A month after I graduated high school and just about a week past my eighteenth birthday life was about to become interesting. My dad's best friend had asked me if I would maintain his swimming pool and work in his yard while he and his wife went on vacation for the next two weeks. Tall pine and oak trees just outside the fence and stretching back several feet surrounded it insuring privacy. I was free of course to use the pool.
I got the idea that going around the property naked would be a trip. It was just a question of building up some courage. I started modestly at first, going nude only inside the house. That felt great. By the third day I had begun working naked outside, leaving my clothes inside the back porch.
I am five foot eight with a fairly good, albeit lean, physical build. I weigh 145 pounds. My circumcised cock measures a good six inches.
It was fairly early in the morning of my third day when I picked up the net and began skimming leaves and buds from the surface of the water. I held it's long handle clumsily across the pool but quickly adjusted to it. The automatic vacuum moved slowly across the pool floor.
There were other small jobs. Finished with the pool I began pulling up the clover and grass clumps that seemed to be everywhere between the flowers and along the fence. Starting directly beside the round white patio table I worked my way around the pool.
Voices next store sent me hurrying into the house to put on my clothes. Though they were quite far off outdoor nudity was new to me. I had the uneasy feeling that they were watching and ready to gossip if not already gossiping.
While I was inside wearing just my jeans with no underpants I helped myself to a coke and drank it slowly. How long do they plan to stay out there? Suddenly it occurred to me that there are too many trees between their back porch and me.
By day four I had grown a little bolder. Arriving on the property at eight, I immediately stripped naked and left my clothes inside the guest bedroom. Within just a couple of minutes I was outside swimming.
After swimming for about twenty minutes I started working again. There were some hedge bushes beside the driveway that needed to be cut. That job took a few minutes plus a few more to pick up the cuttings. By nine thirty I had finished.
Those dark blue trunks had to come off. Hurriedly I returned the equipment to the shed under the deck then returned to the swimming pool. The bathing suit came off.
This is better.
Having finished the yard work, I could spend my days enjoying the pool. I relaxed in a chase lounge.
I come from a close nit family though I do not tell mom and dad everything. Good heavens, I can't tell them about this. They would make a fuss and that's the last thing I need.
I had been home for about a hour when my mother inquired.
"How's the yard work going?"
"fine," I replied.
"The Jamisons will be home in another week. They'll be happy to see the nice work that you did."
Since the age of fourteen I had been cutting lawns on my own street. Aside from making my reputation as a good worker the job put more cash in my pocket then most boys my age. Mr. Jamison had offered me big money for this current job.
Ted Jamison is a man in his mid forties and quite handsome. His hair and eyes eyes dark brown. His face is square shaped and his nose straight. He said once that he's 44 so I took his word for it. He is my height but a bit heavier.
He keeps himself fit. I had seen him jogging at times and he mentioned something about going to a gym during his younger days. He also mentioned playing high school football as a wide receiver.
The second week had passed. Laying in the chase lounge I had not given any thought to the Jamisons returning. Instead, a little sleepy because I had not slept well the night before, I closed my eyes in the chase lounge. I was aware of the sound of car doors and footsteps but gave that little thought.
Suddenly I became aware of a hand closed around and stroking my rapidly stiffening cock. I opened my eyes to the last thing I ever expected.
It's Mr. Jamison! He stood over me naked.
"I spend a good deal of time myself out here naked when the wife's not around. I've been wanting a cute boy for a long time."
When I didn't react he continued to stroke my cock until it swelled to the full size and went erect. Though I had never told anyone I had always dreamed of a cute boy taking me, and having his way with me. I wanted him.
Ted pressed his body against me and his lips against mine in a passionate kiss. Mouths opened and tongues pushed inside licking. His hand continued to stroke my man meat while his other hand slid under me to find my ass. Making love to a 44 year old man is so cool! I'll bet not many eighteen year olds have this chance.
He sat up. Eagerly I spread and lifted my legs. Grabbing me by the ankles he rested my legs on his shoulders.
Now I felt the seven inches of his swollen and throbbing organ pushing into my tight virgin asshole, stretching it, rubbing against flesh, making it tingle, and ultimately going deep inside me. The pain was mitigated by the feeling of intense pleasure. The huge cock slid slowly back and forth for probably two minutes or better. I did not count the seconds but just took him and voiced soft guttural moans.
"Don't stop! Keep fucking me!"
"Oh baby I've been looking forward to this with a cute boy since forever."
Suddenly I felt love juices surging inside me. He pulled out leaving cum oozing from the hole. I lay there, looking up at him and smiling. Will I ever have this again?
"It will be easier the second time because your hole is widened. The dick will fit better."
Fantastic, I thought. There will be a second time.
"What would your wife say?"
"I don't give a crap. I'll most likely admit that I like boys and ask her to divorce me."
I kissed his mouth again, this time deep, lingering for several seconds. My hands made small circles on his chest while my thumbs raked up and down over his nipples.
"May I ask how long you've been married?"
"Eighteen years. Since I was twenty six."
An interesting irony, I thought.
He moved off and sat back on the lounge next to me. It was not a moment too soon. Following his lead I quickly put on the trunks he brought me. They were my own of course. A moment later Jill came outside in her lime green two piece and sat with us at a chair beside the table.
"How was the trip?"
"We had a great time."
She had no clue that her husband just had great sex with me and was considering leaving the marriage. I could see that in the way she acted towards him.
A few days later
My cell phone placed on the hood of the car rang while I played basketball at end of the driveway. The rendition of Sweet Dreams by Roy Buchanan identified the caller as Ted Jamison.
"Hi," I said. "What's going on?"
"Jill's at her girlfriend's house. It's her Bingo night and I need some company."
A few moments later I arrived. After a brief nude swim we walked inside the house and into the guest bedroom.
Ted took me against his body, slid a hand down to my ass and squeezed gently. His other hand cupped my balls while we kissed with mouths open. I wanted it lying on my side. He obliged. His monster cock slid easily into my orifice. His rhythm was slow and steady.
Neither of us paid any attention to time passing as we lay on the bed caressing each other. A kiss on my cheek was followed by another and another. He touched his lips against mine.
The opening front door was barely audible. Then footsteps grew louder. The guest bedroom door opened. The shit hit the fan.
"Oh my God!" shouted Jill.
I sat up, jaw dropped and wide eyed. Jill's temper was rising fast. Ted sat up staring at her. All he could say was, "divorce?"
"Ted just go and take your young boyfriend with you! I won't even fight this!"
Grabbing my clothes quickly, I dressed and headed for the door.
Within a half hour after the shouting I was home in my own bedroom with my concerns. What would dad say about my sexual proclivity? How would he react to learning that I'm having an affair with his high school classmate and best friend?