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Is it blackmail if you enjoy it? (Pokemasterj x FutaFanatic)

Pokemasterj

Pokemasterj

Super-Earth
Joined
Sep 12, 2012
Location
Liverpool, Britain.
Jamie sighed as he checked the bedroom door was closed behind him, biting his lip. He'd been planning on this for a long, long time, but now that it was finally here he was terrified. It wasn't his first foray into crossdressing, and in all likelihood it wouldn't be the last. He hoped so, at least.

But it was his first time doing it with his girlfriends clothes. If she came home early, if he didn't hear her come in, he was fucked. Which is why he was being so cautious. First things first, panties. A simple, no nonsense black pair fit quite snugly over his shaved crotch, keeping his genitals contained. Secondly, knee socks. Blue and black stripes, just the thing to warm him and look great- Jamie always did love it when she wore them.

After that, it was pretty quick to finish off. A short, dark blue skirt- the kind you'd wear to treat your other half, not wear in public. Normally, at least. A bit of make up, just to make him that bit more feminine, topped off with bright blue lipstick. And finally, a tight blue t-shirt, easily covering his flat and feminine frame, unlike his girlfriends rather busty chest.

He smiled as he looked in the mirror, turning around slowly to admire how he looked. "I look great..." Jamie smirked, sighing happily.
 
And just like he hadn't hoped for his girlfriend came home early from work. Her shift ended because of a mishap that fucked up the whole builing, an electrical failure cut all the power to the place. So with a smile on her face, she was hoping to enjoy some time with her boyfriend and catch a hot relaxing bath with him before she had to make dinner. But what she would come home to would be something that made her life that much hotter in the future.

When she walked in the door and noticed the man's shoes on the floor she smiled, licking her lips."I'm home baby!"She called, letting him know she was there as she made her way to her bedroom. Her room was only a short ways from the front door, her footsteps getting louder and louder as she got closer."You here Baby?"She called again when she got no answer.
 
Oh, fuck. Fuck, fuck, fuck with a serving of freshly made fuck on the side. It was too late to change, he knew that. Jamie gulped and his face paled, contrasting even further with his dyed purple hair and hazel eyes, making him look like a corpse drained of blood. A rather attractive corpse, in his opinion, but he looked like a corpse nevertheless. Now, if he knew what was going to happen soon, Jamie wouldn't care that much. He'd probably embrace it with open arms.

Human nature is to fear the unknown, the new, the confusing. So he was poised to reject what was about to happen. "Y-Yeah! Just, um... Gimme a few minutes, honey! I'm not decent!" Jamie's voice squeaked as he spoke up for her sake, panic paralyzing his feet. What to take off first? Where to put the clothes? She'd know what had transpired if the clothes Jamie liked the most were scattered on the bed. His heart was pounding, his brain was demanding him to strip. But his muscles refused to listen, his arms didn't move. He was well and truly fucked.
 
When she heard his from coming from her room she narrowed her eyes a bit. He was rarely in there just for the fun of it, especially when she knew how he loved the things she dressed in which she did special for him. But when the door was shut she sighed a bit, her hand taking hold of the door knob."Come on now baby I've seen you naked before so why hide?"She asked as she opened the door, peeking inside with a smile.

But that smile faded a bit when she saw her boyfriend, dressed in her clothes and dolled up like a pretty girl. she could only stand in shock for a moment, anger, confusion and even arousal setting in at the site.But rather than get the yelling and smacking he thought he would get, Kim looked at him, moving closer with each step she took."Ohh hoo!! now you've gone and done it baby!"She mocked, stopping a foot or two away from him."Why are you dressed in MY clothes when I told you not to?"She asked with a growl.
 
Any other time, any other situation, Jamie would be overjoyed to see Kim home from work early. A lot of the time she was too tired to talk much, so they ended up just resting with one another, a head on the others lap. Today? Not so much. A whimper escaped Jamie's lips and he backed up a step for every one his beloved took, voice stammering as he finally worked up the will to explain.

"I-I.... I was gonna do it as a surprise f-for you!" He squeaked once more, grasping for an answer other than that he loved dressing in a womans clothing. "Rembember? I f-found your crossdressing porn a while ago..."
 
She giggled as he tried to find an answer, nothing that sheered away from the fact that she knew about his fetish, she knew he loved the idea of dressing up like a woman. but it only turned her on, making her wonder how far he would take the role as she moved closer to him until he found himself against the wall."Don't play dumb baby I know you love this stuff..o just admit it instead of lying to me.."She told him, pressing her chest against him before gripping his cock through the panties he wore. If he wanted to dress like a sexy little girl then she was gonna show him how to act like one.
 
Jamie went to protest once more, defiant even knowing that it was useless. That was stopped, however, as Kim grabbed his cock. A gasp escaped his lips that was followed by a moan, legs shaking. Just dressing up like this was getting him hard, let alone her touch. "N... No... I don't..."
 
She giggled, kissing his neck as she took his own hand and placed it firmly between her legs, letting him feel the raging massiv hard on she had."Amit it to me baby and I'll show you what its like to be a naughty girl."She told him, seeming to let him enjoy his little fantasy, though it came with a price she wasn't going to let him refuse. All she needed to do was take a few steps back once he was completely erect for her and he would be hers after some well taken photos
 
Jamie purred weakly as Kim kissed his neck, the warmth and gentleness of them always inspiring a surge of lust and affection within him. If she hadn't done that, there's a chance he could have resisted her teasing, her temptation. But the body is weak, of course. He nodded after a few moments, squeezing her cock- the look on his face when he found out she was a futa, and bigger than him at that, was one of shock and arousal.

"I... I like it." Jamie nodded meekly, cock straining against the borrowed panties. "I like... I like to crossdress, Kim."
 
Kim smiled when he gave in, loving the way he admitted to it before she gave his cock another rub before pulling away, her monster throbbing and ready to teach her boyfriend a lesson."Since you like to dress like a girl how about you be a good girl and get on your knees for me..It's time I teach you how to act like a proper woman."She told him as she dropped her shorts and her panties to the ground. what he was met with was a nice thick 10 inch cock and was almost as thick as her fist.
 
Gods, she was large. Larger than any other cock Jamie had been with, although that wasn't exactly an illustrious gallery- two similar ex girlfriends and one failed foray into prostitution when money was tight. With a loud gulp, he sank to his knees before Kim with a nod of his head, subservient expression gradually crossing his face.

"I... Uh... You're going to be gentle, Kim, right?" Jamie asked, blushing softly. They'd slept together before, of course, but he was always the tiniest bit emasculated by her dominance and size. Plus, obviously, he'd never been dressed as he was now, hands on her thighs.
 
Kim laughed when he assumed she'd be gentle, her hand slowly stroking her monster to full attention, pre cum drooling from the tip." And Why should I be so gentle when my boyfriend wants to dress like a naughty little girl hmm?"She teased with a smile, rubbing her pre cum coated cock against his face."Lets see how good you can suck my cock first. Then we'll see how gentle I will be with you.."
 
"I... Okay." Jamie gave kim another nod and kissed her head, licking up the precum from the underside of her head. He trusted her. She'd never shown a cruel side to herself before, or he thought at least. Shouldn't be... Difficult. Just a bit tricky. It's a matter of relaxing your throat, after all. Sure, she's huge. Sure, his mouths kinda small. But it'll be okay. Probably.
 
She watched him, licking her ips with a bit of a grin, a hand holding the back of his head."Get to sucking me baby or I'll fuck your mouth. I'm giving you the chance to be a proper girl and servicing me. or should I just turn you into my dirty cock slut?"she teased with a smirk, licking her lips with a giggle, her cock throbbing with need. Her balls were swollen as well, desperate to empty its contents.
 
Jamie considered answering Kim, but... It'd be a bad idea, in the end. She was a woman of her word, with all that it implied. If she said she'd turn him into a slut, she'd do it or die trying. Nodding with a weak smile, he slowly took Kim's cock into his mouth, still unused to her length and girth. As most people would be, in all likelihood.

Jamie's eyes closed and his hands moved to rest on his girlfriends thighs, humming quietly around her shaft as he began to bob slowly, trying to stay calm.
 
The moment he took in her length Kim moaned, smiling happily as she gently ran her fingers through his hair. Mmm good boy baby.."She praised with a lustful growl of excitement. his hums made her moan louder, her cock twitch as she bucked forward lightly, forcing him to take in even more of her cock."Mmmm yes, suck your girlfriend's big cock like the good girl you are.."
 
Jamie gagged slightly as Kim's hips rushded forward, not expecting the intrusion of her cock. He whimpered but managed to keep his actions up, forcing down any panic that threatened to rise within him- in this situation, the best thing to happen for him was to get Kim off as quickly and efficiently as possible. And, to do so, he began to suck her off quite rapidly, cheeks red.
 
As he sucked her off she moaned, licking her lips with a pleased giggle."That's a good girl, sucking my cock good and hard. Lets see if you can play the part as good as you look."She praised, her cock throbbing in excitement against his lips as they worked her. She dreamed of doing this for so long, to have her lover all over her cock. But of course not like this..she preferred it with his own cock buried down her gullet too but that was for another time.
 
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