Disclaimer: Readers of the previous Jerry stories know what to expect here. Any new readers be warned, gay and bisexual themes feature in all of them. This one even includes some cross-dressing, all in good fun of course.
This story can be read and enjoyed (hopefully!) as a stand alone tale, but is the first of the series which would really be understood better if the previous one was read first, or after.
This story comes to you because of an email sent anonymously. Thanks for the suggestion whoever you are.
On with the play.
*****
"Oh ... oh ... fuck me."
Jerry tried to ignore his sister's cries.
"Yes ... harder ... deeper."
Not particularly loud cries, but the door to her bedroom next door stood open. Plus something about the sounds of sex captured the 18-year-old's attention and held it in a vise.
"Fuck me ... fuck me ... fuck me."
"How long could it go on?" he wondered. It seemed to be going on forever. Longer than the first time, this time went on and on, lasting at least twenty minutes so far.
"I'm ... going ... to ... come ... again," his sister, Diane, cried a little louder.
"Yeah ... me ... too!" said a louder deeper voice.
Jerry's ears perked up at the sound of Tom's voice. The sound of flesh slapping against flesh and his sister's words made it possible to follow the progress of the couple's lovemaking. His sister's partner made many sounds of pleasure, but uttered few intelligible words. When he spoke, the words always seemed to announce an imminent climax.
"Oh ... Oh ... Oh!" cried his sister.
"Here ... it ... CUMS!" said Tom. Counting those brought on by her blowjob and first fuck, this one would be the third.
"OH YEAH!" said Tom.
"OH GOD!" cried Diane.
There followed a jumble of words, phrases and sounds Jerry couldn't make out. He knew they conveyed feelings of extreme satisfaction. He couldn't help but feel jealous. Not of Tom, but of his sister. "Imagine receiving three big loads of Tom's semen," Jerry thought, reaching down to give his stiff penis a rub.
Jerry lay on his bed practically naked, his only clothing a pair of pink socks he knew Tom liked. The only light in the room came from the open door. Since this light originated in his sister's bedroom, it cast very little light. Even in the gloom he could see the pale skin of his body clearly. He gazed along its nakedness to his small erection.
"Did you enjoy your reward?" Diane asked.
"And how!" came Tom's reply.
Jerry failed understand the question or answer, but he was use to that. People seemed complicated beyond his comprehension and would forever be so, unlike Mathematics. Understandable with study and a little work, math made sense.
"Go get him," Diane ordered.
Jerry heard a deep chuckle from Tom. He looked to the door with a surge of anticipation.
"Oh ... and have him put these on," she added.
"Nice!" said Tom.
Jerry wondered what they were. It sounded like Tom liked them, so probably he would too.
He expected this request of his sister, but not the tone of command. While she prepared for Tom's arrival she mentioned she would have him come in when done fucking Tom. At the time he winced at the crudeness of the word, but now he could think of no better word for the activity he'd just listened to.
"You'll want to see him won't you?" she asked. There could only one answer to that.
The thought of seeing Tom again made him happy enough to put up with Diane's teasing. As he watched her applying makeup, she wanted to see how he would look like with his lips painted bright pink. He thought they looked ridiculous, but she seemed pleased with the effect.
"Why don't you leave it on. I bet Tom will like it," she said.
Now waiting for Tom to appear at his door, he hoped his sister was right. He thought it a silly idea for a guy, even a gay one, to wear lipstick.
"Hey little buddy, are you in there?"
The room darkened as a tall powerful figure filled the doorway. Tom's body was silhouetted by the faint light coming from his sister's room. No details could be seen, but clearly the man stood there naked. The 18 year-old athlete displayed an unusual state, an unaroused state. There between two massive thighs, Jerry could see the silhouette of the man's dangling cock. It looked big even like that.
His sister answered a question Jerry asked himself everyday for the last two weeks. How many times could Tom climax before he lost his erection? Apparently, three times would do the trick.
"Holy cow," he thought.
Something else was different about Tom. Jerry wondered what, then realized his friend wore no shoes. "You're naked,Tom," he said. For the first time Jerry saw him truly naked, not even wearing shoes or socks.
Tom laughed. "Yep, sorry to shock you, little buddy," the big guy said. "I can see you're not," he added pointing at Jerry's pink socks.
"Quit hiding in there and come join us," Tom said, relaying Diane's message. "And put these on please," he added tossing something small and roughly ball shaped towards the bed.
Jerry tensed as it flew at him, but when it landed on his chest, it proved to be very light. Tom demonstrated his athletic ability in a small way by the perfect toss. Before Jerry could compliment him on it, the big man returned to Diane's room.
Jerry debated with himself for several moments. Should he go to his sister's room, or not? After their lovemaking he would definitely be a third wheel. He'd told Diane he wasn't jealous of her doing it with Tom. That turned out to be untrue. Could he pretend it didn't bother him to hear how much Tom enjoyed it?
"Let's see what she wants me to wear," he thought, "Maybe it will make a difference."
He got up from the bed and flicked on the lamp on the nightstand. The garment was balled up and folded in on itself so Jerry needed the light to see how to undo it. He managed to figure out the topological puzzle in no time and shook out the silky fabric.
From the moment he felt its light weight and saw its blackness, he suspected it would be this very garment. His favorite one of all the nighties owned by his sister. Something fell to the carpet when he shook it, something black and lacy. He knew it too as the pair of panties his sister wore yesterday when teasing Tom. Diane knew him better than he thought possible.
Jerry knew all of her clothes having used his task of cleaning her room to explore. He tried on the black baby doll he held the first time he got to be alone with it. He liked the way it felt on his body, light and airy. He liked the way it felt against his naked penis. He really liked those things about the garment, but he also knew how ridiculous he looked in it. How could Diane expect him to wear it in front of Tom? Not to mention in front of her, what could she be thinking?
He didn't yet know how the panties would feel, but he could imagine. His penis would be snugly contained within the soft lace. At least its small size wouldn't be so obvious.
As if compelled, he slipped the lingerie on, feeling it fall softly over his nakedness. Shivers of excitement ran through his body caused by its teasing touch. Yes, he loved the feel of it.
Then he gingerly stepped into the panties and drew them up his long skinny legs. They didn't fit him as well as they fit Diane. His sister was wider in the hips than he, but she didn't have to fit a penis in when she wore them. They fit loosely, but Jerry thought they would stay up. They made him feel deliciously naughty.
"Come on little buddy. Get a move on it," called Tom.
"I'm sure you look darling Jerry. Let us see please," his sister said.
He couldn't resist Tom's call. Plucking up his courage and avoiding even a glance at the mirror, he walked to the door. Hesitating between the rooms long enough to draw in a deep breath, he wondered what he would do if they laughed.
"I'll die," he thought.
When he stood in the doorway he felt as if spotlighted on a stage. The naked couple on the bed, his audience, made it seem so. As he waited breathlessly for a reaction, mainly from Tom, the blood rushed to his cheeks.
"Wow, Jerry! Very nice!" said Tom.
Jerry could breathe again, but his face continued to heat up.
"My god, Jerry. You're so pretty. I'm so jealous of your beautiful red hair," said Diane.
This from his gorgeous sister would be quite a compliment if Jerry happened to be a girl. but he wasn't. Even so it came as a relief since he'd half suspected it to be some devious prank from his sister.
"He looks like your cuter younger sister," said Tom with a glance at Diane lying next to him.
"It may be true, but you shouldn't say it out loud," she said giving one of his nipples a twist between a finger and thumb.
"Ouch!"
"Serves you right," Diane stated.
After the initial reaction Jerry looked at the naked couple before him. He noticed they were very comfortable with each other. More than he thought possible for two people who met only the day before. Even if they'd just spent over a hour doing it with each other. Then again, what did he know about people?
They lay side by side on their backs. Tom's left arm under Diane's head while Tom's rested against the headboard. Both of them perfectly at ease with the naked display of their bodies. Both bodies shaved hairless, except for Tom's sandy crew top and Diane's luxurious honey-blond mane. His sister's breasts stood firm and perky, but Tom's cock lolled limply in full view.
Jerry's sister looked small beside the powerfully built youth beside her. Being two inches shorter than Diane, he realized how tiny he would look laying next to Tom. It excited him to think of it.
"The pink socks are a nice touch. They match your lipstick," Diane said.