I was just going in for a few drinks during happy hour. Not long after I'm sitting at the bar, a few glasses of wine in me, I lovely lady dressed in a skirt, heavy on the makeup sits down next to me and I offered to buy her a drink. I couldn't stop looking at her bright red lipstick, fantasizing her leaving a red ring on my dick. Well, after a few drinks and some chatting she asks if I want to another place that has cheap wine. Of course I accept, slightly buzzed, my male mind is thinking I might get lucky my first time here. she calls an Uber, and next thing I know we're at her apartment. 

     Sitting on the couch, we're sipping wine, chatting, then she leans over and starts kissing me, I immediately respond with my tongue deep in her mouth, both of us moaning loudly. She starts rubbing my inner thighs and quickly up to my now erect cock. Without hesitation, she unzips my pants pulls out my cock ad starts licking and sucking me. Not believing my luck, I grab the back of her head and help her bob up and down on my rock hard cock. She sucks so good, definitely not an amateur. She looked up at me as she cupped my balls as she was playing with them, squueezing them, I couldn't hold back any longer and let out a load moan pushing her head hard down on my cock, choking her as I filled her mouth and throat with my hot load.

     She lifted her head up, looked me straight in the eye with my cum, dripping from her lips and said, "ohhh daddy, you liked that didn't you?" My head spinning from an incredible blow job and the alcohol, I said Yes baby, pulled her face to mine ad kissed her deeply, tasting my own cum from her lips and mouth. We continued kissing ad groping, my cock was getting hard again, must be the alcohol talking, I was carressing her chest, feeling her small breasts with hard nipples, I pulled her blouse open to suckle on her tits, and started to slide my hand up and down her thighs, under her skirt, getting closer and closer to her sweet spot, then I went for it, grabbed her panties and felt her raging hard on. She looked me in the eye to see my reaction, but I was so horny and buzzed, I just kept going. Pulling her cock out form the panties and stroking her as we kissed deeply, our tongues dancing in our mouths. I had to taste her pre cum, so I leaned down ad for the first time in my life, I was sucking a cock. I've tasted my own precum and cum, but never no oe else. I was afraid I was liking it, and I was. I couldn't believe it, one of my deepest darkest fantasies was coming true. By now my cock was so hard agian, I just pushed her down on the couch, slid her panties off, but kept the skirt on, it was pure eroticism. I placed her legs over my shoulders and put the head of my cock at her boy pussy entrance, rubbed it a little, letting my pre cum be the lube, the pushed the head of my cock in her. She winced and moaned a little as I pushed in and out, little by little, an inch at a time, till I was all the way in. It was then I looked at her pretty face, her lipstick smeared, her smile, those eyes, ad she said, "do it daddy, fuck my sissy ass", with all the passion I had I began to fuck her in ad out, deeper and harder, we were both moaning and breathing so heavy. "Yes, my sissy bitch, you like that, you like daddy deep in your boy pussy". "Fuck yes daddy, she said do it harder, deeper, I want all of you daddy." As I was fucking her boy pussy with all I had, I looked down ad saw her hard cock was leaking pre cumm all over her stomach. I grabbed her cock and started to strke it timed with each puch of my cock deep in her ass, then I felt her cock twitching in my hand as she shot goobs of cum up her belly, alll over her skirt and blouse. That was more than enough for me, I pounded her 1 or 2 more times. grabbed her hips, and held my cock as far into her tight ass as I could, filling her with another load. I collapsed on top of her for a minute, as she carressed my face and said "thank you daddy, you took my anal virginity and I loved it" 

     I decided to see her a few more times over the weekend before my work meeting and each night was one to be remembered. I fucked my forst sissy, and loved it, sucked my first cock, and drank her cum on the second night. Next time I go to Nebraska, maybe I'll be bold enough to ler her fuck my ass.