Gail Force

by Jennifer White

 

Brain re-added the numbers in his cheque book again. He sighed. He would barely make rent for his apartment this month, but how was he going to eat? By the time he paid all of his bills, there wasn't much left. If he couldn't afford his meals, he certainly wasn't going to be able to afford going out and having any sort of fun.

He couldn't just tag along with friends, then not eat dinner or not drink. He wouldn't be able to afford the cover charge at the hot nightclubs. And what if he met a pretty girl? He couldn't' afford a drink for himself, let alone have the money to buy her one. He felt desperate now. No social life for him!

As much as he enjoyed being out on his own, he knew he could never move back in with his folks. He had ignored their pleas for him to go to college. Now he was stuck with a job that wasn't all that great, and didn't pay as well as he would like. It had seemed like lots of money at the time, but now, looking back, it was all a mistake.

But if he did move back home, he'd never hear the end of it. So he needed to do something else. But the job market was very tight, and it would be very difficult to find another job that paid even what this one did. He felt trapped in it. He was too tired after working long hours of physical labor every day, so a second job was out of the question too.

But then, he had an idea: what if he got a roommate? He could let someone else stay with him, and sleep in the second bedroom. He could charge them rent, and with the extra money, he'd be back on his feet! He'd be able to afford all the things he needed and wanted. His life would be good again.

Immediately, he rang the local newspaper, and placed an advert, looking for a roommate.

 

* * *

 

The first couple of people to respond to Brian's ad, didn't turn out to be so good. One was a couple with two young children - not what he was looking to live with! The next one had a dog, but no pets were allowed in his apartment. The third one was really creepy, looking like he might be into drugs or worse. Brian wanted no part of that!

As person after person answered his advert, his disappointment grew. He was about to give up completely, when he got one more call. It was from a woman, named Gail. He agreed to meet her at the coffee house across the street from where he lived.

As he sat at the table waiting for her, he pictured her as being a loser too. Probably obese, or some strange defect making her as undesirable as the others. But what if she wasn't? It would be exciting to live with a girl, since he was in the market for one! But he didn't dare get his hopes up.

He looked up to see a woman enter through the doorway, and his heart almost stopped. She was tall and thin, with long full jet black hair. Her face was gorgeous, with lots of makeup, in just the right places. She was wearing tight blue jeans, high heel shoes, along with a pink and white corset, that showed off her impressive breasts and her deep cleavage. She walked right up to his table, taking small tight steps, swinging her hips as she moved.

"Hello" she said, recognizing the bright red shirt he told her he'd be wearing. "I'm Gail. Nice to meet you."

"Brian" he said, extending a hand. He was barely able to get the word out of his mouth, he was so taken with her!

"So" she said. "What do you want to know about me?"

"Everything!" he thought, but didn't dare say.

"I just wanted to talk for a while, to see if we might be, um, compatible as roommates."

"Oh I think we'll be very compatible, don't you?" said Gail, batting her eyelashes.

"Um... yes!" said Brain. "When can you move in?"

"How about now?" she said. "I have several boxes in my car out there on the street. Would you be a dear and carry them up to the apartment for me?"

"Certainly!" he said.

It didn't even bother him that she was sitting there, sipping espresso, as he did all the hard work, lugging up box after box from her car. He had a roommate now, and she was hot! It didn't even occur to him how easily she had already manipulated him. He was already putty around her finger, already falling in love with her.

 

* * *

 

Brain arrived back home after work. He was amazed when he walked through the door. He could smell cleaning solution. Everything looked brighter.

"How do you like the new curtains?" said Gail.

"They're wonderful! But you didn't have to buy new ones."

"Those old ones were dirty and dingy. I couldn't wash all the grime off of them. The last resident here must have been a smoker. So I bought new ones."

"They're kind of pink, aren't they?" asked Brain, unsure if he liked them.

"My favorite color" replied Gail. "Plus, they'll go with the decor, once I get my lamps and my couches out of storage. Yours are all old and falling apart. You wouldn't mind me having them here would you?"

She smiled, and batted her eyes at him. How could he tell her no? His stuff was old and ratty.

Gail turned in a flash of skirts, and then looked back over her shoulder to smile at him again. That move really got to him! More and more, he was sure that she liked him. And he was head over heels in love with her. Already, she had allowed him to see her going around the house in her casual clothes. He had even gotten a glimpse of her walking from the bathroom to the bedroom, wearing just her nightie.

The day that she had walked out of the shower with just a towel wrapped around her (and one wrapped around her head, to dry her hair) was also exciting for him. Just one garment standing between his eyes, and her perfect body. He hoped that soon he'd be able to see all of her.

Gail was so kind. She kept cleaning up the place, making it look nicer. She was considerate to Brain. For example, one day she talked with him, making an offer.

"I know how it feels to be hard up for cash" she said. "And I know that you work hard, but you're struggling. Listen. Why don't you save some money, by just using my shampoo and conditioner, instead of buying your own? And there really isn't room for two bars of soap. So just use mine. That will save you a little bit here, and a little bit there."

"Wow, thanks" said Brian.

It did bother him a little that her shampoo smelled like strawberries, and her soap smelled like roses. But it was free, so who was he to complain?

 

* * *

 

Brain helped Gail move her furniture into the livingroom, after he hauled his old things to the trash. They were all secondhand or worse, and it was time to let them go. Gail's things were much nicer, and with the pictures she brought in that he hung up for her, it did give the place a sense of decor. It did bother him a little that all of her things were kind of "girlie", but he wasn't in a position to argue. Plus, if it kept her happy, then he was happy!

Now there were fresh cut flowers around the house all the time, scented candles burning, or the smell of perfume in the air from her bedroom. Much better than the scent of stale beer that used to permeate the air! Everything looked so much brighter, and more cheerful. She did a marvelous job with all the chores.

But one day, the dishes were piled up in the sink. Gail pointed to them.

"I just got my nails done today" she said. "Would you be a dear and do the dishes for me?"

"Not a problem" said Brian.

Gail had been cooking for them, to save on expenses, so that he didn't have to eat out as often. He loved seeing her work around the kitchen wearing her pink and white apron with the frilly edges. That really turned him on for some reason. She always wore something sexy and exciting, it seemed like!

"You know" said Gail, "It would seem to be fair if we started to split the chores around here. I've been doing so much, but I would think that we both should contribute. Does that seem fair to you?"

"Of course" said Brian, who had been skating by without doing housework for a month since she moved in.

"I'm glad we see eye to eye" she said, her face glowing with a smile. "Why don't you take over the dishes, vacuuming, and the dusting? Oh, and you can clean the bathroom, doing the tub and the toilet. I always hated that job."

"Sure" he said, eager to please her.

"Now let me show you how to do the windows properly" said Gail. "There were lots of steaks in them when I moved in. I'll show you how to make them look nice."

Doing the windows hadn't been on the list, but Brian wasn't about to argue. Now with her standing so close to him, showing him what to do. She even touched her hand with hers, and guided it along, sending chills up and down his spine.

 

* * *

 

As the days went by, it seemed to Brian like he was starting to do more and more of the housework. Like one day when she asked him if he would "be a dear" and take out the trash for her. He was glad to do it, because it pleased her so much. When he'd do something like that for her, she would give him a hug now, or a pat on the rear.

But somehow, once he did a chore for her, it became his. He hadn't even really noticed, as he gradually started to take over all of the chores in the house. But he had a hard time saying 'no' to Gail! He wanted to please her, and stay in her good graces.

One day, Gail came back from the Laundromat with two baskets full of clothes.

"I'm in a bit of a rush" she said. "Would you mind helping me fold them and put them away?"

"Sure" said Brian.

He folded his boxers, and put them in a pile. He sorted his socks, and paired them up. Then he folded his undershirts. But now, there were all of her things. He felt a rush of blood to the head as he handled her panties for the first time, carefully folding them with his trembling hand.

He picked up one of her bras, and he could only stare at it. This was the thing that wrapped around those perfect breasts of hers! He was kind of freaked out to handle it.

"They're just clothes" said Gail.

"I know, but..." stammered Brian.

 

Gail sighed.

"Here" she said. "Let me help you."

Brian expected her to fold the bra for him. But instead, she reached down, and pulled off his T-shirt!

"What are you doing?" he said, as she started to guide his arms through the loops of the straps, and then pull it around him. He went in a moment from thinking she wanted him, to having her put a bra on him!

"I'm teaching you that they're just clothes" she said, as she gave him a soft kiss on the cheek, while she adjusted the straps over his shoulders. "I want you to be comfortable when you have to touch my frilly lacy things. And there is no better way for you to learn than this."

She pulled his T-shirt back on. She was standing to close to him! He could feel the heat from her body, and occasionally, the tips of her boobs brushed against him, sending chills up and down his spine.

"Its such a turn-on to finally have found the gentle man I've always looked for" she said now. "One who is confident enough in himself to let me put a bra on him, and not freak out about it. A guy like that could go a long way with me."

She put her hand on his back, right where the bra connected, and she kissed him now. Not the peck on the cheek that she gave him before, but a real kiss. A deep kiss, sensuous and emotional, with all her heart. Brian got hard as a rock from it, and his heart raced.

Gail let go, then walked slowly out of the room. She turned to blow him a kiss, as she looked back over her shoulder. Brian was stunned. He continued to fold and sort her clothes, his hands trembling. She had kissed him!

In fact, as he worked, she walked back into the room at one point. She put her hand on his back again, and once more, they shared a deep kiss. Brian was floating, as he savored her touch. He started to put the clothes away, with her showing him where things went in the different drawers in her room. He had never been in her room since she moved in. Now she was kissing him, and showing him where she kept her intimate things!

As Brian prepared to go put his things away, Gail once more touched him on the back, then kissed him deeply. When it was finally time for him to go, she whispered in his ear.

"When you go to bed tonight, put the bra in with your clothes. That will always remind you that it is just a piece of underwear. Nothing to freak out about. Right?"

"Right" he said, as she let his hand go, and he left her room, feeling on top of the world.

 

* * *

 

The next day, Brian was doing the dishes, when Gail walked by. She put her hand on his back, and he melted, waiting for her kiss. But she let her hand go, shrugged her shoulders, and walked off. He was confused. She had kissed him yesterday, why not today?

And the day after that, when he was vacuuming the rug in the livingroom, she again walked by, and put her hand on his back. She moved it up and down once, but then walked off, again shrugging her shoulders.

"What's wrong?" asked Brian, upset that he wasn't getting her kiss again.

"It's just clothes" she said quietly, walking off.

Brian froze. She meant the bra! She was looking for the bra under his shirt, and since he didn't have it on, he wasn't getting her kisses. She wanted him in a bra! She wanted him to wear it when he did housework! He was upset and confused. How could she want him to wear it?

But on the other hand, she had said that she wanted him to learn that it was "just clothes". Was she going to go that far to teach him a lesson? But then there was the important factor of getting her kiss. He decided that he'd do whatever it took to be intimate with her. Even if that mean wearing her bra when he did the housework.

So he stopped, when into the bedroom, took off his shirt, and put the bra on himself for the first time. He had to struggle a few times to get it closed right. The first time he got one of the little hooks into the loop on the other side, it was in the wrong one. But eventually, he got all three of them hooked up correctly.

He returned to the housework. Sure enough, when Gail walked by, she put her hand on his back. Now she felt something there under his shirt. She smiled, then put her arm around him, and rewarded him with a deep kiss. Her body was pressed up against his, and he got fully aroused, right away.

"You don't know how much that turns me on" she whispered into his ear, as she rubbed her hand along the strap across his back. "The fact that you'd wear that for me really tells me how much you care. I like that."

They kissed again, and she ran her hands all over him. Brian had to close his eyes, as he felt the pleasure course through him. She liked him! She wanted him! He vowed to always put her bra on when he did housework for her, if that was what it took to win her heart.

 

* * *

 

It had been about a week after Brian started to always wear the bra when he did housework. Each time, Gail had touched his back to make sure he had it on, then she had kissed him. With this positive reinforcement, he now thought nothing of wearing it around the house; it was just a piece of clothes, as Gail had said.

So it wasn't a total shock when came home one day to find that there was another bra laid out on his bed for him. It was brand new. It was pink, frilly, and very padded. But that wasn't the shocking part; laid out below the bra was a pair of matching panties, with the same color and the same frilly pattern.

Alongside the matched set was a note on scented paper. In a neat feminine script, it read: "For you my sweet. You know how I am so big on being neat and organized. It just seemed so wrong to match your boxers with a bra. Now you will match better, and I'll feel better about you. Love, Gail."

Love? Sweet? She'd feel better about him? While the thought of putting on panties was quite daunting, Brian was exploding inside with the possibilities of the pleasure he'd feel with Gail, if they truly did hook up. Seeing her every day going around in her skimpy clothes just made him want her more; he had to have her! She was offering him a chance to get closer to her. He knew this was a test. And he knew that he was going to do it, because nothing was going to stop him or get in his way. Not male pride, not anything.

He put on both the new bra and the panties, then put his own clothes back on. To his horror, you could see the bra a bit through his shirt, because the padding made it look like he had little boobs of his own, and the lacy pattern on the front showed right through his shirt.

But nobody would see him, other than Gail. And it would be a good thing if she saw him like that. Then she'd know, without having to touch his shirt to check on him. The panties felt strange. They were so soft compared to his boxers, and so snug. And then there was the lack of a fly in the front. They didn't feel bad, but they didn't feel right either. It was so strange knowing that he was wearing a full set of underwear meant for a girl.

He looked at the list of chores that she had written out for him for the day. First up was dusting the shelves in her room, followed by cleaning a couple pairs of her shoes. Then the dishes. Lastly, he was to cut up the veggies for the salad they'd share for dinner. He had a lot of work to do, so he went right to it.

Brian was in the kitchen, chopping up the celery, when Gail came home, loaded with shopping bags. She put the bags down, and came over to greet him. She put her arms around him, her hands running up and down the straps going over his shoulder. She gave him a big kiss, then she whispered into his ear.

"Are you wearing the full set?" she asked.

"Yes" whispered Brian, nodding.

"Show me" she said.

 

Brian undid his belt, the unbuckled the top of his jeans. He unzipped the fly a little, revealing the lacy pink pattern of the fabric hiding beneath. Gail smiled, and put her hand down there, touching him, making him get as hard as a rock.

"I just knew that you'd do it for me" she said breathlessly. "I had a feeling that you might be the one."

The one? Him? She wrapped her arms around him, and rewarded him with another deep kiss. As they embraced, her hands were all over him. They ended up on his chest, her thumbs massaging his nipples through the padding of the bra. Somehow, it was such a turn-on! No woman had ever touched him in that way.

"Time to get back to work" said Gail, sounding disappointed that she had to pull away from him. "I've got a chore to do too. Then we can have dinner together."

Brian went back to work on the celery, as Gail picked up the shopping bags, and headed off towards her bedroom.

 

* * *

 

The next morning, Brian took a shower. But first, he had to take care of himself. He felt so much pent up arousal from being with Gail so much, he had to get a release. And so, he did it himself. Then he showered. He wrapped himself in a towel, and whistled as he walked into his bedroom.

He opened up his dresser drawer, and he was literally shocked by what he found: instead of his usual jumble of boxers and socks, his dresser drawers were neatly organized now. But his boxers were nowhere to be seen. Instead, the neatly piled underwear all panties. All of them! And on the right was a stack of neatly folded bras!

Brain just stared. Gail had replaced all of his undies with new ones. Female versions of what he normally wore. She wanted him in panties full time! He literally had no choice now, but to put them on. He had nothing else. Every pair she had purchased was frilly, lacy, pink and pretty. Some were thong style, and so tiny that they would barely cover anything at all! Brian's mind raced as he picked out a pair, and put them on.

He was totally into her, and wanted to be a couple with her so much. But did he really have to do this? Why would she want him to wear panties every day? It was strange, but she was so hot, and he was so in lust with her, that he did what she wanted.

He looked up, startled to see that Gail had walked into the room.

"Do you like your gift?" she asked.

"I don't quite know what to say" he responded.

"I was so overjoyed that you were willing to dress so nicely for me" said Gail, "I just wanted to reward you. I love the thought that you're wearing such sexy underwear all the time. It drives me wild, and makes me think about you all day long at work."

Brian was again stunned. He really didn't know what to say! He just stood there, as Gail closed in, put her arms around him, and gave him a deep kiss. Soon, her tongue was inside his mouth, exploring. By the time she let go, Brian was so revved up, that it wasn't going to be a question anymore about if he was going to wear panties every day. If they drove her that wild, he would do it, for sure.

 

* * *

 

Brian was so happy with how things were going. He and Gail kissed all the time now, or held each other. She was letting him touch her now, in special places. She would massage his nipples, as she let his hands start to explore her body. Today, they were sitting together on the her couch, which she brought there to replace his. It was pink and white striped, with a set of rose embroidered pillows, with lacy edges sitting there for decoration.

Brian had hardly noticed, as she had gradually moved more and more or her things into the apartment. In fact, if a guest were to stop by for the first time now, they would undoubtedly come away with the impression that it was a woman who lived there.

But this didn't bother Brian, he was too excited about being with Gail. They went to the movies one night, and walked hand in hand down the street. All of the guys started at him, jealous that he had landed such a catch. And now, she wanted to meet him for lunch, so they wouldn't have to be apart all day long! Brian was floating, as he walked into the bistro, waiting for her.

Gail showed up a few minutes late, shopping bags in her hand, as usual. She told Brian to look in one of the boxes inside, because she had just bought something for him. He looked inside the box, and seemed puzzled. There was a shirt, but it wasn't the type he normally wore. It had long sleeves, which seemed very large, like they'd fit loosely. The cuffs were rather ornate, as was the little collar, which was just in the front. The buttons seemed rather large too, and the area around them was almost frilly.

"I don't know" he said, looking at it. "This looks more like a blouse than a shirt."

"That's because it is a blouse" said Gail.

"And you want me to wear this?"

"Yes" she said. "Just when you do housework. Notice how sheer it is! I'll be able to see right through it, so I can be sure that you've got on your special things. Now look in the next box."

In the next box, there was a pair of pants. But not like any pants that he owned! The bottoms of the legs flared out so wide! And they seemed so narrow up at the very top. They had a very wide belt with them, which was leather, with a fringe, and a large buckle in the front. As he stared at them, he realized that they were women's pants.

"They'll be so tight on your cute little butt, that I'll see your pantyline right through them!" said Gail.

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

"You're really hurt my feelings if you didn't wear them for me" said Gail, sounding hurt. "I spent a lot of time and effort to pick out a nice outfit for you, and this is how you thank me?"

"It's not that!" said Brian. "Its just that these are... rather feminine."

Gail looked at him and sighed.

"They're just clothes" she said. "Or would you prefer it if I had bought a skirt for you?"

"Okay" said Brian, giving in. "I'll try them on when I get home from work."

"And you'll be wearing them when I get home?" said Gail, her voice perking up.

"Yes..." said Brian, sounding defeated.

"Mmmm. I'll be thinking of you all day now. Thinking of you wearing your new outfit, and how you'll look in it when I return home. I don't know if I can resist you much longer."

She licked her lips, as she looked at him with mischief in her eyes. Needless to say, Brian was now fully aroused, and there was no way that he'd dare not wear his new outfit.

He and Gail talked as they ate their lunch. But suddenly, Brian looked at his watch, and stood up.

"Oh no, I'm going to be late!" he said. "My boss warned me that I've been late a couple of times already, and he'll be watching me closely."

"You'd better get going then" said Gail.

Brian hurried off, thinking of why he had been late so much lately. Usually, it had something to do with Gail. He might be on his way out the door for work, when she'd ask him to carry something upstairs for her. Or she might have an emergency, and ask him to be a dear and run to the corner store to buy something she needed. He always did as she asked. And as a result, he had been late for work several times. Now he was on thin ice.

His boss was quite angry with him, and gave him a stern warning. Brian felt lucky that he hadn't been fired. He was going to have to be more careful, so he didn't lose his job! With the local economy, if he lost that job, it would be almost impossible to find another one that paid as well. If he could find one at all, that is.

When Brian got home from work, he undressed, and put on the new outfit that Gail had bought him. The pants seemed so strange, the way they were cut. They were wide enough at the hips to be comfortable, but they got quite narrow up at the top, making it hard for him to even get into them.

The wide belt felt strange, as did the fringe on it. The way the pants flared out at the bottom too was foreign to him. He didn't like it at all. Nor did he like the top, which seemed to be too frilly. He also didn't like how short it was; it barely came down to his belt line. He couldn't tuck it in, as he did his own shirts.

And when he looked in the mirror, he could see his bra right through it! The material was white, but sheer, and there could be no doubt to anyone looking at him, that he was wearing a bra. He thought that the whole outfit made him look like some kind of sissy or something. He sighed. If that was what Gail wanted...

He found the list of chores, and went right to work. Half an hour later, Gail came home. She seemed overjoyed to see him dressed like that, and she pulled him away from the ledge he was dusting, and she pulled him into her bedroom! They made out for quite some time, when Gail handed him a condom, and told him to put it on! He was of course completely hard by then, so he easily slipped it onto himself.

"Now put your panties back on" she said, which he did, not understanding why. She continued to kiss him, and started to massage his nipples, right through his blouse and bra. Then one of her hands moved down, and touched him between the legs. She started rubbing there, as she moved her mouth down, and started to nuzzle him on the neck.

"Do you want to be mine?" she said.

"Oh yes" replied Brian.

"Even if that means wearing the clothes I pick out for you?"

"Yes" he said, not wanting her to stop what she was doing to him down below.

"Mmmm. You are the one" she said, as she squeezed him so tight that he exploded inside his condom. That kept his panties from getting all sticky, keeping him clean. Gail told him that in time, they'd go further.

"Bit by bit, we'll move forward together. I want it to be really special when we go all the way. Don't you?"

"Yes" said Brian, overjoyed at the thought of getting even closer to her!

 

* * *

 

The next day, when Brian returned home, he went to change into his outfit for doing the chores. But when he opened up his closet door, he was very much surprised. Instead of his usual collection of clothes, they had all been replaced! Every single shirt of his was gone, replace with blouses, cami tops, tank tops, tube tops, and more. His pants were all gone too, with women's pants hanging in their place. Gail had replaced his entire wardrobe!

He picked out one outfit that didn't look too feminine, and put it on. Then he started on his list of chores for the day. Gail went crazy on him when she got home. She told him how much she loved how he looked like that. She took him by the hand to his bedroom, and she helped him by showing him several outfits he could wear to work, which wouldn't tip anyone off as to the fact that they were women's clothes he was wearing.

He had never thought of wearing clothes like that outside of the house! But now he really had no choice; she had got rid of all his male clothes. He stared at the curvy jeans and the pants with the zipper in the back. Was he really going to wear those?

His attention was ripped away, as she showed him his new collection of shoes. None were high heels or anything scary like that. But they were all shoes made for a woman. Head to toe, she wanted him to go to work in clothes, none of which were made for a man! He knew in his heart that he just couldn't do that.

And so, the next morning, after she dressed him up, he looked in the mirror, and gasped. He looked like such a little sissy! Everyone would laugh at him. He decided he just could not do it. He picked up the phone, and called work to tell them he was feeling sick. Then he'd have a long talk with Gail.

"If you're not here in five minutes, you're fired!" steamed his boss after he heard that Brian wasn't coming to work that day. Excuse or not.

"But I live half an hour away" he replied. "And I'm sick."

"That's it" said his boss. "You're never coming in again. You are officially fired."

He slammed the phone into the receiver. Brian stood there, and started to cry. He had just lost his job. And now, he'd never get another one that paid enough for him to keep his apartment. That meant he'd lose Gail too! He was about to lose everything he had. And he was dressed in women's clothes, so he didn't even feel like he could go out of the house.

Gail heard the crying, and came running into his room.

"What's the matter honey?" she said.

"I just got fired" said Brian. "I lost my job. Now I won't be able to even afford my half of the rent. I'll have to move out. I don't know what I'm going to do."

"Look at me" said Gail, wiping a tear out of his eye. "Don't think like that! It isn't all that bad. I can afford the rent myself. You don't have to pay me. You can just live here with me. I'll give you more housework to do, and maybe you can do some typing for the letters I need to dictate for work. You can pay me back by doing that for me during the day. Then at night, we can be together. What do you say?"

She was offering him a chance to become both her maid and her secretary. He would be completely dependent on her for everything. But he wanted to be with her so much! And he had a chance to do that now. The tears were still flowing, when he told her "yes".

 

* * *

 

Brian didn't even argue with her that night, when she returned from work with a shopping bag. She had pulled out a black skirt and a pair of nylons, and she had told him that she wanted him to dress nicely for her, if he was going to do the work around the house. He just nodded his head.

"Of course, I'll expect you to shave your legs. You'd look silly in these with all that hair."

He just nodded again. It didn't matter now. He felt so small, like he was nothing. He had nothing. It was easy for her to mold him into what she wanted him to be.

When she came home from work, and found him wearing the skirt, cleaning the floors, Gail was all over him. She pulled him into the bedroom, and he couldn't believe it when she started to go down on him! He felt terrible to be wearing all those female clothes, but there she was sucking off him, her hands all over his nipples, as usual.

He came really big, and he collapsed into an embrace with her after she swallowed it all.

"Mmmm" she said. "But you know, all that hair of yours down there gets in the way. You should trim it into a little neat rectangle, like I do."

The next time he showered, Brian was using the pink shaver on himself, down there between his legs.

 

* * *

 

Brian had been Gail's maid and secretary for a week now. While he was getting more used to being in a skirt, it wasn't as if he liked it or anything. However, he did like the reward he got at the end of the day! Without fail, she had gone down on him. That was so wonderful, but he wanted to go further with her. He wanted to feel himself up inside of her sweet pussy.

So when she brought home makeup for him, or suggested that he should start to paint his nails, he knew that she was pushing him further, but that his reward would be greater. He didn't even argue the day she came home with a large pair of fake boobs, to go inside his bra. Without argument, he just put them in.

Soon, he was wearing jewelry too, and Gail was spending time with him, teaching him different techniques for making his hair and makeup look good. She had bought a wig for him, but she told him she hoped he could let his own real hair fill out soon, so he could get a perm, and not need the wig anymore.

His first lesson on how to walk in high heels had gone rather well. And now, she told him that he should wear them all the time, to get better at walking in them. All week, he went around wearing skirts and blouses, nylons and pantyhose, wearing pumps and mules. All week, he had worn makeup. His nails were painted bright red. He was looking more and more like a real woman.

But ever since he had lost his job, he felt like he was in a haze. He had become so passive, and he didn't understand why. He should have been resisting Gail at every move. In his mind, he realized that she was trying to turn him into a woman! Yet for some reason he could not understand, he wasn't trying to resist her. He wasn't saying no. He just did what she told him.

"I'm having a diner party" announced Gail later that day. "I've got a new uniform for you to wear, so you can serve my guests."

She handed Brian a hanging bag. He opened it, and gasped when he saw what was inside: a maid's uniform. It was jet black, with what seemed like a very short skirt, a plunging neckline, and a frilly white apron. There was also a white cap to wear on your head, and white lace gloves.

"I'll want you to wear your darkest nylons, and your highest heels with this" instructed Gail. "I've laid out the menu plan in the kitchen. Hors d'orves, salad, main course, and dessert. You'll serve my guests drinks, take away their dirty dishes, fill their water glasses, and whatever else is required."

Brian just nodded his head. He was still staring at the maid's outfit, wondering how he could bring himself to wear it.

"Look at me. Look into my eyes" said Gail.

Brian looked over, and locked his eyes onto hers.

"You've been so good, since you've become mine" she said, putting a hand on his cheek. "You've done everything I've asked of you. This will be asking a lot, to show you off to my friends, as my personal maid. This will be a big step for you. When they see you, everyone will know that you are completely mine."

Brian nodded.

"But before we make any more plans for the dinner party, we need to talk. Tell me something. Do you like being mine?"

"Oh yes" he said, trembling as she touched him. "I love being yours"

"Good" replied Gail. "I knew it. I just wanted to hear you say it. Now tell me. Are you willing to go all the way? Do you really want me? Are you ready to share my bed?"

"Yes!" said Brian, now ecstatic. He was finally going to have her! She led him by the hand into her bedroom, and closed the door, then the shades. She walked up to him, put her arms around his neck, and kissed him on the lips. Lipstick touched lipstick as they gently met.

"Do you know why I've been dressing you up like you are" she whispered. "Do you know why I want you to wear makeup and go around in high heels?"

"Because you want me to be a girl" said Brian.

"That's right, my love" she replied. "And if you're going to go all the way with me, then you need to take the next step towards femininity too. Each time you've done something to make yourself more like a woman, our relationship has gone further, hasn't it?"

"Yes" he said.

"And if you are to be completely mine, in every way, and if you are to be my lover as well as my servant, then you need to commit to me. And you need to commit to living full time as a woman. So tell me. Are you willing to become my woman?"

Brian was so hard now! He wanted her so badly! Every fiber of his being ached for her. He just had to get inside her pussy. He couldn't resist her.

"Yes, I am" he said with a firm voice.

"Excellent" she replied, her face lighting up with a smile.

Gail reached down and removed her skirt. She wasn't wearing anything underneath. She got onto the bed, and spread her legs wide open.

"You've got me all wet already, just thinking of you as my girl" she said, licking her lips.

Brian removed his skirt, and pulled down his panties. He was hard as a rock, and so ready for her. He reached up to remove his blouse, but she told him not to. She motioned him to join her on the bed, which he immediately did.

Gail used her hand to gently guide his fully erect penis into her pussy. He slid in so easily. His eyes closed, as pleasure surged throughout his whole body. He pulled back so he could thrust, but Gail held him close, and didn't let him.

"Slowly. Gently, my love" she said. "Tell me that you are a woman now."

"I am a woman" said Brian.

Gail smiled, and guided him back, then forward for a sweet thrust deeper into her.

"You are a woman now" she said. "From now on, your name is Tammy. Tell me who you are now."

"I am Tammy" said Brian. "I am a woman."

She allowed him another thrust.

"You are mine Tammy. You belong to me. You live only to serve me."

"I am yours" said Brian. "I live to serve you."

He was rewarded with another out-and-in thrust. He was on the verge of coming. He was going to let himself come with the next thrust, but Gail made him wait a while.

"You are Tammy now. You are a girl. And you are mine. Tell me again and again. Tell me that you are my woman!"

"I am your woman!" said Brian. "I am Tammy. I am yours."

"Again, louder!" she ordered.

"I am your woman! I am Tammy!"

 

She made him say it over and over again, louder and louder. As he screamed that he was a woman, she let him start to go in and out again and again, until he could no longer take it, and he let himself come inside of her. Brian was so happy, even if he had just sold his soul, promising to be her woman.

"Now Tammy, I am going to test you, to make sure you will live up to your vows. Get down on your knees, and lick my pussy. I want you to make me come again and again! And I want you to suck all of those nasty male juices out of me. You got me all dirty. You are my maid, so now you need to clean me up. Now."

Brian got down on his knees. Gail held him by the head, as he licked her pussy.

"More gently, my love" she said. "You're a girl now too. You should know how sensitive your pussy is."

Brian could only look up at her as he licked and licked, listening to her telling him how he was a girl now, and how he was all hers. When Gail finally was too sensitive for him to lick anymore, she pushed him away.

"Open the top drawer of my night stand" she said. "I have something in there, special, just for you."

Brian got up. He opened the drawer, and he gasped when he saw what was inside. A black leather harness that would go around your legs, and tie up at your back, with a buckle like a belt. The front of the harness had a large flat area, poking out from which was a large realistic strap-on dildo.

Brian picked it up gingerly, as if it would bite him, and he handed it to Gail. She smiled as she put it on, then squeezed a little bit of lubricant onto it. She used her hand to rub it on all over, and it looked like a man when he was masturbating himself. Brian's eyes were wide, as she pointed to the side of the bed, and ordered him to lean over.

He closed his eyes as she came around from the back, and very gently started to push it up into him. He felt a strange new sensation of pleasure, as it hit him just right. She started to gently thrust it in, deeper and deeper, harder and harder.

"Now you are a woman" she said. "From now on, if you're to penetrate me in the bedroom, you will have to beg for me to do this to you first. Only after I get to f*ck you, will you be allowed to do the same for me."

She reached around, and cupped her hands over his large fake boobs.

"In time, the hormones you've been taking will make real boobs start to form here, so you won't have to wear these anymore."

"Hormones?" said Tammy.

"Yes" she replied. "Female hormones. You've been on them, ever since I arrived here. Don't you remember each night when I come into your room, wake you, hypnotize you, and get you to take your pills? Haven't you wondered why you have been so passive, and why you've done everything I've asked of you?"

Tammy's mind raced. She couldn't remember nightly visits from Gail.

"Search inside yourself Tammy" she said. "You'll find something interesting there: I implanted a command so that the moment I penetrated you, you would forget that you were ever a man. Soon, you won't remember anything, except for me, how much you love me, and how much you want to serve me."

"I was never a man!" said Tammy, feeling upset that Gail would insult her like that. She had always been a girl! Yes, she had a strange growth between her legs, but that wasn't anything that surgery couldn't fix!

"Tammy, do you remember when you first wore a bra?" said Gail.

"Yes" replied Tammy. "When I was a little girl. I was jealous that my sister had boobs. I wanted them too! So I started to wear a bra all the time, hoping that would make them grow faster."

Tammy was tired of being so flat-chested. She decided right then and there, that she would ask Gail if she could go get implants. She wanted to be stacked, like Gail was. Tammy looked up to her so much! She wanted to be just like her.

 

* * *

 

The party was going well. Tammy was just bringing out the dessert to the six guests, plus Gail who was having a ball playing the role of hostess.

"Your girl is very good" said one woman. "How does one afford a live-in maid these days?"

"Oh, I have my ways" replied Gail.

As Tammy did the dishes, some of the guests started to leave. Those that remained wanted drinks, so Tammy was again called into service. There was one man and two women left by now. She brought them drinks, napkins, or anything else they asked for. Gail had a little bell she would ring when Tammy's services were required. Tammy was very happy to serve the guests, because she knew it made Gail so happy.

"We'll take our coats now" said the one woman, as Tammy responded to the bell again. She went to the coat closet, and brought both of the women their coats. She held the door as they walked out, saying their good-byes. Now only the man remained, still talking with Gail.

"Tammy, we'll be in my room for a while" she said, as she led the man by the hand down the hall. "Please put away the leftovers, and then you can vacuum and clean up everything else."

"Yes Ma'am" replied Tammy. She knew to use a more formal address to her Mistress, when guests were around.

Tammy watched as the man excitedly entered the bedroom. But she couldn't even think about what was going on in there. There was work to do! She was soon on her hands and knees, cleaning the floor, and making sure everything was spotless.

About an hour later, Tammy was putting away the cleaning supplies, as she finished her work for the day. She stood up at attention, when she heard the bedroom door open. The man walked out, his hair all mussed up. Tammy smiled when she noticed the outline of a bra underneath the man's shirt. There were two gently bumps on his chest as well. No doubt her Mistress had done that to him.

"He thinks nobody will notice his boobies" whispered Gail, causing Tammy to giggle like a little girl.

Tammy got the gentleman his coat, and showed him out the door. She smiled. She loved it when her Mistress brought a man over, and turned him into a woman. It was exciting to see! Even if it meant that Gail was being intimate with someone else, it was rewarding to see what she could do to a man.

"You've been a very good girl all night Tammy" said Gail. "Is there something I can do for you now?"

"Please Mistress, please f*ck me" said Tammy, falling to her knees. "I love you so, and I just have to feel you inside me. Nothing makes me feel more like I am yours, then when you're thrusting into me."

"All right dear" said Gail. "Go get the strap-on ready. I'll freshen up. Then I'll do you all night long. You can even sleep at my feet tonight, since you've been so good."

"Oh thank you!" said Tammy. "I'm so glad that I'm yours. You make me so happy."

Tammy ran off to the bedroom. She couldn't wait.

  

  

  

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