Category: gonewildstories

[MF] My first time being pegged

At the time this took place I was a single guy in my thirties, just out of a relationship and starting to experiment and try out new things.

I got chatting to a local woman, around my age and a bi blonde BBW. She hinted that she had a strap on which she’d only used on other women, but she was looking to change that.

We met for a drink in a bar near me the first time, then headed back to my place. I won’t go into detail on that one, but it was a lot of fun and led to us arranging to meet a second time a couple of weeks later.

She texted me on the day to confirm our arrangements and ask if she should bring anything? I replied “maybe a bottle of wine?” and then quickly added “and your strap on…”. Her reply was simply the grinning devil emoji.

When she arrived she had brought that bottle of wine so we had a glass and chatted a little first. When we had finished the wine she excused herself to go to the bathroom and told me to wait for her in the bedroom… Read more »

When WE got offered $ for sex [MF]

This story is fucking weird. Keep in mind we were in a very interesting place with a slightly weird culture. Certain things got lost in translation, but I swear I just often got into fucking weird situations with this person. We were both reckless so we did things that often put us in the line of fire, but I swear he just attracted trouble.

Anyway, I was once at a hotel bar with this guy I was dating. We were flirting pretty openly and kept making each other laugh. We were actually being so goofy it was almost a scene.

We were celebrating this article I wrote so I was pretty dolled up. It wasn’t anything too crazy but I was in a black dress and heels. It may or may not have been low cut. He was in a suit.

*I’m not sure if this is relevant, but it is possibly worth noting because shit gets weird.*

Also, my date was hella hot. Women openly hit on him in front of me and we often got stared at. It’s a fun reality of being with a super hot person- it makes people weird. Read more »

Solo play while writing erotica + a FWB encounter [masturbation] [FM]

Recently my best friend gifted me two nights in a fancy room at the Cosmopolitan to go and recharge by myself. I’d put off scheduling it for a while, but then I got an order for a custom erotica that takes place on the strip! It felt like the universe was telling me to go enjoy, so I did.

As soon as I got to my room, I stripped naked and put on a short silk robe I brought with me. I took in my surroundings – a huge, plush bed, big velvet chair and floor to ceiling windows. The bathroom was dark and sensual, complete with a rain shower head, my favorite. I was really excited to shower but I was starving so I ordered room service first.

As I was waiting, I read over the custom erotica commissions I planned to work on. I wrote down some ideas and notes to revisit later, and let my customers know I’d be starting their pieces tonight. As is always the case, I was already kind of turned on reading about their fantasies. When the room service was delivered, I jumped, I was so engrossed in what I was doing. Read more »

[MF] 15 min hookup

I had been chatting online with a woman 10 years my senior for the last several weeks. I am [M 34] and she is [F 44]. I met her on a fetish site that we both belonged too. In her profile she stated that she was married, but her husband was not capable of satisfying her sexual needs and she was strictly looking for fwb and hookups. She had pictures of her body on her profile so I knew that she had enormous tits. She was a thick bbw but definitely not fat. Anyway we chatted for a few weeks and sent each other dirty messages and pics throughout the day.
We had tried to meetup a few times, but things never seemed to line up until last Friday. We had be sexting all day long. She would sneak off to the bathroom throughout the day and sent me a pic of her fingering herself and one of her enormous tits. I replied with dirty texts about what I would like to do to her and a pic of my hard cock.
After several texts we realized that we were going to pass each other on the highway on our ways home. I suggested that we meet up just say hi. Plus I wanted to see her face which I hadn’t seen yet. For all I knew she had a body and a but-her face. She responded that she was up for it, and she had a place in mind that was a little more secluded in case we wanted to do more than say hi. I agreed, but I let her know that I only had about 15 min because I had to get home for commitments I had later. She agreed.
I found my way to the park where we planed to meet. I waited about 10 min and was about to give up and leave when I saw a car approach. The sun was glaring off her windshield so I was not able to see her until she stepped out of her car. Damn!!! She was a bbw with a gorgeous face. I smiled and waved at her and she walked over and jumped in my truck.
Not a word was said, she just damn near sprang forward and started to make out with me like we were a couple of teenagers. Fuck was it hot, and she was a skilled kisser. I massager her tits through her shirt and then unbuttoned her blouse to get access to her ample cleavage. I kissed my way down her neck and pulled her huge tits out of her lacy bra and sucked and made out her gorgeous breasts. I sucked, licked and massaged her tits for about 5 mins until she pushed me back and told me to get in the back seat. She told me she needed more room for what she was going to do next and the console was getting in the way.
I climbed into the back seat at record speed and she followed. She tugged at my belt and popped the but and unzipped my jeans. She grabbed the waist of my jeans and boxers and pulled them both down to my knees. She wrapped her fingers around my cock and leaned forward and engulfed the head of my cock in her warm wet mouth. Fuck!!!! My eyes rolled to the back of my head as she took my whole cock down her throat and ticketed my balls with her tongue. I had never felt something so amazing. Without any hesitation she started to bob up and down on my cock from tip to base. She worshiped the length of my cock for about two mins and I let her know that I was going to cum. She didn’t let up so I ran my fingers through her hair as I blew rope after rope of cum down her throat. Even after she had swallowed every drop she did no slow down, and I had to pull her off my cock because I was so sensitive. I told her that I wished that I would have lasted longer. She told me that she was making sure that I came quick because I said that I only had 15 minute, but next time she wants to know what my cock feels like filling her pussy. With that she gave me a kiss on the cheek and got in her car and left. Read more »

I [f] took a once in a lifetime experience and entered the glory hole

I (f22) went to this apartment party and everyone was talking about this glory hole in a closet door that was in the bathroom (like you had to walk through the bathroom to get to the closet). There was writing that said “glory hole” above in with arrows on each side. I think it was meant as a joke or prank somehow. Buuuuttt…. I was a little drunk and curious and kinda horny; so I considered. After thinking about it so much I felt like I had to do it. When else would I be able to try this (something I’ve fantasized but been too scared to try) in a somewhat controlled environment like this) So I snuck into the closet and locked the door. I was on my phone for a while realizing I only had my one drink with me and no way to get more I waited. Eventually I heard the door open and close and a guys asking “anyone there?”. I replied “yeah I’m here” (I was afraid he might see me if I moved to much or got closer to the hole and so he knew I was a girl).Then he said “really your sure?” I just said “yeah” kinda quickly (I was nervous and I didn’t want anyone to recognize my voice either) eventually he unzipped and put his dick in the hole. I thought I would hesitate but I think the build up nerves kinda jolted me into action. I immediately moved up and blow his as best as I could. I guess word got around because guys started coming in after that some saying hi first some just going for it. I stayed in for the rest of the party. Leaving might mean getting caught. Once it quieted down I heard a someone come in and tell me I could use the shower and everyone was going to bed if I wanted to leave and shut the door. I didn’t shower but cleaned up as best I could waited a few minutes and ran for my car. Read more »

Fucking [M]y coworker [F] raw… while our other coworkers fucked in the next room

When I was in my early 20s, I worked at a tiny marketing agency on the West Coast with a woman named Catalina (or Cat, for short) who was a few years older than me—a completely stunning half-Argentinian woman with small but perky tits and the most amazing ass. She started about six months after I did, and we mostly worked on different accounts, but we hit it off and started flirting at work immediately.

The office culture involved VERY late hours and a pretty intense “work hard/play hard” atmosphere. One night, after working late, a big group of us—including Cat—decided to go out for happy hour and really tie one on.

Eight (or so) of us started off the night at a favorite nearby watering hole. A few rounds later, two had gone home and the remaining six of us took the party to a second location, a bar with a large outdoor space in a semi-residential area.

Cat and I had been flirting pretty heavily all night… and by now, we were both pretty drunk. We sat down next to each other, and at one point she touched my leg just above the knee while laughing at something I’d said. Read more »

best friend asked me to sit on his brothers lap [FM]

My best friend Peter and his girlfriend Anna wanted me to come to their lake house for the weekend. It’s a super nice place in a secluded, quiet town. I was worried I’d be an annoying third wheel, but he said his brother Sam (who i’ve always had a crush on) was coming too, and I was excited.

They agreed to drive and I thought they’d pick me up in his girlfriend’s SUV, but when they arrived the were in his truck, which only has front seats and barely fits the three of them.

“Sorry, we can scoot over, I think you can fit” my Peter said as I rolled my eyes.

We tried but it was just too uncomfortable, and my friend jokingly said “You can just sit on Anna’s lap, or Peter’s.” Anna is fucking tiny, like maybe weighs 100lbs soaking wet. I’m not all that much bigger than her but knew I would crush her, so I just said “Whatever” and climbed into Peter’s lap.

We drove for a while and at first I was trying to sit on him soooo lightly, like almost down toward his knees, but the drive was long and I started to settle in slowly until my ass was fully pressed into him. Read more »

helping a friend… [MF]

My wife and I were extremely sexual. We had all forms of sex and different positions and different places. While we were very adventurous we didn’t share it with many people for some obvious reasons. My wife however did share some of our adventures with one of her friends. She was a very sweet girl who came into the LDS late in life. Her husband and her married during a season that he was not active. After a couple of years of being married he felt like they needed to be back in the church.

Prior to being with him she was very very sexual. Even though he was away from the church at the time he was still pretty conservative and what he would and would not do. One of the taboos that he refused to take part in was anal sex. Which was a problem for her because she absolutely loved it. She would regularly masturbate when he was at work just to fill her ass. But I was getting to the point where her dildo was not enough. Read more »

What my friends dont know happens during calls [FM]

Most of my friends don’t know that whenever I am on call with them and my boyfriend is in the room – we are most likely doing something that they don’t want to know.

I was on call with my friends a few nights ago. It was just a voice call luckily or else they would’ve seen me and my bf both naked. As we talked, the topic of sex and dicks came up and we all talked about how much they turn us on. As we were talking about this, I was stroking my boyfriend’s dick feeling him get harder and harder as I explained how addicted to dick I am. As they were talking about their sexual experiences I muted and went down on my boyfriend. He tried ushering me off to go talk to my friends but I didn’t want to. I craved for his dick in my mouth. He began putting his hand on my head pushing my head down to get his whole dick in my mouth. I got a bit too into it and was gone for a while so my friends called out for me and said “nah shes prob just sucking his dick” and suggested that we turn on our camera to give them a free show. Im pretty sure they meant it as a joke so we didn’t turn on our camera, but maybe we should’ve and had a mutual masturbation session. Read more »

[MF] 26/24 Second Date Gets Unexpectedly Extended

I went on this second date with this architect a few years back. She was blonde, thin, thin, straight hair, blue eyes. Nice face and body overall. Her boobs were small but perky, and her ass was round.

We’d had a nice first date at a bar. I was pretty hesitant at the time on first dates, so all we did was hug, but she was very touchy during the date, putting her hand on my knee, taking my hands in hers, really looking at me eye-to-eye.

I wasn’t really thinking about sex with her, mostly just actual dating, but the second date was just okay, and I didn’t want to waste our time anymore. She’d bought a bottle of wine. We went to a BYOB Mexican place, and had a fine time, but afterward, I dropped her off at her car (we’d met at a nearby parking lot because parking sucked near the restaurant). We made out for a bit, initiated by her, and she got in her car. Read more »