She’s out of my league, and wants to prove it: Anna, the instagram model, and her girlfriend need a host [FFM]

I told you the story of [how I met Anna](https://www.reddit.com/r/gonewildstories/comments/o822m2/a_league_of_her_own_how_i_m_started_this_long/), a woman who is way out of my league. I’m a network engineer, living in a smaller touristic town; she’s living in a bigger city, and has quite a full life.

However, I see her often in my town – being relatively close to the capital it gets a lot of visitors, and it’s quite a coveted destination in both winter and summer. This happened five years ago, in the summer. Anna was visiting with her friend, taking a break from her job. She just found out she was pregnant (and she confessed that she had no idea if it’s her fiancee’s or his father’s). She stayed for a few days before reaching out – I still had her Tinder, but she confessed she was a bit under the weather.

[M]y [F]irst Night with the Acrobat Part 2

Here is a link to part 1. I highly recommend you read that first.

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[https://www.reddit.com/r/gonewildstories/comments/o880ty/my_first_night_with_the_acrobat_part_1_long/](https://www.reddit.com/r/gonewildstories/comments/o880ty/my_first_night_with_the_acrobat_part_1_long/)

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At that moment I fully committed (please dont do what I did and be fucking safe when fucking strangers for the first time) and threw down the condom I was about to open and positioned the head of my once again rock hard cock right against her dripping pussy from behind, now completely bareback…

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I pushed my cock into her and parted through her tight pussy lips until my cock was fully inside of her. I knew it was so wrong but I have never gone raw with a stranger this fast and it felt so fucking good I didnt even care. I pulled her body close up against mine as I started fucking her in standing doggy. Her back arched so that I could kiss her as I fucked her as well as choke her which she loved. A started to push her ass back against me which only made it feel that much better. She wanted me just as badly as I wanted her.

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I [M] jacked off while a friend [F] watched and masturbated

A few years back I was visiting some friends at an old college friends house; she was one of my wife’s old roommates. We had gotten pretty drunk and the crowd had thinned down to me, my friend, and a married couple that I often post about. We were all pretty drunk and in our underwear. My friend was a large but cute girl, and we were all sitting on the couch playing with her ample breasts that she had out for display. The other girl there was pretty petite, so she was shocked at how large and soft her tits were and couldn’t keep her hands off them. It was a very sexually charged atmosphere and my married friend continually hinted that her husband should pull his cock to show everyone how massive he was. He wasn’t feeling it, so he declined, much to our chagrin. After pulling his wife away, he left us to our own devices and drove his wife home.

“Okay, here’s some blankets for you. I’m going to bed.” My wife college roommate was still only wearing panties and standing in the living room with a pile of sheets in her arm. She helped me make the couch into a bed.

I [M] cheated with my ex [F] through college

I (now a 23M) would have the nastiest sex of my life with my ex (now a 23F) while dating my girlfriend at the time as 19 year olds

Don’t take this as an endorsement for infidelity, I was 19 and foolish and would never do this now, but it was fun while it lasted.

I dated a girl all through high school, we can call her Allie. Allie was about 5’8”, medium length dark brown hair, curvy, and very innocent looking. I was the only guy she had ever been with. Then, she cheated on me in college and we broke up. After some time, I started dating another girl I had met, we can call her Katie. I would run into Allie almost every day in college, as our classes were near each other and my fraternity was often involved in socials with her sorority. One day at a social, she pulled me into the hallway so we were alone, sat me down and said she wanted to apologize for everything. I told her I forgave her and we could move past it. We stood up and hugged and went back into the social.

[F]un summer break during college. Part 1

Here is another story, or rather relationship my husband is always interested in hearing more about. It was my most sexual summer in college so I’ll tell it in parts.

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A little backstory

I went to an In-state university and ended up conveniently becoming best friends with a girl from the next city from mine, let’s call her Amanda. It actually was even better than that because I lived on the far side of my town and was actually closer to her town than my own.

I had a lot of classes with Amanda that sophomore year and when the school year was over, we made plans to hang out all summer.

That first weekend I went to meet Amanda at a local bar in her town and was surprised to be introduced to dozens of friends from her high school. Since it was the first weekend home, I should have figured it would be a reunion, but it was fun to see who she was friends with and there were a couple cute boys in the group as well.

[F]UN ON VACATION. WEIRD TIMES PART 2 [GROUP]

PART 2- IT’S NOT DONE BUT THE RESPONSE WAS GOOD SO I DIDNT WANT KEEP EVERYONE WAITING: ([Part1Here](https://www.reddit.com/r/gonewildstories/comments/oa7n5o/fun_on_vacation_weird_times_group/?utm_medium=android_app&utm_source=share))

Justina & I are making out, and I feel a hand rubbing my pussy from the back. It’s Leon, rubbing my clit and kissing my behind. Justina moves my hair out of my face, and whispers that she wants to see me cum. Leon hears this and positions himself under me. I’m now sitting on his face, grinding on every inch of his tongue.

Justina is now playing with Dave, bobbing her head up & down on his cock. I’m watching with envy and his hard dick makes his way to mouth too. I spit on the head of his dick and swallow him hole. He lets out an “omg,” then Juliana smiles and joins me. We suck his dick together, while Leon licks my clit directly. I can’t focus – My chest is warm, my legs go stiff, and I start shaking, barely able to kneel anymore. Leon is rock-hard, and lays me down. His eyes run up & down my body, and he spits directly on my pussy ready to fuck me again. The first thrust sends chills down my spine, he keeps fucking me deeper and deeper..I feel my eyes rolling to the back of my head & another orgasm about to take over.

I [M] finished inside the annoying guy’s girl [F]

Restrictions lifted and my friends and I decided to go book an cottage in cottage country. It was mostly guys with a few of their girlfriends and some of their single friends. All in all, it looked like it was going to be fun at least. Lots of quarantine sexual tensions rising, I was hopeful something would happen.

One of the friends in my friend circle is a dick. Let’s call him Paul. I really don’t like him if I’m honest. Growing up he was a total dick, liked to bully a lot, and now surprisingly has confidence issues. But from time to time needs to assert his dominance and make sure we know he is alfa. Then a few hours pass and he tries to be vulnerable. He’s kind of weird like that. Only reason why we’re in touch is because of our mutual friends, otherwise we don’t have a relationship.

Paul brought the girl he was dating, they weren’t too serious or anything by the sound of it. I instantly recognized her. We used to play tennis together in high school and we kind of had a thing for each other, we’d give each other compliments a lot. Really cringey and dumb, but we were kids.

My first time with a trans woman [MF]

So as the title says this is the story about my first sexual experience with a male to female transsexual, so if that isn’t your thing I’d recommend not reading this story. I’ll call her Megan. Also if I say anything that isn’t the correct term or you find offensive I apologise, I’m not 100% clued up on all of this, so just leave a comment or dm me if I say anything wrong. I’ll try and remember to refer to her penis as her clit, and her asshole as her pussy because that’s what she liked me to call them at the time.

I first met Megan on a dating app and instantly saw how gorgeous she was, she had shoulder length brown hair and piercing green eyes. Nice plump lips and a cute button nose. She was about 5’4 and very petite, her legs and bum were nice and toned from working out and her boobs were about 34C and looked very natural. Obviously I was very interested in her when I first seen her profile and had to message her. I honestly didn’t expect a reply as I thought she was way out of my league, but to my reply she messaged me back within 5 minutes. We chatted on the dating app before moving to WhatsApp.

Teasing Each Other All Day [FM]

My partner has had a few very stressful weeks, just busy at work leading up to a big (online) event. Last weekend was the first weekend we have just to ourselves, so we decided to make the most of it. Saturday morning we woke around 7:30 and popped some edibles; an hour later, after going back to bed, we went outside to toke and drink some coffee on our patio.

He made breakfast, and we got ready to head out. It was so humid—the air just felt heavy, and the sun is hot—the kind of weather where you know you are going to be sweating no matter what.

He’s wearing a light pair of baggie shorts and t-shirt, and I’m in a long linen dress. Just easy, breezy. Pleasantly stoned, we decide to take a walk—maybe go get some granita at a pizza place in Little Italy. When we arrive, we order some granita and head to a nearby park to enjoy it. The park is just slammed with people—lockdown restrictions ended recently, so people are just out, enjoying themselves. We found a little bench to sit and savour the granita.

I Fucked My Therapist Pt. 4 (4/5)[MF][taboo]

I sent him a text the night he broke up with me professionally. I sent him a picture of me in Hello Kitty underwear, and he said “I think I’m going to like being friends with you.” God, I wanna cry thinking about it. The release. I wanted to see him as soon as possible. But with the pandemic going on, I knew the possibilities of seeing my still married former psychiatrist were going to be limited. So I got a room at the Chateau Marmont. “To write in.” But he could come over and have dinner with me, if he’d like. And he did.
I got a one bedroom suite with a living room and dining room. I felt like the ghost of Marilyn Monroe. I was impeccably groomed. Waxed, shaved, hair washed, make-up done, starved to death. I wore what he had mentioned in his story, the outfit I wore when I told him about my crush on him. The crush that wasn’t really supposed to be a crush. Just transference, remember? That’s what the videos had said. Something he was supposed to fix. But the outfit. Cream and burgundy plaid skirt, black ribbed Reformation top, black thigh high socks, hair in a 60’s half-up ponytail ala Brigitte Bardot. Underneath I wore black panties and a black lace bra that I knew he would see. I wanted him to see.
He showed up at my hotel door with takeaway dinner. To-go cocktails I wouldn’t drink because I don’t drink. I’m fun that way. It was the first time I had seen him in civilian clothes. Jeans, t-shirt. He looked even taller out of scrubs. I wanted him to push me against the wall of the hotel and stick his fucking tongue down my throat. I didn’t want dinner. I couldn’t have eaten if I tried. I only wanted his cock in my mouth.
We sat at the dining room table, awkwardly, picking at our dinners. I don’t think either of us were really all that hungry. I was too nervous, too fucking horny. He told me nothing was going to happen between us that night. He wanted to be good. He was still married. I doubted that. Why would he come to my hotel room if he wanted to be “good”? Couldn’t eat. Did a magic trick for him. It’s weird, but sometimes endearing. He was a bit of a nerd, and he liked it, watching me struggle to shuffle the deck of cards with my sweaty, anxious hands. We ignored our dinner, sat on the couch and looked for something to “watch.” He showed me pics on his phone of his dog, his friends, what his life was like outside of the office. We got closer and closer. His hand on my thigh, my hand on his thigh. Holding hands. I wanted him to kiss me, but again he said he wanted to be good. No he didn’t. He just wanted to make me suffer. Wasn’t that what he had done up until now? We got even closer. I smelled his neck as he held me close to him. I straddled his lap, and he picked me up and sat me back in my spot. No, he was going to be good. But still, his hands were on me, still he breathed in the smell of my hair. He was teasing me, and I would’ve done anything for him. In that moment, I would have done anything. I was his.
I asked if we could lay down on the couch, we could. Closer. I told him I was going to take off my clothes. I wanted him. And I did. I undressed for him until I was in those black panties and black lace bra. I laid back down next to him, and he couldn’t stop himself then. He put his hand on my stomach, sliding it down and into my panties, feeling my wet pussy for the first time. I could hear him groan with delight. He had me where he wanted me. I was literally in the palm of his hand. I turned to him and said he may as well kiss me now because his hand was down my panties. And he kissed me. Laying down on the couch in a room at the Chateau Marmont. He kissed me. It was happening. I wasn’t crazy. He had wanted me. It was more than a fantasy. It was happening. This was happening.
I asked if he wanted to move to the bedroom. He did. I was dizzy and stumbled my way there, balancing myself with the walls. I hadn’t really eaten much that day, and I was lightheaded from this fantastical reality. Fuck, I wanted him. We kneeled on the bed facing each other, kissing, as he took off his clothes. I pawed at his belt, and looked up at him for permission, he said I could take it off. His pants came off, and he was naked in front of me. His cock was beautiful and thick. I knew it would be. He puffed up his chest, like he was trying to appear buff for me. He was already buff. I thought it was bro-y, but fuck it. I was going to fuck my therapist. Finally. After all these months of fucking agony. My panties came off. We touched and kissed each other until he pulled me to the side of the bed. He was going to taste me. He looked at my pussy, and at me, and said, “beautiful.” He thought my pussy was beautiful. I had imagined him saying those words over and over again in my obsessive thoughts. My pussy was beautiful to him. And he licked me. He tasted me. Put his finger inside of me while he did it. I moaned and squirmed on the bed. I wanted to cum in his mouth so fucking badly, but all the Prozac I was on, that he prescribed me, wasn’t having it. I couldn’t cum, and I laughed it off and said it was his fault. He had done this to me. Put me on Prozac. His name were on the bottles I had packed.
He got on the bed, and I swallowed his cock, gazing up at him with my big, winged eyeliner eyes. His cock in my mouth felt surreal. It was everything I had dreamt of. Hearing him moan, tasting his precum on my tongue. I looked up at him, and he asked me, “so do you want this thing in you now?” I’m not even kidding. Those were the words he chose. I think I secretly knew then that all of this would fall apart. But I said yes, and I laid on my back as he penetrated me for the first time. It took my breath away. A few days ago, this man had been my therapist, and now his cock was inside me while his name was still on my prescription bottles. I already suffered from derealization and dissociation, and I floated out of my body once his cock was inside of me. I don’t remember much else. I do remember thinking it wasn’t as good as I had imagined. It wasn’t at all like I had imagined. But I was devoted to him, and I couldn’t care fucking less. I had finally made it. This was the hill I would die on. He didn’t cum. He said it takes a lot for him to cum. But I think he was nervous. A little freaked out. He had cheated on his wife with his younger, obsessive barely former patient. I would hope he was a little freaked out. But maybe I’m giving him too much credit. We cuddled. We talked, and then he was gone. I didn’t sleep much that night.
The next day, I didn’t do anything but write about it in my journal and lay by the Chateau Marmont pool listening to Leonard Cohen, hoping he’d text me. My life as I had known it was over. That day was the first day of the next phase in my life. A phase where Sean and I met again in the botanical gardens, we held hands, we kissed, and we wondered what we would do next. We talked about our future together. We met again at a beach hotel, at the alleged suggestion of his wife. For him to take a break, but he said that she probably knew I would be there. And we laid on the beach on a bed sheet, he rubbed sunscreen onto my legs. We ate Mexican food, and we made love and laid in bed talking for hours. Yeah, we made love. It was better than the first time. More intense. And I came in his mouth. And he came inside me. Then my husband left me, for reasons that had nothing to do with Sean, but our relationship together was the catalyst. It would’ve happened without him, but Sean pushed it right over the edge. Sean asked for a divorce, and his wife left for her hometown. And it was just us for awhile. After all those months of obsessing. After all those things he had said. After telling me there was a 99% chance it would never happen. After telling me maybe in another life. I was finally his. He told me he knew he was in trouble when he met me. Knew it then, but he tried to fight it. He liked my persistence and the playlist. It was the playlist that made him realize that this was different.
He suspiciously closed down his private practice. He said I didn’t have anything to do with it; he had been planning on it for months. Uh huh. He didn’t make as much money with a private practice as he would elsewhere. His friend, a lawyer, told him he didn’t have anything to worry about with me. He would be safe. When did he ask him? Right before he gave me his story and decided we should be friends. He knew what he was doing. My friend, the one who recommended Sean to me stopped, talking to me. I would learn months later that before Sean stopped treating most of his patients, she had confronted him about our relationship together, and Sean had accused her of harboring romantic feelings for him, too, and reacted as if she were merely jealous. I didn’t understand why she or anybody else would have a problem with Sean and I being together. To me, I had the power in the relationship because I had the ability to end his entire career. But no, that power belonged to him, too.