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This happened to me at age 17, and is also the story of how I lost my butt cherry.

Growing up, my dad was always close to his younger brother. We lived close by, and our two families would hang out quite frequently.

My uncle (Chuck) had one son, and so did my dad. And when our families got together, my cousin and I would always have to share a bed.

Where we would fuck around.

This started at age 10 or so, but continued through high school. Naturally it started with more innocent touching/looking, but by 14 it was full on blowjobs.

Anyway, I knew that my uncle and cousin had a close relationship. In fact I had heard stories from my dad how my uncle would share beer and pot with my cousin.

Who knows how close they “really” were— but I suspect now that they discussed what my cousin and I used to do.

Fast forward to age 17 and a ski trip to Minnesota. My father, uncle and I were the only ones going.

(My cousin hurt his knee skiing the prior year and since he still played sports, he didn’t want to go)

As luck would have it, my dad throws out his back while shovelling, less than a week before the trip was planned. Rather than cancel, it wa now just uncle and I.

We end up sharing a motel room, and there is only one bed— why would we need two?

My uncle and I had always gotten on very well— he was a big joker and storyteller. Always a lot of fun to hang with.

The first night we played cribbage and watched TV— and drank. Yeah, he gave me a couple cans of beer, and I had really never had more than a sip before.

Well, it comes time for bed and he strips down to his tighty whities only.

Now, my uncle had spent a lot of time in the Navy and was still on decent shape at that time. Furry chest, some belly on him, and arm tattoos.

This probably explains my fetish for these things to this day.

I’m in a tshirt and pajama bottoms. We crawl under the covers and turn off the lights.

Unfortunately I’m buzzed and can’t stop thinking about seeing my uncle’s bulge in his undies. I’m hard and I am fixated on his junk.

I listen to him, and his breathing gets really deep. And that’s when I decide I just want to touch it.

I figure I can always pretend it happened while thrashing about “in my sleep”.

Slowly I reach over and make my way to his crotch. I can feel the heat coming off it with my fingers.

I’m so nervous that I’m almost shaking, but eventually I reach his cock.

And he’s rock hard!

I feel the head of his cock is straining against his underwear, and a slight wet spot at the tip.

I gently stroked and felt along his erection, not believing what I was doing— not daring to breathe.

And that’s when it happened.

Uncle Chuck sat up slowly, and in one motion pulled the covers down, rolled me onto my stomach, and got on top of me.

He started dry-humping my ass with his hard cock. But this didn’t last long.

He got up, pulled down my pajama bottoms, pulled down his underwear and got down to business.

I was scared shitless at this point, because I had never been fucked and this was all happening so fast.

He “may” have used some spit on his cock, but I don’t remember him being very slick.

What I do remember is the pain of his dick pushing into me, basically tipping past my sphincter.

I know I cried out on pain, and my uncle didn’t seem to care. With one hand he propped himself up, while the other shoved my head into the pillow.

Then he started fucking.

There was nothing gentle about it— he just started pistoning my asshole. Every thrust hurt.

I honestly don’t remember much besides fear and pain— and also some deep, secret pleasure that I wasn’t sure I wanted to acknowledge.

My uncle was basically raping my ass—and some part of me was kind of enjoying it!

Pretty soon he was fucking like a sewing machine, and I remember just praying for it to be done.

Then he slams into me and grunts quietly a few times and I know what’s happening. My uncle is cumming in my butt.

After his spasms subside, he yanks out of my ass, and hits the head to clean up. Never saying a word.

I didn’t move.

He climbed back in bed, and that’s when I went to the bathroom. I sat in there a long time. I cried some.

And then I jacked off.

And cried because I jacked off thinking about it.

I didn’t get a lot of sleep that night.

The next day we skiied and pretended that nothing happened.

And then that next night we fucked again— only this time he made me suck him first. And I was sure to get him really nice and spitty.

After that ski trip, we only fucked around a few more times. There just weren’t many opportunities.

I still Jack off sometimes thinking about Uncle Chuck and how he basically started my love of bottoming for furry, tattooed daddies with bellies.

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