Tony and Alicia Celebrate Halloween

The pants Alicia picked out were a bit big and barely hung on her hips. She went to the closet and retrieved a pair of suspenders Tony sometimes wore having him help her put them on. The suspenders framed Alicia's breasts under the oversized dress shirt. Tony couldn't believe how attractive Alicia looked in a men's suit. If it hadn't been for the ridiculous cage on his cock Tony surely would have jumped Alicia by now. Alicia topped off her outfit with a black double breasted jacket and black heels. She quickly put up her hair pulling it back into a tight bun.

Alicia took Tony's hand and led him over to the mirror. With his heels on Tony towered over Alicia but in her mind it was important for him to see who was wearing the pants tonight and more importantly who wasn't. The exercise wasn't lost on Tony, he was the "girlie girl" and Alicia was the "butch". Alicia then led Tony to the bedroom door, she thought she felt him slow a little but he managed to keep up. Alicia had to resist the urge to look back and check on him, she was the one in charge tonight and he would simply have to follow.

"Be careful walking down the stairs in your heels." Alicia said as she walked down them first to show Tony how to do it.

Tony held the railing tightly and cautiously stepped down the stairs. They made a quick stop in the kitchen and headed out to the car. Tony was thankful that their nearest neighbors were too far away to see him walk out the front door to the car. As usual Tony headed to the driver's side door.

"Umm, where are you going?" Alicia asked. "You don't think you're going to drive in heels do you? What happens if we get pulled over? You don't have your wallet or license with you." Alicia even jingled the keys at Tony, he didn't have those either.

"You've got a point there." Tony replied softly as he headed to the passenger side of the car.

"Let me get that for you." Alicia said opening the car door for Tony. "Remember to sit and then swing your legs in."

Tony didn't know how to react to Alicia opening the car door for him. It would have been a feat to get it done with the nails he had on his hands as it was. He slowly sat and swung his legs in much to the delight of Alicia who closed the door and walked around the front of the car to the driver's side. When she walked past the front of the car Alicia looked at Tony sitting in the passenger seat and smirked. As they pulled out of the driveway Tony got a bit nervous, it was late in the day but the sun was still up. He began to fidget in his seat and looking all around.

"You okay?" Alicia asked knowing Tony was nervous about being seen.

"What if someone sees me?" Tony asked nervously.

"Open the glove compartment," Alicia said heading towards the nearest town, "I've got a pair of sunglasses in there."

Tony quickly opened the glove compartment pulling out a large black and rhinestone studded pair of sunglasses. He immediately balked at the idea of putting them on until Alicia spoke again.

"We have to stop by the store," Alicia informed Tony with a wide smile he didn't see, "we don't have anything to drink for tonight. Plus, you're wearing women's clothing and shoes, do you really think putting on sunglasses will be too much?"

"I guess you have a point there." Tony said humbly.

Tony relaxed a bit knowing Alicia wouldn't make him walk through the store like that, he may have felt ridiculous in them but at least he wouldn't be easily recognized! Then again he questioned whether she would make him follow her through the store, the thought terrified Tony. Alicia pulled into the parking lot of the store parking down by one end instead of the open spot in front of the door.

"Want to come in?" Alicia asked almost laughing.

"No thank you." Tony replied softly.

Alicia headed out to the store leaving Tony feeling very alone in the car. He tried to relax but it wasn't easy as he felt eyes everywhere were looking at him. The only good thing to come of this was the fact that if it were possible his balls and penis had retracted into his body! It felt like Alicia had been in the store an eternity when two adolescent boys walked by the front of the car. They made no secret of looking at Tony who immediately flipped down the sun visor to pretend to look in the mirror. When he actually did look in the mirror he noticed how open his blouse had become and knew the boys had both easily seen the hot pink demi bra from several feet away. Tony went to button the blouse up further only to find the remainder of the buttons were missing. Thankfully Alicia returned moments later with a bag which she put in the back seat.

As they drove Tony relaxed a bit and noticed the tell tale signs of their body language. Alicia drove with one arm resting on the open window and her legs spread in a typically masculine pose while Tony sat with his hands in his lap and his knees pressed tight together. Somehow he had gone from being a borderline type A personality to near woman in the course of an hour!

Approximately 20 minutes later Alicia pulled into the driveway of the house the party was at and shut off the car. She reached over and squeezed Tony's hand reassuringly. Alicia had seen Tony's trademark cockiness was no where to be found, it was time to reassure him a little.

"No one will know about the cage under your skirt as long as you are careful when you sit." She instructed. "Other than that just relax."

"Okay," Tony replied quietly, "I will."

Alicia got out and grabbed the bag in the backseat as Tony fumbled with the door handle of the car. Once again Alicia had to open the door for him and even extended him a hand to help him out. Tony was thankful for the hand despite feeling futher emasculated. Alicia continued to take the lead escorting Tony to the front door and ringing it.

"Oh my God Tony is that you!?!" Jane the woman answering the door squealed with delight. "Look at the two of you I always LOVE your costumes!" Alicia let Tony walk in first and greeted Jane. "How did you ever get him to wear that?" Jane asked much louder than Tony would have liked.

"Oh it took a good deal of work," Alicia replied, "but he's being a very good sport about it."

"Well that's great!" Jane replied with a big grin. "What did you bring?"

"Just a couple bottles of wine," Alicia replied handing Jane the bag with a wink, "no beer for Tony tonight, at least not with those nails."

Tony wondered how much of his blush was hidden by the makeup he had on.

"Come this way you two," Jane said leading them to the kitchen, "we'll get you some drinks so you can join everyone else. It's so nice out I decided to have the party in the back yard!"

Tony could hear the echo of his heels as he walked, the fact that there were 3 sets of heels echoing down the hallway was another reminder for Tony that tonight things were different. Then he remembered Alicia's promise, she was going to fuck his brains out and make it all worth it. Alicia was always good for her promises.

Alicia noticed that once again Tony was somewhat lost. She handed him a glass of white wine which he took without even looking at it and then escorted him to the back door. The sound of his heels on the concrete were like thunder as he walked across the patio. Tony looked at his buddies as he walked out with Alicia only to then realize he was carrying white wine in a glass with lipstick on it!

The two of them mingled together for a while until Tony got tired of comments about how sexy he looked and went off to chat with the guys. It wasn't the easiest thing to do dressed as he was and drinking white zinfandel instead of a hearty beer but he tried. Of course he took some good natured ribbing from the guys he was with but they knew him well enough to know he would do anything for Alicia and this was one of those things. Every so often Alicia would come by and give him a new plastic cup of wine and slowly Tony relaxed about what he had on as much as he could. She would also discretely pinch his butt or kiss his ear causing his cock to stir in its cage. After a while standing outside on the concrete patio made his feet ache terribly and he wasn't sure but it was almost as if his stockings were sagging. The feeling was irritating but he wasn't about to pull them up while he and the guys talked about tomorrows football match ups!

Tony was beginning to feel the effects of the wine and a full bladder when Alicia patted him on the ass. Without a word she took him by the hand to lead him back to the house.

"Where are you two off too?" One of Tony's buddies called out.

"You know us girls," Alicia replied, "we can never go to the bathroom alone!"

That brought the group to laughter well after the two of them entered the house while Tony closed his eyes silently wishing he could disappear. Alicia led Tony to an upstairs bathroom and slipped inside making him stand at the door. Tony was definitely feeling relaxed from the wine and had a nice little buzz which was making the whole being dressed as a hooker a little easier to deal with. He wasn't completely sure but one of his toes may have actually fallen asleep as well.

"Okay," Alicia said walking out of the bathroom, "your turn."

"How am I going to pee with this thing on?" Tony asked. "Can't you take it off for me now?"

"It has a slit in the front for you to do your business." Alicia replied, "just make sure you sit down so you don't spray all over the place and use the toilet paper to wipe up after."

"Are you serious?" Tony asked a bit agitated. "You mean pee like a girl?"

"I did tell you I'd make it worth it didn't I?" Alicia asked sliding a hand up Tony's legs and unzipping the slits in his skirt. "Don't you believe I'll make it worth it?" Alicia continued letting her fingers find their way to Tony's hot pink covered crotch while she nuzzled into his neck.

Alicia fondled Tony's cock and balls through the material and cage as best she could feeling him start to get aroused. Alicia was amazed how wet the front of Tony's panties had become obviously from his leaking precum. For a moment Tony began to enjoy that arousal then the stark reminder of the cage returned with the clamping sensation of his growing penis. The glazed over look returned to his face, time for Alicia to reassert her dominance.

"Now go in there and do what I said." Alicia said sternly leaning back and staring into his eyes while giving his balls a squeeze.

The squeeze wasn't hard but by this point Tony's balls were so swollen they ached! Tony knew it was no use and entered the bathroom to do as he was instructed. Tony stood in front of the toilet for a moment wondering what he was supposed to do. Did he pull the skirt up or down to sit? Alicia had never been big on sharing bathroom time like that and he respected her wishes but as a result he was completely lost in what happened next. Finally Tony gripped the skirts hem and pulled it up to his waist. His next challenge was pulling down the panties enough to free himself. The garterbelt covered the top of the panties so he had to tug them from the bottom. He pulled them down as far as the garters would allow and finally sat. Peeing in the plastic sheath was an odd sensation to say the least, Tony was thankful that the slit was large enough to keep it from backing up like a stuck drain. He removed some toilet paper from the roll and wiped the sheath clean. The whole experience was not lost on him, having Alicia help him out of the car was one thing this was even more emasculating than he though possible. After he flushed the toilet Alicia knocked and quickly walked in the door. She helped him fix his panties, tugging them securely in place for him, and zipped the slits to his skirt.

"How are you doing?" Alicia asked.

"My feet are killing me and I think there's something wrong with my stockings." Tony replied sheepishly.

"What's wrong with them?" Alicia asked suppressing an overwhelming need to laugh.

"They feel like they are slipping down or something." Tony replied unable to believe he was talking to Alicia about stockings he had on and how they were slipping.

"They do that from time to time silly," Alicia replied bending down and tugging one of his stockings up slowly, "you have to adjust them every so often."

"Well isn't that what the rubber grippers are for?" Tony asked suddenly enjoying the feeling of Alicia's fingers on his nylon covered legs.

"Yes but they don't work great." Alicia replied looking up and seeing the glazed look slowly appear on Tony's face.

She began to use it to her advantage and began slowly tugging the stockings up making sure to rub her nails over the fabric lightly. The glazed look turned to discomfort before she even got to his other leg. Then Alicia felt her pussy twinge and knew she needed a little attention. She quickly adjusted his second stocking tugging them both up high and turning Tony towards her so she could lean on the vanity. When Alicia quickly took off the suit jacket and flung the suspenders off her shoulders Tony wasn't sure what to make of it. With the suspenders off her shoulders the pants immediately fell to the floor around alicia's ankles.

"Get down on your knees quickly." Alicia hissed. "Now! I'm soaked and you need to give me some relief."

Alicia kicked off her left shoe and thrust the nearly opaque briefs down her legs taking her left leg out of them and leaned back on the edge of the counter. Tony, who was amazed how horny he was at this point, thrust his face forward burying it in Alicia's pussy. His desire even shocked Alicia who was brought very quickly to orgasm. Tony didn't stop after the first one and kept licking away with that glazed look in his eyes. Like before with her breast all of Tony's sexual energy was transferred through his mouth to Alicia's pussy and clit.

"Mmmmmmmmmm," Alicia moaned softly, "that's it Tony, make me cum and I'll make you cum later tonight."

Her words spurred Tony on, his tongue concentrating on flicking her clit rapidly. Tony's cock was aching in its constraints but he continued to lick Alicia as he attempted to ignore the pain.

"Ohhhhhhhhhhhh yessssssssssssss!" Alicia groaned biting her lip to keep from screaming.

Alicia humped Tony's face gripping his head with both hands as she came again quickly. Tony sucked Alicia's flowing juice as if it were life giving water. She had to push Tony back from her pussy as he wasn't about to stop. It took a couple of minutes for Alicia to catch her breath in the meantime Tony continued to stare at Alicia's dripping pussy through glazed over eyes.

"Help me get dressed." Alicia instructed trying to steady herself and her voice.

"Yes Ma'am." Tony replied sadly reaching down and helping Alicia step back into the white boxer briefs.

"Don't worry," Alicia said reveling in the control she had right now, "you'll get plenty more later."

Tony pulled up Alicia's bottoms and helped her step into the pants as well pulling those up and adjusting the suspenders for her. Alicia didn't have to do much for herself as Tony took care of it all, the only thing she had to do was step back into the heel she had kicked off earlier. She looked at Tony's face and kissed him softly on the lips.

"We've got to fix your face before you go downstairs." Alicia said picking up a small towel. "I don't want everyone knowing what we've been doing up here."

Alicia wiped away her wetness from his face and reapplied the foundation and lipstick as needed. It amazed Alicia how much she was enjoying being in charge. Here was Tony who was at this point so horny he had saturated the front of the panties he had on and so willing to please he had brought her two very quick and hard orgasms within seconds. To top it off rather than ask about his own relief Tony instead helped Alicia dress to the point where she only had to step into a shoe! Alicia gave Tony a quick hug, as her hands moved over the back of Tony's bra straps he came up with a devilish idea. Alicia quickly adjusted the right shoulder strap of Tony's bra loosening it slightly.

"Ready?" Alicia asked looking into Tony's eyes again.

"Yes." Tony replied softly realizing he now had to go back out and stand on his aching feet on the concrete patio. "But Alicia my feet really hurt and there's no way I can undo that ankle strap with these nails."

"Just sit at the little bar they have sweetie," Alicia replied making sure the zippers were all the way down on Tony's skirt, "just keep your knees together so no one sees your little secret."

"Okay." Tony replied dejectedly hoping to get a reprieve from the heels. "Little secret?" Tony asked. It was the first time Alicia had refered to his cock as anything but her monster in years.

"Oh you know what I mean," Alicia said with a wink, "the cage silly."

Alicia had to smile as she reveled in her control over Tony. She looked him over one more time making a few slight adjustments before giving her nod of approval. When she was satisfied she took Tony by the hand and led him to the door of the bathroom. As she opened it she was shocked to see Jane standing outside the door.

"And what were you two up to?" Jane asked with a playful smile.

"Oh simple wardrobe problems," Alicia replied with a smile, "sometimes they just can't dress themselves."

Tony just blushed behind Alicia and continued to follow her. On the way down the stairs Tony felt the bra strap fall off his right shoulder. He had seen Alicia adjust hers a ton of times and simply pulled it back up not questioning it. By the time he went through the kitchen it happened again.

"I need to get us some refills," Alicia said stopping at the refrigerator, "go and grab the empty seat at the bar before someone else does."

"You want me to go out there alone?" Tony asked unsteadily.

"Oh go on ya big girl!" Alicia chuckled. "We've been here for over an hour already, everyone's seen you by now. Just keep your legs together when you sit.

Alicia gave Tony a playful but firm spank and sent him on his way. She watched Tony cross the patio slowly and then try to figure out how to sit at the high stool in front of the outdoor bar. At least twice he had to adjust his bra strap before finding a way to slide into the seat. Alicia couldn't help but chuckle to herself as she poured two more glasses of wine for them. She could tell it was taking a lot of effort for Tony to keep his legs together he kept his hands together over the skirt to keep anyone from being able to see up it as well. The only time one hand left was to pull the bra strap back up onto his shoulder.

Eventually Alicia decided it was time to join him. She strode confidently and got to Tony about the same time as one of their acquaintances named Jill.

"I have been dying to ask," Jill started slightly slurring her words, "what are you dressed up as darling?"

"Tony is a hooker," Alicia replied handing him a red plastic cup of wine, "and I'm his pimp."

"Well you look adorable!" Jill exclaimed placing her hand on Tony's left thigh. "I mean really," Jill's hand slid up and down on Tony's leg, "just adorable. Oh my God are your legs shaven!?!"

Tony closed his eyes hoping Jill would quiet down and keep her hands to herself. Her hand slid down to Tony's knee and then straight up his skirt. Tony felt his cage tighten again and hoped that Alicia would take care of Jill while he concentrated on his other problem.

"Oh my God they are!" Jill said in amazement. "That's just sexy."

"Careful now Jill," Alicia said grabbing the woman's wrist keeping her hand inches from Tony's plastic cage, "remember I'm the pimp here. Any further is going to cost you."

Tony sat petrified he was about to be discovered, Jill was drunk enough that if she felt the hard plastic of his cage she'd announce it to everyone. Only the falling bra strap provided distraction for Tony. He slowly reached up to fix it with one hand while keeping the other between Jill's hand and his once again aching cock.