SissyMandy – Tamed By A Cougar

Anal

I was so excited when Mistress drove into the parking lot at the mall. Our destination is Victoria’s Secret, where Mistress Virginia is the manager. But this isn’t a shopping trip, and we’re not here to buy clothes. We’re here because Mistress has a delivery to make, and that delivery, is me.To say I’ve been excited about my very first sissy date would be an understatement. I’ve been excited about it ever since Mistress told me she’d arranged it. But now, with my high heels clicking on the pavement as I walk around the car to join Mistress, my body starts shaking as the reality of the moment hits me.”Nervous?” Mistress asks.”Kinda…” my voice trembles, “I didn’t think I would be, but suddenly I am.””Relax, you’ll be fine. Every sissy gets butterflies when she realizes she’s starting a new career.””A new career?””Yes, darling, your new… umm… ‘dating’ career, we’ll call it. It’s not like you haven’t known this was coming.””I knew it was coming, Mistress, and I’ve looked forward to this day. But I really messed up when I got mad about not getting to wear my bra, and I’m scared about messing up again.””Don’t worry, Mistress Virginia knows this is your first time. She’ll understand if you mess up. As long as you learn from your inevitable mistakes, that’s all a Mistress could ask. Did you learn anything from that little temper tantrum you threw about having no bra?””Yes, I learned at least one very important thing.””And that is?””I learned that everything you make me do is always in my best interest, so even if I don’t see it at the time, I won’t question you anymore about anything.””Anything else?””Well, I think I know now, that I can’t make my own decisions about these things, because my brain doesn’t always work too good. Marci says her brain is like that too, so I know I have to depend on you to tell me what to do.””Don’t worry too much about your tiny little sissy brain. You won’t be needing it much anymore. From now on, your only purpose is fucking, not thinking. Thinking only gets you in trouble. A sissy’s brain only works well when she thinks about making herself pretty, and pleasing anyone she’s having sex with. Is this understood?””Yes, Mistress.””Yes, what? Tell me what you understand, and how you are to think.””I’m only happy when I’m making myself pretty, and when I’m having sex. Gee… when I think about it, just thinking about sex makes me happy!””In fact, Mandy Parker, your entire life revolves around sex, isn’t that true?””I guess it does. All I think about anymore is sex. I’m getting a boner thinking about it right now.””Silly sissy,” Mistress chuckles, “save that little boner for Mistress Virginia. She just might want to play with it tonight.””Oooo…” I giggle, “I sure hope so!””What a little slut!” Mistress laughs and pinches my nipples. “Feel better now?””Yes, Mistress, much better. I think I was just thinking too much.””All you need to think about is being a good little whore for my Mistress tonight. Your little sissy brain can’t handle much more than that.”Now, when we get in there… remember to keep your spine bent backwards, like I stretch you in bondage. That’ll keep both your ass and your tits stuck out to advertise yourself. If you see a guy you think you’d like to fuck, wiggle your tits at him, just for practice. Just be careful you don’t give yourself a boner, or you’ll give away that sissy surprise you have between your legs.””I hope I don’t get a boner, cuz I’m so in love with my tits, I might wiggle them at every guy I see!”~~~~~Well, even though Mistress made me feel better, I still have a few butterflies as we enter the mall. I mean, what sissy girl wouldn’t? I’m still very self-conscious about my appearance when I’m cross-dressing in public, because I’m always afraid the real girls will know I’m a şişman gaziantep escort fake girl.I’m not so worried about the guys, cuz I’ve already noticed them eyeing my nipples as they pass by. This one guy was really hot, so I wiggled my tits at him like Mistress said. I felt really cool when I did it. I don’t even care how tiny my tits are compared to a real girl. I love them, and to me, that’s all that counts.And then there’s Mistress Virginia. I already met her a few weeks ago, when Mistress brought me here to buy sissy bras and panties. She was so nice to me, and I really liked her, but I had no idea at the time that I was going to have sex with her. I mean, she has to be at least sixty years old. I didn’t even find out she’s a Mistress until tonight, and a Matriarch Mistress at that. I guess in the Hierarchy, she must be like the Mistress of all Mistresses, right?Fuck… this is so overwhelming for my little shrinking sissy brain.~~~~~My heart is pounding when we walk into Victoria’s Secret, the ultimate sissy dream store. My sissy collar feels heavy around my neck, because it reminds me of what I’m supposed to be tonight, a human sex toy who’ll do anything and everything that is asked of me. The only question is, what will be asked of me, or should I say, demanded of me?It makes me nervous to think about it, until I remember what Mistress told me in the parking lot. Thinking only gets me in trouble. Marci always says that us sissies shouldn’t even try to think, so I just get into the moment, and gaze at all the wonderful clothes I see.”There you are!” I hear Mistress Virginia’s surprisingly familiar voice.”Good evening, Mistress,” Brenda says, “I brought you my sissy toy to play with. As you can see, she’s progressed quite a bit since you saw her last.””Indeed she has,” Virginia says as she eyes me up and down.”Twirl around for me, Miss Mandy. Let’s have a look at you.”I’m not sure how I’m supposed to twirl right here in the store, cuz you know, someone might see me. Luckily, with this being so close to closing time, I only see two other women, and they’re busy looking at clothes. So slowly, I turn around in a circle. It’s not really a twirl, but it’s the best I can do.”Very nice, princess,” Virginia approves, “you’re maturing quite well. I do like your outfit, but I’ll want to glam you up a bit. Why don’t you go look at dresses while your Mistress and I have a little chat. You and I will intimately get to know each other later.”~~~~~”My girl does good work,” Virginia compliments Brenda on my progress.”You taught me well, Mistress. I hope she pleases you tonight.””I’m sure she will. How’s she doing with the nectar?””I’m taking her into the shower a couple times a week now. She’s even started swallowing more after I told her there’s female hormones in it.””They always fall for that one,” Virginia laughs.”Yeah, I put some in her belly before we left the house.””Oh God, this is going to be fun! It’s been a while since I’ve had a piss slut to play with.””I’m surprised you haven’t been training one for yourself.””No, Bren, at my age, it’s easier to just rent one. Training those little snots day in and day out isn’t something I want to do anymore.””I can’t blame you. If you’d seen the hissy-fit she threw when I wouldn’t let her wear a bra, you woulda died laughing.””The little cunts sure get attached to their titties, don’t they? Remember, I told you I’ll pay you for the time she spends with me.””I could never charge you, my Mistress, after everything you’ve done for me. There is one little favor I’d like to ask of you, though.””Anything at all, Bren, just name it.””Put Mandy under the ‘forever a sissy’ spell, and tell me how she reacts.””Oh, hell, I was gaziantep şişman escort going to do that anyway! I just love convincing a new sissy that she’s a teenager, and will be for the rest of her life.””We’re still getting together Wednesday afternoon, right?””It’s on my calendar, lover girl. I can’t go too long without having your lesbian tongue between my legs. You’re so damn good at it.””Why shouldn’t I be damn good at? You taught me everything I know. Have fun with Mandy. I’ll come by in the morning to pick her up.”~~~~~Meanwhile, I’m lost in a world of my own as I browse through the gorgeous dresses they have here. I fell in love with this black one the very instant I saw it. As I imagine myself wearing it, I’m starting to realize how much fun it is to forget about thinking, and just be an air-headed sissy girl like Marci.Escaping the responsibilities of the real world, like the bullshit I’ve been dealing with since I started working for my dad, appeals to me. How nice it is to dream about a world where all I have to do is look pretty and have sex.”See anything you like?” Mistress Virginia comes up behind me.”I like everything I see, Mistress. Can I call you Mistress?””It’s required that you do. Of all the dresses you see, what’s your favorite?””Oh, that’s easy, Mistress. I fell in love with this black one the moment I saw it.””It would look very elegant on you with your blonde wig. Here’s one in your size, why don’t you try it on while I close up the store?””Are you sure? It’s not like I’m gonna buy it.””Haven’t you been taught to never question a Mistress?””Ooops… I forgot. I’m sorry I made such a stupid mistake.””That’s okay, hon. Now run along to the dressing room and try on your dream dress.”Oh my God…! You’d have to be in my body to even begin to experience the thrill I’m having! This is like the most beautiful dress I’ve ever seen! I can’t believe I’m even going to try it on! Holy fuck…! The price tag is like… three hundred dollars!I swear, within five seconds after closing the dressing room door, I’ve ripped off my skirt and cami, and I’m stepping into this dress! Fuck! The fabric feels so luxurious, and I feel so beautiful! I know I’ll never own anything like this, but just having it on, if only for a minute or two, gives me a thrill to die for. I can’t reach back to zip it up, so I step out to let Mistress help me with that.”How do I look?” I ask Mistress as I’m beaming from ear to ear.”It looks like that dress was made just for you. Let’s zip you up and check the fit.”It feels like even ten times better after I get zipped up. I about faint when she takes me over to the mirror. Actually, I should say mirrors, because there’s one in front of me, and on both sides.”How do you like your dress?””It’s so perrrr-fect!””It does looks good, but it’s far from perfect. Your boy-body wasn’t built to wear a dress like this. See how baggy it looks around your hips and ass?””Yeah, but I can’t do anything about that.””Yes you can,” she winks. “All you need is a few accessories that every cross-dresser should have in her wardrobe. Take off your dress, honey, right here, and everything else. Stockings, panties… everything.”A little shocked, I want to ask if I can at least go into the dressing room. But I’ve already crossed one Mistress today, and I’m not about to piss off another, especially a Matriarch, the High Priestess of the Mistresses.There’s an intensity in her eyes as she watches me strip in front of her. Feeling the warmth in that intense stare, I melt right into her when she hugs me and gently kisses my forehead. She tells me how beautiful I’ll look in that dress as I stare back into her mesmerizing eyes. Then, unexpectedly, her hand firmly cups gaziantep şişman escort bayan my balls.Fuck… all of a sudden… Boing!… up springs Mandy’s clitty!”Does this excite you…?” Mistress chuckles. “You little whore.”I’m totally speechless, standing here buck naked in front of a sixty-year-old woman who’s tracing her fingertips up and down my hard four-inch shaft. Being called a whore feels a little humiliating, but at the same time, it’s also a total fucking turn-on!”Are you embarrassed being naked in front of an old cougar like me?” Mistress asks as she squeezes my ball sack.”A little bit.””There’s no reason to be embarrassed, honey. Your clitty is one of the prettiest I’ve ever seen, and with just a little work, you could have the most beautiful sissy body.”You’re going to be my sissy whore all night, so you better get used to parading your naked body in front of me. Embarrassment is one emotion that sissy whores are not allowed to have.”Come with me, whore. Let’s get you glammed up.”She then squeezes my balls really hard before wrapping her hand tightly around my sissy shaft. That big hard-on I had? Well, that disappeared in a flash when she squeezed my balls so hard I could’ve screamed. I’m back to my three limp inches as Mistress pulls me by the clitty to the lingerie department.’Fuck…” I think to myself, ‘Marci’s gonna be so jealous when I tell her about this! I’m inside Victoria’s Secret… fucking naked… and being lead around by my clitty!… by a Mistress!'”Put these on,” Mistress interrupts my thoughts and throws a package of sheer black nylons in my face. “I’ll be right back.”I can tell these must be really expensive nylons as I roll them up my smooth legs. They’re tighter than anything I’ve worn so far, but my legs have never looked better, and they feel like heaven! I no sooner get them on, before she comes back with a weird-looking, flesh-colored pair of panties. At least I think they’re panties.”Ever seen underwear like this before?” she asks.”Umm… no. Are they panties?””In the sissy universe, we call these padded pussy panties, and they’re a sissy’s best friend when she dresses. They’ll fill out your dress in the ass and hips where your sissy body can’t yet. They’ll also hide your pathetic excuse for a cock and make you look like a female. See here…? There’s a camel toe pussy impression built right in.””Wow…!” I’m totally amazed. “I’ve never seen anything like this!””Trust me, doll, there’s a lot you haven’t seen yet. Do you know how to wear a gaff?””I’ve worn one a couple times.””There’s a gaff built into these pussy panties. See if you can get ’em on while I find a corset that’ll fit you.”Now, I haven’t worn a corset since the first time they dressed me up and took me to that sleezy motel to get gang banged. I hated it then, and I cringe at the thought of wearing one now. But I know I better just pretend to like it, because the way Mistress just squeezed my balls, I’m afraid to cross her.By the time I’ve figured out how to get myself into the padded pussy panties, Mistress comes back with a black corset. I’m staring down at my crotch, running my finger between the fake pussy lips built into the panties.”Already fingering yourself?” Mistress laughs, “Don’t tell me that doesn’t turn you on like nothing ever has.””I like it, Mistress. I like it a lot!””Most sissies do. Pretty soon you’ll be wanting transition surgery so you can have a cunt of your own.””I don’t think I’ll ever want that, Mistress.””You can say that now, but you have no idea what you’ll be wanting a year from now,” she tells me as she tightens the corset around my waist. “Has Mistress Brenda started you on hormones yet?””I think I’m starting estrogen tomorrow.””Have you been taking blockers?””No, but I’m taking sissy pills.””Sissy pills are blockers, you stupid cunt.”I had no idea what the sissy pills are, and at this point, I’m beyond caring. I know that everything Mistress does is for my own good, and that’s all I need to know. It’s getting hard to breathe as Mistress finishes tightening the corset and slaps my ass.”There we are,” she stands back to look at me. “See what the corset and pussy panties did for your figure?”

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