Ch. 01: Several Firsts with a Friend - Sex Stories

Ch. 01: Several Firsts with a Friend

I'd like to share some stories. I've had some interesting experiences that are much too sensitive to easily share; so I've bottled them up for years and years. I'll start with my very first sexual experience and progress through a history of unique encounters.

Firstly though, every detail is absolutely authentic and factual. Second, certain details have been left out to protect identities, especially of the women in these stories who aren't aware I'm sharing them.

I'll take you through my first, which was actually several firsts in one, then go over my wonderful first experience through the world of online hook ups, and finish up with a story of how perfectly great sex can be ruined by what happens afterward. I hope you enjoy.

I was about 19 and shy... really shy. That shyness was oddly enough part of the reason I was so horny. I know, 19 year old guys are always horny. But you have to understand I was on another level. You see, not only was I a virgin but I hadn't even kissed a girl. So there I was, a sad little 19 year old with a tent pole in his pocket 24 hours a day.

I was at a party having a good old time. I'd met some new people and chatted with old friends. One new person was a woman who happened to be a friend of a friend... of a friend. So yeah, very distant in degrees of friendship to say the least. We chatted and she was very nice but I wasn't likely to see her ever again. Not only were we separated by our line of mutual friends but also age. She was 30 ...

... years older than me. If you're doing the math in your head, she was 49. Anyway, we went our separate ways and that was that. Or so I thought.

As it would turn out, the world is pretty small and we kept running into each other. Sometimes it was at a party, sometimes at a restaurant, you just never knew. And I'm not talking about bumping into each other a few times in a few months. I'm saying I probably saw her monthly for a span of almost three years. We actually got to know each other and got along very well. We would talk about all kinds of things including my shyness and lack of a girlfriend. We'd bump into each other at the bar once I turned 21, have some drinks and have a good old time. We even exchanged phone numbers and hung out together, just the two of us.

One day, she calls me and asks if I want to hang out. I was headed to the gym and wanted to stick to the plan. She understood and asked if she could join. I saw no issue and had her meet me. I was allowed one guest so she got in with me and we started doing some cardio and chatting. It was late, maybe 9:00 PM. The room was dark and so was the outside world barely visible through the glass store front.

We were on the stair climbers chugging away at a leisurely pace when we got onto one of our typical subjects which was my love life or lack there of and that's when she surprised me.

She told me how she understood how I felt and that she wanted to be that person I needed. My head began spinning. I tried to ...