There are some men who look good in women’s clothing, but for the most part there is nothing about this sexual interest that appeals to me. Being bisexual, I thought that I might find this combination of male and female attractive, but my equipment was just confused. I came to accept that I enjoyed being with men who were masculine and women who were feminine. I had also discovered that I never had any problems finding a man for sex, but finding a woman was much more complicated. As a result, there were periods where I was without female companionship for longer than I wanted.
During my Covid-19 travels in the US, I had accepted that it was very unlikely that I would be having any sex with a woman. Even male and female couples were unlikely since a lot of people were being very restrictive about meeting new people. My desire to be with a woman was increasing and I felt my loins longing to locate a receptive female. Some of the smooth male crossdressers were becoming appealing.
There was a profile of one tan skinned male with many pictures of him in panties and garters. He was in his middle 40’s and had a slender, smooth body. I knew that if I mostly interacted with him from behind, my equipment would be fooled enough that I could function. My biggest concern was hair. Chest hair or facial hair would destroy the illusion of this man being a woman and I might not be able to function. Eventually my needs outweighed my anxieties.
I sent a note of interest and Tim quickly responded with equal interest. He wondered if I were open to doing a flip fuck. Long ago I had had a relationship with another versatile man and we used to fuck each other during the same session and it was very hot. I always had to penetrate him first, because my erection was difficult to maintain once I had been fucked. He was younger and virile so he didn’t have any performance problems.
I responded that I was more interested in taking him from behind and he decided that that would be fine as long as I would suck him. I always enjoyed a nice cock in my mouth so this was an easy arrangement for me. Tim also wanted to host and I totally understood the need for a crossdresser to be in his own environment for getting dolled up.
We made a plan for an hour later and since he was on the other side of town, I needed to get myself cleaned up quickly and be on my way. It was not difficult to find the small house where he lived in an older residential area. Neither of us was wearing a mask when he welcomed me into the house. Tim was wearing black tights that were pulled down to reveal his ass where he had on white lacy panties. He was wearing a matching white bra and had long, straight black hair. It appeared that the hair was real and that improved the feminine illusion. He had a soft, voice with a subtle lisp. When he flicked his long hair away from his smooth face, I noted red nail polish on lengthy nails. Now I was confident that we were going to have a successful session.
Tim invited me into a small side bedroom where he put on a black light that highlighted the white garments and softened the overall light in the room. It seemed that some of the paintings on the wall were also responding to the black light creating a very sensual atmosphere. When Tim turned around to reach for something his smooth ass cheeks were presented for my pleasure. I was not shy about coming up behind him and squeezing that smooth butt. He wiggled for me and I pressed the bulge in my denim shorts up against his stimulating body.
He turned to sit on a small sofa that was covered with a sheet. I dropped my shorts exposing my partially engorged cock. Tim gently lifted up my shaft and placed his red lipstick covered lips on the head of my cock. Once my dick was in his mouth, one hand with the long nails stimulated my testicles. He took more of my cock into his sexy mouth and sucked on it as he withdrew. I pulled his head into me and he took most of my shaft while my hands enjoyed the softness of his long hair. I knew that the hair would also stimulate my balls when all of my cock was inserted.
It wasn’t long before I was at my full seven inches and thinking about how hot it would be to penetrate that round ass. I removed my shirt and stood before him naked while he pumped up and down on my dick. His oral skills were good and I knew that he could have made me orgasm, but I needed to see and feel my cock going in and out of his smooth ass. Perhaps Tim sensed that I was close and he directed me to lay face up on the sofa.
I did as suggested thinking that he might straddle my body and rub my hard on against his ass. I was surprised when he took his big cock from behind the white panties and put it in my face. His cut dick was a thick seven inches and I was happy to open my mouth for him. He got longer and thicker as I sucked on him and it was a little difficult to be relaxed in that position. Tim was aggressive in face fucking me and I reached for my shorts where there was a small bottle of poppers. I was no longer worried about my performance concerns and knew that the inhalant would relax my mouth to take him better.
Tim also took a hit of his own poppers before he returned to filling my mouth with that attractive cock. He leaned over and sucked on me while I took him on. I was able to reach his ass cheeks and rubbed them sensually. I played with his smooth hole which I wanted to take. I slipped his cock out of my mouth and licked his balls. I was so aroused by his oral attention and my sense of being with a female that I pushed him further so that my tongue could reach his anus. I licked with vigor and wet the area so that one of my fingers could penetrate him. This was the most successful crossdressing session that I had ever experienced. I felt like I was with a smooth man who was transitioning to being a female. I even enjoyed the masculinity of his beautiful cock aggressively plunging into my throat.
I knew that I wanted to penetrate him and sensed that my oral and digital attention to his ass had made him ready for me. “I really want to fuck you,” came the words from my mouth as I lifted him from my raging hard on. He took direction well and placed himself into a doggy position on the edge of the couch. He took another hit of poppers while I slid my shaft up and down his smooth ass cheeks. I used my middle finger to make sure that the opening was ready for some manly cock. I pushed in just the tip and waited to sense if he were comfortable. I felt his ass cheeks relax and pushed in halfway before making another check on his comfort zone.
I smacked that hot round butt alternatively left and right to distract him from my cock plunging in the rest of the way. I was very stimulated by Tim’s attire and attitude and wondered if I were going to have to reevaluate my thinking about crossdressers. I moved into more forceful thrusts and enjoyed hearing my balls slapping against the sexy cheeks. I reached underneath and cupped his bra which felt like an A cup woman. I pulled the bra lower and twisted the nipples with my fingers. He had full nipples that seemed to be sensitive as he squeezed my cock that was occupying his ass.
I placed one foot on the couch and pushed his head down to change the angle of penetration. I was sorry that there wasn’t someone there to take pictures of our sexy activity. I continued to thrust alternatively with force and with gentility. I pulled all the way out and plunged back in with a single push. Tim was a hot fuck and I was very stimulated.
“Come sit,” he directed in his soft voice. I complied and he moved to a kneeling position between my legs. He took my swollen shaft into his mouth and sucked with vigor. I knew when he took another hit of poppers that he wanted to take my load into his mouth. His sucking became more intense and I had to hold onto the sheet on the sofa. I rocked my body left and right as Tim mercilessly took my dick into his warm mouth again and again. The sensations were very intense and I knew that I couldn’t hold out much longer.
I gave my body over to the sexy, sensual man on his knees in front of me. I felt huge pulses of cum shooting from my cock into the waiting mouth. I let go of the sheet and pulled his head down all the way onto my shaft so that the head of my dick pressed against his throat. He took all that I had and pulled his head back for some air. I exhaled deeply and pushed from my lungs the longings that I had just fulfilled. All of my needs had been met and my body sank into the soft cushions on the sofa.
Tim withdrew his sexy mouth and licked his lips. I hadn’t noticed but while he was taking my load, he had been stroking his own shaft. He had orgasmed noiselessly into a towel on the floor. His exhale was softer and gentler than mine. “Thank you,” he spoke with a wide grin showing his white teeth in the black light. “That was great,” I returned.
Unlike my usual self, I didn’t have a battery of questions to ask Tim. I didn’t feel as though I were intruding but I just sensed that we were done. I located my clothes and sandals while Tim headed for the living room. We had a brief parting there and I exited the house, hearing the door lock behind me. Before I turned on the engine in my car, I sat and thought about my experience. I felt sexually very satisfied and sensed that I had met my need to have sex with a woman even though Tim was just a crossdresser. In that respect, this was a very new experience. With other crossdressers I always felt the presence of a man. Somehow this man was able to fool my sensors into feeling that he was a woman. Perhaps I had removed another limitation.