I'm a 37 year old lifelong bachelor who suddenly found himself raising two kids after my sister passed away. I love my nephews and there was never any question I'd accept responsibility for them. Their father was never around and my mother has earned a rest after raising three kids of her own.
It was a definite change in lifestyle. I'd always been use to coming and going as I pleased. Now I needed to arrange a baby sitter whenever I wanted to go out evenings. The sitter turned out to be a fifteen year old girl named Jenna, who lived a couple of streets down from me.
I interviewed a handful of potential sitters but Jenna struck me as the most responsible. She seemed more mature and serious minded. She obviously liked children and the kids liked her. I have to admit I liked her too. She was short, cute in a geeky sort of way with her granny glasses and big book she always brought along on sitting jobs. She had dark brown (nearly black) hair and big blue eyes that were expressive and full of good natured humor. She had a splash of freckles across her nose and cheeks and a toned slender body. I often mused if I were still a teenager she'd be exactly the sort of girl I'd want for a girlfriend (not that I'd ever have a shot - in High School I was the fat kid in the Star Trek t-shirt that always showed up to dances alone).
I'd gotten into shape as an adult, but I was still the lonely fat kid at heart. I hadn't had much of a sex life or many relationships in the nineteen years since I'd walked across that stage and accepted my diploma.
Jenna and I got along well. She sat for me on a weekly basis (sometimes multiple times per week) through the summer as I treated myself to movies or went on dates with women I met at online dating sites. I never really met anyone I was interested in. They all had major flaws, which was probably why they were on those dating sites. So I'd come home and pay Jenna and sometimes we'd just sit and talk for an hour or more. She was genuinely interested in my life and I in hers.
I found out she was having problems with an emotionally abusive ex boyfriend who had moved away but continued to harass her through near constant texts, tweets and Facebook posts. She had nearly been brainwashed into believing she was responsible for all the pain and distress she had suffered (and continued to suffer) at his hands. I convinced her to be strong and kick the bum completely out of her life. I told her she was an amazing young woman and any guy would be lucky to have her. She'd blush when I'd say such things and go home with a skip in her step.
Before too long she had developed a crush on me. I spied little hearts on her school work bearing both mine and her initials and notebook paper where she had practiced signing her first name with my last name, over and over again.
Eventually a night came when I ended a date much earlier than typical, because I just wasn't enjoying myself. The woman who had sounded so sweet and charming over the phone had turned out to be anything but. She was already three sheets to the wind when I picked her up for our date and drank even more once we arrived at the restaurant, becoming loud, obnoxious and rude.
Jenna listened as I detailed the hellish date experience and slid close to me on the couch, patting my hand.
"That sounds horrid," she sighed.
"It was, trust me on that," I smirked. "I'm done. These dates just aren't working. Maybe I'm meant to be alone."
"Or maybe your meant to be with someone that you won't find on that cheesy dating site," she suggested.
I shrugged. "I'm not much of a social butterfly. I doubt I meet her."
She reached up and tilted my face toward her own.
"What if she's sitting right here in front of you?"
I stared into her clear blue eyes.
"You?," I asked. "But... Jenna, you're only fifteen."
"Age is only a number," she shrugged.
"You know what else is a number?," I asked rhetorically. "Twenty. As in the number of years I could get for being with a fifteen year old girl."
She laughed then, a real belly laugh, hand covering her mouth. I couldn't help but start laughing too.
"Silly," she said after a moment. "Whose going to know? it's not as if I'm going to broadcast to everyone, hey! I'm in love with the sweetest, most amazing guy on the planet and he's old enough to be my dad!"
I blinked. "In love?"
"Totally," she replied. "With all my heart."
"I...don't know what to say," I said.
"Then don't say anything," she smiled. "Just kiss me."
I looked around. "Where are the boys?"
"Asleep," she nodded toward their bedroom down the hall. "Been snoring their little heads off for more than an hour. Now mister, are you gonna kiss me or not?"
I leaned forward and kissed her full on the lips, savoring their warmth and the sweet candy scented flavor of her breath. She opened her mouth to allow my tongue in. We kissed deeply. When I pulled away her eyes were closed.
"Oh wow....," she sighed. "You kiss great."
"Do I?," I grinned.
"So, you came home really early and I'm not expected back home for at least another couple of hours," she said after a moment. "You want to have sex?"
I blinked. "Man that escalated quickly!"
She laughed. "What?"
"We went from a kiss to let's have sex in like three minutes," I said, smiling back at her. "Have you ever even had sex before?"
"No," she shrugged. "But that's what adults do right? I'm mature, you said so yourself. I think I'm ready. Most of the girls at school have already done it. Some even have kids."
"We're not having kids," I waved a hand dismissively. She laughed again.
"Of course not, but that's why they made condoms right?"
"And Plan B," I said. "Do you really want to? I mean, do you know what your asking?"
"I'm not stupid or a child," she sat back, arms folded. "I know what I'm asking, and I want to. I want my first time to be with you. A man that knows what he's doing and not some boy from school that won't know anything and will brag to everyone how he 'nailed' me."
"Ok then," I stood. "Sit tight. I need to drive to the pharmacy. Back in 30 minutes."
The entire drive to the pharmacy was a battle of wills. My brain against my cock. "This is stupid, This is stupid, This is stupid." I kept saying as a mantra of sorts. But my cock would have none of it. It just kept reminding me of how sweet that kiss was and how warm and wet and inviting her mouth had been and how I'd be able to run my hands and mouth all over that firm tight fifteen year old body.
Plan B and condoms in bag, I stepped back into the house about a half an hour later half expecting Chris Hansen to step out from behind a doorway and say "You sick fuck, explain yourself!"
But Chris Hansen wasn't there. Just Jenna and she was smiling and waiting.
"We should go into my bedroom," I suggested. Jenna got off the couch and grabbed my hand and kissed my cheek and fairly bounced down the hall beside me, eager for the new experience she was about to partake in.
Inside the room I shut and locked the door and pulled the sheets back on the bed. I asked when Jenna's parents would expect her back home and we set my alarm clock. Then we undressed and I finally beheld her naked body. I felt myself immediately growing stiff. She had small perky tits with dark Hershey's kiss nipples and a shaved pussy. I stared at the slit and wanted nothing more in the world than to eat her right then and there. I had her get onto the bed and lay on her back. I got on my knees and lost myself in the act of cunnilingus. She moaned and moved in response to my touch, arching her pelvis almost humping my face as I greedily sucked at her wet pussy. After I'd satiated my desire to taste her virgin hole, I crawled on top of her and licked, kissed and nibbled all over her body from her neck and ears to her collar bone and breasts, down to her flat tummy.
Changing places I guided her in the act of fellatio. She licked and sucked my balls and kissed my hard shaft before taking me into her mouth and bobbing her head up and down until I came. Finally I slid deep inside of her. She gasped and clamped her eyes shut. I fucked her nice and slow. When I came and rolled over on my side, I saw she had bled onto my sheets. But she was smiling at me, despite the tears of pain in her eyes. "Can we do it again?" she joked.
Since that night we've remained a secret couple. How long will it last? I really don't know. But I love her. In fact, I'm crazy about that little blue eyed girl. Her 18th birthday can't come fast enough for me.