My First Girl Kiss:
Ah, how clearly I remember my first girl kiss…..

Back in high school, my closest friends and I had a ritual - every single Friday, after we got out of work, with out fail, we would go to Friendly’s. It started out as just Elizabeth and I, because I liked a boy who worked the fountain, and we figured that it wasn’t stalking if you were eating a meal. Eventually, the boy and I became friends, and we smoke pot together now

After Friendly’s, we would either all go to a movie, go bowling, play pool, or, most commonly, go back to my house and play games. Monopoly and the Game of Life were popular.

This night, it was Monopoly. Elizabeth and her boyfriend, Eleanor and Ryan, (dating at the time) and poor poor Jeanette, who always wound up seeing way more than her poor, prude virginal eyes ever wanted to see. (We worked together at the library you see, and sometimes she would come out with me, Ryan, Millicent and Princess Donna, and get stuck watching porn with us)

Now, when we played Monopoly, we played dirty. We played to win. It wasn’t uncommon for me to take off my shirt at key moments to distract the male players from their game, or to offer a peak as part of an exchange deal. “Ok. You hand over Oriental Ave and the Water Works. I’ll give you Illinois Ave, $50 bucks, and, I’ll take off my shirt”

Its an effective strategy. Once I find another chess partner, I plan to apply it there if I can.

Anyway, Eleanor, as you might remember from my first orgy post, was one of the first girls I ever had a crush on. I though she was so smart and beautiful, and we hung out a lot. Back in the day, hormones and friendship got confusing. “Do I want to hang out with her, or shag her? Damnit. I’ll have to try both.”

And we were a pretty sexually open group. Sometimes, shit would happen. For Ryan’s birthday, Millicent, Princess Donna, another girl and I bought him his favourite porn stars pussy. (Those things are pretty damn life-like! I mean, except for the part where real pussies don’t usually vibrate on their own.)

So, he rocked it for us. Twice. (Ryan had some damn good stamina and recoil for a teenager. I really ought to have shagged him back then, but alas, I was in a mono-long distance relationship.)

As for me, I spent most of high school not just openly, but flamingly bisexual. I hit on everyone, especially the girls. Girls were always the most fun to flirt with. I could be over the top and they usually thought I was just kidding.

So yeah, stuff would happen, and generally, it was all good.

Back to Monopoly: There we were, six of us sitting around the table, and Eleanor and I needed some properties to complete monopolies, and Elizabeth’s boyfriend had them. We offered him Monopoly money, but he didn’t need it. We had no properties he wanted. He’d already seen our boobs. Finally, I yelled at him

“Look, if you make this trade with us, we’ll make out!”

I’ve never seen anyone give up Boardwalk in a game of Monopoly that fast or that easily.

Eleanor was already in my lap, and without saying anything, she turned to straddle me. Then we kissed

I can prove it. I have a photo.

Photobucket”>

We also got Ryan and Elizabeth’s boy friend to kiss. I lost the photo of that one, unfortunately.

The First Girl to Seduce Me:
Virginia was a ’straight’ friend of mine.
(I got a lot of ’straight’ girls, back in the day)

I remember that she had the most adorable nose. It was a perfect little ski jump, turned up just a bit at the end, and a very light smattering of freckles on her fair skin. She was curvy and blond and had gorgeous blue eyes. (Yet another high school friend I couldn’t figure out if I wanted to befriend, or date.)

Virginia turned up outside my house at about 2 in the morning, after having just drove about 4 hours by herself on the way back from a trip. She wanted to tell me about the trip, and the boy she met.

We talked so long, that it was almost 3:30 when she rose to go, but she was weaving and sleepy and in absolutely no state to drive. I insisted she stay, and pulled out the trundle bed, turning my twin into a full. I gave her some pyjama pants and we curled up and went to sleep.

A few hours later, I awoke with a hand in my pants and hot breath on my neck. Shit, I was a horny teenager. I’m not gonna complain. I reached back into her pants, and worked on returning the favour.

What else could I do?

We both came, and the drifted back to sleep.

In the morning, we didn’t talk about it, we never talked about it. But god that was hot.

The first girl I went down on:

The first girl I ever ate out was wearing a school girl outfit. TOP THAT!

I went to two proms. I went to my own prom, and Elizabeth’s prom, the prom in this story, the year after mine.

I went with a girl named Jessica, who I totally wanted to nail. This story is not about her. After prom, we took the limo into NYC and went to a hotel we had booked. Unfortunately, I passed out drunk first, and could not try to bone Jessica.

However, the next day at the play we went to, I ran into other friends I knew at intermission. Dan and Charlotte were staying the night again in a different hotel. After Elizabeth, her beau and Jessica went home, I went over to Dan and Charlotte’s.

Her uncle worked for the hotel, so they were in a really swank suite.
Charlotte ran to change and show off her new ‘outfit’.

I had brought over the beer and vodka we didn’t drink the night before, so I cracked a few open. Dan and I were sitting on the bed, bullshitting and such, when Charlotte came out wearing the school girl outfit.

It was one of those skanky little outfits they sell at lingerie stores and sex shops, but it looked cute on her. I was also fairly drunk and horny, which may have coloured my vision.

I handed her a beer, a Hoegaarden, or however its spelled. A nice Belgian beer. She drank, and we all talked some more, exploring the room and all the outrageously expensive things in the mini fridge and mini bar.

Charlotte said she didn’t like the Hoegaarden, and was going to dump it. Now, where I come from, dumping beer..it just isn’t done. You get a beer, you better damn well drink it.

“How about this, you finish the beer, and I’ll go down on you.”
I didn’t think she would actually take me up on it, but she finished the beer, and so I honoured my part of the deal.

Charlotte laid back on the bed, and I ran my hands up her smooth legs, flipping up the little plaid skirt, while Dan settled on the bed next to us, propped up on a pillow to watch. (He was very nonchalant about the whole thing. But considering that he knew me, he wasn’t surprised. Hell, at the very beginning of the same school year, a friend and I gave him a double blow job.)

She wasn’t wearing anything underneath. I ran my thumbs up her smooth pussy before parting her lips, admiring the contrast of my long silver nails against her naked flesh. I started with light licks, and she proved to be very sensitive, and a squirmer. I slid my arms under her thighs and around her hips to hold her down, and I went to town.

She buried her hands in my hair, and I felt her muscles tense, trying to buck against my hands, but I was stronger than her. Instead, she wrapped a leg around my head, pulling me closer to her. I think Dan started playing with her breasts through the little white schoolgirl top.

To this day, I can remember her sweet gasps and moans, the tightening of her thighs around me, as I ate her to a writhing orgasm or two.

After I disentangled myself from her, I cleaned up, and Dan and I left her to rest while he came with me to hail a cab.

“So…that wasn’t weird or anything, was it?” I asked, thinking he might be annoyed that I just shagged his girlfriend.

“Hell no, that was awesome! Plus, you got her started for the night. Now I don’t have to do as much.”

I really hope he was joking about that last part. But, teenage boys are lazy. Such is life.

He finally managed to hail a cab, and I caught the drunk train back to Long Island with some friends who were also in the city. We were all drunk, sitting on the floor, while I was crowing about just having eaten out a school girl. Several drunk men hollered their appreciation.

Ah, memories!