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 asleep 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 asleep. 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 unconsciously 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 sleeping 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 scraping 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?"

I shrugged.

"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 force 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 drunk, 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 drunk 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 scrape 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.