The Last Time I Babysat Part 1

 Thank you for all your lovely comments. I am glad you are enjoying my captions

Babysitting wasn't a regular earner for me. In fact, I hadn't done it in years. But money is money and despite making quick bucks selling nudes of a few ex-girlfriends on OnlyFemmes, I was still hard up for cash. That's why when the text came asking if I would look after Rebecca one Saturday evening I said yes with no hesitation. It was a bit out of the blue. Rebecca had been a cute little kid when I had looked after her back in the day but that seemed like an age ago. Surely she was old enough to stay home by herself by now... Apparently not! Besides, what sealed the deal was her older sister. Christina was certified hot property and I feel no shame in telling you that I watched her getting ready to go out with her friends with my jaw on the floor every time I was round there. I even caught her coming out of the shower one time. Reading the babysitting offer back again on my phone, I hoped to God she still lived at home.

My prayers didn't go long unanswered as she opened the door to me moments after I pressed the doorbell. She was exactly as I remembered her – utterly gorgeous and it suddenly occurred to me that now I was in my twenties I might actually have a shot with her.

“Christina, wow! You look amazing!” I smiled at her. She seemed to blink with surprise but quickly regained her composure and invited me inside. Just like old times she appeared to be getting ready to go out and there was an open bottle of wine on the kitchen counter. She offered me a glass. “Sure,” I nodded trying to play it cool. “Where is Rebecca?”

“Around here somewhere,” Christina grinned handing me the drink. “You know what kids are like – they get everywhere they're not supposed to.” She watched intently as I took a long sip of wine and I tried to act like I did this kind of thing all the time. I managed right up until the room began to spin...

I awoke with a throbbing headache. Not only that but all the skin on my body felt like it was glowing – as if I had just pulled a giant band-aid off. Groggily, I rolled over to find Christina sitting over me with a razor in her hand.

“Shit!” she tossed the blade into a bowl of hot water next to a tangle of spent waxing strips. “Looks like I got the dosage wrong!” Before she could react, I stumbled to my feet. It was then I realised I was completely hairless from head to toe. Not only that but a pair of tight satin panties clung to my newly smooth backside. What the fuck was going on here?! I tried to run but my legs felt like jelly and the world sloshed around me with the after effects of whatever Christina had given me. I moved in the direction of what I thought was the door but giddily sprawled onto the sofa instead. Feebly, I tried to clamber over the back cushions to put furniture between myself and the crazy bitch that had drugged me. However, my burst of energy spent, I only succeeded in flopping forward and presenting my pantied butt pathetically in the air to my captor. “Bless you,” the girl giggled behind me, “but we're not done, not by a long SHOT!” There was a sharp pinch in my ass and then everything went black.

Neighbourhood Watch

 

“Remind me because I think I'm going giddy in my old age, but why do you shave their heads first?” Martha looked over the paraphernalia sprawled across Molly's kitchen table. Over the decades, the two women had shared many meals here, but now it was home to a cut-throat razor in a bowl of foamy water, a mug of tea with a saucer of freshly pruned leaves and of course, a make-up bag of epic proportions.

“Oh Martha...” Molly smiled sweetly at her dear friend. “Why, it's to help the wigs stick longer of course. The glue just sets so much better to the scalp than it does to hair. Besides, they could just cut that off, couldn't they?” She turned back to her project and gave the blank-faced boy a knowing look as she continued to work her pencil around his painted lips.

“Of course, silly me...” Martha chuckled as she admired her friend's work. “Wait, I know this one. Leo, isn't it? My granddaughter says he's a right nasty piece of work. Always taking money off the neighbourhood kids. Probably shoplifts too.”

“Oh, he's money motivated alright,” Molly sighed. “All I had to do was offer him money to cut my grass and you could practically see the dollar signs in his eyes. Probably had designs on my purse when my back was turned too. I know his sort. Plenty of them have come through this kitchen, as you know. A mug of my home-grown tea certainly made him more obedient.”

“He'll have a shock when he wakes up!” Martha reached over to stroke the bead necklace wrapped around the boy's neck. Her hand moved to the faux-fur jacket and then the shimmering twenties style ballgown. “Oh Molly, don't you remember when we used to dress up like this?”

“Oh, he's awake already,” Molly sat back so Martha could get a good look at Leo's vacant gaze. His eyes stared out lifelessly from behind layers upon layers of cosmetics and his bottom lip hung open as if weighed down by the pink gloss. “Can't you see the look in his eyes? My tea doesn't put you to sleep. It just makes you compliant. Leo here is aware of everything but can do nothing. Hence the wide-eyed 'dying on the inside' look. I'm just finishing up and then I'll send him off home. By the time he regains control, half the neighbourhood will have seen him.”

“Do you think he will learn his lesson?”

“I'm not sure it matters,” Molly put the pencil back it her giant makeup bag. “After his parade home no one is going to take him seriously as a bully ever again. Besides, like I said, the glue sets really nicely to the scalp, the makeup is my permanent stuff and there's always this little trick...” The old woman pulled out a tube of glue from a fold in her apron and squeezed it liberally over the zippers on the back of dress and the fronts of the high-heeled shoes housing Leo's feet. “He'll still be in this dress by the time he gets to our age,” she joked. “Won't look half as good though...”

Mirror, Mirror...

 Thank you for making me feel so welcome to be back

Michael gazed into the hand-mirror for the ninetieth time that day and for the ninetieth time that day, he didn't recognise the face staring back at him. The sweet little nose, the delicate chin, the exquisite cheekbones – all expertly crafted works of art, things of pure beauty...but none of them were his. Like much of the rest of his body, they were the result of state-of-the-art enhancements from the finest surgeons in the country. His body had been cut up and crafted into something spectacular by leaders in their fields. The problem was Michael didn't want any of it. Same as how he didn't want the sheer nightgowns, or the designer lingerie or even his pink painted nails. He didn't want it at all. But the mirror did. And that was all that mattered...

The hand-mirror had been a Mother's Day gift. He had been searching all day for a present for his Mom when he stumbled upon a boutique on the edge of town. The mirror had called out to him from the front window of Gloria Honeypot's Emporium of Fun and Folly and he knew he had found what he was looking for. Little did he realise at that moment that the mirror too had found its target.

Michael's mother never did receive her present. Just one look into the silvery glass was enough to lock him in. One glance and he was immediately compelled like some kind of jewellery box marionette to create something worth reflecting back. Merely a passenger behind his eyes, he had observed his body as it slipped into a nearby store and purchased cosmetics and a lacy dress. He wanted to scream as his feet marched him home to try on his new wares in front of the mirror. More than anything else, the compulsion to look at his own reflection was overwhelming. That night he had watched on in horror as the hand-mirror like some kind of demanding mistress forced him to dress himself up – constantly checking how he looked in its gleaming face as if he were being inspected. If only it had stopped at that...

The mirror clearly had loftier ambitions for whom should be allowed to stare into it. Michael looked on in dread from within his own betraying flesh as his body emptied his savings on a more complete wardrobe overhaul and then began to schedule appointments with doctors about hormone treatments and finally even surgical operations. Over the past six months he must have seen his reflection a million times and each time it looked different – softer, more feminine, strikingly beautiful even. Finally after half a year, all he had to show of his old life was an empty bank account in his own name and a tiny bald cock shrivelled by multiple rounds of hormone therapy...

There was a loud thumping on his apartment door and Michael looked away from his reflection at last. His heart began to pound and his arm involuntarily placed the mirror carefully down on the dresser. Suddenly he longed to be back standing in the middle of his room staring at his refection. It was at least better that what was about to happen. As he reached to open the door, he knew he would be looking at his face again in that glass shortly – only when he did it would be glazed in the cum of the man standing at his door.  

New Orders

 So it's been a while, eh? Almost eighteen months... I'm really sorry about that. I got a pretty big promotion this time last year and simply put, I just don't have the time and energy to work on these big interwoven 25 caption seasons anymore...let alone the caption a day thing I had going on in like 2015. I'm much more inclined right now to do some online gaming right now after a long day at work rather than yet work sitting in front of a computer typing.

That said, how about we change things up so that this doesn't fade into the sands of time. I can't promise season after season of content. But, I can manage a caption a week. How about Missy Mondays? That's a thing. right? Well, it is now! I hope you enjoy, and love you always.

zoli

ames looked at the screen in confusion. A browser was open to the home page of retail titan, Glamazon, and even though he was clearly logged in, his store credit balance was showing as zero. What the hell?! He needed that money! Badly! Times were tough and he and his girlfriend, Sophia, were struggling to make rent as it was. They simply couldn't afford for credit they had planned to spend on basics to go missing like that. Frantically he clicked into his account page and his profile flashed up. Suddenly it all made sense as he realised what had happened and he let out an audible sigh. However, his relief quickly faded to horror as the full understanding of what it meant materialised.

James had a second Glamazon account – one that Sophia didn't know about. Money was scarce and the belt was tight but that didn't mean the temptation of online shopping went away. So, whenever James wanted to defy his frugal partner and treat himself, he logged into his second account and scheduled some orders to arrive when he knew she would be out. Fool proof, as long as he always remembered to log himself out – and as long as his order history didn't include a bunch of forced-feminisation ebooks he absolutely didn't want Sophia to know about. Wondering how obvious it was he had purchased the erotica, he clicked onto his orders page and his heart pounded in his chest as it quickly became clear his girlfriend had already seen it.

Another thing that was clear was the sexy lingerie Sophia had ordered on his account was meant for James – the inclusion of blonde hair-extensions and high heels in his size made sure of this. What was less obvious was how his girlfriend planned to get him into said underwear. He assumed she would blackmail him with his smut collection, in which case he would just refuse and deny everything. If only...

“Sweetheart, stop hiding,” Sophia taunted him from behind, “I want to make sure all our neighbours see what a hot little sissy you make. Don't make me tighten that corset even more!” James gulped and forced himself to totter in front of their large arched window. He could barely breathe as it was and the skin on the small of his back was pinching under the white satin. Surely people in all the other houses on the street had seen him by now. He felt totally exposed in every direction – the glass, his bare waxed skin...even the sheer panties packaging his ass cheeks up for his girlfriend's appreciation. “Come on, sissy, give me my money's worth!” James glanced back with a bruised expression at the mention of their finances. Sophia had never had any intention of keeping his secret. Instead she emptied his bank account via his Glamazon account on a collection of sexy and suggestive outfits. If he didn't like it, he could leave. Not that there was anywhere he could go without a penny to his name. Sophia's name was on the rental contract and so she effectively owned him if he wanted a roof over his head. “Come on, my slutty whore,” Sophia sneered at him, “I want everyone to see my sissy wife to be. I wanted you to buy we a ring but instead you spent all our money on sissy porn so consider this our engagement, only I'm not asking and I won't be the one wearing a dress down the aisle!” James's knees knocked within their silk stockings as he began to understand just how much his dirty little secret was a secret no more...