A while back I had separated from my husband and moved in with my friend Debbie. I wasn't sure how long I would be there, but had an open invitation to stay as long as I needed.

Debbie had an older house in the Village that she was renovating into several apartments. It was perfect.

Tim was her first tenant, a college student as well as a very talented carpenter. He had long, brown hair that he kept in a ponytail, and wore jeans and an old button down dress shirt. He grew up working with his father on a construction crew, and knew every aspect of the building trade. In exchange for his rent, he was doing most of the renovation, occasionally calling in an electrician or plumber when necessary.

Debbie was one of my best friends in college, and although we kept in touch, I really didn't see much of her after I got married. She was tall and slender, with beautiful, auburn hair and a fantastic figure. I secretly had a huge crush on her back then, but was afraid to tell her for fear of losing a great friend. She worked in Manhattan as a fashion designer and was out of town during the week. I hardly saw her during those two months which was OK, because I needed the time to figure things out.

I did see a lot of Tim, my new roommate, and we became friends very quickly. I wasn't sure if he was gay or not, but he never pried into my personal life or asked me out. It was both comfortable and a little frustrating. I'm used to more attention, and the fact that Tim didn't seem interested was almost insulting!

I began to wear more revealing clothes and sort of flirt with him without actually flirting. He would talk about school, and life as if I was one of his buddies. Maybe he was just very shy. Either way, he was great company and always there to talk to about my failing marriage when I felt like it.

After a while, I'd worn everything I'd brought with me and wanted to go home to get some fancier clothes. It looked like I'd be staying a while. I had already brought two suitcases full of things, but since I was going to be staying with Debbie for a while I wanted more.

Debbie had the washer and drier set up in a spare room that we could all share. I threw in a large load and piled the rest of my stuff on the old couch that we used as a table. I needed to run home for an hour or so while my asshole hubbie was at work.

Once home, I found what I wanted and stared at my still full closet. There, at the bottom, was a French maid's outfit still in the box. Well, hubbie wasn't going to be seeing me in that for a while. Maybe I could give it to Debbie as a gag gift. I'd LOVE to see her in that!

I went downstairs and sorted through the DVD's of our last vacation. I wanted to look at them again and try to figure out what was left of our relationship, if any. I looked at the clock and realized that over an hour has passed. Maybe I should call Tim to make sure he doesn't put my clothes in the drier. I don't want to be buying new things right now.

“Hi Tim? This is Teresa.”

“Hi, where are you?”

“I just ran home to grab a couple of things. Whatever you do, don't put my things in the drier, they all have to be hung, OK?”

“Yeah, no problem. I can do that for you if you like.”

“Um, alright, sure. See you in a bit.”

What a nice boy, I thought.

When I got back to Debbie's, Tim was in the kitchen having pizza. My first instinct was to go see what a mess he made of my clothes. Putting my suitcase down, I said hello and took off my jacket.

“Hi Teresa, I put your things in the master bathroom.”

“Thanks Tim, that was sweet.”

To my surprise, my blouses were hung perfectly on the shower curtain rod. Everything straight, evenly spaced, even the hangers were facing the same way! This kid was good!

He was doing a wash of his own so I figured I'd watch the DVD's, and finish my laundry later.

“If you're not busy Tim, I have some movies of my last vacation you can watch with me.”

“OK, but I never finished hooking up the DVD player. We had it fixed a while back.”

“Oh, never mind then, maybe another time.”

“No, it won't take long. I don't even remember why I didn't do it last time. Just give me a few minutes.”

“You're really handy to have around ya know?”

“Yeah, I guess.”

I made myself comfortable on the couch and took off my shoes while Tim went to work. He had pulled out the whole player and began messing with the wires.

“If it's a big deal don't worry about it Tim.”

“Almost there, this cable was never connected that's all.”

Finishing up, he put the player back and tried it. Nothing.

“The cables must be loose”

He knelt down again, kind of squatting, when I noticed something odd.

I saw what looked like his underwear showing and giggled to myself. They were bright red, just like my Victoria's Secret, cheeky panties, that I had left in the laundry room earlier.

Was it possible?

“Be right back!” I said, and went back to check. I remember leaving my panties all together for washing. I didn't see them anywhere, but rather than spend a half hour searching I thought I'd find a more interesting way to see if Tim was actually wearing my panties.

When I came back into the living room he was still bending over and struggling with the cables. I could clearly see that they were panties, and very likely mine.

“How ya making out there Timmy?”

“This is a pain in the ass, no wonder I never finished.”

“Speaking of a pain in the ass....”

I reached over and grabbed the waistband, pulling them up with a healthy tug.

“WHOA!”

“Cute panties hun, I have a pair just like them!”

“I don't believe this, you're wearing my panties from the laundry room! Get up.”

He was facing the wall and wouldn't look at me, couldn't look at me.

“Turn around.”

He turned around to face me but his eyes were on the floor.

“Go ahead, tell me what the fuck you think you're doing.”

“I'm sorry”

“Are you? This changes everything Tim. I don't think I can trust you anymore. When Debbie gets home in a few days the three of us are going to have a long talk about this. I guess you've been dressing up in her things too huh? Oh she is gonna freak!”

“No....I....it was just this one time Teresa...I....I don't know what I was thinking. It just happened.”

“It just happened? Are you fucking kidding me? You just happened to take my panties from the pile in the laundry room, then just happened to put them on and walk around in them? Do you want to be a girl Tim? Is that it?”

“No....I just....no....”

“Sit down here and explain this to me then. Come on. You're a crossdresser aren't you? You like to wear girl's clothes and pretend you're a girl, go ahead, admit it.”

Silence.

“I don't care if that's what you like to do, but stealing my things is wrong. You violated my trust. I thought we were friends.”

“I'm so sorry Teresa, it was just....I....I couldn't help myself.”

“You do like to dress up as a girl, right?”

Silence

“OK, don't talk. You can keep those panties as a going away present. I'm going to call Debbie and leave her a message. You can explain it to her. I have to get out of here for a while. I think I may be passing your Father's construction site. Maybe I can bring the guys coffee and we can all have a nice, long talk.”

“OH GOD, OH GOD, p....p....p....please don't do that Teresa, I'll tell you everything. I'm so sorry.”

“You already said that Tim, or should I start calling you Tammi? I like that, Tammi. I'll bet you make a cute girl Tammi!”

“OK, OK, I do like to dress up once in a while, but I swear I never tried on any of Debbie's clothes. Its, uh, its just something I, Oh I don't know how to explain this.”

“Let me help you, I do have some experience in this area. You are obsessed with women's clothing, especially lingerie. You fantasize about dressing up completely, from panties to stockings to a dress, and makeup. Have you ever worn makeup Tammi?”

“I can't believe this is happening. I am so sorry Teresa.”

“STOP SAYING THAT! Do you fantasize about dressing up as a girl, from head to toe?”

“yes”

“Well alright then. I think it's about time you did, and I'm going to help you every step of the way. Would you like that Tammi?”

“I just couldn't.”

“I understand. Not a problem. Your Dad's working over on Main Street in Port Jeff now right? I think I'll just get black coffee for the guys, and bring some milk and sugar. Is it muddy there? Do I need boots?”

“Please Teresa, you know that would destroy me. What can I do to make this up to you?”

“I simply want you to see what its like to get all dressed up. Maybe you won't like it as much as you think. Come on, it will be fun. And it will be our, little secret.”

“but I....I'll be...I'll have....”

“I know sweetheart, you'll have a big, hard-on. Its OK Tammi, I know all about sissies. This will be fun, you'll see. Now take off your shirt, pants, socks and shoes. And get your hair out of that ponytail.”

He looked at me with a mixture of terror and resignation. I just smiled and waited.

Then he began to take off his clothes.

“I'll go run the bath for you and we'll get you all shaved smooth, like a real girl.”

“Wait Teresa...”

I thought he was going to need more persuading, so I went back inside to help convince him. His jeans were off and he was standing there looking very embarrassed.

“What? Oh my God, your legs are already shaved! Take off your shirt.”

His chest was shaved as well.

“Well, well. It looks like you take this a bit more seriously than you told me. Wait a minute, did Debbie tell you that I'm a makeup artist?”

“yes”

“AHA! I think you planned this whole thing didn't you? You wanted me to catch you right?”

I thought he might cry but the bulge in his, I mean my panties told me to continue.

“This is just crazy Teresa. This is sick, I'm so sorry. I'm a freak and you must hate me.”

“Don't be silly Tammi, do you think you're the only boy in the world that likes to dress up as a girl? Because you're not, believe me. Did Debbie also tell you that I'm a Dominatrix specializing in sissy training?”

“uh huh.”

“Aw, all you had to do was ask my little princess. We're going to have a ball, just me and you. Now finish undressing and I'll go get some things for you to wear. And leave the panties on. Be right back!”

“Now, the first thing I want you to do is begin to speak like a girl, OK? You are now Tammi, and you need to talk like Tammi from now on. Everything you say must be in a soft, feminine voice. Got it?”

“uh huh, I guess so.”

“NO! Try again. Say: Oh yes Teresa, I'll be a good girl. Go ahead, say it.”

“Oh yes Teresa, I'll be a good girl.”

“Not bad, we'll work on that.

Now, I brought you a special bra to go with your panties. Put it on and I'll help you adjust the straps.”

He quickly put it on and looked puzzled.

“That's a fancy one isn't it? I wanted you to have something special. Now turn around and I'll show you how it goes. You have so much to learn about being a girl don't you Tammi?”

“Yes, I suppose I do,” he said in the cutest little voice.

“Excellent! You're a very fast learner.

I know you don't have any breasts yet sweetheart, but I think for now you should just get comfortable and we can fix that later. Wait, put these rolled up socks in the cups. There, that's better isn't it? Now, Rub your hands over your new breasts and tell me how it feels. Go ahead.”

“I love it! I love my new breasts.”

“Good girl, such a good girl. Next, I have a blouse for you. I think you're gonna love this one. Put it on and let's see how you look. Its pretty isnt it?”

He fumbled with it for a couple of minutes and looked at me for help.

“Come over here baby, it goes over your shoulders like this, see? How does it feel Tammi, are you starting to feel feminine?”

“Yes I am, its a lovely blouse, thank you.”

“Oh you're adorable! You've been dreaming about this for a long time haven't you?”

“Yes Teresa, I really do want to be a girl.”

“I know honey, I know. And I'm just the one to help you make all your dreams cum true.”

“I want you to relax completely, OK? It's just me and you here and no one is ever going to know. I want you to enjoy every, single second of this.”

“I love you Teresa!”

“Sure you do honey, and I love my little sissy girl Tammi! I'd like to do something with your hair, maybe give you some nice bangs. Would that be alright?”

“Yes Teresa, I'd like that very much.”

“I thought you might. I guess I should have done that before you put your blouse on. You don't want to take it off again do you?”

“Oh yes, whatever you think is best.”

“Such a good girl. Let's go up to the bathroom and I'll see what I can do for you. Follow me.”

“What do you think? I just cut off a little bit. You have such pretty hair, you really do. Maybe one day we can take you to the salon for a perm or a different style, would you like that?”

“I think I'm going to faint now Teresa. I....I didn't think, Oh my, I feel dizzy...”

“Shhhh, it's OK Tammi. Everything's going to be OK. I know you're worried about going back to school, and when we're all finished I promise to help you look the same as before, more or less.”

“OK Teresa, shall I put on a skirt now? What about stockings, or pantyhose?”

“One step at a time baby girl. I want you to get comfortable with this a little at a time. You're wearing panties, a bra, and a blouse, and now its time for makeup. Let's go back into the living room. Now Tammi, I'm going to help you with your makeup this time, and later on I'll teach you to do it all by yourself. Lets start with the eyes. You're in good hands sweetie, just relax and trust me.”

“I trust you Teresa, I really do.”

“Good girl Tammi, now I want to tell you something very important. You're a big girl now and if you like to dress up you should. There's nothing wrong with it. Its not a bad thing, and you're not a bad person, do you understand?”

“I guess so Teresa, but I'm so scared. What if my friends find out, and my family?”

“You can't worry about what other people think your whole life. You have to learn to do what makes you happy. For example, I'll bet lipstick makes you happy, am I right?”

“Oh YES! Can you show me how to put on lipstick?”

“I sure can! You just keep talking like a girl, and wearing pretty things, and soon you'll feel more and more like a real girl, I promise. Is this the first time you've worn lipstick?”

“No, but my hand starts to shake when I hold it, I just get so nervous.”

“I know honey, I know. There's nothing to be nervous about now, nothing at all. After I finish your lips, we'll add a bit of blush, and then move on to your fingernails. Would you like that? We can paint them the same bright red as your lipstick.”

“Are you sure the door is locked Teresa? I'm really a little worried now. I mean, if someone came over and saw me like this, I mean....”

“OK, I'll tell you what we can do. I'll put a coat of clear sealer on your nails, we'll let that dry, and then you can decide about the nail polish. Oh, and here are a couple of rings that might fit. Never underestimate the importance of accessories.”

“Thank you Teresa, thank you for everything. Really.”

“Oh you're welcome Tammi. It's my pleasure.”

“I think I have the perfect skirt for you to wear with this blouse. And maybe tights would be better for you than pantyhose. I have all different colors too, you can try some on and we'll see what looks best.”

“This is just fantastic Teresa, I really mean it! It's all like a dream come true for me!”

Suddenly we heard someone wiping their feet on the doormat outside, and we both looked up.

“OH MY GOD-OH MY GOD SOMEONE'S HERE!”

“Oh stop, its probably the Postman. I'm having my mail forwarded. You just sit right here and I'll take care of it.”

“I'm going to hide, I'm frightened Teresa!”

“STAY-RIGHT-HERE. I told you I'll take care of it and I will.”

The door opened before I got there, and Debbie walked in carrying her overnight bag.

“Hi Deb, how's it going, back early this time huh?”

“Yes, its a long story Teresa, I'm beat.

I figured it was too late to hide Tim, and he was going to be seen as Tammi, so I just waited for Debbie's reaction.

“Traffic was murder, one of these days I'm going to start a business at home, and....What the....”

Tim did not look well. In fact, I was sure I saw his hands shaking as he tried to cover his face.

“Is that, OH MY GOD, THATS TIM! Uh, is there a specific reason that he's dressed as a girl Teresa?”

“Why yes there is Deb. I caught him wearing my panties, and he told me he's a crossdresser. So I did what I do best, I helped him.”

“But Teresa! You said this was our secret,” Tim whined, hands still covering his face.

“Well that was nice of you Teresa,” Debbie said calmly. “Does anyone feel like getting Chinese takeout? I'm starving.”

Tim's mouth was open and he stared at us in disbelief.

“You mean you're not mad?”

“Why would I be mad Tim, I mean Tammi? I like you, I trust you, and you're a fantastic worker. When the apartments are ready for rent I'm going to need a manager, and I'm hoping you'll take the job. You can wear anything you like, as long as its tasteful.”

“I just remembered Deb, I just happen to have a gorgeous, French maid's outfit in my car. Tammi can wear it to clean the apartments. Weekly maid service would be an added bonus for your tenants, and I'll bet Tammi would just love that! What do you think?”

“Sounds good, I was thinking chicken and broccoli, what about you two?”

“I'd like the shrimp lo mein and an egg roll. Tammie, What do you feel like having?”

“Anything Teresa, I think I already have everything I could ask for.”

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Tim finished the renovation shortly after I moved out. The apartments all rented out easily, and Tim became the manager and maid. He is continuing school on a part time basis and majoring in psychology. The last time I spoke with him he was dating one of the tenants, a man called Horse.

Don't you love a happy ending!

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