Frannie's Femboy

byBiDrew42©

When I was finishing high school, I did a lot of different jobs to raise money. I mowed grass, worked part-time on a construction crew, and pumped gas, all to raise funds for college. I had been accepted to the college of my dreams on a partial wrestling scholarship, but my parents weren't going to be able to help with the other expenses. While I hoped to eventually turn the partial scholarship into a full one, I was doing everything I could to raise enough money to avoid missing a year.

In addition to all the other jobs I was working, I was offered a job as a babysitter. My mom knew a single mother in the apartment complex we lived in. She had a young son and she needed someone to watch him on Friday and Saturday nights. My mom suggested it was an easy way to earn some extra cash. I definitely wanted the cash, but Friday and Saturday nights were party nights for me and all my friends.

Despite my hesitation to give up my weekend nights, one day after school I went over to meet the woman who wanted to hire me. She lived a couple of buildings over from ours, so I walked over and knocked on the door and it was opened by one of the most beautiful women I had ever seen.

She was tall, 34 years old, well-built with large breasts, long blond hair, and gorgeous blue eyes. She was wearing a mini skirt and I remember thinking that she had the most beautiful legs I had ever seen. I was instantly attracted to her. She smiled and said her name was Francine, but told me to just call her Fran or Frannie. She invited me in and introduced me to her son Caleb. He was a good-looking kid with blond hair and blue eyes like his mother. Frannie and I sat at her dining room table and she asked me a little about myself and then told me that she would need me to babysit on Friday and Saturday nights beginning at about 8:00pm. She didn't know how late she would be but would try to be home by 2:00am. She offered to pay me $5.00 per hour if she was home by 2:00am and $10.00 per hour for every hour or partial hour if she came home later than that. I did some quick calculations and said that was fine with me. She smiled her dazzling smile and said she would see me Friday night at 8:00.

I showed up at her house promptly at 8:00pm on Friday night. She answered the door wearing only a bra and panties. I was somewhat taken aback since I didn't know her at all, but she waved me in .She apologized for her appearance but said she was running a late. As she trotted back to her bedroom she told me she had fed her son and I just needed to entertain him until nine or so and put him to bed. She raced back into her bedroom and left me standing there with an erection. Seeing Frannie in her bra and panties and smelling her wonderful perfume had made my cock swell.

Frannie came back out a short time later wearing a very short mini dress and she turned around and asked me to zip her up. I did as she requested, and I loved the feel of her silky soft skin against my fingers. When I had zipped her up she turned around and asked me how she looked.

"Beautiful," I managed, trying not to stare at her cleavage but failing miserably. Frannie laughed and told me I was sweet, and then she was gone.

I played with Caleb for about an hour, and then put him in bed. I read him a story and he was asleep before I finished. I put away the toys we had played with and sat down to watch TV. After a little while I pulled down my pants and jacked off thinking about Frannie. I had her amazing body in bra and panties firmly in mind while I stroked myself.

After I spurted and cleaned up, I went exploring. It was a small two-bedroom apartment, but when I entered Frannie's room the first thing I noticed was the lingering smell of her perfume. The room was a disaster, with clothes strewn all over the floor and bed. The first thing I noticed was a pair of panties wadded up on the floor between the bed and the bathroom. I picked them up and shook them out. They were simple white cotton panties, but they were very skimpy, and they had the word 'Friday' printed on the elastic waistband.

I realized she must have worn them to work that day and I tentatively lifted them up to my face and sniffed them. The first thing I smelled was her wonderful perfume. Then I sniffed the crotch, and it was the most wonderful smell I had ever experienced. Frannie smelled amazing.

I stood there sniffing her panties for several minutes and then I crawled up onto her bed amidst all her clothes, pulled down my pants, and jacked off again after wrapping her panties around my cock. I was careful not to get any cum on the panties, and afterward I lay there with her panties over my face and just enjoyed the scent of her. After a while I masturbated again, and then got up and put the panties back on the floor where I'd found them and exited her room. I watched TV until she arrived home at 1:00am.

When Frannie arrived I stood up to greet her. She looked a little disheveled and smelled like booze. She asked how her son had been and I told her we had played with his toys for awhile and he had gone right to bed at 9:00. She gave me a $20 bill and told me she would see me the following night at 8:00.

I walked home from her apartment to mine, happy I had some cash and anxious to get in my bed so I could masturbate again. My mother was waiting up for me and asked if everything had gone well and I said that it had. I showed her my cash and she asked me if I liked Fran. I said she was a very nice lady. Then I got in bed and jacked off again thinking about Frannie in her bra and panties.

The next night I arrived right at 8:00pm. Unfortunately, this time Frannie was fully dressed in a black mini dress. She looked beautiful and I told her she looked nice. She smiled and told me I was sweet. As she left she told me her son could stay up until 10 if he wanted too and then she was gone.

I watched TV with Caleb and we played with his toys for awhile, and then I got him into bed and read him a story. As soon as he was asleep I put away the book and went into Frannie's room. It was a lot neater than it had been the previous day and there were no dirty panties readily visible. I went into the bathroom and looked around. I found the dirty clothes hamper and went through it, coming up with the same pair of panties I had sniffed the previous day and another pair that she had been wearing when I arrived the previous evening. The second pair was lacy and black and very sexy. I sniffed the white panties first, and they still smelled wonderful. Then I sniffed the black panties, and they smelled incredible as well. If anything, her scent was even stronger. I went out to the bedroom with both pairs of panties, stripped naked, and climbed onto her bed. I wrapped the white panties around my sniff cock and placed the black ones over my face and jacked off. After I came and cleaned up, I stood up and put her black lace panties on.

Frannie's panties felt amazing. I loved the silky feel of them, and after I positioned my cock and balls so they weren't hanging out the sides, I thought they looked good. I stood in front of the mirror that hung on her bathroom door and admired myself. I was small for my age, only 5'7" and weighing 130 pounds, but I was lean and muscular. I had been on the swim team and wrestling team for all four years in high school, and I also ran the 1500 and 3000 meter races on the track team. I loved the way Frannie's panties felt on my cock and balls, but I also thought I looked pretty good in them. I was soon hard again. I wore the panties and nothing else for about an hour. I also explored her room and closet some more. I went through her underwear drawer and discovered a large collection of sexy panties, bras, garters, stockings, and other items I didn't know the names of. What I did know was that I would be trying some or all of them on in the future.

Under her bed I found a box that contained three vibrators, a string of Ben-Wa balls, three butt plugs in various sizes, and a huge, life-like rubber penis. There were also some bottles of liquid with names like 'EZ Glide,' 'Love Rub,' and 'Edible Lube.'

I picked up the rubber cock and it was pretty amazing how life-like it was. I was also amazed at the size of it. It seemed huge compared to mine. I lifted it up to my nose and sniffed it, but it just smelled like rubber. I picked up one of the vibrators and examined it, noticing a small button on the bottom of it. I moved the button to the on position and it began vibrating like crazy. It seemed Frannie liked her pleasure.

I tested all the vibrators, and then put them away as I had found them. I removed the panties, and then decided to jack off again. This time when I came I was horrified that I had got a little cum on Frannie's panties. I wiped it off with toilet paper, but they still looked stained. I thought about washing them in the sink, but didn't know how I would dry them after. In the end, I just tossed them back in the hamper and hoped Frannie wouldn't notice. I got dressed and went back out to the living room and watched TV.

When Frannie got home that night she was very drunk. It was 3:00am when she came in. She smiled at me and managed to extract my pay from her purse, and then she asked me to help her into the bedroom. I let her lean on me as we headed down the short hallway and into her bedroom. I turned on the light and she plopped down on the bed with her legs hanging over the end. Her short skirt rode up and I had an excellent view of her panties, this time red lace.

She told me to take off her shoes so I did, leaning in close to her crotch for a better look. I inhaled deeply and could just make out the same scent I smelled on her other panties. I could also see a couple of pubic hairs sticking out the sides of her panties. I wanted nothing more than to bury my face in there but didn't dare.

When I had her shoes off I stood up to go, but Frannie was struggling to sit up and asked me to unzip her dress. She turned slightly and I unzipped her. She started struggling to get the dress off and I asked if she needed help. She smiled at me and asked me to help her up. I pulled her to her feet and she pulled the dress down over her shoulders and then over her hips. It hung up on her hips and she shook her ass a little as she struggled to remove it. I was rock hard watching this performance.

And then she was standing in front of me in her bra and panties again. She looked incredible, and I was hoping she would remove them as well, but she fell back on the bed and told me she would see me next Friday. I turned and walked out, turning off the light behind me. I locked the front door on my way out, went home and jacked off.

The next Friday, after I had her son in bed, I went into her room and stripped naked and dressed in a clean pair of panties while I explored. I had found basically all there was to find. I dug a pair of soiled panties out of the hamper and sniffed them while I jacked off wearing her clean panties. After I came, I tried on a bra. She had huge tits, so I didn't like the way it looked and stuffed some toilet paper into the cups. I liked that look much better.

I didn't know what was getting into me. I had never had any desire to dress in a woman's clothes before but now I couldn't seem to stop myself. I loved the way her bra and panties felt when I had them on, and I really loved the way her soiled panties smelled. I made sure to put everything back the way I found it. Several weeks went by and each Friday and Saturday night I became bolder, dressing in bra, panties, garter, stockings, and heels. I was slender and not quite as tall as Frannie so when I started trying on her mini skirts and dresses, they fit pretty well also. I loved how sexy I felt in her clothes and loved how my legs looked with her heels on.

On Friday nights, Frannie would come home a little tipsy. On Saturdays she was usually pretty drunk when she got home. She occasionally asked me to help her undress and get into bed, and I was happy to do so. It didn't take me long to figure out that when she was really drunk I could get my face real close to her pussy when I removed her shoes so I could breathe in her wonderful scent and she didn't even notice.

I started wearing a pair of her panties home when I left on Friday nights and I would return them on Saturdays. I knew she always washed her clothes on Sunday so I would take a pair of dirty panties from the hamper, put them on instead of my own underwear, and return them the following night. I loved the way I felt in them.

One Friday night, I was wearing a pair of her sexy panties, a garter, stockings, and a bra when I remembered the box under her bed. I took it out and examined the contents again. This time, one of the vibrators had something brown on the end of it. I looked closer and sniffed it, and it was shit. I quickly realized that she had been inserting the thing in her ass. I picked up another of the vibrators and sniffed it and it smelled like her pussy. I wondered if she used them at the same time. The big rubber dick also smelled like her pussy that night, and I guessed she hadn't washed them after the last time she used them. I wondered what having a vibrator up my ass would feel like.

I pulled down the panties and, using the same vibrator she had used in her ass, tried to insert it into mine. I didn't have much success until I remembered the lube. I opened the tube of EZ Glide and applied it to the vibrator, and then eased it into my ass. The lubrication made all the difference, and it slid right in. I kept a firm grip on the base, and turned it on. It felt incredible. I held the vibrator with one hand and stroked my cock with the other, and before long I shot an enormous load of cum onto the carpet. I extracted the vibrator from my ass and turned it off, wiping it clean with toilet paper.

Then I picked up the huge life-like rubber cock. I held it in my hand like I held my own when I masturbated. It was heavy and didn't feel nearly as life-like as it looked. I raised it to my mouth and licked the head. I could faintly taste Frannie's juices but mostly it tasted like rubber. I briefly entertained the notion of inserting it into my ass as well, but decided to leave that for another night.

I put all the toys away and then slipped on a pair of her high heels and put on some bright red lipstick and a blond wig. I felt very feminine and looked very feminine as well. I wondered if other people would think I looked like a girl dressed like I was.

I jacked off again, and then I carefully put everything back the way I had found it. I kept the panties on and pulled my shorts up over them, stuffing my own underwear into my pocket. When Frannie got home she paid me and kissed me on the cheek, which she had been doing since about the second week, and I went home and fantasized about her while I jacked off again.

The next night I repeated my cross-dressing after Caleb was asleep, this time wearing a sexy bra and panties, cream colored pants and blue flower print blouse. I put on a short red wig, high heels, and red lipstick again and thought I looked amazing. I thought I made a very pretty girl. I wore her clothes for a couple of hours, jacking off a couple of times, and put everything away just as I'd found it.

When Frannie got home that night she was shit faced. I had never seen her that drunk and she could barely walk. I practically had to carry her to the bedroom. I didn't even wait for her to ask anymore, I just helped her out of her clothes and helped her into bed. On that night, she flopped back on the bed with her legs spread wide and started snoring almost immediately. I knelt between her legs and removed her boots, and then moved my face right up into her crotch. I inhaled deeply, loving the scent of her pussy, and then I licked the crotch of her panties. She moved in her sleep and let out a little moan and I was afraid she would realize what I had done, but she started snoring again right away so I risked a second lick. It tasted as wonderful as it smelled. I reached a hand up and slipped a finger under the edge of her panties, watching her face for any indication that she was awake, but she didn't move. I slid her panties aside and had my first look at her pussy.

It was beautiful, of course. She was neatly trimmed at her bikini line but pretty hairy on top. I couldn't really see anything but her bush, but I loved the way it smelled when I leaned in close and inhaled deeply. I pressed my face into her bush and loved the way her soft hair felt against my face. I stuck my tongue out and probed in her hair a little, seeking her pussy, but then she grunted and twitched, and I pulled back quickly. I was too afraid to try anything else.

I sat her up and unzipped her dress, then wrestled it off of her. I loved the way she looked in her bra and panties. Before I lay her back down I looked at the back of her bra to see if I could get it off easily. It didn't take much to figure it out and I soon had her bra unsnapped and removed it as she fell back onto the bed. I stood holding her bra while looking down at her perfect tits.

They were magnificent. I have no idea what size they were and as the years have passed they have no doubt become bigger in my mind, but I thought they were perfect. Her skin was very pale, but her areoles were very dark and her nipples were big. It was cold in the room and I watched in amazement as they became erect. I thought her breasts were the most wonderful things I had ever seen.

I reached out and touched the one closest to me and loved how soft it was. I moved my finger up to her nipple and was amazed at how hard it was. I was simply overwhelmed by her beauty and wanted to start sucking her tits right then. I was about to lean down and take one of her nipples into my mouth when she grunted again and rolled over away from me.

I stood there admiring her backside for a few minutes, wondering if I should try anything else. In the end I just dropped her bra next to the bed, hoping she would think she had removed it herself when she woke up in the morning. I left her room, turning off the light and closing the door behind me.

The next Friday when I arrived at Frannie's house she was wearing a bra and panties again. She asked me to come back to her room because she wanted to talk to me before she left. I was afraid that she knew what I had done to her while she had been passed out the week before and she was going to fire me. In her bedroom, she sat at her vanity table and continued putting on her makeup.

She said, "I wanted to apologize for coming home drunk last Saturday night. I know you helped me get into bed, and I know that's not in your job description. I'm sorry I put you through that and I promise I won't let it happen again."

"That's okay," I said, desperately trying to think of a way I could convince her to keep coming home drunk so I could do more of what I had done the previous weekend.

"No, it's not," she continued. "I shouldn't even be sitting here in my bra and panties while you're here."

"Really, Frannie, it's okay. You've been very nice to me and I like helping you. And I don't mind that you're in your bra and panties. I like that you feel comfortable around me.

"I'm sure you don't mind seeing me like this," she laughed. "Most boys your age wouldn't mind. I'm glad you like to help me but I will try not to put you in that position anymore, okay?"

"Okay," I replied.

She looked at me in the mirror and her smile slowly disappeared. "Now I need to ask you a serious question," she said. "Did you take off my bra last Saturday night?"

I started to lie and tell her that I hadn't, but it seemed like she already knew. "Yes," I replied, not looking at her.

She sat there for a few moments not moving, and then I heard her stand up. She moved over and stood in front of me and then reached out and lifted my chin up so I was looking at her.

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byBiDrew42© 28 comments/ 259368 views/ 337 favorites

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