[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 »

[MFF] The gift of lights, camera, action!

A little primer for this next one. When I’m not up to my elbows in con happenings, I work as a freelance photographer and occasional IT drone.

I feel pretty awful about this one, really. I crossed a personal line, and despite the fact that I’ve crossed that same line again a few times since (with the same person), it’s never been anything that I was actively getting off the the wrongness of. I know that’s kind of a buzzkill before a story like this, but I feel it’s warranted. Anyway, disclaimer aside, here we go.

I was at con with some friends of mine. There was a couple (Rob and Jen), and 2 other friends, one male (Ben, not important here), and one female (Heather, definitely important here.) They were/are not a couple. We had a suite with a sitting area that had a pull out sleeper couch and a cot in it, and two bedroom areas, each with a king size bed.

Rob and Jen took one bedroom, and I took the other, because I was the one who got us the sweet room upgrade. Ben and Heather were left to figure out things in the sitting area. Rob and Jen also worked at the con, Ben and Heather did not. We all got settled in and hit the bar. Nothing exciting happened that night. Read more »

making a new friend [MF]

So this story is about the first time I had sex with my current fuck buddy. We’re both seniors in college and have been regularly fucking for almost two months now. I had posted a while back about one of our encounters and had responses asking for me to tell you about my first time with him. Here goes.

I had been out with some girlfriends that night, bar hopping, getting tipsy and generally enjoying the night. I had been texting him continually, letting the alcohol make me flirtier than usual. We had been talking for a while, teasing each other. I knew I’d get to play with him soon – I’d been dying to get my hands on him and told him so. Usually I’m not so forward but he was responsive to it, asking where my group was headed next. We were on our way into a bar that has a huge space for dancing. When my friends and I walked in, I could instantly feel the pounding bass moving my body. Surveying at the crowd around us, I was surprised when my eyes met his dark ones across the floor. Read more »

I had the best dream last night… I got to take off every piece of that suit. [MF] [Fdom]

I started by kissing you so passionately while I undid each tiny button on that vest. I let my tongue dance with yours as I slid your vest down off your massive shoulders, pressing my body firmly against yours so I could rake my nails up your muscled back and around to your chest. With a devilish smile and a quick kiss I undid your tie and used it to blindfold you, savoring every second of your grip tightening on my hips. My lips against your neck I mumbled to you to undo your cuffs, and my kisses followed my hands down your body as I undid your shirt. Any type of undershirt you may have had on was coming off fast; all I wanted was to have my mouth on your bare chest.

Goddddd I was so happy to finally be able to take off your belt. Belt, button, zipper, then dowwwwwn onto my knees as I took your pants to the floor. My nails dug into your ass hard enough to make you gasp a little, which only made me smile more as I traced the outline of your dick with kisses through your boxers. I moved my mouth up to kiss your hip bones, your breathing increased as I slid off your boxers and let your dick rest against the side of my face. I fucking love teasing you….I wanted you to beg for me. Read more »

Vacation Fun [MF] (part 2)

The following day, I wake up pretty late and spend most my time at the pool with my family. Emma is working all day, so I don’t see her much. On my way back to my room, I cross paths with Emma. We chit chat about last night, we both had fun and make plans for tonight. I tell her that I will probably be at the bar around 10:30 and I tell her to put on a bathing suit because we are going in the hot tub when the bar closes. She agrees and we go our separate ways.

When I get to my room, I am rock hard just from seeing her, thinking about last night and imagining what’s going to happen tonight. I hesitate to rub one out but decide not to. I don’t think I’ve ever been that hard, without the presence of a woman next to me. Not masturbating in the shower was tough and it made me horny all night.

Dinner goes by as usual. I see her in line at the buffet. She is dressed in casual pants and a t-shirt and she looks amazing. Her pants are tight and you can see her amazing ass. Her t-shirt doesn’t reveal much but you know that something big is hidden under there! Read more »

How a MILF at a softball game wanting cock saved my marriage (LONG – x-post from r/truebigdickstories) [MF] [Cheating] [Group] [Swinging]

I’ve been posting on r/truebigdickstories and it was suggested I post here.

Long story short, I’m 47, a widower, and fighting cancer these days, and I’m recalling my previous experiences, focusing on the big dick centric stuff b/c of that sub. But I was kind of a slut in my younger years, having slept with 100-ish women, and being endowed (9 inches or so) played a role in some of that. Most of it had nothing to do with that, but whatever. Anyway if you want to see more, see my post history.

And I know I’m wordy — I’ve tried to go out of my way to make it short. It’s still long though — I tried.

Before I get to it, I need to explain how my wife and I got together.

When I was younger (high school and mainly college), I slept with way too many women. Over 30 or so… I can’t really keep track. I had lots of girlfriends (call me a romantic, but most of the girls I slept with were girlfriends). I tried not to sleep with random girls who weren’t girlfriends though it did happen 10 or 15 times, sometimes on accident and sometimes for sport. But I did go through girlfriends like water, I’ll admit. Read more »

New roommate doesn’t like pants [MF]

Many years ago I went through a few roommates in the span of a couple years. I first moved in to the place with a friend but he got a job out of state so he moved. The next joined the Peace Corps. I pretty much had a new roommate every 6 months, though none of them left because of me. It was never hard to find someone to fill the space as the rent was dirt cheap and very convenient for commuting. Since we paid the rent in cash (part of why it was so cheap) my landlord said he didn’t care who moved in as long as the rent was paid. Most of the roommates were friends or colleagues so I didn’t have to screen for crazies too much. One of my roommates, Jaime, was a friend of a coworker’s friend. She was medium height with dirty blonde hair. Full Bs and a small ass. I had met her once or twice but not much more than a “Hi.” 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 »