Reconnecting with my old boss

By Jim MacIntosh

Published on Nov 20, 2016

Gay

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I worked in retail when I was 18. I had sex with my male supervisor. I was timid about it at first. He made advances on me and I turned him down. I was afraid of what people would say if it was public that I was sexually attracted to men.

One night he and I were closing. It had snowed all day. Before I got off work I asked if I could go warm up my car. I worked in the stock area and we were allowed to park out back. Literally nobody ever goes back there except for delivery drivers. I went out back and my doors had iced shut. I had gotten the ice off the handle and door but couldn't get the door open.

Rick, my boss, suggested me leave my car there and come back in the morning. It was supposed to warm up and that would thaw out my door. I said, "It's 11pm and my parents arent gonna want to get out in this." He said, "So stay at my place." I thought about it. I didn't really have a choice. I picked up the phone and called home. I told my parents the situation and told them that Rick was gonna let me crash at his house.

Rick hadn't tried to put any moves on me in a couple weeks. I wasn't sure what was going to happen. We finished up and I rode with him back to his apartment. We went inside and sat down. We ordered a pizza and watched a movie. During the movie he said, "I kinda want to do something but don't want you to punch me." I said, "It's your place. I'm a guest. I'm not going to punch you." He said, "You sure?" I said, "Yeah. Positive."

He got up and walked up to me. He got on his knees. He unzipped my pants and pulled them down. He took my cock in his hand and started to suck it. I was a ball of nerves up until his mouth hit my cock. Then it felt amazing. He sucked it for a few minutes and then said, "I've wanted to do that for a year now. Well, time for bed." I said, "You want me to just crash here on the couch?" He said, "Well you can or you can sleep in bed with me." I said, "I don't have anything to wear." I was just wearing my work clothes. He said, "Well, you can sleep naked. I will be."

I followed him into his room. He said, "Just take your clothes off and put them in that chair. I'll be right out." I got naked and got in bed. He came out of the bathroom naked. He was hung! I hadn't seen a cock that big. I never measured it but he was about 7-8 inches soft. Probably 9 inches hard. I wanted that cock in my mouth. I sat up on the edge of the bed. I pulled him towards me and started sucking his dick.

He got in bed. I didn't want to stop sucking his dick. So we swapped ends and 69d. I wasn't completely clueless on being with another guy but my experience up until that point was mutual sucking with my best friend during junior high.

I was getting close to cumming and Rick new it. He stopped and said, "I don't want you to cum just yet. I want to fuck you. That ok?" I said, "It sure is." I was laying on my side. He started to tongue fuck my asshole. Man it felt good. He slid a finger inside and sucked on my balls. Then he put a second finger. Then he asked me to get on my hands and knees. He leaned over and got some lube out of a drawer. He put some on his cock and also fingered me with some. It had a numbing agent in it.

He got on his knees behind me. He pushed his cock to my asshole. He slowly slid it in. It didn't hurt but didn't feel good. Kinda weird feeling. I could feel when the head was inside me. He then eased all 9 inches inside me. I asked how much was in. He said, "It's all inside." I said, "Oh nice. That wasn't so bad." He grabbed my ass and slowly started to fuck me. This didn't feel bad at all. The more he did it the more I liked it. Soon he had a good pace. He said, "Play with your cock baby."

I got myself hard again. I had my face on my side buried in a pillow. I was jacking off while Rick fucked me. He grunted that he was about to cum. I was too. He said, "Can I cum in your pussy?" Never had anyone refer to my ass as a pussy and I rather enjoyed it. Sounded sexy. I said, "Yes baby. Cum in my pussy. Oh god I'm gonna cum soon." He said, "Quick. Get on top of me."

He layed on his back pulling me back with him. I spun around to face him. He held my sides and kept fucking me. I was still jacking off. He had to fuck me another couple minutes due to the position change. He then said, "Oh god I'm gonna cum." He pumped his cock in me a few more times then he went stiff. I could feel his cock throb as his load shot inside me. Then j was ready. I said, "I'm gonna cum now." He said, "Shoot it all over me." I was furiously jacking off and then clenched my buttcheeks around his cock and shot my cum all over him.

We had to get in the shower after that. He helped me clean out his load. We washed up and got back into bed. We spooned that night to sleep. Both still naked. The next morning I woke up before he did. I could feel his morning wood between my butt cheeks. I reached back and positioned it to my asshole. I backed up against it. His cock going into my pussy woke him up. He rubbed my shoulders and kissed the back of my neck and said, "Round two?" I said, "Yes please." He said, "We gotta be quick about it. Gotta be at work in an hour and a half." He fucked me side by side. He pulled out before he came.

On the way to work I said, "I don't want the guys to know what happened. Would be weird." He said, "Yeah. Until you get promoted, I could lose my job so we have to keep it on the down low."

The weeks after that my temperament changed. I went from him hitting on me and me shutting it down to me saying things like, "You couldn't handle me if you had me." The guys just thought I was maturing and calling his bluff. Meanwhile, I was going over to his house a couple nights a week.

6 months later my gf and I broke up. Was a friendly break. She was going away to college and we didn't want to try a long distance relationship. That and I was now at Rick's place 4 nights a week. I ended up quitting that job a year later. I was gonna go to college and it was out of state. The last day I worked was memorable. I was just about off work and Rick said, "Well, it was good working with you. If you make if back in town and want to come back, you are welcome." I said back, "oh I'll be back. Someone's gotta keep that cock of yours drained." I grasped his cock through his jeans and we kissed. I didn't look back as I walked off but Rick said everyone was in shock but nobody said anything about it.

So I went away to school. I graduated and ended up getting a good job back in my home town. 10 years passed and I happened to be on Facebook one day. It dawned on me that I hadn't thought about Rick at all. Then one day I decided to look him up on Facebook. He had an active profile. He was still in town. I sent him a message. He was working at his own restaurant as owner and gm.

I told him that I had gotten married. He was still single. He asked if I was straight now. I said, "Don't think I'll ever be completely straight." I hadn't told Rick about my escapade with the other couple my wife and I hung out with on the weekends. I asked if he was busy that weekend. He mentioned being off that Saturday. I asked if he wanted to get together and catch up. He said, "Get together where?" I said, "Well, I was thinking at your place." He said, "And what kind of catching up?" I said, "I wanna see how good your cock feels in my pussy."

Saturday couldn't come soon enough. I was thinking about the dozens or hell hundreds of times we had sex. I drove to his house. Knocked on the door. Soon as he answered it I kissed him. We were making out like junior high kids. We couldn't get undressed fast enough. I was wearing shorts and a tank top. He had on a robe with literally nothing on underneath. I dropped to my knees to suck his dick. He held my head as I worshipped his cock. He said, "Damn baby. I missed you." I said with his cock still in my mouth, "I want you to fuck my pussy. I havent had dick in over a year (a fib) and I need it.

He took me to the bedroom. He bent me over the bed. He pushed his cock (with my saliva as lube) into my eager asshole. I get fucked just often enough so that it doesn't hurt going in anymore. He said, "Oh god. So tight." He held my sides and fucked me hard. I begged for more. I wanted his cock so bad. He fucked me a good 20 minutes. He then said, "I'm gonna cum baby." Didn't ask to pull out. He just emptied his load inside me. I was still horny as hell. I flipped onto my back and he sucked me off. That magic mouth of his was amazing. Didn't take me long to cum.

Afterwards we were laying on the bed side by side. He said, "Wife know you are here?" I said, "Yeah I told her I was coming over here to visit after work." He said, "What does she think is going on?" I said, "I told her that you and I chatted and I was gonna come visit after work today. When she asked what you and I were gonna do I told her I would probably be out of my clothes before I got all the way in the door." He said, "So she knows we had sex?" I said, "Yep. I told her about you and me before we got married. Said that I hadn't seen you in forever but if I ever saw you again you would be the guy that I would get naked for."

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