Jessica's Decision
Copyright© 2019 by Gigolo joe
Chapter 1
Coming of Age Sex Story: Chapter 1 - My next door neighbor, Jessica, has decided that I will be the one to usher her into adulthood. But at fourteen, it's just so wrong!
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Ma/ft Consensual Romantic Heterosexual Fiction Cream Pie Exhibitionism First Masturbation Oral Sex Public Sex Small Breasts Slow
I’d known Jessica from about the age of four, when her family had purchased the house across the street from us.
It wasn’t long before my wife, Karen, and Jessica’s mother, Tiffany, became fast friends.
Jessica’s father, Mark, was always busy with work, and aloof when home, so we never saw much of him. It really wasn’t a surprise when he divorced Tiffany for a younger, more petite woman.
Tiffany was an attractive woman, with curves in all the right places. She was carrying just a hint of extra weight, but you’d have to be insane to consider her fat.
My wife, on the other hand, was carrying enough to be voluptuous, which frankly was far more attractive than the stick Mark left Tiffany for. Karen was an incredible woman, sporting a PhD, but playing the part of Susie Homemaker gladly. Her job as a special needs teacher was challenging, but rewarding at the same time.
There were special training classes she would have to attend a couple times a year, I’d usually go camping with our son, David during those periods.
David was two when Jessica moved in and she had taken a keen interest in him. Though he was two years younger than her, they played like the best friends they were; so it was no surprise that Jessica spent a lot of time at our place, especially with Tiffany working.
Jessica was a precocious child, she always seemed to know how things worked; she held a deep understanding of the universe, and she and Karen could talk about almost anything. She had few friends as she didn’t fit in with her peers; her body was undeveloped, she stood about four feet five inches tall, she looked much younger than her fourteen years. There was a smattering of freckles across her pert nose, and she usually wore a plain set of glasses beneath her brown tresses.
Recently, I started to notice little things she did; she would cling to me when Karen wasn’t home. She and david would snuggle on either side of me watching tv, or sometimes it was just her while David played with legos.
Then I noticed her wearing more skirts and dresses, the waist would be pulled up high, leaving the hem so high on her thighs I could see her underwear.
One time, she bent over to pick something up in front of me, and her skirt rode up over her bare ass revealing the fact she was wearing no panties.
I said “Umm; Jessi, I think you forgot to put on your undies.”
She turned red and pulled her skirt down.
“Dontcha think maybe you should take care of that?” I asked.
She was clearly embarrassed, but she gave me a wry smile and scampered off to her home. When she returned, still glowing red, she pulled up her hem enough to reveal some plain yellow panties.
That goofy smile never left her face, but her hem was now several inches lower.
Going into the summer, little incidents like this happened seemingly randomly, though never as brazen as the panty incident. Sometimes she’d wear a top too large that when she got close, I could easily see down her chest, not that she had any breasts yet to speak of, but her nipples would be clearly on display. She didn’t wear a training bra, yet.
Tiffany wasn’t a bad mother to Jessica, she was just busy. When she started to get a personal life, Jessica began spending even more time with us, spending some nights and weekends over.
We took the spare room, which we had been using as an office, and added a fold up bed, so she wouldn’t have to sleep on the couch.
In the middle of August, Karen announced she would be taking a training course the last week of August, a week before school started.
I figured Jessica and David were getting too old to share a tent, so off to the local sporting goods store for two new tents. They’d be comfortable for a single adult, roomy for a single child, and perfect for the two of them.
I loaded up my truck and the four of us headed to the airport. We said our goodbyes to Karen and made the four hour drive up to the river and our favorite camping spot. Jessica had taken Karen’s spot up front and was chattering about this and that. I couldn’t help but notice the hem of her already short jeans skirt had ridden up her thighs exposing the dark blue panties underneath. Her ill-fitting top dipped down too low in front, exposing both her nipples for anyone to see.
I laughed internally, I wasn’t sure if she was oblivious, or trying to attract attention. I really didn’t know who’s head she was trying to turn, though. David was just a kid and didn’t regard her as an attractive female. It couldn’t be me, could it?
Could it?! Everything started to click into place; the little ‘accidents’, her clinginess. Was she infatuated with me? She was far too young to be sexually aware, wasn’t she? But this was Jessica we were talking about. If any fourteen going-on thirty year old girl was going to do it, it would be her.
So Jessica had some kind of crush on me. It wasn’t unheard of, quite natural actually. I wasn’t too sure about the flashing, but what was I going to do to defuse this situation without breaking her heart?
David was here, so we weren’t alone, but I really needed to confirm this, then let her down gently.
“Matt? Matt!!”
“What?!” I cried.
“I asked you if you thought I was ready for a training bra?” She asked.
I looked down at her; she had pulled her shirt up, but was trying to squeeze the breasts she DIDN’T have together.
“Uhh, you probably should ask your mother or maybe Karen about that, I really don’t know.” I looked in the mirror at David; he was immersed in whatever video game was on his tablet. He seemed oblivious to anything Jessica was doing.
The remainder of the trip was uneventful, we arrived at our spot overjoyed to find it vacant, though later than I liked.
“Ok, go pick out your spots!” I cried, and both David and Jessica lugged the boxes containing their new tents out of the truck.
We had been coming to this spot for the last twenty years or so, the area was surrounded by blackberry bushes, the sand was similar to what you’d find on a beach. There were little alcoves in the brambles on different levels to pitch multiple tents.
I dragged the large box containing my tent to my favorite alcove. I took the shears I had brought just for this purpose and cleared the area of stray blackberry vines.
“Ok, I found a spot!” Shouted David.
I looked up and laughed. He had chosen a spot three hundred yards away. Jessica stood watching us, it was obvious she was waiting to see where David settled.
“Not good, unless you want to be turned into bear poop!” I shouted back.
David growled and returned, all while I started assembling my tent.
“Ok, how about here?” He called.
This time he was about thirty yards from the river, and about seventy five yards from me.
“That’ll work!” I said.
Now that David had chosen a spot, Jessica chose a spot between David and I, five yards from me. The truck was about ten yards from me.
Down near the river, almost directly across from David, was the fire pit. There were sitting benches someone had built around the pit, and the trees lining the river had counters built onto them many years ago.
I got my tent up quickly, and stocked it with all my things. The tent could accommodate four people easily, but would be more than comfortable for me on the queen size foam mattress.
Finishing that, I went over to help Jessica with hers.
“Point the door at yours, ok?” She asked.
“Ok.” I said. Odd request, but ok.
She asked for the shears, so I handed them to her, and went down to help David.
“He was struggling with his tent and had made a mess of it, so I helped him get it up. The blackberry vines were encroaching, so I went up to get the shears from Jessica. I then noticed she had cut a trail between our tents. I really didn’t know what that was about, but whatever.
I got David’s ‘yard’ cleared as the sun set, and went to start a fire. I had brought some wood, but not enough for the entire trip.
“Guys, we’re going to need wood, go find some. But don’t go too far!” I said.
They both groaned, and went off to find wood.
With the fire burning, I went to the truck and got tonights provisions. I locked the remainder in the cab.
I was cooking dinner when the kids came back with a couple armloads of sticks. I knew they’d have better luck in the daylight, so we sat down and ate dinner.
S’mores came next, then bed. I put out the fire, locked the leftovers and dishes in the cab, and kissed David goodnight.
It was no big deal to kiss my son goodnight, it was a nightly event. Jessica got the same treatment when she stayed over. This night though, she turned and kissed me on the lips. She held it until I broke it. She looked crestfallen as I said goodnight to her.
I still wasn’t taking the situation seriously; Jessica just had a small crush on a man that had been a positive male role model for most of her life. She had just turned fourteen the month prior; I’m sure puberty had started, her hormones were probably going crazy. It was just puppy love...
I had drifted off to sleep when I was awoken by Jessica’s zippered door. Moments later I heard her whisper loudly; “Matt! Matt! Are you up?”
I turned on the light and opened the door. She came bounding in. I zipped the door back up and laid back on my bed.
Jessica was standing above me in an orange nightshirt that came to her mid thigh. It looked like it was a year or so too small for her. The tightness of the cloth, plus the shadow of the light exaggerated the dimples and curves of her body. I must’ve missed her recent development, because where she used to look like David; skinny and featureless, she was starting to fill out.
“I’m ... scared. Can I sleep here with you?” She asked.
I opened the covers and she threw herself under them. She was facing me with her knees in my belly. I was shirtless and wearing my cotton bath shorts. But she’d seen me that way many a time.
“What’s scaring you?” I asked.
“There was a noise ... umm...”
She struggled for a minute, and in the dim light I could see her face turning red. She was getting hot and I began to worry about a fever.
“No, I’m sorry, that’s a lie.” She said.
Intrigued, I propped myself up on my elbow.
“What’s a lie?” I asked.
“I wasn’t scared of anything; I just wanted to cuddle with you.” She said.
“Well, Jessi, I don’t know that that should be a problem, but some people might find it inappropriate.” I explained.
“Why?” She asked.
I thought for a moment.
“Well, I’m an old man, you’re a young girl. We’re alone in a tent. It might look bad.” I said.
She snorted derisively, “I’m not a child; I know about all those things. I’ve even read my dads playboy books.” She said.
Now it was my turn to blush.
“Jessi. I’m too old, you’re too young.” I said.
“Bullshit!” She cried.
“Language, young lady!” I said, surprised. In all her life I’d never heard her cuss.
“Bull-SHIT! I’ve been flirting with you for the past year! You think I didn’t know you could see my undies? You think I just ‘forgot’ to put on panties that day?!” She cried. Oh shit, I was in trouble.
“Keep it down, you wanna wake up David?” I said.
“I know how all that stuff works, I think about it all the time. I want you to do it, nobody else.” She cried.
I was desperate to extricate myself from this situation, I was mentally grasping any thought that might change her mind.
“Karen! What about Karen?!” I asked.
“What about Karen? I’m not going to tell her. I wouldn’t tell a soul.” Jessica whispered.
Fuck.
“I love you, Matt. I’ve been in love with you since I was seven.” She said.
“I love you, too, Jessi. More than you can ever know. But I’m in love with Karen.” I said, sadly.
“Who says you don’t have to love her?”
She asked.
“How did you feel when your father left you mom for a younger woman?” I asked.
“Scarecrow.”
“What?” I asked.
“Dad left mom for a scarecrow.”
I was astonished for the moment. Then I pictured the skinny little stick’s face on a scarecrow and I lost it. Jessica started giggling along with me for a while.
“Do you love me?” She asked, her voice hardly audible. Nary a hesitation, I could answer honestly; “With all my heart and soul.” I said, kissing her forehead softly.
“But I love Karen, too, and I’m not going to leave her.”
“Do you love her so much you’d never cheat on her?”
How the hell could she know?! I was no saint; I had committed adultery several times. This didn’t change how I felt about Karen, I loved every aspect about her except sex. Sex with her felt more like a chore than a pleasurable event. But she was perfect for me in every other way.
“What could you possibly know about adultery?” I asked.
“Are you saying you’ve never cheated?”
She had me dead to rights; I had no idea how she could’ve known. Maybe she had seen me bring someone over, which I’d only done twice.
Maybe her mother knew? If so, then Karen would know. But Karen wasn’t the type to let it go. Love and sex to her were one and the same. I, on the other hand, could separate the two; they could be mutually exclusive.
Any of my mistresses could attest that I always told them my family came first. It was just sex.
She was waiting for an answer. I knew better than to lie to her, all I could do was pull rank.
“That’s none of your damn business, missy! Where’d you hear that, anyway?!”
She flinched and turned away.
“I knew you’d say that...”
After a minute it was clear she was silently crying, her body shaking. I had blown it; her heart was broken and our relationship would never be the same.
I wrapped my arms around her and hugged her close, pulling her to cry into my shoulder.
“I’m sorry, baby girl. Do you know how many years in prison I’d get?” I asked stroking her back.
“About ten years, if the other inmates didn’t kill you” She said after a minute.
Now it was my turn to flinch. She really had thought of everything.
“I really don’t think you understand everything that goes into this.” I said. She pulled away and stared into my eyes.
“We’d kiss, French kiss. You’d rub me ... down there. We’d take off our clothes and I’d spread my legs. You’d get between them and push your penis into my vagina VERY gently.
It would hurt a bit, but you’d be gentle. You’d start thrusting and I would orgasm, then you’d orgasm. I haven’t had my period yet, so you can’t get me pregnant.”
Holy shit, she really had planned this all out.
“Like I said, there’s a lot more to it than just that. When your hymen breaks, it’ll hurt a LOT. You won’t enjoy it at all. And how the hell do you know about what an orgasm is?” I cried.
“When I was eight, I was jumping on the bed. I accidentally did the splits and tore something. Mom took me to the doctor, they said I tore my hymen.
After a few days, I was feeling around in there to see if I could feel the tear. It felt really good, so I kept doing it. I had my first orgasm, later, I learned what felt good, and what felt REALLY good.
I know what an orgasm is...” She said with that wry smile again.
“Why would you want to do this to Karen?” I asked.
“I wouldn’t be doing anything to Karen. She would never find out.”
“You’re saying you wouldn’t be trying to steal me away from her?”I asked.
She shook her head.
“No. I like what we all have. I just want a little more.” She said.
“Do you know how crazy this all sounds?! It wouldn’t even fit inside of you!” I cried.
She grinned.
“I’ve seen you; it’ll fit.”
The fuck?!
“When have you seen my penis?” I demanded.
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