I had been babysitting Stefan for the last two weeks, and having fun with him, when one night after an evening of spanking, masturbating, and anal sex he was getting ready to go to bed.
"Hey! Guess what?" Stefan blurted.
"I told my girlfriend what you and I do at your hideout and here when you babysit me."
I all of the sudden felt a shiver run through my body when he made that announcement.
Looking at him I said, "Why did you tell her that. What if she gets mad at you and tells her Mom. She might turn around and tell your Mom and then my parents and then we all be in big trouble."
"She won't tell on me."Was is confident answer.
"And why not?"
"Cause she told me things she has done that her Mother and Daddy don't know."
Mutual blackmail, cute.
"What has she done that her parents don't know about." I wanted something to hold over her just in case.
He went on and told me how one day she charged the local boys to look at her panties. Extra if they wanted to touch it. Another time, she had let boys touch her bare bottom, again, for a fee.
As I listened to this I asked myself, what kind of town did my parents move me to.(Sheeesh!)
"But you know what else we did?"
"One day, when Mom was at work, we went down to my basement and show each others pee pee and coo chee."(Kids and their words for dick and pussy)
"Anything else?" I was pumping him for more info.
"Well, after I met you and started playing the games, a couple of days ago I tried playing 'doggie' with her."
"Really!" Now my cocklet was paying attention.
"And did she like it?"
He lowered his head. "No! My peep pee wasn't long enough to go inside her."
I snickered to myself but I knew that this was important to him.
"Well, don't worry about it. As you get older, your pee pee will get bigger."
"You think so?"
"Oh yes. So don't get upset. Ok?"
"Ok." I noticed though he was still thinking about it.
"What are you thinking/"
"I was just wondering something."
"Could you show her what it feels like to be played spanked, doggie, and playing with her coo chee? I think she might like it."
Be still my beating heart.
"Well, I don't know. Did you tell her all that we do when we are alone?"
"And what did she say?"
"She thought it would be fun to try."(Down boy! Down!) I yelled at my cocklet.
"Well. Ok, if she is willing to try it, I'll do it."
With that, Stefan jumped up and gave he a hug. "Thank you, big brother . I appreciate it."
I then proceed to ask Stefan about his girlfriend.
He told me that her name was Christine but she liked to be called Chrissie. She was six years old, like him, and the same height as he. She had, what Stefan called, a Betty Boop like face but with sandy hair. She also wore glasses and had a bit of an overbite. The rest of her I could discover on my own. I told Stefan to tell her to me meet me at the gate two days from now and to come alone so that way she would not feel uneasy in front of Stefan. He understood. I told him that would give him time to find her and tell her that I said is ok for her to come over. After our talk, I put Stefan in bed, said goodnight and he went right to sleep.
Two days later, I was sitting on my back porch waiting to see if she would appear. I thought she might have had second thoughts. After a few hours, I was just about to give up when I heard a light knock on the gate.
I went toward the gate, and opening the panel, I looked out
There standing in front of me was Chrissie. She had ridden her bike here and was now standing by the gate and holding her bike. She was looking up at me and smiling.
"Hi!" she said in her little high pitch girl, voice. "You must be David." Then looking around, she said in a low voice. "My boyfriend Stefan sent me."
"Oh yes! He told me about you. I'll let you in."
I closed the panel and open the gate and stood to the side. "Come in."
"Thank you."(Very polite) As she went by me, I took a quick look outside to see if she was alone. After making sure, I quickly closed the gate and locked it and went back to meet Chrissie.
She had parked her bike where Stefan had done before(Stefan must have told her to) and was now standing by the garage door waiting.
I unlocked the door and let her in. She thanked me again and went in to the hideout. As she went in I took a good hard look at her.
She was as Stefan had described. She was wearing a girl's pocket T-shirt with a Barbie logo on it. Her pants were capri shorts. These were the type that unbutton on the side. She was also wearing white socklets and blue sneakers. As she continued walking into the room, I looked at her ass. She had a nice rounded bottom that looked to be firm. She showed signs of being out a lot because she had a nice tan on her.
She went over to the boxes of toys and comics. She approached the comics and bent down to look in. When she did that, I noticed her ass slowly spread till it look like she would burst out of her shorts. By now my cocklet was getting stiff in my shorts.
She straighten up and turned to look at me. "You have a nice hideout." Then she saw the chocolate in the bowl. As she approached it, she looked at me and said. "Stefan told me that if you grab the chocolate out of the bowl without you saying ok, that you spank the person for it. Is that right?"
So saying, she reached out to the bowl and grabbed a handful. I stood there watching this little minx get into trouble on purpose and I laughed to myself. She ate about four bars and put the last two in her left pocket. "Am I a bad girl now?"
I walked past her and sat down to look at her at eye level. As soon as I did that, I grabbed her by the arm and pulled her toward me.
"Why are you doing this?"
She looked at me with a confused look and said. "Stefan said that If I misbehave, you would spank me and then play nasty games with me including doggie."
"And that's what you really want to do?"
She nodded her head vigorously.
I slowly brought my hands around her waist and slowly pulled her toward me, my hands slowly moving down and cupping her bottom.
"Chrissie." I started, "do you like being spanked?"
She nodded her head. "Stefan and I have played spank games were he spanks me. It makes his pee pee stiffen and makes my coo chee tingle."
That explains a lot.
"So! Are you going to spank me then play with my coo chee and doggie me?"
"Stefan did tell you what doggie is, right?"
She nodded her head again. "That's were you put your pee pee in his bottom hole and move it in and out till you both explode. He also told me that you play with his pee pee while you doggie him so he can explode with you."
"Did he also tell you that I have to get your bottom hole ready for that?"
She nodded again. "He told me about how you use a butt tickler on him. It sounds like fun." Then she lowered her head and said. "I don't know how you are going to play with my coo chee since I'm a girl and don't have a pee pee like Stefan."
I snickered to myself. "Don't worry. Even girls can have fun."
She lightened up and said. "Really! Cool. Can we start now."
She really wants this.
"Ok. We'll begin by you taking off all your clothes now."
With that, she stepped away from me and removed her T-shirt. I took it and hung it on the back of the chair. She then started to unbutton her pants and removed them. Again, I grabbed them and hung them up with her shirt. She removed her last piece of garment a pair of frilly pink panties. I took the last piece and added them to the rest.
I then gazed at this naked little lolita.
She had a rather flat chest but still nice for her age. As I continue my gaze I noticed that her belly button was an outtie. Still looking further I saw her little bald pussy. It pouched out just a bit so it was bit prominent. Her skin was flawless. I noticed that she had white areas at her chest were her nippies are and around her midriff.
I told her to turn around and when she did I gazed at her round bottom. Her bottom was round and seem to have a bit of a overhang were the legs met her bottom. I told her to bend over and touch her toes which she did without hesitation. In the bent position, her cheeks spread apart giving me a great view of her rectum and pussy.
I just sat there and just looked and thought what delicious things I was going to do to this willing little girl.
I reached out and pulled her toward me. She stood up, and shuffled back towards. As soon as she was in my arms, I reached out with my hands and began to play with her nippies.
At first she was confused, but, when my hands began to rub and flick her nippies, she inhale and moved her ass back into my crotch. I continued to rub and tickle her nippies the whole time she was grinding her ass into me and getting me hot. The little minx was now breathing heavily.
As I continued playing with her nippies. My right hand moved down looking for her pussy. As soon as I felt her slit, I began to rub it and got her motor running. She was still grinding her ass against me and moaning out her lust. After a few minutes of rubbing her pussy, I felt her button coming out to play. I move my right hand towards it and began to frig her.
She let out a yelp then looked at me, her mouth and her eyes wide open.
All she could do was nod her head and breathe hard. She then laid her head back on my chest, closed her eyes, put her hands on my thighs for support, and spread her legs wider so I could have full access to her.
For the next few minutes, I continued to make her realized that she did not need a pee pee to have fun. Between I playing with her nippies and pussy the little girl must have thought she was in heaven. Finally, after a few minutes of this intense attention on her charms, she arched her back and yelled out. "I'm explodingggggggg." Then collapsed in my arms.
As Chrissie caught her breath, I took the opportunity to pick her up and place her over my lap. Once in position, I looked down at her cherubic bottom. Her cheeks parted as soon as I draped her over my lap. I was going to enjoy spanking this girl's ass and, after it was rosy red, I was going to slide my cocklet into that ass. Speaking of sliding, I reached out and spread her plump cheeks. As I looked down I saw an entrance worth fucking. Her little rectum was slightly open in this position. I could see how pink her insides were. The other thing that I noticed was a slight scent of roses wafting out from her cheeks. I guess she must have borrowed some of her Mother's rose water and drizzle some in her cheeks. Such a proper lady.
As she slowly regain some consciousness, I opened the drawer and pulled out the Vaseline and sharpie, I opened the other drawer and took out the paddle ball paddle. Once I had what I would need to play with her I began to rub her round cheeks.
Finally, Chrissie began to stir. At first she was trying to figure out why she was in this position till she realized that she was across my lap and naked. She looked over my shoulder. "I like what you did to my coo chee and boobies." She felt my hand rubbing her bottom. "Are you going to spank me now?"
"Not yet." I said. "I thought I make your bottom hole ready for the doggie later. Ok?"
"Are you going to use the butt tickler?"
"Yes I am."
"Ok. I'm ready."
With that, I reached for the vaseline and, after opening it, I smeared some on my middle finger. She raised herself a bit and watched the preparations.
"Are you going to put your finger in my bottom?"
"Yes I am."
"Will it hurt?"
"Only if you don't do what I say. Ready?"
She laid down again. Her head and arms draped over my thigh. "Ready." she said with a hint of nervous in her voice.
I spread her cheeks apart and, bringing the middle finger up to her soon to be entrance, I tickled her anus. Just like Stefan she wiggled and giggled across my lap and said. "That tickles."
Once her entrance was lubed, I began to slide my finger into her little hole. Her rectum gave rather easy, although I could hear from the other end a few sounds of discomfort.
"Yessssssssss!" Was her response.
I continued pushing in till my finger hit bottom(Literally). I didn't move it letting her get accustomed to the invader. At the other end, I heard her taking shallow breaths. After a few minutes I slowly began to pull the finger out of her hot, smooth, clinging butt hole. When I had the tip at the entrance, I then moved it back in. I felt her grabbing my legs with her hands and trying to get acclimatized to the feelings in her asshole. After a few minutes of massaging her rectal walls, I pulled the finger out. As it left, I saw her rectum go back into its original position.
After wiping my finger off, I picked up the sharpie and lubricated it. Before I stated I decided to distract her of what the sharpie was going to do to her. So I lifted her up and draped her over my left thigh. That would give me access to her pussy. She looked over her shoulder with a quizzical look.
"I'm going to put the butt tickler in. I thought you would like me to tickle your coo chee." When she heard that, she smiled and nodded her head.
"Ok then. Here we go."
I spread her ass cheeks apart and put the sharpie up to her rectum. Rubbing it at the entrance I saw her relaxing. I then pushed the sharpie in till it was halfway in. Again she hissed out her discomfort but did not complain. Once the sharpie was in, I reached around her waist and and after finding her pussy, I began to frig her again. She let out an "Ooo" when I did. At the same time I began to move the sharpie in and out of her asshole.
The little minx was wiggling over my lap making sure that my fingers tickled her pussy. In the meantime, the sharpie was doing its job of opening her up while at the same time it got her accustomed to things going in and out. As my fingers found her clit again and began to frig her, I watched how the sharpie went in and out of her rectum. She seem to caress the sharpie with her butt lips so much so that I couldn't wait to fuck it.
Meanwhile at the other end, the owner of that butt hole was letting me know how much she was enjoying this new game. She let out moans and groans with an occasional "Yes." in a low voice. As she got closer and closer to her second virginal orgasm, her head slowly raised up till finally she let out raucous shriek and then collapsed over my thigh.
As she laid across my thigh, I pulled out the sharpie with a plop and put it up on the stand. I lifted her up and once again, I put her over my lap. It was time for the young lady's spanking.
Rubbing her bottom, I waited till she came down to earth. When she did, she looked over her shoulder and realized she was in the same position as before.
"Ready for your spanking, naughty girl?"
She gave a me looked of both fear and excitement and nodded her head.
"Alright. Here we go."
Smack, smack, smack, smack, smack, smack, smack, smack, smack, smack, smack, smack. I decided to start with a dozen crisp smacks to her rounded little butt. Overtime my hand made contact with that delicious little girl flesh it would wobble and come back into its original position. I rubbed it a bit before I gave it another dozen. So far, Chrissie seem to be enjoying the attention.
Smack, smack, smack, smack, smack, smack, smack, smack, smack, smack, smack, smack. The little minx laid across my lap and, except for an ouch or two, she was accepting this spanking. I rubbed her pinkened cheeks for a bit then began again.
Smack, smack, smack, smack, smack, smack, smack, smack, smack, smack, smack, smack.. By now her cheeks were a dark pink and still she didn't show any major reaction. Although a few times, I swear she raised her bottom towards as if she was telling me she wanted more.
At this point, I picked up the paddle and rubbed it on her dark, pink, bottom. She turned her head to see what I was rubbing. I held it up so she could see it. When she looked at it, she looked up at me and nodded her head slightly. With that, she turned, lowered her head and waited. The little minx could take it. I was beginning to like this kid and so was my cocklet.
Whack, thwack, smack, whack, whack, whack, whack, whack, thwack, whack, whack, thwack. By now, her bottom had a light red color to it. I put the paddle down and rubbed her bottom.
She slowly turned and looked up at me. I could see tears in her eyes. "Can you give another 12 with your hand. I'm a very bad girl." Then she went back into position and waited.
I wasn't going to deny her her wish so I gave them to her only light this time.
After I did, I began to rub her bottom again. She turn and looked at me. "Thank you. Am I a good girl now?"
"Yes you are."
"Does that mean that you'll tickle my coo chee and doggie my hole too?"
"Yes." (My cocklet was saying yes too)
"Good. I want to feel what my boy friend got."
"And so you will."
I lifted her off my lap and carried her to the ottoman. Once there, I draped her over the ottoman. Her ass in the proper position to receive my cocklet. She stayed in the position I put her and, except for her plump ass moving a bit, did not move. Getting the Vaseline, I dropped my pants and undines and approached this willing little girl. She kept looking at me. In particular my cocklet. The look on her face made her wonder if she would be able to take it.
Still looking at me she said, "Are you sure that big thing is going be able to go into my little hole?"
"If you do what I say, it will." I reassured her.
I dropped down to my knees and instructed her to spread her legs, which she did willingly, although she still had a look of doubt on her.
Once she spread her legs, her cheeks opened enough form me to see her rear opening. I coated my cocklet with the Vaseline, and taking a dollop, I applied it to her rear entrance and slipped my finger in to lubricate her some more. With everything ready, I said. "Ok Chrissie, Just lay your head down on the ottoman and relax. I'll do all the work. Ok?"
"Ok." sounding not quite convince.
I scooted forward, and aiming my cocklet at her hole, I began to slowly press in.
At the other end, I heard a low, long, moan coming out of her as I kept pushing into her not so virgin asshole. As I kept pushing in, her sphincter muscles began to massage my cocklet like it was an old friend. When I finally bottom out in her anal sheath, I thought I was in seventh heaven. My hips were up to her cheeks and it felt wonderful being deep in this six year old girl's ass.
"How are you doing?"
She looked over her shoulder at me and even though her face told me she was uncomfortable, she said. "Are we doing doggie now?"
"Should I pull out?"
"No! If Stefan can do it, I can too." (Brave girl.)
I stay deep in her ass enjoying how her ass muscles were massaging me.
Finally, after a few minutes of blissful squeezing by the little minx, I grabbed her hips, leaned over and said. "Ok, here we go,"
"Ok!" She yelped out.
So I began slowly fucking her little asshole. God! It felt good being inside this girl. I slowly built up speed. All the time watching how her very stretched putties caress me as my cocklet slid in and out of her.
After a few minutes of loosening her asshole with my pistoning I brought my right hand around and, finding her clit, I began to frig her clit in rhythm to my ass fucking.
As soon as she felt her clit being played with, she raised her head and said. "Oh My! Oh Ooooooooooo!"
I fucked her ass faster as my hand continued to rub and frig her clit. Her little ass shaking and taking the slaps that my hips were applying to her.
This went on for several minutes. She uttering O's everytime my cocklet went in, her ass and my cocklet making squelching sounds due to the lubrication, slapping noises from my hips as I continued to smack her ass cheeks. Once in a while, her little asshole would make a small farting noise form the air being trapped in her rectum.
Finally, with both reaching out peaks of pleasure, I fucked her faster and worked on her clit till we both achieved our orgasms and then collapsed.
Catching my breath, I felt her asshole still spasming around my cocklet. As I slowly came down, I didn't feel my cocklet getting soft. In fact it seem to be getting hard again. Chrissie noticed and looked over her shoulder at me. "You're getting hard again, she said, "What does that mean?"
I just looked down at her and said, "It means we are going to doggie again." A lustful smile on my face.
She looked at me with a look that told me she did not expect that. "You mean you are going to doggie me again?"
"Yes I am."
"But! My hole is sore. It will hurt."
"I'll rub your button again. That will help."
"No it won't. My coo chee is also sore from all the rubbing."
"Than that leaves one place I have not made sore."
"What is that?"
With that, I reached for her nippies and began to rub and flick them. As soon as she felt that, she pushed her ass back on me and let out an "Oh".
So once again, I began to fuck her ass.
As I pistoned in and out of her well used asshole, I continued to play with her nippies. As she felt this, she once again, began to wiggle her ass and occasionally push it back to me. As we continued this second bout of anal sex I continued to worry her nippies and would sometimes reach down between her legs and flick her clit. This new assault on her lolita body was making her moan and give out keening noises as she slowly began to head toward another orgasm with me.
We reached our orgasms at once, Her sphincter muscles really squeeze my cocklet so hard I thought she was going to shoot me out of her. This time, I felt my cocklet slowly easing out of her ass. Wow! that was intense. My first double ass fucking in the same ass. A First!
After my heart slowed down, I got up and walked over to the chair and sat. Reaching over for the paper towels, I began to clean my rather sensitive cocklet of the Vaseline and her own ass scum(Is it feasible to have an ass orgasm?). When my cocklet was cleaned and was dressed, I went over to Chrissie with some towels to clean her up. I knelt down behind her, and speading her cheeks a bit, began to wipe our her asshole and ass cheeks. My luck was still with me, even after being ass fucked twice, her asshole showed no damage.
Once I cleaned her, I went back to the chair and sat. I was blown after that bout.
My little lolita began to stir. She slowly got off the ottoman and leaned back on her knees. As soon as she did that, she shot up and grabbed her bottom. She slowly got up still holding her bottom and saw me sitting on the chair. As she walked over, she gingerly took small steps till she was finally in front of me.
Looking up at me and still holding her butt cheeks she said. "Did you doggie Stefan twice like you did me?"
"No." Was my response. "You are the first one whose hole made me do that."
Still holding her cheeks, she said. "I guess that makes me special, huh?"
"I guess it does. Did you like it?"
Still holding her cheeks she lowered her head and with a coy smile said, "Yeah! Kinda."
"Would you do it again?"
Her head shot up on that one. "You mean now?"
"No, no. When you feel like it."
At that point, she rubbed her bottom a bit and said. "Yeah! When I feel like it. Right now, my hole, coo chee, and boobies are a bit sore."
"Whenever you are ready."
I reached over and gave a her a couple of pieces of chocolate for her trouble. She took them and ravenously ate both thanking me as she did.
I grabbed her and put her on my left thigh. I wanted to check her no longer virgin asshole. After spreading her cheeks, I didn't see any rips or tears on her butt lips but I'm sure her anal passage is a bit raw from the ass fucking.
Giving her cheeks a few light taps, I set her down on the floor and proceeded to give her her clothes. As she got dressed I felt that I would have to thank Stefan tonight for sending her over to meet me. Once she was dressed, I pulled her toward me and gave her hug, my hands slowly moving down to cup her round bottom. After I hugged her, she pulled me down and planted a kiss on my left cheek and thank me for introducing her to what Stefan was talking about.
As she left the alley, I started thinking that maybe, one of these days, I might have both her and Stefan come over together so we could have some real fun(Or at least I would have some fun).
But right now, I need to take a shower, eat something, pack my tote bag, and get ready to go babysit the little imp.
I said it once and I'll say it again.
I LOVE THIS TOWN.
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