Category: gonewildstories

[TM] first time meeting with a guy when crossdressing

Hey all. I’m a first time poster so on this sub so please be patient with me. This is the true story of my first time getting fucked and also my first story I have written.

So some backstory. I’ve really liked crossdressing ever since I was young. I stopped for a long time but have recently picked it back up again and now I can’t stop. Started playing with toys, plugs, dildos but it never quite satisfied me. I needed the real thing so here is how it happened.

I was away for work so luckily I had a hotel room all to myself. Obviously because of this I took all my girly clothes and toys with me. After work my colleagues wanted to head out for some drinks but all I could think about was getting back to the hotel and getting dressed up to play with my toys. After more drinks than I should have had we ended up calling it a night and I headed back to my room very drunk but excited get dressed up. Read more »

[MMF] girlfriend had sex with drug dealers

I’m not quite sure if this qualifies as a confession.

My girlfriend has always had an adventurous side. She’s always been very open about her sexuality and willingness to try now things. I love that about her.

She’s 5’1, mixed race, curvy, with probably the best ass I’ve ever seen. I love her very much.

We’ve been dating for 3 years. It started at university. I had known her before that and I’d always know that she was a stoner. When we started dating, that’s one of the first things she told me.

When we became serious, she encouraged me to try it. Eventually I gave in and would smoke with her. I had never done drugs before but doing it with her was fun. Quite often,she would offer to go buy the weed because she had been buying from the dealer for a long time and got better prices. And she did. She’d often come back with enough weed for us both and it would occasionally be discounted, or even free. I never thought anything of it. But every time I bought the weed I paid full price. The dealer is a very dark skinned Indian man. He’s skinny, but short, with a moustache. His partner is a white guy, who’s quite muscular, is 6’0, with blonde hair. They’re nice enough guys. Read more »

[MF] Hot sex with my (30F) boyfriend (27M) on the couch

As always, scroll to the dashes to skip the backstory and get straight to the sex.

I went to my boyfriend’s place for a date night the other night. I dressed up for the occasion in an irridescent deep red bias cut dress which falls just past my knees. I look great in this dress – it simultaneously flatters my tall, slender figure and well proportioned curves while somehow still leaving everything to the imagination. I paired it with black platform shoes, a black collar with small chains dangling from it, and a pair of high cut black mesh panties from Victoria’s Secret. No bra, I find them uncomfortable, plus I have (average sized) perky breasts, so it doesn’t make much difference to my appearance.

When I arrived, we decided to have a glass of wine together in the living room before he made us dinner. A glass somehow turned into a few glasses, as we were deep in conversation, and time passed quickly. We were both getting pleasantly tipsy when he leaned in to kiss me. It started as a quick, closed-mouth kiss. Then another. Then another. Until, almost simultaneously, we both put our wine glasses down on the coffee table and began a heated make-out session. Read more »

I [M]29 slept with a colleague [F] on a work trip.

Sorry in advance for the long story
This all happened almost a year ago. My work had bought out a competitor and assembled a team from different locations to help with training. The person in charge of the trainings had us all meet for dinner prior to the first day so we could all meet each other and thats when I saw her lets call her Kristy. Kristy was a 5’2″ latina in her early 30s with size 44f breast and an ass to match. After getting to know one another over the first few days we all started to loosen up and started going out together to see the city and find places to eat and drink. After one particular night of drinking in the hotel lobby many of us were tipsy and most of the group called it a night but Kristy said she wanted to keep going and since I wasn’t working the next day I figured why not she offered up her room and her bottle of crown so we went up to her room, a few more mixed drinks later and we ended up in her bed just talking about the job and enjoying each other’s company when out of no where she straddles my lap and we kiss deeply she stops and whispers in my ear “I’ve been waiting for this since we got to her room” at this point I’m rock hard and I know she can feel it since she keeps rocking her hips and letting out small moans after making out for a while she works her way off my lap and down and is on her knees and telling me she needs me in her mouth and pulls my pants and boxers down and in one smooth motion has half of me in her mouth and slowly working the rest of it she is hungrily sucking my cock just focusing on making me cum and once I felt that sensation and was about to cum she takes me down her throat and lets me shoot ropes deep in her while she swallowed every last drop. Once I came down from that mind blowing blow job I said it was her turn she looks up at me and says not tonight she needs to be up for work in the morning and tells me to get dressed and kicks me out of her room.
There are more stories from this trip if this one gets enough positive feedback

[MF] A great way to be woken up

About a year ago, my then girlfriend stayed up late because she had the next day off work. I had the next day off as well but I was tired so I went to bed around 1 am. At around 3 am I slowly started to wake up. I didn’t I know what was going on , but I felt very horny, and I felt something rubbing up against my bare cock.

As I started to come too, I remember hearing my gf saying “baby baby can you woke up, I want you”. As I come too what was rubbing against me was her ass. She had pulled the front of my underwear down and was sliding up and down on my cock. My cock was firmly between her warm ass cheeks.

She didn’t realize that I had woken up yet, so I reached around her, sliding my hand between her legs. I pulled her deeper into me. She was so wet that she had soaked through her panties. I whispered into her ear, “where do you want me baby”. She let out a moan. She replied saying, “I want you in me baby. I want you in me…. no condom “.
This was a big surprise. Read more »

[MF] the time i got my shy gf to be more slutty around my friends..

So ive been dating my gf ashley for 5 years now and shes always been the shy, reserved type of girl. But recently we’ve been trying to spice up our relationship and i was starting to convince her to be more open and show herself more. Now ash is 5’6, blonde hair blue eyes, on the petite side, small but perky tits, nice thick ass, quite a few tattoos.

So a few weeks ago a bunch of friends invited us to go on vacation with them all up at this lake. They had rented a house on the water. There was like 5 couples, and probably 8 singles. We spent they first to days just catching up and partying. On that Saturday morning most of us went into the town to shop and i saw this bikini shop and convinced my gf into letting me pick out her new bikini. I found a skimpy one size to small bikini and had her try it on. WOW! It barely covered her small tits and the thong practically disappeared in her ass crack. She was hesitant but after some convincing she agreed. While paying for it on the counter was these things called pasties. Its a waterproof sticker you put on your nipples that covers them up. So i bought a bunch of them. Read more »

My lingerie model BDSM relationship [MF]

A few years ago I started dating a girl who worked as a manager at Victoria’s Secret. Her body was amazing and she had a cute face with soft brown eyes. She loved to have me sit on her bed and watch her as she modeled the newest VS lingerie by crawling around and posing for me on her bedroom floor. There always came a point where she was on her knees in front of me, mouth gaping and watering, not saying a word, silently begging for my already pulsating cock.

The first few times I started off gently. I’m not massive, but I’m hung pretty thick so I didn’t want her to choke on it. After a few times I realized the more aggressive I was, though, the more she liked it. I grabbed her hair and fucked her mouth harder. “Harder. Harder. Make me gag! Choke me with it!” – she begged for more every time. Each time I exploded down her throat I realized she was drenched from choking on my cock. That made me instantly hard again and I would fuck her pussy and ass just as hard. Read more »

[FM] I (19f)ucked my mom’s boyfriend (57m)

This morning I had sex with my mom’s boyfriend. It all started a couple weeks ago when I matched with him on tinder. At first I was angry that he was obviously cheating on my mom. Then I was intrigued that we matched. I didn’t message him. He didn’t message me. He just started acting very awkward and distant around me.

A couple days later I snuck into his laptop and looked at his browsing history. It was full of dating sites and local escort listings. He had also been looking at my Facebook photos. On that same day he searched up blonde teen on pornhub (I’m blonde)…

I watched a video that he obviously picked right after he had been looking at my Facebook photos… It was a young girl who looked alot like me getting fucked. I know I should have been horrified… But I wasn’t. Quite the opposite. I masturbated and imagined that he was on top of me. Read more »

[FM] Getting my sweaty pussy locked after the gym!

I stopped by my boyfriends place for a quickie after going to the gym yesterday. I didn’t shower becuase I was horny and wanted to hurry and figured my bf would fuck me in the shower if I asked. I was really sweaty from playing basketball and remembered thinking how much I smelled in the car driving to his place.

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While when I got there before I could say anything he had me on the ground with my legs in the air and his face buried in my pussy. He sucked my clit and locked me all over from my ass to my pussy.

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He even told me how good my pussy smelled and tasted. I’m not sure if he was just being nice or not :)

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I just got turned on while i was writing about it. I would not mind to have some fun online right now. HMU!

I [F] had sex with my friend’s Dad to avoid getting in trouble

I tried putting this in r/confessions, but it was removed. This is a real confession, and I was 19 when this happened.

I was at my friend’s house playing with a tennis ball, killing time while waiting for her to finish work. The ball bounced off the wall, and right into her brand new TV.

Her Dad came rushing and he was extremely angry when I confessed to what I had done as he had paid a lot of money for it, and threatened to tell my friend that I trashed her room. We agreed that if I had sex with him, he’d absolve me of any blame. We did, and I still regret it.