Princess Bet

Make sure you word your bets correctly!

What’s that?  Oh, it started over a bet.  You see, I told Ron that I could make anybody over into a princess.  He knew damned well that I meant any of the women that come to my salon, but he just had to up the ante.  He got me to agree to his terms and to be honest, they were kind of fun.  He said if I couldn’t make him over into enough of a princess to win that comicon contest, I’d give him a blow job.  So I got to work.  I put him in a corset, put a wig on him, made up his makeup beautifully, put him in a dress and entered him in the contest. 

 

Hmm?  Oh, I don’t know.  I mean honestly, he was cute and funny and I probably would have blown him if he’d just asked, but he was such a jerk.  He worked against the costume every chance he got.  He pulled the dress down so people could see his flat chest, he talked in his lowest voice possible, and just before the big stage contest he went in and washed the makeup off.  He still looked cute, but he still lost.  He cornered me once we got back to the studio and was so cocky about ‘winning’.  That’s when I took it into overdrive.  I told him that he never put a time limit on the best and that I’d enter him into the contest next year and that would give me twelve months to get him into better shape. 

 

Of course, he tried to wiggle out of it.  But I had taken enough photos and made up a twitter post of him ‘coming out’ to everybody.  You know how macho he was.  He couldn’t stand the thought of anybody thinking of him as a sissy even for a moment, so he went along with what I said.  Each weekend I had him over and we worked on his princess exercises.  Walking in heels as that would give him more shapely legs and push his rump out.  I started corset training him so that I could really get him down to an hourglass shape.  We even worked on his voice.  Oh, you bet I took photos and videos each time.  Every time he balked, I made up a new twitter post to show him that was more and more convincing.  That’s right, the blackmail became more effective the longer he did it. 

 

So, the next contest came up and bless his little princess heart Ron really tried.  I thought we actually had a good chance, but that was the year Helen came in and… well, she was just gorgeous.  What?  No, I planned on letting him out after that.  He’d gone along with everything I’d asked for a year with barely any protests and as long as he agreed that we’d both lost, I’d go with it.  But he just went back to cocky Ron instead of pretty Ron and demanded I give him his blow job then and there.  That’s right, I upped my game and figured if this was going to work, I’d need more than weekend with him.  He spent days in a row with me.  His corset training really started to come in as his waist shrunk down and stayed that way without it on.  Yeah, he had to buy new pants but honestly at that point I had him an entire new wardrobe.  Skirts, dresses, stockings, panties, bras, lingerie.  All in the prettiest princess pink with laces and bows and silks.  I made him grow out his hair so we could ditch the wig.   He was so cute when he begged me to not dye it platinum blonde, saying it was already hard to explain the other changes to his work and girlfriend, so I just went for that pretty brown he has now.  Sadly, as much as he tried, we lost the next year too. 

 

Nope, he tried to absolutely refuse.  How?  Well, I told his girlfriend Lucy.  Yeah, she got in on the act.  It really helped that she was his boss’s daughter so if he wanted to keep this away from work he’d need to keep her happy.  No, he did that all himself.  Once she knew, he thought it would be better to let her think he was just exploring this side of himself instead of admitting I’d blackmailed him.  Lemme tell ya, she’s a real minx and took the game to a whole new level.  I didn’t even realize she what she was doing until I noticed he was walking so much more girly.   It turns out she was making him wear a butt plug almost the entire time.  And when I made him shave all his body hair away, she loved it so much that she made him get it lasered away permanently.  Nope, the blackmail was still good as he was trying to hide all this from his work and his family.  I think our little princess is quite the bimbo as honestly, he believed that the hormones Lucy put him on would be temporary.  Anyway, I honestly thought we had it that year.  It was almost perfect, but I guess he’d pissed off Lucy that morning so as he went up to do his walk across the stage she turned on his vibrating plug to full intensity… yeah he tripped.  A more graceful princess won that year.  

 

Nope, that was all his choice.  It was getting more and more difficult for him to look masculine at work that he thought working from home was a good idea.  I don’t think he thought it through as Lucy and I could now do anything we wanted without worry of making him ‘manly enough for work’ in the morning.  I told him he was going to be my pretty princess twenty-four hours a day, seven days a week, except for when he went to visit with his family.  Well, it was kind of a Cinderella package as he was my maid most of the week.  No, that was 2020 so the con was canceled.  He cried and cried as Lucy and I figured we’d take advantage of the extra year.  I mean at first I was happy with just some falsies, but his hormones gave him the cutest pair of budding breasts that I figured we’d take advantage and give him augmentation surgery.  I swear, I only signed him up for a cute C cup but Lucy talked to the surgeons the week before and gave him those.  Nope, those are full on F cup beauties now. 

 

So last year the con wasn’t canceled, but it was held remotely.  We had a nice video presentation, but another contestant took it further. She actually filmed her entry in a castle with a cast of people all acting like she was a real princess.  She won with all the votes.  Now, I can’t remember the last time anybody even thought he was a man under all that femininity.  I’m not sure we could do anything more to fool anybody.  But bringing more reality into gave me the idea that’s guaranteed to win it.  I mean, who’s the obvious candidate to win a princess contest?  A real fucking princess! 

 It turns out that there are quite a few princes who secretly want an American bride.  And after I got through to some I found two that were really excited to have one with ‘extra’ parts.  I won’t share names as I don’t want the loser to be known, but I’m setting up dates with our princess and a prince from Thailand and one from Liechtenstein.  Lucy and I have been working with Cecilia… oh that’s what Ron goes by now as that would work better as a princess name… to better please her future husband.  Each night we get Cecilia on a ‘date’ with one of us playing the part of her beau.  Lucy is concentrating on the anal sex as she’s already worked so hard with those plugs to open Cecilia up down there.  I’m working more on a demure attitude and how to fellate her man.  I swear, she can get me to cream as I watch her bob up and down on my strap on. 

 

Yup.  So, both princes are aware that they have to propose and marry our princess before November when the con is.  They’ll each get three dates with Cecilia.  Once we have a winner and they propose, then we’re a shoe in to win.  I mean come on… how can a real princess NOT win at that point?  Hmm?  What’s that?  Oh, I told you, if I can’t make Ron pass as a real princess I’d give him a blow job.  Oh, what if I win?  Well, I hope it’s obvious now that I WILL win, but if I remember right he’ll pay me twenty dollars.  You’re right, I should add inflation to that as it’s been six years now.  And it’s not like his husband won’t be able to afford it!