Frannie's Femboy

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 kids?"

"I don't have any kids," he laughed and I blushed. "Sorry, I was just kidding," 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 rape," I said.

"It's the worst thing that can happen to a girl," Frannie said. "And if he raped 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.