One Slip

by Jennifer White

      

Ever since he was a young boy, Brent had been fascinated with girls and their clothes. At the age of seven, he used to put on his sister's dresses and walk around his room pretending that he was a girl too. The first time he wore a dress it made him get all hard, and he just loved how it felt to be feminine.

As he grew up, he still retained his love of femininity. But as he grew into an adult, he realized that his desire was to date girls. He liked being a woman, but he could never see himself with a man. No, he needed to be with a female partner, even if sometimes he wished that he was a girl too.

When he met Sheila in college, she swept him off his feet, and they fell deeply in love. A year after graduating, they were married, and now they lived together in a nice house in the suburbs. They both worked, and they were both happy in their lives. For a while Brent had harbored a wish that Sheila would somehow be into his fantasy of dressing as a woman, but if he did something like rent a movie where a man dressed up as a woman, she never showed any signs of interest. Sadly, he let himself forget his fantasy. She was too straight-laced, and she would never go for that. He gave up all ideas of ever dressing up again.

* * *

One day, Sheila called Brent at work.

"Don't forget that we've got the costume party at the Johnson's tonight" she said.

"I've got it on my calendar" he replied.

"Did you decide what we're going as?" she asked.

"I've been too busy" he replied, a little annoyed that she was bothering him with this at work. They were *her* friends. Why did he have to do the planning for their stupid party? She knew that he didn't like to go to something like that. He was just doing it for her. Now she was nagging him. He was late for a meeting, and he wasn't very happy about it all.

"Look, I have to go" he said.

They said their good-byes, and he hung up. He headed down the hall for his meeting, and continued on with his work day.

* * *

After dinner, Brent dreaded what was to come next. Sheila would have picked out some stupid costumes that they would have to dress up in, and then go to the stupid party with her stupid friends he didn't like. At least they would have something to drink. He felt like he needed a drink, right away. He followed her upstairs after they put away the leftovers and washed the dishes together, as they always did.

"Do we really have to go?" he said, the disappointment showing in his voice. "You know I don't like this kind of thing."

"Yes we do" she replied firmly. "I told them we would be there. And Betty is a good friend of mine, even if you don't like her."

"What if we just say I'm sick?" he asked.

"We can't back out now. I promised Betty that I would bring snacks. And she has done so much to prepare for the party. Do you really want to ruin her party by us pulling out at the very last moment? Do you want to make me look bad to all of my friends like this?"

Sheila could really lay on the guilt. Brent sighed. There was no way to win an argument like this with her. He had to give in. As he always did.

"Okay, we'll go" he said. "But I'm not staying there all night."

"Very well" said Sheila in a tone that told him that they *would* stay, until she was good and ready to leave.

 

The entered the spare bedroom, where Sheila had laid out their costumes. There was a tuxedo with a top hat, along with a white bridal gown. Great. They were going to go as a bride and groom. Brent though that it was pretty lame!

"I don't know..." he said.

"Well, you didn't think of anything better, so we're going with my idea."

"Yeah, I guess so" he said glumly. "It just seems so... predictable."

"I understand" said Sheila. "That's why there is a twist!"

"A twist?" asked Brent.

"Yes dear. Tonight, *you* are going to be the bride. And *I* will be the groom."

Brent was stunned. It was like his inner fantasy had suddenly come to life! Sheila was going to dress him up as a woman! But then he was going to have to go out in public like that. But he had always wanted that in a way too. He didn't know what to say. But he realized that he had better not let on that he *liked* the idea. Then he'd have to admit to his wife that he *wanted* to dress up as a woman. That was something he needed to keep hidden from her!

"Now Sheila..." he said.

"There isn't much time" she snapped, cutting him off. "We need to get you in your costume. Take your clothes off, and we can get started."

Brent grumbled, but didn't put up too much of a fight. He had to let her think this was *her* idea, and that he was resisting her. If he just caved in and did it, then it might look like he *wanted* to let her dress him up. And he had to avoid it appearing like that! Yet, he could hardly contain his excitement.

As he removed his boxers and took the white silky panties from Sheila, he was so excited that he forgot not to let himself get hard, and his penis started to stiffen. By the time the ever so soft fabric of the panties was wrapped around him, his penis was getting quite hard indeed. As he took the bra from her, she couldn't help but notice the growing bulge inside his panties.

As Brent pulled the bra on, he made an even large mistake. Having worn one countless times, he could put on a bra without thinking. He simply reached behind himself, and hooked it up. It was a major slip on his part! Not only could Sheila see that he had become completely aroused by putting on her undies, but he had put the bra on himself so easily, that there could only be one explanation: he had worn one before. Enough times to be good at putting one on! She remembered struggling to learn at first, after she graduated from her training bra.

Sheila had sometimes wondered about Brent. Her girlfriends all complained about how their husbands would never like to go shopping with them, particularly for clothes. But Brent never complained, and she didn't have to drag him along. He also seemed to know a lot about women's clothes, but he had always said it was because he grew up in a house without a father, surrounded by three sisters and his mother. That and a few other subtle things had made her start to suspect that he was holding something back. Part of her reason for picking the bride and groom costume was to find out for herself. There was no doubt in her mind now: Brent liked to dress up as a girl.

She would proceed with her plan.

"These are called breast forms" she said, handing a pair of realistic fake boobs to Brent.

"Do I have to wear them?" he said, trying to act like he was protesting.

"Yes dear. They're needed for your costume."

Sheila wanted to be careful not to let on that she knew. Not yet.

Brent put the breast forms into his bra, and pretended to be disgusted as he looked at himself in the mirror.

"I look foolish like this" he said. "This is crazy."

In his mind, he was thinking that he looked foolish because of all the hair on his chest and legs. If he could only shave it all off, *then* he'd look much better. He decided to back off on the protesting though. He didn't want Sheila to get a change of heart, and tell him he didn't have to go like that!

Piece by piece, she dressed him up in his wedding gown. When she was done, his skirt billowed out around him quite wide. He wore elbow length white gloves made of a soft, lacy material. She attached hair extensions to the back of his head, then did them up and added a veil that covered both the back and sides of his head, then added a tiara in the front.

Sheila sat him down, and started to apply makeup to his face. After a layer of foundation, she used quite a bit of rouge to give him cheekbones, along with a shiny pink lip gloss. She applied some glitter to his face, then went to work on his eyes. She outlined them with a pencil, then applied mascara to make his lashes look long and dark. She applied pink over his eyelids, blending to a more muted shade above them. Then she used a pencil to darken his eyebrows, more so on the insides, so they looked like they got thinner as they went out to the edges of his face.

She had him put on a necklace, then she clipped two sets of earrings onto him. The effect was stunning. He looked as much like a woman as it was possible for a man like him to be. Sheila insisted that he hold a bouquet of red roses, while she snapped several pictures of him (over his mild protests). As a final touch, Sheila gave him a pair of white heels to put on. He slipped them on his feet, wondering where she got a pair in his size.

"Oh dear, can you go to the closet and get me one of your white dress shirts for my costume?" she asked.

"Certainly" he replied, standing up and gliding into the closet. Sheila watched him walk, and again her suspicious were confirmed. He had definitely worn heels before. There was no stumbling, no teetering. He moved too confidently in them. Her mind was sure now. Brent had spent considerable time dressed as a woman.

Sheila took off her clothes. She had Brent help her wrap an athletic bandage around her boobs, to help press them flat and hide them. She then donned a T-shirt, followed by one of Brent's white dress shirts. She put on a pair of his boxers, black socks, and then pulled on the pants to the tux. After putting on the tie, she added the jacket and the black shoes. She was starting to look like the groom now.

Next, she put on light makeup. It surprised Brent to see her doing that, since she was supposed to be the man. She took Brent's wallet, and slipped it into her back pocket. Then she handed him a white purse, and told him to guard it with his life, as a real woman would. He nodded. He was going to get to carry a purse!

"How should I hold it?" he asked, pretending not to know.

"Like this" she said, showing him.

"Oh, I see" he replied.

It was time to go now. Sheila took the car keys from the counter.

"I'll be driving tonight" she said. "I'm the man of the house, and you are my lovely bride."

Brent shivered all over. This was too good to be true! The layer upon layer of crinkly material under his dress hid the fact that he was as hard as a rock now. The way his full skirts swished, brushing against his nylon-encased legs, it just made every sensation even better. How good it felt for him to have large boobs on his chest (even if they were fake). They looked real enough, and it just felt so good to have two large mounds there, for the first time in ages. He almost skipped along he was so happy, to have makeup on his face, the scent of floral perfume wafting about from *him*, the light tickle of the veil on the back of his neck... he could hardly contain his excitement.

And now he was going *outside* like this! As Sheila held the car door open for him, it again made him shiver. She was treating him like a *lady*. He had never felt so feminine before in his life. As she got in to drive, he had to control himself, not letting on that he was enjoying this more than anything he had ever done with her before!

"When we arrive at the party" she said, "I will go by the name 'Sheldon'. And you will be 'Brenda' tonight."

"Brenda" said Brent. His wife was giving him a girl's name! He decided right that he wasn't going to need to drink all night. He already felt better than any alcohol or drug could ever make him feel.

"You look ravishing tonight, Brenda" said Sheila in a playful tone of voice.

"And you're so handsome, Sheldon" said Brent.

"I have the prettiest bride in the whole world" said Sheila. "I'm one lucky man."

"And I am such a lucky woman to have the hunkiest man in the world as my husband" said Brent, although he didn't like how that sounded. All of his life, when he imagined himself as a woman, it was never with a man.

They arrived at the Johnson's house, and there were already dozens of cars parked all over the street. Sheila went around and opened up Brent's door, helping him out as a gentleman would. They walked up the steps, and Sheila didn't miss that fact that even on steps, Brent did just fine walking in heels. Of course, going down steps was harder. She couldn't wait to see how he did at that!

They walked in the door, arm in arm. Brent caught sight of all the people there. There were women in various outfits ranging from a maid, to a cat, a nurse, a witch, and so on. As for the guys, one was a construction worker, one was a footballer, there was one dressed as spiderman, another as a doctor (obviously with the nurse), and so on.

It dawned on Brent that every single one of the man had one something manly. He was the only one not looking macho. Instinctively, he knew that he had to avoid being alone with the guys. They would be merciless, and give him a hard time about being dressed as a bride! He stayed close to Sheila, knowing that it would keep any such taunting to a minimum.

Soon enough, as often happens at parties, there were groups of just guys hanging out, while other clusters were all the girls. A few mingled, but it was mainly single gender groups. Except that Brent was staying with the girls all night long. They all took to his costume, complimenting him, and telling him how courageous he was to wear something like that. Often, they'd compare his outfit to their own wedding gown, and reminisce about back when they first got married.

Sheila noticed how well 'Brenda' seemed to blend in as a woman. Brent wasn't a guy sticking out like a sore thumb among a group of girls. Instead, he was able to join in as if he was one of them. He was quite popular with the women at the party, and she was happy to leave him for a while, talking gowns, corsets, trains and bustles with the girls, while she went to get some drinks. She talked with some of the man as she sipped her vodka-spiked fruit punch. Many of them made teasing references to Brent.

"Talk about pussy-whipped" said one of them.

"Yeah, I'd never let *my* wife do that to me!" added another one.

Sheila just laughed, and hung out, acting as if she was "one of the guys". She kept an eye on Brent, watching him stick with the girls all night long. They way he stood, the way he held his hands... it was all too good. He didn't look like he was a man in a dress; he had the posture and mannerisms of a woman. That wasn't something that could be learned in one night, on the fly, with no coaching on her part!

When it was finally time to go home, Brent seemed almost reluctant to leave the company of all the ladies. He had fit in so well, and had such a great time getting to be a girl, while hanging out with 'other' women. He followed Sheila back to the car. As before, she treated him like a lady, holding the door open for him. As they drove home, she asked him about his night, and he told her how nice all of her friends were.

The arrived back home, and she let him in the door. She took him by the hand, and smiled.

"Now it is time to consummate the marriage."

Once inside the bedroom, she took charge.

"Brenda, reach down and take off just your panties. Then get onto the bed for me."

Excitedly, Brent did as she asked. He was as hard as a rock again, having built up a sexual tension all night long. He laid there on the bed, waiting for her to make the next move. Sheila dropped her pants and removed her boxers. Then she climbed on top of Brent, mounting him. He slid into her pussy easily, since it was so lubricated already.

"You're a *woman* now, Brenda" she said. "And *I* am the man. You are my pretty little wife, and I am your husband."

She bounced up and down on him once, sending waves of pleasure through him.

"I love it so much that you have become my little flower, my delicate girl. You are so feminine! So pretty. I love so much seeing you with big boobs on your chest. I'm so glad that you're my woman. I absolutely *love* you as a woman. You are Brenda now. You are a woman. You have become *female*. Now you are a girl."

Brent couldn't help it; he exploded in the biggest orgasm he ever had in his life. Sheila bounced on him a few more times, until she too had come. When she was done, she remained on top of him, and held his hands down by the wrists.

"You really like being a woman, don't you?" she asked.

Her voice wasn't mean, nor was it accusing. She just said it calmly, stating a fact.

"Yes" said Brent, "Tonight was a lot of fun."

"It really turns you on, being a woman, doesn't it?" she asked.

"Yes" he replied.

"I can tell this isn't the first time for you" she said.

"How..." he started, but she cut him off.

"A woman can tell. I just want for you to admit it to me."

"Okay" said Brent. "I like being a woman. I've been doing it since I was a young boy, but I've never told anyone, not even you. When I fell in love with you, I promised myself that I was done dressing up, forever. I never touched your things. I never gave into temptation. I kept all of my love for you only. But there *is* a part of me that likes this *so* much. It has always been my fantasy, but you can understand why I've never told you. How can a husband tell his wife that he wants to be a woman sometimes? You could have been mad. You might have left me. I just could never tell you. I'm so sorry."

"I really want for you to be happy" said Sheila. "I'm so glad that you were finally able to share this part of yourself with me."

"I don't want any secrets between us" said Brent.

"Just tell me" she asked. "When you're a woman, do you ever have any feelings for man?"

"Not at all" he said. "I only like women. I guess that makes me a lesbian or something."

 

Sheila laughed. She leaned down and kissed Brent hard. She still had his wrists pinned down, and he didn't offer any struggle to resist her or to try and take charge.

"I want for you to be happy" she said. "I want for you to be able to express your feminine side too. So a few days each month, lets make a date for us to stay home, so you can be Brenda. I'll love you, help you, and support you. I like how it feels to be the man, so when you're Brenda, I'll become Sheldon. I am going to make you feel like a woman, and I will be your man."

"When I was a girl, I used to sometimes dress up in my brother's clothes. I liked how it felt to be a boy. But when we got married, I vowed to put away *my* fantasies forever, and never dress as a man again. I gave in a little when I picked the costumes for the party tonight. It was so lucky that you're just like me. I guess we were made for each other."

"I love you" said Brent.

They kissed again, and spent an hour snuggling before they undressed, and finally went to sleep.

* * *

In the morning, Sheila started off the day with a request that made Brent almost swoon with pleasure.

"Why don't you take a bath, honey" she said. "Why don't you shave your legs for me. And get rid of all that yucky chest hair, and under the arms. I have some Nair under the sink, if you'd rather use that. It's your choice."

"That sounds fun!" he said.

"Great. Make sure you use my bath oils, to make your skin nice and smooth."

Brent was in heaven as he removed all of his body hair, as he had longed to do for years. After he was done in the tub, it took some time cleaning up all of the hair he had just removed! Sheila had laid out a bra and panties for him, which he gladly put on. He was disappointed when she gave him his own blue jeans and shirt to dress in though.

But after breakfast, his spirits were lifted when they went out shopping for clothes. Sheila would pick out something and show it to him for his approval. Then she'd find one in his size, and add it into the cart. He could hardly contain his excitement as she started to build up his feminine wardrobe, item by item.

They also went to the cosmetics department, and she picked out an assortment for him, so he would have his own things. She bought night creams for his face too, along with all sorts of accessories. The next stop was at a store that sold wigs. She told the clerk that her husband wanted her to wear a long blonde wig, and could he help pick one out? Of course, the wig wasn't for her, it was for *him*. But she didn't embarrass him in front of a stranger.

That night, after they ate dinner together, she showed him how to put on his face cream. Then she had him put on his brand new pink silk nightie, along with a pair of panties. They made love, both wearing just their nighties, and went to sleep in each others arms.

"Tomorrow, we'll do each other's nails" she said, before they drifted off to sleep....

* * *

Add day on Sunday, Brent got to be Brenda. Sheila seemed to delight in teaching him about how to do his nails properly, his makeup, and fashion trends that had passed him by since the days that he used to dress up. Brent was wearing pantyhose, a tight black dress, his new blonde wig, and a pair of pumps.

"When I saw you walk in heels so well" said Sheila, "I knew."

"Oops" said Brent. "Well, its all for the best that we know about each other now."

"Tell me, what is your ultimate fantasy as a woman? I want to have some fun! Tell me what your imagination craves."

Brent paused for a moment to consider.

"I guess it would be a lesbian fantasy" he said. "Something like this. I'm a woman, going to a salon to get my makeup done. My makeup artist, who is a real hottie, keeps complimenting me as she does my face. She's real close to me, her boobs almost touching me, as she works on the last details. She says I look so irresistible that she *has* to have me, even though she's never been with a woman before."

"Then we kiss, touch each other all over, and start to undress. I go down on her, and make her come again and again. She tells me how much my pussy is turning on her on, and she goes down on me, while massaging my boobs. I came again and again. That would be my fantasy."

"Lets make it happen" said Sheila. "Go take off your makeup, and come up to the bedroom. I'll be the makeup artist. What's my name going to be?"

"Kristi" said Brent.

"And are you okay with Brenda? I never asked before."

"Yes, that's fine. I'm glad you picked out such a nice name for me."

"Wonderful. See you in a few minutes, Brenda."

Brent went to the rest room, and used the makeup remover with some cotton cleaning pads. Then he washed his face, which now seemed so dull, since it was devoid of any makeup. He dried himself off, using a patting motion as Sheila had taught, instead of wiping as he used to do. He had to keep his skin looking smooth and wrinkle free now!

He went upstairs, where he found Sheila all ready for him. She motioned to the chair in front of the lighted makeup mirror, and asked him to sit down.

"Hello" she said. "I'm Kristi, and I'll be your makeup artist for today. Won't you have a seat, Ma'am?"

"You can call me Brenda" he replied.

"That's a lovely name" said Sheila. "What can I do for you today, Brenda?"

"The works. Make me look beautiful."

"As you wish" said Sheila, as she got started.

Sheila did Brent's makeup, going for a glamorous look this time, as opposed to the everyday makeup job she had helped him with that morning. She chatted as if he was a woman, asking if he had children, sisters, and so on. Sheila made lots of small talk as the applied all of the powders, pencils, sticks and such to his face.

When she was done, Brent decided that it was the best he'd ever looked in makeup, even better than when he was a bride the other night. Sheila hovered over him, and he could see right down her shirt that she wasn't wearing a bra!

"You're so delicious, that I want to kiss you" cooed Sheila in a low tone of voice.

Brent moved his lips closer to her. Suddenly, they kissed. And then they proceeded step-by-step, exactly according to the script which Brent had laid out. As he went down on her, he imagined that he too had a pussy. He imagined that when she did him in a few minutes, it would be her sucking on his clit. He touched her breasts, and imagined that his were *real*.

And so by the time that it was her turn, he was so aroused that it didn't take much at all to make him come. Sheila smiled and licked her lips once she was done, then stood up over him to kiss again. Her hands were all over his large fake boobs. As she put her tongue into his mouth, he could taste something strange and foreign. He wondered if he was tasting his own come. It didn't matter though, he felt like such a woman at that moment, he ignored it, and just enjoyed the kiss and all of the attention from his wife.

* * *

Going to work on Monday as just a plain man felt dull to Brent by comparison, after his wonderful weekend as a woman. But he could hardly go into the office, and tell everybody that he was 'Brenda' now! Now, he needed to work, so that meant he needed to be a man again. Just thinking of the fun they had over the weekend made the work day crawl by so slowly!

That night, Sheila said nothing about him being Brenda, and he didn't want to push it, so he just went through the whole day as himself. She *had* said a few days a month, after all. And she had just allowed him to name his own fantasy, and live it out. He of course was very willing to help clean up after dinner, and share with the "woman's work" of the house!

 

The entire week went by like that, crawling along, dull and gray. Brent could not wait until the weekend, so he could once again bring out the woman inside of him. Now that he had been able to so fully express his feminine side, life seemed empty without it.

* * *

On Friday morning, Sheila hinted that they would do something that night. When he got up to take his shower for work, the bottle of Nair was sitting there at the door, where he would be sure to see it. He gladly put the smelly cream all over, and let it set in, before he jumped in the shower and rinsed off whatever hair had tried to grow during the past week. He loved how it felt to be smooth all over!

Work went by even slower still, except for one bright spot when Sheila called.

"Hello Brenda, its Sheldon" she said. "I've been thinking of you all day."

"The same with me" he said. "I can't wait to see you tonight."

"You know how last time we did *your* fantasy?"

"Yes" he said.

"Tonight, its my turn. We'll do what *I* have been dreaming of."

"That seems fair" he replied, as his mind started to spin. He wondered what sort of wonderful thing she might want to do!

Brent could not take his eyes off the clock. When at last it was 5:15 and he could leave for the day, he was *so* excited! He practically ran to his car, and drove home as fast as he could. He dashed into the house, where he found a note sitting at the table.

Brenda,

Go to your room, and put on the outfit I have selected for you. Then meet me in my room - Sheldon.

 

The guest bedroom had become "Brenda's room", with "her" things being stored there now. He wondered what kind of outfit she might have picked out for him. Something they already bought? Or something new? He was excited to find out. He went up the stairs, and walked into his room. Everything was all laid out for him nicely.

First, he put on the red lacy bra, with scalloped edges. He put in his breast forms, and it looked so wonderful there on his chest! There were no panties, but there was a pair of dark stockings with wide elastic at the top, so they didn't need a garter belt! He put those on, and moved on to the next item, which was a waist cincher. It was quite tight, and difficult to close around him, but it did flatten his tummy, and make it look a little bit as if he had curves.

Then he put on the skirt, which was very short. It was hot pink, with two layers of white lace hanging below the hemline, as if he had a slip on underneath, and it was showing. It was quite exciting to wear, and it didn't even cover the top of the stockings. The last item was a pink cami top, with lacy trim across the bottom of the v in the neck. It featured an embroidered floral pattern, and it fit quite tight, making his fake boobs really stand out. The straps were so thin that they couldn't even hide the bra straps.

Brent did his makeup, put on his jewelry and his wig, followed by a new pair of six inch spike heel shoes! They had a pointy toe, and they looked so exciting. He had never worn a shoe with that tall of a heel! He loved how he looked, although he thought it was a bit of a clash to have on an outfit that was almost like a younger girl would wear, but with the heels and stockings. Oh well, it was Sheila's fantasy. Whatever she wanted, she would get.

He put on the long red "press on" nails that he found on this makeup stand, and marveled at how his hands looked with long red nails, perfectly shaped into ovals. He looked in the mirror, and felt so feminine. Just one thing bothered him: without any panties, there was nothing to hold his penis in place. It was really hard now, and it made the skirt stand out in the front, where it poked out from him.

He took tight little steps towards their bedroom now, and knocked on the door.

"Come in, Brenda" said Sheila's voice.

Brent entered the room, wondering what would come next. The lights were very dim, with only one small candle burning, and he couldn't see more than just the outline of Sheila, over by the far wall.

"I told you how I loved to dress up as a boy when I was younger" she said.

"Yes" he replied. Just like how he liked to dress as a girl.

"And tonight is *my* fantasy night" she added. "You agreed."

"Yes" he said. "I'll do whatever *you* want."

"Excellent. I'm glad you understand. Now listen carefully. This is *my* fantasy, and this is exactly what I want for you to do."

Brent nodded, ready to listen. As Sheila started talking, he was shocked at what she was asking of him. But he couldn't say no to her, she had been so kind to him, and had done so much for him. As disgusted as he was, Brent was going to have to go along with her scenario, as much as it sickened him. He was trembling a little, not sure how he was going to endure this experience.

She turned up the lights a little, and it was time to start. When he caught sight of her, he gasped. She was standing there, wearing a man's suit and tie. She even had on wing tip shoes. She must have been wearing some sort of padding, to make her look like she had a masculine silhouette. But that wasn't the shocking part.

It was her hair. It was almost all gone! She had cut her hair very, very short. It was neatly parted to the side, and her face looked so boyish! She had one some makeup including around her eyes on darkened lips, but that just made her look even more androgynous somehow. Now Brent had to go along with her scenario. It started with her *forcing* her husband to dress up as a w for the first time. He had to act as if she had just *made* him dress that way, under threat.

"You are Brenda now" she said. "You are a woman."

She took a picture of him with a digital camera.

"If you don't do exactly as I say, this picture will show up on your boss's desk tomorrow. And your brother's email. And your parents too. Along with the dozens of others I took with the hidden camera as you dressed up. If you don't obey completely, I will ruin your life. You're my slve now Brenda. Get down on your knees."

Brent lowered himself. He didn't like this at all. Being a woman didn't make you weak! But it was her fantasy, and he had to do what she wanted.

"I will do whatever you tell me" he said, playing along.

"Good, slve" she spat, as she reached into her pants pocket. She pulled out a large, realistic looking dildo. It had a bulging vein in it, and everything.

"Show me how weak you are" she said. "Show me that you're not a man anymore. Suck this for me."

Brent took it from her, and reluctantly started to slide it into his mouth. How could she want for him to do this?

"Look at you, all pathetic and weak" she said. "You're sucking on a dick now! That's right honey. A dick. You are so weak."

She took a picture of Brent, as he continued to suck.

"That will be quite an addition to my library. I think I'll send *that* one out first, if you ever disobey me in any way. You're going to learn that *I* am the man of the house now. That's right. I'm no longer a woman. I've become a *male*. I've been taking male hormones for weeks now, and you didn't even know. I'm going to go get my breasts removed, so when I start pumping iron, I'll have a nice masculine chest. But meanwhile, the female hormones I've had *you* taking will start help you to grow a *real* pair of boobs on your chest. That's right dear, you're getting *real* boobs. Soon, you won't be able to hide them. They're going to be nice and full and firm, right there on your chest. Soon, you're going to *need* a bra all of the time. I'm becoming a real man, and I'm turning *you* into a woman."

Brent felt quite conflicted as Sheila said all of this. Sucking on the dildo sickened him, as did the thought of her destroying her natural beauty, and masculinizing herself. He had no idea her fantasy ran this strong! He didn't mind her telling him that she was going to turn him into a real woman. In a way, it was arousing to hear. But her becoming a man? That was something he certainly didn't want!

"Now admit to me that you like sucking dick" said Sheila suddenly. "Admit to me that you like man."

Brent hesitated for a moment. He would never do that! That wasn't how he felt. But he *was* role-playing right now. So he did as she wanted. With some well-acted (he thought) hesitation in his voice, he said "I admit it. I like men. I like sucking dick."

"Good" said Sheila. "Because now you're going to suck mine."

 

She unzipped her pants, and reached inside. She worked something through the fly of her boxers, and out through the fly of the pants. It was enormous, even larger than what Brent had just been sucking on. Another dildo. But this one was somehow strapped onto her, so that it looked like she had a penis! A huge one, fully erect, and pointing right at him.

"Suck my dick, baby" she said, as she took a step towards him.

Reluctantly, Brent opened his mouth and reached up with his hands to guide it in.

"Don't close your eyes" she ordered. "Look at my dick as you suck on it. You can't even get all of it into your mouth, can you? But I can tell you enjoy sucking on it. Suck me harder baby. Make me cm in your mouth."

That really turned Brent's stomach! But he kept on sucking, as she wanted.

"Moan for me baby" said Sheila. "Let me know how much you enjoy this."

"Mmmm" said Brent, who then made some moaning noises as he continued to suck.

"I can tell you really like dick" she said. "I can tell how enthusiastically you're sucking on my penis. Mmm, that feels so good. Now stand up, so I can make a *real* woman out of you."

Brent stood up, and Sheila pushed him hard onto the bed, face first. She lifted up his skirt in back, and he felt her hand smear some sort of cold gel back there. She was going to put it into him now! And he had to take it, because it was what she wanted!

"Put this on" she ordered, handing him a condom "I don't want you messing up my bed.".

He quickly slipped it on.

As soon as it was on, she pushed him over again, and a moment later, he felt her exploring him from behind with the tip of her strap-on. She found his opening, and she gently pushed it forward into him.

"Relax your muscles" she said. "It will only hurt if I'm I have to force it in. Relax, and let my dick up into you. That's it baby. You're a woman now, so this should come natural to you. This first time is the hardest. Next time, I'll go in much easier. Soon, I won't even need to lubricate you. You'll become so nice and receptive. All of the boys will love fucking you."

Brent did *not* like how that sounded!

"Tell me you love to feel a dick up inside of you" ordered Sheila.

"I love feeling your dick up inside me" said Brent.

"Tell me again that you desire only men."

"I only desire men" he replied.

"Tell me that I'm your man, and you're a woman now!"

"I'm a woman now, and you're my man" he echoed.

"You're going to be a woman forever now. You're never going back to manhood. That part of your life is over. From now on, you're only going to be allowed to be a woman."

She reached around him, and started to rub his penis, encased in the condom. As she thrust into him, he couldn't help it as his sexual tension built and built, until he exploded in ecstasy, into the condom. Sheila kept pumping him, until he screamed out. Finally, she withdrew. She reached around him, and removed his condom. Then she walked over to the table, where another dildo was waiting. She fiddled with something he couldn't see, then she returned back to him.

"Suck on this" she said.

Obediently, he put it in his mouth. He could see her standing over him, her huge strap-on pointing right at him as he sucked. Suddenly, he tasted something. The same taste as the one kiss from the week before, after she had gone down on him. He was sucking in his own come! It was gross, and his face wrinkled in disgust.

"Ah, you can taste your come" she said. "Good. I hope you like the taste. I'm going to teach you how to really please men. When I have them over here, you will suck them, just as you did me. Some will want to come in your mouth. Some might want to take you from behind. Either way, the boys will really like a nice compliant girl like you."

After Brent had sucked all of the white sticky fluid out of the dildo, Sheila laughed.

"Oh, I forgot to tell you. A few hours ago, I had a man over here. A *real* man. I let him come in my pussy. You just sucked out *his* come. I threw yours in the trash. You've just sucked what he left inside my pussy. Until I become fully male, only *he* will be allowed into my pussy. He might want to come inside of *you* too, so you need to be prepared to please him."

Brent was just in shock. Sheila's fantasies were so extreme! How could she have hidden all of this from him? He watched amazed as she removed her business suit, to reveal that underneath she was wearing a leather outfit, like a domme. She replaced her wing tips with boots that included five inch heels. She opened a drawer, and removed a whip.

"On the dresser are pills for you to take. female hormones. From the moment you take the first one, the feminization of your body will commence fully. There is also another pill. A testosterone blocker, that will stop all effects of male hormones on you. Take that one too, so that your feminization can go faster. You will be a woman forever, from this day forward."

Brent took the two pills, and swallowed them. Then he got on his knees as she had wanted, and kissed her boots.

"I am all yours" he said. "I am your slve."

 

There. That was everything that she had asked him to do. Now this terrible fantasy of hers was all over. She seemed so into it! She was almost acting as if this was real. He felt nervous for a moment. What if this wasn't a game for her? What if this was what she really wanted! He gasped. What had he done! She was seeing another man now! He had just lost his wife! Tears started to well up in his eyes.

Suddenly, Sheila's whole demeanor changed.

"Don't cry, its just a fantasy, a game!" she said, as she sat down next to him.

"You talked about another man...."

"It was just part of the game honey. It's not true. I wouldn't want to be with anyone but you."

She took a handkerchief from the night stand, and patted his eyes with it.

"Don't cry, you'll ruin your pretty makeup."

"Why did you have to do that to me?"

"It was always my fantasy to be the man. I always dreamed of taking a man, and turning him into the woman. Men have this strange thing about their women, where they view them as almost property. In order to strip away any male feelings you were harboring, I needed to make you feel like you had completely lost control of me, and that I was no longer yours. It was meant to crush the man inside of you."

"It was certainly effective. This was so extreme..." he said.

"I know. I'll never go this far again. This was my one and only time to get that out of my system. Yes, I'm going to want to be a man sometimes, just as you want to be a woman. Yes, I'm going to wear a strap-on, and I'm going to want to have you suck me, or for me to put it up into you. But I will never again treat you like that. I want to be a loving man for you. I'm sorry. I didn't mean to hurt you like that."

Brent wondered how the thought of Sheila fucking him with a strap-on in a loving way, suddenly sounded appealing to him. He never would have believed he would ever feel that!

"You cut your hair..." he said.

"Yes. I had always wanted to see what it felt like. It will grow back. I was thinking that you should let yours grow out though, so you won't need that wig anymore. I'd love to see your hair looking long, pretty and feminine."

"What about work?" said Brent.

"You can get another job. One where they don't know you're a man. We can change your legal name, you know. We can let you live your entire life as a woman. We'll be together always, two women completely in love. Just that sometimes I'll be the man for the night. But you know me. I want to look pretty. I'm too much of a girl inside to go through with it, like in the fantasy tonight."

"But you want me to be a full time woman?" asked Brent, stunned.

"Yes, I do. I like you better that way. In fact, I'd love it if you ever did decide to go on female hormones, so you can *really* begin a feminization process. That part of my fantasy was very much true. The more female you get, the more it makes me feel like I'm your man. I would love to see you with real boobs on your chest. I would love to see you become more and more feminine, until you're more a girl than I am. What do you say? Do you want to become Brenda full time? Or should we forget all of this, so you can go back to being a man."

Brent's mind flashed with the images of himself at work all week, feeling so trapped in the dull existence of a man. Or the wonderful feelings he had as a woman (except when Sheila had gone too far in her fantasy). There was no choice, really.

"I will become a woman, for you" he said.

"I'm so glad" replied Sheila. "I know a doctor we can go see tomorrow, to get you started. You're going to become a *real* woman now! I'm so happy for you. We are going to be so happy together."

Brent put his arms around Sheila. He could feel her strap-on poking into him.

"You're getting me all hard" she said.

Brent reached down, and began to stroke her there. He noticed there was a hold below it, allowing access to her pussy. He buried his head down there, and started licking, even as his hand continued to jerk off her huge fake penis.

"Oh, you're making me feel like a man!" she said, as he jerked harder and harder, licking her clit more and more.

Before the night was over, both of them made each other come, and they fell asleep together, he in his skirt, and she still wearing her strap-on. From that day on, their lives were never the same.....

 

 

  

  

  

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