Emma's Summer Babysitting Job?

by scouries

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Heterosexual, Cuckold, Lactation, Pregnancy, Exhibitionism, Size, .

Desc: Erotica Sex Story: Twenty something year old married woman, vacationing on a Massachusetts island,meets the boy she'd babysat for years earlier. And disccovers that the little five year old boy who'd frolicked nude on the beach has grown into quite the handsome teenager. Grown in every way! Will his boyish charm lure her away from her husband?

1 - Hopkins Island, Massachusetts Mid July 2009


"Mrs. Pemberton-Smith," I answered with a quick nod of acknowledgment as I handed Emma and her friends a menu each. "Mrs. Connors ... Miz Burton," I added as I looked down at the three twenty something year old women I'd known all my life. I was grinning.

"Matthew Liam Hopkins?" Emma Pemberton-Smith, nee Kruger, said as she jumped up from her seat, the surprise clear in her voice. "What are you doing here?" she asked as she enveloped me in her arms.

"My god it is," Trudi Burton said as I felt the eyes of all three examining me.

"Not little Matty? What happened to you?" Jackie Connors said. She, even at her age and married for four years, was still, with her pixie face, the cutest girl on the island.

Of course I blushed. "Ha, ha. So, all of a sudden I'm that hard to recognize," I finally asked. But I knew there was no way I was going to stop them. They were famous teasers and together in a group were unstoppable.

"Gawd, Mom and Katie said you'd grown up, but not--" Emma started as the girl I'd loved since I was two years old pulled me even closer.

"They didn't say he'd become Mr. Hunk though," Jackie interrupted.

We were on Hopkins Island, an island sitting in the Atlantic, a twenty minute ferry ride from the mainland, an island that was named for a great, great, great, great grandfather of mine and which was famous for the wide pristine beaches that circled it.

Eight miles long by about two wide, it was home to about two hundred permanent residents, most of who lived in the small port of Couries, and who lived off the tourists who flocked there every summer.

People like my family, and Emma's and Trudi's and Jackie's, who'd descended from the earliest owners, and who now owned ninety percent of the three hundred some cottages that were sprinkled along the shoreline. People who spent most of the year in Boston or New York or Philadelphia, but who each summer flocked back to the island. We were a group of families who'd intermarried extensively in the early pioneer days before dispersing out into the bigger world. Emma and I had figured out years before, using old genealogy tables one of my great aunts had collected, that we were fourth cousins once removed.

The three girls I'd just handed menus to I'd known all my life. Six or seven years older than me they'd been part of the landscape of my summer months for my first sixteen years.

Emma, our closest neighbor, had become my babysitter whenever mom had needed one in those long ago years. But she'd been even more than that. The fact that my mom, still a teenager, and only nine years older than Emma, a girl she'd looked up to all her life, had mothered a child was an irresistible lure to the young girl who lived two hundred yards down the beach.

She'd become a part of our little family. Mom and Emma and I. Emma had spent as much time in our kitchen cooking pies with mom as she had looking after me.

"Gawd I've missed you soooo much," Emma said as she gave me another hug. I inhaled her presence even as I felt her breasts against my chest; she was the girl who'd always smelled better than any other. She'd been holding me in her arms since I'd been a week old.

"Hah, you shouldn't have run off and married that--"

"Ooooohhh Matty, if only you'd been a little older," Emma cooed in my ear before releasing me. Her friends laughed. I smiled, but not inside.

As I served the three of them their drinks and lunch we all caught up to date on each other. Where we were living, school details, marriage status, babies etc., etc. It was something that happened a thousand times between returning islanders in those first days back on the island each summer. A trading of news and gossip that caught us up on people we hadn't seen since the year before.

"What are you doing here anyway?" Jacqui finally asked. Instead of admitting that I was doing a favor for my girlfriend, the daughter of the restaurant's owner, I just told them that a friend had asked me to fill in for him for one shift.

"Are you going to be staying out on the island all summer?"

"Yeah, mom's given me a hundred jobs to do around the cottage."

"How is your mom?" Emma asked.

"She's working ... she'll be here this weekend."

"Clark too. But tell your mom I'll be over to your place Saturday morning, first thing," she promised. "And you too. I want to see you, we have so much to catch up with. Come to the beach tomorrow," she insisted as she looked up into my eyes. I nodded. "Promise?"

2 -The Next Day

"Hey," I said when I'd gotten within ten feet of her. She was sitting in a beach chair, her toes dangling in the breaking surf. I'd been walking towards her with the sun at my back.

"Hey you," she answered back when she finally recognized me.

I was eighteen. Emma twenty-five. She was wearing a skimpy yellow bikini. There wasn't one girl on the island who'd have looked better in it.

"You shouldn't be allowed out in that," I told her as I sat down on the towel next to her.

"Why not?" she asked. Meanwhile she slowly arched her back in a languorous stretch that tested, almost to the breaking point, the strength of the clasp that held the bra together. I was surprised by her pose, although I'd seen her flirt before, the big difference in our ages, and our relationship – young boy and babysitter – had precluded any sort of even mild sexual interaction between us in the past.

"Twenty-five year old married women shouldn't be teasing poor little innocent thirteen and fourteen year old boys. You might just ruin them for life," I teased as my eyes flicked over the body in front of me.

"I don't see any fourteen year old boys." She let her eyes drift down over me as she said the words.

"Their mothers have locked them all up."

"I didn't ruin you for life when you were thirteen," she challenged as she unconsciously moved into another pose that highlighted her body.

Little did she know I thought to myself. "You're still the most beautiful girl on the island."

"Yeah right." Emma's eyes were shining.

"I've missed you. Gawd I've missed you," I told her as I let my hand rest on her knee for a second.

"It's too bad you're still not seven years old. Clark and I would baby sit you any time your mother wanted."

"So you don't approve of the eighteen year old model?" I asked.

"The eighteen year old model is more than just fine," she answered with her nicest smile. "In fact he's pretty darn handsome."

"You should have waited."

"I should have ... but I was swept off my feet ... by the sexy and debonair Mr. Pemberton-Smith ... how could I refuse?"

"Yuck! By the way, how is the wonderful Clark these days?"

"Don't be a bad boy Matty," she admonished. We were teasing. We both knew each other too well. But there was something new, something that had never been there during our first fourteen years together. And it was directly related to the part of my anatomy that was rapidly stiffening in my shorts. It had never been part of our relationship before.

"He's the perfect husband," Emma added. I stuck my finger into my mouth and simulated gagging.

"Shut up, he is," she insisted.

"Yeah and apparently I've got to play mister debonair in the semi-finals of the club championship this weekend."

"I know. He's so excited," his wife answered. "He's wanted to win it for years. You should have heard him when he won his last match. I've never seen him so happy."

What an asshole I thought. Fuck, this guy's married to a goddess and the best moment of his life is winning a quarter-final match in the Hopkins Island Country Club's Championship. "He doesn't have a chance," I boasted. I wasn't planning on letting Clark Pemberton-Smith, a lawyer for crying out loud, beat me. Not now that I'd seen Emma again.

"That's what daddy told him."

"Your father told Clark he couldn't beat me?" Emma nodded yes. I laughed. I'd always liked Emma's old man. "That must have made his day."

"Daddy said he played with you a couple of weeks ago and you looked unbeatable."

"I'll bury poor old Clark."

"Don't you dare! You should let him win, it's only fair. You're younger; you'll have lots of other chances."

"Are you saying you really want me to let Clark win?"

"Yes you should. For me. For all I did for you." The challenge, the calling in of long ago earned IOU's was clear in her voice.

I swallowed the quick refusal that had rushed to my lips. Then thought a second. Then decided. "Okay, if you ask me I will," I invited.

"Ha, you'd never let anyone win. Why would you?" Emma couldn't hide her sudden suspicion.

"For you. And because you happen to be the second favorite person in my world." She knew my mom was number one.

"I bet. You probably have girlfriends around every corner."

"Well of course you would have to agree to a few of my terms."

"I knew it! Like what?"

"Well I've got to get something in return for my letting such a wimp win," I answered.

"Wimp! Hah, he'd probably beat you anyway." We were both teasing. And we were enjoying it.

"He always gets nervous under pressure."

"He does not, he's always been good at games," Emma protested. I said nothing. "What are your terms anyway?"

"A kiss from the pretty princess," I said, then I puckered my lips and kissed the air twice.

"You're nuts."


"And what?"

"And a whole Emma Kruger raspberry/strawberry combo homemade pie hot from the oven."

.... There is more of this story ...

The source of this story is Storiesonline

For the rest of this story you need to be logged in: Log In or Register for a Free account