Story 1: (M)y (f)irst time bareback – with an ex-gf in HS

Angelina (I called her Ang for short) was a normal girl from the Bible belt South where we both grew up and went to school together and began dating Freshman year of high school. She was a red head with green eyes, about 5’4″, 34A breasts, wide hips, and pretty skinny. I was a 5″8″ skinny band geek and runner. We took each others virginity about a year later and a year after that we broke up. By our senior year we were friends again but in a casual way. As graduation approached we found ourselves at the same party with some band friends and at one point wound up sitting next to each other. We chatted and had a few laughs as we drank the cheap wine someone had smuggled out of a local grocery store. There were no parents in the house, just a dozen or so band geeks – nothing to worry about.

Story 1: Teen cousin-in-Law, pt. 1

I guess I’ll start at the beginning, with my first encounters.

As a 13 year old I was a still slightly awkward 8th graded with zero female experience. An honors student in band and still in glasses, I didn’t garner much attention, nor did I have the confidence to go seek it outright. Average height, slightly skinny, nothing spectacular or bad, just an Average Joe teenage boy. This was the early/mid-90s and we lived in a rural area, before the internet, and I’d seen maybe one Playboy in my life just a short time before this takes place.

That summer before 9th grade I got contact lenses, which helped. And then my uncle and his wife and two teenage daughters came to stay with us for a week. The oldest was around 19 while the youngest was a few months older than me and had just turned 14. I’ll call her Mary. She was a very pretty brunette, brown eyes, shoulder length hair, with A or B cup breasts already and a nice, athletic body. After the initial get-to-know-you couple of days we got along pretty well. (The daughters were from my uncles new wife from her previous marriage, so they were not related by blood at all – so though I’ll just say cousin for shortness, she was an “in-law”, just to be clear.)