Author: Restless_13

The time I [m]et an innocent virgin [f]rom reddit.

This isn’t the only time I met someone from reddit, and it’s not the most X-rated story, but it’s something fun I thought I would share. I was innocently browsing r/drityr4r (the only way to browse this sub is innocently) and I saw a post with a title something like **19 [F4M[ Ca / Online – Sheltered virgin, needs help**. When I opened the post the girl said she was Muslim, a college student, lived at home with her strict parents and had basically no experience with men, and was looking for someone to at the very least discuss some of her fantasies with her.

Now, first of all.. I’m too old for this girl. But I thought I could lend a helping hand (I’m nice like that..and a bit evil), so I wrote her offering some advice and maybe some dirty talk. To my surprise she quickly wrote back and said I was one of the few non-dick pick or overly aggressive replies to her post and she was happy to chat and see where things led. While we were both in California, it turned out she was more than 300 miles away from me, so anything in real life seemed out of the question. This led to weeks of chatting on kik and getting to know each other with some light sexual flirting, but nothing too much. She really wasn’t experienced with men at all and seemed to get quickly uncomfortable when the texts became too sexual, so I backed off. Oh, and her name was Alya. Read more »

[M]y [F]irst love was a stripper

This story is from my early 20s, so it’s not recent, but it is something I wanted to share the story of. This is about my ex-girlfriend Cindy, or we can call her by her stripper name, Cinnamon. Cindy and I were high school sweet hearts. We met when we were 16 and had a mostly normal teenage relationship, except that we grew up Hollywood adjacent and were into the club scene a bit. We had a good time exploring sex and new desires together. She always had that stripper’s body, and would give clumsy, but well intentioned lap dances as she treated 18 year old me to a special occasion.

But then it all came crashing down. We had our problems, I didn’t know how to really treat a woman yet and she was a bit of a wild child I couldn’t fully tame. She had been acting weird, being hard to get a hold of and I confronted her. Some club promoter she met in Hollywood had seen her dancing in a club and offered her a chance to move to Vegas and work at his club. Yes…a strip club. But he supposedly had a lot of connections in the dance industry and he was going to make her a star. It was something out of a bad 80s movie and she was falling for it hook, line, and sinker. The more I tried to convince her he was a sleaze, the more I seemed like a jealous immature thing she needed to get away from. And one day…she was gone. Read more »

I [M]et up with a high school [F]riend I hadn’t seen in 15 years, right after a break-up

Something magical happens when you change your relationship status on Facebook. Old (female) friends come out of nowhere to make sure you’re “doing ok”.

Becca wasn’t by any means my high school sweet heart. We traveled in overlapping social circles, but barely crossed paths during school. But we both thought the other was attractive and this led to a few random kisses and touches exchanged at random parties as we got high together. It was so very high school. But that was ages ago, and we are both functioning adults and that was a different time and a different life.

She messaged me only a few days after my status change.

Becca: *“OMG, I can’t believe you’re single, I would see your posts and always thought you two looked like the perfect couple”*

Me: *“Well, sometimes things aren’t as they appear. I’m just trying to get my new life straightened out”*

I had been with my ex (lets call her Beelzebub) for nearly 10 years. A dead bedroom and constant bickering over money (she wanted more), sex (I wanted more) and a lack of common ground (we both needed more) had eventually lead to our going separate ways. Read more »

That time [M]y date said she has a thing for [f]ooling around in public.

“The thing that really turns me on, more than anything, is fooling around in public. That’s why I always wear dresses, if I like someone”.

Katie had leaned over to whisper that in my ear, so it wasn’t obvious to anyone else in the bar. I nearly choked on my beer, not because it was too unusual for someone to have that kink, but because we were only about an hour into our first date. And well..she was wearing a dress.

I looked Katie over again, she was a cute dirty blonde with freckles from too much sun doting all over her nose, but they just made her look even cuter. She was wearing a loose fitting sundress that had spaghetti shoulder straps, but otherwise it didn’t show any cleavage or any leg. It was a respectable first date dress, that didn’t predict what Katie had just said to me. Read more »

That ti[m]e in Vegas, I met a girl in a gold dress [f]rom Ireland

It was my friend Dan’s birthday and he wanted to go to Vegas for the weekend. So on Friday morning we loaded up my car and made the drive from LA. When we got there we did what any exciting people would do and took a nap before we woke up around 5pm and went down and hit the bars.

Dan’s not the best at drinking too much and by 11pm he looked like he’d had enough. He was looking dizzy and bloated and was talking about going back to the room for a quick nap. I told him not to, that there was way more fun to be had, but he quit on me and made his way back. That left me drunk and very solo in Vegas at 11:30 at night.

I wandered around a bit, going from MGM to NYNY, sitting at their little casino bars and sipping my beer because I wasn’t sure how much more I could drink. Then my luck changed. As I was sitting at the circle bar in NYNY, a booth to myself, a group of Irish tourists asked if they could jam into the booth with me. It was 2 guys and 4 girls, so the odds were in my favor right? They were mostly in their 30s, and I could barely understand their thick accents. Read more »

[M]e and the married Canadian mil[f] I met in Vegas

My best friend Dan and I went on our annual guy’s trip to Vegas. As usual Dan was pressing hard to meet someone to have a 1-2 day fling with, but I was mostly along for the ride. Ready for some serious wingman duty, drinking and naps by the pool.

On our second night there, around 10pm (after some serious pregaming), we hit the bars and just had drinks and talked to people. After a few hours, Dan met someone, a cute latina girl named Jackie and they were chatting it up pretty seriously. So I did what any good wingman would do, I said I needed to use the restroom and I just never came back.

I walked down the strip to another hotel, and another bar, and kept up the drinking, but with a party of one. I keep myself pretty entertained and am good at talking to strangers once I have a few drinks in me, so it’s not sooo bad. This threesome (two girls and a guy) start talking with me as they were waiting for their drinks at the bar. Once the drinks arrived one of the women motions to a booth and says I should come drink with them. I’m more than happy to oblige. The women are fairly conservatively dressed and in their mid to late 30s. The guy seems a little out of place as he’s dressed up to go clubbing and maybe 10 years younger than all of us. Read more »

That time [M]y internet date was a little [F]orward, and asked to see my cock.

Internet dating is always rough, sometimes it’s just boring meet and greats over a drink, where they feel more like an interview than any sort of date, and you just become numb to the possible romantic aspects of them.

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This one was no different. Her name was Marissa, she was 29 years old, an aspiring actress by day and a waitress by night. She’s a caramel colored Mexican girl, with short dark, straight hair, a very cute face and some slight curves. She’s very cute, but not the kind of girl you stare at from across the bar. She was pleasant to talk to, sarcastic and smart, but the whole date felt rushed. She had to get to work at 8pm at a restaurant nearby, so we met for happy hour after I got off work. The conversation wasn’t remarkable and there didn’t seem like there was time for any connection to form. I think we’d both been doing this internet dating thing too long. I think she only agreed to meet because the bar near my house is close to her work. I’m several years older than her, and it’s showing in our conversation..

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[M]e and the Japanese Mil[f]

Saki “What do you mean you’re breaking up with me?”

Me “Well, we don’t really talk much, and I only get to see you every other weekend”

Saki “That’s not fair, you know I can’t see you as often as I’d like to”

Me “It’s not just that, all we do is hangout and have sex, which is nice. But I think I’m looking for something more serious”

Saki “I’m coming over… I’ll be there in 30 min”

Me “I don’t think that’s a good idea”

Saki “I’m coming over”

“click”

So, the back story here, I started dating this Japanese woman named Saki, from an internet dating site. She was cute, sweet and very quiet. Saki was about 5’4” with long straight black hair, perky B cup breasts, a thin waist and curvy hips. She was 33, and had a 10 year old son at home. When she was 20, she had married a much older American business and moved to the US to start a family, the move to America worked out, but the marriage didn’t. That’s how I came to find this Japanese Milf on the dating site I used. Read more »

[M]y innocent date [F]rom a meet-up app went very wild

One night I was board and sitting at home and I opened a “hook up” or “meet-up” app that I have on my phone. This app tells you who’s online and what their distance is. I see a few cute women nearby and one that’s only 0.4 miles away. Well, there’s a bar about 0.4 miles away, so I take a chance, maybe she’s hanging out there.

Her name is Angela, and she’s a 27 year old Latin girl. Her profile doesn’t really say much beyond that. So, I text her “Hey… How are you tonight?”. About 15 minutes go by and she texts back.

Angela “Hey.. I’m doing good, how are you tonight?”

Me “I’m good, but a bit bored. I’m about to walk to Qs (a bar near my old apartment), and have a beer. I’m only mentioning this in case you’re feeling brave and want to walk into the same bar I’m sitting in and have a drink with a total stranger”.

Angela “hah! Good to know. You have fun getting a drink by yourself”

Me “I was simply being neighborly, trying to make some new, local friends” Read more »

That time I went on [M]y [F]irst real internet date

Ok..here we go. In some of my previous stories I mentioned that a lot of my shenanigans were after a long relationship I had ended and I was out exploring again. Well, now, I’m going to tell the story of the wonderful, sweet and sexy girl that was the person who I dated right after that break up.

A little background. I was with my ex for nearly 10 years and she was a strong type-A personality who had always planned and dictated most of our lives together. I think she even planned the 1.5 years of ignoring me sexually that led to our break-up. During that 1.5 years, I developed a wandering keyboard (online shenanigans), but those are stories for another time. After the break-up, move-out and fresh start, I found myself looking to date for the first time in a long time. I signed up for one of those free internet dating websites that a friend recommended. I posted a few pictures where I looked thinner and younger, wrote out my stats, was fairly open in the profile that I wasn’t looking for anything too serious at the moment and that I was just out of a long relationship. Read more »