Tag: Girlfriend

Daddy gives me a punishment. [Gay] [Mm] [bdsm] [Mdom] [oral] Daddy gives me a punishment.

It was a Friday afternoon in the summer. I had been invited over to my friend Riley’s house for the first time to stay the night. I headed over to his house around 3 PM. It was nice a nice and warm day and we went outside and walked to the park, hung out and came back around dark. When we came back his mother had made us dinner.

She had cooked some hamburger helper and had the table set. Me and Riley sat down and ate with her. We ate for probably about 30 minutes and then decided we would go play some Halo in the living room because that’s where the biggest TV in the house was. We played Halo until about 2 in the morning and then his mom walked in.

“Time to go to bed boys.” She said in a hushed voice. We complied and headed to Riley’s room where there was a bed big enough for 2 people to sleep. I laid down on the left side of the bed and then he got in the bed and turned the lights out. Read more »

My Upside Down backwards infidelity (PART 1)

So to start this story off some context is needed. 7 months ago I moved away to school being forced to leave my girlfriend of 6 months behind but remaining committed to each other. a month in she came to visit me and admitted that she had cheated on me with one of my best friends and his girlfriend. Naturally I was devastated but after a lot of deliberating I decided that I was willing to try again being that we had our own sexual history with this couple. Over the course of the next month and a half it came out that she had lied and had actually hooked up with my best friend two other times including once just before I left. She claimed it was because she had a history of messed up choices and bad relationships and it was her only way to feel close to me while so far away. I went through a heavy depression and did a lot of shit I wasn’t proud of, disowned a lot of friends who had become included in the lies, breaking a lot of things and cutting. I looked for every opportunity to cheat on my girlfriend to level the playing field and feel better to hopefully help me move forward with her but it was difficult while attending third year university. Read more »

Downtown drinking turns into 3some with wife and a close friend (MFF)

Just getting this out there and so I can remember it for the future.

Backstory – So it’s Saturday before Easter and my wife and I go downtown for drinks with our friends (8 people total). None of us have kids, all in our late 20’s, and family gatherings later in the day on Sunday. We all decide to make it a great night of beers, shots, and bar hooping downtown with all staying at an amazing 5-star hotel in the heart of the city. We all got our own rooms and my wife has been baby crazy lately and ovulating to make it a perfect night to have some crazy sex b/w the 2 of us.

Bars Read more »

Stacy in the Stocks – Mff – Bondage

The party was large. A select group of select kinky people. A sex party. An orgy. A no holds barred kink fest. About 60 of us. I won’t dive into the details as it would take paragraphs. They are real, they are still active and the only reason I would ever think about moving back to that city.

Stacy and I were dressed to the 9’s for it, the annual charity party. I in a rented tux with a black domino. Her in something that barely deserved the title little black dress. Her lovely large breasts ready to pop out of it and the skirt so low that no one had to ask “is she wearing panties?” The answer, as almost always, was no. Her high heels made her legs and ass look lovely and the only with the black matching domino and wicked smile, it wasn’t hard to see why she still holds a special place in my heart. Read more »

Cabin in the Woods Ch. 02 [mfff]

Zack awoke to a warm, wet mouth clamped around his cock the next morning. He groaned, feeling the tongue of the mystery girl swirl around his cockhead.

“Chloe?” Zack guessed, his forehead throbbing with a hangover from the sex filled night before.

“Nope, Samantha.” He opened his eyes to see the head of a bespectacled brunette spinning around him.

“Oh.” Zack closed his eyes and recollapsed on the bed, the events of the past twelve hours swirling around in his head. He’d driven to the cabin with his best friend Ashley, his cock-hardening crush Chloe, and Samantha, the nerdy brunette currently bobbing her head on his dick. He’d seen Chloe naked, fingering herself to the thought of him. Heck, he had seen all three of them in the nude, and stuck his cock in them one hole or another at the card game turned orgy the previous night. The last thing he remembered was crawling into bed with Ashley in his arms, her soft auburn hair splayed around his cheeks as she whispered into his ear. Read more »

Giving [m]y girl[f]riend her first oral sex and orgasm.

(NOTE: Quite a bit of build-up in this story. Scroll down to the line break if you want to skip it.)

My girlfriend and I were both out of college, but still in our early 20’s. I’d just returned home from a week-long business trip, which was the first time that my girlfriend of just over 3 months and I had really spent any real time apart since we’d started dating. The night before I’d left for that trip had been a great one — [she gave me my first blowjob](https://www.reddit.com/r/gonewildstories/comments/1psv3j/remembering_my_first_blowjob_mf/), which was also the first one she’d ever given.

She hadn’t wanted to do anything else that night other than cuddle. The next day (a Sunday), I left for my trip but I made sure that flowers were delivered to her so that she’d know that I was thinking about her while I was away.

I returned home late on a Friday night, so it wasn’t until Saturday (exactly a week later) that we were able to see each other. That Saturday night was one of those perfect early-in-a-relationship nights of sexual tension and excitement, when you know sexy things are going to happen but a big part of the fun is the anticipation and lead-up to it. My girlfriend was house-sitting for a friend of hers that weekend, so we had a house all to ourselves for some alone time on Saturday night and all day Sunday. Read more »

She squirted on me, so I came on her [M21/F18/F21]

This story is 100% true and happened to me when I was in college. It involves a couple of girls from my previous story (https://www.reddit.com/r/gonewildstories/comments/4buyd3/hot_tub_fuck_machine_m21f20m21f20m20f18m23f21/): my girlfriend Lilly and a mutual friend of ours, Ella.

Ella had only just turned 18 and was an insatiable nympho. She had drunkenly confessed that she was attracted to both of us, particularly Lilly. She was a little on the larger side: she had a bit of a belly, but also had enormous G-cup tits and a pretty face. She held her weight well, her entire body felt soft yet firm, she wasn’t floppy or saggy anywhere. I had never particularly been into larger girls until I fucked Ella in a hot tub a few weeks earlier. It was a completely different experience fucking someone a similar weight to you and there were so many curves to caress and hold on to.
On the other hand, Lilly was a much more slight and petite girl, she was curvy in her own way, with shapely D-cup tits and voluptuous butt. She was a beautiful mixed race girl with lovely caramel skin (ie think Mia Khalifa in the face, even down to the nerdy glasses). Read more »

How I [M] banged my high school valedictorian [F]

Recalling the following events in my life has made me truly appreciate the phrase “getting lucky.” Every time I think about it, I realize how lucky I am to have such a hot memory of this amazing girl.

I grew up in Colorado and went to a pretty big high school, with several hundred students in my class. The valedictorian, who gives the last speech at graduation, is determined by final (highest) GPA. During my senior year, we found out about a month before graduation that our valedictorian would be a girl named Valerie. I had never heard of her, but I found out she was a quiet Asian girl in my grade. Apparently most people weren’t surprised, as the people who knew her said she was brilliant.

Fast forward to graduation day:

I was sitting with my classmates (alphabetically seated) in the audience, waiting for my name to be called to walk across the stage. I was surprised to find that I actually had never seen or met a handful of the kids who were graduating with me. This was surprising, as I considered myself social (played varsity basketball and went to parties) and thought I had spoken to everyone at least once. Clearly I had thought wrong. Read more »

The time I (accidentally) kept a crossdresser in chastity for over 50 days [M27, T23]

This story took place in June, July and August 2015. It was between myself and a crossdresser I’ve been meeting for a few years. She’s called Kyla – and I might as well shout out to her as she’ll be reading this story. If you have any questions for her, post below and I’ll try my best to get an answer. Kyla is 23 in this story and crossdresses only part time, really as an outlet. We’ve had a few deep meaningful conversations over the years and I’ve learnt that Kyla would transition but for the good things she’s got going in her life. She lives as a male, has a good job, a good family and good prospects. She doesn’t want to rock the boat too much.

I don’t think I could really say I “live” in the UK. I’m usually travelling with work so only spend perhaps ten days per month in England, and sometimes that time is in London hotels as I stopover. I do have a nice house though that I enjoy returning to when I’ve got time. When I return home I also enjoy getting Kyla to come over for a good, lengthy, overnight session. She’ll come already dolled up, will bring an overnight bag and we’ll eat, fuck and sleep until the next morning. Read more »

Lindsay and Leah in the pool (another theatre kid adventure) [M18] [F18] [F18]

This is my second post and it’s even longer than the first but hopefully you all will enjoy it as much as the first. If you want to read that post here is the link: https://redd.it/4bq4dz

A recurring theme in these posts is that these stories all involve friends from my high school theatre clique. This particular story takes place the summer after graduation.

In the town where I grew up, every teenager aged seventeen to twenty (boy or girl) is on one mission: the quest for alcohol. My parents weren’t around a lot when I was that age so my house became a regular party spot where we could drink and not get caught. We also had a lot of alcohol in my house accumulated from parties my older brother threw. I was sitting on a gold mine. Read more »