Category: gonewildstories

Hottest night of [M]y life, totaly unexpected threesome with two [F]riends [F]

I’ve been reading this sub for a while and considering telling this story.

At the time this happened I was 21 years old, and while I have had a lot of sex in my life before, all of it was within three relationships. This story happened 4 months after my last relationship ended, and I wasn’t really doing great in getting to know girls, so I had no sex in those 4 month. But then one day a miracle happened. I was sitting at home and it was already late, so I tried to sleep. Somehow I couldn’t fall asleep and was lying awake in my bed at 1 am when my phone rang. I had totally forgotten that I offered two friends (Maria and Lissy) of mine to sleep at my place if they are having troubles to get home, as they were living outside the city (I didn’t expect them to accept the offer). I answered the call and when they asked if they could sleep at my place, I accepted.

When they arrived I realized that they were both drunk, having a really hard time walking straight. I led them to my room and offered them my bed, which is easily big enough for two, and told them I’d get a mattress for myself. Read more »

Weird but hot? I fucked my girlfriend next to her sister, who was being fucked by her boyfriend. [mf] [mf]

This story happened some years ago, and it was awesome and weird at the same time. My then girlfriend Julia was an amazing girl. We had a fun relationship but it ended very abruptly. She was hipster, but in a good way. She wore little make up but was still extremely sexy and sexual. She had an amazing body, curvy with amazing big breasts and ass.

We were both out of town (and out of country) students in this city and we met through mutual friends while partying. Her parents had plenty money and rented her an amazing apartment together with her sister, Christina. Christina was dating Luiz, a very cool but shy guy who lived in Mexico at the time. Luiz tried to come over as much as he could, but she had a hard time with the long distance and time difference thing. Read more »

Fucked my heavily pregnant friend last night

This happened last night an I thought I should share it with you. Quick bit of background first. I'm a 6ft plus skinny guy, I do a lot of cycling so in pretty good shape. Been single for about 6 months and loving it. My friend Danni iv known since college so best part of 15 years. We fucked a couple of times when we were at college and super drunk. She's only a small thing just over 5ft skinny covered in piercing an tatoo. She has always been a bit of a wild one an a great friend. Last time I saw Danni was almost 6 months ago when she was just pregnant. she has this asshole of a boyfriend who none of us really like but she is infatuated with him. Fast forward to last night. I go to hers for a cup of tea, very English I know! We talk regularly but iv not seen her in ages. When she opens the door damn she got so big. The look on my face didn't hide what I was thinking. Obviously she had a big bump but her ass legs and especially her tits had gone huge. Her small frame accentuated the new curves. Wow look at you was the best I could manage. She just laughed it off as she invited me in. We had a couple of brews and we're chatting about all sorts of stuff . Our conversation eventually turned to sex . Danni was interested in my being single exploits , which I was happy to share with her . When I quizzed her she confessed things weren't going well with her and Paul the asshole boyfriend, he was working away loads an didnt seem up for anything when he was home , and she was horny almost all the time and was having to take care of herself. I shared my disbelief at this telling her how hot she looked which she did, especially her new massive tits. Read more »

That time I flew a sub in for the weekend (M/f) (Bdsm)

Long time lurker, first time contributor.

In the late 90s I was in my early 30s, newly divorced, living in a small town with an almost non existent population of single women. My ex was awarded our friends in the divorce and I felt bored and trapped and had little to do beyond driving my kids everywhere they needed to go on the days they were with me and when I wasn't working.

I was a temporary IT guy and spent a lot of time in front of a screen both at work and home. In my need to connect with anyone I discovered chatrooms, messenger, ICQ, online backgammon and long list of other places where lonely people went online. I lurked in chatrooms and did things that you do when you are anonymous, bored, discovering for the first time what other people thought about sexually and able to type 60 wpm with your left hand. At night I could be found typing away trying to keep track of multiple messenger conversations, a backgammon game or two and illegally downloading pictures, videos and stories of an adult nature. I trolled for (a fishing reference not the creature under the bridge) what I certainly hoped were women in chatrooms with titles that told you what the kink du jour was. Read more »

My [F]avorite ti[m]e visiting ho[m]e

To give you a little background on me, I come from a small Colorado town which has close to 8000 people. It's not much but most people like the scenery and the area is nice. My HS class was only 150 people so you can imagine that it is one of those towns that everyone knows everyone. I moved away after High School and went to university and then moved to Denver for a job. I was able to drive down for family holidays and this past thanksgiving I did. I came back on a Wednesday afternoon and hit up some of my HS friends on Facebook. There is a tradition where everyone goes out to party and gets drunk on thanksgiving. I wanted to join in since the past few years I wasn't able to. My friend Jenny who still lived in town offered to drive so I could drink and I gladly accepted.

There are only a handful of bars so whenever you go out you will most likely run into the same people every time which is great because anytime I come home it's like a small reunion. We had all the hugs and "what have you been up to" along with a lot of Coors and Jack Daniels. Two guys from my HS are there and we all play catch up. Tony and Billy will be there name for anonymity sake. Read more »

Third (and best) time visiting a hooker

EDIT: First time visiting a hooker

Second time visiting a hooker

My experience with the memorable handjob by my busty friend in Pimlico provided plenty of wanking material for the following months. It was my default memory anytime I jerked off without porn and I'd replay it over and over, picturing those milky white tits and my cum glistening on them.

I moved to Finchley in North London not long after. My new place was big and soulless, my housemates friendly enough though. One of them was a girl called Sarah who was a bit chubby and had decent sized tits. She was timid and quiet and her boyfriend spent a lot of time at the house. I once caught a glimpse of her naked arse through her slightly ajar door. I stopped and looked but as quick as I had spotted it she had moved out of view. I would often find myself staring at her bosom when she wasn't looking, imagining my cum spraying as she wanked my hard dick. It was pure fantasy though. There was no way anything would happen there. Read more »

How I [21M] cheated with my high school best friend (21F)

Hi everyone, it’s my first post on Reddit and english isn’t my native language so please tell me if something sounds weird !

The story I’m about to tell you happened a few years ago. I was hosting an Halloween party at my parent’s house (we have a nice place with a pool and not a lot of neighbors, so ideal to party !) and my girlfriend back then couldn’t come because she was studying really far away.

It was basically me, my sisters and 30+ friends of us, including some of my girlfriend’s friend and my best friend Anna.

Anna and I knew each other since the first year of high school, we used to take the same bus every day for at least 45 min. We always sat next to each other to talk, so we deeply knew each other personality, private and sex life.

She’s a petite blonde with a great body (I’d say a good B/ small C cups) and she exercise regularly. I’ve always thought that she was hot but never really wanted to date her because I knew she was not really the "faithful" type (sweet irony). But sometimes, listening again and again to her story describing precisely what she was doing with her body was a big turn on, I can’t deny. Read more »

Craigslist Experience [23M/26F]

Lurked on craigslist for a while today seeing what there was to see. I'm pretty good at weeding through the trash there and blasting out messages where appropriate, and I've had some really good experiences there. I'm always looking for amateur types who have obviously "never done this before", and wind up nervous in person. I've got at least one other great story I can recount, and a few lesser stories, but this is about today's.

So, I found this girl offering "stress relief", made it clear she's really into giving oral and would go out of her way to meet up. She seemed pretty genuine, and all the little tells were there that this would be legit, but also likely competitive. One of the secrets to Craigslist is to refresh often, and be the first message, which is exactly what happened. We chatted a bit, she asked for a little help (40) and made it clear that we were only looking at oral. I figured that I might be looking at a pretty good deal here, I've seen much worse being offered and demanded. Told her I was down, and then I popped the big question I had on my mind, and the one that would determine exactly how good of a deal this was: Read more »

Housewi[F]e fantasy [M]et

I came home from work this afternoon and decided to make dinner for my boyfriend. Dinner was in the oven and I was cleaning the kitchen when he walked in. The kitchen smelled amazing and I handed him a glass of wine to go with my own. I start to scrub the floor in the kitchen- I tend to be a very messy cook and mopping while standing just doesn't get the job done. So I am on all fours scrubbing the floor and hear my bf walk up behind me. "Don't touch me" I playfully warned- he never listens….

He starts massaging my ass through my pants when I looked back at him and told him I didn't have any underwear on. He slowly slipped his hand in the back of my jeans and continues to massage my ass. Eventually pulling my pants down around my knees, he kneels down behind me and pulls my ass cheeks apart and covers my asshole with his mouth, while slipping a finger into my aching pussy. He finger fucks and kisses me until I am rocking back and forth against him, begging for more. He undoes his pants and pulls me onto his cock, hard. I came almost as soon as he was inside of me, and then again, and again. We fucked hard on the kitchen floor next to the meatloaf baking in the oven. When he was about to come- I spread my ass cheeks apart and told him to cum on my asshole. His cum feels amazing in between my ass cheeks and running down my legs. I didn't want to stop- I used his cum as lube as I fucked my asshole with a finger until I was spent. Read more »

The unexpected happy ending.

I'm a happily married 40 something man with two wonderful children who experienced the best massage of his life. The day started off like any other day with running errands and getting lunch. I had an appointment with my massage therapist that I was looking forward to. I've been going to her off and on for the last few months when my back and shoulders were hurting.

She is 6 foot 1 with long tone legs, short hair and 34 D cup boobs. She always wear yoga pants that show off her ass and a tight shirt that made it hard to relax and enjoy my massage. The last few visits we would flirt back and forth some but nothing to risqué.

She instructed me to get undressed and get under the covers face down. I did as instructed and waited for her to get back into the room. I was thinking about how hot she was looking when I heard the door open and she said "What seems to be hurting you today"

"My shoulders and my glutes hurt" I responded. Read more »