My first cross dressing experience led to my first gay experience [MM]

This happened quite a few years ago when I was 19. Up until this event, I was pretty bi-curious but, coming from a small country village, didn’t have the means or ability to explore that curiosity. This happened my first year at uni.

I’d done my best from starting at Uni to be a social butterfly. I accepted any and all invites to party, spent probably far too much time in the pub and I made a lot of friends. There was one, we’ll call him Rick, who I was especially enamoured with. He was tall, muscly, with a little chin beard and long hair. We struck up a great friendship but I never had the courage to tell him just how attracted to him I was. I, for the sake of comparison, was a clear 6 inches shorter than him, rather slim and basically his exact opposite.

Drinks with my old friend

Nonfiction story that happened to a friend of mine, with names changed.

It began when I had too much to drink. My boyfriend wasn’t with us tonight because in all honesty he doesn’t know my friends that well. It was me and him and our good friend Rose. Rose and I had been drinking a fair amount and we began to feel tipsy. It was fun seeing Rose like this, she was more confident and way more flirty. She shamelessly made jokes about bedding Jay, and he would just laugh them off. He offered to stay sober to help us drive home. After we started feeling a little drunk, we asked him to drive us to Rose’s house where I would spend the night. Ride home alone in Jay’s car? After I’ve been drinking? I know my boyfriend wouldn’t say a word but I could read it on his face that he wouldn’t like that. And I don’t like making him worry. He’s probably already worried enough about me out here with these two.

[M] 29 I fucked an Ex Pornstar.

Back in 2012 when I was 21, my fantasy became true, and I fucked an ex pornstar. The better part about it is when I was younger I would masturbate to a video I had of her from a popular adult site.

My cousins GF went out to Vegas to visit and friend and called me to tell me her friends Roomate used to be in porn. She knew I was an openly sexual person and thought I’d appreciate it. I laughed when I learned it was someone I was actually familiar with and used to masturbate to regularly. I never thought I’d have the opportunity to meet her.

[FF] Two older gals JILL off together and have a light pillow fight while hungover. Day four/last day of my cruise.

I was in the last day of a cruise with my best friend Stephanie. We are both 48, I’m newly divorced, she’s just split from her husband. I’m a blonde taller, chesty, I shave myself bald now that i’m single. She’s thicker, brunette, sassy.

No men, or sex today. We are very hungover, 3 days have caught up to us. We have plans to go out but just lounge around and tan. The booze has caught up to us. I’ve always gotten this thing called the “hangover hotts”… i get so horny hungover.

My pussy aches and tingles, and i usually smell like a party, stale beer, cigarettes, messy makeup, hair a mess, sweat.

I woke up maybe 4 – 5 am. Stephanie asleep in her bed. We both had sex the night before, with same guy (check my history to read about it). I wake up horny, and silently rub my pussy, still horny from not cumming last night. I try to be quiet, Stephanie asleep, pitch black, as I finger myself.

Hailey Gets Some Help [fff] [Masturbation]

My two friends and I climbed up the stairs to my room after a quick orgy at my sexy black neighbor’s house. Y’know, like ya do. We originally went over for ice cream, but one thing led to another and the three of us took turns blowing him until eventually my friend Courtney took his massive dick for a ride followed by Jasmine. Being the stud my neighbor is, he managed to blow two loads and filled both of them to the brim with cum. Unfortunately for me, we had to go before I got any for myself.

“Seriously, if you don’t marry that man, I will,” my friend Courtney said. Both she and Jasmine were walking like they’d just spent the better part of the day riding a horse bareback. I guess in some ways they had.

“I can’t believe we just did that,” Jasmine said, flopping down onto my bed to relax.

“Yeah, me neither,” I replied as I flopped down next to her.

“Can I borrow a fresh pair of undies? I’m leaking,” Courtney said.

“Yeah, you probably will till tomorrow. He’s a heavy cummer,” I said matter-of-factly, “Top left drawer, help yourself.”

My First Orgasm That Made Me [F]20 Actually Cry and Squirt Immensely.

Super new to this sub, not sure if this is the right place to post this. I’ve just never had an orgasm this amazing, and I’m gushing to tell anyone.

I’ll start out with saying that no man that I have been with ever really made me cum. I still love sex, but I had to forget about ever orgasming with my partner. I started to think that I was broken, not sensitive enough anymore, or something. I feel that many women can relate to this. However, that all changed when I met my current boyfriend(23).

At the beginning of our relationship, the sex was just like with how it would’ve been anyone else. I would focus on pleasing him, which really does turn me on by itself. Still, a lady’s gotta cum herself sometimes, right? So, after any intense sesh, I would masturbate. This really turned my boyfriend on. Seeing me writhing and moaning his name while touching myself made him wanna see what I would look like actually climaxing.

The Cage [DDLG] [BDSM] [Petplay]

“ZZzzzzssst, ZZZzzzzsssst”. Daddy was using a power drill to screw in the last of the hardware on my new present. I could hear it from down the hall in Masters bedroom, my cartoons turned down especially low. I bit my lower lip in nervousness. “What was it, it must be big?” Daddy started talking about it after I had gone outside to play without alerting him the other day while he made breakfast. He had frantically ran around the house looking for me before spotting my black wide brimmed sun hat with pastel pink bow bobbing up and down by his bedroom window as I picked flowers for him. He rushed outside a worried stern look on his face as he pulled me up by my wrist “baby you broke a rule, that’s very very bad, Daddy was so worried!” I smiled meekly and shoved the daisies I had picked into his chest my hands lightly dusted with the deep mahogany bark and flecks of dirt lining our flower beds. He sighed “we need to teach you a lesson about wandering off little one and I have an idea.”

My alone time[f]

When I’m alone I like to have time with my pussy and trying new thing. This day I was really horny but I didn’t know why.

I went to my room and sat on my bed scrolling through Reddit looking at Dick’s and pussy and all sorts of sex but none of it was working. I decided I’d use myself as my porn. I opened my legs outside and lubed up my pussy ready for a pounding. I put one finger in and it felt great and kept going until I had about 3 fingers all stroking and pumping making me wet and wanting more. I’d never fisted before I wanted to try. I slowly put more and more in until my fist could fit it was painful but I loved the feeling of pain. I pushed up and down going harder than ever before using my self. I reached an orgasm and started to feel the need to piss but I carried only because if I needed to piss it would just make it hornier. I exploded with a squirt of juices and continued to keep pounding my pussy. U felt violated and it felt amazing. I could stop. I came for a second time but no squirt this time. It was amazing and wanting the whole experience I slowly and hesitantly put my fingers up to my mouth to taste an essence of my own joy and all my work.

Testing Forbidden Desires [Step Fantasy] [MF] [BDSM]

As long as Emily could remember, she had always had a thing for older men. Not really old—she was only eighteen after all—but, like, dad old. Men in their mid-to-late thirties. Twice her age was her sweet spot, she thought. The confidence, experience, authority that came with age was always more appealing than the naivete and cockiness displayed by her peers in the halls and DM’s. That isn’t to say she was sexually inexperienced with her own generation. She’d been with several guys from nearby highschools (she never wanted to get involved with ones she also had to sit in class with) and even two from the university over Spring Break. But she had yet to explore the frontier of her ultimate fantasy: being with a dad.

She wasn’t into *actual* incest, despite what some of her internet history revealed.

Not that it mattered; she didn’t have a dad. Well, not really. Her biological father disappeared when Emily was four after her mom found out he had been having an affair for ten years and even had a second family. It was just the two of them until her mom married Jay when she was a sophomore. Emily was pretty indifferent to his typical stepdad personality. She didn’t have that clichéd enmity towards the man like in all the teen movies, but she just didn’t connect with him either. He was a roommate who paid all the bills and fucked her mom. A lot.

Two’s Company, Three’s a Crowd Pleaser

This is based on a follower’s submission. Feel free to send me more

*

“Maybe tonight I get to cum inside you?” Nick raised his eyebrows with a grin.

Priya rolled her eyes in response and gave his leg a whack under the table of the busy bar. It was worth a try, again, to see if she’d changed her mind; she was down for almost anything, but apparently she enjoyed teasing him with this one particular fantasy.

“Have you guys seen the girl behind the bar?” Tom grinned as he took his seat in the booth. With one hand he sipped his beer, and with the other he motioned towards a short, brunette girl serving drinks.

“She’s cute,” Priya nodded.

“Bro, she’s rebound material,” Nick winked.

For the first time Nick saw Tom blush. Tom was a player, at least before he met his ex. Since the breakup he’d been out of the game and Nick knew it was time he get back on the field.

“Tom, dude. You’re hot, she’s hot. You guys need to smush.It’s basic maths.”

“It’s been a while,” Tom shrugged.