Because of my background and the fact that I was somewhat shy growing up, I didn't really pursue girls to the fullest until the end of high school. This is when I started dating my first true girlfriend. We'll call her Ash. I was a senior in public school and she was a junior at our church ran private school.
Ash was a redheaded beauty. Her dark red hair flowed halfway down her back and made her emerald green eyes that more intense. She tanned somewhat regularly so, her lightly freckled skin was actually a nice golden bronze. Her body was one of the tightest I've known. Her stomach was flat and her legs were long. She was about 5'7" and couldn't have weighed more than 115lbs. Her figure was curved perfectly with nice 36" hips and 25" waist, topped off with perfectly round 34D breasts. I remember the first time she coerced me into playing with them. I couldn't get enough. Being that she was so young, they were extremely firm and perky. They didn't sag in the slightest. They sure were fun to play with.
I, on the other hand, was a lean 170lbs at 5'10". I wasn't extremely muscular, but I was tone. I hit the gym for about an hour every weekday morning. I had a short, messy hair style. My hair is a very light red, nearly blonde. My mom always said I was a strawberry-blonde. Ash got me to start tanning, so my skin was also lightly freckled and bronzed. Neither of us were too tanned like the leathery people you see, just enough as not to be pale. My eyes are blue or green depending on what they decide to be each day. My cock is straight, right at 7" long, with a diameter somewhere between that of an old half dollar and silver dollar. If you don't remember those, just assume they're huge. ;)
Ash was somewhat more experienced than me. Like I said, I was a late bloomer. She was actually my first real kiss. She on the other hand, had kissed several guys and even gave head to a couple with her girl friend. As we would soon find out, we were both a couple of repressed nymphos just waiting to get out. We first kissed about a week after we started dating. A week after that, we were making out every chance we got.
At first, we would just sneak in a half feel of each other's butts or the side of her boob. That led to hands up the backs of shirts. Eventually she talked me into taking off her shirt and just doing whatever I wanted with her boobs - we rationalized it as a scientific experiment of sorts. You have to remember that this was all very wrong to us. I was extremely sheltered and her dad was actually an evangelist. Her breasts were great. I caressed them gently, molded and kneaded them, even kissed and sucked on them for a good hour.
Finally, one weekend a couple months after we'd started dating her family went out of state because her dad was invited to preach. Since she had to stay home for school and work all alone, we talked my parents into letting her spend the night at my house. This wasn't the first time this had happened. She spent the night a few times because of similar reasons. She would sleep in my sister's room on her futon in the room right above mine.
Friday night we ended up being the last ones awake because we were watching a movie in my room, aka making out. We were getting pretty hot and heavy when my parents came by and said they were going upstairs to bed and Ash needed to be pretty close behind. By that point we had gotten really good at breaking off the make-out sessions in a hurry - which is what we did when we heard them getting close. We told them that the movie had just started and we really wanted to see it. They said fine and told us that Ash needed to go to bed as soon as it was over. They didn't really have a reason not to trust us - other than the fact that we were teenagers. But we were both good kids.
At that point we knew we were alone and could really get into making out. So, we did. Our lips collided and our tongues mingled. We couldn't get enough of each other. We tossed and turned, rolling all over the floor onto one another, pressing our bodies as close as possible. Our hands started to wander as we breathed heavier. She began to feel my chest under my shirt as I was unfastening her bra beneath hers. As I unfastened her bra, she got the idea and removed her hands from my shirt, and pulled hers over her head. Her shirt and the bra were not far behind.
Since she was now topless, it was only fair that I be as well, so she then proceeded to remove my shirt. She was now on top of me and we were both moaning as we kissed passionately. I pulled her close to me, savoring the fantastic feeling of her flawlessly smooth, young skin rubbing against mine. She then started doing something that would soon become so familiar in our make-out sessions. She began rubbing her crotch up and down my leg instinctively. It was as if she couldn't help it. She couldn't contain herself. To this day, it is the biggest thing I miss about Ash - her pure sexual desire and energy. For a woman to be so lustful to do whatever it takes to get herself off is the biggest turn on I've ever experienced. I think that is why I love "slutty" women so much now.
I bent my knee as to raise my leg for Ash to get more leverage as she pleasured herself. My raised knee caused a bend to form between my pelvis and my upwardly stretch thigh. It was the perfect nook for her to settle her humping into -right next to my crotch. By this point my cock was so hard it was begging to burst out of my pajama pants. It was thrilling to know her pussy was grinding right next to my dick as she straddled my leg. At the same time her large breasts were gliding back and forth against my chest. At this point, she was getting pretty hot and moaning more and more as I began to kiss and suck at her neck and chest for all I was worth. Her breathing became heavier as I grabbed her by the ass and helped push her pussy up against me. As we kept this up, I took my hand and slid it down her pajama pants and under her panties grabbing her bare butt.
Suddenly, she stopped and asked me if I'd like to continue without clothes. I told her I'd love to. Lying side by side we then helped each other out of our pajama bottoms and underwear as we continued to maul each other with kisses, licking, and groping. Once we were completely free of our clothes we pressed together tightly and explored each other's bodies with our hands as we passionately continued to lock lips. I remember feeling that the butterflies I'd felt being with her the past few months had taken a huge dose of steroids that night. I was almost shaking with nervousness and excitement. I reached around and grabbed her ass. Her cheek, now free of clothing, spread as I pulled her into my granite member. She moaned into my mouth as she felt its length pressing along her stomach.
After a bit, our hands finally got the courage to find the spots we'd both been wanting touched so badly. We were still kissing passionately, but we had rotated our hips away from each other slightly to allow access to each other's pleasure spots. As I reached my hand down, I rubbed across her midsection and slowly worked my way down. At last I reached her mound, sparsely covered in short red hair. As I worked my way down further, I slid around to her inner thighs teasingly. As I caressed them, she spread her legs, encouraging me to reach between - to touch what we both longed to be touched. I glided my hand upward until I brushed against her labia. She breathed heavily into my mouth as I started to palm her hot cunt and rub up and down it.
She then proceeded to slide her hand down and lightly walk her fingers on and around my member. She lightly caressed it and swirled her fingers around my balls, cupping them from time to time. Eventually she wrapped her hand around the base of my cock and squeezed it gently as I started to protrude my middle finger slightly into her slit as I rubbed up and down, still cupping her pussy. It felt wonderful. I had masturbated for quite some time, but her soft delicate hands felt infinitely better stroking my cock than did my own. She lightly glazed up and down my shaft, randomly giving it slight squeezes of pleasure.
I started to push my finger into her wanting hole when she stopped me. I was confused at first. Then she explained she had been fingered by one guy before who obviously got a little over zealous because it had hurt her, rather than pleasure her. After she explained her hesitance, I assured her that I would go slowly, stopping at the first sign she gave me. She then became cautiously optimistic as I slowly slid my index finger into her now soaking hole. She tightened her grip on my cock as I carefully pushed inward, probing her virgin pussy.
Since we were both inexperienced and this was completely new to us, we decided to experiment. At the time, as with most of the year following that we dated, we were not aware of clitoral stimulation (this is funny now looking back that we didn't recognize that was what had gotten her off when grinding against my leg). We both knew about the clitoris, but Ash hadn't had much success in getting off using that method in the past. So, since I had heard about the G-spot in my biology class, we decided to try and find it. I would alternate sliding my index finger in and out slowly and rubbing the "roof" of the inside of her vagina where I'd read that the G-spot was supposed to be located. She said she enjoyed both equally, so I continued to alternate, giving variation. Eventually I switched to my middle finger in order to reach deeper.
Though, well lubricated, her tight pussy wrapped snugly around my single finger. I couldn't believe how wet and hot it was inside. It felt amazing to be feeling the inside of my girlfriend's hot pussy - the first one I'd ever felt. Her breathing got heavier and shorter as time progressed. She held her grip around my cock for quite some time as if it were somehow muffling her cries of ecstasy.