Author: jakebrooklyn

One of the greats [MFF]

*You gotta do what your heart tells you to do. Let me tell you somethin’ right now. You’re only allowed three great women in your lifetime. They come along like the great fighters, every ten years. – A Bronx Tale*

Times have significantly changed since 1960. People are more promiscuous. While there still is a stigma against sleeping around that exists in our culture, it is thankfully becoming increasingly accepted to have a lot of sex. Maybe not as much as I have, I’m positive that I’ve had partners that never would have even breathed the same air as me had they known how much fucking I’ve done, but a lot. However Sonny’s quote rings true to me when I think about blow jobs.

I had fucked Joan a few hours before. That story will come later. Joan was a friend of Sarah, my girlfriend at the time, and in town for the weekend. And for the record, Sarah was present when I fucked Joan, it was that kind of relationship.

We didn’t really have any plans for when Joan was in town, which ended up being a good thing, as we ended up having copious amounts of sex. And while the sex was memorable and fantastic, Joan’s blow job ranks as one of the greats. Read more »

All night long [MF]

Emily was a dirty whore.

And I don’t mean that in the “I was drunk, and she left me at the bar” kind of dirty whore. Nor in the “Oh you like that, you slut, you dirty whore” kind of dirty whore. I mean she turned tricks for money, and she wasn’t the kind of person one would call clean. A dirty whore. Literally.

But she happened to be one of the few people I’ve ever met whose libido matched mine.

This story starts late on a Wednesday night. I was bored, horny and at home. And being that it was nearing midnight, things were winding down for me so I could get some sleep before the next day. I was wasting time on my computer, surfing around, and looking at porn when I got an email.

EvilOrchid has sent you a message

I had sent her a message on a random dating site a few hours earlier. She looked really cute from her pictures. Spikey black hair cut short, cool tattoos and piercings, and a devilish grin. She liked my message/profile, and was wondering what I was up to. Obviously, I thought this girl was cute, but it was late, and was I really interested in having a first date with her? Of course I was. Read more »

She loved how my cock curves [MF]

I’m not even sure how I ran across Lee Anne, but I think it had something to do with the fact that she went to the same school as my then girlfriend Sarah, though they didn’t know each other. But we chatted and realized that we lived only a few minutes from each other. I asked what she was doing for dinner, she said nothing but she had to study for some test later. Sounded fine to me, how about we get some pizza delivered? Great.

My first thought was “That was really easy”. The second was “Ahhh college”. I had only graduated about a year earlier, and was flirting with the idea of grad school. And like many before me, I didn’t have the easiest time in the world transitioning between the two. Sure adult life was cool with its having a job, and responsibility and what not, but college had girls that invite you over to sit on futons and eat crappy pizza. Life may be a series of choices, but I was attempting to have my cake and eat it too. Read more »

We had just met [MF] [MFM]

We had just met.

Despite previously talking to Jin via email, we had just met.  Jin was married to Umi, and they were exploring their sexuality.  They liked the idea of swinging and curious about cuckold relationships but didn’t know where they wanted to go with it.  I liked that they both seemed to be on the same page and going into deeper facets of their sexuality with their eyes open.

We had just met, but I had watched Umi work the room.  She was expressive, nervously talkative, and cute.  Jin was always by her side, but let her do most of the work.  He was there for her, but she was in charge.  She was clearly looking for something.  I think girls that take charge of the situation are undeniably sexy.

No formal introductions were ever made.  I never shook Jin’s hand, nor asked if I could get Umi a drink.  Watching how they acted and approached guys and couples was enough.  If they didn’t know who I was, they would hopefully find out soon enough. Read more »

Keys [MF]

Whenever Sammie asked me how big my cock was, she wanted me to estimate its sized based on the space between keys on the keyboard. I suppose this his how some people thought, back when hooking up with people from the internet wasn’t as established as it currently is, and every phone didn’t have a camera built-in.

“Does it go from the “A” to the “K”?

“I don’t know how big your keyboard is.”

“They’re all about the same.”

“…”

“It’s probably only “A” to “J” isn’t it?“

“Hold on.”

“My guess is “A” to “;” but I have no idea how big your keyboard is, so it could be bullshit.“

“Wow, “A” to “;”! You’re going to split me in two!“

It went on like this for awhile. Sammie lived nowhere near me, and we didn’t talk that often. But every now and then we’d chat. She’d ask me about my cock, I’d tell her, and she’d tell me all the wonderful things she was going to do to it. This all sounded great in theory, but it’s not like I was going to fly out to see her any time soon. Would she bring a keyboard into the bedroom to see if I was telling the truth? It all changed when she said she was going to be visiting her sister who lives in my area. Read more »

Nothing is sacred [MF]

It was Christmas Day, and I was in high school. I had a long distance relationship with this girl Tina. The relationship was a bit strange, as many relationships in high school are, where I never really felt like I knew much about her. We chatted online. We talked on the phone. Didn’t matter. Without hanging out in her presence or with her friends, it was a different kind of relationship. I was the guy on the side, the x-factor, the unknown.

We had times when our relationship was incredibly sexually charged, and had times where it didn’t factor in. Sure, that’s how real life is sometimes, but like most teenage guys, my libido was often in overdrive. So much that I went out to visit Tina for Christmas.

Dinner was pretty boring. Her dad clearly didn’t trust me, and her mom wasn’t too fond of me either. They did their best to discourage anything from happening between us, and did a pretty good job for the most part. Needless to say, I walked around with an granite-like erection most of the time. If I were a teenage daughter’s father, I wouldn’t like that about me either. Read more »