High School Archives — Page 554 of 805 — NSFW story

Paint [M]y [F]ace

Hi,

First of all, let me just tell you English is not my first language, so i’ll probably write a few mistakes.

I’m from a small city, and when I went to university I moved to a big city. Luckily (or not), I moved to the same city as my high school girlfriend.

Because we were very young, we decided not to move in together. Needless to say, one year later we broke up, it was not a dramatic break up, we just had different lives and objectives.

A couple of months later, I was working part-time at a clothe store in a big shopping, and become best friend with a gorgeous girl I’ll call Ana.

Ana was beautiful, 5’3″, blonde with great tits (not huge, but perfect to her body), and a smile to die for. Of course I knew the moment I met her that she was way over my league.

I’m not ugly, I’m just a regular guy, and this is a 10/10 girl. Read more »

Ivy’s fall from Innocence [Prologue]

Cameron sighed out in frustration at the amount of work on his desk that needed to be done here at his office as he sat back in his leather recliner chair on the 90th floor. It had hardly been a week since he accepted the General Manager’s position here in this city that is their major HQ hub of the entire asian region. Having taken over from a less competent predecessor that had fumbled things up so badly, the powers that be decided they couldn’t trust in that person anymore.

Hence here he was now, it was a huge promotion that was sure but given that he had no wife made it easier to make the decision to move to Asia. Swivelling his chair around so that he was looking out of the window pane’s of his office down at the city. Lights were already coming on all over as the distant sun started to set over the far horizon. Seeing this scenery reminded him to check the time as bringing up his Breitling watch which was showing it was already 6PM.

*Guess I should probably head on over there.* He thought as he got up from his chair as he straightened his suit & tie before heading for the door. Read more »

[MF] The barely legal virgin Catholic schoolgirl

Continuing on with some of my Craigslist personals (RIP) best of, is every dude’s bucket list entry, the schoolgirl virgin. She answered to a pretty generic ad, so I figured it was probably fake. I don’t remember it word for word, but it basically said “I just turned 18, I’m tired of waiting, and I want to be fucked.”

As I said, I was hesitant at first, partly because I still didn’t believe it, partly because of her age, and also I had never been with a virgin before, so didn’t know what to expect. We continued to talk and I confirmed she was definitely real. She was a Latino girl, pretty cute, a bit chubby, but pretty nonetheless.

I wanted to make sure this was one hundred percent something she wanted, as there is no going back, you know? She wanted it, badder than I even imagined. So she tells me goes to a local Catholic all girl high school and we arrange for me to pick her up after she gets out on one of my days off. Read more »

[M]y [F]irst time was a big disapointment

This is not a story with crazy and wild sex but the real story of my first time ever sleeping with a girl. But i thought it would be at least interesting to write something different. I never really had a clue what to do when it came to girls when i was younger, a mix of no experience and being a tad socially awkward . High school went by without me having kissed a girl, let alone have sex. But as i got older i got more confident which was probably helped by me starting to working out and lifting weights. I’m more of a late bloomer when it comes to sex.

Lets call her Megan, we met online and started texting. I thought she would have been out of my league but we got along well and continued texting and getting to know each other. I could make her laugh and i guess she thought i was an interesting person. An oportunity arose when my parents went on holiday and i had the whole house to myself for a week. I scraped up the courage and asked Megan to meet up and she said yes. She started calling it a date instead of a meet so things were going well. We also talked about relationships and sex, i told her i never had sex before so she was aware of that. She was a lot more experienced than me. I felt like we knew each other pretty well before meeting up. Read more »

18 year old virgin completely soaks through her pajamas during foreplay. [MF]

So this is something that is seared into my memory and I think about it often. This happened on more than one occasion but I’ll just share the most intense time.

I (male) was dating a girl, we’ll call her Elizabeth, her middle name. We were both 18 and fresh out of high school. We considered ourselves Christian’s and attended church on sundays. We tried to live like good little Christians, didn’t drink or smoke and were saving ourselves for marriage.
I’m was, fit, brown shaggy hair. She was probably 5’3, 100lb. Toned legs, great firm butt, A cups, auburn hair, impeccable smile and perfect skin.

I lived with my parents and she lived with her friends mom since she was going to college in a city kind of far from where she grew up. Read more »

How I transformed from a timid and shy wife to a confident, cuckolding, wife! [F]

So, I am constantly asked and DM’d by women who want to hear my beginning story. The how and the why part of my lifestyle. They always look for advice and I love giving it to them! So I figured, I would start at the beginning and share my life story from when I started to cuckold my husband! I will try to make it as sexy as possible but I want to get all the details right! One last thing. This story is addressed to all the ladies who are or have ever been in my shoes. Please, make yourselves happy.

I was just a normal cooperate house wife. I left home after graduating high school early at 16. I studied cooperate management and business administration in college and soon found myself working for a few start ups at just 19 years old. I lived and breathed that white collar lifestyle. I grew up in a very very religious house hold, which ended up pushing me away from organized religion. I was taught that anything to do with a woman’s happiness was inherently a sin. But when I was 14 and I was in a jacuzzi late at night alone and when I turned on the jets (like any economically conservative teen would do in a rich hotel) I felt some thing. I was told it was naughty to have those feelings, but why did it feel. So. Fucking. Good? From that moment on I knew it was time for me to hurry through high school and live my life free! Read more »

Ending a 3 year dry spell [MF]

I wanted to share a story from my early 20s. There’s a little bit of back story but I hope you enjoy.

When I was in high school I did not have much luck with the opposite sex. College was a different sorry, but I ended up breaking up with an emotionally and physically abuse girl and it put me into a bad state of depression. I ended up gaining a ton of weight and had body issues.

After graduating college, I decided to try and get fit again and I ended up shredding a ton of weight and I started talking to this very cute little Latina woman, 23 years old, under 5’3” very curvy in the right places. We were taking things slow but hitting things off really well. I felt a deep connection to her but she was very hesitant to be in a relationship because she had just ended one with a very manipulative guy and abusive guy. Read more »