I remind my best friend of the time she watched me fuck my girlfriend, and get rewarded with a cumshot [Group]

The following is a follow-up to [Cuddling with my best friend and my girlfriend gets me horny, which I satisfy by orgasming while locked around my best friend’s body [Group]](https://www.reddit.com/r/gonewildstories/comments/du8bwy/cuddling_with_my_best_friend_and_my_girlfriend/). This happened two months ago, when my best friend Kaitlin and I were planning to go for a socially-distanced walk together. I’m going to try something new, and rather than write a narrative I’m just going to transcribe our texts. Quotes are Kaitlin, non-quotes are me.

So I just chitter-chattered with Emily.

And she says that you’re welcome any time (of course lol) do long as I get cleaning done before we go for a walk.

IDK how much time you have / want to spend with me.

> Oh how delightful would it be if you lived on the first floor and I could talk on the phone while watching you clean in a French maid’s outfit ?

> But back to reality

Bold of you to assume I’d want you to watch me on my hands and knees in any sort of outfit at all ?

> Ahaha is it actually so bold?

[MF] Met a Slutty Teacher During the Pandemic

Skip to the *** to skip the back story

COVID has fucked my sex life up until recently. If you’ve read any of my past posts, you know that my main source for sex is my work travels. Not only did the pandemic end my work travels, I decided that living in a downtown highrise wasn’t the best for me anymore and bought a house. Since all the gyms were shut down, I started running through the neighborhood and lifting weights in my garage.

Having had no sex since the pandemic started, I caved and about three months ago I decided to try the hookup apps again. I was glad to match with a few people, including Andrea, a beautiful blonde 2nd grade teacher that lived in an adjacent suburb. We exchanged phone numbers, some casual messages, and SFW photos, but I could tell she was (rightfully) nervous with the pandemic going on. I was too.

Losing my [M] virginity to flatmate [F]

I am in my early 30s and I am from India. I wanna tell you the story of losing my virginity at 23.

I was dating this girl (lets call her Shalini) from Chennai during my bachelors and we were in love. I dated Shalini for more than 5 years but we never had sex (we both were virgins). There was all this cultural barriers like “we should respect each other” and “we should only have sex after marriage”, etc. and I was naive to believe/follow all this.

After graduating and working for few months in India for an IT company, I moved to a European country for my masters. She moved to US as she decided to do her masters there. After she moved to US, we both became really jealous and we started making each other’s life miserable. Ultimately, we broke up when she told me that she had slept with a guy (a senior from our college). I was broken and I was in depression for 6 months. 

I [F] gave my master [M] his first rim job in a public park

Re-posting from another sub since my master and I met up in the same park today, and both reminisced about how this was one of our best experiences together.

———

For the past few years, I have had a master in my home state. He and I grew up together, and I had an unrequited crush on him in high school. We kept in touch through college and after, and we would talk about how badly I wanted him to fuck me. I am technically a virgin, so he was always wary of being the dreaded “first.” As a compromise, he offered to spank me one night, and eventually I turned into his pet.

Ever since then, we would occasionally sext while in separate states and hook up when we were together. I have been training my ass for him to fuck eventually, and I love sucking his dick. We have talked about our fantasies to each other—including a threesome and me licking his ass.

[M26] I got birthday sex from my ex[F25] on my way home from my birthday party [MF]

So for those of you who follow my posts, this is the same ex who dressed up as Harley on Halloween a few stories ago.

So as per my title, this took place on my birthday a little while ago. Was a great night, and was surrounded by all my friends and coworkers buying me drink after drink. That night my ex was running late. No biggie I told her, I knew she had to work. The night continues with a few pool games and she finally shows up. At this point I’m at least 12 shots in and am planning on calling it a night soon.

One round later, I do and everyone begins to leave. We are the last 2 in the bar together and share one drink together before we call it night. Now to get back to her place which is closest we have to cross this park. Not exactly dense woods but there is enough coverage and rarely anyone goes there at night past 10. She apologizes again for being late to which I again reassure her it’s totally fine and she responds “I wanna make it up to you”. Now when she said this i immediately assumed she meant when we got back to her pace which, hey……I’m down, but it didn’t workout that way.

[F] 29- Asian – photographer

I am a terrible story teller, so hope you bare with me.

this was just pre-covid my bf brought up that this was one of his fantasies.

I have been always self conscious about my body, but as we discussed it more, i understood his reasoning and decided to take it a but more serious.

He has done some photography work and know a female photographer who he worked with before. He reached out and luckily she agreed! and for free too! it was something that she wanted to creatively challenge, but never had an opportunity.

cutting to the day of the shoot. I was nervous as heck!! i had stayed over the night before. woke up. and he says “i don’t want to have a hard on during the shoot. It will be super embarrassing. Can we do it now before she comes?”

so… we had a quickie. a good one. we take a shower and get ready for her.

about an hour later, she arrives. we chat! she is such a sweatheart. brought coffee and timmies to ease us in and make us feel more comfortable, which totally helped.

I [F] Cheated on my Boyfriend with a much older [M]an [FM]

Told this story to a guy I met on Whisper, he told me to post it here so I will. I’ll add updates every so often as well :)

Backstory: I’m Sarah, 21F originally from Ireland but living in America, blonde hair, blue eyes, B cup tits, 135 lbs., been told I have a thick ass ;) On this occasion I was wearing a tank top with an unzipped jacket and black leggings with a thong underneath. I have a boyfriend that cheated on me with my sister once, I gave him a 2nd chance but I’m going through a slut phase lately so I think it’s time for revenge. Anyway onto the first story.

Story: I was out with my friends on a Saturday night, we left my boyfriend at home and went bar hopping, we have a different designated driver each girls night out, so when I say we drove I mean she drove I’d never drink and drive. After a few bars I was decently drunk, not enough to cloud my judgement but enough to make me a bit more fun than I usually am. This bar was pretty packed even with covid being a thing. I was sitting at the bar with my girlfriends (on the 2nd to last stool with one seat left open to the right of me) talking about different topics like work drama, office romances and boys (typical girly gossip).

My rude customer fucked the shit out of me [F] [28]

[https://imgur.com/HcvCGpB](https://imgur.com/HcvCGpB)

Hi loves, Nina here! If you’re new to my posts, here’s a quick recap of who I am. I’m 28 years old, Lebanese and I’m a sex worker based in Toronto, Canada and I recently separated from my ex-husband after a terrible falling out. I never spent any time in the work force and finding a job in the pandemic has been a challenge to say the least, especially given that the jobs most suited for my qualifications (waitressing, retail, etc.) are tough to get into in the current economic climate. As a result, I took up sugaring, followed by full on escorting to ensure my needs are met. 

I used to get the majority of my clients through various dating sites, but lately have become increasingly reliant on clients in and around my neighbourhood and have managed to build a fairly decent book of returning clients, with a steady flow of new ones. Most of my clients are relatively vanilla, in that there’s the occasional spanking, hair pulling, etc., but nothing too unusual. I tend to not write about these situations, but rather write about instances where I felt the strongest emotions – whether it be happiness, anger, sadness, fear, or of course, sexual arousal. This particular story is of a recent encounter with a client I had seen once previously.

[F] My (19F) First Photo Study

Sometimes I like to be the center of attention… It isn’t often but every now and then I get that itch to just have eyes on me. At 19 I attended a university that was across the street from an art institute full of bustling future artists and baristas. They taught what I guess people consider a renowned photography course so there were tons of students wandering around this side of town photographing anything they could. Every year though there would be a human anatomy study that was worth a large chunk of whichever semester you took it in. The human anatomy class was well known for having a grading curve that started with the photographer taking mirror shots at the bottom, and having raw nude photography of women at the top. I guess it was to weed out the slackers and to praise those that put in the effort. This caused many sleepless nights for these students due to the sheer difficulty of finding volunteers. Well, at least it did until I came along.

 

[F] The first time I had sex with someone other than my boyfriend… it was incredible.

Going to write this while it’s still etched in my mind, just gonna be straight up honest here. I’m writing this for my own masturbation material so it’s gonna be pretty explicit, it is true though. Fair warning, this is long.

Small bit of context. Boyfriend of 11 years dumped me with no explanation, we were each other’s first everything’s so this was all a new experience. After he left me I went to a hotel, went on tinder and found the first guy that caught my eye and invited him over, he quickly accepted. Also, this happened about two weeks back.

Once he arrived we said our hellos and all that, after a while of small talk I told him my situation so he’s aware, he told he knows I’ve only had sex with one man and I’m in a the middle of a breakup etc and if I want to back out or just watch a movie we can do that. I said no, I was determined to follow through. I was actually a little offended that he was talking to me like I was innocent so I began to feel up his crotch and I straddled him.