Exploring My Feminine Side Ch. 03

After gaining confidence I was on a role but Bob suddenly stopped returning my messages. I wanted more so I fired up the laptop to browse the gay classifieds. I came across an older man who was looking for a crossdresser to come over and make out with him. We chatted a little before he sent over his address and I got on my way.

Gary was a widow who lived alone in a small one bedroom apartment located on the second floor of a two story apartment building. He was not bad looking for sixty-seven and very sweet. He invited me inside and after greeting each other we walked back to his bedroom and removed our clothes before getting into bed.

We made out and explored each other. He found my asshole and I was playing with his dick. I started down towards his dick and began sucking him but after a while he was still just as limp. I asked him to hump me and he obliged for a short time then wanted to suck me. Gary was not very good at giving head as he would only take the tip. As soon as he tasted my precum he took my dick out of his mouth and began jerking me off which was not working. I sensed he was over it and asked him if he wanted me to help. He agreed and I took over until I came all over his bed. Gary got a towel to clean up my cum while I got dressed to leave. We said our goodbyes and I never wrote him again.

About a month later I reached out to an impatient man I had talked to via a gay dating site I had created a profile for. I trusted Neil for some reason and was still determined to have a more satisfying sexual experience with a man. Coincidentally it happened to be my 38th birthday and I had an itinerary that did not include getting fucked by a man. I would have to plan this right and get on with my day as if it did not happen.

Neil was about sixty years old and single with an average body and about a six and a half inch beautiful cock. He had been gay his entire adult life and had never been seriously involved with anybody. He lived alone in a cute two bedroom house on a dead end with his dog. I got up the nerve to knock on his door and Neil greeted me with a sexy mischievous smile before inviting me in.

Neil was all business. As soon as he closed the door behind me and without saying a word he walked down his hallway to his bedroom and got naked before making himself comfortable in bed. By the time I got my clothes off to join him Neil was already hard and ready for me.

Without making out first I went straight to work sucking his dick. At first I was in between his legs on all fours with my ass facing away from him. I don't remember how it happened but next thing I know my ass is facing him while I continued to suck on all fours. I could hear what I knew was the flip top cap of a bottle of lube being opened and a moment later I could feel the cool wetness of my ass being lubed up with Neil's fingers. Sucking cock with my ass getting fingered was too much for me, I was burning with lust. I asked Neil if I could get on top and feel him poke at me for a bit. Being unprotected I had no plans on letting him penetrate me but my ass was so slick and relaxed that he almost instantly popped past my sphincter. I hurt bad for a little while and while I was waiting for the pain to subside I did not realize I was slowly sinking down on his shaft. Before I knew it Neil was balls deep in me and had bottomed out. I sat there for about a minute taking in the sensation of being filled by a man. Neil noticed my dick was still rock hard which really turned him on. I began working his cock with my virgin ass and he began thrusting in me shortly after. Neil and I found our pace. I was so hot and felt so sexy, being fucked felt much better than I had imagined. I could feel Neil working harder and increasing his speed and knew he was getting ready to give me his cum. I decided to try riding him fast and hard. Milking his meat with my virgin ass as fast as I could smashing down hard on him I knew he was getting closer. After about a minute of this Neil stiffened and thrust hard causing his back to arch and I knew he was pumping me full of cum. The whole experience was amazing but feeling his strong dick twitching inside of me while being filled with cum put me over the edge. I leaned back and bared down on him before exploding all over his belly.

We looked at each other smiling then Neil asked me to clean him up. I leaned down to give him a quick kiss before letting his hard cock slip out of me before making my way down his chest to the cum mess I had left all over his belly. As I licked my cum from his body I could feel him squirm slightly as if I was tickling him. When I was done cleaning up his belly I lovingly cleaned up his cock with my mouth and continued sucking until he was soft. I got dressed and left him quietly.

We talked about our date later that night. He told me how good I was and we made plans to see each other again the following day.