Caught Out, Made Over

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans from the shemale porn on the tablet in front of me. It was an awkward situation to say the least, but it wasn't my own pain inside that I was aware of (figuratively, or literally); it was how much I'd hurt Cat. She stood at the door from the hallway, suitcase in hand and mouth agasp. With only a seconds hesitation, she'd dropped her bag, then came at me with a haymaker of a swing that any wrestler would be proud of, a crazy hard punch to the temple, followed by darkness...

********

It had all started years ago, probably 20 odd years ago. When I was in my late teens, and I first found my Dads stash of porno mags, I would look through them for hours, not just staring at the girls all naked inside, but more at the beautiful ladies in their lingerie, stockings, corsets, all begging wantonly for some attention. When I did eventually get a girlfriend and lose my virginity, I kept a pair of her undies, and I would wear them to bed when ever she wasn't there. My addiction deepened at university, where I would steal my housemates knickers whenever we had a houseparty (trying to cover my tracks). I loved the feeling of the lace sliding over my body, or the feeling of the g-string riding right up my crack.

It was that year that I sucked my first cock- home after a long weekend of drink, drugs and dancing, John and I had crashed in my bed, when I was awoken by him playing with my penis. I was still high and couldn't get hard, but I sucked his sweaty meat like my life depended on it, him spraying his salty cum into my mouth after only minutes. I swallowed it down like I had with my own cum so many times before.

I'd started playing with my own ass by then, first with a finger or two, or maybe with a hairbrush handle when I was in the shower. Fruit and veg became very important in the shopping list too. A carrot or banana? No problem. A cucumber? No worries. If it was round or vaguely phalic, it went up. I've had coke cans, condoms filled with apples, even did the post on my bed. I enjoyed the feeling of being full when i came, but it was only a few years into my marriage to Cat when I learned of prostate orgasms.

We'd met thru work, hit it off, and within a couple of years we were walking up the aisle. Tall, blonde, nice big round tits, everything I'd ever wanted in a wife. Well, wouldn't let me play with her butthole, but I guess you can't have everything. We bought toys for each other, and when our experimenting progressed, I bought us a strap on dildo, the kind that the dildo slots into what are otherwise a pair of panties, the Sasha harness from SpareParts. She was a little taken a back, but rolled with it when she saw how much I enjoyed the butt fun. I never managed to prostate orgasm when she was in the saddle, but when I fucked my ass with a dildo I could easily make myself cum. It felt amazing, but I wanted to be more passive, have myself fucked to orgasm instead of masturbating. Cat worked away from home so much, but I'd never cheat, my focus became getting myself off, out of my control.

I turned my attention towards making a fucking machine to do the work for me. A lot of Googling and a few experimental builds brought me to my creation; Fuckosaur, using sewing machine parts and some odds and ends from the garage. Oh, well it was amazing. I could stay on my back for ages, or doggy style getting pummelled, only slowing to add more lube. I was getting closer to the big p-spot "O", but never quite got over the edge.

By this time I was watching more transexual and sissy porn, seeing them getting pummelled, streams of jizz pouring out of their cocks was hot and always made me jealously horny. I followed some video advice and bought a chastity cage, so I could focus on my rear end. I got different length, girth, material, colour dildos and butt plugs. The hypnosis videos I was watching recommended I dress more girly, so I ordered some outfits online, picked up some heels from a thrift-shop. I even got some silicone boobs too, oh-boy! They felt amazing!! They bounced just right when they were swinging around in my bras, they felt as real as I could ever think of. Don't get me wrong, I'm not passable as a woman, nor ever will be. I don't want to be one forever, I just enjoy it when I can. And speaking of which, I had a couple of days to myself coming up- I can't rememer why Cat was going away this weekend; either work or a training camp for her netball team. Either way, I knew I had a bit of preparation ahead.

On the Friday morning after She'd kissed me goodbye and left for work "Bye babe, I'll see you on Sunday!" Within minutes I was locked in my cage. I took a nice hot shower and gave my bumhole a shave. The sensation always gets me hard, so I distracted myself with a little enema; can't have a nice anal session slowed down by making the wrong kind of mess can we?!

After getting nice and clean I lubed up my medium butt plug, and slipped on my nice red lacey panties. I couldn't fully go en femme with a day of work ahead, regardless of how little work I was going to get done, but I did put on a pair of stockings underneath my trousers.

It felt like the longest day in history, but at least the bus ride home gave me a nice feeling through my plug; it was almost like the driver knew and was hitting every pothole and speedbump with gusto. It'd been over a week since Cat and I last fucked, so by the time I got in through the front door, I was dripping wet in my cage & panties. I couldn't shed my boy clothes fast enough. In fact, time for a wardrobe change. Cheerleader has always been a favorite, and by the time I was finished, even if I did say so myself, I looked hot! My boobs tucked into my purple and white crop top, above my purple, white and gold mini skirt, itself only just long enough to cover my purple thong that encased my little caged cock, down to my white thigh high socks and purple high heels. Add in some lipstick & mascara, perfume & blonde wig, and I was ready to fuck my way thru the athletics team!

Alas, I'm no cheater, and I'm home alone. I do however, have a whole internet of sissy porn, and my lubed up Hoodlum 11 inch bbc mounted on my fuck machine. I loaded up a bunch of my favorite hypno, sissygasm, shemale, bbc and gangbang vids, then pulled out my plug before opening my bottle of poppers for a couple of strong hits. Whew, they are always good, my head throbbing as I eased myself back towards the tip of the huge phallus. I keep pushing backwards, my eyes roll, and all of a sudden my ass opens up to the brute. I can't think of anything other than what's filling my ass right now. I can just manage to twist the dial a bit to start off the machine.

Oh. My. God.

At first, it still feels tight, my hole stretched, almost stinging as the dildo thrusts in and out. As I get more used to it, the pain is still there, but more numb, leaving me to focus on the filling I'm getting.

I'm relaxing more and more, slipping into who I want to be.

Each breath gives me aftershocks of the amyl, sending me closer to who I want to become.

I can feel every inch, rib and vein of that cock as it slides back and forth, over and over, nudging my prostate every single time.

I can feel myself getting closer with every second, my ass clenching and starting to spasm, I'm tingling everywhere, I'm sure I can hear ringing in my ears, but it's different, it's not ringing, it's keys... and I can hear voices...

"... of course it'll be fine, he's probably online playing his computer games, and there's plenty of room. I'll set up the... ... what the fuck?"

I couldn't do anything other than freeze. I couldn't disappear, and I sure couldn't hide the moaning from the porn in front of me, or the pounding my prostate was getting. Dazed, high, and a bit confused, I moaned and came hard, squirting my cum all down my thighs, the cupboards and floor.

Cat took two steps forward, then knocked me out cold.

... ... ...

...I was having the strangest dreams, being used over and over, relentless on my butt, never stopping or slowing down. In my dreams, I could feel myself reaching another crescendo, cumming like a girl, squirting more juices from my little clitty...

"Oh my god, Cat, he just came again!"

"Seriously? He could never manage twice with me, I guess now I know why."

"Mmmmphhhh... Ca..."

"Hey, he's starting to wake up."

Cat strode over, and sat on a stool across from me. She turned the dial on the sex machine to 0, Hoodlum instantly grinding to a halt at near full extention, impaling me against the kitchen bench. There was little I could do but stay bent over the counter.

"Well hello, Alex, it seems we need to have a little catch up. First of all, I'm sorry that I hit you. You see, it really took me by surprise, finding you... like this..."

She paused and took a little sip from her wine glass. I'd noticed that two of her friends from netball, Kylie and Becca, were here, but it only just registered that they were sitting on the couch, glass in hand, hanging on our every word.

"Not that I need to explain myself to you, but I got the call that Coach had had an accident, training camp was cancelled, so we weren't going to drive out there. I did try to call you to let you know Kylie and Bec were staying over tonight, but obviously you were a bit busy..."

"... it's not as bad as it looks..." was all that I could pathetically muster, before I trailed off.

The girls all had a bit of a chuckle at that.

"Well, it looks pretty bad from here, honey."

"And it looks like you've been VERY bad from here!" piped up Kylie, "That dildo is huge, I don't think I could take that whole thing in my pussy, and he's got it up his ass to the hilt!". Again, they all had a little laugh at that.

Cat continued: "She's got a good point there, honey." nodding. "And it's all starting to add up. You've always loved me in lingerie, but you buy more than I ever get to wear. Is some of it actually for you?"

I nodded sheepishly.

"And, a bit of manscaping is kind of normal I suppose, but seeing you shaving your butt-hole is a bit different."

More sniggers from around the room.

"But when you brought home that strap on cock thing to get me to fuck you with, I should have known you were gay."

"I'm not gay!" I protested, "I...I was bored with you travelling and just trying to get myself off."

"Well, I think that Alice has gone a little too far through the looking glass to be able to say she's straight. I reckon most guys would probably go out with mates for a few beers, and go home for a wank. Not dress up like a cheerleader so they can fuck themselves up the ass!" A few tears rolled down my cheeks.

"A strap on cock?", asked Kylie.

"Shit, that's hot. Dan would've never let me anywhere near his butt if I'd tried." replied Bec.

"That's a shame, he had a great ass! I've played with Matts' bum a bit, mostly just a finger with his blowjob, but a strap on cock sounds really hot. Can I see it?".

"Of course, Alice here won't mind, will you Alice?"

Cat was looking and talking to me, waiting for an answer.

"Erm, no Miss." It just slipped out, I can only think it was because of those sissy videos I'd been watching.

"Miss? Ha! I like that. In fact, yes, that works very well, Alice. I think it's time I had a little fun out of all this. You need to do bit of cleaning up around here. I guess this is your little sex toy bag here?" as she lifted up the bag, more of my guilty sins spilled out on to the table.

"Fucking hell, Alex, I mean Alice, you could start your own sex shop with this lot!" There was certainly an array of toys; dildos, butt plugs, chastity cages that were now too big, corsets, stockings, heels, soiled panties...

"Yes," Kylie said as she walked up to the table to have a good look at my collection. "I think you've got plenty of making up to do. But not looking like that mess." She picked up one of my larger butt plugs, a heavy black studded number I saved for special occasions. She walked over to where I was still impaled, bent over the counter and she crouched down behind me. I couldn't see what she was doing, but when she stood up, and put the butt plug on one of the bar stools, it was shiny and glistening, apparently coated in a mixture of lube & my own cum from the floor and cupboard. "It's time for a real make over, but you need to clean yourself up first. Get that dildo out of your ass, and replace it with that plug, now."

It really didn't matter who was in charge, but what was clear, was that I was not. I twisted the dial for a fraction of a second, my fuck machine pulling back enough that I could dismount Hoodlum. After two orgasms and at least an hour of being filled, my poor ass felt empty. Kerry moved towards me, grabbed both my shoulders, and pushed me back and down over my plug. It slid in with only the slightest of resistance, but still a gentle moan from me, and a subtle twitch from my little cock. It did not go unnoticed.

"Fucking hell, this little tramp loves it!" Bec exclaimed. "So where do we start?"

"Let's see what we have to work with. Strip." Kylie was really taking control. She's a bit bigger than Cat, maybe a size 14 or so, but being about 5'10", a very nice "hour-glass" figure. Even in the awkward situation, I was still looking at her nice full breasts, and round ass in her tight jeans. "Stop ogling at me, and get those sissy clothes off NOW!". For the second time tonight, I stripped off, the only items left were my wig, cage and plug.

"So Alice," Cat began, "explain this little cage thing that you're wearing. Why are you wearing it?".

There was no point in holding back now, so I started laying it all out. "I was trying to reach a prostate orgasm. I saw that the best way was to lock up your cock so that you can't be tempted to play with it, and then just concentrate on your butt."

"So you can't take it off right now?" asked Bec. She leaned in closer to get a better look. I've always found her hot in a kind of girl next door sort of way, a little shorter than Cat, but still well proportioned with a nice rack and brunette hair tied back in a ponytail. I'd often fantasized of fooling around with her, but this was not how I'd imagined her bending over in front of my dick.

"Not without undoing the lock."

"I guess you'd need this key to be able to do that?, Kylie stood there with my key, picked up from off the table. She handed it to Cat. "I think this belongs to you..."

"Yes, it does. Thank you." She eyed me up and down with disdain. "But it needs work. There's too much body hair," as a grin spread across her face. "He always wanted me smooth and bald, I think it must be good enough for Alice too. Let's go through to the bathroom."

The ladies all grabbed their wine and started down the hallway. After the big dildo fucking I'd had, and now a girthy butt plug, there was not a shred of dignity in how I walked naked to follow them down to the en suite. Cat was rummaging through the vanity, and when she found what she was looking for, squirted some cream from the tube into my hands. "Rub that in to wherever you can find hair, the rest you're going to shave off." I stepped into the bath and started rubbing the cream in and around my cage, balls and butt cheeks. Within seconds it was starting to really smart as the hair began to dissolve.

I was ordered into our open shower, the scene of many a time that I'd watched Cat lathering up and shaving her legs; now I was about to too. I'd never done it before, and with adreneline rushing through my body, my hands were shaking.

"Here, let me do this for you, honey", offered Bec, as she took the razor from my fingers. She was smooth, and calm as she worked from my thighs down to my ankles. Fuck this was so hot. I'm a mess of emotions right now, from being high and horny, to caught red-handed and ashamed, now excited for the moment as I'm starting to experience my dreams and fantasies, unabashed. "There we go, nice and smooth. You've actually got a pretty nice pair of legs."

"We're not finished yet," Kylie interrupted, "there's your chest and under your arms still. Can't have a pretty girl with hairy pits now, can we...?"" She started foaming up my chest, diligently shaving and rinsing as she went. She was not as gentle as Bec had been with me. Cat by now had finished her wine, and had filled her glass again. She stood in the doorway taking a sip.

"I'd like to see you in this little number," holding out my red corset with the black bows. Actually my favorite outfit. "Dress to impress me." I took the lingerie from her, as she turned and drifted back to the lounge. I heard the stereo come on as she found some tunes. Kylie stood behind me and helped me into the corset. Bec disappeared, then returned with my breastforms, black stockings and red strappy heels. I tucked in my boobs as Kylie pulled really hard on the laces at the back; I could barely breathe! As I sat on the toilet seat to put on my stockings, I'd almost forgotten my butt plug; again I couldn't help but groan as it hit my swollen prostate. Lifting one leg at a time for the stockings and heels, only served to put more pressure on my gland. And wow, stockings on shaved legs really are next level, the feeling as the material slides over my skin is to die for. I've never felt them like that before, now it's with permission, or more by demand, that I've shaved my legs.

"You're looking sexy, honey," Bec commented, "but we just need a little more make-up to turn you in to a gorgeous girl, how does that sound?"

"That sounds perfect." I replied with a timid smile.

She grabbed the foundation, and straddled my thighs. Light brushes coated my cheeks as blusher went here and there, mascara at my eyelashes, a luscious layer of cherry red lipstick. Straightening my wig, and with a light brush of my blonde locks and we were finished.

"Done. You're ready, baby girl."

If I thought I looked good before, I was damn right stunning now. I'd never in a million years dreamed I could look this good, but here I was, oozing with sexiness. If I didn't know, or my little cage wasn't visible, I'd have thought I was standing in front of a high-class hooker, not a mirror. Getting caught by my wife had been an idle fantasy of mine for years, but actively walking out to her dressed en femme really was making my heart beat triple time.

What I was greeted with as I entered the lounge was an incredibly sexy sight in itself; Cat was sitting on the couch, computer open pornos playing, with her hand down the front of her jeans.

"Well, don't you look like the perfect little slut." I didn't know what to say. "All of these hormones flying around has got me hot as fuck." Cat was shuffling her jeans and panties down. "I need my pussy licking right now, don't come up until I tell you."

Damn, she'd never talked like this before, but I didn't need asking twice. As I knelt before her to part her thighs, the heat coming from her snatch was immense. I could see her pussy juices dripping down her cheeks. I dove in to find her cunt was already really swollen, her clit standing erect. I licked and sucked and chewed and nibbled as best as I could, though she was grabbing the back of my head, really humping against my face. It was a scramble, but it seemed that within just a couple of minutes, she was screaming as an orgasm tore through her body. Her thighs clamping my head, I could barely breathe, or lap up her juices fast enough.

"Mmmnnnn... thank you, Alice. Now I think you need to say thank you to my friends for helping turn you into a proper pretty girl tonight." I stood and turned, Cats hot juices still coating my cheeks. Her friends had obviously been enjoying the show; Kylie had had her hand down her pants, Bec playing with her own nipples through her top.