Sissy Shopping with Princess T

This time I saunter out of the dressing room confidently instead of treading out cautiously. I twirl around without being told, showing off my little sissy ass to Princess and the random store employee.

Princess lets out a low whistle of approval. "Yes, sissy! That is what I like to see!"

Her words please me, but I blush nonetheless. I turn in her direction and see a new woman standing behind Princess, carrying some garments of her own to try on. My confidence waivers momentarily. The new woman glances over at me and to my surprise she does not seem particularly shocked. She makes quick eye contact eye contact with me, flashes a quick smile and tries to get the attendant's attention.

The attendant seems more flustered than me as she turns to assist the new customer. Princess ignores them both as she beams at me.

"Walk toward me and bit and then turn and walk back to the dressing room," she instructs. I quickly comply, strutting like a runway model. As I turn, I pause and look back over my shoulder. All three woman are staring at me. Princess looks as happy as I have ever seen her, a carefree smile gracing her lovely face. The customer has a shy, bemused smile, as if she is enjoying what she is seeing but trying not to get too involved. The dressing room attendant still looks as if she is trying to suppress a laugh. I turn my head away from them and strut back to the dressing room. Once the door is closed behind me, I feel a shock of disappointment that I have to put man clothes back on. I quickly do so anyway and hurry out to Princess carrying both negligee's.

We both agree that the pink one is more suitable, and Princess begins to look for stockings and a new pair of panties for me. I stand obediently behind her carrying my negligee while she rifles through the selections. At one point the customer who saw me at the dressing room approaches. She is middle aged with long brown hair and a pretty face. She is dressed casually in jeans and sneakers with a modest dark blue blouse. "Hey there little sissy," she said quietly while browsing the panties next to me. "I enjoyed your little show. My husband likes to wear my panties sometimes but I don't think I could ever get him to show off in public like that."

I glace over toward Princess to see if she has any instructions on how to handle this situation. She keeps looking through undergarments as if I am not there.

"Thank you Ma'am. I am glad I didn't offend you," I say to the lady.

"Far from it. I am glad you have a women to pull out your sissy side. It would be a little creepier if you were here trying on lingerie on your own. Having a woman guide you just makes it seem more wholesome and makes you seem less threatening."

"Thank you. I have bought panties for myself before, but wouldn't dare to use a dressing room to try on lingerie without a woman's guidance."

"That's a good boy," she replies with a chuckle. "As long as you keep obeying your Mistress and doing what she says, other woman can enjoy you without fearing you. Emasculating men is very sexy to me."

"Sissy!" Princess calls to me, holding up a small pink thong. "I think I have found the panties to match your negligee." The woman talking to me laughs softy and moves off to another part of the store.

"Yes Princess," I say. "Those are very nice." She hands them to me and I carry them with my pink negligee, feeling more and more at ease.

Princess soon finds me some pink stockings to complete my outfit. I am very excited to try on all three pieces at once, but know this is not the place. After completing my outfit, Princess decides to get some lingerie for herself for a date she has later that night. She doesn't ask my opinion on anything as she adds a black push up bra, some sheer see through panties, a garter belt and some sort of lace up corset to the pile that I obediently carry.

"I bet you would like to see me in some of these outfits, huh sissy?" she teases me as we finally head toward the checkout.

"Yes Princess, that would be amazing."

"Well you will have to be a very good boy to earn that right. Princess only dresses sexy for real men." We are in line at this point and two young women behind us in line, maybe in their early 20s, snicker audibly. I overhear one tell the other that she needs to find a sugar daddy who will pay for her lingerie. I fight the urge to look back at them and keep my eyes forward, darting them from Princess to the rest of the line in front of us.

Princess greets the cashier casually, but says nothing humiliating as the young, pretty brunette rings up the purchases. At one point the cashier does shoot me a little knowing smile, as if realizing that some of the items are for me. After all, my little pink negligee would not come close to containing Princess T's busty chest. The total comes to a little over $200. Obviously more than I want to spend, but how could I put a monetary price on satisfying such a unique and perverse fetish? It is probably not a coincidence that the cashier bags my items and Princess's item separately. Very perceptive of her.

After we leave the lingerie store, we make a quite detour to the food court where I purchase Princess a coffee. She does not ask if I want anything and I do not take it upon myself to order something on my own. I simply pay and follow in step behind Princess as she walks back to the car.

Once at the car, I open the door for Princess first and then place the purchases in the back seat. As I do, she calls me over to her.

"You were very obedient today sissy. I am proud of you," she says. She is sitting in her seat with the door open, but still has her feet on the concrete. "I am going to give you a reward for your behavior. Get down on your knees."

"Yes Princess," I reply eagerly, quickly dropping to my knees in the parking lot. Thankfully the space next to us is empty and there is plenty of room for me to kneel in front of my superior.

"Good boy," she responds to my rapid action, patting me on the head. "Now I know you probably wish I was wearing open-toe shoes but it is simply too cold for that. And I think your slutty little mouth would still be honored to kiss my feet. Isn't that correct?"

"Yes Princess!" I reply again, even more eagerly this time.

"Very well then. You may kiss my shoes sissy." She makes no effort to raise her shoes, so I drop my head down to the concrete. I am on my knees in a dirty mall parking lot with my ass in the air, tight red panties sticking out of my pants. I give one long smooch to each shoe, wanting to do more but not sure how much I am allowed.

"Keep going sissy," I am instructed from above. "Shower my shoes with your kisses of gratitude until I tell you to stop."

I need no more encouragement. I kiss up and down her right shoe. From toe to tongue and from side to side. After a few seconds I can taste my own saliva on the canvas surface. Sneakers have a unique flavor that I do not enjoy as much as heels or bare feet, but it feels so incredible to be kissing Princess T's out in public. Sooner than I would like, she commands me to switch to the other shoe. I shower it with kisses just as eagerly as I did the first. I am tempted to start licking at one point, but resist the urge as my orders were just to kiss.

"Enough sissy. You may stop." My heart sinks a bit. I was enjoying myself far too much. "Hurry up and get it the car, I need to be getting home." I scurry around to my seat, start the car and we drive off in silence.

When we arrive back at Princess T's, I hurry over to open her door for her. "Bring in my bag of lingerie and the bag from the sex store," she instructs me and she walks off toward her apartment. I quickly grab the requested bags and follow her.

Once we enter, she immediately orders me to strip to my panties. After I have shed my man clothes, I take her purchases upstairs and lay them out of her bed. I cannot help but fantasize about how incredible Princess will look in her new sexy outfits, but I understand how that privilege is reserved for real men. I spend a minute or two arranging the outfits neatly on her bed and hurry back downstairs.

Princess T is sitting on the couch on her phone. The butt plug we purchased is out of the bag and sitting on the coffee table in front of her, along with a bottle of lube. She looks up at me from her phone.

"Before you go, I want you to put your plug in sissy. You really need to start stretching yourself out."

I wince involuntarily at the thought but approach the table.

"Leave your little panties on, just move them to the side. I am going to film this for my friend. She'll get a big kick out of it."

Princess has one friend that she occasionally updates on my submissive adventures. I have never met her and most likely never will, but it thrills me to have a stranger laughing at me. Out of habit, I drop to my knees in front of the table to pick up the plug and remove it from the plastic casing. I struggle for a moment, but eventually free the plug. Holding it in my hand, I gaze up expectantly at Princes awaiting further instructions.

"What are you waiting for sissy?" she asks impatiently. "Lube it up and stick it in. I don't have all day. I have a date soon and I don't need you taking up anymore of my time."

I quickly coat the plug with a thin layer of lube and rise to my feet. I have put a butt plug in before, but it has been some time. I squirt a little lube onto the fingers of my right hand and pick up the plug and pull my panties to the side with my left. I sense Princess raising her phone behind me to record. I begin inserting the index finger of my right hand into my tight little hole. It opens up a little easier than I anticipated. I rub the lube around the circumference of my hole, moaning slightly in pleasure. I bend over a little, exposing my hole more to the camera. My right finger exits my hole and starts to hold my panties to the side. I approach my hole with the plug using my left hand. I start the insertion slowly and my moaning increases. Princess chuckles a bit behind me. The first inch or so of the toy glide in easily before the pain starts. I press a little further, yelp in pain, and remove the toy slightly.

"Hurry up sissy," Princess directs. I ease the toy back in further. The pain intensifies, but it is not unbearable and a sliver of pleasure remains. I feel a bead of precum start to drip from my still flaccid penis. I persistently push the head of the plug in. Soon the width has stretched me out sufficiently and the plug pops in up to the base. I let out another little moan, more of pleasure than pain.

"Good sissy," Princess compliments. "Now turn around." I turn and see her phone held up, pointed right at me. She laughs and comments on the precum stain obvious in my panties. "Looks like sissy enjoyed herself today?" she inquires.

"Yes Princess, very much."

"Good. Now get dressed and get out of here," she says, her voice suddenly cold as she lowers her phone. "You may remove the plug before you go to sleep but not until then. You can practice on the toy with your mouth if you want, but do not text me and certainly do not send me pictures or videos tonight. I will be busy. I will contact you sometime tomorrow with further instructions. Do you understand?"

"Yes Princess!" I reply enthusiastically as I quickly put my man clothes back on. "Thank you for everything Princess T. I had an amazing time," I stammer as I head to the door. Princess simply nods at me as I let myself out.

The plug shifts and causes a little discomfort as I lower myself into my car seat. It is going to be a difficult night plugged without being allowed to contact Princess. I will be thinking about her out on her date all night, but I will obey her and not initiate contact. At least when I get home I can put on my full new outfit. And I have a dildo to start training my throat. Maybe it won't be such a bad night after all.