Author: jakebrooklyn

Bellissima [MMF]

Years ago, I had a long day at work, and was getting a drink at a bar in midtown after. Needed to decompress a little before heading home.

There were sports highlights on TV. I was watching part of a soccer game, and when watching a particular play said, “that’s bullshit!” probably a little too loudly.

And this guy sitting like fifteen feet away was like, “You’re right that was bullshit.” And I was a little embarrassed about how loud I was but said, “Yeah it was.” But he continues, “Do you know how I know?” No. “I used to own a team in Serie B. And it was 20,000 Euro for a yellow card, 50 for a red.

To which I had a hard time believing. But he spoke a little bit more of that experience, and he may have been telling the truth. So I was willing to go with him on this.

We talked some more. He was staying at the hotel attached to the bar, in the penthouse, here on business. And he was here with his wife, and asked if I could help him out with a problem he was having. I said I’d try. Read more »

black scrubs hide wetspots [MF]

As soon as she left, my pants hit the floor. Immediately. Partially because I felt the intense need to get off, and partially because she wanted me to. Commanded me to. I was rock hard in a matter of seconds. Smelling her on me. Feeling the sting of my nipples. Freshly bitten. I had to suck the cuff of my jacket because I wanted to taste her more. The feeling is intoxicating. It consumes me. I had to go for it. Hard. Two hands. Working myself. Eyes closed thinking about how amazing it’s going to be when it’s her body on top of mine. Needing her, but knowing that she wants me to feel like this. To be left lacking. In a frenzied state. Desperate for her touch. It became too much. I erupted. All over my hand, wrist and shirt. Had to go to the bathroom to clean it all off. And as she reads this, she might be getting on the train, and she’ll probably feel the mess left behind from all the times she squirted on me. I hope that it fills her mind with wonderful, lascivious thoughts.

A play in two acts [MF]

**Round 1**

During the courtship process, I told her that I’m well endowed. Not to brag, but more to make sure we’re all on the same page. It’s really frustrating to find out that I’m too big once everybody is naked. It’s also frustrating to find out I’m too big ahead of time, but this way saves time. And if you could be anything, you should be efficient.

The first date went really well too. Cocktails, chatting, flirting, laughing touching. Pandemic pay have taken its toll on a lot of things, but NRE is still really fun. She was feeling it as well. So much so that after we finished the third round, she said that her office was right around the block and asked if I’d like to check it out. Yes. Yes I would.

She’s a therapist and had a nice, minimal office. Leather couch and chair. Book case. Window with a view. She walks to the window, and I approach her from behind. Caress her waist. Kiss her neck. She turns, gets on her tip toes and kisses me back. It’s always cute when they do that. Kissing leads to more kissing. Lip sucking. Ear lobe biting. She turns the air on, as the window is steaming up. Read more »

[MFF] Only in New York

This is a true story that happened in a time before Covid. Everybody was well over 18 at the time this took place.

A wonderful perk of my last job was that I got to engage with a lot of vendors. I’ve heard stories about how things were back in the day with lavish expense accounts, and how things aren’t the same now. And that certainly may be true, but in my experience, there are still some vendors who really want to show clients a good time.

One of these vendors was a decent sized engineering startup that I’d built a relationship with over the previous few years. Due to them being based in California, we didn’t see each other in person very often, but when we did, it was always fun. Good food, good drinks, general revelry.

On this particular trip, the vendor, who we’ll call Austin, was going to do something like a tour of his NYC-based clients. Not a bad gig showing clients a good time and strengthening their relationship. So on Monday, I went out with my colleagues for dinner and drinks. As always, it was fun to catch up on their dime. Read more »

So, how slow do you like it? [MF]

The first girl I had sex with, when we were 18, gave me an incredibly slow hand job. Her pace excruciating. It was like stroke. Wait one to two seconds. Stroke. I was over her, one knee on either side of her hips, while she was laying on her back.

Maybe she had gotten advice that young guys cum fast, I don’t know. But this was agonizing. The entire thing took around 80 minutes. It was kind of like edging, but there wasn’t the up and down and back up again. This was like the most gradual incline ever.

When I finally, finally had an orgasm, it was a truly amazing feeling. Like those shampoo commercials where the woman immerges from a waterfall and tosses her hair. I leaned my head back and closed my eyes, as it was so overwhelming.

Only there was no cum. I was no stranger to jerking off, and I knew what an orgasm felt like. But this was perplexing. It seemed like there should have been a lot what with all the build up, but nope! So I kind of snapped out of it, and then leaned down to kiss this wonderful girl who made me feel so amazing. Read more »

Not Always But Often (long) [MF]

Dancing is a cliché that’s often used in movies to show two people falling in love. I’m fully aware that there is a culture of people that go out to clubs for the express purpose of dancing. In fact, I’ve done it before, but it’s not a habit of mine. This story does not start at a dance club.

Instead it begins at a hotel. Funny, that’s often where they finish, but this one starts there. I wish it were an extravagant hotel. Or maybe a super-modern one. But this hotel was none of these. It was in a suburb, on a road with a lot of big name hotel chains. The parking lot needed paving. The location wasn’t particularly convenient. The hotel was chosen due to its cheap price.

Your circle of friends may have different ways of gathering, but I’m in one that enjoys getting together for a long weekend at a hotel every now and then. It’s an excuse to drink, act recklessly, reminisce, fuck, and drink some more. While I don’t often go to these weekend excursions, due to finding them to be a little tired, they’re enjoyable every once in awhile. Read more »

[MF] Rae wanted anal

If you were a cute girl and you came up to me on the street and asked “Will you fuck me in the ass,” chances are I’m going to say yes.  There would be an accompanying stare of disbelief and lust, because these things don’t happen to me very often, but I’d be into it.  However if given the choice, I generally prefer vaginal sex.

One of the functions of the vagina is to make penises feel good. And they succeed.  This might be a bit obvious, but I love the feeling of having sex.  Not that I don’t love a lot of the other aspects of sex, but the sheer physical pleasure of repeatedly thrusting my cock in and out of a girl is amazing.  Wars have been fought over it.

From what I can tell, a lot of people seem to really enjoy the taboo of anal.  No matter how advanced our culture becomes and how laid back people can be about sex, there will probably be the element of feeling dirty associated with anal sex.  Don’t get me wrong, I love feeling dirty, it turns me on like few things do.  But anal has never really fascinated me with its “wrongness” the way that other things have. Read more »

The Quickness [MF]

Sullivan and I had sort of an on again off again relationship. Most of the time we were off, but the times when we were on were great. I have one in mind that I’d like to share.

We had already fucked several times prior to the Saturday night we were to hang out. Sully was interesting in that she enjoyed short but intense bouts of sex. I’ll delve into that in more detail in a bit, but it’s worth mentioning that we both knew going in that we were hot for each other, and that we probably had only actually had sex for about an hour total.

She lived on campus at the time, and we went out to dinner at one of the restaurants a few blocks from her dorm. We chatted, talked about school, had a few beers, nothing out of the ordinary. But the entire time we seemed to be really absorbing each other’s conversation, and gazing into each others eyes. The vibe I got from her was that she was partially “I am really into you” and “I really want you into me”. Read more »

What lies beneath [MF]

Even now as I think back about my one night stand with Francesca, it seems slightly surreal. We met online, and agreed to meet up for a drink and a movie. Not dinner, we didn’t want to make that kind of a commitment without even knowing each other, just a drink.

We met at a very non-descript bar. I ordered a Long Island Iced Tea, and she had a glass of white wine, which both felt appropriate for the summer. Sometimes the get to know you chit chat of when you first meet somebody can be very banal, and sometimes it can be excited. This was part of the former.

Where we grew up, what we do now, where we went to school, all that stuff. Yawn. Not that this wasn’t all good information to know. But I was already starting to get that cookie-cutter feeling, and we barely even knew each other.

I did learn that she had been broken up with her ex for about six months now. She mentioned that she sometimes had a hard time staying away, but kind of let her voice trail off. Clearly the single glass of wine and our half hour of conversation wasn’t enough to pry whatever was behind her words out into the open. To be honest, I wasn’t really concerned. If she wanted to tell me, she would. If she didn’t, she didn’t. Read more »

Window of opportunity [MF]

Good things take time.  Great things happen quickly.  Knowing when the latter has become the former is a truly an art form.

This is what I knew about Elena…  She was cute, she lived near me, she had an on again/off again relationship with some guy I didn’t know, and she was cute.  While I have hooked up with women from every stage of relationship from just dumped to just married, not all situations are created equal.  I find that women in relationships often have a lot of baggage, and it is not always worth dealing with.  Frequently it is, but in Elena’s case, I just wasn’t that into her.

Yeah, she was cute, and we always had a flirtatious relationship.  But she wasn’t a head-turner, she wasn’t especially smart, and she often complained about her boyfriend.  Enough for me to roll my eyes whenever she’d bring it up, but not enough to stop me from talking with her when I got the chance.  But when I found out that he was out of the picture, I knew that I had to take the initiative. Read more »