First of many 4

I forgot I was even using these stories as a sort of diary of my youth, but recently found them again, I suggest before reading read the previous "chapters".

In last chapter we left of with Mary and I's first experience with anal, I will skip over most Mary stories from this point as we had sex hundreds of times thru out high school and after, may hit later on some of the highlights thou.

I also had several girlfriends which i'll skip over as these are story's of firsts and highlights, thou all great in their own way, not all are as memorable.
A couple brief girlfriends-

Kim- She was one of the thinnest woman I would ever date in my life, almost anorexic she had the smallest breasts i'd ever encountered something like an -A cup, but there ass and pussy more then made up for it, she was very demanding, our first and only time having sex she made me eat her for something like 30-40 mins before I got mine, I will say being so skinny her pussy was extra tight. Before we broke up, she did give me one first, she always like me to driver her car, and one day as we were cruising, yes we used to all "cruise" when I was a teen. She started touching and rubbing on me as i drove, I told her cut it out or i'd pull over, she said I can give you road head? "excuse me whats that then" I said, she then unzipped me as I drove, pulled
out my dick, and lowered her mouth on me and proceeded to show me that she could indeed suck cock. (she hadn't up to this point). So here I am driving her car, her vigorously sucking me, I quickly pulled down the first side street I saw and slow rolled down itI told her I would cum soon, so pulled to curb and stopped, she pulled her mouth off me and jerked me onto my stomach. Go to find out after she didn't really like giving blowjobs, and hated taste of cum.
We did not last much longer.

Keely,
Another short lived was Keely, oh my god was she hot, we met during in school suspension we started chatting, next new we set up a time to meet for a "date", back then a date was simply meeting for a party or hanging at the mall.
After a few dates and some one off kisses and gropes, (god her ass was amazing in a pair of tight jeans), we were parked in my parents mini van down road from her house before I took her home I was getting towards second base, (hands under her shirt), feeling her tits when she while kissing me unzipped me, pulled me out, slip in between seats got on her knees, and took my in her mouth.
This wasn't the first cock in her mouth I could tell, but she was not experienced either, but oh the pleasure that vixen gave me. Thinking back on it i can still remember her taking my hand and putting it on the back of her head to guide her, pumping in and out of her mouth, thou she couldn't take me all the way soon had me edging close to explosion, I started warning her but she did not let up at all. Soon I was there, flooding her throat, she swallowed and swallow, gulping as much as she could. In the end she had cum dribbling out the corner of her lips. She sat up, wiped her lips, drank some coke, I remember her swishing it in her mouth before swallowing, I tucked back in, we kissed for several more minutes and I asked when do I get a repeat.
The only other experience Keely and I had, as I found out later she really wasn't a very sexual person, when alone in my parents basement I finally got to fuck her, but it was a very uneventful experience.

Stacy,
In my group of friend I became friends with a mutual friend of a friend you know how it is when young everyone knows everyone. Well Stacy and I had partied several times, back then if you weren't going to "cruise" you went to the pool hall and shot pull. Well I invited Stacy on a Pool Date, it being winter couldn't do much cruising just the two of us.
I picked her up, we stopped and grabbed some fast food, remember we were teens we didn't have money back then, or much that is. We sat in car eating and talking, chatting about what we wanted to go do other then pool if pool hall was full, we didn't want to sit around doing nothing, in my best attempt to sound joking I said "we can just go park and make out instead" with a little laugh.
Stacy said something like " I'd rather do that to.". we did several back and forth before i actually got up the guts to kiss her, well in this burger joint parking lot next thing you know i'm sliding my hands up her shirt, kissing her, feeling her C cups tits soft and pliable in my hands. She finally pulls away, saying "people can see, lets go somewhere else". So off in my parents minivan we went, we went into a back alley parking at a closed business off the beaten path, you could only see our tire tracks in the snow so we knew we wouldn't be observed.
I leaned over and started kissing her again, she said, wait here and jumped into the first row of the back seat, I started climbing back, she said "wait, and turn up the heat". I did as instructed and watched as she took off her coat, unbuttoned her blouse fully, reached back and unsnapped her bra and removed it. Throwing her bra on the passenger seat, I then climbed finback, she started kissing me roughly and whispered "you didn't let me take off my panties". I thrust my hands up her skirt and grabbed the sides of her panties pulling them quickly off, I then started kissing away from her lips, and down to her breasts, I sucked on them very briefly knowing something else was awaiting me, she had great breasts, C cups at least, most teens you know have firm hard breasts her's actually being quite large were very soft and a bit saggy but wonderful as I licked and sucked on them.
I quickly moved down, hiking up her skirt, and not waiting for more foreplay dove in, best way I can describe what I did was not oral sex as much as sucked her pussy, the second I hit her hood she screamed in pleasure, I don't believe I left that spot, I sucked, and nibbled, she flooded my mouth with her wetness but nothing like a squirter. She orgasmed hard pulling my face into her pussy grinding my mouth on her clit and with giant gasps and pants finally released me. I kissed my way up her stopping for a suck on her nipples, then finishing at there lips, she whispered.fuck me..
Continuing our deep kiss, I pulled down my slacks, revealing my hardness, I started rubbing my head on her soaked pussy lips. Up and down I rubbed, pausing time to time at her canal. She whispered "get a condom i'm not on the pill", I quickly pulled one out of pocket, trying my best to open it and roll it on with out breaking our kiss. I told her "what do you want?", She replied "fuck me hard"and that I did.
As soon as my cock was covered I did not hold back I plunged completely into her in one push and started to pound away, I couldn't have stopped if I wanted to. We instantly generated heat in that van sweating and pounding, windows were completely covered in fog we both were panting so hard.
I liking different positions asked her to bend over, she slid of seat and leaned over it, again I plunged in and pounded away, I think back to my teen years and now realize thou I was good with my mouth, true sex I was not good at, it was just push and pull at varying speeds, she did not mind. I pounded her to another orgasm finally proclaiming my need to cum, and with one last push flooded that trojan to the maximum holding capacity.
The best was soon to come, not the best sexually, after I came, not wanting to make a mess in the car, I pulled my pants half up, and got out in snow to pull off the rubber, once it was deposited in the parking lot I saw something that started me giggling which soon turned into laughter, when asked "whats so funny" I made Stacy lean out and look, the van had slide 2 feet side ways in the snow, you could see it in the snow tracks going side waysher and I had made our mark.
I don't remember why but this was Stacy and I's first and only sexual experience but oh it was one to remember.

I hope you are enjoying the stories of my exploration and conquests during my high school years, there will be more to come.