Shadow Day

My daughter informed me that her friend, James, wanted to ask a favor. They were both in 8th grade and had to ask to “shadow” someone who worked in a job that they thought they might like to do “when they grew up.” James wanted to know if he could shadow me for a day. I agreed. A few days later, James came to the house to work out the details. The assignment was to spend the day watching what I did, and write a report about it. He asked what he should wear (I explained business casual - khakis, a golf shirt, etc) and when I had to be at work (I usually got into the office around 9 and left around 6. I enjoyed having the office to myself for a few hours, as most of my coworkers came in early and left between 3:30 and 4:30.) We got everything arranged and I cleared it with my boss.

The next Thursday morning, James arrived at my door, ready for the day. He was dressed in a pair of khakis that really showed off his young ass, and a kelly green golf shirt that really looked good on him. I should mention, he is a ginger with copper colored hair and bright green eyes. His skin is liberally speckled with freckles. I’ve known him for several years, his parents having a house down the block, and but only recently have I really noticed what a handsome guy he is growing into. I wonder sometimes if he and my daughter were “more than friends” but I would never ask. If she wants to volunteer that information sometime, I have made it clear that I am open. Since her mother left us when she was little, I’ve always tried to be open about things (in an age appropriate way of course!) and so I know that she knows about sex. I also made it clear that when she decides to be sexually active, no matter who she chooses as a partner, I will support her. The medicine cabinet is stocked with condoms and lube along with the products she needs for menses. I also have been open with her about the fact that I am bisexual and that I date both men and women.

Anyway, my daughter had already left for the day to shadow the mom of another friend, so it was just me and James. We drove to the office and spent the day. I worked (at least tried to) and attended meetings all with James by my side. At first it was difficult to keep my mind on work with him right there, and I berated myself for wondering what he looked like under those tight chinos and bright green shirt, but after a while I was able to concentrate more. He asked questions and he even made some suggestions at one point when I was having trouble with a particular problem. Before I knew it, it was late afternoon and people were leaving for the day. Soon it was just the two of us in the office.

I was finishing up a task when I noticed that James wasn’t in his seat. I vaguely remembered him mentioning using the bathroom. So I got up and went to the men’s room. Through the door, I could just barely hear a soft grunting. Curious, I slowly pushed open the door enough to see in. There was James, standing in front of the mirror, his khakis around his ankles, shirt pulled up, slowly pulling his cock. His eyes were closed. He would occasionally give a soft grunt or moan. My cock immediately got hard. Should I go in? I hesitated until I heard him softly moan my name.

I wasn’t sure what to do, so I let the door close and then more noisily opened the door, giving him enough time, I hoped, to get himself arranged. When I came in, he was at the urinals, acting like he was pissing. His pants were still around his ankles and I got a view of his firm tween ass and legs. I stepped up to the urinal next to him, but far enough back so that he could see when I pulled my still hard cock out of my pants. I saw him look while trying to not let me see and I turned so that he could get a good eyeful. His eyes widened and then he looked in my eyes. He looked shocked. I smiled.

“Sometimes, after everyone leaves, I come in here and toss a load. I hope you don’t mind.” I stroked my cock as if I were going to toss off a load into the urinal. He watched me stroke it and turned slightly, so that he was standing at a slight angle to me. I gave it a few more strokes then used my finger to scoop up a bit of the precum from the tip. I licked the precum off my finger and I could see hunger in his eyes.

“Can I…?” he asked quietly. I nodded and he bent down enough to give the tip of my cock a lick. I moaned encouragement.

“Since it’s just us here, why don’t we go and get more comfortable?” I suggested. I knew that there was a couch in the executive offices. I had used it a few times for late afternoon hookups. It wasn’t the most comfortable thing but at least you could stretch out enough to be comfortable.

He pulled up his khakis and I led him to the office. Once there, I shut and locked the door. It never hurts to be careful, especially with someone as young as James. I quickly stripped off my clothes. It didn’t take James long to do the same and I had a chance to really check out his young body. His chest was athletic and smooth. I remembered that he played soccer on weekends. He was thin with a flat stomach and the bony hips that boys his age seem to get. His cock, which was pointing straight towards his stomach, was about 5 inches long, uncut, and surrounded by a small bush that matched the copper hair on his head. His balls hung low and appeared to be hairless.

I stepped up to him. He was probably a good foot shorter than me, so I had to bend down but I pulled him in and put my lips on his. We were soon kissing and tongue wrestling. His body felt small and soft against me. I loved the feeling of him against me. I broke the kiss and swiftly knelt in front of him. I took a few seconds to really look at his young cock before leaning in and licking it from the base to the tip. He put his hands on my shoulders. I took one hand and peeled back the foreskin to reveal the pink tip, I took his whole length into my mouth, feeling the tip at the back of my tongue. He wasn’t big enough to trigger my gag reflex and I felt his bush tickling my nose, He moaned, saying my name. I reached around and took his cheeks in my hands, pulling him harder against me.

As he was a young guy, I knew he would likely cum quickly but be able to get hard and cum again without any problem. I started pulling him into my mouth, feeling his firm ass cheeks in my hands. I could feel his balls slapping my chin. Within minutes he was tensing up and I knew he was close.

“Im my mouth,” I said around his cock and went back to working his shaft for all I was worth. He let out a high pitched moan and I felt his cock pulse, coating my tongue with his seed. I sucked and licked until I had gotten every drop. When I let go of his ass, he stumbled back and sat heavily on the couch. His eyes were unfocused and there was a sheen of sweat on his chest. I wanted to lick that sweat off but instead I let him catch his breath while I enjoyed the taste of his load.

When he had calmed down and was breathing regularly, I sat next to him on the couch. We talked for a bit about him, his sexuality, and what we had done. He admitted that he had had a crush on me for a few years. I asked if he was gay, he looked thoughtful and finally said, “I’m not sure. I like a few girls and would like to fuck them but I also like older men like you.” He then told me that he had accidentally slipped to my daughter that he thought I was hot and she had told him that I was bi but didn’t know if I would be into someone so young. I replied that I am not normally, but I admitted to having thought about him for a few years as well.

By now his cock was once again hard and ready. I asked what he wanted to do next. “Would you..” he hesitated. I told him he could ask me anything and that if I didn’t want to, I would suggest something else. Looking away, not able to meet my eyes, he softly asked, “would you fuck me?” I turned his head back towards me and kissed him gently.

“Yes,” I answered. I went to a nearby cabinet where I kept supplies for my afternoon rendezvous. I retrieved a condom and some lube. I started to open the condom but he stopped me, saying that since it was his first time, he wanted me to breed him. I made sure he understood the risks. I regularly got tested for STIs and HIV but that didn’t mean there wasn’t some risk but he said he was ok with it.

I told him to get on his knees on the couch with his arms on the back. Then I got down behind him and used my hands to pull open his muscular cheeks. His ass was amazing. I was practically drooling just looking at it. I leaned in and started licking his hole. James gasped and pulled away from me, but I pulled him back gently. I licked again and this time he moaned in pleasure. I took my time and really ate his ass. After a while I was able to push my tongue past his sphincter and could taste the inside of his ass. He began to stroke himself but I made him stop.

Feeling like his ass was prepped enough, I stood up and liberally applied lube to my cock. I was as hard as a teenager. I stepped up, put my left hand on his shoulder, and put the head of my cock against his pink rosebud. “I’m going to go slow, but it might hurt a little at first,” I told him. “Trust me. I won’t hurt you but if you are in a lot of pain, say something.” James nodded. I began to push against his hole. It was slowly succumbing to my hard cock but I also felt him trying to move away. I held on to his shoulder and moved with him. After about 20 or 30 seconds, I felt the pop as the head of my cock entered him. He gave a loud cry.

“It hurts!” he said, trying to get away from me. “Take it out!” I kept my cock steady with just the head inside and told him to relax and breathe. I didn’t move, though I could feel his ass clenching and unclenching around my cock. Finally he relaxed. I asked if he still wanted me to take it out and he shook his head, “no.”

“I’m going to go slow,” I assured him. I pushed my cock in about half an inch, and pulled it back. He tensed again but relaxed. “Are you ok?” I asked. He nodded. I did this again, pushing a little further in and again pulling out to where my cock head was against the inside sphincter. This time he released a little moan of pleasure. I smiled. “Ready?” I asked and again he nodded.

I pushed in further, maybe half of my cock in his tight hole, and pulled back. This time, as I pushed forward, he pushed back against me. I began to gently fuck him, not going deep, just keeping things slow and steady, until he was consistently pushing back to meet my thrusts. I paused. “I’m going to go all the way in,” I said. “Are you doing ok?” In a moaning voice he said, “hmm, yeah…”

I put both hands on his hips and slowly pushed forward until my pubes were nestled against his ass cheeks. He moaned even louder and reached again for his cock. I stopped him. Then I pulled out and began to push forward, fucking him slowly. We soon got into a rhythm, with him pushing back against me as I pushed forward. I picked up the tempo and soon I was fucking him hard and fast. I hadn’t had such a sweet, tight ass in a long time and I was enjoying it.

Suddenly I felt his ass tighten and he let out a loud moaning scream. I had a feeling he was having a prostate orgasm and I kept the pace going as he sprayed his load all over the couch. “Good thing it’s easy to clean,” I thought. When he was finished I knew I was close. I began to stroke in and out, pulling my cock almost completely out before slamming it back. Every time I hit his cheeks, he would moan in pleasure.

“I’m close,” I said. Sweat was dripping down my chest.

“Breed me, daddy,” I heard him say between moans, and that did it. Hearing him call me daddy pushed me over the edge and I pushed my cock all the way into him. I felt my balls tense up and my cum spilling into his guts. I rocked back and forth, feeling the intense pleasure of his young body.

When I finished, I collapsed on top of him. We kind of fell over and I rolled, pulling him with me, so that he ended up on my lap, my cock still buried in his muscular ass. I pulled him close to me, and he leaned back so that we could kiss.

I held him there as my cock deflated and finally slipped out of him. Then he turned so that he was sideways on my lap and we kissed some more. I wanted to stay there with him forever. It was magical. Amazing. His body firm, his skin soft, his scent filling me senses, and his kisses so gentle and loving. I knew it was getting late. I had him stand up, then I bent over and licked his cum off of the cushions. Holding it in my mouth, I kissed him again and shared it with him.

“I need to get you home,” I said reluctantly as we got