Caught by Neighbour Ch. 04

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My problems get worse... but it's not all that bad.
2.8k words
4.61
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28

Part 4 of the 4 part series

Updated 10/19/2022
Created 01/29/2012
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Morning. I blinked a few times and then opened my eyes, and lay there snug under the covers and listened to the pelting rain. I stretched my legs, and felt the delightful silky feeling of freshy waxed skin sliding against the sheets. It was a Tuesday, but I'd no intention of going to work - actually, I'd just about given up for the time being and told the office I was suffering from serious flu. What I was really suffering, of course, was from a surreal parallel life that I'd stumbled into, one where I dressed like a woman, acted and looked like a woman, and of course, went round to my neighbour's house and had sex like a woman at just about every opportunity I could get. I smiled at the thought, running one hand down under the covers, feeling the silky nightclothes and panties that I'd gone to sleep in, and my freshly waxed crotch, which was swelling already.

Since that remarkable dinner at the Italian restaurant, I'd seen Gary each day - mostly at his house, sometimes at mine, and was already busy on the internet ordering up more and more makeup, lingerie and other clothes to help me more convincingly play the part of 'Jane'. It wasn't clear to me that I looked completely passable just yet, but that only seemed to encourage Gary, who took pleasure in reminding me - often - that the rest of the world thought I was still just a regular married guy.

I started at the thought, remembering my single biggest problem, which was that my wife Sam was due home from her work trip on Friday night. I imagined I could explain away the waxing - after all, it was becoming a bit of a trend among guys - and I'd made sure to send my internet purchases to a post office box, but it was going to be pretty hard to explain why I was spending all my time round at Gary's place. I also hoped Gary wouldn't be insisting on the "walk of shame" I'd had to do quite a number of times, tottering from my house to his and back in high heels and a coat which barely obscured the outrageous array of women's clothing beneath - some of it torn and on more than one occasion, smeared with his cum and mine. I knew I would have to broach the subject sooner than later, and I dreaded it.

I got up, showered, and considered the day ahead. When I'd left Gary's the night before, he said he would be at work the whole day, so I had some time to catch up on a few work things that I really couldn't let slip - supposed flu or not - and do a bit of cleaning up. I checked that the right blinds were down, and then rifled through Sam's wardrobe, coming up with a matching floral bra and panties that I'd always liked the looks of. I pulled them on, stuffing my cock down between my legs until it softened enough to get the panties fitting better. After a quick spin in the mirror, I also decided to practice my makeup, and splash on a little bit of perfume. The only dilemma now would be how long I could last before needing to masturbate - I didn't like my chances of making it very far past breakfast.

But as I sat in the study and tried to concentrate on a set of spreadsheets, unexpectedly the doorbell rang. My heart leapt, wondering in rapid order whether Sam had come home early, whether Gary was paying me a surprise visit, or whether it was just the postman. I snuck to the window and peeked out, annoyed to see that it was Earl, a rather fat and greying retiree from across the road.

"Damn," I said under my breath, because it was pretty obvious I was home. I raced to the bathroom and quickly scrubbed my face, whipped my bra off, and threw on a bathrobe. The doorbell went a second time, and I called "Coming!".

"Hey John, how you doing?" said Earl, once I'd opened the door.

I coughed and put on my best impression of having just climbed off my sickbed.

"Not great actually," I said, "Come down with the flu."

"Yeah? Hey that's no good," he said. "Uh... hey can I come in for a few minutes? I needed to talk to you about something."

I groaned inwardly. Earl was an OK guy, but I really didn't want to get stuck with his company half the morning.

"Uh, sure - would you like some coffee?" I said, and he said he'd be glad. I took the opportunity to throw some clothes on en route to the kitchen, deciding to leave the floral panties on under my jeans, just for the thrill. We made small talk as I got the coffees sorted out.

"John," he said eventually, "What's troubling me is that I've got some problems with my business - you know the little start-up I've been running since I pulled out of Omcorp?"

I did know - he'd retired after many years at the software company, and with some pretty serious cash behind him, and was now amusing himself running a small development company that made business applications. I'd assumed it wasn't making nor losing much money, but given my background in accounting, I now suspected things mightn't be going too well.

"Did you want me to give you a hand with the accounts Earl?" I asked, but he shook his head.

"Oh no, not at all - it's quite silly actually - I need some help with the admin. I've picked up a few clients recently, and hired a couple of people, and I want to get hold of someone to do the paperwork, grab the phone, that sort of thing."

I frowned, and suddenly felt a prickling sense of unease.

"And the thing is," he said, leaning forward conspiratorially, "I want to hire someone pretty good looking!"

I stared at him for a moment. "Um... I'm not sure that - you mean you want me to recommend a receptionist?"

"Well, yeah. But the thing is, I've been wondering lately who that chick is that's been visiting you over here."

I feigned confusion. "What, Sam?"

"No, no - I know she's a away," he said, and winked. "I mean that hottie I've seen coming in and out the last week - you don't know if she's looking for some work now, do you?"

It finally dawned on me what he was up to - he'd spotted me coming back from Gary's, and obviously thought that I had a hooker paying me housecalls. One who would clearly be out of a job in about four days' time. My mind raced - I was relieved on the one hand that he hadn't worked out what was going on, but I didn't exactly want our neighbours to think I'd been spending the time whoring. Although I barely suppressed a grin at the sudden thought: that's exactly what I've been doing!

"Oh... uh I've had a family friend come round a few times, you probably mean her - Louisa," I said, hoping this sounded convincing. Bloody dirty old man - I wished he would finish his coffee and go away.

"Louisa?" said Earl, "Well it could be, I don't know. I'm not too troubled what you call yourself to be honest."

I blinked and stared at him.

He gestured with his head at my coffee cup, and to my horror, when I looked down, there was a clearly visible lipstick smudge on the rim.

"Err..." I said, "Yes, she's... used my, ah, she's come for coffee..." but trailed off as he grinned at me.

"I have a lot of free time these days you know John," he said, "so I like to sit by the window and watch the world going by. Some pretty interesting things go by, I reckon."

Earl chuckled.

"Anyway, you're a good guy, and I'm not trying to make life difficult for you. I just wanted to let you know I know - and it's OK."

"Great, well... thanks," I said, "and look I don't mean to be rude, but I've got a lot of things to get done today..."

"With your flu, you mean?"

"What?" I said, remembering too late to keep up the pretense. "Yes, well... I'm feeling a bit better today but..."

"Actually the other thing was, John," he cut in, "I'm kind of starved for company these days, and you know that a guy can get kind of lonely."

My eyes were probably widening comically at this point. I gripped the table with one hand.

"So... you know," he went on, "I was thinking that we could come to an arrangement. I won't tell anyone about what you're up to, and you won't tell anyone about my new lady friend - Louisa, or whatever her name is. Got ourselves a deal?". He chuckled loudly to himself.

"Seriously, you're a bit slow on the uptake," he said, pushing his chair back. "How about you show me where the bedroom is, and get young Louisa to come pay me a visit?"

I was truly stunned... not caught by one neighbour, but now two? This seriously couldn't be happening. And where Gary was a masculine, muscular domineering specimen of health, Earl was a disgusting old man, and a fat one at that. I shuddered to think what he'd look like with his clothes off, and then realised I was probably about to find out. I found myself walking to the bedroom in a daze, shutting myself in the bathroom, and trying not to think what I might see as I heard him walking into the room and settling onto the bed. I had a few things strewn in the hamper that I'd been planning to wash - some stockings, a skirt and various panties, so I fished them out and dressed myself, settling for a bra on the top, and a short skirt that barely covered my ass, leaving the floral panties on that I'd started the day in. After a pause, I decided to re-do the makeup as well.

I stepped out of the bathroom, and found him lying on the bed, fat stomach up in the air, and a surprisingly big cock protruding from beneath it. I was taken aback - Earl must have been nearing sixty, but he clearly wasn't suffering from any problems down there. In fact, his penis was impressively thick, and I was shocked to realise I was getting a little hard myself.

I smiled then, because it seemed that one thing was pretty consistent in all of this - I truly fancied being dominated, and the dirtier the situation, the more it turned me on. Earl smiled at me, and I smiled back, trying my best to look pretty.

"That's a very large fat cock you have there, sir," I said, "does it need to be taken care of today?"

He grinned. "It certainly does," he said, and waved me forward.

I knelt down beside the bed, and, looking him in the eye, reached out and brought it to my lips, kissing the top of his cock, which was already glistening with a bead of pre-cum. I made sure he could see it trailing from my lips as I lifted my head again. Earl's eyes half closed, and he reached out and pushed my head down, hard, so that his cock slid deep into my mouth. It was thick and hot, and tasted much better than I'd expected, and I began to work it, sucking and licking as he lay back and gasped in pleasure.

"You have a great ass, you know," he said as I bobbed up and down, "I'd like to see some more of it."

"Mmm-hmm?" I mumbled, and climbed up onto the bed. After a thought, I crawled around him, lips still fastened round his cock, and then straddled his head, giving him a close-up view of it, right up my skirt. I felt his hands slide up the back of my thighs, and begin caressing my ass through the panties. I sucked and licked, and gyrated my hips, and tingled with pleasure as I felt him pull my hips downward and bury his face into my ass. There was a delicious wet feeling as he wasted no time getting to work with his tongue, and I fancy I squealed like a little girl when he pulled my panties to one side and wormed it directly into my asshole - I nearly blew a load in my panties right then.

After what seemed like a delightfully endless time - me writhing on his soft belly and inhaling his penis, him opening my anus and defiling me with his tongue - he began to push me down the bed, and I felt him struggling to get to his knees behind me as I ended up on all fours towards the bottom of the bed. I knew what was coming, of course, and I wasn't disappointed.

With a few quick movements, he was kneeling behind me, and his big cock was forcing its way up into my ass - with me pushing back against him, perfectly happy to get as much as possible of it buried deep inside my chute. His stomach was literally weighing down on the small of my back, but I wasn't so much appalled by this, as thoroughly turned on. In my head, I was the dirtiest of street hookers, being paid to take it from behind by this awful, fat old man, and it was sexy in the most sordid way possible. Even having got a little used to Gary by now, I felt a bit dizzy at the waves of pleasure I got as Earl's cock slid in and out of my rectum, the sides stretching to accommodate, and I worried I might cum all over the bed before he'd even got close. But then I heard his breathing getting ragged, and with a gasp he clutched my hips, jammed my ass back against him as hard as he could, and bucked and bucked as he emptied his nuts into me with a shout. I was wrenched back and forth a few more times, amazed that an older guy could deliver so impressively.

When he was done, he pulled out and pulled my panties back into place, smiling as I looked over my shoulder at him.

"Well.. that certainly was worth the walk," he said. "But what about you?" He nodded at my crotch, where I still had a raging hard-on that needed some attention.

"Uh... well...", I said, "What would you... I mean..." I had no idea if he planned to go any further.

"Oh I like to watch, too," he said, "So I'll tell you what - just wait there a second, and I'll be right back."

I did that, lying on my side as he pulled on his pants and left the room. I could feel my ass twitching, and wondered how much of his cum I'd be draining back out of there shortly.

Clearly Earl had had similar thoughts, because he came back carrying a drinking glass, and I realised exactly what it was he liked watching. I grinned. There was no need for him to explain.

I squatted on the bed, skirt up around my waist now, and beckoned him over. He pressed the glass up under my ass cheeks, and with some careful pressure, I felt his jizz start to leak back out of me. I used one finger to help, and was startled at the volume that began to collect. I wondered how long he'd been saving it up. There was one particularly strong squirt, and in a few moments, I was holding the glass up, and it was holding a decent few mouthfuls of semen. I smiled at Earl, and pulled my cock free of my panties.

"Perhaps I should add a bit to this?" I asked, and he nodded.

"Yeah, you do that," he said.

I reckon it took about eight strokes, before I blew a load so hard that my head span. The glass swam with both loads of cum, and before I had time to think too much about it, I looked him in the eye, and drained the lot of into the back of my throat, and swallowed.

"Fantastic!" he said, when I'd finished choking it down, "I'll be looking forward to next time."

As he got his clothes on and left, I looked at the clock and realised half the morning was gone. I'd got none of my work done, was no further advanced in my thinking about Sam, and now I had a much bigger problem on my hands - not only keeping Gary happy, but satisfying my dirty old neighbour as well, who unfortunately seemed to share a few tastes of my own. I stripped off and made my way to the shower. Those bigger problems could wait - for now I had some more immediate mess to clean up.

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AnonymousAnonymousabout 3 years ago
Caught

My first dressed as a women full on make up an clothes i got caught by my older neighbour I had never had sex with a man or wanted to But now caught and hopeing he wont tell any one.I was now black mailed by him for sex.He took me over to his house fully made up and dressed.He told me he now owned me and we were going to now be husband and wife.I started to cry and was up set but that did not work.He took me to a bed room striped off my dress and panties.He striped naked and now for the first time i saw his big cock.It was 3'' round and 7 to8'' long soft.He layed me on the bed with my head hanging over and pushed his cockk down my throat and made me suck it and swallow his cum.After that he fucked me and made me suck his cock again and again all night.I now am his fuck toy wife to service him and any of his friends that want me.

AnonymousAnonymousover 3 years ago

I'd rather be a bitch and be used by these men than fuck my own wife.

lingerie65lingerie65almost 6 years ago
Sloppy seconds ?

Wow such a fat and dirty old man to be f***** by but I truly enjoyed not only going down on his delicious dick but also getting f***** by a doggy style, but having such a thickly meaty dick in me will always make me feel like a complete woman

cdCindy1cdCindy1over 6 years ago
please continue

I can't wait to read the next chapters (it's been too long since this one -- please PLEASE PLEASE write the next chapter). I too am a closet CD who is also married. I would love to have 2 neighbours with big fat cocks to suck and to fuck me. I would also love it if my wife came home early one day and found me in our bedroom sucking Gary's cock while Earl was fucking me from behind. Then my wife would realize and know that I am truly a sissy faggot husband -- AND I LOVE IT !!!

Please continue. All of us horny readers can't wait.

AnonymousAnonymousalmost 7 years ago
This.

MORE!... please

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