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?'