[Thank you for all of the comments on my "Sisters By The Pool" series! I never dreamed I'd immediately make the top rated stories of the month. I will be working on part three soon. I just wanted to take a break and come out with some new stuff. As always, if you want to send me personal comments or messages or anything fun you can PM me on here - thanks for reading!]
Every guy growing up seems to have a switch that flips from 'too scared to talk to girls' to confident and ready for anything.
I've always credited Deb for finally flipping my switch.
It's embarrassing to admit that it took until about midway through high school for this to happen, but better late than never, right?
She was just a freshman that landed in one of my elective classes, but you wouldn't have known it by looking at her. She had natural, long blond hair and green eyes. I'll admit it though, the first thing I noticed was her large bust, which must have been a full C, pretty impressive for a high school freshman. She must have been one of those girls that developed back in middle school that everybody hated.
It was just the luck of the draw that she sat down next to me on the first day, and on that first day, we had to do a one on one learning exercise right off the bat. Instead of doing it with any of the multiple people I knew in that class, I was gracious enough (*wink*) to volunteer to work with the girl who didn't know anybody.
And so my friendship with Deb was started. Over the first few months of the school year, we became close friends, the type that poke each other and always sit together and everybody thinks you're going out even though you're not kind of thing. In fact, she may have flipped my switch too hard, because I was considering her and three other girls, and couldn't decide which one to make a play for. I tried all sorts of games to figure it out, and couldn't really come up with an answer. I eventually settled on someone else, which turned out to be a horrible mistake.
Stop me if you've been here before yourself. I had a girlfriend, and she was single. We broke up, and she found a boyfriend. I found someone else, right around when she ended her's. It was a frustrating cycle that left us as great friends, with high sexual tension, without a way to act on it. By the end of the school year, we were basically best friends, and both in relationships that were getting long term, but also kind of unhealthy.
Unfortunately, it led to a night that I'm not very proud of. While we were both in these relationships that were heading south, we hung out together in her neighborhood one night. We went to the park, and although we didn't do much, I did get my first experience at touching breasts of that size.
It was a relatively isolated incident. After my relationship ended, I did have her over once or twice for more fondling sessions, but nothing beyond that.
Finally, after a year or two of struggling to keep in contact, we decided to hang out again. I picked her up and we drove around the city, reminiscing about times we had and catching up on failed love attempts. It was obvious that we wanted to act on the extreme amounts of sexual tension that still existed. I ended up parking my car in a dark area and we both went to my back seat. For all the growing I had done, I was still stupidly shy at times, and we both struggled to make much happen. We did finally kiss for the first time, and made out for a while, before it got late and I took her back home.
Summer came and, after a few more months of not doing anything, I invited Deb to come over to my house. It was a hot, sunny day when she arrived. I made sure to have her come over on a day where my parents weren't going to be home until late.
She walked inside wearing a tank top and shorts. Her breasts were doing that lovely thing where the tops press up and over the neck of the top. I gave her a hug and felt them press against my chest.
"So what do you want to do?" she asked, smiling at me.
"Oh just watch some tv," I laughed and brought her into my room.
It was at least partially true. I flipped the tv on, which was playing a marathon of a certain show that I'll never forget or stop associating with her.
We sat on the bed, playing around for a little bit, going back and forth between kissing and tickling each other. Finally I lifted off her shirt and took her bra off. It was really the first time I had been completely exposed to her breasts, which I lustily paid attention to, with tongue flicks across her nipples and taking as much of her large chest into my mouth as I could. As I did this, I dropped my hand into her shorts and gave her clit some attention.
"It's about time we did this," she looked at me seductively.
"We better make up for lost time," I winked.
I pulled off her shorts and hipster panties, finally getting a full look at her naked body. She wasn't a twig, but that was good. She wasn't overweight, and the average build had definitely gone to the right places. She was shaved and looked as tight as could be.
"So what are you going to do with me?" she teased and looked up at me from my bed, where she laid on her back.
I kissed her and then kissed all over her neck, making sure to ramp up any final sexual tension that may have existed. My hands very infrequently strayed from her breasts, which I used partly as a balancing area. I rubbed the head of my cock against her soaking wet pussy, and she arched her back, trying to take me inside. I still teased her, and she started to whimper.
"What the fuckk," she whined.
Then, before she knew what hit her, I slammed my cock into her pussy.
"OH FUCK" she screamed as I entered her, as her large breasts immediately started to bounce from the force. I grabbed onto her chest and started to hammer away at her pussy, twisting her nipples between my fingers as I fucked her hard. Then she turned on the dirty talk, something I didn't even realize she had.
"Holy shit your cock feels so nice in my pussy," she moaned. "I've dreamed of fucking you for so long. My body is yours; you better not stop."
"Fuck yeahhh," she yelled as her first orgasm hit, sending her pussy into a spasmatic rage on my rod.
After she came down from her first orgasm, I put her onto her hands and knees in front of me. She had a great ass, which I spanked a few times before entering her from behind. My cock slid back inside and made constant contact with her g-spot. It wasn't long before she was cumming again, humping back against my cock as her vaginal muscles gripped me tightly. I helped the pace, pulling back on her breasts with each thrust, fingers tight around her nipples.
I laid her back on the bed, still facing the other way, as I lifted her leg up and slammed my cock back inside her. I grabbed her breasts with one hand and playfully put my hand on her neck, bringing her face back closer to mine. I turned her and we kissed as she moaned against my mouth. Whenever she opened her eyes, she seemed to be lost in a world of ecstasy, with a glossed over look that was almost devoid of reality.
Her pussy felt amazing. It was so tight, and with each thrust I could feel her walls expanding to accommodate my cock. It was like sliding into a hot, wet glove that fit perfectly, and I knew I wasn't going to last all day. My arms wrapped around her body and I brought her down onto my cock repeatedly, her lips parting to my cock's demands each time. As I started to get closer, I bit her ear and asked if I could cum inside her. She paused a few seconds, seemingly weighing thoughts in her head, before nodding with an innocent look.
I put one hand on her breast, and had my free arm wrapped tightly around her body. I violently brought her down on my cock once. "Holy fuck," she moaned. A second time; "FUCK," she screamed. A third time; "OH MY GO-AAAAHH" she yelled and cried out as my cock exploded inside her, rapidly shooting thick ropes of hot, sticky cum deep inside her pussy. I kept her buried down to the base of my cock as each stream of spunk found a deeper crevice of her pussy. She went weak with exhaustion and I held her body in place, feeling each spurt of my cum ooze into her. I completely flooded her pussy, and watched as it started to quickly leak out.
We started to kiss again and I left my cock inside her as we dozed off for a little.