Gay - cross dressing – femboy - feminization – blow jobs – anal sex – hand job – lingerie
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 k** 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.
"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."
I would have done anything for her at that point so I slipped the panties down and stepped out of them, standing there with my cock dangling. Frannie walked over to me and said 'Nice, but not too big that we can't hide it. I'm going to touch it for just a second, okay?" I nodded and she told me to spread my legs and when I did she reached between my legs from behind and took my cock in hand, pulling it back between my legs and tucking it up tight into the space between my balls and ass. I had started to get hard the moment she touched me and soon my cock slipped back out to where it belonged and stood at attention.
Frannie giggled and said we were going to have to work on that, but that she was happy she had that effect on me. "Did you like when I touched it?" She asked.
"Yes," I replied.
"May I touch it again?"
"Please," I practically begged.
Frannie reached down and took my hard cock in her hand. She put her other hand on my shoulder and began slowly stroking my rock hard cock.
"Does that feel good?" She asked.
"It feels really good!" I replied.
She stroked me several more times and I fired a load all over her hand and thigh.
"I'm so sorry!" I exclaimed, horrified.
Frannie laughed. "Don't worry honey. That's what's supposed to happen."
"I know, but I got it all over you."
"It's alright," Frannie said. "I like it on me."
Frannie went into the bathroom and came back with some toilet paper, first cleaning my cock and then cleaning her hand and leg. Then she told me to get dressed, so I did. She walked me to the door and before she opened it she kissed me on the lips again.
"I'll see you next Friday night, sweetie," she said and kissed my lips again.
I walked home with my mind full of the things Frannie had done to me that night. I wanted her to touch my cock all the time, and I wanted to touch her as well. More than anything, I wanted to make her happy. I would do anything for her.
The next Friday night I arrived at Frannie's house just before 8:00pm. Frannie opened the door wearing only panties and I gaped at her big breasts.
"Get in here before someone sees me," she whispered, smiling at the look on my face.
I stepped inside and she closed the door behind me, and then she leaned forward and kissed me on the lips, letting her soft lips linger for several seconds. My cock had started to swell when I saw her tits, but when she kissed me I was rock hard. I followed her back to the bedroom after saying hello to Caleb as I walked past his room.
Frannie had her clothes laid out on the bed and beside them was another outfit. She pointed at a black leather mini-skirt and peach-colored blouse with a pair of white lace panties and a matching bra on top. There was also a pair of black stockings and a black garter belt and a pair of knee high black leather boots. The short-haired red wig was on a wig stand on the dresser.
"That's what I want you to be wearing when I get home tonight, honey. Do you like it?" She asked.
I had barely been able to take my eyes off her tits but I said that I did like it and I would be wearing it when she got home. She smiled and stepped close to me and asked if I wanted to touch her boobs. My only response was to reach out and cup them in my hands, squeezing gently, and then pinching her nipples between the thumb and index finger of each hand. Frannie moaned and whispered "harder" so I squeezed them a little harder and she moaned.
"That feels so good, sweetie," she said, breathing hard. "Harder!"
I thought I was going to hurt her but she only moaned more when I pinched her nipples hard.
She let me pinch her nipples for a few more minutes before she gently took my hands and eased them away from her breasts. She leaned forward and kissed me on the lips, and I was surprised when her tongue brushed against my lips.
"We'll do some more when I get home tonight," she said, breathing hard as she pulled back. "Don't forget to put on your makeup."
Frannie started to dress and I helped her fasten her bra, and then zipped up her dress when she pulled it on. I helped her put on her shoes and then she put on her wig and touched up her makeup. I walked her to the door and she kissed me on the lips again and then she was gone.
I played with her son for an hour, read him a story and he went to sleep. I couldn't stop thinking about what Frannie had meant when she said we'd do a little more when she got home. I went into Frannie's room and stripped out of my clothes. My cock was hard and I was dripping, so I jacked off and then cleaned up before I started getting dressed. I slipped on the panties and loved the way they felt on my cock and balls. I was rock hard again in no time, so I lay on her bed with a pair of soiled panties and jacked off, this time actually coming into her panties. Then I put on the bra, garter, and stockings.
I went to the makeup table and tried to remember everything she had taught me, but I didn't look as good as I had when she did it for me. After that I stuffed my bra, put on the blouse, and then stepped into the mini skirt and pulled it up, zipping it on the side. After that I put on the boots. They were black leather with four inch heels and came up to just below my knees. There were lots of laces and it took me awhile to figure out how it worked, but I soon had them on. I almost fell over when I stood up, but I managed to stay upright and practiced walking around in them for a while until I got pretty good at it. I spent a lot of time admiring myself in the mirror. I loved the way I looked and felt in her clothes and makeup.
It didn't take me long to realize that I had gotten dressed way too early. It's not that I minded being in the sexy clothes, but I had to sit around and wait for several hours for Frannie to get home.
About 11:30 someone knocked on the door. I thought Frannie had come home early so I opened the door without asking who it was. It wasn't Frannie – it was one of her neighbors. He had dark hair and he was tall, and he was wearing only a pair of shorts. He was very hairy but also very muscular. His eyes opened wide when he saw me.
"Uhhh, hi," he said. "Is Fran here?"
"No," I replied.
"Who are you?" He asked, looking me up and down. I had never been looked at like that by anyone before. It made me feel warm and tingly inside.
"I'm the babysitter."
He smiled. "Wish I had a babysitter like you when I was little. You're gorgeous."
"Thanks," I managed to say. Did he really think I looked that good?
"Do you always dress so sexy when you babysit?"
"Sure, why not?" I replied.
"I think I need you to babysit for me."
"Okay," I said. "How old are your k**s?"
"I don't have any k**s," he laughed and I blushed. "Sorry, I was just k**ding," he said lamely.
"No problem."
"I just stopped by to see if I could borrow some milk," he said. "Can you help me with that or should I see Fran in the morning?"
"I think I can help," I said and stepped back to let him in. He had a plastic cup in his hand which I assumed he wanted to put the milk in. I took it from him and walked into the kitchen. He followed me, and when I turned he was clearly staring at my ass. I opened the refrigerator door bent over further than I needed to, and took out the milk carton. When I turned back around it was again obvious that he had been staring at my ass. There was a bulge in his shorts that hadn't been apparent before.
I filled up the glass that I had placed on the counter. I held the glass out to him and he took it, and then he asked, "How old are you?"
"Old enough," I replied.
"Damn,' he said, and laughed. "Old enough for what?"
I just smiled at him and escorted him back to the door. He turned to me on the way out and eyed me up and down again, said "Damn!" and walked over to the stairs. I watched him go, admiring his ass, and then closed and locked the door.
I was absolutely thrilled that he had believed I was a girl and that I was sexy. I couldn't wait to tell Frannie when she came home. I was horny again so I went into the bedroom and hiked up my skirt, slid my panties aside, and masturbated into the same soiled panties I had already spurted into that night.
Frannie arrived home at 12:45, which was earlier than normal on a Friday night. I stood up and arranged my clothes when I heard her at the door and was standing by the couch when she came in. She looked at me and smiled, and then closed and locked the door and walked over to me.
"You look beautiful, honey," she said and kissed me on the lips.
I wrapped my arms around her and kissed her back, and she dropped her purse and put her arms around me as well. This time when her tongue brushed my lips I parted my own lips and she slipped her tongue into my mouth. I thought it was the most incredible feeling in the world, and I moved my tongue to meet hers. We kissed for several seconds and then Frannie pulled back and looked at my face.
"You did a good job on your makeup, sweetie," she said. "We need to fix a couple of things, though."
"It doesn't look as good as it did when you did it last night," I replied.
"That's because I've had a lot more practice than you," Frannie replied and led me by the hand to the bedroom. "Pretty soon you'll be doing it even better than me, because you will learn what looks best on you and how best to accomplish the look you want."
While she fixed my makeup, I told her about the guy who came looking for milk. Frannie went very still when I started telling her, but she relaxed when she heard what his reaction had been.
"Well, I guess that turned out okay," she said, "but please don't open the door for anyone when I'm not here, okay? Especially when you're dressed like a girl."
"Okay," I replied. He said I was gorgeous and sexy."
"You are, baby," Frannie replied. "But guys like him can be dangerous. Some guys do terrible things when they're alone with a young, sexy girl, and that's what you are now."
"I know a little about ****," I said.
"It's the worst thing that can happen to a girl," Frannie said. "And if he ****d you and found out you're not really a girl, he might beat you or even worse. Guys tend to react badly when they find out the girl they thought they were fucking is really a guy. We girls have to be careful, okay?"
"Okay," I replied.
She finished applying my lipstick and stood back to look at me. "Perfect!" She pronounced.
She had me stand up and walk around in the boots, and she gave me some tips on walking in heels as well. When she was satisfied, she asked me if I still wanted to go out with her the next day dressed as a girl. I said I did, and she told me that she had already told my mom she was going to take me out for the day and that I should come over about 10:00 to get ready.
Frannie asked me to unzip her dress, which I did, and she removed it and then sat on the bed so I could remove her heels. When I looked up she had removed her bra as well. I stood up and asked if I could touch them and she said yes and that from now on anytime she took her boobs out I was welcome to touch them. I reached out and fondled her beautiful breasts, squeezing them gently, and then pinching her nipples. She told me to pinch hard and I did, and she moaned and closed her eyes.
After several minutes of that, Frannie was breathing hard. She pulled my face close to hers and we kissed again, using our tongues like we had before. This time when she pulled back, her face was flushed and she was breathing fast.
"I want you to do something for me, honey," she said.
"Anything," I replied.
"You're such a good girl," Frannie said and smiled at me. I smiled back and she said "I want you to suck on my nipples. Will you do that for me?"
"Oh yes, Frannie!'
Frannie lay back on the bed and I climbed up beside her. She told me she wanted me to first kiss her boob all over and then kiss her nipple, and then she would tell me what to do next. I lowered my head and kissed her breast just above her nipple, and then I kissed it all over. After several minutes Frannie told me to kiss her nipple so I did. I loved the taste and texture of her hard nipple. My cock was rock hard and had been since I had first touched her breast. I could feel my pre-cum oozing into her panties. Then Frannie told me to open my mouth and wrap my lips around her nipple and gently suck on it. I did as she requested and she moaned with pleasure. Then she told me to suck harder, and then harder still. After that she told me to bite on her nipple and when I tentatively did so she told me to bite harder. She was breathing hard and moaning a lot now. I looked down and saw she had a hand down her panties and was rubbing her pussy. Then she cried out and her body started shuddering and I thought I had hurt her. I asked if she was okay and she said that she was and explained what an orgasm was, telling me it was basically the same as when I jacked off and spurted.
"That was great, honey," she said. "That felt really good. Do you want to do the other one?"
Of course I did! I moved around to the other side of her and repeated the process on her other breast and she rubbed her pussy and soon had another orgasm. When she stopped shuddering, she smiled at me and said "Now let me do something for you. Lay down on your back."
I did as she instructed and she lay down beside me and started kissing me again. At the same time she reached under my skirt and into my panties and took my hard cock into her hand.
"You're really wet," she said between kisses. "It's great lubrication."
She kissed me with lots of tongue as she stroked my cock and I came just a couple of minutes after she started. I was still hard so she did it again and I came a second time about five minutes after she started. Then she raised her hand to her mouth and licked some of my cum off of her hand.
"Did you like that?" She whispered into my ear.
"I loved it Frannie!" I replied. "Do it again, please!"
Frannie laughed and reached back into my panties and said, "Maybe later. This little guy needs some time to recover!" She licked her hand clean and then kissed me, and then she stood up.
Frannie looked at me for a second and said "Would you like to see my pussy?"
All I could do was nod my head yes and watch as she slid her panties down over her hips and down to her feet. She stepped out of them and stood up and I had my first really good look at her pussy. She had a lot of hair, so all I really saw was her bush, but my cock began to stir as I stared at her blond bush. She saw my cock swelling and laughed and told me I was amazing.
Frannie climbed back up on the bed and lay down beside me. She told me to get down between her legs so I could have a close up view. When I was in position she spread her vagina apart with her fingers so I could see better and I was fascinated by the pink flesh, the little knob at the top, and the dark hole that looked so inviting. Her scent wafted up and I inhaled deeply.
"Oh, Frannie!" I exclaimed. "That smells so good!"
Frannie laughed. "That's good. Sometimes it can get a little stinky down there."
"It smells wonderful."
"Explain what you see," Frannie said.
"The outside looks like big sideways lips," I said, and Frannie laughed.
"That's called the labia," she explained.
I knew all this, but she seemed to enjoy explaining it to me so I played along.
"There's a big hole at the bottom, and I can see a smaller hole above that."
"The big hole is the vagina," she continued. "That's where your cock goes when a man and a woman have sex. The little hole is called the urethra, and that's where my pee comes from. What else?"
"There's a little knob at the top that looks a little bit like the top of my cock, only smaller."
"That's called the clitoris, or clit for short. The reason it looks like the head of your cock is that it's very similar. When a woman gets sexually aroused, it swells, just like your cock does when you get aroused. It's the most sensitive part down there. It feels very, very good when you touch it."
"May I touch it?" I asked.
"Yes, you can touch it," Frannie replied.
I reached out and touched her clit with the tip of my index finger. Then I pinched it gently between my thumb and finger.
Frannie twitched and said "That's it. That feels nice."
I pinched her clit again and then she told me to rub it in circles with my finger, which I also did.
"Don't get scared if I scream," Frannie said. "When I come, I sometimes scream or moan loudly."
I rubbed my finger rapidly all over her clit, which grew just like she said it would and became harder. After several minutes Frannie was breathing hard and arching her back and then she did scream and clamped her legs together, grunting and shuddering.
Despite being told not to, I thought I had hurt her and started to pull my hand away. Frannie grabbed my wrist and pulled it back and told me to keep rubbing. I did as she asked and she bucked and shuddered for almost a full minute. Then she lay back on the bed and said "That was wonderful."
I was very pleased that she liked it. After Frannie settled down a bit more she told me to stick my finger in the big hole. I did so tentatively, and exclaimed out loud when I felt how warm and wet it was.
"That's where my cum comes from," she said. "When I have an orgasm, which is what I just had, my juices flow heavily from my vagina. It's the same type of fluid that comes out of you when you're leaking, not the gooey white stuff like your cum. Taste it."
I licked my finger tentatively, and loved it. I stuck my whole finger in my mouth and licked her juices off of it, then asked if I could taste some more. She laughed and said to go ahead so I inserted my finger in her pussy again and then licked it clean. I repeated that process twice more before she told me to stop.
"It would be a lot easier if you just lick my pussy," Frannie said. "If you want too."
I really wanted to, but said, "I have never done that before. What do I do?"
"Just get your face close, and slip your tongue in there," Frannie replied.
I moved forward until my face was close to her pussy and put my tongue out and licked her labia. It tasted amazing, and I licked all over her labia and inserted my tongue into her vagina. Frannie was moaning again and she told me a few things to do. After several minutes she told me to move up and lick her clit. I did as she instructed and then she told me to flick my tongue over it as fast as I could.
"And put one of your fingers inside my pussy," she said.
I slipped an index finger inside her and flicked my tongue over her clit. She was moaning and moving her hips and she told me to move my finger in and out while licking her vagina. I did and few seconds later she had another orgasm, this one even longer than the first. She clamped her legs around my head and it actually hurt a little she was squeezing so hard. But I kept licking and poking. When she was done she unclamped her legs and sighed and said "That was great, honey. You're very good at that." I was very pleased.
I moved up beside Frannie and she put her arms around me. She said, "We shouldn't be doing these things, you know?"
"Why?" I asked.
"I'm so much older than you," she replied. "People don't always understand when two people who are so far apart in age enjoy having sex together."
"But I don't want to stop doing it!"
Frannie sighed. "Me either. So we won't stop, but you have to promise me you won't tell anyone about the things we do."
"I'll never tell, Frannie, I promise." I said solemnly.
"I promise never to tell either," Frannie said, and she kissed me on the lips, slipping her tongue into my mouth. I kissed her back and hugged her tight. I would do anything for her.
After that, Frannie gave me another hand job and I came again. She licked her hand clean and then licked my cum off my belly as well, telling me it was delicious. After that we got up and removed our makeup, and then I removed my lingerie and dressed in my own clothes. After another really nice kiss, I went home after telling Frannie I would see her at 11:00 the next morning.
Back at my apartment I masturbated before going to sleep. I couldn't get Frannie out of my head. The things we had done that night were the most pleasurable I had ever experienced. I was nervous about going out in public dressed as a girl the following day, but if Frannie thought it was possible, I was willing to try it. The thought of going out dressed like a sexy girl was thrilling. I also knew I would do anything Frannie asked me to do.
The next morning I dressed in jeans and a t-shirt, said goodbye to my mom, and walked over to Frannie's apartment. Frannie was wearing a robe when she let me in and she kissed me on the lips and asked how many times I had jacked off when I got home.
"Only once," I said, and Frannie laughed.
I said hello to Caleb, who was playing in the living room and I followed Frannie back to the bedroom. Once we were in the bedroom, she closed the door and slipped out of her robe. She was naked and looked more beautiful to me than ever. She told me to take off my clothes so I did, and then she asked if I wanted to lick her pussy before we got ready. I replied that I did.
We got up on the bed and I ate her pussy. She was already wet when I started, and she told me what to do again and she had three orgasms before she told me to stop. I loved the smell and taste of her and could have happily spent the entire day between her legs. My cock was rock hard and dripping and Frannie told me to lie on my back. Then she got between my legs and took my cock in one hand and licked the pre-cum off the head of my cock. Then she swirled her tongue around the head of my cock while squeezing it and moving her hand upward. I felt more pre-cum ooze out, and she licked that up as well.
Then Frannie ran her tongue down one side of my cock and up the other several times, and then she pressed my cock against my belly and licked underneath my ball sack, and it felt wonderful. After that she swirled her tongue around my balls, and then sucked gently on each of them. Then she opened her mouth and swallowed my cock and I came in her mouth. Frannie looked up at me and swallowed my cum, drinking every drop. It felt wonderful, but I hadn't wanted it to end so fast. Frannie seemed to sense that and said she would do it for me again later.
"That was amazing, Frannie," I said when I could talk again.
Frannie laughed, still holding my cock in one hand and licking it occasionally.
"What are we going to do about this?" Frannie asked. "We can't dress you up like a girl and then have your erection ruin everything."
"Maybe another blowjob would do the trick," I said, helpfully. Frannie laughed again and let go of my cock, and then she stood up and held her hand out to me.
"Let's get ready, shall we? "She said.
We went into the bathroom and cleaned up, and then we put on our lingerie. Frannie had picked out a red bra, panties, and garter for me since I had cum all over the one's she had picked out for me the night before. She also gave me a pair of sheer black stockings. Frannie had black lace lingerie for herself. She also picked a couple of pairs of white cotton panties to stuff in my bra.
"We'll buy some inserts