[B/S] A Familiar Connection – MF, Slow Buildup – Part 1 of 4

(As always, please pardon the grammar errors. This chapter is pretty tame, but it’s setting the stage for our fun.)

I woke up and checked my phone, reviewing the new e-mails in my inbox. One e-mail was from the resort hotel that I was scheduled to visit in three weeks. I reluctantly opened it, already knowing what it would say: “we’re sorry, but with the current COVID outbreak, we’ve cancelled your stay.” Although this was expected, I was still disappointed. On the positive side, I now had a week of vacation scheduled which I needed to fill.

But before we delve deeper, I should provide some background. My name is Harry, I’m a mostly-heterosexual 34 y/o man living in San Francisco. I’ve lived in the Bay Area most of my life, but have never settled down or gotten married. I enjoy the city’s active social scene, and the adventurous playmates I’m able to spend time with. Since my girlfriend and I broke up last January, I’ve been in a bit of a sexual lull because the swinger clubs are closed (fuck COVID). I had hoped to meet some people at the resort, but that’s no longer an option.

My gf gave me the most stress relieving sex ever [MF]

This is my first time posting here but I wanted to share my story

So I was having a really tough day at work. You know the usual with the boss getting on my back and it being extremely busy. So im talking to my girlfriend about it and she told me that she would try to make my day better when I get home. Usually she does things like play video games with me, massages or a nice movie night. But this was something different.

When I was on my way home she told me she had a surprise for me and that she couldn’t wait to show me. When i got home and I opened the door to her sitting on the living room couch under a blanket. When she got up she was wearing red lacy lingerie the opens up on her tits, pussy and ass. The honestly turned me on pretty fast because she had big round tits, and nice fast ass and a great body. She was wearing the shiny red lipstick that she wears when she goes out.

[MF] Truth or Dare turned into a Cucking session.

Backstory: It was my friends (M) 18th Birthday, I (M) was 18, his G(F) (at the time) was 18. We had a little get together, a fun day, Bowling, Laser tag etc. And then had a few drinks. After the rest of our party left we went to his to chill, me, him and his gf. We got a few drinks in and we’re having a bit of fun. We decided to play truth or dare.

The game: So it started off pretty innocent, taking it in turns, the first few turns were just truths, “Have you ever stolen?”, “Have you ever cheated on a test?”, “What do you think of Cats?” Etc. Harmless fun.

We got a littler drinker, and the truths got a little more risque, “Have you ever masturbated to a girl in college?”, “Do you find my mum attractive?” And the big one, from my friend, in a way to try and humiliate me in front of my GF (Rumours were I was tiny) “How big’s your cock?”. This is where things got interesting.

Poker Night

*It all started with a Royal Flush.*

Naomi grins at him like the Cheshire Cat.

*No one ever gets that hand. Ever. The odds are so slim. But somehow tonight Jake managed.*

Naomi, the girl he’s spent the last ten years spoiling, is no longer grinning at him.

She’d told him before he left that she was going to meet the girls. She’d been giddy with excitement all day. He’d said that was fine, he was playing poker with the boys.

*He should have seen the way they smirked at him. “Sky’s the limit,” is what Paul had said.*

He looks down at his knees. It’s the easiest thing to do. It’s bad enough hearing the laughter.

*He thought there was a chance to win big money. He thought Brad might even put his watch on the line.*

*He had been so very wrong.*

A hand grabs his chin and lifts his face.

“You’re missing the show,” Jake frowns as he holds Tim’s face firmly.

Tim tries but he can’t roll his eyes enough to avert his gaze. Naomi is dancing around on the rug. Paul, Brad and Liam are sitting on the sofa cheering her on.

Classroom Fuck-Circus [Mind-Control][Anal Toys][Free Use][Orgy][Humiliation]

In my senior year of high school, I stupidly enrolled in a “Writing the Essay” college prep course. The class was comprised of four guys, counting myself, and six girls, all of us seniors. Our teacher, Mrs. Floyd, droned on wearing a stupid grin about what to expect our freshman year and how important these skills would be. I paid a third of attention, my focus divided between ogling at my female classmates and tinkering at a certain device under my desk.

My step-father worked at the NSA, and always kept his work squirreled away upstairs. By happenstance, I went to look for a pen in his office and stumbled across documents pertaining to radical sound research. I took a picture of the papers on my phone and disappeared into my room. The analytics described a device that could subliminally message a massive group of people. Using my relatively strong computer skills, I devised a smaller device that would work on a select group of people, say ten, but with greater effects.

The Pregnant Woman on the Ferris Wheel [M/F] [Public] [Oral]

It was a sweltering day in the middle of July, and FunWorld was packed. I was accompanying my girlfriend Lisa and her parents, who annually met extended family here for reunions. Lisa and I had been together for a little over three years. These familial gatherings were a fairly exhausting exercise, putting on a nice face and talking about my job or whatever other trivial tidbit to 20 different 2nd tier cousins. Standard obligatory boyfriend stuff, but I was still relieved when Lisa and I could break off and do our own thing.

The sun was hanging sexily low in the sky, bathing the amusement park in that magic, yellow-orange, late afternoon summer light. It made Lisa’s platinum blonde bob glisten. We got a funnel cake and sat near a directory sign that laid out the major landmarks of the park.

“What do you feeling like riding?” I asked her.

“Ooooh The Devil’s Dirge!” she excitedly suggested.

This coaster was the park’s newest attraction: one of those towering, loop-filled, highest-allowable-speed-and-height kind of monstrosities.

“Yeeesssss! Think the line is still super long?” We’d considered riding earlier, but the wait was around 3 hours.

The Auntie Story #1 [FM]

As promised u/deodek and u/Azzurri1 on the latter’s contribution [https://www.reddit.com/r/sexstories/comments/hptjzn/my_sexual_exploits_all_real_experience_1_my/](https://www.reddit.com/r/sexstories/comments/hptjzn/my_sexual_exploits_all_real_experience_1_my/)

– here is the first part of *my* auntie experience. Further details regarding follow up at the end of this story.

**

This experience is written from memory. It happened decades ago and my memory may have altered a few things to make it easier on myself. Technically my aunt did nothing wrong and age is not an issue where I live. With regards to the latter I will not be specific other than I was a teenager. You can place the actual age where you want.

*Quick background (or jump to the **):*

My uncle lived with a new girlfriend Lisa who was about 10 years younger than him and about 11 years older than me.She worked in pre-schooling and as our own school had a week each year for us – as pupils – to try out different trades, I was offered a week at her job.

At the time of this episode my uncle, Pete, and now aunt, Lisa, lived in a flat with a master bedroom, a hallway, a small bathroom, a kitchen and a big living/lounge room.

[Group][MF] Had an unexpected somewhat orgy with former college classmates

Long post. My (25M) English and grammar are not the best so sorry for any errors. This happened last week Friday and the decisions made were definitely not the best. All the names have been changed and since none of them use Reddit I thought I’d post here because I just had to share this crazy story. For a bit of background, I live in South Africa and in my experience (I’m black btw), people are not too open about sex here as it is, let alone group sex. The idea of it was just a fantasy I had had and was sure would never come to fruition. My classmates and I were closer than normal and were somewhat friends but not really. As far as I know, none of us had been sexual with each other the entire time we were in university/college. The group was me and 3 other guys and 4 girls and most of us had not seen each other since graduation.

The first time I [M] fucked my [F] girlfriend in the ass

Obligatory but this was some years ago. My ex and I were both 21 at the time and had been dabbling with anal sex but with no success. This was mostly because of our inexperience at the time with anal foreplay. She’d always reluctantly plead in previous instances to go all the way but I’d always shut it down when her body language showed physical discomfort.

Flash forward to the day it finally happened. We were at a holiday party at my parents’ place and because it had been a while since I’d lived there, they converted my room into a game room. That said, a few drinks in we moseyed upstairs to what used to be room and started going at it full tilt. Next thing you know we hear footsteps coming upstairs so we retreat to what used to be my closet and close the door before anyone comes in. The parents were playing poker downstairs so my mom sent the teens up to play pool/Xbox, etc., leaving us stuck in the closet.

[MFF] The Saga of Sally – Interlude – Meat in a Middle Aged Sandwich

(Welcome to the Saga of Sally. Except it’s not Sally this time.

I am recounting my long on-and-off relationship with a girl called Sally. I recommend starting from the [start](https://old.reddit.com/r/gonewildstories/comments/hsqikr/mf_the_saga_of_sally_cumstained_jeans/) – each piece will link you to next part at the end. However since I am working through my life chronologically occasionally they’ll be “Sallyless Interludes” if I think there was a sexual encounter worth writing a story about. This is one of them. **There was no cheating on Sally. I could never cheat on that absolute goddess. At this point, we had broken up since we were living in different countries.**)

This is just a short one.

Those of you who read my first story about Ana will know that I have some experience with age gaps. I’m embarrassed to say that this wasn’t the biggest age gap I had as a sexual experience. I was certifiably a depraved young man that would fuck anything.