Tony and Alicia Celebrate Halloween

"You know I do trust you." Tony replied smoothly enjoying the attention being paid to his crotch. "But this is going to be tough to deal with tonight."

"Just leave everything to me." Alicia replied turning to get the next item out of the bag.

Alicia had to pause for a moment, this was new territory for her. Normally if she and Tony played bondage games she was the one in cuffs. He enjoyed tying her from time to time and she enjoyed being tied so it worked. This time it would be her in charge and while Tony had always said he'd wanted to try that it would take her a bit out of character to make it happen. Alicia took a deep breath and retrieved the panties she had picked out for Tony to wear.

Tony didn't look down to see what he was stepping into, he wanted Alicia to see that he did trust her enough not to question what she was up to tonight. Plus this was the first time she had taken the lead like this and he was beginning to enjoy it. He had always told her that he liked her to try to be a bit more aggressive sometimes but she had never acted on it until today. He realized that the blow jobs to distract him and the way she had dictated what they did today, even her wearing the shirt the way she was, were all ways she had controlled him. He was nervous and excited but knew that she had to be even more nervous and excited than him.

Of course Alicia would continue to use distraction the entire night to keep Tony in line. Even now as she began to pull the panties up his legs she let her face and hair graze against his cock to keep him excited. Alicia pulled the hot pink lace boycuts up Tony's legs and tugged them neatly into position. Underneath the pink lace his cock was still rock hard. Alicia retrieved a matching garterbelt and affixed it to Tony's waist before securing the stockings to it. Next came the matching front close demi bra, Alicia had found natural looking breast forms to fit inside the C cups. With the lingerie in place Alicia stepped away for a moment so that she could see how he looked. Tony took the opportunity to look over at the full length mirror in the room but realized it was covered by a sheet. Obviously Alicia had done last night or this morning while he was doing something else.

"Alicia," Tony replied sheepishly, "do you realize how much shit I'm going to catch tonight in this outfit?"

"Oh come on," Alicia replied batting her eyes and squeezing his cock with one hand, "it'll be fun!"

"Fun for you!" Tony replied enjoying her paying attention to his straining cock. "I have to see my buddies dressed like this!"

"You'll be fine," Alicia replied rubbing Tony's balls through the pink lace boycuts, "plus I'll be there."

"And what are you going as?" He asked quietly.

"Well you're going as a hooker," Alicia said squeezing and rubbing still, "and I'm going as your pimp."

"Alicia!" Tony replied unable to hide his shock.

"Listen Tony you are right." Alicia responded. She knew it was a make it or break it moment and if she was going to keep control of the evening she'd have to act now. "You can't go like this. I mean look at you," she said taking a step back, "you're hard as a rock and practically busting out of those bottoms!" Alicia pulled the boycuts down enough to let Tony's cock spring out. "Look at my monster here," Alicia said grasping it gently and stroking it slowly, "how am I going to hide this under a skirt?" Alicia turned slowly and began to lead Tony towards the corner of the bedroom by his cock. "Come with me, we have to fix this now."

Tony couldn't do anything but follow. He assumed Alicia would take care of his hardon the old fashioned way, she was mostly naked and holding his cock as it was. In the corner of the bedroom was a small refrigerator. Alicia stopped Tony near it and reached inside grasping a handful of ice cubes. Tony almost let out a yelp as Alicia rubbed the ice over his cock and balls. It took some time but eventually his raging hardon subsided. Alicia checked on it from time to time her aching fingers would be worth it if she could get him flaccid enough to fit in the next item she wanted to put on him.

"Jesus Alicia you're gonna make it fall off!" Tony said faking a shiver.

"Just about there Lover," Alicia replied, "don't worry I know how much ice you can take. Plus you freeze me all the time."

"Yeah but you love how I warm you back up!" Tony said with his typical cocky attitude.

Tony smirked thinking about the number of times he had rubbed ice on his cock until it ached only to warm it back up by slipping it inside Alicia. How she'd wiggle and squirm from that! The mini fridge was a must for them, they always had wine, champagne, ice, cool whip and other 'bedroom foods'.

"Close your eyes," Alicia instructed pulling the ice away, "and don't open until I say."

"Okay." Tony replied once again trying to prove his trust for her.

"And don't think about sex or I'll have to get more ice!" Alicia exclaimed.

Tony just laughed and tried to think of something else. Little did he know Alicia's heart was pounding. She had thought about what she was going to do dozens of times over the past few weeks but now that it was actually time she was trembling. Behind the flower arrangement on the fridge she had hidden her most shocking purchase ever, a male chastity device. It was clear plastic and would cover her monster with a sheath while attaching to a loop she'd have to put his cock and balls through. Alicia started with the loop slipping Tony's balls through it first and then feeding his cock through the snug hole.

"What is that?" Tony asked wondering what she was up to.

"No peeking," Alicia trembled through her reply, "promise not to peek?"

"I promise." Tony replied sincerely.

Tony was back to enjoying Alicia being in charge and decided he could handle a little good natured ribbing for what she would do when they got home tonight. Alicia applied some Vaseline to Tony's shaft before quickly slipping the sheath over his cock and putting it in place. It fit snugly but it fit and that was all that mattered. It would hurt like hell for him to try to take his cock out but she knew that he wouldn't do that and ruin her fun. Alicia finally took a small brass padlock and fixed it to the clasp locking Tony's cock up for the near future. Finally she took the key to the lock, which she had put on a long gold chain, and put it around her neck so the key hung between her ample breasts.

"Okay, open your eyes." Alicia said with her heart pounding in her chest.

"Alicia what in the hell is that!?!" Tony said looking down at the clear plastic cage on his cock. "You can't be serious!"

"Actually I am very serious," Alicia replied tugging Tony's panties back in place, "I have the key to that lock and if you want it off you will behave and let me have my fun."

Tony knew he was really and truly at Alicia's mercy. There relationship was based on trust and whenever either of them wanted to try something new the other always went along with it. More to the point Tony was usually the one coming up with it and Alicia always went along, how could he not go along with her now? He felt his cock stir in the plastic cage and test its bounds. The cage held his cock tight causing increasing discomfort. Tony had to concentrate to keep it from getting any bigger as the bigger it got the more uncomfortable the cage became.

"Okay," Tony replied sheepishly, "tonight is whatever you want."

"I knew you'd see it my way!" Alicia said leaning in and kissing Tony while reaching around and giving his butt a squeeze. "And don't worry; no one will know you have it on. It'll be our little secret."

"What's next?" Tony asked wondering if he should.

"Time for makeup," Alicia replied with a big smile, "come with me."

Alicia led Tony by the hand to the bathroom where she had a small makeup table and stool. Instead of sitting so he could see the mirror Alicia had him face away from it before slowly straddling his lap. The brief glimpse of Alicia's mound and breasts made Tony's cock stir again. He could see this would be a never ending battle to keep his cock under control tonight. Alicia leaned in close and moved everything she needed within easy reach before beginning. Tony sat still and endured the constant shifting and movement of Alicia as well as her applying what felt like layer upon layer of makeup. His main concentration was keeping his penis in check which wasn't easy. Every move Alicia made seemed to excite him, just the simple act of her leaning and reaching behind him made his cock stir.

"There we go," Alicia said triumphantly, "all done!"

Before Tony had a chance to look Alicia ushered him out of the bathroom, the only thing he saw in the mirror was that the hot pink lace boycuts he had on only covered about half his ass. He loved that look on Alicia but never thought he'd see it on himself. As they walked back into the bedroom Tony looked towards the full length bedroom mirror which he remembered Alicia had covered. Alicia obviously didn't want him to see what he looked like until she was ready. She positioned him near the bed where the brown bag was within easy reach. He wondered what else was in store for him in that bag; it had already produced the lingerie he was wearing. Alicia turned him so his back was to the bag. She was amazed how compliant Tony had become since she put his cage on him, she'd definitely have to give it another try soon.

"Put your arms down at your sides." Alicia said softly letting her fingers glide lightly over Tony's abdomen.

He followed her direction and soon felt a satin type fabric being pulled up his arms. Once again the twinge inside his panties kept Tony's attention away from what was going on. By the time he had everything back in control Alicia was buttoning the bottom 3 buttons on a semi sheer white blouse stopping just below Tony's hot pink bra. As he looked down at it he noticed Alicia wrap something else around his waist from behind.

Alicia had noticed that if she did the slightest thing to tease Tony that his concentration would be lost directly afterward for at least a minute. She had noticed it as she slid the blouse up his arms and as she had applied his make up. Of course she attributed that to the cage he had on. In stories she read online about men who had worn them the overwhelming consensus was that it made them more docile and also distracted them by making them concentrate on not having an erection as even getting a little excited proved painful. Alicia tested this one more time by leaning forward and kissing the back of Tony's left ear before giving it a little lick and a nibble. Tony moaned slightly but then was "gone" again.

The nibble on his ear was a soft spot for Tony and always excited him. No sooner had Alicia's teeth left his ear Tony felt the rumbling in his loins. Once again he had to concentrate to prevent a painful erection. Alicia slowly moved around Tony's side to his front and could see the concentration and lost look on his face, he was thinking about something else. Alicia looked down and noticed the front of Tony's panties were already moist with precum, she had never felt so in control before. As he was distracted Alicia fastened the fake leather skirt around his waist and tucked his blouse into it. The skirt had two zippered slits up either side that went all the way to his hip; she zipped them both down tightening the skirt against his thighs. She only had a couple more things to put on him then she'd be able to stand him in front of the mirror to look at himself. Her dressing Tony like this wasn't about humiliation as neither of them had ever been big on that, for her it was much, much more about control.

While he was still a bit distracted Alicia led Tony by the hand to the chair in the corner of the bedroom and had him sit. The tightness of the skirt kept his legs pressed together which would actually help later at the party. With Tony seated Alicia walked back to the bed and reached in the bag for a few more items. She looked over her shoulder to see Tony watching her intently and with a wicked smile Alicia raised her heels off the floor, arched her back and leaned forward tugging the oversized shirt up enough to give Tony a good look of her ass and some of her pussy. Alicia stayed like that for a full minute pretending to search in the bag. When she turned back Tony once again had that glazed concentration look on his face. Alicia hurried back to him with the bag removing a package of hot pink press on fake fingernails. Tony would barely notice his hands moving as Alicia affixed each of the nails to his fingertips. The last few items would take the most distraction though. Alicia removed them from the bag and set one on the floor as she took the other one, which was a long and curly blonde wig, and got it ready to put on his head. Alicia stood and straddled Tony's legs deliberately positioning her breasts in front of his face.

Tony went to move seeing a flash of yellow headed by his head when all of a sudden one of Alicia's hard nipples was thrust into his mouth. He sucked and nibbled it trying to enjoy the nipple while still keeping control of his rebellious appendage. Tony was amazed how the sexual energy had amassed while he was caged and now was brought forth to Alicia's breast. His mouth worked in perfect harmony, tongue, teeth and sucking to bring pleasure to Alicia the only way he could. Alicia was amazed as well.

Alicia was thankful that Tony's hair was short as it made putting the wig on easier. She moaned slightly at Tony's efforts to suck her breast into his mouth but finally had to pull away. Immediately after pulling away Alicia saw the glazed look on his face but with a hint of discomfort. Obviously his cock had gotten too hard in its cage and was pressing against the hard plastic walls. Tony closed his eyes and leaned his head back trying to suppress his trapped erection. Alicia seized the moment and dropped to her knees flinging open the shoe box she had placed by Tony's feet. She quickly slid his feet into the black patent heels quite thankful that the size was just about right and then fastened the small ankle straps which would hold them in place. For Alicia the ankle straps were a must. Tony would never be able to take them off with the fake nails in place instead he'd have to ask someone to help him with it. He'd never ask one of his guys friends with at the party to do it or one of their wives so he'd have to ask Alicia and she wasn't going to let him off the hook that easily.

"Okay you're all done," Alicia said standing triumphantly, "want to take a look?"

"I'm really not sure if I do or not." Tony said a bit nervously. "Am I wearing heels!?!"

The look of shock on Tony's face was priceless and made Alicia giggle. She didn't really know leading up to today if she could take charge like this but now that she was she was reveling in it.

"Come on," Alicia said lifting Tony's hand, "no time like the present to try them out. Oh and be careful if you have to itch your face with those nails you have on."

Tony slowly rose to his feet looking at the hot pink fingernails on his hand as he did. He slowly shook his head wondering how he would ever make it through the night. The new shoes slid a bit on the carpet of the bedroom causing Tony to take shorter steps in the 3" heels. He wondered how long he could go before he could take them off. Alicia stood him in front of the full length mirror she had covered with a sheet the previous night and walked to the side of it.

"Ready Baby?" She asked beaming.

"I think so." Tony replied sheepishly.

Alicia pulled the sheet away revealing Tony's costume.

"Are you seriously making me go out like this?" Tony said looking at his reflection.

Tony was torn over how he looked. From the neck down he may have passed for a woman but his face certainly wouldn't. The 3" heels along with his 6'4" body ensured no one would think he was really a woman. Still it felt odd and almost sexy to feel the fabric against his skin. The heels gave his legs a different bit of definition and the skirt was long enough to cover the stocking tops but not by much. The breast forms Alicia had picked out gave his chest a real appearance and the hot pink bra was visible under the blouse. Tony shook his head at his thoughts about how he looked. Alicia walked up to Tony and wrapped her arms around him laying her hands on his pleather covered ass.

"You bet I am," she said giving his butt a squeeze, "and later I'm going to fuck your brains out to make it all worth it."

"If you say so," Tony said leaning down and kissing Alicia's lips, "but that had better be one hell of a fucking!"

Alicia giggled again kissing Tony back, he had no idea what kind of fucking he was going to get but she would definitely keep her word.

"Okay," Alicia said releasing Tony, "practice walking back and forth a bit while I get ready. I certainly can't bring you to the ER dressed like that!"

Once again Tony did as he was told and began walking slowly back and forth. The slippery heels and tight skirt kept his stride short as well as slow and deliberate. Alicia noted how it made his walk a bit sexy. She removed the dress shirt she had on and walked over to her dresser. Alicia had always been in the habit of dressing from bottom to top and today would be no exception. She retrieved a pair of black knee high socks from her dresser and sat on the bed to put them on. Tony then learned how to walk in heels and a skirt while concentrating on his penis not getting hard. It took more coordination than he thought as he walked breasts first into his dresser.

"Be careful sweetie." Alicia said looking over at the completely flustered Tony.

Alicia stood up and walked over to Tony's dresser, making it a point to have him walk around her naked body, and opened the top drawer. She retrieved a pair of white micro-fiber boxer briefs from his drawer. If he was going to wear women's undies she might as well wear men's she thought. Alicia stepped into the boxer briefs beginning to slowly pull them up her legs and turned to see Tony standing with the glazed look on his face. Alicia had a feeling she'd see that look a lot tonight. Then the idea struck her.

"Well if you are just going to stand there," Alicia said leaving the briefs below her knees and turning to face Tony, "then you might as well help me get dressed."

"Okay." Tony replied as he sheepishly walked forward and stood in front of Alicia.

Alicia turned her back to Tony allowing the briefs to fall to her ankles.

"Go ahead," she said looking over her shoulder, "squat down and pull them up."

As Tony moved to squat her could feel all his femme clothing adjust and shift with his body. The boycut bottoms tugged further between his butt and the skirt rode up his legs. He soon stopped thinking about any of that because as he lowered his body Alicia arched her back sticking her ass out at Tony positioning it inches from his face. He felt his cock press against the cage and groaned in discomfort. Still Tony pulled the briefs up Alicia's legs slowly suffering through the pain to feel her soft skin in his hands.

"And now my tank top." Alicia instructed handing Tony a white ribbed tank top before thrusting both of her arms straight over her head.

Tony couldn't help but watch her breasts jump as Alicia's arms shot upward. His cock ached and he could feel precum puddling in the front of his panties. The ribbed tank fit Alicia's body like a glove showing the subtle curve of her breasts and her hard nipples. Tony's eyes completely glazed over while he helped Alicia into her men's dress pants, dress shirt, and tie. Tony was certain that when his cock burst free of it's cage he'd be erect for hours, then he'd really be able to show Alicia who was the man!