“How did I get myself into this?” Terry Griffith asked herself for the hundred time that evening. “I must’ve been out of my mind.”
Not long ago, Terry Griffith had been the belle of Edwina Pearl High School, nearing the end of her senior year. She had it all, looks, charm and a really great guy in the person of her boyfriend, Kevin—a college freshman. To most of her girlfriends, this would’ve been more than enough. But the 18 year old had a dream—the dream of becoming a reporter.
With that in mind, the long haired brunette had entered a writing contest sponsored by the Sun Tribune. The prize a summer internship at the paper. She’d poured everything she had into her story, so it was shattering when she looked at the two winning entries posted in the display case for the Pearl Diver. Neither of them was hers.
“I’m not there.” she said unbelievingly to her best friend, Denise.
“Why aren’t you there?” the attractive blonde asked.
“Neil Perlow and Joseph Dreyer?” Terry said as she read the names of the two boys who had won.
Leaving Denise behind, Terry then had gone to the office of Mr. Raymaker, the school paper’s faculty adviser, to ask what was wrong with her story. She thought she had her answer in a comment she overheard another teacher making as he walked in with Mr. Raymaker.
“Then I had Terry Griffith for fourth period civics.” the teacher had said. “Did you see what she’s wearing ... the legs do not stop. I say we flunk her, keep her here another year.”
Mr. Raymaker had laughed at the suggestion.
That little comment carried a lot more weight than Raymaker’s statement that her article was good, but just not outstanding. That and his suggestion that she should have something to fallback on if she couldn’t make it as a reporter.
“You’re a pretty girl, you could be a model.” He had suggested.
Her mood hadn’t been improved later that day when she was swimming with Kevin. She was looking for sympathy and understanding, Kevin, however, was more interesting in getting the strings of her well filled bikini top open. He agreed with Raymaker’s suggestion that she was pretty enough to be a model.
“Besides, models make some pretty nice bucks.” Kevin had added.
“You don’t think I could do it either?” Terry had asked.
“Well no, that’s not exactly what I said ... exactly.” he replied.
“Yeah, well it was close enough.” Terry said, just before she asked the tall good looking hunk to leave.
Kevin was a little reluctant to go, seeing as Terry’s parents were away on a trip and she and her younger brother, Buddy, had the house to themselves. Of course the only part of the house Kevin was interested was Terry’s bedroom. But she was adamant and he finally left.
The final straw was when she walking into Buddy’s bedroom and found every free space on the wall had been covered with nude centerfolds. Her brother was a 15 year old virgin, and as horny as that combination could be.
“Your room is why my life is totally screwed up.” Terry announced as she looked around at the collection of exposed breasts and other female assets. “You guys think beautiful women are nothing but decorations—total airheads.”
Buddy’s feeble explanations that he also loved these women for their minds fell on deaf ears.
“I write an excellent article and just because I’m cute, no one takes me seriously.” Terry said.
“And somehow you find the courage to go on living.” Buddy said sarcastically as he leafed though another centerfold magazine. “You’ve got guts!”
“Sometimes I just wish I was a guy!” Terry mused. “I bet if a guy had turned in that same article it would be on the way to the Sun Tribune right now.
At that moment, an idea was born.
The idea was both daring and insane. Made possible only by the absence of their parents. With her brother’s helpful hints and a few layers of loose fitting clothing, Terry became one of the guys. Of course her long beautiful locks had to go, but the short boyish haircut was a small price to pay for her dream. Forging her parent’s signatures, she had transferred across town to Sturgis-Wilder High School.
Of course there were also a few minor problems - like which restroom to use. And avoiding gym class where her nude presence in the locker room couldn’t be explained. Yet with a few awkward moments at the beginning, ‘his’ masquerade was succeeding. Then she became involved with Rick and Sandy.
Terry had met Rick Moorehouse ‘his’ very first day. Tall, dark haired and extremely good looking, he was the type of guy Terry could immediately fall for. Of course that was the Terry who wore a dress and panties, not loose slacks and fruit of the loom briefs.
Still they became friends, a somewhat unique experience for Terry. It was strange to talk to a guy who wasn’t trying to get into her pants. She wished it could be more, but Rick only had eyes for Debra Strobich. Even worse, Rick had caught Terry sneaking looks at his cock. First in the bathroom at school and then again one afternoon he changed clothes in front of ‘him’. He was convinced that Terry was gay.
Sandy, on the other hand, was proof that she had succeeded in her masquerade. Also from day one, the cute brunette had been hot for the guy she described as a fox who dressed like Elvis Costello and looked like the Karate Kid. She had told her best friend that she was going to get him.
All of this had brought Terry to ‘his’ current predicament. Sandy had cornered Terry into going on a double date with Rick and her cousin. It wasn’t until they’d met the two girls up at “The Cave”, an actual cave cut into the side of a hill which doubled as a popular make-out spot, that Rick found out that Sandy’s cousin Jill was only 13 years old.
They’d been sitting around a campfire for almost an hour, talking and drinking a few beers. Jill of course had to settle for cokes. Getting a prearranged signal from Sandy, Jill suggested that Rick take her for a walk, saying that she thought Sandy and Terry needed their privacy.
“Hey wait, where are you going?” Terry called out as Rick stood up and began to head for the mouth of the cave. “Hey man, don’t leave me now!”
Rick looked to Sandy who gave them a playful wave good-bye. The smile on her face told him that his friend was about to get lucky.
“You kids have fun, huh.” Rick grinned as he picked up one of the lanterns they’d brought along and Jill followed him out into the darkness.
“They left me.” Terry said with an alcohol heightened sense of disappointment as ‘he’ rolled over onto ‘his’ back.
“It’s okay, I’m still here.” Sandy said reassuringly as she leaned over ‘him’. “Nice fire.” she added as she snuggled up against her date.
“Sandy, this really...” Terry implored as Sandy shushed ‘him’ and told him not to talk and started to plant kisses on ‘his’ cheeks.
“Sandy, this is a big mistake.” Terry repeated as ‘he’ pushed away the arm she had wrapped around ‘him’.
“Maybe, maybe not.” she replied pulling herself right back. “Only one way to find out.” she laughed as she tickled Terry across his stomach, catching ‘him’ off guard.
“Sandy, Sandy really...” Terry called out as ‘he’ tried to stop laughing.
Terry’s laughter turned to panic as ‘he’ felt Sandy’s hand slide down ‘his’ pants. “Sandy, get out of there.” ‘he’ cried out.
When her hand withdrew, she was holding a pair of sweat socks that had been stuffed into ‘his’ underwear. Before Sandy could comment on her discovery, Terry forced a laugh and said.
“There’s really a very a good explanation for that.” ‘he’ laughed.
“I’m flattered.” Sandy beamed, cutting off Terry in mid-laugh.
“You are?” Terry replied, somewhat confused.
“But you don’t have to do this to impress me.” Sandy added.
“I don’t?” Terry asked.
“No, I like you a lot.” Sandy continued.
“I think I’ll take one of those beers now.” Terry said, trying to change what had long since gone beyond just an awkward situation.
“It’s okay.” Sandy smiled as she handed ‘him’ another beer. “I mean, how small can it be?”
Terry chuckled as ‘he’ popped open the beer and said. “Don’t ask.”
“Then I’ll just have to find out for myself.” Sandy quipped as Terry brought the can of beer to ‘his’ lips and took a long drink.
Before Terry could react to what Sandy had said, the long haired brunette had again slipped her hand down into ‘his’ pants, causing Terry to jerk back and drop the beer.
“Oh shit!” Sandy cried out in a mixture of shock and confusion as her hand slid past a small mound of pubic hair and closed on what she expected to be a cock and balls. After a brief moment of confusion, she realized what she had grabbed.
“Sandy, I can explain!” Terry called out as ‘he’ backed away.
“Explain?” Sandy repeated, a look on her face that was a mixture of both confusion and anger.
“Just give me a moment.” Terry pleaded. “I promise you, I can explain everything.”
Sandy listened in fascination as Terry told her tale, noting that ‘his’ voice was now higher. She had to suppress a giggle as Terry told her about having to adjust to using the boys’ bathroom. Also about Rick’s conclusion that Terry was gay because he caught ‘him’ again staring at his cock that afternoon when he changed clothes.
.... There is more of this story ...