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SissyMandy - Inching Towards Destiny

"We knew we were going down this road. Now there's no turning back."

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Oh, dear… where should I begin? The moment Cheryl brought me home from our epic hot date in San Francisco, I knew that dramatic changes were taking place. But I guess I should first tell you what happened between me and Kristy this morning, after my coming out sex party last night.

After the Alpha t-girls had fallen asleep, Kristy and I were still buzzing on ecstasy, so we sauntered into the living room for some quiet kissing and caressing. We pleasured ourselves into the wee hours, enjoying intimate fellatio until falling asleep in an entangled embrace.

I thought I was having an erotic dream when I woke up, but it was Kristy, loving on my cock. What a dreamy way to start the day, I thought, and asked if I might return the favor. She said she didn't really need it; she was just doing it because she woke up feeling love for me.

I had mutual feelings for her, and I know you'll probably think this is stupid, but after talking about it for like, maybe two minutes, we fell in love. Crazy, I know, after just one night, but sissies are vulnerable to falling in love with just about anyone they get in bed with. Sissy love isn't like your normal, heterosexual kind of love, so it's not like we wanna run off and spend our lives together.

So when the t-girls woke up, Kristy took a shower with Cheryl, and I showered with Rachel. We knew they'd be wanting to fuck, which was totally cool with us, because, well… sissies are always horny, and always eager to breed.

After we satisfied the Alphas' libidos, Kristy let me try on some of her clothes, and gifted me with this cute, sunny-bright summer dress she had, that happened to fit me perfectly. She said she wanted me to think about her whenever I wore it, so needless to say… I wore it home.

On top of that, we had the best time doing makeup together. Kristy's mastered the art of makeup, and she gave my face the prettiest look to go along with the cute dress she gave me. In my freshly-fucked state of mind, I felt so beautiful, and so proud to be sissy-gay.

So why am I telling you this? Well, I saw a 'For Sale' sign staked in our yard when Cheryl pulled into our driveway. Several of the neighbors were outside working on their front lawns, and Sherry was visiting with a neighbor lady across the street.

Just a normal Sunday afternoon in Anytown, USA. Normal, except for the 'For Sale' sign in my front yard, and normal, except for me, Mark Harrell, arriving home dressed as Mandy Parker, my up-until-now secret identity.

There I was… all dolled-up in full makeup, and wearing Kristy's bright summer dress, in broad daylight! I almost pooped my panties when I realized my predicament, and figured I was fucked. Cheryl then told me everyone's gonna know sooner or later, and that I shouldn't be ashamed of what I am.

Fuck, I thought, easy for her to say. I'm the one who lives here, and had to make it into the house without being noticed by the neighbors. Luckily, Brenda saw us drive up and opened the garage door, but I still had to dash twenty yards in high-heeled boots to safety.

I thought I'd freak out, but I didn't. I was vulnerable, but I didn't care. I don't why, but something just clicked in my brain when I stepped out of the car. I proudly strutted my stuff like I knew who I was, and confidently pranced right into Brenda's arms as the garage door closed behind me.

~~~~~

"Welcome home, sissy-poo!" Brenda greets me with a long, loving kiss. "Was it fun being away from home?"

"Oh, wow… San Francisco was mind-blowing, to say the least. I'll probably never be the same."

"It's an entirely different world, isn't it? I knew you'd love the change of scenery. And do I detect a slight change in your voice?"

"Yeah…" I giggle, "Does it sound good…? Cheryl taught me how to talk this way. I learned so many important things last night about the sissy lifestyle."

"Tell me the most important thing you learned."

"That I'm gay. I learned the difference between regular gay, and sissy-gay."

"Mandy declared herself as queer last night," Cheryl reveals, "so we gave her three girl-cocks to celebrate the occasion, one of which belongs to her new sissy girlfriend."

"Congratulations, sweetheart!" Brenda praises me. "We've both known you were queer for a while now, haven't we…?"

"Yeah… I guess it's official now."

"I'm so very proud of you for coming out, and Sherry will be, too. Sooo… who's your new girlfriend?"

"Her name is Kristy… and oh my God… she is totally hot! She's like, everything I want to be. We're already in love."

"How neat…! Now you're in love with two sissies, and I bet there'll be more. It won't be long before you have your own circle of sissy friends."

"I hope so. I love having sissy girlfriends like Kristy and Marci."

"Kristy's been on estrogen long enough to grow her sissy titties," Cheryl tells Brenda, "so we talked about that on the way home. Mandy wants to accelerate her transition, if it's okay with you."

"Yeah," I get excited, "can I please do it? I wanna be like Kristy, as fast as I can!"

"It's fine by me," Brenda consents, "if that's what my baby really wants."

"I do! I do! I wanna be like Kristy so bad!"

"Okay, Mandy…" Brenda brings up a sore subject, "I'll approve of you going on full hormones, but only if you'll give up your resistance to going in for laser treatments to permanently remove your ugly boy hair."

"Geez, Mistress, it's so scary to have every little hair pulled out."

"It's not that bad," Cheryl says, "I've had it done."

"Mandy's such a pussy when it comes to pain," Brenda chides.

"Kristy's done it," Cheryl tells me, "and pretty much every sissy who's serious about the lifestyle gets it done. Why would you want to spread that disgusting Nair shit all over your sensitive skin, when you can just get rid of your hair for good?"

"Well, I really do hate using Nair, and if Kristy's done it, then okay, I guess I can do it."

"Trust me, girl, if you commit to the lifestyle like Kristy has, you'll be so damn hot in a few months… you'll forget you were ever a boy. And don't worry… I'll guide you through every step of your sissy puberty."

"Thanks, Cheryl," Brenda whispers as she gives Cheryl a kiss, "for the support you've given Mandy. Can I do you a little favor in the bedroom?"

"I'd love to, Bren, but I really need to get back to Alameda, so I can rest up for work tomorrow. And honestly, after last night's romp with the sissies, I'm not sure I can even get it up. Can I take a rain check?"

"You got it. I owe you a blowie."

"Bye, Mandy," Cheryl embraces me for a final kiss, "you were fantastic last night. I'll be looking forward to our next date."

"And see Rachel and Kristy again?"

"Oh yes, baby, that's a given. You're in love with Kristy, and in case you didn't notice the obvious, I'm also in love with Rachel. We'll definitely be partying with those two hotties whenever we date."

"You and Rachel…?" I blush. "Oh my gosh... that's so hot!"

~~~~~

I'm so excited as I head to my bedroom to unpack, I just have to stop in the bathroom to check myself out. I love how pretty I'm already starting to look, and the very thought of taking more estrogen to grow my tits has me pulling my dress out to pretend I have them right now.

"You're gonna be so sexy with boobs." Sherry suddenly appears in the doorway as I'm prancing in front of the mirror.

"Sherry!" I shrink with embarrassment.

"It's okay, sexy. There's nothing wrong with pretending you already have tits."

"Sorry, you kinda startled me."

"Nothing to be sorry about. I came home when I saw you and Cheryl drive up, cuz I missed you last night. Did you have a good time with Cheryl?"

"I had the best time ever!"

"Got lots of cock, I bet."

"Oh, yeah… mostly girl-cock. I met Cheryl's t-girl friend Rachel, and her sissy wife Kristy. They were so hot, and I fell in love with Kristy."

"So I take it you had a girl-cock foursome?"

"Oh, fuck, did we ever! It was amazing!"

"Will you tell me about it?"

"I dunno… it's kinda private. I mean, some of the stuff sissies do in bed might gross you out."

"Oh, c'mon... I'm your wife, for fuck's sake. Not much grosses me out anymore, so it's not as if I'm going to be shocked. Tell me about it, Mandy, I bet it's good."

"Well… would it bother you if I told you I came out as gay last night?"

"Bother me?" she laughs. "Are you kidding? Sweetheart, anyone who's infatuated with cocks like you are, is probably gay. So what…? You're gay, and I'm lesbian. That makes us both bisexual queers.

"I'll tell you something… I'm becoming more of a lesbian every time I sleep with another woman. So I think it's very fucking hot that you love dick, because the more you fuck like a girl, the more female you become, and your lesbian wife loves you more and more because of it.

"I haven't told you this before, but I've had this secret desire to watch you with a man. I wanna see him fuck you, right in front of me, and I often wonder, honey, if you have secret slutty desires you might be wanting to tell me about. So… do you?"

Oh, God... I do have this one slutty secret I've been wanting to tell her about so damn bad, but Brenda doesn't want her to know yet that she pees in my mouth. So reluctantly, I just answer, "Not that I can think of."

Sherry has this evil look in her eye that I don't think I've ever seen before. It's a look of pure lust, with a distinct hint of jealousy, and it gets more intense as she raises my dress and slips her hand into my panties.

"Tell me about your hot foursome last night," she playfully demands as she squeezes my balls. "I wanna hear you tell it in your new girl voice. Tell me about it, Mandy, and maybe we can do the same stuff when we go to bed, cuz Brenda wants us to sleep together tonight, just you and me. Won't that be fun?"

Oh fuck… knowing that Brenda's gonna let me sleep alone with my wife turns me on something fierce, so of course, I start telling Sherry about last night's sexual goings-on. She listens intently as I tell her how I lured a man into a bathroom, and sucked his cock in a toilet stall.

She starts stroking my dick when I tell her about me and Kristy sucking each other, and holy fuck, when I tell her about me sucking all three of them at the same time. She drops to her knees, gets under my dress, and starts sucking my cock!

Oh, my fucking God…! Watching Sherry's head bobbing under my dress as she deep-throats my four inches is so fucking hot!. We've never done it like this, and I have to say, it's pretty fuckin' cool.

"Keep talking, babe," she says as she sucks, "this is making me wet!"

I noticed she got really hot when I told her about how Kristy sucks dick to give pleasure, so I tell her how Kristy sucked me after we'd both been fucked a bunch of times. I describe every minute detail I can remember, and as I'm telling her this, she sucks me the exact same way as I'm describing how Kristy does it!

Fuck, this is good. She must be jealous of Kristy, the way she seems to be competing with her, trying to do everything I describe just a little bit better than Kristy did it. Should I tell her about Kristy sticking her finger up my butt? Hmmm… maybe not. I don't want to gross her out and ruin the moment. Maybe I'll tell her about the ass-play later, when we're in bed.

I tell her instead about Rachel's gorgeous girl-dick, how I sucked it, and how good it felt when she fucked me probably a half-dozen times. Hearing about Rachel's cock really turns her on, and she sucks me better than she's ever sucked me before. I'm trying not to think about Rachel as my turned-on wife deep-throats me, but it's impossible not to do.

Oh, damn… as I grab Sherry's head and mouth-fuck her like I fucked Kristy's mouth, she purses her lips so tightly around my hard cock that I don't think I can last much longer.

Kristy was definitely right about sissies with tiny cocks. Now that I'm a sissy, I don't have to prove a manhood I never had, so it's actually more of a blessing than a curse, because with only four inches to swallow, I get deep-throated all the time!

Sherry knows me so well, fondling my balls as her tongue flutters all over my stiff little prick. She's doing everything better than she's ever done before, and just like that…

"Ohhh…fuuuck..!" I grimace as I explode in her mouth!

"Mmmm…" she moans under my dress.

"Did you like it?" she giggles as I help her to her feet.

"Oh, God, that was the best blow job you ever gave me!"

"Am I as good as Kristy?" she winks. "Cuz if I am, there's more where that came from."

"Want some?" she then opens her cummy mouth before I have to answer that uncomfortable question.

It's strange, I think, as we kiss and pass my wad back and forth, that we've never snowballed before, not until I told her about me doing it with Kristy. I wonder if there's more slutty things we'd both like, but just haven't explored the deepest depths of our dirty little minds to find out. I hope there is, cuz there's nothing I'd like better than to do some of the kinky shit I've seen on porn with Sherry.

We snowball my wad until we swallow it all, and then just stare at each other, speechless, probably thinking the same dirty thoughts, until Sherry breaks our melancholy bliss.

"Where'd you get the pretty dress?" she wonders. "Did Cheryl buy it for you?"

"Kristy gave it to me. Do you like it?"

"I do. It fits your sissy personality very well. The neighbors were quite impressed, I'm sure."

"They didn't see me, did they?"

"Are you kidding? I know Margaret saw you prancing into our garage, cuz I was across the street visiting with her when you came home. She didn't say anything to me about it, but you know she's on the phone right now, spreading gossip about us. Let's go talk with Brenda about that. We have some exciting news to tell you."

~~~~~

"You probably noticed that I put the house up for sale," Sherry says as we enter the living room, where Brenda sits on the couch with her laptop.

"Yeah, what's up with that?"

"Well, you know we've been house hunting," she says as we sit on either side of Brenda.

"We found our perfect property last week!" Brenda claps excitedly. "I made a cash offer above the asking price, and the owners accepted. So we're moving as soon as escrow closes."

"Where are we moving to?"

"That's none of your sissy business right now. You'll see it when we move in, after Sherry and I have it painted and furnished the way it needs to be to suit our needs. The owners gave us permission to start remodeling right away when I put up cash to expedite the escrow process, because we need to get out of this fucking neighborhood as soon as possible."

"The neighbors have been asking me about you, Mandy," Sherry tells me, "wondering why Mark isn't around much anymore. And with gossip-queen Margaret across the street seeing you in a dress when you came home, it won't be long before everyone knows.

"I'm not worried about it, because we were already going to move. You shouldn't have to hide it, and I don't want you to, because Mandy's the person I want to be with, not Mark. I'm in love with Mandy, and I just don't have those same feelings for Mark anymore."

"I guess I can't blame you. I don't much like being Mark anymore, either. I've never felt more alive than I do when I'm Mandy."

"It's good you feel that way," Brenda then gives me some startling news, "because we've decided that it's time for Mark to die. So when we move, none of Mark's things are moving with us."

"What…? Not even my work clothes?"

"You'll wear Mandy's clothes to work," she snickers, "or you can just quit your job. It's your choice, but either way, your male clothes are going bye-bye... for good."

"B-but… what am I gonna tell my dad?"

"As always, sissy girl, Mistress has already figured that out. You'll tell him you're coming to work for me."

"As what, your whore?"

"In case you haven't noticed, sweetie, you're both already my whores, but that's not a legit job you can tell anyone about. So listen, here's the new legit, and keep this to yourself, because I don't want people knowing this about me.

"When my parents suddenly passed years ago, they left me a sizable inheritance, enough that I don't have to work. I only took a job as a futures trader at the bank, because I didn't have a sissy at the time, and I was getting bored. But now I have you two, so when my offer on the house was accepted last Friday, I quit my job at the bank.

"Trading securities happens to be a special love of mine that my father taught me at an early age. He was an expert trader, and I'm pretty damn good at it myself. I'll be setting up a day trading office in the new house to trade for myself, and you, Mandy, are going to masquerade as my assistant. I'll teach you a few basic things, so you can talk about it like you actually know something.

"Aside from that, you and Sherry will be spending your time pampering your hot little bodies, so you'll be the hottest babes on the Hierarchy circuit. Another one of my loves, which will greatly benefit you both, is extracting money from wealthy bank accounts, and I want my babes commanding top dollar."

"When is this all going to start?"

"Very soon, after we get moved. Sherry's already started her career when she was paid to spend the night with the Harrisons. I whored you out for that gang bang with Marci, but that hardly counts, because you've matured so much since then.

"The Harrisons want you both for a weekend trip they have coming up in a few weeks. That'll happen after we've moved, but before you and Sherry go on that trip, you have some details that need taken care of."

"Like what details?"

"Like quitting your job, for one. And for right now, putting your blonde wig on for me. I need to get a picture of you not looking like a slut."

"What for?"

"Nevermind what for, just get your ass in there and do it. I have things I want to do tonight."

~~~~~

"Do you really think she's ready to quit her job?" Sherry asks Brenda after I've left the room.

"She's never been ready for anything, unless we've pushed her into it."

"At least we've got a few weeks before we move. She'll have to tell her dad somewhere between now and then, which isn't going to be easy. She'll probably need help figuring out how to do it."

"I wouldn't worry too much about it. These things have a way of working themselves out."

"Well, next weekend, hopefully, she'll be doing that favor for Janine I told you about, so her mind will be occupied with other things, if we can just get her to quit her job."

"After spending the night with Cheryl and her tranny friend, she'll do it. She's found a classy sissy role model in Kristy, to go along with that slutty whore Marci. With sissy friends like that influencing her, she's completely committed to the lifestyle, so she'll do anything we want.

"We've turned her into our little whore, so concerning that favor for Janine, don't ask her, tell her. She's yours to take advantage of when you want something like that done."

"Okay, if you think I should, I'll just tell her. I'm your whore, too, Mistress, so I'll do anything you want, just like Mandy will."

"I know you will, love, but please, never think of yourself as a whore. In the Hierarchy, sissies are whores, and females are escorts. There's a distinct difference between a common street whore and the high-class escort you'll soon be. That difference is the clients you serve, and the money you'll be making, as soon as you get over your little problem."

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"I know… Lyla Harrison talked to me about it when I spent the night with her and John."

"I want you to work on it with Mandy, while I spend the next few nights with Virginia. Her little dick is a good size to loosen you up. I want you only having anal sex with Mandy, until taking it in the ass becomes as natural to you as fucking with your pussy. Mandy can probably teach you a lot about it."

"Yes, Mistress, I'll learn to like it. I already promised John I'd let him take me that way on our next date."

"Most of your resistance, honey, comes from the propaganda the church has been feeding you all your life. Get over it in your head, and you'll be amazed at how good it can feel to let your body naturally indulge in a man's ultimate sexual pleasure. A professional escort knows how to use her back-door pussy to extract riches from their wealthy clients. How do you think Lyla got to be so rich?"

~~~~~

With my face made up this way, I can't believe how cute I look with the long, blonde hair of my wig brushing across my shoulders. God, I'm loving this lifestyle, and I want to grow my hair even longer than this. I'm so excited that I decide to put on my padded panties, a different bra with my false tits, and parade around my room for just a bit before going back to the living room.

"How do I look?" I ask as I walk in on their conversation. I'm not sure what they were talking about, but I sense a bit of trepidation in Sherry's demeanor. That all goes away, though, when she jumps off the couch to hug me.

"You look so hot, honey!" she giggles as she takes my hands and presses them against her ass.

"I'll never be as beautiful as you, but I'll be the prettiest sissy I can possibly be."

"You make each other beautiful when you're together, and happy," Brenda then says as she gets up to hug us both. "You're gonna be the cutest couple when I present you to the Hierarchy."

"I feel like it's always been our destiny," Sherry reflects, "like it's always been meant to be."

"It's for sure the destiny I've been grooming you both for, and three of us will go far together. You'll see it more once we get moved into the new house."

"I wish you'd tell me where it is," I tell Brenda.

"Sissies wish for many things," Brenda playfully sneers, "but the only wishes that come true are those her Mistress sees fit to come true. We have much to do before we move in, the first of which is to get a picture of my beautiful sissy.

"Stand back against the wall, gorgeous girl, so I can snap your picture against a plain background."

I have no idea why she wants my picture like this, but I'm afraid to push my luck by asking, so I just pose with several facial expressions as she takes about a dozen pictures from different angles. When she's done, she quickly grabs her purse and kisses us both goodbye.

"Have fun, you two," she says as she leaves. "I'm off to see Virginia. While I'm gone, you're each other's whore, so keep that in mind when you go to bed tonight. I might see you in the morning, and I might not. Toodle-doo…!"

~~~~~

"She sure left in a hurry," I mention to Sherry.

"Virginia's her Mistress, honey. They've been in love for years, so Brenda's always excited when she gets to be with her Mistress.

"You wanna go out to dinner? You must be starved."

"I am, but I don't mind. I'm getting way skinny, so I can transition into a total girl for you."

"I do want you to be a total girl, except for when we go to bed. You have a very pretty cock, hon, and I'm gonna keep that male part of you for my own pleasure."

"She doesn't let us sleep together very often, so please, use me any way you want."

"She hasn't been letting you sleep with me because she and I are lesbian lovers, so she's mostly kept me for herself. Now that she's trained most of the male out of you, and you know your proper place in this lesbian household, she'll let you sleep with me more often.

"I love the beautiful girl you're turning into, and I get wet when I think about how hot you'll be when your physical transition is complete. I'm wet enough fuck right now, but we better get something to eat first, or we'll wear ourselves out before we even get into it.

"I so need to get out of these grubby jeans, and put on something nice," she giggles, "because you look hotter than me, all dressed up like that."

"I'll never be as hot as you," I tell her as she's changing clothes.

"In my eyes, honey, you already are."

~~~~~

Sherry lets me wear a pair of her earrings that go well with my blonde wig, and they look super-hot dangling an inch below my newly pierced ears. I can't describe how sexy I feel, walking into one of Sacramento's finer restaurants as a hot babe with Sherry.

It's so exciting, turning men's heads as the waiter takes us to our table. I'm feeling like eye candy, as they fondle me with their thoughts. We doused ourselves with perfume before we left, so I'm sure we're also leaving a strong scent behind us. It's all so much fun, wiggling my butt as I strut in my heels, but being a girl with my true-love Sherry is the most fun of all.

"I want you to order your own food," Sherry says as we look over the menu. "The more you practice your sissy voice in public, the faster it'll become second nature to you."

"I can do that. I've never felt more like a girl than I do right now."

"You look confident, sweetheart, and that makes all the difference. I was thinking, would you like to go on a date with me next Friday night?"

"Sure. Where to?"

"There's a lesbian bar downtown that Brenda and I go to. I thought it might be fun to go dancing and show you more of my lesbian side. Maybe we can even find a lesbian chick to have sex with in a motel, if you're game for something like that."

"As long as I'm with you, I think I can handle it, if a lesbian can handle a sissy."

"You'd be surprised how many lesbian girls are curious about trying it with a sissy. Look at Janine, she certainly liked it."

"God… Janine," I sigh, "I still can't believe I actually fucked her."

"Believe it, Romeo, cuz she wants it again, probably on a regular basis, and I'll let her have you whenever she wants it."

"She is the sweetest person on earth. I'll never be able to pay her back for everything she's done for me at work."

"You never know, hon, she might have a favor you could do for her."

"I'll do her any favor, any time, that's for sure."

"Remember you said that," Sherry chuckles, before quickly changing the subject. "Hey… I wanna take you shopping for clothes next week."

"I'd love that. You know how I like new clothes."

"I should tell you… Brenda's gonna throw out your cheap bimbo outfits before we move. She said you've matured enough now that you deserve a more sophisticated, higher-class wardrobe. Besides, you'll need it when we start whoring for the Hierarchy."

"You mean I'll be whoring… you'll be escorting."

"An escort is just a fancy label for a high-priced whore, babe. I know what I'll be, a whore, same as you. If everything goes right, we'll only be doing it five or six years, while we're still in our twenties.

"Lyla Harrison told me that once a whore gets to be thirty, her clients start ditching her for the younger babes that are always coming up through the ranks. Lyla recommends that during our prime earning years, we should fuck as many clients as we can, so we'll be financially set for life before our clientele drops off as we get older."

"I bet Brenda's probably going to keep most of the money we make."

"No, she isn't. You have no idea how rich she is, honey, money means nothing to her. She's assured me that everything we make will go into an account she's already set up for us.

"She's been grooming us for the Hierarchy because she thinks if she brings two new whores into their fold, they'll promote her to a Matriarch Mistress, like Virginia is. She wants that status symbol more than any money she could ever make.

"All we have to do is be good little whores and spread our legs for wealthy Hierarchy clients. We'll be living the high life and raking in the big bucks, while living off Brenda in the huge house she just bought. Wait till you see it, hon, it's gonna blow your mind!"

~~~~~

We drank almost a bottle of wine with our dinner, so we're both feeling frisky as we stroll through the parking lot towards her car. Sherry's looking better to me than she ever has, and that's saying a lot. I can't figure out why people are staring at Sherry's hands latched onto my elbow, until I realize how I'm dressed.

We look like a lesbian couple, and Sherry's unashamedly flaunting it. Shit, last night I was in San Francisco, walking through crowds of gay men with Cheryl as a gay sissy. And here I am tonight, in Sacramento, walking amongst straight people with Sherry, as a lesbian! Changes are definitely happening in the way I think, cuz it feels so hot being with Sherry like this in public.

"I want you to ruin me when we get home," Sherry snarls when we get in the car.

"Ruin you… how?"

"You'll see, my sissy stud!"

It's hard to describe the look on Sherry's face as she stares at me over her shoulder, but it's the sexiest, most evil look I think I've ever seen. She places my hands on her tits as she speeds home, and by the time we get there, I'm into her panties, fingering her wet cunt. She could have pulled into the driveway, but she parks on the street instead, apparently to attract the attention of a neighbor, peering at us from a window.

"The neighbors already know about you, Mandy," she says defiantly, "so they can be embarrassed about it, not us. We're not even going to try hiding it any longer.

"Fuck 'em, if they don't like it," she giggles, "cuz we're moving away soon, and whores like us just don't care."

~~~~~

As soon as we get in the house, before I even think about the bedroom, Sherry stands in front of me, hiking her dress above her waist. She parts her legs to reveal her sopping wet panties wedged into the smooth cleft of her pussy as she throws her dress to the floor.

Running her hands over her thighs, then up her waist as she reaches behind to unclasp her bra, her firm, bare tits fall free as her bra falls to the floor. She fixes me with the biggest grin, and slinks towards me.

My body starts to shake as she takes off my dress and throws it on top of hers. She reaches down and touches her fingernails to my thighs, raking them upwards along my trembling body, making me shudder as electric shocks of sensation fire through me. Attacking me with a passionate kiss, she removes my bra and throws it on top of our heap of clothes.

Then she turns and rubs her ass against my dick. Moans escape my lips as she starts grinding on me. My four-inch shaft springs free as she shimmies my panties to my knees and cradles my cock in the crevice of her crack.

"Here," she purrs, "is where you're gonna ruin me, with your dick buried in my ass."

"But, I thought anal wasn't your favorite thing."

"It hasn't been," she whispers in a serious tone, "but it's gonna be. When I dated the Harrisons, John wanted to fuck me in the ass, but I was afraid it would hurt too much, so I didn't let him. He was okay with it, because Lyla was there, so he fucked her ass instead. But I didn't give him every bit of me, so I wasn't the best whore I could be.

"Since then, Brenda and Lyla have both told me that the richest whores got that way because they know how to take it in the ass. I figure if I'm gonna be a whore, I'm gonna make as much money as I can, while I can.

"I need to learn how to do it without it hurting, so I'd like you to help me learn to like taking it this way. Show me how you do it, baby, make me want it, every time I have sex with a man."

I'm at a loss for words as she tells me this. All I can do is hug her tight, holding her in my arms until she grows impatient. She kisses me, softly at first, then hungrily, holding my head in her hands while her tongue dances with mine. Her succulent lips drink me into her welcoming mouth, as if it were the first time we've kissed.

I'm shaking with arousal as we break our lip-lock to take a breath of air. Sherry takes my hand and leads me past my bedroom, where we've had our sex ever since Brenda moved in with us. My heart skips a beat when she takes me into their bedroom, which has been off-limits to me unless Brenda invites me in. I've not slept alone with Sherry in this bed since she and Brenda claimed it as their own.

"Oh God..." I sigh as she stands next to the bed, waiting for me to make a move. My eyes are glued on the fullness of her tits, jutting proudly out, capped with puffy, rosy areolas and thick upturned nipples. My own nipples are firm and erect as I gaze at my wife's beauty.

I'm distracted by the sway of her tits as she bends over to slide her panties down her legs. As she widens her stance, my eyes focus on her sweet pussy, all wet with arousal, with her needy clit peeking out from its hood above her swollen labia. My instincts tell me to go for it, but before I can, Sherry reaches down and grabs my sissy dick.

"Let me get you ready to take care of me," she giggles with a twinkle in her eye.

My four inches of manhood point to the ceiling as she drops to her knees to suck me. I gasp at the feel of her hot breath as she licks the pre-cum oozing from my slit, shuddering to the sensation of her warm, wet tongue sliding down the underside of my rock-hard dick.

This is the third time I've been sucked today, and it's driving me crazy as Sherry sucks and slobbers all over my little boner. I could take this all night, but I'm already so close to cumming, and I need to save it for what she really wants, to get fucked in the ass.

I reach under her armpits to raise her off her knees. She kisses my sweaty flesh on the way up, stopping to bite my nipples before our lips meet again in passionate kisses. I gently insert one finger, then two, into the slick folds of her dripping cunt as our tongues dart back and forth. Her body shakes as I finger her pussy-hole while rubbing her clit with my thumb. Sherry gasps and shivers with delight as I ease her onto the bed and we continue to kiss.

Pumping my fingers into her hot pussy, we kiss for a few seconds more before I surprise her and pull back abruptly. She doesn't have time to think about it as I slide down her body and bury my face between her legs. Minutes after l start flicking my tongue on her swollen clit, her body erupts in orgasm.

"Oh my God, Mandy…!" she screams, "Oh, fuck… Yes, yes, yesss…!"

Her sweet girl-cum floods my mouth as I lick her hole and lap away at her swollen nub. This is awesome, intoxicating even, to hear her choked little cries as her orgasm runs its course. I love this, and I love her. I lose track of time and space as I lick her pussy with longer swipes, licking lower, until the tip of my tongue reaches the prize of the night, her pink little butthole.

Sherry's body thrashes as I give it a long, wet lick. I'm not too experienced at eating ass, but I remember vividly how Rachel ate mine last night, and I'm pretty sure I duplicate her moves. Sherry's pink little star pulsates with excitement as I probe into it with the tip of my tongue. A few minutes into licking around her ring, and doing everything I remember Rachel doing to me last night, Sherry's panting and hooking her hands to the back of her knees, pulling her legs back to give me better access to her butthole.

As I lick around her hole, I tease my finger into her, driving her wild as her tight anal muscles relax and stretch around my knuckle. Edged on by her moans, I gently insert a second finger, wiggling them around inside Sherry's hot ass, just the way I like to be fingered before I'm about to be fucked. I lick around her dilating ring, getting that pretty pink rosebud all moist and relaxed.

"Uuuuh… God, Mandy…" she whimpers as I lick around her relaxed hole. "Oohhh… my fucking God…! It feels so good. I'm ready, baby. I need your cock in me, I need you to fuck my ass!

"Nightstand," Sherry mumbles out as she rolls over on her stomach, "second drawer."

Opening that second drawer, I fumble through their dildos and toys until I find what she wants, the lube. It takes my breath away to see her getting on her knees, raising her ass, and arching her back to tilt her rump upwards as she rests her head on a pillow. She's ready, willing, and wanting to be taken, by me, a hot little sissy with a stiff little dick.

I feel like a stud as I walk towards her on my knees, squirting lube in the palm of my hand, thinking that this is how I look when I offer my ass to a man. She reaches around to spread her cheeks apart as I give her star a few little licks before greasing her barely-used butt.

She whimpers as I press my head into her, fearing the pain she's experienced the few times she's let a man enter her this way. My tiny dick slips right into her relaxed little hole, and she moans with delight as I work it in and out. My dick probably feels like a finger to her, but her sweet ass feels like a tight pussy to me as her hot hole squeezes tight around my sissy shaft.

"Oh, damn," she moans, "that feels so good, Mandy. Fuck me a little faster, a little deeper."

Well, shit, I can go faster, but my four inches are already buried inside her, so I'm as deep as I can go. She doesn't seem to mind as I pick up the pace, knowing there's no way I can hurt her. Her hips rock up and down as I pound her from behind. Fuck, I hope she's liking this as much as I am, cuz this is heaven for me.

It's a good thing I've already cummed twice today, cuz it's gonna take more stimulation to get me off, so I can fuck her longer. But after hardly getting any sleep last night with the t-girls and Kristy, I wear out after ten minutes of fucking her. Sensing my exhaustion, she pulls her ass off my cock and turns around to kiss me.

"That feels so good, honey," she coos.

"I'm sorry I wore out."

"Don't be sorry, babe, I still have energy. I'm gonna ride that little stinger you got, cuz you've helped me discover the pleasure I can have when we do it this way."

She lays me on my back, and envelopes her tight little hole around my dick. Her head falls back with pleasure as she rides my boner, her tits jiggling as she bounces up and down. I'm thrusting into her rectum the best I can, and it's not long before I'm in perfect sync with her slamming, downward plunges.

She starts fingering herself, pressing her thumb to her clit and rubbing away with abandon.

"I'm close, baby," she moans as she pushes three fingers into her dripping pussy hole. "Oooh… yeah… I'm cumming, baby! Fuck fuck fuck fuuuck!"

Her orgasm overwhelms her, and all I can do is grab onto her tits as she shakes and convulses to what must be a glorious orgasm. It's such a privilege to watch my wife let go like this, and I'm wondering if anal orgasm feels the same to a woman as it does to a sissy.

It really doesn't matter, because we've both just had the best sex we've ever had. She collapses on top of me, panting and heaving for air as I hold her tight.

"God, baby," she whispers with broken breaths, "why haven't we been doing this all along?"

I can't answer that question, but I can tell by the joyful look on her face… we're going to become experts at the art of sodomy.

Published 
Written by Jilluvscox
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