Trophy Husband

Cherry kissed and gave Jeffrey a hug, "Let me know how your fitting goes with the tailor today. He has some lovely ideas for you." She gave a pat to his firm bottom and watched it as he turned and walked to the door.

Cherry insisted her husband get fitted for a new wardrobe. They were newlyweds and absurdly in love. Cherry is a business woman and dresses attractively. She is 32 but looks closer to 23. She loves her husband Jeffrey who is 21 with a smooth body, slender and fit. He is younger than his wife and a perfect match for her taste. The way she kisses, caresses, and whispers little secrets to him turns him on. Jeffrey was beginning to think he had a permanent hard-on, as he always had her on his mind.

As he would soon find out, Cherry loved to watch men have sex. She loved seeing their naked asses, and full frontal male nudity, in various predicaments, and loved to see men sucking cock and balls. She would share watching porn movies with Jeffrey depicting men seducing twinks for their first time swallow, and first time anal. She loved to see the reluctant feminization of young men in porn movies, and loved to watch fashionable exotic sissies and fem boys give public blow jobs.

It would become obvious, that she wanted Jeffrey to be her fashionable cocksucker, her exotic sissy cuckold, and trophy husband. He would be her ass kisser. She wanted to see him suck and swallow cum as often as possible. And she would always have video cameras capturing all events.

Cherry sent Jeffrey to the Clothes fitting.

Jeffrey walked into the high class fitting tailor for men, right on his appointment time.

A voice called out, "Hi are you Jeffrey? My name is Victor. Come on in and let's get acquainted for your fitting. It is always a good idea to know a little bit about each other before we start to get the right sense of mood and style. Cherry gave me instructions on what styles, patterns, and colors to look at. Of course there is much more to it than that and we will find the perfect combinations for you so that when you walk into a room you will get everyone's attention."

Victor noticed Jeffrey was young, slender and had a smooth effeminate look to him. "Let's go into the fitting room and take some measurements." Walking into the fitting room with Victor, Jeffrey noticed there were mood lights. The lighting was a bit subdued, but there were two windows. One window was on the wall on each side of the corner of the building over looking the surroundings from 21 stories up. It was raining heavily outside giving a nice drumming effect on the windows, and setting the mood and desire to be warm and naked. The windows were fogging slightly.

Jeffrey was comfortable with Victor from the first minute. Victor guided Jeffrey with a hand on his waist showing the fitting room. It was warm and cozy but large enough for a chase lounge with a soft fluffy covering, a fitting table that could double for a desk, and a massage table that could fold out to a twin size bed. Out of one window he could see another building close enough to see people in their uncurtained windows. The other window, facing another building, had a view over a raised court yard a couple stories below.

As the rain pelting against the windows had a dreamy effect, there was also a light and relaxing back ground recording playing that sounded like small waves breaking on a beach. The room was just big enough for a clothes rack, some shelves and drawers. The end of one of the shelves there was a serving ledge with a small sink. A smaller door by the main door was positioned like a coat closet. Victor said it was to a full bathroom with shower.

At the sink, Victor produced two glasses and filled them with drinks. "Here," he said, "This will help relax you, then we will take some preliminary measurements, and try some fabrics I want to show you. We have all day, and Cherry said you can stay overnight if you want. We will try different positions and styles, so I will need you to eagerly follow instructions, and don't worry you will have complete privacy. Finish that drink, and here is another." The drinks were strong, and Victor had discreetly mixed in meth powder. Victor knew after the drinks Jeffrey would have less inhibition, heightened desire, euphoria, the ability to have long periods of uninhibited sex. With his looks, Victor estimated that Jeffrey likely already had compulsive sex binges. After these drinks Jeffrey might be willing to try things that he wouldn't otherwise The new clothes would assist his eroticism with high energy tweaking. His sexual prowess could get addictive quickly, and would enhance his mental and physical functions. Victor predicted that Jeffrey would be even more affectionate and euphoric.

Victor got a measuring tape from a drawer. "Sit over here for a minute and I will help take off your shoes while you finish your drink."

Jeffrey liked the deep soft carpeting and watched as Victor helped him with his shoes, and socks. He obediently followed Victor's instructions and stood by one of the windows while Victor proceeded to measure his height. There was a height gauge built into the window frame, and a base on the floor to stand on. Victor begins to take a series of pictures.

Victor said, "Now let's get your inseam. I can tell you are comfortable with me measuring and lightly touching. You can touch me if you need to, anywhere you want." Holding one end of the measuring tape at Jeffrey's heel, he traced the cloth tape smoothly up the inside of Jeffrey's leg. "This might tickle a little." He drew it up to the crotch. "I have to take up the slack in your pants to make a good measure. It won't take but a minute." His fingers holding the tape brushed up against Jeffrey's balls. "Spread your legs a little."

There was reverberating thunder outside which made Jeffrey's bare balls tingle in the cool humid air. The blasts of thunder and lightning with crashing rain against the windows made the warm hand of Victor exploring and surveying his crotch feel comforting.

For certain parts of the body, Victor liked to use a clear plastic measuring tape, and he would wet the area with a wet finger, or his tongue, to make the tape stick to the skin.

Victor complimented every part of Jeffrey's body, including the smell. He complimented the touch and feel, with his ooohs and ahhs, and the taste of his skin, when placing the tape measure.

Jeffrey followed the instructions and moved his feet a little more apart. This was the first time another man had touched him, even if it was through clothing. He felt disciplined to obey instructions though and loved all the compliments Victor was giving him.

Victor could feel the rounded contour of Jeffrey's balls through his pubic hair. He was gentle and felt his way behind the balls where he wanted to measure to the perineum of his crotch. Noting the measurement, he let his finger travel a little further. He could feel the rounded beginning of his butt cheeks, and a warm feeling and indention where his asshole was. "Shift your weight from one hip to the other so I can characterize how your body moves."

Jeffrey shifted his weight from one side to the other with Victor's hand in his crotch and finger pushing the indention of his asshole. He felt a little delicate and effeminate in the hands of Victor.

"Lift your crotch in the front, and then arch your back." Victor was getting a feel of Jeffrey's crotch front to back. He could feel Jeffrey was starting to get warm there and his cock was starting to engorge. "Don't be embarrassed if you start to get turned on. It happens to everyone." He was encouraging Jeffrey to be sexually open and free.

"Okay, let's get a measure of your waist and crotch." Nonchalantly he drew the measuring tape around Jeffrey's waist. "This is your belly button height, right?" From where it came around Jeffrey's back, he measured from there down the ass crack, pressing the tape measure between his cheeks, between his legs, and up to the belly button. He had left his hand in the butt crack to make sure the tape didn't move.

"With your body type we with use a white silk spandex blend that will have just the right cling for your shirts. That will be sexy to the women and show off your abs. The men will notice your physique. With the pants we will use medium gray colors and a scrunch back style. It will look so sexy even the men may get aroused, and they will look twice to make sure of what they saw. So with that, let's take off your shirt."

Victor let Jeffrey watch as he slowly looked up and down his chest. Victor noticed the bulge in Jeffrey's pants was getting larger. Victor traced his fingers up and down the sides of Jeffrey's chest and finally slowly traced down from the neck through the chest hair and all the way down to the waist. Then he let his fingers drift down either side of his crotch. He could feel the heat from Jeffrey's crotch building.

Jeffrey accepted another mixed drink from Victor. The drinks had an intoxicating taste and he drank them down easily.

Victor said, "Feel how alive your senses are when you feel the caressing touch of my fingers anywhere on your body. It's the sensitivity and how you feel that makes the clothing styles come alive. Let's take these off," he said as Jeffrey's pants seemed to just float down. His feet lifted automatically to let the pants off. As Victor moved up and down Jeffrey's legs Jeffrey noticed with intensity that Victor's cheek brushed against his penis through his underwear. "Now these," announced Victor as Jeffrey felt a slight movement then cold air as his underwear seemed to float like a leaf to the floor.

As Victor rose again his face brushed against Jeffrey's now hot dick. "Your skin feels nice and soft against mine," he said, as he made a slow up and down movement against the cum vein of Jeffrey's cock. Teasingly he kissed Jeff's upper leg close enough that Jeffrey could almost feel the wetness of his kiss on his dick, which began to strain in anticipation. "It is the touch that really sets off the sexy sensitivity of the clothing," said Victor. While his face was still dangerously close in front, Victor sensuously let his hands travel the contours of Jeffrey's upper legs and hips around where the body curves artistically into the cheeks of the butt.

His hands drifted softly along the bottom getting personal with the firmness of the flesh every centimeter of the way. His hands cupped the cheeks lifting and playing the contours and feeling the increased warmth as he got closer to the treasures. With the butt cheek in his palm he let his index finger drift into the crack until it lay along the depth of the crack. He could feel the heat of the starfish, and of the exotic perineum skin.

Victor kissed around to the cheeks, and then licked with the broad side of his tongue as if to confirm the firmness, heat, and exotic tastes. Kissing again toward the front he could feel Jeffrey flexing intensely the closer he got to the goal. Almost close enough to kiss the head of his cock, Victor stood up and had Jeffrey sit down. Jeffrey realized with surprise that Victor had somehow shed his clothes and was totally naked with him in the office.

Victor reached over and got another drink for Jeffrey. "Open your mouth and close your eyes. Remember how sensitive the skin was?" Jeffrey nodded remembering how intense the feeling was when his cock brushed against Victor's face.

Victor brought the glass to Jeffrey's mouth and let him take a sip slowly. As he sipped, Jeffrey could feel Victor's cock lightly bump against his face. As he sipped again he could feel the cock lightly rub up and down on his face. He took another swallow of the drink, mouth open, and keeping eyes closed. The cock was rubbing closer to where his lips were touching the glass. Soon he could feel the cockhead against his lips as he sipped more. Victor rubbed the glass across his lips softly back and forth. The feeling was hypnotizing. Then Jeffrey realized the glass moved away for a few seconds while the cock head took its place slipping slowly back and forth, gentle and warm against his lips. The glass touched against his lips again as if to give another sip. Jeffrey separated his lips slightly in anticipation, but instead of the glass he felt the liquid drops from the cock head feeding the gap of his lips. The tip of his tongue explored the sensation on his lips as the head of the cock started to caress across but firmly pushed in. Jeffrey used his tongue to see if it was just the tip of the head that was coming in, and then discovered the entire head of the cock had come in. He licked and wetted it so it would slide easily. This part was natural and intuitive.

"Keep your eyes closed. Taste and feel every part of it in your mouth. Take your hand feel and explore my crotch, and with the other hand feel every bit of my ass," instructed Victor.

This was the first time Jeffrey had done anything like this. The close feeling of another person was thrilling, and Jeffrey enjoyed every part of it all. Jeffrey felt Victor tense up, and his cock got harder in his mouth. He could feel the heat coming off the cock in his mouth. As his lips squeezed the cock he could feel the throb of the cock and cum vein pulse. Cum started shooting into his mouth. He sealed his lips tighter so he wouldn't lose a single drop. Victor was pulling his head strongly. Jeffrey held on to the ass cheeks. This was his first time sucking cock. He didn't dwell on it. It just felt natural.

"Keep it in your mouth, taste it well before you swallow," Victor commanded. "Lick it clean." He loved to teach straight guys how to swallow cum.

Jeffrey was enthralled with his first time swallowing cum. He memorized every move from the throbbing cock and pulsing cum vein on his lips to the jets of warm cum splashing in his mouth, and the unique taste of it.

Jeffrey hadn't thought of Victor or the things they were doing as being queer, it was just the process of being fitted, and getting the enhanced and sensitive feelings.

When Jeffrey was done, Victor kissed his mouth first, and then started kissing downward.

Jeffrey's cock was as hard as stone. Letting Jeffrey watch, with elegance Victor licked up the large drop from the top of his cock, and started licking the cock head. It was not just throbbing but was starting to jerk. Victor used a topical anesthetic, and a topical muscle relaxer to massage Jeffrey's anal ring, and then grabbed a tube of lube from the shelf and lubed Jeffrey's asshole generously, while in the front he was teasingly licking and passionately blowing on the shaft. Every blow of cool air on his cock caused Jeffrey's cock to flex and jerk.

Victor covered the cock with his open mouth and breathed air in and out around it. Victor could feel the asshole get more relaxed and finger friendly. He circled the anal ring around playing it like a miniature ballet dancer, twirling about in a dance.

Jeffrey almost couldn't stand it. Then he felt Victor's finger sliding in his asshole and he knew he was getting a prostate massage for the first time. This was the first time he had ever been fingered.

Victor kept it up until Jeffrey's whole body was shivering and tensing. Victor closed his lips and sensuously caressed Jeffrey's cock with his lips. He felt Jeffrey's body trembling and felt his cock starting to jump around in his mouth.

Holding his ass, with finger inserted, Victor could feel him clinch his ass tightly.

Suddenly there were explosive volleys of cum shattering against the back of his mouth, some going straight into his open throat.

Jeffrey was extremely fatigued now and Victor let him lay on the Chase lounge face down over the hump with the meaty part of his legs draped over the sides. His ass crack was giving memorable visual invitations.

Victor told Jeffrey as he was falling asleep, "Relax, most men will fall asleep during a massage." The rain was still drumming the windows, the relaxing recorded sound was of ocean waves breaking gently on a beach. It was hypnotic to Jeffrey.

Victor tailored an entire set of clothes while Jeffrey slept, using the measurements and reflecting on the sensitive moments. He made the custom tailored shirts, the scrunch cheeky pants, and fitted some slightly raised heel dress shoes that hinted the styling of high heels. Socks were chosen to match the slacks.

As the ocean waves continued to crash on the beach in the recording, and the rain continued a sleepy beat on the windows, Jeffrey dreamed the waves were crashing on his ass and he could hear and feel a sensual spanking sound as they slapped on his ass. In his content sleep he could feel the pleasant splash smack like washing a baby's ass, pushing him forward slightly each time in rhythm with the waves. Contently Jeffrey gave a pleasured moan.

Job well done, Victor was getting his reward as his bareback cock slid in and out comfortably and his waist was spanking Jeffrey's ass. He watched his pubic hair and belly smack gently and rhythmically on the tight, almost seamless ass crack. He grabbed an ass cheek with each hand and started fondling them as his cock danced around inside.

'***

Before the conference started, Jeffrey was well rested. He had slept very well. Victor had bathed and dressed him. Victor had tailored cheeky scrunch panties with a tempting panty line. He felt of Jeffrey's ass while he fitted and placed the panties. This made Jeffrey more effeminate and a cross dresser to a degree. He used a body cologne that would be attractive to men or women, and he just dusted Jeffrey's shapely lips with lipstick. With his business casual jacket and tailored shirt, Jeffrey looked like a model from the page of a book.

Cherry was all smiles as she introduced and showed off her husband to conference invitees. Women from across the room looked, and admired. They all wished for a dreamy cuckold. Men discreetly looked on with interest at a pretty butt, and privately desired to see it naked. Jeffrey was drawing a lot of attention as intended.

As Jeffrey moved about the room he could feel the hands of women groping and feeling him with fleeting ecstasy. Below the line of sight, he also felt men's hands firmly exploring his ass, cock and balls. Man or woman, he felt some hands caress his crotch.

The women giggled as if they hoped the play wouldn't stop. The discreet men kept a lingering feeling as if they wanted more.

'***

The convention hall attendees milled around and casually made impromptu conversations about style, looks, and thrilling sexy designs. There were a lot of greeting hugs, some of which were as personal as the conversations.

"Do you eat pussy?" one woman asked Jeffrey.

Daisy a younger woman saw another woman tug Jeffrey into a corner, lift her dress and plant Jeffrey's mouth on her pussy leaving only a fluff of pubic hair all around his mouth. She was jealous. She watched as the lady sat back and she could easily see him start with a lick to the lovely crack of her ass and over her tight brown wrinkles to the splendor of her beckoning vagina, and then the broad side of his tongue opened her pussy lips and the black diamond of her pee hole, until it came to the majestic pinnacle of her throbbing noble clit knob. With incredulity she watched as he licked up a flow of white pussy cream, and opened her pussy for more. She could see right into the depth of her pussy.

"I eat pussy too," Daisy desperately called out to the woman. It looked so sexy it turned Daisy on. She wanted to do it, even though she had never done anything lesbian.

Daisy was intent on coming back around to this lady. Daisy adventured around until she came across Cherry. They introduced, although Cherry already knew who she was. "Let's come in here," Cherry said, and ushered Daisy into a small private conference room. The conference rooms were all equipped with high definition video camera, from different angles. Also every conference room was supplied with a gift basket containing, anal lube, throat lube, topical muscle relaxer, and topical anesthetic. Daisy started to get comfortable but almost overwhelmed by the richness of the whole event. Cherry said, "Come here," and lifted her dress up in the same position she had seen earlier with Jeffrey. Daisy could see her brightly colored nano glitter sparkling aristocratic panties with a glistening bow. Cherry pulled the panties down in the front. Daisy could see the pussy cleft with a dark secret valley in between all the brush. Trance-like Daisy drifted close and as if in a dream her mouth was suddenly covering Cherry's pussy. She felt pubic hair all around her mouth, chin, and cheeks. Soon like an explorer her mouth and tongue were charting every secret crevice with lust.