gonewildstories Archives — Page 3102 of 5640 — NSFW story

Sneaking around with [m]il[f] housesitter

My mate has been with his wife since we were all 16 and I have known her for over 20 years now. When we were 23 her mother was housesitting this big house for a client and a few of us went there for a barbecue.

The housesitter must have been between 45 and 50. She was in good shape and sexy in a cougar way, a hot mom whose wealthy ex husband had divorced a few years before when we were finishing school. She was in between boyfriends and definitely enjoyed having a few young guys around.

Her older daughter and her friend would have been about 25 and they went out to a club while the rest of us ate dinner and drank wine out on the balcony. Everyone else went to bed quite soon after dinner, leaving myself and the housesitter out on the balcony finishing the wine.

We started looking at the stars and when I turned down from looking up she pulled into me. I was pretty drunk and was living in the moment so I kissed her back in a deep, sensual way that lasted a while. Read more »

[M]y landlord wants to [f]uck my girlfriend…and he fondled her (part 2)

My girlfriend and I were sitting on the back porch drinking wine. We hadn’t had sex since Brad fucked her in front of me a week ago and I was ready to make a move tonight. I was staring at her hips in her shorts, admiring her when she snapped me out of it.

“I need to tell you something”.

“What’s up?” I responded, feeling nervous.

“The other day when I was tanning without a top on-“

“When I ate you out in our backyard?” I interrupted with a smile.”

“Yes. Our landlord Alfie watched the whole time. I saw him up in the window. He saw my boobs and everything.”

I tried to remain cool and collected. I knew he had been watching, I had moved to give him a better view of my girlfriend as she came. She continued.

“And then yesterday when I was bringing the groceries in he came over to help carry the bags in. After he was done we were talking by my car and he asked how big my tits were. Before I could even react he reached over and grabbed my boob. He started playing with them. Read more »

[MF] The Rebound (or how I stuck my dick in crazy)

Her name was Becky and she had been friends with Jess for years and had also been with one of my good friends for years. After things fell apart with Jess and I, she was also freshly separated and she made it a point to come to my comfort. Becky was a tall and busty milf (her son was two at the time and they shared custody,) with long sandy brown hair that fell between her shoulders, her bust was easily between a G and H, although she hid it well. She still had a bit of baby weight everywhere, but again she wasn’t unpleasant to they eye. Read more »

Back to Becky’s (part2) [MF]

Part 2 of a [fun morning at college](https://www.reddit.com/r/gonewildstories/comments/hi8puq/my_backrow_fumble_with_becky_mf/)

It was a five minute bus ride from the campus back to Becky’s house. After a little initial awkwardness, laughing at having just got each other off in the lecture theatre, we started making out on the bus. All was quiet when we got back to Becky’s, her usually busy house was deserted with her housemates all out at classes, and we headed straight up to her room. I was already turned on from the ride home and my cock was throbbing in anticipation before we’d reached the top of the stairs.

We dropped our bags, kicked off our trainers and started kissing, quickly undressing each other. Becky unbuttoned my fly and reached inside my boxers again, excitedly stroking my cock. Stepping out my jeans,I stood behind Becky, pulled her vest over her head, and slipped her bra straps off her shoulders, eager to see and play with her breasts. I reached inside her bra to squeeze her breasts before undoing it completely to free her huge tits. Kissing the nape of her neck, my hands roamed over her chest, squeezing and caressing both breasts, marveling at the size of them, and tweaking her large, pale pink nipples to erect points. Becky reached behind her to play with my cock and tugged it out through the boxer fly. I began teasing down her knickers which she helped off and I pulled her close to me. My hot, veiny cock pressed into her back, a breast in one hand and my other spreading her wet pussy lips. Read more »

Massage Parlour Rimjob [MF]

I was on the way home after a bachelor party. It had been a boring bachelor party and as always because I was hungover I was horny as hell. I decided to stop at a local massage parlour that is on the way home and got an hour-long massage.

Sexual encounters are standard at this massage place so a sultry looking Asian girl showed me to the room and asked me to undress. There is a shower attached to this particular room so I always take a shower, firstly so I’m always clean and secondly to have an excuse to be naked under the towel when the masseuse returns to the room.

The massage went as usual, starting on my neck and back and working her way down my body. As she finished with my back, she removed the towel and started to massage my bare arse and legs. Her fingers lingered and brushed the inside of my thighs which she moved apart, lightly touching my balls and perineum. By the time she asked me to turn over I was hard as a rock. Read more »

[MF] Car Park anal and cum in mouth in 18 yo school girl

Reena was 18 at the time. She was half Pacific Islander and half Indian was in her last year of high school. I was in my first year of university and we had started chatting through a hook up site (pre tinder). She had green eyes and dark brown curly hair with brown skin and full lips. She had boobs and hips, but was still slender, as teenagers are.

We first met at the movies one night and starting making out immediately once we got in there. She jerked me off for a while while I fingered her, but then we got conscious of being caught so we stopped. After the movies, we went to my car and she blew me in the car park, finishing me off with her hand so I had to drive home with a load of drying cum all over my tee shirt. Read more »

[M] A Dare I Did

So, when I was young and playing Truth or Dare with my cousin and some family friends at our family’s vacation home. Actually at this point it had just become dares. There were rules in place and suffice it to say it was much easier to do this dare than face the consequences of not.
So, I got dared to run to this corner gas station, that no longer exists last time I was there, and steal a sign, then run back. Keeping the sign as proof.
Sounds simple and easy enough, it was the middle of the night after everything was closed after all. There was one small catch. The reason it was easier to just do this dare was because of the rules. There was a rule that said you could get out of any dare by removing an article of clothing, but you couldn’t cover any part of your body that clothing had been covering and you couldn’t put any clothing back on. Also, if you’re naked, you can only not do the dare by quitting and doing a much more difficult punishment dare. At this point, I was completely naked and not allowed to even put on shoes for the run. Which really was more of a half jog after that assertion. I had completely misjudged the distance I would be running too. It ended up being 2.8 miles there and back. I got seen by at least some people in a tent. Who knows who else. Here is the actual route. I was reminiscing and actually found the Route as best I could on Google Maps. Read more »

(PART TWO) My VIRGIN roommate takes my girlfriend (How my attempt to cuck myself went too far) [MF]

[Part one can be found here.](https://www.reddit.com/r/gonewildstories/comments/hod86t/my_virgin_roommate_takes_my_girlfriend_how_my/)

I was alone in my apartment for the next few hours, while they did – wait. What *were* they planning on doing tonight? It was in that moment that I realised I had no idea where the two of them were going for their “date.” I hadn’t thought to ask Chelsey, or Luke for that matter. *Doesn’t matter,* I thought to myself as I settled down with a drink, and as I did, my mind began throwing out all kinds of wild possibilities as to what they were getting up to. I tried to keep them within the realm of plausibility. How much would Chels be flirting with Luke? Would he flirt back? What would they talk about? The various scenarios ricocheted around my brain, and as they did I felt myself becoming increasingly turned on at the not-knowing of it all. The being left in the dark. The what ifs, even if they did sometimes seem far-fetched. Read more »