Transforming Brent Pt. 04

In the morning I showered and dressed casually as directed by Mistress Wendy. My new black skinny jeans and a plain blouse with light day make up and my cork wedges. Some jewelry and my handbag and I was ready. Mistress wore leggings and a tunic top with her long hair tied up in a bun. Wearing flats, she was still much taller than me.

We had a light breakfast before our limo arrived and enjoyed a quiet trip to the train station. There was a nice little shopping district surrounding the depot. Having some time to kill we decided to check it out. We ended up picking up a couple of bottles of fine wine and some flowers for Miss Katherine and headed back to the station.

We were soon boarded and on the way to the city. I was still a bit nervous when I was out in public dressed entirely feminine. My voice appeared to be my biggest weakness in passing fully, but I rarely got a strange glance. I guess most people observing me just thought I was a homely woman. But at least I had beautiful hair and a beautiful wife. My thoughts changed to Mistresses promise of unlocking me and the sex we would be having soon.

"So Brenna, you seem to be in a good mood today. Care to share your thoughts?"

"Oh, just the usual Miss Wendy. I was thinking about how beautiful you are and how I am looking forward to finally being unlocked."

"I see. And how do you feel about our new lifestyle? I know its been quite a change for you."

"It has been and still is quite a change. Not one that I was ever expecting, that's for sure. But I think Katherine was right all along. When I was younger I always did like feminine things. I even dressed as a girl, or a witch on Halloween a few times and really loved it. I loved the feeling of the sexy girdles and stockings and things but after high school I just forgot all about it. After-all, that wasn't how young men were supposed to be. These past few weeks have opened up all those sexy feminine feelings again. It's nice to be dressed as a normal woman instead of a maids uniform or that silly little girls dress though."

Mistress laughed at that. "I'm so glad to hear that darling. Things have definitely been more exciting of late. But don't get to used to dressing as a "normal" woman. It won't be happening very often."

"Yes Mistress."

"And something else you need to know Brenda. Kate has been involved with the bdsm community in the city for many years, especially with the leather dykes. She likes you Brenna. Mostly because you are my partner. But she has very specific ideas on how a submissive should behave. You will do well to obey her."

"Yes Mistress. I kind of got that feeling from her. What we have done has been pretty sexy and I will always do my best to keep you happy."

"Okay we are almost there. I will call an Uber, while you get our luggage together."

"Yes Ma'am," I responded as the train pulled in to the station. It had been a while since I had been to the city. The sights and sounds, all the shops and so many people. It was going to be a fun 10 days.

It was about 1:30 in the afternoon when we arrived at Kate's building. She had the penthouse apartment on the 40th floor with a beautiful view of the ocean and the city. As Mistress Wendy had texted her, she was waiting for us at the entrance. After hugs, she even helped me with the luggage and led us to the elevator. Her suite was enormous, with 3 bedrooms, 3 full baths, a formal dining room, modern kitchen and a living room and TV room. She even had a private office/den off of the master bedroom.

She had a partially enclosed patio that wrapped around 2 sides of the penthouse, with plantings, seating and a BBQ grill. It took up half of the top floor of the building. After giving us the apartment tour, she showed us the year-round rooftop pool, hot tub and gym that took up the rest of the floor. They were for the use of all tenants in the high-rise.

Back in her place, I set Mistress Wendys bag in Katherine's room. Turning to me Kate said," Brenna, unpack your lady's clothing. You can hang things in the walk-in closet and use the empty drawers in the bureau there for her other things. Then take you bags to the first guest room down the hall and unpack your things."

"Yes Mistress Katherine."

"Seeing that it is a nice sunny day, I put out something for you to change into. I want some private time with Wendy so you can go out on the porch and get some sun. There are a few joints on the bar out there, and a comfy lounge chair. Before you go outside, bring us some wine. You may have a glass too.

"Yes M'lady."

My bedroom had a nice double bed with a very sturdy wooden frame, and vanity, and a small walk in closet. It was decorated more like a little girls room, with ruffled drapes and bedding, and a soft pink carpet. On the bed was a hot pink 2-piece bikini for me to wear. I put away my clothes and went to the kitchen. I found wine glasses on the bar and poured 3 large ones. Putting 2 on a tray I knocked on Mistress Katherine's door.

Told to enter, I found them cuddling under the covers already. I brought them their wine and modeled the swim suit for them, and was told to go away for a while.

"Mistress, do you have any sunblock I can use?"

"No Brenna, but it wont be to long, so don't worry. Now run along little girl!" I left them to their fun and went outside. It was a nice late summer afternoon alright. Lots of sun and great views. The lounge chairs were as soft as a bed. I laid back and lit a joint, enjoying it between sips of wine. I was pretty stoned and set a lounger flat to relax a little and think how nice it would be to get the cage off later. I hoped Kate didn't wear Wendy out too much. Lol.

"Brenna! Hey Brenna, wake up," I heard as Mistress Wendy was pushing on my shoulder. "You don't want to get a sunburn out here." After smoking that joint I must have fallen asleep for a bit. "Take a shower and then meet me in your room. Katherine is taking us out for dinner."

I showered and met mistress in my room. She was dangling the key for my chastity from her finger. On the bed was the pink and white dress with the full petticoats. "Lets get you unlocked and dressed for dinner Brenna."

"Oh dear, do I have to wear that to a restaurant Mistress?"

"Of course you don't Brenna. If you want to stay in chastity you can wear the clothes you wore on the train. I will just tell Kate to put the key back in the safe for a few more weeks. By the way, those tan lines look very girly on you."

"Yeah about that, I didn't plan to fall asleep outside. I will wear the pretty dress please unlock me?"

The first thing she had me put on was a tight little panty girdle. Before pulling it all the way up, she forced my sissy eggs up into their sockets and tucked my clitty back between my legs. Then with the girdle pulled up there was no sign of my male parts at all. Pink pantyhose shimmied up my legs followed by the fluffy petticoats. A cute little training bra covered my darkening tan lines and then the dress that buttoned up the back. A pair of black Maryjanes on my feet and then mistress did my makeup. By the time she rouged my cheeks I looked like an adolescent girl standing next to my much taller wife/mistress.

After dealing with a few interesting glances and some laughter from others on the elevator ride down from Mistress Katherine's suite, we were headed to a local bistro a few blocks away. I had a Mistress on each side of me holding my hands. They kept up a brisk pace and encouraged me to skip along between them like a little girl might do with her parents. It had been a long time since I had "skipped" so concentrating on doing it right kept me from noticing the passerby's odd looks.

I was pleased to see that the bistro was dimly lit, and we were soon seated in a comfy booth. The waitress smiled as she brought our menus, and looking at Wendy and Kate said, "hiya I'm Isabelle, and I will be your waitress tonight. Here are the menus. After glancing at me she added, "would you like a children's menu for your daughter?" I blushed at the comment and was about to say no when Katherine said that would be fine.

I know she saw me wince at that. I was hungry and wanted one of the nice steaks I saw at a table we passed by. When the menu was brought over Mistress Wendy reached for it. "Watch your manners Missy, or we will have her bring out a highchair for you."

"Yes Miss Wendy, I will be good and act my age." Wendy ordered salmon, and Miss Katherine ordered prime rib. Then she ordered a child's tuna salad plate and milk for me. I was bummed but I tried not to show it. At least it turned out to be made from fresh tuna. Even more humiliating was that they each had a nice wine, while my milk was brought in a large pink sippy-cup.

We strolled slowly back to Kate's, doing some window shopping on the way. "Brenna, I made an appointment for you tomorrow morning at a local salon. They will do laser hair removal for you. They tell me that with the new equipment that after just 2 treatments you will never have to worry about shaving again. And we will never have to feel your stubble."

"That's really cool Mistress Katherine. I know I don't have much of a beard but it will be great not to have to shave my face anymore. Thank you so much."

Finally back at the apartment, Wendy put the leftovers in the fridge and we went on the patio and enjoyed some wine and weed. "So Wendy, I guess you are going to give Brenna a treat tonight."

"Yes, I did promise to let her enter my cunny tonight. We really need to make it special as it is probably her last time. But I am sure she will be happy when we are done. Now Brenna, we are going to get changed into something more comfortable. Finish the joint and have some more wine until we call you in."

"Yes Mistress Katherine and Mistress Kate." I could feel the excitement begin to grow in my girdle but could not get stiff. I will admit to wiggling it between my legs with two fingers for a minute though.

I was shocked by a voice and realized there was an intercom speaker on the porch. "Brenna come to Mistress Katherine's room now!"

I put out the joint I was toking on and went in. I was walking on air believing I was finally going to get to fuck my wife again. I had been a few months now and I was so happy. After knocking on the door and being told to enter I was stunned at what I saw. My Mistresses had put on the hottest, sexiest outfits. Oh my. My sissy clitty fought against the girdle.

"Come over here so we can undress you little girl. Tonight you get to pretend you are a man one last time."

I was soon naked in front of two beautiful women. Each at least 8-9 inches taller than me in their spike-heels. Between the scent of their perfume, the smell of the leather they wore, or just their absolute beauty, I was harder than I had been in weeks. Well that's not really fair to say, as I had been in chastity for the last couple of weeks.

"Time to get you into bed Brenna. Lay down on your back," Mistress Wendy said as Mistress Katherine fastened leather cuffs to my wrists and ankles. A leather belt with rings on each side was buckled snugly at my waist. On my back on Katherine's large plush bed, my wrists were soon attached to the headboard above my head. My ankles to each bottom corner. Straps from the sides of the bed were attached to the rings at my waist and tightly secured. OK, I wasn't going anywhere soon. Mistress Wendy stood on the bed over me and and slowly removed her panties. Then turning to face my feet, she just as slowly lowered herself down to my face. I inhaled her aroma as her moist pink pussy lips settled on my mouth. Yes I knew what to do. I felt her soft hands stroking me. "If you cum, you don't get to fuck me Brenna. Remember that." She took me in her mouth and sucked almost all of me into her. Omg! Must be what heaven feels like I thought. I tried to move my pelvis to increase the action but I was bound to tightly. I knew I wouldn't be able to last long and concentrated on licking her to an orgasm.

That worked a bit and I felt like I could hold off for a while. But then she started toying with my sissy hole with a finger and I was in trouble again. Mistress must have sensed me getting close to the point of no return and abruptly stopped touching me. She climbed off of me and turned to Kate, "lets go have some wine babe, I need another glass. Don't go anywhere Brenna, I'll be back soon."

I laid there helpless while they shared some wine and probably another joint. Returning to the room, mistress grabbed some lube and went straight for my clitty. I guess I should say her sissy clit nowadays. "ready for round 2 baby? I know I am. I guess I I can make you squirt I won't have to let you mess in me later. Just lock it back up and be done with it," she said with an evil grin. Her hand was pumping me again. Slowly at first, then she would grip it harder and speed up. All I could do was lay there and try not to go over the edge. I thought about everything I could to avoid it. Geico ads. Yes, how many different ones could I remember. That should keep me calm. Then she used her palm softly on my clitty head. Oh Fuck. This is driving me mad. She must have been teasing me for half an hour. But then, she stopped again.

Mistress Katherine handed her a Hitachi vibrator and a strap. After wiping the lube off of me she held the vibrator in place and strapped it to my clitty. She flipped the switch and I felt it through my hard on and throughout my body. My Mistresses left the room after telling me they would be back in a short while. I lied there with the voices in my head and the vibrator humming away. It was keeping me quite near the edge.

Through the open door I could hear the sounds of my 2 Mistresses making love. More torture for me, imagining just what they were doing. Mistress Wendy finally re-appeared in the bedroom and removed the vibrator, then released my bonds. "Time for that fucking I promised you Brenna. You better enjoy it like its your last, because actually it will be." She stripped naked and climbed into bed with me. We kissed and caressed each other like young newlyweds, with me finally entering her love tunnel.

We fucked slowly at first playing with each others nipples. "You feel so nice Brenna. Are you going to miss this in the future?"

Not really believing it would be my last time fucking my wife I replied. "Oh yes my darling Wendy, I will always miss it. I'm sure we will be trying things even hotter in the future, but I love for ever."

"And you know you are going to lick me clean after you squirt, don't you. You know I hate being messy like that sissy?"

"Yes Mistress Wendy. Whatever you desire."

"You are going to be a kept woman, Brenna. Hot and horny all the time. You will be such a good little girl when we finish changing you. I mean training you. Hee hee."

"Mistress, yes Mistress. I am so hot I feel like I will explode Mistress. Please let me squirt soon Mistress?"

"Soon baby girl," said Mistress as she slid a hand down to her clitty to stimulate it as we fucked. "Tell me you belong to me and will be a good girl for me and Kate. Tell me what I need to here and you can squirt, sissy."

"Please Mistress, I only want to serve you both and be with you always. Make me your little sissy girl. I want to be your little doll."

"Yes Brenna, you will be. Now cum for me my slut. Cum in me for the last time. Give that clitty up forever with your cum!"

And I did. I blew a load that didn't seem to stop. I almost passed out from the force of it. Oh fuck that was incredible. "Thank you Mistress. Thank you Mistress," I barely vocalized through my panting.

"You are very welcome Brenna. It was nice too cum together like that. I will remember this day fondly."

She finally pushed me over on my back again and crawled up to my mouth. "Time to clean mommy up baby!" And she moved her swollen pussy lips to me. I would not have resisted anything from her at that moment, and was quite surprised at how much cum I had filled her with. As I was slurping up my mess from her cunt I felt my hands being reattached to the headboard. Obviously by Kate this time. My feet and waist were soon tied again as well and mistress rolled off of me.

With a big smile on her face Mistress Katherine was looking at me with a suspicious smile. "I understand that penises are really sensitive after they squirt Brenna baby. Is that true?"

"Yes, Mistress Katherine. I have heard that and can testify to its truthfulness."

"Well good, because I have always wondered about just how sensitive they get. I hope you don't mind if I try it for myself. Oh, but look at you all tied up like that. Looks like you don't have a choice do you."

She put some lube on her hand and started to play with my spent clitty. It was still semi erect and even her smooth hands felt like needles rubbing me. I was helpless in her hand, being bound as I was and she was driving me nuts. "I wanna try to make you squirt again sissy. Can you do that for me baby?" she teased. I was moaning, trying not to scream from her teasing touch. Mistress Wendy had grabbed a leather cock ring and snapped it shut around the base of my clitty, making it stiffer and easier for Mistress Katherine to manipulate.

I was in the midst of a serious dilemma. Her one hand stroking me while the other palming the tender head. Stroking and tickling. A fingernail across the slit. Pumping harder as Mistress Wendy wiped my sweaty brow. I was trying not to cry. My suffering was bringing huge smiles to both of my Mistresses faces. Without a warning my clitty started to squirt again. I was squirming like I had been slapped in the eggs. I came without pleasure, without trying. She had milked it out of me. Not as much as earlier but still a decent load. I had never cum twice in 20 minutes in my life before.

Then the words I never wanted to hear. "Let's try for a third one sissy. You know most women can have many orgasms in a row. I wanna see if you can too." And she started stroking me again. I couldn't take it anymore.

"Please, please Mistress Katherine, no more. Please lock it up in the cage. You are gonna drive me mad. Please Mistress. Oh please stop." I don't want it anymore. Please just lock it away," I cried.

Seeing the tears on my face, she finally relented. Mistress Wendy removed the leather cock ring and cleaned me up with a soft cloth and Mistress Katherine retrieved the cage from the side table. As she applied the cage she mentioned that, "This is a new cage Brenna. Its just a little smaller and has these cute little spikes inside at the end. But don't worry, as long as you don't get hard in there, you will never feel them." With that she slid the catheter tube down into my clitty and fitted the metal tube of the cage over it. She slid the lock in place with a key, before they opened my bonds.

After a quick shower, I put on a lovely purple nightgown that was waiting on my bed. I found My Mistresses in the living room. "Brenda, you have been a very good girl today. And I bet you are actually pretty hungry and maybe a bit tired. I knew you were disappointed in not getting the dinner you wanted. So you will find I the fridge a nice prime rib dinner from the restaurant. We had them pack one for you and slipped it in so you thought it was our leftovers.

"Kate and I are going to bed. You may eat then watch television if you like before you go to bed. Remember, you are having a laser session in the morning."

They both kissed me goodnight, patted my chastity through my gown and went to bed. Damn that steak was good. I was famished and enjoyed it with some wine. After a little MSNBC I crawled into bed. Tomorrow the adventure would continue.

To be continued. Reviews welcome.