Author: unholyintentions

I gave a guy my panties in an underground parking lot downtown [FM] [then 22F, 42M]

Posting this now because, if my memory does not fail me, this happened exactly 10 years ago today.

In my youth, I had a talent for meeting up with older perverts (thank you, Craigslist). I once met a rare and extremely handsome man. You know, that type that looks like y’all’s favorite retired unretired football player. He said he was single and free of STDs. I did not believe him for one minute. Still, I was young, dumb, and horny.

For some reason, Mr Stereotypically Handsome didn’t compel me when we met up. I knew I would ignore his future messages. Something about one’s budget getting spent entirely in the looks department. But he had driven a while to meet me, and I did not want to go empty handed. I asked where he was parked.

His car was at in the underground parking in the tourist area downtown. The area that was packed full on that hot and humid summer weekend. Read more »

One night stand [FM] [20s] [femdom, male dom? You decide]

It’s hard to pinpoint the things that built the mutual interest. Maybe it was the beauty of his facial features, the sight of the gorgeous muscles down his neck, while he listened intently to the friendly banter. Maybe it was her laughter, unabashed. I think it was the boldness of the anecdote she shared, and how he was the first one asking follow-up questions. The point is, as the evening went on and the music got louder, their positions in the room shifted gradually until they ended up next to each other.

It is easier to pinpoint the moment of declaration, of implicit understanding. Her gaze met his, quiet, almost a cold refreshment in a room too humid and hectic. It didn’t leave him when his hand reached hers. It was the igniting touch, the launch of a rocket on a mission to reach the heights of outer space. He leaned into her ear.

“Do you have any place you need to be tonight?” Read more »

Fondled and fucked at a summer music festival [FM] [then 22F, 50sM]

*I got inquiries about my post-boat sex adventures with the Craigslist DILF. As always, I am eager to please. In retrospect, I am realizing our encounters had a healthy dose of kink. Today’s story involved a fairly large and famous summer music festival, his hands on my body on the festival lawn, and his dick pumping me full of cum afterwards in the hotel room.*

Boat-and-summer-festival DILF raised the bar for my future dates by being 1) decent 2) an excellent communicator. After he fucked me on the boat, he was careful not to drop the ball. His messages were short (but insightful), sweet (but kinky enough), constant (but not burdensome). He responded appreciative and promptly.

“Have you ever been to [locally famous outdoor music festival?]”

“I haven’t, why?”

“I think your body on the lawn would make everybody’s day more beautiful.”

I may have many shortcomings, but I am good at landing on my feet, especially when it comes to sexual opportunities. I knew DILF wanted to play with me in public and I decided on the panties I would wear. Read more »

I [then 22F] fucked a 50-something on his boat [FM] [full story]

*This is the more detailed version of my slutty confession earlier today.*

———

Today I am thinking back to the summer day that I met up with a 50-something year old who responded to my ad on Craigslist. I had low expectations, but the chat was nice, and after dinner we walked along the piers.

“Would you like to go on a ride? I could take you to my boat.”

“You have a boat? I’d love to see it.”

Always an expert at first Craigslist date safety.

​

I know I post a lot of age gap stories, and it might come across as if I were perpetually chasing older dick, but I can say in retrospect it was a very legitimate date. I mean, I wasn’t doing *all* the thinking with my pussy. His Craigslist response was insightful and the conversation over dinner was great. He was excellent at flirting and I had fun dressing the part. Hair down, great face, a very flattering summer dress: purple, form-fitting, clinging onto the right curves. He was smart and quite the respectful gentleman. All this said, who am I trying to kid? I had posted the Craigslist equivalent of a RAOBJ. Read more »

The time I hooked up with an older man at a BBQ [FM] [F26, M42]

I love American BBQs. They’re kind of family settings, but it’s also kinda okay to flirt. You get to share good food and meet new people. In my case, I’ve never been a fan of cornhole, so I adapted it into a game more akin to my interests. Fortunately, one of the DILFs was very willing to give my holes the most thorough beanbagging.

This was a warm summer day a few years ago, and the flirting started as very innocent and friendly banter over our respective contributions to the BBQ potluck. He wanted to know my salad dressing recipe and I praised his sliders. As the afternoon went on, we continued chatting: He was a recently divorced dad, living on his own when his kids weren’t around, and just trying to have a fun summer. The perfect opportunity to strike.

“Are your kids with you this weekend?”

“No. They’re with their mom. I’m all by myself until tomorrow night.” Read more »

I didn’t let a guy’s literal guns ruin our hookup [FM]

Maybe I should have posted this one on July 4th to celebrate what makes the United States unique, but I guess I can share it now: I once hooked up with a guy who had rifles hanging from his living room wall.

We met on Reddit when I was on a work trip in his city, and he turned out to be pretty cute and experienced in bed. When we got to his place I didn’t notice the guns initially. How does one not notice rifles hanging from a wall, you may wonder, and I don’t have a satisfactory answer. Dumb slut brain will never focus on what’s most important, I guess? I only saw them when we were half-naked after minutes of making out.

I would love to say that was enough to get me to leave, but of course I serviced his dick until he was rolling his eyes constantly and bucking his hips to reach deeper in my throat. He wasn’t outstanding in bed, but it’s always fun to be with the type that knows how to slap and choke. Kind of tracks with the whole gun display thing, I guess. Read more »

I deepthroated a neighbor in his car [FM]

I deepthroated the older guy on the beach, I deepthroated the designated driver. I am on a kick lately fapping about my past deepthroating glories, and today I thought of the time I deepthroated a neighbor in his car.

Full disclosure: we lived within a couple of (walking) minutes from each other, but we actually met through Tinder. On our first date, I did not feel compelled to return for a second one, but I was horny and so was he. So I started planting seeds in the dinner conversation.

“So what are you looking for on Tinder?”

“I don’t know, I’d like to find a girlfriend, have a good time. How about yourself?”

“I am only looking for a good time.”

As it happens, none of us could host that night, so he offered to drive me home. I accepted, and it immediately became obvious that driving me home actually meant driving to the marina in our area first. Hmmm. I was no teenager, you know? But I looked down at the bulge in his pants and it was easy to accept the deal. He very visibly had a huge cock. Read more »

I deepthroated the designated driver — My first deepthroating ever [FM]

*Disclaimer: Alcohol mentions and descriptions in this one. Do not assume you can drink like I did and not get drunk; I have long since lost that superpower. Also, to my fellow cumsluts and deepthroating lovers: do not mix deep cock with alcohol if you want to keep your doctor away.*

——

One of the most memorable slutty nights in my youth took place during a bar and nightclub crawl. I was in my late teens (in a country where that’s past the drinking age), oddly unaffected by copious amounts of alcohol, and completely attracted to the designated driver of that night. He was someone’s brother: a few years older, edgy, handsome.

I did not plan to remain sober in bars 1, 2, or 3, where I had the same drinks as everyone else. For whatever reason, I felt absolutely nothing. Designated Driver noticed this — he remarked how I was holding conversation as if I had consumed nothing. Maybe it will hit me later, we thought. Read more »

I deepthroated an older guy at a beach near me [FM]

Some years ago, in a particularly dry season for my sex life, I kept my eyes open in dark corners of the internet to see what was new. Man, some people put some really risky stuff out there! I read those mostly for entertainment. Mostly.

There was a guy who used to post a lot in an area near me. He invited people to masturbate with him in his car at the beach early in the mornings. I thought that was pretty ballsy and kept scrolling.

But they say repeated exposure normalizes things, and I started to wonder what this guy’s rise and shine routine was like in practice. You probably see where this is going… one day, curiosity got the best of me.

I set my alarm and went to the beach, dressed in sports clothing. I went for a light jog. There were many places he could be parked, and I didn’t really know what to expect. Because it was so early, there were few cars, but I had no idea of how to find him. I had not reached out for more details. I jogged slowly a couple of times and found a handful of cars with single men inside, but nothing that would give him away. I gave up that day. Read more »

I always said no to hooking up at work [FM]

Have you ever realized mid-fuck that you’re in trouble? That this was all too reckless?

Maybe it was when you were copulating in a slightly too strong state of inebriation. Maybe it was when his wife opened the door while you held your lips to his pubes. Maybe it was when you finally realized you were balls deep in the ex that had broken your heart but still used you for loans and booty calls.

I had this sinking realization when I heard the snap of the condom against his cock in the darkness of his hotel room. When he whispered in my ear that I felt better than he had imagined it.

I had it when I saw him at work again not long after. When work colleagues mentioned him in conversation years after the fact.

To be honest, though, I had it long before all that. I first had it when our eyes met on the first day of the conference, just after he walked over to tell me he had looked for my name in the conference participants list. He had always been the handsome coworker who treated me differently, who kept pointing out all the things we had in common. Read more »