The Night I Crossed a Line I Can’t Uncross

The Night I Crossed a Line I Can’t Uncross

Our friends and their eighteen-year-old son have been staying with us for the week. They’ve been sleeping in our kids’ rooms with Andrew in my daughter’s. We’ve had a lot of fun with everybody here, but I wanted something more.

Ever since they got here, I’ve been watching him. He’s lean and good looking. And when he was in his bathing suit, his body had the defined muscles of a healthy youth. He’s quiet and shy but seems like a good kid.

I found I couldn’t stop thinking about Andrew. When I’m at work, I kept picturing his ass and how it would feel to be inside him. And last night, I jacked off with the image of making his pucker spread open with my cock. I wasted the largest load I’ve had in a long time into the toilet. And I’m sure he’s thinking the same thing. I’ve caught him checking me out on the sly, but he looks away every time I do.

Last night it happened. He’d taken a shower, and we met in the hall. He had a towel wrapped around his tight body and smelled fresh and clean. His eyes looked up at me, and I put my hand on his shoulder as I passed by. Later, I was lying in bed with my dick like a titanium flagpole. Heather was asleep and snoring a little. I weighed the pros and cons of waking her up and taking care of myself, but she was as likely to turn me away as not.

I rolled onto my side and pressed my stiff cock between her ass cheeks, hoping she’d get the hint. But she didn’t wake up. I left myself poking into her butt and weighing my options. Jacking off next to her was always possible, and I’ve done it many times before. It’s fun, but nothing like the real thing.

My next idea was to go into the bathroom and deposit another load into the toilet. Thinking that was the best I was going to get, I pulled back the covers and swung my legs over the side of the bed. But something took over me. I reached into the nightstand and took out our bottle of lavender scented lubricant.

Instead of going to the bathroom, I walked down the hall to the room where Andrew was sleeping. I stepped inside and closed the door, trying not to make any noise. The door squeaked quieter than a mouse. Andrew breathed in and half-sat up alert in bed.

“Shhhh,” I said, holding my finger to my lips, although he wouldn’t be able to see it in the dark.

He didn’t move as I crept to my daughter’s bed and pulled his covers back. As soon as I did, the smell of a young man filled my nose. I pulled down my own pajamas and set my cock free.

I’m bigger than most guys, and this was going to be hard on Andrew, but I’d go slow. With my large hands, I grabbed both sides of his hips and turned his body so that he was on his knees. He didn’t protest or say anything as I manhandled him into place.

The twin-sized bed with princess sheets creaked as I knelt between his calves and feet. My throat was tight, and my heart was pounding as I pulled his boxers down to his bent knees. His ass was pale and hairless in the moonlight, and I couldn’t wait to pump my sperm inside him. But I’d built this up for a week and wanted to savor everything and take it slow.

With my right hand, I reached between his legs and caressed his balls to wake him up. His cock started filling with blood, and I reached forward to stroke him a little. His dick inflated the rest of the way, and a slick coating of pre-cum appeared on the tip. I wiped it all around his glans until it was all worked in like lotion.

I worked up a large reservoir of spit in my mouth and wiped it all over my cock. I sucked my cheeks and produced another gob and drooled it between Andrew’s dewy ass cheeks. He responded by spreading his legs a little further apart and pressing his face into the pillow.

I clicked the cap back on the lube. In the dark, I wasn’t sure how much came out. I wanted to make certain I squeezed out enough to enable my thick cock to fit into Andrew’s virgin ass. When my organ was well lubricated, I smeared the rest along his ass crack and found his hole.

I let my middle finger drag along the pucker and then dipped inside. I’m guessing it was his first such penetration, and he arched his back like a cat. I relished the sensation of his tight sphincter grabbing me. I dipped the tip inside his barrier and worked the lube around.

Before I knew it, I was lubricating deep inside his rectum with my entire middle finger. I was more than ready, and my slippery dick pulsed in anticipation. I pulled it down and directed my phallus towards Andrew’s loosened hole.

He was so fresh and tight that I worried I wouldn’t be able to fulfill my fantasy. I’d have to satisfy myself with a blowjob or by having him jack me off. But I remained determined. Little by little, the tip of my shaft spread his star-gate. He pressed his face further in his pillow, and his fists grabbed the sheets as I shoved myself home.

I used my left hand to squeeze his ass cheek open, and my right to aim my dick. Either his asshole relaxed, or it tore open, but my cock head passed his sphincter all at once. Andrew cried out a little but didn’t protest.

I pushed my hips into him, and my lube-slick cock slid deeper inch by thick inch. He was so snug that every part of my cock stretched his firm young flesh. I straightened his colon, intent on getting all ten inches inside.

When I was balls-deep in his butt, I grabbed his hip bones with both hands and pulled myself a little deeper. He whimpered a little, but Andrew was a good boy and didn’t cry out. I didn’t want his mom to hear me take her little boy in the room next door.

My balls brushed his down below, and his hairy testicles tickled mine. Now I was sure he was a virgin. With slow strokes, I pulled myself out and began fucking Andrew’s ass.

After the initial shock, he never complained or cried out. My strokes became long and quick as I pulled myself as far as I dared and then slipped back inside. Our nuts started bouncing off each other as I picked up the pace and urged myself to completion.

As I grew close, I spit in my hand and reached around to grab Andrew’s prick. I had to know what his hot orgasm felt like when it pulsed through my fingers. I pushed myself all the way into him and held there while I jacked his smaller meat.

As a teenager, he was always ready for sex. It only took a little stroking before his hot seed pumped through my fingers and down into my baby girl’s sheets.

Once his spigot had run dry, I resumed fucking his ass. I dumped my load in his colon for his digestive system to absorb. I let the shock waves pulse through my cock. I wanted to make sure all my nutrients were in him before pulling out.

That part hurt him more than the other, and I had to pull out slow as a snail. As I did, he whimpered into the pillow. When I had removed myself, I climbed from between his legs, and he curled up on his side. The room reeked of sex, but there wasn’t anything I’d be able to do about it now. I pulled the covers back over him and put my pajama bottoms back on.

As quiet as possible, I opened the door and tiptoed back to our bedroom. I put the incriminating lube back in the drawer and got back in bed with my wife. I worried whether Heather would smell him on me. And I hoped he was the kind of guy who kept a secret.

As I stared at the ceiling, I reflected that that was everything I’d hoped. I haven’t fucked a virgin ass in a while, and it was good to bury my nut in a fresh hole.

Maybe I should suggest they stay with us another week, I thought.