Little Man Pretty Girl Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I wanted to keep my lips down at the bottom of her shaft but my need for air was too great so I slid back up. When my lips reached the flare of her head Janie fired another squirt of come into my mouth. She then took her cock in hand and while I kept the head in my mouth she pumped several loads of hot cum into my mouth. I tried to hold her load in my mouth so I could show her it like she did to me, but with her big head in my mouth there wasn't much room for cum. I had no other recourse then to swallow some of it down.

When Janie stopped cuming and I could feel her shaft start to soften I pulled my mouth off and looked up toward her face. Janie looked down at me with glazed eyes and smiled. I open my mouth so she could see the cum that was left in my mouth then with exaggerated movements I swallowed down her load.

Janie held out her hands and I crawled into them. She kissed me on the forehead and said, "God that was good did you enjoy doing that." I nodded my head and Janie said, "I thought so you did it so well for your first time. I think you're a natural at cock sucking and believe it or not but that's a good thing especially if your going to do it often. Now give me a few minutes and I'll return the favor."

"You don't have too I can wait till later or you can fuck me like you did in my dream."

I felt Janie tense up slightly before she said, "What dream baby girl."

"It wasn't really a dream I just had this vision that I sucked you off and you fucked me, but that was before I knew you had a cock," I told her.

"Honey I don't have a cock and neither do you. We girls have clits. Give me a few minutes to rest then tell me about this vision."

Janie may have thought she only needed a few minutes rest but the next thing either of us knew it was late morning. I woke up first but my movements woke Janie. We kissed good morning before we got out of bed to pee.

Janie sat on the commode first to drain her bladder. When it was my turn I stood in front of the commode but Janie stopped me by saying. "Baby girl only boys stand to pee. Girls have to sit so it doesn't run down their legs."

While I sat to empty my bladder Janie pulled out a clear plastic bag that had a long tube attached to it. She filled it with water and added a little bit of soap. Once she was done filling the bag she said. "I'm going to show you how girls like us have to clean ourselves before we take a shower. We also have to do this whenever we make a poop.

Janie told me to bend over the vanity. She then took the nozzle and after lubing it slid it into my ass. Once the nozzle was in me she open a valve on the tube and I instantly felt warm water fill my rectum. Not knowing what was going on I asked her why we had to do this.

"We need to keep our pussies clean so if our boyfriends come over we'll be ready to fuck them. You don't want you boyfriend's cock covered with anything nasty do you." I wasn't sure if I wanted a boyfriend but I didn't want her clit cover in shit either so I told her no. "Of cause you don't so we do this each morning and anytime we feel the need."

While I drained out my enema Janie filled the bag once more. Once more I was bent over the vanity and filled. After three enemas I was proclaimed clean then Janie gave herself three while I was sent into the kitchen to start breakfast. She wanted to eat before we showered together because she wanted to teach me how to put on my makeup today.

Janie and I sat down at the kitchen table to eat wearing satin robes and panties. Once we were settled she asked me about my vision. I told her what I saw and when I saw it.

After I finished telling her about them she said, "I guess I owe you an apology. You see you didn't have a vision your were remembering what we did together. Just before we left the club the first night we met, I slipped something into your drink. It was meant to relax you and lower you inhibitions. It also makes you forget what you did while the drug is in your system. You see when I saw you at the club I wanted to have sex with you but I didn't think you would want me when you saw what I was. I was pretty sure you would like dressing up as a girl but I couldn't be sure you would want to have sex with me before I got you to change. So you only vaguely remember what we did. I'm sorry I did that and I promise to never do it again."

I didn't like that she drugged me, but there wasn't much I could do about it. I also didn't want to ruin what looked like a good relationship with something that was passed us. I told her I forgive her and we wouldn't mention it again. Janie seemed relieved that I took it so well and she came over and kissed me.

After breakfast was over we went and took a shower together. We washed each other off and did each other's hair. Half way through the shower Janie dropped to her knees and took my clit into her mouth. She gave me a slow blowjob while massaging my anus with her finger. I held out pretty well until she slid her finger into my asshole. When she did this I instantly blew my load into her mouth. After, we kissed and shared my load like we did the day before. This time I expected it and I enjoyed it.

As soon as we got out of the shower, dried off and in panties and a bra Janie rolled my hair with the curlers. She didn't want a repeat of the day before. She next sat me down in front of the full size mirror so I could see everything she did to me. When she did my eyes she did one and had me do the other one. Mine didn't come out anywhere near as good as hers did. She then had me wash off my eyes so I could start again.

It took most of the day before I finally was able to do it as good as she did. When she asked what I wanted as a reward for learning how to put on makeup I told I wanted to ruin my lipstick by leaving most of it on her clit. Once she had my hair out of the curlers and brushed out we made our way over to the bed where I once more sucked her off till she came in my mouth.

After I sucked her off Janie noticed my hard on and asked, "Would you like to fuck me? It's been a while since I had a girl to make love to me."

"I would really like to try it but I doubt I'll give you any pleasure," I told her dejectedly.

"It's okay baby girl I'd like to try it anyway. Besides you're going to lick me back there first aren't you. I really like that," She told me. I hadn't thought of that but I was willing to try it. I knew she was clean and I was willing to try anything she wanted.

Janie rolled over and offered me her bottom or as she wanted me to call it her pussy. She did have one beautiful bottom. Her cheeks were soft to the touch and firm like two ripe melons. I started out kissing each cheek over and over until I cover each one with kisses. After both cheeks were thoroughly adored I moved to the crack between them. I started by licking the crack lightly with feather like strokes before I started to delve deeper into the crack.

Once I was as deep as I could go I spread her cheeks apart and licked her anal star. As soon as my tongue touched her sphincter Janie moaned deeply and she wiggled her bottom on my tongue. I coated her hole with saliva and even kissed it reverently.

But that wasn't enough for Janie as she moaned she said, "Come on Baby girl slid your tongue into me." Call me stupid but I didn't think about sticking my tongue into her.

I tried to push my tongue into her but it wouldn't go in until I rolled my tongue into a tube and pushed it in. Janie squealed instantly and shoved her bottom back toward my face as she said, "Oh that's it baby girl fuck me with your tongue shove you tongue into my pussy. God that feels great."

With her praise ring in my ears I started to fuck her hole with my tongue. Over and over again I plunged my tongue in as deep as I could and Janie screamed for more. I tongue fucked her till my tongue became too weak to move. Janie then pulled her ass from my face and said, "That was good baby girl, now give me your clit."

I knelt up and quickly pulled my panties down out of the way. I spread Janie's cheeks apart and pushed my little clit up to her hole. Her hole open easily and my little clit slid in about an inch. I heard Janie moaned and tell me to give her all of it. I slid in another inch and she had all I could give her.

I started sliding my clit in and out. Though I couldn't go in too deep it still felt great. Janie hole was still wet from the oral attention I had given it and her insides were extremely warm. And the fact that I was fucking something other than my fist was almost more than I could stand. Janie's right hand came up under her and she started stroking her clit. She was moaning sweetly and her hole was squeezing my clit.

I tried to last I didn't want this to end but I couldn't hold out. With in a few minutes I felt my orgasm building and it swept over me like a tidal wave. I told Janie I was going to cum and she told me to fill her. Almost instantly I started to squirt my juice in her and Janie started moaning that she was cuming to.

After dumping my load into Janie's bottom, my clit quickly soften and was expelled from her hole. Janie came at much the same time and after pumping her load on to the sheets she slid into a prone position. I rolled over onto my back next to Janie.

Once Janie recovered from her orgasm she pulled me into her arms and said, "That was nice I hope you enjoyed it as much as I did."

"I did thank you for letting me do that I've never done that before," I told her.

Janie kissed me sweetly and then said. "I guess we need to change the bed linen. You also need to wash your face and redo your make up. And since you weren't thoughtful enough to clean up after yourself I guess I'll have to douche."

I wasn't sure what she meant till we went into the bathroom and Janie filled the enema bag. She told me she did this to clean out her pussy so she didn't drip. After a quick shower we changed the bed linen then I sat and did my makeup while Janie when looking for something for me to wear.

She came back with a short white skirt a pink V-neck T-shirt with lace on the collar and a small pink bow at the bottom of the V. For shoes she gave me a pair of white tennis shoes. I looked at the clothes and asked, "I guess we're not going out tonight?"

Janie giggled and said, "No baby girl we're not. I have a job to do tomorrow and I need my sleep. I hate working on Sunday but it's the only day I can get at the computers. We'll stay in tonight and watch a movie so I can get to bed early."

Janie ordered a pizza and opened a bottle of wine. We sat in her living room and watched a sci-fi movie on TV. We found out that we both loved sci-fi movies and we talked on about them till eleven o'clock when Janie said it was time for bed.

We changed into nighties, Janie wearing a red one and I wearing a white one. We lay on the bed and started kissing. I wasn't long before I had Janie's hard clit out of her panties and was slowly stroking it to hardness.

It was Janie who stopped me by telling me to turn over on to my tummy so she could play with my pussy. I knew what was coming and I was frightened. I had heard that this could hurt and knowing Janie's clit and how small my hole was I knew that it didn't seem feasible.

But Janie knew what she was doing. First she reached into the bedside table and brought out several dildoes in various sizes. She also brought out a bottle of lubricant. After getting a hand towel from the bathroom Janie slid two pillows under my tummy to elevate my bottom.

Janie then wedged my legs apart before lying down between them. She said. "Don't be scared baby girl I've done this before and I know how to make this a wonderful experience for you. Besides this won't be your first time."

The next thing I felt was Janie's lips on my left cheek. She kissed it tenderly telling me I had a beautiful pussy. She continued to kiss each cheek and ran her tongue over each one. I though it was nice but it didn't do much for me. That was until I felt her tongue slide between my cheeks.

When I felt the wet warm tip of her tongue slide a fraction of an inch into my crack I couldn't stop the moan from escaping my lips. She ran her tongue from the bottom of my crack up to the top and she went deeper on each pass.

When her tongue touched my hole the moan that came out of my mouth sounded more like a squeal. I could almost here Janie giggle at the noise I made. But what was even better was when she slid her tongue into my hole. That was like nothing I ever felt before.

Janie tongue fucked my asshole for a few minutes then I felt her slide her tongue out and something else slid in. At first I wasn't sure what it was but after I felt it move I knew it was one of her fingers. She moved her finger in and out a few times before I felt something cold and wet drip on to my hole. I turned to look and saw the bottle of lube in her hand.

Janie smiled down at me and said. "How you doing baby girl I'm not hurting you am I?"

"God no I don't think I ever felt this good." I told her as I tried to wiggle my ass for her.

Janie giggled and said. "I knew you would love this. You're a sissy slut just like me."

If some one had called me a sissy a few days ago I would have punched him. But when Janie said I was a sissy slut just like her I felt pride in the fact I was like her. Deep down I knew it was weird to feel that way but I couldn't help myself. I wanted to be whatever she wanted me to be.

Janie finger my hole first with one finger before she added a second one. She also used lots of lube and worked it into my hole. I felt her shift on the bed and then she said. "Okay baby girl I'm going to use a dildo now. It's the smallest one I have so you shouldn't feel any pain."

I turned back to look at her and she showed me the dildo. It was very thin almost as thin as my own clit. But it was also six inches long. It was bullet shaped coming to a tapered point.

Janie smiled at me before she pointed the dildo point down and lowered it toward my ass. I turned my head around and I pulled the pillows and hug them to me. I felt Janie's fingers leave my hole and in less than a heart beat I felt the tip of the dildo enter my hole.

The dildo slid into my hole with out any pain. The only thing I felt was a slight full feeling when she pushed it in deeper than her fingers had gone. It also made me feel like I had to go to the bathroom. I want to try to push it out.

Janie moved the dildo in and out going a little deeper each time. The feeling was strange but oddly it felt good and I soon started to like the full feeling. After a few minutes of this I felt Janie move once more and I quickly turned my head.

Janie now held a different dildo. This one looked more like a real cock. It had a mushroom shaped head and I could see what looked like veins running up the side. But this one was thicker than the first one. It was almost twice as thick.

When she pulled out the first one I felt my asshole clinch up as if to stop it from leaving. When I felt the second one at the entrance to my hole my hole remained clinched and Janie said. "Relax baby girl, if you don't it'll hurt."

I tried to relax and I did only barely when I felt it force opened my sphincter. I felt my hole open around the head then snap close around the shaft. The feeling I had to go to the bathroom came back again. But that quickly left and I was left with a feeling that was wonderful.

It's hard to explain the feeling I had as the dildo was pushed into me. The fullness I felt was wonderful and the way it was moving was like nothing I ever felt before. I also felt the tip go in deeper than the last one had.

When I felt the Janie start to fuck me with it I started to whimper. Not from pain but from the pleasure I was receiving. I also felt my hips start to move in rhythm with Janie's fucking.

This wasn't lost on Janie either as I heard her say with a giggle. "You love this don't you baby girl. I can tell you're going to be a slut for a cock in your pussy." I thought to myself, if they all felt like this one I would be.

A few minutes later I felt Janie move once more. This told me that she was going to change dildoes again. I knew this would be the last one before she tried to put in her own. I also knew that this one was a lot bigger than the one she had in me now. I didn't bother to look back.

I felt Janie pull out the dildo and instantly I felt the head of the next one force me open. There was a slight discomfort at first but once the head was in I felt nothing but pleasure. It was different then the other two. First of all it was warmer. It was also thicker and it seemed harder. But it did feel better. It was definitely something I could learn to love.

I felt Janie move and with out thinking I said. "No please leave that one in for a while longer. It feels so much better then that other two."

Janie giggled and said. "Don't worry baby girl I'll leave it in I just need to get into a better position."

I didn't know what she meant but I really didn't care as I felt the dildo move even deeper into my hole. I felt Janie's hand on my hip as she pushed it in deeper than either of the other two had. It was the best I felt so far and my hips started to move to her rhythm.

I soon heard Janie start to whimper as if she was getting some pleasure from this. It wasn't until I felt one of her hands on each of my hips that I realized that it was Janie's clit inside me and not a dildo.

I tried to turn my head and I barely got it turned enough to see her. Through half closed eyes I saw her smiling and I saw her hips moving. Janie was fucking me and I loved every second of it.

When Janie saw me looking at her she said. "Do you love it baby girl do you love my clit in you, do you love me fucking you."

"Yes Janie." I cried. "Yes I love it. I love your clit in me and I love you fucking. Please fuck me. Fuck me deeper and harder."

Janie did what I asked, she pounded her clit in and out of me at a faster and faster rate. She also went in deeper and deeper till her hips were slamming into my ass cheeks.

There was no pain only the pure pleasure of having my asshole reamed. I never knew anything could feel this good. I never knew I could enjoy anything this much. My own clit was rock hard and I could feel it hitting the pillows that were propping up my hips.

Janie started moaning and soon she started grunting in a very unladylike way. She started cussing and she told me what a wonderful fuck I was. She called me a whore and a slut.

When Janie's hips started to lose her rhythm she screamed, "Fuck baby girl I'm going to cum I'm going to cum in you pussy. Are you ready for me to cum in your pussy?"

Of cause I wasn't ready I would never be ready to have her stop fucking me I wanted her to fuck me forever, but I told her to cum in me. I told her I wanted to feel her cuming inside me. I wanted her to fill me with her cum.

Janie slammed her clit into me as deep as she could go. I instantly felt a warm feeling start to spread in my rectum. At the same time I felt myself start to cum. I felt my clit expel a load on to the pillows that were beneath me. The overload on my senses was too much for me and I passed out.

I woke up to the annoying sound of the ringing of the alarm clock. Before I could even move I heard the alarm grow quiet. Janie kissed me on my forehead and said. "Go ahead and sleep a little longer baby girl. I wake you after my shower.

What seemed like only seconds later I felt Janie kiss me once more and say. "Come on baby girl it's time to get up."

I open my eyes and saw that Janie was already dressed in a white blouse and a tan skirt. Her makeup was already on and she was putting on earrings. She told me to clean up and take a shower and she'll be right back.