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Me [M] roleplaying teacher for my widow student [F] – Part 2

If you’ve read the first part of this, [here](https://www.reddit.com/r/gonewildstories/comments/egomgd/me_m_roleplaying_teacher_for_my_widow_student_f/), this is the second hour of the same “session”.

So carrying on from *exactly* where we left off. Anne was in a crouching position – her legs open, still wearing the skirt, but with no underwear. Her left hand was vicariously rubbing her clitoris, as I was unable to reach. I was standing up, my cock standing to attention as she had been bobbing on it. In her mind, the choking sounds, mixed with moans, and her rubbing herself was getting me off – it was.

But I had to continue the role of the teacher. “Anne, are you sure this is appropriate? You should be studying.” I lifted her back into her chair and pushed the seat towards the desk. I opened the laptop to greet her with porn. As Anne is Asian, she prefers Japanese girls getting their gaps eaten out by horny Japanese men. The moans filled the office. I looked down at Anne’s hand. She was rubbing herself under her skirt, almost breaking character, she just looked at me and said: “Just fuck me. I’m horny now.”

My reply: “No. We’re not done here, yet.” Read more »

[MF] Christmas vacation back in town where I grew up culminated tonight.

I’m a 31 year old white guy. I’ve lived outside of my hometown since University. I have spent the last few days at my parents for the holiday.

A few days ago I posted on social media that I was going to be in town for the holidays. I received a few surprising likes from a few ladies I went to highschool with.

A few nights ago I get a DM from a girl who was once best friends with the girl I dated way back in highschool. I was incredibly attracted to my girls best friend but never said anything because I was with her best friend.

To make a long story short. This girl and I DMd all night where we shared stories about the good times.

She ends up telling me about how my ex used to brag about our sex life and what she was told by my ex. She ends up saying “I bet you probably have more than a few options but you should come by my place tomorrow night.” Read more »

Me [M] roleplaying teacher for my widow student [F]

My girlfriend (widow) I’ve wrote about a few times now on this sub, I’ll call her Anne. She disclosed she had a teacher/student fetish. We’re brand new to our relationship and in the honeymoon stages of experimenting. I decided to really go the whole way and give her the roleplay that she has always wanted.

I was dressed smart – a blazer, shirt, smart pants, a belt, while Anne was dressed as a schoolgirl, albeit a slutty one. She wasn’t wearing a bra and was in a shirt, short skirt and socks. I’d told her to take her shoes off before she entered my classroom. I was the teacher. This was the classroom. No, this was detention. Anne’s fantasy was barely a fantasy and was now extremely real.

I started a countdown clock from 2 hours. I handed Anne a piece of paper. “Write the following: I’m a bad girl. I will do what my teacher says”. I told her to write it immediately and she did. Anne could see the clock right in front of her. She was in detention – that was my theme for the roleplay. I’d set up the room to resemble a teacher’s office – study books, a table, pens, a laptop. Anne had no clue what I was going to do during those 2 hours, all she knew was that I was the Dom and she was the sub at my mercy. Read more »

My girlfriend told me to date my old female coworker [FMF] part 2

When you look back on your life, you can find significant moments that completely altered what may be in store for your future. This is often referred to as the butterfly effect. Kate told me to date Iris, and now here I am with Iris looking at me while her mouth is around my cock.

Let me back up a bit, and if you haven’t read part one yet. You may want to https://www.reddit.com/r/gonewildstories/comments/e5b61a/my_girlfriend_told_me_to_date_my_old_female/

The fight between Kate and me a few weeks back no longer lingered in the air like a giant balloon. Kate and I were strong, stronger than we give ourselves credit for. Neither of us looked in the mirror confused at who we saw looking back at us.

Growth was prevalent in this situation, growth with Kate, growth with Iris, and lastly, growth with myself.
Iris was becoming more a part of our regular routine, we all knew how to handle the situation that we made for ourselves. We even adapted to the point of all of us hanging out together and talking. We brought Iris around more often to make my roommates not think anything of it when they saw us together alone or with Kate. Read more »

[MF] public car sex

start by saying this is a true story about me and my ex.

I had just graduated high school and she was still attending it. We didn’t have a place to fuck so I would borrow my sister’s car, and we would fuck in it on a road that was barely used.

One time, when we were particularly frisky we went there to have some fun, and we noticed there was a cop car parked at an intersection near our parking place. If we tried anything, he’d be in eyesight though it was dark. We decided to try making it first to see what happened. He didn’t move. So we got brave. I played with her tits as she pulled out my dick. Soon she was going down on me with enthusiasm. Being weak to my desires, I stripped her naked and got naked as well. We moved to the backseat, and soon I was fucking her raw. The cop still didn’t move. We kept the car rocking for 30-40 minutes before I busted inside her. The thrill of getting caught made it so much better. We got dressed and drove off. The cop did not follow.

I Wanted [M]y [F[riend for Lunch

For mental image’s sake: I’m 6’1, fairly athletic build. She’s about 5’10, slim build with a large chest and tight ass.

She and I go back and forth sexting a bit one work day and I tell her I think I’ll have her for lunch. She likes this idea and I head toward her house for lunch and I text her my eta, telling her to be in her bed, naked, plug in her ass and playing with herself however she likes, but that she can’t come until I’m there.

So I walk in the door, greet the dog, let the tension build for her waiting in the next room and walk in to see her tight ass in the air, chest down and looking toward me at the door with her hand on her vibrator pressed in between her legs. I smile, tell her shes a good little slut, and undo my belt as I walk towards her. By now she’s eager so she sits up and helps undo my belt and fly and pulls down my briefs in one go, letting me spring out and into her eager mouth.

First Anal [FM] From the Cougar Chronicles

Sorry if this is long, first time sharing something like this.

My friends tend to wonder why I date younger guys. You would think me being the older one, I would have more adventures under my belt. Truth is, I was a very late bloomer (we just won’t go into that). But I’m not sure that is the reason for dating younger guys. That may never be answered. But one experience with a younger guy stands out (ok there may be more than one). My introduction to anal came from a younger guy. I was 38 and he was 25. I met K through a dating site. He was the gym rat type, between work and school (he wanted to be an EMT), all his free time was spent in a gym. So, I was surprised he took an interest in me. Even though I go to the gym, I am definitely not the gym body type. I go to the gym so I can survive a disaster movie and eat Nutella. Turned out we did have a great love of movies in common. I would say after a couple weeks of texting, our texts became more and more less PG. There are probably some fun photos of me circulating out there somewhere, if I find out they are making money, I need my cut. So, one text leads to another, a couple of phone calls too. I even got lectured for leaving plastic water bottles in my car and still drinking from the bottle. Read more »