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.

Part 2 with me [M] and the milf Filipina [F]

I promised part 2, so here it is. Raw and honest. All parts of this are 100% factual minus her name. Let’s call her “May”

If you read part one, some of you lucky guys got to see a pic of her legs. All I can say is: she’s extremely light weight-wise, no fat on her. She looks like an Asian pornstar looks. I couldn’t believe I was going to be fucking her. But, I was. We’d planned it. Although there was one issue. Her daughter had to come over too because her father was away on a trip.

So anyway – May (approx aged 27) brings her kid with her to my place. We put some TV on for the kid and I walk out the room. I ask May whether it’s appropriate we fuck eachother because it felt awkward with her kid being in the same house. May dropped to her knees and started unzipping me (outside the dining room). I picked her up so her legs are around my waist: “Guess it’s ok then?”

My [M] Sex with a slim, toned, milf Filipina [F]

As promised, more stories. This is very recent, last 6 months or so. I met a girl on tinder. She was an easy 10/10 body and 7/10 face. A pretty Filipina with small but very firm tits, and a body that would probably make a gay man straight. And to top it off? She was a sex addict. But let’s not get ahead of ourselves!

There was a catch. She had a kid. And if that wasn’t a big enough of a catch, she told me she lived with her ex. I thought it was all a bit weird but hey, my life isn’t perfect so I stuck with it. The kid was 3, so we decided to go on a first date without the kid and just see whether we got on well.

It turns out we got on like a house on fire. She laughed at all my jokes. I laughed at hers. We even walked from bar to bar linking arms. First date! Crazy I know. Anyway, we walked along a canal and I stopped her and said thanks for the date. I give her a kiss which ended up in a lot of touching in public – me running my hands down her tight hourglass body and pulling her into my now-hard groin area.

My [M] second night with the widow [F]

Due to the popularity of my first post, I’ll follow it up with one more. If you’re interested in hearing (reading) more, I can tell you about other girls I’ve been with, but I’m just following up with this one because people really seemed to get off over my first post.

So, my girlfriend (the widow), Anne, she invited me back over. I pretty much knew what was going to happen – but she didn’t. Back in my youth (15-25), I was addicted to sex. I started fairly young. I learned how to pleasure a woman so I wanted to give Anne a sneak preview of what lays in store if she stays in a relationship with me.

So I’ll cut to the chase. We ended up in the bedroom. She took all her clothes off – I didn’t mention, but she’s Asian. So just imagine a tight Asian body – perfect skin – no fat – just a flat stomach, small but perky breasts, which don’t sag – I’m just trying to describe her perfectly. Now not to sound racist (I can’t be can I, I only really date Asian women), but some Asians don’t have a big booty – and my girlfriend doesn’t have a huge ass, but she’s shapely. When she turns to the side, her curves are undeniable.

I [M] fucked a Widow [F]

I’ve never posted anything like this before – especially not on reddit. I was debating with myself whether I should. But honestly, I’m blown away (no pun intended) by what happened and feel the need to share this. It’s 100% true and not a single part of this is false – so this isn’t some weird fantasy I’ve had, it just kinda happened.

I met a woman 5+ years older than me on a dating site. It turns out she’s a widow – as of her early 30’s. She hasn’t slept with anyone in 5+ years since her late husband passed (found that out later on). But essentially, I told her we’ll take things extremely slow. Following a very long term relationship that broke up, I wasn’t fully over it mentally and that I always find a strong relationship happens when you don’t rush things.

Anyway, this is where the story heats up. Date #4, I go to her place. She lives alone, and still has pics of her late husband around the house. I felt weird, almost a bit like I was stealing another man’s woman. Which I’m not, and would never do. But I felt slightly upset and uncomfortable. But we ended up cuddling on the sofa and having a few drinks. She confessed to me she hadn’t had sex with anyone since he passed, but she had kissed 1-2 guys in those 5+ years.