My Airbnb host just jerked me off… [MF]

I booked an Airbnb up in the northwest for the week since I’m going to a wedding this weekend. It’s sort of a lodge type deal up in the woods. I checked in yesterday afternoon, it’s run by good looking woman in her early 40s.

I didn’t have much planned for the day and once I put my things in my room upstairs I walked down to the main floor to get a lay of the land. The first floor has a little makeshift bar area, and I took a seat there to check my phone. The host came down and asked what I was up to today. She was really friendly and apparently she had the day off of work from her regular job.

We made some small talk and she asked if I wanted a drink. I said sure, and she made me a G&T as well as one for herself. We chatted for a while about the area, and after a couple hours we were a little tipsy. She said that she was going to go for a swim and hang out on the lake and asked if I wanted to join. We were getting along pretty well so I said sure, but I needed to run upstairs and put on a bathing suit.

I fucked my girlfriend’s college dorm roommate… while my gf was off in class [MF]

The story starts off the night before this happened…

I went to a different school than my girlfriend Haley, but I was in town for the weekend visiting. Haley was a dark, busty brunette. We had been dating for a couple years and regularly visited each other during the school year. I’d never met her dorm mate before, but from what she would tell me I knew that they didn’t get along at all. Haley would regularly complain about her and was hoping to switch to another dorm room before the school year ended.

I made the drive out to her school for the weekend on Thursday, and we didn’t have much planned aside from going to a house party with some of her friends that night. The drive took longer than I expected and by the time I parked on campus, Haley was ready to head to the party.

We had a good time at the party and got pretty drunk. Her friend gave us a ride back to the dorm building after and as we were walking down the dorm hall, Haley warned me to be extra quiet when we went inside so that we didn’t wake up her roommate and piss her off. We unlocked the door and walked into the pitch black dorm and got in bed as quietly as we could.

Anal virginity taken by my married neighbor [MF]

I moved back home after college to look for a job and save some money. I didn’t have a car just yet so whenever I would browse tinder or the other dating apps I always kept the radius really small. As a younger guy I was always into older women (who isn’t?) so I didn’t have an upper age limit in the search settings. Maybe I’d get lucky and match with a hot MILF!

Sometimes when I would be watching tv I’d just swipe right on my phone, not even looking. I was laying in bed, checking my notifications when I noticed I had a new match. The picture looked really familiar so I clicked on her profile. The age said 41, her name was Jen, and I knew I had seen her somewhere before, I just couldn’t figure out where. She had black hair, big tits, and was pretty busty. I thought to myself ‘fuck it’ and messaged her.

Me: Hey there :)

Jen: Hey neighbor ;)

Blowjob with an audience [FFM]

Mia was my date to our company Christmas party, and her friend Anna was my coworker’s date since he didn’t have anyone to bring. My coworker got too drunk and went home, and Mia and Anna stayed over at my place. Mia slept in my bed and Anna slept out on the couch. I woke up really hungover but Mia was there to take care of me. I had my hands behind my head while my cock knocked at the back of her throat.

Her spit ran down my shaft and across my balls as she worked me with her mouth. My eyes were closed and I let out a groan as her warm mouth and wet lips pumped my head and shaft. That was when I heard my bedroom door creak and to my horror Anna popped her head in. Mia quickly pulled her head up and yanked the blanket up over my crotch.

“Are you guys up?” She asked as we lay frozen staring at her.

“Yeah, just got up,” Mia replied. Her hand moved onto my saliva-drenched shaft under the covers and squeezed.

My married neighbor took my anal virginity [MF]

I moved back home after college to look for a job and save some money. I didn’t have a car just yet so whenever I would browse tinder or the other dating apps I always kept the radius really small. As a younger guy I was always into older women (who isn’t?) so I didn’t have an upper age limit in the search settings. Maybe I’d get lucky and match with a hot MILF!

Sometimes when I would be watching tv I’d just swipe right on my phone, not even looking. I was laying in bed, checking my notifications when I noticed I had a new match. The picture looked really familiar so I clicked on her profile. The age said 41, her name was Jen, and I knew I had seen her somewhere before, I just couldn’t figure out where. She had black hair, big tits, and was pretty busty. I thought to myself ‘fuck it’ and messaged her.

Me: Hey there :)

Jen: Hey neighbor ;)

Blowjob with an audience [FFM]

Mia was my date to our company Christmas party, and her friend Anna was my coworker’s date since he didn’t have anyone to bring. My coworker got too drunk and went home, and Mia and Anna stayed over at my place. Mia slept in my bed and Anna slept out on the couch. I woke up really hungover but Mia was there to take care of me. I had my hands behind my head while my cock knocked at the back of her throat.

Her spit ran down my shaft and across my balls as she worked me with her mouth. My eyes were closed and I let out a groan as her warm mouth and wet lips pumped my head and shaft. That was when I heard my bedroom door creak and to my horror Anna popped her head in. Mia quickly pulled her head up and yanked the blanket up over my crotch.

“Are you guys up?” She asked as we lay frozen staring at her.

“Yeah, just got up,” Mia replied. Her hand moved onto my saliva-drenched shaft under the covers and squeezed.

My friend offered me unlimited blowjobs for my birthday [MF]

For background on how Mia and I started hooking up see [here](https://www.reddit.com/r/gonewildstories/comments/qpmlqi/my_longtime_friend_blew_me_just_minutes_after_her/)

Last year, some friends and I went out in the city together for our birthdays since they fall within a couple of weeks of each other. Mia and I had been hooking up for a few months at this point, but we kept it casual on the relationship side and she wasn’t able to make it out that night because she had to go to a family party. It was probably a good thing because whenever we want to a party or out together we couldn’t keep our hands off each other. If we went to a pool party shed be touching me under the water or if we were at a bar she’d be trying to drag me into the bathroom. More on that in future stories.

We went out way later and drank way more than we should have. I think it was around 4am by the time we all headed home. I passed out as soon as I got to my place and woke up with a searing headache around 9 or so. It was the kind of hangover where you feel so immobile to the point of not being able to crawl to the kitchen to get some water. I didn’t want to move. I checked my phone and saw that Mia had already texted me asking how my birthday went.

My longtime friend blew me just minutes after her boyfriend broke up with her [MF]

Mia and I were friends since middle school. We didn’t hang much during our college years since we weren’t in town at the same time often, but after we graduated we lived nearby each other and reconnected. We shared some friends and would go out together as a group in the city often. I had a place with some roommates in the city and she lived in the suburbs not too far away. It was common for all of us to go back to my place after the bars closed to either continue the partying or to just crash and go home in the morning.

Mia was a really sweet girl. She was a bit of a hippy, had very dark hair and was on the skinner side. She had dark eyes to match. She didn’t have a huge ass or tits or anything but she never wore a bra, so it was common to see her nipples poking at her shirt. Her lips made up for it though as she had big, thick lips that would probably make any woman jealous.

I fucked my FWB in front of her friends at a party [MF]

For background on how I met Mel (name changed) [see my previous post.](https://www.reddit.com/r/gonewildstories/comments/irflde/my_first_craigslist_hookup_mf/)

Mel and I hooked up pretty often for a few months. Her roommates were usually gone so I would come over to her place and we’d mess around in her living room or bedroom then go our separate ways. If you haven’t read my previous stories about her, all you really need to know is that she loved sucking cock, to the point where 90% of the time we hung out I would get blown and leave. We had only fucked once up until this point.

When we weren’t hanging out in person we’d sext and talk about what naughty things we wanted to try. We were both really into voyeur-type kinks. The idea of being watched always turned the both of us on. She’d asked a few times if I’d let her blow me in front of one of her guy friends, and although I thought the idea was really hot I always chickened out on actually following through and setting it up. I knew she probably hooked up with other guys and that was fine with me since we were just friends with benefits.

Getting to fuck my boss’s 18 year old daughter [MF]

Back when I had just turned 21, I worked as an intern/junior sales guy downtown. There was a bar in the lobby of the big building that we worked in, and it was a routine for some of us to go down there after work on Thursdays and Fridays for a few drinks before going home.

I had been working at the company for close to a year and my boss liked me enough to join me and some friends that worked nearby for drinks every so often. Friday came around, and Dan (my boss) asked if I was planning on getting drinks after work. I said I was and that my buddy Kris who worked nearby would be joining as well. Dan mentioned that his daughter would be joining us because she was spending the night in the city to go to a concert with some friends.