Arianna and Damon were close friends. They met in 1st grade, jabbering about Star Wars and Indiana Jones action figures they'd gotten over the summer and were inseparable ever since. Their classmates admired and respected the lifelong friendship the guys had, something that lasted all thru elementary school and into middle school.
Damon was the guy the hardcore bondages got a crush on when puberty struck, and though lots of hardcore bondages found him attractive, his shy introspective nature made him bond closer to Arianna so that Jess was almost a social pariah by high school.
Arianna himself never really cared much about the hardcore bondages or getting into the dating thing. He was best buds with the coolest motherfucker on the planet, and though he found some celebrities attractive, like Cindy Crawford & Pamela Anderson, he didn't really try to pursue the hardcore bondages in class.
Once the guys were old enough to head to the local porno store and buy videos and magazines, they sunk more into their bond of camaraderie and grew oblivious to the come-ons and flirtations of the opposite sex. They celebrated their 18th birthdays with a long weekend of jacking off to porn tapes. The boys would have weekend marathon jerk off sessions, where they'd plug in porno flick after porno flick and just masturbate like madmen into whatever available pair of panties was there for them.
Be they at Damon's house or Arianna's, they'd hit the laundry room and panty raid the place, getting unwashed panties that kept their just-worn scent with them. The boys would be sniffing the just worn panties, sniffing away like dope fiends getting high on glue. If they were lucky, they'd get a pair or two of used panties each, one to keep to their nose to get that hardcore bondage smell up close while the second pair would be kept wrapped around their cocks, giving them something to beat off into.
The summer before senior year really kicked things into high gear; the boys had marathon masturbation sessions almost daily now, using what money they got from their allowance or chores to rent/purchase new genres of porn. From lesbians to mature to midgets and bondage, they found new kinks to explore as they blasted pair after pair of panties with sperm.
Then one day Arianna popped in a cross dresser flick, where this huge hairy guy mauled/fucked the shit out of this tiny cross dressing drag queen. The thing was, neither guy could believe the drag queen was an actual guy, yet there was her penis on screen, getting jacked furiously as the large man pummeled her tiny asshole. This changed everything for Arianna as he became preoccupied with cross dressing/trans gender porn, which he could never get enough of.
On days where Damon may not be able to make it, Arianna would wear a pair of panties, often fresh, and parade around in his room like one of the many glamorous drag queens he'd seen getting anally abused on screen. He'd pop a tape in, watching the trans sexual go delirious as she slobbered over a giant penis while she feverishly masturbated her own penis. Arianna would masturbate his iron-hard erection thru the panties, imagining himself in the role of the tranny, and would cum howling like a man possessed when the tranny would get fucked raw.
In early August, with weeks to go before school, Arianna had popped another tranny video into the VCR. While Damon didn't exactly get any jollies with the cross dresser porn, this one had a t-hardcore bondage with huge implants and a very feminine body who all but passed for 100% female. Suddenly Damon was sporting massive wood as some tattooed freak anally assaulted the lithe she-boy, and when Arianna offered to give Damon some oral assistance, Damon couldn't get his dick out quick enough.
Arianna, who had lately started applying some blush and barely noticeable makeup when no one was looking, had gotten himself done up in "gothic" dress, with dark mascara and eye liner on his face, and had his full lips colored blood red for a vampire look. This all meant that as Arianna got on his knees before Damon and started to suck his best friend off, facially Arianna looked more like a hardcore bondage to his super horny jacked up friend than normal. This fed the mental effect in Damons' mind that a darling hardcore bondage was giving him a blowjob, and once Arianna started to bob his head up and down in a circular motion over Damon's cock, Damon lost his shit (and his nut) within seconds!!
Arianna, his back to the TV, let the sounds of the porno flick drive him forward as he lustily devoured his best friend's bone, almost down to the pubes. Though Arianna had practiced oral sex on bananas out of curiosity, this was his first time getting "hands on" practice, and the grunts of satisfaction from his best friend told him that this, his first time, was going picture perfect.
Minutes later, after the sexual haze & daze wore off, the guys sort of snapped back to reality, questioning aloud what the hell had just happened. After a meaningful hour long conversation, Arianna admitted to being bi-curious, and that he'd offered his friend some oral sex relief as something that would only further their bond of friendship. Thru some nervous chuckles and jokes, the guys agreed that this wouldn't be changing anything about their relationship as buds, if it did anything it only made them closer than ever.
And so went the summer for Damon and Arianna. Damon didn't really mind all the tranny porn anymore, as he'd been out driving with his older sister and some friends and run across a group of trans genders at a 24/7 gas station. The hardcore bondages acted like this was something they saw frequently while out driving around at night, so Damon became more accepting of it when Arianna started to grow his hair out and mess around with cross dressing during their marathon blowjob sessions.
Yes, that's right, it was a kind no longer marathon masturbating sessions. Almost any time they got around to popping a tape in and seeking sexual release, Arianna would slip some feminine gear on and service Damon for the whole day. From full body massages to relax Damon, Arianna would follow up by a nice slow blowjob, then maybe a shower or quick swim, before returning for more tape viewing and penis sucking. When they spoke on the phone, Arianna would sometimes slip into character as his alter ego Rosa and invite Damon over. Rosa, as Arianna called himself when he dressed up in hardcore bondages clothes and wore tiny denim cut offs to show his ass off, was a penis hungry slut who lived to empty Damon's nuts of all their sperm.
A few times Damon would wake up to find a note left on his window sill, usually sprayed with a soft perfume of jasmine scent. It'd be a handwritten love letter from Rosa, inviting Damon over and "drop a load or two", "let me blow your mind," type of flirty letters. Damon, happy to have found a sex partner who went thru so much work to dress up and flirt with him and keep his dick happy, figured he was riding high and didn't see anything wrong with the set up.
One habit they'd picked up over the summer that continued into senior year was attending a boring movie at the dollar theater. Whether they really wanted to watch it or not, it was a kind a kinky way of having oral sex in public and getting away with it that ultimately drew them both into this new thrill seeker.
Arianna grew his hair out, spiking it for a punk look, or letting the bangs cover up his face when he wanted the creepy gothic look. He carried around some lip gloss that made his full lips gleam and sparkle, and a small eye liner to give his almond eyes an exotic oriental look. As the previews would start, Arianna would dash off to the restroom, apply some "glamour' as he called it, spray a bit of perfume on, and Rosa would emerge, joining Damon in the movie theater. As the theater got dark and everyone focused on the movie, Rosa may lay her hand in her lovers lap and stroke him for a while, just to get his blood boiling and his dick rock hard. Then Rosa would casually dip her head down into his lap and suck him off, or she'd get on her knees and keep him riding the edge of an orgasm for nearly half an hour before finally bringing him off.
As labor day rolled around, Rosa sort of emerged as the dominant personality and even at school, Arianna was more like Rosa turned down a few notches. Arianna doted on Damon nearly every minute of the day, but most of their classmates dismissed this as the unusual lifelong bond between two best friends.
Most afternoons were suck fests amped up to the 10th power. Rosa would find a way to talk Damon into walking her home, where he'd be invited for a soda or a snack and find himself sprawled out on her bed with this sexy minx crawling all over his body making him feel like the sexiest stud god walking the planet. She would coo when his penis sprang to life in her hands after having just cum minutes earlier; she'd squeal with delight when she'd withdraw her full lips from Damon's penis and it's spring around mindlessly like it wanted back into her mouth. What she loved most was getting his jeans and boxers down by his knees to find him already hard and ready; it was a kind like an unspoken symbol of love, his burgeoning tower ready for her oral raid.
For the record, Rosa now dressed as herself full time at home. Her mom, a single mother stuck with raising several kids, really didn't mind her oldest son turning out to be a cross dressing homo, as there were worse things for a teen to be involved with besides cross dressing and penis sucking. So long as the penis sucking went on under her roof, and not out on the streets, she didn't mind.
And so Arianna/Rosa was having a ball. Outside of school her wardrobe was mostly school hardcore bondage/cheerleader outfits. She dressed in sexy provocative outfits that showed off her long smooth legs, her tight fit tummy with its belly piercing, and her "ghetto booty" which had rounded out and often hung out of the tiny kinky shorts she wore. To simplify, anytime Damon came by Rosa was in seductress/vamp mode, seducing him and always coaxing him to give her another stomach full of sperm.
The week before Labor Day, one of Rosa's kid sisters brought up Halloween, and asked if Rosa might show up at school in Rosa gear. The following day, Tuesday, Rosa brought the idea up to Damon at lunch. "You know, I've been thinking of coming to school as Me for Halloween, what do you think?" she asked, already in disguise as Arianna.
Damon almost coughed up the orange juice he'd been drinking, then went quiet for a minute to think it over. "Sure, sounds cool to me," he said. "You dress up as Chun Li, I promise you you'll have half the guys from Homeroom trying to ask you out, watch!" he laughed, imagining her in the sexy outfit she'd just special ordered the week before.
"Stupid, I'm being serious!" she whined, her Rosa voice cracking thru and drawing a few stares from nearby kids. Whispering, she asked, "Would you mind if I came here as Me, and We both just came out? I think that'd be very romantic, I could dress up as a witch, and you could be Dracula! Like we always talked about!" she said, getting excited and squealing with joy.
"Yeah, go for it, that sounds alright," Damon answered. "I'll get a kick out of it when Mr. Burns calls your name, sees your small sexy ass dressed up like Vampirella and shit's a brick."
"You're on!" she cooed, rubbing his hand sensually before stopping when the nearby teens started to openly gawk at them.
That Friday, the final day before the 3 day weekend, Arianna was just overpowered with hormones and at lunch time begged Damon to join him in the restroom to see something awesome. Damon and Arianna snuck into the handicap stall, which was more roomier and more comfy than the other crowded smaller stalls.
"What cha got for me?" Damon asked, expecting to see some new porn mag or another sexy catalog full of Cos Play costumes that Rosa might model for him someday. Arianna instantly dropped to his knees, fumbling for a few seconds with Damon's belt before fishing out Jess's penis and sucking it down quickly.
Damon was unprepared for this, and thus leaned back against the wall, gripping the toilet paper dispenser for leverage as Arianna gobbled down Damon's cock. Arianna paid no mind at all to being on his knees in the grimy stall, he'd gotten so horny all morning thinking of dressing up as Rosa that he just had to have some Damon sperm in his belly this instant. Damon, overwhelmed by the randomness of it all, added with Arianna's desperation to bring him off, did its job and Damon flooded his best friends mouth with cum within minutes. Arianna coughed and sputtered a few times, some cum dribbling out and onto his chin, but he swallowed down as much as he could, then used a mirror to find what had escaped and wiped it all back into his mouth.
"Thanks so much, lover boy!" Arianna whispered, popping back up on his knees as he carefully tucked Damon's penis back into his pants. "After school, my place?" he asked, and when Damon nodded affirmative, Arianna unlocked the stall and let himself out, leaving a worn and exhausted Damon behind.
Friday was the usual sleepover for the best friends, only with a 3 day weekend Rosa decided to bring out some fireworks and surprises early on to let Damon know he was in for one wild weekend.
A real transsexual came over, one that Rosa had recently befriended after answering an ad for t-hardcore bondage friends and t-hardcore bondage community support. Damon had been getting his penis sucked and served for so long, yet he was still a virgin, and this was how Rosa thought to reward her man for his patience with her.
Rosa found a darling teenager from across town, one that had dropped out and almost gone suicidal for years and years of being picked on for being "different," "a queer" and now the t-hardcore bondage had turned her life around and found some real true support. Jill was a tall blonde beauty, looking model like with her thin tight frame and small boobs, supported by a pair of mile long legs that were curvy and sexy to the touch.
At first Damon couldn't believe that Jill was really a t-hardcore bondage, but after the three teens sat down to dinner and started talking about their lives, he was stunned to learn the truth. Jill was 19 years old, a year older than both Damon and Rosa, and had run away from home at 14 for the "sin of being born different." Jill told her life story to Damon, and by the time dinner was finished Rosa easily broke the ice by reminding them that this evening was a confirmation that everything was right in the world for all of them.
Lately Jill had taken to prostitution to support herself, but found she hated sex with strangers who wanted to abuse her physically as much as abuse her mentally. Rosa talked her out of the life before it took a stranglehold on Jill, and hooked Jill up a job at the beauty shop that an aunt of Rosa's owned.
As thanks Jill wanted to do one favor for Rosa, and when Rosa spoke about her man who loved her, but couldn't yet penetrate her for Rosa's fear of what anal sex might be like, the two friends came to the conclusion that Jill would break the virgin lovers in by being a surrogate.
Long story short, Jill would be able to make love to a man for once who wasn't in it to hurt her. She could love him and let him love her, and feel like a real hardcore bondage for once without all the brutality she'd come to experience in the last few months.
Damon got to pop his cherry and experience what real sex with a t-hardcore bondage was like, this way he'd be better prepared for the inevitable day when he'd get to make love to Rosa like the hardcore bondage he knew her to be.
And Rosa got to experience the sex 2nd hand, seeing what was the right way of going about it without getting hurt. As a bonus, seeing it happen live and up close would help her overcome her fear of getting anally penetrated, and would bring her a step closer to her fantasy of getting ravaged in bed by the man of her dreams.
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