A few months after my divorce, I lived with a friend while the ex moved out. I had enjoyed a great sex life with an equally horny and gorgeous gym friend. Neither of us wanted commitment, just fun and frequent sex. She departed a week before to take a promotion in another state. I found myself easing back into porn and masturbation to soothe the daily urges. It didn’t take long before I returned to my favorite guilty pleasure genres. I alternated between trans, crossdressers, and gay. I had to keep it quiet and low-key since I lived in the guest bedroom at my friend’s house.
Finally, the ex told me she was out of the house and settled, so I returned to start refurbishments and put the house on the market before my job relocation within the coming year. I packed up my belongings and returned to the large house devoid of all the pictures and memories. There was sparse furniture, a computer desk, and a bed, not much else besides the basic appliances.
I found a pile of her old clothes at the bottom of the master bedroom closet, consisting of a short tennis skirt and a loose tank top I don’t recall her ever wearing. Since I was alone, I quickly rummaged through the rest of the pile and found several pairs of panties, a dress, random shirts, and all the lingerie I had bought her over the years. Sorting through the clothes aroused me more than it should, but I was still a horny bachelor in sex catchup mode. I hooked up my computer at the desk and started with the closest fantasy on my mind, cross-dresser porn. I watched video after video of CDs stroking through panties or lifting their skirts exposing panty clad asses. I began to envision myself in their shoes and ponder the sensations going through their bodies. I felt an urge to feel what they felt, all dressed and in various self-pleasuring sexual positions, submitting to unconstrained desires.
I looked over my shoulder at the pile of clothes and thought, Why not? I grabbed the panties and pulled them over my hard cock. I then pulled up the short skirt and put on the tank top, leaving my midriff exposed. It felt feminine and sexy, and I quickly empathized with the internal passions of cross-dressing. I returned to the computer desk and moved to men fucking crossdressers. I watched a well-endowed man bend over a crossdresser, hike her skirt, pull aside her thong then push his cock in. One camera focused on her face while one showed a birds-eye view of his cock entering her. The look on her face was both total submission and intense pleasure.
I was rubbing my cock through the panties the entire time. I stood up and removed the skirt to give myself easier access. I also grabbed the 5-inch suction dildo from my bag and lubed up my ass. I stuck it firmly on the chair, moved the back of the panties to the side, lowered myself onto it, and began to slowly ride up and down. It wasn’t long before my cock twitched and I was shooting my load through the panty waistline up across my stomach. I dipped my fingers in the trail across my stomach and slowly tasted myself while catching my breath. Exhausted and spent, I eased the dildo from my ass and the chair and reflected on what had just happened. I reminded myself I was free to explore sexually, yet torn by internal feelings of guilt and fears of where this could lead.
I put my clothes back on and resumed working around the house. I kept pondering what it must feel like to be crossdressed and used as the object of male desire. The expression of pleasure on their faces was drilled into my memory, seeing the intensity of both submission and physical pleasure. I couldn’t help but contemplate whether the physical, mental, or emotional aspects most enhanced my fantasy. I have always felt a little bi-curious, but never seriously pursued experimenting. The more I contemplated, the more I realized this was the ideal time to try it.
I sat back down at the computer before I went to bed that night and wrote up a brief online ad stating I was a mid-thirties bi-curious male looking to experiment. I didn’t add any pictures as I wanted to remain anonymous, acknowledging I may not have the courage to go through with it. I posted the ad in the gay classified section, then I put up my computer. I was still hyped up in fantasy mode, so I decided instead to head out for a beer with some friends.
I woke up fairly early the next morning and immediately checked my inbox while enjoying my usual coffee. There were several replies ranging from short to long. I read each several times, but kept returning to the same one. He sent two pictures, one of a headshot and the other of a porch overlooking a pond adjacent to a pasture. The text stated he would meet up for a beer and see where our conversation led – no pressure to go further than the beer. I went about working around the house while working up the courage to write a reply. I have never found myself sexually attracted to another man, but the thought of crossdressing in a role was dominating my curiosity. I finally replied, and we agreed on the following evening at a local pub.
I walked in a few minutes early and easily recognized him from his picture. I sat on the bar stool beside him and introduced myself. I ordered a beer, and we began with random small talk. After the bartender served up my second beer, he could see my nerves were easing and leaned in and told me he was interested. He slowly put his hand on my thigh under the bar and asked if I was willing to take the conversation further. He said he was a top and was willing to take it slow as long as I was comfortable, but there was no pressure to take it that far.
We ordered another round and kept talking about everything from sports to jobs, and my comfort level increased with additional liquid courage. His hand continued to ease up my thigh and slightly brushed my crotch several times. He suggested we cash out as he had to work the next morning, but invited me to stay at his place the following weekend. He said he lived alone in a rural area, and no one would notice anything. He patted me on the ass as he stood to walk away and winked.
Needless to say, I went home and jerked myself to 2 orgasms. The following days progressed slowly as I kept dwelling on his statement that he was a top. Was I a bottom? Would I have the courage to go through with this? Would it change my entire worldview? Could I muster the courage to drive out to his place?
I sent him a short note Thursday evening stating I was still interested and would accept his offer for the weekend, still feeling uncommitted at this point. He told me to pack a weekend bag and gave me directions to his place. I left work early Friday afternoon and went home to pack. I was a ball of nerves and had no idea how to pack for this type of weekend. I put the panties, skirt, lingerie, and tank top at the bottom of my bag, covered by 2 days of normal clothes and my hygiene kit. I nervously got in the truck and headed out. It was a half-hour drive into a rural area, which assisted in my decision to go forward.
I finally arrived at the final turn. It was a long gravel driveway between two fenced pastures winding a half mile up to the house. The home was nestled back in a clump of trees and was quite private. He met me on the porch wearing shorts and a tank top and hugged me before inviting me inside.
I dropped my bag in the doorway, and he gave me a quick tour of the house. We ended up on the back porch, and I recognized the isolated pond from his pictures. He said he had lived alone in the house since his parents passed and continued to run the farm. Following small talk, we went into the living room and he turned on the big-screen TV. He pointed to a bookshelf full of porn DVDs and told me to pick out what to watch. I settled on a vintage 4-hour transsexual video.
He grabbed us a few beers, and I guzzled the first quickly and began sipping on the second. He sat next to me on the couch and started caressing my legs. When he inquired why I chose a transsexual video and not gay, I told him about my ex’s clothes and the intensity of feelings when I masturbated while crossdressed.
I was feeling buzzed, horny, self-conscious, and just awkward. He stood and asked if I wanted to go to the jacuzzi down by the pond since the sun was setting, and continue to talk as it cooled off. He went and came back with a paper bag and told me to go put on its contents. I went into the bathroom and pulled out a green bikini from the bag. I hesitated for what felt like hours, but only minutes. The beer and the horniness finally won and I undressed and began to unfold the bikini.
The bottoms pulled up and fit nicely, although my semi-hard cock made it awkward to adjust. The back was a thong, and it felt quite sexy snugged into my crack. I finally figured out how to tie the top behind the neck and back. It took some struggle and adjustments, but I finally got it on. There was also a short white silk robe in the bag that I put on over the bikini. I refused to look at myself in the mirror, quickly gulped the rest of my beer, and walked outside.
He was sitting on the top of the jacuzzi in board shorts and no shirt. He had long, wavy black hair, a shaved face, and an athletic, hairless torso. Although I wasn’t quite attracted to the full male form, he looked great. He handed me another beer as I approached while complimenting me on my wardrobe. I climbed up and sat next to him with our legs submerged in the jacuzzi. He placed his hand on my thigh and another around my back.
He leaned over and kissed me on the ear while rubbing my back through the silk robe. He slowly pushed my cheek around and began kissing my lips. I closed my eyes and opened my mouth and let our tongues intertwine. I quite enjoyed the feel of his lips and began to put effort into our passionate kiss. I quickly lost the conscious thought that I was kissing a man and was getting quite turned on.
He broke the kiss and backed off the jacuzzi, standing up behind me and began kissing the back of my neck while bringing his hands around and caressing my chest through the robe. I pulled my feet up and swung around, facing him, and stood up and again kissed him passionately. He slowly undid the robe and slid it down my shoulders, leaving me in the bikini, facing him while we continued our kiss.
His hands drifted down my shoulders and caressed the small of my back and down my cheeks. I could feel our hard cocks lightly touching through the fabric. He pulled me into him tightly and began grinding while he cupped and massaged my cheeks hanging outside the thong. He broke the kiss and asked if I was ok. I nodded yes, and he gently pushed down on my shoulders.
I instinctively squatted and kissed my way down his rock-hard stomach. He pulled down his board shorts and his cock sprung free. It was a nice average circumcised cock underneath a neatly trimmed bush. I took in the view and the moment, slightly hesitating about my next move. He took the lead and grabbed his cock and began rubbing it around my face in circles slowly reducing the circumference until he was pushing against my lips. I opened my mouth and he slipped the head passed my lips, inserting and withdrawing a few times.
I began to gently suck taking in the mental notion I was in a bikini, on my knees, with a cock in my mouth. I slowly took more in and began to embrace giving the blowjob as I had received so many times before. He began to moan and thrust toward my throat as I would bob up and down. After a few minutes, he withdrew his cock and reached down and pulled me back up, standing face to face. He kissed me passionately as he led me across the porch to the railing.
He turned me around, facing the darkness with my hands resting on the railing as he slid the thong to the side. I felt his tongue work its way down my back and encircle my hole. He then began to lick my hole passionately, bringing forth a pleasure I had never experienced. I began to breathe heavily and reached back and spread my cheeks to give him better access.
He continued to lick and kiss my hole, releasing pleasure I had never known. The sensation was amazing as I felt saliva run down the back of my legs. He slowly alternated, replacing his tongue with a finger, and began to slowly penetrate my hole with one, then two fingers. I was in pure ecstasy and felt my hands tighten their grip on the railing as I was moaning in pleasure. I remained relaxed and focused on the pleasure his mouth and fingers were creating and the twitching of my rock hard cock.
He slowly kissed his way back up my back and then reached over my shoulder and grabbed my hand from the railing and spun me around. We resumed kissing as our cocks slowly rubbed against our bodies in a grinding motion. I continued to dwell on the thought that the mouth I was kissing had just licked my ass.
He broke the kiss and led me back inside and upstairs to a bedroom. He slowly pushed me onto the bed while he retrieved lube and condoms from the top of the dresser. He laid them on the bed and pushed me backwards with his bodyweight onto my back and slowly kissed his way down my stomach to my cock. He eagerly sucked my rock hard cock and began massaging my ass with his finger underneath. The sensations were overwhelming and I told him I was about to cum.
He released my cock and it snapped back against my stomach. He reached up for the lube and put a good amount on his fingers. He pushed my knees up towards my chest and began rubbing the lubed fingers around and into my ass. He proceeded to insert two fingers and held them there. He asked if I was ready, and I merely shook my head up and down. He moved up to my head and put his cock close to my lips. I resumed sucking his cock while mentatlly comparing his size to my dildo. He pulled back and rolled on a condom and applied more lube to my ass and his cock.
He again pushed my knees back towards my chest and positioned his cock at the entrance to my ass. He pushed slightly and paused, allowing me to adjust to the pressure. The head of his cock popped past my sphincter on the second push and I buckled at the pain. He stayed still and reached down to stroke my cock. The pain slowly subsided, and I nodded for him to continue. He continued to push and pause until I felt his balls against my ass. He slowly lay down on top of me, my legs wrapped around his sides, and began to kiss me passionately. Here I was, laying on my back, a cock buried in my ass, passionately kissing a man, trying to comprehend the flood of new sensations.
We remained still, kissing for several minutes before he propped himself up and began with slow, short thrusts, ensuring he stayed deep within me. I could feel the fullness in my belly and noticed most of the pain had subsided, replaced with internal feelings of pleasure I cannot accurately describe. I again dwelled on my current state, laying on a strangers bed in a green bikini with a cock thrusting in and out of me. The mental picture turned me on more than any other sexual adventure, as the physical pleasure brought on new sensations.
He braced himself upright while pushing down on the back of my thighs, me still on my back, and resumed long, hard thrusts. I reached down and grabbed my cock and began to stroke in tandem with his thrusts. Then it happened… subtle at first, and then building stronger than any sexual sensations. I stroked quicker as I felt my orgasm start to build. He sensed it as well and began thrusting faster. With every stroke, I felt a wave of internal pleasure from my ass pushing out through my cock. I felt the cum start to shoot in long thick strings launching up my chest, under my neck and even landing on my face. It was a full-body orgasm like I had never experienced.
He pulled out his cock and ripped off the condom while climbing up towards my head and pushing his rock hard cock in my mouth. He furiously fucked my mouth until I felt his cock start to expand and then exploded into my throat. I tried to swallow as much as I could while still dizzy from my orgasm. He soon collapsed beside me on the bed as we both panted in recovery.
After half an hour or so, he rolled off the bed and grabbed a few beers. He told me to change into whatever I brought to sleep in, and we could resume our fun in the morning. I went to the bathroom and picked out a nice black lace skimpy top and bottom to replace the green bikini. I lay down beside him on the bed and we drifted off to sleep.
I slowly opened my eyes as the sun came through the window. My ass felt a little sore and my cock felt raw from the intense stroking. I reached down and felt the black lace top and bottom and noted how sexy they felt first thing in the morning. It was then that I noticed the dildo still suctioned to the headboard and slowly adjusted to the reality that I had failed to respond to another opportunity. Everything in the old house suddenly seemed familiar. I was once again alone in a familiar place. I got up and walked over to the computer and looked at my draft reply to the meetup… maybe one day I would stir up the courage to hit send.
