My Luckily Unlucky Summer

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I came back from my freshman year at the university knowing my family had moved into a smaller house. Some of my stuff had been put into storage but my bed, dresser and a few other necessities had been moved to our old neighbor’s attic apartment. I had mixed feelings about all this. First off, I loved the idea of being on my own. On the other hand someone must have found my porn collection when they moved my stuff. That could lead to some embarrassing conversation later. Who would it be with, my mother (god I hope not) or my dad who would give me a lecture about safe sex and respect again? Needless to say I got the hell out of there as fast as I could and drove over to my new place.

The Smiths were an elderly couple that we had lived next door to my entire life. I was expected to mow their yard weekly, keep the pool clean, and trim the bushes around the property in exchange for my free rent. When I got upstairs I could hardly believe my luck. I had my own outside entrance so I could come and go as I please. I remembered when they added this room. It had its own bathroom, a kitchenette set up behind a half wall and another semi-partitioned off space for my bed. My parents had put my old tv and dvd player in there and the Smiths were paying for cable and their internet connection had wi-fi. I was set.

“Hey Mark.” I turned around to see my landlord’s granddaughter Cheryl standing in the door. “Looks like you got the lucky draw. I was hoping I would get this place but my parents wanted more control over me so I will be settling in downstairs.”

“Sorry about that Cheryl. I wouldn’t even be in this situation if my parents had not sold the house. Not that I’m complaining anymore. You going to be here all summer again?”

“Actually, I am going to be here for the next few years.

I am enrolling in college this fall and not all of us got into your precious university. Maybe when you leave for the fall I can move up here.”

“Well, you’re welcome up here anytime. My parents left me my tv and dvd player and I can run my online account to the tv.”

“What, no girlfriend to get jealous?”

“What girl could hold a candle to you?” Did I mention Cheryl is a world class hottie? She was my first kiss several years earlier but we had never gone any further. We were best friends even though we only saw each other each summer for the last dozen years. She came to visit her grandparents so we got to hang out. A long distance romance would have been impossible but our friendship was immutable.

“Oh Mark, I have missed you.” With that she came up to me put her arms around my neck and drew me into a brief kiss. “By the way, your sister dropped that box off for you.”

She indicated a familiar box she had left on the landing outside the door. “She said it was private, that your parents couldn’t know about it, and I should make sure you got it personally. So, is it porn or drugs?”

My blush said it all of course. “Well, it’s not drugs so you don’t have to worry about the police raiding the house.” I walked over the the door and grabbed the box.

I brought it inside and threw it on the couch.

“I guess everyone needs a little something every once in a while, eh Mark?” Cheryl asked giving me a wink. “I mean, who doesn’t help them self to a little self gratification? So, which is your favorite? C’mon, you can tell me, your bestest friend…”

My mouth was catching flies. As she was asking these questions Cheryl was bent over my porn box, her hands on her knees, her arms mashing her tits up and almost out of her low cut t-shirt. She looked up at me and smiled knowing full well I was looking right down her shirt. “Someone likes what he sees,” Cheryl gestured and the tent in my shorts. “This one looks good, maybe we can watch it sometime.” With that she walked over gave a peck on the cheek, shoved the dvd down the front of my shorts and walked out the door.

To say I masturbated then and there is like saying the sun is hot. I locked my door, dropped my shorts pulled out my steel hard cock and wanked away for a mere 30 seconds before shooting a load into the toilet in my new bathroom.

My cell phone went off while I stood there recovering indicating a text message. It was from Cheryl, of course. “Hope you are enjoying your private time, I know I did. Thought you might like a picture of what you were staring so intently at a few minutes ago.” And up popped a picture of Cheryl on my phone. No, not a nude, but close enough… she was wearing a bikini that left little to my imagination. She must have taken it in the mirror. A second text came through just then, “join me in the pool?”

A minute later I heard a splash out back and looked out my one window. Cheryl was indeed taking a dip but not in the bikini. She was wearing a modest one piece more likely to please her grandparents. I went ahead and stepped out of my shorts and slipped on my baggie swim trunks, hoping that if I did get excited it might not be as obvious or hard to hide. Growing casino siteleri up next door the daredevil in me had discovered the fun of jumping off the roof of the Smith’s house into their deep end. This had served me well in high school as I never feared the high dive and gotten me all conference honors. Landing feet first in their deep end rarely took me all the way to the bottom as they had an extremely deep pool. I climbed on the railing outside my door and slipped slowly over the roof. I waited until she climbed onto the float before my leap. As I rose to the surface I could see the surprise and excitement in her eyes.

“I can never get up the nerve to do that. I always get up there walk to the edge and change my mind.”

“I hope you don’t chicken out of everything. There might be a few guys out there with some serious problems if you do.”

“Wouldn’t you like to know…”

It’s the way we were, always flirting, never going to the next step. After that first kiss years ago we had not even come close until just 15 minutes ago. “Sure I would. Tell me everything.”

“You first.” Its like we were 13 and playing truth or dare. Actually that sounded like a good idea.

“Ok, ask whatever you want. If I don’t answer you can dare me to do something. But then I get to ask you something. We keep going until one of us quits.”

“Whatever… I bet you quit first.”

I was holding on to the side of the float while we bantered back and forth. “We’ll see who quits first. The loser has got to do something crazy though.”

“Ok, you’re on. First question, did you just spank the monkey after I left your room?”

“What do you think?”

“Answer the question… before or after I sent you the picture?”

“To tell the truth, before you sent the pic but I almost had a second go after seeing that bikini.”

“My turn, did you get yourself off thinking about me jerking off?”

“It takes a little more than thinking about you to get me off, dear. But yes, I managed a little excitement while you were wanking away…”

“Did you…”

“Nuh-uh, asked and answered. My turn. How many girls have seen you and or touched you naked from the waist down?”

“That’s a toughie… you have to have the exact number?”

“Don’t be crude. If you turned into the male version of a slut over the last year at the uni I withdraw the question.”

“Actually, I was trying to figure out if my aunt also washed me as a baby or not. Other than that, my speedo slipped down one time at a diving competition, but I am sure you are referring to the number of women that wanted to see my engorged manhood…”

“Quit stalling or I call a dare.”

“Fine, give it your best shot. I’ll take a dare from you.”

“What? No answer? Fine then. Until we get out of the pool, you have to pull your trunks down to your knees. That way if my grandparents come out you can get them back on quick enough.”

“Wait a minute… That’s picking up the pace a little isn’t it?” I was actually happy with the dare. It sounded like we were going to enjoy our afternoon and hopefully the whole summer.

“Well, if you want to quit already…”

“No, just making sure you know what you are getting yourself into.” I reached down and slid my trunks down.

I was still right up against the pool float and on the other side of it from the house. Still, Cheryl could catch a water blurred gaze at my hardened member.

“Let’s see, for my question, I want to know how many guys have made it to second and third base with the lovely Cheryl.”

“Cheryl who, Tiegs?”

“I believe I am referring to the Cheryl in front of me.”

“Over or under?”

Zing! That went sent a jolt through my body.

“Stalling! Guess you get a dare as well.”

“No, wait, I’ll answer.”

“Too late, c’mon, out of the water.”

“Where are we going?” It was then that I realized I was having trouble wading through the pool due to my suit dilemma and I started to pull them up. “Not so fast big boy, not til we are out of the pool.” As we walked though the shallow end my stiff cock broached the water plane like a killer whale. and splashed back down with each step. Cheryl covered her cute mouth to hide her smile and her arousal. At least it distracted her from where we were headed, the roof.

“You are so going to pay for this,” I said as I finally pulled my trunks up. The head of my swollen cock still stuck over the waistband and there was no repositioning it.

“It looks cute, like you have a mushroom growing out of your stomach.” We both had a laugh at that but then we approached the stairs. “We’re going up to your apartment for my dare? I don’t know about that.” Her voice told another story but that was not my intended destination although thinking back it might have been just as well.

“Nope, the roof. We’re jumping off together.” She shrunk back a step.

“I don’t think I can do it.”

“Of course you can and I’ll be there with you. Besides you don’t want to be the one to quit do you?” slot oyna With that she stepped in front of me and climbed the stairs. She jumped up on the railing and proceeded onto the roof without so much as a glance back at me. She made it all the way to the far edge of the roof and froze. Again.

“I can’t do it. Anything else, within reason. Hell, I’ll take two dares.” I shook my head. “Two dares and another question I have to answer,” she pleaded.

I looked around for a few seconds as if contemplating my response, “Ok, two dares and a must answer.”

“Ok, let’s get down from here.”

“Not so fast, I’ll take that first dare before we go. I want to see and taste that beautiful pair of breasts you have been teasing me with all afternoon.”

“What? Up here? The whole neighborhood can see!!!”

“Actually, no they can’t. I looked around and those trees grew in over the last couple of years and blocked old man Grizzard’s house. The peak of the roof blocks the rest.”

“What’s your second dare?”

“Let’s get this one out of the way first. Then we’ll go down and relax and continue our game.”

“How long?”

“How long what?”

“How long are you going to play with my titties?”

“As long as it takes, I guess…”

“That’s not very reassuring.”

“Do you want me to call stalling on you again?”

With that she leered at me and pulled the strap of her one piece off her shoulders and peeled her suit below her breasts. They did not have a bit of sag to them. Her aroused nipples belied her trepidation. I cupped her left breast in my hand and felt the softness of her skin. I knelt down in front of her and kissed her right below the center of her heaving chest. I pulled her down on her knees as well. She let out a relaxing sigh. I put my other hand in the small of her back and drew her closer to me. I looked up into her eyes and saw the desire I had always hoped was there. My palm caressed her hardened nipple and her body gently shuddered. I took the other nipple in my mouth and flicked it with my tongue. Once again her body shuddered and she pulled my head to her chest making me engulf her whole breast. My cock was gushing lubricating fluids so I straddled her leg and gently rubbed my partially exposed erection against her thigh. I could feel the need to explode building up but I wanted her to feel the same. I took the other breast out of my mouth and blew gently on it creating a cooling sensation. I took the other breast in my mouth and slid my hand on her back beneath the material of her swimsuit. This caused her to jump at me, lifting her hips and thrusting. She pulled my face up to hers as I humped her leg and we shared a passionate kiss our tongues intertwining. I went to the next step and slid my free hand down the front of her suit. Just as my fingers found heaven her body spasmed like never before and I felt her juices flow over my fingers as my cock shot a load of semen over her suit and stomach.

My middle finger must have brushed across her clit because the next thing that happenedwas her body flailed out of control knocking me backwards and toward the edge of the roof.

I felt myself falling. With a last second effort I pushed off from the roof and prayed my trajectory would get me safely to the edge of the pool. I was so close. Just a couple more inches would have saved my ankle from shattering on the concrete edge. I heard a splash beside me and saw my dearest Cheryl coming to my aid. She had paused long enough to pull her suit up which is a good thing because my screams of pain had brought her grandparents outside quickly. I could feel the pain in my ankle radiating up my leg. Cheryl’s grandfather jumped in the pool fully clothed and dragged me to the shallow end.

He was a strong man but there was not getting me to the car so they had to call an ambulance. Cheryl was sobbing uncontrollably at this point saying it was her fault.

I of course had slipped into shock to mask the pain and waited quietly for the ambulance. Cheryl’s grandmother kept me focused enough to keep me from passing out. I’ll just skip the next 24 or so hours because its kind of embarrassing making up lies to your parents about how you stupidly tried to get Cheryl to jump off the roof and wound up falling instead and how the operation to put my ankle back together took so long and and the pins and the hospital bed, the pain killers, etc. My next coherent pleasant memory was Cheryl standing by my bedside with my favorite breakfast chicken sandwich.

“I am so sorry.”

“Really its not your fault, Cheryl. It was my stupid idea. My stupid fault.” I stopped. She was crying.

“Are you in any pain?”

“No, they got me pretty doped up. Hope the parents don’t come and start asking questions again. I might blurt out the whole truth. Do they have any idea what we were doing up on the roof?”

“No, but your sister might now since she’s sitting over there.”

“This is all her fault anyway for giving you that box.”

“My fault?!? You’re just lucky I found it canlı casino siteleri and not mom. Anyway, you’re secret is safe with me. I sure don’t want Cheryl giving any of the dirt she has on me to our parents.”

“How long am I going to have to be in here?”

“Just a couple of days, then mom and dad plan to take you home. Lucky me, I’ll get to take care of you while they’re at work…” My sister sounded too pleased, not.

“Or you could stay in your new apartment and I can take care of you,” Cheryl threw in. “My summer classes will let me be there early in the morning and all afternoon.”

“But I was supposed to take care of the house in exchange for rent.”

“You know my grandparents better than that. They will feel guilty since they partially blame me for what happened.”

“If they ever found out what really happened you’d both be out on the street,” my sister chimed in again.

I stared my sister down, “I guess they better not ever find out.” She looked away. I think I won that one.

About that time my parents and Cheryl’s grandparents came in talking like they already had everything planned out. Turns out I would not be truly mobile until the middle of the fall semester due to the reconstructive surgery. My parents had already agreed I might as well stay in the apartment because the only option in the new home was either my sister’s room or the couch. Neither made anyone happy. I would have to either take a semester off or attend the local college for the fall as well. I could take some core classes that were required and would easily transfer. They had already talked to the registrar at both schools. “How long was I out? You guys have already planned my next 6 months!”

“Son, it seems we should have had more say in your planning to begin with,” my dad replied.

“Lot of good your planning did here.”

“Son, I hope that’s just the drugs they have you on and not your smart mouth. I can always break the other leg for you.”

As it is, I was not quite sure myself. I pretended to doze as they continued their planning. Cheryl eagerly jumped at the chance to play nurse maid to me. “Well the insurance will cover just about everything and the scholarship stipend will cover the rest. And there is a class he was thinking of taking online this summer that looks like a lock now,” I heard the rest of my life being planned.

Cheryl did not leave my side except to go home and sleep for the next four days. I think she would have slept in my room if her grandparents had allowed it, but that would not have been proper. A nurse came through and showed her how to clean my leg which I could not reach since it was suspended in mid-air. The rest of my body, she said, I could take care of myself, sponge bath style until the doctor cleared me to stand long enough to shower. The thing I dreaded most of course was bed pan duty. And despite my dazed self, every time I smelled Cheryl’s perfume I would start getting a little wood and was unable to relieve myself without leaving evidence for the nurses.

A week later it was time to go home. The ambulance was used because it would take two good sized guys to get me up the stairs and into my new bed. Thank god they gave me some pain killers before that started. The pain killers knocked me for a loop and so by the time I was aware of my surrounding my family had gone home and Cheryl’s grandparents had turned in leaving the two of us alone.

“Hey, babe.”

“Oh, Mark, you’re awake again. Would you like something to eat?”

“No, I’m not really hungry. Everybody gone?”

“Yeah, it’s almost 10pm. I told my grandparents I would wait til you woke up again before coming down. The EMT’s said it might be as late as midnight and it would be better if someone was here in case you needed anything.”

“So, I can keep you here for two more hours without arousing suspicion? Excellent!”

“Just what did you have in mind?”

“Well, I still have a dare and a must answer question for you and I have been thinking about both for the last four days.”

“But I jumped off the roof after all!” Her protest was lame and had no conviction to it. She was looking forward to what was coming as well.

“Do you want the dare first or the question?”

“The question I guess.”

“Ok, here goes. How many guys have you given a happy ending to?”

“Does the roof count?”

“Yes, I guess I got my happy ending before I fell off the roof.”

“That would be my second then. But the first one was really unintentional. I had been dating this guy and he grabbed my hand and wrapped it around his ‘giant slab’ as he called it and used my hand to jerk himself off. It was the last time we went out too. I can’t say it was very much fun for me. And his prick was not as large as yours. He was proud of it though.”

“Sounds like a real asshole. Ok, ready for the dare?”

“Yeah, I guess so.”

“Well, I would like a sponge bath. A real sponge bath. I am tired of cleaning myself and getting no relief for the last week. And you have to be naked while you do it. And I need a happy ending. You have no idea how much I need a happy ending right now. I think that one nurse was intentionally taunting me, trying to get my blood pressure up.”

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