Contradictions

Losing Their Virginity

For the next few months, all Jamie could think about was getting a blow job—whether he was jerking off or not. He pictured it with every girl in the magazines and most of the girls he knew at school. He played the scene that Rick had described over and over in his mind. He just couldn’t get it out of his head. He was so desperate that he even considered proposing mutual blow jobs with Billy Macintosh, but he couldn’t work up the nerve to suggest it to him. Then, one day, it happened—on one of his dad’s desks in the storage room!

He had been making the moves on Maggie Spolsky for several weeks. He had gotten to first base, then second. About two weeks before he turned 16, when they were making out in the storage room, he decided to skip third and go straight for home. Just like Rick had described in his story, he pulled off Maggie’s pants and panties and dove straight for her pussy. She was too shocked to object, and when she found out how good it felt, she sure as hell wasn’t about to stop him. He drove her to the brink of madness with his tongue, and when she came, he thought she would bring the whole work crew down on them. (It’s a good thing all the sawing and sanding in the shop drowned out their noises.)

Now, it’s my turn, just like Rick had said. Jamie dropped his pants and locked onto his target, but Maggie ordered him to stop. He said all the stupid things that Rick had told him not to say, and he eventually found himself standing over Maggie with his dick in her face. To make a long story short, he got his first blow job. It felt fantastic, of course, but somehow not quite as great as he expected it would from Rick’s description. He was thrilled that he had passed a significant milestone in his life, but even more than that, he was downright giddy over the prospect of telling Rick what he had done. Rick congratulated him on his conquest, but he also chewed him out for not learning from his mistakes.

Maggie confided in her best friend, Kelly Hooper, and on Jamie’s sixteenth birthday, Kelly told him that she wanted to stop by the shop and give him a present. He didn’t know why she would be giving him a present, but he said, “Sure, come on over.” When she arrived, she asked to see “where it had happened.” He escorted her to the storage room. “Uh, you said you had a present for me?”

“Yeah.” She dropped her pants to reveal a lacy pair of panties with a red ribbon tied around the waist. “Happy birthday, Jamie.” And that was the end of his virginity. Ah, sweet sixteen! A week after that, he deflowered Kelly’s sister on the very same desk.

Of course, Jamie told Rick all the details, and Rick was proud of him for the way he had handled himself, following his advice those times.

Now that he had become a man, he decided that he needed to adopt a man’s name, as Rick had done when he lost his virginity. Rick suggested that Jamison Sherwood take the name Woody.

“Very funny, Rich-HARD,” replied Jamie. He considered James but decided that it was too formal. Finally, he settled on Jay.

“Well, I don’t see what’s wrong with the name Jamie,” said Mrs. Sherwood when Jay proclaimed his new name, “but if you want to be called Jay then that’s what we’ll call you.” She rolled her eyes when she turned to Mr. Sherwood, though, as if to ask what was going on with her son.

Mr. Sherwood said nothing to his wife, but he had a hunch. He recalled the day he had informed his parents that he wished to be known as Walt instead of Wally, and he suspected that his son had been motivated by the same kind of experience.

Walt Sherwood sat down with Jay for one of those father-and-son talks. He didn’t try to tell Jay about “the birds and the bees” because he was sure that Jay already knew the basics from sex education in school and from being around some of the guys in the shop. Instead, he talked about responsibility. He told Jay that he was proud of him as a boy and that he expected to be proud of him as a man. Though he pledged not to spy on him, he did say that he would be watching him to see how he handled himself, not just with his school work and his job, but also with the girls he dated and with his mother. “If you continue to treat your mother with respect,” said Walt, “I will know that you are treating the girls in your life with respect.”

Jay had very mixed feelings about the conversation with his dad. On the one hand, he felt embarrassed, but on the other hand, he felt proud that his father was talking to him man to man. Jay would always look up to his father, but now their relationship was on a different level.

After he lost his virginity, Jay suddenly became very popular at school. All the girls wanted to date him, and all the guys wanted to be his friend. Unfortunately, between school and work, he didn’t have much time to take advantage of his new-found popularity.

In addition to telling Rick about his initiation into manhood, Jay also told Billy Macintosh. Prior to that, Billy had begged Jay to relay every detail of the stories that Rick had told him. Jay pretended to get tired of it after a while, but the truth is that he loved telling those stories—partly because he loved them, and partly because in telling them, he could relive the experiences of being with Rick. After his trysts with Maggie and the Hooper sisters, though, that’s all Billy wanted to hear about. He worshipped Jay the way Jay worshipped Rick. Actually, Jay felt sorry for the kid, so, on Billy’s sixteenth birthday, just a couple of months after his, Jay asked Billy to come down to the storage room with him. Billy expected to look at magazines, jerk off, and listen to Jay retell Rick’s stories, but when they got there, he was surprised to see that there was someone else there. “Billy,” Jay said, “This is Kelly.”

“Nice to meet you, Kel…. Wait.” Billy looked at Jay. “You mean, THE Kelly.”

“That’s me,” said Kelly. “Jay has told me about you, but he didn’t tell me how cute you are.”

Billy got all flustered, but he also beamed, much like he had done when Jay initiated him into masturbation.

“I think Kelly has a birthday present for you, Billy, so I’m gonna leave you two alone and go back to work.” Billy didn’t hear a word he said. He was transfixed on Kelly, and his imagination was running wild at that point.

When Kelly left the shop about an hour later, she winked at Jay on her way out. Then, Billy came out from the storage room. “Thank you, man. Thank you, thank you, thank you. If you ever need anything, you just let me know, and it’s yours. Anything. Cash, a car, a kidney! You just let me know, and it’s yours.” Later, Jay learned that the reason Billy and Kelly had been in the storage room for an hour was that she first sucked him off and then, when he got a second erection, she let him take her.

When Billy stopped by the shop the following week, Jay wasn’t surprised to find him still glowing, but he was surprised to learn the details. It seems that he had gone over to Kelly’s house, but she wasn’t home. However, her sister was, and…well, the rest is….

Then, a couple of weeks later, Billy surprised Jay again by telling him that he had done both sisters together! Jay was pretty sure that Billy had made that up from some of the pictures they had seen in the magazines, but he pretended that he believed him and let him have his moment of glory. Billy also let it be known that thereafter he wished to be known as Bill.

[Author's note: In Chapter 5, Jay visits Rick's apartment and gets an eyeful and an earful.]