It's been a while since one of these, so an introduction.
While I keep a lot of my work, and my sissy husband's life, private, throughout this year I have opened up to a very close group of friends and invited them into my world a little.....One or two didn't take to it, and one even fell out of touch with me, which is her loss. I'm not ashamed of who I am or how I live. My secrecy is merely to protect my son's innocence for as long as possible.
Anyway, as well as letting them have a, sometimes discreet--- but not always --- giggle and laugh at my sissy husband, I also pushed a little and let them take part in some of your games by creating Sissy Humiliation Evenings. Nights out for us women, and sometimes my sissy husband and a husband named Bradley (both their only to further our amusement) in which I share a sissy client, her adventures and pictures.
The original idea was that these women were every-day, vanilla folk, but gradually, particularly Miss Amy, they have become more open, enamoured even, by what they have seen. Maybe one day I'll need to recruit fresh blood from my circle of friends, but for now.....
Sissy Tina.....
.....was to face myself, Miss Amy, her husband Bradley, and Lisa....Tina (my school teacher friend) had called at the last minute to cancel. I laughed my ass off when she said she was really sorry, but she'd rather be out with a real man than one of my sissy girls. Turns out she's been getting serious with her new boy-friend and she had a valid point. She assured me she'd had a great time at our other get-togethers and that this was just a blip. I don't doubt her.
For this evening, I picked a little bistro/restaurant. One of those places that can't quite decide what it wants to be. A coffee shop in the day-time, serving a little more food than most. A trendy little gathering spot at night, focusing more on meals and alcohol. It was a quaint little place, not too far from the water-front. So we had a little walk catching up, before we sat to eat.
So, Miss Amy and Bradley....She had become seduced by my world, and while I wasn't mentoring her, as such, she often came to me for advice. I'd seen Bradley, perhaps willingly, take the first steps into feminisation, and fall deeper under the spell of his wife as he accepted more and more who was wearing the pants and who was wearing the panties in their relationship. It was all a secret as far as he knew....But, of course, our little group all knew he was now wearing his own bra and panties, tights/stockings most days. He was still in that bitchy little crying phase, where most days come with a protest, but the pathetic whining was getting less, Miss Amy assured me. He was becoming quite the good girl from what I heard. Only a matter of time before I suggested a pro-noun switch.
And Lisa....A swim instructor who was dedicated to her job. All heart. She was single, but confessed she was enjoying more flings than she used to, and that her behaviour was becoming more flirty and open. I'd noticed a change in the way she dressed when I saw her. Playing with her image a little, exploring looks....
"Is this our latest girl?" she asked, spinning the picture toward her. She had done a few of these now, and seemed very comfortable.
I nodded as the waitress dropped off our starters. I loved this bit....I caught her do a little double-take at the sight of the sissy in the tutu. This time she didn't say anything. I wondered if she would. I watched her return to the kitchen and saw her nudge one of her colleagues. They both looked at our table. I smiled to myself.
Word was already spreading about Tina, who you can follow on twitter @AperolTina.
"Yes," I told her.
"Why's she got on a tutu?" Bradley asked. I loved him to bits. He was still forthright. All bluster as if he was the man amongst us. Over-compensating to hide what he didn't know we already knew. He had gone from being genuinely flustered at these gatherings, to desperately hiding his own girly nature.
"Well, cross-dressers and sissies begin dressing for a variety of reasons. For Tina it began when she watched the girls in her school getting to wear cute little ballet shoes. She dreamed she could have a pretty pair of her own one day, and her very own tutu so she could become a ballerina."
"Beautiful," Miss Amy grinned. "She'll be ready for auditions soon. Maybe that dream will come true."
"Or maybe you could enrol her in classes," Lisa suggested.
I nodded. That was one of the beautiful things about these little gatherings, especially when the subject is an active client like Tina who has many games ahead of her. They read all this, get excited by it, and wonder.....will Mistress really do that to me? What have I got myself into? How far will she go?
I guess you'll find out soon, Tina....Lol....
Bradley laughed. "It would have to be an adult school."
He, too, seemed very comfortable on these evenings now. Not the flustered Bradley that used to join us. Of course we knew why. I watched Miss Amy rest her hand on his shoulder, massaging his bra strap, starting to fiddle-
"Stop!" he quietly exclaimed, and Lisa and I looked at him as he brushed her arm off. Miss Amy laughed.
"So ladies," I smiled, making no exception for lingerie wearing Bradley. "What would you do with that?"
"Cage her," Miss Amy said instantly. "That little thing deserves to be locked away."
"Yes," Lisa nodded. "Cage her and lock away the key. That way she has to do what she's told."
I smiled. "She's quite well behaved already. What about you, Bradley? Would you like a sissy blow-job from Tina."
At this Miss Amy couldn't contain her laughter. Bradley glared at her, not knowing how much we knew.....from his dress code to his, well, short-comings.
"I doubt she could handle me," he boasted.
"Whoa!" Lisa grinned. "Look who has a high opinion of himself."
Behind him, Miss Amy was holding her thumb and finger in a tiny gesture. I was amazed at these women, once so timid about what I did, now embracing it and talking dirtier than myself sometimes. Especially Miss Amy.....who was dying to say something, but waited as the waitress cleared our plates, taking a moment to look and smile, and then delivered our next course of food with a fresh round of drinks.
"She needs to take her fist out of her mouth and have it stuffed with cock," Miss Amy finally said, the notion bursting out.
"Like this, you mean?"
I dropped my next picture on the table.
"You think she could swallow that?" Miss Amy asked, and then noticed Bradley staring. "Big, isn't it?"
He nodded, almost dreamily, and we laughed.
"I bet she's experienced," Lisa said. "I reckon she swallowed that fucking thing whole. Am I right?"
I grinned and revealed a piece of paper from my handbag. "Her words.....I sucked my first Cock when i was 17. I walked the parks in ********** and one night a stranger asked my for a cigarette, I gave him one and he said thank you and by the way nice stockings you are wearing pretty girl. I thought I must die and began to stammer but he said 'Hush, little Girl. I love what I see.' He took my hand and hold it. I got normal and he asked me if I want to be a girl and I said 'yes Mister'. He asked me if I want to be a real girl and stared in my eyes and I said yes. He took me by my hands and said so get on your knees little Girl and I did staring at his dick covered from his trousers. He opened the zip and a big cock, much bigger than my little clity, popped out to my face. He had not to say anything. It was natural for me to lick and suck his nice cock, the first time I felt really girly. Minutes later he said I will cum. 'Look in my face Girl,' I did and he took his dick out of my mouth and cum on my face. A lot of cum covered my face my lips, my eyes. It burned like hell....And I loved it. He fed me his cum and I swallowed all. He said good bye slut and walked away."
They sat for a moment in silence and then Miss Amy and Lisa burst into laughter.
"So romantic," Miss Amy said.
"It's her Hallmark card moment," Lisa laughed.
Bradley raised his hand, almost asking permission to speak in the hysterics. I nodded, pleased with this approach from him. It might just be subconciously, but he was learning his place..
"Did she see him again? It was his first so that would be nice, I think."
Miss Amy punched his arm, not believing what he was asking.
"No, Bradley," I said. "It turned out she'd wandered --- supposedly unwittingly --- into a gay pick-up area. She sucked loads of cock since, but never found that first one again."
"Poor baby," Lisa grinned, tears in her eyes.
"She still goes back now. Hoping she'll see the one," Miss Amy smiled, and they both broke up again.
I continued to read from her messages: "That was the first time I sucked dick and swallowed cum Mistress. Since this day I was a cock addicted and cum loving whore Mistress. The most recent dick was a stranger I met on internet. We managed a meeting – he came with his car and I go in fully dressed. I started sucking his dick, suddenly he took my head and face fucked me really hard – he came within seconds. All the cum went right away to my stomach it was really awesome."
"This is so funny," Lisa grinned. "Between us, I always found it gross....I doubt I'll ever do it again. Yet this sissy can't get enough."
"And more and more people are finding out about her," I noted, "and what she loves so much. And I don't just mean this blog. Or who sees her out here tonight."
"What else are you up to?" Miss Amy asked.
I took a sip of wine. "She's my work-place sissy toy."
"What does that mean?" Bradley asked.
"She only plays with her in work," Lisa chimed in.
"Kind of," I said. "But it's a little more fun than that. She receives a lot of her instructions through her work email address. It's a proper one, too. She works at a museum, so it's clear to see it is her official email."
"But," Bradley stammered. "Her messages might be monitored. It could get her in real trouble."
"Bradley," I soothed, "don't you think that's what she ultimately wants? She's playing sissy exposure games, humiliating stuff, in her place of work with her colleagues. Men and women."
"But-"
"Oh, Bradley," Miss Amy grinned. "Are you being all protective?"
Lisa laughed.
"That's not all, Sir Bradley, Knight and Protector of Sissies," I chuckled. "I also have her talking about who she is, what she enjoys.....often with relevant subject headings. And she has to keep the messages in her in-box for anybody to see and get curious about. Sometimes her tasks are in the subject line."
"So what do you have her do?" Sir Bradley, Knight and Protector of Sissies asked, as the waitress approached.
"Deserts, anybody?" she smiled uncertainly, taking in the pictures.
I looked around.
"No takers," I said. "We'll settle up when you get a second. Sorry about this."
"No problem so long as you're discreet. It's kind of funny, I guess," she said, looking again. "He's cute and funny in that tutu."
After she left I told them some of the things I'd had Tina doing.
A little lingerie wearing.
Some feminine etiquette. Sitting like a woman, using the toilet like one. Standing and walking like a woman.
Wearing clear nail polish.....Soon to be colored.
"The basics. Sissy girl has to run to the rest-room often to send evidence of what she's doing. Soon, I won't let her hide so much. I've got a great poll running so in the immediate future she'll be padding her bra, using a handbag-"
"Padding her bra?" Lisa laughed.
I nodded. "My girl's going to have big tits for a week or so. Maybe for good. She's had a period-"
"Gross," Lisa said.
"From the look of this picture, she doesn't need to pad her bra!" Lisa cried out. "What's that about?"
"You know how sometimes you get sensitive nipples when you're on?" I couldn't help but laugh. "Well she got sensitive nipples that day. And a sensitive clit."
"Ouch," Bradley whispered.
"Is she a good girl?" Lisa asked.
"Pretty much. I think I've only had to really punish her once."
Miss Amy leaned forward, getting interested. "What did you do?"
I shared another picture.
Lisa exclaimed: "Ewwww! At least warn us next time."
"I gave her permission to cum....But only by masturbating with a heat gel as a lubricant."
Bradley laughed boisterously. "Well she fooled you then. I bet that's easy and she got to have an orgasm."
I silenced him with a single look.
"I'm sorry," he said.
Miss Amy shook her head. "Maybe you'll find out how easy that is later."
Bradley turned sheepish.
"Poor Bradley....Going to get his burn on," Lisa smiled. "Poor Tina, too. It must be so hard for a sissy girl like her. Longing to please, but also she must be afraid of being spotted for real, even though it's what she thinks she wants. Do you think she'll do good?"
"I expect her to.....If not, because of our arrangement, she'll be exposed to the people she works with whether she likes it or not."
"That's a bit hard-ball," Bradley noted.
"Sounds fun, though. Makes it more interesting. A little blackmail mixed with her devotion to stop her from being naughty. I like it," Miss Amy told me.
"She sent a little present for you all," I told them and removed the final picture, as the waitress left the bill, genuinely smiling at what she saw.
Everybody in my group started laughing.
"Oh my God! She's such a keeper," Miss Amy assured me.
"Happy Christmas, Tina!" Lisa exclaimed.
And then, as we stood, as had become our tradition on these public occasions, we left the pictures behind after I settled the bill. I don't know what will happen with them....I know on one night they were displayed in a staff room; other times likely thrown away.
I left a tip for our waitress and smiled. She returned the look...I doubted they would be thrown away tonight. Happy Christmas, Tina, indeed. And to you all.....
Mistress Brianna xx