by John Dylena
Looking at his reflection again, he now looked like a woman. The wig and the makeup did their jobs, completely hiding any masculinity he had left. While not as good as Jessica’s work, his makeup was leagues better than what he’d managed on that fateful night.
His eyes turned to his bed and the remaining items. He put the bunny ears on and followed up with the cuffs and tie. Fortunately, the bow tie was high enough on his throat and hid his Adam’s apple.
All that was left were the shoes. He reached into the suitcase and pulled out the very last item: a black shoebox. He tossed the lid aside and looked at the contents.
It was a pair of red five-inch heels. They were shiny patent with a round toe. They shined in the sunlight that filled his room. He grabbed them and slid them onto his feet. They were a perfect fit.
Walking in heels was another thing he did when Jessica and Susan were gone. He would wear the heels and practice walking in them until he perfected it.
He stood up and looked at himself in the mirror. He looked like the kind of chick that men drooled over on the pages of magazines and at the old Playboy clubs.
Outside on the couch, Jessica and Susan were debating. “So what do you think he dressed up as?” Susan said.
“I don’t know, he’s been very quiet in there.” Jessica replied. Their voices were hushed, but Allen could still hear them in his bedroom.
Before leaving his room to reveal his choice in costume, Allen walked into the bathroom and double-checked his makeup and overall appearance. He walked slowly and quietly, making sure the heels wouldn’t click on the tile.
Susan and Jessica quietly sat on the couch and waited for him to come out. The sound of his door opening and the clicking of heels on the hardwood floor announced his presence.
“OH MY GOD!” Susan shouted, her jaw on the floor.
“Wow, I can’t believe how good you look,” Jessica said.
Susan got up and ran over to him, inspecting every inch of his body. “You look amazing,” she said.
“You’re not grossed out, are you?” he said, red with embarrassment.
“Grossed out?! Hell, if I didn’t know better, I’d say you were one-hundred percent woman. That outfit is hard to pull off for a guy.” She felt up his costume and inspected his groin area. “It’s still there, right?”
“Oh yeah. I'm wearing a false vagina.”
“Really?! Like the ones that make you pee like a girl?”
“Yep,” he said, blushing again.
“I must say, Allen, you look good, and those breasts are nice, too,” Jessica said. “Susan, come with me.” She grabbed her arm and they headed off to the kitchen to discuss something privately.
Allen sat down on the couch, keeping his legs together. The feeling of the pantyhose on his smooth skin gave him goose bumps. A few minutes later, the two ladies exited the kitchen and stood in front of him.
“Susan and I would like to propose a deal,” Jessica announced.
Allen narrowed his eyes. “What is it?”
“Tonight, we are going to watch you very carefully. If you make more than five mistakes while acting like a woman, you fail. If you make fewer than five, you win, and you get a special gift from us.”
Special gift? Allen’s mind ventured into the gutter. Quick and dirty images of the three of them in a threesome filled his mind. Oh, how he would love that.
“Mistakes?” he asked. “Like what?”
Susan chimed in. “Doing things a lady wouldn’t do: burping aloud, not sitting with your legs crossed or together, using your male voice… basically not acting ladylike.”
“What's the punishment and reward?”
Jessica grinned. “It’s a secret.”
“I won’t agree if you don’t tell me—”
“Look, you pretty much agreed to this deal the second you came out of your room dressed like a slut. You don’t want anyone knowing you’re a guy, right? Then just agree.” Jessica said bluntly.
Allen was taken aback by her comment. A moment ago, she had been saying nice things about his costume, and now she was practically blackmailing him. Susan gave her a strange look.
“Okay. I accept,” he said. He didn’t like this. It was never a good idea to go along with a deal where you didn’t know what the outcome would be. For all he knew, it could be a lose-lose situation. Then again, it could be something else—something he’d always wanted.
“Oh, and be careful tonight. With that outfit, I'm sure you’re gonna get a lot of attention. If you need anything, don’t hesitate to ask us.” Susan added.
Jessica nodded in agreement. There was something off about her. She was almost defensive. Was his plan backfiring? Was she totally turned off by him now that he wore this costume?
“Now, what name goes good with your costume, because we can’t call you Allen all night.”
“What about… Amber!” Susan said. Like the color of her hair.
“Yes, Amber, I like the ring of it. When people ask who you are, you are our old friend Amber, visiting for the holiday. Allen went to his own party. So, you excited for tonight, Amber?”
“Yes,” he said with a girly voice.
The two women laughed, giddy with excitement. Susan mixed a drink for the three of them. Tonight was going to be something else, and Amber wasn’t too sure what was going happen.
As the sun went down, the hired help appeared. The bartender set himself up in the corner of the living room, and two large bouncers went over the invite list with Jessica and Susan. They were friendly with the two ladies, and after Jessica and Susan introduced to the two men to Allen, he learned that they were the security detail that had worked the event during the previous years.
In order to smooth things out with the neighbors, they were always invited. In the usual event that the party got loud and out of hand, they always informed the local police beforehand, as well. A cop would occasionally stop by and do a quick walk-through to let the party-goers know that they were watching.
Two hours after the sun went down, the place was packed. There were a lot of people, and it was an even split between men and women. All through the night, Allen spotted women that he would love to get to know better, but he was a woman for the night. If he tried hitting on them, there would be consequences. Besides, even if they were lesbians, he wouldn’t want to deceive them.
Jessica and Susan were right. Many times, Allen caught the men staring at him. He could feel their eyes fondling every part of his body. At the beginning of the night, he clung to Jessica, but as he had more and more to drink, his anxieties weakened and he became more carefree. That was when he started getting into character.
Feeling lively, he got up onto the dance floor started dancing. Fortunately, he wasn’t the only attractive woman there, but when a guy got close, Allen went along with it and danced. A lot of bodies were bumping up against one another and he could’ve sworn someone had grabbed his ass, but he ignored it.
“Wow, look at her go,” Jessica said, pointing Amber out to Susan.
“Yeah, she’s been doing a good job all night.”
After a while, he stopped dancing and grabbed a bottle of water and plopped down on the couch. It was starting to get late and people were leaving.
As the party wound down, Jessica and Susan stayed by the door to say goodnight to each of their guests. Each one thanked them for another great Halloween party. When the last guest left, they paid the bartender, security, and DJ and they also left, thanking them for the invites. When everyone was gone, they locked the door behind them and sat back onto the couch.
“Another successful party.” Jessica said, hovering by the couch.
Susan held a trash bag in her hands. “Only one guy had to get tossed out this year.”
“That bartender was cute.”
“What do you think, Amber?” Susan said, tossing some red cups into the filled bag.
Allen grinned. “It was a lot of fun. I think I lost myself in it.”
“Oh ye
ah, you did.” Susan winked. She handed Allen a glass of water which he eagerly drank. The party had left him parched and incredibly thirsty.
“So in the end, you only made three mistakes,” Jessica said. “Congrats, you won! Now it’s time for your reward for acting so feminine tonight. Follow me.”
The three of them got up and headed into her room. Allen started to feel a bit lightheaded, but he passed it off as exhaustion mixed with alcohol.
“Here, let’s get you out of that outfit,” Susan said, and she and Jessica helped him remove the bunny suit until he was standing in front of them in nothing but his pantyhose and heels. They told him to close his eyes, and as he did, they both slipped out of their outfits and into some sexy lingerie.
He opened his eyes to see both of them wearing strap-ons. Something stirred inside of him. He stared at the black rubber dicks and his mind was torn. Somewhere deep down, it was almost as if he wanted it.
What is wrong with me?! I don’t want this! But I can’t control myself!
“Let’s get you into something a little bit more comfortable, shall we?” Jessica got up off the bed and pulled a box out from underneath. Susan helped Allen out of the pantyhose and high heels. Jessica dumped the contents onto the bed. It was a prostitute outfit.
“Let’s give the poor thing a chance to breathe, shall we?” Susan said, pulling down the bodysuit. Allen stepped out of it.
Jessica giggled. “My, my, if I didn’t know better, I’d say we have a shemale on our hands.”
She grabbed the various garments and began dressing him. Allen stepped into black fishnets, his current state of mind making him easily suggestible. Even with the influence of the alcohol, Allen went along with it, hoping that somewhere down the line there would be a threesome and the two ladies would take turns pleasuring him. Sure, he would be dressed like a woman, but a threesome was still a threesome.
He didn’t know the half of it.
Jessica tossed him a red thong and he put it on without hesitation.
“Put this on,” Susan ordered as she handed him a red tube top. He stepped into it and pulled it up to his chest and over his breasts. The top left a lot of his stomach exposed and just barely covered his breasts. “Looking sexy already, don’t you think?”
“Yes, she does,” Jessica said.
She handed him a black mini skirt and he put it on. It clung to his hips and the straps of the thong were pulled above it. The skirt was very short, and the tops of the stockings were clearly visible. Jessica reached into her closet and pulled out a pair of six-inch clear heels.
“Perfect,” Susan said as Allen slid the heels on. They walked the new Amber over to the mirror and showed her the new costume. “What do you think, Amber?”
“I look so sexy,” he said with the girly voice.
“Now that's our Amber,” Jessica whispered into his ear.
They led her out into the living room and played some music. “Dance for us, dance like the slut you are!” The two women ordered.
He followed the beat of the music as he began to dance and move like a stripper. He twisted and turned his body, occasionally sticking his ass out and arching his back, showing off his breasts. There must’ve been something in that glass of water, as Allen’s mind was floating in an erotic cloud. He didn’t care about having a threesome anymore; he was having too much fun dancing like a stripper while dressed like a whore.
“This is starting to turn me on!” Jessica said, sitting on the couch.
He walked over to Jessica and climbed on top of her, straddling her. Putting his arms on her shoulders, he moved his body to the music. He leaned forward and they locked lips. Jessica’s hands squeezed his ass as their tongues danced. Allen was getting what he wanted, but Allen was at another party. Amber was staying for the night.
Susan bit her lip as she watched the two of them kiss. Her body squirmed as she lusted after him, her jealousy reaching its limits. She stood up and pulled him off of Jessica. She held his hand, bringing him into the center of the dance floor. Wrapping her arms around him, she danced.
Jessica, wanting to join in, got up and went behind him and the two of them sandwiched him, dancing on both sides until the three of them merged into one being, moving and flowing with the music. Then Jessica stepped back and lifted off his miniskirt. She playfully smacked his ass and he moaned.
Susan backed off of Allen as Jessica stepped in front of him. She looked down at her strap-on. Allen followed her gaze downward and eyed it.
“Do you want it?” she whispered into his ear. “Go ahead.”
He did want it—no he craved it.
Jessica returned to the couch and sat down, spreading her legs. Allen knelt down in front of her and played with the rubber dick. He licked the bottom of the shaft and kissed the tip. She nodded and he went forward, wrapping his red lips around the toy.
He slid down it, going as far as his throat would let him and pulled back. His head went back down the shaft, going further, longer. Pulling off, he licked it once more and went back down on her after a couple breaths.
In no time at all, his head was bobbing up and down, going all the way to the base. It was a double-ended dildo, and Jessica pulled her head back, moaning with pleasure. Susan vanished at the beginning of the blowjob, but Allen didn’t care. He was too enthralled by the beautiful woman in front of him and her big cock, so absorbed by it, that it wasn’t until he felt the cool sensation of lubricant on his ass did he realize that Susan had returned.
He took his mouth off Jessica’s strap-on and looked back at Susan. She had a sly grin on her face as she lined up behind him, the tip of her strap-on an inch away from his ass.
Jessica pulled his head back onto her rubber dick and he continued sucking her. Susan squeezed Allen’s ass as she plunged her toy into his virgin asshole. He moaned, but his voice was cut off by the dick in his mouth. She slowly slid in and out of his man-pussy, going further and further each time. When his asshole was properly stretched and the black dick was up to the base in his ass, she increased her speed.
It seemed that her strap-on was also double sided, for as she fucked him, she moaned with pleasure. Allen’s mind was floating in a sea of erotic ecstasy. In his mind he was Amber, a slut with a dick. She was getting penetrated on both ends and she loved it. Jessica pulled out of Allen’s mouth and he let out girlish moans of pleasure.
“Ahh, yes, fuck me!” he said in his female voice.
Jessica removed her strap-on and shoved her wet pussy in his face, wrapping her legs around his head, silencing his pleasure-filled cries. His tongue slid into her warm pussy and she cried out with joy as he pleasured her.
Allen’s body betrayed him as his dick swelled in the thong. The smell of Jessica’s cunt was intoxicating, even more potent than the alcohol consumed at the party. Their voices and cries grew louder as all three neared climax. Susan smacked Allen’s ass as she pounded it harder, the other end going deeper into her pussy.
Jessica yelled as she came onto Allen’s face, triggering Allen’s own climax. He blew his load; the tiny thong provided no resistance to his throbbing member. His thick white cum sprayed all over the hardwood floor. Susan squeezed Allen’s ass as she came, her fluids coating her end of the double strap-on.
“Clean up your mess, Amber,” Jessica said in between gasps.
Susan pulled out and fell onto her ass. She watched Allen turn around and lick up his cum like a dog. She wanted to laugh, but her exhaustion was too much and she barely made it onto one of the chairs before falling asleep.
Jessica laid down on the couch and fell asleep too, dreaming about Allen.
Allen was too exhausted and out of his mind. He didn’t know where he was or who he was. He climbed onto the other end of the couch and passed out, sleeping a dreamless sleep.
He woke up the following morning with the mother of all headaches.
He sat up on the couch and looked around, but couldn’t remember where he was. His location flashed back to him af
ter a moment of confusion, but what didn’t come back were the events of the previous night. After the party, it all became a blur, and he couldn’t remember anything. All he could tell is that for some strange reason, his butt hurt and his jaw was sore.
He stood up and wobbled to his room, so out of it that he didn’t notice the clothes or the heels he was wearing. He entered his room and out of the corner of his eye he saw his reflection. Not recognizing it, he turned towards the mirror and saw himself and the outfit he was wearing.
“What the fuck!?” he said, noticing the prostitute outfit.
Patting himself, he looked down to see that it was in fact real and not a bad dream. He frantically removed the tube top, slid off the mini skirt, and as he straightened up, he got dizzy and extremely lightheaded. He stepped backwards and collapsed.
When he came to, he was lying on the couch. The prostitute outfit was gone. He was wearing a t-shirt and jeans.
“You all right?” Susan asked, handing him a cup of coffee.
“I think I had a bad dream,” he replied.
“Did it involve you dressed like a prostitute?
“So, it wasn’t a dream.”
“Nope, it was real all right” Susan replied, sipping her coffee.
Jessica stood next to Susan. “How did you like your reward?”
Allen sat up quickly, the ice pack on his forehead landing in his lap. “You call that a reward?!”
“Well, yeah. You acted like a woman so well that we rewarded you with the greatest feminine experience: sex as a woman.” Jessica nodded.
Allen fell back down, holding his head with his hand. “Holy hell… what would’ve been my punishment?”
“Womanhood training,” Susan said. “You would’ve had to dress as a woman for a week straight and engage in all aspects of a woman’s life. Either way, you would’ve had sex, but if you’d lost the bet, you would’ve been glad to do it and we wouldn’t have had to encourage it, like last night.”
“No wonder I can’t remember last night. You roofied me.”
“It wasn’t a roofie, but a hormone cocktail. Something to get you in the feminine state of mind.” Susan replied, grinning.
