Pride Story

100% true story. I was a late boomer. I always dated girls growing up but had fantasies about men from time to time. I'd always think about being a bottom and what it would be like to suck on and fuck a cock and I'd have the craziest orgasms on my own but I'd never actually had sex with a man until I was 23. I had a job for about a year out of school doing insurance stuff when I made a couple mistakes at work in the same week. I was called into my gay boss's office and chewed out about how I wasn't focused. I was looking at a sit down with HR if I didn't shape up. Rich was about 50, divorced, and since living with a guy named Harold. A big guy, I'd fantasized about Rich on more than a few occaisons but was not thinking about that at all as I went home that night afraid for my job. Rich was hosting the department Christmas party a few weeks later so I went with an extra nice bottle of wine prepared to smooze.

I should have been prepared for much MUCH more. Throughout the night people talked bullshit and introduced spouses and ate fingerfood. As people began to clear out I'd been caught in a real long conversation when I realized only about 5 or 6 people were still there. Two of us began helping clean up and after bringing a garbage bag out into the garage I went back into the house and asked Rich for a glass of water before hitting the road. I looked around and didn't see anyone else around when Rich suddenly began talking about what a great party it was and how he thought it went well, but that it was a shame everyone had gone home. Realizing we were alone I had a pang of heat go through me as part of me thought about those times I'd fantasized about sucking Rich's dick and having him suck mine. He said we should sit down in the den so I follwed him in and sat on the couch. He began telling me how I had potential but just wasn't focused and keeping my eye on the ball. He suddenly excused himself and went upstairs. Sitting in his den I suddenly got REAL hard. I fought it and cursed it. I didn't want to embarass myself or do anything stupid. After a few minutes he came back downstairs and went in the kitchen, talking all the while about random work stuff. He returned to the den with 2 glasses of wine and sat down next to me on the couch. My hand was almost shaking as I took the glass and I didn't know why.

After taking a sip he suddenly put down the glass and looked me right in the eye. He said he'd seen me look at his crotch more than once in team meetings and that I pursed my lips when I did so. I didn't know what to say and I froze. He asked me if I was gay and I said no and he just stared at me. I then said I'd thought about what it would be like but never had been with a guy before. He smiled and said he could fix all my problems at work and that he'd always look out for me - but that I would have to do something for him. I took a big swig of the wine and tried to act matter of fact as I asked what that would be. He said that I would have to be his bunny. His boy toy. And noone had better find out. I completely froze and couldn't speak. He stook up and took my hand and said to follow him. Part of me wanted to run out the door and say Fuck This. But I didn't. I went upstairs with him and he led me to the guestroom. Bringing me into the bathroom he showed me some mascara and lipstick on the counter. He then pointed to some lacy things on the toilet seat and told me to take off all my clothes and put on everything I saw. He closed the door and I stood there in terror, but I was so unbelievably hard and part of me REALLY wanted to do this. I was trembling as I put on mascara, eyeliner, lipstick, thigh-high's, thong, bra, and finally a blond wig. I'd never worn womens clothes before but when I looked at myself in the mirror I couldn't believe how much harder I got. I was almost popping out of the thong as I took a depp breath and opened the door.

Rich was on the guestroom bed wearing a bathrobe. He looked like he'd just showered and he called me over. Sitting on the edge of the bed, he pulled me close to him and had me straddle him. He looked me in the eyes and told me to tell him I consent to getting fucked by him any way he wanted. I thought my heart would beat out of my chest as I said yes. He immediately began kissing me, hard and deep with his tongue while squeezing my ass cheeks. It was so unbelievably better kissing Rich than any girl I'd ever kissed. He spun me around and pulled my ass cheeks up to his lap as he pushed aside the thong and began fingering me. I'd never felt that kind of pleasure before and I came a little as he fingered me deeper and deeper and then put some lotion in my asshole. He ripped the thong right off me and tossed me next to him on the bed on my belly. He ate my asshole as I lay there enjoying every minute of it. Turing me over he began sucking my balls and then my 7" cock. I came almost immediately - for longer than I ever had before. He drank every bit of it and stroked me to keep me hard.

He then climbed up me until he was on top of me with his 8" dick right in front of my face. Lying on my back, he started doing push-ups while fucking my mouth and I gagged. He pulled out of me and yelled at me that I was going to learn how to take a cock. Scared I jumped back but he grabbed me and pulled me off the bed making me kneel. He stood in front of me and told me to look up at him and beg for his penis. Terrified I didn't know what to do. Before I knew it he had his dick in my mouth and he was holding my head fucking my mouth, telling me to just open my throat and use my tongue. He slowed down telling me he was going to train me to suck him dry and I was hard again, excited at being told what to do. Feeling like such a little slut had me ready to blow as I gradually got the rhythm and action of taking his cock 3/4 to tip over and over. He came in my mouth and I almost gagged but swallowed it when he told me to. I couldn't believe what I just did. I had just swallowed Rich's cum dressed like a pole dancer and I had enjoyed it. Smiling, Rich told me to stand and I did as I was told. He told me I was going to be a good little twink and that he was going to come by my apartment once a week and have some fun with me. I didn't argue as he turned me around and pushed me down on the bed.

He got on top of me and I felt the tip of his cock press on my asshole. I suddenly thought to tell him he should have a condom and he told me that he was in charge and I would do as I was told. I cried out loud as he broke right through and I felt pain I'd never known before. He kissed my neck and told me that I'd feel fine in a few minutes and that we were going to take it slow right now. Within 5 minutes he was fucking me at a steady pace and the pain was going away. He had me ride him for 15 minutes before he pinned my ankles up by my head and railed away at my throbbing asshole. He came in me twice and pulled me close to him, almost crushing me as he did so. He whispered to me that he would take care of me and watch out for me and that in return I would let him do this to me anytime he wanted. I was spent from pleasure and didn't respond. He then got off the bed and opened an entertainment center I'd paid almost no attention to until this moment. He pushed some buttons on a cam-corder and next thing I knew video of him fucking me silly appeared on the TV. He told me with a smile that made my cock quiver that our new little video would be his insurance policy. I fucked him for 3 years before finding a new job and a new cock I absolutely love to service.