I had to sit out a year from college for lack of funds. I got a job working in the mail room of a large bank. The head of the mail room was a man in his fifties, he always wore a shirt and tie. One afternoon, I was sorting mail and he walked up behind me and reached up over me to grab some mail to check to see how I was doing. He pressed against me, holding me against the table.

One of the other guys who had worked there for a while told me to watch out, he wanted to fuck me, so watch out.

The days went by and one afternoon I told him that I was looking for a vacuum cleaner. He said that he had one that he wanted to sell, I could come by and look at it. I went over to his apartment on Saturday afternoon, he was in casual clothes, shorts and a shirt, and he showed me the vacuum cleaner, an upright and said he wanted a hundred dollars, but I could pay it off at twenty a week.

I was holding the handle when he grabbed my cock. He said that a nice boy like me could pay it off another way, he had grabbed me hard and pulled me towards him and he tried to kiss me. He had my cock in his hand and he said to settle down, he kissed me, and he said we were going to get to know each other really well. He sat down on a kitchen chair and called me over and unzipped my pants and took my cock out and he gave it one long suck. He undid my pants and pushed them down alone with my underwear and started sucking my cock.

I was hard, and him sucking my cock didn't help. He told me to get my shoes off he wanted to see me totally naked. While I got undressed he took off his clothes and he called me over to his bed. He told me that he liked to kiss, so he got me on my back and kissed me while he stroked me. He was hard and I could feel him against my leg. He bent down and sucked me, and got around so I could suck him too. His cock was hard when I put it in my mouth, I liked it, he was hard and I could get a good amount in my mouth.

After a while, he told me to lay on my stomach, he squeezed some lube between my cheeks and used his finger to get it into my ass. He told me he liked it if I was flat on my stomach with a pillow under my hips. He got on and fucked, it went in like a piston and he started to fuck. I was used to guys more my age, but he had a manner of fucking all to his own. When he finished fucking, and pulled it out he was still dripping cum, and I had shot what I had into the pillow under me. He told me that there was lots of cum in that pillow, that's why he liked it under me, he liked young boys, they came a lot and he liked his pillow that way.

I did OK in the mail room, I spent Saturdays or Sundays with him, I never took the vacuum cleaner, I just borrowed it from time to time. He loved to kiss and fuck, and from time to time I would suck him off. My coworker had been right, he wanted to fuck me and I wanted him to fuck me, from that first day when he rubbed his cock up against my back. He had a lot of practice, and he loved to have me fill his pillow with cum, God knows how many guys had filled his pillow, it was his treasure trove of cum. He slept on that pillow every night. A couple of times that he got me to cum out in the open he licked up every drop. He said that the smell of cum gave him strength, which was OK with me. Any way I could help, he was strong, and he liked to fuck.

Comments

Anonymous

by Anonymous on Mar 19, 2018 at 10:37 AM

Reminds me of when I was 19 and working in a office. I was a virgin and an older guy that worked there had his eye on me. I talked to him at work a bunch but never thought much of it. Till one day I was gonna walk home like normal and it was raining. I lived 4 miles away and normally walked. This was in Columbus, Ohio. He offered me a ride so I wouldn't get soaking wet. So got in his car and asked if he wanted anything for the ride. He said no but was wondering if I was straight or gay. I was kinda shocked he asked that but I told him I've never really thought about that. He asked well who do you have set with and I said no one, I'm a virgin.

Fast forward three months he invited me to come to his place after work, he needed some help in his yard. No problem I said I just would need to put on different clothes first. He drove me to my apartment and I said you can come up if you want while I change. He stood there talking to me as I took off my dress cloths and I sat them on my couch. Walked to my closest in just white briefs and a white shirt to get some jeans. Saw him staring at my underwear.

At his place I helped him then before he was gonna drive me home he came in for a kiss. I was kinda turned on buy it and he kept kissing. He undid my jeans and let them fall to the floor. Off came my shirt and he was rubbing my bulge through my underwear. He took aff his cloths and was standing in his boxers. He said to me I can tell your fresh out of high school and still a virgin. I looked at him and he said Hanes white briefs, still wearing virgin underwear that your mom bought you.

He got me naked, laying on my stomach on his bed. He grabbed his tube of ky jelly and spread my cheeks. He squeezed out a bunch onto my hole and fingered it in. That felt pretty good actually. Then he got on top of me a d told me to relax a breath or it will hurt. Felt his head penetrating me and I was biting my lip. It hurt. He slowly slid his shaft in and he stopped. He told me to relax, his cock was about 7” long and I felt his bush against my ass so I knew he was all the way in. Then he started going in and out like a piston till I felt him cum in my ass.

He pulled out my now sore ass and said your not a virgin anymore. I didn't cum so he told me to flip over and he gave me a blowjob, I cummed within seconds. He handed me my briefs and said put them on just in case some cum drips out. He drove me home after that.

About a month later after work he asked me if I enjoyed our time we had. I said other than the sore ass I had for a few days afterwards yes. He told me the more I bottomed the less I'd be sore, I have to get used to being fucked. So I started getting fucked regularly by him. Something about my tight young white briefs wearing butt taking his big thick hairy dick low hanging boxer wearing big balls load in my ass felt right.

He fucked me a few times a week till I graduated college and moved for a job. Miss his cock in my regularly but I do travel to Columbus a few times a year. He's much older now, he's 76 now and I still let him fuck my ass when I'm there. He still is intrigued that I still wear white Hanes briefs when I undress for sex and how tight my hole still is. Last time he fucked me was December and I'm looking forward to the next time we can meet up.

I have a nice tight 20 year old bottom for myself now

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Anonymous

by Anonymous on Mar 20, 2018 at 6:05 AM

I turned 18 and my father sent me out to work. I got a job on a construction site as a gopher. There was an old man, to me, who worked there and he bossed me around. One day I was in the storage shack and he came in and closed the door. He swung me around and told me that I was pretty and he wanted my ass. He was strong and he held me down and told me we could do it his way or my way, but either way he was going to get a piece of my ass. His lunged to kiss me, I moved my head aside and he kissed my ear. He got mad and told me to hold still and he kissed my mouth. After he kissed me he told me to get my pants down and turn around we were going to fuck. That fuck is seared into my mind, it hurt so much and it felt so good. In my mind it lasted forever, but maybe a minute or two, he finished and he pulled out and told me I better wipe my ass. I was still trying to pull my pants up and he leaned over me and kissed me again on the mouth and told me again I was pretty. When I was outside again and the foreman was yelling at me to bring him a tool I was still trying to clear my mind, I had never thought of myself as pretty. Now that I am a whole lot older and I see some of these high school boys running around I know what pretty means. I could use some of that ass. In any event today I know that the foreman knew what went on in that shack, it was part of the job and you don't disturb a man when he is taking care of business.

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Anonymous

by Anonymous on Mar 21, 2018 at 8:04 AM

I was thirteen when my parents divorced and due to lack of money I lied about my age to get a job at a nearby fast food restaurant. Mom knew about it and reluctantly signed the necessary work permit required for fifteen year olds to work part-time.

The night manager got into my cute little tighty-whities the first week, popped my cherry bottom quite painfully. I actually started liking our trysts, quick and hard the finish warm, wet and soothing. I think Mom must of known, my underpants full of his cum three nights a week told all when she did the laundry!?

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Anonymous

by Anonymous on Dec 9, 2018 at 6:34 AM

#3 - Bullshit, Mr Tighty-Whitie.

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