MBA turned Sissy then Shemale!

by Small Penis


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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

These stories are the artistic expression of the authors who wrote them. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this post, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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It hadn’t always been like this …

I have an MBA and stock options in several extremely wealthy businesses.

I also have B cup breast implants, a 3 inch cock, enhanced lips, and a majority of the time I’m servicing my old co-workers. C’est la vie I suppose.

Where to begin? I suppose I should just start at the beginning and end at the end. I worked as an executive at a company that made high-tech computers for the military-industrial complex. We made a fortune on bids and then years later we would sell the stuff to the private sector, it was pretty great. I don’t know the first thing about computers but I do know a lot about business and, while I may have been an asshole then, I definitely made sure that work got done.

I was toned, ripped really, dark skinned for a white guy, and I had a nice 8 inch cock that I treasured. I never sexually harassed an employee, I never sold a bad product knowingly, I never did anything that makes powerful men like me into sissies in the literature. It’s actually simple: I’d always wanted to be a submissive little cock whore but I’d been compensating. I compensated pretty well though, I’m retired at this point; the CEO didn’t want his second in command coming in in stockings and bras anymore, but I’ve got more than enough money to live comfortably as a sissy for the rest of my life.

What did happen was fairly simple. I decided I’d go and get my nipples pierced. I was a high-powered executive at 28, damn good looking, and rich. It was essentially the only thing I could do to make myself more appealing to the ladies, I like to please.

When I got to the piercer’s shop I told them what I wanted and the simpering male secretary brought me to a room in the back where I was to wait for the piercer. When she came in I realised she was gorgeous. Her name was Candi and I was basically in love with her the moment she walked through the door.

“So you want your nipples pierced?” she asked, shutting the door behind her and turning a lock.

“Yeah, I thought it would look good. Women like that sort of thing don’t they?” I asked.

“Do you really need to worry about what women like?”

“What do you mean?” I was a little confused.

“You pulled up in a Bentley, you’re wearing an Armani suit, and from the bulge in your pants I’d say you’re well endowed. Is there any reason you’re trying to make yourself -more- appealing to women?”

Wow. She’d hit the nail on the head!

“Not really I guess, I just figured if I want the best woman I should try to be the best man I can be.”

“How cute. Frankly, I think nipple piercings are a little feminine. You should get a tramp stamp and a naval piercing too.”

She seemed like she was being a bitch but I wasn’t going to take that. She was too beautiful, in that greco-Roman sort of way, to be a bitch.

“Well maybe I will. Kind of edgy, don’t you think?” I retorted.

She looked at me and cocked an eyebrow. I got a hardon then and there and prayed she wouldn’t see it.

“Someone likes being talked back to,” she said, pointing to the erection. Damn.

“I’m just … you’re hot, what can I say?”

“Baby, you don’t need to say anything, should we get to piercing?”

That was a relief. I climbed into the chair.

“Take your shirt of please.” she said. I did as she asked and she cocked her eyebrow again. If I’d been less of a man I may have shot my load in my pants right then.

“My, we really do work hard, don’t we?” she asked, running the pen she’d been writing on a clipboard with down my six-pack.

“I work out every day, but not as much as I should. I’m kind of lax.” I said.

“This isn’t lax, Mr. -”

“Johanson.” I replied.

“Mr. Johanson. This is dedication. Take your pants off please.” She ordered.

“My pants?” I asked, confused.

“Yes please. I can’t do a naval piercing with your pants on.”

That didn’t sound like a good reason at all, and I didn’t want a naval piercing to begin with. I took my pants off anyway, it seemed like she was just trying to get me naked and I didn’t have a problem with that.

Once I’d gotten my pants off I cursed myself. I’d forgotten that I was wearing one of my girly boy short briefs. They were probably women’s cuts with a pouch added in, but even that wasn’t much. My throbbing hard-on was plain as day and the underwear were less than masculine. I wore them on days I wasn’t planning on having sex, they’re more comfortable and have way more support than regular men’s underwear.

“Jesus.” she said. I was starting to feel more than a little embarrassed.

“What?” I asked, trying to play it off, “they’ve got more support and they’re comfortable. It’s not all about style.”

“Those are as close to panties as you can come darling.” she replied, “But I applaud your bravado, I think it’s hot you’re willing to look like a fag for comfort.”

“Excuse me?” I was offended.

“They’re gay honey. Those are gay men’s underwear. Don’t try to deny it either, you say the little bitch we have working the front desk, he probably owns the same pair. I think it’s cute.”

She smiled at me for the first time and it was a warm smile.

“Just take them off, your cock is straining to get out and there’s no reason for you to be uncomfortable.”

“I don’t know if that’s, um, appropriate.” I said.

“Babe,” she said, putting a hand on my inner thigh and leaning in close to me, “I’m going to jerk you off, do you really want to turn that down? Be a good boy and take that big dick of yours out.”

She was so forward, it was turning me on. When I got my underwear off she leaned over again and sucked the precum off the top of it, licking around the head before going all the way down and coming back up again. She started to jerk me off, using her spit as lube.

I came in about 30 seconds and felt embarrassed. I’d been so hard since she’d walked in I couldn’t contain myself.

“I’d like to do something for you,” I offered.

“Alright,” she responded, “since you came so quick you can lick your cum off my hand. After that we’ll do your piercing’s and then you can come to my place and cook me dinner.

For some reason I was already licking the cum off her hand so when she offered to have me over I responded with a simple “Mmm hmm,” my mouth full of my own seed. It tasted good, I’d never had cum before but it was enjoyable.

“You can lick the rest up off that six pack of yours.” she said. I did.

As she got her piercing equipment together we were oddly silent, I was mostly scouring my stomach for cum to consume and she didn’t have much to say. She pierced my nipples, then my naval (which I went along with for the hell of it.

When I was leaving I wasn’t sure what to say, so I just said, “bye.”

“Oh, Mr. Johanson, the receptionist will have a package for you to wear to my place. You can put it on outside the door if you like, but be wearing it when I answer the door. Are we clear?”

“You just have clothes lying around for me to wear?” I asked, kind of creeped out.

“No. You’re going to wear something of my secretary’s. Good afternoon.”

I shut the door and went out to the front desk to pay. I looked at the secretary, he was slightly built and pretty feminine, especially his attire.

“I’m supposed to ask you for a package?” I said.

“I have a boyfriend,” he replied.

“I meant a package of clothing, from your boss.”

“I don’t know what you’re talking about.” He was snippy.

“She said that I was supposed to get something of yours to wear.”

“What the Hell? She’s so weird. I guess, I only brought a sexy little outfit to please my boyfriend though. He’s a black guy and you know how they like their boys.”

I didn’t know how black men liked their boys but I was clearly going to find out.

When I showed up to her house I felt awkward and silly. I was wearing a gstring (I didn’t even want to know if it was used or not), a pair of booty shorts with the word JUICY on the back, and a tight shirt that barely went halfway down my torso. I looked like a slutty high school girl had picked out my wardrobe.

I knocked on the door and when she answered she didn’t even acknowledge that I was dressed like a sissy, she looked me straight in the eyes, smiled, and beckoned me to come in.

“I know I said I’d have you make dinner, but I actually have that under control.” she said.

“Oh, well that’s good. Why am I wearing this?” I asked.

“You’ll see darling, don’t worry. Now, would you like to have something to eat?” she asked.

“I suppose, I’m actually kind of hungry.” I replied.

We went into her kitchen and I nearly fainted. Standing there at the table was a completely naked Hispanic man with a dick that made mine look like it belonged on a toddler. He’d apparently cooked the meal and put it all on the table, the seating was for three.

I was about to leave when my reasoning told me just to stay. Nothing bad was going to happen and if things got out of hand I could always leave. I didn’t know anyone in this part of town so they wouldn’t see me in my getup. I’d be fine so I sat down at the table across from Darlene and next to the Hispanic man.

“This is David, David meet Mr. Johanson. Mr. Johanson, David.”

“Nice to meet you David,” I said.

“Same to you, Mr. Johanson.” he said, eyeing me up and down. I felt small even though this man was skinnier than me. It was his dick, it was overpowering.

The meal was delicious and I made sure to tell David after the first couple of bites. I was extremely impressed. We all discussed piercings and other things. I started to notice that I was getting a little tired and that I couldn’t help but stay semi-stiff throughout the meal. I began to suspect there was something in the wine but felt too good to do anything about it.

Just when I thought I was being paranoid I felt David slip his hand under the table and start caressing my dick.

“You’re pretty hung for a white guy.” David said.

“Oh thanks,” I said, and winked. I should have been turned off with a man jerking me but for some reason it seemed alright.

I looked across the table and noticed that Darlene was gone, I wondered where she was until I felt her head in my lap. She also was playing with my feet but everything felt too good for me to worry about it.

David had gotten up and started caressing my nipples, Darlene had pulled my semi-erect dick out one leg of my booty-shorts and started to lick it.

At that point I sort of blacked out for a bit, I’m not sure what happened but when I looked down next I noticed a lot of weird things had happened.

I was in a slightly different spot; the other side of the table to be precise, and my legs were propped up on the table. My legs had been shaved, along with the rest of my body apparently, and were stuffed into a pair of clear plastic fuck me pumps, at least 4 inches with platforms.

My clothes had been removed except for my thong which had been pushed aside to make way for Darlene’s giant dildo which was sliding in and out of my lubed up asshole with ease. It was probably the most pleasant feeling I’d ever had, aside from David’s big warm cock completely filling my mouth. I also realized that my hands were playing with my nipples, rather than my cock. As a matter of fact, no one was touching my cock.

It was at that moment I erupted in ecstasy in the most amazing orgasm of my life. Nothing had touched me and yet there I was, cumming like there was no tomorrow and spraying globs off cum on my own face and chest. I tried to smile as I closed my eyes and continued sucking David’s dick like my life depended on it.

Suddenly I heard Darlene start laughing and David followed.

“He comes like a girl, don’t he?” David said.

“Just like a girl, except he’s got that big dick.” Darlene said.

I’d never thought about it, but I didn’t like having a dick, it was kind of a downer. Well, maybe not -having- a dick, but being as big as I was certainly was. I’d always hoped for a smaller dick, something maybe 4 or 5 inches, but I’d never really thought about it.

I heard Darlene cum from fucking me with a strapon and a few minutes later I felt the hot sticky mess of David’s cum as it oozed down my throat and a little escaped my mouth. He pulled his cock out of my mouth with a pop and I smiled, letting it run down my chin, and lay back with my eyes closed.

I began to think about my life. I was in control of just about everything but suddenly I was out of control and in a submissive position. I loved every second of it. I especially loved it when Darlene had made me feel humiliated by the fact that I came from being fucked in the ass.

It dawned on me that this was really what I wanted.

“I want to be like this forever.” I said, looking up at darlene who was removing the strapon.”

“I figured.” she said.

“You knew?” I asked.

“Not really. When you came in I started to guess and figured I’d have you over for dinner and maybe we could fuck. Of course, I figured I’d be cumming from your dick, not vice-versa, but whatever. We drugged you of course,” she said.

“With what?” I asked.

“Oh nothing really, an old herbal remedy. It makes you succumb to your desires. It doesn’t make you stupid though, if you hadn’t wanted to do something you wouldn’t have done it. Actually, if you remember, you didn’t want David to fuck you with the high heels your wearing, you thought it was weird being fucked by shoes.”

I did remember, although only vaguely. That made me feel a lot better.

“I didn’t really plan on having you just move in and be my sex slave though. I like fucking with a strapon, but I need a man inside me sometimes.”

“Well,” I said, stroking my cock to erection again, “There’s David here, and then again -”

I got up and crossed the room to her, very steadily on my new heels, and slid my cock into her tight pussy.

“Oh.” she gasped before she kissed me passionately. David came up behind me and slid his giant cock into my ass. I was worried about his not wearing a condom, but I assumed he was clean, I didn’t really care that much anyways. When he came in my ass it only sealed the deal for me, all that warm sperm in my butthole felt amazing.

It’s been 2 years now and my changes are complete. No hormones or anything like that. I’ve had some lip implants, B-cup breast implants, butt implants, liposuction and muscle removal to give me that slim figure, a slight facial feminisation, and a radical new therapy to shrink my dick.

Essentially they castrate me for a week and pump it full of a chemical that causes the muscle to break down. I’ve gone from 8 inches and thick to 2 inches and more of a slim size. I can still have sex with Darlene and bring her to climax, but I’m so small we have to be scissoring. It kind of turns us both on, having sex like a pair of lesbians. I always love the way my little titties jiggle while I’m making love to her.

David is the man of the relationship, we’re both considered his wives. Essentially Darlene is the dominant one and I’m the sissy one. I stay home all day and do the chores that need to be done, which arne’t many since we have a maid. I’m thinking about letting her go though, for an immigrant she sure is judgemental. I realize I still look like a man, and I realize I enjoy the humiliation of walking around the house wearing girly clothes that show off my almost permanently hard (thanks to viagra) 2 inch dicklet, but that’s no excuse to scoff at me and mutter ‘sissy’ under her breath when I give her an order.

I did try firing her once though, and that didn’t work out too well. She’d simply grabbed my by the balls and looked me in the face. She said, “You’re not going to fire me, you little man bitch.” And then she started to jerk my little clitty off with her thumb and forefinger. It had been poking through my microshorts, there’s a hole cut in them so my little thingy can get the air it so desperately needs. Anyways, as I was shooting my pathetic little sissy load down towards the floor she’d made me repeat again and again that I was the bitch of the house and that I would never, ever speak back to her again.

She made me get down on my knees and lick my cum off the carpet, thrusting her duster into my loose boypussy and of course Darlene had come home at that precise moment, seeing me licking my own sissy spunk off the floor with a feather duster sticking out of my ass. That was the last time I wept and it was the last time I ever asserted myself in my own house. They, the maid and Darlene, had been laughing so hard. Even my humiliation didn’t help, it only caused me to let another small stream of cum ooze out of my now pathetic cock onto the floor as I came again from the insults.

Of course, Darlene couldn’t help but start inviting my old coworkers over. People I went to college with, people I gave orders to, people I directed around the office on mediocre chores that I was either too busy or too lazy to do myself. They would all come to my house and see me in whatever sexy outfit I was wearing (always with a hole for my stiff 2 inch erection to poke out and embarass me more) and invariably begin laughing and making jokes about my new situation.

“Show us the tits, boss.” One of my old temps had said while he forced me to ride a gigantic black dildo he’d stuck to the wall of my living room while him and his college friends beat their dicks off sitting on my sofa. I’d pulled down my chemise and let my soft, supple breasts jiggle as I pumped the rubber penis in and out of my bubble butt.

When I’d had a little sissy orgasm and made a mess on the floor they all started laughing except for one, who’d started to cum as well. He looked at the temp who used to work for me and said “You used to take orders from him?”

“I may have taken orders, but look who’s sitting on a dildo performing for us like a slut now.” he’d replied sarcastically, “I’d never wind up a sissy bitch like him.”

Unfortunately he hadn’t been paying attention and came at that moment, covering his own face in cum. After the show was over he’d lingered for a bit before going to his car, he’d been the last one to finish washing the cum off himself in my bathroom. I stopped him as he was leaving and stood there absentmindedly rubbing my tiny erection.

“You know,” I’d said, “If you enjoyed the insults they were giving you, you might think of joining me here. I’d love to have a girl friend.” I smiled and reached out to grab his cock.

“I’ll … I’ll think about it,” he’d said rapidly before running out the door to his pals.

He lives with us now, crossdressing full time. He’s the one on the hormones, he really went whole hog. I’m just upset his titties are bigger than mine, and that his penis is still big enough for him to fuck me. I thought he’d be my sissy pal, not my shemale master. I guess I’ll be forever at the bottom of this totem pole but regardless of my status, I’m just happy I can have hot cum in my ass as often as I want it.

I love my tiny dick, my new breasts, and my sissy wardrobe. Being a girly boy was really all I ever wanted, I’m sorry I fought it for so long.

4 Comments

  1. Loved your story those are the things that make me so horny reading id love to be made into a lesbian sissy and also pleasure gay men while dressed in female clothes thank you ill be back to read it again as i cream my panties

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