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Jayphil
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@random
01 Jan 2017 1:38PM
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My DP partner and I got invited to a house party last night for NYE with about 50 people there. We got there around 6 already buzzed and so was most of the party. Unfortunately we saw someone there we had DPd before with her new boyfriend. It was really awkward at first but she came over and introduced him to us. We shook his hand and she pulls me aside and asks us if we'll fuck her again while he watches. Uhhhh yeah sure I guess I respond. I give my buddy a heads up and she leads us to an unoccupied bedroom with a fouton. We're in the middle of DPing her and I feel a tap on my shoulder. It's her boyfriend and he's got another couple from the party that wants to join us. I see that the it's the couple that owns the house and they tell us that Brianna(the woman we're already fucking) told them about her experience and it's always been something that they wanted but didn't want to use Craigslist or a stranger. Mind you we DPd Brianna only for one night and I got her pregnant(didn't keep it) because I didn't wear a condom when I came(I took it off and the reason for the awkwardness). I told the couple that we will come inside her and they needed to be okay with that and they were. I pulled out of Brianna's ass to watch the wife undress and as soon as her panties hit the floor she's mounting my cock. She was so much tighter than Brianna and she knew how to work my cock without me doing anything. Her husband is just standing there stroking his cock and I motion him over to put it in her asshole. This guy had a giant cock and I could feel it slide inside her already cramped pelvis(she was easily only 5 feet tall and 100 pounds. She came in the first 10 strokes and holy shit did she gush everywhere. After about ten minutes of him just punishing her asshole she started working both of our cocks together and I tell her that I want her to sit on her husbands cock while I try to make him come while fucking her pussy. I know that he's on the verge of cumming so she fits his cock inside her ass and leans back to present her beautiful pussy to me. I immediately started to fuck her as hard and fast as I can and after about 2-3 minutes she has a quivering orgasm which makes him and me cum. I pulled out and before she can get off of her husband my partner is inside her. I sit down on the fouton to recover and I'm just watching all of the fucking going on. Brianna and her boyfriend started fucking next to me and she starts blowing me to get me hard again...it works.
I got behind her and started fucking her asshole which made her boyfriend cum. She's disappointed because she's almost there so she slides him out and I slide in. I remembered that I wasn't about to cum in this girls pussy again and risk her getting pregnant again but she felt so good that I didn't care and I fill her up. I hear my buddy cumming inside the wife and Brianna notes that it's 1130 so we go watch the ball drop. Brianna cleaned up before but Andrea(the wife) just pulls down her miniskirt, fixes her top and hair and heads out full of cum.
We watch the ball drop, enjoy the music and I'm watching Andrea look sexy as fuck. I call Ryan over and tell him I had a great time but I didn't get to try out her asshole like everyone else did. He tells me to go upstairs and he'll send her up. I tell him to send her over and she can lift her skirt up in the back. He smirks and goes to tell her. She comes over and she tells me that she doesn't like the idea but I assure her that if she looks like she's just dancing with me, my buddy and her husband no one will notice. She complies and I slide out through my zipper and into her asshole. The two other guys run blocker as she proceeds to work my cock until I pull her hips to leave a balls deep creampie. She started to slide her skirt down and my buddy is inside her for the next 15 minutes. The husband wants a turn but she says she's too soar so he fills up her pussy instead. Finally she's able to pull down her skirt and we can see our cum running down her legs as she makes her way to the bathroom. We say goodbye and tell them thanks and to tell their friends. Here's to hoping for new and exciting holes to fill up this year.
Anyone else have any other stories?

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Anonymous
@confessions
23 Aug 2025 12:24AM
• 534 views • 7 attachments
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My Puerto Rican GF/Baby Mama used to be a backpage escort/prostitute. Thats how I met her, then we became friends then lovers. First night I fucked her I gave her an extra $50 to hit raw. She told me not to cum inside her but I definitely didnt listen. She was BIG MAD. She almost went to call her pimp for the violation but I talked her down.
After that I became one of her regulars and she kept getting +$50 from me and asking me not to cum inside her but I never listened. Eventually she just accepted that I was gonna creampie her and stopped asking. She also just started letting me creampie her mouth and ass without complaint. After a while we became friends, fuckbuddies, then also lovers. For a while she continued to prostitute while I was with her and I became her "manager" then she aged out of the game. Now we're just chillen doing our thing... We live together now.

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Anonymous
@confessions
16 Jul 2011 12:18PM
• 840 views • 0 attachments
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I confess that last night I had the most random, fast and satisfying sex I have had in a very long time.

Twice a week I buy lotto tickets at the local Circle K and there is a southern transplant there.

I always pay for lotto in 50 cent pieces and she has started to remember me.

Yesterday afternoon for some reason I got to the counter and let out my worst fake grit-eater dialect and asked "How yall doin darlin?"

She laughed and then in my native Midwestern Fargo dialect I asked for the tickets and told her to have a good weekend.

She thanked me and volunteered that she was off weekend. I said jokingly, we should do something.

She flat out told me, come back at 10.

I went home and told the wife about this little exchange, and since we are swingers, the wife told me to go for it, that she probably going out with one of her boy toys anyway..

So I went back....

J came out of the store and waved me over to her car on the dark side of the store. We got in and she immediately slid her jeans and panties off and straddled me, I pulled out my cock and she jammed her pussy down on me and started an internal squeeze that felt good.

I started to stroke her and she stopped me, she wanted to make me cum just by squeezing me... and she did just that..

After I came in her she got off me and sat on my legs, still facing me and started twirling herself. I asked if she wanted help with that, she said no... finished herself off with a screaming orgasm.

She thanked me for trying to help told me that the only way she can get off is my masturbating with fresh man cum from inside her pussy.

She then said we will do this again, but if you act like an asshole or try to get possessive or be my boyfriend, I wont do it anymore. I told her that's cool I am married and a swinger, I can fuck her anytime emotion free. She liked that....

So then, like a complete idiot... I said to her... I have to ask why... She is about 22-25ish thin, black hair, big blue eyes and average leaning towards pretty and I am the standard Motherless man, short, fat, over 45, balding, etc... I know I should not ask that question and just accept she deigned to fuck me, but we all make mistakes..

She simply said... "you made me laugh."

Then she said she was hungry and had to go, see me Tuesday for tickets... my cue to get the fuck out of her car..

About an hour after I got home the wife came home packed full of creampie from her toy and usually I grab some sloppy seconds... last night I turned it down and she said, oh... you went back to see her... Yup! She made me tell her the story while I fingered her.

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Anonymous
@confessions
02 Jun 2012 10:40AM
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I confess last night I went to Tres Equis and watched an older 50's couple through a peep hole as she fucked a stranger, He lasted all of 2 mins. After he left I went into the private video room and licked her ass and bald pussy clean. Eating her creampie. Then I fucked her myself and left another cream pie inside her. A third guy went in after me, a black guy and he tried to fuck her but couldnt get hard. I went back in and cleaned my own mess for her.

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@confessions
29 Jan 2012 11:20AM
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I SO want to offer a "normal" woman 50 bucks to let me creampie her pussy. The problem is, I'd love it if she weren't on birth control.

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