Sexual Reflections: (M)y First Time | 2016

I am writing down my sexual (mis)adventures as a way to preserve and reflect on my memories. I have had so much sex of that everything becoming a lot less clear than I'd like. There's a lot of things I've done that I'm not proud of, but it was these experiences – the good, the bad, and everything in between – that have molded me into the sexy, confident person I am today.

About me: I'm 6'2'' with piercing blue eyes, brown hair, and a lanky frame. Only recently have I begun to fill out with muscles. Think of a much more awkward Beau Mirchoff and you'll have a close enough idea of what I look like.

A few other things bear mentioning: I went to a strange, tiny high school that for some reason was mostly male. As a result I didn't have much experience with girls, and having sex with a girl from my school simply wasn't going to happen. I also have a very high libido, and sex is almost always on my mind. I used to (and still do!) read everything on sex. However, these conditions made my teenage life almost unbearable; I was some kind of weird kinky fish flopping about in a sexual sahara desert.

My first time: Somewhere in my hormone-filled brain two neurons rubbed together and a basic idea formed. I had some money but no sex while somewhere a girl had some sex but no money. Perhaps if I hired an escort I could finally, finally have sex.

The escort was named Monica. She was in her late 30s, about 5'5'', curvy and a little bit chubby but not unpleasantly so. She was latina and had long black hair. She was well-reviewed and reasonably priced. She laughed when I said I wanted to make an appointment with her, and asked if it was my first time doing this sort of thing.

I got lost on my way to her apartment. Whenever I called Monica for directions – after fucking up her previous ones – she would ask me if I was playing games with her and I would assure her, scared, that I was not.

When I first walked through her door, the first thing I noticed was that the pictures she used in her ads were much better looking. And younger. I didn't care though, I just wanted to finally be inside of a pussy, any pussy. Monica immediately asked to see my id. I was 6 months away from being 18 at the time (and I looked like a 15 year old) but she just glanced at the birth date and asked me if I was a cop as she handed it back.

We made incredibly awkward small talk as she sipped a huge rum and coke, and then all of the sudden she started to climb the stairs to her bedroom. I followed, my face only a few feet from her firm ass, my cock rock hard, and my mind in a state of excited disbelief.

I placed the envelope with the money on a bedside table then slipped off my clothes and waited on her bed. She wandered over to the stereo and turned it on. Spinning around she started to strip. My eyes greedily took in her tan body and its curves as it was slowly revealed. When she finally peeled off her panties my eyes were glued to her shaved pussy. She crawled towards me, naked, and popped my hard cock into her mouth. It was a lot more under-whelming than I had imagined. After about a minute of her sucking me off, I felt the desperate urge to cum. In order to make myself last, I suggested going down on her, something I had always dreamed about doing.

She flipped over onto her back, and I kissed my way down from her full breasts to her pussy. She tasted like lotion, at least until I started running my tongue along her pussy in a rough approximation of cunninglingus. Her pussy tasted like skin. After about 2 minutes of eating her out, which she pretended to enjoy, I decided it was time. I fumbled on a condom, took a deep breath, and slid myself deep inside of her. As her surprising warmth enveloped my cock I again felt under-whelmed. A sort of this is it??? feeling took over but was quickly replaced with pleasure as I continued to fuck her. Too quickly, actually. After at most a minute I came hard. And that's how I lost my virginity.