Tony and Alicia Celebrate Halloween

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Tony is dressed as a hooker, but the real surprise is later
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Ice_Tease
Ice_Tease
135 Followers

Author's note: The Tony and Alicia stories are more about experimentation between a loving couple than hard core stories in a certain category. If you are looking for a hard core crossdressing story this is not the one for you. If you want a story of a guy who will do anything for his girl to include dressing as a hooker and strapon sex then please enjoy it!

*

Tony and Alicia met 5 years ago at a company Christmas party. Both had stepped outside for a breath of fresh air and begun talking, 3 hours later shivering and with numb feet they reentered the building to find the party had broken up and they were the only two left. Since that night they had hardly been apart a single day. Three years ago they married and moved into a quiet house in the country sitting on 5 acres of land. Their friends thought it was the perfect house for them because they both preferred the wide open spaces to city life and were always more comfortable in jeans and t-shirts. Tony and Alicia knew it was the perfect house for other reasons as well.

The property bordered wetlands which meant they had all the privacy they could have imagined as their nearest neighbors were over ½ a mile away. The 45 minute drive meant that their friends and family couldn't just drop in whenever they wanted and had to call first. Tony and Alicia took advantage of their new found privacy by sunbathing nude and skinny dipping in their large in ground pool as often as possible. On several occasions Tony and Alicia even bound one another too one of the lounge chairs teasing and fucking for hours.

Tony had just left the military when he started at the same company Alicia worked for in the sales and marketing department. He was 6'4" tall with an athletic but not overly muscular build. Alicia loved his deep blue eyes, long arms and large hands. He had a cocky attitude that she found attractive and felt that she and Tony were soul mates. She also loved his 7" cock which she nicknamed "the monster". After several years with the company Tony had become the sales and marketing manager, a position which required a bit of travel which ultimately turned out to be a very good thing.

Alicia was 5'9" with a long lean body, long blonde hair and voluptuous D cup breasts. Tony loved to comb, wash and stroke Alicia's long hair and made her promise more than one time not to ever cut it short. Alicia had grown up in the city she worked in but was always a bit of a tomboy. While she did prefer jeans and bare feet too dresses and heels she had a taste for tasteful and sexy lingerie which Tony enjoyed seeing her in. She started at the company as a bookkeeper and moved her way up getting her CPA just before meeting Tony on that fateful night.

To their friends Tony and Alicia were quiet and fairly average. None of them would expect that certain evenings of the week the couple would sit in their living room and watch porn or videos of themselves having sex on their 47" flat screen TV. Nor would they expect that when Alicia had the opportunity to accompany Tony on his business trips they would scout the area beforehand for new sexual adventures. It had started with trips to sex shops to buy toys and moved up from there. Tony and Alicia enjoyed expressing their love and trust of each other sexually. All one had to say to the other was "tonight I want to try something different" and no matter what it was the other went along with it willingly. Their trust for each other was so deep it didn't matter what the other suggested. After they tried something new the two would curl up in bed, or wherever they happened to be, and talk about what they had just done and what they enjoyed or didn't. It was rarely something they didn't enjoy.

Halloween had always been a fun time of year for Tony and Alicia as it marked the beginning of the holiday season as well as signaled that winter would be coming soon. While they loved the winter they always had more than one opportunity to travel to warmer climates and when they traveled they always had fun. Halloween also was an opportunity to push the envelop a little with their costumes. They kept things low key enough so their friends wouldn't be overly shocked but they were often shoe ins for best costume. A few weeks before Tony had tried to lay claim to who would be selecting the costumes this year but Alicia stood her ground and was able to take control. He didn't select overtly slutty costumes for Alicia but he was proud of her and the way she looked and liked to show it off. Doing that at a club thousands of miles away from home was one thing, doing it with your close friends who have no idea about your extra curricular activities was something completely different! The bottoms on last years genie outfit kept riding up on Alicia exposing far more of her rear end to people she'd known for years and who thought of her as a quiet straight laced country girl. No, this year costume duty would be all hers! Ever since relinquishing control of costume selection Tony had been trying to find out what Alicia had in mind.

The morning of the party Tony and Alicia awoke in each other's arms as they did almost every day.

"So are you going to tell me what I'm wearing tonight?" Tony asked knowing Alicia's response.

"No," replied Alicia as her hand glided down Tony's abdomen to his crotch, "you only have a few more hours to wait so be patient."

"You know I'm not a patient guy." Tony whispered closing his eyes and enjoying Alicia's hand stroking his cock.

Tony had figured out over the weeks that if he mentioned the Halloween costumes that Alicia would distract him by at least playing with his cock. Feeling her begin to kiss her way down his body meant that Tony was going to get the full version of her distraction.

Alicia slowly pushed the sheet down and turned so that she leaned over Tony's thighs. She kissed up and down his shaft teasing the underside with her tongue and getting him nice and hard. Tony loved the way Alicia worked his cock with her mouth, it wasn't just the sucking, it was the way her tongue swirled and twisted like a snake over his shaft that drove him nuts. What was even better was that Alicia loved sucking his cock so she was always enthusiastic and willing to do it, it wasn't something she had to do but something she enjoyed doing. Alicia gurgled and slurped Tony stroking him with one hand as she did.

"Mmmmmmmmm you are my favorite little cock sucker." Tony moaned.

Alicia simply smiled and continued her distraction, she never minded being referred to as his little cock sucker, to her it was a compliment. She watched his body react to her mouth and could tell that Tony was not far from cumming. That was fine, she had a lot in mind for him today to get him ready for the party and this was just the start. Tony's hands moved into Alicia's hair stroking it and keeping it out of her way. She took that as the signal and pumped her mouth up and down on his shaft. He never had to hold her head and push her down; she always knew just what he needed. Although there were times he did that but not during a morning blow job.

"Here it comes Baby!" Tony called out just before the first hot jets of cum shot into Alicia's mouth.

She sucked and swallowed as quickly as she could feeling her mouth fill with his warm seed. There was something powerful about giving an amazing blow job for Alicia maybe that was why she enjoyed it so much. Alicia swallowed the last drops and continued to suck Tony, milking his cock with her tongue, until he was soft again. When he was she gently laid his cock down and kissed her way back up until she put her head on his chest again. Their two naked bodies intertwined both of them physically and emotionally satisfied.

"So," Tony said softly, "what am I wearing tonight?"

"Oh you!" Alicia replied playfully slapping Tony's chest before sliding up and kissing him deeply.

Eventually the two of them got out of bed, Tony pulled on a pair of boxer briefs and Alicia put on a dress shirt of Tony's that she loved. They headed downstairs and made breakfast enjoying coffee and bagels on the back deck in the mid morning sun. The two lovers lounged most of their morning away, laundry and cleaning would come tomorrow, Saturdays was just for the two of them. They relaxed sharing a pot of coffee on the deck while holding hands. Thankfully it was still very warm for a late October day, with the sun overhead Tony and Alicia stripped and laid in the sun naked. They tanned for a couple of hours before Alicia finally stood up and took Tony by the hand.

"Time for a shower." Alicia said picking up his underwear and her shirt and carrying them inside.

Tony kept his hold on her hand and followed closely behind. Showers for them were always kind of a ritual. The shower in their master bedroom was large enough not to need a door or a curtain and had two showerheads as well as a small teak bench with a handheld showerhead near it set lower. Alicia turned on the shower heads and adjusted the water to the right temperature before leading Tony into the shower. She washed his body thoroughly imagining the fun she would be having with him in a few moments. Tony was still unsuspecting as to what was in store for him while he lathered Alicia's long blonde hair. Alicia tilted her head back and pressed into Tony's hands as he massaged her scalp.

"I do love when you do that." She cooed.

"I know you do." Tony smiled. "Trust me, I like doing it too."

Tony rinsed Alicia's hair and conditioned it before washing her body. The body wash they used smelled like cotton candy but the scent was just faint enough that no one noticed it on Tony. Then came Tony's favorite part, Alicia shut the water off and sat on the teak bench spreading her legs. Tony took a razor and shaving cream from under the bench and started on Alicia's right leg. He slowly lathered the leg and shaved it using the hand held showerhead to rinse her leg off when he was done. This process was repeated on the other leg and then up to her thighs. When he had completely shaved and rinsed her thighs as well Tony lathered up the area above Alicia's clit and began delicately shaving her pussy bald. She preferred it bald but sometimes Tony liked to try to sculpt designs into her blonde pubic hair. Finally when he was satisfied Tony rinsed her off.

"Time to check my work." Tony winked.

"Oh don't worry," Alicia replied with a smirk, "I wasn't going to move until you did!"

Tony leaned forward and softly kissed the area he had just finished shaving. As expected it was as smooth as a baby's bottom. He had been shaving Alicia for a while now and had become very adept at it. Alicia leaned back on the bench supporting herself with her elbows as Tony kissed his way lower finally flicking his tongue over her clit.

"That's not where you shaved." Alicia moaned as Tony licked her again.

"Want me to stop?" He asked playfully.

"Not a chance!" Alicia replied.

Tony licked her clit slowly at first, long lavishing licks up and down it, making Alicia breathe quicker and rock her hips with his tongues movement. His hands moved up the backs of her thighs lifting her feet off the tile floor of the shower. Alicia crossed her ankles behind Tony's back and let her legs fall open. Tony slipped his hands to Alicia's pussy spreading her open gingerly with his thumbs before plunging his tongue inside her. Alicia lay back on the bench and used one hand to hold Tony's head in place while she teased and tugged her nipples with the other. Alicia let out a long and loud moan letting Tony know she was close. He slid his tongue back up to her clit which he flicked as fast as he could. Tony took his right index finger and plunged it into Alicia's pussy as well, that was all she needed.

"Ohhhhhhhhhhhh! Uhhhhhhhhhhhh! Tonyyyyyy!" Alicia groaned.

Tony continued to lap Alicia's flowing juices until she was done. He took the handheld showerhead and rinsed her lower body one more time while she lay on the bench and recovered. Finally he stood and extended his hand to help her to her feet. Tony wrapped his arms around her and kissed Alicia softly slowly turning her to change spots with her. When their lips parted Tony slowly sat on the bench where Alicia had just been and leaned back on his elbows.

"Today we are doing something just a little different." Alicia informed Tony as she stepped out of the shower area and walked to the vanity.

"What do you have in mind?" Tony asked watching Alicia's butt wiggle as she walked.

"You'll find out soon enough," Alicia replied taking something from the vanity and turning back, "suffice to say you'll also find out what you are wearing tonight very soon too."

Alicia walked back with whatever she had picked up behind her back. Tony had learned not to question her and to just go with the flow. That was how their relationship worked and how they were able to constantly experiment with different sex games and roles. Alicia knelt between Tony's legs and produced a pair of wet/dry clippers just out of Tony's view. When he felt the clippers down by his ankles he sat up quickly to look.

"What in the world are you doing?" He asked as he watched Alicia remove large tracks of his dark leg hair. "What kind of costume are you putting me in?"

Alicia just grinned and continued to go about her shaving. In no time at all Tony's left calf and shin were left with nothing but stubble.

"Think about it," Alicia said trimming his other leg, "what guys shave their legs?"

"Besides not this guy I'm not sure!" Tony replied still somewhat in shock of what Alicia was doing.

"You do trust me right?" Alicia asked playfully.

"You know I trust you more than anyone else ever Alicia." Tony replied. "You just have me wondering what you are up to now."

"Maybe I'm having you go as Lance Armstrong," Alicia said with a wink, "it's very possible in the bedroom I have a pair of spandex bicycle shorts and spandex shirt for you with one of this little hats they wear."

"Oh I can see that going over well." Tony laughed imagining standing around drinking with their friends in skin tight spandex.

"Okay, maybe I'm having you go as that Olympic swimmer guy," Alicia continued teasingly as she began to trim his thighs, "and you'll be wearing a little blue speedo all night!"

"I can't wear that!" Tony replied sharply.

"That's true," Alicia answered never stopping her hands from trimming, "where would you put your wallet after all?"

Tony didn't find much humor in wearing a blue speedo either. The idea of standing around in a small swim suit that hid nothing didn't appeal to him in the slightest! Once Alicia got to the top of his thighs it was easy, that was the area she typically shaved daily as it was. With the long hair removed Alicia started again at his ankles with shaving cream and a razor. She replaced the blades often to keep them fresh and made sure to rinse his legs after a couple of strokes of the razor. Alicia took her time, after all Tony had been shaving her legs more often than she had, she didn't want to knick him after all. Tony finally leaned back on the bench and just let Alicia go about her business. Alicia had Tony stand and turn around so she could make sure the back of his thighs matched the rest of his legs, when she was satisfied she had him turn and sit again so she could shave his crotch. Tony actually enjoyed this part. Until he met Alicia he had never thought about grooming that area of his body. A few months after their first being together Alicia commented that Tony should shave his crotch hair. Tony had replied that if she wanted him shaved then she should shave him, much to his surprise the next evening Alicia did just that! It took a little getting used to but he found it comfortable and enjoyed the look, plus it gave him the excuse to shave Alicia as well. Checking his work afterwards became an additional bonus he enjoyed greatly.

"There we go," Alicia said triumphantly as she rinsed Tony, "all smooth."

As Tony and Alicia dried off she caught Tony looking in the mirror at his hairless legs. Alicia took some moisturizer that she usually used on her legs and began to spread it on Tony's. Normally she used a non-scented moisturizer on his crotch but today she decided to go with coconut scented body butter. She loved the smell of coconut and the body butter would help soothe his legs.

Alicia then sat at the makeup table in front of the large mirror and held up a brush for Tony. "Do you mind?" She asked playfully.

"Of course." Tony replied enthusiastically taking the brush from her hand.

Tony brushed out Alicia's hair starting at the back and working to one side then back to the other. Alicia applied the body butter to her bare skin as he brushed out her hair, the mirror in front of her allowed Tony a full view of her naked body which excited him considerably. When Tony was done he helped her rub some of the body butter on her back as well.

"Ready?" Alicia asked pulling the dress shirt she had worn earlier on and buttoning a single button well below her breasts.

"Ready for what?" Tony asked glancing down at his shorn legs.

"It's getting close to 6," Alicia said turning and hugging him, "time to get dressed!"

"I can hardly wait." Tony said rolling his eyes as Alicia once again took him by the hand and led him to the bedroom.

"Have a seat on the bed I need to get your stuff." Alicia said letting go of his hand and walking into their walk in closet.

Tony sat on the edge of the bed looking down at his legs. He wondered what Alicia was up to and was hoping she wasn't up to anything too crazy. He knew he'd get payback for the genie outfit the year before! Alicia came back out of the closet with a large brown bag and set it on the bed far enough away so Tony couldn't see what was inside it. She had planned ahead for this and knew how to keep him distracted. Whenever she moved or had to do something she did it in such a way to make the front of the dress shirt fall open enough to give him something to look at. Even after all these years Tony would still try to look down her shirt whenever possible. He didn't even notice Alicia opening a new package of black lace top stockings with seams up the back.

Alicia walked over and stood between Tony's legs leaning forward enough to give him a view straight down her shirt. She brushed her lips lightly against his face before heading to his ear.

"Just keep in mind," she whispered closely, "I do love you."

"I love you too." Tony replied softly not looking away from Alicia's chest.

Alicia slid down until she was kneeling on the floor and began rolling one of the stockings out of sight. She could see out of the corner of her eye that Tony had already become quite aroused but she had planned for that. The only question was could she go through with it? Alicia slid the first stocking onto Tony's foot and quickly slid it up his leg. Before he realized what she was doing it was already past his knee.

"You are kidding me right?" Tony asked shocked by what he was seeing.

Alicia left the still partially rolled stocking above Tony's knee and moved to the other leg without a word.

"Alicia," Tony rebelled, "I can't go out like this!"

"Stand up sweetie," Alicia replied getting to her feet, "and you can't complain until you have the entire outfit on."

Never the less Tony stood allowing Alicia to pull the stockings up into place. Alicia made sure that as she turned her long hair brushed against Tony's now hard cock, just that slight sensation kept him from speaking. Alicia now knew she was in control. The insides of the lace tops had elastic which held them neatly in place. Alicia cupped Tony's balls and rubbed his rock hard cock looking into his eyes.

"Trust me," Alicia said with a gleam in her eye, "I will make it alllll worth it in the end."

Ice_Tease
Ice_Tease
135 Followers