tagTranssexuals & CrossdressersLike Mother, Like Sissy

Like Mother, Like Sissy

bydarkheathyr©

The following tale of sexual depravity contains adult material. If you are under the legal age for your area (generally 18 or 21), or object to explicit sex, stop reading NOW. Otherwise, if erotic situations and taboo acts turn you on, then please enjoy yourself. The characters and situations are, of course, completely fictitious.

Feel free to post or archive, as long as the story remains intact and unmodified, and my contact information is attached. Otherwise, this work should be considered copyright 2011 Sissy Princess Heathyr.






I never knew my dad.

That's not an excuse for what I've become – and that's not to say I need an excuse – it's just a simple fact that some people find relevant when trying to examine what I've become.

Anyway, he was killed in a plane crash before I was born. Technically, he was killed in a plane crash while I was being born, but he died without knowing that. He'd been overseas at a business conference when my mom called to tell him she was going into labor, and had boarded the first plane he could back to North America. Ironically, it wasn't that long, turbulent, twenty hour flight that killed him, but the short little jaunt between New York and home on a twin-engine commuter plane.

I've seen photos of him, of course, and I've even see a poor copy of a commercial his company did where he walks on camera, shakes a football player's hand – an enormous black hand, not that has anything to do with what I've become either – and says, "Hello."

Hello.

That's the only word I've ever heard him speak, and it turns out that was actually dubbed over by one of the other guys in the firm, after my dad's death. So, really, I have a few photos, a bad video, and someone else's voice to account for my memories.

I regret never knowing him, but I don't regret what I've become.

As for my mom, she was a struggling medical student before I was born. She wasn't studying to be a nurse, but an actual doctor. It was almost unheard of at the time, but she has always been a strong, confident, independent woman who knows what she wants – and is not afraid to go out and get it. She wanted to be a doctor, and that's what she was going to become. The pregnancy put a temporary halt to her studies, but she had been determined to return to school the semester immediately following my birth.

Unfortunately, my dad's death put an end to those plans, but it also meant she never really had to worry about it. Even as a junior executive, my father was heavily insured. The company insured all of its employees, with additional policies on those who were required to travel for work. I don't know what the actual dollar value was, at the time, but I know my mom was smart enough about investing the two payoffs to never have to work again.

You don't care about any of this, of course, but it's important that I establish the proper expectations. When I tell people who I am and what I do, they automatically assume I came from a broken home and an unhappy home life. They assume I must have grown up in abject poverty, watching my mom do whatever it took to put a little stale bread reheated Kraft Dinner on the table. The imagine all number of daily abuses, and assume that I must have suffered tragically to explain what I've become.

I want you to know that is so not the case!

Even without a dad, I wouldn't call our home broken. My mom and I were very close, as much best friends as were family. There was nothing sexual or inappropriate about our relationship, so get your mind out of that gutter, but we have always been very honest and open with each other about sexuality. That, I will admit, likely has something to do with what I've become, but only in that it has allowed me to embrace my place in life without fear or shame or doubt.

As for poverty . . . well, like I said, my dad's insurance policies left us very well off. In the time it took for a single stupid goose to fly into the plane's right engine, our house, our car, and even my dad's boat were all paid off. That meant my mom only had to worry about utilities and food, and the interest from the insurance settlement alone covered that and more. I wouldn't say we were rich, but we were very comfortable.

I distinctly remember the first time I saw my mom come home with a man. I was twelve at the time, and finally old enough to stay home by myself. Of course, I had to keep the doors locked, the window shades down, and the television on in the living room. My mom even had the gardener – a mean looking black man who, in hindsight I still suspect was doing more than just trimming the bushes – come over around ten o'clock to move the cars around in the driveway, and then exit through the back yard. I'm not sure any crook is really stupid enough to fall for that ploy, but it seemed genius to me at the time.

Anyway, I should have been in bed, but I decided to stay up late to watch the late-night talk shows I heard other kids raving about at school. To be honest, I really didn't see what they thought was so great, and was actually on my way to bed when they came in.

My mom was dressed in a gorgeous red cocktail dress, with shiny red heels and a matching purse. I'd watched her get dressed and do her makeup before she left, and helped her to pick out the shoes and purse. Before you start smiling and figuring you suddenly have me figured out, I wasn't queer or anything like that. I just enjoyed watching the act of transformation my mom went through once in a while. She was an attractive woman around the house, but she was an absolute stunner when she went out. Even as her son, I could appreciate that.

She'd always been a pale woman, blessed (or cursed, depending on when you asked her) with freckles all over her body. Seeing her come through the door, though, with that black man towering over her, she looked like such a tiny little ghost. I'd never really thought of her as short, just normal, but either she was really short or he was really tall, because she looked like a child as she turned around and stepped into his arms.

Over the next few years, my mom would bring home a lot of different men. Some were tall, some were short. Some were skinny and wiry, others were muscled and bulky. Some dressed like the teachers at school or the men at the bank, and others dressed like the kids at school or the punks looking for a purse to snatch outside the bank.

What they all had in common – that I could see, of course – was that they were black. The fact that there were all extremely well-hung and full of cum was something I wouldn't discover for a few years yet.

It was the summer of my fifteenth birthday when I finally, fully understood my mom's relationship with these men. We were out laying by the pool – me out in the sun, her beneath the biggest patio umbrella you'd ever seen – when I caught a glimpse of something on her back. Curious, I waited until she rolled over to pick up her soda, and then leaned in for a look.

It was a tattoo. The very idea of such a thing on my mom's backside thrilled me. Tattoos were dangerous things, the kind of things you saw on dangerous people. I'd never known anyone with a tattoo until then. Her tattoo was a red heart, about four inches wide at the top, set in the very small of her back. It would have been hidden by anything other than a bikini bottom, so I couldn't even guess how long she'd had it. I understood the heart, of course, but I couldn't make sense of the lettering inside.

' W4BBC' was written inside that heart, in carefully drawn, very feminine, stylized lettering.

We'd never had any secrets between us, and she'd always welcomed any questions I might have, so I asked her what it meant. For the first time in our lives she paused, as if she might not answer. I was devastated. What could be so horrible that she couldn't even speak of it to me, her son? I mean, I knew tattoos for dangerous people, but had she done something wrong? Was she ashamed of the beautiful artwork that adorned her flesh?

I remember how she looked at me, as if she wanted to tell me, but was afraid. She looked so excited, but she also looked scared. I smiled, and started to tell her it was okay if she didn't want to talk about it, but she shook her head, laughed at herself, and then invited me to sit on the end of her chair so we could talk.

That was the afternoon that she told me, proudly and openly, that she was a Whore 4 Big Black Cock. That's precisely how she said it. Whenever my mom used those words, you heard the capital letters at the start of each one.

Whore 4 Big Black Cock – that's what the W4BBC stood for, and the heart around it represented the fact that she loved everything about being a Whore 4 Big Black Cock. It had all started quite accidentally, with that first date I witnessed a few years ago (as it turned out, even she had been afraid of the gardener). She'd never intended for it to happen, and hadn't gone looking for it, but that first Black Cock had been so Big, she knew she could never give it up.

She told me to think of my own cock at its hardest – she'd seen it very well the night we had 'the talk' and probably a few times after, through my open bedroom door at night – to imagine it twice as long, and to imagine it as three times as thick. That, she told me, was only the beginning. She told me to think of my messiest orgasm – she emptied the garbage and cleaned my sheets, so she knew what I was capable of – and then imagine each one making twice the mess, and then imagine having five of them at once.

That, she assured me, only began to explain her addiction to Big Black Cock. She loved it, it made her happy, and she was not at all ashamed to admit that to me.

With what little I knew about sex at the time, that made perfect sense to me.

It didn't suddenly fill me with a sense of inferiority, or suddenly crush my masculinity. I didn't feel the least bit insulted by the comparison to my own cock, and honestly didn't feel as if there were anything wrong me with. Instead of making me feel small and weak, the conversation simply informed me that black men were bigger and better. There was an 'average' or 'normal' size somewhere between us, and I knew that I fell pretty close to that mark - they just exceeded it.

There was no sharing of intimate details, no reminiscing about past lovers, just a very frank discussion about what she loved and why. To a neighbor peeking over the fence, we could have been talking about the weather, the shape of the clouds, or what we were going to have for dinner that night. When you lived such an open and honest relationship as we did, conversations like that really weren't a big deal. It explained the tattoo, helped me to better appreciate the men she brought home and, most importantly, confirmed that my mom was a happy woman.

When you're fifteen, living at home, and politely aware that you have it better than most of your friends, your mom's happiness really is important.

*******

That's part of where my story starts, but to understand how quickly and how drastically my life would later change, you also have to understand other half of my story.

From the moment puberty hit, about a year before the W4BBC tattoo revelation, I'd been a very happy little sissy cross-dresser.

Now, this might be something you can blame on being raised by a single mom, but I don't know that our situation had much of an impact on things. Really, I think I would have developed my fetish for femininity regardless, even if I'd been raised with a strong father figure and a few older brothers. It was nothing that my mom forced on me, but it also was nothing that she discouraged.

The more opportunities I have to meet with other sissies, the more I love her for that attitude.

By the time we had that conversation by the pool, I already had a closet full of feminine attire that was almost as well-stocked as my closet of masculine attire. It was a closet I only explored around the house, but I was okay with that. I could spend all day trying on outfits, feeling the caress of silk and satin across my skin, and enjoying the delicious thrill of high-heels on my feet. I hadn't yet begun experimenting with makeup, but I'd watched my mom transform herself enough times that I felt pretty confident I could do it – and do it well – whenever I felt like it.

Whereas my mom was a bold woman, commanding and strong in reds and blacks, I was a soft little sissy, submissive and meek in my pinks and yellows. There was nothing in my closet that couldn't be considered soft, sweet, cute, or adorable. Dressing started out an entirely sexual experience, I freely admit, but it soon became something that I did to relax, de-stress, or just feel comfortable.

It just felt right . . . it just felt like the real me. It was nothing I really discussed in detail with my mom – it was enough that she accepted it – and I certainly never brought it up in front of my friends at school. In fact, I laughed along with them whenever a lisping, prancing, gay sissy showed up in a movie, even as I secretly studied his every word and his every word to see what fell into my definition of myself.

I laughed, but I also learned . . . with none of my friends the wiser.

By the time my life changed forever, I was spending my every moment inside the house dressed as a girl, and had even ventured out to the mall a few times with mom to go shopping.

*******

Thanks for sticking with me through all of the boring stuff, but I think it's really important to understand that even the most seemingly normal, well-adjusted, happy boy can become what I am today.

In fact, if you're reading this, it might very well be that you're on your way to joining me. If so, then please accept my sassiest, silliest, sissiest squeals of congratulatory glee. There really is nothing better, although I'm glad most boys don't see it that way.

That just means more for me (or us, if you really are on your way to joining me)!

It was the night of my eighteenth birthday party that circumstances conspired to change my life forever. At the time, I was absolutely devastated that my friends had all backed out of my weekend birthday celebration – all for good, entirely valid reasons – but I had tried to soldier on anyways. Unfortunately, a weekend in a private, well-stocked party pad wasn't nearly as exciting as it seemed without company there to help me enjoy it.

So, when it became clear on the second night that no latecomers would be joining me, I headed home to raid my closet. If was going to be alone and drunk, with access to a well-stocked bar and pay-per-view television, I was going to get dressed up and enjoy it.

The first thing I noticed when I got home was the number of cars parked around our house. Our driveway was full, the front lawn was covered, and both sides of the street were occupied from the stop-sign on Park, to the yield sign on Strauss. My mom was clearly having a party of her own, and the last thing I wanted to do was intrude. I almost headed straight back to the party pad, but by that point I'd played through the weekend so many times in my head that I needed to grab some things from my feminine closet first.

It gives me chills to think how my life might have been different if I really had turned around.

Strangely, the main floor of the house was dark. Other than the kitchen, the lights were out, and there wasn't a soul to be seen. I figured they were partying out back, so I hurried up the stairs to my bedroom. When I got to the top of the stairs, I saw the sliver of light from beneath my mom's door, and heard the noises coming from the other side. It wasn't that they were loud or rowdy or anything like that. In fact, as she told me later, the men themselves were being rather quiet, never talking to one another, and only whispering to her. As for my mom, she was a little too occupied to be speaking . . . if you know what I mean.

If you don't, then I really don't know what to say, other than to hope the surprise is a pleasant one. I know it was for me!

Of course, I knew none of that at the time, but knew well enough not to disturb her. As open and honest as our relationship was, our one rule was that closed doors meant privacy. If doors were open, we were both free to come and go as we pleased. Bedroom, bathroom, laundry room, den, it didn't matter. Day, night, morning, afternoon, or evening, it was all the same. Naked or clothed, alone or with company, an open door was an invitation.

A closed door, however, was a polite sign that we wanted a little privacy – and we both respected that.

I went down the hall to my room and made sure the door was closed behind me. If she had a guest in the house, I didn't want him wandering into my room by mistake, especially while I was getting my clothes ready. I spent the next half hour in the closet, pulling clothes out, holding them against one another, keeping some, and putting the rest back. I had it in my mind that I wanted two sets of outfits, with a little room to improvise, depending on my mood.

First, I wanted a cute, sexy, college girl outfit in case I got drunk enough to leave the party pad. I knew that was a possibility, and it excited me. For that, I had a few very short skirts, some tight blouses, knee-high socks, and my eighty-dollar Victoria's Secret pink panties.

Second, I wanted something slutty and sexy for being alone in the party pad. For that, I grabbed my second favorite corset (I needed somebody to lace me into my favorite), two pairs of fishnets, a garter belt, and my frilliest, laciest, sissiest panties. After, for relaxing, I grabbed an adorable pink peignoir set that my mom had just bought me, but I hadn't yet had a chance to wear.

I had everything packed, then decided I really did have to be prepared if I was going to go on a drunken stroll around town. So, I left the overnight bag on my bed, and then made my way down to the bathroom to borrow some of mom's makeup. Halfway down the hall, though, her bedroom door opened and two of the tallest black men I had ever seen in my life walked out.

I'm not sure why I panicked, except that I didn't want to intrude on my mom's fun. I quickly ducked into the hall closet and watched through the crack to see if they had noticed me. As they passed, I got my first close-up look at big black cock . . . and what a look it was. Obviously, I couldn't measure them, but I'd put them both at about 9 inches long, and so thick it would take both hands to masturbate them. More than that, their balls were absolutely enormous. I swear you could have taken my cock and balls, balled them up, and stuffed them into either man's sac, and still have room left over.

I didn't find them particularly attractive or anything, and certainly didn't feel a sudden urge to jump out and devour them, if that's where you think I'm going with this. Instead, I simply admired them, appreciated them for their beauty, much like I'd appreciate a priceless sculpture at the museum. Yes, they were big and they were beautiful, and I could certainly understand why mom was a proud whore for big black cock, but seeing them didn't suddenly turn me gay.

The moment they disappeared down the stairs, I rushed to the bathroom, grabbed the makeup I needed, and then headed back to my room to finish packing. While I was there, I suddenly heard a group of deep, male voices coming down the hall, accompanied by mom's giggles of amusement. I couldn't overhear everything they were saying, but apparently they had dared her to do something with a drive thru, and she was determined to collect on the dare. I peeked outside my room and counted at least a dozen black men, not including the two who had already gone downstairs.

I gave it ten minutes to be sure they were gone, and then emerged with my overnight bag, ready to head back to the party pad.

Report Story

bydarkheathyr© 19 comments/ 182950 views/ 72 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel