Tag: Girlfriend

These boots were make for walking…and fucking – How I [M] fucked a MILF [F] and picked up a fetish

I was 24 and fresh out of University, and started a job with a fairly large company.

My time with the ladies at uni hadn’t been prolific – I’d slept with 2 people in the 4 years. My main reason for this spell was my self-confidence…I had none! I was about 15 stone (210lbs or 95kgs for those in the new world) heavier than I am now. Girls rarely looked at me, and those who did would let my advances down with “I bet you give great hugs”. So I rarely tried anything.

I started work and there weren’t any in the office of a similar age to me. There was one woman in the office who caught my eye – Claire.

Now the first thing I’ll say is that Claire was not technically a MILF…she had no kids, however she was 12 years older than me and very attractive, so MILF will do for a description.
Not long before I started with the company, Claire’s husband had walked out on her and moved to Portugal to live with a girl he met on a boys holiday. Read more »

[MFF] – Met up with a couple, took the girl home with us

Hi GWS. I wanted to share another story the sexual adventures that my girlfriend and I have recently started embarking on. Forgive me, for I am not a writer and have an affinity for using long sentences and passive voice. All the name of sexy time. Long read, but I hope worth it. Enjoy!

My girlfriend and I have been together for over 5 years. When we started dating, the whole internet dating scene was still very young, with only notables like OkCupid and Match.com being around. We always felt like we missed out on the proliferation of dating apps, mostly notably Tinder.

A couple years ago, we decided to try our hand at finding either another female or another couple to expand our sexual horizons and quickly found 3nder. Basically, Tinder for couples looking for threesomes, foursomes, and moresomes. The app has since renamed itself due to a lawsuit from Tinder, but it will always be 3nder to us. Read more »

[MT] Dating a (trans)woman in grad school. Nobody knew she was trans

Warning: this is long.

I went to grad school for art education.

During my final semester I got to know and date a beautiful girl named Tanya. Though my friends got to know her slightly and my family met her at graduation, none of them – to this day – know that she was actually a trans woman.

I didn’t know either at first. All I knew is that I was smitten with the girl who sat down next to me on the first day of a required liberal arts elective.

Her body was the first thing that got my attention. She was short, maybe 5 foot 3, with a petite frame and tiny little shoulders. But she was also busty, wearing what I later learned was one of several very lacy 32D bras over a fabulous pair of implants.

That first day she wore a tight short sleeved top with a very high collar neck – horizontal black and white stripes – that looked startling with her curves. Down below, she wore big ruffled cargo pants that actually complimented the look in a weird way. Her hair was shoulder length, black with artsy streaks of dark purple. Read more »

Free use on my university campus (true story!)

Hey guys. First off, this story is true. It happened about a half hour ago in a Canadian University campus. I’m not gonna put in any names or anything, in order to protect my own anonymity (this is a burner account and I have a girlfriend), and also to not ruin a good thing.

When you find a slut in the wild, and I mean a *true* slut, (the one who doesn’t care about anything but a belly full of cum) you just don’t let that go to waste. There’s nothing better in the world than crazy pussy, and if you can get that without the ramifications, you better hop on it.

Everybody wants to find a pussy in a wall. Everybody wants that anonymous fuckhole sometimes. Maybe your girlfriend doesn’t give great head, maybe you’re single and need to get a nut off for stress purposes. Whatever your reason for it, sometimes you need a bit more warmth than good ol’ Palmela Handerson is capable of giving. Read more »

While my father slept. [Fm] [Fdom, Msub]

My parents had been divorced since I was about ten. It was long and messy, but irrelevant. The important thing is that my father remarried during my senior year of High School. They had met online, and had dated about a year, which was quick. After I first met this woman, though I knew what had gone through my father’s head.

Natalie was several years younger than my father, and at 48 she looked stunning. Had she any kids, she would be the personification of a MILF. She dyed her hair a dark red, and kept it shoulder-length, which perfectly framed her face. Not that her face needed help drawing attention. She had the most beautiful milk-chocolate eyes. Great men had broken down locking with those eyes. That was if they made it past imagining her thick lips wrapped around their dicks. Read more »

[MF] [public] That time my girlfriend and I accidentally put on a show for some drunk college kids

I had a lot of fun writing my first post here and got a really positive response, so I thought I’d share another story. As before, I’ll mark the beginning of the sexy stuff with a row of hyphens.

This was about two years after my last story. Immediately after graduating I moved back home to look for a job, and it wasn’t exactly going great; I’d picked an easy major because I grew up hearing how important it was to “just get a degree,” and I didn’t do any extracurricular activities while in school (not the kind you’d put on a resume, at least), so my prospects were almost nonexistent. I was living at my mom’s house with her and two of my grown siblings, one of whom had a toddler of her own (I wasn’t the only one in my family who had trouble getting their act together and adulting up). I was working as a janitor, saving money and thinking about what I should do next. Read more »

I’m too young for sex :( pt. 23 [ff]

The weekend had been one of the best in my life, but then Monday morning brought me another pair of ruined panties. For the first time since my very first period, I was completely taken by surprise by its arrival. Usually I got crampy or moody just before it started, but I’d noticed nothing this time. Then I remembered the wonderful side-effect of having an IUD.

School that morning felt different. I had a girlfriend named Samantha Juliet Green and we had spent a wonderful weekend getting to know each other better. Joe liked her a lot, I could tell. He treated her almost like he treated his best friend Mark. Mom put her to work doing chores right along with me, which in a perverse way showed how much she liked her. Dad kept his distance until the topic of professional baseball came up. Then Dad and Sam had a lively chat about which teams were going to the playoffs in the fall.

After I hit my locker before lunch, I practically danced into the lunch room. When Sam caught sight of me, her eyes sparkled and she stood to hug me before we sat down. Some of the smirks around the table told me they knew all about us becoming intimate at this point, but I didn’t care as I dug into my sack lunch. Read more »

The Long Trail [MF] [Fdom]

Almost a year ago I broke up with my long-term girlfriend. If it is ok with you, I’d rather not mention her name because, well, I took some rather drastic measures to try and forget her. How drastic, you ask? Ok, after six months of self-indulgent misery I decided to go for a walk. A long walk… a very long walk. Six months ago I began a 12 month walk along the Appalachian Trail – 2190 miles across 14 States. At the time of this tale, I was roughly halfway finished after starting out in Maine and was roughly near Harrisburg, Pennsylvania (I think, anyway, there are very few signposts out in the wilderness.) During that time I became a different man. I’m 29 years old, medium height, fair complexion and most women would probably think that I was reasonably attractive. I say reasonably, because I’ve not always been that way these last few months. Sometimes I rock a ludicrous hillbilly beard because, well, on the long trail personal grooming is not the first order of business. Also, I often smell a bit – its honest and fresh BO of course, because washing and bathing is to be found only where you can find it. At those times when I can’t stand myself looking or smelling like a polecat I take myself into some small town and get a haircut and wash my clothes. Other times I mostly just strip off and jump into some beautiful and clean mountain stream when the weather is warm. If the mood takes me and the scenery is kind I may spend a few days letting my body recover from the endless tramping up and down the mountain tracks. Back home I own a small software company. You would never have heard of it, but it has made me more money than I can usefully spend. As a company director I had been living a soft life and, well, I used to be a tiny bit pudgy. No more though. A thousand hard miles behind me and an avoidance of all form of modern conveniences such as fast-food or motor vehicles, I have never been fitter. My body was as hard as a slab of concrete. Read more »

My first meet and fuck. [FM]

This was a few weeks ago. Some of you may not find this going wild but it is for me. I have always known the girls I fuck for a while before we have sex, thats just how I am, I’m not much of a slut.
So the story goes, I am drinking with my friends J and B at my house and J invites a girl over lets call her L. So J says L is his Bothers girlfriend so no one should fuck her. The night goes on and everyone is drunk, talking and having a good time. Eventually its just me L and B (B is a girl). Me and B are asking L personal questions because both of us just met L. While we are asking her questions and leaning more about her, I start to realize that something isn’t adding up. She is talking about a brake up a lot when she is supposed to be dating J’s brother. So B asked her if her and J’s brother are still together and she said that they haven’t been together in a long time. L is about 5’5 with B size tits and a nice ass and very fit body, point is she is very cute! This is when I decided that I would give fucking a her a chance. I thought J must of gotten some facts wrong and misunderstood the dynamic of L and his brothers relationship. B ends up going home and J passes out so its just me and L. We are having a great time talking and smoking cigarettes on the back deck of my house. Its kind of cold out and I am in shorts and t-shirt so I am shivering and we are sitting on a long bench so she scoots over and wrapped her legs around me to warm me up. Me not being a idiot noticed that she was fitting with me so I kissed her and we ended up making out. The more we kissed the more I could tell she wanted me, so I started rubbing her pussy through her leggings and she starts to moan so I don’t stop until we both realize that we are still outside and there are better places to fuck then on my back deck. We go up stairs to my room and we both begin to kiss and undress each other. When both of us are naked she lays me on my back and starts to suck my dick. God damn is she good at sucking dick!! After she feels like I am good and ready she starts to ride me like I have never been ridden before. After a while of her riding me I decide it’s my turn to be on top, so I flip her over and begin fucking her in the missionary position and this when she cums and claws the living hell out of my back!! I mean that shit hurt!!!!! But I didn’t let that distract me from making L scream like a banshie. A while later I pull out and finish on her tummy. After we are all done, we start talking and I find out J told L to play along with the story about her and J’s brother dating because J wanted to fuck her that night.
His plain didn’t work that well. I met her and fucked her 4 hours later. Thats the quickest I have ever met someone and fucked them.