Sissy Shopping with Princess T

I excitedly pull my tight red lacy panties up over my small, limp penis. They feel so nice. Tight, but soft, containing the perfect amount of room to hold my little package. My penis does not attempt to get hard despite the pleasure, if anything it seems to shrink a bit in order to fit more comfortably. This was my first time seeing Princess T without her instructing me beforehand which pair of panties to wear. I certainly had many pairs to choose from, most of which she had seen before. I was under the assumption that it was expected I would wear panties to all of our meetings.

The thought had crossed my mind to ask Princess T if she had any particular pair in mind for this meeting, but I reached the conclusion that if she had a preference, she would have made it known. Princess T was not much of a phone talker. She desired real life service and was not particularly interested in drawn out text chats where I ask for permission or guidance regarding the mundane details of my pathetic life.

All I knew of our meeting today was that we were going shopping. There are a couple things she had mentioned about us acquiring before, but I had little idea where the day was headed. I was nonetheless excited. Even driving around to buy groceries or pick up laundry with Princess T would be the highlight of my week. Despite her lack of text communication, she was always on my mind and being allowed in her presence was always a treat.

Once my red panties were secure, I quickly threw on a pair of khakis and debated whether to wear a T-shirt or a dress shirt. I was moderately accustomed to having my entire wardrobe selected for me by dominant woman I had served in the past, so I found it a bit stressful to make such seemingly simple decisions for myself. Making decisions was not my strong suit. I preferred to follow specific instructions. My ultimate goal was to find a woman to marry who would enjoy making such decisions for me, effectively controlling every aspect of my life. Princess T was fully aware of this desire but we were still at the very beginning of the dating process.

After checking the temperature and seeing it was a bit chilly, I elect to wear a black sweater that I considered more fashionable that a majority of my Goodwill dominant wardrobe. I put the sweater on over a black T shirt and leave my house hastily. The last thing I needed was to be late picking up Princess.

I pull up to Princess T's apartment 20 minutes prior to the instructed meet time. Better safe than sorry. It shows dedication as a submissive to arrive early, an example of how her time is superior to mine and how simply waiting for her is a more valuable use of my time than anything I could be off doing on my own. The text I send as I park is not replied to immediately. I simply wait patiently in my car, listening to music, trying to limit my excitement and stay calm and humble for Princess's arrival.

A little over 20 minutes passes before Princess replies saying she will be out soon. Another 10 pass before I am finally graced her presence. She walks out briskly, not exactly in a hurry, but walking with purpose and no nonsense.

She sports a simple white tank top that contrasts beautifully with her luscious dark skin. It was not low cut enough to be cleavage revealing, but just seeing any amount of the flawless ebony skin below her neck draws me wild with lust. Over the tank top, she wears a dark blue sweater. Even with my limited knowledge of fashion, I'm quite sure that her sweater is more fashionable and more expensive than mine, but I still feel a small beam of pride that I have seemingly dressed appropriately for the occasion.

Over her toned, muscular legs she has on form fitting, but not quite tight jeans. They make her thighs look like absolute heaven, the place where I want to go when I die. Or simply the place where I want to die. Try as I may to control my sexual thoughts, her thighs drive me absolutely wild with lust. I am unable to get a view of her ass as she strides confidently toward me, but I am quite sure that it looks as fantasy inducing and heart stopping as the rest of her physique. She completes her outfit with a pair of low cut sneakers, the same color as her sweater. The foot fetish part is me was briefly disappointed that I do not get to see her sexy toes nor a sexy high heel, but I am able to quickly dismiss any thoughts of negativity as I scurry out of the car to open her door.

"Good sissy," is her only greeting as she graciously slides into the passenger seat. I hurry back around to the drivers side, get in, start the car, and await orders on where to go.

"First, we will be going to a sex store. You need a butt plug and a dildo to practice on, so that you are ready when the times comes for me to fuck you."

I shudder a bit at the matter-of-fact way that she says this. It is the same tone of voice as if she said she needed to go pick up dry cleaning.

I had some prior experience with stretching my little hole, and had been pegged a few times before, but none recently. I was a little skeptical and not fully excited about entering this cycle again, but I was more than willing to try to loosen my hole if Princess T wished to lay her claim to it. I wait about 30 seconds to see if she will name a particular sex store nearby, but she merely glances at me expectantly as if she does not know why I have not left yet. I quickly type 'sex store' into my GPS. It corrects to 'adult store' and shows one 3 miles away. I take off in that direction as Princess T stares wordlessly out the window.

The ride is silent, not exactly awkwardly so, but short of comfortable as well. My mind is racing through all sorts of thoughts. Part of me wants to ask Princess if I should put music on, but I know she doesn't like the same type of music as me and am not sure what I could put on without asking what would please her. I am starting to learn that the fewer questions I ask Princess T, the better. She is obviously comfortable sitting in silence and if she wants to change that she will certainly let me know. My desperate, eager to please mind continues to over analyze everything.

Despite the number of thoughts my mind is able to nervously run through, we arrive at the store quickly. Princess T gets out herself, not waiting for me to come around to open her door. Her time really is quite valuable. She strides briskly toward the door and I meekly fall in step behind her. It must be obvious to anyone witnessing this simple stroll who is in control.

Upon entering the store, Princess does not break stride, heading directly to the back right wall where the dildos are. Here she pauses for a moment as her eyes scan the selection. Without a word, she selects one and hands it to me. It is dark brown, 8 inches long and quite thick. Probably about twice the size of my penis overall, length and width accounted for. It also contains a suction cup to stick to a floor or table to allow one to lower their mouth or hole onto without the use of the hands. Having handed me my future weapon of ass destruction, she begins to peruse the butt plugs.

There are not as many plugs as there are dildos, yet it takes her slightly longer to make a selection. Once again, there is no asking of my opinion. She simply shops as if I am not there. It isn't long before she hands me a 4 inch plug, with a slightly wider base than ones I have used previously. A small pit of fear begins to build in my stomach but I do not dare voice my hesitations. Princess T simply walks toward the register. I follow, my head down, without a word.

Princess approaches the counter and greets the cashier, a youngish white girl, a little on the bigger side, with streaked pink hair and at least 7 earrings in each ear. I don't hear the details of the greeting. My face flushes red as Princess steps aside for me to place my purchases on the counter.

"My little sissy has some practicing to do," Princess says to the cashier with a smile. It's the first time I have seen her smile all day and it is while she is talking to someone other than me.

"I see that." The cashier giggles and makes eye contact with me in a way that is both loving and condescending at the same time. "That is kind of a big plug to start with for a beginner," she adds, part in amusement part in genuine concern.

My blush deepens. I start to mumble a response, but Princess T cuts me off. "He isn't exactly a beginner. He's been fucked before, haven't you sissy?" My embarrassment turns closer to shock. This is the furthest Princess T has ever gone in dirty talk and she is doing it in front of a stranger. The pit of humiliation in my stomach begins to expand and I feel my repressed little dick start to grow in my panties.

The cashier laughs again and eyes me questioningly. I somehow am able to find my voice. "Yes, I have been fucked before, but it has been awhile. I trust that Princess T knows what is best for me and that these toys will be fine for my training."

The cashier nods knowingly. "Well that's good. Your total will be 65.43."

Damn, more than I expected. But when you are broke and spend all your excess money on dominant woman, everything seems to cost more than you expect it to. Though all the humiliation of the experience, I had not yet considered the financial ramifications of the situation. Not that $60 was a huge loss, but it was only the beginning of the day of shopping. I was quite sure I would end up spending much more than that on Princess before the day was through. I insert my card into the chip reader. The cashier hands me the bag containing my items. As the card processes, she looks me up and down with the same mixture of amusement and condescension.

"That's a pretty cute little sissy you have there Ma'am," she says directing her gaze toward Princess T. "I bet she looks really cute with a dick in her mouth." She called me she! My dick begins to harden with more enthusiasm. What was once a small pang of humiliation in my stomach now washes over my entire body. A stranger, a girl I have never met, just said I would look cute with a dick my mouth.

Princess T takes the comment in stride, appearing neither upset or shocked that the cashier would speak this way. "I certainly hope to find out. He should have my dick in his mouth soon if he continues to behave himself. And perhaps a real dick one day if he is able to consistently please."

My card goes through and the cashier hands me the receipt. "Be a good little sissy for your Mistress."

"Yes Ma'am," I reply submissively, dropping my eyes down to the the receipt. I want to be strong enough to look her in the eyes as I say this, but just can't bring myself to do it.

"Thank you very much," Princess T says to the cashier and she turns and heads towards the door. "Hurry up, boy, there is much more shopping to do and not much time."

I manage to bring my eyes up to the cashier. "Thank you," I manage to eek out weakly.

"You're welcome little sissy boy," she replies with a playful smile. "Enjoy stretching your little ass."

I simply nod at her and follow Princess T out of the door. She taps her foot impatiently by the passenger seat. I rush to open the door for her, literally run around to the other side and get into the car, tossing the bag in the back seat.

"Now to the mall," Princess T states with authority, making no mention of our first shared experience of public humiliation.

I type the name of the nearest mall into the GPS and begin driving in silence to the next destination.

When we arrive at the mall, Princess instructs me where to park. After I do so, I quickly hop out of the car to open her door for her. This time she waits for me to arrive. She slides out of the car gracefully, without a word.

Even though I have been in her presence for some time now, I am briefly stunned by her beauty as she begins to walk toward the mall, once again paying me no mind. My eyes are drawn to her ass despite my best efforts to divert them. Her ass and thighs move in such a hypnotic, seductive manner it seems she must be sashaying, walking with exaggerated steps, to highlight her assets, when really she is merely walking quickly and with purpose. Her body possesses such a natural grace to it that it is hard for me to look away or think of anything else. I break my trance the best I can and begin to scurry after her.

Just as she did before she walks directly to her destination, not showing any hesitation or breaking stride. This time the destination is a lingerie store. Upon entering, she slows her steps and begins to peruse the selections. She never looks back to make sure I am behind her, she just inherently knows that I am. I mean, how could I not obediently follow such a sexy, confident, alpha female? After a few moments she finally speaks.

"We will get you one sexy negligee, one pair of panties and one pair of stockings," she informs me matter-of-factly.

"Yes Princess. That sounds nice," I reply meekly. I am quite thrilled on the inside, but do not yet have the conviction to express myself with that inner excitement in this public setting. The store is moderately crowded but no one has looked my way. I do notice that there are no other males in the store shopping with their girlfriends or wives. Just a little sissy with his dominant Princess.

Her first selections are negligees. She picks out two, one pink and one black. The pink one contains very small and frilly bra cups with a little white bow between them and a see-through flowing gown that didn't look very long to me, maybe going down to the top of my thighs. The black one flows a little longer and has an opaque black lace design over parts of the gown. The bra cups are a little larger and less frilly. The pink one wraps around the back of the neck while the black one has simple on-the-shoulder bra straps. Princess hands them both to me.

"Go try these on sissy," Princess ordered. "And come out so I can see them on you."

"Yes Princess," I reply even more meekly than before. I walk over to the dressing rooms carrying both negligee's over my arm. Princess remains browsing, but I assume she will be over shortly.

The lady standing at the dressing room counter is a busty, well built, middle aged white woman. Her dark hair is pulled back in a simple bun and her wears a no nonsense expression on her face. She looks as if she could be the straight laced mother of the more rebellious sex store cashier. She glares at me with hard brown eyes, as if I am trespassing somewhere I don't belong. And I suppose I am. I feel creepy, out of place, and uncomfortable. Different emotions than the humiliation I felt at the sex store.

I will myself to proceed. Princess knows what is best for me. I approach the counter timidly. "I would like to try on these two items Ma'am?" I say hesitantly, almost as more of a question than a statement.

She glares and me and almost imperceptibly rolls her eyes. "Follow me," she says in a commanding but matter-of-fact tone. I follow her with my head down, focusing on her feet. She is wearing sensible brown pumps. Nothing that would draw particular attention typically, but I find myself wanting to suck on her heels while she ridicules me for being such a sissy. Her purposeful steps stop at the third door in the long line of doors that line both sides of the walkway. "In here. And please make sure you keep on all underwear. Nobody wants your nasty little penis to touch these fine fabrics"

I feel a burst of humiliation rise, pushing aside the out-of-place discomfort and replacing it with the type of discomfort I crave, not that it feels any more comfortable. The lady gives me a defiant stare, as if she is daring me to challenge her.

I merely say, "Yes Ma'am, of course," in my meekest submissive voice and enter the room, closing and locking the door behind me.

Once inside the dressing room I take a deep breath and take in my surroundings. There is a large mirror, two hooks for hanging clothes, and a small ledge. Since the negligee's are not on hangers, I place them on the ledge. I strip down to my panties, leaving all my man clothes on the floor.

I pick up the black negligee and slide it over my head. The material feel so unique on my skin. So soft, but also forbidden. I pull the negligee all the way down, ensuring that the bra cups and straps are lined up properly. My breasts don't quite fill the bra but it still cups them nicely. For as long as I have been wearing panties on and off for dommes, I have never tried on a bra before. It is certainly a unique feeling. I allow myself a glace in the mirror. I look ridiculous. The outline of my red panties is just barely visible through the translucent material. The end of the nightgown cuts off about where I stop shaving my legs. I shave my groin area and upper thighs in an attempt to look more like a sissy when I take pictures in panties. But below that my legs are covered with splotchy, gross man hair. The contrast is certainly dramatic compared to the soft feminine cloth above it. I wonder if Princess will like the contrast or if eventually I will be instructed to shave my entire body.

Time to find out what she thinks. I open the door and peek outside. Princess is waiting by the counter talking to the woman who led me to the room. I can't decide if I want to know what is being said, or if it is best that I am unable to hear.

Princess sees me peeking out the door. "C'mon out sissy," she bellows. "Let's see how that lingerie looks on you."

I step outside the dressing room. My cheeks begin flushing red as I take a few small steps towards the counter. Princess does not move any closer to me. She wants me to be as exposed as possible. I hear a quick burst of sound to Princess's right and turn to see the dressing room attendant with her hand over her mouth. She is attempting, and failing, to hold in her laughter. Her head turns to the side.

Princess looks me up and down with an amused smile on her face. She doesn't say anything for a few seconds and I am not sure what to do. Finally, she looks me in the eye, "How do you feel wearing that negligee, sissy?" she asks, with just a hint of taunting in her voice. The attendant's stifled laughter grows louder at Princess's question.

"It feels nice Princess T," I murmur, barely audibly. I can feel my little dick start to stir in my panties. I pray it isn't visible, but know it most likely is with so little coverage.

Princess's eyes move down to my crotch. Uh oh. She notices I'm getting hard. She smiles. "Hmmm I think it looks okay on you. You obviously look ridiculous but I enjoy that. Let's see if the pink one looks any more natural on you. All sissies love pink don't they?"

"Yes Princess," I nod my head nervously and begin to retreat into the dressing room.

"Wait a second, sissy," Princess commands. I stop and turn to look at her, humiliated but also incredibly turned on. "Give me a twirl. Let me see your cute little sissy tushy." The attendant lady makes no move to cover her laughter now. She is laughing full force and her body begins to shake. I worry about drawing more attention to myself, but for now all I see are her and Princess. I take a deep breath, move one step closer to my tormentors, and give a little twirl. I'm sure it is more ridiculous than sexy, but I do actually enjoy it despite how clunky I feel.

Princess joins the attendant in laughter. "Very good sissy, now give me one more."

I twirl again, a bit slower, trying to wiggle my ass at the same time. The laughter of both women increases. I make eye contact with Princess. She seems genuinely amused and appears to be having a good time. That pleases me. She ushers me back to the dressing room with her hand through her laughter.

I re-enter the dressing room and close the door. I hear their laughter subside, hear some mumbled dialogue that I can't discern, and then more laughter. My dick is caught it its semi-hard state. It will not grow fully erect or subside to its limpest form. I pull the black negligee off, carefully fold it and place it on the ledge. I stand for a moment in just my panties, taking a few deep breaths. Attempting to enjoy the moment. This is something I have secretly desired for a long time. A fantasy is coming true. Sure, it was scary and awkward and humiliating, but I needed to embrace those feelings and not shut them out. Feeling a bit reinvigorated, I begin to put on the pink negligee. It feels just as soft and sensual as the black one, but seems as if it is a better fit. The smaller bra cups support my man boobs nicely. The gown is shorter and cuts off higher on my leg, showing my shaved sissy thighs. The crotch area is far more see-through, showing off my red panties even more. I look at myself in the mirror and enjoy what I see. I just need a wig and some lipstick to look like a full blown sissy.