Trading Places at Boarding School - Cover

Trading Places at Boarding School

Copyright© 2020 by Sterling

Chapter 3

Erotica Sex Story: Chapter 3 - Twins Jason and Julie are stuck at conservative, religious, same-sex boarding schools. They are so horny that they devise a plan to secretly switch places to satisfy their desires. A good time is had by all, but with both student bodies having only rumor to guide them instead of accurate sex education, there are complications.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Teenagers   Consensual   Romantic   Heterosexual   Humor   School   Brother   Sister   Group Sex   First   Masturbation   Oral Sex   Pregnancy  

Jason felt nervous as he approached Julie’s dorm. He knew which door to use ... up one flight, down to room... 27.

He used the key to get in, and saw Julie’s roommate Melissa at her desk.

“Hey, welcome back,” she said, eyes still on her phone.

“Good to be back,” said Jason in the high voice he had practiced.

“You have a cold or something?” asked Melissa.

“Um, yeah, I guess a little...”

Melissa looked up. “Wait ... you’re not Julie, you’re Jason! You really did it!”

Melissa stood and backed up from the desk to stand with her back against the bureau.

“I knew you two were talking about it ... but ... there’s a boy in my bedroom!” she said, with a mixture of excitement and nervousness. “Even if he is wearing a skirt.”

Jason looked down. Sure enough, he was wearing a skirt, and he felt a brief flash of shame.

“I promise I’ll give you all the privacy you want,” said Jason, letting his voice sink to its normal register.

“Oh, yeah ... I’m sure you will ... it’s not that, it’s just ... I’ve gotta go.” With a smile she brushed past Jason, shutting the door behind her.

Jason unpacked. Another couple skirts, a couple bras, pre-padded, but boy undershorts. Julie had boy undershorts to help with her disguise. Jason couldn’t go that far. His boy stuff just wouldn’t fit inside panties.


“You’ll never believe it!” said Melissa, rushing into Linda and Nancy’s room. “Jason came back in Julie’s place!”

“Oh, wow!” said Linda.

“You’re kidding...” said Nancy.

“No! He’s got the skirt and sweater -- he really looks a lot like her!”

“So ... he’s going to be your roommate? Sleep in the other bed? Just a few feet away?”

“I guess so ... what else could we do?”

“And he knows how horny you are!” said Linda with a smirk.

Melissa gulped. “Yeah.” Julie had reported the conversation between her and Jason in October, about everyone at both schools being so horny. Surely she had mentioned Melissa by name to her brother, she being perhaps the horniest of them all.

“So, are you going to let him do it to you?”

“I ... I don’t know.”

“A bit more scary when it really might happen, eh?” said Nancy. They had all heard Melissa talk about how she couldn’t wait to ditch her panties, spread wide, and welcome some guy into her vagina -- that is, the huge, pulsing penis that stuck out the front of him.

“What about pregnancy? What if I got pregnant? That would be the end...” Their conservative parents would all have a major cow if any of them got pregnant. They had sent their daughters to a single-sex school with strict visiting rules -- as in no boys in the dorm, ever.

Linda said, “My big sister Rachel -- you know, the married one -- she’s told me about sex sometimes.”

“Yeah, we know,” said Nancy. Linda had relayed a lot of what her sister said ... it was the main way they knew about what sex was really like at all.

“But about pregnancy ... She and David have been trying for over a year now, and no baby. She says it’s a lot harder than people think. She said she thinks they warn us about pregnancy just to scare us.”

Nancy said, “I read in a magazine that you can only get pregnant during your period. Nature gives you a sign to let you know when it’s time. So you can do it without worry the rest of the month.”

“Really?”

“I’m sure.”

Melissa’s period had ended ... what, a week ago? Something like that. So that was no excuse. She said, “And you remember what Julie used to say, about ‘genuine rape’? How it’s really true that you can’t get pregnant unless you want to? That guy in Congress let it slip, then they all made him shut up because they don’t want us to have sex. It’s a sin ... and if we’re not afraid of getting pregnant maybe we’ll do it.”

“So, you going to let him do it?” asked Nancy.

“I ... I don’t know. Maybe he won’t want to. Maybe he’ll think I’m ugly.”

Linda said, “You know that’s not true ... how Julie showed him pictures of us on her phone, and asked him what he thought, and he said he’d love to do any and all of us.”


Melissa and Jason were uneasy with each other the rest of the day. Jason kept his head down mostly at dinner, with his hand nervously near his face. His hair was long enough to provide some cover too.

After dinner they looked at the assignments on their phones, worked on problem sets or read textbooks or finished unpacking. When it was time for bed Jason said he’d use the handicapped restroom, telling Melissa he’d be a while. She figured he wanted to give her plenty of time to do anything private she wanted. She was in bed when he came back, and she kept her face to the wall while he changed. The lights went out at 11 -- school policy. The phones went dead at that hour too. Jason and Melissa lay in their beds quietly.

“This sure is weird,” said Melissa.

“I’ll say!” said Jason. “We boys dream about maybe finding some girl in a corridor of some building and sneaking a quick kiss...”

Melissa laughed. “Yeah, us too. And of course Julie talked about you.”

“And she talked about you too!” said Jason. “Some kind of private stuff.”

There was a brief pause. “Was she kidding when she said what you think about all the time?”

“No! And here we are.”

“I’m so nervous ... But maybe we could get in the same bed and just hug?”

“Sounds great!”

Jason crossed the room and Melissa pulled back the covers to let him in. They were both in flannel pajamas. In the semi-dark they could barely see each other’s faces.

Jason said, “Maybe a kiss?”

“OK,” said Melissa, “but I’ve never done that.”

“Me neither. But it can’t be too hard.”

At the touch of Melissa’s lips Jason shuddered and felt Melissa squirm. His cock was already hard, and now his whole body burned with desire, his cock most of all. She suddenly pulled him tight against her.

“Who am I kidding with kissing? I want your thing inside me -- so bad!”

“Really? Don’t we have to do other stuff first ... like touching you to get you ready?”

“Maybe sometimes, but not now.” Her hand found the bulge Jason’s stiff cock made in his pajamas. “Oh, God, put that in me now! Don’t make me wait!” She turned onto her back and he heard rustling of cloth as she got ready. He pulled his own pajamas and underpants down.

It was obvious what to do ... He turned over onto her and shuddered when his hand felt the place between her legs ... no cock, no balls, pure female ... Hair, but right there in the middle ... he pressed and his finger indented the flesh.

“Let me help,” said Melissa, and he felt her fingers down there touching herself and then her fingers on his cock. He pushed forward and met hot wetness. He pushed more and the wetness gave way and surrounded his tip. It was amazing! As he kept pushing, her vagina gave way and hugged his shaft, slick and hot.

“Oh, God!” he said, and pulled his cock back out, then plunged in again. He’d jerked off, of course, but this was nothing like that. His body rose to ecstasy without him even thinking about it, and after withdrawing once more he surged his cock in deeper as it began spurting, over and over again -- he’d never felt so good in his life. As the spurts died down he relaxed and withdrew, Melissa’s pussy giving him the same wet, tight embrace on the way out.

Melissa hugged him tight. “You did it! I’m not a virgin any more! I’m so glad!”

“Yeah, it was great!” said Jason.

Melissa hesitated. “But...”

“Something wrong? Was I no good?”

“Oh, no, you were fantastic! It’s just ... you know, our religion. Sin and all that.”

“Oh, yeah, that’s true. I figure we have to kind of pick and choose. I figure everything they tell us about sex is wrong. The other stuff ... sure. I masturbate, and I don’t feel guilty about it any more. Do you?”

“Um, yeah, I certainly do it. And don’t feel too guilty ... mostly.”

“Yeah, me too. But the stuff comes out, of course.”

“Think of it this way ... spilling your seed is a sin, but putting it inside a woman -- that’s blessed -- the holy sexual act!”

“Yeah, but --”

“Stop thinking so much.”

He felt Melissa reach down and find his penis. It was already half hard, and her touch finished the job.

“And if you’ve already sinned once, it’s not much worse to do it again,” she said playfully.

Jason smiled, turning over onto Melissa. She started guiding him in, but he brushed her hand away, saying, “Let me figure this out.” He found her opening -- the stunning smooth wetness that started in the middle of hair. “That’s so amazing, how we fit together!”

He shoved in. It felt just as fantastic as before, but this time he knew what to expect. He surged in and out, over and over, trying different rhythms and stroke lengths and angles. Fast little in and out right near the opening, long deep strokes, pauses ... They all felt great ... The pleasure built more slowly.

“It’s great,” said Melissa. “It’s wonderful feeling all these different ways, but there was one thing you did ... would you be willing to do that one more?”

“Sure!” said Jason.

“Slower, but when you’re in all the way, stay that way for a few seconds before going out again? Don’t go out too far ... Yeah, like that! Wow, like that!”

Jason did just what she said, over and over again. It felt great, and he heard her gasp and wriggle and moan, more and more, and then suddenly she let out a tremendous gasp. Orgasm! He had made his partner come! He kept doing it the same way. Melissa looked very happy and relaxed, and she said, “Now the way you like best ... I mean, take your time, whatever you want, I’m just hoping you’ll come ... Oh, shut up, Melissa.”

He kissed her and smiled. “I love everything you say.” He didn’t need any more encouragement down below. He plunged into the welcoming pussy hard and fast, long and deep, and then climaxed again, spitting more sperm way up inside Melissa.

When they had both calmed down, Jason said he’d need to get some sleep, so he returned to his own bed and didn’t stay awake long, relaxed and happy as never before in his life.

He was startled out of sleep to feel Melissa crawling into bed behind him. It was just starting to get light outside. “I don’t ever get to hug anyone,” she said. “I love that ... even that.” He realized that she didn’t have any pajamas on. “And for both of us to be totally naked ... that would be amazing.”

Jason agreed, and soon shed his pajamas and underpants, but his cock quickly got stiff. Melissa spooned against his back and made a contented sigh. Before even two minutes, however, he felt her hand gently creeping down to his cock, which betrayed his sexual desire.

“Sorry,” he said. “This was supposed to just be a hug, but my body ... you know.”

“Why don’t we practice hugging face to face, with me on my back?” Was that a hint of a smirk on her face?

That sounded great. When they got in position, he hugged her, while down below his stiff penis ended up pressed against the innermost part of her thigh, right up so close to where it belonged...

He said, “Oh, that’s so great. Your skin and all, but...”

“Are you thinking naughty thoughts?” said Melissa playfully.

“Yeah...” said Jason.

“Let my naughty part give your naughty part a hug...”

Jason smiled and felt Melissa’s fingers guiding him. He shoved. It went in ... it felt fantastic.

“Hugging is great, but I couldn’t help think of your penis most of all ... going in and out, just like nature intended.”

Jason rowed in and out in silence, blissful.

Melissa said, “I’d be happy to lie like this and feel you fucking me for hours -- oh, that’s so naughty to say! -- But you can finish up any time too.”

“I’m fucking you. You mind I say that?”

“No! You are fucking me. Keep fucking me.”

“OK, I fuck you. I fucked you. I have fucked you. I am fucking you. I will fuck you. Fuck...”

Melissa laughed. “Oh, fuck grammar. Fuck me.” She lowered voice to a grunt, “Fuck, fuck, fuck!”

Jason joined in with his own, “Fuck, fuck, fuck!” even lower. Down below, his cock kept fucking in and out of her, over and over again.

“How about this?” he said. He began the same motion that she had loved the last time.

“Oh, that’s nice, but you don’t have to. I’m not sure anything will happen...”

“But I want to...”

“It’s OK, really...”

“Shut up and get fucked.”

Melissa grinned at that and relaxed. “OK, fuck me however you want. You can be the boss. The fucking boss.”

Melissa kept looking relaxed, but she also seemed more excited. Gradually it built. Then she shuddered as she came again. As they fucked, the sky was getting lighter and he could more clearly make out the girl beneath him, a perfect female to his eye. Lovely breasts, lovely shoulder-length light brown hair, eyes closed but face relaxed with pleasure, and then down below, of course, the spread legs, the pubic hair, but out of sight, that magnificent vagina that hugged him so tight and hot. He chose a faster, harder rhythm.

“So handsome,” she murmured. “So strong ... so stiff...” She giggled. “Let me watch you finish up ... I want to see it.”

They locked eyes as his strokes got more urgent and stronger, but then he couldn’t help closing his eyes as he concentrated on the fire in his loins. What would he do if it really was all up to him? He went faster, deeper, harder ... oh, so fast, oh so deep, oh so hard. He grimaced. The climax approaching, then the culmination ... ecstasy, twitching, a few more clots of sperm delivered.

When he opened his eyes, Melissa was smiling brightly. “Wow! That was so cool!” When he started to withdraw, she said, “Can you stay inside a while? I’d love that.”

Jason decided he’d love that too, and he was aware of his body locked together with this female, languid and without a specific goal in mind, just fitting together and complementing each other. He felt his cock getting smaller. That was natural after he jerked off, but was it natural when it was inside a girl? It kept shrinking. Then she coughed, which pushed it right out of her.

“Uh, sorry,” he said with confusion.

“That’s fine” she said. “Your thing has done me three times tonight. I think he’s allowed to take a little rest.”

“OK, glad to hear it,” said Jason.

“At the end there it hurt a little,” she said.

“Oh, sorry! Why didn’t you say?”

“Because I didn’t want to. You were so ... ferocious. Hurting felt good just then. Does that make sense?”

“I don’t know, but it’s just if it ever...”

Melissa put her hand over his mouth. “I know, I know. I could have told you, and I know you would have stopped instantly, but I made my choice -- and I’m glad I could tell you that too!”

“OK,” said Jason from behind Melissa’s hand.

They lay beside each other and Jason dozed off, awoken finally by Melissa’s alarm. Time to face a new day.


Melissa joined Nancy and Linda in their room when class was over.

“You did it, I can tell!” said Nancy. “You look ... happy all over.”

Melissa grinned. “Is it that obvious?”

“Yes!” agreed Linda.

“So, what was it like?”

Melissa gave a brief summary.

“Three times! You did it three times?” said Nancy.

Melissa shrugged. “It felt great. It still feels great.”

“I want a turn!” said Linda.

Melissa suddenly sobered up. “He’s mine!”

“No, he’s not! Remember the deal? How he wanted to do every one of us? You can’t hoard him to yourself!”

“But ... I’d want him for my boyfriend ... I’d almost marry him ... Does that sound crazy?”

“Not crazy, but not exactly realistic. But as for keeping him for yourself, I’d never tell what you’ve done, no matter what. But the word will get around. You think the other girls will be happy with you hogging him all to yourself?”

Melissa bit her lip. “I guess you’re right.”


When she came back to the room Jason was studying.

“So, you get to choose which girl you want to sleep with tonight.”

“Oh ... oh! It was so great with you...”

“Yeah, but they all want a turn. I can’t blame them. It’s not like you and I can get married or anything.”

“Yeah, OK,” said Jason, grinning.


Jason picked Linda, so she came to his room near bedtime, swapping beds with Melissa for the night.

Things were much less awkward and tentative, because they both knew what they were there for.

They both got naked. Linda had bigger breasts and hips, but she was still plenty sexy. That place between her legs, the part that looked hairy but on just a little exploration revealed something so hot and wet and welcoming -- that was the center of the universe. His cock didn’t go in right away, so he tried stroking her down there with his fingers, over and over again. Linda smiled and after just a couple minutes said she thought it would work better now. This time his cock went in and she winced. He instantly stopped and looked at her, questioning.

“No, no, keep going!” she said.

His cock went in -- and it was heaven just like Melissa’s vagina. After a couple minutes of very satisfying in and out, he asked her if there was something special she wanted.

“Not sure what you mean,” she said. “I just want to have sex. And it’s great so far.” She smiled.

Jason bored into her with lustful enthusiasm, pounding and pounding with rising pleasure until it broke in waves of pure satisfaction, his penis delivering its gobs of stuff deep in her pussy. He’d now scored with two girls!

Linda looked content, but returned promptly to Melissa’s bed and fell asleep before he did. He would have done it again, but ... no need to get greedy.


Nancy was next. She was a fine, interesting girl, with a great sense of humor and interesting opinions. She had a great smile. But laid out below him on the bed, all he saw was her welcoming pussy opening, then all he felt was his cock easing through the opening into the vagina inside, easing further and further in. Each vagina was a little different, but they had an awful lot in common. They were exciting places that made him and his cock feel fantastic, made him thrust and hump and penetrate deeper and then shudder with amazing pleasure as he delivered sperm way up inside. Nothing had felt so good and right in his whole life.


When the class was working, Mrs. Green approached Melissa and said, “You look happier ... did something good happen over Christmas? Your work is better too.” She used a quiet voice but the rest of the class could hear.

“Oh, nothing I can think of,” said Melissa nonchalantly.


Gretchen excitedly let herself into her room and shut the door. “Anne, you’ll never believe it! It’s not Julie, it’s her brother Jason! They swapped places!”

“You’re kidding!”

“He and Melissa must be doing it. But not just them, I can tell from the way they look -- Linda and Nancy are in on it too!”

“We should tell -- this isn’t right.”

“It’s not up to us to rat on them! I’m going to go ask them about it.”

Gretchen hurried down the hall and knocked on the door to Melissa and Julie’s room.

“Who is it?” came a voice that was like Julie’s, but not quite. The door opened just a crack.

“Is Melissa there?”

“No, she’s down at Nancy and Linda’s. I’m kind of busy with stuff, sorry.” The door shut again without her ever getting a glimpse of Julie -- and it wasn’t Julie, of course, it was her brother Jason.


“What’s up?” asked Linda when Gretchen appeared.

“I know it’s Jason who came back in Julie’s place. And he’s staying with you, Melissa.”

“You wouldn’t tell anyone, would you? About Jason being here?”

“Of course not! Did you have sex?”

Melissa paused. She said, “Yeah” tentatively, but then said “Yes” and then “Yes!”, with a big bright smile. “He’s done me and I love it. I love it so much! He’s done Linda and Nancy too, and we all love it. We girls dream about it and think about it and maybe even play with ourselves, and think we have to wait until we get married. But ... it’s so wonderful ... You want to try? Find out what sex is like? You can’t get pregnant unless it’s your period.”

“Wow, that’s...” Gretchen squirmed her hips.

“Yeah, we all feel like doing that...” Nancy imitated Gretchen. “You’re a young woman and your body is all ready for sex, and all the uptight grown-ups say you have to wait, wait, wait. It’s fantastic to actually do it.”

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