A while ago, when Lo and I first met up with the protégés, Zach and I had a nice little chat about our sexual proclivities. My theory was and is that the things we obsess about as adults have their origins in our formative sexual experiences. While talking with Zach, I was reminiscing about the girl who stole my virginity and then proceeded to crush my loving heart. (“Stole my virginity” is hardly an apt phrase. I was eager to get rid of it!) It had not occurred to me at the time that there may be other, more subtle seeds that were sown in my libido that blossomed into an infatuation with nymphomanical women drawn to living the lifestyle of a hotwife.
But then Lo took pity on our friend, Professor Smith. One night, when I was making passionate love to Lo and she was whispering in my ear about helping dear Dr. Smith to find release from his long sexual frustration, an image and snippet of conversation buried deep in the recesses of my memory was triggered.
It was the same year I had lost my virginity. There I was, fifteen, and out with my two buddies — Ryan and Peter. They were both seniors and I was a sophomore. I looked up to Ryan with unquestioning admiration. Ever since I was a freshman, my first day of high school, he kindly took me under his wing and showed me the ropes. He taught me how to cut class, the shortcut to the convenience store to grab a sandwich and smokes, he let me drive his car in the parking lot, instructing me in the basics. When it snowed, he would take us out into the same parking lot and we’d do donuts for hours on the slippery surface, fishtailing and skidding around like kids in their big, motorized toboggan.
To this day, I have no idea why he was so kind to me. He had a generous nature and there was no one in the school who had a bad thing to say about him. His best friend since childhood was Peter — also a senior. Peter was, in many respects, the opposite of Ryan. Whereas Ryan was good looking and “cool” — whatever that meant to us back in high school — Peter was quite unattractive and a “nerd.” Peter had some terrible acne, he was about forty pounds overweight. He dressed slovenly, showed no personal attention to grooming, and, to complete the picture, he played the tuba. He didn’t just play the tuba. The tuba was his life. He was an award winning tuba player. Such accolades, however, didn’t make him any more attractive to anyone.
Yet Ryan, unfazed by the court of public opinion — even in that most harsh and unfair court called high school — stuck by his buddy and stuck up for him. It was a true bromance that was lovely to see. Somehow, for reasons unfathomable to me, these two seniors were more than happy to include me, a mere freshman, in their little club.
In addition to Ryan and Peter, by the time I came on the scene, there was also Jackie, Ryan’s girlfriend of about a year. Jackie was a tough, rough, brunette who was the star of the girls’ soccer team. She played trumpet and also was on a girls’ rugby team. I’ll admit, I had a crush on this sexy senior. I’m sure it showed. But I wasn’t alone; Peter also had a crush on her. She was, in so many ways, “one of the guys.” She hung out with us and reveled in our adolescent humor and poor manners. She accepted everyone for who they were, perhaps because her tomboy persona set her apart from the other preppy girls of the school. She wasn’t going to be one to judge since she was frequently on the receiving end of judgment from her peers.
Now that I’ve introduced you to all the players of this stroll down memory lane, I shall relate the inciting moment. It was a dreary autumn day. Ryan, Peter, and I were in Ryan’s car, getting high in the parking lot of a state park. Peter was monologing about his unpleasant family situation. His parents would have been better off divorced and they treated him and his siblings as so much extra baggage. As Peter’s rant continued, he touched upon all the other aspects of his life that sucked — his failing grades, his lack of money, his unseemly appearance, being overweight, being a virgin.
And that’s when Ryan said the words that I, a fifteen-year-old virgin myself at the time, could not believe I was hearing. “Do you want to fuck Jackie?”
“What?” asked Peter.
“Do you want to fuck Jackie?”
“No. I mean, yes, I do. But, if you’re really asking, no.”
“I’m really asking.”
“Stop fucking with me. I’m high and this is a mind trip.”
“No. I talked to her about it. And. . .”
“Talked to her about what?”
“About fucking you.”
“Yeah, I asked her if she would fuck you.”
“Why the hell would you ask her that?!”
“Because, I think you need to pop your cherry and move on. It would be a real confidence boost for you. Plus, she’s fucking amazing in bed.”
“I’m sure she is — don’t think I haven’t imagined what she’s like in bed.”
“OK,” I said, “this is getting weird.”
“But she’s your girlfriend,” continued Peter.
“So?! Don’t you think that would, like, fuck everything up?”
“What would it fuck up?”
“Our friendship, your relationship with Jackie, I don’t know — those are the two biggies I can think of.”
“No,” said Ryan nonchalantly, “it wouldn’t fuck up anything. It would unfuck you up.”
“Fucking your girlfriend would unfuck me up? That’s the most nonsensical thing you’ve ever said, on so many levels.”
“All I’m saying is, if you want to, you can.”
“It is tempting,” said Peter.
“Then do it. I’ll talk to her tonight and I’ll let you know when and where.”
Well, I don’t remember the rest of that day, but the next weekend I was out with Peter and I asked him, “So, did you take Ryan up on his offer?”
Embarrassed, he said, “MmmmHmmm.”
“You did?! Tell me about it!”
“He asked Jackie again and she said, ‘Sure.’ Ryan came back to me and told me that she’ll be at his house after school on Friday. He’d go out for a couple of hours and she’s all mine if I want. I was tortured by the choice. He told me this on Wednesday. I kept going back and forth in my mind. Eventually Friday came around and I thought, ‘Well, I’ll just go over there and talk with her.’ I showed up at Ryan’s house and there she was, wearing only her panties and bra. I tried to talk with her and she just led me into the bedroom and got on her knees. She looked up at me and said, ‘I’ve always wanted to be the first with someone.’ When she pulled out my pud, she put it in her mouth.”
He stopped talking.
“And?” I asked, on the edge of my seat.
“And, with one lick I came all over her.”
“Oh my God! No!”
“Yeah. I couldn’t help it. I’m lucky I didn’t cum in my pants before she undid them.”
“So, that was it? You’re still a virgin?”
“No, that wasn’t it. She was very good about it. She smiled, licked what she could, cleaned up, and then we lay in bed. It didn’t take long before I was hard again — especially because she got completely naked in bed — and, well, I had her.”
“Yeah. She was amazing!”
In retrospect, I probably could have had Jackie too, but at the time I was too proud for a pity fuck. I wanted my first time to be with someone I loved. Silly me.
All’s well that ends well — Jackie and Ryan continued dating until she went off to college. Ryan and Peter remained the closest of friends. And I found my first love and she ripped my loving heart right out of my chest, but that’s a tale I’ve already told you.
[Read more at: mysexlifewithlola]