Stepmother's New Male Maid!
Looking at myself in the mirror now, well, let's just say it's
hard to remember myself any other way. I was having some trouble dealing
with some issues and found a good therapist, and after a few months an
absolute flood of childhood through adolescent memories came back, some in
erotic dreams, some daytime revelations, and I realized how much my mother was
right about me, although I did resent it a lot at the time.
First of all, Mom and Dad divorced when I was very young, and somehow dad
got custody, remarried what I call mother now, divorced again when I realize
he wasn't really up for the kind of relationship my lovely but dominant stepmom
had in store for him.
At first my stepmom, Helena Maxwell and her daughter Tiffanny, one
year younger than I was, took very little note of me, leaving me to the
succession of sadistic boarding schools dad had me enroll in, so I only
saw their act during vacations, but to give them credit they waited until
I was nearly full grown giving me a chance on my own.
Helena was absolutely gorgeous, and her daughter Tiff, a blonde sweet
tease, and there was never any question who ruled the roost in the big house
from the divorce settlement. One of the things I had found humiliating
was Helena's favored use of corporal punishment, and not a little erotic,
especially when Tiffanny was in attendance, and she always seemed to be.
It brought back buried memories
of similar sounds from the bedroom, where of course I know now that
poor(lucky) dad was receiving his weekly reminder on Friday nights.
And even then, Tiffanny was in attendance, only a girl herself at the time.
In my teens I was getting into trouble, the academics were okay, but the
teen jocks I had been holding my own with were now bigger than I was. To make
my life worse I was being humiliated at home and at school because like my dad,
I was not going to be a big strong guy. I stopped growing at 5'6, didn't have
to shave like my dad and was slim with an oval face. On top of which Helena
insisted I wear my light brown hair in a longer style than was fashionable
at the school. I began to act out with acts of vandalism on my bullies and of
course got caught, not too bad a charge, but a bully who had been pestering me
for a year got some damage to his car, and of course Helena was sent the bill,
thus begins the real story!
"Yes mother!" I was always afraid of Helena and also attracted to her,
as I stood on slightly trembling knees at semester break in the living room
as she sat in front of me, her short skirt revealing his lush crossed legs
and high heels, as she read me the headmaster's report.
"Of course you will be punished for this!"
"(gasp) Y-yes mother!"
"But you knew that. No," she paused, looking at me appraisingly, biting her
full lower lip, I waited in silence for the verdict! "I am thinking we need to
make a change here. Do you really like going to Raithbold Academy, Timmy?"
I was astonished to hear her actually ask me. I confessed I hated it!
She smiled, "your'e getting in trouble there, and probably will continue.
If I allow you to attend a local public school do you think you would do better?"
My heart leapt with joy! "Oh yes, thank you mother. I promise I will!"
"But, on one condition, you have shown you need firm guidance and a change,
and from now on, you must be completely obedient when either I or Tiffanny
tell you something, or I will send you to military school at once!"
I shuddered at that thought. "Mallings Military Academy just happens to
have an opening, and it will make Raithbold look like a vacation!" She smiled.
'Please, don't send me there, mother!"
"That's up to you. Do you know that your father wanted you to attend that
school, 'make a man out of you'(she said this in a mocking low voice),
is what he used to say. I thought it silly and inappropriate then and still do."
"And now that your'e almost grown, you remind me of your father. I liked the
way he looked even though, (smile) it wasn't at all manly! In fact I thought he
would have made a lovely girl. Unfortunately we did not agree on that, and,
I nodded, not sure then what was going on.
"Probably because he had a son who he wanted to grow up to be all the things
he was not, and here you are, and appear to be just the opposite!"
I said nothing, as she chuckled, having a thought.
"White males are so silly in their pretended self deception, don't you think,
"Um, w-what, mother?"
"Oh, you know I date only big Black men now, in fact I did when I married your
father. Some would say I only married him for his money,..." I said nothing,
always having suspecting her of that anyway!
"But, like several of my black loving girl friends, I wanted a change at home
that only a sweet whiteboy could provide! I wish it had worked out! But now..."
she looked at me a little oddly, up and down, "I'm going to make a lot of new
rules for you to allow you in our house, and if you want to remain here and
attend public schools you will obey each and every one!"
'And the first is I and Tiffanny are tired of having to change our ways just
to suit you!"
"Y-you do?" I was astonished.
"We live in Florida, we have a pool and private back yard, we girls are used
to wearing rather revealing clothing at home!" I felt my heart beat faster,
licking my lips thinking of her and Tiff in bikinis.
"And our, um, lifestyles are naturally going to continue as usual, even with
"Yes mother, of course!"
"I frequently entertain lovers, big black studs in fact, and Tiffanny,
even though I think is just going through a phase, has a 'special' girlfriend,
you may have seen her around last spring break!"
I was instantly thinking of a luscious blonde babe, Daphne! I mentioned
the name and Helena nodded and smiled.
"Yes that's her, and she frequently sleeps over, so this is really a housefull
of women who are used to being ourselves, and you, well, you are a teenage
male thrown into it!" Wow was my imagination working over time, and I began
to get a bulge just thinking of the possibilities.
"Of course, mother, you should not have to change at all, it wouldn't be
"Your'e right, Timmy, I agree. You are the one intruding into our life
and we should not have to make adjustments. To be fair you are the one who must
adapt and change for us girls to be comfortable, if your'e willing that is.
Otherwise, perhaps your father had a point about military school!" She
smiled a little smugly, knowing she had me at her mercy.
"Yes, um, no, I-I mean, I would change, anything you think is good!"
'WE will see. We'll discuss this further, later. And of course tonight is
not Friday but we will do your discipline to get it over with and naturally
it will be more severe because of this bill for this stupid trick with a
I groaned, feeling ashamed now of that stupid stunt!
'And, it's been a long time, but since you are going to live with us,
I think Tiffanny should be present for your discipline sessions from now on!"
Moaning, I tried not to look disappointed, but she raised a warning finger,
"remember, you promised to adapt for us, and obey all the rules. And Tiffanny
always loved watching those sessions when you were younger. I think it would
be good for your training and it just wouldn't be right excluding your sister,
don't you think?"
"Yes mother!" I said resignedly.
"Very good, and now, while I think how your'e going to be trained, I'm
going for a dip in the pool. In fact you may come too, did you bring
a bathing suit?"
Eager to see her in a bathing suit, I was embarassed to say I had none.
"Oh, well, during the summer we frequently wear bikinis a lot. I'm sure
your'e very interested in seeing us in them!"
I blushed and she smiled. She looked at her watch and stood up,
"I'll see if I can find something that can fit you, I mean I can't have
you naked, except obviously during your discipline!" I would be naked!
I remember her making me take my pants and underwear down and lay across
her bare lap, and she always would hike her skirt up so it was my flesh on her
smooth thighs. I waited in the living room until a few minutes later, she
called me into her bedroom. She was in a walk in closet, and came out in the
tiniest string bikini I had ever seen and just wearing heeled beach slippers.
She smiled at my gaping and my instant boner that I tried to conceal.
"You obviously approve of my suit!"
Her big firm 40inch breasts swayed, pretty much only the nipples
covered, and when she turned around, her butt floss on her gorgeous butt
covered practically nothing. I realized belatedly I had never been in
her bedroom, and my eyes turned to some odd things she had pulled out of
a drawer. A rattan cane, strap, paddle, handcuffs and other things, plus
a device I could not understand the function of!"
"I see your'e looking at the toys! We'll introduce them to you tonight
during discipline. Now, one of my boyfriends did leave his bathing suit
over, but I don't know if it will fit. Why don't you slip your clothes off now!"
"(Gasp) N-now, in front of you?"
"Yes, of course, silly. I'm your mother, technically stepmother after
all. If I ask you to strip or anything else I expect instant obedience!"
I nodded hastily. I was already hard looking at her mesmerizing curves
and not having jacked off because of my roommate situation at school and
schedule for the last week, I had full balls. Blushing furiously,
dropping my pants and underwear, I moaned as she made me turn to face her,
unsuccessfully trying to hide my erection but looking at her body made it
She smiled smugly. "Naturally you have an erection, I really should
have expected it. Come over here now!" She sat on the edge of her bed
and I came nearer, my hardon at level with her as she pursed her lips
"I-I can't help it, mother, please!"
"Your father used to say the same thing but I tamed his nasty swollen
member. In any case I can't possibly slip a bathing suit on now. Put
your hands in back, now!" I swallowed and did so. She picked up that
odd looking piece of plastic and straps, frowning as she saw my hardon.
'Is that the bathing suit?"
"Of course not, stupid boy! It's a chastity belt, to keep naughty
boys privates from showing too much! It did a nice job taming your father
and I know it will help you also!"
Her soft but strong hands on my genitalia were shocking, and her
squeeze on my scrotum and shaft made me moan and cry out, but she smiled
as she did so.
"I-your'e hurting me...!"
"Hardly, but it is nice doing this again. Got to soften you up, you
naughty boy, oooh, does that hurt? Does this then? Hmmmmm?"
I was trying not to cry when she smiled in triumph, my erection had
dropped, and she quickly and deftly tucked my penis over and fastened it in
a plastic contraption. I instantly began to harden again but couldn't achieve
a full erection.
"There now, very nice, almost wouldn't know you wore it, clear and
very hard see through plastic. Of course your testicles are free to be
as swollen as they like, but of course, (smile) a male doesn't ejaculate
with his testicles!"
'n-no, I g-guess not!"
Smiling up at me, she took a tiny padlock out of a drawer, and locked
the shaped cylinder into place. Showing me the tiny key, she slipped it on
a bracelet on her left wrist. "Oooh, that brings back memories! Do you like
"W-well, I-I don't know, but...!" The shock was settling in that it was
permanent, at least until she decided to unlock it!
She cupped my already swollen balls and smiled, hefting them with appraisal.
"From now on of course, all your ejaculations will be earned. Your testicles
will get nice and big and blue too, that will be nice! I love white boys with
blue balls, and you'll be surprised how regulating a young male like this
will help your training too! It's really for the best!"
'And of course you won't be allowed to ejaculate in the usual sense anyway,
even if you do earn it. You will be given milkings, just to relieve the pressure
a tiny little bit, the way I did your father!"
'Y-yes, but how, I mean...!"
"You can urinate through the hole there,and it should be easy to
keep clean, but of course once a day you will be unlocked in the shower, supervised
by either myself or your sister to make sure you don't get naughty with yourself
I gasped with shock, and then she came back with a what I thought was a tiny
"I'm sorry, Timmy, I really thought I had a male's bathing suit, but I
guess I was wrong, but I do have something that will cover up your chastity cage
if your'e so sensitive about it!" She smiled and showed a nylon bikini bottom,
really just a sheer triangle and a thong in back. "And after all, you really
have to get past this male identity thing anyway to live here, Timmy.
I loved your father, but he was such a sweet sissyboy in truth, just like you are.
In fact I tried to convince him he'd make a much cuter girl and have a lot more
satisfaction too, but,(sigh) some people just don't have the discipline to
take the best course for them, do they, Timmy?"
"I-I d-don't know, um, ma'am!"
"But your'e not like that, are you, here, let me slip this on, that's a good
sissyboy!" Wincing at her expressions, the words about his father and being
a girl just sinking in, he looked at himself in the mirror with the lavendar
trianble for his genitals, and he gasped. His swollen testicles stuck out
on each side, hanging down, just separated by the thong. His chastity cage
was covered, barely.
"Oh, I-I don't know, mother, it's so, so small and revealing!"
"Only us girls will see you in it, dear. Oh yes, lift the leg, tight fit
perhaps, no, not really. Of course you aren't hung like black lovers.
Turning to the mirror, I saw with horror I was wearing a thong and my
white muscular buttcheeks were completely bare.
She tsked,looking at me critically. "Of course, all this nasty hair will
have to go, all hair except on your head" She added a little primly, "those are
the rules, plus wearing chastity belts; it helps fight chafe and infection."
"And I know the girls will be much more comfortable with you being, shall
we say, restrained!" He groaned, knowing how much this will amuse them.
"And of course," she laughed, "I know that part that covers your penis is
small but the nice part is it can't get much bigger now that you have the
chastity belt on. We don't have to worry about you getting
a nasty erection, now do we?"
Moaning, I shook my head.
"And I think we all will like seeing your nice swollen testes on display
I couldn't believe how ridiculous I felt like this as she said this,
but when she turned to go to the pool and I looked at her thong backside, I
winced for the first time feeling the constriction of my chastity tube.
I got harder, swelling inside it, but as much as I tried to push out the
tube, I couldn't straighten up, and it hurt, but also felt kind of good,
as I was able to expand a little. And then when I saw my stepmother's body
now in glistening white firm skin, voluptuous curves, and a wet bikini, it
just got worse, but I had to look. She laughed when she saw me, and complimented
me on making my balls even bigger. I knew Tiff was a notorious tease, but now
I knew where she got it from.
And afterwards, having waited on her by the pool, fetching drinks and towels
and things, she had me accompany her back to the bedroom.
"If you behave yourself, Timmy, you will be given extra priviledges.
Like if you earn it, you can help us girls, as a, well, lady's maid.
Wouldn't you like to see us in the nude, help us in the bath?"
Ooooh, I didn't even know I moaned out loud. She laughed, but
said I couldn't be a proper maid unless I changed somewhat.
Reaching into the laundry hamper, she removed a pair of silk bikini panties
she had worn the previous day. Taking them, I imagined them on her lush body,
imagining they were still warm.
I looked at her questioningly, "you want me to wear...!"
"Panties, of course, Timmy. Now don't you want to see me in the nude?"
"Oh, yes, ma'am!"
(Chuckle) "Well I can't let a boy do that, but for a well mannered maid
who knows her place, perhaps! Besides, I think it will be good for your
With that I took my wet bikini bottom off and replaced them with her
white silk panties, and once again, my big balls hung out the sides.
"Are you still concerned about your testicles hanging out?" I confessed
I was. I think it was okay in the pool, but what if someone came in.
'All right," she sighed, and went into the other room. Shortly she came
back with a little lace apron, and tied it in back.
'Now, isn't that better?"
'Now, listen Timmy, I think the sooner you get over this male thing the
better. None of us girls are interested in you as a boy. We just can't use
you like that. But as a girl, we have a place for you and you'd be much
happier I think!"
"I-I'll try, mother!"
"Good, that's all I ask!"
"(Giggle) LOOK AT TIMMY!" Turning with horror I saw Tiffanny in the
doorway, her big breasts pushing out the sheer sweater, and then, Daphne
came in and added her own giggles. I said nothing as mother explained about
my new duties and changes, and of course while I just blushed, the girls
seemed to really enjoy this new aspect of their lives, especially the part
where I was to be the new maid at everyone's command.