The Time I had a Threesome with a Wannabe Pornstar and a Virgin [FFM]

A few years ago, I basically had a sugar mama. Let’s call her Jen. Jen was 5-6 years older than me, established in her career, and around the big city on an international assignment for a year in finance. She liked luxury bags, tight fitting office clothes, getting plowed, and avoiding cooking. Physically she was slim yet busty, with long dark hair, and the kind of ass you can’t have without hard work.

In contrast, I was a student living in a college town who didn’t quite have his life together. I liked professional women, and met up with Jen via a dating app while visiting the big city. There weren’t sparks quite yet, but after a few days we learned that we matched each other’s sexual tastes quite well.

We proceeded to get into a pretty regular routine: every couple of weeks, I would travel to the big city and stay at her place. Being on an international assignment, she had an amazing apartment paid by her company and it was fun to be in. She would pay for expensive ingredients, I would cook with them. She would buy me some nice clothes, I’d wear them for her. She would buy some sex toys, I’d help her use them.

28 [MF] Giving “Innocent” Korean girl a Creampie on a Fist Date

It’s been a while since I’ve written here, but a friend told me they wanted to read another story about my experiences. So here we go (:

One night not too long ago in the great city of San Francisco, I met a cute Korean girl on bumble. Let’s call her Soo.

Soo was a very diligent tech worker in the city. Her profile was barebones, with cute-type photos that shouted the “mainland girl” aesthetic. Frilly clothes, pale makeup, red lip.
Physically you couldn’t tell much from the photos, but it was a fine risk to take.

Soo wasn’t the best texter; in fact, she’d be be in the running for the worst. Still, we managed to have the regular cordial chat one expects on these sites. But given how she had a more innocent aesthetic, and I know that I tend to give innocent vibes on dating sites, I went out of my way to let her know that I was nowhere near as innocent as I looked. She replied that is ok, but she is very innocent herself.

I Regularly Teach Virgin Women How to Suck Cock [MF]

Admittedly this will be a bit different than my other posts in that it is an amalgamation of experiences, as opposed to one particular one.

I wanted to write about it because several people were surprised that I do this, and expressed interest in learning more. If there is a better subreddit for this, please let me know!

So over the last year or so, I have been on dating apps and Reddit regularly. Once in a while I meet women, who for whatever reason (religion, fear, life constraints) are still virgins.

People looking mostly for casual sex like myself would often stop the conversation there. Instead of that, I ask them about why, and how that has affected their dating life. These women often communicate how they are scared of any sexual situation, because they don’t trust themselves to be able to say no without bothering their partner.

I actually care a lot about women being able to safely explore sex, so sometimes I will offer to teach these virgin women. I believe that the safest way for a woman who doesn’t feel super comfortable saying no to avoid having sex with a dominant partner is to get him off in a different way. So that ends up being the focus.

A Steamy Conference Hookup a Full Year in the Making [MF]

I haven’t written in a while, so thought I should get back on the ol’ horse.

If you haven’t read my other stories, I’m a tall, nerdy guy in his 20s with a big cock.

This story happened a couple years ago, while I was in grad school. In my field, there’s a big annual conference that plenty of people go to. It’s mostly business, but once in a while you can find someone fun ;)

At this conference, I was at a networking event for job search. Par for the course, company representatives were swarmed by desperate job seekers, and I needed a break on the sidelines. While there, I noticed someone else on the sidelines: tall, professional dress, tanned skin (she was middle eastern), long dark hair, and striking green eyes. Let’s call her Layla.

I started chatting with her, making small talk about how palpable the desperation was. Layla laughed, and we had a good conversation related to our own research and work aspirations. When it was time to head out, I gave her my card, and we promised to follow up to share some research papers.

Being a Boy Scout, but also Ramming my Student as a TA [MF] [Long]

This story happened a few years ago. I was in University, and in a position to be a TA for a course. Please note that, unlike some of my other stories, this one is mostly about a tense buildup, as opposed to the actual sex.

It was the start of the year, and I was back on dating apps. I met a girl on an app, and decided to get coffee. Let’s call her Misty.

I was happy to learn that Misty was even prettier in person than in her pictures: she was a fit asian with a small frame, perky b cups, and a nice little ass. The most attractive parts about her, though, were her big round eyes, and infectious smile. I later learned that she used to be a cheerleader, and really had a cute girl next door kind of vibe.

We talked about the normal things, and were having a really good time. I went on to ask about what courses she was taking. She told me she was taking x, y, z and biology 101 (note: course name changed for obvious reasons). I started to sweat a little, and ask her who her professor was (there were at least 4 different profs teaching it). She said Mrs. Hullabot’s, and I sweat even more. Finally, I asked her section number, and she said “2”.

An Evening of Strip Chess Gone Right [MF]

Admittedly, this post will be nerdier than some of my others, but this was one of my most enjoyable experiences.

A couple years ago, I was flirting with a girl from a dating website via text. Let’s call her Sasha. Sasha was a tall south Asian beauty, with long hair, big lips, and and a wonderfully thick ass.

Sasha was always playful via text, and we had a good rapport. We had met up for a couple dates, but nothing phyiscal had happened yet. Our texts often dabbled into the sexual realm, but not too far. At one point, she asked me about sexual fantasies, and I disclosed that I loved the idea of adding stripping and sexual favour dynamics to chess.

She grew very interested in this idea,while simultaneously talking a lot of shit about how she would destroy me in such a chess game. After a few days, I described a set of rules, and told her to come put her money where her mouth is.

Handcuffed and Creampied her in a Starbucks Bathroom [MF]

A lot of redditors enjoyed my last post, and encouraged me to share other experiences. Quite a few come to mind, but I’ll stick to sharing this one for now.

This was a couple years back, and I had been casually dating this girl I met on a dating app. Let’s call her Ashley. Ashley did office work at a pretty boring big company; she had to dress up in heels every day, do repetitive work, then go back home.

Physically, she was asian, medium build, pretty face with big lips, and an ass that she clearly put a lot of hard work into. Wearing a pencil skirt and heels all day, she got hit on a lot.

For those who don’t remember, I’m tall, white, nerdy, and hung. Of relevance to this story is that I almost never dress up (don’t need to for work) and get to take long lunch hours.

Ashley and I had been intimate before, but everything had been pretty vanilla. She expressed an interest in kink related things, though, and that was something I intended to pursue.

A Female Redditor Came to Challenge my 8 inch Cock [MF] (raobj x-post)

Around a week ago I put up a post on random acts of blowjob for women looking for a challenge https://www.reddit.com/r/RandomActsOfBlowJob/comments/9q0nv6/m4f_toronto_looking_for_an_actual_challenge/

Basically, I’m hung and tough to make cum from a blowjob overall, and wanted to see what local lady redditors had to offer.

I received a message from a local redditor that night. She was nearby, sex positive,and very confident in her oral skills. She asked me how long it usually takes me to cum with someone skilled, and after I said it was 20 minutes, she declared she could do it in 15. I liked her style, and thought it would be fun to make a little deal:

If she made me cum in 15 minutes, she got the the badge of honour of having done so (I offered for more, but she said she would simply be happy with milking the cum out of me).
If she couldn’t, however, I got the right to do whatever I liked with her that was non penetrative (and somewhat reasonable; we agreed on a safe word).