The Regular

by Jennifer White

 

I had always loved dressing up in girl's clothes, ever since I was young. I'd sneak into my sister's rooms, and 'borrow' their pretty things for myself. Even now, as an adult, I had my own collection of women's clothes, which I'd wear at home at least a couple of nights a week. Nothing turned me on more.

I'd imagine that I was a woman, and I'd make myself come. Nothing was more satisfying for me than that! But there was a problem: I had lost three girlfriends over the past few years, when I had tried to introduce crossdressing into our relationship. They just didn't seem to go for that. I was dating a sweet girl now named Kerry, and I didn't want to lose her. But I felt such a need to have a real woman involved with my fantasy.

 

And that was when I came across my idea. I would live out my fantasy, but not with Kerry. I would find someone else, for just that purpose. You see, on the south side of town, past the railroad tracks, there was an establishment which looked like an ordinary bar. But all the regulars knew what went on upstairs.

For the right price, Madam Lucy would let you have half an hour with one of her girls. Or a full hour, if you were willing to pay for it. And so, with money in my pocket, I drove there one stormy night. I had a couple of drinks at the bar to get my courage up. And then I went upstairs.

Madam Lucy paraded the available girls out for me to pick my favorite. Now frankly, some of them were past their primes, and showed it. Some looked too young for me. Some just didn't seem pretty, even after 2 shots of whisky. But then there was Mary.

Unlike the other ones, she seemed pretty and sweet. She had curves, but she wasn't heavy. She had long flowing hair. And she was busty. Everything I liked in a woman. So naturally, I selected her. I paid Madam Lucy. Then hand in hand, Mary and I walked off to her private room so we could get down to business.

 

"I came here" I said, "because I know that you are discrete."

"I never kiss and tell" Mary said.

"Good. Because I'm going to ask you to do something unusual, and I don't want it to be repeated outside this room."

"I'll do almost anything" she replied, "as long as it doesn't involve me being in pain, or anything that would leave a bruise on me."

"No" I said, "it's nothing like that."

"Tell me" she said, as she slipped out of her skimpy dress.

It took a lot for me to say what I wanted. I had never fully admitted it to a woman. But it was made easier by the fact that I was paying her for this. She wouldn't run out on me, as the others had.

"I want you to be on top of me" I said.

"Sure, I do that all the time" she replied.

"I want you to put your hands on my chest, and I want you to play with my nipples."

"Okay" she said, her tone of voice seeming to say "That's not so bad".

I took a deep breath.

"And I want you to tell me that I'm a girl. I want you to tell me that you're turning me into a woman."

"Okay honey, if that's what turns you on" she said, as she unzipped my pants.

 

Moments later, there I was, with a pretty woman on top of me, pinching my nipples, and telling me that I was becoming a woman! I was so elated. I don't think I had come that hard since I could remember! It was so good, that I made an appointment for a few days later. I would have loved to do it every day, but I only had so much spending cash!

 

I returned, and did the same scenario with Mary. And it was as good as the first time. And three days later, I was back again. But when we were done, she surprised me by asking me something.

"If you want to *really* feel like a girl" she said, "the next time you come in to see me, I expect you to be wearing panties."

"Sure, darling" I said as I kissed her.

 

Wow, how exciting this was! I felt so turned on by it. I made an appointment with Madam Lucy for the very next day in fact. I went to the store before it closed, and I bought a fresh pair of panties for myself. A black thong, with silver rhinestones.

The next day, I showed up to see Mary, wearing the panties under my blue jeans. I couldn't wait to show them to her. She smiled when she saw them

"Good girl" she said. "But I can tell that you just put them on. Next time, you need to wear them *all* day long, so you'll be thinking of me, and how you'll feel when I'm on top of you."

 

The thought of that was exciting, and I was even more turned on as she did me.

"You're becoming a girl now" she said. "*My* girl."

Bang! I came so hard. I almost cried, it was so good.

"Next time you come to see me sweetie" she said, as I was pulling on my panties, "I expect to see you in a bra too. What kind of girl goes around without a bra on? And you need to wear it *all* day long too."

 

And so I of course did that the next time, a couple of days later. How dangerous it felt to have a bra on underneath my clothes! I did think of her all day. The anticipation was enormous! And so when she did me, I came even harder this time. It kept getting better and better! I was overjoyed. I was starting to fall in love with Mary.

 

* * *

 

Each time I visited Mary, she would give me another assignment. One day, she told me to start shaving my legs, that that she expected me to be smooth, soft and hairless, if I was to be a girl for her. She ordered me not to cut my hair anymore, so it would grow out long and full, so she could style it. I was shaving my chest now too, and my underarms.

All of that was great, but I was afraid that I might start to get jaded, and it wouldn't be as much of a thrill anymore with her. But I was so addicted, I couldn't stop coming to see her. I quit going out to fancy dinners, to save on money, so I could see her more often.

And I was rewarded, because the next time I went to see her, she had a present for me. I opened it up, and found that she had bought for me a pair of A-cup sized breast forms! They looked like women's boobs, but they were a small size, like a girl just starting to develop.

"You need to wear those all day, before you come in to see me Caitlin" she said.

"Caitlin?" I replied.

"Yes. A girl needs a girl's name, doesn't she? And when you're with me, you are Caitlin."

 

Wearing the little breast forms was a thrill too, because it made me feel like I might get discovered! But nobody seemed to notice them, which was a relief too though. I didn't want to get caught. But the *possibility* of being caught was a big turn-on.

Mary had me start to arrive to see her wearing stockings and garters under my clothes. Or pantyhose and a corset. Each little thing was thrilling, and she always managed to make me come really hard. But then one day, she had another present for me. More breast forms, but this time in a B-cup. And they had large, prominent nipples on them, which would show through if I wasn't careful.

 

For the first time, I had doubts. Someone would be sure to notice the bumps on my chest if I wore those! And so I took the day off of work, so I wouldn't be caught with them. I did get some strange looks from the other customers waiting for their girls. *They* noticed. And I didn't like it.

I told Mary about it, after she made me come. But she just told me to be quiet.

 

Now I had been asking her out for some time now. I was in love with her, and I wanted to be with her all the time. But she had refused my advances. But this evening, she asked me something that made my heart skip a beat.

"Caitlin, I've got the day off tomorrow. I want you to meet me here, and then we're going out."

I was too overjoyed to even think of asking her where we would go. And of course, I showed up on time. I wasn't going to miss a date with her!

 

She drove us across town to a white house.

"Is this where you live?" I asked.

"No. My friend Anne lives here. She runs a small beauty salon here as a side job. We have an appointment with her."

"I don't know" I said. "I hate for other people to know about my dressing up."

"She already knows. I told her all about you" said Mary. "So you don't have to worry. She will treat you like a girl when you're here. And she made sure there are no other customers. It's just me, you, and her. Okay, sweetie?"

"Okay" I said.

 

I went inside with her, feeling very nervous.

"Mary!" said Anne, rushing over to give her a hug. "And this must be Caitlin."

"Yes" I replied, sheepishly.

"Nice to meet you" she said.

"Same here" I replied.

 

Mary went first, getting her hair cut. I watched as Anne worked on her hair, explaining how she was doing it in layers, and how she was styling it. Now it was *my* turn. I hadn't cut my hair for a month, at Mary's request. It wasn't long or anything, but a bit shaggy looking. Kerry had been nagging me to get it cut.

Now Anne was talking to me, as she worked on my hair. She put some smelly stuff in it, and seemed to take forever to get it done. When she finished, I saw myself in the mirror, and I was horrified!

 

First of all, I had blonde highlights now. Secondly, my hair swept over the side of my face, and curled up in back. My hair was short, but it was *definitely* a feminine cut. There was no way I could go out in public like this!

But that wasn't all that Mary had her do. She plucked my eyebrows a little, and then she gave both Mary and myself bikini waxes. Ouch! It hurt, and I almost cried in front of them. I had never realized how painful it would be!

 

After Anne put makeup on my face, I went upstairs with Mary, who gave me a freebie.

"You're going to wear your hair like that for me" she ordered. "And you'll arrive with makeup on your face from now on."

 

* * *

 

Mary started buying clothes for me. Women's clothes. At first, they weren't too obvious. The first blouse she picked could have been a man's fashion. And the first women's pants she gave me weren't too obvious. Even the women's shoes she bought me didn't attract attention in and of themselves. But with everything together, I was getting some stares at work.

I was going to tell her that it had to stop. But when I showed up that night, she told me something.

"Do you realize that you're not wearing anything male at all? Nothing! You're dressing as a woman now, full time. You *are* becoming a woman now, Caitlin."

 

It was the best session yet! And so I found myself unable to protest, as she started me wearing more makeup, perfume, and my first jewelry. But when she bought me C-cup breast forms, I freaked out. I couldn't hide those! Everyone in the lobby would see that I had boobs under my blouse. Not to mention the fact that she was giving me more and more feminine styling in my clothes.

The pants I was supposed to wear for the next session were 3/4 length capris. And that made my shoes look obviously like women's shoes. Again, I felt like I had to tell her that it needed to stop, but the sex was so hot, that I couldn't do it. I was fully addicted to her now.

After she got off of me, she presented me with another present: a gaff. A device I was to wear between my legs. My manhood would tuck up into a hole, and the gaff would keep it out of sight, making it look like I was a woman.

 

"Tomorrow, you will wear this all day, along with this new outfit" she said, handing me a pretty white skirt and a red silk cami top. "And you will be in full makeup. You will arrive here at 7:30, after waiting for me in the lobby for one full hour. Do you understand Caitlin?"

"Yes" I said sheepishly.

 

I took the day off work, so nobody would see me like this. They were all talking about me now, I was sure. There could be no hiding it anymore. But I couldn't go into work wearing a skirt! No way. So I did it at home.

Sitting there in the lobby, dressed fully as a woman, was quite an experience. The regulars looked at me, and shook their heads. They had seen me gradually transform into a more and more feminine person. But the men I didn't recognize started at me. They weren't sure if I was a feminine guy, or an ugly girl.

At long last, Mary came to get me. It was quite a relief to get out of the crowded room, and be alone with her! I was ready for our usual, but after she got naked, she ordered me to get on my knees. She spread her legs wide, and told me that I was a girl now, and I would please her like a girl. With my tongue.

I did her, tasting her juices, plus whatever was inside her from the other men she had seen that day. But her obvious pleasure kept me going. I was really turning her on now.

 

When she was done, I was *so* ready to do our usual. But instead, she had another idea.

"Take off your panties. Pull your skirt up, and lean again the bed" she said.

I did as she asked, and gasped when I saw her wearing a strap-on. She looked so powerful, with that *thing* sticking out in front of her. That made me feel so weak. I could see what she wanted to do. Moments later, she had it inside me, and I was moaning with a mixture of pleasure, pain and fear.

Then finally, I got my release. Incredibly, I came even harder than ever before. I was in tears when we were done.

 

"I have a present for you Caitlin" she said. "I want you to put it on now."

She handed me a new garment; a glamour dress. It was pink and sparkly. The neckline in the front had a deep V, which would have revealed my boobs, if I had real ones. She broke out a bottle of champagne, and we toasted each other, drinking a couple of glasses each.

 

That was when Madam Lucy walked into the room.

"Hello Caitlin" she said.

"Hello" I replied.

"I have a proposition for you" said Madam Lucy.

"A proposition?"

"Yes. We need a new girl here. One who can fill a very special need for us."

"Yes...." I said, wondering why should would tell me about this. What did it have to do with me?

"There is a lot of demand from customers, for a girl like *you*. They've been asking me, since they've seen you sitting in the lobby, looking all pretty like that."

"No" I said in shock and disbelief. "I can't do that!"

"When Mary first came to work for me, I sent her to a clinic" she continued. "In fact, most of the girls here get some plastic surgery when they first start out."

"You had surgery?" I asked to Mary.

"Yes. I had a boob job, and I had my nose reduced."

"If you come to work for me" said Madam Lucy, "I'll pay for you to have a nose job too. And a bb job. And hip implants, your chin fixed up, not to mention laser hair removal so you never grow a beard again."

I was too stunned to answer.

"I'll put you on female hormones. I pay for birth control for the girls. So its only fair that I pay for your hormones too. Now some men would love you like that. But some would love it if you went further."

"You mean...."

"Yes. The operation. I can have you made into a real woman. If you were willing to do that, you could make a mint."

"We get to keep 50% of what we're paid, minus rent for the room" said Mary. "Its a good deal. Better than most Madams give the girls."

"You could make more money than you do at work now, plus you could live out your fantasy of being a girl."

"Plus, you'd work with me" said Mary. "We'd be best friends. You could even move in with me, so we could commute to work together...."

 

It was all too much. My fantasy come true, all day, every day, with no shame. Better money than I made now. And I'd be with Mary all the time. How could I say no? I agreed, and after shaking hands with Madam Lucy, we all toasted with the remainder of the champagne.

 

* * *

 

I sold all my things, except my women's clothes, and I moved in with Mary. I'm on hormones now, but with just a couple weeks of time, I haven't seen any changes yet. Today, I'm very hungry, because I'm not allowed to eat before they operate on me. This will be the first of many operations, but I'm really excited! Soon, I'll look on the outside as feminine as I feel on the inside.

I've started my new life. I am Caitlin now. And I love it.

 

The End

  

  

  

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