My First Time With A Man

When I was 18 in 1978, I had a summer job in a public office. There was a pretty diverse mix of people who worked there. After about a month, I got to know many of my co-workers and got along really well with them. There was this one guy who was always really friendly and personable. He is the kind of guy everyone likes. Well, this guy came into the mail room one day where I was assigned to sort incoming mail. He started getting frisky with me which made me feel uncomfortable. It wasn't that I didn't want the attention, but I didn't want to get caught fooling around. He was tickling me and hugging me. After I got him to stop for a second, I asked him what he wanted. He responded with, "Your virginity". I felt my cheeks burning with a blush and I felt so embarrassed. He left at that point and I thought about what could have brought all of that about. I never let on that I was bi or a crossdresser. Everyone thought that I was straight and asking me about girlfriends. I never came on to this guy. I conducted myself in a totally professional manner the whole time at work.

Several days later this guy I'll call Charlie approached me and asked if I would like to come see his bar. I found out he owned a bar on the coast near where he lives. I also found out he is gay and his bar caters to gay men. I wanted to keep my relationships with people at work completely professional, but Charlie kept working on me until I gave in and accepted his invitation. It actually took him a couple of weeks to convince me to spend the day with him.

I was still living at home and had to figure out a way to get to Charlie's place without anyone knowing. I lied to my family and told them I was going over to a friends and won't be home until late. I really hoped that no one would call and look for me. I would have had to come up with another lie.

I packed my tiny mint green Speedos since I knew the bar was on a beach and my tan women's high heeled wedge sandals in a backpack. I wore these in other stories I've posted on this site. I put on a pair of short cut off shorts, guy's tee shirt and flip flops. I had arranged to meet Charlie several blocks from my house in case anyone I knew saw me get in the car with him.

On the ride to Charlie's bar I thought about how safe it would be. No one knew where I was going and I didn't know where I was going. It turns out Charlie's bar is on the coast about 30 miles from my house. The place is sort of a dive. There were six or seven guys there drinking and talking. When we walked in everyone greeted Charlie. Then Charlie said, "Look what I have here". That comment really threw me and I got really scared. I had always been curious about gay sex and wanted to experience it, but I didn't want to be raped. I heard gay sex can get pretty rough. I was still young and didn't know a lot about that lifestyle. Charlie saw my uneasiness and tried to calm me. He put his arm around me and offered me a drink. I basically stood there trembling and speechless. Charlie continue to comfort me and got me a rum and coke. I had also never had any alcohol before. The drink was both bitter and sweet to me. I actually kind of liked it and wound up having two.

So now I've been at the bar for about an hour and a half. I started to feel a little more comfortable. I think it may be because of the two drinks. I was definitely feeling buzzed. Charlie asked if I wanted to go for a walk down on the beach. I thought that would be a good idea. I could use the fresh air and clear my head.

Charlie had looked in my backpack and found my Speedos and heels. He asked if I would like to change into my swimsuit. I was kind of pissed that he took the liberty to look through my stuff. I told him it was overcast and a little cool to be wearing that. Charlie really wanted to see me in those Speedos. He was hugging me, calling me baby, and really trying to get me to change. My head was spinning now. I was so confused. On one hand I wanted to do what Charlie asked because I thought it would be fun. On the other hand I was scared because I had never done anything like this before. I knew this was leading to a sexual encounter and wasn't sure if I should walk down that path. Things were moving so quickly. I eventually relented and agreed to wear the Speedos and heels. I asked to change in private so Charlie let me use his office.

I locked the door when I went into Charlie's office and took my clothes off. I slipped into the Speedos and tucked myself carefully into the suit. I was wearing a ring and the suit is tight which made me really stand out. After slipping on my heels, I put my tee shirt back on and went outside. I was really trembling at this point. All those guys out there were going to see me and I wasn't sure what was in store for me.

Charlie met me outside the door and tried to comfort me again. He had another drink in his hand for me. I knew better than to have taken it, but I was so nervous I need something to calm me. Charlie then said, "No, no, sweetie. You need to lose the shirt". Charlie took my drink and lifted my shirt off. I don't know why I didn't resist him. Maybe I had too much to drink or I just gave in to his persistence or I just plain wanted whatever was going to happen happen. To this day I cannot figure that one out.

When I walked out to the bar area, all those guys were hooting and hollering. Someone had put money in the jukebox and music was playing. It was "Saturday Night Fever". Charlie tried to convince me to dance, but I resisted. I just wanted to get some clothes back on and leave. I kept going back and forth between going along with Charlie and leaving and going home. Charlie got me to dance to the rest of the song which seemed like an eternity. There I was bumping and grinding in my Speedos and heels in a gay bar. The place went wild with the half dozen guys there. They wanted me to dance more, but Charlie told them that was enough for now and that we were going for a walk on the beach.

I finished my third drink and was out the door and on my way down to the beach. I remember it being really chilly. I crossed my arms for a little warmth. When we got to the beach, I took off my heels and Charlie and I walked for a bit holding hands. He eventually put his arm around me and told me I was a little trooper for going along with his wishes. He also told me how happy he was and how he was enjoying my company. Charlie is so smoothe I just ate up all of his bullshit. There I was almost naked and he was fully clothed. I can't believe I went along. I put my heels back on for the walk up the hill to Charlie's bar.

It was about 5 PM now and there were a lot more people in the bar. I pretty much drew everyone's attention in there. I wanted to make my way back into Charlie's office so I could get some clothes on, but Charlie had other ideas. He just led me around introducing me to everyone. I felt really uncomfortable wearing a skimpy swimsuit in front of all those guys. Charlie was also caressing me and just touching me all over. The only part of me he didn't touch was my crotch. His hands were constantly on my *** and chest. It was uncomfortable in that this was all new to me, but I also really enjoyed being touched gently like that. It was a real turn on and my Speedos weren't concealing my excitement.

Before long and after a couple more drinks, any guy who wanted to was touching me. I think I was being a tease and the guys were buying it. At some point, I began kissing some of them. I don't know when, but I remember Charlie taking me to his office. He asked me if I was enjoying myself which he knew I was now. Charlie locked the door and began really caressing my body. He was also starting to take his clothes off. As buzzed as I was I knew what was coming and I didn't do anything to stop it. I think I wanted it. When Charlie was naked, he started kissing me deeply. I was kissing him back too. After several minutes of this I took Charlie's **** in my hand and began to pleasure him. He was totally excited and pretty big. I eventually got on my knees and started to kiss Charlie's **** and rub it over my face. I heard Charlie tell me to put him in my mouth. When I did I realized how well endowed Charlie really was. I was trying to open my mouth as wide as possible and he filled me completely. I couldn't get much of Charlie in my mouth before he was gagging me with that massive ****. It wasn't long before Charlie pulled my Speedos off of me. He bent me over a chair and started kicking my love hole. It was totally erotic for me. I am really sensitive there and I was in heaven. Charlie also took me in his mouth and pleasured me for a bit. It wasn't long before I climaxed. Charlie then said, "Now it's my turn". I thought, "Oh yes. I'll suck you and swallow every bit". To my surprise Charlie bent me over the chair and started to rub his **** in the crack of my ***. I was totally surprised when he penetrated my love hole. I thought he was just going to rub himself against me and have me finish with my mouth. When he entered me I screamed. My entire body tensed and I tried to push and get him out. Charlie thrust again and again until he was completely in. I had never felt pain like this before in my entire life. I was terrified, crying and begging for him to stop when I could get words out. I was struggling to breathe at this point. Charlie began to pump me which really hurt. I passed out fairly quickly.

When I woke up, I was on the floor wearing only my heels. I was freezing cold and my *** hurt and was on fire. I tried to get up, but when I moved I would cramp up. I lay there for a while before Charlie came back in. He sat me up which really hurt me. I let out a small scream. At least he held me and made small talk to me to comfort me. I just sat there crying. I don't know how long I sat there like that, but when I composed myself enough to get cleaned up I realized how much *** came out of my stretched out ***. I kept dabbing myself there with a towel and it kept coming. Every time I pushed more came. I was afraid that Charlie took me more than once or that others took me too. I couldn't conceive that much *** coming from one man.

After I put myself back together, I asked Charlie if he would take me home. Charlie said he would only if I put my bikini back on. I couldn't believe this. It's like 9 PM and he wants me to wear a bikini? I tried to talk him out of it, but he would not relent. I gave in, slipped into my Speedos, and stuffed my other things into my backpack.

Charlie dropped me off several blocks from my house at my request. I still didn't want to chance someone seeing me. I got out of his car and realized how wet my bikini was. *** was still draining out of me. I wonder what his car seat was like. I got dressed at the corner where he dropped me off and started my walk home. I was hoping that my family would be asleep when I got there. I could barely walk in in my condition.

When I got to my house the lights were still on. I just wanted everyone to go to bed so I could get in undetected. I waited and waited for what seemed like hours. It was probably on an hour. I kept walking around the block so as not to look too suspicious. I didn't want to draw any unnecessary attention to myself especially since I was in short cut offs and it was pretty chilly out.

I finally got in after 11 PM. Everyone had just gone to bed, but I think my parents were awake. Luckily, they did not want to come and see how I was or find out what I did all day. I was a mess and in no condition to talk to them.

I slipped into the shower and got cleaned up. My *** hurt like hell and burned when the warm water and soap made contact. Touching myself there, I realized how stretched out. There was still *** leaking out. I got dried off, put on a pair of cotton bikinis and went to bed.

When I woke up the next day, I was unbelievably sore. My ******* was really swollen. I was walking a little funny and my parents noticed. I told them we went for a long hike yesterday and my legs were really sore. It hurt when I sat down so I couldn't sit for long. I tried to shift my weight from one side of my *** to the other, but it didn't help much. I had to go back to work the next day and wondered how that would work out not being able to sit for long.

I went to work and ran into Charlie on the way into the building. He asked me how I was so I asked him how he think I felt after having a new ******* ripped. He laughed and told me he had a great time and thanked me. I guess I had fun overall. I have had other encounters with men since and they are all different. I am in heaven while having sex with some of them and it just plain hurts like hell with others. I am very submissive and do enjoy a little discomfort, even pain, but I don't like prolonged intense pain. It's just one of those things where you don't find out until it's too late.

Hope you enjoyed my little first time adventure.

dondonna415 dondonna415
51-55, M
1 Response Sep 11, 2012

That's a helluva story. Thanks for sharing