tagTranssexuals & CrossdressersHigh School Love Ch. 04

High School Love Ch. 04


The last chapters of "High School Love." Like I've said previously, this is the end unless I get enough feedback to continue this story. I've already got a few shorter ones I'll be posting soon and another rather long one (longer than this) that's similar to HSL, but I think better.

The couple brings in a new friend for some fun, hope you all enjoy!


The next day Jamie and Emily hang out a lot. They talk about what happened and Jamie's feelings toward Emily. Emily admits to liking Jamie as well, but she doesn't even know it until she admits it. Later that day Emily tells Jack what's happening with her and he smiles and thanks her for her truthfulness, and won't mind knowing what Jamie thinks of him.

The next couple of days the three teens hang out with one another but nothing really transpires between the three of them. But on Friday, things change. The three are at Emily's place as usual, watching TV. When Emily begins, "So... Jamie, I've told Jack about you."

Jamie looks over at the other two, stunned, and afraid.

"It's okay, he's okay with it. I told him how I felt about you too, and he's okay with that too."

"You are?"

"Yeah," Jack says matter-of-factly.

Jamie looks down, quite bashful of the situation, and thinks. "Um... so what happens now?"

"Well," starts Emily with a smile, "what do you think about Jack?"

"Um, he's cute I guess..."

"I guess?! He's the cutest guy at our school!" gushes Emily. Jack smiles and thanks her. "How about this, come over here."

Jamie does so and stands in front of the two. Emily stands up next to her and grabs her hand gently. She smiles at her and leans in for a kiss. The two girls kiss for just a moment before Jamie breaks away giggling. "Now before we go any further you need to know something about me," begins Emily. Jack takes his queue and stands up next to the girls and holds his girlfriend's hand.

"You see," Jack smiles, "Emily here is a very special girl."

"Yes, I am, and you need to be open minded about this if you really want to start something with the two of us."

Jamie listens intently, with excitement and with confusedness, "I don't quite understand..."

"Here, I think we should go to my room," says Emily with a gentle hand. She leads Jamie and Jack up to her room. Jamie giggles at the sight of all the pink and frilly in her room and gently takes a seat next to Emily on her bed. Jack accompanies Emily and stands by the bed, still holding her hand.

"Before we start anything, I need to know that nothing in here leaves this room, understand?" Emily says with a light fierceness in her tone. Jamie nods and waits patiently. Next Emily stands next to Jack and smiles at him. He smiles back and nods.

Emily faces Jamie with tears building in her eyes and begins again, "Okay, I'm not what I seem..." Emily then takes her hand and unzips her jean zippers. She wiggles her tight fitting jeans down her soft smooth legs and steps out of them. In her cute cotton pink panties, Emily grabs the elastic and gently tugs them down. She parts her legs slightly as she bends over and pulls them down, just like the first time she revealed herself to Jack. Once down to her ankles, Emily steps out of them and slowly straightens herself in front of Jamie. Before standing completely straight, Emily looks up at Jamie and waits for her expression as she slowly shows her secret.

Jamie gasps and covers her mouth as she sees Emily's tiny cock standing at attention. "Oh my god!!! I had no idea!" says Jamie.

"So what do you think? Even though I have this, I am a girl," defends Emily.

"She is the best girl a guy could have," adds Jack.

Jamie sits there in silence thinking and looking at Emily's secret before saying, "I like it, I think it's cute!" Jamie nearly leaps off the bed and stands on her knees in front of Emily. Her mouth is right at her erect little cock and she gently kisses the tip. Pulling away, "cute!!! Does it work?"

"Yes, but that's as big as it'll get," says Emily.

Jamie doesn't say anything; she moans quietly and opens her mouth to take Emily's tiny cock and balls in her mouth. Emily moans as Jamie engulfs her genitals in her warm mouth. Jack takes a seat and watches his girlfriend receive pleasure from another girl. However this only lasts for a few moments before Jamie gets up and starts stripping her clothes.

Before anyone knows it, Jamie's completely naked. Her perky little breasts bouncing as she jumps on the bed with a huge smile. Emily climbs on the bed as well and lies down. Jamie immediately jumps on top of Emily and starts kissing her with as much passion as she can afford. She gently grinds her hips into Emily, moaning while doing so. The two girls make out while Jack starts getting undressed as well. He joins in relatively quickly and lies on his back next to Emily. Gently rubbing his hand on Emily's thigh, Jack watches as the two girls madly kiss each other.

After a while Emily pushes Jamie off, "Let Jack join too."

"Oh yeah! I almost forgot!" she giggles. Jack eagerly grabs Emily and pulls her over so she straddles him. Her hair in his face, he smiles up at her, "I love you so much!"

"I love you too Jack," she smiles back. She giggles quietly feeling Jack's erect member on her butt.

Before anything starts, Jamie interrupts, "Can I watch?"

Jack is a bit embarrassed but Emily chimes in, "Sure." Jamie jumps off the bed and finds a chair nearby. She comfortably plops her cute little butt down and spreads her legs wide. Emily smiles at her as she gets ready for Jack. She lifts up and grabs Jack's cock. Emily teasingly flicks it between her butt cheeks before she finally presses it into her love hole. Within a few attempts Jack sinks his erect cock into Emily. She moans out as her bowels accommodate Jack and she happily sits back and rests her body on top of Jack's chest.

Emily wraps her arms around Jack's back and clenches her thighs around his waist as she slowly pulls out and pushes back in. The couple gently fuck for a while feeling the sensations in their loins when they hear a burst of moans escape from across the room. The two look over and see Jamie furiously fingering her pussy. Emily smiles and looks back at Jack, "We'd better hurry up and catch up!" with that Emily lifts her body a little and allows Jack to give her a thorough pummeling.

Jack gives a few slow deep thrusts, just to test the waters, before he gives Emily a pounding of a lifetime. Within moments Emily's already gasping for air and moaning in obvious approval, "Holy shit!! Fuck that hole!!! Fuck it!!! Fuck it!!!! FUCK IT!!!!!!" The two sweat profusely, but don't mind, as their bodies are one.

Another burst of moans disrupt Emily and Jack and they look over again to see Jamie squirming in her seat and moaning hysterically. "Oooohhhhh!!!!!!!" moans Jamie as a splash of liquid gushes from her pussy.

"Oh please fuck me Jack!!!!!" begs Emily. Within another few moments Emily's breathing is at her highest and her loins are burning for release. "Oh Jack!!! Don't stop!!!!!!"

"Come on baby, cum for me," he grunts.

"FFFFFUUUUUUCCCCCCKKKKKKK!!!!!!!!!!" groans Emily as her tiny cock erupts thick globs of cum. She spews out thick ropes of cum all over Jack's chest and stomach as he fucks her for all she's worth. Emily's asshole involuntarily clenches and unclenches as she cums and causes Jack to moan out, "OOOOOOHHH!!!! BABY!!!!!" he too explodes coating the inside of Emily's bowels with thick creamy goo. The two lovers lie there, slowing their thrusts until they reach a stop.

"Wow! That was hot!" exclaims Jamie. Emily looks over, just remembering that they have company, and meekly smiles. She gracefully dismounts and lies next to Jack. She wipes her bum hole with her hand and licks any traces of Jack's cum. "Can I try?" asks Jamie.

"With who?" asks Emily.

"Either one, I don't care, I just want some of that!" she giggles. Emily is completely exhausted and recommends Jack take her. He smiles and beckons for Jamie to join them. She happily obliges and jumps on the bed, instantly straddling Jack, just like Emily previously did. She giggles as Emily's cooling cum coats her thighs and pussy mound. Jamie hungrily grinds her pussy on Jack's stomach, moaning, and leans in for a kiss. The two hesitate, but Emily ushers them on. Before they know it Jamie and Jack are making out furiously.

Jamie does her best to get Jack aroused again and is pleased that it doesn't take long before she feels his hard cock on her smooth round butt. "Oh is this big boy ready to go already?" she giggles.

"Mmhhmm," moans Jack. Taking the signal, Jamie grabs a condom and wraps it around his hard shaft. With little effort it's on and she lifts up a bit and guides his cock. Finding it she slips it up her hungry pussy and gently pushes all the way down until she's resting on his lap. Just as Emily and Jack did earlier, Jamie lifts herself and starts impaling her pussy. Jack is surprised by her aggressiveness as she takes long quick strokes moaning in obvious pleasure.

"Mmmm," moans Jamie, "This is way better than masturbating!" Jack only groans as he tries his best to hold off his orgasm. Jamie's moans and breathing get a bit quicker and her thrusting becomes more pronounced. Emily sees this as well and joins in. She scoots over to her friends and gently rubs her hand over Jamie's perfect round ass. She gently rubs it for a while before her wandering hand eventually reaches Jamie's butt hole. Emily slips a finger in Jamie's rosebud and she yelps out in pleasure.

"Do you like that?" asks Emily.

"Oh yes! That feels amazing! Do it faster!" moans Jamie. Emily complies and slips in a second finger.

"Oh my god!!! Yes!!!!!!! Fuck that little ass!!!!!!!' moans Jamie. Emily and Jack work in perfect tandem as they get Jamie off within a matter of minutes.

"OOHHH YEEEESSSSS!!!!!!!" she screams. Jack feels Jamie's pussy spasm and he can't hold himself together through her orgasm.

"I'm Cumming!!!" he moans. Jamie bounces off, quickly rips the condom away, and then swiftly slips her mouth over him, gulping down his seed with ease. Jack shoots three thick ropes of cum to the back of Jamie's throat. She hungrily slurps all of it down without missing a single drop. She sucks him until she's completely sure she's emptied Jack.

"Oh my god, that was amazing!" groans Jack.

"I know!" smiles Jamie. Emily and Jack are completely stunned as to how quickly Jamie's become a little slut. The three take a quick nap together before heading home for the night.

Chapter 9

The final day of school finally arrives and all of the students are giddy with excitement. Emily, Jamie, and Jack spend one more night all together, Emily and Jack more than once, from their last love making session before their final day of school. With the final day here, many students are saying their good-byes as many of their friends leave to different colleges. The same is for Emily, Jamie, and Jack. Emily and Jack are going away together at the state college while Jamie is going away; out of state to Chicago.

The trio head back to Emily's when Jamie giggles.

"What's up?" asks Emily.

"Oh nothing," giggles Jamie. The rest of the trip fills with chatter among the two girls until Jack breaks it up by announcing that they're at Emily's.

As their usual routine for the past two weeks, the three friends plop down to some TV, with Emily and Jack cuddling up close to one another while Jamie sits nearby hugging a pillow. They watch television until around dinner time when they order in a pizza.

After dinner things get a bit more intimate as Emily attacks Jack's tongue. The two make out furiously while Jamie watches with a huge smile. Jamie's quite surprised when she sees Emily push Jack onto his back and starts dry humping him. She only imagines what's happening underneath her short skirt; Emily's small scrotum and penis slowly getting hard in her panties under her skirt. Her mind races along as with her heart as she imagines this.

Jamie awakens from her sexual trance from a loud moan. She smiles some more as she sees Jack fondling Emily under her shirt and wishes Emily was doing the same to her. Unable to keep to herself Jamie plunges a hand down her tight khaki shorts and rubs herself feverishly. Within moments she's writhing in ecstasy. She holds off her orgasm though and pulls out her soaking hand. Jamie quickly climbs on the same couch as the others and snuggles up behind Emily. She fondles Emily's butt under her skirt and enjoys the silky panties she's wearing.

"Mmmm, I think these would be better taken off..." she whispers. Emily stops her dry humping and lets Jamie pull her panties down from under her skirt and then throws her panties on the floor. Emily yelps as she feels Jamie's tongue lapping at her asshole. "Wow slow down there," Emily snickers. Jamie continues her assault until Emily gets off Jack.

Emily and Jack sit up and rip each other's tops off until they're both bare-chested. Just as Emily falls back on top of Jack again Jamie chimes in, "can we try something new?"

"Uh sure, what'd you have in mind?" asks Jack.

"Well, let me show you..." giggles Jamie. She leaves for a moment and returns with a dildo and harness in hand. "I want to fuck Emily!"

"OOOHHHH!!!! Yes! YES!! YES!!!!!!" beams Emily. Jamie quickly takes off her shorts and panties and puts on the harness and playfully strokes her fake cock. She climbs onto the couch and pushes Emily onto her back.

"Get your fucking skirt off now!" demands Jamie. Emily smiles and unzips her skirt and lies back on the couch. She presents herself to Jamie who wastes no time and guides her silicone cock to Emily's asshole. Without any lube Jamie forces herself rather vigorously into Emily who groans in discomfort. Emily's a bit taken back by Jamie's aggressiveness and whimpers slightly as Jamie thrusts the six inch cock all the way in. Emily closes her eyes as Jamie begins, groaning with each thrust.

"Mmmm you like that bitch?" asks Jamie bluntly.

"Mmhhmm..." moans Emily.

"You like how I'm fucking you, you little slut..."

"Oh yeah..."

"Open your eyes and look at me while I fuck you!" orders Jamie harshly. Emily does so and sees fire in her eyes as she works her asshole.

"Please! Slow down! It's too much!!!" pleads Emily.

"Why? Are you gonna cum?"

"Uuuuhhhhh... it's... too... much..."

"Yeah, take it bitch!!!!"

"UUUUUUHHHHHHH!!!!!!!!!" Jamie looks down and watches as Emily's tiny cock spasms and three ropes of cum squirt out of her cock and onto her belly.

"Yeah, look at that! I made the little bitch cum," grunts Jamie.

"Please stop!!!" begs Emily. Jamie finally slows down and finally pulls out. Jamie giggles, "That was fun!" changing her mood almost instantly.

"Uuuggg, it felt good, but girl, you're rough!"

"Yeah, well I like it like that."

"Well if that's the case," buts in Jack. He pushes Jamie onto her back and rips off the dildo harness in one smooth stroke. In a matter of seconds his pants are off too and he's guiding his ragging cock into Jamie's tight pussy.

"Ooooohhhhh sssshhhhiiiittttt!!!!" groans Jamie. Her nearly virgin pussy struggles to take Jack's six inch cock. His girth stretches her uncomfortably, like the first time, and Jamie tries to pull away, but he's having none of that, Jack pulls her back into him until he's buried his cock as far as it'll go.

Jack starts pounding Jamie's pussy just as roughly as she'd pounded Emily. "How do you like that you fucking slut!!!" he yells. Jamie squirms on the couch trying to get away from Jack's relentless thrusting. "OOOOHHHH FUCK!!!!!" screams Jamie. She spasms on the couch as her orgasm overtakes her. Her earlier stimulation coupled with her arousing fucking of Emily is just too much for the little girl as Jack hits home with each deep thrust.

Jack's nowhere near orgasm and keeps plowing away at her tight little pussy. "No one calls my girl a bitch and gets away with it!!!!!" he yells. Jamie can't contain herself and cums again. Hearing all this dirty talk and taking this pummeling by Jack's thick cock is just too much for her.

Emily recovers and kneels beside Jamie, gently kneading her breasts. She kisses her friend and gently strokes her limp cock. "Come on Jack, pound that girl!"

"Oh baby!! I'm cumming!!!!" Jack erupts inside of Jamie. He sends five thick loads of his seed deep inside Jamie's womb before he slows to a stop and pulls out. "How do you like that... bitch."

"Mmmm, that was fucking amazing!!!!! You made me cum so hard!!!!!" she giggles.

The three lie together, cuddling up, while they recover from their orgasms before Jamie scampers off for a moment. She prances back, still naked, and with a huge smile as a devious idea strikes her. "You know... that harness allows the wearer to put his, or her, dick in to the dildo... I was thinking; why not let Emily try it on me?"

"Oooohhh I like that!!!!" Emily ecstatically jumps off the couch and grabs the harness. She lets her limp cock into the dildo and adjusts herself, "not a bad fit."

"So Jack, are you ready for round 2?" asks Jamie.

"Uh I guess," he says while still recovering, "why, what'd you have in mind?"

"Well, since you guys think I'm such a slut, I think it's only appropriate that you treat me like one. I want you two to both fuck me, at the same time!!!!"

"Wow!" shouts Emily.

"Uh... okay..." says Jack quite stunned by this seemingly shy girl.

"Now since you've already fucked my pussy, Jack, I want you to fuck my asshole now. And Emily if you don't mind, I want you to fuck my pussy."

Emily, "Oh goody!!!"

Jack smiles and wonders how this is all going to work. His questions are answered surprisingly quickly as Jamie helps Emily into the harness and then pushes her onto her back on the couch. She giggles as the dildo points straight up from Emily's hips and she straddles Emily over her belly. Her naked bald pussy drips with anticipation on Emily's pierced naval and wastes little time with any teasing. In a moment's notice, Jamie sits back and plunges her aching pussy on Emily's thick cock, moaning in apparent approval.

"Mmmm, your cock feels sssssooo nice in my pussy!"

"I bet it does! Now kiss me!" moans Emily. The two girls make out frantically while Jamie slowly gyrates her hips over Emily's dildo. Jack can't take anymore of this and kneels on the couch behind the two girls. He marvels out Jamie's cute little butt and smiles to himself seeing her pink asshole seemingly winking at him.

Jack takes his hands and gently glides them over Jamie's round little butt cheeks. He smiles hearing her moan in ecstasy. "Yeah, you like that you little bitch."

"Mmmmhhmmmm," she moans still kissing Emily. The two girls jab each other's throats with their tongues and sloppily attack each other's breasts as well.

All of a sudden Jamie pulls away. "Are you gonna put that in me or what?"

"Wow, slow down there," Jack defends, "I'm just getting ready." Jack lubes up his cock, stroking it as he does so and then points his cock at her asshole. Jamie moans at the touch of Jack's cock and braces herself for the pain. Jamie pulls away from Emily and tries to relax as best she can when the tip of Jack's penis tries to invade her asshole. Jack is familiar with this resistance as he quietly chuckles to himself before finally breaking through. Jamie grunts quite loudly in pain at first, but her little body relaxes as the widest part passes her anal ring.

"Oh my fucking god!!! You're sssssoooo fucking big Jack!!!!!! UUUUUUGGGGGGGHHHHHHH!!!!!"

"I know, he is big!" smiles Emily.

Jack keeps pressing his cock deeper and deeper into Jamie until he's pressed his pubic bone to her butt. "Oh man, you're even tighter than Emily."

"No way!" gushes Emily.

Jamie just groans and tries to get comfortable but it's impossible with two thick meaty cocks in her tight holes. To fight the discomfort Jamie begins rocking back and forth on top of Emily. This helps tremendously as the two cocks lovingly pleasure her filled holes. Jack gets the signal and starts to slowly push and pull out of her. Emily does the same as well, slowly gyrating her hips in rhythm with her two other lovers.

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byf1dude_lotus© 6 comments/ 37881 views/ 16 favorites

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