I 37[M] had an old school caveman encounter with coworker [34] F.

I’m going to be posting a few of my previous encounters to hopefully give people something fun to read. This will be #1.

First off I am not the greatest with monogamy and haven’t been the best human being but these sexual encounters hold some fond memories.

I worked for a shitty outlet store and hired a few friends that I’ve worked with before to make things a little better. I ended up hiring my cute assistant manager from one of my old jobs as we always flirted and talked a lot about sex when we were alone. We never made moves on each other because we were both married. Also this was a few years ago so we were younger than ages listed.

Now we will call her “Carrie” for the story sake. Carrie had just separated from her then husband and was becoming increasingly flirty. She would come in wearing short dresses and really loose tops. She had small tits and never wore a bra. She is short and skinny as hell so it worked for her. Carrie is about 5’1 and 100-110lbs. I on the other hand am not small. I am 6’3” and about 240 at the time. I would also joke with her that because I’m a bigger guy it didn’t translate where it counted. She would just laugh and say yeah sure.

When my 30[F] husband 40[M] doesn’t let me cum

I am a squirter. I drench the bed, I can cum over and over and over again in minutes. My husband loves when I soak his cock while it’s inside of me, when I’m on top of him, any time really. But between sex blankets and sheets, it can be a pain in the ass (and not the fun kind).

On the same token, if I’m not allowed to cum, it builds up so bad. Everything feels fuller, deeper and drives me wild. There was a time where I felt I was entitled to cum (how wrong I was), and if he came first, I expected to be finished off. Until I learned how incredibly intense edging is. And how much hotter it is when my husband gets to cum and I don’t.

We like to play games centred around it. And when these start, my whole day and night is focused on him (can last a whole week if he deprives me that long). I become obsessed with the thought of him taking me from behind, throat-fucking me or just unloading his cum all over my face. Even walking down the stairs is a heightened experience. I’ll be doing laundry, and think about how he could tie me up with whatever piece of clothing ends up in my hand. By the time he gets home, there’s not a damned thing he can ask for that I wouldn’t do in that state. 

I [M] was the “house boy” for a house of sorority girls [F]

When I was in college, my fraternity had a partnership with a nearby sorority wherein we’d send over one of our newer members to act as a “house boy.” This guy’s job would be to visit the sorority house a couple times a week and do menial chores, such as vacuuming and laundry. My sophomore year, that turned out to be me.

The sorority house had 8 residents or “housies.” They were split among 4 bedrooms on the second floor, which were connected by a common hallway that led to the bathroom. The first floor had the living room, chapter room, kitchen, etcetera, and the laundry room was in the basement. All these areas became my responsibility.

I tried to be mature and respectful, but things went about as you would expect the first few weeks. Despite the free labor, some of the housies resented the lack of privacy from having a guy around so much. Whenever I’d knock on a bedroom door, there’d be a delay as the occupant got herself “decent” before letting me in to gather laundry or throw away trash. I never saw a housie anything less than fully dressed, even when hanging out on a lazy weekend. Even after a shower, they would come out of the bathroom fully dressed.

[MF] Taking her virginity / holiday fling

(If you want to skip the intro go to the …..)

When I was 21 I went on my first proper lads holiday with 7 other friends to a party island. We stayed in a hotel full of similar aged groups all with the same intention of getting blackout drunk every night. It was one of those hotels with holiday Reps, and as none of us had been here before we decided to go out with them for the first few nights.

So we leave the hotel on our first night with about 25-30 other people from our hotel and the Reps lead us to the first bar. As soon as we get the first lot of drinks in the Reps start to pull people to the middle of the bar to play a game, which I didn’t know was going to be happening lol. Both me and my friend were picked and despite our efforts to get out of it we were being pushed in by the rest of our friends. The game was to pass ice cubes along a line of people, but by only using your mouth (it’s been done on some tv shows apparently). Grim for anyone involved but clearly funny to watch.

That one night from my student days I’ll never forget [MF]

This happened to me 7 years ago while I was doing a degree in NYC. One of the girls in my class had a birthday party, and my buddy that I usually went with on these social gatherings were out of town. So, I decided to go by myself. When I arrived to the party, I was in one of the scenarios where I couldn’t quite figure out where to start. Everyone had already started to group up. For an introvert like me, that’s the worst kind of situation. I tried to join a few conversations, but it wasn’t panning out that well. So, I went to my buddy alcohol to make the threshold lower. I brought some mixing stuff, so I decided to find a corner and make some drinks. After having a few few quick shots, a beautiful girl walked up to me. It was Marsha from one of my class. Beautiful blonde Ukrainian student. Beautiful thin body. She asked if she could join me. I’m like sure, and poured her a drink.

I told my boyfriend about my first lesbian experience [FF]

Ever since my boyfriend gave me a [fake threesome](https://www.reddit.com/r/gonewildstories/comments/k7e0ly/my_first_fake_threesome_her_pov_mf/) that I’ve been wracking my mind on how to do the same to him since he told me his fantasy was to have a threesome with two girls.

 

I considered buying a fleshlight but I would’ve never been able to replicate the feeling of getting licked by two tongues, nor could I grow an extra pair of breasts for him to suck on. I even briefly considered hiring an escort after reading a post about it here on reddit. Alas, I chickened out.

 

It was not until the office Christmas party that I saw the light at the end of the tunnel.

 

Half an hour into the party and I spot my old roommate Cee from college chatting with a coworker. I excitedly told my boyfriend that there was someone that he had to meet and dragged him over. As soon as she saw me, she hugged me and giggled and joked how tall I had grown in the past year.

 

Kitkat at Home [M] and [F]

It was a mild summer night when P. and I were driving towards a restaurant outside of town. Between shifting gears I started to caress her thighs and started smiling mischievously when I noticed the fishnet stocking pattern under her long black dress. “Tonight will be a good night” I thought to myself just when I noticed P.’s hand reaching for my crotch. Getting my penis massaged I turned into the restaurants’ car park then left the car and started walking towards our table P. on my right side and a rocking hard boner in the centre.

What followed was a pleasantly uneventful dinner including lustful glances and drifting thoughts on what was to come this evening. But before leaving the restaurant P. went to the bathroom and when she came back it was her having a mischievous smile on her face. I looked her in the eyes, placed my hand on her ass and quickly noticed the reason. I felt the round silicone form of her Analplug and got immediately turned on by her wearing it in public.

The biggest cock I’ve ever seen and failed to suck [MF]

This is the story about the only time I tried and failed to suck a cock it was so big. I went to a very large university with D1 athletic program which had a great program in many sports and many students went on to be professional athletes after graduating.

Anyways, one night after I spent the day at the football (American) stadium watching our team steal a win from one of the best teams in the division, needless to say we all went out to celebrate and party really hard. Fast forward to a group of friends and I walking down the street headed to a house party a little off campus and met a group of men decked out in all of the university athletic apparel so we new instantly they were all athletes.

Flash forward to a few hours later and a few of my friends I hit it off with some of these men so ultimately I invited one of them back to my apartment for some fun. He was somewhere in the range of 5’10-6’0 and was so fit, in talking rock hard body, 8 pack abs and absolutely stunning to look at. When I got him into my apartment and we immediately started making out heavily. I reached down to feel his sick through his Nike sweats and just thought to myself “holy.fucking.shit” it can’t be that big.

Hotel fun [MF]

reposted from my deleted account

So there I was traveling again. When I check into hotels, I always make it a point to be nice to the workers. You never know what you’ll need. At this particular hotel, when I checked in the cute host (Melissa) was like “whoa you’re tall”. I am 6’4” so it’s not like I haven’t been told this before. She let out a short little laugh, like she was embarrassed she said that. I played along and jokingly said “whoa you’re shorter than me”. She was quite short … no more than 5’2”. She had a cute, young face, with long straight black hair. I couldn’t tell much more because she was behind the counter, of course. As I got my key, she asked if I needed anything for my stay … sadly I couldn’t not come up with a witty comment. She did point out that because of my Platinum status, she had upgraded me to a pool side suite. I rarely use hotel pools but was grateful anyways, as I like the extra space.

[F] 18 – Naughtiest thing I’ve ever done

I used a pestle to play with my asshole because I didn’t have a dildo. It burned at first because it was recently used to crush peppers so my ass was on fire. I poured a lot of extra virgin olive oil, cuz I’m virgin. I got used to it and came twice without taking it out. I also put another object in my pussy and humped my pillow with both holes stuffed. When I tried to pull it out, I couldn’t feel the tip. I guess the contractions of my orgasms pulled it in so far I almost lost it in my ass. I went to the toilet to try to push it out like shit and it came out with some shit stains on the end. I figured it would be too gross to continue using it for food so I hid it in my book bag for a while. My cousin who liked herbal stuff asked where the pestle went so I fished it out, washed it, and gave it to her.