Caught Again – A Quick Story Pt. 05

AUTHOR'S NOTE: Hi folks. The basis of this story is true. I was working in my shop dressed as described, and a neighbor came by. The naughty parts are just a fantasy I cooked up.

Well, it happened again.

It's not that I'm not careful, and it's not like I go around throwing myself at people, but this stuff just seems to happen to me.

I was working in the shop behind my house. Things were getting old and ratty, and the place needed a new coat of paint and a little organizing. I'd gotten out my rollers and brushes and pans, bought a couple of gallons of paint that would be durable and not show the dirt too bad, and I was painting away. I like painting, and I'm pretty good at it.

I was wearing my old painting clothes, Dickies blue uniform pants and shirt, spattered with many colors gathered over the years. Underneath, of course, was a different matter. You know I like panties and bras and sexy lingerie, and I wear them most of the time. Lately I've been buying bodysuits. I like them sleeveless, with a thong back and snap closure at the bottom. I often wear one around the house. Above the waist they can pass at a distance for a man's muscle shirt. Below the waist my cheeks are on constant display, and the thong rides between them, reminding me of the hole there I allow others to use. The occasional slide of fabric across that hole, especially when I bend over, is delicious.

This day, it was my white bodysuit under the blue painting clothes. Showing through the open collar at the top of my shirt, it looks exactly like a man's wifebeater shirt, but it's thicker, and softer, and much more comfortable. Like the rest, it has a thong back and is always a sexy reminder of my desires.

A guy from down the street stopped by to see what I was up to. We had met a few weeks before when I was getting my mail from the mailbox on the street and he was walking his two dogs. He had noticed the shop and stopped to talk about it, as he was considering having one built. He'd been passing by again today and noticed the door to the shop was open. He hollered as he approached and I invited him in.

We talked as I continued to paint. Like most men, Steve is a bit taller than me. He's got the nice slender figure I like in my sexual partners. I'd noticed it, but today I was concentrating on my work, not looking for cock.

We talked about the weather, Steve's planned shop, what I was going to do with mine. Then I made a mistake. The afternoon was getting warmer, and I decided to take off my painting shirt. I did think about what I was wearing underneath, but thought it wouldn't be noticed with pants on. Like I said, it just looks like a singlet above the waist.

What I didn't notice was that it had ridden up a bit, and the open sides had slid above my belt line. I was just talking about tools and didn't notice Steve's gaze had locked on my waist. He got a puzzled look on his face, then he started laughing.

"So you're the guy!" he said, and continued laughing. Now I was confused.

He walked over to me. "My wife has a few outfits just like this," he said. He put one hand down by my side, and pushed one finger through the opening at the bottom of my bodysuit. Then he did the same at the other side and pulled up the edges of the bodysuit. It gave me a bit of a wedgie, pulling on my cock.

Then he let go and told me, "I've heard there was a bisexual guy here in the neighborhood who crossdressed. I'm guessing that's you."

Well, like I said, caught again. No sense in being embarrassed about it. I just smiled and said, "Yup. That's me."

Can I see?" he asked. He was smiling, so I didn't think he was going to beat the shit out of me. What's more, there were undertones of genuine interest in his expression. To put the frosting on the cake, he reached down and adjusted his cock through his jeans.

Okay, I thought, let's show him my best side. Turning around, I looked back at him over my shoulder as I undid my belt and zipper. I unbuttoned my painting pants and slowly began lowering them. I made it a little sexy, sliding them side to side and rocking my hips as I very slowly dropped them down below my ass, then let them slide to a puddle at my feet.

"Yup, just like the ones my wife wears," he said. "and they're just as sexy on you as they are on her.. That's a really nice ass."

I wiggled my ass a little bit, and smiled to let him know I enjoyed the compliment. He reached down and unzipped his jeans. I know an invitation when I see one, so I stepped out of my pants and wriggled my way over to him. I stood really close, put one hand on his chest, and looked up into his eyes as I reached in through his zipper and the opening in his boxers to grab his cock.

He really did like what he was seeing. He was hard already, so hard I had to use both hands to drag his prick out into the open. He smiled down at me as I stroked it for him, then put his hands on my shoulders and gently pushed down. That was all the encouragement I needed to go to my knees.

I pulled his balls out into the open. I held them in one hand while I stroked him with the other. It was a respectable size, about 6", circumsized with a beautiful flaring head. I prefer cut cocks -- for some reason the head is more pronounced. I like putting the head in my mouth, licking it, then putting my teeth down gently right behind the flare and sucking it hard.

I did that to Steve, and he smiled down at me. Then I took more of him in my mouth, licking the underside with my tongue. He tasted wonderful, fresh and very clean, like he was just out of the shower. I worked at generating as much saliva as I could, wetting and lubricating his pretty rod. I sucked him in right to the opening of my throat, licking the underside, and then I clamped my lips down hard, sealing him in my mouth. I slowly withdrew, keeping as much suction as I could, until only the head was in my mouth. I repeated this several times, then stroked him in my hand while licking his balls. He was shaved, so sucking his balls into my mouth one at a time was a pleasure.

"That's good, baby," he said. "My wife won't suck, and I miss it a lot. Keep going -- get me really hard."

He seemed awfully hard already, but while I'm not in any way submissive, I do like to please. I took him back in my mouth and started pumping away, using my hand and my mouth together to simulate my boy pussy. My own cock was getting hard, and it had slipped out the side of my bodysuit. The fresh air felt good on it.

Steve moaned his pleasure. Reaching down, he undid his belt and jeans. He pushed them down. I took my mouth off him long enough to get him out of his boxers as well. Everything went to his knees, and I went back to sucking him.

He had what seemed to be an unmoveable smile on his face, but he closed his eyes and leaned his head back. He moaned again and put his hands on the side of my head. I let him take control, and he started fucking my mouth, sliding in and out. I circled my finger and thumb around the base of his dick, squeezing and releasing. With my other hand I caresed his balls, then reached behind them to tease the soft skin of his perineum. I kept pouring all the saliva out that I could generate, until it was dripping off him as he skull-fucked me. The top of my bodysuit was getting very wet with my spit.

I pulled off just long enough to say, "Do you want to cum in my mouth? I'll swallow it all if you do...." Then I grabbed his hips and drove my mouth back down onto his cock. He understood what I meant - that that he had options. I wriggled my butt a little to reinforce the invitation.

He looked down and me, and his smile got even bigger. He nodded, wiggled his eyebrows in a funny way, and said, "Wanna fuck?"

I held his cock in my hands, licked the head and smiled up at him. I just nodded. He took hold of my shoulders and pulled me to my feet. Turning me around, he grabbed me by the hips and pulled me back against his cock.

I had a piece of shop equipment that I'd designed just for this moment, and I pulled away to set it up. I'd built a couple of sawhorses for the shop, exactly the right height for me to lay lengthwise on one, giving me something to hold on to while making my ass available. Setting one in the middle of the shop, I leaned over and assumed the position. I looked back at him over my shoulder as I rested my belly on the crossbar, my feet alongside the sawhorse feet. I put both hands on the cross piece, then smiled and wiggled my ass again.

Steve laughed, then slipped out of his pants and boxers and advanced on me, his hard prick leading the way.

"Close the door," I said, "I might get loud." When I'm in this mood I tend to giggle girlishly, as I did now.

He detoured to close and lock the door, then came to my ass. I felt very slutty, and loved it. He squatted down behind me and separated my cheeks with his hands. "Yup," he said, "snaps -- just like my wife's." He deftly unsnapped the bottom of my bodysuit, releasing my cock and balls. He pushed the back strap up under the top. For a moment I thought he might play with my cock, but he was clearly only interested in my hole.

He spit on my boy pussy twice, then rubbed the spit around and into me with his thumb. I've been fucked enough that my hole seemed to draw him in. He stood up and I reached back to hold my cheeks apart for his entry.

His cock was still wet from the sloppy blowjob, but he spit once more into his hand and added a last bit of lube to his dick. Then he stepped forward, his feet touching mine, and placed that pretty purple helmet against my hole.

"Keep it open like that for me, baby," he whispered. Holding my hips and hands in place, he gently pressed forward. The head slipped easily inside me, and now it was my turn to moan. God, he felt good!

He slid in until he was about halfway inside, then started fucking, going deeper with each stroke.

"I haven't fucked a sissy since I got married," he said, "I'd forgotten, but damn, this feels good."

"Good for me too, Steve," I replied "Fuck me good."

Deeper and deeper he pressed, until I felt his balls hit me. He started to go faster, and I pulled my hands free to hold onto the sawhorse. I arched my back and looked back at him. I smiled and mouthed "Fuck me."

He kept long slow strokes, pushing downward into my ass. I squeezed his prick with my internal muscles in an irregular pattern, milking his cock.

"God, I missed boy pussy," he breathed. "I'd forgotten how good this is. JJ, your ass is amazing!"

"Show me," I said, "Fuck it good and cum inside me!"

He started slamming into me, and now I moaned loudly. I wiggled my ass as he pushed into me again and again, changing the angle of his cock inside my hole. I continued squeezing him. I lay my head down on the bar. I'd sanded the whole thing very smooth -- don't want splinters at a time like this.

His hands gripped my hips roughly as he fucked me. I pushed back against his thrusts. Our spit was barely enough lube, but he was drawing the juices from inside my hole. Each thrust made my boy cunt burn with friction.

His downward angle pressed against my prostate as he thrust. My cock hardened and twitched, begging to release a load of cum. Behind me Steve put his head back. His mouth was opened as he gasped for breath. His eyes were closed as every bit of his attention went into his prick and my grasping pussy. His balls banged against my shaven perineum.

I thought for a moment that without the rubber feet I'd put on the sawhorse, we would have skidded over to the workbench by now, which made me giggle again.

"Do you like this cock in your ass, JJ?" he asked, bringing me back to the task at hand.

"I love it," I replied. "Pound me hard and fill me with your cum! I know you like girls like me. You've been looking for me, haven't you? You heard there was a CD here, and you couldn't wait to find and fuck me!"

"Yes, yes," he said. "I love being married, but I've missed sissy pussy. I'm gonna fuck you through the floor and fill your cunt!"

He continued pounding me, testing the limits of my hole and my fucking horse. My cock twitched again and again, I could feel my balls drawing up against my body, and I thought I might cum soon -- a rare sissygasm, induced solely from being fucked.

"You're gonna make me cum," I said. "Fuck me harder, make me spurt all over the floor!"

"Yes, baby," he moaned, "Take my hard prick!"

His hands on my hips were almost pulling me off the floor as he pounded my hole. I could feel his thighs twitching when they slammed against mine. Suddenly there it was -- he hit exactly the right spot inside my ass, and my cock exploded. "Cummmmiinnnng" I groaned. Spurts of cum flew everywhere beneath me, wetting my legs, puddling on the floor.

As I came, my sphincter musles clenched around his cock, spasming in pleasure.

"Holy fuck!" he cried. "I'm there -- I'm gonna fill your fucking ass!"

I felt his cock swell and twitch as he pushed his cum deep into me. He slammed into my ass again and again as his load filled me.

He came to a stop as deep inside me as he could get. He let go of my hips and put his hands on my lower back, leaning on me as he regained his breath.

"Fuuuucccckkk...." he said, and I knew exactly how he felt. He took a couple more long slow strokes into my ass, feeling the immense pleasure of the soft friction on his dick. My hole had relaxed, and I could feel drips of his cum sliding out and down to my balls.

"That's amazing, JJ," he said softly. "I'm glad I figured you out."

"I loved it, Steve." I replied.

He withdrew his softening, messy cock. I got off the sawhorse and found a couple of clean rags. I tossed one to him, and wiped the cum off my asshole with the other. I knew his load would continue to drip out of me for the rest of the afternoon, a feeling I looked forward to.

"I hope we can do this again," he said softly, his voice lower and somehow affectionate.

"I'd like that," I said with a smile, "but keep it to yourself. If there's a constant parade of cocks out here I'll never get anything done."

We both laughed. "Don't worry," he said. "My wife would never understand this. I'm sure I can count on your discretion too."

"Completely," I told him. "I don't want to cause anybody trouble, or do anything that might cut off my supply of cock."

We laughed again.

I snapped the bottom of my bodysuit closed. I felt the first drops of sperm leaking into it from my ravaged hole. Steve put his underwear and pants back on as I stepped back into my painting pants.

Now we were just two guys standing around a shop again, though with suspiciously happy grins on our faces. I opened the door, peeking out first to see if anyone was watching. No one was in sight, or hopefully within hearing distance.

We talked for a few more minutes about the shop. Then Steve said, "I need to get going. I need to clean up and walk the dogs before she gets home."

"Well, you know where I am," I replied. "Come... by anytime."

We smiled that secret smile at each other, and off he went. I went back to painting with my asshole stretched, dripping, and very happy.