Caught Again, a Quick Story

By J J

Published on May 19, 2024

Transgender

Caught Again, a Quick Story

CATEGORY: Transgender/TV

Story codes: M/M oral

AUTHOR'S NOTE: Just a quick little story idea that came to me today. I've been writing the next chapter of "Sandy's Journey" in my head, and I should put it into electrons later this week.

Just another one of those days -- a quiet Sunday at home. I'd been doing some housekeeping, watching TV, napping, all dressed in women's lingerie.

I used to crossdress a lot, but I gave it up years ago, figuring I no longer had the figure or face to get away with it. Then, a guy I've been hooking up with lately asked me if I liked panties.

"Well, yeah, but I haven't done that in years," I answered.

"Would you do it for me?"

"I'll have to do a little shopping, but I think I'd like that," I told him.

So, a little shopping. I found to my delight that in this wonderful internet era, you can buy lingerie sets specifically tailored for male anatomy. Ohhhhhh.... I bought a couple of sets, and some thigh-high stockings. The next time he came by, I wore a pink set with black lace edging. Boy, did he get hard in a hurry. I'd forgotten how much I liked the feel of them, and started wearing them sometimes when I was alone.

Anyway, back to today's tale. I was lounging about in one of the white satin sets, thong panties with a lace front and a matching bra. I don't care for the "pouch" panties, preferring something that supports my boys a little more. Wearing them all day is like mental edging, building up to when I masturbate, sit on a big toy, watch porn, and cum heavily.

My doorbell rang. Now I'm not entirely stupid -- I keep something handy to cover my femme goodies if needed. In this case it was a terry robe, and I wrapped it up tight with the sash. I checked through the peephole, and it was one of my neighbors, a guy a few years younger than me, taller (most men are), but with my same middle-aged bulge. Like most neighborhoods, we aren't really very close, and I tend to keep to myself. I knew his face, but couldn't remember his name.

I unlocked and opened the door with a smile and a "Hi", and he said, "Hey, I'm Jeff -- we live across the street?"

"Sure, what can I do for you?" I asked.

We're going to be out of town for a few days, and I'm expecting a package. Would you mind keeping an eye out for it and putting it away until I get back?"

"Sure," I said, "Happy to help."

"Thanks," he said, and reached out to shake my hand. His handshake turned out to be quite vigorous, and the front of my robe opened slightly. I didn't realize it, but my bra was showing.

"What have we here?" he said. Releasing my hand, he took the lapels of my robe and pulled it open, revealing my bra and panties. Oh, shit, I thought.

"Now the last time I saw a guy dressed like you," he continued, "he turned out to be one hell of a cocksucker. I'm willing to bet you are too."

with that he put his hands on my shoulders, gently easing me back into the foyer. He closed the door behind him and locked it, then undid his belt and zipper. He pushed his pants and boxers to the floor, and his hairy cock was right there in front of me.

"I figure you want to," he said. This will just be between us, I promise."

I'd been thinking about cock all day, and I'd been unmasked (disrobed?), so I couldn't see any reason not to. I got down on my knees, kneeling on the front of my robe. I took his meaty, soft cock in my hand and stuffed the whole thing in my mouth.

I held his balls in one hand and began giving his rod the vacuum cleaner treatment, sucking hard. My other hand went to my own body. The satiny cloth of the bra really made my usually insensitive nipples quite perky, and I took turns pinching each one, then rubbing my package through the panties.

He had the slightly musky smell of a man who bathed that morning, but got a little warm in his boxers. He wasn't the type to manscape, and his hairy bush stuck out in all directions. I prefer shaved, because I don't like getting hair in my teeth, but suckers can't be choosers.

His rod came to life in short order -- I mean quickly, because it wasn't short when it came to order. About 6", with a respectable girth. I expect he made his wife very happy. Right at the moment, it was making me happy, in expectation of a mouth full of warm cum.

I took his rod in my hand, pumping it into my mouth. He spread his legs, and I reached through to take his ass cheeks in my hand, squeezing one side and then the other. Then I slowly traced the crack of his ass down past his hole to his perineum, where I stroked and teased, getting him up for a real mouth-filling orgasm.

His breathing increased, deep and powerful. He took my head in his hands and fucked my mouth. I let him. He was pushing into the opening of my throat, but the angle was wrong for me to swallow all of him. I just let him punch the head of his prick against the opening again and again.

My cock was getting hard by this time under my manual stimulation. I pulled the front of my panties out to give it room, then let them snap back with about 3" of me exposed. The rubbing of the satin against my balls was wonderful. I bounced a little and squeezed my thighs together to excite myself.

"You are a goooooooood cocksucker," he said. "Keep going. I'm gonna fill your mouth here in a minute. From what I've seen so far, you'll want to swallow it."

He was right. I guess I wasn't so complicated after all. I was just a garden variety cock slut.

He was still fucking my mouth, pushing his hips forward to ram it into me. I tightened my lips to increase the friction, making my mouth a pussy for his cock. I had my thumb and finger around the base, jerking it as he thrust into me. With the other hand I teased his balls, squeezing them a little, teasing around behind them, even scratching them a tiny bit.

"Here we come, JJ," he rasped. His body started to tense up. I could feel it in his thighs against my arms. I could see his belly sucking in.

He fucked my face harder, and I had to work to hold my throat closed so he wouldn't gag me.

"Mmmmmmm. Mmmmmmm. MMMMMMMmmmm. Nowwwww!" and with that I felt spurt after spurt of cum spilling into my mouth. He held my head all the way down on his prick, making swallowing difficult, but I pulled back a little and got almost all of it. Just a tiny dribble escaped the corner of my mouth. Then he released my head. I gathered up the errant cum with my fingers and put them in my mouth.

"Clean me up good," he said. "Liz will be home soon, and I don't want to smell like cum."

I licked and sucked every bit of his softening rod, collecting every trace of my saliva and his cum. I ran my tongue around its hairy root to make sure.

"That was great, JJ, and I'm glad I got to know you a little better," he said as he pulled up his boxers and pants. He buckled his belt and started to turn towards the door.

"You know, that guy was an awesome fuck too," he said, smiling at me. "We'll give that a shot when I come to pick up that package."

He laughed and let himself out, leaving me there on my knees, unsatisfied, precum dripping from the head of my dick. Well, I thought, that's some serious edging. Time to get out one of my toys.

Next: Chapter 2


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