Author: YouCantSeeMe91

My First MILF [MF]

My name is Andy. I grew up in a very religious household, so I was a late bloomer. It took me until college to have my first kiss, and I didn’t lose my virginity until I was twenty-one. Since then, I’ve been doing my best to catch up. This is the story of the first time I slept with an older woman:

As I’ve mentioned in previous posts, I’m in the Army. That experience led to a lot of opportunities to travel, see new things, and meet new people. It is not, however, particularly conducive to dating. Fortunately for me, I had plenty of friends who were happy to set me up with people they knew.

One of these friends was an older woman named Janet. I was over at Janet’s house, having a beer with her husband, when she mentioned that she knew a woman who was looking to date. Janet asked if I was comfortable with a woman having kids, and being a little older. At the time I was 24, and the woman with whom Janet was setting me up was 37, and had a 17-year-old son. I told Janet that I was game as long as she was a cool person. Read more »

Making the Good Little Christian Girl Mine [MF]

My name is Andy. I grew up in a very religious household, so I was kind of a late bloomer. It took me until college to have my first kiss, and I didn’t lose my virginity until I was twenty-one. But since then I’ve been doing my best to catch up. This is the story of the second woman I ever slept with.

In college, I was a member of a Christian outreach group for high school students called Young Life. I’m sure that plenty of people are aware of it, but essentially it’s a weekly club event where high schoolers come and play games, watch skits, sing songs, and hear a brief message about Jesus from one of the college-aged leaders. It was always a lot of fun and while I don’t currently consider myself a Christian, it was a big part of my college life.

There was this high school girl that attended every club, as well as our weekly bible studies. Her name was Rosie, and she had the greatest pair of tits I have ever seen. To this day they’re still my favorite. But she was in high school and I was in college, and there was a very strict policy against doing anything romantic with the Young Life attendees. So, like any good Christian I did the right thing and masturbated to thoughts of her constantly. Read more »

[M]y [F]riend is a Phenomenal Wingwoman

My name is Andy. The events of this story take place a few years ago. I was about to leave for Afghanistan, and things were intense over there so I was very anxious about the whole experience. Military people will be able to relate; it’s a strange balance between being nervous for your own well-being and being ready to go because it’s kind of the entire point of military service. This strange dichotomy had me very worked up emotionally to the point where I was on edge for the entire month leading up to the deployment.

A couple days before shipping out I grabbed dinner with my best friend and his girlfriend. They both immediately picked up on my emotional state and reached the same conclusion: I needed to get laid. My buddy and I are not from the town we’re stationed in so it fell to his girlfriend, Perla to come up with potential options for meeting a young lady. Fortunately for me, she is one of the coolest women I know and immediately pulled out her phone and began going through some of her friends’ pictures on Facebook. After a little bit of scrolling, she perked her head up and looked at me. Read more »