Category: gonewildstories

So my last story on this sub enjoyed a bit of popularity. I decided to share the story of how I lost my virginity.
So I was a bit of a late bloomer. I was 22 at the time and the year before, I made out with an older woman and I basically found something out about myself that day. I like cougars, so naturally, I set up a cougarlife.com profile. It didn’t take long for me to connect with a much older woman. She had a gorgeous pic and we would chat all the time. We exchanged numbers and after a little while we decided to meet. She lived like 90 mins away and she decided to drive on up to see me on a weekend. We met at a local park on a Saturday and we walked around and talked. We got frozen yogurt and started talking about my favorite topic, standup comedy. We came to my place to “chill and watch Netflix.” It wasn’t lost on her. I had just gotten a new stethoscope at the time (nursing school) and she was in the field so I showed it to her. She asked to listen to my heart. “wow. It’s going so fast. Your lips just look so kissable” she said. It took what felt like an hour for me to get the courage to say “then why don’t you just kiss them?” But I did. And she did. We went to my room. I took off her bra with one hand. Still proud of that lol. Her breasts were very large and smelled like lotion, not to mention the undeniable and intoxicating scent of pheromones. We make out for a little bit and she instructed me to take her pants off and go down on her. I have poor coordination. To hit the clit with my tongue, I decided to rub it with my finger and follow my arm and hand down to my to tongue. But it did the job. She even though it was charming. She asked “how do I taste?” And I just said “like the ocean” and continued on eating. I started fingering her and remarked that “it really does feel like warm apple pie” and that made her laugh quite a bit. But I kept going. I was on a mission. I felt her pussy tighten up and I freaked out. I immediately withdrew my fingers. I didn’t expect it. She was annoyed but understanding. And momma didn’t raise no quitter so I got back on the horse and finished her off. She then started working on me, and I started making these horrendous noises like a cat immigrating its owners orgasm. She thought it was rad. I was just such a fuckijg virgin and she loved it. Then, for the next few hours I was mainly fingering her and eating her out while doing things to her nipples like sucking and rubbing. That was nice. And she had me whisper Russian poetry in her ear. Idk what that was about but that’s cool. No skin off my back. This whole time, I can’t cum. Way too nervous even though it feels incredible. I tried to put on a condom but made the mistake of unrolling it all the way and trying to stretch it over my dick. She helps me out on the other one. We start penetrative sex and she’s uh…well, let’s say cavernous. Plus the condom. No sensation. She had to keep fluffing me and it just wasn’t going anywhere. We were both really tired by then and hungry, not to mention I was in a bunch of pain. I I cooked up some hash browns from scratch and she left. Then I jerked off and turned the night sky white. We still occasional hi via text. The end. Read more »

I’m getting a masters degree through an online program and found myself super horny before a midterm. How midterms work online is that a proctor (usually my attractive male TA but sometimes the professor or a sub), will webcam with you, have you scan the room with the webcam, and then keep watch as you complete the exam. I thought this would be the perfect opportunity to be a little naughty.

The morning of the exam, I cleaned up my bedroom and my desk, being careful to look neat and prepared. I then went into my closet and pulled out a thin, black, long-sleeve shirt with a deep scoop neck. I put that on without a bra. It was tight enough to be revealing of my hard nipples underneath, but casual enough to provide plausible deniability. My legs were mostly going to be off camera but I put on a short jean skirt to go with it. No panties of course. I was getting wetter and wetter as I got dressed to the thought of teasing my proctor. I then sat at my desk working the angle to give my proctor the best downward view of my cleavage. About ten minutes left before the exam, I pulled out a dildo and played with myself on my bed. I was so wet, I left a little pool that would for sure be obvious when I gave my proctor a scan of the room. Read more »

After posting a few stories about my past experiences with a coworker and good friend, I had a few redditers reach out, mostly of the would-you-like-to-see-my-dick variety. One guy slid into my DMs and was a decent human. This is our story.

I was working from home on a Thursday and mostly pretty bored. After dicking around for a few hours, I saw a DM. It was the first time I had that happen on Reddit. It started mostly with small talk and a little flirting, but he wasn’t overly aggressive. We exchanged the fact that we were both married and not looking for anything other than possibly chatting. We talked back and forth throughout the day and things got more sexual. He confessed that he was getting off on my stories and it made me wet to think about him cumming based on my writing. He signed off after he came, but things definitely escalated the next day. Read more »

So a couple weeks ago I remade my tinder in hopes of getting better matches since the last time I did was about a year ago. Boy was I right about that. First day i had over 50 matches. Out of those 50 there was 1 girl who really stood out. She was a tourist from Brazil, half Brazilian half Japanese and man was she beautiful. We talked for a while and after said while it became apparent that she wanted to meet up in person. I had work all week so we planned on going to the beach on the following weekend.

Upon meeting up she was even more pretty than I could have imagined. Like 10/10 and her cute personality was an even huger plus. Her English was decent but from time to time she would mess up words which was an even huger turn on. So we drove down to the beach, walked around and got to know each other. I’m a pretty shy guy but lucky for me she was in fact not shy at all. As we were sitting on the beach eventually she turned to me and in the cutest voice imaginable she said she would like to kiss me. Having no objections we began to make out on the beach. Read more »

So, this is’t my wildest story, but one of my most recent ones (and partially incomplete).

I was flying home to see my parents. Typically, I end up sitting next to men or people who never talk (I am not much of a talker either), but this time, I ended up sitting next to someone cute. Even better, she introduced herself to me and we started talking. Turns out she was flying to Europe for a 3 week backpacking trip. This was a good starting point, and we talked about our previous experiences, crazy travel stories, music, etc. Without noticing it, my hand ended up in hers and I was caressing it.

Unfortunately, the plane ride was short and I didn’t press my luck. I did want to rub her thigh, however, never did get a chance. Once we got off the plane, we walked and talked together and I helped her get in the city (she was staying there temporarily). We hugged, and I kissed her on the cheek (god how I wanted her right then!). That weekend, we texted each other intermittently, but never did meet up. After she left for Europe, we lost contact. I still fantasize about the what if. Read more »