from Kate

Dear Helga,

I apologise for leaving it so long to write this letter. Its been a work in progress for a while now. I've tried hard to cover as many things as possible, and hopefully meet on a few promises I've made. To myself, to you, and for the benefit of the site. First of all, you'll be pleased to hear that my training of Tiffany is going very well. There are, as with any relationship, setbacks every now and then, and she will try and fight me on certain things, but at this stage, the fight inside her is very little. She is now completely financially dependent on me which is very sexy, and she becomes very upset at certain moments when she catches herself being left with no choice but to act in a feminine manner without my say-so, which gives me genuine chills down my spine to witness this change in behaviour. Compared to the person she used to be, I would say she is almost completely broken and submissive. And I will relish the challenges that this will bring, in trying to come up with fresh ways to keep it that way, and I hope I can do that with your help.

I'd just like to talk a little about how Tiffany's birthday went. I had packed Tiffany's presents and sissy clothes into a hold-all. I'd locked the bag, so Tiffany couldn't see what I'd packed for her big day. I got her to carry it and put it in the car, and we were off to Becca's. Tiffany was extremely quiet on the journey over, but that was fine. I didn't engage in conversation with her, I put the radio on, because I didn't want to alleviate any nerves she might have had.

When we got there, Becca came out to greet us. She wished Tiffany a happy birthday. Tiffany looked at me, and I raised my eyebrows. Tiffany very quickly performed a curtsey. I told her that was pathetic, and promised Rebecca that she was far more adept when she was in dresses. With that, I ordered her to get the bag from the boot, and we went inside. Indoors, Polly, Rebecca's sissy maid, was standing there in a lovely frilly maids outfit, thick make-up and wig, holding her hands at her front. I looked at Tiffany for her reaction, since she hadn't known there would be another sissy here. She was trying to stay composed, but she was going quite red, which always happens when she's nervous.

Polly waited politely for Rebecca to introduce her before she curtseyed to Tiffany and I. Rebecca said, "Polly, this is Tiffany. It's her birthday today. Wish her a happy birthday." Polly then leaned in towards Tiffany. Tiffany quickly took a step back, but I pushed her back in. Polly looked at Rebecca who urged her. Polly leaned in again, and pecked Tiffany lightly on both cheeks, making us both chuckle. Rebecca said, "Now Polly, Tiffany will be helping you out in the kitchen, and then after lunch, we're going to play some party games, where we're going to find out which one of you makes the best sissy. I for one can't wait to get started so chop-chop." and with that she dragged me in the lounge, where we chatted while the two maids got to it. Rebecca had drawn the lounge curtains to keep prying eyes at bay, and we could still see our sissies down the hall through the door. One time, Polly tried to shut the kitchen door, but Rebecca stopped her short.

I let Tiffany stay in her male clothes over the lunch (she was wearing panties underneath) since there was plenty of time for fun afterwards. Polly had prepared a roast dinner for two, and made sandwiches for herself and Tiffany. A little cruel, yes, but we felt it set the tone for the day. When we were done, we told them to leave the dishes, we'd get to them later. Now it was time to get down to business. We took both sissies upstairs in separate rooms and stripped them of their clothes. The beds had been stripped, and the sheets were in piles on the bed, which would play a part later on. I think Polly and Tiffany were both expecting to be put into something girly, but I just opened the hold-all and handed her some high heels. Tiffany, stood there, in just a chastity device, asked me what else I'd packed for her. I told her that was for later. Right now, she'd just be wearing these shoes, same as Polly.

Tiffany began to beg. She got down on her knees and pleaded not to go through with whatever we had planned. Her voice began to crack, but I wouldn't be bargained with, and I shouted at her, telling her while she was a guest in my friend's house, she would not let me down and behave so childishly. I found it very satisfying having her stand before me in nothing but high heels. I believe the herbs that I still have her take nightly have made her gain weight, but on the plus side, that weight is going to her chest as well, so I'm hoping that this will continue, and once she's lost all the weight around her middle, she'll have a nice set of breasts for me to make fun of. I remember getting quite frustrated at the process. I consider myself a patient person, but when the progress is so slow, I must admit, I have looked a couple of times into surgery, despite saying many times before that it wouldn't be the sensible road to go down. But to my mind, after financial dependence, the next big step to ensure that she will always be my slave would be forced boobs. She still has no idea what I've been planning, she just assumes that the smoothies and the special diet are to make her lose weight. She has no idea its the reason she's putting it on. I have started adding fennel to as many meals as possible too, after reading about it's success on a blog by a transsexual performer. So hopefully these two ingredients together will speed the process along in no time.

Once we were ready, both sissies took turns going steadily downstairs in nothing but heels and chastity belts. I could see Polly practically bursting out of her device which looked very uncomfortable, and Rebecca teased her about it, stroking it to make it worse. Rebecca had told me in the past that Polly had asked to be treated this way, she just didn't realise Rebecca would get SUCH a kick out of ordering round a submissive. I could also see from the awkward way she was walking that her device had been fitted with a butt plug too. We went back into the lounge where Rebecca had produced an A3 sheet with the heading "The Sissy Games" in glitter, and then divided the sheet up neatly into boxes and categories (Rebecca had told me afterwards that she'd had Polly do the graph over and over until she was satisfied) with two columns running down the centre. One for sissy Polly, and the other for sissy Tiffany. I could see Tiffany looking at the different boxes, trying to glean what the day held for them. They read, in order, "exam", "cleaning contest", "make-up contest", "charades" and "karaoke". Tiffany looked crestfallen. It was fantastic. Rebecca laid out the rules for them. Today they would both be taking part in a sissy contest for our affections. We would be the judges for each challenge, and whichever sissy is crowned queen of the sissies, will be the winner. The winners prize will be allowed to wear male clothes for the rest of the day. The loser, however, will have to be punished.

Understanding the rules, they went to the dining table where we had placed a table mat with pieces of paper stapled together laid face-down, at either end of the table, along with a hard chair and a sisal doormat on top. One of these was mine from home, that I'd had wrapped up in the hold-all. I wanted Tiffany to feel right at home. We explained that the papers were exams, and that they had an hour to complete it. We told them that there was to be no conferring, so we gagged each of them, and told them to take their seats, which they did, very carefully. We'd given them each some coloured pencils, scissors, glue, a copy of a women's magazine each, and a pink and blue pen. They didn't know it, but if they chose the blue pen they'd have a point deducted before they'd even started. We put the clock so it was on the hour, and told them they could start. It was brilliant. They both turned their sheets over in such a hurry, as though they were sitting a real exam (which they were I suppose). It was such a proud moment to see such a submissive act.

We sat in the next room, drinking wine and laughing while our two girls were hard at work. Then the time came for them to put down their pens and for them to swap their papers and grade them. We reminded them to be absolutely fair, but that the loser will be punished by the end of the day, and this exam will definitely determine how the rest of the day is going to go, and that the loser will be severely punished. It would be fun to check afterwards to see if they had been unfair to each other when they were marking, but when we went through them ourselves we found they had both been very honest. They both passed the first test by signing their papers with their real names, "Tiffany" and "Polly", and they both wrote their answers in pink pen, not blue (our girls are certainly learning). Polly wrote her name with a star instead of an "O" which we decided deserved an extra half a mark for cuteness. They marked the multiple choice and then had to stand before us and read the others essay answers out which we graded. Polly had written the most, she was clearly more okay with this than Tiffany, since she'd only wrote about a paragraph, and even then had crossed out a lot of sentences along the way. The final challenge was a drawing contest on the last two pages. We used passport pictures of the two girls and then the outline of a body. They were then to design and colour-in their ideal nightwear and daywear for us, and cut out their ideal haircut from the magazine and stick it on their heads.

Unfortunately, I can't take credit for this, it was Rebeccas inspired idea. She just said this is something that we can hold over them for years. A hard copy of something that we can use as evidence of their sissyhood, that we could throw back in their faces and say that this is proof of the sissy they are. It was so much fun. I know I promised photos. Don't worry, many photos were taken, so I will get my chance to prove that I'm no faker, but I never got my own digital camera. We used Rebeccas phone for the day. I took the copy of Tiffanys exam home with me (at the moment the questions are stuck to the fridge, with Tiffany's drawing next to it. At the bottom of the doodle I've written, "Tiffany, Aged 29" just to embarrass her) but Rebecca has photos of both exams.

Back to the exam. Tiffany had designed a very plain pink bra and panties for nightwear with fluffy cloud-like frills, and for daywear, a long, what I can only describe as a prom dress with a blonde Afro which was very funny. Polly had gone for a lovely powder blue babydoll which didn't even cover her belly, and for daywear she'd gone for a classy black hobble skirt with a pearl necklace and a beehive. Needless to say, Polly won, but we didn't give her much more credit, just because she was a better artist and had more taste since we decided that this was more the sort of outfit that a mistress would wear, not a sissy maid, but I told Tiffany we might just try and make her dream of a prom dress and Afro into a reality one day.

The scores were as follows. Out of a total of a possible 30 marks, Tiffany scored a disappointing 14, whilst Polly took the lead with an admirable 20 (and one half), and we marked them down on the chart. I told Tiffany that if she wanted to have a nice birthday, and not be punished, she had better start taking this more seriously. Next up was a cleaning contest. We flipped a coin, and Tiffany won the toss. We told her that since she won the toss she could decide which thing to clean. She could choose either the dishes from lunch, or making the two beds upstairs. Tiffany decided to take the dishes. I told her this would also mean drying the dishes and putting them in their correct places. Tiffany realised her mistake. This wasn't her house, she'd have no idea where everything went, but we told her it was too late, she'd just have to do her best. I took a little maids apron and tied it round Tiffany's waist, and handed her a pair of marigolds. She looked precious. We told them the first to finish would win five points and the loser would have five deducted from their total. They were both to finish their jobs, and then we would inspect their work and for every indiscretion they would have another point deducted. I watched Tiffany, whilst Rebecca lead Polly upstairs. I shouted up the stairs, "On your marks, get set, GO!" and our two girls began their work. Tiffany had to fill the tub up first which set her back. She asked if she could remove the gloves because she said they were slowing her down but I told her no.

Not surprisingly, Polly ended up winning, but I was surprised by how quickly she seemed to manage it. Becca must really have had her practice her bed making. When Rebecca called down to let us know the news, Tiffany was drying the pots. She tried to put them in their right homes, but she kept looking at me. I asked her if she forfeited the challenge, and she nodded meekly. This brought her down to 9, whilst Polly was racing ahead with 25 and a half. But everything changed when it came to inspections. I didn't have to look hard to find faults since Tiffany had given up, and we decided to bring her total down to 5. Polly was equally disgraced. In her rush to finish first, her work was quite shoddy, and we brought her total down to 16. We updated the chart, and went onto the next task. "Make-up".

We decided that they have probably had quite a lot of practice at this stage doing their own make-up, not perfect by any stretch but efficient. But by having another sissy in the room, we could make them practice putting make-up on each other. We tossed a coin, which Tiffany won again, and she decided to go first, probably overcompensating to make up for the last two disappointing rounds. We reminded her that despite Polly having had more points taken off her, she was still well in front. We told her that this would be her chance to make those points back. We would be grading their work out of ten this time. No points deducted. They had ten minutes each to make the other sissy look as much of a sissy as possible. Tiffany got started. She had a selection of garish make-up to go at from Polly's own collection, and began very delicately. Tiffany clearly felt uncomfortable doing this to another man, and I took every opportunity to make fun and tell her that it would be easier to apply if she sat on Polly's lap. Every now and then one of us would chime in with how much time she had left to go. She didn't do too badly, I might say, and we gave her a respectable 7 for her efforts. In the last few seconds she added big rosey cheeks for Polly which we agreed made her look more like a sissy. Then it was Tiffany's turn to sit in the hotseat and get a make-over. Polly was quite capable applying make-up, and she went for a much tidier, more classy look than Tiffany had gone for. Despite her doing quite a good job, we felt that we could be a little cheeky, and we gave Polly a 4. Polly complained, but secretly our rationale was that we still wanted to appear as if we weren't going in Polly's favour just for the sake of it. If Tiffany just gave up and accepted her punishment, then there'd be no contest and that wouldn't be any fun.

The scores were now Tiffany-12, Polly-21. Next up:charades. Each sissy would perform 3 charades. I would tell Tiffany what to act out for Rebecca, and she would tell Polly what to act out for me. If both me and Rebecca guessed it in under three minutes, then they would win five points. So a total of 15 points was up for grabs. Both Becca and I had opted for very typically embarrassing choices, and to save some time, I'll just tell you what they were. I'm sure they speak for themselves. I got Tiffany to perform "Bosom Buddies", "The vagina monologues" and of course, "Breakfast at Tiffanys". Rebecca got Polly to act out "Desperate Housewives", "Some Like It Hot" and "9-5" (which was the only one I got right). Tiffany got all fifteen points, which was lucky since she had the more embarrassing clues. I was very pleased with my choices. As you can imagine, my sissy standing there naked, acting out bosom buddies, and being forced to point at her penis for "vagina monologues", and herself for "Breakfast at Tiffany's" was a pleasure. She was left with no choice but to admit who she now was. This bumped Tiffany up to first place with 27, as opposed to Polly's 26. It was neck and neck going into the final round, which was perfect for our plan.

We decided that this would be a good time for a little break before Karaoke (for Rebecca and I, that is) and time for Tiffany to open her birthday presents. Rebecca ordered Polly to go make some tea and bring Tiffany's birthday cake. We teased Tiffany whilst Polly prepared the tea, asking her if she was having a nice birthday, and telling her that she was so close to winning the contest, and how well she'd done, pulling it back into first position. She thanked us politely, and answered all our questions satisfactorily, probably scared that it might be a trap and any false moves at this stage might result in her losing the contest. We teased her by making her stand before us while Becca and I ran our hands up her bare thighs, making her uncomfortable in her chastity. We gave Tiffany her gifts which included a brand new sissy dress, a pink collar and leash, a riding crop that I had made her choose especially from a range of punishment instruments, and some hair products from Rebecca.

Polly returned with a tray of goodies whilst Tiffany was unwrapping her things. She set the tea down, and she poured each of us a cup (we allowed the girls to kneel on the floor while they drank, we said the tea would be good for their vocal chords) then we lit the candles and all sang happy birthday to Tiffany. The cake was just an ordinary chocolate cake, with 'Happy Birthday Tiffany' iced in big letters. I could tell from her face that she was mortified. Becca and I took a slice each, but told the girls that they could have theirs later, after the contest. We began giggling uncontrollably, which clearly unnerved the two sissies. I got a few other items from home out of the hold-all that I'd brought to complete the outfit, and we got Polly to help Tiffany into her new things, which they did without a fuss. I think Tiffany was quite happy to be in clothes after spending the day naked. It was nice to see her getting into her frills so readily for once.

Finally we told them the final round had come to compete for our affections and win the sissy contest. Karaoke. Each sissy would sing a song of our choosing, and we would grade them out of ten. We would be giving points based on enthusiasm, dancing, tone and accuracy. Becca had borrowed the karaoke machine from a friend, and after some technical difficulties, we got it working. It was quite loud to start off with, and we were a little concerned about neighbours hearing us, but we got it about right in the end. We flipped a coin, and this time Polly won the toss. She asked that Tiffany sing her song first. Tiffany rustled up to the mic and we told her her song would be "Independent Women" by Destiny's Child. Tiffany was monotone, she swished her skirts to try and curry favour, and we told her to wave her arms about and dance for us. All in all, it was very funny, and she had pretty much sealed her fate with her dreadful performance. We gave her a 4. She knelt on the floor, and caught her literally biting her nails a couple of times as Polly took to the stage, and sang her song (an obvious choice, and I'm sure it's a cliche in petticoat punishment circles, but it's a must) "Man, I Feel Like A Woman" by Shania Twain. Polly had put on a high pitched voice, which sounded ridiculous, and she walked up and down in her high heels in a provocative manner. She was clearly quite enjoying herself, and who were we to tell her otherwise. We encouraged her, as poor Tiffany just sat on the floor, horrified.

We put them out of their misery, after a long pause and a bit of preamble, we revealed that Polly had been given 6 points. Just what she needed to win it by a nose. Polly was very reserved, but was clearly hiding a smile. We made a big show about how disappointed we were with Tiffany, but congratulated Polly on her win, and for being the biggest sissy. Rebecca took her upstairs for her prize, while I prepared Tiffany for her punishment. I locked Tiffany in her new collar and leash, and tied her hands behind her back. I told her how disappointed I was in her and that she had better make it up to me. I said this punishment was for her own good, she clearly wasn't nearly as much of a sissy as I'd hoped and so we'd have to see what we could do about that, starting now.

I dragged her upstairs, placed a headband over her eyes to blindfold her and knocked on the door. Rebecca told us it was okay to come in and I swung the door open, wrapping my hand around the leash just in case there were any problems. I led a worried Tiffany through the door (I could hear her breathing heavily) and I saw Rebecca smiling, holding her camera phone, a finger over her lips and she locked the door behind us. I told Tiffany she could take the blindfold off now. She did, and Rebecca took a photo of her reaction as she took in the scene. It was priceless. Tiffany went bright red and began to tear up. What she saw was Polly, now removed of her high heels and chastity, and now wearing a pair of Y-fronts. She had now become the man that we'd promised her she'd be if she won, except that she was tied to a chair, blindfolded and sporting a massive erection through her briefs.

Tiffany looked pleadingly at me, and began to blubber, finally beginning to understand the situation. She shook her head as tears streamed down her face, streaking her make-up, and struggled to form a coherent sentence. Rebecca just beamed, snapping photo after photo. Tiffany pleaded and asked her not to take any more pictures, she was trying to remain as polite as possible, but when I nodded in response to her shaking her head, and Becca kept taking pictures, she lost her temper, and began to shout, begging not to make her do this, and why were we doing it.

She even tried to grab half-heartedly for the door handle a couple of times, but I blocked these attempts. I stood my ground and slapped her across the face. She was becoming quite hysterical. I told her that it was for her own good, and it was her own fault. Throughout the day, she had performed below par, and not satisfactorily at all, and by doing this it would teach her a lesson of what happens when sissies perform badly. So now she would give sissy Polly her winners present. She would perform oral sex on Polly until she came. Tiffany tried to beg some more, and I just whispered in her ear that she should weigh up her options quickly, and it would only be as bad as she made it.

This subdued her somewhat, and I kissed her on the lips to encourage her. I tugged on her leash and dragged her over to the bound Polly. I ordered her to begin by kissing Polly. This resulted in another round of tears, but I slapped her and told her to stop being so dramatic. She knelt down and pecked Polly on the cheek. We pushed her head in properly and told her to kiss her like it was her last kiss. Tiffany winced and then went for it. Rebecca and I laughed as Tiffany stumbled about with her hands behind her back trying to make out with Polly. Polly received it fairly well we thought, clearly quite aroused by the situation. We ordered her to lick Polly's naked body, which she did, screwing up her face, she ran the tip of her tongue over the parts of the body we asked her to. Then we threaded the leash underneath Polly's legs, and out the back, so that Tiffany was facing what she'd dreaded. Tiffany gagged, and for a second I thought she was going to throw up, but Rebecca had just one more trick up her sleeve to make it more embarrassing for her.

She took a slice of Tiffanys birthday cake, and stuffed it down the front of Polly's Y-fronts, rubbing it around his cock, and crumbling the cake so it left an even bigger bulge. Rebecca whispered in her ear, "Happy Birthday Tiffany. This should make it taste better for you. I know we promised you a piece of cake, well there you go. You're not to stop until you've eaten every last bite, and that includes Polly's gift for you". And with that, I yanked on the leash from behind Polly, holding her and whispering in her ear, and Rebecca pushed Tiffany's head forward further into Polly's lap. Struggling to catch her breath through her tears, Tiffany put her mouth around Polly's cock and slowly began to suck her off. Whether it was a reflex, or whether she was just following our orders, she stopped every now and then to lick around the shaft and eat her cake too.

"Don't forget to blow the candle out, darling" I said. I admit, I'd been sitting on that one for so long, but it felt so good to finally say it. Tiffany was truly mine to do with what I wanted. When Tiffany was up and running on her own, without the need for any force, Rebecca came round to where I was standing, and together we whispered sexy things into Polly's ear, touching her to help her come.

It wasn't long before Polly started to shift and wriggle slightly in her chair, moaning and making low grunts of pleasure. This went on for a while until Polly muttered, "Quicker". Without missing a beat, Rebecca pushed down on Tiffany's head and said, "You heard the winner, she said quicker". With this, Tiffanys head began bouncing up and down, and a couple of times Polly flinched, presumably because Tiffany had caught her with her teeth (after all, she's not used to it... yet) Rebecca began twisting Polly's nipples and this seemed to tip her over the edge completely. Her body shuddered and tensed, and the chair scraped along the floor as she exploded in Tiffany's mouth. Tiffany pulled away the minute she ejaculated, but there was still come dripping around her mouth. She hadn't dodged it. We ordered her to eat up, which she did begrudgingly, gagging every now and then, but she ate it. We then let her stand, and she stretched off, eyes red and puffy, and mouth glistening and full of cake crumbs. Rebecca took a picture.

We complimented her on how well she'd done, and asked her whether she liked her birthday cake, to which she quietly nodded. But we said that Polly was still in a passive position during a blowjob, and we were certain that since she'd won the sissy contest that she'd like to hold onto her masculinity for just a few more hours. I got the hold-all and took my strap-on from out of it, dangling it in front of her. Tiffany didn't cry this time, merely looked at me, broken and just nodded, accepting. We untied Polly and told her to bend Tiffany over the bed she'd made earlier, lift her dress up and perform anal sex on her using the strap on.

I reattached the ballgag in Tiffany's mouth, which made her splutter a couple of times (presumably a result of the blowjob). And then, without our asking to, she bent over the end of the bed. It was Polly's turn to look at us pleadingly this time. She didn't tear up, she just said that she wasn't sure she could do it to another man. We snapped at her that she wasn't a man, and if she didn't want to be the man anymore then we'd put her in dresses and subject her to the same torment. Polly cleaned up a bit first, and then put the strap-on on. She lubed up and lifted Tiffany's skirts, inserting the strap-on gently inside her. Tiffany moaned for the first couple of times as she became accustomed to it, and I could see Polly was being very careful not to cause Tiffany any pain. Rebecca, without missing a beat ordered her to ride her as if she would never have sex again and to spank her ass. I told Tiffany that she needed to moan as if in ecstasy. This spurred Polly on. By hearing Tiffany moaning pleasurably, Polly must have felt more comfortable with what she was doing. She began thrusting the cock back and forth into Tiffany's ass. After a few minutes, the moaning sounded vaguely like screaming, and we told them to stop.

We congratulated each sissy, kissing them and hugging them for such a good job, and then we showered them both off separately, washing the day off. They both seemed completely subdued from their day, and I hugged Becca goodbye, because it would be a while till I next saw her. I thanked her so much for possibly the greatest birthday ever, and got Tiffany to do the same. It was back into male clothes for the journey back and it was another quiet ride, with just the radio to keep us company. When we got home, Tiffany automatically got the hold-all from the boot, and took it upstairs without a word. I was smiling triumphantly at how much of an effect the events had had on her, and as I ordered her back into female clothes for bed, I said to her,

"Don't worry's your 30th next year..."

Kind Regards,


Thank you for your letter Kate. Wow! Where do I begin, what a wonderful letter, I really appreciate the amount of time it must have taken you to write. Your detailed description will add so much to the site's archive. You two are so imaginative, inspired really.

Sissies are so much fun to play with, not at all like the boring husbands they used to be, when other wives read this I'm sure many will wonder if they can have the same submissive partners you two have. This will really inspire them.


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