tagTranssexuals & CrossdressersDerek & Amy: Boys Night in

Derek & Amy: Boys Night in


Tonight is the night Matt learns how to be a true lover. Before, he had his wife Amy to hold his hand when they played with Mistress Derek but tonight, he's all on his own. Before Mistress Derek arrives, Amy prepares Matt using the instructions she received from him. Matt is to be dressed in a sheer, pink babydoll top with fluffy breasts and matching panties. Along with that, he is to be in a poofy blond wig and matching pink marabou slippers. He is to have his collar on marking him as Mistress Derek's property and is to be on his knees once his mistress arrives at their home. Amy, Mistress Derek's lover and another of her playthings, knows that if Matt isn't up to her mistress' exacting standards, she will pay for it as well though she doesn't mind it as much. They first make sure Matt is shaved from head to toe. Mistress likes his girls to be shaved regardless of their gender.

Once Matt's skin is smooth as silk, Amy begins to dress her husband up as the pretty little thing their mistress loves. They start with the lingerie: easy to get on and easy to get off. It's simple enough that it conveys the proper amount of femininity and vulnerability befitting of a slave. Next is Matt's collar. The collar is pink with "Derek's" written in bright, shiny diamonds. She is required to wear it whenever she's at home and especially on nights like this one. Last are the slippers. They're simple three inch marabou lounging slippers for getting around. Her mistress also demands her girls always be in heels when in her presence. Along with the collar, Matt is required to only wear heels when at home. Mistress expects her slave to one day be able to walk with perfect grace and femininity in the highest of heels much like a good girl should. Given that she has only been Mistress Derek's slave for a short time, she can't be expected to have mastered them just yet. Matt doesn't realize how lucky she is that her mistress is so forgiving. The last is the blond wig. Matt doesn't know it yet, but Amy has dressed her husband up to look like a fembot from the Austin Powers movies. What better way for a mistress to play with one of her toys than to have look like a submissive robot?

A little while later, Amy gets a text on her phone from Derek saying he's walking up to the house. This was Amy's predetermined cue to take Matt to the designated play area, blindfold him, and have him wait until his mistress arrived. As soon as she staged him, the doorbell rings.

Amy goes to answer the door and sees her friend and lover Derek standing before her in his drab jeans and black, metal t shirt along with the brown combat boots he wears every day. He has a large gym bag slung over his shoulders which no doubt contain all of his playwear. They greet each other with a hug and a deep sloppy kiss. Amy can feel the tight corset Derek has on under his shirt that Katy helped him put on earlier. Trailing behind Derek is Katy, one of his and Amy's plaything. She hasn't been fully collared yet but she knows her place in the group. Amy greets Katy with just as deep a kiss but not nearly as passionate as her one for Derek.

Derek asks if her slave has been prepared as ordered. Amy responses that she has been and is waiting in the guest room as ordered. Derek hugs Amy and whispers "Good girl" into her ear knowing that it just drives Amy crazy. With that, Derek dismisses Katy and Amy for their girl's night. He gives Amy another passionate kiss and reminds her to have fun. He does the same to Katy except he grabs her by her long, raven hair, looks deep into her eyes and tells her to be a good girl for Amy otherwise she'll have to deal with him later. She appropriately responds with equal parts terror and lust and follows Amy out of the door.

With the house empty and his slave waiting with baited breath, Derek begins to make her transformation. She takes of her shirt to reveal a tight leather full corset top with eight attached garters. These are covered by a black, satin thong that accentuates the natural curves of her ass while showcasing the bulge of her cock up front. Attached to the garters are the sheer black stockings she prefers to wear over her smooth legs. Inside the bag are her white seven-inch stiletto, thigh high, lace up, stripper boots with a two inch platform pointed sole. Normally she would find such clothing to be gaudy and un-ladylike, but tonight is all about being a girl to the nth degree. She completes the ensemble with a tight red dress that it almost see-through. It does nothing to hide the curves of her erect cock. She completes the ensemble with black, PVC, elbow length opera gloves.

Eschewing any make up, she goes to the room where her slave Matt has been staged by his wife and was eagerly awaiting her arrival.

While walking towards the room, the distinct sound of stilettos echoes throughout the house, a sound that has Matt instantly excited. As per Derek's instructions, Matt's cock was to be open and ready for use. Upon entering the room, Derek sees the beautiful creature sitting in a chair, blindfolded and ready for her use. She walks over to her and takes her by the hand, leading her to the center of the room. Derek orders his slave to remove the blindfold and present herself. Matt goes to her knees and removes the blindfold. She then kisses both of her mistress' boots and says, "Good evening, Mistress. Your slave is as you demanded and is ready to be used however you desire." This always makes Derek's cock jump a little bit and is clearly evident through her tight dress.

Derek orders her to stand and gives Matt a deep lingering kiss on her bright red lips. She takes time to explore her slave's body. The feeling of the PVC mixed with the nylon of the babydoll make both our cocks twitch especially when I start grinding mine into hers. We kiss for so long that Derek almost forgets why he's here. Taking Matt by the hand, he leads her back into the living room and orders her to sit on the couch next to him. Though not dressed as one, Matt still sits down, crosses her legs, and folds her hands like a proper lady. Derek stands in front of her with her shiny white boots reflecting in the light and explains the plan for the night.

"Matt, you have proven yourself to be a proper slave and lady to me, but there is still more for you to learn. Though your wife has done an excellent job of helping you along your path of femininity, she still cannot properly train you to please me as I demand. Among the duties I demand of you is to be my lover just as your wife is. I demand that my lovers and slaves be the absolute pinnacle of femininity, even ones such as you. If you hadn't noticed, I told your wife to dress you as a fembot. The reason for this is twofold. The first reason is I like the look. It was the ultimate height of femininity in that retro sixties style that has always aroused me. The second reason is that's what you're to be in my presence. You're to be an empty headed bimbo who responds only to my commands and lives only to please and arouse me while with. That is why tonight is all about teaching you what I'll expect of you as my lover much as I taught your wife. I know you know how to suck my cock, but you have not learned how to arouse me. There's no point in having a slave if she doesn't know how to excite her mistress. This is why I directed your wife to dress you as she has. I love sheer clothes on my girls. It leaves almost nothing to the imagination while leaving all of the best parts to it as well. I can see your beautiful body through that mesh, yet I cannot see your clitty or your breasts. This is the tease. A common tease that men desire is a lap dance which is what you'll be performing for me tonight. I know you've been to enough strip clubs and have ogled the dancers while getting one. Tonight is your turn and I will do the ogling." Derek then reaches out to Matt and pulls him to his feet.

They swap positions as Derek pulls out his iPod and plugs it into a nearby dock. A few turns later and "Feel Like Makin' Love" by Bad Company comes on. Matt stands there unsure of what to do. Derek tells him to just relax, feel the music and think about all of the strippers he's seen give lap dances. With that, Matt begins to relax and start swaying his hips about to the music. He also begins rubbing himself up and down getting his cock hard. The already small spot of precum on his panties gets wet again as he moves toward Derek. As the song continues, he gets more into it. His inhibitions go out the window as he starts grinding his ass against his mistress' crotch getting her all hot and bothered as well. She even attempts a few booty pops during the chorus. No sooner than she started grinding her ass into to Derek's crotch, she turns around and straddles her grinding their cocks together yet again and swiping their wetness in the process. She's not the most graceful about it, but that's not the point.

Still unknown to her, the point was for her to learn how to obey her mistress' demands without question or suffer the consequences. Mistress Derek doesn't believe in punishing a slave purely for sadistic glee, but she has no problem dishing out discipline when needed. It's beginning to seem as though Matt is such a submissive little slut willing to do anything for his mistress that it might not be a problem.

The song ends and Matt stands there partially out of breath and horny as hell but being a good slave, he immediately puts his feet back together, crosses his arms, and bows his head.

"That was good for a first try," his mistress says, "but of course you could use some more practice. You're going to need it because this isn't the only time I plan on you doing this." Derek rises from the couch. His heels click across the floor as he walks behind Matt. He reaches his hand down to Matt's ass and rubs it through the sheer materials before gives it a little swat. It's not enough to cause a lot of pain, but just enough to focus Matt. Derek hugs Matt from behind, rubbing his panty and dress clad into Matt's ass. He pulls his head up and starts kissing his neck before saying

"You've gotten your mistress very excited right now. You were so fucking hot doing that dance that I can't wait for your wife to see it. Next time we'll try the slutty school girl or the naughty nurse. You'll look so silly and will probably be embarrassed but goddamn will it excite me. You have me excited right now. I think I want to make you my proper lover now."

As Derek says this, he slowly reaches around front and starts stroking Matt's cock. It is hard instantly and is soaked in precum. Derek pulls his hand out and admires its glow against his shiny gloves. He runs it between his thumb and index finger stretching it out. He sticks his thumb into Matt's still panting mouth and Matt happily cleans it off. Derek does the same with the cum on his index finger. After that, he releases Matt and pulls him by his collar to the bedroom where Matt was staged earlier.

As soon as they're inside, Derek pounces on Matt and starts kissing him like an old lover he hasn't seen in years. They passionately explore each other's bodies for a minute when Derek pulls away. He looks at Matt who just reeks of desire for his mistress and orders him to his knees. He commands him to start worship her boots and legs. Matt does so instantly. He starts at the toes and works his way up and down. He makes sure to lick the backs and up and down the heels. Derek lifts his foot up and Matt takes the heel into his mouth and worships it like a seven inch stiletto cock. He slowly pulls it and works his way around the back of the boots all the way up to where the stockings and boots meet.

Derek turns to him and rubs his raging boner on his slaves still well made up face. He does this for a little bit before shoving it into Matt's mouth. Matt hungrily swallows it down like times before and starts pumping away at it like the cure for cancer is in his mistress' balls. Knowing she won't stop unless told, Derek pulls Matt away and orders her to get on the bed. Without being told, she immediately gets on all fours with her ass in the air. Derek is please that his slave read his mind, but because she was not told to do so, Derek must administer punishment.

"Did I tell you to get on all fours, slut?" he yells.

"No, mistress" he responds meekly putting the pieces together.

"You'll have to be punished for thinking for yourself around me."

"Yes, mistress."

"I think you'll get twenty swats for this." That said, Derek swats Matt's panty-covered ass with his PVC gloves. She receives ten swats on each cheek. Her ass is almost as red as her face for committing such an egregious offense against her mistress and her cock his even harder and oozing precum.

"Next time, your balls will get the swats instead of your ass, slut."

"Yes, mistress. I'm sorry, mistress."

"You're fucking right you are. Since you're already there, I may as well do what I was going to do now anyway." Derek licks one of his fingers and starts working Matt's tight asshole. He starts to moan even more when his mistress slides the second finger in and starts working his prostate.

With Matt's asshole warmed up, Derek pulls his panties aside and lubes up his cock. With a few thrusts, he's in and slowly starts pounding away. Matt is now panting pure lust as he takes his mistress' hard cock, slowly, deeply and hard in his pussy. This isn't the first time they've been together, but this time, it actually feels like they're making love instead of just fucking. Derek's thrusts are slow and sensual like he's trying to bring his lover to a slow and prolonged orgasm. His hands hold gently onto Matt's hips as he gently massages them with his gloves along with using them to explore his lover and slave's lingerie clad body. As he continues to thrust away, he reaches around and plays with her nipples. All she can do is moan in approval.

Derek abruptly stops and tells Matt to lie on her back. Mistress wants to stare directly into her slave's eyes as she fucks her slave to orgasm. He reinserts his hard clit back into his slave's boy pussy and watches her face and cock both jump at the same time.

This time Derek starts pounding away at Matt while stroking his cock. Derek strokes Matt until the brink of orgasm only to stop again and kiss him deeply or bite his nipples. For five minutes Derek tortures his slave like this until Matt can take it no more. Matt leans up and looks into his mistress sadistically lustful eyes and begs his for her permission to cum. Derek never told Matt that he has to do this, but he smiles at the thought. Just for that, Derek not only grants his slave permission to cum but rewards him further by pulling out of his slave's pussy and shoving his cock into his slave's mouth right before he cums but telling her not to swallow while finishing her off with his hands.

He then gathers all of the cum off his girl's babydoll and stomach and scoops it into Matt's mouth so there's now a cum cocktail swirling around in the spent slut's mouth. Mistress Derek leans over her looking directly into her gorgeous eyes, then gives her a deep, loving kiss taking some of the cocktail into her mouths. She swishes it in her mouth a little bit then spits it back into her slave's mouth. "Swallow" Derek commands. Matt does so in one eager gulp then opens her mouth to verify that she has taken the gooey load down her throat.

Satisfied that Matt has done all that was ordered of her tonight, Mistress Derek grabs her by her hands and pulls her into a deep embrace. "You're my good girl" she coos into Matt's ears and she pulls her in for another deep kiss. They both strip and take a shower together. Still the slave, Matt bathes her mistress properly from head to making sure to pay extra attention to her cock and asshole. Once she finishes her mistress, Derek steps out and leaves Matt to finish herself off. When she gets out of the shower, Mistress is there in a black satin baby doll and matching panties and a glass of wine. She beckons Matt over to her and hands her a glass of wine along with a matching babydoll in pink. They both put on put on matching kimonos from Amy's closet along with two pairs of ballet flats.

They go into the living and cuddle while watching some TV for a few hours until Amy and Katy return. It's hard to tell what they did while out, but given that Katy is still wearing her Japanese school girl outfit and Amy is still wearing a black basque top and mini-skirt with her three inch booties, I'm sure it was something fun. "How are my girls?" she asks as the two walk in and see us embraced on the couch like a couple of old sweethearts. "Fine" Derek replies as he greets her with a deep kiss. He then turns to Katy and greets her the same way still tasting the distinct flavor of Amy's pussy. Amy leads Katy to the showers while Derek and Matt continue to sit on the couch and make out. About half an hour later, Amy calls out "Oh girls" and Derek and Matt head to the bedroom. Amy and Katy stand there also in babydolls of the same style as Matt and Mistress Derek. Amy's is red and Katy's is pink like Matt's. This was all part of Mistress Derek and Amy's plan to get all of them together in the same outfit and show the slaves what their color is. They all admire each other before retiring for the evening.

Matt goes with his wife Amy, and Katy goes with Mistress Derek. More moans are heard throughout the evening and it is doubtful any of them got much sleep.

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byKalira© 1 comments/ 18692 views/ 3 favorites

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