A brief history of nearly all my sexual conquests. [Part 1] | 2016

Let me preface this by stating that all names have been changed, the details however have not. In some of these stories I will very much be in control, an alpha male who dominates and teaches girls what to do and how to do it. In other stories, mostly from when I was younger, I make mistakes and things don’t quite go as expected. Nonetheless each girl I have had sex with in some capacity gets a mention, including those who I’d rather forget. Enjoy!

Rachel

I lost my virginity to my second girlfriend, Rachel. At the time I was in my mid teens, while she was two years younger and very well developed for her age. Rachel was short, with dirty blonde hair and plump C-Cup breasts, she was more also more sexually experienced than I was, having already lost her virginity to an older guy the year prior. We had been dating for nearly a month before we were able to get some real time alone together and previously we had no opportunity to progress past kissing and the odd clumsy grab of her still developing breasts.

With her mother sleeping in the bedroom adjacent Rachel and I removed each others pants and begun to kiss each other with a feverish lust. My cock was hard in anticipation for what was going to happen and pre-cum soaked my briefs, causing a wet sticky mess against her leg. As we kissed I fumbled around in the darkness for my jeans, my left hand feeling around in the darkness while my right hand massaged her wet mound. Finding them I reached into the pocket and removed a condom from the back pocket which had been specially purchased for the occasion. With a nervous laugh I broke away from her, rolling onto my back as I fumbled with the packaging.

Placing it on the tip of my penis I began to roll it down, just as we had been taught in school. Unlike school however the excitement had caused me to place the condom on the wrong way. Barely able to think properly due to the blood flowing from all extremities towards my member I flipped it over and begun to hurriedly roll it down over my cock until it was sitting just how it should be. I turned to Rachel and begun to kiss her, rolling my body on top hers in the process. I felt her hand reaching between us, snaking between our stomachs as she reached out for my cock. As she graspe it in her hand she begun to guide it downwards, towards the wet patch between her legs and I felt my cock hit the out part of her glistening labia. After a few moments of awkward fumbling she eased me inside of her and I let out an audible sigh. This is what sex feels like. The warmth of her pussy felt much different than her enticing but not overly brilliant blowjobs. I could feel the wetness as I began to thrust, near ecstatic from the occasion. And then it was over. In no more than four strokes I had finished. As I came waves of cum shot from the end of my penis nestling itself in the tip of the condom, while another wave washed over me. A wave of embarrassment. I had barely even began to get a rhythm going and now it was all over. Thankful Rachel was very understanding and, while our relationship only lasted another five months, we got to explore plenty of things for the first time.

They say that your early experiences in life play a pivotal role in developing your fetishes and for me this is very much true. Role play, where she was a naughty school girl who needed inspections of her cunt, ass and boobs to ensure they were clean and well-presented led to my desire for domination and administering punishments. Our raging teenage hormones meant that we had sex just about anywhere we could, including several public locations such as an empty carriage on a train, in a river and on a golf course. We also experimented with anal, when we were both drunk and feeling rather adventurous. Using a bit of spit and a lot of juices from her pussy I slid a finger in and out of her ass while I fucked her from behind. A short time later a second finger began to penetrate her soft, delicate little bud until both fingers were easily sliding in and out of her. As my cock moved from her pussy to her ass she gasped. In my excitement I had thrust it inside of her ass all at once. As she begun to tense up I could feel her asshole tightening around my cock and I began to move, placing my hands on her hips to make myself more comfortable while I fucked her in her virgin ass from behind. Truth be told the next couple of minutes were a blur. I fucked her perhaps a little harder than I should have since it was our first anal experience but she was either too aroused or too drunk to notice the bit of pain that went with the rushing sensations. As I began to feel a familiar sensation building up inside of me I bagan to thrust harder, having little disregard for her comfort. I came deep inside her ass and we collapsed together into the bed, panting furiously as we embraced one another. The next day she struggled to walk without pain and that put an and to our anal exploration. That was Rachel.

Edit: PM's welcome!