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The first time, a tale of pain and pleasure  

DoesItMatter38 40M
0 posts
3/26/2019 6:53 pm
The first time, a tale of pain and pleasure


For all those that asked, here is how the first time happened.

It was another typical Saturday night and the guy I had met a few weeks before asked if I wanted to take off, I did and off we went. We start getting out on these back roads and I ask him where we are going. He said to his place he’s got something to show me. So I’m cool with it, not a thought in my mind of what’s to come. We get to his house we go in and he tells me to sit so I do and he’s gone for a bit. When he comes back a few mins later he’s got some porn mags. We chit chat and laugh a little as some time goes by, still not a worry in the world.. he says he wants to try something, follow him. He takes me in his room, and now I’m getting nervous. He tells me to sit at the end of the bed and I do.

When he turns to face me, he’s got his dick out, already hard and is playing with it. I’m starting to lose my mind. As he gets close to me, he grabs my head and pulls it to his dick. I say hell no man and he grips even tighter and says “suck my dick or I’m going to tell everyone you’re a fag. I know now hindsight being what it is I should have taken off right then and there, but the threat shook me and I pictured it in my head loosing all my friends being laughed at…

So, I attempted to blow him, it was a total shit show to say the least. After like 30 seconds.. he let go and pointed to some clothes he had laid out on the bed and I just never noticed until that very second. And told me to change into that and lay face down on the bed and said he would be back.

He walked out and at this point I’m about in tears, scared to death a million things going on in my head. Trying to run away never even crossed my mind. Not that I think I could have any way, the only window was one in the bathroom and it was tiny. Not to mention we were in the middle of nowhere, no cell phones…

Anyway, I did as he said, it was a pair of black pantyhose and like a black knit sweater dress thing. I laid down and waited for what seemed like an eternity. Eventually he came in and straddled me between his legs and started rubbing my ass. Then he slid the dress up and the tights down under my butt. He had some sort of lube, I could hear the bottle open and stuck a finger in me. I yelled and tried to get up but he held me there, jammed it even deeper and told me to relax or it was just going to get worse.

I knew what was coming at this point, so I just buried my face in the pillows and gave up. Then he was laying on me and whispered to relax baby. I could feel his dick poking around and I hoped it would never find it, but it did. And he pushed hard, I started crying the pain was blinding. When he was all in he just sat there for a minute and then went to pound town.

The pain never stopped, and I never got hard, but a few minutes into the pounding, it happened. I will never be able to put into words just how good it felt for about 15 seconds. I started cumming I could feel the sperm squirting on my balls, but I was not hard, and the orgasm was amazing. Not like jerking off or cumming in a pussy, better somehow.

When he finally did cum I could feel it, it burned so bad, ill never forget that. He stayed inside till he went soft then got up got dressed and walked out of the room. I laid there for a few minutes trying to recover. I got up went to the bath room took off those clothes and wiped up. That’s when I noticed all the blood. The bleeding lasted a couple days and the tenderness stopped the next day.
I got dress walked out to the living room where he was and reminded me about him telling everyone before basically pretending the whole night never happened. He brought me home and that was that.

It took a few weeks, but I eventually decided I really liked it and wanted to do it again. And that’s how it went from then on. A few times a week he would take me to his place, id go change and assume the position. It took a few months before the pain turned into severe discomfort, but it did and it got a little easier to do as the months passed. I did not cum like that first time for several weeks and I never told him about it because I was<b> ashamed </font></b>by it.

Any way that’s it. I’ve dealt with this in therapy and don’t really want to get into this. Its just so you understand why I am the way I am.

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