All characters are over 18.
*
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 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..."
