The best, and the worst sex of [m]y life

This happened over 10 years ago.

I just got into the university and my friends and I drove a couple of hours down to this house party in a smaller town not too far from where I live.

The house was located at this farm, and the house was so large, it could’ve been a motel or so (if I remember it correctly, there were over 10 bedrooms) and the lounge area (there were multiple lounges) I hung out was possibly as big as the flat I was staying at the time.

My friends have told me, before we got there, that it was a party hosted by a group of farm girls and practically we were the only guys (and his other friends) who will be there while the rest of them will be the girls.

A little note, I was the only short, chubby and awkward Asian guy (sadly, this hasn’t changed much) among all African men, who were, without being objective, quite good looking and fit guys (I don’t have any reservation of commenting on physical attractiveness of men. It is what it is, come on now).

Beach Repairs for my MILF FWB [MF]

After my latest hookup with Kat and Erin, I was riding on “cloud 9” and figured Kat would be good for a couple weeks because of closing out the school year and other things going on in her life; well I was wrong. Saturday afternoon, Kat called me, which was very rare, she explained that in the divorce, she had also gotten the small beach condo that they bought right after she got her first teaching job. They had used it as extra income through rentals. Apparently, the housekeeping service called her that morning and said there was some damage from the last guests, but the usual handyman was backed up with all the rentals opening up with the easement of Covid restrictions. Kat asked me if I would mind going over with her to look at it and fix a couple of small things. I agreed and she said she would pick me up on Sunday morning and we would be back on Monday morning.

(M)y coworker’s (f)irst time at the strip club [MF]

My career involves a good amount of travel and entertaining. In one of my past companies, I had a Russian coworker named Dahlia. Dahlia is a smoking hot blonde girl, who prides herself on fitness, has great perky tits, and an ass that shows off how fit she is. She looks like Evan Rachel Wood in my opinion. Her thick Russian accent is the icing on the cake.

Quick description of myself. I am about 6’3”, slim but toned from lifting weights, and I always have some sort of stubble facial hair. People play the celebrity look alike game with me a lot. The most flattering one that I like to believe is the most accurate (even if it’s not) is Ryan Gosling.

When Dahlia first joined the team, we had a happy hour event and noticed she was a little flirty and touchy after a drink or two. I was surprised since I knew she was married. Her and I continued to have a good work relationship, but never more than that. She would call me for advice and I would see her at events here and there. She continued to be a little flirty, but I always just assumed that was her personality.

Creampied the Preacher’s Daughter After a Wedding [Long] [MF]

My first year out of college, I went to a wedding as the +1 for my friend Dee, because she didn’t want to show up alone and have to deal with the annoyances that were childhood friends and acquaintances asking about her personal life. This isn’t about my friend, so I don’t need to describe her. The wedding was a big one. Lots of people and it was held at the church the bride had been a part of for years. Everyone was familiar with each other aside from the occasional date (myself included).

At the reception everyone went through the traditional steps, toast, first dance, respective parent dance, bouquet and garter toss, then cake. That’s when the fuddy duddy folk started leaving. I had enjoyed a few drinks by that point because I wasn’t socializing, might as well imbibe. Once the older crowds started leaving, I joined in on dancing with some of the younger crowd since the music got better and the liquor-aided confidence got stronger. At one point I turned and was face to face with a cute tight-bodied brunette. She was maybe a foot shorter than me, cute big eyes, wearing a cardigan over a camisole with a perky pair pushing against the buttoned sweater. She had a cute floral skirt and a pair of black leggings under it down to her calf boots. I took her in quickly with my eyes and saw a firm bodied beauty, but young. I held out my hand and asked if she was old enough to dance with me. She blushed and said she’s 19.

[M]y [F]irst time with my ex wife

My relationship with Kristina had been an interesting one.  We met in college when some mutual friends were actually trying to set us up with other people at a party.  We spent the evening talking and found that, at that time, we had some common interests and goals, and eventually made our way back to my house.  Since I was one of the older guys in my house I had the privilege of having my own room. That had some great benefits on this night and a few others.  When we arrived to my room I opened a few beers and we carried on talking for a while on the couch, and eventually things progressed to us kissing, and pawing at each other like teenagers.  We continued the fondling in a slow escalation with our hands over our clothes, but soon I had a hand under her sweater and felt the softness of the skin on her back, and as that happened we turned so that my back was against the back of the couch so that she was all but laying on me.  She in turn, reached down to stroke my length over my jeans, then began to fuss with my belt buckle.  Ultimately, things progressed to the point to where she started to slide off of my lap and to her feet, but not before she took hold of my shirt and pulled it over my head.  Once standing, she walked over and locked the door, turned and walked back toward the couch grabbing her beer.  She steadied herself, took a big drink, looked back at me and winked.

Getting dirty after cleaning up at a festival [MF], [hookup], [oral], [rimming]

The other day, a friend and I was talking about whether the ongoing quarantine will have any lasting effect on the younger generation´s hookup culture, which led to us to reminisce about our own chance encounters and random hookup from our younger days (i am in my middle thirties now).

One such memory occurred when I was in my early 20s, visiting the Roskilde Festival here in Denmark. For those of you who don´t know it, Roskilde Festival has a large camping area surrounding the festival site, and for me, partying in the camping area has always been at least as important than the music.

One morning, or rather one day at noon, I was getting up after a night of intense partying, and thought it would be a good time to visit the communal showers on site to clear up. I still felt lightheaded after a night, that had only left me with unclear memories about what had happened. One thing was clear though – I had been somewhere with a lot of glitter, as I was more or less covered from top to toe.

[Group] The Ball That Wasn’t

Hello everyone! I hope your lives of social distancing are going well, and I hope you have some time set aside to read, because the story I’m about to tell here won’t take just a couple of paragraphs. It’ll involve a little bit of set up just to let you know what happened.

This is a true story, something that I really did, but that I can scarcely believe. It happened not very long ago, just before all this pandemic madness made social contact much, much more difficult.

So I’m 30 years old, and I’m part a really close friend group of two guys and two girls, of which I’m one of the two girls. We’ve known each other for a very long time, though I’m a slightly more recent addition as the other three have known each other all the way through high school. The other woman in the friend group I’ll refer to as S. The two guys I’ll refer to as B and Tom. S & B are in a relationship, and have been for a very long time!

S also has a best friend I’ll refer to as K, who I’m also very close with, and who joins us to hang out occasionally, though not all the time.

Reconnected with a former school bully [FM]

Hi, I hope everyone’s doing ok ❤️.

I’m a trans girl, one year on hormones. Before hormones, I was always small, feminine, and sensitive, so I got bullied a fair amount, with guys calling me gay. Ironically, I was completely straight. In any event, there was this group of guys who would torment me a lot in middle school. Even then, I was smaller than the other guys, so they’d take my lunch and make fun of my inability to stop them. One of them was named Pablo. They were all muscular, and tall, especially compared to me. I vividly remember how much I hated and feared them.

Fast forward to a few weeks ago. I’m one year on hormones, and my sexuality has completely shifted. Whereas I used to be exclusively into girls, I’m only into men, and really only into macho alpha males types. It’s been really bad the past two months.

I’ve been very fortunate that I’ve always had low T levels, so a few months ago I started being able to pass more consistently. I started using dating apps to connect with guys, and I even hooked up with a guy a few times before the quarantine.

The Story of [M]y [F]irst Internet Hookup

So this is the story of the sluttiest thing I’ve ever done.

I was 22 at the time. I was just out of a 5 year relationship with my first and only high school girlfriend, and i was truly single for the first time since becoming an adult. Our breakup was less than amicable, seeing as how we were both trying to end our first relationship and had no real idea how to go about it. Needless to say, it was a rough patch, and without going too much into detail, suffice to say I was in the mood for some exploration. This led me to OkCupid. And OkCupid led me to, for the purposes of anonymity, Toni.

Toni was an older woman. Well, at least it seemed that way to me at the time. As a 22 year old man, 9 years seemed like a huge gap. However, this just added to her allure. I had never been with someone who wasn’t my own age, and she seemed so confident and sure of herself. Little did i know that this night would be the start of a long and lustful fondness for older women. Toni was my first match on OkCupid, and she sent me my first message. Her agenda was summed up very succinctly in 4 words:

My wife’s fantasy [Group]

Our fantasy [group]. Tell us what we should tweak to make it even more fulfilling.

The night finally arrived! I have been planning this night for a long time. My wife Gracie has been teased with little details, but does not know the whole plan.

I instruct Gracie to take a long bubble bath with a glass of wine and get herself ready. While she is bathing I lay out her outfit for the night, matching black lace bra and thong, stockings, knee high boots, sexy maroon dress and her remote control vibrator. I take a shower and shave which is made difficult because I can’t stop looking at Gracie, knowing the night we are going to have.

After her bath I watch her getting dressed. Gracie is the most beautiful woman I have ever met. 6’tall brunette with legs that go on forever, sexy hips, B cup breasts and a pussy that’s I cannot keep my mouth off of.