Transforming Brent

I was escorted to the back of the salon and told to sit in a very comfy padded chair. "We just need to trim your brows a little bit honey. They are a little bushy right now."

She told me to hold my head still and close my eyes. With a small scissor, she trimmed them down a bit. Peeking through my other eye. I saw her approach again with what looked like a Popsicle stick covered with hot wax. She spread it over the top of my brow, pressed a cloth on it and yanked. She then applied more wax under the brow. Soon she grabbed tweezers and pulled a couple of strays, then rubbed a soothing lotion over them I was sure she removed them completely. When I was allowed to look in the mirror I saw 2 cute arches over my eyes.

Wendy came to inspect. "Oh, Brenna, they look wonderful. It really opens up your eyes."

"But what about work?

"That won't be an issue. Eyebrows grow back."

Finally, we headed home, stopping to get take out at a nearby Thai restaurant. I had been humiliated enough for one day I guess. After putting away our purchases, we shared a bottle of wine relaxed a bit.

Finally, Wendy set down her glass. "So, are you ready to give your retirement notice on Monday, Brenna, and commit to being our girl, or do you need more convincing that it is your destiny?"

"Don't you think it is kind of sudden. I mean what will all our friends think if I just change overnight into a female? It just seems odd, that's all."

"It's not as sudden as you may think Brenna. Wendy and I have been working on this for a few months now and it is time you accept your proper place."

Wendy left and returned to the room with a small bag. "Take off your shorts and panties Brenna."

I soon stood there in my tee shirt with the bra still on under it.

"I want to prove how well conditioned you have become. A year ago, would you have worn panties or a bra? Would the feel of a pair of soft panties excite you?"

"No Wendy, you know I never wore them before."

"Let's see how you react to these." Reaching into the bag she removed a pair of pantys. They were soft and pink with little white polka-dots and a black and white lace down the middle and over an opening in the back. She draped them over my penis and it immediately erected fully.

Grabbing my hardened tool rather firmly, she stared deep into my eyes. Increasing the tightness of her grip she claimed me. "I think we have our answer right here in my hand Katherine. Hard as a rock!"

"Yeah, it's pretty obvious how much he loves them. It's time for her next gift I think.."

"Definitely. Let's do it."

I reached back in the bag and took out the chastity cage we purchased at the fetish boutique. I took hold of his sack and applied enough pressure for him to feel. It wasn't enough to shrink him down so I squeezed harder until he started to double over in pain. His, actually now my, cock started to shrink rapidly. I forced the balls through the metal ring and then with a quick lick on the head to lubricate it, tucked it through. I pulled the length through and before he could get hard I slid the metal tube down over the length.

The tube slid into place on the ring and I slid the key into the locking mechanism. After a quick twist of the key, I pulled it out and set it aside.

"Now my dear sissy, this belongs to us, not you. You may earn its freedom someday, but I wouldn't expect you will be wanking for at least a week or so." I gave it a few tugs to show Brenna how secure it was and then told her to step into her new pantys.

Seeing the cage she knew she was defeated. She slipped the panty up her legs and settled them around her hips. The cage did make a bit of a bulge in front, and I heard a whimper as she was obviously trying to get erect in it. The conditioning she had to be excited by wearing pantys would be causing her pain until she earned her release.

"Ow, oh Miss Wendy, it makes my cock hurt. Will you please take it off? I will behave, I promise."

"Get used to it sissy, that's staying in place until you have earned your release. That means being on your best behavior, quitting your job and becoming our sexy maid, and becoming the sissy girl that Katherine and I wish to mold you as. Once we are convinced you are serious about being a good girl for us, we will consider releasing you from it. Have I made myself perfectly clear Brenna?"

As I teased my fingernail across his scrotum, he realized how helpless he now was. "Yes Miss Wendy and Miss Kate I will be on my best behavior and do as you wish," was my response. But my thoughts were that as soon as I get a minute to myself I am going to have to figure a way out of this chastity. I was then led to the master bedroom and told to be quiet and stand still.

Katherine moved the vanity chair to the end of the bed and was attaching something to it, as Wendy put the blindfold over my eyes. She told me to undress her completely, and I did so without seeing her. Next, I had to undress Katherine. I had never seen her naked and would not be tonight either.

I was guided back to the chair and told to sit slowly. As I got close to the seat, I felt something coming through the hole in the back of the panty.

"Sit gently Brenna. I need to make certain your dildo lines up properly for you to enjoy this."

I moaned and shook my head no, only to receive a quick slap to my panty covered balls. I guess it was Katherine that pushed down on my shoulders, forcing me to the seat and the dildo up inside me for the first time.

A couple of things for you to remember, Brenna, your cock and balls will only be referred to as a sissy clit and sissy eggs in the future. And Wendy and I will be called Mistress when in the house and Miss Katherine or Miss Wendy when we are out. We are now going to have really hot sex on the bed in front of you. If you were a true sissy we would allow you to watch. But, because you think you are still male, you can't.

"I hope you don't get too excited in your cage while we have our fun," she said as she kissed my cheek softly. While she said that Mistress Wendy cuffed my hands behind my back and slid her pantys over my head settling the crotch over my nose.

Her scent drove me wild and caused another painful erection in my cage. I heard the bed springs squeak as they climbed into it. I must have sat there for 3 hours, listening to the sounds of 2 hot women having sex so close to me. My mind was going nuts trying to imagine what they were doing. My sissy clit was as hard as the cage would let it be. It would hurt like crazy and soften up and a minute later back to trying to get hard again. An endless cycle.

Finally, my wrists were released and the blindfold removed. Mistress Wendy stood over me and pointed at my pantys. They were soiled with precum and not just a small amount.

"What is this mess in your panty, sissy?"

I don't know, I am sorry Mistress. Really."

"Well only a sissy would mess her pantys with a dildo up her ass and her clitty locked up, dontcha think?"

"Would a man mess in a pair of pantys, Brenna?"

"No Mistress."

"Would a real man have a dildo in his ass and be tied to a chair by 2 women?"

"No Mistress."

"So what does that say about you Brenna?"

"I guess it means I'm a sissy Mistress."

"Well, if you only "guess" then you will just have to stay in that cage a while. At least until you really believe instead of just guessing."

Fuck, I thought, I just shot myself in the foot there. I gotta try and get ahead of the curve with them of I will never get this off. It's like they are always a step ahead of me.

"OK sissy, off to the bathroom with you. You can remove and clean the dildo and get ready for bed. The pantys stay on and I will put a nightie on your bed." Mistress Katherine remained covered up in the bed until I was gone from the room.

I found a short pink nightie that was open in the front, and slipped it over my head, and hopped into bed.

My Mistresses came in a few minutes later in their dressing gowns. Wendy placed the earbuds in my ears as she had for many weeks now. Katherine had two clear cone-shaped plastic things with her. She rubbed some kind of cream into my breasts and placed a cone over each. She attached a pump to the end of one and started to squeeze the handle. It drew the air out and sucked my breasts up into the cones.

"If we do that regularly, she should get a bit of breast growth in a few weeks. Then we can decide if we want to continue the growth with hormones or implants." It was probably good that I could not hear her with the earbuds in place. I was kinda shocked to see how big my tits looked all swollen in there. I would be a long almost sleepless night between the pumps and the cage.