My Saturday Night: my virgin ass gets fucked and stretched out for the first time…and i loved it [FM]

Part 1: The Greeting

I stand by my back kitchen door, lights off, dressed in a black fishnet teddy covered in a cheap maid costume with red high heels, waiting for my guest to arrive. It’s been months of dirty messages and pictures being exchanged, months of talk about what we would like to do to eachother followed by masturbation shared through snapchat; I’m not sure what’s going to happen but I know I’m getting fucked in the ass for the first time tonight. 

[M] My very interesting anal masturbation experience which someone almost walked in on

I wanted to masturbate anally and my didlo is pretty long but I was bored of a normal position and wanted to try something new for deeper penetration. Put up a dildo behind me and wedged it between two boxes stacked on top of each other (no suction cup) and used pillows below my knees to adjust the height and just went doggy style at the dido moving my hips back and forth. Wanted the dildo to go deeper and this seemed like a good position for it (turned out to be an excellent position for maximum deepness). Used a latex glove’s finger to cover the thing as a condom and coconut oil as lube while doing so. Result, absolutely no regrets.

My girlfriend limited the amount of times I could finger her ass so I made it count. [MF][Anal]

A bit of background, for a long time my girlfriend Rebecca and I couldn’t have vaginal sex so we made up for it by doing a lot of butt stuff. You can read my previous post for more back story.

I love fingering Rebecca’s ass and she likes it too. I still do it quite often but there was a time when we first moved in together that I went overboard. We were fucking all the time and I would finger her ass all the time even when we were cuddling watching tv or just lying in bed. It was fun at the beginning and she was loving it too but after the first week the magic started to wear off a bit.

So the next day, she said I needed to cool it with how often my finger was ending up in her ass. I told her that was fair because I had been going overboard a little. She said that she was going to give me a limit of three times a day that I could do it and to “make it count”.

I just let a random guy from Grindr take my anal virginity [MM]

inb4 ‘you should have used protection’ etc etc, but I couldn’t sleep and I felt SO horny and experimental that I just let a guy from Grindr book me a taxi to his – when I got there I immediately stripped off, he spat on his dick to lube it, and he fucked me. It kind of hurt, but he wasn’t too big, and it felt good too – and he came inside me. I’m now at home and I’ve got his semen spilling out of my butthole. It’s so hot, not gonna lie.

Taking Mckenzie’s lesbian virginity [FF] (xpost from stupidslutsclub)

So awhile ago I went to my friend Emma’s birthday party. For those who don’t know Emma is one of my best friends and is largely a part of why I am the way I am today. She is the one who pushed me out of my shell and forced me to get with my first ever girlfriend.

We have always been close and shared basically everything together. We would always tell each other our dream what’s going on in our lives, our dream, fantasies ect. Even though I’m a slut with most of my current friends she and I never have had a physical relationship. There are just some people that though you like you don’t really think of getting together in that was you know?

The reason I’m telling you this is because being at her party was the last place I expected to be meeting some girl I would soon be fucking. The party was fun but pretty laid back and after awhile Emma and her boyfriend (Who I introduced her to by the way. Don’t say I never did anything for her in return) Introduced me to this cute girl Mckenzie.

Threesome Rules [MMF]

This is part two of my threesome in Las Vegas last weekend with Penny and Pat. It is written by Penny….

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As I begin to write about what happened when the three of us got inside the hotel room I realized that it seems like it was planned or staged which in a way it was. In the weeks leading up to the trip the three of us spoke in depth about the ‘rules’, our boundaries and our turn ons. Although, after the three of us got along so well in the pool, and Dave’s experience I think it probably would have gone the same anyway.

Having an extra guy has been a fantasy of Pat and I for years. We’ve both spoken about it a lot. For me, the idea of watching Pat with another guy is probably the hottest fantasy I have. For Pat, watching me with another guy as well as having me ‘spit roasted’ (Pat and a guy both fucking me and me sucking the other off) is his fantasy. And… Pat

I think it shows how amazing Pat and I are together when both our fantasies are of the other person.

Cheating With My High School Friend [FM, Oral, Anal, Cheating, Cum Play)

This is a partially true story, however I make it change a little bit to make it more readiable

Its long because I want to keep my fantasies and past experiences on record.

*

“What do you mean you cannot be there in that day?” “Sorry darling I cannot leave work until Wednesday”

Me and my boyfriend arranged that beach vacation one month ago. It was already just for 5 days and he already told me he cannot get out from work in the first two days. I was not angry but confused about what I’m going to do. We already paid the hotel so we decided its better I go early and stay for 2 days until he come. So I hit the road early on Wednesday morning and reach Antalya in a hot afternoon. I quickly chekced in and wear my bikini to head to the beach. Even I’m a little chubby I always feel good in bikini, feeling fresh air on my ass cheeks and my boobs jumping slowly in each step. I get out from building and when I’m really close to beach I met with Cenk. A friend from high school. I remember him being a silent boy who is good friends with everyone but still with low grades.

A date with domination [MF, Mdom, anal]

She stepped into the shower and let warm water bubble over her neck. It was unusual for her to be home first, although the directions she had been given were quite specific. Her thoughts lingered on his message. Only a week before she would have considered it most unusual, but the events of the last few days had introduced a new and exciting perspective to their relationship.

Earlier that week something inexplicable had happened, something so strange it felt almost dreamlike. The following day they awoke, unsure if had really happened. He described the experience as a trance. Some part of him that had always existed in his subconscious but never truly manifested itself. It took control of his body and spellbound he acted upon his darkest urges. The devil inside him dominated her, animalistic, used her for his satisfaction. That encounter prompted a rediscovery of her kink for domination and her appetite lingered on, unsatiated. The results were electifying. All she could think about was that evening, replaying over and over again in her mind.

First anal with my ex [MF]

My ex-wife and I had a lot of problems, but none of them were in the bedroom.

First, the usual descriptions. My ex is a natural redhead, who, throughout our time together, weighed about 100-110 lbs, and has B to small C cup tits and a decent ass. I’m a little heavier than average, with an average sized cock. We usually had pretty intense sex, often lasting 1-1 1/2 hours with multiple orgasms for her. Since I am both a gentleman and a pervert, my bedroom rule is if it feels good, do it. She often got nervous trying new things, but once she got over her initial nervousness, there was very little she didn’t like. This is about the first time we tried anal sex, which became our favorite thing for a straight week.

Due to several reasons I won’t go into, my ex had to have surgery which forbade us from having any kind of vaginal intercourse for about a month. My ex, being extremely horny, did not take this well, and decided it was time she give into my desires of “more than just a tongue or finger (and she loved a tongue or a finger, but was nervous going further).” She was determined to be penetrated during the month, and I was only too happy to be the one to do it.

We fucked in her car surrounded by a crowd of people. [MF]

To understand a little better, you should read [this one](https://www.reddit.com/r/gonewildstories/comments/8rhk13/taking_an_old_friends_virginity_one_summer/?st=JINLBLFV&sh=bd875fc5) first so theres context.

Me and Heather had been at it for about a month now. She knew what she liked. I knew what she liked. At this point we had done pretty much everything minus anal. We fucked in a pool, jacuzzi, the shower, her house, my house, other peoples houses, but tonight would be new for both of us. I had a show to play. I was filling in for a friend of mine who had knee surgery so he couldn’t play drums for 6 weeks. Not my style of music, but we go back and I said I could fill in while he’s out. Heather had never seen me play live before so she asked if I mind. Of course not. I play in front of strangers all the time.