When I was a young man, just learning about girls, during summer break from school I was doing my chores around the house. I had many hours every day where I was home by myself. I was taking the trash out to the alley one day and heard the neighbors jacuzzi bubbling next door to my house. There was a wooden fence atop the brick wall between the two homes. There were a few spots in the fencing where I could peer into the neighbors yard and see what was going on. I heard some noise coming from the hot tub. Finding one of the spots in the fencing I saw the lady of the house getting out of the jac... Continue»
Caught by Neighbor
- 1 -
It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not for the first time, I stopped in front of a mirror and pulled my tracksuit pants down, admiring the bright pink, silky panties that I'd been walking around in all day.
I'd been cross-dressing for many years before I met Sam, but it really wasn't her thing. So I tended to keep it to myself, waiting for the chance to be alone now and then, dressing in all sorts of tight and skimpy lingeries, and sometimes indulging in fingering my ass, or using something bigger with the help of a little lubricant. I'm a happily straight, married man, but I just liked the sensation of feeling like a woman, and the feeling of being fucked like a woman. Some of my best orgasms came when Sam was away, when I could roll about on the floor in silky, lacy clothes, and give my lubed-up asshole a solid object to slide onto.
I had to sort out the washing today, and I stepped outside around midday to hang out a load. It was the usual mess of towels, sheets, underwear and so forth - always more than I'd planned on, and it always took me a while to hang out. It was hot, but there was a nice breeze blowing, even though our back yard was pretty sheltered. The fences were all fairly high, and there wasn't any obvious points where neighbours could see in. I wished that I could get Sam a bit more comfortable with the idea of taking our lovemaking out there, but she felt like a neighbour might poke their head over the fence. Part of me got a little thrill about that - I imagined being underneath her, and seeing a neighbour's head come into view. I would lie there and fuck her, not saying a word, while perhaps the neighbour would be stroking himself too - or herself!
At this point I began to feel particularly turned on, and I tugged the back of my tracksuit pants down to bare my pink panties to the world. The feeling of the cool breeze blowing against my silky ass caused my cock to press harder against the front of the panties, and with a sense of thrill, I pulled my tracksuit completely down, and stepped out of it. I glanced around nervously, then continued to peg the clothes, feeling a nervous tingling and an urgent need to relieve myself of the pressure. For a few minutes, I worked up and down the line barefoot, and then bent down to pick up the empty washing basket.
At that exact awkward moment, with me bent over presenting my panties to the air, a voice said "Hey John... oh!", and I span around in shock. Right behind me, looking over the fence, was my neighbour Gary.
I didn't know Gary at all, beyond exhanging the odd hello. He had moved in a few months before, and although our back fence was shared, it was high enough that you had to stand on something to see over. He seemed a solitary sort of person, and I'd made little effort to invite him round. This wasn't exactly a great way to commence the process!
I went bright red - I could literally feel my face heating up - and I quickly thrust the washing basket in front of my groin to try to hide the view. He stared at me with his mouth open, as I scrabbled for my tracksuit pants and backed hurriedly inside. I banged the door shut and stood against the wall, my heart thumping in panic. What on earth could I say - I'd simply have to avoid ever talking to him again! Any sense of eroticism had certainly gone out of the moment for me, and I went quietly to my room and tucked the panties away again, all the time feeling a vague nervousness as if someone was watching me. After a little while I snuck carefully to the window to check, but he'd gone away. I didn't collect the washing until it was dark, sneaking carefully out and making as little sound as I could.
I went to bed that night hoping to wake up and find it had all been a nightmare, but unfortunately that wasn't the case. My nightmare was just about to begin.
- 2 -
The next afternoon, as I was washing dishes, the doorbell rang. My heart stopped, as I wasn't expecting anyone. I checked the monitor, and sure enough, it was Gary. I didn't know what to do - it was obvious I was home, given the car was there and the windows open - but I didn't think that I could face a conversation with him. I stood there indecisive, and the doorbell rang again. His face in the monitor seemed neutral to me - perhaps he'd come to apologise for peering over the fence? I couldn't just hide there in the kitchen, so I swallowed hard, and walked down to open the door.
"Hi", I said, giving a weak smile, but unsure what to say.
"Oh hey John, I'm Gary - your neighbour from over the back?"
"Yeah I know," I said, and then after an awkward pause, "uh - come on in".
I held open the door and he came in. I hadn't really noticed in the past, but he was quite tall and well-built, and very swarthy. There was a certain no-nonsense look about the guy, and any vague thoughts I'd had overnight about intimidating him into silence over the incident quickly faded. Besides, he seemed very friendly.
"Would you like a beer?" I said. "I was just going to watch the football."
"Sure, if you don't mind" he said.
I fetched a couple of beers, and we sat down in the lounge with the television on. As we made small talk about the game, I wondered if this was his way of breaking the ice; letting me know there wasn't a problem and he was comfortable with what had happened. So I was a bit shocked when the conversation suddenly took a different turn.
"John you live here with your wife Sam, don't you?" he said. "Sorry, is that her name...?"
"Yeah that's right - Sam. It's err, short for Samantha."
"She's not around at the moment?"
"Err... no, she's on a business trip."
"Oh OK, sure. And does Sam... I'm not sure how you put this, does she know that you do the washing in her underwear?"
I literally choked in the middle of taking a swig of beer, and tried to disguise it as a coughing fit. Gary simply looked at me calmly, as if he'd asked me what time I liked to have dinner. I grabbed a napkin and wiped beer off my chin and the bottle, trying to figure out what to say.
"Heh, yeah I didn't think so. It's kind of secret stuff, right?". He seemed understanding, and it suddenly occurred to me that maybe what I'd stumbled across was another cross-dresser. It seemed a good idea to draw this out.
"Yes, that's right. You know how it is, right - there's some stuff that you don't exactly want to, you know, advertise. So - well, look, I'm sure she'd be find with it. It's just that...". I trailed off, as an odd look had come over his face.
"Yeah I thought so - you wouldn't want to advertise it to her. Or for anyone else to do that. I mean, just say someone was to mention it to her by accident?". He was staring at me in a pretty frightening way, and I suddenly had a horrible sinking feeling in my stomach. I knew just what was going on here, and I was suddenly terrified. Of course I didn't tell my bl**dy wife that I liked to walk around our back garden in her panties; she'd walk out in an instant. My life with Sam was a great one, don't get me wrong, but her taste in sex was pretty simple - basic missionary, the odd bit of fooling around, men are men, women are women, and there's only one hole that is appropriate for putting things in. If Gary was here to blackmail me, he'd gone right for the jugular, and I was in a really awkward spot.
"What are you saying, Gary?" I said, trying to sound confident, but already feeling a quaver creeping into my voice.
"Just this," he said, leaning forward, "I looked over the back fence yesterday to say hello, and I saw you bending over next to your washing line with a pair of bright pink panties on. And I'd say that means you're a fag of some kind, and that your wife doesn't know. Now I reckon you'd like to keep that little secret a secret, am I right?"
I stared at him, gripping my beer bottle. I couldn't think of anything to say."
"Am I right?" he repeated.
"Y-yes" I said.
"Good", he said. "So we can probably cut to the chase here a little bit. There are some things that I'm going to get you to do, and you're going to be pretty happy to do them - at least that's what I think. Because if you don't, then I'm going to haVe that conversation with your hot little wife Sam, and I'd say that might be the end of your happy marriage."
I thought about that, and the voice in my head said he was probably right. How on earth had I got myself into this situation? It was a disaster. The whole thing brought on by a stupid decision to put my secret habit on display. Why couldn't I have simply watched some porn and masturbated and then chosen to go outside for the housework. And now I was being blackmailed and threatened by this guy, with nothing I could do about it.
"What do you want?" I said.
He smiled. "Pretty simple - I didn't get much of a look at your underwear when you ran off inside yesterday. So go and put it on. Do you have a whole set of stuff somewhere?"
I nodded reluctantly.
"OK - so I'm going to finish my beer, and you can go and get changed. You've got about 5 minutes."
"Is that, err... that's all, right?" I said.
He ignored me, and after a moment, I went out of the room and down to the bedroom. What an awkward situation. It was hard to read what he was up to - I'd expected a demand for money, or anything, and now he wanted me to cross-dress in front of him? And yet he didn't seem to want it for a sexual purpose; at least not as far as I could tell. What would I know - the last thing I was interested in was another guy's turn-ons. I hoped like hell he didn't want to get into some sort of sex game. I stood there in my bedroom, with all of these thoughts flashing through my head. In the end, I just figured maybe he wanted to embarrass me. Well, what the fuck. I took off my shoes, jeans and t-shirt, and took the pink panties and bra out of their box. I carefully hooked the bra together then wriggled my arms into it, then pulled on the panties. To my embarrassment, my cock had gone rock-hard as usual, and I desperately tried to shove it down between my legs to hide this. The last thing I wanted was for him to think I was turned on by dressing up in front of him.
"That's it?" said Gary from right behind me, making me jump in shock. He'd walked silently into the room while I was dressing.
"I know that's not the whole of it," he said. "I asked if you had a whole set."
"What do you mean?" I said, knowing exactly what he meant.
"John, don't fuck with me, OK. If you're going to lie and muck around, it's very simple. I will tell your wife. So stop thinking I'm an idiot. I'm saying I reckon you've got other clothes in here that you like to dress up in - shoes, stockings, whatever. Put it all on, so you're dressed up like a woman, how you would if I wasn't here. Do you get that?"
"Yes," I started to say, then to my shock he slapped me violently across the cheek, making me stumble. My hand flew to my face and tears sprung up.
"What the hell?!" I squeaked.
"Do you get that?" he said again calmly. "Because I'm not a guy you want to fuck around. So get on with it, or you'll really get what's coming."
I was terrified by now. This tall, strong man was standing over me, while I cowered in front of him wearing a pink bra and panties, and I could see there was a genuine threat of v******e in his eyes. I had no choice at all. I quickly went to the cupboard and picked out the rest of my set of clothes - a garter belt and thigh-high stockings, and a pair of high heels, all carefully hidden underneath other things, until now. I nervously put it all on, while Gary stood with arms folded, watching.
"That's... that's it", I said. I was mortified to see that my hard-on hadn't gone away, and while I'd been dressing, it had worked its way out again, bulging lewdly out the front of my panties.
"That's better," he said. "Now come over to my place."
"What?!" I said.
"Come on over. I don't care how you get there, but I'll see you in five. OK?"
I took it that the "OK" was rhetorical. I simply nodded, and with that, he walked out.
- 3 -
After a little bit of thinking, I pulled some clothes over the top of my lingerie, put the high heels in a bag, and then walked around to Gary's house and rang the doorbell.
He opened the door. "Come on in," he said casually, as if nothing had happened. "And get that stuff off. Go in the main room."
I went into his living room, and took off my pants and sweatshirt again. I put the high heels back on, and stood there. I could see myself in a mirror, and felt an awful combination of being completely terrified at the situation, and rather turned on to be dressed up in a slutty set of women's underwear, with my ass jutting out, and another man about to walk in and look at me. I pressed one hand down on my groin, trying to calm down my raging hard-on again.
Gary came in, and stood there looking at me. To my distress, he was holding a camera now. "I'm going to get you to do some modelling, and I reckon you can figure out the right moves," he said. "Just basically look like a slut, and I'll do the pictures."
"I don't want that," I said, and then cowered when he took a threatening step towards me. I could see what might happen.
"OK, sorry, sorry," I said. "I'll do what you say."
I shut my eyes and tried to imagine he wasn't there. First, I spread my legs apart - wider than they needed to be, with the added lift of the heels making me feel stretched and open. Then I cupped both hands to my "tits", lifting the bra cups up as if lifting my breasts for display. Then I started to move around, stretching and turning, presenting my ass, pouting my mouth, and so on. Gary quietly took photos, and I knew that my life as I knew it was coming to an end here in this stranger's front room.
After a few minutes he had me stop, and then came what I'd really been dreading.
"Go down the corridoor," he said, "and go into the bedroom."
My eyes probably bulged, and I felt that I couldn't breathe. But I found myself tottering towards that room, in a complete daze. Gary followed me, and shut the door behind us.
"I liked your posing," he said. "You looked like...". There was a pause, as he kicked off both his shoes and bent down to take off his socks. "Like... I guess like a bitch," he went on. "Do you feel like a bitch?"
I stared at him, watching him pull off the shirt he was wearing. Underneath, he was muscular and had a thick hatch of chest hair. His stomach was flat, and I couldn't stop looking as his hands went to his belt buckle.
"Do you feel like a bitch, John?" he said.
It was as if I was floating above the scene, all of a sudden. I tried to swallow, my mouth extremely dry. I stared at his muscular torso, and at his hands as they began to unbuckle his belt.
"Yes Gary," I croaked. "I uh.. I feel like a fucking bitch. Are you getting your cock out?"
My head throbbed with rushing bl**d as I mouthed this shocking invitation, and even as I spoke, I had sunk down on my knees. My cock was raging against my panties. John undid his belt and jeans, and took out his penis. It was shockingly large and vulgar, and I fixated on it, noting in extreme detail the way it thrust out, slightly upwards, circumcised, with his hairy balls tucked tightly underneath. On the tip of it, a bead of liquid had formed. I stared at the liquid - his cum - another man's cum, and I knew that I wanted to lick it up.
"You are a bitch, John," he said. And I'm going to fuck your face with this cock. Now, come here, and suck it into your mouth - and don't even think about stopping until you've finished drinking me, do you understand?"
I shuffled forwards on my knees. I wanted to take his cock into my mouth, and be dominated and used by him. I had no idea what it meant for my previously sane, happy life, but I really just didn't feel like I cared. Gary stepped out of his jeans, leaving him standing there, naked, hands on hips, and waiting for me to service him. I reached up with my right hand, and wrapped it around the base of his cock. It was shockingly hot, and I could feel it gently throb in response. My other hand crept round behind him, and grasped one cheek of his ass. His ass felt hard in my hand, strong, and manly. I pulled his groin forward and into my wide open mouth.
The hot cock slipped into my mouth, filling it completely. It took a few moments to even work out how to go about things, and I felt Gary grip my hair with one hand to control my movements as well. I let my tongue lick at the underside of his penis, while trying to keep my mouth wet enough to make it slide on his shaft. He stepped forward and bent his knees, his other hand joining the first. Now I felt completely subdjudated, as he started to slowly hump his cock in and out of my mouth, with soft grunting noises. And as I sucked, he talked to me as well.
"I'm looking down at you here, John," he said quietly, "and I'm seeing you acting like a whore for me. You're dressed up in your pink panties, and I'm looking down at your ass. I think when we're done here, I might need to see your ass a bit more, don't you think, John?"
"Mmmm hmmm," I said, stifled by the penis which was slowly working in and out of my mouth. I tried not to gag. I felt wetness in my panties, as my cock leaked pre-cum."
"And when you show me your ass, John, what do you think I'll be doing, do you think?"
I pulled back my head and looked up at him, meeting his gaze. Spittle ran from his cock head to my lips. "Will you be touching this cock?" I said, trying to sound as sexy as I could. I ran my tongue over my lips.
"Yeah I'll be touching it," he said, pulling my head back onto his cock again. He started to thrust harder into my mouth, making my eyes water as I choked on it, and he kept talking in time with each thrust.
"I'll" Thrust "Touch my cock" Thrust "And you'll pull down" Thrust "Your panties" Thrust "And I'm going to jam. My cock. In you. So hard. So fucking haaaaaauh uh uh"
His voice twisted, his hands pulled my head viciously forward, and suddenly jets of pulsing hot liquid were spurting into my throat, as he mercilessly jammed his cock in as deeply as he could, not seeming to care that I was struggling and couldn't breathe. I clutched desperately at his wrists, but he had closed his eyes and was making guttural moaning noises as he filled my mouth and throat. I was seeing stars by the time he let me go, and I collapsed into a coughing fit, tasting the unpleasant salty cum as it sprayed back out of my mouth. Some had gone into my nasal passage, and I'd definitely swallowed some. It took minutes before I could even roll over and sit up. Gary was sitting on the bed, watching me, and wiping his cock on the sheets.
"That was nice, John," he said. "I think you'll be very good at this sort of thing, don't you?"
I couldn't look at him. I didn't say anything. My cock had gone limp during the choking fit, and I must have looked a ridiculous sight, my panties wet with my cum, and my face half-covered with cum and spittle, which had also dripped onto my chest. I stared at the floor.
"Heh," he laughed. "Well I bet you're sorry this ever happened, by now. But don't worry too much - you know your secret is safe with me."
"I... I need to go," I said.
Gary waved a hand dismissively. "Off you go, John. Let me know when Sam gets back, won't you? Just in case I need to borrow some sugar, or something."
I nodded disconsolately. I slowly picked myself up, pulled on my pants and sweatshirt, and made my way home.
- 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 f***ed to give a blow job to my neighbour.
Well... had I been f***ed? 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."
"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 f***e 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.
Caught by Neighbour Ch. 03
- 1 -
When I woke up, I momentarily had no idea where I was. It was dark, apart from the blue glow of a clock radio, and I could hear deep breathing. With a start, I realised that I'd fallen asl**p in Gary's bed. I took stock of the situation quietly. I was still dressed up in lingerie, and my bra was digging into my chest painfully. At some point I must have pulled my g-string back up, though it did little to cover up my hairless, naked cock and balls. Next to me, Gary was lying naked on his back, fast asl**p. I couldn't tell what time it was without moving, and I didn't want to risk waking him up. What to do?! Could I sneak out and go home without him noticing? Was it still the same evening? I had no idea.
I noticed there was a strange feeling in my ass, and I gently crept a hand down there, only to feel a mixture of crusty dried semen on my ass cheeks and g-string, as well as a fresher, wet, sticky mess that still seemed to be leaking out of my hole. Gary must have pumped a serious load of cum into me. As I thought about this, I u*********sly rubbed the cum around with my fingers, and then without thinking, brought them up to my mouth to taste it. It had a pungent taste, but not completely unpleasant. I felt a swelling in my crotch, and realised I was enjoying the sensation of tasting the cum that had leaked out of my ass. Rather than feeling ashamed, I felt extremely turned on by it. I couldn't help smiling to myself as I pictured the evening's events, and Gary ploughing his huge cock up into my ass as if I really was a sexy woman he'd brought home to bed.
I looked over, and admired his sl**ping form in the soft blue light. Stretched out on the bed, his stomach looked hard and muscular, and even while flaccid it was obvious he had a serious package downstairs. I lay there, half wanting to run away, and half wanting to reach out and touch him. After a few minutes, I realised I had stopped thinking about the first option altogether. Well, why not? I tentatively crept one hand out, and then stopped. If it were me, I thought, what would I really like to wake up to? I grinned to myself, and got very carefully onto all fours, turned around, and lowered my face carefully down over his groin.
As I did this, movement caught my eye, and I noticed a mirror in the open wardrobe, which I didn't recall being open before. By positioning myself carefully, I was able to look directly into it, and see my own face, well shadowed, and the bra straps across my shoulders, as I lowered my head and stretched out my tongue. I touched it very, very lightly onto the head of his cock, and then gently kissed it a number of times, before starting to suck lightly on the tip. I was rewarded with a gentle swelling, and I looked up into the mirror to watch myself take the head inside my mouth. I wished I could also see what I looked like from behind, with my cum-smeared, g-string clad ass propped up in the air for anyone to take advantage of. I had a huge hard-on myself now, and Gary began to stir as I experimentally lowered my head right down and tried to deep throat him. I couldn't get more than two thirds of his shaft in my mouth without gagging!
I turned my head slightly and saw that he had opened his eyes and was looking at me, not saying anything. I felt a sudden thrill - here we were, me dressed in sexy, spoiled lingerie, in his bedroom in the dark, where nobody would ever see what was going on. It felt like the first time I'd been laid, all over again - only now I was the girl. I touched my oozing ass again, and then, taking control, I got up on my knees, turning my back on Gary so that my ass was facing him, and carefully straddled his groin. He still didn't say a word, but gripped me lightly by the hips as I got into position. I held his cock with one hand, feeling my own saliva coating it, and drooled another large wad of spit onto my fist. I let his cock slide through my fist, marveling at how red hot and slippery it had become. Then I carefully guided it up between my cheeks. I pulled the g-string to one side, and mounted him. This time, the mess of saliva plus the cum in my ass helped him slide into me with far less resistance, and I pressed down until my ass cheeks came to rest against his stomach and groin. He groaned appreciately, and I looked to one side to see myself in the mirror again. I liked what I saw - in the faint light it was hard to tell that the slim figure straddling Gary was another man; I might almost have been a shapely woman with flat chest and short hair. Except of course for the huge tent in the front of my groin!
The feeling of his huge rod up my ass was amazing. It felt as it it was poking right up into my stomach, making me feel slightly sick. I began to gently rock myself back and forth, feeling the g-string catching on his cock and scr****g back and forth. I stretched forward and gripped his shins, giving me more leverage to fuck myself back and forth. Soon he was helping in the process, guiding my hips and grunting quietly, and within minutes, I felt him starting to tremble before he bucked his hips and blew another load of cum up inside of me. Before he could soften, I grabbed my own cock through my underwear and quickly jacked myself to a ferocious orgasm too, the cum blasting out through the filmy front of the g-string and coating my fingers. I turned to look at him, biting my finger and smiling shyly in my best impression of a naughty girl, and he laughed out loud. I knew then that whatever ideas I'd had about extracting myself from this situation had fled. In fact, I wanted more.
- 2 -
I woke the next morning to find that Gary had got up and dressed himself for work, leaving me curled up in the bed. He walked in and looked at me.
"Well that was some evening, hey Jane?"
"You said it," I smiled, stretching out before an uncomfortable sensation made me realise my cheeks were literally stuck together with dried cum.
"I have to go to work," he said. "You can go home."
I felt disappointed! "I don't think I can go in to work today," I said, "I think I'll just head over to my place. You don't, um, have some clothes I could borrow do you?"
He chuckled. "Not so keen to parade yourself in the street, huh?"
"OK, well, get what you need out of the drawers there."
"Perhaps you'd, uh, would you like to perhaps come over for dinner tonight?" I asked.
He thought about it, then said "Sure, but I hope that you'll be dressed appropriately."
"Appropriately?" I said, unsure.
"Yeah - I mean it's nice when you're all dressed up like a slut," he said, running his eyes over my soiled outfit. "But I reckon you might need to find something nicer to wear for dinner."
"OK," I said. "Well, come round at 7.30 and I'll do my best."
He went out, shutting the front door, and I did my best to clean up and find some clothes to put on. As I showered, I wondered at the situation. He'd seemed incredibly aggressive towards me that first night, but it seemed hat now I was co-operating with him, he was behaving in a much more pleasant fashion. What kind of guy was Gary? I had no idea. He seemed to get off on dominating me though, and right now I wasn't complaining. I just had no idea what I was going to do when my wife arrived home - which was only four days from now.
I made my way home and rang work, telling my secretary I'd come down with flu and thought I might be out of action for a few days. Then I set about raiding Sam's wardrobes for everything I could find. Until now, I'd always stayed away from her things, fearing that I might be caught out by the odd stain, stretch or ladder. But right now I didn't care. Over the course of the day, I assembled any number of possible outfits, before settling on a black dress which was stretchy enough to squeeze comfortably into, with a pair of sheer stockings and black heels. I took some time to run a shaver carefully over my legs to keep them as smooth as possible.
- 3 -
When the doorbell rang, I met Gary with a big smile. I'd done my makeup as best I could - a better effort than the previous day - and splashed on some of Sam's perfume, too.
He raised his eyebrows in surprise. "I didn't realise you were dressing to go out!" he said,
"Err... no we're eating here - I just thought you wanted me to dress nicely tonight?" I said, uncertain.
"Hell, why waste a good outfit!" he said. "Come on!". Before I knew it, he'd grabbed me by the hand and was towing me outside towards what I assumed must be his car. I was too stunned at the time to realise he must have driven it around the corner to my house deliberately. He opened the passenger side door and bundled me inside, slamming the door. I was grateful to realise the windows were tinted.
As he started the car and pulled out into the street, I summoned some courage to protest. "Gary, please," I said, "I can't go out in public like this. Can't we please go back home?"
He looked over at me. "What's the problem? You've got your dress and makeup on. You look like a hot date to me - hell, I'd do you!". He laughed at his own joke, and I felt myself blushing despite the situation.
Then to my relief he smiled, and said "Don't worry - I've brought some things to help you out." He pointed to a small sports bag in the footwell, which I opened to discover contained a wig of short, silky black hair, and two squishy items that I suddenly realised were fake breast inserts.
"I'm taking you to a restaurant where they know me well, and we've got a private dining room. So just keep your head down while we're getting seated and I'm sure nobody will notice."
I spent the trip there using the small mirror in the passenger sun shade to try to position the inserts and wig to maximum effect, but by the time we pulled up, I wasn't convinced I looked like anything but a guy in women's clothes. Gary seemed more impressed though, remarking that it was such a fine effort I needn't bother ducking my head. And as we entered the restaurant, to my horror he took his time greeting the owner and several waiters, introducing me as his new girlfriend Jane, and generally making it impossible for me to hide. But to my surprise, they greeted me warmly and didn't appear to notice anything amiss - the owner Geoffrey even giving me a peck on the cheek!
We were finally steered towards a small private dining room at the back, which had a small couch-style seat for me, and a comfortable chair for Gary. Geoffrey introduced our waiter, Charles, who was a tall, dark-haired young man with muscles rippling under his black t-shirt. I couldn't help feeling a bit weak looking at him, and wondered if this was what women felt when they talked about going "weak at the knees". Perhaps I was only imagining it, but I could have sworn he was checking out my legs and backside as he got us seated. Water and bread were served, but I took the first opportunity possible to slip out to the bathroom to check my outfit. I almost used the men's by mistake, before tottering into the ladies and checking in the mirror to see that my wig and makeup were OK. To my surprise, I was starting to see why nobody had commented - in the mirror I saw a young woman; perhaps not the most attractive, but with a certain cuteness about her. I was actually looking far more like 'Jane' than 'John'! I carefully checked my inserts were sitting correctly in my bra, then smiled at myself in the mirror and practised a little wink. The noise of someone approaching the door startled me though, and I quickly left as an older lady opened the door and walked in.
"Ah, here she is!" said Gary as I returned. Charles was discussing the wine list with him, and they appeared to be on very friendly terms already, though Carlo called him "Mr. Davids", which I realised was Gary's last name. "Jane, I was just saying to Charles here that he has a very Italian look about him - don't you think?".
"Mmm-hmm," I nodded, not daring to try to actually sound like a woman.
"Well I couldn't help asking him, and it turns out I'm right - tell her your real name, Charles."
Charles laughed. "It's actually Carlo. But my mother wanted me to fit in at school, so..." he shrugged.
"Do you like Charles better, honey? Or Carlo?" asked Gary. I glared at him, realising he was trying to f***e me into talking. I took a quick swig of water to cover my mouth, and mumbled "Carlo".
Gary laughed. "See! I told you. Jane has a real thing for Italians you know."
"Oh really?" chuckled Carlo, raising an eyebrow. If I'd been uncomfortable before, I was now bright red with embarassment, and wished I could disappear into the seat cushion.
"Well, I'll be back shortly for your order," said the waiter, and thankfully left.
Gary continued to chat to me as if nothing had happened, and as the meal progressed, he plied me steadily with wine and good conversation, and I actually started to relax and feel comfortable playing the part of Jane once more. Before I noticed it, I was completely d***k, and staggering into things as I got up to visit the bathroom again. Gary was clearly enjoying himself too, taking every opportunity to touch my legs under the table, and make completely inappropriate comments to Carlo. I couldn't help but enjoy it when Gary started implying I was terrific in bed, and asking Carlo to agree that I made a pretty sexy girlfriend. Thinking back later, I never even noticed that I'd started joining in the conversation with Carlo, and he'd not batted an eyelid at my deeper than normal voice. In fact, he seemed to be flirting with me too, taking each opportunity to touch my arm or shoulder, or brush against me as he served us. I had the opportunity to feel his very solid muscles press against me more than once.
Then just as dinner was ending, Gary looked at Carlo, and said, "So tell me honestly Carlo - what do you think of young Jane here - do you think you would like to get her into bed?"
Carlo laughed, and shocked me by saying "Well of course, Mr. Davids. You're a lucky man." He gave me a very suggestive look, and instead of being offended, I felt myself getting uncomfortably hard in my pants, and not for the first time that evening. The image of Carlo without that tight t-shirt on was starting to seem quite an attractive one.
"Well go on Jane," said Gary. He leaned over the table. "You know what you'd like to be doing."
"S-sorry?!" I said, looking from one of them to the other.
"I thought you said you were looking forward to eating some Italian tonight?" said Gary. My eyes must have nearly bulged out of my head at this, but when I darted a look at Carlo, I realised the two of them were quite serious. And worse, from where I was sitting, I had a direct line of sight towards Carlo's crotch. He had taken off the apron he was waiting in, and even with the black slacks he was wearing, there was no mistaking a huge bulge in the front of them. I sat there paralysed, with no idea what to do next. It was all playing out under the fog of who knows how many glasses of wine, but two things were pretty clear to me: one was that Gary was expecting me to go down on our waiter for his entertainment, and two was that I was still hard as a rock at the thought of it.
"I'll help instruct you dear, don't be shy," said Gary. "First, why don't you get down on your knees on the floor."
I hesitated just a little, but then slipped out of my seat in a daze, taking up a position in front of Carlo, who smiled down at me.
"That's it," said Gary, "now I know you're good at this bit. I think Carlo has a very special dessert for you that you'd like to taste."
I just nodded, and then looked up at Carlo submissively, allowing my mouth to half open. I reached up and slowly brushed my palm over his crotch, feeling the stiff penis inside his pants. He inhaled sharply, and I grinned. I carefully unbuttoned his slacks, and then slowly unzipped him, causing his underwear to bulge out through the opening. As Gary watched, I used both hands to position Carlo and gently bit down on the whole package, tasting the heady combination of cotton, sweat, and the unmistakable scent of his engorged penis and balls. Carlo groaned in appreciation, and then I couldn't delay any longer. I popped his cock out of his underwear, pleased to discover it was not only long, but also extremely fat, and wet with a strand of glistening pre-cum. I thrust my tongue out as far as possible so that the glistening strand fell along it, then proceeded to assault his cock with the most ferocious, wet, sloppy headjob that my mouth could manage. With one hand wrapped around the base of his cock and balls, I gobbled him in and out, deliberately letting some drool run down my chin. I squeezed his heavy balls gently at first, and then harder until he hissed in appreciation. Now and then I nearly gagged as he began to thrust into my mouth as well. Suddenly I realised that he'd gripped me by the hair to control my bobbing motions, and my entire wig had come off in his hand! I froze, not daring to look up.
Then to my surprise, there was a booming laugh from Carlo! "I thought as much," he chuckled. "Go on, don't stop now - I'm just getting ready to go."
I looked over at Gary, and saw that he had taken his pants off while this was going on, and was stroking his own cock while I was servicing Carlo. "Don't stop Jane," he said, "I want to see you take that cum all over your face."
That got me going even more strongly than before, and I started jerking Carlo off furiously, with my mouth wide open about an inch from his swollen cock head. With my other hand, I reached round and clawed my fingers into his ass crack, so that my longest finger was pressing into his hole. He started groaning in excitement, and then shouted in joy as a hot jet of cum squirted straight into my mouth and nose. I recoiled reflexively, but he had grabbed his cock as well now, and guided it as his hips bucked, shooting rope after rope of sticky hot cum onto my face. I couldn't believe how much he had to give, and ended up with one eye glued shut, making it hard to see exactly what the results had been - but I certainly felt like I'd been thoroughly glazed. The smell of the cum was overpowering, and it had a strong thick saltiness which I could imagine being unpleasant if I wasn't so incredibly d***k and horny. Right now I just wanted to gobble it all up. Suddenly I felt strong hands grab me and pull me roughly to my feet, before Gary was shoving me down over his dinner chair and ripping down my stockings and panties. Next thing I was being unceremoniously buggered by Gary, his own large cock skewering me repeatedly as Carlo's cum dripped and splattered off my face. My hands grabbed for support, while I also tried at the same time to sc**** Carlo's cum from my face and stuff it into my mouth. Within moments, Gary roared and jammed himself as hard as possible into my anus, and I could feel him bucking furiously as he coated my insides with his own cum.
We lay there, panting, while Carlo tried to make himself respectable. Finally, Gary eased himself out of me, and we each tidied our clothes, gasping. I tried to wipe myself clean with a napkin and glass of water, while Gary indicated I should sit down at the table again. Head spinning, I sank back into my seat, and before long, we were being served dessert wine and cheeses as if nothing had occurred. Carlo's cum started to dry on my face despite my best attempts to clean it all off, and I started to feel Gary's jism leaking out of me and pooling in my panties.
Eventually I confided to Gary. "Baby, um... I'm getting very... sticky in my pants." To be honest I was somewhat liking the sensation, due to the fact my own unsatisfied cock was still tenting my dress.