Girlfriend Archives — Page 964 of 1305 — NSFW story

Fucking While Her Boyfriend Was Outside Looking For Her [FM]

I’d been seeing this Puerto Rican girl, we’ll call her Mia, for almost a year, on-and-off. She was a good looking woman, short with a round ass, dark skin, long, kinky hair and a sense of humor. Single mom around 29 or so, I was about 24. It was nothing serious, no real “dates”, but some nights when her ex-husband had her kid she’d just come hang out and then we’d go out for coffee in the morning.

We’d met on our commute, had taken the same train most mornings, she liked to talk but when I asked her to get a drink after work she’d blown me off with the “I live with my boyfriend” thing.

Then, when I quit that job, we lost touch but a married friend of hers had developed on me through MySpace. The next time that friend drove to visit Mia, she ended up messaging me and spending most of the next two weeks fucking like crazy.

That, I guess, caught Mia interest. She’d kicked her boyfriend out and I think it bothered her that I’d been interested but ended up in bed with her friend. The first time she came over for “dinner”, she’d made a point of telling her friend where she was going – and telling me she’d told her, with a little smirk. Read more »

[MFM] Girlfriend couldn’t wait for me to get started so she let me join in with her date when I got home! (groupsex, cuckolding)

My girlfriend Kate had set up a date with another man (calling him Ryan for simplicity) and I ended up being called in to work that afternoon. I text her to let her know and she asked if she should cancel or if I would be back. I let her know to keep it on as I wouldn’t know how long I would be until I arrived at work. I texted her when I arrived and let her know I shouldn’t be too long. She texted me back “well I’ll keep things on then. Do you mind if he gets started early? ?” I told her to go ahead, as long as the fun isn’t over by the time I arrive. I push through work and head over to Kate’s apartment. I text her on the way to let her know, she tells me “just let yourself in when you get here babe” and that was it. Read more »

[MF] last sexual encounter

Heyy.
So I shared about W, this would probably be the last post about him, seeing how our affair ended.

A little background, after the two acid trips, I did some research on psychedelics and came across Dmt. I ask him about it. We came to conclusion that he was able to make it. He bought most of the stuff needed except he was missing one ingredient which was pickling lime.

It was October 19th. We googled where to find it and literally went everywhere in search for this damn pickling lime.

Before we actually met up tho, W made it clear that he didn’t want to fuck, that that’s all we do. In my head I’m thinking, that’s the main reason we meet up. Ahaha. But I guess he wanted a break from the sex? It baffled me, but whatever, I had to respect the fact that he didn’t want to fuck.

We traveled to Home Depot, Michaels, Walmart, and even food for less to find this damn pickling lime. No one had it! Until our last stop was Walmart and they said that the Walmart in Downey had it. So we bust a mission and get in the car, drive on the freeway. Read more »

[F]. A wild 3some, and my first fisting.

I met this guy at a friends party and wet for it off right away. He was from Boston, working in Montreal on a contract. I ended up sleeping with him that night back at my place when he drove me home.

The next day he tells me that he has a girlfriend, but that they are in an open relationship. I didn’t honestly buy it, not did I really care. I wasn’t looking for a bf and in do enjoy my 1 night stands. It’s not the first time that I sleep with married guys, and it never bothered me. In my opinion if they don’t cheat with me, I’ll be another girl.

Anyways, sex was very good with him, so when he asked if we could see each other again, I was fully up for it.

This went on for about 4 months. Seeing him a few times per week. We would go out for drinks, dinner, sometimes it was just sex. Basically a sex friend. He kept taking about his GF and insisted that she was OK with him sleeping around and that in fact he had talked to her about me. Again, I pretty much ignored the conversation. I didn’t need him to justify his actions. Read more »

Had [M]y way with a virgin sissy in a Dallas hotel room

Playing with people on Reddit is damn near impossible. If you find someone near you or just willing to play virtually there is a higher than they flake out than on any other platform. Fetlife or Tinder are much easier. But there are less people on Fetlife and less kinksters on Tinder. So I end up here.

Lena was posting pics when she first caught my eye. This wasn’t the normal guy in panties stuff. These were full blown photo sets from the lips down. Skirts. Blouses. Dressed. Heels Stockings. Lingerie sets with matching garter belts. It showed dedication. I noticed we were in the same city. And so I messaged and we started chatting.

Some elements of her story were typical. She liked to dress up. She was curious about men, but had never been with one in any capacity aside from a little oral exploration, but that was way back in college before she started dressing up.

I was more fascinated by the atypical things about Lena. That she’d first started crossdressing when a girlfriend has requested it. That the woman had taught her how to dress and do makeup. That she’d been fucked with a strap on regularly. Read more »

[MF] The One (And Only) Time I Cheated: Sleeping Between My Ex-Girlfriend And Her Friend

When I was 18-years-old, I landed my first legit girlfriend. I say “legit” because I had dated before, but never started a relationship. Tara was one year older than me at 19 and played tennis at a small college three hours outside our hometown. We had been friends for a year or two and then one day we were like, “Hm. Maybe we should fuck,” and that was the start of a beautifully dramatic relationship. Tara’s best features were her legs and ass. I suppose it was all the tennis. She had smaller than average tits and a pretty standard face. I DON’T KNOW IF THAT SOUNDS MEAN! It’s not meant to be. Obviously I was attracted to her.

Our one year relationship was a tumultuous one. It was long distance for the most part as she was in college and I was still at home. Admittedly, since I was just an 18-year-old little douche, I was a bit jealous. I thought about all the guys at her college. All the older dudes who were probably more experienced than me. My silly paranoia created a few fights, but I wasn’t the only one adding unnecessary stress to the relationship. Tara had some personality disorder. I’m not going to claim to know the specifics behind it, but her father was a high-functioning alcoholic and her mother was out of the picture. She, understandably, had some issues. Read more »

Up Against The Wall [MF]

“So long, first apartment. I’ll miss you,” said Tyler Avery in a distant, but resigned tone.

“Technically, it’s a dorm room, Ty,” said Lindsey Bailey, his bemused girlfriend of the past two years.

“Call it whatever you want. It’ll always have a special place in my heart.”

“Despite the moldy showers and lousy heating?”

“Especially because of the moldy showers and lousy heating.”

It might have been a strange sentiment to have, holding an undersized and unremarkable apartment in such high regard. Tyler certainly didn’t blame his girlfriend for being eager to move out the day after they graduated college. However, he couldn’t help but have some personal attachment to his first ever home away from home.

“This is where I finally grew into who I wanted to be,” Tyler said to himself. “I got to reinvent myself within these walls. I became someone I could never have been anywhere else.” Read more »

The Sissy Journal Vol 001

Day : 03/13/2019

Time : 1:30 PM

How : Gr****r

Where : His Place – House

Name : ? 001 ?

He hit me up on gr****r. We chatted and swapped pics. Sent girly pics first, then boy pics. He wanted to meet up right away.

I went over to his house in boy clothes. He lives only a few blocks away. I walk in…

As tall as me. Olive / white skin. Chubby Hairy Daddy Bear. Glasses. Cute.

We sit in the front room and I light a joint. We puff it once before clothes start coming off. I show him my freshly shaved legs and asked if I shaved all the way to my ass. Of course I do and he wanted to see. I strip completely and turn my ass in front of his face while he sits on the couch. He touches and spanks my ass. Then he stands up and takes his pants off. OH MY GOD, HE IS UNCUT!!! I have never sucked an uncut cock, so I quickly get on my knees to give it a try. LOVE IT!!! He likes deep head. He wanted to fuck me, and tried a few times, but I wasn’t “ready” ( I explained it to him after ) for anal. He stood over me and worked my mouth and throat till he was ready to cum. Asking where I wanted him to cum, I opened my mouth and stuck out my tongue. I let him cum in my mouth and kept in in for a little bit after. I spit it into a tissue that was in my jacket pocket. HOT ONE, HAVE TO DO IT AGAIN! Read more »