[FM] How I actually ENJOYED losing my virginity to an older, married co-worker (Long, teasing, vanilla, but almost didn’t fit)

*[I’m in my mid-20’s now but this is about how I lost my virginity. I’m sure that’s never been done here before. I hope you guys find it interesting even though it’s all completely true so nothing too crazy happens. As long as you don’t think infidelity is crazy. I think I kept all references to it above the dividing line. If you get bored by the long set up, the action also starts after the long dividing line.]*

__

Due to a combination of overly protective Catholic latino parents and having a relatively introverted personality, I made it all the way to 18 before I had sex. I’m aware it sounds conveniently like a porn. That’s just coincidence. The guilt from aforementioned Catholicism played a role too probably. I don’t know about other Catholic teenage girls but I never let it stop me from going right up to the edge of having sex with whatever boy I was attracted to when they took the initiative in trying to fuck me. I’d do anything except actually them. Soooo it was just very frustrating *(for them)* make out sessions and maybe oral for the one or two that I liked enough for it.

19 [FFM] I put on an erotic show with my sister for cash…

***EDIT: Link to Pic in comments***

I moved out on my own at 18. I’m a part time student aiming for a degree in hospitality management. I work part time for a major luxury hotel. My side hustle is dancing. It’s how I pay my bills. I started the summer after I finished high school. I got in at a good club with no experience because my sister Mary already worked there.

Nobody loves stripping. Anyone who claims to is lying to you and maybe their self. Sometimes I meet rappers or athletes and I like most of the girls and hanging out with them back stage. But there’s nothing sexy or fun about grinding your ass on a guy you normally wouldn’t spend 30 seconds talking to. It’s a shady gig, but it pays well.

And grinding my ass is originally now I made the most money. I got tips on stage. Typically dancing as a girl-next-door type, wearing all white or a school girl uniform and pigtails. But that’s all a show to sell the lap dances. Mostly I hate that part. Although sometimes it’s fun if the guy is hot or just shy and acts like it’s a real thrill for him. It’s the ones who leer or grab that make it a chore.

[F] Proving him wrong

Last night I decided to teach my bf a bit of a lesson. First a bit of a backstory, to set the scene a little better. We’ve been cuckolding for a while, it’s something we both enjoy, and helps me have a little fun whilst I’m away at uni. Seeing as we’re quite sexually open, it’s should come as no surprise that we watch a fair amount of porn. One of my favourite genres is interracial, however my partner isn’t the biggest fan. He will often say when watching how it’s all angles, and the old adage of black guys being bigger isn’t true. Anyway, back to last night.

I’ve been back at uni a few weeks, but haven’t really been out much, I always try and settle back in first and just get comfortable being away from home. Last night I went out with flat mates, just to a local bar. We met up with some friends of one of my flat mates, and just had the general kinda sporadic night out you’d expect from uni students. One of the guys from the other group and I got along quite well, and as drinks flowed the flirting started. I messaged my bf a pic of me and the guy in question together at the bar saying ‘maybe i’ll find out if the stereotype is true’ he replied with the expected response of telling me it wasn’t and to be ready for disappointment.

Fucking the Irish girl at work – long [MF]

Its been awhile since I posted my last story. So insanely busy, but I wanted to keep documenting and sharing some of my experiences. Some are probably wilder/better than others, but I can get to them.

This one was a lot of fun though. It happened a couple of years ago. I was 26, she was 23. I had taken a job over the summer period at a bank during the semester break. It was a really dull job, pure data entry. Take loan applications in paper form, transfer all the data onto the system, and repeat. It was the sort of job that after awhile you could just stick headphones in and listen to music and do it on auto pilot. Not challenging, but perfect for something over the break. Because of the nature of the job it seemed to attract a lot of travelers, people on short term contract. The office, or at least the department, was filled with a pretty big mix of all sorts .. which was nice hearing all these different accents.

[MF] Went down on a woman while she was on the phone with her husband

So this was a pretty out of character for me I’m usually 100% against cheating and usually don’t pursue married women. This was about 9 year’s ago and I was 23 at the time.  This was without a doubt the hottest experience of my life. 

So I was out drinking with my friends and we were sitting at the bar next to a group of women and I happen to be sitting next to this gorgeous lady. She was shorter than me about 5’4″ I’m 6’0″ had long dark hair with subtle highlights. I have a hard time placing her ethnicity I would guess a mix between Asian and South American. She looked amazing, the perfect amount of curves in all the right places, wearing a tight dress. 

As the night went on we would chat once in a while with each conversation got longer and longer. Her name was Jen and she was hanging out with friends she hasn’t seen in a while. Later in the evening both our groups filtered out and our conversations became more and more flirtatious. At one point I decided to go for it, I place my hand on her bare thigh a whispered “do you wanna get out of here?” She smiled, showed her ring, and said she’s married. I took my hand off off her leg and apologized saying I didn’t notice.

Married couple at a sex club [MF]

My wife, Meghan, and I have had a great sex life in all our years of marriage. After kids things didn’t stop, but there are quite a few barriers to everything we want to do. Traveling as a family is a lot of fun, but good sex requires a bit of creativity on the road when the whole family is confined in a van or hotel room for extended periods of time. Sex at home is a bit easier. We can’t have long sessions on the kitchen counter, backyard or anything, but locked bedroom doors kept us each able to satisfy the other without fear of interruption.

However, every once in a while we can negotiate with the grandparents and get a few days for a kid free vacation. Last year we were able to swing one of those trips. I was traveling to a new city for work and Meghan was going to come with me a few days early so we could have some fun together in a new place.

Bo and Me, Chapter 1 — It (f, mast, nosex)

*Turns out the reason these kept getting automatically deleted is because I derped and put links in the OP, lol. Link to Chapter 2 will be in the comments once it’s up.*

# Chapter 1 — It

I love the library. We go almost every Saturday — Mom, my little sister Bo and me. Even Dad tags along sometimes, but today he’s gone fishing with friends, so it’s just us girls.

The library’s almost on the other side of town, but since it’s a small town, it’s just a twenty-minute walk, most of it through the park. We cross the river twice, stopping on the bridges to look out for some fish of our own so we can tell Dad later. Mom’s really good at spotting them “sitting” in the stream. Sometimes it takes Bo and me half a minute to see them even after she’s pointed them out.

They built the library on the top two floors of an old monastery. I mean really old — it was built in the year 803. Last year, there was a festival celebrating its 1,200th anniversary. They had a booksale and a big cook-off, and at night they played movies on a large screen in the garden.

Ana in the Park [MF] public

Ana was my first. And if you read the previous story you know I was dumb and thought I could do better.

Ana was 19 at this point, Brazilian and curvy in the best way. Round ass, decent tits and olive skin. Her hair was long and always done up in a “come mess it up with me in bed” kind of way. She was just all woman and knew what she wanted even at a young age. She had a confidence about her that I actually wouldn’t see for years to come.

Fast forward now to maybe 9 months or more since I ended things with her. I don’t recall who contacted who. But we had agreed that I would pick her and go for a drive and just talk.

It was rather uncomfortable in the beginning but she looked amazing getting into the car. She had her usual super tight jeans and a loose shirt that cut low into her cleavage.

It was near the end of summer and she was tanner than usual. I knew she loved to tan nude (where or how she was able to do this I have no idea) and all I could think of was her perfectly tanned breasts.

A [MFM] from my GF’s past

So my gf has every dirty picture that has ever been sent to her saved on her computer.

She knows I get off on knowing about her past so we occasionally go though her collection of nudes and she tells me some stories about the guys. (she’s been with a lot of HUGE, like monster cocks).

Yesterday she told me the story of Ryan, the only boy she ever dated that had a small dick. Ryan was nice but couldn’t ever get her off or make her happy sexually. After weeks of trying she convinced Ryan to have a MFM threesome with her to “spice things up.” The only condition was the other guy had to be from a different school (they were high school seniors AND 18 YEARS OLD at the time). My GF knew about a guy named Jake with a massive dick from the next town over from a friend who had dated him (and openly bragged about Jake’s dick).

My GF had hung out with Jake as part of a friend group several times. They were friendly and she knew he would be down, no questions asked.

S.M.O.M.S: Ingrid, Ch 7. [Fm, reluctant, oral, anal, slow, mast, mdom]

S.M.O.M. (Ingrid) by DiscipleN

 

 

Chapter 7

 

That was my low point. My spirit was crushed. I would have fucked dogs and homeless people if my son had told me to. That night, I woke up Garrick and cried in his arms until sunrise. He took the day off. I didn’t answer his questions until mid-day.

“I’m not going to tell you what happened, Garrick.” That was my answer. “It happened. It was my fault and only my fault. I can’t make up for it. All I can hope is that time will help my mother to forgive me.”

“Where did it happen?”

“In the house, somewhere.” I told my husband.

“Where was Andrew?”

“In the hall bathroom.”

“Did anything get broken?”

I glared at him.

“Yes. Okay.” He backed away, releasing me. “You and your mother are unlike any other family I’ve met. I won’t ask again. You know I will do anything to help.”

“I know. You’re already helping.” I sighed, already missing his arms around me. “I’m afraid helping me will only hurt you, at least for a while.”