Caught by Neighbour Ch. 02

Story Info
Gary organises a date.
3.5k words
4.64
81.1k
33

Part 2 of the 4 part series

Updated 10/19/2022
Created 01/29/2012
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

- 1 -

The next day I woke to the sound of birds outside, and sun streaming through the windows. It was Sunday, and normally I'd have been up and about early with Sam. But with her still away, I'd slept in late. I lay in bed, unmoving, stunned by the previous day's bizarre events. I scarcely believed it had happened, and yet knew that it wasn't a bad dream. In the light of a new day, it didn't feel good at all - for all my years of secret fantasies, I'd never admitted them to anyone, let alone acted them out, and now I'd been caught cross-dressing, photographed posing in women's underwear, and then been forced to give a blow job to my neighbour.

Well... had I been forced? There was a guilty twinge in my groin as I remembered sinking to my knees in Gary's bedroom, and the shocking things we'd both said. And hadn't his ass felt kind of sexy in my hand?

Christ! I sat up and jumped out of bed, shaking my head. This was a nightmare, and come to think of it, I'd also cheated on my wife. What would I do when she got home? I couldn't lie to her, but I couldn't admit what had happened, either. I needed to think of a plan, desperately. But as I went round the house doing chores, and then headed out to read the paper, I couldn't think of a single thing I could do. I had no idea what Gary might do with the photos - they might be in a safe, or hidden anywhere in his house, or they might already be online somewhere. With those photos in his keeping, Gary had me in his power completely.

Anything and everything could be at risk - my safe job as an accountant in the city, my standing with friends, even my marriange. It seemed all I could do would be to confront him - yet I was scared to do it.

When I returned home for lunch, my heart jumped. There was an unmarked envelope on the doorstep, and I just knew who would have left it there. Glancing around nervously, I took it into the front hall and opened the letter. It simply said "Call me", and gave a mobile number. I sat at the kitchen table and stared at it for a long time, and then got my own mobile out and placed the call.

"Hi, this is Gary," he said after a couple of rings.

"It's John," I said.

"Thanks for calling John," he said, "I enjoyed having you over last night." It was shocking how confident he sounded; there was no preamble or skirting the topic, and I immediately felt unable to take control of the conversation.

"You looked nice in those clothes John," he said, "but I'm expecting a better effort for our next date."

"Next..? Uh, better effort?" I stuttered.

"Sure. I mean, you have some nice lingerie, but I'm not used to girls who are - how would you say - a little on the hairy side."

"Sorry?"

"Hairy. I'm going to expect you to work a bit harder on getting ready next time."

I swallowed nervously.

"So, first of all, I'm expecting you at my place tonight at 8pm. I expect you made up properly - I'm sure you have everything you need round there, right?"

I goggled as Gary proceeded to reel off very explicit instructions - I was expected to present myself at his house, dressed up in stockings, suspenders, high heels, bra and g-string, with my legs and body completely shaved of all hair; supposedly to be a more suitable "date" for Gary. And on top of this, he suggested I might need to work on some makeup. I thought all this might be possible, but then he really shocked me by adding: "Oh and John, I don't expect to see you turn up in those ugly tracksuit pants again. When you walk round here, I want you wearing what I just said. Do you understand?"

He hung up, leaving me sitting at the kitchen table, heart thumping.

- 2 -

I must have sat at the table for half an hour, wondering what I could do, with nothing springing to mind at all. Perhaps I should go along with his instructions tonight, just to buy some time? I certainly had the clothes I needed, tucked away out of sight in a couple of spots round the house. And Sam's part of the bathroom cupboard was brimming with lipsticks and other girly makeup. But the legs - What could I do?! I pulled up the leg of my jeans, and pondered the healthy layer of brown hair. Going at this with a razor would be an all-day job, not to mention I'd never done it before and was likely to cause all manner of nicks and cuts. How on earth does someone shave the back of their knees, for example?

I looked at the clock - it was already 1.30pm. It was time for a snap decision, and I decided that hair removal cream would have to do. I rushed out to the car and drove to the supermarket, nervously checking the aisles until I found what I was looking for - a squeeze back of foul-smelling cream that promised to remove all hair with the greatest ease. I threw a few of them into my basket just in case, and then grabbed some other random items in case other shoppers might wonder why a man would come all the way to the shops just to stock up on hair cream. At the counter, I studiously avoided making eye contact while a girl processed my items.

As a I drove home, the next problem struck me - Sam was coming home in just a few days. There was no way hair could grow back in days, surely? I tossed around some ideas: could I avoid being naked until it grew back? Ridiculous. Make up some excuse for why I had to do it? Hardly. The least-worst idea I had was to make up a story about starting up my bike riding again; though when I'd enjoyed it a few years before, I'd never seen the need to go 'smooth'.

Well, it would have to do. I made a mental note to dig out my bike gear and leave it lying somewhere prominent.

When I arrived back home, I went to the bathroom and stripped off, carefully reading the label, which had all manner of warnings - including that I should test the cream on a patch of skin first, in case of any allergic reactions. But it was well after 2pm now, and to hell with that. Also, though I didn't like to think too much about it, I was starting to feel a tremor of excitement again, and I looked guiltily down at my cock, which was standing thoroughly to attention. As I squeezed out the cream into one hand, I admired myself in the mirror - not the most athletic guy, but slim, and lightly muscular. As I bent down to start slathering the cream on my ankles, another guilty thrill washed over me, and I stuck my ass out a little, imagining that I was being watched.

It was awfully tempting to start stroking myself as I lathered my body all the way up to the next. I paused briefly at my groin, then thought - to hell with it! - and also massaged a healthy wad of the cream into my pubic hair.

I spent an unpleasant ten minutes waiting for it all to dry, wrinkling my nose at the chemical smell, and then stepped into the shower and started wiping the cream off with a cloth. I was thrilled to see the hair coming away with it, and within a few minutes, I was washing off the last of the cream under the shower,and cleaning up the odd missed bit of hair with a razor. The feeling of washing my groin was exquisite, as my soapy hands slipped all over my cock and my balls, and when I finally climbed out and looked at myself in the mirror, I was amazed.

How much of our manliness is defined by our hair? I'd never have thought so, and yet when I stood there admiring my smooth, pink legs and body, I felt awfully like a girl. My cock, half flaccid, seemed small and delicate now it wasn't bedded down in a mess of curly pubes, and I played absently with it, even tucking it between my legs, out of sight. I felt I was ready.

- 3 -

For the rest of the afternoon, I snuck around the house trying to work out what to wear, and how I might go about the makeup. In the end, I decided on some red lipstick and black eyeliner that were in a box in the bathroom cabinet. The eyeliner was difficult, but when I was done, I was happy with the effect.

My short hair didn't look the part, but I didn't have a wig, and at least the makeup made my eyes and mouth look a little feminine. Next, I laid out the clothes - for this part, I took down an old suitcase from the study that was supposedly filled with old magazines, but actually was my hiding place for my favourite outfit: a complete matching set of lilac and black lingerie that I'd bought online, complete with suspender belt and thin thigh-high stockings.

I carefully hooked up the bra and suspender belt, then rolled each stocking up my leg with great care so as not to catch my toenails on them. Then I attached the suspender clips, and stepped into the g-string. The feeling of the g-string sliding up my stockings and hairless thighs was heavenly, and I had to leave my cock poking out the top while I first positioned it - I was far too hard to even fit them on at the front! I delighted in the guilty pleasurable feeling as the lace trim tucked itself away between my ass cheeks, rubbing lightly against my asshole at the back. I turned around a few times in front of the mirror - yes, I was ready. And it was nearly 7.30pm.

Now for the challenging part - getting round to Gary's house.

Gary's house was actually on an adjacent side of the block - but being a long property, his back yard extended directly behind mine. So there wasn't a long way to walk. But the sight of a man wandering around in women's lingerie at 8pm on a Sunday wasn't exactly the sort of thing my neighbours would turn a blind eye to. I debated covering up, then shivered when I remembered Gary slapping me the last time I'd disobeyed instructions. How quickly could I move in the high heels, I wondered? I'd certainly practiced walking in them around the house many times, but the last thing I wanted was to sprain an ankle and need rescuing by a passer-by. Fortunately, it was getting dark outside.

I did a last check round the house, deciding at the last moment to take one of Sam's old handbags from her cupboard, so I'd have something to put my house keys in. Then to help summon the courage, I stopped by the liquor cabinet and took a healthy swallow of Vodka. I was as ready as I'd ever be, so I stepped out onto the front porch, and quietly closed the door.

Outside the evening was still warm, but dusk had fallen, and a cool breeze was starting to spring up. It blew lightly across my smooth ass cheeks, and it was thrilling to be outside, exposed to the world like this. I snuck to the front gate, looking carefully around and listening for cars or people walking.

Thankfully it was quiet as could be, and with my heart hammering in my chest, I began to clop carefully down the footpath towards the corner.

It was amazing to feel the way my ass and hips jutted and rolled as I walked, and I couldn't help accentuate it a little as a went, even though a part of me was screaming in panic at every tiny sound. I wondered if the sound of my high heels would drown out the noise of an approaching jogger, or a car rolling quietly, and I walked as fast as I could to Gary's, breathing a huge sigh of relief when I was in his front garden and out of sight from the street.

I stood there, clutching Sam's handbag, and wondering what would be in store for me.

- 4 -

I carefully climbed the front steps and pressed the bell. Shortly I heard Gary's footsteps approaching, and he opened the door. He was wearing a pair of light trousers and a shirt, open at the next to show his chest. He looked me up and down, while I stared at my feet in embarrassment.

"Not bad - not bad at all," he said. "Come in."

I walked inside and put down my bag, and he closed and latched the front door with a rather final-sounding click.

"Just so that we have some privacy," he said, and inclined his head at the locked door. I gulped.

"Now would you like to have something to drink, J-", he said, then stopped. "You know, I don't think we should go calling you John - you hardly look like one anymore, do you." He looked thoughtfully at me, then said "I think we'll go for a simple swap - you can call yourself Jane."

"OK," I tried to say, but my throat had gone so dry that only a squeak came out. I tried again: "OK - and yes, could I have a small drink please?"

Gary led me to the lounge room and sat me down while we went and made a couple of spirit mixers; I had no idea what, but anything would do just then to calm my nerves. As he handed mine to me, I looked up and caught an eyeful of his groin, which was bulging. When I looked further up at his face, he was grinning. "I'd say someone is pretty pleased with your outfit, Jane," he said. "Maybe you should finish that drink up as quick as you can." He tossed his back with one startling motion, then took my hand and pulled me to my feet and I gulped at my own drink, the alcohol stinging my throat. Thankfully the earlier vodka was doing its work - I felt a warm buzz already. Gary stood back, admiring my outfit, and gestured for me to turn around. I was shocked when he stepped close behind me, and grabbed on of my ass cheeks, squeezing it roughly. His other hand slipped around and rested possessively over one bra cup.

"You look delicious, Jane," he said. "Do you feel as sexy as you look?"

I didn't say anything, but I didn't resist as he pressed up against me. I could feel his hard-on pressing neatly between my cheeks, and my own penis was in great danger of popping completely out of my underwear.

"I think you best head down to the bedroom," he said, and once again I found myself walking down there in a daze, this time with Gary fondling my ass as I walked. I couldn't stop myself from rocking it back and forth with each step; I was blazing hot now with the desire to get this over with - my hair was nearly standing on end, and I knew that I'd come here to be fucked.

Gary guided me to the side of his bed, and pressed me down so that my face was against the covers, my hamstrings stretching as my ass jutted into the air. I heard him removing his clothes, and then the snapping sound of something opening. He carefully pulled my g-string to one side, and then I jumped in shock as something cold was drizzled directly onto my asshole.

Gary chuckled. "As juicy as you look, I think a little bit of lube is in order, don't you, Jane?"

Not waiting for a response, he began rubbing it around between my cheeks with one finger, and I groaned helplessly at the pleasure of having my ass played with. When he suddenly probed into my asshole several times with his finger, I trembled, and felt my cock begin leaking pre-cum. I hoped I wouldn't blow my load before he'd even begun. I snuck a look behind me, and saw Gary smearing the lubricant onto his cock - I'd forgotten just how big it was, and I felt a sudden stab of fear - he was easily larger than the little dildos I'd previous played with, and I shrank my hips away involuntarily. But it was too late for that.

Gary peeled down my g-string, leaving my wettened asshole exposed, and then gripped my left hip with one hand. I felt him step close in behind me, then the obscene pressure of his engorged cock head pressing against me. He used his other hand to guide it to my anus, and I yelped as he started to force himself into me.

How can I describe this? It was painful, and yet thrilling. It seemed he would never fit into my tiny hole, but nonetheless it slowly began to stretch as the lubricant did its work. With relentless, slow pressure, he pressed harded and harder, and my asshole stretched painfully. I began to panic that it might tear, but then just as I was about to scream for him to stop, there was a blissful release as the head of his cock popped through my sphincter muscles, and Gary grunted in satisfaction. He pressed me down onto the bed, pushing harder again as his meatpole started sliding deeper into my ass. I bit down on one fist, half in agony and half in ecstasy - it seemed that his enormous cock wouldn't stop until it reached my stomach. Then finally Gary was all the way in, and he was on top of me, his groin pressed right up against my ass.

"Oh, oh, oh" I whimpered quietly, and he chuckled again.

"Shuffle up a little," he said, and together we awkwardly lifted my hips so I could move more fully onto the bed.

"Good," he said, "and now I want to fuck you - hard".

Then Gary began to do just that, first pulling his huge cock slowly back out of my ass, then grinding it just as deliberately back in, gradually picking up a rythym as I grunted and sweated beneath him. I felt an incredible rush of pleasure every time his shaft drove up into me; I felt full to the brim, and started to press my ass back to take as much of it in me as possible. Soon, he pulled me up onto my hands and knees for even better access, splaying my ass

cheeks open and gripping a fistful of my hair with one hand for leverage. I was beyond caring now, and I loudly moaned and begged him to keep fucking me, to fuck me deep in my ass, that I wanted him to come right inside of me. I grabbed wildly at my crotch, and without even stroking myself, I felt my own orgasm ripping through me. I exploded onto the bed sheets, ropes of come spattering everywhere, and so utterly consumed that I felt my legs shaking involuntarily and my asshole clenching in time with the spurts of cum.

"Oh my GOD!" shouted Gary, as he felt my asshole gripping itself onto his cock. To my surprise, he reached down and turned my head to one side, and brought his mouth down to kiss me. I responded eagerly, my mouth crushing against this, and our tongues slathering at each other, as he drove his cock faster in and out of my ass. Then he pulled his head back, nearing his climax, and I knew he was about to fill me with his cum.

Gary's hips slammed up against my ass a final time, and I fancied I could almost feel the hot cum spurting up inside my bowels and he jammed tightly against me. We stayed locked together like that for what seemed like minutes, then he carefully withdrew, sliding out and leaving my ass feeling empty and gaping.

I felt a small trickle of liquid running down onto my balls - whether semen or sweat, it was impossible to tell.

Gary rolled off me, and I lay there on his bed, breathing hard. My stomach was now glued to the bedsheets with my own sticky cum, my stockings were sopping wet with our combined sweat, and my g-string was hanging lewdly round one ankle. My ass, meanwhile, felt open and ravaged, and I marvelled to think that deep up inside me there was a huge wad of another man's cum.

For now, my broader problems were farthest from my mind, and I simply lay there, face down, and enjoyed the feeling.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
lingerie65lingerie65almost 6 years ago
Loving how he fucked me.

I'm so turned on by jane's sexual enjoyment of having a thick dick in her, I'd sure wish it was me that was filled by that beautiful piece of meat.

AnonymousAnonymousalmost 11 years ago
Great!

Loving your writing as I go through chapters!

Great descriptions of everything. And the smells and other senses are brought in nicely..

Psychologically (ha!), the idea of how one feels a hairless guy is a good realization.

But mostly, I'm just tenting my panties, barely holding on!

AnonymousAnonymousalmost 11 years ago
turned me on

This story was great. It turned me on so much. It reminded me of when my hot stud of a neighbour fucked my man-pussy the first time. Now he fucks me regularly and I suck his cock while my wife watches. Please tell more stories lilke this one.

AnonymousAnonymousabout 12 years ago
Good story

Have Gary have a "poke him" party for Jane with 6 to 8 guys and make it an all night bang!

FRSWRITERFRSWRITERabout 12 years ago
Nice

Very nice, need to see the next part soon i hope

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
A Sissy's New Daddy Billie is forced to be a sub-sissy.in Transgender & Crossdressers
Turning Him Into A Whore She turns him into a trick turning whore.in Transgender & Crossdressers
My Husband’s Birthday Sexual humiliation for his birthday gift.in Transgender & Crossdressers
More Stories