Something a little different this time. Typically I gather a few friends from our regular group and I take along some pictures. We'll chat about the girl in them, discuss her, have a good laugh at her expense.
Tiffani (UK sissy, not the recent US one) asked if she could spend a week with me while she visited her flat (on-line, not in person), and could part of her arrangement include her very own Sissy Blog entry. So rather than just take along her pictures, I decided we would discuss her experience, too.
With me on this evening was Miss Amy and her husband, Bradley. Their relationship had been evolving over the last few months. My good friend Miss Amy was becoming more dominant and taking much more of the lead in their relationship, and in their bedroom. She recently confided that Bradley was regularly wearing his own panties now --- rather than occasionally wearing her own --- and that he believed nobody knew. His own.....I wondered how long it would be before we had a special gathering for Miss Amy's husband.
And Tina was with us. She's a school teacher. Ages 4 to about 11. She's cute and sexy in a girl next door way, and has gradually become more adventurous.
None of this group are as naive as they used to be, but Bradley still maintains a shocked 'how can they do that?' attitude, much to our amusement when he gets flustered, because we know the road he seems to be on.
One drink down at one of our local pubs, we began as I described first meeting Tiffani and then her drive to her flat.
"I had her stop at the first services she saw, change into her lingerie and heels, and then enjoy a break at one of the coffee shops or restaurants."
"Sexy little outfit," Tina smiled.
"She liked that one a lot," I told them.
"So that's in a public restroom?" Bradley asked rhetorically. "At a service stop on the motorway?"
I nodded anyway.
"And you made her sit and walk around in her heels?"
"She was scared of public humiliation. Obviously I let her put her top and jeans back on.....But, yes. This was a good little test for her."
"They're well obvious," Bradley exclaimed. "Loads of people would have seen."
Miss Amy punched his arm playfully. "No different than when I caught you in mine."
Bradley turned bright red. "You did not!"
"Really, Bradley," Tina giggled. "You're just becoming one of the girls over the last month or so."
"Shut up," Bradley said. He drained his glass and headed to the bar for another drink.
"Don't forget us," Miss Amy called. She picked up the picture. "So this girl did good, then. Going out in the heels. Barely feminized otherwise."
"As she was heading away from home it was a good opportunity to push her a little. She was very brave. I made her stop at every services she saw on her journey. Just to get out and wander around the stores. And she did."
"That takes courage," I continued. "Putting yourself out there like that. Knowing there's a good chance you will get mocked."
That is something we've spoken about before, and even though we all have a good laugh at you, teasing and tormenting, we have very big respect for most of you, expressing yourselves the way you do. As I do, for the clients I work with.
"So what happened when she got to the flat?" Tina asked, as Bradley returned with our round of drinks.
"Yeah, she's pretty and all, but I want to get to the good stuff," Miss Amy echoed.
"I had her strip down to her lingerie and she spent the evening like that, hoping nobody knocked on the door-"
"Cute," Bradley said.
"-playing sissy dog," I finished.
Bradley spluttered his drink.
"On all fours, barking her answers. It was so fucking funny," I told them.
"What does she have on her chest?" Bradley asked.
"They're her inserts," Tina told him.
"She wants to have big tits," Miss Amy laughed, and then asked: "Did she have a collar and leash?"
"No. We had a few shopping trips planned. And it was on my list for her to buy. There was also an adult store nearby. But we had to change plans slightly. You'll see why later."
"What happened?" Tina asked.
"Later," I promised. "I haven't finished about my sissy dog yet. She was such a good doggy. The flat had a balcony so I made her sit outside a while in the cold for anybody passing to see-"
"-and then I sent her to bed."
"What's with the padlock?" Bradley asked.
Miss Amy smiled. "That's her cage."
"Her what now?"
"Her chastity device," Tina grinned.
"Her little clittie trap. To stop her playing with it," Miss Amy laughed.
Bradley put his drink down. "You mean to tell me.....She was going through all this and she couldn't even get herself off?"
I grinned. "Some girls like that."
"I have no idea why," he said, shaking his head.
"They're not my favourite, but the chastity device also had spikes," I told him.
"What?"
"So that if she does get excited-"
"No," he held up his hand. "Shut up."
The keys for the cage were locked away and guarded by a timer. Tiffani was well and truly stuck in it. But there was to be an ironic twist later.....
"What happened the next day?" Tina asked.
"Hold on," I said. "Still not finished with my sissy dog."
They looked expectantly.
"Well, a sissy dog can't pee inside," I told them. "When she wanted to go in the middle of the night I had her go out onto the balcony."
"It must have been freezing," Tina said.
Bradley stood to get our next drinks. "What's with the jug?"
"She's going to drink it," I told him.
He sat, empty glasses in hand.
"Brad?" Miss Amy managed, stifling her giggle.
After a long pause, he managed: "I'm not thirsty any more. Is this for real?"
"I let her add a little lemon. Pee in the bottle. Add a splash of lemon and then pour into the sports bottle. And, yes, she drank every drop."
I elaborated a little more about Tiffani. She didn't just want to play dress up or sissy dog. She wanted me to take control of her life for that week. Make all kinds of decisions for her. From bedtimes and curfews to what she would eat and drink.
"But why in all the world would you make her drink her own pee?" Bradley exclaimed, and the others hushed him when the people on a nearby table looked over.
"It's what she wanted and well within her limits," I explained. "I enjoy my work, and while I've never made anyone drink their own pee before, I'm a facilitator and like exploring new areas. If you desire something and I'm interested, I'll try to make it happen for you. So long as nobody is hurt along the way and you don't talk outside my own limits."
"So she wanted to do that?" Bradley asked, dumb-founded.
"Absolutely," I nodded.
He stood. "I need that drink."
"And eat pet food," I said.
He sat down again. "Fuck me and all that's holy."
"Gently with a chainsaw," Tina giggled, nudging him.
"It's not funny," he said, looking at me. "For real?"
"For real," I confirmed. "The next I had her stock up for the week with groceries. Including Pedigree dog food and Felix cat food. Different canned flavours."
Bradley shook his head and went to the bar.
"I was also going to have her shop for lingerie because she was still in the same panties as her drive and-"
"Ewwwwww" Tina gasped, not particularly blinking at pet food, but repulsed by dirty underwear. "She hadn't changed?"
"She wanted to be a dirty slut. To really feel it. She was in that set 24/7 for a couple of days."
"Did she still go to the adult store?" Miss Amy asked.
"Well, she wasn't going fully dressed as a woman, so I had to feminize her a little first. She had to shave......"
"......and then she had to paint her nails."
"Pretty," Tina said.
"What did she get at the adult store?" Miss Amy asked.
"Well, I had her have a good chat with the staff, making sure they saw her nails, and she came out with these......"
"Bet she was excited," Miss Amy said.
"A little too excited. She couldn't wait to get her hands on the cock and ripped into the box before she had permission. So then we found a use for her new 'Bitch' paddle before I had intended."
"How?" Tina asked.
"Self-discipline. I had her do it herself, harder and harder. She squealed like a girl. Surprised you didn't hear her. Several sets until she was nice and red. Hurt her to sit."
Bradley was finally back.
"Ouch," he said, sitting down.
"I was out that night, and when I had returned something had happened."
They all sat forward.
"I'm compassionate. I switch on a dime between being strict and holding somebody's hand if they need it. Tiffani was struggling a little. Having fun, but finding it hard to reconcile that with the feelings she has for her wife."
Tina raised her hand to her mouth again, this time with concern. "I never thought about that. The emotional struggle some people must have."
"Well, that's just it, Tina. Sissies and cross-dressers are people, too. Not just objects for derision. Regardless of how much fun that is for some. Or cruel and malicious for others. Some love who they are, but for others there's a pain. A conflict. Some will be open about who they are with their loved ones, But others hide, live in secret. Which puts pressure on themselves about who they are."
The night had taken a serious turn.
"What happened?" Miss Amy asked.
"Tiffani pulled out of the week. We were still in touch and chatted. We still had a little fun. But the time away, what she was doing, was too immense for her to handle. And again, with good reason."
"Has that happened before?" Tina asked.
"Occasionally. I always encourage my girls to open up and talk if they need to. For most this is a fun game their wife won't play, so some suffer from guilt. Inner conflict can be tough. Tiffani opened up a little and I'm happy she did, and felt she could, so I could watch out for her as much as possible from my end. But to finish it wasn't an easy decision for her."
"Is she okay?" Bradley asked.
"She's good," I assured him. "And Tiffani still had some fun left in her."
"Tell us," Tina said.
I laughed and reminded them about the timer guarding the keys to her cage. She couldn't go immediately home because her tiny clit was locked away and she couldn't free it. She decided to stay at a friend's house, still near her flat, for a couple of days.
"So she had ordered a maid's outfit for her time away. I had already told her that when she picked it up, she would have to try it on in-store."
"No, you didn't," Tina grinned.
"I wanted her ready to work."
I received this.....
"Oh my God!" Bradley exclaimed. "What did the staff say?"
I couldn't help but think that maybe one day he would find out for himself, and exchanged a look with Miss Amy.
"The staff were cool about it," I assured him. "Tiffani was mortified by the idea, so it was a big step. She did great and enjoyed it once she was in there. The staff didn't bat an eyelid."
"It takes all kinds to keep the world spinning," Tina elaborated.
"Exactly," I agreed. "And a lot of people in the stores are starting to see that. Still a long way to go, but things are moving in the right direction."
"What else did you do to her?" Bradley asked.
"Not much. I'd been tweeting her adventures, but she was ready to go home. She waited out that timer so she could get out of chastity, and then got back to her wife."
Bradley drained his glass.
"She paid me some real nice compliments about my work. I was really pleased that she's stayed in touch, even just when interacting on twitter. Means I know she's okay despite her little personal stumble."
"You have emotional investment in your work," Tina said, perhaps only realising for the first time how compassionate I can be with my girls.
"Well, respect is a two way street. A lot of Mistresses would do good to remember that," I said.
It was late. Conversation turned to other topics and soon after we headed for home. That night Tiffy had responded to something I had tweeted and I knew everything was alright in her world.
So there it is......Another sissy.......Another night of humiliation and chat.....If you want to take a turn, DM on me on twitter or shoot me an email.
Stay happy. And be kind to yourselves.
Mistress Brianna xx