I've got the worst case of the butterflies as I'm driving off to work this morning. After my fabulous sissy-gay weekend in San Francisco with two trans girls and another sissy, it's no wonder I'm so depressed about returning to the straight world and wearing a business suit.
The panties and nylons I have on underneath do help, but it's not just the male clothes that repulse me, it's the whole notion of pretending I'm still a straight, heterosexual male. I mean, I'm so far into the sissy lifestyle now that I can't even imagine being a straight person anymore.
It's always a bummer on Monday mornings when I have to shed my exciting Mandy Parker identity to become boring Mark Harrell again, but at least Sherry and I were excited this morning about the new house that Brenda just bought. I'll be their full-time sissy when we move in, but my excitement about that is tempered when I remember Brenda saying I'll have to quit my job before that happens.
I do hate my job, and I'll gladly obey my Mistress, but the thought of having to tell my dad I'm resigning terrifies me. I'd put it off forever if I could, but Mistress is always two steps ahead of me, and has already taken that option off the table.
She's getting rid of all my male clothing before we move, so if I don't quit my job by then, I'll have to wear my sissy clothes to work. There's no fucking way I'm ever showing up at work in a dress, and you'd think that's why I've got the butterflies so bad as I'm pulling into my reserved parking space at my dad's company, but actually, I'm nervous about something else.
What scares me at the moment is Janine, the last person on earth I ever imagined I'd have sex with. It seems like a lifetime ago after my slutty weekend in San Francisco, but it was only last Friday when we found ourselves in bed together.
As one might imagine, once you've had an unexpected sexual encounter with someone you work with every day, the relationship is forever changed, which is why I'm so nervous about it. Sherry did say that Janine liked it and wants to do it again, but it's been an entire weekend since she's seen my pathetic little dick, so how do I know she hasn't changed her mind?
My nerves are on edge like never before, but sitting here in my car pondering over it isn't helping my situation, so I might as well just go in and face the music before I'm late for work. I guess the worst that could happen is she'll never talk to me again, right?
~~~~~
Oh dear… as if I'm not already nervous enough, it seems I'm attracting the attention of every girl in the office the moment I walk in. They're no doubt staring at my pixie hairstyle, and I bet they've been gossiping about me since they first saw it last Friday. I sure hope they don't notice the diamond studs in my newly pierced ears, because that would suck even more than the gossip about my hair.
"Good morning, Mark," Janine greets me like she does every morning.
She smirks when I can barely say 'Good morning' in reply.
"We need to go over the Delta contract first thing, f you don't mind."
"Y-you mean like… right now?"
"That would be best," she smiles as she gathers her papers and follows me into my office.
She usually leaves the door wide open when she comes in to go over work, but this time she closes it behind her.
She then sweetly says, "Good morning… Mandy."
It's good my office doesn't have windows, because as I turn to face her after hearing my sissy name, she comes up and plants a big, wet kiss on my lips.
"Hey, babe…" she smiles seductively, "I've been dying to see you."
"Y-you… still like me after what we did Friday?"
"Listen to you… of course I still like you. Didn't that kiss just tell you something?"
"Y-yeah, I guess… it's just that… you know… I never thought you and me… would ever… ummm…"
"Be lovers…?" she finishes my sentence for me.
"Y-yeah… I was afraid you wouldn't want me again after seeing my tiny dick."
"Listen," she says as she presses her hand into my crotch, "big cocks don't impress me like they once did. I prefer tongues now, and yours more than makes up for your cute little penis. Sherry and I have been wanting to tell you about our affair for a while now, but Brenda wanted us to wait until she felt the time was right."
"Brenda… I figured she probably arranged the whole thing."
"Yeah, she arranged it alright. You're not mad at us for tricking you into it, are you?"
"Naw… Brenda's always tricking me into shit like that. I was just embarrassed when you found out I'm a sissy, especially after you hid your face the whole entire time I was licking between your legs."
"Sweetheart, I've always known you're a sissy, and if you'd known it was me under the sheet, you might have chickened out. And besides, I was as nervous about it as you were, but wasn't it fun once we started getting into it?"
"Well, yeah… it was definitely fun, and I liked it a lot, b-but… what do we do now?"
"Isn't it obvious what we'll do?" she grins. "I'll be coming over to your place instead of meeting Sherry at a motel every week."
"What…? Y-you mean… you do it with Sherry every week?"
"Pretty much every Wednesday after I get off work, for about six months now."
"So that's why Sherry's never there when I get home on Wednesdays?"
"Yup… that's why. My mom thinks I go out with the girls after work on Wednesdays, so she picks up the kids and watches them for me while your wife and I indulge in lesbian sex."
"Do you see other girls besides Sherry?"
"I don't have time to see other girls when I'm basically raising three kids by myself, but I'm looking forward to Brenda joining us at some point."
"Do you know that Sherry and Brenda sleep together every night like they're married?"
"Yes, I know… they've been in love for over a year now. But Sherry's also in love with you just as much. That sweet girl has enough love for many relationships."
"I know that's right. I guess I've become the same way. This probably sounds weird, but I'm in love with two sissies and a gay man, all at the same time."
"It's not weird if Sherry's okay with it. You two have a beautiful open marriage arrangement. I'd love to have a marriage like that."
"Sherry told me you're not happy with your husband."
"I'm not," she sadly sighs, "but let's not get into that right now. We better get some work done before people start talking."
"The office girls aren't already gossiping about us, are they?"
"We just did it last Friday, so they couldn't possibly know, but we mustn't show any affection towards each other when we're around them, or those nosy bitches will start getting ideas. I can't afford to lose my job if your dad happened to get wind that I'm sexually involved with his son and daughter-in-law."
"Well, we won't have to hide it for long, cuz we're moving in a few weeks, and Brenda's making me quit my job before we do."
"Yeah… Sherry told me all about it. I'm happy for you two, but I'm also sad that we won't be working together much longer."
"Hey… maybe I can talk my dad into giving you my job when I leave."
"I won't hold my breath. Your dad is such a chauvinistic asshole, I doubt he'd even consider promoting a woman to a higher position. I've been looking for a better-paying job, but I'm stuck here until I can find something. Anyway, let's get this contract done before I start getting sad about my situation."
Janine quickly changes the subject to focus on the contract, but my mind remains focused on her. I know her husband cheats on her, and I also know what a hot babe she is in bed, so I can't help but wonder why he's not banging her every night. The way she avoided the subject told me it's probably none of my business, but I'd like to make it my business if there's any way I can help her.
I can tell she's hungry for affection by the way she lets me run my hand between her legs as she stands next to my chair. She's also not shy about sticking her tits in my face as she bends over to point out where I have to sign the contract. It's all I can do to keep my hands off them, and I don't mind admitting that by the time she prances her hot ass back to her desk, I've got a stiff hard-on going on.
~~~~~
Since I didn't get shit done last week, there's plenty of paperwork stacked up on my desk, but the only thing I can think about fucking Janine. I know I'm addicted to sex, like every sissy is, but sometimes I wish I could think about something else once in a while. I'm shuffling through the papers, trying to at least look like I'm getting something done, when my dad pops in without even knocking.
"Mark," he says in a stern tone of voice, "come down to my office. We need to talk."
Oh shit, I wonder what he wants to talk about. My hair? Probably. Should I just tell him I'm going to quit and get it over with? Brenda would be proud of me if I did, but I don't know if I have the guts to do it.
My worst fears are confirmed the very moment I take a chair in front of his desk. He's absolutely livid as he lays into me about my pixie hairstyle, telling me I look like, and these are his exact words, 'A god-damned queer!'
I try to lie and tell him that Sherry wants my hair this way, and I'm doing it for her, but he'll have none of it. I end up taking his bullshit for a good half-hour before he tells me to change my hairstyle… or else. I don't think he noticed my earring studs as I sulk out of his office, because he would have really blown his top if he did.
I'm so mad at myself for not standing up to him, but I've never been able to stand up to him my entire life. I wanted to tell him so bad that yes, I am a queer, and proud of it, but I'm such a pansy that I could never say anything like that to my dad.
~~~~~
Seeing the stress I'm in when I get back to my office, Janine comes in to ask what's going on. I tremble as I tell her how my dad just reamed my ass, and it hurts to tell her that he said I look like a queer.
"Well," she says, "aren't you?"
"Aren't I what?"
"A queer, just like everyone else you have sex with, me and Sherry included."
"Yeah, well… I did come out as gay over the weekend. I kinda knew I was, and when I was giving head to a guy I'd just met in San Francisco, it became crystal-clear how gay I am."
"It's okay, Mandy, you don't have to hide it from me. I already knew you love having sex with men, and now you know about me loving lesbian sex. No one here besides us knows about it, so it's not something we should worry about at work.
"And don't worry too much about your dad, baby, because in only a month, you'll be Brenda's full-time sissy. So one way or another, he won't be running your life anymore."
Placing my hand to her breasts, she then kisses me and says she wants me to join her and Sherry Wednesday night when she comes over for sex. I'm feeling much better as the day goes on, but I can't get anything done the rest of the day. I just sit at my desk staring at the mess of papers in front of me, scared about how I'm going to tell my asshole dad that I'm quitting.
I'm still pissed at myself when the workday finally ends, but I do find solace in what Janine told me as I'm driving home; that even if my simple sissy brain can't see right now, somehow everything's going to work out. Janine's always been my best friend at work, and I'm grateful to her for making me feel better when she comforted me after my humiliating experience with my asshole dad.
Oh my God… now I'm so excited as I realize I'll have both her and Sherry in bed on Wednesday night. Can you imagine me with two hot babes…? It'll be like having my own little harem!
Sexual thoughts suddenly flood my perverted sissy brain to the point where I'm not thinking about my asshole dad anymore. Thinking about how Brenda's arranged my entire life to revolve around sex gets my clitty so hard, and all I want to do is live as a girl and be her sissy slut. Even if it means risking never seeing my mom and dad again, I'll still do it for my Mistress.
~~~~~
"Hi, honey," Sherry kisses me when I get home, "how'd the day go?"
"It was alright," I shrug, "until my dad called me into his office and reamed my ass out."
"About your hair?"
"Yeah, he was pissed about it. He said I look like a queer and ordered me to get a different haircut."
"I never have liked your dad. You should have just told him to fuck off, cuz you know you're going to be quitting soon."
"I know, and I wanted to tell him so badly, but I'm such a pussy that I couldn't."
"It's understandable, so don't worry about it too much right now. I've been dying to know… how did things go with Janine?"
"Oh, God… I was so worried she wouldn't want me after seeing my little clitty, but she didn't seem to care about my size. She really helped me after my dad chewed me out, and she wants me when she comes over Wednesday night for sex."
"You shouldn't be surprised, I told you she has a crush on you. She's had it ever since we started our lesbian affair. Her prick-of-a-husband neglects her, so I told her she could jump in bed with us as soon as Brenda approved it. I also told her how good you lick pussy, and she found out Friday that I wasn't lying."
"Mmmm… she did say she loved my tongue, and I can't wait to eat her out again."
"You'll have to wait until Wednesday for that, but my pussy is available right now. After this morning, I've been craving your tongue all day. You wanna have some fun?"
"I'd love to, but let me get out of this disgusting suit first, so I can feel like Mandy again."
"Let's undress in the living room. I have to tell you what Brenda and I did today."
"Where is Brenda?" I ask as we head to the living room. "She's usually here when I get home."
"She's staying with Virginia for a few days, so we can be alone and fall in love with our new lifestyle."
"What new lifestyle?"
"Don't be so stupid," she giggles as we sit on the couch. "You know what lifestyle I'm talking about."
"Oh, yeah, the prostitute lifestyle."
"We're not just prostitutes, babe, we're high-class Hierarchy prostitutes. When we get moved into our new place, everything we do will be about making ourselves hot little whores for the Hierarchy. I'm so excited about making money for the first time in my life."
"It doesn't bother you that you'll be spreading your legs for anyone?"
"Not in the least. Brenda and Virginia have been training me to perform any sex act a client might ask of me, which is another reason Brenda's giving us this time to be alone. Anal sex, as you know, has never been my thing, but Brenda wants me to get good at it, because that's how the experienced escorts squeeze the big bucks out of their clients."
"You weren't just pretending you liked it when we did it last night, were you?"
"Of course not, honey, I loved it last night. It's just that in order to be a great escort, I'll have to learn to love it with men I might not particularly like. I can't be my best at something unless I truly love it, so how about you teaching me how to love anal like you do? You wanna fuck my ass again?"
"Right now?"
"Why not…? You better decide before I change my mind."
"Whores like you can't change their minds. You have to do it… on command."
"That's right, babe, but you'll never have to command me, cuz I'll always do it for you. Now shut up and train your whore wife to love it in the ass."
~~~~~
I loved licking Sherry's pussy before I left for work this morning, but with everything I had to deal with today, I haven't thought about her too much since then. But Sherry lets me know she's been thinking about me all day as she pulls me into her and starts unbuttoning my shirt. I respond with kisses on her forehead, around her eyes, then down to the tip of her nose.
She's got my shirt open as I kiss on her cheeks, then lets out a soft moan as I kiss down her neck and lift her t-shirt to expose her bra-less bare tits. I never really appreciated the beauty of her breasts before I became a sissy, but I worship them now as I dream of growing my own. She's appreciative of my suckling and nibbling on her firm nipples as she removes my shirt and goes for my belt.
When she gets my pants undone, I stand up to let her strip me down to panties and nylons. It feels so damn good to be my natural sissy self again, with Sherry biting at my hard sissy shaft through the fabric of my panties.
"Oh, God, babe," she moans, "I just love the smell of your cock mixed with the feminine perfume you use in your sissy-puss."
"Janine's hot ass turned me on so much at work today," I mention for some unknown reason, "that I almost went into the bathroom to finger my sissy-puss."
"You'll have her hot ass Wednesday night, so how's about taking care of my hot ass right now."
"Sorry, I didn't mean to get distracted by Janine."
"It's okay, darling, I want you to get turned on to Janine. You're gonna have so much fun with her as you get more tuned in with her vibes."
The very next instant, she pulls my panties down and her tongue is all over my cock. This is when I love having such a small dick, because she can take my entire package into her mouth, balls and all. I squirm as her tongue darts behind my balls, then swirls around my shaft and back around my balls again.
After a few minutes, she's got my pulsing clit-shaft ready to blow, and stands up to remove her t-shirt while I help her out of her jeans. As we embrace with her nipples brushing against mine, I fantasize again about growing my own tits, hoping I'll someday have breasts as beautiful as hers.
Laying her on the couch, I kiss on her nipples and finger her pussy until she takes my finger and guides it to her tight little asshole.
"This is where I want it, babe," she giggles. "Brenda wants us to have anal sex while she's away, and I already told you why."