For Miss Amy - Crossdressing

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A Standalone Story involving Miss Amy and Her boy.
1.7k words
3.69
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Part 3 of the 15 part series

Updated 06/10/2023
Created 03/24/2021
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He felt silly standing there with Mistress looking on as the gurl's, Shawna and Yvonne. Two lovely trans gurls who he loved like sisters slowly massaged the sweet-smelling lotion into his skin, making him smooth.

When Mistress had told him Her plan for him for the upcoming Party She was having, he had blushed. Cross-dressing had never been a fetish of his, of course as he well knew, that didn't matter. What Mistress wanted, Mistress got. So he stood there being prepared.

He couldn't help but look over that the frilly, lacy black and white French Maid's costume he would soon be wearing to serve Mistress's guests, and his blush only deepened, making Mistress chuckle softly and whisper, "don't you just love your uniform, pet?" She laughed when he blushed even redder if that were possible.

Soon the gurl's announced they were finished, and Mistress nodded, "Excellent gurls, time to get our little maid bitch all prettied up."

Next came the makeup. First the base, then, eyeshadow, and mascara. He could barely sit still for it, but Mistress's touch on his shoulder stilled him and the gurl's got his eyes looking smokey and sexy. At least, that's what they said.

Next came the rouge which gave him a nice blush to his cheeks, not that they weren't red enough, he thought. A bright red lipstick that Mistress called "cocksucker red" let him know exactly what his mouth would be ultimately used for that evening. They painted his fingernails and toenails a bright red as well.

After that, they slipped some smoky thigh high stockings with garter belts up to the middle of his thighs. Then attached them to the black garter belt they had adorned him with.

A black lacy thong came next, tucking his shrunken, chastised "clit" Mistress had called it and making the panties as smooth as possible, no easy feet considering the size of his balls, but an ice-cold package of frozen peas made him shrink up even more and some skin-toned tape flattened him out as much as possible. The effect was that it was a lot more smooth than he imagined.

A set of fake tits were then applied to his chest. This was made in an exceptionally cruel way. The gurl's applied the glue to his chest for it, Then attached two clamps to his nipples. Each clamp had a spring on them, and were attached up inside the false breasts to another spring on inside the nipples. Mistress had explained that if someone pinched those false nipples, then he would feel it in his own tits. She Herself tested this theory after the gurl's had applied the breasts to his chest and smiled when he moaned softly and whimpered in that delightful way he had when She played with those sensitive little buds.

Next came the bra to match the panties. It was half-cup, so the nipples would be easy to play with. The gurl's then placed a tight waist cincher around his middle, tightening it until he thought he would be cut in half. But with the breasts and his own full ass it did give him an hourglass figure.

A low, cut French maids uniform, it was so short as they pulled up, the skirt part didn't even cover half of his ass. Straightening the sleeves over his shoulders and zipping the dress up. He realized that if you just pulled down the front of the dress a bit, and bent him over, one could fuck him, and play with his tits without even undressing him. It was truly an "all-access" uniform.

Once he was dressed, they sat him back down and one of the gurls got a pair of high heels. He would spend the next few hours just practicing how to walk in those abominations of femininity, but with the little padlocks that was placed on them, the gurl's assured he could not take them off. Mistress had relented and only made him wear the 5" heels as opposed to the 7" ones She had originally wanted.

In preparing for this, Mistress had had the gurl's shave his head as well, and next, Yvonne applied a light glue to his hair, then fixed a blond wig over his head, and pressed it firmly into place. The glue drying would ensure that no matter how hard his new hair was pulled, it would remain in place. The wig was fixed into two pig tails and with the make up and outfit, he looked 20 years younger.

Having him stand up and walk around the room, Mistress gave instructions on how to walk like the little sissy bitch he was now, and the gurls helped him by walking beside him and using their hands to help him learn how to sway his ass when he walked and how to be properly slutty.

"After all," one of them said, "you want to attract those delicious Men that will be at the Party, don't you, slut?" They all laughed at his scowl, and Mistress smacked his ass and said, "Twirl for me, pet."

Nodding her satisfaction with his twirl, She then told him to curtsy. This took him several dozen tries before She announced Her satisfaction. She then instructed that Shawna help him learn to walk properly in the heels while She took Yvonne along to help Her get ready for the Party.

Later that evening as the guests mingled, submissive girls and boys were whipped and fucked, he circulated throughout the room curtseying to guests and offering them refreshment, lit their cigarettes, and got groped a LOT.

"My what lovely tits you have, whore!"

"What a cute little tushy you have, slut! Is there a tight little pussy hidden in there?"

"Suck my dick, slut." This was a very common phrase, and once uttered he simply sunk to his knees, freed the Man's, or Transexual's member from its confines and went to work eagerly, giving the type of sloppy blowjobs that were expected from one dressed as he was. He had been instructed to hold the cum in his mouth until he could get over to where a cup had been set aside for him to spit it in. Mistress was saving it all up for some humiliating thing to do to him later.

The Party wore on into the wee hours of the morning. No one was flagging or getting tired and the sounds of screams and moans could be heard all around. He had about 20 loads and the cup was nearing the brim as he spat the 21st load into it and Mistress came up behind him.

"Excellent, pet," She exclaimed. "So very proud of your eagerness!"

He blushed and fixed his make up with the kit the gurl's had stationed there while Mistress rubbed his as-yet-unused butt.

"Attention revelers!" She announced in a loud voice! Your attention please!"

As everyone turned to look at Her, She took his collar in one hand and the cup in another and walked up onto a mini platform and made him kneel. Grasping one of the pigtails of his wig She tilted his head back and spoke.

"During the Party here, my darlin pet has sucked off quite a few cocks and has saved all that sweet cum up in this cup. I am so very proud of his skills as a dirty little cocksucking whore that it is time he was reward for all that. So, Ladies, if you would there is still a bit of room in this big cup, please come and add some spit to it as well or anything else You feel like adding."

Mistress then spit in the cup and held it out. He watched in horror as every Femdom in the room giddily came forward and spit in the cup, one even lowered it between Her legs and lets some piss dribble into it as well.

Once it was almost overflowing Mistress raised it high and said what he very much feared She was about to say:

"Open up, pet, I know You must be terribly thirst!!"

To the cheers and applause of everyone in the room, She then upended the cup over his open mouth, and let it drain down telling him to "gulp it all down like the eager little cum, spit and piss junkie you are, my little cunt, then me and some of the girl's are going to gangbang that sweet little sissy pussy you've got waiting for us!"

He closed is eyes and tried not to think of the liquid pouring down his throat until the cup was empty. Mistress finger came up and scooped a bit off his chin and pushed in to his mouth where he sucked it off Her like a good bitch, then She dragged him to a fucking bench, bent him over and proceeded to penetrate his sissy pussy with Her big, black strap on. Another Woman stepped up to his mouth, and soon he was choking on Her cock, while two others grabbed his hands and made him stroke theirs.

Thrust, slam, harsh smacks to his ass, harsh pinches to his nipples, gurgles and groans coming from his battered throat. He was well-fucked as woman after woman used him as the meat in their gangbang sandwich. Calling him degrading names like cunt, whore, slut, bitch, cockgobbler, and cumrag became a new favorite. The other partiers watched for a bit then resumed their own fun, until soon he noticed that the dicks going into his mouth didn't have that rubbery taste, and the hips slamming against his shaved flesh had more hair on them.

He realized that the Women had finished and the Men had taken over the gangbang. Soon cum was flooding down his thighs and chin and he was exhausted, held up only by the bench and the firm grip on his pigtails.

Finally, it was over. He was draped over the bench still, falling in and out of consciousness, when he felt gentle hands helping him up and undressing him. Shawna, Yvonne and Mistress took care of him, showering him, soothing him and putting him to bed in his little cage. Mistress murmuring, "you can clean this mess up after some rest, pet. I am so very proud of my good...girl."

She said that last with an evil little grin and kissed his forehead as he blushed, then covered him up and bid him goodnight.

He fell into an exhausted sleep, dreaming of hundreds of cocks both real and fake all coming at him at once. He woke wondering when the next party would be and if he could do this again.

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