Category: gonewildstories

[M]y first time with a woman of color [MF]

This was years ago, but still a fond memory. Please pardon the formatting; I’m typing this on my phone. Sexy times will be after asterisks.

The party had died down, and most of our guests had left the apartment, except for my roommates’ dates and a couple other stragglers. One of them was a girl I had a huge crush on in high school, but never had the grapes to actually act on, even though I felt we had chemistry. She had fallen asleep in an armchair in the corner, with her jacket over her legs like a blanket.

When the last of our guests were leaving, I woke her up to see if she wanted a ride home, but secretly wanted her to stay. I never could shake the crush I had, and she was so beautiful. She asked if she could sleep there, because she was too tired to drive and didn’t want to leave her car at the apartment… Score one for me. Read more »

[MF] “You’re famous among my friends now” – A wild night with the divorced comedy club host, Part 2

*(For the first part,* [click here](https://www.reddit.com/r/gonewildstories/comments/11dezrg/mf_one_rule_no_kissing_a_wild_night_with_the/)*)*

“My friends are flying in tonight for the weekend, I have 2 hours if you want to grab a quick drink,” Kathy texted me just after I finished work, a couple of days after our wild (first) night together.

“Sure, let’s meet at [whatever bar I chose] in half an hour!” An unexpected drink with Kathy? Ok, could be worse. It was Friday night and I was planning on a night in the city solo, which was how I met Kathy in the first place.

I threw together an outfit and headed to the train, heading to the bar we decided to meet at, and within minutes, I recognized the curves and the blond hair walking towards me.

“Wow, you look amazing,” I stared Kathy’s body up and down, admiring the tight olive green dress that hugged her curves admirably.

“Thanks handsome, so do you,” Kathy returned the favor, staring me up and down. We sat at the bar and ordered a first round of drinks.

“Just so you know,” Kathy said assertively, “you’re famous among my friends now.”

“Haha, why is that?” I replied sarcastically. Read more »

I LOVEEEE hooking up with older guys! [F]

Ever since I turned 18 I’ve been craving and fantasizing getting fucked by a guy that is a lot older than me for some reason! I went on tinder for the first time and matched with a 40 year old guy. We flirted for a bit and eventually we set a day to meet up. Today i invited him to my parents house while they were gone on vacation and he was SO hot. We started making out and he slowly started to strip me completely naked. I pulled down his pants and I started sucking his huge dick! He started pounding me from the back as hard as he could and was smacking my ass to the point where it was covered in red marks. He said he always wanted to cum in a fresh teen pussy before so I let him! After he pulled out, it was dripping out so much lol it was just leaking. I’m really glad I’m on birth control now!

[M28] One of my dirtiest confessions I have is of being picked up by a couple at a gym for a threesome, but it goes somewhere a little unexpected… [MMF]

This is a little detailed and specific type of fantasy scene. It’s probably a decent fit for /r/SluttyConfessions, because it definitely feels a little slutty.

A gym couple that I’ve made small talk with for a while approaches me on a Friday night and straightforwardly invites me back to their place for drinks for the evening. Let’s call them Valerie and Drew.

It’s fairly obvious what Valerie’s intent is for the night from how she’s talking to me, and hints from past exchanges, but I’m down to go along with it. Casual hookups or being the third for a couple aren’t exactly my thing, but she’s pretty attractive with a great body. And awesome tits, so it’s a pretty hard invitation to turn down.

So I agree and we head back to their place. we’re a few drinks in and talking, Valerie’s being super handsy with both of us to get things going, and her top is coming off too. Her tits are quickly pouring out of her bra and out for show. They’re genuinely amazing, round, perky – perfect. She’s the perfect mix of hot and cute too. We play around with her great pair for a bit and then she gets down to business and pulls us out, blowing the both of us alternately there on their couch, and stroking the other who isn’t being worked on at the moment. Read more »

The rookie 32[M] in Sacramento with a redditor 22[F]

Let me start off by saying, I’ve never had casual sex before. I got married young because of a religious background and was faithfully monogamous during my marriage. Now, however, I’m living a little. Dipping my toes in the water, if you will. To see a little (Or lot) of what I look like, check my post history.

To begin, I had an overnight trip out of town. Just one night, no time to really see any sights. The only fun possibility lay in time with a new friend back at my hotel. Not one to miss an opportunity in life, I posted on the local gone wild page to see if there was any interest. I got some bites. One couple wanted me to be a part of their quest to turn straight boys bi. Other couples were interested in some group fun. I was looking to dip my toes in the water however, not dive headfirst into the freaking amazon river. The winner for me was Nevani. She was young, had a pretty face, dark skin, and what I understand the kids say is a “thicc” booty. She was busty, and adventurous. On the night in question, I messaged her at 9:30 PM. Nevani responded and agreeably said she could be to my hotel in about an hour. She was just leaving a friend’s birthday. Perfect. This gave me time to finish my beer and salad. Read more »

[M] How I became a bisexual

So it all started when I was a young teenager (now 38m) and I had a very promiscuous and adventurous girlfriend. I’ve always been very open minded sexually, however I considered myself to be heterosexual. My girlfriend at the time seamed to be far more experimental and confident when it came to her sexuality than me. She was bisexual, into assplay, pegging and MMF, anything kinky really. So most times during sex together she would try “assplay” on me, however at that time I had never done it and I wasnt that comfortable with the idea, untill….
…One night we were at her house drinking and doing ecstasy together. We started some hot & heavy sex and next thing I know she had her vibrator inside me and she was really going for it lol. Woh, I wasn’t sure at first but I could see how much it was turning her on so I thought, fuck it! I completely surrendered and let her do what she wanted to me. Once I relaxed… omg I was in total HEAVEN!! I couldn’t believe that I’d been missing out on this feeling. Gosh, I wanted this feeling more and more. Obviously from this point onwards my views on assplay changed, we would do it all the time. I no longer felt any stigma towards it, I actually fell in love with the pleasure. And on-top of that I began to have other feelings, I felt that there could potentially be something else going on sexually with me, I didn’t know exactly what that was at the time, but I’m definitely excited and nervous to find out. This girl was my first love and I fell so deeply in love with her. But, unfortunately the relationship only lasted a few years. I didn’t know it yet but that relationship would kickstart the beginning of my sexual journey. Read more »

[MF] Fucking my ex’s friend after breakup (M21/F21)

You can read my previous story with my ex C [here](https://www.reddit.com/r/gonewildstories/comments/11bsgze/mf_my_gf_f21_gave_me_m21_a_blowjob_in_the/?utm_source=share&utm_medium=android_app&utm_name=androidcss&utm_term=1&utm_content=share_button). We were fantastic and going really strong for a few months but then COVID hit us and she moved in with her family to a far away city. We tried the long distance thing for a month but it was taking a toll on both of us so we decided to end the relationship. But we stayed as friends throughout so it didn’t feel any different anyway.

When in college (before the COVID saga) I was in good contact with a lot of her friends, especially with V. She had taken a liking to me, being very close to me and opening up to me more than her own friends (This had made C pout in jealousy a couple of times) But I never let it go anywhere beyond that. I had C and I wanted to keep it that way.

Cut to now, a couple of months after ending it with C, I get a text from V saying she’s in my city for some work and asked if we could catch up. I’d love that but the cafés or pubs weren’t yet open back then. She had a plan for that. She invited me to her hotel room. Read more »

The UPS helped get me o[f]f

Last week I ordered a bunch of items from Lovehoney so I could keep my content spicy for my adoring fans. A [10” dildo](https://www.reddit.com/user/random_spotonthemap/comments/11fdkcu/got_a_new_toy_who_wants_to_see_me_use_it/?utm_source=share&utm_medium=ios_app&utm_name=iossmf), some new panties, nipple clamps, some fishnets etc. The package was set to be delivered by UPS yesterday so I got naked (except for my panties) sat on my couch, around the time they normally arrive hoping I’d catch my [hot UPS guy](https://www.reddit.com/r/SluttyConfessions/comments/116qpmw/i_39f_forgot_that_i_was_supposed_to_have_a/?utm_source=share&utm_medium=ios_app&utm_name=iossmf) and got busy.

I started fingering my tight wet cunt, [orange panties](https://www.reddit.com/r/naturaltitties/comments/11ejsnf/ootd_squeeze_my_tits/?utm_source=share&utm_medium=ios_app&utm_name=iossmf) shoved to the side. I was so soaked thinking about him coming up on me “accidentally.” But it wasn’t an accident. I had this planned. We had already been flirting every time he stopped by and he caught me outside without a bra on last week and stared at my full tits while we had a little chat. Read more »

I [M] 18 fucked my [F] 27 whore teacher pt 1.

Maths is hard and so is my dick for Miss Amber (not her real name for privacy) . She has double D cups and triple c thiccc thighs and just a fucking perfect body. I can not focus on my work because all I do is stare at her, drooling. Many of my classmates had to repeat the year because they couldn’t focus properly. And I think she knew that very well and enjoyed it; she wants students who stare to repeat the year with her so she does everything she could to make that happen. She would purposely wearing tight fitting clothes, low crop skirts and sometime coming in without a bra. She would constantly bend over in front of students who needed “help” so that they could see her cleavage dead on, and I could swear I see her smile a little whenever a student “accidentally” bumped into her ass or caught someone staring. Read more »

[MF] High school Fun Ch.1

We met during theater, she was an innocent freshman and I was a perverted sophomore. Both of us being in the production that year, allowed us to the “exclusive” cast after party. Everyone had heard rumors of what these parties were like, but first year in theater for me I wasn’t sure what to expect.

There was a bit of booze, and just a lot of kids having fun. Loud music, tv, just hanging out. It was getting late and her parents were coming to get her. We’d flirted and been into each other the entire production but this night it all changed.

I walked her out about 15 minutes before her parents were expected to roll up. We talked a little, then started to make out. Total high school make out session. Wide open mouth from her, tons of tongue! It was wet and wild!

I decided to be brave and see what else might be wet….I slid my hand down her pants, and into her panties. God damn! She was drenched!!! I fingered her for a good 5 minutes before she came all over my hand. Withdrew my hand from her pants so she could gather her self, I sucked my finger clean, and we waited for her parents. Read more »