Category: gonewildstories

Boyfriend’s Brother [MFM]

When I was younger I was dating a guy who was my age, that had a 28 or 29 year old brother, who was basically just a slightly more rugged looking version of my boyfriend. My boyfriend lived with his mom cos we were still in high school but his brother lived in an apartment a few towns away. So one day my boyfriend and I are alone at his house because his mom was out for whatever reason, so we’re taking advantage to fuck somewhat loudly on his bed. He made me cum twice, fucking me missionary before cumming himself. I could have still kept going but I was happy that he was happy and didn’t mind it was over in only 20 minutes.

He rolled off of me to reveal his brother standing in the doorway, watching us with a smirk on his face. He walked over and I was too shocked I didn’t even attempt to cover myself. He looked at my boyfriend, shook his head, and said “come on man, a bitch like that still has so much fuck in her yet, if you don’t get your cock in her now I will.” My boyfriend told him I’d cum twice already and I was fine, so his brother walked right up to me and touched my pussy, and I shook under his fingers. Read more »

Takeout sex with an older man [FM]

Warning graphic sexual descriptions:
I was 18 by the spring of my senior year and working as a hostess at a restaurant. That’s when covid hit and the restaurant stopped allowing customers inside. The owner turned the restaurant into to-go orders only but fortunately,, the owner was adamant that he would not let anyone go during this hard time and said we would all be needed when things returned to normal. The only major change was we closed a few hours earlier and I was now running food out to cars as well as helping with the phone orders instead of seating the restaurant.

The New schedule was a problem for me. I relied on my Dad to take me to work before his evening shifts and my mom to pick me up when she got off work. She is a nurse and wasn’t able to get off any earlier to accommodate my new schedule so I started having to wait a few hours for her to pick me up. There was a starbucks close by that I would walk to and wait for her. Inconvenient but not the worst thing to have to do. Read more »

[MF] Maeby we should lockdown.

At this point it’s around Early march 2020 when the lockdowns started. Me and Maeby have gotten into a pattern of  being humans about once a week but never on the same day or same hour it was all up to her really. It was while I was peeing. She had her usual firm grip at my base. It usually take me a minute to pee so we chat.

Josh: so I was thinking about the lockdowns and I figured you would want to go stay with your parents to help them out cause they’re older.

Maeby: I thought I would stay here with you for the same reason?

I mean I’d hoped she’s stayed because if she didn’t I’d have to go live with my parents cause I would have no night care if she left.

Maeby: plus Tony’s parents wanted him upstate at their cabin where they think they are safe from the virus haha. So I’ll have no where to go and since you work online and I’m going to school online now I can work for you 24/7 till the lockdown is over if that’s something you want. Read more »

Getting [F]ucked when his dad walks in.

I had gone over to my boyfriends house to spend some quality time and watch a movie.

I was wearing a short knee length pleated skirt, I love wearing those so much. We went to the downstairs family room to watch a movie. Don’t even ask what the movie was I don’t remember. We started making out right away. His hands were all over me.

I climbed on his lap and kissed him deeply while I ground against his crotch, we used to dry fuck all the time before finally starting to have full sex it was so naturally us.

I could feel he was pretty hard.

I unzipped his pants and pulled his cock out of his fly.

Sliding my panties to the side I sat on his dick.

We kissed as I rode him.

Then I heard the door open.

There I was sitting on his lap, our lips locked together as his dad walked in. We both froze waiting.

He saw us and said sorry and went back upstairs.

My skirt hid everything. I’m certain he thought we were just kissing. Read more »

[FM] My Ex and his Dad in the Same Day (Part 4)

I’m writing this down post-sex, because I never want to forget how amazing today was. I feel like an absolute slut, and I love. I’m currently naked, my pussy filled with cum (and a little bit sticky from our combined juices on my pussy lips and thighs). Mr. Jack is snoring away next to me.

It’s been a while since I last wrote. Parts 1 to 3 are on my profile. I know I didnt finish the last story. And I’m going to skip the details of the last time we had sex, mainly because I cant remember the specifics anymore. Lets focus on today.

I started this morning with another dick inside me – Mr. Jack’s son, and my ex/fwb, Devaughan. I hadn’t planned on seeing either of them today, but I had a day off. I was running errands close to Devaughans place, he texted me, and I popped over to say hi. We hadn’t seen each other in about a month, and its been even longer since we had sex. Read more »

How I (21m) became fuck buddies with my boss (30f) PART 3 [mf]

It’s been awhile since I wrote about my boss Rachel so here’s another one for old time’s sake. If you haven’t read the first 2 parts I suggest at least the first part for context and the 2nd if you’re a degenerate like me who just likes to hear about people fucking. Enjoy!

At this part of the FWB relationship with Rachel, I did in fact receive the job role I wanted with higher pay thanks to Rachel. I was her direct report now so at work I did whatever she told me to but outside of work and in the bedroom she did whatever I told her to.

A couple of weeks after I was transferred to Rachel’s team, I was working when she called my register and said she needed to schedule a meeting with me to discuss my training progress and sales numbers. It was late in the evening (for business hours) and I told her there were only 2 of us in that area for the rest of the night and she said to let my coworker know I had to meet with her and that she asked them to cover the floor until I returned. Once I passed on the message, I walked upstairs to her office to meet with her. I walked in, while her back was towards the door. She told me to shut the door while continuing to type away on the computer. I did as instructed, and soon as the door closed she turned to face me. Read more »

Breaking the bed [mf]

I had my gf at the time over once while my parents were out, and of course we were taking the ample opportunity to go to town.

Halfway through pounding her from behind, my fucking bed frame snapped in one corner and fell in, causing us to both fall of the bed! Of course we panicked at first and then laughed, but that didn’t stop us from picking up from our interruption.

Once we were finished, we threw the bedframe out and I moved out soon after so I never got a new one.

[FM] [F23] Hot 2AM time!

My boyfriend had gotten a little drunk and fell asleep in my bed. At 2:00am I wake up to him making noises. He asked me if I was a wake I said yes he came over and spooned me from behind and wrapped his arms around me. He started playing with my chest and I could feel his hard on against my ass which made me super wet. He slid his hands in my pants and started rubbing my pussy and feeling my wetness turned him on more he pulled his pants down and put his dick between my ass cheeks and was moaning against my ear. He stuck his dick in my asshole and started fucking my tight little hole. He rubbed me till I came then pulled out and I went to turn over and suck him and he came all in my mouth. After I sucked him off two more times throughout the morning! It was so sexy!

Life as a College Cuckold Boyfriend [consensual] [long] [some foot fetish] [MF]

*Note from the author: This story ended up being almost 3 stories in 1. Future installments will probably be a lot shorter, but leave your feedback below in terms of what you’d like to see. Note that this story includes more foot fetish content than my last one, but it is mostly in the last 1/3rd. While this story is a continuation of my last post, it should stand alone well enough to be read on its own.*

Now that I’ve told [our origin story](https://www.reddit.com/r/cuckoldstories/comments/m7zj1t/how_a_threemonth_breakup_made_me_a_cuckold/) to positive reviews, I can start getting into some of the other experiences Chloe and I have had over the course of our relationship. I think one of the things I’m most grateful for in our relationship is that we found and embraced this kink very young, whereas many don’t find it until much later in life. This allowed for a variety of experiences that usually only exist in fantasy, like the one below. Read more »