Tommy and Jessica - A Love Story
by pflinders

Chapter 1: First Love

I'm Tommy. I'm 14. I'm a normal kid, I guess. I like sports and video games. And I'm starting to like girls, to notice girls. Nothing serious. I just like to joke and hang around and have fun. I do odd jobs in the neighborhood for some extra cash. And I've done some babysitting. Mostly the two boys next door. These boys have a playmate, Jessica. She's 8 years old and lives across the street. Last week her parents needed a sitter on short notice and asked me.

Jessie is a bubbly and fun little kid and kind of cute. I guess I kind of like to watch her. She always wears dresses. She likes to look pretty and that makes her stand out. Sometimes over the past few weeks I was sure she was crushing on me. I thought that was sweet.

Jessie played outside with the neighbor boys and me as she had often done. We went in for the pizza her parents had delivered. Afterward she wanted to play a video game with me, some Barbie thing. I told her that it was boring and dumb and too girlie for me. She said, "Well, I'm a girlie girl and I like it. This is my game and I want to play this!" Then she started teasing me, "What are you, Mr. Macho?" She poked me and I poked her back and this led to a tickle fight. She tried to get away from me so I chased her. But she let me catch her and tickle her some more.

She ended up on the floor. Her dress was up and her legs were open. I was looking. Her underwear was kind of loose on her and I could see under the edge a little. Jessie saw me looking. She liked me looking but she teased me about it, "Take a picture. It lasts longer." She started moving her legs and her hips a little and had her mouth open licking her upper lip. I don't know if she was trying to be sexy, but it was sexy to me. This lasted just a few moments. Then she said, "Tickle me again!" I tickled her chest and her sides. She writhed and laughed but I kept my eyes on her lower parts. I was liking the show. It was the first time I'd had such a show. "Or maybe you should take a video." Then she said, "Tickle my feet!" With this she jumped and moved even more. I caught a glimpse of her crack. My heart was pounding. I was getting very excited. "Tickle my legs!" I walked my fingers up both her legs to her inner thighs. With this she screamed and jumped up like she was going to try to get away again, but she just landed on all fours laughing. She even had tears in her eyes.

Her dress was way up now around her chest, her white cotton panties completely exposed. I thought she was finally done but then she said softly, "Tickle me all over Tommy!" I tickled the back of her legs and her pantied bottom and her sides up under her dress. I let my face touch her butt. She rolled back over and I tickled her tummy down to her lower belly and she slapped her legs together. Then I forced my hand between her legs to tickle her inner thighs again. But she grabbed my hand with both of hers and held it tight for a few seconds. She stopped struggling and so did I. I was scared that I had gone too far.

I couldn't believe what happened next. Jessica pressed my hand into her crotch and said, "Tickle me there, Tommy, and tickle me naked."

"Jessica!" I pulled my hand away. But then I watched her pull off her panties and start to play with herself. My jaw dropped.
"Tickle me like this, Tommy. I like this kind of tickling the best." My God! She wants me to masturbate her!

"Jessica! Are you sure?"

"Yes, Tommy, please will you? I tickle myself like this every night. But I want to see what it feels like for someone else to do it to me."

So began my first real sex with a girl. I had never before even seen a girl's privates except for sneaking peeks at my dad's Playboys. At first I just kept watching her explore the pink wet lips with her fingers. I saw the little nub that she especially liked to concentrate on, her clit. Then I put my fingers in with hers. She let me take over. I fingered Jessica's pussy. I masturbated her but she kind of guided my hand some of the time. She started to moan and rock her hips. I was lying next to her and her face was even with my chest. My shirt was open and she turned her face into it and started to kiss me there. Suddenly she tensed up, let out a loud moan and had an orgasm. Then she relaxed and I felt something warm and wet ooze between my fingers.

Jessica looked up into my eyes and smiled. "Leave your hand there for a while and kiss me." She kissed me with little puckered up pecks. I liked this but then I began to respond with more passionate ones. She started to rub herself against my hand again. She came up for air after a bit and gave me a loving smile with a quiet laugh. I took the opportunity to ask her where she learned how to do all this.

"I mostly taught myself after I saw some sexy stuff on Daddy's computer. My mom works nights and Daddy does some surfing while she is gone. I snuck into his den after I was supposed to be in bed. He had the lights dark and some loud music playing so he didn't hear me. I saw Daddy playing with his peter. Some video was playing of a guy tickling a woman like we were doing. It looked exciting so I tried it on myself when I got back to my room. I loved it."

We went back to kissing and rubbing. Then I felt Jessie's hand explore my stomach down to the crotch of my pants. She found a hard-on to beat all. She stopped kissing me and asked, "Do you want me to tickle you naked?" Before I knew it she had my shorts unzipped and her hand in my pants. She got up and pulled my shorts and underpants off. She sat down next to me and began to jack me like she knew what she was doing.

"Your peter is kind of cute. Can I kiss it?" She started kissing the tip of my cock, more puckered pecks. Then she opened her lips a little and let it rub against her teeth. Next she licked it several times with her tongue. This about drove me nuts! Finally she took the tip into her mouth. I felt her suck just slightly and I lost it! This surprised her and she pulled off and watched my cum squirt out and run down on her hand. She said, "Wow, that's cool!" She licked and tasted it again. "Eewww! It tastes kind of icky but it tingles in my mouth!" But then she started to lick and suck up all she could find.

"I thought you said it was icky."

"I always lick my fingers after I tickle my vageenia. That is icky, too, but I like doing it. I like the tingly feeling your stuff has. I like that it came from being sexy with you." I looked at my sticky fingers and looked back at her. I started to lick them and she giggled. "You're finger lickin' good, my little chicken." We both laughed.

She climbed on top of me wrapping her legs around my waist. We kissed some more. I could taste my cum on her lips. I slipped my tongue between them. She opened and gave me hers. We kissed and cuddled a long time and dozed off.

I awoke with a start when I heard the garage door opening.

"Oh shit!!" I jumped up and quick got into my clothes. Jessie's mom called for us. I walked downstairs. "Jessie's getting ready for bed. She's brushing her teeth." Then I realized my hair was mussed and my face sweaty. I was scared as hell that she would suspect something. "Mom! Tommy was so much fun! I want him to be my babysitter forever!"

Jessie slipped something into my hand and winked as she passed by me to her kiss her mother. I swallowed hard and stuffed them into my pocket. It was her panties!!

Chapter 2: And the Woozle

I was babysitting the neighbor boys again the other day. I took them down the road to the park so they could play in the playground. Jessica was along again as usual. I really enjoy having her around, especially now that I'm her "favorite babysitter." She likes to tease me now and get me all hot and bothered. That day she was making her skirt flip up every time she came down the slide. She had flowery nylon panties kind of half on half off her butt so that they were really loose in her crotch. Once when she was climbing back up the slide she giggled and said to me, "I saw you peeking!" in a singsongy voice and winked at me.

"Damn, I forgot my camera," I returned, remembering what she said the last time. She made sure I got lots of free peeks after that.

They have a porch-type swing there, too, that looks out over a pond. I sat down on it and Jessie joined me lying sideways with her head on the armrest. She had her knees up and slightly apart. Her panties were still loose, hanging about an inch out from her crotch. I slid my hand down to the seat so that it was touching her butt and the loose panties brushed against the back of my hand as we swung. She started to open and close her knees and I could see the soft skin of her pussy lips. Then Jessie said, "The view is beautiful here, isn't it."

"The closer view is quite pretty, too," as I used a finger to pull her panties to one side.

She giggled, "Naughty boy." I gently pressed the back of my fingers against her little box and she responded by opening wide and raising her hips a little. And the rhythmic swinging was warming me up very well.
When we walked back the long way through the woods. I saw some deer tracks and pointed them out to the kids. Jessie said, "Do you think it is a Woozle?" and laughed.

"A Woozle?"

"You're not afraid of a Woozle are you?" She laughed even louder. She kept saying "Woozle" over and over again. I was starting to get annoyed.

"What the heck is a Woozle?"

"You know, the scary animal in the forest from Winnie the Pooh. Pooh and Piglet got lost in the woods and kept going around in circles. They saw their own tracks and got scared thinking there was a Woozle going to eat them."

"But what is so funny about a Woozle?" She pulled my arm so she could whisper in my ear, "That's what I used to call my vageenia!"

"Oh." But I was still confused.

The boys picked up some sticks and started fencing with them. Jessie and I sat on a log.

"My mommy told me how I gave it that name. My daddy called it my wiz hole. When I was potty training he'd always say 'be sure you wipe your wiz hole.' So I started calling it my wizzle. One day Mommy was reading the Woozle story to me from the Pooh book. I laughed. 'Pooh is afraid of a Woozle?' She didn't understand at first but I guess from then on I had switched from wizzle to Woozle for the name of my vageenia. That became my favorite story and I would laugh hard every time she read it.

"Well, after that Mommy bought me all the Pooh stuffed toys. One day I was playing alone in my room with my Pooh bear and I made like we were lost in the woods. I said, 'you're not afraid of the Woozle, are you? You don't have to be afraid.' I pulled my panties off and showed him my Woozle and touched his nose to it. I liked that. I started rubbing his nose in my Woozle. I decided that he really liked my Woozle. 'Do you think there might be some hunny in there?' I'd have him say. The next day I announced to my mom that Pooh was no longer scared of the Woozle." I chuckled.

"Pooh's nose started to get dirty and sticky because I sometimes put hunny on my Woozle for him. But Mom would wash him. I eventually wore his nose clear off!" She laughed. "I didn't start using my fingers until I saw Daddy's computer videos.

"Tommy, you're not a-scared of my Woozle are you?" She said this in a 4-year-old girl voice. She lay back on the log, lifted her skirt a little and spread her legs exposing her still-loose panties. She was quiet for a while and I just stared.

"You are a-scared. Do you wanna kiss my Woozle like Pooh?" She pulled her panties to one side and spread the lips with her fingers. My heart was pounding. I couldn't resist. I touched her pussy again lightly with my fingers. "C'mon, Tommy, kiss it!" She was right. I was scared. "Tommy's a-scared of the Woozle. Tommy's a-scared of the Woozle," she sing-songed.

"Shh! Not here, Jessie, the boys will see." But the boys had taken off following the deer tracks. I could hear them but they were out of sight. Jessie had pulled her panties down to her knees now and was fingering her "Woozle." I said, "Ahh, what the fuck!" I got on my knees and pulled her panties the rest of the way down. "Ummm! You used a dirty word! I'm tellin'." She still used the 4-year-old girl voice. "Jessie, it's a dirty thing we're doing!" She smiled.

I pressed my lips to her "Woozle" and I was almost overwhelmed by the smell and the feel of her little body. I kissed her there repeatedly and hard. She started to moan. But then she said, "Taste it, Tommy, lick my Woozle, 'Do you think there might be some hunny in there?'" I licked her little cunt; I felt her clit throbbing against my tongue. I flicked it several times. She went, "Ooh! Oooh! Ooooh!" Then I found her cunt hole and stuck my tongue in as far as it would go. She tensed up three times and then locked my head between her legs. She screamed and almost broke my neck when she had her orgasm. And I came in my pants.

The boys heard the scream and I heard them start running towards us. I quickly helped Jessie pull her panties back up. She smiled at me and giggled. The boys ran up and asked what happened. Jessie said, "We saw a Woozle and Tommy chased it away!"

As we walked back to the house, Jessie announced to the boys, who were walking about 20 feet ahead of us, "Tommy's not afraid of the Woozle any more." She smiled and winked at me. "But maybe I should be afraid of the Woozle! It almost broke my neck." Jessie laughed.

I whispered to her, "There definitely was some hunny in there." With that Jessie slapped me on the butt.

Then she saw the wet spot on my tan shorts. She whispered to me, "Did you pee in your pants?"

"Well, ...something like that." I pulled my shirttail out to cover the spot. She was quiet for a second then it dawned on her, "Ohhh!" She touched the spot and brought her fingers to her nose. Then she tasted them. "There is definitely some honey in there! ... Tommy-boy, I want those underpants. Remember, I gave you mine the other day." I blushed and she laughed at me. "I guess fair is fair."

Chapter 3: Christopher Robin Meets the Woozle

Jessica is just a little girl. Eight years old and I'm 14. But I'm falling in love with her big time. She's kind of blonde and has the cutest laugh and the prettiest smile. And she's a total tease. She drives me nuts with her teasing, but she always surprises me and gives me more than I could ever dream.

Her dad called me yesterday to baby-sit her again. I'd had baseball practice that I was supposed to go to but I didn't want to say no. Not after what happened the last time. I talked my mom into letting me skip the practice.

I walked across the street to her house. This time I remembered my digital camera. After Jessie's dad gave me instructions and told me he'd have a pizza delivered like last time, he left and Jessie noticed my camera. She said, "Cool! Let's go out in the backyard and play on the swing set." I took lots of pictures of her with her skirt flipped up and of her backside as she would climb up the slide backwards. She had grayish blue panties on and they were tight. But I could definitely see the contours of her pussy lips when she would spread her legs for me and of her butt. I'd zoom in for close-ups. I loved it.

We stopped for a while and she looked through the pictures I had taken.
"I never knew what my bottom looked like."

"Cutest little butt I'd ever seen," and I cupped her little ass in my hand under her skirt. She wagged it for me a little and I slipped my fingers up underneath. She jumped and said, "You goosed me!" We laughed.

We heard the doorbell ring. It was the pizza. We sat in the living room and ate it while we watched some cartoons on TV. We got to the last piece and she grabbed it before I could.

"You want this piece, Tommy?" I reached for it but she pulled it away from me. She kept teasing me with it. Finally she lay back on the couch and pulled her skirt up. She smiled and placed the slice of pizza on top of her panties. "Go ahead, Tommy, take a bite of my slice!"

"God, you're such a tease! But let me take a picture first." She posed for me with a big grin on her face. That done, I took a big bite of the pizza and chewed it with my mouth pressed against her panties in her crotch. "Mmmmh, you must really be hungry!"

"Yes, absolutely starving!"

"Well, then, shut up and eat!" She fed me the whole slice like that and when I took the last bite she grabbed my head and heaved with her hips as I could tell she was having a huge orgasm. When it was over she relaxed and I took a picture of the big wet spot and pizza stains between her legs. Best pizza I ever ate!

"What should we do next, Tommy? I know. We could go to my room and play supermodel." I liked her suggestion. We went up to her room and she changed into some of her prettiest dresses. She put on some of her play makeup and made sexy poses in her dresses. I told her how sexy she looked in all of them. "You like sexy, huh? My mom's got some pretty linjuree. You want me to try some of them on?" So she took me up to her parents' bedroom.

She found a lacy see-through peach-colored teddy in her mom's drawer. She took her dress off and started to pull down her panties. I said, "Wait! Do that slow and sexy so I can take some pictures."

"Oh, like I have seen on my daddy's computer." Boy, did she ever do such a hot striptease! She slipped the teddy on but it was way too loose. She had to hold the bottoms up. But I had her lay back on the bed with her legs open wide. I took lots of close-ups of her pussy through the see-through. I told her to put her hand in and touch herself. More close-ups of her masturbating. It was great! I unzipped my shorts, pulled my cock out and started masturbating with her.

"Try something else on." She found a red elastic thong and put it on. This actually fit her. First she posed on all fours exposing that beautiful bare butt of hers. Then she turned over and fingered herself both over and under the thong. And I kept jacking myself while I watched. I asked her to put her black dress back on. I thought it would look great with the red thong. It did. Jessie is just like a natural when it comes to modeling. I took lots of pictures.

"Tommy, let me take some pictures of your peter." I lay back on the bed and held my dong straight up. She took a few pictures and said, "Let's take your shorts off so I can see your cute nuts." Off they came. A few more pictures then she started stroking me and playing with my nuts. All of a sudden she grabbed my cock and yanked.

"Ow, that hurt!" and I jumped away from her. "Why the hell did you do that?"

"I'm sorry, I was just playing. Do you want me to kiss it?" She grinned. "Jessica, that is sooo unfair!" She laughed and resumed stroking me. "Oh my, was that bad little girl mean to you?" When she kissed it she said, "There, there, little boy, does that feel better?" Then she took the head of it into her mouth and sucked. "Fuck, yes, it feels better!"

"I've decided I'm going to call your little guy Christopher Robin."

"Why's that? Why not Tigger? You've seen how he likes to bounce!"

"But it's your hand that's doing the bouncing. We can call your hand Tigger."

"Oh, yeah, he bounced you earlier when he goosed you!" We laughed. "I want to call him Christopher Robin 'cause he's your boy-thing and he should have a boy's name. Besides Christopher Robin was never afraid of the Woozle."

"Christopher Robin it is then. You know he has just been dyin' to kiss your Woozle."

Jess straddled me then and started rubbing her Woozle on my Christopher.

"Wow! My Woozle thinks this is awesome!" I told her, "Christopher is loving it too. But he's afraid he might get hunny all over your mommy's linjuree." I helped her get out of the thong and we resumed what we were doing. She put her hands on my shoulders and leaned forward. That made it easier for me to move with her. Just a few minutes and Jessica had another orgasm and mine followed right after. Jessie took some pictures of me with cum all over my tummy before she licked up all the hunny.

"Jessica, this is so amazing! I bet you there isn't another babysitter in the whole state who gets to be sexy with his little girl. And you know what? I think I am in love with you."

"I love you, too, Tommy." We lay naked in each other's arms and she smothered me with kisses.

It was 9 o'clock and her daddy had told me Jessie was supposed to go to bed at 9:30. He would be back at 10. We straightened up her parent's bed and Jessie put the 'linjuree' back in her mommy's drawer.

"Hmmmh. What do you think this is?" She handed it to me. "It's a vibrator. A dildo. Girls sometimes use them to play with themselves with." I switched it on and handed it back to her.

"Cool. You mean my mom uses this on her vageenia?" She touched it to her cunt. "Wow! That is sweet!"

"Better put it back in the drawer. Your daddy will be home pretty soon."

Ten minutes later she was in her nightie and I was tucking her into bed. She was acting just like a little girl again, not like the supermodel or porn star she was earlier. I gave a kiss and a hug.

"We're boyfriend and girlfriend now, aren't we?"

"Yes, but maybe we shouldn't tell anybody, okay? Some people wouldn't understand."

"Okay, Tommy, I love you."

"I love you, too, Jessica." We kissed some more and gave each other the tongue. I couldn't resist putting my hand down to fondle her pussy again. She responded immediately and, with just a few rolls of her hips, was soon experiencing her third orgasm. This time I licked up the hunny. "Goodnight, My sweet love."

I downloaded the pictures to my computer when I got home. I looked at them all again and jacked off to them.

Chapter 4: The Big Surprise

Jessica came over to my house the yesterday. Both my parents work so in the summertime I am home alone. Jess knocked on the door and when I opened to her she ran at me and jumped into my arms. We kissed but then I asked her what that was all about. She just said that she loves me and that she missed me and that she was very happy that we could be alone together.

"I have a big surprise for you!" She pulled some magazines and a DVD box out of the canvas bag she was carrying. It was a couple porno magazines. The DVD was hardcore. "I found these in my daddy's den. He had them hidden. They're awesome! They have people being sexy in them and really fucking! Do you want to look at them with me?"

"Whoa, Jessica, these are really dirty!"

"Yeah, like the stuff we have been doing and the stuff we haven't done yet!" She had a point. But I thought, "Holy shit!" I had never seen a porno movie before and had only peeked at the Playboys my dad had when Mom was in the hospital when I was 10. He caught me with them and I've never seen them around the house since then.

We sat down on the couch and she opened to the first spread.

"Look at this! It has two girls licking each other's vageenias and playing with vibrators." She pointed at one of the girls with a vibrator deep in her pussy. "I can do that now, Tommy. I have been practicing. You want me to show you? I brought Mommy's vibrator with me, too." She reached for her bag. I said, "Maybe later."

I was flushed and terribly nervous. Jessica noticed this and put down the magazines. She got on my lap facing me and just hugged me until I relaxed. Then, without saying a word, she sat back and looked at me, caressing my face and my hair.

"You're still afraid of the Woozle, aren't you?" I nodded. "You know, you are a lot like Piglet." She kissed my cheek and hugged me again.

"I really like being sexy with you, Jessie. But pictures of other people doing it are kind of scary to me all at once and by surprise."

"We don't have to look at those," and she started kissing me and gave me her tongue.

"Maybe we can, though, after we..." Jessica finished my sentence, "...after we fuck!"

Jessie pulled her dress off over her head. Then she pulled my shirt off. She scooted back, leaned forward and started kissing and licking my nipples. God that felt good. She got up on her knees and caressed my head while I sucked her nipples.

"Can Christopher Robin come out to play?" She got down on the floor and pulled my shorts off with my underwear. She kissed and played with Christopher until he got good and hard. Then she stood up and modeled her panties for me. "You like these? Last time we were at the mall I asked Mommy to buy me some pretty underwear like she has and she got me these." They were white and lacy and see-through.


"You go ahead and take them off for me." I kissed her belly and I pulled them off very slowly, caressing her hips and her ass and her legs as I did so. She got back on my lap. Christopher and the Woozle kissed and we kissed with our tongues.

Jess lifted herself a little and held Christopher and rubbed his head in her Woozle. She put the head in the Woozle's mouth and started to press herself down on him. I said, "No, Jessie, it will hurt you. You're too small."

"Didn't I tell you? I have been practicing with the vibrator." She spit in her hand and got her Woozle wet with it. She spit again and rubbed it on Christopher. She pressed him into the mouth again and this time he slid in. "Oooohhh!!"

"See, Piglet, Christopher can take care of the Woozle."

Jessica and I were fucking. We were fucking for real! It was unbelievable how good it felt. Jessie was holding her breath and sucking air in through her teeth. She was smiling and laughing at the same time. Then she'd exhale really hard and start over again. Sometimes she was almost jumping up and down on me. A couple times I fell out and she laughed and put me back in again. All of a sudden she stopped moving and kissed me hard with a loud moan. She was having her orgasm and I could feel her cunt throbbing around my cock. Just as her throbbing stopped mine started. Shooting my nut inside her was so amazing! But then Jessica exhaled with a big "Aaaaahhhh!" Her body tensed up and I felt her throbbing again. She was having a second orgasm!

We held each other for a long time. We were both covered with sweat. Jess giggled when I got soft and slipped out of her pussy.

"I think the Woozle won," I told her. "Christopher won. He just got tired after the fight."

"They both won. And it wasn't a fight."

"Tommy, I love you." "I love you, too, Jessica. You're an amazing girl."

Unbelievable. I had been fucked by an 8-year-old girl!