Strange Evening

By crim

Published on Apr 4, 2023

Gay

In less than 24 hours, I had experienced a homosexual, bi-sexual or just a full-fledged sexual experience that I had never contemplated and now I was agreeing that I would take the feminine/submissive(?) role in what might be a relationship. It was mind-boggling.

It was nearly 11:00 Saturday before we completed the early morning ?activities? and I was dressed in yesterday?s suit. Charles had kept my underwear and the ?commando? feel was a little odd.

He suggested that we go get me some weekend clothes and so we went to my condo. Upon entering, I got us both a beer and went to my bedroom to get some clothes. Charles followed me and directed me in my clothing choices. I selected, at his direction, some shorts with large loose legs, jeans and a pair of khakis along with a variety of casual shirts?again, no underwear. I changed into a pair of shorts, my deck shoes and a shirt, but Charles decided that we should initiate my bed and we both removed our clothes.

Charles pulled back the covers and sat on the edge of the bed and seeing just his glance, I dropped to my knees between his legs and moved my mouth to his cock. I licked and nipped at his cock enjoying the texture and feel and then began to slowly suck his cock, drawing it deeper into my mouth. When I did not think, I could take any more, Charles grabbed my hair and firmly, but forcefully forced my head down until my nose was in his pubic hair. When I did not gag, I felt an unexpected sense of pride and then began without his prompting to piston my mouth up and down and swirling my tongue all around his hard cock. I felt him tense and pushed down with all my might, but Charles had other ideas and pulled me up until just the first inch or two was in my mouth and, while demanding that I look at him, he said that I was to hold his cum in my mouth. As he released, he let out a long moan and I struggled to do as he asked. When he pulled his cock from my mouth, I gazed at him, begging for direction and then he smiled and nodded. At this, I swallowed his ejaculate as if savoring a fine wine.

In a completely unexpected move, Charles went to my dresser and, after rummaging through my drawers for a minute, presented me with one of my jockstraps. He instructed me to masturbate and cum into the cup, then put it on along with my clothes. Charles dressed and left the room and, god help me, I did as he instructed. The feeling of wearing the cum filled jockstrap was both exciting and a little humiliating, but I had agreed to be the femme and wanted to see where this would go.

We left my condo and went to have lunch at a little place near the park. It turns out that the caf‚? was run by a lesbian couple that bought their employee shirts and kitchen attire from Charles. Charles was greeted with hugs by all of the employees, both men and women, and I was greeted warmly and with ?knowing? smiles. It was as if they knew my role without having to hear a word.

We sat at a table on the patio overlooking the park and, from the table, we could actually see Charles? place across the park. We had a light lunch and, as we got up to leave, he took me into his arms, right there in the open and kissed me. This startled me, but when the employees cheered and applauded, I could only smile. At that moment, however, I decided to join in the fun, so I spread my arms and took a deep bow. At this, there was more applause and then hugs from everyone.

Charles and I left holding hands as we crossed the park to his place. From straight to openly gay or bi in 24 hours?who knew!

As we entered Charles? apartment, we stripped off our clothes and moved to his hot tub and as we sank into the water, Charles pulled me to his side where we began to kiss and fondle each other like teenagers out at their favorite parking spot.

After about « hour, Charles stepped out of the tub and walked naked across the living room and down the hall. I, without even hesitating, admired his body and began to play with my cock, just thinking about what had been going on during the last 24 hours. Charles returned carrying a tube of lube and told me to lean over the edge of the tub with my elbows on the deck and my ass out of the water. I looked into his eyes and then moved into position. Without so much as a word, Charles pushed the lube into my ass and, I guess, massaged some onto his cock. Then, in one thrust, he drove his cock completely home in my ass. As I grunted, Charles grabbed my hips and began to pound away, taking his pleasure in my ass and telling me not to cum until he said so. It took all of my resistance to hold off, but I did and then I felt Charles? hot juices flood into me. The sensation almost put me over the top, but I held off and the sense of pride in doing so brought me almost as much pleasure as the orgasm would have. I was now, for whatever reason, letting someone else make the decisions and letting myself go. This sensation was new and exciting while a little scary.

When we got out of the hot tub, Charles? cock had begun to shrink, but I was still rock hard. While I was hoping for relief, Charles had other ideas and he placed a leather strap around my cock and balls at the scrotum, thus keeping me hard and in need. When I asked about this, Charles smiled and said that delayed pleasure was often the best. I was not sure that I agreed, but I was coming for the whole ride and could only accept what Charles wanted.

We sat, naked, in the living room during the rest of the afternoon, with Charles occasionally fondling my cock to keep it hard while we listened to music and watched a little television.

At about 7, Charles announced that we had to get dressed for dinner and the night out. He pulled me to my feet, kissed me, squeezed my cock and beckoned me to follow him down the hall.

When we got to the bedroom, Charles pulled on a jock strap of his own and then turned to me. He took a pair of my shorts and had me put them on. He did not like the length, so he began to roll the legs up, but that had the effect of making the leg openings tighter, so he had me take the shorts off and then took a pair of scissors and cut the shorts off to, what many would consider an obscenely, short length. I put them on and commented that if my cock were not erect, it might show. Charles smiled, had me take the shorts off, took off the strap and then had me masturbate into my hand. Once I ejaculated, Charles had me lick up my own cum and then put the shorts back on?I was right, when sitting the end of my cock showed. I finished dressing in a golf shirt and my deck shoes, as instructed. Charles had me leave the room and when he came into the living room, he was in tight leather pants and a tight t-shirt. I stood and walked to him, looked into his eyes and moved into his arms, giving him a deep and lingering kiss.

As I stepped away, Charles said that he wanted me to pull my longish blonde hair into a pony tail. I looked at him sheepishly and did as he asked.

We went downstairs and got into his vehicle for the night, his pickup truck.

Looking at Charles, I asked where we were going and he said ?Liz?s Bistro?. As we rode along, I could not help but look at the both of us and how we were dressed and mouth to myself ?Liz?s Bistro.? This was going to be some place, I was sure.


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