Tag: Anal

Cheating on [M]y Gf with my [F]riend’s Mom in High School

So I'm 26 now, but this happened my senior year of high school, when I was 18.

I was a senior in high school and I was dating a sophomore who was 16. It was great, she was hot, but I've always had a fetish for older women. One of my friend's mom, Abby, was one of my friends on AIM. We were also Myspace friends but we only spoke on AIM. We chatted on AIM because I was in a band and so was Abby's son, who was my buddy, and compared notes about local gigs we played and potential recording studio possibilities. It was all pretty innocent until one night I felt bold and comfortable enough to let slip that I liked older women. She would say stuff like "I bet you get plenty of girls your age," but I would persist that I would still prefer hooking up with someone older. Read more »

[M]y first bisexual encounter [NSFW]

(PMs very welcome)

The situation first started a long time ago when me and my friend were in elementary school. Me and my friends used to have sleep overs and do the whole truth and dare thing, where we would get naked and jerk it, but never anything sexual with each other.

One of my friends was a year older than us, so he hit puberty first and a couple of times when it was just me and him, he would get his dick out and it was much larger than any of my other friend's that i had seen. Nothing sexual happened between us, I was just intrigued by the size of his penis.

One day as a joke he pulled it out in front of me and started stroking it for a few seconds while i just watched. He put it back in his pants pretty quickly. Nothing else happened from there.

Flash forward 8 years, and this scenario had been in my mind for years. I would jack off to this quite regularly, the thought of his hard penis and possibly getting off together. but i had a series of long term relationships so never said a word, and handled them as fantasies pretty well. Read more »

My[20/M] first time with a thick girl[20/F] [Part II]

This is the second part of my story posted here, and the last part of what happened that night. Just as a recap, I’m Mike, about 5’11” and 130lbs on a good day. Dark brown hair that’s usually in a fauxhawk-esque poof, hazel eyes, and big lips. I know it’s cliché for this subreddit, but I’m a little under 6.5”, and I curve up some. Thea was a girl I met online (OKCupid, if you care). She was 5’ 8”, with C or D cup boobs. Dark, frizzy hair, gorgeous face, and wore glasses.

Thea and I loaded our blankets up into the back of my car. We were still slightly on our high from banging each other, and we didn’t want the night to end so early. I looked around on my phone at the map, looking for a place that would be out of the way, but I wasn’t familiar with that part of town, so I asked her to navigate. As we drove, we talked about things that turned us on. She was very into bondage and discipline, whereas I had been in a very tame relationship previously. I told her I’d try anything once, and she quickly agreed that so would she. We were quiet for a moment, and then she asked if we could try anal. I had lube, so I told her as soon as we found a place to park I would be happy to oblige. Read more »

How I want every time to be… and I am a guy, [mf] [anal][oral]

Looking into her hungry eyes, I was all to anxious to get to bed with her. Knowing exactly how I get when I am manic, my stamina has been able to last up to 12 hours; I approach her an gently kiss her lips, once and twice. I slowly kiss down her neck and lightly tickle her neck with kisses. We seperate and I slowly pull up her shirt while gently running the palms of my hands up each side of her body and over her arms as I remove the shirt. Repeating the process with me, she runs her hands slowly up over my abs, up my chest and over my arms. Read more »

I married a slut [MF] obedient, submissive, fisting]

The woman i married had a large sexual appetite, she also happened to have very loose sexual morals. Actually she was kinda innocent of the world, almost everything she knew about sex had come from sneaking her fathers porno tapes from his collection, the pervy guys she was friends with in school and the creep she'd gone out with during college… no one had ever so much as hinted towards the idea that sex was anything but extreme and all the time.

She was kinda shy when we first met though, it took me a long time to realise she was up for basically anything – i should have twigged when she agreed to do anal so soon, and so readily. When i got around to asking if she'd done it before she told me her college boyfriend used to do her in the ass all the time. She was great at blow-jobs too and eventually i realised she really didn't mind if i pulled her head hard into my crotch and choked her while i came, if that's what i wanted then she was fine with it, again i discovered being choked on a cock was another thing her boyfriend had taught her was a normal part of sex. Read more »

Last weekend’s fuck [m/f] (aka I love anal!)

I wrote out this story via text message, then realized I should share it here also. Enjoy.

So I'd barely seen my boyfriend all week. And naturally we couldn't wait to get our hands on eachother.

Took a long hot shower, with some extra soaping between the ass cheeks. I was so clean & so dirty, all at the same time :)

I started out sucking his cock messily as my asshole got stroked. Then he started sliding a thick finger in and out, just teasing my tight hole

I couldn't stop moaning, and flipped around on all-fours so he'd have better access. Between asshole and pussy there was an entire hand stuffing my holes.

I rubbed my clit as he fucked my holes with his hand, stretching me out. It was almost overwhelming, and I couldn't help quivering and shaking!

Eventually it was clear he couldn't wait to get that cock in me. And I couldn't wait to be filled up properly.

We started with my pussy and he pounded me hard. But it didn't take long before I asked him to Please Fuck My Ass! Read more »

Megan: My sex goddess

My first story about Megan was here And after a suggestion, I thought I would do another.

If you read the first story… you'll know that Megan was one of my sisters friends. I was a couple years older, and after she graduated we spent probably a year and a half in bed together. She was insatiable and I was… well a horny 20 year old.

Now, Megan and I never had a title… we had at least agreed that we would only be having sex with one another… but we weren't an official couple. Yeah, we did a lot together… but she felt titles were the means to an end, so to speak. I really enjoyed her company… and the sex, so I didn't disagree.

We always had pretty good romps while we had sex… usually going 45 min to an hour. She was the type that had an orgasm very fast… usually after only a few strokes… which is why I guess she loved it so much. I would usually have 2 within that time which was usually pretty awesome. Read more »

Some more exploration of a married couple to share with all of you [MF]

Hello again! We earlier published our first post to this subreddit and received very kind feedback and messages, some asking for more. So we thought we would write a post about our experience last night, since we had so much fun writing the first one.

As you may have read in our first post, we are a 30 y/o husband and wife, who are looking for more ways to experiment and explore. We are very sexual, but also very shy. That is why we thought this subreddit, and perhaps DPP (dirty pen pals) would be a good outlet for us. We've recently started to act on some of our urges, fantasies, and desires more than before, as we further settle in to our marriage. We loved sharing our experience of our first threesome with you, so we thought we would take some time to share another first with you from last night. Read more »

Craigslist Success [M/F]

Almost two weeks ago I posted an ad on craigslist with a few pics and the description beginning with, “I want you to cum for me.” I had posted on the site before, only to receive replies from bots and men asking if I’d consider letting them suck me off. The very few times women that had actually responded, resulted in a few pic swaps and sexting. However, this Thursday night a woman responded with actual interest in meeting up. She asked if being with an older woman would bother me (her 32 and me 22), of course not. We traded pics, chatted a bit, and actually agreed to have me over at her place Saturday night. I don’t have a whole lot of sexting experience, but apparently I’m pretty good at it as she said she couldn’t wait until Saturday and asked me if I could come over that night instead. As Friday seemed to drag along, we continued to text and at one point simply asked “Do you like anal?” I found an actual woman, with a high sex drive, who liked anal. Jackpot. Read more »

“Uh, if he’s going to rim you, I want to do it to you first.” [MF] [rimjob] [facesitting]

"Uh, if he's going to rim you, I want to do it to you first."

We, that is myself Robert and my wife Amanda, were sitting around in our office watching some Netflix on my computer. I held her phone in my hand; she was letting me read the dirty chat she'd had with a potential side piece on Tindr. We have an open marriage and always share our adventures, rare that they me be, with one another. They had been chatting together the better part of the day so it had been quite a bit to read through, but I had gotten just as turned on by it as I knew she was. Until he started talking about rimming her.

I couldn't help but feel a tiny twinge of jealousy; my love for my wife's ass is well-known but I had never been able to indulge in any kind of back door play. We had talked about anal sex, of course, but she wasn't into it. In general, it wasn't her thing. More specifically, my cock is too thick for her to even consider it. It was never important enough to matter, so it just became something I'd joke about with her from time to time, knowing that particular door was closed. Read more »