[MF] Finally having amazing sex with the woman I saw every day

Several years ago, I worked in an old-school, 70’s style office building near town that was two stories and a maze of sidewalks, staircases and little alcoves. It was kind of a cool building. To get to my office on the second floor, I had to walk down this one sidewalk every day that went directly past a hair salon. There were four women that worked there, which I knew from coming and going every morning, noon and night for several years. There was one in particular that I thought was cute. I’d say she was early to mid 40’s, shoulder length brown hair, with a nice body that kind of gave off a little bit of a hot MILF vibe.

What I found most attractive about her, however, was that she was friendly. Although we never actually spoke to each other, we always smiled, nodded, waved, or otherwise acknowledged each other every time I walked by. I had this feeling that she didn’t do that with everyone, so it made me fee special.

I often fantasized about her when masturbating. Stroking myself to an intense orgasm while imagining what it would be like to be with her.

[MF] A slippery one from India

I’m finding that writing about my experiences is not only enjoyable for myself, but others too, so I guess I will keep them coming :)

Continuing to post for sexual encounters on Craigslist, this time I was looking for actual sex. Never knowing what the responses were going to be like, I received one that sounded legit. It was from a grad student at the nearby university. She didn’t have transportation, so asked if I would come and pick her up. Sounded fair.

We spent a couple of days chatting back and forth via email before we could get together. Things were going well, and we both expressed an interest in just having some good, no-strings-attached sex. Her name was Naya and she was from India. She looked really cute in her pictures and I was really looking forward to her.

I drove to her apartment to pick her up and was excited to see that she was quite sexy in person. Short, petite, long black hair, dark skin, brown eyes. Very pretty. She hopped in the car and we immediately became very comfortable with each other. About 10 minutes into the car ride, she placed her hand on my cock and asked if I wanted a blowjob. I wasn’t expecting that, but I was happy to oblige.

[MF] Meeting an older woman in the hotel bar on a work trip

Lately, I’ve been trying to rank my sexual experiences in my head, and think this is probably the hottest one on my list – probably because it was something I had kind of always fantasized about.

I travel a lot for work (events, conferences, training sessions, etc.) and went to a conference one fall in Pittsburgh. It was at a nice, full-service hotel downtown. One of my favorite things to do while traveling is enjoy some cocktails at the hotel bar and/or wander around the neighborhood looking for a great local place to relax. On this particular night, I chose to do the hotel bar, and I’m glad I did.

It was relatively quiet and Monday Night Football was on at the bar, so I sat down and had my usual – an Old Fashioned. I was just chilling out, nursing my drink and alternating between watching the game and scrolling through my phone. That’s when a nice looking, older woman came in and sat next to me. I kind of just glanced in her general direction and smiled, not wanting to seem rude and ignore her, but also not wanting to make her uncomfortable with too much attention.

[MF] A different kind of Craigslist Casual Encounter

OK, NGL, my story about my first Craigslist Casual Encounter brought back some good memories, so I think I’m just going to document the ones I remember here.

This next one was a little off the wall, but again, it was Craigslist and anonymous, and I was just starting to really explore my kinks and sexuality, so I thought ‘what the heck’. I posted that I wanted to shave a woman’s pussy. I didn’t get any responses initially, so I just kept renewing that post until finally someone responded, intrigued at the idea.

Her name was Megan and she was a 21-year-old that lived a couple of hours away out in a very rural area of my state. She seemed cool, inexperienced, a little shy, but eager to have some fun.

We made plans to hook up at a hotel – one of those old school, single-story motels in the middle of nowhere with exterior doors into the rooms, etc. I almost chickened out halfway up there.
When I got closer, she texted me to meet at a gas station up the street from the hotel, and she told me what she was driving.

[MF] My first Experience with Craigslist Casual Encounters

This was way back when Cragislist Casual Encounters was a thing, and I was really reluctant to look for sex on the internet, so I started slow. It was a post inviting a woman to come and watch me masturbate. It had always been a fantasy of mine and just thought that was a low key, easy way to start.

To my surprise, I received a response that same night from a woman named April. We chatted back and forth several times and set something up at my apartment the next evening. She had shared a picture of herself and I thought she was average, but had some nice big breasts. Most of all, she seemed very eager and turned on at the idea of watching me.

We had set a time for her to come over, and I had started masturbating and edging a while before that so I would be really horny and turned on by the time she rang my doorbell.