Emmas adventures and misfortunes
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Emma's Summer Babysitting Job? free porn video
1 - Hopkins Island, Massachusetts Mid July 2009
"Maaaaatt?"
"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--"
"And what?"
"And a whole Emma Kruger raspberry/strawberry combo homemade pie hot from the oven."
"A whole pie just for a silly golf game?" she asked in a tone that said, 'are you nuts'. But then she started to laugh. Then she leaned over and gave me a quick kiss on my lips. Not quite a boy/girl kiss but somehow more than a babysitter or brother/sister one.
"So does mean we've got an agreement?" I asked.
"Yes, but it's going to be an Emma Pemberton-Smith pie," she said as she jumped up and ran laughing into the surf. "And don't you dare tell him," she yelled back.
"It wasn't a very good kiss," I complained as she dove into the waves.
I was in love again. And that was before she came running out of the surf, with droplets of water flying off her athletic body, with her breasts straining as they jiggled, with the darkness of her aureole showing through the thin yellow material, with her long curly blond locks dancing in the sunlight...
... and then she threw herself down onto her back next to me on the beach towel. "I LOVE THE SUMMER," she yelled to me and the gods above as she spread her arms and legs in an invitation to the sun to ravish her. The clearly outlined camel toe of her sex was the only invitation I watched.
"Shall I cream you?" I asked as I reached for the tube of lotion.
"Just you remember Matty Hopkins that I'm a married woman."
"Yes ma'am," I answered as I squeezed the tube.
I spent about two hours with Emma on the beach that day. I creamed her front and then later her back. She did the same for me. And it wasn't like it was when an eleven year old Emma Kruger had put sunscreen on four year old Matty. And we both knew it.
We swam. We laughed. We remembered. And for the first time we flirted. And there was absolutely no doubt in my mind that she knew what effect she'd had on me. Or that she'd enjoyed it.
But Emma Kruger was now Mrs. Clark Pemberton-Smith. But as I walked home that afternoon I knew that it didn't matter ... I knew I wanted her more than any young boy ever had...
3 - Golf Sunday, July 19th
Clark Pemberton-Smith wasn't that bad a guy. Or so everyone said. The prick!
Like Emma I'd known him all my life. Like Emma and I, he too was a descendant of one of the original families. He was three years older than Emma and close to ten older than me. I'd seen him on the beach, at parties, out sailing, throwing a football on the beach and everywhere else on the island all my life. He'd even been a day camp councilor for the younger kids, including me, when he was seventeen or eighteen.
I didn't like him. Never had. Well maybe that's not true. Maybe I only started disliking him when he started hanging around Emma. I'd known nothing about the whole sex thing of course. What seven or eight year old boy does? But somehow I'd sensed that Clark was up to no good with my baby sitter, with my friend, with my almost sister. I didn't know how or why but I knew he was a danger to her. And hence to me and mom.
Of course he really wasn't! He was just a horny teenager who all of a sudden had realized that the young girl, some three years younger than he, had all of a sudden become the prettiest and most desirable girl on the island. Something every other guy had realized at about the same time. Honestly, looking back, I only disliked him because it was his interest that Emma returned.
It really wasn't until Emma was sixteen or seventeen that they started to go out as a couple. And of course that just ratcheted up my dislike of him even more.
And Clark knew I didn't like him. I'd overheard him talking to Emma once, when she was eighteen or so, when he'd asked her, "What is with that little prick, every time I come over he--"
"Don't call him that, he's my favorite little almost-brother, I love him," my baby sitter answered.
"Almost brother! He's a jerk. Christ, did you see him, his little hands curled into fists the second I came into the room. It's like he's trying to protect your honor."
"And what's wrong with that?" Emma asked.
I was eleven that summer, Clark was twenty-one.
Emma married him three summers later. By that time I'd come to understand what I was losing. She danced with me at the reception. And in her white gown and with her shining, happy eyes she'd broken my heart. Late into that night, hours after the reception had ended, I'd sat crying in my mother's arms on the beach that fronted our summer home.
Clark called me on the following Friday night, right after he'd arrived on the island ferry, to arrange the match. Sunday morning at nine a.m. was arranged. And as I biked over to the islands golf course on that Sunday I was still debating with myself if I should let him win. And my indecision had grown even greater after we'd played nine holes.
"You don't have to do it you know," Emma said to me seconds after her husband and I had finished the front nine.
"Don't have to do what?" I asked back.
"He shouldn't have said that." Even though he was a pretty good player, in fact he was a good all round athlete, Clark was one of those guys who gets nervous on the golf course. And when he got nervous he talked. And that day he talked to his golf ball, to his clubs, to the five or six people who were following us around, and of course to me. He was big time nervous!
It turned into one of the least enjoyable nine holes I'd ever played. And it had ended with him saying, as we were walking over towards the snack hut, that maybe it would be better if I just conceded now. 'Hell, why waste any more time kiddo, once I get ahead I'm unbeatable'.
I had let him win the ninth to go one up. Even Emma had cringed when she heard his words.
"Clark just can't help himself," I told his wife.
"I'm just saying I won't hold you to our deal."
"A deals a deal," I answered. "Besides, I already collected part of the price."
"It doesn't matter." I could see that Clark's talking and boasting had bothered her more than it had me.
"So do you want the kiss back then?" I then pursed my lips and kissed the air.
"You're crazy." There was a wry smile on Emma's lips.
"I'm still going to let him win ... but my price has gone up," I added, then turned and started towards the tenth tee.
"Gone up where?" I heard behind me.
I kept the game close. In fact I was one up after fourteen. I let him win the sixteenth so we were even with two to play. He cheated on the seventeenth hole! The fucker actually cheated. He thought he'd got away with it without anyone seeing him. But, from twenty yards away I'd spotted it when he'd nudged his ball with his foot and turned a horrible lie in the rough into a good one. Emma saw it too. I could see she was going to protest, even call her husband out on it, but before she did, I shook my head no.
We halved the seventeenth and so went to the final hole even. A final hole on which Clark, in spite of a case of nerves that caused him to bogey the hole, won the match when I, who seemingly choked, took four to get down from a greenside bunker and handed my opponent the victory.
Clark couldn't stop from crowing when my putt slid by on the high side. And he couldn't help announcing to the crowd that had gathered around the eighteenth green that this brilliance and experience had carried him easily to victory over the callow Hopkins boy. 'The young pup's still got some growing up to do', Clark announced as he escorted me from the green.
Emma couldn't meet my eyes. She knew that the young pup wasn't happy.
4 – The Pond Thursday July 22nd
"Guess what I brought besides the promised pie," my favorite married woman asked me as she dismounted from her bike and leaned it against the side porch. She was wearing a pair of tight orange shorts and had unleashed her long blond curls; they seemed to be dancing as they trailed down her back. Her full, high breasts were straining against the white bikini top that was attempting to hold them in. She had come to pay her debt.
"Your infamous beauty?" I suggested.
"Ha, ha," she answered as she grabbed the hamper from her bike basket and walked towards me.
I just had on a pair of cut-off jean shorts. I'd been splitting logs for the woodpile when she'd pulled in and the sweat was pouring off me.
"You're sweaty, you've got all sorts of little pieces of bark and wood on you," she said, then gingerly leaned in and quickly plucked a couple of wood chips off my chest.
"You missed some," I answered. I'd have willingly stood there and led her pick stuff off my body all day.
"Do you want to eat now or swim first?" she asked.
"C'mon, we'll go have lunch at the pond, I'll wash there," I said as I took her hand.
Mom's end of the island, an piece of land inherited from her grandfather to the chagrin of many other family members, had only a modest cottage on it but did have its own pond, one of the few on the island, as well as, due to its location, almost complete privacy. The most valuable piece of real estate on the island, it had been left to the unmarried mother who'd had a child out of wedlock when she was sixteen years of age. A granddaughter who'd been nurtured by her loving grandparents after her parents had rejected her. The land, and a relatively large trust fund, had then been left to mom when they'd died in a tragic car accident when I was only four.
Emma Kruger was no stranger to the pond. In fact, besides my mom and I, she was the only person on the island who'd had free reign of the Hopkins acreage over the years. We'd spent a hundred afternoons there during my boyhood.
"He was an ass, he shouldn't have said those things," Emma said as we walked hand in hand through the copse that rose just west of the cottage.
"He cheated," I accused. "That'll cost you," I threatened.
"That's why I brought sandwiches too."
"Hah! Sandwiches? You're going to have to do better than that," I snorted as we broke through the last of the dense foliage and found ourselves in a sun filled glade about a hundred yards in diameter. The pool, fed by a trickling creek, was surrounded on all sides by a ring of wild, waist high summer flowers.
"Oh my gawd ... I'd forgotten," Emma said as she stopped to take in the vista before her. "Eden must have been like this," she finally said as she let me retake her small soft hand and lead her down the overgrown path that led to the water and the small sunning platform I'd built two years earlier.
"You better not eat any of the forbidden pie then," I suggested.
"It was an apple mister smarty pants," she teased back. "When did you build this anyway? It's great," she asked when we broke through the waist high moat of flowers and she saw the new construction.
"You didn't ever get over here at all last year? Or the year before?" I asked as we stepped up onto the twelve by twelve platform that jutted out into the pond. Two Adirondack chairs sat regally looking out over the water. A three foot diameter matching table sat between them. "We build it two summers ago," I said as I walked over to the waterproof storage locker that was camouflaged by the thick grass at the end of the platform.
"Clark had that assignment in Europe two years ago ... then you guys weren't here last year," Emma answered. Mom and I had taken a trip across America the summer before and our two quick early trips to the island hadn't intersected with Emma's. And when we'd gotten back for the last two weeks of August she'd already gone; only her sister and her parents had still been here.
"You could have used it," I said as I pulled out the cushions for the chairs as well as the two foam mattresses that served as tanning beds.
"I'm always afraid to bring other people up here. It's yours and your moms place."
"And yours too."
"Not anymore," Emma answered, a touch of sadness in her voice.
"Always," I said as I threw the two mattresses, covered in a soft, bright, floral patterned cloth, down onto the platform.
"We should eat first," Mrs. Pemberton-Smith announced as she set her picnic hamper down on the table.
"I stink, I'm going for a quick swim first," I answered as I dropped my jeans and dove into the cool water. I was down to a pair of white briefs, briefs I almost lost as my body knifed into the water.
"Are you coming?" I yelled when I finally surfaced twenty-five feet out from the platform.
"You're just wearing your underwear," Emma complained as she pushed her tight shorts down her thighs. Her bathing suit panties matched her white top. Both in color and skimpiness.
"It's a bathing suit," I corrected.
"Is not," Emma yelled back as she ran across the platform and hurtled herself through the air. Ems had been a champion diver in high school. She sliced into the water with perfect form.
"It is underwear," she insisted five minutes later when we found ourselves back on the dock.
"It's a combination underwear/bathing suit, it's a new style ... from Poland," I answered as I wrapped a towel around my shoulders. I knew she could see the outline of my penis through the wet cloth.
"Poland? Yeah right," she scoffed. "It's very immodest. And you certainly shouldn't be parading around in your skivvies in front of a married woman," she said as she laid out the sandwiches and pie on the table.
"You shouldn't look then. And besides look who's talking." I let my eyes drift down over her dripping body. Slowly.
"What?" she asked but couldn't completely stop the blush that had started to leak into her face. "For your information young mister Hopkins, this is a perfectly respectable bathing suit from this summer's collection of--"
"Of swingers international?" I supplied, then stuck out my tongue.
"Ha, ha. No my fashion challenged little friend. It comes from Jean Paul Gaultier. Who just happens to be a leading French designer. Stylishly chic women all over Europe are sporting this look this summer." Emma, who had always been one of the most casual, less pretentious girls on the island, was clearly getting a little embarrassed with my inspection.
"Well at least it must have been pretty inexpensive."
"Why?" She almost stamped her foot. Her nipples, surprisingly big ones, and clearly excited, were now poking out through their thin, wet covering.
"There's not much material you had to pay for." I suddenly knew she'd spent time before coming over trying on her various bathing suits. That the selection she'd finally made reflected a desire to wow me. An unconscious or conscious desire I wondered. "Besides," I added, "didn't I read somewhere that all French women go topless?"
"Shut up you." Emma was through taking any guff from me. And she couldn't help adding, "And this is coming from some guy who prances around in Polish bikini underwear in public. Gay Polish underwear," she said derisively. I turned around and faced away from her and before she could add another word, I pushed my underwear down my legs.
Her, "Maaaaaaa ... aaaaatt!" was echoing around the lake as I wrapped my towel around my waist.
"I'll let them dry while we eat," I said as I hung then on the arm of the chair. "Do you want me to hang yours up too?" I asked.
"Perv!"
We ate and talked, talked and ate. We'd hardly said two words to each other over the preceding three years but we had a lifetime of memories to talk about. We were both really, really happy for that hour or so. In fact I realized that I'd not been as happy since the day she'd married Clark four years earlier.
We talked about my mom, about Emma's job, about the many days the three of us had spent at the cottage, on the beach, by the pond, and at the grotto.
"In every picture from back then I'm naked," I complained as we compared memories. "You and mom are sitting around and two or four year old Matty is running around starkers."
"That's not true," Emma said laughing.
"And you and mom are naked in most of them too."
"We were not!" But the truth of the matter is that my mother was, and still is, a nudist at heart. And any time she and I, or even the three of us, had been at the pond or the grotto, she'd always gone naked. As her young son did. Even Emma, up til she was about ten or eleven, was usually without clothes when we were swimming. After that, with a teenager's modesty, she clothed up.
As I looked at Emma as we talked that day I wondered if she still sun bathed 'au natural' when no one was looking.
"Mom said you took Katie out a couple of times last summer." Katie was Emma's younger sister, but still almost two years older than me. I'd wondered if Emma had heard about us. I could see my old babysitter wanted to change the subject.
"Not really ... we didn't date, we just hung out a bit. At a couple of barbeques, campfires. All the kids were there."
"Dad said he was hoping you two would get together."
"She's too old for me."
"No she isn't. You would have been perfect for her."
"She'd just broken up with that idiot McLeod guy. That's the only reason she even looked at me," I said deprecatingly. "He wasn't very nice to her."
"I never liked him," Emma agreed. "Katie would have been lucky to have you."
"I talked it over with mom."
"You talked what over with your mom?"
"I don't know. Everything. Whether I should go out with Katie. If it was okay given everything else. And if I should..." I let my words hang.
"Should what?"
"After one campfire, after the kids and most of the adults had left ... it was right near the end of August. We'd had a few beers..."
"Yes?" she encouraged when I hadn't gone on for a while.
"We made out a bit."
"A bit what? What'd you do?" I didn't answer. I wanted Emma to have to work to draw every word out of me. And knowing Emma, and how curious she was, I knew she'd try.
"Did you neck or something?" Could Emma be jealous I wondered. Then realized I hoped so.
"A bit." A shy response.
"More than that?"
"No, not much. It's private, it's between just me and her."
"But she's my sister."
"We really didn't do anything, I'm serious," I said after another long silence.
"You must have done something."
"I wanted to."
"But you didn't?"
"I thought if we did it that it wouldn't be fair. That I'd be taking advantage of her."
"It? Do you mean--"
"Mom agreed with me."
"You told your mom?"
"I tell her everything. I always have."
"About girls? Sex?" Emma couldn't hide her disbelief. I knew I'd got her hooked. And I immediately decided to set it.
"I have ever since I did it the first time."
"Ever since the first time you did what?" I let Mrs. Pemberton-Smith stew. "Your first time with a woman?" she eventually asked.
"Yeah. It was sorta weird. She was an older woman. Married. It was a surprise. I didn't plan it or anything ... then I felt bad about it ... guilty. But it felt so good." Emma almost choked in her rush to get her questions out.
"How old was she?
"Who was she?
"She was married?
"Do I know her?
"Was this last summer?
"Was it on the island?"
"Mom was mad at first," I said softly. "She was a year older than mom."
"You slept with someone older than your mom? She was in her thirties?" Incredulity leaked from Emma's voice. I nodded. "What did your mom do?"
"Yeah, her early thirties," I conceded.
I watched as Emma did the math in her head. "How old were you?"
"Mom and I had a long talk about it. We finally agreed that it was okay as long as I told her everything that happened. She said sex wasn't something to be ashamed about."
Nadene
- 12.03.2021
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