Feminising a Homophobe
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Feminising Adam free porn video
Meeting Mistress
Sixteen-year-old Adam walked hand in hand with his mum across the park. He was wearing his favourite shiny pink leotard under the school blazer, white shoes with kitten heels and white ankle socks.
He took small steps to avoid his tiny boy-clit rubbing up another erection inside the soft fabric.
“Look at that lady in the black leather, what's she doing to that older lady on her knees, mummy?”
“They look like Mistress Anna and her sub, Suzy,” Mum replied, trying to shield her son's eyes.
As they approached, Anna called his Mum by name.
The last time Anna had seen the fiery redhead was at the Club, strapped down half-naked to the spanking bench; the red leather harness bralette only adding to her nakedness.
Master James had taken particular delight in raising the colour of her buttocks to match her long red hair.
“How does she know you, Mum, do you work together in Andover?”
“Yes, that's it, baby,” remembering the excruciating pain from the nipple clamps in that next scene with Anna.
“Hi Mistress, this is Adam, and he's really keen to get onto the office ‘work experience’ programme. Shall I send him along on Monday?”
“Sure, baby girl,” Mistress replied, planting a soft kiss on her neck and rubbing her bottom, “I never forget a pretty co-worker. Give her a business card, slut, so she's got my number."
Suzy fumbled around inside her bra, pulling out a slightly crumpled card and proudly handed it to Adam. “Here you are, little man."
Adam read the card aloud: "Anna Dominatrix - Discreet Personal Services." He blushed red, trying to memorise her private contact details.
“Not that one, stupid.” Anna slapped Suzy, grabbed the card, and replaced it with the boring one, just saying 'Ms A Adams - Personal Assistant’ and the office phone number.
“So, Adam, tell me, why do you like wearing girls' clothing?"
Anna had unbuttoned his blazer and was admiring his cock flattened inside the snug leotard.
Mum explained it had started when she had taken him to dance lessons, and he tried on tights for the first time. After that, he would run around the house in his big stepsister's thong, even stealing her bras to wear stuffed with pink socks.
Adam was delighted when sis gave him her old shiny dance leotard. He loved to watch his flat pubic area in the mirror, with his cock safely tucked out of the way between his thighs. Mum sometimes let him watch her showering; then slapped his bottom for cumming in the sink.
Mistress Anna gave Adam a small shiny metal cock restraint. “Here, baby, wear this over the weekend and we'll soon have you acting like the girl you want to be."
“Thank you, Mistress,” his mum replied. “I'll make sure he has it on for the interview on Monday, and perhaps his new pink skirt if he's good."
Monday Morning
Adam arrived bright and early for his ’interview’ on Monday morning, wearing a short pink top over a heavily padded bra, a short pink skirt, matching tights, and those lovely white shoes.
He stood meekly at the reception desk, averting his eyes from the constant stream of health workers, some of whom paused to check him out. “Come up to my office later, little girl,” said one man, “it’s on the top floor - just ask for Master James."
Adam assumed he had misheard ‘Mister’, looking up replied, “Yes, Sir.” Feeling a strange tingle in his crotch.
Mum had only allowed him ten minutes out of the cock cage all weekend, for one quick wank and now he was getting desperate.
The male receptionist guided him towards the lifts, then decided that the stairs might be better for the two short flights up to Anna’s desk. The lower part of Adam’s bottom wiggled deliciously for him, inside the thin white tights, fully visible under the short pink skirt.
The interview was a mere formality, but he struggled with the application form at the Gender and Age questions.
Anna said, "Just leave them blank, nobody would ever notice."
Adam was set to work delivering the internal mail and was horrified to see the first envelope addressed to Master James, so it was true. “Do I have to, Miss?”
“Of course you do, Adam, it’s all a good experience. Here’s some lube and make sure he uses a condom, we don’t want you spreading anything nasty around the office."
Forty-five minutes later Adam returned, the knees of his pink tights all scuffed and a rather large hole in the back when he bent over Anna’s desk for inspection. She smoothed more lube into his sore, gaping butt hole. “Oh dear, little Man, this does look tender. Let me give you some relief."
Mistress undid the lock on his cock cage, letting his pent-up erection grow in her hands. “There isn’t that better, you lovely boy.”
He only lasted thirty seconds of gentle rubbing, even Anna was amazed at the quantity of sperm he released into the carefully positioned tissue when the phone rang.
It was her boss Suzy, better known as ‘posh slut’. “Send him in here, now. I need to check out his oral skills."
“Come back at lunchtime, Adam and we’ll get you some new tights, these are a disgrace."
Next door, 'posh slut' was sat behind a large desk, legs apart, no knickers, stroking her engorged lips. “I was watching you on the top floor, there are cameras everywhere. I think you did very well for the first time. Now you need to learn to suck pussy. Get your head in here."
Luckily Adam’s older stepsister had let him practice on her a few times and he quickly picked it up again - running his tongue through the slick folds and around the hard nub.
“Good girl,” she panted, “that’s very nice." Her fingers were running up the back of Adam’s neck, “Keep sucking, you can use your fingers too if you like.”
Adam bunched his fingers together, just like his stepsister had shown him, and was amazed that his whole fist was swallowed up by the first adult cunt he had ever fisted.
Much later, Adam, moved away, his face coated in lady-cum, very pleased with his first morning.
“Okay, you can get up now, why don't you take those ruined tights off, then you can paint your toenails for me."
Adam sat uncomfortably on the leather sofa, knees drawn up to reach his toes, displaying a delicious slice of slapped buttocks.
“We'll have to buy you some stay-up stockings for those lovely smooth legs. Hmmm, stockings and a thong, how do you fancy that, little girl? The thong can hide your little boy-clit, we don't want that popping out if you get excited. Perhaps we can even find you a small butt plug for that pretty pink arse. Now bend over and grab your ankles, I think we need to inspect those bruises."
Adam bent over, gripping his spread ankles, Suzy's face only inches from his reddened bottom. He jumped when her tongue made contact, then relaxed until he felt a hand squeezing his balls.
“Oh shit, Miss, you mustn't do that. I might cum all over your sofa."
“Don't worry, little lady, I love the taste."
Adam's knees buckled as Suzy's cool tongue pressed into the heat of his rosebud. Her other hand collecting the pre-cum leaking from his boy-clit tip. “Turn around, little man, let mommy drink your lovely sticky sperm."
Adam's cock erupted as Suzy's tongue made contact with his slippery tip. She gulped most of it all down, the remainder splashed onto her white blouse. “Naughty boy, now I'm going to have to take this off. You can finish off between my tits if you like."
Of course, that was the moment that Mistress Anna knocked and walked straight in; Suzy on her knees, topless, holding her bare breasts wrapped around Adam's sticky cock.
He was holding her head, covering her ears, so she didn't hear Mistress until she shouted, up close. “What the fuck are you doing to him, boss? I think I need to discipline both of you right now."
Suzy meekly lay along the back of the sofa, Mistress tightening the straps across her back and legs.
Adam ejaculated with every slap on Suzy's bare arse; Mistress Anna was magnificent.
He couldn't imagine why she was so angry, then it was his turn.
He offered his sore bottom, but she turned him around and slapped his balls very hard three times. The sperm stopped erupting, all he could manage was, “Sorry, Mistress, it won't happen again."
“Come on, we need to get you some proper falsies, we can't have a flat-chested girl pretending to serve.”
Mistress Anna dragged Adam off to the sex shop ‘An Amazing Fantasy’ in town.
Sex Shop
“Good morning, love,” Emma called from the back of the shop.
Then, “Oh, I'm sorry, Mistress Anna, I hardly recognized you in office clothes."
Emma only worked in the shop occasionally to satisfy the needs of particular clients; swapping her intimate massages for advising on the use of some special sex toys.
Taking Adam’s hand, “And who is this lovely sixteen-year-old boy dressed as a girl?”
Emma thought he looked particularly cute in his pink skirt and white shoes.
“Come here, Little Lady, I don’t bite. Well not often, I understand you need some false tits. I’ve got just the thing for you out the back."
Adam timidly pulled the thin pink tee-shirt over his head, submitting to whatever Emma had in mind. She found a junior-size flesh-colour push-up, half-cup bra, which stuffed with extra silicone breast enhancers gave him a moderately plausible bust.
Emma stripped off his skirt and torn tights, while Adam admired his new tits in the full-length mirror. Emma managed to re-attach the straps on the matching pink bikini bottoms to tie up and hold his cock flat at the front, but fully expose his butt for adult use at the back.
The outfit was completed by a black fishnet bodysuit, a tight black micro-length skirt, split at the back and black fishnet stay-up stockings.
“Now you need to learn to ‘present’, baby girl. Down on your knees. Legs together, chest out, hands behind your back. Yes, that’s it. Keep your eyes lowered until your Master or Mistress gives you a command, then what do you say?”
“Yes, Mistress?” Adam grinned, loving so easily becoming submissive.
“Good girl, Adam. Suzy said she taught you to lick pussy this morning, so now you need to try the other place."
Emma lowered her tight white leggings and pushed her bare butt into Adam’s face.“Eat this, baby. Stick out your tongue. Don’t forget, hands behind your back."
“Yes, Mistress."
Emma couldn’t resist checking out her physical arousal level as Adam’s long tongue described a figure of eight between her cheeks, dipping into her butt hole on each sweep. She sucked her sticky fingers nearly clean, then reaching around the back, smeared the remaining juice into her cleft for Adam to lick out. He was learning fast, forcing Emma up onto shaky tiptoes as her orgasm unexpectedly hit, her thighs went to jelly as the spasms rippled outwards from her sensitized clit.
“Good girl,” Mistress Anna pulled aside the curtain, watching as Emma came back down to earth. “You have trained him well, baby. I could hear that orgasm from the other side of the shop."
Anna grabbed Emma by the cunt, “Perhaps you'll make a Domme one day. So now he is competent at cunnilingus and anilingus; just fellatio to go."
On hearing ‘cunnilingus’, Adam crawled forward to place his face between Emma’s thighs, looking up pleadingly. “Please Mistress, I want to arouse you again."
He started lapping at her pubic mound like a kitten; Emma opened her knees wider to give him better access. He dived in tongue first, bumping his nose against her hard clit. “Sorry Mistress,” he mumbled, swallowing down a mouthful of girl-cum.
“Good boy, perhaps we’ll call you ‘kitten’, Would you like that?"
Adam nodded his head vigorously, bringing his hands up as paws; Anna was very impressed, kissing Emma deeply and lifting the hem of her crop top. Emma’s generous 34B bra-less tits fell out into Anna’s hands, tweaking her hard dark pink nipples as their tongues clashed.
Emma had no idea she could cum again so close after the butt-licking; flooding kitten’s mouth and screaming into Anna’s, whose own succulent tits were now pressing into hers.
“Wow, he is good!”
They hurriedly dressed and walked unsteadily into the main part of the sex shop.
“I think these will do the job,” said Anna calmly, picking up a variety of cock-shaped dildos with suction bases.
“Very popular choices, they are colour coded for size. Pink is the easiest for him to swallow, through the moderate reds for practice, right up to the black monster, called the jaw-breaker for obvious reasons."
Anna flashed her gold store card at the machine and they left hand in hand, Adam carrying the pink carrier bag stuffed with dildos.
The male receptionist had been replaced by the Butch Security Guard, demanding to see Anna and the kitten's ID. She dragged Adam into her lair to make an ID card. A smear of eyeliner, black lipstick, and nail varnish, and the look was complete, Anna could hardly keep her hands off her perfect little sixteen-year-old sub, gently massaging the inside of her own thighs.
The photo for the card front was a fairly regular head and shoulders shot, making certain it showed the top of the kitten's breasts. She bent him over the desk for the rear photo, the jewelled butt plug clearly visible between Adam's bare cheeks. There was no name on the back of the ID, simply 'Property of Anna Dominatrix’.
The guard proudly hung the new ID card around the kitten's neck, adjusting the lanyard so it swung between her cute breasts on every step.
As soon as they got back to the safety of her office, Anna stuck the smallest pink dildo onto the metal filing cabinet for Adam to practice on, while she locked the others away for use at home.
Kneeling beside the cabinet, kitten looked gorgeous, taking the pink cock dildo to the back of her mouth and gagging at first. Drool ran down her chin and neck, which Mistress wiped off. “Good kitten, that is lovely. Keep sucking and we can try the next size soon."
The desk phone rang, it was Suzy, her boss, “Where the fuck have you been for the last two hours? I needed you here for a client meeting, and last month's figures… and what's that funny slurping noise? Have you got another sub in there again? I'm coming in, you'd better be dressed."
Adam looked up from his enforced cock sucking practice to watch Suzy kissing Anna, tongues clashing, hands cupping buttocks as she forgave her lover.
“This little beauty is now called 'kitten’ and is learning fast. I think we should leave early today and show her the toys in our bedroom."
Back Home in Smannell
Suzy took kitten into the bathroom, making him kneel and watch her showering, soaping her breasts, and letting him lick her thighs, but no higher. Anna changed into her red leather Basque, displaying her gorgeous breasts, long boots, and matching strap-on harness, trying out the jawbreaker just for size. She loved the feel of its heavy balls between her legs and the girth of the shaft in her hands.
Anna was never going to use it on kitten, just wanting to remind him and Suzy who was the boss in the bedroom. They both looked suitably shocked coming out of the ensuite bathroom, kitten tried to hide beneath Suzy's breasts, promising to be good.
Anna swapped the dildo for an average-sized red model, sitting on the edge of the king-size bed.
“Open wide, baby girl. Let’s see how much of this one you can manage."
Adam rolled over onto his hands and knees, taking the cock into his mouth, desperate to please Mistress.
Suzy removed kitten’s jewelled butt plug and licked it clean, before replacing it with her tongue.
“Oh, you do taste nice, little girl. I’m going to eat you until you cum. Shall I release him, Mistress?” Holding onto his tied-up cock.
“Not yet, lover, let's keep the boy-clit for later. Right now I fancy that pretty arse. Hold him down, this might hurt a bit."
Anna slowly pressed the strap-on dildo tip between kitten's soft pink buttocks, pulling backwards on his bra strap to impale it fully.
Suzy offered up a breast to his eager mouth to muffle the screams, she slapped him each time he bit a nipple.
Just before they all fell asleep exhausted but happy, kitten pulled out a present from Emma for Suzy. It was a tiny vibrating egg that, popped inside a thong, would keep all her piercings standing to attention to give maximum pleasure all day.
“Thank you, Emma” breathed posh slut. “I love you."
Then Anna found the remote control and set it on slow. “Thank you, Emma, you filthy slut."
Meanwhile, across town Master James was already planning how Adam could best serve at the upcoming office party for Suzy's retirement.
Emely
- 02.04.2021
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- Category:
- Office Sex
