Roly-Poly Jessi

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Roly-Poly Jessi
Roly-Poly Jessi

The wholesome teen slid a slender dildo into her pussy with one chubby hand. Her roly-poly body jiggled and shook as she stroked; sending the dildo in and out. The other hand was behind her rounded bottom with one of her fingers deep in her hungry ass. She moaned and groaned… interrupted by several short bursts of giggling. She peeked at her laptop; her secret boyfriend was watching intently, eyes wide.

She opened her chubby thighs so her neighbor could see her better. She hoped he could see how wet the dildo was. She moved the dildo from her pussy hole to her ass hole. It nearly disappeared between her plump butt cheeks. She plunged her stubby fingers into her pussy. She convulsed… flooding her hand. Once she had recovered, she sat up and put her wet fingers into her mouth making sure he could see and imagine what was on her tongue. She blew him a kiss and turned off her computer. She was exhausted and went to sleep immediately.

Her friend looked down at the floor in front of him; his cum was lying there in thick heavy clumps. He thought back to just a few months ago…

Elaine, his neighbor, called and asked a big favor. Her sitter had deserted her (like her husband) and she needed somewhere to park her daughter for about 15 minutes a day, from the time the school bus ran until she got home. Since I worked at home, would it be OK if I watched Jessi briefly each school day until she could find another sitter? I said that I would be willing.

I would be more than willing… since I had a little thing for Jessi ever since she was born. Jessi was one of the most spectacular young girls I had ever seen. Her face was angelic. She had these big bright blue eyes; she looked almost startled even when she was just sitting quietly. Jessi had short naturally curly blonde hair. She had the most wonderful smile with perfect teeth. Her lips were full and naturally deep pink. Her skin was creamy white with a light dusting of small brown freckles on her face and shoulders. But what attracted me the most were her plump curves. Don’t get me wrong, she was not fat, just pleasingly plump. Her mom was the same delicious way so it was a very natural condition for Jessi.

Since I had an outdoor pool, I had a wonderful opportunity to watch her in a progression of swimsuits over the years. It seemed that as she got older, her mom bought smaller and smaller suits. This summer Jessi paraded around in front of me in a thin dark purple bikini. Most of her glorious bubble butt was naked. Her round belly protruded in front of the bikini brief.

Jessi’s breasts resembled jiggling mounds of gelatin. As she jumped and moved, they seem to have a life all their own. More than once, she had to stuff one of them back into her top. I could almost think she popped them free just to tease me. She certainly took her time replacing it when her mom wasn’t looking. Afterward, I caught a smile directed to me. What was she thinking? Why was she teasing her neighbor, her honorary “uncle”, her “bestest” friend in the whole world!

I had a tough time not drooling in front of Elaine. Moms normally do not like men drooling over their daughters. Go figure! I would have to disappear into my bedroom for some hand-pounding relief so many times when they visited.

It was not enough, I must tell you!

Since Jessi’s pussy lips were plump, she displayed a secession of incredible camel-toes in her summer shorts. Sometimes when I knew they were going to visit, I would wear a jock strap under my briefs… and it was still difficult to hide my erection!

The next afternoon, I was looking forward to Jessi’s visit. She ran from the school bus yelling “Uncle Dave, Uncle Dave”. I met her at the door and she jumped into my arms. I carried her inside and took her to the kitchen for milk and her favorite chocolate chip cookies. While she ate, we talked. Jessi laughed and smiled… stealing my heart for the millionth time. I hated when it was time for her to leave and she seemed to be sad also.

The next afternoon, she told me she had a secret she wanted to tell me. She seemed so serious but she had a mischievous smile on her pretty face.

Jessi: My secret is that I love you, Uncle Dave.
Dave: I love you too, Sugar. You are my favorite girl.
Jessi: No, I don’t mean like that. I REALLY love you. I want you to be my boyfriend. I want to kiss you and hug you. I want to do mommy and daddy things with you. I want to get naked for you. Would you mind?
Dave: That sounds wonderful, Sweetie, but men my age are not supposed to be boyfriends of girls your age. I can only be a SECRET boyfriend.
Jessi: What is a secret boyfriend?
Dave: The only people who can know are the two of us. Not mommy, NOT ANYONE!
Jessi: I won’t tell a soul!
Dave: What do you want to do first?
Jessi: Will you kiss me?
Dave: Climb up on my lap like a good girlfriend.
Jessi: Go slow with me; I never had a boyfriend before.
Dave: I never had a girlfriend as beautiful as you either.

Jessi grinned… until I covered her lips with my mouth. While I kissed her, I ran my hands up and down her back, across the top of her butt, across her sweet tittie mounds, and along her soft legs. She was panting by the time her mother blew her car horn. She whispered “I liked everything we did” before sliding off my lap and grabbing her knapsack and rushing home.

Within a week, we had a new routine. Milk and cookies were a thing of the past. As I closed the door behind her, she took off for my bedroom, throwing her clothes in every direction. I followed; picking up her clothes, knowing that following this trail would lead to nirvana. I tried to stay close enough to watch her ass cheeks wiggle and bounce. She would jump onto the bed on her back, opening her arms and legs, beckoning for me to hurry.

I guess over the years she had eaten so many sweets that every part of her tasted delicious. Even when I sent my tongue deep into her pretty ass hole, she tasted like warm cookies. Her pussy seemed to be filled with honey. Even her soft, puffy nipples tasted like strawberry gum. I let her pick some part of her body for me to please each time: her mouth, her puss-puss, her butt cheeks, her asshole, her toes, her roly-poly belly; wherever she needed her secret boyfriend to pleasure her. She seemed to prefer her two love holes most often, which were my special choices also.

Jessi was my candy store of happiness. But, I had only 15 minutes in her special store every day. I was frustrated and it seemed that Jessi was frustrated too.

One day Jessi told me that after her mom went to bed, she spent nearly every night playing with her pussy and wishing that I could see her. I said that I wished I could see her too…

I had a sudden idea. I asked her if her laptop was in her knapsack. When she said yes, I spent some time installing and activating an App that would allow us to see and talk over our computers. Her on-line name was “Chunky Monkey” (she laughed at that) and I was “SB neighbor” (SB meaning Secret Boyfriend).

Jessi told him that she couldn’t wait to try it that night.

It was about 11 o’clock when he got the call. Jessi was talking softly so he turned up the volume.

Jessi: Hello SB.
Dave: Hello, Miss Monkey. (Jessi laughed.)
Jessi: I locked my door but I’ll still better talk quietly.
Dave: Sounds like a good idea. Do you have something special to show me?

Jessi undressed, but this time I was treated to a slow unveiling. She licked one finger from each hand and rubbed them on her nipples. She cupped her breasts and held the puffy wet nipples out to the camera.

Jessi: I wish you could kiss them. They tingle.
Dave: Tomorrow, Sweetheart. I promise.

Jessi lay back and opened her pudgy legs. She held the lips of her puss-puss wide open with her fingers. Then she closed them. Then opened them again. She continued playing this game with her sweet cunt. Then one of her fingers disappeared inside. She pumped for a while and then located her sensitive clit. Jessi would flick it for a minute or two then plunge her finger back inside. Soon it was two fingers, then three. That was as many as she could take.

Dave: I have something special to show you after school tomorrow.
Jessi: Show me now! Pretty please!
Dave: It’s a surprise. It will take some of your sweet kisses to make it appear so you will have to wait.
Jessi: OK. See you tomorrow, don’t forget my surprise!

The next day, Dave stripped and sat on the bed next to Jessi. Jessi sat up and stared. Dave took her hand and placed it on his cock.

Dave: This is my pee-pee, sometimes called a penis, peter, dick, or cock. I would like for you to call it “cock”. Right now it is soft and small but, with some help from a beautiful girl, it can do a trick.
Jessi: What do I do? (In a small quiet voice.)
Dave: I want you to kiss it and lick it.
Jessi: OH, MY.
Dave: You don’t have to…
Jessi: But I DO want to. How do I start?

Within a few minutes, Jessi started to see (and feel) a change in Uncle Dave’s cock. She licked it more and planted soft warm kisses on it. Dave told her to open her mouth and take the end inside and suck on it. Jessi did. Dave was in heaven. While she was sucking, he told her how wonderful she was and how much he loved her. Before Dave climaxed, Elaine’s car horn blew and Jessi had to rush to get her clothes on. Dave climaxed even before Jessi could get through her own front door.

That night Dave performed while young Jessi watched and fingered herself. Dave stroked himself and eventually shot a load of cream into the air. Jessi marveled at the sight. When he calmed down, he picked up some cream on one finger and put it into his mouth.

Jessi: What does it taste like?
Dave: Like LOVE.
Jessi: Can I taste it?
Dave: If you work hard after school tomorrow, I may be able to give you some of my love.

Dave warmed up by watching some porn and stroking his cock before Jessi arrived. A little work on her part and Dave fountained into her mouth. She gagged for a bit but kept swallowing until it was all gone. She went home in a daze. Her mother asked her why she was smiling so much but Jessi never answered, just smiled wider.

Dave got some good news the next day. Elaine called and said she had to take someone’s place at a work conference this coming weekend and wondered if he could keep Jessi from Friday afternoon until Sunday night. Dave was happy to say yes (really happy).

Dave thought: A whole weekend, I’ll have to do some planning but this weekend my little munchkin is going to lose her virginity (front and rear). Oh Joy!

When Jessi got the news, she shivered all over for the two days until Friday.

Friday after school, Jessi arrived and was unsure exactly what to do. She was excessively quiet and reserved. Jessi might have been uncertain, but I had everything planned. I took her out to dinner to a great Italian restaurant. It wasn’t long before she was laughing, giggling, and talking up a storm. My love-buddy had reappeared.

When we arrived home, I told her that I wanted to take a shower with her. She thought that was a great idea. Shortly, both of us were naked and wet. I marveled at my sweet neighbor. Foamy soap slid down her ample curves, along her pinkness until it dripped on the shower floor. She looked like a wet sea otter. I slid my hands and fingers all over her curvy body as I washed her. She laughed and shook with pleasure. Her face had the biggest smile. I turned her sideways to me and took a long look at her shape. It was perfect. Jessi had the most wonderful bulge at her belly and the side view of her ass was exceptional. I slid one finger inside her pussy and one from my other hand into her ass. Jessi shook like a bowl of jelly. Her eyes were closed and she was panting and squealing with joy.

I let her enjoy that for several minutes then had her face me. I took each one of her nipples between my thumbs and index fingers. I pinched her nipples, gently at first, then harder. She went up on her toes and shook harder.

I released her and soaped up her hands. I took each of her hands in one of mine and showed her how to wash me. In the course of her bathing me, I had her finger my ass, wash my cock and balls, and pinch my nipples too. When we were clean and dry, I carried her to my bed.

I had soft music playing and candles burning. Vases of flowers perfumed the air. I kissed her and caressed until she begged me to do more.
I had her lay across a pillow putting her round plump ass into the air. I caressed and kissed her beautiful butt cheeks. I pulled her cheeks apart and gazed upon the pinkest, tiniest, and tightest tail hole I had ever seen. I was struck dumb in awe. I showed how to bring her own hands back and hold her sexy ass wide for me. I kissed her little ass star and she squealed with pleasure. Her body shook with delight. I was in love.

I reached for the oil and lubed up my fingers. I gently slid one into her pretty ass. I went slowly but she had no problem taking the whole finger. I twisted my finger inside her and fucked her with it for several minutes. I could see her pussy get wet. Her smell was intoxicating. I breathed deeply. She was awesome. I took out my one finger, re-oiled, and inserted two fingers this time. She opened as easily as before. I twisted my fingers inside her. She grunted and told me how wonderful I was making her feel. I finger-fucked her faster and faster until her ass hole was so hot, it felt like it was on fire. She had stopped shaking or moving, just lying there enjoying my attention, holding her butt cheeks wide for me. I kissed her little star again and used three fingers up her ass. I was shocked when I had no difficulty pleasuring her with three. She had such a hungry little piggy ass. After some time, I thought she seemed to be ready. I moved closer and rubbed my cock head across her ass hole. Her hole opened as if asking me inside. I pushed and my head entered her. Her ass hole swallowed my cock head with ease.

Jessi: I feel so full, daddy.
Dave: You just called me “daddy” sweetheart!
Jessi: Is that OK? (In a quiet voice.)
Dave: Of, course. I would be honored to be your daddy and your secret boyfriend.

When she smiled, I slid another inch up her ass. I slowly entered her over the next ten minutes or so. When my belly was pressed tightly against her butt, I began a slow love ride in her ass. I rode her for some time before pulling out.

I had her roll over and spread her legs. I inserted my cock slowly into her pussy, spreading and filling her. I began slowly as before and then rode her faster and faster. Her belly and titties shook and bounced. She gasped and panted.

I sprayed her pussy full of cream. Her eyes widened in surprise when the pressure hit her. I swear I could see my supply of cream inside her just by looking at her bulging belly. As we drifted off to sleep, I heard her murmur something like “I’m looking forward to tomorrow.”

Jessi was so very greedy!

Reposted 6/1/16

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