A Real Life Story of Bad Sex

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Disappointing first time sex with my best friend.
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r543d
r543d
22 Followers

Tonight I knew was going to be the night. I could feel it. I don't think that we could ever be in a relationship together after all the years we've known each other but there was a definite sexual tension building between us all these years. Sometimes, looking back, I find it hard to believe that we didn't fuck each other earlier considering the many nights we've slept in the same bed with each other. I suppose it was that kind of 'Code' you have with someone of the opposite sex when the friendship level hits at a certain point. Tonight however, we hadn't seen each other in years and earlier we got off to a promising start.

She came close to sucking my cock after we got out of the hot tub earlier tonight. I was so hammered by all the alcohol we drank, I didn't really think anything of it though. She asked if she could kiss my hard on as I was drying myself off and I let her. That's all she did. If I was a bit more coherent I probably would have told her to just suck on it but the booze must have kept me from taking it that far.

We went out to the bar down the road. A long time hang out spot for me. She was too tipsy to drive home even though she lived a few miles away. In the town we were hanging out in, it was wise to take no more chances than needed. Besides my family was on vacation and I had the whole house to myself so I invited her over to spend the night.

Feeling a little tipsy myself, we stumbled in the door and wasted no time getting to my bedroom. We took off our clothes rather quickly. By this time in our 7 year friendship, we were used to seeing each other naked. She was a short girl, 5'4", with an upper c size rack, long red hair and an average looking body. Average enough to make any straight guy want to do her.

Given her sexual history, she's no prude. I was a bit intimidated to be honest. She had a lot of experience in the bedroom compared to the handful of women I had been with. I was hoping I could perform up to her expectations.

She laid on her back as I positioned myself between her legs and we locked tongues for a little while. Making my way down her body, kissing every inch, I came to her pussy. It was one of the most impressive looking one's I've ever seen. It looked like a porn star's pussy. The lips were surreal.

I went down on her for a good 15 minutes as she laid there moaning and playing with her tits. I did all I could to make sure I got it good and wet before I stuck my cock in it. Normally I would have concerned myself with some type of condom but that idea was totally overlooked (Thanks to alcohol) as my 7 inch thick cock slowly moved in. Her pussy was small and tight. Unexpected from someone who has been with more guys and girls then I can count. It was a tight and awkward fit. I had to work it for sometimes before I could take on even thrusts. Her pussy was dehydrating and I found myself wetting it with my mouth every now and then.

She climbed on top of me and began to ride my cock and it kept falling out every few seconds. Whenever she tried bouncing on it fast I felt like it was going to break off. It kind of hurt. I was not being turned on at all. I was trying to find pleasure in some unexpected pain. She couldn't believe that my cock was too big for a comfortable fit. She then went on her hands and knees and told me she wanted me to put it in her ass and so I fucked her ass for a while. She was enjoying it more than I was before she told me to fuck her sideways while laying down. I fucked that pussy for a good half hour. Even though I had a few false warnings, I couldn't cum for the likes of me. Maybe it was the booze or I just wasn't getting a good fuck.

We took a breather for a while and went out on the front porch to have a smoke. We discussed the past and how we finally are now fucking each other after all this time. I told her that I wasn't sure if I could go any further tonight (Actually I knew I could but I wasn't really enjoying myself). I mean, touching her body and licking her cunt was a big turn on but my cock wasn't happy.

Laying down back in the bed, she looked up at me and told me she wanted to give it another 'Go'. I told her that I wasn't sure if my dick would feel the same way for it was a little soft. She then told me she had a secret to get it hard again and she began sucking my cock.

Well, at least she was doing something really good that felt awesome! She really gave a good blow job. Actually the best I ever had at that point in my life. It was so good I told her I was about to explode and she had me cum all over her tits, face and she had me put what was left on her tongue so she can swallow it.

We went back out for another cigarette and she told me she wanted to cum one more time. I told her I think that I was probably done with that for the night but agreed to do what she wanted, whatever it took to get her to come.

I fucked her for a good 45 minutes when we got back to the room. She came hard. Just as the sun was coming up for the morning. We fell asleep embracing each other. About a week later she talked me into having sex with her again. I hesitated at first but agreed thinking that maybe that one night a week prior was just an 'Off Night'. This time she interjected a tiny red vibrator that stimulated her clit as I went down on her and it stimulated my cock as I stuck it inside.

The sex wasn't that much better the second time around but I must admit but I did drop my load in her tight twat a lot faster than last time.

Sex did change the future of our friendship. Mostly because it wasn't really that good. Looking back I might have been a little too harsh in judging her for it as I slowly distanced myself away from her (And for the fact that I met the woman who would soon become my wife a few weeks later).

Years later we met up again after both of us had gone through a divorce. She was engaged and I was single. I visited her at her house when her fiancé was at work (He worked the third shift). As much as we reminisced about the past and no matter how hard she tried to seduce me there was no way I was caving in to her sexual needs (She was kind of a nymphomaniac). She pulled out a big black dildo and tried to talk me into helping her with it as we watched porn online but there was no way I was going to do anything of the sexual nature on her bed, with her having a fiancé and for the fact that our past sexual experiences was anything but pleasant.

I don't see too many stories (actually no stories, if there are any) about bad sexual experiences, so I felt obliged to post mine. Yes they do happen and even though having sex with most of my female best friends ended up being anything but disappointing. Shit happens like the story I just told.

r543d
r543d
22 Followers
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AnonymousAnonymousabout 3 years ago

Does a porn star's pussy look radically different than any other woman's pussy? What would make a pussy look particularly "impressive"? LOL

" my 7 inch thick cock" Wow - 7 inches THICK? How bizarre. I doubt any condom could fit that.

So your cock was too big to fit comfortably in her vagina (you do realize women deliver 9lb babies that way?) so she wanted it in her ass, with no lube and that was better? You also seem not to know that you don't take your dick from her ass to her vagina, as that could cause a massive infection.

I have the feeling you have never actually had sex, except with your hand, since you seem clueless about it. Your grammar is also very poor. I suggest you do some research before attempting to write anything else, even if it all is just fantasy.

AnonymousAnonymousabout 7 years ago
True confessions

Drunken, dehydrated, loveless sex is pretty awful? Who knew?

Thanks for your testimonial.

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