I had just turned 18 and got a summer job with a close cousin, 1st cousin in fact. It was a retail job and turned out I was really good at it, he owned a tourist type business that only opened summer months, then closed during the winters. Back east, winters were harsh, tons of snow and very cold at times, so no tourists around, except those who liked to ski or do snowmobiles.
As said, I was good at sales, and only 1 other staff member brought in slightly more than me on a daily basis. My boss/cousin is about 15 years older than me, married, 6 kids. At times, he would load up his goods and we'd go to a festival or conference and sell things. To save costs, we would share a room of course, just him and I.
I looked forward to these trips because of an experience I had with my boss/cousin at his house. His wife and he had broke up once, and she left to see her family and took the youngest kids with her. They later got back together, but he was home alone for almost 2 weeks. The only 2 kids that stayed with him were his 2 oldest boys, one 19, the other my age, 18.
I was a bit clueless and never for a moment thought any of them had gay tendencies. Even for myself, that part had only been recently awakened because my brother had took my virginity. But I wasn't really "out" if you will, after all, you don't come out and say "Oh by the way, my brother is my lover too." So it was a deep dark secret for only my brother and I.
Back to my boss/cousin.
While he was home alone, sulking, basically, wanting his wife back. He got drunk one night, really hammered. I had stopped in to get my pay and there he was, a mess, talking about how much he missed his wife, blah blah blah. I'm thinking "just give me my check and I'm out of here."
He insisted I stay and console him. He really was a mess, and looked pathetic crying. So I grudgingly stayed, trying to talk to him in a supportive way and suggesting things to win his wife back so she would come back home with the kids.
I sat beside him, rubbing his back and such. After quite a few beers, he asked me if I could help him get into bed, so I did. I didn't drink anything with him. I helped undress him, take his shoes off, etc. Before I could turn away and leave, he pulled me into bed with him.
He started to kiss me aggressively, groping me also. I'm 18, so boners were pretty much instant at the least amount of attention.
Next thing you know, I'm fully naked too. We're writhing around in bed, he was quite assertive, and his cock was the biggest I had ever seen (to be honest, I hadn't seen many at that point.) He definitely was bigger than my brother, not so much in length but thickness. Not quite like a beer can but maybe a bit thicker than a red bull.
He would be the 2nd guy to fuck me next to my brother. Man it hurt. He fucked hard too, don't think he was aware how big his cock is for an anus, a woman's vagina is naturally more able because kids plop out of those. Eventually he shot his load in me, then rolled over and fell asleep.
I slept over next to him naked. I had forgot that 2 of his sons had stayed behind and weren't with their mother. Turns out, the oldest boy, 19, had watched us fuck. The bedroom door had been slightly cracked, house was dark, and because I was wrapped up rolling around in bed with my boss/cousin, I hadn't heard the oldest boy come home.
Because I would travel with my boss/cousin, when we all woke up in the morning, my boss/cousin just acted like there was nothing to explain or hide. He didn't flinch a bit and did great at pretending there was nothing wrong. So I said my good mornings, then rushed out.
A few weeks later, I was chatting with his son, when he disclosed he saw his dad fucking me.
I thought he would be pissed, after all, I'm cheating with his dad on his mother, but no, I was surprised by his reaction. I would have thought the double whammy of the cheating, plus seeing his dad fuck a guy would have thrown him over the edge, but instead, he said he found it hot, and wanted to try it with me, but with me topping him.
His cock was not at big as his dad's, more my size, 6.5uc, he is cut. He only seemed to want to bottom. So I lost my virginity again topping for the first time. It was fun, not quite as intimate as sex with my brother, like I said in my other story, my brother was my best lover ever, even to this day.
He was very interested in details about his dad, I mean although he saw his dad pounding my tight hole, he didn't see how big his dad is because it was dark in the house plus the door merely cracked an inch. He seemed to get off knowing how big his dad is, and I think deep down, he wished his dad was fucking him.
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