Frannie's Femboy

"Why?" She asked softly.

"I'm so sorry," I said. "I know I shouldn't have, but it looked like the straps were digging in to your skin and I didn't want you to be uncomfortable."

She looked hard at me.

"Sorry, I said again. "You're so beautiful I just wanted to see what you looked like without your bra. You're so beautiful and I'm just a dumbass.'

She looked at me with a small smile and said, "Thank you for saying I'm beautiful. And you're not a dumbass. You did what any normal boy your age would probably do. However, you should never take advantage of a girl or woman who is not entirely in control of her faculties. Do you understand?"

"Yes," I replied. "I'm really sorry. I guess I'm fired?"

"No way. I still need a good babysitter, so don't worry about it anymore. Let's make a deal, alright? I will try not to come home too drunk anymore and if I do you will only help me if I ask you to. Okay?"

"Deal," I replied and she shook my hand.

"And one last thing," Frannie continued. "If you ever want to see my boobs, just ask. I may not show them to you right then, but I don't mind if you have a look every once in a while, okay?"

"You're the best, Frannie," I said and hugged her. She hugged me back briefly and then told me to go sit on the bed while she finished putting on her makeup. I did as she requested and was fascinated as I watched her apply her makeup. She talked to me while she worked, asking me how I was doing at school, if I had a girlfriend, what I liked to do when I wasn't in school or working, and where I wanted to go to college.

I answered all her questions and asked her a few of my own. When I asked if she had a boyfriend she laughed and said she had a different one every weekend, but none of them were worth keeping. When she was done putting on her makeup she turned to me and said "Done. How do I look?"

"You are the most beautiful woman I have ever seen," I replied truthfully.

"Thank you!" Frannie replied with a big smile. "You're a real charmer. I wish you were older. Hand me that dress on the bed."

I stood up and picked up the dress, a light blue mini, and walked over and handed it to her when she stood up.

"Frannie?" I said hesitantly.

"Yes?"

"Can I see your boobs?"

Frannie laughed out loud and handed the dress back to me. Then she reached behind her back and unfastened her bra and slipped the straps off her shoulders and slowly lowered it until her breasts were fully exposed.

"What do you think?" She asked.

"They're beautiful," I responded.

Frannie pulled the bra back on and said, 'Don't you tell anyone I showed you my boobs. Everyone will want to see them. Zip me up, sweetie."

I zipped up her dress and she went into the bathroom and put on her red wig. I told her she was beautiful again and she picked up her purse and I followed her out to the living room. At the door she turned to me and said, "Don't forget our deal."

I said I wouldn't and she leaned forward and kissed me on the corner of the mouth and then she was gone. I touched the spot where her lips had just pressed against mine and thought she was the most wonderful woman in the world.

That night after Caleb was asleep, I went into Frannie's room and stripped naked, and then put on a pair of her sexy panties and a bra, stuffing it with some of her other panties. I then sat at her makeup table and used the same lipstick she had used and put it on my lips, trying hard to remember how she had applied it. Then I put on some eye makeup and eyeliner as I had seen her do. I didn't do a very good job, but when I put on a miniskirt, blouse, and high heels I thought I looked very much like a young woman.

"I'd fuck me," I said as I turned to look at my ass in the mirror.

I got up on the bed and masturbated, fantasizing about Frannie's perfect tits. I had a serious crush on her, and I also enjoyed wearing her clothes very much, especially the lingerie.

After I removed her clothes I started removing the makeup. It was more difficult than I thought and I had to wash my face several times to get it all off. I put her clothes back where I had found them, and then got a pair of her panties out of the hamper. I inhaled the crotch deeply, jacked off again, and then put the panties on and got dressed.

Frannie arrived home about 3:00am. She was a little tipsy, but not drunk. She once again kissed me on the corner of the mouth and asked me to help her remove her shoes. She led me into the bedroom and sat on the bed, and I removed her shoes. She smiled down at me and when I had her shoes off she stood up and asked me to unzip her dress, which I did. I was standing very close to her when she turned back around and slipped her dress off.

"Wanna see my boobs again?" She asked. When I said yes she laughed and asked me if there would ever be a time when I didn't want to see them.

I thought about that for a minute and said, "No, I guess I will always want to see them."

Frannie laughed again and turned around, telling me to unfasten her bra. I gladly complied, and when I had her unfastened she turned and removed her bra completely, standing a foot away from me wearing only a sexy pair of panties. My cock was rock hard and I was falling in love.

"Beautiful," I whispered.

"Wanna touch them?" Frannie asked.

"Yes," I replied breathlessly.

"Go ahead."

I reached out with both hands and gently placed them on the sides of her breasts. She was warm and her skin was soft and her breasts were soft as well. I moved my hands around a little and then gently squeezed. Frannie sighed softly and after a few moments of squeezing I gently squeezed her nipples between the thumb and forefinger of each hand.

"Ummmmmm," Frannie moaned, "that feels nice."

She let me fondle her breasts for a couple more minutes and then she opened her eyes and looked at me and said that was enough. I immediately removed my hands from her breasts and she pulled on a t-shirt. She was breathing heavily and my cock was rock hard. Frannie looked me in the eye and then sat down on the bed. She patted the bed next to her and told me to sit down. I did as instructed.

"You're a good boy," Frannie said when I sat beside her. "I wish you were older."

"Why?" I asked.

Frannie laughed and said, "Because I would rock your world!"

She took my hand in hers and said "Please don't ever tell anyone about all this."

"I won't tell anyone, Frannie," I promised, and she leaned forward and kissed me, this time full on the lips.

"See you tomorrow at eight?" She asked.

"I'll be here," I said and Frannie smiled at me as I stood up. I watched as she lay down on the bed and pulled her feet up. I covered her and she thanked me and then I left, turning off the light on my way out.

I jacked off several times that night. I couldn't stop thinking about Frannie's perfect tits and how good they felt.

The next night I arrived at Frannie's house promptly at 8:00pm. She met me at the door wearing bra and panties again, invited me in and kissed me on the lips when I was inside and she had closed the door. She was in a rush but asked me to come to her room. She stepped into a flower print dress and pulled it up, and then turned so I could zip her up.

"I promise not to be drunk when I come home," Frannie said as she picked up her purse.

"It's okay, Frannie," I said. "I promise not to do anything if you do come home drunk."

"Good," Frannie smiled.

"Have fun," I said.

Frannie kissed me on the lips again and then she was gone. I locked up after her and spent a couple of hours playing with her son and his toys, and we played hide and seek, and after he was in bed I read him a story and he went to sleep. I went immediately to Frannie's room, stripped out of my clothes and put her "Friday" panties into the hamper, and then picked out my wardrobe for the evening.

I picked a sexy pair of red lace panties and matching bra, along with a matching garter and red fishnet stockings. I found a beautiful red miniskirt and a white see through blouse, and a pair of red leather four inch heels. I put on the panties and bra and stuffed it, and then I pulled on the stockings and figured out how the garter worked, attaching the clips to the stockings. Frannie wasn't a lot bigger than me – she was only a couple of inches taller and our bodies were about the same size, except for her big breasts. I adjusted the panties I had stuffed into the bra and then sat down at the makeup table. I put on lipstick again and then eye shadow and eye liner. I jacked off once at the makeup table, squirting my cum into the thick carpet underneath the table.

When I had my makeup on, I stood up and dressed in the miniskirt and blouse and slipped on the four inch heels. I was still learning how to walk in them but I stood up without killing myself and stood in front of the full-length mirror. I thought I looked damn good and I felt sexy as hell. For the first time I wondered if a man would find me attractive dressed as I was. I got up on the bed and masturbated. As I lay there thinking about Frannie's big boobs, I fell asleep.

Frannie came home a little after 3:00am, unfortunately just a little tipsy and not blind drunk, and I was sound asleep on her bed wearing her clothes and makeup with a wad of cum-filled toilet paper on the bed beside me.

Frannie shook me awake. I was lying on my back with the skirt hiked up to my waist and the panties pulled aside so my soft cock was visible. When I woke up Frannie was sitting on the bed beside me and I started and tried to get up. She put her hand on my chest and held me in place and told me to just relax. My heart was racing and I was scared to death and started to cry.

"Aww, honey, don't cry," she said. "I'm not mad at you. I promise."

She kept her hand on my chest and gently stroked my cheek with the other hand as I settled down.

"You made your makeup run," she said quietly as she looked at me.

"I'm so embarrassed," I said.

"Don't be, honey," Frannie replied. "You look very nice."

I smiled feebly at her. "Do you think so?"

"Yes," Frannie said, "you look very beautiful and very sexy. Very feminine."

It was then that my cock began to swell and I realized that it was exposed. Frannie saw the look of panic in my eyes and she looked down at my stiffening cock.

"Well at least that's normal," Frannie said reaching down and arranging the panties so my cock was covered up. In doing so her hand had touched my cock and it felt like an electric shock.

"You must think I'm a real freak," I mumbled dejectedly.

"Not at all, honey," Frannie answered. "A lot of boys dress up in women's clothes."

"Really?" I sniffed.

"Really," she replied, "And I'm not mad. But I think you need to tell me if there's anything else going on here that I don't already know about."

"No, nothing else. I just like dressing up in your clothes and then ...., you know, jacking off while I think about you. Oh, and sometimes I wear a pair of your panties home on Friday, but I always bring them back on Saturday."

Frannie smiled at me. "I guess that's okay too," she said. "I assume you found the box under the bed when you were looking around?"

"Oh, yeah, I forgot about that. Sorry."

"Well," Frannie said, "this was quite a surprise. How long have you been dressing up in my clothes?"

"A long time," I muttered. "At first it was just the panties, and then the bra, and after that I just wanted to see how I looked with girl's clothes on."

Frannie sat there staring at me for a few minutes, and I began to get nervous again.

"What am I going to do with you?" She asked herself quietly. "Well," she continued in a louder voice, smiling now. "Stand up and let me have a look at you."

She stood and held out her hand. I took it and she helped me get up. I was a little unsteady on the heels but she helped me stand up straight, then tugged the miniskirt down and adjusted the blouse. She stood back and looked at me with her hands on her hips.

"Very nice," she said. "You look very feminine. We need to fix your makeup though."

Frannie took me by the hand and led me over to the makeup table and had me sit down. She turned the chair so I was facing her and took a Kleenex and a bottle of something and told me to close my eyes. When I did she cleaned the makeup off of my face. Then she said she was going to show me how to apply my makeup properly.

"First," she began, holding up a small round container with a silver top. "We put on a little base."

Using her fingers she dabbed the skin colored cream on my forehead, the sides of my nose, and on my cheeks. Then she rubbed it in, making sure it blended in with my skin color.

"Next, some blush." She showed me another small round container, and then opened it and dipped her finger in. "Smile," she said, and when I did she dabbed the blush on my cheeks. "Always smile when you put the blush on. See where it is? That's where it goes and the best way to figure out exactly where to dab is to smile first. Got it?"

I nodded and she blended the blush in with her fingers, gently rubbing upward toward my temples as she worked.

"Next, we put on the eye base," Frannie went on, showing me another small jar. "You have a nice tan so we'll use a champagne color. Close your eyes. We dab this on the eyelids, and work it in with your finger from just above your lashes to just below your eyebrow. Now open your eyes and look."

I did as instructed and looked in the mirror. I already looked much better than I had when I applied the makeup. "Wow!" I exclaimed. "What a difference!"

"There are lots of steps, but it's pretty easy once you learn," Frannie went on. "Soon this will be second nature and you will be applying makeup without even thinking about it. Next we use a cream shadow." She showed me the container. "And dab it on. We use this little brush to get it in the creases, and our fingers to smudge it down over the lids, like this. Take a look."

"Next we use a little powder eye shadow so the cream won't smear and just pat it on with this little brush. And to make your eyes look bigger, even though you already have gorgeous big eyes, we pat a little gold cream shadow on the center of your eyelid, and then using your finger or a small brush, run a little along your lower lash lines, like this. Perfect. Take a look."

I looked and couldn't believe the transformation. 'Wow,' I said again. 'That's amazing.'

"You look amazing, honey," Frannie stated. "Now, we use this brown liner pencil and run it along your upper lash lines, like this. Always make sure the pencil is sharp. Then brush it up toward your lashes with the shadow brush. Then, we put two coats of mascara on the upper and lower lashes, like this. You have such beautiful long lashes. I'm jealous!"

I looked in the mirror again and couldn't believe my eyes. I could have passed for a beautiful girl. Frannie was smiling at me when she saw how excited I was.

"And the last step is lipstick," she went on. "You like the red, so we'll use that. Make a kissy face." I did, and she laughed. "Okay, we start in the center, and work our way out. Just blend it out. Then use your finger to pat it in place. That will make it last. Okay, that's it. Let me fix your wig. Now take a look."

I looked in the mirror and was astonished at the transformation. I turned back to Frannie and she was smiling at me and said, "You're beautiful, honey. You could pass for a girl."

"I look like a very pretty girl," I said in amazement.

Frannie had me stand up and gave me some tips for walking in the high heels. Before too long she said I was strutting around like a natural. She had me try on a couple of her other wigs and we both liked a short haired, strawberry blond one. Then she helped me adjust my clothes and stood back and gave me a critical look.

"Hmmmm," she said and walked up to me. She reached down and touched my erect cock through the skirt. "You would have to do something about that if you wanted to go out in public like this, but I can help with that too when it's not so hard."

She eyed me critically and said," I am certain you can pass for a young woman. You're very feminine, you're very pretty, and you're voice isn't too deep yet. We don't need the boobs to be so big, but I think we did a good job. We might need to pluck your eyebrows a little but maybe not. What do you think?"

I turned to look at myself in the mirror and had to agree – I looked like a very pretty, very sexy, teenage girl.

"I really do look like a girl," I said, wonderingly.

"A very sexy one in that skirt," Frannie replied. "We might have to dial the sexy down a little bit, although teenage girls are dressing like that all the time now. The boys are going to love you."

I thought about that last statement for a moment. Did I really want boys loving me? I decided I needed to think about that some more. I was actually thrilled that Frannie thought I looked good enough to make boys love me. I had done some experimenting with a male friend of mine, and although the experience had ended rather badly, I had definitely not ruled out further experimentation. I know I felt very good dressed in sexy clothes and with the makeup on. I fleetingly thought that it would be fun to fool the boys I knew.

After I had modeled for Frannie and she had pronounced me passable, she told me she wanted to take me to the mall the following Saturday dressed as a girl. I was a little nervous about that but readily agreed. Frannie then sat on the bed and motioned for me to sit next to her.

"Let's get some ground rules straight," she began. "No one can ever know about our special relationship. You can't tell anyone that you dress in my clothes and masturbate on my bed, or wear my panties home. You can't tell anyone I walk around in front of you in my underwear or show you my boobs or let you touch them. We may do a few other things together as well but if we do, you can't ever tell anyone. Okay?"

"Okay." I replied.

"I like you a lot, honey," Frannie said, "and I want our special relationship to continue. But if anyone ever finds out about all this we'll both have some serious explaining to do."

"I'll never say a word, Frannie, I promise. I like you a lot, too. I'll do anything for you."

"We'll see," she said, and I wanted to ask her what she meant by that, but she moved on quickly.

"Okay, next," she went on. "I don't mind if you keep trying on my clothes, wearing my panties home, and masturbating on my bed. You've been pretty discreet about it and I still wouldn't know what was up if you hadn't fallen asleep, although I have noticed some suspicious stains on my panties lately when I do the wash. You can keep doing all of that if you clean up and put everything away after. You can wear my makeup and wigs in the apartment. If I take you out dressed as a girl, you have to wear what I say and do what I tell you when we're in public, okay?"

I nodded my head that I understood everything.

"So, we are in agreement?" Frannie asked.

"Yes," I replied.

"Good." Frannie leaned forward and kissed me on the lips, this time letting her lips linger for just a little while. "Let me show you how to remove that makeup and get you changed so you can get home."

Frannie stripped down to her bra and panties, and I stripped down to my bra and panties and the garter and fishnet stockings. Frannie looked at me critically and said I was passable in lingerie as well, now that my erection had subsided. She showed me how to remove the makeup, and she removed her own as well. Then she told me to remove the lingerie.

I removed the garter and fishnets, and then the bra and I stood there shyly waiting for her to turn away.

"Sorry," she said. "I want to see. I need to know if I can hide your cock away while you're in public so we don't have any embarrassing incidents."