Fantasy Fulfilled

He stood on the sidewalk in front of the club, trying to keep a smile as he watched people going past him. His hands pulled nervously down on the hem of his very short club dress. Some people walking past smiled at him, a girl walking past with a couple of girlfriends grabbed his ass and giggled, but most people paid no attention to him. Maybe that made sense. Melinda told him he looked very feminine now, except for his very flat chest

Andy, or as his wife was calling him when he dressed femme, Mandy, looked down. The very sheer bra he wore under the dress was only to provide the feeling of wearing a bra. All that showed were two very noticeable nubs where his hard nipples pushed out through the thin bra. Farther down there was a small bump in the stretchy material to mark the locking fixture of his chastity cage. From there the plastic curved down and was not an issue. Melinda chose plastic in case there were metal detectors

He looked at the doors once more, then at the stamp on the back of his hand, and wondered if she would be coming out with "them" or if she would get him and take him back inside. She had told him to go outside while she negotiated the terms. He shook his head. He was the object of a contract now. Was it time to say stop? He remembered how it started

It was a cold day in mid-January and he had come home from work early. That gave him a chance to set the table and start putting together a dinner. In their four years of marriage, and two years together before that, he hadn't made many dinners, so it was still a treat for him. He went to the basement and chose a bottle of wine. When he came back up, she was home

After a quick hug and kiss, she took off her winter coat, gloves, scarf, and hat and hung them up. She glanced out the window and saw a man carrying a heavy box up to their house, then walking away with nothing. She called out that they had a package and headed for the door only to find him in front of her, opening the door

"Andy, what are you doing? The package is for me and I'm stronger than you anyway."

That cut him. "What do you mean, you're stronger? I can get this and I'll hand it to you, ok? It's only right for the man to do the heavy lifting."

It was a great plan, though she complained about stereotypes and chauvinism. The problem was that he could get one side up, but couldn't lift the whole box. He felt her watching him as he tried, tried something different, again, but she never said a word. Finally, he stood up and looked at her. "Ok, if you're so strong, it's all yours." He stepped back

Melinda came out onto the porch, tipped the box up, gripped underneath, grunted, and stood up. "Get the door, please honey?" Her voice showed the strain, but she held tight

Andy froze for a moment, but the look in her eyes brought him out of it and he opened the door, following her inside and being grateful when she let him help her put the box down in the living room

"Aren't you going to open it?" Andy was curious, but also willing to let it be a surprise, or even just private

Melinda looked at him. "Maybe a little later. I'm still a little upset about that men are stronger comment. I make more money, I'm higher in my organization, I own this house, and I'm stronger. Maybe I need to make it a real challenge for you."

"Ok, that's not fair. I work, and I think I work hard. You're also two years older, so you had a head start."

Her smile faded to a frown. "The fact remains, I picked up the box after you did not." She hesitated, obviously wanting to add more. "I want to challenge you to a battle, one on one, to see who is stronger. I've had a fantasy for a little while now, and if I win, I'd like to see that fantasy come to life."

He hesitated now, looking at her, not sure where to go. A fantasy? He looked at porn, and there was a particular type with wives with fantasies. "Tell me about the fantasy before I agree or not."

She leaned against the box, hands on the edge next to her hips. "You probably aren't going to like it, but if you hear it all, maybe you'll agree." She looked down, then back into his eyes. "Ok, I saw something about a year ago and just got curious. I don't even remember how I got there, but there was a caption on the link that caught my attention." She took a breath, he kept waiting

Another deep breath. "Anyway, there was a girl getting spit roasted, guys front and back, and she seemed to love it. Oh, I so wanted to know what it was like, live, but I wasn't going to cheat on you. So I got to thinking, I could watch somebody else. And then I thought, well, is it cheating if a guy is done by guys?"

Andy stared blankly, letting it sink in and trying to imagine she had said something different. "You want me to let two guys fuck me? You're right, I don't like it." It was flat, like somebody else was using his mouth. "You want me on hands and knees, taking cocks in my mouth and ass."

She shook her head once. "In fairness, not exactly. I just know I'm curious and I'm not going to cheat on you. I don't know where you can go to actually see three people fucking live. So, you know, it kept coming back to you. Feminize you, go out, find two guys, and, well, spit. Roast. But not forced. I would never force you or coerce you. That's why the challenge. I thought, maybe if you knew the stakes, then lost, you'd be more likely to agree, and then I'd have six months to feminize you and have you accept the idea."

He crossed his arms and leaned against the door frame. "I think the word you want is cuckold."

Now her hand went up. "Ahh, no. That is not what this is about. I'm not cheating, remember? No making you watch me with another man. They need to understand it's not me, it's you. Or whomever. I chose you because, well, I love you, I don't know anybody else I can ask, I mean, ok, it's messed up. But it's the best I can come up with."

Still struggling with the whole thing, Andy shook her head as if to clear it. "You love me, so you want to watch me take two men. You know I'm not into men, right? We both look at porn. You know where that stuff leads, right? I thought you were my girl and I was your guy."

She paused. "Do you have a problem with feminization? Ok, wide eyes but no response means maybe not. It's just a role, dear. I have girlfriends and don't need you to be another. Why don't we do a challenge, when you lose we start the process, and you can tell me to stop it any time. If you don't, in early August we go to New York and find some guys who can follow the rules."

"New York? You know people there?"

Melinda smiled. "No, honey, it's because we DON"T know people there. With millions of people it's unlikely anybody we know would recognize us. Oh, of course you'd continue as Andy for work, but when you get home, you become Mandy for the rest of the day and on weekends, if we're home. Now, the challenge?"

His arms went up in resignation. "Fine, you seem stuck on this so let's do it. I don't know why I'm arguing what won't matter anyway. Arm wrestling?"

His wife approached and kissed him, running her hands through his hair. "I'll have to ask my stylist about convertible hair so you can be he and she with the same hair. Let's go to the table."

The couple was the same height, so their arms matched well. They clasped right hands and started a short timer. When it sounded, both pushed. For a while, they held nearly constant, then Andy started to feel a panic as he watched her begin to slowly push him back. He looked at her elbow, still solidly on the table, and pushed back. For another moment, his retreat stopped, then it started again. As she gained leverage, he lost advantage and the arc picked up speed

As soon as his hand touched the table he released, his arm sore from the effort. She suggested using left hands to give him another chance to prove his claim and they started. He pushed her for a few seconds, leaning her back noticeably, but then she increased her effort and held him. He began to tire and then the arms were back to vertical. Then his arm was leaning back

Half an hour later, he looked at his face in her mirror. His eyebrows were a little narrower and shaped with a pencil. Eyeliner gave his green eyes a new intensity and a dark eye shadow gave just enough mood to seem to lift his eyes a little. The redness of his cheeks wasn't entirely from blushing, nor the red of his lips being his natural color. His hair, normally parted on his right side, now swept across his forehead from his left and brushed back over the tops of his ears

"Well?" Melinda asked as she stepped back

Suddenly he felt very tense in his throat. They had a good relationship, even if this was somewhere off the charts, but he was determined to be honest. "She's kind of pretty," he admitted

Melinda had her phone out, making a call. "Yes, hi, I'd like to order two large pizzas for delivery."

He listened to her, a pit forming in his stomach as thoughts raced through his head. She had kissed him before sitting him down, explained everything along the way, and now suddenly ordered pizza. For delivery. He watched her in the mirror

The call wrapped up. "Thank you. We'll be watching. Now then, honey, you think pretty, I think she's hot. I have a question for you, and please, be very honest. Do you think you can open the door and take the pizza when it arrives?"

His eyes widened and he began mumbling and stumbling over words. She held up her hand. "Ok, that would be a no. Honestly, honey, it's not a problem. I would have been surprised if you had jumped up with a smile and ran to the door to wait. Now, how about if you stand at the far end of the hallway?"

He stood and looked at her. The face wasn't hardened, no smile or twinkle. It seemed to be a simple question that he could refuse. That reassured him and he told her he was really nervous. They discussed it and he finally agreed to stand in the kitchen, in view of the door, but with the kitchen light out. He would feel exposed, but the delivery person would be unlikely to notice the makeup

The driver turned out to be a woman, so he relaxed even more, then more when his wife carried in the pizza, kissed him, slipped her tongue into his mouth, and began opening his pants. He suggested they focus on hot pizza. She replied that he deserved a reward. She pushed his pants down as she lowered herself to the floor

When she stood to kiss him after finishing her task, she kept her lips closed, delivering a traditional old-movie kind of kiss. As she pulled away, she said, "One day, I'll open my mouth. I hope you'll be ready. It will always be your taste. Always."

Every chance they had for the rest of the month, she did his makeup. Andy started getting used to the look of Mandy when he looked in the mirror. A piece of him even marveled that he looked so pretty. He imagined he could attract interest while being absolutely terrified of it at the same time

Melinda had talked about it to prep him and had bought additional panties and bras. They were the same height and he had a slim build, but the hip to waist to chest proportions were a little different and she made the adjustments. In February, she had him start wearing panties and bras at home, even getting some inserts for Valentine's Day so his chest looked more feminine. She told him if he lost two inches on his waist, he'd look better. Four inches would make him pretty good. On Valentine's Day she walked out of the bathroom in a heart costume, he wore the arrow sleeve she had given him and nothing else, and they had wild sex for over an hour

March brought him the very thin bras with flat lace or fabric that could stretch to hold a small breast. He was told to start wearing panties and bra under his clothes all day. Andy also went to his wife's stylist, who trimmed his hair so he could part it as a man or bring it straight down in bangs as a woman. Either way would show off his shaped eyebrows. Mascara came on the weekends. Melinda put him on an exercise program and to keep him going, she did it right along with him. She loaned him one of her leotard and tight sets while they exercised so he could see himself looking sexy

April brought tucking. She told him to watch some videos, she gave him the tape, and he started tucking. Using the bathroom was a problem and she began talking about cages. He said he understood, but didn't want anything pink. One night she gave him a blowjob and as they lay together afterwards she described how it felt. She turned to kiss him and he accepted her tongue. She smiled. Another night they fucked and she described the feeling of penetration. She bought him some new skirts that were shorter than what he had worn before. Mid-month, he was introduced to garters and stockings

By June he thought he could see a difference from the exercise. She had him wear pantyhose at work and bought him some choke and lace collars to wear at home. One evening she brought out a six-inch dildo shaped like a penis. She sucked it for a while, then stroked his hair and offered it to him. He hesitated and she just kept stroking his hair, telling him it was ok. Eventually he licked it, then took the head. Melinda told him to watch while she demonstrated how to love a cock, then they passed it back and forth for a while as she trained him. The dildo was shoved into her already-wet pussy and given back to him. He smiled and was much more aggressive. Then they fucked and held each other

Heels training came in July. He would wear the heels and a short dress or skirt and she would walk him around the house. That was when they noticed the bulge from the cage lock, but decided it was small enough they would just put up with it. He thanked her again for making it black. It was obvious and yet didn't scream sissy. He was learning to deep throat the dildo and she brought out an eight-inch version for further training. That was when the smaller dildo went into the harness she bought and he was introduced to anal sex. She started him doggy and eventually had him flat on the bed, legs spread, her breasts on his back and her hair falling around his face. He loved that feeling and the prostate massage made him orgasm the third time they did it

She had worked on his voice and his walk and mannerisms since April, but now she wanted him to do it outside of the house. They went to a mall 20 miles from home and, despite being dressed as a man, she wanted him to talk, walk, and behave like a woman. It led to laughs and giggles and pointing, but she just held his hand or put her arm around him and reminded him it was just for a few hours

At the beginning of August she told him that the New York trip was coming. He needed to take Friday off next week, and she showed the matching dresses she had purchased. Hers was a black club dress, his was a wine red. He thanked her again for not going pink. She also gave him a thin leather collar with no adornment except a ring in front holding a bangle that said, "Loved."

The night before they left, she had him wear his sexiest lingerie and behave entirely as a woman. She had him suck her 'cock' and take it up the ass, all while wearing his cage. Then she had him give her oral until she came twice. As they relaxed, she took off his wedding band. As he nervously watched to see what she would do, she put it to her lips and kissed it, then slipped it into her very wet pussy. After a few seconds she took it out and slipped it back onto his finger, sliding on easily with her personal lubrication coating it. "They will always go together," she whispered

After checking in at the hotel, Andy became Mandy and they went out for dinner. There were a few looks, but either the anonymity of the big city or her training kept the looks, and especially giggles, to a minimum. Saturday Mandy wore a flowery top and miniskirt as they went sight-seeing and shopping. Only once did his voice slip and the only reprimand was a soft slap on his ass. Dinner was kept small because Andy was feeling more nervous and let his wife know it

"Honey, it's my fantasy, and you've done an amazing job becoming Mandy. Still, if you aren't comfortable, if this is going to mess you up, at any point, stop the action. I promise I'll agree and it's done. I'll try to negotiate in advance, but the guys might want something in payment if we stop. I won't give up my pussy, but please understand if I feel I need to do something else for them."

They went back to the hotel for final makeup and prep. When he came out of the bathroom, she had a small case for him. He opened it to see a ring with a diamond. She explained that his ring was the only truly masculine thing still showing, but she didn't want him without one. He smiled as he removed his manly ring and let her slide the feminine one onto his finger. They kissed and walked the four blocks to the club she had selected

The cover was paid, they got some drinks, then danced. A couple of guys came up and danced with them, but when they found out Mandy was a guy, they left. Later three guys came up, but when Melinda explained their situation, they left. It was almost an hour later when two guys, one a few inches taller than the couple, the other muscular and a few inches taller than his friend, came up and asked to dance. Soon they had split into two pairs, the taller one settling in with Melinda since her four-inch heels made her taller than Mandy in her two-inch heels. Andy felt his stomach tighten when he saw his wife pull the guy's head down, then being caught off guard when the shorter guy grabbed his head and pulled Mandy's lips to his for a kiss. Andy had been prepped for this, but to actually be kissed by a guy was still a surprise. He took it, but didn't return it very well

When they broke it, the guy moved his mouth to Andy's ear. "You guys married?" Andy tensed, wondering if the guy realized he was a man. "Hey, it's cool. She and Trev are talking, so I'm guessing she's the lead in your relationship. She give you the collar?" Andy nodded. "It's nice. Says a lot."

The conversation was broken up when Melinda and Trev walked over and Melinda said she needed to talk to the guys. That was when she told Mandy to wait in front of the club. Again his stomach tightened. It was one thing to be with her, but now she wanted him alone, as a woman, in public with people walking past all the time

Another pat on his ass turned him around. It was a man with graying hair and a large smile. He looked at the collar. "Somebody already claim you? That's a shame. I like sissy boys." He leaned closer. "I like to break them completely." He laughed and walked away

Finally he saw Melinda coming out of the club, Trev on one arm and Carlos, as he learned the name, on the other. She was smiling, as were the men. "We're all set," she told him. "Let's go."

Trev slipped his arm around Melinda's waist and she looked at him. "No lower, am I clear?" He smiled and nodded. Carlos put his arm around Mandy. He hadn't been trained for this so he watched his wife leading the way and tried to put his arm the same way

They had walked only a few blocks when Trev's hand slid down onto an ass cheek. Melinda stopped and turned to him. "Which part of no lower was so hard to figure out? I thought I made myself clear. Do I need to tell you to go fuck each other?"

Andy was surprised by how firm she was being. He had expected this to be total humiliation, and here she was missing a chance to have her ass handled in front of him.

Trev put his hands up and took a step back. "Ok, ok. I get it. You're just so hot and it's hard to accept that you were totally serious. I mean, we've never done this, but in the vids the chick always wants the sissy totally broken. I'll try to remember that's not how you're playing this."

After a short hesitation, she let him put his arm around her waist again and they continued to the hotel. Minutes later they were in their room and Melinda was locking her purse in the safe. She went to her bag and pulled out a video camera