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SissyMandy - Undercover Sissy

"I'm sent on a mission... to catch a cheating husband"

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Oh boy, here I go. As Sherry's taking me to the Hermitage Bar in downtown Sacramento, I'm just hoping I can pull this off. The only reason I'm even going is because Sherry and Jeannie talked me into spying on Jeannie's husband two weeks ago.

Jeannie (her lesbian nickname) is one of Sherry's girlfriends. They've been intimate lovers for the past six months or so, and ever since she started coming over on Wednesday nights for sex, I've been joining them for threesomes.

Jeannie's husband is a cheater, which is what initially drove Jeannie towards lesbianism after years of sexual neglect and deprivation. Now, one doesn't just become bisexual unless part of them was already leaning that way, so when Sherry introduced her to the lifestyle, Jeannie naturally embraced it.

Janine (her real name) works with me at my dad's company, and we've always been the best of friends at work. Then, a few weeks ago, our relationship became sexual in nature. You already know from previous chapters how that all came about, so suffice to say that I now call her Jeannie whenever we're alone at work, and when she comes over on Wednesdays, oh my God… she's a different woman.

Jeannie's been talking to a lawyer about divorcing Brent. She wants to fuck him over in court for all the pain he's inflicted on her and the kids, but unless she can prove his infidelity before a judge, she won't be able to get the settlement she wants. This is where I come into the picture.

They talked me into it the first time we got together for a threesome. Well, they didn't actually talk me into it. It was more like Sherry told me I was going to do it, and that was that. Anyway, I'm supposed to go into the Hermitage Bar where Jeannie suspects Brent picks up his women, to somehow catch him in the act.

A scary proposition for sure, sissy me going into a men's hangout all by myself. The thing that scares me the most about doing this is passing as a female in a bar frequented by horny men in various stages of intoxication.

I've heard about sissies getting beaten up by men who've reached into their panties expecting to finger a pussy, but discovered their sissy surprise instead. So yes, I know the risks involved if I don't come off as totally passable, but nonetheless, here I am, because I'm a sissy, and sissies do what they're told.

~~~~~

Sherry and Brenda helped ease my fears last week when they took me shopping at the mall for the slut clothes I would need for this operation. Brenda had taken me to a wig shop the day before, and when I saw this beautiful, strawberry-blonde wig, I fell in love with it.

The shoulder-length blonde wig I usually wear looks good on me, but this one has long curly locks that drape over my shoulders. I felt so sexy when I tried it on, I told Brenda I just had to have this wig. She said I've been a very good sissy lately, and happily shelled-out six hundred dollars without even batting an eye.

So I'm wearing my new wig with heavy makeup, dressed in my fancy jeans with padded panties underneath. I have b-cup false tits under my red camisole, and of course, my black leather, high-heeled boots. We're on our way to see Mistress Virginia at Victoria's Secret, and I'm feeling pretty confident about my public cross-dressing, when a strangely familiar, female voice calls out from behind.

"Sherry?" the woman says. "Is that you?"

'Oh my God,' I panic, 'I fucking hope this isn't who I think it is.'

My faint hopes are quickly dashed when we turn around… and shit… there's my mom!

I'm instantly shitting a ton of bricks as my face turns every shade of red. I'm so embarrassed, caught red-handed by of all people, my own fucking mom!

"Well, hello, Ellen," Sherry courteously acknowledges her presence. "What brings you to the mall?"

"My shopping addiction," she laughs, "you know how it is."

"Indeed I do. We're shopping for clothes ourselves."

"A girl's favorite pastime."

"Ellen, you've met our roommate Brenda, and this cute girl is Mandy, a friend of Brenda's."

"So nice to see you again, Brenda," she says to Mistress.

"And it's a pleasure to meet you, Mandy. Are you from Sacramento?"

"No, ma'am," I politely say in the highest-pitched voice I can, "just visiting. I live in the Bay Area."

"Brenda," Sherry then says to Mistress, "you and Mandy can go on ahead if you want. I'd like to catch up on a few things with my mother-in-law. Wanna meet up at Vicky's Secret?"

"Let's do that," Brenda replies. "Bye, Ellen, nice to see you."

~~~~~

"Oh. My. Fucking… God!" I freak out as we're walking away from my mom, "I think I just died a thousand deaths!"

"Oh, c'mon," Brenda chuckles, "your mom didn't have a clue she was talking to her son."

"I'm not so sure! And how did you meet my mom!"

"It's none of your sissy business how I met her. What's important is she didn't recognize you."

"Well, even if she didn't recognize me, it still freaks me the fuck out!"

"I think the hormones you're taking are starting to affect your emotions. All sissies go through the emotional change before they notice the physical changes."

"Well…" I concede. "Maybe. Kristy did tell me about the change, and I have been feeling different lately."

"You're turning into a girl, babe, so embrace it. Your tits will be coming in next."

"I can't wait for that!"

"It won't be long, hon. When I take you to see Cheryl next Friday, I'll have her pump 'em up as much as she can."

"Oh, goodie! And I'll give her a nice blow job for it."

"Not if I blow her girl-dick first. I owe her one, you know."

'Rats!' I think. 'Mistress likes girl-dick, too.'

~~~~~

Unbeknownst to me, Sherry's talking to my mom about their own little secret—me!

"So now that you've seen her," Sherry asks my mom, "what do you think about your new daughter?"

"Wow. I can't get over how cute she is! I always knew Mark was different from the other boys when he was growing up, and now I know why. She doesn't suspect that I know about this, does she?"

"Oh no, she has no idea. We're just now building her confidence about being out in public, so we won't tell her about you knowing until maybe after we've moved into the new house."

"Whatever you girls think is best. I still have to figure out how I'm going to tell her about my secret."

"I'm sure you and Sarah will find the right words when it's time to do that. I'm just worried about how the dad is going to take it."

"Fuck the dad!" Ellen hisses. "All that bastard has ever thought about is himself and that damn business!"

"I better go catch up with the girls."

"Okay, honey, I'll let you git. Thank you so much for letting me see the new side of my son… errr… I mean… daughter."

"Happy to do it, mom. Tell Sarah I said hi."

~~~~~

"Hey girls," Sherry meets up with us at Victoria's Secret, "have you bought out the store yet?"

I'm in no fucking mood for chit chat. "Jesus, Sherry. How the fuck did that happen? What did my mom say? Did she know it was me? Fuck… I am so busted!"

"Relax, baby, she doesn't have a clue. You're so passable now that not even your mom can recognize you. And oh… that was a good fib when you told her you live in the Bay Area."

"I was so freaked out, it's all could think of to say."

"It was brilliant. You're learning how to tell convenient little lies to get yourself out of a jam."

"Well, hello, Hotwife Sherry," Virginia comes over after helping another customer.

"Hello, Mistress. Are you getting Mandy all fixed up?"

"Oh, yes! She'll be the hottest slut in town with the outfit we picked out. C'mon back to the storeroom with me, girls, I want to show you something I just got in last week.

"I can't put these on display," she says as we follow her into the storeroom. "I only show them to my sissy customers, for obvious reasons."

I'm getting excited as she gets a box from a shelf way in the back, cuz it'll be something for me, and I bet it'll be good.

"Look at this," Virginia says with a little chuckle. "Have you ever seen such a realistic prosthetic vagina?"

"Oh, wow!" I can't believe my eyes. "Is it like a pussy thong?"

"It's much more than just a thong, dear. It has a built-in gaff to comfortably tuck your clitty away, and when it's glued to the skin, it uses your nuts give it a natural mound shape under your panties. You'll love how it shows a prominent camel toe under tight jeans or hot pants. Don't be shy, girls, go ahead and feel it."

"Geez," Sherry giggles as we touch it, "it feels like the real thing."

"It's amazing what they're doing with silicone and latex these days. A guy can finger it through a sissy's tight jeans and think it's a real cunt."

"Do you want one, Mandy?" Brenda asks me.

"Y-yeah… of course I do!"

"They're kinda pricey," Virginia warns.

"How much?" asks Brenda.

"Four-fifty."

"You mean, four hundred and fifty dollars?" I gasp.

"Each one is handmade."

"We'll take it," Brenda approves. "My sissy needs a pussy."

"Must be nice to be a rich bitch," Virginia chides Brenda as they go to the cash register to pay.

"This rich bitch is also your bitch, my Mistress."

"That's the best part," says Virginia. "I'm so proud that over the years, you've learned to value the finer things in life besides the millions your parents left you."

"You've taught me well, Mistress. You saved my life."

"And you've brought me much joy, my child. Let's see… your total comes to six-hundred and twenty-seven dollars. I dropped the cents as a special courtesy."

"You're so kind," Brenda laughs sarcastically as we head out the door with my new slut outfit and awesome fake pussy.

~~~~~

"Hot bitch, hot bitch…" Sherry teases as she comes into the bathroom to check on me getting ready to do this special favor for Jeannie today.

"As much money as Mistress spent on my skimpy outfit," I say as I'm checking out my naked body in the mirror, "I should look like a hot bitch."

"It's quality stuff, babe, and you've lost so much weight that you've got the body to wear it now."

"Yeah. I've been noticing that some of my clothes that fit me tight six weeks ago are practically falling off me now. I just weighed myself, and I'm down to a hundred-twenty-two pounds from one-forty-three."

"That's great, hon. You're getting to be so skinny that your rib and hip bones are even starting to show, which will accentuate your tits when they start growing. And your nipples, babe, they look so luscious after whatever Cheryl did to them."

"I didn't know she was going to do it before she put me to sleep, but she used this stuff called Juvederm, I think she said. They use it to give women fuller lips, but she injected it right into my nipples!"

"I'm telling you, babe, your nipples look so hot that some girls would be jealous. Your tits could probably fill an A-cup right now after Cheryl pumped them up yesterday."

"Yeah," I giggle. "Brenda said I shouldn't wear a bra today. What do you think?"

"I think she's right. You might as well show 'em off while you've got 'em. They'll look hot under the tight-fitting pullover top Virginia picked out for you."

"I can't wait to wear it. You wanna help me get this fake pussy on and glued in place before I get dressed?"

"I might have to suck you off first. Is that okay?"

"You treat me too good," I giggle as Sherry drops to her knees.

"Nothing's too good for my sissy husband. I'm more in love with you than I've ever been."

~~~~~

My fake pussy was expensive to buy, but it was so worth it. It tucks everything away in total comfort, especially with my clitty being so limp after Sherry sucked me off. When she glued it in place, the color blended right into my skin, and from a distance, you'd never guess it's not a real girl's pussy.

It's weird how losing weight is such a gradual thing that I hardly noticed my day-to-day progress. Sure, I knew the numbers on the scale were going down, and my clothes are fitting a lot more loosely, but I didn't realize just how far I've come until I see myself all glammed up in the mirror, dressed in my new, tight-fitting slut outfit.

I don't know if the estrogen is already starting to re-shape my legs, but they feel so comfy and look so feminine encased in my black, thigh-high cotton stockings. The three white bars on top hotly highlight the ten inches of sexy leg showing below my super-short, faded denim jeans that are frayed at the bottom.

My hot-pants-style jeans are skin tight, with a twenty-eight-inch waist I couldn't have worn two months ago. I've got a prominent, natural-looking pussy impression showing between my legs, and my pumped-up titties give me a petite, but definite bust line under the tight fit of my black pullover top. My nails are painted black to match, and with the slutty makeup Sherry put on my face, everything about me just screams sex!

When Brenda sees me and says she's proud of the skinny bitch I've become, I can't resist taking a selfie of myself to send to Kristy and Marci. Before we leave, Mistress tells me she's just opened an account for me on the Grindr website. I've never heard of it, but apparently it's a social network where queer people go to hook up. The three of us laugh when she tells me my username: MouthPussy. Is that not a riot?

I don't know why Brenda does some of the crazy things she does, but everything she does has a designed purpose. She told me to remember that username, because it's gonna come in handy as I get more into my whore life. Little do I know… that username will come in handy today.

~~~~~

"How are you feeling, honey?" Sherry asks as she parks across the street from the Hermitage Bar.

"Nervous."

"I can't blame you, but I think you'll be fine. See that black Dodge Ram in the parking lot? That's Brent's truck, so we know he's in there."

"Okay," I nervously tell her as I step out onto the street, "I guess it's time to do it. Wish me luck."

"Your super-hot looks are all the luck you'll need. Act like you know you're hot, and you will be. Remember, I'll be right out here the entire time, so don't hesitate to text me if you get into trouble."

~~~~

I'm beyond nervous as I enter the dimly-lit bar. It's hard to focus on anything as my eyes adjust to the light, but I do notice a guy off to the side flirting with a girl who's dressed as slutty as I am. I'm making quite a commotion with my platform high-heels clicking on the wooden floor, which unavoidably attracts the attention of two guys sitting at the far end of the bar.

"Whatcha drinking, beautiful?" one of the guys yells out to me.

"Strawberry daiquiri," is the only drink I can think of to say.

"Put it on my tab," he tells the bartender.

Oh, shit. He's getting off his barstool and walking towards me. Fuck. it's Brent! I recognize him immediately from the picture Jeannie showed me. He's not gonna try to pick me up, is he? But why else would he have bought me a drink? I don't see any other girls in here, and shit… he's definitely got his eyes on me! I have to think fast, make up a story, invent a white lie, anything to fend off his expected advance.

His is eyes are drawn to my fake pussy outlined through my super-tight jeans as he approaches me, and then I don't mean to, but when he starts staring at my sissy tits, I can't help it. I just automatically pull my shoulders back to advertise my hot nipples pressing through my tight top. Shit, I know I shouldn't have done that, but it's what I've been programmed to do.

"What's a gorgeous girl like you doing in here on a Saturday afternoon?" is his opening line.

Geez… he's so close with his elbow resting on the bar that just the smell of alcohol on his breath somehow triggers the insatiable lust for cock that's been embedded in my one-track sissy brain. It's telling me to let him come on to me, and shit… I almost do! Luckily, I come to my senses just in time to catch myself succumbing to my sissy desires.

"I'm just waiting on a date," is the first thing I can think of to say.

"Boyfriend?"

"You might say that."

"Might?" I unintentionally trigger his interest.

"Well…" I stumble on my words. "Today's boyfriend, at least."

"What about tonight's boyfriend?" he asks, as if I'm a whore, which of course, I am.

"I'll have to see what develops."

"Tell you what, honey," he says in a macho tone, "they call me the Spoiler. If nothing develops, and you're looking for some action, I'm here to help."

Then, like a chauvinistic pig with an evil grin, he grossly runs his hand between my legs and pokes at my fake pussy.

"I can make this happy, darling," he says, and then he pokes at my nipples!

"Think about it," he chuckles as he heads back to his buddy, leaving me dumbfounded.

I'm thinking about it, alright. I'm thinking he's the asshole Jeannie says he is, and now I can't wait to bust his ass. I take my free drink and saunter over to a table by the wall, sipping my daiquiri and getting my cell phone camera ready in case another girl walks in, and he does the same thing to her.

Unfortunately, an hour goes by, and no other girls come in. I'm getting kinda bored, so I text Sherry to report on the lack of action.

'You still out there?' I text.

'Yeah, babe,' Sherry texts back. 'Any luck?'

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'No. There's only one other girl in here besides me. But I can see why he gets a lot of chicks. He's kinda good-looking. He even tried to hit on me.'

'Don't let him get you.'

'No chance. He did buy me a drink, though.'

'Be careful, babe.'

'I am. Gotta go… he's coming towards my table.'

'Put your cell camera on video, so you can record what he says.'

'Got it.'

Sherry's so smart. I would never have thought to do that. I barely get my cell video going and put away in my clutch purse, when he arrives with a fresh drink in his hand.

"Your glass is empty," he says as he sits right next to me. "I brought you a refresher, because I'm such a nice guy."

"Thank you, sir," I say, because, well… what else could I say?

"The name is Brent, hotcakes. What's your name? Or can I just call you hotcakes?"

"No…" I start giggling. I can't tell him my sissy name, so I make up one. "My name is Tina."

"Where's your Romeo boyfriend, Tina?"

"Ummm, it looks like… I got stood up."

"It happens. Known him long?"

"No. This was supposed to be our first hook up."

"So what happened?"

"Maybe he got cold feet?"

"A hot babe like you? Don't bullshit me, Tina. I can tell when a chick comes in here to get laid."

Fuck, I can't believe I'm actually talking to this jerk. But I know everything he's saying is being recorded, so I keep talking to him. He comes on strong, and after a while, I'm having trouble resisting his moves as he inches his chair closer to mine.

"C'mon, Tina," he then says as he grabs my inner thigh under the table, "tell me why you really came in here."

Things are moving too fast for comfort, but he's a good-looking guy, and I hate to admit it, but I'm getting horny. I'm already talking to him, flirting with him, actually, so why not make up a line and see if he falls for it?

"I was supposed to meet this guy here," I say like an innocent girl, "but it's too embarrassing to say why."

"Don't be shy, baby, you can tell me."

"Well… well… you're not an undercover cop, are you?"

"You're not a whore, are you?" he starts taking the bait. "No, I'm not a cop. Now spit it out, are you a whore?"

"Well… kinda, b-but, I only do it at the end of the month when my welfare money runs out."

"You don't look like a welfare bitch with those fancy clothes."

"B-but… that's my problem. I spend too much on clothes. I mean, I do have to look good in my line of work, don't I? But then I don't have enough to feed myself. That's why I have to turn tricks, part time, of course."

"So what was this 'part-time' trick with Romeo supposed to be?"

"Just a little blow job."

"What about this hot pussy?" he comes on stronger, pressing his finger right into my fake cunt. "You don't sell that, too?"

"Please don't touch me there," I whimper. "I mean, yeah, I do sell it, but I'm on my period right now, so I can only use my mouth. I really need fifty bucks, cuz I haven't had much to eat all week."

"Fifty bucks?" he laughs. "For a cheap blow job?"

"Well, sometimes I'll cut my price when I'm hard-up, like now."

"Tell you what, Tina, you're lucky I don't discriminate. I don't mind paying for it if nothing else is available, so I'll give you twenty if you'll come out to my truck and polish my nob."

Oh, fuck, what did I just do? Did I just proposition the guy? Shit… I didn't think he'd actually go for it. Gotta think fast, gotta brush this guy off.

"Only twenty?" I act like I'm put off, hoping to chase him away.

"Trust me, hotcakes, once you've had my meat in your mouth, you'll be wanting to pay me!"

With that, he grabs my hand and forces me to feel his cock, and oh my God, it feels gigantic! Fuck, I just can't let it go as my sissy hormones shift into 'must have' mode. Sherry's gonna kill me for this, but I can't control myself.

"I might be willing to do that," I say rather shyly, "but you have to promise me one thing."

"And what would that be?"

"You stay out of my pants. I normally wouldn't mind, but like I said, I'm on my period, and it's kinda messy down there right now."

"Don't worry, I never touch a bitch when she's like that."

"Pay me first."

"You don't trust me?"

"I can't take chances. I've been ripped off before."

"Shit," he grumbles as he reaches for his wallet, "ain't this a bitch?"

"Can I use the restroom first, so I can check my Tampon?" I ask as he hands me the twenty.

"Go ahead, but don't take all day."

~~~~~

I scurry into the ladies room and immediately text Sherry. 'Still there?' I text.

'Yeah, what's going on?'

'He's taking me out to his truck.'

'Mandy… you bitch. Don't you dare fuck him!'

'I'm not, it's just a suck. He made me feel his cock, and then I couldn't say no. He's even paying me twenty bucks. Make a video of us going out to his truck.'

'Good idea, babe. Be careful, I don't want you getting hurt.'

'Gotta go. Watch for us.'

God, after thinking about it while I was texting, I can't believe I'm doing this. But I can't turn back now. Mistress Virginia says I should always live in the moment, so I might as well enjoy this moment. He's an asshole, but he's got a nice cock, and that's all this sissy wants.

~~~~~

I act like a horny bitch as I prance back out to where Brent's beginning to salivate at the thought of fucking my mouth. My phone's still recording everything we say, so I put my arm around him as we head out the back door to the parking lot. Knowing I've got his guard down, I then sweet talk him, just to see if I can get him to confess anything.

"Can I ask if you're married?" I start out.

"She is, but I'm not."

'Bingo!' I think, before following up with… "A cheater, huh?"

"Some call it cheating, I call it spreading the love. Not many women have experienced what the Spoiler can do."

"I'll bet," I keep stoking his ego, "doesn't your wife give you any at home?"

"I haven't fucked that bitch in years, and why should I? She'd just pop out another kid I'd have to support for eighteen years. Who needs that, when there's other bitches I don't have to worry about getting preggo on me."

We're almost to his truck when I notice Sherry's positioned her car to an ideal spot where she won't be noticed, but still able to see everything we're about to do. Hoping she's got her video going, I put both my arms around him, and when I do that, he squeezes my ass as I hang on him all the way to his truck.

"Take your top off," he orders the moment I get in.

"Well, suppose I can, but I usually charge extra for that."

"Extra? Just to feel Tina's tiny titties while she blows me? Don't make me laugh."

"Okay, okay, so I was robbed in the tit department. Please don't make fun of me when I'm trying to get in the mood."

"Sorry, baby," he apologizes as I take off my top to expose my sissy breasts.

"Small, but cute," he compliments my sissy tits. "Love the nipple rings."

"Yeah," I giggle, "I had to do something to make 'em more noticeable. You wanna kiss a little first? It helps get me in the mood."

"You're lucky I didn't just kiss that cute face in the bar."

"I wouldn't have minded."

He all of a sudden takes me in his arms and gives me slobbery kisses all over my face. Oh, yuck! This guy is definitely not a kisser. I kiss him back a few times as his hands grope all over me, but I get zero pleasure from it.

Then he starts slobbering all over my tits, which I kinda enjoy, because I've never had a man on my tits when they're pumped up. I stay as close to the windshield as I can, so Sherry can get a good shot of him doing that. In less than a minute, he's grossing me out so much that I reach for his zipper, desperately wanting to just suck him off and get it over with.

"Oh God," I fake-pant to him, "how did I get so turned on?"

"I told you, no bitch can resist the Spoiler."

"Phew! I see what you mean. I'm so ready to suck your cock now. I gotta have it, like right now!"

"It's all yours, you little whore."

What an insult, but what the fuck. At least he won't be kissing me with his cock in my mouth. He tilts his seat backwards and folds his hands behind his head as I unzip his pants. His shitty kisses must have turned him on, because he's pretty hard when I take him out. I'd usually want to pull my man's pants down, so I can enjoy his entire package, but not this guy.

His cock is nice, but not as nice as I thought it would be. Somewhat disappointed, I stroke him a few times before lowering myself to lick around his head. Not bad, really, once I forget who I'm about to blow.

"What's the matter, bitch?" he grows impatient. "Don't tell me you're afraid of my monster."

"But it's so big!" I tease.

"They don't call me the Spoiler for nothin'," he laughs as he slaps my ass. "Now suck it… bitch!"

Shit… that did it. Now I'm gonna make him cum fast as I can, just to deprive him of his enjoyment. I start bobbing my head up and down on his rock-hard shaft as he moans like a sissy to the pleasures of my pussy mouth. I'm bobbing up as high as I dare, hoping Sherry's getting this on video.

He grabs my head and forces me all the way down, and I let out fake gags to make him feel more macho. It works like a charm as my tongue wraps around his shaft.

"Woo-hoooo!" he yells as I quickly get him to cum in my mouth.

He's breathing hot and heavy as I swallow his generous load, and then, like a true asshole, he raises my head and shoots the last two ribbons across my face.

"Something to remember me by, hotcakes," he laughs as I raise my myself up in my seat.

"Did you like it?" I ask as I gather myself.

"Not bad, but I've had better."

"I'm better in bed than I am in a truck, Mister Spoiler."

"Fair enough. I'd like to get you in bed and work your twat over. You game?"

"Maybe. For three hundred."

"Ain't that a little steep?"

"Not for all night. But I'm guessing you probably can't get away from your wifey for an entire night."

"The hell I can't! That bitch doesn't run my life! I just tell her I'm going fishing overnight with the boys, and the bitch never knows the better. What's your cell number, so I can text you?"

"I don't give out my cell. I only talk to my dates on Grindr."

"What the fuck is Grindr?"

"A website where I find my hook-ups. There's lotsa chicks like me on it."

"Oh yeah? I'm always on the prowl for pussy."

"There's always tons of pussy like me on Grindr. Just sign up, and it's easy to score. My username is MouthPussy. You can reach me there."

"Okay, I'll sign up and hit you there. How about setting something up for next weekend?"

"I'm not sure, I'll have to check my appointment calendar. Hit me up next week and I'll let you know. I'm usually only available in the daytime, cuz, you know, I work most nights."

"Speaking of work, I gotta get going. The wife thinks I'm at work."

"Okay, I need to get something to eat, now that I've got money. Where's my top?"

"This?" he holds my top and pulls it away when try to get it.

Then the prick laughs as he throws it out the window. "Go get it… MouthPussy!"

Fuck, how embarrassing. I have to get out his truck topless, and walk twenty feet just to cover myself up. Luckily, I don't think anyone besides Sherry sees me picking my top off the pavement, but as a final insult as I'm putting it back on, he starts his truck and hits the gas, squealing his tires as he peels out of the parking lot.

~~~~~

"What a jerk," I tell Sherry when I get into her car.

"What a careless bitch you are!" she angrily scolds me.

"What?"

"You know what. You shouldn't have taken a chance like that. What if he had found out you have a cock?"

"I told him I was on my period, so he wasn't about to reach into my panties."

"You little fibber!" Sherry busts out laughing. "I should be mad at you, but I can't be, cuz that was a brilliant move."

"Plus, I got lots of dirt on him to give to Jeannie."

"I bet you did. I got everything you did in his truck on video, so Jeannie should have plenty of evidence to use in divorce court. You must be hungry. You wanna get something to eat before we go home?"

"Yeah, I'm starved. I'll buy, I just made twenty bucks sucking that prick's cock."

"Cheap whore," Sherry laughs.

"I felt cheap doing it. That was the first time I didn't love giving head."

"Hopefully the last time. Hierarchy clients won't treat you like that. Brenda says all their clients are thoroughly vetted before they're allowed to date us. They look after our safety."

"That's good to know."

~~~~~

I've got cum on my face and I can't clean up in the car, so we decide to get fast food at McDonald's. Since I've lost so much weight, I decide to splurge, and order a double quarter pounder combo meal. I'm having trouble getting my twenty-dollar bill out of my tight jeans pocket when we get to the drive-thru window, so Sherry just uses her credit card to pay.

When we get home, I couldn't care less if the neighbors see me dressed this way, so I put my arm around Sherry, and we prance to the front door instead of sneaking through the garage. Brenda's in the living room waiting for us, anxious to hear how our undercover adventure went.

She sees the dried cum on my face, and asks me if he shot any into my mouth. I say, "Of course," to which she says, "Don't start eating or sip any of that coke just yet."

Sherry and I wonder what Mistress is doing as she goes to the kitchen and brings back an empty glass. She tells me to spit in it, and when I do, she peels some dried cum off my cheek and puts it in the glass with my spit.

I ask her, "What's that for?" And she says, "Evidence."

"Evidence?" I wonder.

"Yes, evidence. Bodily fluids containing his DNA mixed with yours. It's the best evidence in court to prove he's had sex with you."

Damn, I don't know where Mistress got her brains, but I hope some of her smarts rub off on me. Sherry remembers that I still have the twenty he gave me, and we save that for evidence, too, since it's got both of our fingerprints on it.

All in all, it was a successful day of private investigating, and the best thing I learned was that I'm definitely passable as a chick pretty much anywhere I want to go. All I have to do is forget I was ever a male, and it all comes naturally.

~~~~~

When I get to work the following Monday morning, Janine and I exchange our normal 'Good mornings' in front of the office girls. A few minutes into the morning, she comes in with a contract and closes the door behind her. Janine then becomes Jeannie as I get up to hug her, and she showers me with the sweetest kisses for I don't know how long.

"Oh, Mandy," she tells me, "you are the best friend in the whole world! I owe you a thousand blow jobs for what you did for me with Brent. I certainly didn't expect you to actually have sex with him."

"I didn't expect it either. It just sort of happened. But I found out what a prick he is."

"He didn't use to be that way. When he changed jobs and started hanging around a different crowd, everything changed for the worse for me and the kids. But thanks to you, his world is about to change in ways he's not expecting."

"He wasn't expecting to do it with a sissy," I laugh.

"I wonder what he'd say if he realized he's received oral sex from a biological male?" she giggles.

"He might."

"What?"

"He thinks I'm a whore, and wants to pay me to spend the night with him at a motel next weekend. I wouldn't give him my cell number, but I gave him my username on this gay website, where Brenda opened an account for me.

"He said he'd open an account and contact me there it to arrange the hook-up. I'm going to load the app on my computer, in case he tries to contact me from his work."

"Let me know if he does. That would be even more evidence to give to my attorney."

"You'll be the first to know."

~~~~~

Nothing happens the rest of the day, but I've got the app loaded to alert me if I get any chat requests. I soon get like, two dozen requests from guys wanting to meet me, probably because of my 'MouthPussy' username, but I put them all on 'ignore'.

It's not until Tuesday afternoon when I get a chat request from a 'Spoiler4You' username.

'Jackpot!' I think when the first line he writes is 'Hey, hotcakes, are you on?'

I immediately rush out to Jeannie's desk and ask if I can see her in my office.

"It's him," I tell her as she's closing the door. "You wanna chat with him, or should I?"

"Let me do it," she says as she licks her chops. "This should be interesting."

Oh, it was definitely interesting, alright. Jeannie and I giggle the entire time she's chatting with her unsuspecting husband as he's doing this at work, which would get him in big trouble if his boss found out about it.

You'll just die when you find out what happens next, but I'll have to tell you about that in the next chapter. Meanwhile, if you've enjoyed this adventure so far, please take a second of your time to let me know by hitting the 'like' button below. It's the only way Jill knows if she should continue writing about my sissy life. Kisses ~ SissyMandy.

Published 
Written by Jilluvscox
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