gonewildstories Archives — Page 2348 of 5640 — NSFW story

Wisconsin [F]s introduced [m]e to the world of sex.

I have to warn you, this is not an individual ‘gone wild’ story as much as it is the story of how I had finally ‘gone wild.’ I felt it belonged here because it is the truth – my truth. Rarely is the whole truth glorious. It is often embarrassing, regrettable, or possesses some element one would prefer to ignore or forget. The truth of my sexual development is no exception to that rule.

The fact is I was an extreme late bloomer. I was shy around girls in high school in the early-mid ’90’s. When I tried to talk to them I had no game. Even if I became friends with girls, I was never able to seal the deal and hook up. I played out the textbook psychological defense mechanisms like: having crushes on girls that I would have no chance of getting; the moment a girl expressed or indicated interest in me I’d assume there must be something wrong/unattractive about her; and adopting the ridiculous rule of only hooking up if/when I was in a committed relationship. Hell, I went to my senior prom with an old friend, and thinking back, I’m certain she would have hooked up with me had I made a move, but, of course, I was too much of a pussy. Read more »

Anal fun between my ex and I [F] [M]

We decided that he would finally try a butt plug last night. We had tried before but I had control of it that time, I was very gentle and listened to everything he said. This time, I got him to do all that himself so he could have complete control of it. His arms and hands will listen to his body and they will know, what he’s feeling and he can go at exactly his own pace.

I got out the black butt plug, it has two ball shaped sections, smaller one on top, with a small “handle” that stops it going all the way in and easier to remove. I used my hand to spread a thick lubricant we had purchased for our anal adventures and handed it over to him, to slide inside his anus.

He had been perving at my naked body earlier, whilst I was bending over, getting our sex toys together. Most of them are mine, I’ve been getting a bit greedy for new ones! I bent over and gently held his hard cock, sliding the excess lubrication over it and I started kissing him, so he could relax about doing it and not feel so self-conscious. Read more »

[M]y infidelity diaries: Robin, the [f]inale

*This is part 2, and picks up a shortly after* [*part 1*](https://www.reddit.com/r/gonewildstories/comments/m0yzg0/my_infidelity_diaries_robin_makes_an_offer/)*. It’s the last of my encounters with Robin, though by no means the final tale I have to tell. About me: Tall, dark hair, skinny in my youth but less so these days, with a cock on the small side of average. Oh, and for better or worse, I am a serial cheater. These are my stories — all of them real in every way, except for the names. I’m not sure what I hope to gain from writing all this down; maybe it will be cathartic for me, and hopefully it will be hot for you. Anyway, here’s what happened.*

*- – -*

“You can play with my titties any time you want.”

Robin’s [words](https://www.reddit.com/r/gonewildstories/comments/m0yzg0/my_infidelity_diaries_robin_makes_an_offer/) twitched and frothed in my mind. This was messy, and could only get messier; not only was she my roommate *and* my ex-girlfriend, but I was now dating Anne — and I knew she was uneasy about me living with my ex in the first place. But Robin’s allure was impossible to ignore. So I did what any young and morally bankrupt idealist would do: I waited for a sign. Read more »

Ellie’s[F] End of the School Year Tag Team

**Background:** All events detailed in this story are true. I’ve changed the names of everyone involved and I won’t name the school. If anyone from the area reads this, they’ll know exactly what school it is and who the girl is.

I have a couple of pics of Ellie on my profile page. I’ll post more with additional stories in the future.

I have about five years worth of stories about “Ellie” that I will share. This particular story takes place in May, right before we all left to go home for the summer. Finals were coming up so we all needed to blow off some steam.

**Story:** Once spring workouts had concluded, most of the athletes on campus spent most of their time in study hall trying to retain their eligibility for next year. I was no different. Even though my grades were decent, the stress of finals still weighed on my shoulders. It was a Thursday so I had mandatory study hall until 8:30pm. No phones, just me and my homework.

At 8:31pm I was out the door and headed back to the dorm. I had several texts, but one particularly caught my eye from my roommate Javoris. Read more »

[FF]irst time with another girl

I’ve never really told anyone the dirty details of the first time I had sex with a woman sober and intentionally, and I hope some strangers enjoy the details I told my diary tonight.

She was a friend of a friend. I’m not lying when I say she was absolutely beautiful. She had brown hair that she had recently cut short, which only drew more attention to her gorgeous face. Big hazel eyes, small nose and perfect smile. We both were about 5’5 and 125lbs, and her tits were bigger than mine at probably a full 34B.

She reached out when we were both single saying she heard I hooked up with a mutual girl friend at a recent party. We talked about how she too had hooked up with a girl before and how we both would really like to do it again.

We made plans for her to come visit and she came over and played games and drank with me and my roommates. The night finally got late and everyone went to their rooms. We went back to my room, a little drunk and giggling and nervous. We turned music on and sat on my bed and talked for what felt like ages. We had sobered up, and even brought up the topic- how scary it was, like being a teenager again- and I moved in to kiss her. Read more »

Part 2: The Optometrist visit that rocked my world [MF]

Part 2: The return to the Optometrist

I spent the following week relentlessly fantasizing about and jerking off to Dr. Robbins. My poor cock was getting beaten like it owed me rent. I think during the week I was jerking off 3 to 4 times a day and the weekends were worse. I had to do something. I had to try. I mean she wasn’t offended when she saw my hard-on and she smiled at me after. She was the perfect woman to my hormone riddled teenage mind.

I even went to the drug store and tried different perfumes to see if I could find one like it but to no avail. I knew it was a combination of things that interacted with her body that made her smell that good. It couldn’t just be recreated. I finally realized that I was driving myself insane and had to do something. I wondered if I could get away with accidentally touching her. I mean the little room was dark and we would be so close together. It was reasonable that I may accidentally touch her while moving around to make myself comfortable. I didn’t know what I was going to do but I knew it was going to be something. This next visit was my only chance to be alone with her. If I didn’t do something, I would never really get another chance. Read more »

I[M] “Cheating” on my Fiancee with our [F]riend.

So I am going to start this off with a little preface on my fiancee and I’s relationship. We both are in our early to mid 20’s and have what we call a “semi open relationship” if that is a thing. Basically means that we can pursue sex with anyone as long as the we both agree on that person. Not just a free for all. Anyway thats important to the story as we keep that to ourselves. For this story I will be F and my fiancee will be M. The friend will be D Anyway storytime…

Cut back a couple of weeks and my fiancee and I were having a couple of friends over for a dinner. We do this every few weeks just for fun. Some friends come over and we like to dress up nice, you know suits and dresses, just for fun and have a nice dinner. Everyone started arriving and a we were all gathered in the kitchen and thats when D walked through the door. She walked in with a skin tight red dress, high heels, and cherry ready lipstick. All underneath her beautiful brunette hair tied up into a clean and tidy bun. She looked gorgeous and I couldn’t help but to stare a little bit as she walked into the kitchen. The dress hugging her tight curves. I was struck by her and my fiancee to notice. Nudging me and looking at me. She knew exactly what I was thinking. She know I found D beautiful. Read more »

I [M] fucked a [F] student who was way younger than me

Well, this is a story of some time ago and still now I remember it with a smile.

I was teaching in a private school and my students were all in a wide range from 6-year-old children to 20 something. I taught French and I loved my job, get along with my colleagues and, most important, with my students. I had some difficult cases or sometimes day were rough, but overall I was very happy there.

Teaching to teenagers was challenging: they are in an age were they don’t like to stay in class and, being mine a extra class course, they loved even less spend what they considered their free time studying stupid grammar rules.From my side, I would try my best to not be boring, to keep the classes entertaining and to walk on the line between “we are here to study, your parents are paying money to give you an education” and “OK, stop with past simple, let’s talk about your day”.Sometimes I would have a very good relationship with some of them, sharing their problems or worries, but usually it was all included in the class hours package (well, sometimes I could come across a student while going around and we would say “hi”, but keep going). Read more »