Monday Story - 31 Aug 2026

MY FIRST TIME

I have always been shy. I was heterosexual but I was very shy around girls and not assertive. Consequently I had few dates.

I was reading a local newspaper that was mainly known for their ads. I came across one advertisement that was advertising a local gathering for men who had difficulty asserting themselves. The ad had homosexual implications but the opportunity to attend a gathering designed for shy men overcame any hesitation.

I called the number provided. I was told that I would be provided with a partner when I came in who would guide me through the evening. Everyone would be wearing the bare minimum and I would be provided with my outfit when I came, I was scared of the homosexual implications but gave them my credit card number and signed up for the their party the following Saturday. I can't tell you how scared I was but at the same time I felt a great rush.

I almost didn't go but on the next Saturday I did show up at the address provided. I introduced myself and was introduced to Thomas and was told he would be my partner for the evening. Thomas was a big man with a muscular body. He was wearing a very small tight pair of shorts which bulged at his crotch suggesting that he was very well endowed. He told me to follow him and I got another shock. When he turned around there were large cut outs over his ass cheeks. He guided me to the basement. He told me to put my clothes into the locker and handed me a jock strap. He told me that was my dress for the evening.

He then left, and I started to change. Once again I feared what I had gotten into. I changed slowly and put on my dress for the evening. I then noticed another fellow in the dressing room changing into a jock strap. I went over and introduce myself and asked him if he had ever attended before. This was his first time also. He told me his name was William, but he went by Billy. Unlike me, he had had limited homosexual experience.

We went up to the party room together. I found Thomas and Billy found his partner named Charlie. Thomas took my hand and guided me to a table. By a stroke of luck Billy and Charlie shared the table. We had drinks and conversation. Thomas and Charlie worked in a gym. Billy was a teacher on summer vacation. I worked as a programmer and usually worked from home. After only two drinks, I was feeling somewhat lightheaded. I was also beginning to to feel very horny. I wondered what was in those drinks.

Thomas asked me to dance while Charlie took Billy to the dance floor. I had never danced with a man before, and I did not know what to do with my hands. Thomas pulled me towards him and placed both hands on my ass cheeks. He told me to do the same. I did the same and we were dancing closely groin to groin. I could feel Thomas pressing against me and I was getting really horny. At the end of the dance Thomas lowered his face to mine and I found myself in a full-fledged kiss and Thomas's tongue pressed against my lips. I opened my lips and let his tongue into my mouth where it danced with my tongue.

Thomas then took my hand and guided me back to the table. Another drink was waiting for us. We sat out the next dance and Thomas told me about himself and how he hoped when the evening was over I would return to his apartment and serve him as his girlfriend for at least the next month. He said that he would provide me the nicest outfits. I told him that I had no such plans. Thomas told me the night was still young. I looked around and saw two other boys in Jock straps beside Billy and concluded that there were four newbies at this party. I wondered if they were all getting the same offer.

Then Thomas took my hand and guiding me back to the dance floor. In the middle of the dance Thomas again, sort out my lips. I felt his tongue against my lips and slowly I opened my mouth and accepted him in a deep french kiss. The drinks were really having an effect on me. I had never kissed a man before but after those drinks I was beginning to like Thomas's advances.

We went back to the table, but this time Thomas pulled me towards him, and I found myself sitting on his lap. With the lack of clothing, we were basically cuddling skin to skin. We were soon in a full-fledged embrace. Thomas ran his hands over my entire body and stroked me through the thin jock strap. Somehow, Thomas had let his large cock out of his shorts, and I now felt it pressing against my bottom. I don't know how long we were going at it but Thomas had awaken feelings that I had never had before. I was enjoying our make-out session and wanted it to go on. I had totally lost control of the situation. Thomas told me to stand up and he slid my jock strap down to my ankles.

Thomas led me naked onto the dance floor. By this time we were not the only naked couple on the floor. Thomas had let his large cock out of this shorts and it was huge. I almost thought that it was beautiful. "Touch it", he said and I stroked him while he stroked me. We were no longer dancing but were humping each other in the middle of the floor.

Thomas led me back to our seats and he pulled me into his lap. When I sat back. down on his lap Thomas caressed my whole body and began stroking my penis which was fully distended. Finally, Thomas pushed me to my feet and pressed on my shoulders until I was on my knees. His cock was large and inches from my face. I had never seen a cock this close before. Thomas pressed his cock against my lips kiss it. "Kiss it" he said. I hesitated and he repeated ""kiss it". I felt. lost and brought my lips down on his cock. Use your tongue he said I stuck my tongue out and licked the head. "Now lick the shaft" he said and I was lost and began licking the entire shaft of one of the largest cocks I had ever seen.

"Suck it" he said. I took the head into my mouth then slowly began moving by lips up and down the shaft. My mouth was filled with cock, and I felt helpless to resist. Finally, he pulled me to my feet and told me to get on his lap facing him. I felt his penis at my rosebud and froze. I then felt his penis pushing at my opening and then he was pushing the head past my opening. It hurt, damn it hurt, and I wanted him to stop, but he kept pushing. His penis finally entered me and the pain eased. Soon I felt him fully inside of me moving up and down, up and down. Then I felt him shudder and I could feel his liquid squirting inside of me. I had been fucked. For the first time in my life another man had fucked me. I clung to him and he held me close. He held me and kissed me and I returned his kisses. It seemed like forever but eventually I slowly rose to my feet. He pulled me to him and gave me another big kiss. I didn't want this feeling to end.

Why don't you dance with Billy? He said I looked over and Billy was as naked as I was and obviously had just been fucked also. Billy came off of Charlie's lap and we walked to each other.

Billy and I walked to the dance floor and went into each other's arms. We held each other tightly and made quite a sight with the raging hard ons rubbing against each other and sperm seeping out of our asses. We were both so horny and had no way to relieve ourselves. At this point, I would've done anything to get relief for my poor raging hard on. We rubbed up against each other getting hornier and hornier.

Suddenly Thomas and Charlie appeared and we were again in the arms of our partners. Thomas was naked and I clung to him and pressed my body against him as hard as I could. He began kissing me and our tongues danced with each other. Get on your knees, he said. And then in the middle of the dance floor, I sank to my knees and put his cock into my mouth. People were all around us, but I didn't care. I felt horny and was broken. It wasn't a long time before I felt his cock pulse in my mouth and he shot load after load and my mouth was full of his sperm. I now had his sperm dripping out of my mouth and my ass. "I need relief. I told him". "Are you willing to be my sissy girlfriend and live with me and let me for the next month?" "Yes, I said I will do anything for you". I needed to cum and that feeling was greater than anything else but what was I getting into.

Thomas led me into another room. There was a bed in the room and Billy was on the bed, "Get on the bed in the 69 position" Thomas told me. I moved to the bed and I was soon looking at Billy's cock. "Do not swallow, you girls want relief, you know what you have to do," we were told. I felt Billy take my cock into his mouth and I did the same. I was sucking only the second cock of my life. Billy's mouth felt wonderful and it was not long before I was squirting into his mouth. No sooner had I finished then my mouth was filled with his sperm. Both our mouths were bulging from our loads and we faced our masters for further instructions. "OK, now kiss and let your tongues explore each others mouths". We kissed and we were having our lots coat our mouths and lips and escape onto our chins. It was wonderful but after we were done everyone would know what we did by just looking at us.

"Come on girls" Thomas said as he led us out of the room to where our clothes were. We were each given a sack and told to fold our clothes and put them into the sack. "Are we going home naked?"x I asked. "Of course not," he said and handed me a pair of pink panties to put on.