Tony and Alicia Celebrate Halloween

"Oh dear let me help you with that." Jill said pulling her hand free of Tony's skirt. "Your bra strap is loose," Jill said leaning close to Tony to adjust it, "I can fix that for you."

Tony sat motionless as Jill adjusted the bra strap. Alicia noticed the glazed look in Tony's eyes and knew it was the contact with Jill and not the fear of being caught that had excited him this time.

"There you go." Jill said as she stood back up.

"What do you say Tony?" Alicia asked almost with a scolding tone.

"Thank you Jill." Tony replied softly.

"Wow," Jill replied, "you can really tell who's in charge here."

Alicia slowly pulled Jill aside talking with her softly before dumping her off with another group of people and returning to Tony. The rest of the party went pretty normally with Tony and Alicia catching up with friends and mingling. Tony had the ever present ache under his skirt thankful that relief would be coming soon. A couple times his buddies asked why he was still in the heels and he'd point out the fake nails. They'd ask why he didn't have someone undo the ankle straps for him but weren't willing to help him out if he asked if they wanted to do it. His feet were in hell and he had no idea how women could wear even a 3" heel for hours every day!

Despite his discomfort Tony could feel the wetness of his panties against his bare skin and the ache of his swollen balls in such a confined space. He was incredibly horny and in dire need of some relief. Even Alicia was amazed to discover how excited she was becoming as the night progressed. When they had gone up to the bathroom Alicia hadn't even considered ducking inside and having Tony eat her out but when the opportunity came she just reacted and took it. She was amazed how wet she was even before then!

Towards the end of the night Jane announced who won best costume this year. Much to Alicia's delight and Tony's dismay it was them! Alicia grabbed Tony by the hand pulling him off the bar stool and leading him in front of the group of friends to their raucous applause.

"Thank you all very much," Alicia said cheerfully, "but really Tony has just been a wonderful sport about all this."

Tony blushed as he received a second round of applause.

They were both thankful when it was time to leave. Tony had no problems with Alicia opening the car door for him or letting her drive, he just wanted to get back to the house and have her unlock him! The words of her promise to fuck his brains out rang in his ears over and over again. Alicia was now the one that had to concentrate, she had something special in store for Tony and it took all her will power not to shatter the speed limit on the way home. It came as a relief to the both of them when they entered the house.

"Go upstairs and go to the bathroom," Alicia instructed kissing Tony lightly on the cheek, "I'll be up in a minute."

"Okay, should I get undressed?" Tony replied walking to the stairs.

"Not yet," Alicia replied with a wink, "I kinda like you like that."

Tony turned and walked up the stairs without a word not knowing if Alicia was serious or not. She gave him a couple minutes head start and then went up the stairs to the bedroom as well. The rest of the night was easy compared to what she had to steel herself for now. Alicia walked into the master bedroom as Tony was walking out of the bathroom. She approached him and put her hands on the sides of his legs near the zippers. As she softly kissed his lips she unzipped the skirt all the way to Tony's hips and slid her hands inside.

"Your panties are soaked." Alicia said between kisses as she massaged the front of his crotch. "How horny are you?"

"Incredibly horny!" Tony replied. "My balls haven't been this swollen since high school!"

"I guess I'll have to fix that for you then." Alicia replied pinching Tony's bottom lip between her teeth and pulling it slightly. "Need me to fuck your brains out Baby?" Alicia asked.

"Oh God yes Alicia!" Tony replied unable to hide his excitement.

"That horny huh?" Alicia teased. "Horny enough to beg for me to fuck your brains out?" She said tormenting him further.

"Yessssss!" Tony hissed feeling his cock crush against the cage. "Please Alicia! PLEASE!"

"I will Baby," Alicia replied savoring the control she had over him, "I'll give you all you want and more but first I have to go pee." She said releasing him and turning quickly to the bathroom. Tony was crushed, his relief seemed so close and was now being postponed again. Alicia had the bathroom door almost completely closed but then opened it to look at the still shocked Tony. "While you wait why don't you take off all your clothes and lay on the bed for me." She said with a smile. "Take the nails off first so you can undo your shoes."

Alicia closed the door quickly listening to the hive of activity in the bedroom as Tony got himself naked. She knew he was soaked, horny and incredibly wanting, the fact that he had a decent buzz from the wine helped as well. His actually begging had been a surprise and was a good sign that she'd be able to do what she wanted with him tonight. Alicia removed her heels and jacket letting the pants fall to the floor. She was amazed how soaked she had become and was positive her nipples had been hard all evening long. Alicia sat and took several deep breaths hoping she could go through with the next step of her plan.

Tony had ripped the nails off quickly, they hurt a little but it was nothing compared to the ache in his crotch and feet. After the nails the heels came off, Tony dropped everything where he stood until he began to walk to the side of the bed. He stepped out of the stockings and panties leaving them as a trail to the side of the bed. Tony climbed onto the bed lay naked in the middle of it waiting for his cock to be released. Once again Alicia seemed to be taking forever! Laying there on the bed in the cool room Tony couldn't help but feel the small plastic cage encasing his manhood.

Alicia flushed the toilet and went to the linen closet. There hidden behind the large bath towels was a plastic bag which she retrieved. She opened the bag as quietly as possible and retrieved the two items inside. Alicia put the first one on the vanity and held up the second to make sure she put it on correctly. She had never put a strapon harness on before and she wanted to make sure the straps weren't twisted as she got into it. Alicia stepped into the harness pulling it up to her mid thigh and positioning the medium sized shaft that would go into her pussy in place. It slid in as easily as expected causing her to moan softly as she tightened the straps.

"Tony!" Alicia called out chuckling at her next instruction for him.

"Yeah?" He replied.

"Did you wipe off that make up yet?" She asked full well knowing the answer.

"Uh, no." He replied sitting up sharply and looking at his reflection in the full length mirror.

"Run downstairs and wash it off in the bathroom there would you." Alicia continued as she put the 5" didlo onto the red vac-u-loc mounting of the harness.

"Can't I just use the bathroom up here?" Tony asked hoping for a yes.

"I'm not done in here yet," Alicia replied knowing the inner torment Tony was going through at that moment, "so if you want that thing off tonight you'll go and do it. I've certainly got enough toys to keep me very happy!"

Alicia struggled not to laugh as she spoke. The image of Tony running downstairs with the clear plastic cage and his cock bouncing back and forth was almost too much to take.

Tony got off the bed and looked around for a moment. The only clothing in sight was what he had just taken off and he wasn't about to put that back on! He quickly ran downstairs to the bathroom and scrubbed his face in the sink. By now his dripping precum had all but become a constant stream. He dried his face and looked closely in the mirror to make sure he got it all off. His eyes slowly trailed down to the cage over his cock. It looked ridiculous on him and he was really beginning to hate having it on. The one positive about it was Alicia held the key and he trusted her totally. Tony looked over his face one last time and then exited the bathroom. It dawned on him just how much light was coming from outside the house through the large windows. He knew that the chances of someone being outside looking in was incredibly slim but the thought still passed through is head as he moved quickly to the stairs. How would he ever explain to anyone he knew what the hell he had on his cock or even convince them that he'd never worn it before tonight! Tony tried to ignore his thoughts and brush them off as silliness as he started to walk up the stairs. His thoughts got the better of him and soon he was running up them.

When he entered the room Alicia was leaning against the bathroom door wearing the dress pants, suspenders and tank top. Tony approached her but was stopped by her words.

"Pick up the mess you made," Alicia said sternly, "after all I went through to get you those clothes I think you should treat them a little better."

"Sorry." Tony replied meekly.

He picked the clothing up and folded each item neatly before putting them on the chair in the corner. Several times he saw Alicia out of the corner of his eye as well as his reflection in the mirror, Jill had been right Alicia was definitely in charge. There she stood still fully clothed ordering him around while all he had on was a clear plastic cage. When he was done he walked quickly back to the bed and lay in the middle propping his head up on a few pillows to see Alicia.

"Actually," Alicia said without moving and directing him with a finger, "lay sideways on the bed and hang your feet off the side." Tony was a bit confused but did as he was directed. "A little further." Alicia called from the doorway. "Just a bit more." Tony was practically sliding off the bed at this point and only his feet on the side railing of the bed frame kept him from falling off completely. It didn't matter Tony was so horny at this point he'd do whatever Alicia said no matter how ludicrous.

Alicia slowly walked over and stood between his legs. She tugged him by his hips a little further over the edge. Yes she thought to herself that will work perfectly. She removed the bottle of lube from her pants pocket and placed it on the bed next to Tony's hip.

"How horny are you right now Baby?" Alicia asked letting her hands run up and down Tony's shaven legs.

"Incredibly horny Alicia!" Tony blurted his reply.

"But who's in charge tonight Tony?" Alicia asked gently rubbing his balls with her fingernails.

"You are Alicia!" Tony replied groaning slightly.

"What I say goes right?" Alicia pressed.

"YES!" Tony blurted gripping the bedding with his hands tightly.

"Now I'll let you out," Alicia said holding the key up so Tony could see it, "but you have to do what I say or else it'll go back on quicker than the first time."

"Yes Alicia," Tony replied obviously confused, "anything you say."

He had assumed that when she unlocked him that he would be the one climbing on top of her and fucking her brains out. In his mind when she told him that she was going to fuck his brains out that she meant normal sex. He could not have been more wrong. I any case when Alicia removed the cage from Tony's cock it instantly began to grow almost as if it knew it was finally free. Tony's flaccid cock was soon a raging, aching hard on. He didn't think anything of it when Alicia drizzled lube over his cock and balls, he had certainly done that to her enough times in the past as well.

"How does this feel?" Alicia asked as her hands rubbed Tony's rock hard cock and swollen balls.

"Mmmmmmmmm sooooooooo goooooood!" Tony cooed.

Alicia slid a well lubed finger under Tony's balls and rubbed it around his ass. This wasn't out of the ordinary either Alicia loved playing with Tony's asshole and often pushed a well lubed finger inside him during sex. It took him a little while to adjust to the idea of how much he enjoyed it but that was an issue taken care of long ago. Alicia had often used a combination of fingering his ass and riding or sucking his cock which Tony now more than expected and loved. The combination would work just as well for her tonight.

Alicia rubbed Tony's cock pressing her thumb into the thick vein underneath while slowly fucking his ass with her finger. She only released his cock long enough to pour more lube on the shaft and his balls. Just before returning her hand to his cock Alicia undid the front of her pants freeing the strapon hidden underneath. She continued to stroke him but began concentrating more on lubing and fucking his ass with her finger. At this point Tony was too excited and horny to care he had been denied and restrained all night and craved any attention he was getting.

"Oh shit!" Tony moaned and tensed slightly as Alicia slid a second finger into his ass.

"Reeeelaxxxxx Baby." Alicia said in a soothing voice. "I know how close you are to popping and don't want you cumming too soon. Just relax and enjoy." Alicia stopped her fingers for a moment. "Take a deep breath and let it out." She instructed. Tony did as she suggested and was able to relax. "There you go." Alicia said lovingly as she felt his muscles relax around her fingers.

The second finger in his ass stretched Tony more than he had ever been before by Alicia but after a moment he adjusted to it. Alicia paid more attention to his cock for a moment and then began moving her fingers in and out of Tony's ass again. Tony was experiencing that fat of a penetration for the first time but the attention paid to his cock was enough of a distraction to keep him happy. Slowly Alicia paid less attention to his cock and only moved the fingers in his ass. Tony was still rock hard so obviously he wasn't minding it too much and having the two fingers inside him first would help with the dildo.

When Tony and Alicia first started playing with anal sex Tony had taken his time and gotten Alicia used to it slowly. Alicia was now copying what he had done with her, he was more than use to having one finger inside him, now with two and soon a dildo he would be more relaxed and accepting of it. Even when Alicia felt she was ready for his 7" shaft Tony made her wait until she was comfortable with a slightly smaller 6" dildo. In the end he had been right because when he penetrated her ass for the first time Alicia felt as if she might split in two. He had wanted to make sure she enjoyed herself and took it slow to make sure not to turn her off to the idea totally. She wanted to make sure she did the same with him, hopefully this wouldn't be the first and last time she wore her new strapon.

"Doing okay?" Alicia asked as she lubed the strapon.

"Yesssssss," Tony replied moaning softly, "but I need to cum sooooo bad!"

"Just stay nice and relaxed like that a little longer." Alicia replied.

With the strapon nicely lubed and Tony relaxed there was only one more thing to do. Alicia slipped her free hand under one of the suspenders letting it fall off her shoulder. Then she slowly let her well lubed fingers slip out of Tony's ass while she rubbed the underside of his shaft with her other hand.

Tony had gotten used to the full and slightly stretched feeling of having Alicia's fingers inside him and realized he kind of missed the sensation. He wouldn't have to wait long for it to return.

"Tony look at me," Alicia said softly waiting for Tony's eyes to lock on hers, "just stay relaxed I'll go nice and slow."

Alicia slipped her other hand under the suspender letting her pants fall to her ankles and guiding the dildos smooth head to Tony's asshole. She pushed it slowly inside him before placing both hands on his thighs. It took a moment but Tony finally realized that both of Alicia's hands were on his legs and he was still being penetrated! He tensed for a moment at which point Alicia stopped and began rubbing his cock again.

"Relaxxxxx sweetie." Alicia cooed.

The attention to his cock caused Tony to relax and Alicia continued.

The two of them had talked about Alicia wanting to use a strapon with Tony for quite a while and Tony was okay with the idea. His initial reaction when he realized Alicia's fingers weren't moving inside him was simple panic but now he was more comfortable with the idea. The fact he had a decent buzz and Alicia kept playing with his cock certainly helped put him in the right frame of mind as well. Alicia concentrated on his face, whenever his eyes rolled into the back of his head Alicia stopped to let him adjust to the feeling.

Alicia had given this moment a lot of thought she agonized over what position to have Tony in when she first fucked him like this. Eventually she decided that having him on his back was best because she could watch the reaction on his face as she penetrated him and share the experience with him better.

She was amazed how quickly and easily she was able to penetrate him fully and feel her hips resting against his ass. Once again she paused and let him get used to the feeling.

Tony felt Alicia's body press into his and gripped the bed with his fists turning his knuckles white. He wasn't sure how large the strapon Alicia was using was but it certainly felt big. Tony took several deep breaths and exhaled fully until he was finally relaxed again.

"Are you okay?" She asked.

"Yes." Tony replied breathlessly.

"Take your hands and grab the backs of your thighs behind your knees." Alicia instructed.

"Okay." Tony responded lifting his legs and feet into the air.

He was rewarded with another inch of penetration causing his body to shake. Alicia pulled the tank top off tossing it aside and let down her hair from the tight bun shaking it out so it fell wildly over her shoulders. She poured more lube on Tony's cock and balls letting it seep down to his ass slowly. When she was sure Tony was ready she pulled out slowly and pushed in again. Tony groaned with each slow penetration. Part of the reason Alicia made him hold his legs up was to keep him from stroking himself but also to keep that wonderful feeling of submissiveness he had seemed to enjoy so much tonight. His knuckles turned white from the grip on his thighs.

Tony looked up at Alicia and could feel the power she had. For the first time in his life he understood how it felt to be a turtle stuck on its back. He was helpless, exposed and vulnerable. Moreover he was all of those things for her! In the mean time Tony looked up at Alicia and only saw her dominance. Her hair had fallen wildly over her shoulders and breasts giving her an almost animalistic quality. With each slow thrust her large breasts swayed back and forth. No one would ever mistake what was happening here, she was indeed fucking him in every sense of the word.

He had adjusted to the discomfort of the dildo, actually it had been slightly slimmer than her fingers. The shaft was smooth and filled him easily. Once Tony got over the initial discomfort of being fucked like this he began to enjoy it, he enjoyed giving himself to her like this and he enjoyed Alicia's dominance.

Slowly Alicia increased the tempo becoming pleasantly surprised by the pressure the back of the dildo was putting on her clit.

"How's that?" Alicia asked slightly grunting.

"Ohhhh God Alicia," Tony moaned, "I don't.... I can't.... OHhhhh make me cum!"

Despite what was going on in his head Tony couldn't verbalize what he was feeling. There was the full range of emotions to include just a little humiliation from being so submissive to her like this but he loved it, he truly loved what she was doing to him. Alicia slowly started to stroke Tony's cock never slowing her pace with the strapon. She gripped his leg with her free hand and began screwing him even harder causing him to moan louder. His eyes never left hers.