Caught Again, a Quick Story

By J J

Published on Aug 28, 2024

Transgender

CATEGORY: Transgender/TV STORY CODES: Threesome, M(cd)FF, oral, anal, toys

AUTHOR'S FOREWORD: It seems this little tale has grown some legs. It's become popular, so I'll add another chapter and see what happens. Each of the neighbors in this saga is physically as I describe them. The rest is just fantasy, the product of lots of time alone and my perverted imagination. Don't forget - this site works on DONATIONS. I provide my meager descriptive skills and depraved imagination. You get to cum all over yourself. No bucks, no fucks. Hit the button.

These sleepy afternoons seem to be dangerous.

I don't go hunting for partners here in the neighborhood, but lately all it takes is a quiet afternoon at home and they come looking for me.

I was coming home from the grocery store about noon when I saw Angie checking their mailbox. She waved, then walked over to chat as I pulled into my driveway.

"Hi, baby!" she purred.

She looked like she might just throw her arms around me and kiss me, but she restrained herself out here in public.

"Are you going to be home this afternoon?" she asked. "I was talking with our new neighbor Vickie, and she wanted to get together."

The house next to me had changed hands again -- the fourth time in ten years. They were a young couple, probably in their late twenties. It seemed the house attracted downsizing retirees and first-time buyers. I had met the new neighbors in passing when they came to look the house over with her parents on the day they closed the sale.

(You can read about the previous owners in my story "The Neighbors", which is actually the first chapter in this sordid tale. We'd had some fun together, and I was sorry they'd gone.)

"Can we come over about two?" Angie continued.

"I guess so," I replied. "Is this just for coffee, or is your perverted little mind thinking of play time?"

I smiled at her, and she giggled. "I'm not completely certain, but you should wear something sexy. You know how girls talk. Vickie seems interested in your hobby."

"Okay," I said as I pulled grocery bags out of the trunk. "Two o'clock and I'll put on something cute under my jeans."

Well, here we go again, I thought. This could be interesting. Vickie seemed to be pretty normal, a cute little brunette with a nice figure. Her husband Thornton was a bigger guy, at least six inches taller than me, a little on the heavy side. They were pleasant in the few minutes we'd spent together. Did I have another pair of surreptitious perverts next door?

"Great!" Angie said, with another of her trademark giggles. "I'll see you then." With that she went trotting back across the street with a wave and a giggle.

I locked the car and carried my supplies indoors. After I'd put everything away, I straightened up the house a bit, concentrating on the living room and my bedroom suite, the two places I expected my guests to see. Then I showered and cleaned myself inside and out. Lately I never knew what parts of me my guests might want to visit.

I picked out a bralette and panty set. The panties were a full cut, covering my butt completely. The bralette was tailored for a man, with no breast padding. I really liked this set, pink satin with black lace edging. The satin felt amazing against my cock and nipples. I thought about adding some thigh-high stockings, but decided to wear shorts, so they'd be too obvious. I threw on a set of tan shorts and a polo shirt and sat down to await my visitors.

It was a few minutes after two when my doorbell rang. I switched the TV to a music channel and answered the door. It seemed that shorts and polos were the order of the day, as both women were similarly dressed. Cute little blonde Angie led the way, followed by Vickie, who was almost my own five foot seven inch height. Her shoulder-length brown hair framed a pretty face above a well-proportioned figure. Of course their shorts and polos were tighter than mine, showing off their ample breasts and bottoms.

Angie didn't resist her impulses here in private, giving me a big hug and a kiss on the cheek. New neighbor Vickie went with a handshake, and I invited them in.

I got them settled and poured each a glass of iced tea. We started chatting -- how do you like the neighborhood, what does your husband do, how long have you been retired, all the standard subjects. Vickie proved to be quick and witty. Angie was her giggly self, lovely pleasant company. That went on for a half-hour or more, then Vickie narrowed her eyes as she gazed closely at me.

She was quiet for a moment, then it seemed like she couldn't hold it in anymore. "I can see your bra straps, you know." she said.

"Well, Angie told me the two of you had been talking about me," I said, "And I didn't want to disappoint you." I smiled at her, and she smiled back. Angie giggled.

"What are you wearing?" Vickie said.

"Something pretty, something that I really like." I answered. "Would you like me to tell you about it, or show you?"

Vickie visibly reddened, and her hand came up to her mouth. Once again she was quiet for a moment, then it was as if she'd made a decision, and the words came rushing out. "I've never met anyone like you, and I'd like to see." She lowered her head and in a smaller voice said, "That is, if it's alright."

I breathed a long sigh. Angie and Jeff had seen me -- and done me. Why not show Vickie, and let the chips fall where they may? Well, her husband, for one thing.

"I'm good with that," I told her. "The only question is, would Thornton be good with that? I don't want to cause a problem."

Vickie laughed out loud, a very pleasant sound, and Angie broke into a fit of giggling.

"Oh, he's fine with it," Vickie said. I told him we were coming here, and what might happen. I promised to tell him all about it when he gets home from work."

Okay, I thought, here goes. I stood up and started my own version of a strip tease. I eased my polo shirt up under my breasts, then further to reveal my bralette. I pulled it over my head and dropped it, then hooked my thumbs under the straps and did a little wiggle to the music. Vickie's tongue touched her lips as she watched.

Then I unbuttoned my shorts and slowly eased them down, moving my hips side to side in time with the music from the TV. The situation had caused my cock to swell. I hadn't bothered to tuck it, and it was pressing the front of my panties outward. I held the shorts just above the head of my prick, then quickly pushed them below the tent. Both women's eyes locked on my cock. Vickie licked her lips again while Angie beamed at the sight.

Then I just let the shorts fall to the floor and kicked them aside, striking a feminine pose, my hips turned and thrust forward to emphasize my erection.

"Those are lovely," Vickie said. "I love how the bra is fitted to your shape. Come here and let me feel it."

I wiggled my way to her, standing very close, so that my knees were within an inch of hers. I smiled down at her, and her eyes locked on mine. Her hands went to my thighs, below the panties, then she slowly slid them up to my hips, squeezing me there gently.

"These fit you so nicely," she said, dropping her eyes to stare at my now-hard dick, only a foot from her face. "Let me see the back."

I turned around, again with a salacious wiggle. She kept her hands on the panties as I did, and her fingertips grazed across my ass and my cock. I'd eased towards her, and she spread her legs until my knees were between hers. Her hands held my hips again, then slid to hold my ass cheeks through the pink satin.

"This is wonderful fabric," she said, "It must feel wonderful against your ass."

"And other places," I added, thrusting my hips forward, then back to within inches of her face.

Angie had been watching this scene quietly until now. "And he fills them so well," she said.

"Yes, he certainly does," Vickie answered, sliding her hands inside my panties from underneath, holding both cheeks of my ass. She began kneading them, squeezing, pulling them apart, then squeezing them together.

"This side too," Angie said. Rising from her chair, she came to me and got down to her knees. One of her hands squeezed my cock through the fabric, and she pulled it away from my belly, then put the head in her mouth, sucking me through the satin.

Vickie stood up behind me, her belly against my ass. "Let me check out the bra," she said. She held her hands over the satin cups, then slid them underneath, squeezing my nipples between her fingertips.

Vickie moaned softly as she caressed my chest, then her body pressed hard against me, her breasts against my back while her hips slid side-to-side against my butt.

"Has anyone ever told you you had a wonderful ass?" she purred in my ear. "Thornton's is the best I've ever squeezed, but yours is a close second."

"Jeff really liked it," I told her. I was sure these women had shared all their secrets, so there was no need to cover for him. Both women laughed.

Vickie slid her hands down to my panties again. Both women wanted them off. Vickie slid her hands under them at my hips, while Angie pulled the front out to clear my cock, and very quickly they fell to the floor around my feet.

Angie took my cock in her mouth, moaning softly at the contact and the taste. Vickie grabbed my ass again with both hands. Her touch was more urgent now. She squeezed both globes, then pulled one aside while her other hand swept up the channel between, from my balls to the top of the crack.

"This is lovely," Vickie said, her voice now deep and throaty.

I put my hands on the sides of Angie's head and began fucking her mouth. She caught the rhythm on my first thrust and turned over control to me and my stiff prick. Behind me Vickie continued making love to my ass, squeezing and teasing.

"My favorite part of a man is his ass," Vickie told me. Pressing against me with her hands, she moved Angie and I forward, away from the couch. Then she knelt behind me and began kissing my bottom, moving around, licking slightly. Her hands went back to my hips and she pulled my bottom against her face.

She paused for a moment to pull her top off and throw it on the couch, then went back to honoring my cheeks with kisses. Not to be outdone, Angie stood in front of me and stripped off her polo and shorts. Then she pressed her body against me, her hand holding my prick between our bodies. She reached up and pulled my head down to hers for a long hot kiss, our tongues dueling between open mouths. Today her lingerie was white, a lacy bra and panties. I wondered for a moment if they would fit me.

Vickie pulled my ass cheeks apart, then kissed her way down to my boy hole. Spreading me wide open with her palms, she kissed me there, then began rimming me, moaning softly with each lick.

Angie pulled her head away from mine and whispered, "Why don't we go to the bedroom?" I nodded and smiled. Vickie had heard, and stood up behind me, shucking off her shorts. I barely had time to appreciate her lingerie, black form-fitting nylon bra and high-waist thong panties, before Angie grabbed my cock and started leading me to the hallway. Vickie followed behind, taking a moment to gather up her purse.

When we reached the bedroom, Angie threw herself on the bed on her back, her head hanging over the edge, her mouth open wide. I didn't need direction -- I just thrust my cock right into that hole and right to her throat. In just a moment Vickie was on her knees behind me, once again prying my ass open to lick and suck at the male pussy hidden there.

With my mouth and my ass being pleasured, I was the one moaning. I used my hands to good effect on Angie's breasts, squeezing them through her bra, then putting my hands behind the lace to cup both her luscious mounds in my hands. Angie moaned appreciatively. She brought her legs up then pulled her panties off and tossed them aside.

Her pretty shaved pussy was calling me, but I wasn't the only one. Vickie left my ass and quickly lay down between Angie's legs, using the same oral talents I'd just enjoyed to maul Angie's sex.

"As you can tell, I'm very oral," Vickie said, her voice a rumbling purr, before diving back into Angie's cunt.

I thought I'd make it a daisy chain, so I pulled my cock slowly out of Angie's mouth and approached the other end of the pair. Vickie was laying on her belly with her head buried in Angie. I placed my chest on her back and pulled her ass cheeks apart, aiming to return the favor. Her tight little back door winked at me in expectation, and I licked my way down her crack until my mouth found the entrance. There I used my tongue as she had to tickle and tease her. She spread her legs wide to improve my access and wiggled her lovely cheeks at me.

We stayed like that for a short while, mouths on openings, licking and sucking, the only sound an occasional moan. Finally Angie asked for a change.

"JJ," she moaned, "I want some cock in me. Will you fuck me?"

That was the best offer I'd had all day, and I moved to take her up on it. Vickie knelt on the bed while Angie swung herself around. Still on her back, she pulled the lips of her pussy apart for my entrance. I knelt between her thighs and she pulled her legs up against her chest. Taking my cock in hand, I touched it to the opening. Her pussy was soaking with natural lubrication, and I slid right inside, all the way to the bottom. Taking her ass in my hands I pulled her against me and began a long slow fuck.

Vickie wanted in on the fun, and came around behind me. She asked me about lube, and I nodded to the bedside table. Opening the drawer, she returned with a bottle. I heard it open behind me as my cock continued to exalt in the tightness of Angie's hot little cunt. Then Vickie's lovely tits were against my back, and I felt her lubed fingers running up between my cheeks. She found my asshole, and I felt one, then two fingers enter me. She rubbed her nipples against my back as she fucked my ass with her long slender fingers.

Under me I felt Angie's interior muscles squeezing my prick on every stroke.

"Angie, Jeff is a lucky man," I said, "Your pussy is just magnificent. Squeeze me like that, doll. Keep going." Angie giggled and smiled up at me.

"How about your ass, sweetie," Vickie whispered in my ear. "How does that feel?"

"My ass is an addict, dear," I whispered back, "and right now your fingers are a perfect fix."

"How about something bigger?" she purred.

"Then you'd really be feeding my addiction," I told her. Pulling her fingers out of me, she shifted and got up off the bed, reaching for her purse. It was a large leather thing, very stylish. Reaching inside, she pulled out a dildo with a strap-on harness. She got back on the bed and knelt by us.

"Here," she said, "taste it. I think you'll like it."

Opening my mouth, I took the head inside without loosing the constant stroke of my cock into the amazing pussy in front of me. There was a familiar tang which I enjoyed but couldn't place.

"I was fucking Angie doggy style with it this morning before we came over. That's her pussy you're tasting."

My, my, my, I thought. What this younger generation gets up to!

All this time Angie's eyes had been closed, concentrating on my prick ravaging her insides. She finally opened them to see Vickie wriggling her ass into the strap-on rig.

"JJ!" she exclaimed. "Are you gonna get fucked in the ass? I wanna do that too!"

She pushed at my hips and I dismounted, then she rolled onto her stomach and spread her legs wide. Reaching back, she held her ass cheeks apart, exposing her third hole for my appreciation. Then she wiggled her cheeks at me and squeezed her tightest hole. She looked back over her shoulder at me and giggled, then grabbed a pillow and stuffed it under her hips.

"Here, lover," she said, "Lather that wonderful cock of yours up and stick it in my asshole."

Vickie had grabbed up the lube bottle. "Here," she said, and I turned towards her. She grabbed my cock and held it against the dildo. It was a little bigger than me, about 8", of a thickness I knew I could handle. She poured some lube over both rods and began spreading it. As she did, she leaned in and kissed me, throwing her tongue my way. Our mouths were together for a moment, then she pulled back and smiled at me.

"You heard what the lady said," she smiled. "Stick it in her asshole, and I'll stick this in yours."

I took the lube from her and squirted a small amount between Angie's cheeks and rubbed it into her asshole. I slipped two fingers inside her to spread it out and stretch her out, then moved between her thighs. I leaned forward, pressing the head of my prick against her tightness. With one quick thrust the head was inside her, beyond the muscle rings.

Angie moaned loudly. "Oh fuck, JJ! That's amazing! Now shove it up inside me and FUCK MY ASS!"

Vickie laughed behind me, her fingers spreading more lube on my back door.

I kept up a constant pressure, and inch by inch my dick penetrated Angie's little hole. I looked down at where she was speared. Her hands still held her cheeks apart, and her hole was stretched wide around my shaft. The view was tantalizing, and I could feel my cock becoming even harder as I drove deep into her.

Finally my balls came to rest against her pussy. I would have started fucking her ass, but Vickie was impatient to join the ball. On her knees, she stepped in between my thighs. Angie was almost doing a split, and I spread my legs wider to get Vickie to my pleasure hole. It was my turn to wiggle my ass in invitation, a move that caused Angie to moan as my cock swirled inside her rectum.

I felt the head of the dildo against my boy cunt, and then the same rapid thrust I'd used on Angie forced the dildo inside me.

Talk about wonderful -- my cock inside the hot wet asshole of a pretty little blonde sex kitten, my own ass pierced by an 8" dildo, worming its way deep into my guts, hitting every nerve ending on the way.

Fuck, this was amazing. If I'd known it would be like this, I'd have retired 10 years earlier.

Each thrust Vickie took pushed my cock deeper into Angie's hole, eliciting another moan of pleasure from below me and one from within me. As Vickie pressed forward, the base of the dildo pressed against her clit, and she moaned into my ear from behind. I couldn't tell who was the loudest of the three of us.

Finally I felt Vickie's soft skin against my backside, and I knew she was all the way in. I could feel the dildo deep, deep inside me, stretching me out. It was wonderful. Then I felt Angie's muscles contracting on my prick, and that made it even better. I could have stayed like that forever, but I needed to cum, and for that I needed motion.

I started to pull out, carrying Vickie with me. Then when I pushed back into Angie's hole, Vickie braced herself and remained still. She put her hands down on the back of Angie's thighs, pushing them even wider. I opened wider too, and continued deep into Angie's ass-pussy.

So it was now my job to fuck all of us. As I pushed forward, my cock went deep into Angie. When I pulled back, Vickie's dildo speared me and pressed against her clit. I began a slow, rocking, back-and-forth motion. Fuck Angie, fuck me. Fuck Angie, fuck me.

I don't think my cock has ever been harder than it was then. Angie was talking, a slow, drawled, "Fuuuuuccckkkk meeeeee." again and again. Vickie gave out a little "Oh!" every time the dildo based pressed against her cunt. I became a piston, back and forth between these two women, pleasing them with every stroke, pleasing myself doubly at the same time, my cock and my asshole competing to see who could make me cum first.

Angie continued holding her ass wide with one hand, but the other worked its way underneath to play with her pussy. Vickie seemed to be getting all she needed with the dildo against her cunt. She needed her arms to brace herself against my rearward motion.

My asshole was burning with pleasure, the fake cock pushing deep inside me with every stroke, rolling across my prostate. Angie's anus squeezed my cock every time I moved inside her. I held myself back with every muscle, working hard to induce two feminine orgasms before I had my one.

I took to a long, slow rhythm, fucking back and forth. Angie moaned with each long push up inside her bowels. I could feel Vickie trembling behind me with each push up, the dildo pressing against her pussy.

Then it became too hard for Vickie to remain still, and she started stroking down into my ass. She took control. I pushed into Angie until only an inch of my cock remained outside, and each of Vickie's strokes slammed me down balls deep once more.

Halfway between a moan and a cry, Angie called out, "Oh, fuck, fuck fuck! That's so good in my ass. I'm going to cum this way! Do it, do it!"

That was encouragement enough for Vickie, who just went to town on my ass.

"This is so good," Vickie whispered behind me. "Thornton is going to love your asshole. He's going to want to fuck you just like I am." Her voice turned to a growl as she continued, "What a wonderful ass, JJ! I'm going to cum just from fucking it!"

I was barely holding off my own orgasm when I felt Angie's hole squeezing my cock. She moaned in rising tones, "Ahhhh, ahhhhh, Ahhhhhh!" as she came, and I felt her squirting juices wet my balls.

Hearing Angie come, Vickie became desperate to drive herself to orgasm, and she began pounding my ass. Her breathing rasped as she drove her dildo harder and harder up my boy cunt. Her arms trembled as she fucked me. I surrendered all control to her, concentrating on the feelings inside me and inside Angie.

Vickie yelled out, "Fuck, fuck, oh motherfucker!" Driving her hips against my ass, she came, with my cock balls-deep in Angie's ass, and I was free to climax as well. I pulled back, carrying Vickie on my back, and gave a series of short sharp strokes in Angie's asshole. I quickly achieved release, filling her bottom with my hot spurting cum.

We stayed like that for a minute or so, regaining our breath. Vickie lay on my back. I used my arms to hold our weight off of Angie. Angie's hole twitched in the aftershocks of her orgasm, squeezing my prick.

Finally Vickie disengaged, slowly easing that long plastic cock out of my hole. Then I could pull my softening pole out of Angie, giving her one last sharp stroke and eliciting one final "Ahhhh!"

Vickie pulled me towards her body, and I rolled onto my back between the two women. She kissed me, then leaned over me to kiss Angie.

Thinking of what we'd done and what could be done, I turned my head towards Vickie. "Give me a few minutes to recover and clean myself, and we can put you on the bottom," I said.

Vickie gave a short laugh. "Not today," she said. "My husband and I have an arrangement. Either of us can play alone, but no penetration unless the other is present. Don't worry, there will be another time." Then she kissed me again, and we smiled at each other.

"You really know how to fuck an ass," Angie said softly. I looked over, and she was still teasing her clit with her fingertips. "That's the first time I've ever come from being fucked in the ass." She tucked herself under my arm and kissed me on the cheek, one hand cupping her sex while the other teased my nipples.

"Maybe next time we'll bring a husband or too," Vickie purred. "I still cum best with big cocks inside me." I noticed the statement of multiples, and another steamy vision entered my head.

Vickie rolled off the bed and tip-toed to the bathroom, the plastic cock still swaying with every move of her hips. Her ass looked fantastic from this angle, and I hoped I'd get to fuck it one day soon. Angie rolled on top of me, her sopping pussy against my cock. She kissed my chest, then lay her head on my breast, enjoying the glow of orgasm and the sweet soreness in her asshole.

I heard water running in the bathroom, then a few minutes later Vickie returned, wrapping the straps around the dildo that had just been inside me and dropping it into her purse. "We'd better go," she said to Angie. "I need to get home, and it would be better for us to leave together if anyone was looking."

Angie sighed, then rolled off me. "I was just planning round two," she giggled, "but I guess we'll save that for another time."

We got off the bed, and I grabbed a robe from the closet. It was short, flowered, and feminine. When I say short, I mean my cock was showing beneath the hem. The girls gathered up their clothing and dressed in the living room. Both took their purses to the guest bath to repair hair and makeup, not wanting to look like they'd just been fucking their brains out as they made their way home.

I got two hot tongue kisses at the doorway, then they kissed each other. Neither woman could resist giving my prick one last squeeze. I closed the door behind them and leaned one it.

Jesus, what next, I thought.

AUTHOR'S POSTSCRIPT: These little chapters are kind of fun. I may add more. If you liked it, drop me a note or leave a comment. It's your affirmation that gives me incentive to write them. Don't forget that none of this happens without DONATIONS. If you came reading this, you owe me. Keep my creative outlet alive and hit that button.


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