Exploring With Little Jill  (M,bg,nepi,toddler,exploitation)

by UpsiteDown 



    It had been about a week since my last adventure with little Jill, 
but I hadn’t forgotten my desire to find her a little cock to fuck. 
Mine was still too large for her little body and, while I really 
wanted to take her anal virginity, I didn’t want to risk hurting her. 

    Instead, I set out to find a little boy penis to introduce her 
young vagina to sex. 

    While talking with a neighbor one day, she was lamenting having to 
take her five year old son with her to a dentist appointment since she 
couldn’t find a sitter. I leapt at the opportunity and mentioned that 
I babysat little Jill regularly and her son was welcome to join us. 

    She thanked me for my offer and we made arrangements for her to 
drop off her son the next day.

    The following morning, I went over to Jill’s house to babysit. 

    Jill’s mom was leaving for a two-day tattoo show, so I would have 
plenty of time with my little sex doll. My neighbor showed up to drop 
off her 5 year-old son to join us. He wore blue jeans with a red 
t-shirt and had short brown hair.

   “This is Danny. Thanks so much for watching him.” she said. 

   “Hey no problem. What’s one more little one to look after?” I 
replied and she left for her appointment.

   “Hi Danny!” I said - squatting down to his level. “Let me 
introduce you to Jill.”  I took his hand and we walked to the nursery 
where Jill was playing with a toy pony.

   “Jill?  This is Danny. He’s going to be playing with us today. Can 
you say ‘hello’?”

   “Hewwo” she said - a bashful grin on her face. 

    Danny smiled and sat down next to her - picking up a toy horse. 
I returned to the living room to give them time to get acquainted. 

    When I returned about twenty minutes later, Jill was still 
playing with her pony and Danny was sitting on a chair looking at a 
book he had on the table in front of him. 

    As I approached him, I could see that he had his right hand 
inside his pants and was clearly playing with his little cock.

   “Did you find a new toy?” I asked - pointing to his pants. He 
quickly pulled his hand out and blushed with embarrassment. 

    I sat down in a chair beside him. 

   “It’s okay. You don’t need to be embarrassed. All boys touch 
themselves like that.”

    Still looking down, he said:

   “Mommy told me it’s bad to touch my penis like that. She says 
it’s naughty.”

   “Not at all Danny. Even grownups do it.”

   “Do you do it?” he asked cautiously - looking up at me.

   “Sure. And sometimes, if two people are good friends, they’ll 
even play with each other’s penis!”

   “Really?” he asked - his eyes growing wide.

   “Yep!” I smiled at him. 

    I reached into my own pants and started to stroke my soft 
cock. 

   “See? It’s no big deal. And it feels good doesn’t it?”

   “I like it!” he replied. 

    I could see he was starting to lose some of his fear now 
that he knew he wasn’t in trouble.

   “So do I!” I answered - feigning surprise that we had 
something in common. “But you know, it’s easier to play with 
it if you’re wearing something like shorts instead of pants. 
Better yet, just your underwear.”

   “So you won’t...be mad if I touch my penis?” he gingerly asked.

   “Not at all Danny. As long as you’re here, you can play with it 
as much as you want. You probably shouldn’t tell your mother 
though. She might get upset. She doesn’t understand how good it 
feels.”

   That was enough for him. He got off the chair and wriggled out 
of his jeans - revealing a set of white cotton underpants. I could 
see his tiny, erect cock poking up inside. His hand slipped over 
his cute hairless belly, back into his underpants and started 
massaging his cock again. 

    By now, Jill had started paying attention and came over to see 
what we were doing.

   “I wanna pway!” she announced. 

   “Jill, that toy is only for Danny. Unless..." I paused as if 
deep in thought. “Unless he says you can play with it. Then it 
would be okay I suppose.”  

    I turned to Danny. 

   “Danny? Would you let Jill see your ‘toy’? She’s curious 
because it’s something she’s never seen before.”  

    I was lying through my teeth. But he’d never know.

    Danny gave me a sheepish look - not knowing what to do.

   “If you want to, it’s okay Danny. She’s just curious.”

   “Okay,“ he said. “But don’t tell my mom!”

   “My lips are sealed.” I answered.

    Danny stood up and pushed his underwear to the floor -
stepping out of them. His little bald cock pointing at the 
ceiling. Jill stared in amazement and reached out to touch it. 

    Danny just smiled at her. At first, she gingerly tapped it as 
if expecting it to be sharp - quickly retracting her hand. Seeing 
that it wouldn’t hurt her, she reached back out and wrapped her 
little fingers around it.

   “Does Jill have a penis?” Danny asked.

   “No Danny. Only little boys do. Girls have something called a 
vagina instead.”

   “What’s a vagina?”

   “Here...I’ll show you. Jill doesn’t mind getting out of her 
diaper. Do you Jill?”

    Jill - still smiling and gripping Danny’s cock - shook her 
head.

    I knelt down next to her - just inches from Danny’s little 
boy cock. It was so tempting to remove her hand and take his 
whole cock in my mouth, but I had to be careful not to scare 
him. 

    I undid the tabs on Jill’s clean diaper and set it on the 
floor. Her dress was still in the way so I started to pull it 
off over her head. She sensed what I was doing and released 
Danny’s cock - sticking her arms above her head. 

    Once the dress was off, the naked little three year old 
grasped Danny’s little cock once again. 

   “This,“ I said - pointing to Jill’s undeveloped pussy - “is 
a vagina. All girls have them. But it’s not fair to Jill if 
you still have your shirt on Danny - she’s naked and you still 
have clothing on.”

    Danny obligingly removed his t-shirt - revealing his bare 
chest and tiny nipples. 

    Here I was - a clearly horny, naked five year old boy and a 
naked three year old holding onto his cock. My own cock was 
now hard as a rock, but I wanted to see more.

   “What does a vagina do?” asked Danny - not taking his eyes 
off of Jill’s sex hole.

   “Well, when girls get older they use them to make babies.” I 
explained. "A boy puts his penis into her vagina and that makes 
a baby sometimes. It feels really good for both of them.”

   “Better than playing with your penis yourself?” asked Danny 
in disbelief.

   “Yep. Way better. But at your age, usually people don’t do 
it. Your mother wouldn’t like that since you haven't seen a 
naked little girl yet.”
 
   “But we aren’t going to tell my mom that I can touch my 
penis, couldn’t we just not tell her about that too?”

    This was too easy. 

   “Well...I guess we wouldn’t have to tell her if you’re good 
for the rest of the time you’re here. Do you want to try it 
with Jill? I’m sure she’d like to play horsey with you.”

    Danny - his eyes still transfixed on little Jill’s naked 
body - only nodded.
 
   “Okay. I’ll be right back and we can get started.” I said.

    I quickly headed out of the room to retrieve my bag. I 
opened it and pulled out a tube of KY jelly. Jill was still 
far too young to get wet on her own, and I didn’t want her 
first experience with sex to be painful.

   “Let me put a little bit of this on your penis Danny.” I 
said - coming back into the room. “It’ll help make things feel 
good for both of you.”  

    I opened the tube and squirted a small dollop of lube on 
my hand and, reaching down, I removed Jill’s hand from Danny’s 
cock. 

    I wrapped my fingers around his tiny little shaft and 
massaged the lube onto him. Danny’s breathing quickened as I 
did so. He clearly was enjoying himself. 

    Using what remained on my hand, I rubbed Jill’s little 
pussy lips to get them ready. I wiped my hand on my pants 
leg and wrapped an arm under Jill’s armpits - lifting her off 
the floor.

   “Okay Danny.  When I lower Jill onto your lap, wrap your 
arms around her so she doesn’t fall. okay?”

    Danny nodded - eager with anticipation.

    I lowered Jill with one arm, and using my other, I 
gripped Danny’s cock to guide it into Jill’s waiting vagina. 

    As Danny’s cock met Jill’s pussy lips, he quietly moaned 
and wrapped his arms around Jill’s naked torso. She 
instinctively wrapped her arms around his neck. I settled her 
down until Danny’s cock was fully penetrating her baby hole. 

    Danny was staring down at their union and obviously 
enjoyed what was happening. Knowing that Danny was too young 
to lift Jill himself, I turned to Jill. 

   “Jill? I want you to bounce up and down a bit like your 
riding a horsey. Okay?”

    Jill was smiling and nodding, and started to bounce 
vigorously.

   “Woah whoa! Not so much!” I chuckled. “Do it slowly.”

    She slowed down, and I just watched as this horny five 
year old had his first fuck with a little girl. Slowly, Jill 
bounced up and down on his cock - her eyes now closed. Danny 
pulled her close to him and let his eyes close as well. 

    By this point, I was too horny to leave my cock in my 
pants. I pulled it out and started stroking it - careful to 
not make myself cum. 

    The pair fucked for maybe a minute before Danny started 
to approach orgasm. 

   “I think I have to pee!” He announced - a little worried.

   “No. That’s not you having to pee Danny. It’s natural, 
don’t fight it.”

    Danny’s pace quickened until he moaned and had his first 
orgasm. Since he was only five it was dry, but he had 
pleasure unlike any he’d had before. His arms fell to his 
sides in exhaustion and I lifted Jill off so she wouldn’t 
fall.

   “Did you two enjoy that?” I asked.

    Danny just nodded - his eyes still closed. His little 
cock - glistening with KY still perfectly erect. 

   “Yea!” Jill excitedly proclaimed. 

    I sat down with Jill standing in front of me to examine 
her soft pussy. No blood and no tearing. Just to be sure, I 
delicately inserted my finger into her and felt for a hymen. 
She had apparently already had it broken somehow, because 
I didn’t find anything.

   “Okay. Let’s get you two cleaned up! Danny, your mother 
will be here soon I’m sure.”

    His eyes went wide with fright. 

   “It’s okay Danny. You were good while you were here so we 
can just let this be our own little secret.”  

    Instantly, he relaxed and exhaled. 

    I took them both by the hand and led them to the bathroom. 

    Using a washcloth, I removed all the KY from Danny’s cock 
and sent him to get dressed. 

    I then turned my attention to Jill - wiping down her pussy 
lips and giving them a quick kiss. She giggled and smiled at 
me. 

    I led her back and put her clean diaper back on - followed 
by her dress.

    About five minutes later, Danny’s mother showed up to pick 
him up.

    “Thanks so much for watching him.” She said. “Can I give 
you a few bucks for your troubles?”

    “No no. He was no bother at all and I think he had fun. He’s 
welcome back anytime if he’d like to come. Would you like to 
come play with us again sometime Danny?” I asked - looking down 
at him and winking.

   “Yes!” He replied exuberantly.

    His mom laughed. 

   “Well, sounds like I’ll be dropping him off again! I have a 
hair appointment next Saturday. Would you be able to watch him 
between ten and noon?”

   “Absolutely. But Jill’s mom will be home that day so can you 
drop him off at my place instead? I live right next door.”

   “Sure, and thanks again. See you Saturday!”

    Now I had a little boy and a little girl who weren’t ashamed 
of their bodies and liked to "play." I couldn’t help but think 
of all the fun times we would have together.


THE END

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