[MF] Losing my virginity late and finding out that sex is not that easy

At the time of this story, I was 30 years old and a virgin. I had never had a relationship (still haven’t actually) and also had never kissed or even held hands with a girl. This was primarily because I was a bit shy and had never really put in much effort in trying to get a girlfriend. Also, I wasn’t meeting that many people, so was never in a position where mutual interest could have led to something more.

I had just moved to a new city and country, so I was attending various meetups in order to meet some people in this new place. I met her at one such meetup. She was a 24 year old girl from Eastern Europe, also fairly new to the city. She had dark blonde hair, and was slender and very tall. I’m 6 feet tall, and she was only just a bit shorter than me. We talked for a bit throughout the evening, and before she left she came to find me to tell me something. I’m not exaggerating when I say it went something like this:

[F]uck teasing [F]riends (part 2)

If you’ve read my stories before, you know I have this friend, G. [(Here’s the story so I don’t repeat myself)](https://www.reddit.com/r/gonewildstories/comments/7nrq5p/fuck_teasing_friends/) Over the past few months, G and I have been spending more time together. She broke up with her boyfriend (huge shocker) and needed someone’s shoulder to lean on, someone to drink with, and a nice pussy to rest her warm mouth. I mean place… No, no I didn’t. You could say I was all that and more for her. This is the first time we did anything (we’ve been doing some things)

So we were just hanging out in her bedroom, watching American Horror Story. Of course, the topic of sex came up and she was talking about how her ex-boyfriend loved missionary so much because he got to see her face when she came. I thought it was a bit cheesy but she lives for that shit. Eventually the conversation got back to sex on the screen as I took a swig of rum she brought up for us to enjoy. Coconut flavored. It’s sickeningly sweet directly from the cup and I remarked on this right up until I saw her get up from her side of the bed and climb on top of me. My back resting on her headboard, she looked me directly in the eyes, flipping her brown hair over one shoulder.

[MF] anal breakthrough last night

I’ve been super interested in eventually pegging my husband, but he’s not there and may never be. We had an… incident a couple months ago. I’ve started occassionally rimming him as part of foreplay and spend a lot of time using my mouth on other than just his dick, and his reactions are always so sexy and I’m usually dripping wet only a few minutes in. One night, I was going at him with my mouth and tongue and tried to escalate it. I grabbed some lube and worked my finger in, but was unsuccessful in finding the prostate.

I ended up just thrusting my finger in and out of his ass while giving him head, and for awhile he seemed to be enjoying it but eventually said it was starting to hurt. I pulled out, washed my hands and climbed on top and finished that way. Well, a day or 2 later, he ended up with a massive extremely painful hemmeroid. Like, limping and walking funny, miserable, couldn’t sit down or stand up, moaning and groaning. I called it his”man cold of the ass” because he was so over the top about it. I have had hemmeroids off and on since our first was born, and he’s 12. Roids are not a big deal and should not impact your life to the extent it did for him.

Eavesdropping [FM] [M]

“I’ve always wanted to listen in” he said.

“Like conference in on phone sex or like listen on the phone to people having sex?”

“The Latter.”

I thought about it for a bit. I was definitely interested, and it sounded like something my husband would be into too.

“Let me ask Adam and get back to you. ;)”

—-CONTEXT—–
So I am a late-twenties bi woman, married to the world’s sweetest guy, and we’re not monogamous. I’m pretty pale, curvy, about 5’7, with hazel eyes and really curly brown/auburn hair. Pierced tongue and nipples, 2 tattoos with more to come. Short torso, long legs ? Adam says I have an amazing butt but he’s biased. 38 F cup (GD bras are so fucking expensive)

Adam, my husband, is about 6′ and has the most beautiful stormy blue eyes I’ve ever seen. He’s also got really curly brown hair which is pretty long right now. Average build, and average cock. I can swallow the whole thing if I try, which he’s pretty thrilled with, and I’m definitely more interested in girth than in length (Story for another time).

My [F]irst Affair: The Soccer Player (Part I)

[Note: With the exception of changing his first name, everything else in here is 100% accurate, with absolutely zero embellishment or alteration.]

As I approached 30, I had made the decision to get out of my marriage. My husband and I had grown apart. We weren’t getting along well at all, there were old resentments that constantly came up, we did almost nothing fun together, and we had gone from nightly sex to maybe once a month. I felt completely taken for granted by my husband and the relationship was dying, so sit seem

I’m fairly curvy with big boobs and ample ass. Through running and yoga I had gotten myself into phenomenal shape that spring in anticipation of being back out on the dating market by the fall. I looked good and I knew it.

In June I was out with friends for a bachelorette party when a guy approached me. Dylan had dark hair, green eyes, and very obviously was in great shape. He was funny, confident, and flirty, and I loved his Irish accent and his Dutch soccer jersey. So we chatted for a while. Dylan mentioned he was a teacher at a suburban high school about 30 minutes away. Eventually my group of friends was moving on to another bar, so he asked for my number. I didn’t want to give it out in front of my friends, so I told him I was married. Dylan visibly was crestfallen to hear this, but smiled mischievously at me as we said goodbye.

[F] I help Instagram models escort

First off, I’m a female and I run a real business… producing porn.  I was first hired as an office worker and learned the business from the owner.  He was going through a divorce, and offered to sell me the porn company.  That’s how I got into it.

But as a side gig, I help Instagram models escort and be sex workers.  I help run their social media messaging.  You can probably imagine the amount of solicitations and ‘date requests’ these models get.  

I started by accident.  I have a model friend, and she was already doing this herself.  I’m pretty good on social media, and asked if I could help curate her posts, drive more followers, likes, etc… That’s when I learned that she escorts on the side and that’s when I started to help in that regards.  From there, I met more of her friends, who were in the business, and thus started working with them.  Referrals so to speak.  Like a snowball running down the mountain, all of this gained momentum and now I’m working with dozens of girls.

[MF] Opening Up pt2

[Part One](https://old.reddit.com/r/sexstories/comments/a9zstu/slow_openings/)

I could not get that night out of my head, the next Day Kelly left to go to her parents. I walked her out and Kyle was no where to be seen.

“I will see you Friday babe!” She said as we locked lips one last time, my hands went to the small of her back pulling her in but she pushed me away giggling.

“Text me later!” She winked and walked out the door, I could not resist the urge to watch her tall legs strut down the hall, hips swaying. I closed the door and paid mind to the silence of our apartment. Kyle was still in bed despite it being 1pm now, very unlike him. My thoughts ran to last night as I closed my eyes. I could still see Kellys blue eyes staring at me with my cock in her pretty little mouth. Her cute button nose wiggling when she took me in and my pubic hairs tickled it, her tits bouncing with every movement. I reached down over my boxers feeling myself grow……I rushed to my bedroom and locked it.

[MF] How it started with my cousin

My 20’s were a wild time. When I hit my 30’s I moved to NYC and really calmed down (but what a strange time to calm down!). Recently I’ve been fantasizing about my most naughty experiences, and find myself wanting to share…

Mandy was my cousin via marriage, we were roughly the same age. She’s was super cute nerdy girl that was very physically blessed. She easily had DD’s, a perfect curvy body, and long brown hair. There was always tension between us, but nothing either of us acted on or even acknowledged. Well, until she made the first move. I was having a usual Friday night. This meant hanging out with friends and hitting the bars later to see what sort of trouble we could get into. Of course “trouble” is code for “girls”. I was sitting around a table with a few friends, discussing some new albums, when I felt my phone vibrate from a text message. I was expecting to hear from some other friends about going out that night, so imagine my surprise when I open the text to only see a picture of Mandy fondling her breasts! Mandy was blessed, to say the least. Instantly I feel my cock start to get hard, my face flushing red, and my heart racing…

[F] I’m a female porn producer

A few years ago, if you ever asked me what my future career would be, the last thing I would have said would be a porn producer. It all started when I was working for this modeling company, as an office person. I was just trying to make rent and pay my bills. That’s when I met this guy, who I’ll call Tony. Tony was in the porn business and he needed some help with his paperwork and clerical stuff. Nothing in front of the camera, all behind the scenes stuff. It paid cash, was flexible hours, and I needed the money. ​So I started working with him, and that’s how I got into the industry.

Most of my tasks were all administrative. Paperwork, billing, scheduling, lunch etc… I’m very organized and attentive, so all this came naturally for me. After a while, Tony started giving me more responsibilities, like booking, talent recruiting, screening, vendors. With that, he increased my pay, and I was finally able to get my own apt, without roommates. I eventually left my other job. I’m pretty good at what I do, and it helps to have a female on staff. I didn’t care about any of the content we made, it is what is is. We’re all consenting adults, all here doing a job. It’s actually a really chill and cool place to work.