My Girlfriends Mom; A Week To Never Forget [Part 1]

**Welcome to my very first story!**
For the longest time, I’ve played around with the idea of writing. After running out of excuses, I finally made the decision to just do it.
So enjoy the first part of an upcoming series!

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I have agreed to meet my girlfriend after school. It is a hot summer day and since she has a pool in her backyard, we thought it would be fun to hang around by the pool. Her family is quite wealthy, no one can deny that. It is hard to miss a house that big.

Her father was a successful businessman, but sadly passed away a couple years ago. All his wealth and business were transferred to her and her mother. That means all the money, including her father’s company.

I hang around a lot at my girlfriend’s house, since her mother is always gone for work doing business trips. I have only met her once or twice maybe four times at least in a span of 2 years. But other than that, I did not really have the chance to talk to her properly. Not that I am complaining, I appreciate when I am alone with my girlfriend without constant being watched or questioned by parents like I am up to no good with their daughter.

Billie Loses Her Virginity On An Island Vacation (mf | first time | virgin | celeb)

My first time having sex was when I went on vacation in Hawaii to take a break from my career as a singer, that was currently blowing up. I had just turned 18 years old a few months ago when I was on the plane out over the ocean. The only thing that I could think about was landing and heading directly to the beach. My friend came along with me, so I would not be alone on my first adult vacation. On the plane I was wearing in a large shirt that hung loosely over my body. Matched with an oversized pair of jeans, so that I was able to cover my body from the cameramen waiting for me at the airport exit. They knew I would be landing there sometime today and were determined to snap some photos before I got away to a private resort. Underneath the baggy close I was already wearing my black two-piece bikini that I was ready to feel free in at the beach. I walked past the paparazzi and got into my ride waiting with my friend as the lights flashed from the photos being taken. Once I was in the car, I knew that I was free from the media for the next week. We rode to the resort where we was met by a woman who greeted us. She was the owner and quickly introduced us to the man who would be serving us this week. A man came with a golf cart to pick up our bags and take us to the house we would be staying in a house over the water off the coast. He was barely older than me, maybe being 22. While driving to the home we would be staying at for the week, the driver told us his name was Kane. He was a fit boy wearing a white polo and khaki shorts that seemed to be his uniform for the resort. Kane was a Hawaiian born man from a father from the island and a white mother from Texas. We made small talk on the ride over, also learning that he was the room service man for the resort for the past two years. Promising to bring us anything we needed to make sure the vacation was perfect. We drove across a wooden dock that had houses on stilts over the water. Our place was the last on on the dock, giving us extra room in the water on one side. Kane put our bags in the two bedrooms inside, before reminding us to call for anything and leaving us alone. Rosie started unpacking, but I was just ready to be free in the water.

[FMMM+, Gangbang, Creampie] Crossed “gangbang in adult theater” off my bucket list today

Denver, CO

I went to a popular adult theater in Denver, Pleasures on West Colfax, to live out a fantasy. Overall a fun, lovely experience. I’ll get to the sexual details in a bit, bear with me a bit as I’m exhausted, sore and had, among other things, an intense quad/glutes workout. Didn’t see that coming, and an awesome side benefit.

I’d assume guys go there to get off, but it was an entirely different experience for me…

I reconnected, as I seem to do every six months or so, with an ex boyfriend that means a lot to me — one of those relationships that’s unequal in emotional attachments, as I’ve always loved him and he just really likes my company. So it’s nice for me to see him, but sad as I know he’ll be around for a month or three until he tries to make a vanilla relationship work. Those always seem to fail as his perv side is, in my opinion, a compulsion.

One of his compulsions is seeing me covered in ejaculate. Good, wholesome, safe fun, so why not? I was a little hesitant about going to an adult theater as I’d never been and didn’t want to get “swamped”.

Threesome with my high school friend and his wife

So my buddy from HS and his wife look like the brunette version of Ken & Barbie. They are both fitness nuts and she teaches yoga.

I’m over at their house and we’re talking about dating apps. I tell them how I have an account where I post regular face pics and a separate account where I post shirtless and r rated pics and hint I have a huge cock.

Her eyes light up and right away she says Dave has a huge cock too. Within minutes she is rubbing his cock over his pants while we keep talking and it’s clear something is about to go down.

I take the initiative and just ask if they have ever done any swinging and they admit they have. I tell them that’s hot and I give the impression I’m down if they want to play.

They are on the couch and I am in a chair to the left of them and they start making out and she whips out his dick through the zipper. It’s huge, much like mine and she is playing with it while she asks to see mine. I stand up and at this point I’m already hard so I just pull it out.

Erica, sister #2, part 2 [Str8][Mf]

This story is about the rest of my night with Erica. Since I already covered a lot of the build up, this should be a quicker story. I’ll put the links to the first 2 stories in a comment, but I’ll do a quick overview too. I first dated a girl named Connie while in high school. Later, I started a thing with her younger sister Erica. Erica gave me a blowjob right before we went to a party that her sister Connie would also be at.

So picking up where part 1 left off, Erica and I left my house and went to the party at my friend’s house. When we arrived, the party was already started. We got inside and got drinks, and right away ran into Connie, who had been there for a while already. She gave us a look that said “I know what you’ve been up to, and I’m not super happy about it”. Sensing where that might be going, Erica and I went outside to distance ourselves. We spent some time outside in the pool and the hot tub. It was really nice hanging out with Erica around my friends. She got along with them all well, and we were having a good time.

Twice my age, Two times as fun! [hotel sex], [morning sex], [heels], [mature], [MF]

*I am reposting this story- I shared it a few months ago, but removed it for some personal reasons.*

This is the second and final part of a true story from about a decade ago- for me, a memorable and sex life-changing experience. You can read about our [first encounter here.](https://www.reddit.com/r/gonewildstories/comments/hqecwi/amazing_encounter_with_a_woman_twice_my_age_milf/).

Disclaimers: Names changed for fairly obvious reasons. Additionally, if uninterested in the buildup, readers can skip to the **first and second parts with sex below, as this is a fairly long story.**.

The ‘Cast‘: Me: ‘D’ Six feet tall, 26 years old at the time, athletic white guy. Her: ‘Kari’ about 50+ years old, white, petite and athletic/muscular, sandy blonde hair and about 5’5’ (with A/B-cup breasts).

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The morning I left Kari’s house, she told me she’d keep my number. I wasn’t realistically expecting to hear from her again. At twice my age, we were at such different places in life and I had no expectations of any sort of relationship with her. To quickly recap: I was heavily invested in my new job and she was on the backside of a divorce and teenagers.

I (M18) lost my virginity to an escort

I walked over to her apartment, entered her house and started talking to her. She told me to get undressed and to sit on the bed.

I was scared I wouldn’t be able to get hard but as soon as we started making out my cock shot up. We kept making out and I kept getting harder. My cock was so hard it almost hurt.

She asked me if I wanted oral and told me to lie down. I did and she wrapped her hand round my cock, stroked me a few and started sucking.

It felt so good. Her tongue was the best thing I’d ever felt. She was worshipping my cock and it felt so good. I couldn’t speak because of how good it felt.

She asked if I wanted sex and said yes. She put the condom on me and asked me what position. I said doggy and she turned over.

I started fucking her. At first I didn’t know where to put my hands but I got more comfortable and started feeling her ass.

I got tired so we switched to cowgirl. She was finding me and it felt so good. We were both tired so she stopped after a couple of minutes.

More Fun with the Maid (MF) (oral) (handjob)

I still couldn’t believe the fun I’d be having with the weekly maid. Unfortunately, I was out of the house when she came to clean the next week and doing yard work the following week under my mom’s watchful eye.

It was really hot mowing the lawn that day and would have loved to just in the shower with Elena afterwards.. She was packing up and leaving while I finished up near the driveway. I had been using my shirt to mop my sweat. Elena’s eyes popped out as she walked past to her car.

We were out of earshot of my mom, when Elena said “you look so sexy today.” As usual, she managed to look incredible while dressed normally. “If only we got a moment alone this time.. Maybe next week.”

Once again, mom was in the house, but was locked into conference calls for one of her organizations. I didn’t have my hopes too high, knowing my mom could pop up at any time. I set up in the basement watching tv when Elena came downstairs. Today, she set aside her usual apparel for a sports bra and leggings. My jaw dropped watching her sexy Latin body descending the stairs.

That time I had wild sex with a stranger [MF]

Almost 10 years ago, I had one crazy night. Let me share it with you.

At the end of a business trip in the south, I was looking forward to going home. But the snow up north had another idea.

My flight cancelled, I decided to go to a local nudist resort for a late afternoon dinner. Now I have been a nudist for years, gone to many midwest nude campgrounds and beaches when traveling. My wife knew, so I thought nothing of it. My wife and I , while best friends, never have had the best sex life. Part of that is my work schedule, part is my wife’s body image issues and self-love. She is gorgeous and doesn’t know it. I remind her daily.

I arrive at Caliente resort in Tampa, go to the front desk and ask for a room instead of a day pass( I still to this day, don’t know why I did that) the clerk said that I could get a better rate if I declared I was part of a couple. She smirked and said “what is your significant others name?” I glanced down at her name tag , pinned to a rather thin white oxford shirt that framed her perfect breasts, nipple proudly slipping out with each reach for pen or room key. “Samantha” I said, with a wink, reading her name tag. She giggled and said , “that’s a great name”.