XXX My Sissy Clients
A professional nanny reminisces about her favorite Sissies
Posted on
Add A New Story
I have recently retired as a nanny, though the name I
always called myself was Mummy to my clients.
It was for their pleasure I offered them to visit my
specially made nursery, for two hour sessions, or days, or
weekends, a few even stayed a week at a time.
Over fifteen years I have entertained nearly a thousand
Sissies, and many would be keen to return for 'repeats.'
According to my books one came over sixty times!
I suppose men wanting to play at being sissy are my
typical regulars, but I have some women also, and all start
by either completing my on-line form or doing the same
over the phone. My questions tease out what the Sissy
wants from their stay and whether they want me to vary
their requirements if I so wish, or to stick rigidly to their
own instructions.
I guess that I turned away about one in three inquiries
as I didn't care to meet their demands, most often this was
for sex.
But now it's all over, I have many joyful memories, for I
was nearly always very happy to meet my Babies'
requirements whenever possible, and I'd like to share with
you in confidence five of my favorite Sissies.

I suppose you always remember your First Love. Well,
my first ever customer was special for me, as I was very
very nervous myself, though I tried not to show it, I guess
he knew.
He was Gary, but I always gave my Sissies names, and I
called him Stevie which is my own name, though he didn''t
know that. He just called me Mummy.
He had booked in for two hours, and I welcomed Stevie
to my lovely new nursery as its first sissy.
My customers always removed all their clothing except
underwear in a lobby, then came to me as I sat in the little
nursery. Stevie marched in quite proudly and lay on the
changing mat. Thru her pantie, I remember seeing she
was erect. I admit I hadn't really expected that, though I
suppose I ought to have done. I learned this was more the
norm than otherwise. It almost turned me on.
She desired to be a sweet sissy girl, so I took off her
vest and brought out a sumptuous organza ruffled dress in
pink with white hems as well as a white apron that covered
down to her thigh.
Now I was able to remove her pantie without exposing
her erection, which was something that wasn't part of my
service. I was a virgin myself and had never experienced
any lasting relationship, perhaps that's why I had wanted to
start this nannying role to give myself some fulfilment. Not
that I consider myself unattractive, I'm over six foot with
dark auburn hair, slender and I like to think I'm warm
hearted and loving.
I pulled a soft transparent plastic pantie up Stevie's legs
and up to her waist. She cooed happily, obviously this
wasn't her first time with a nanny. She'd asked for story
time, so I held out my hand and she came and sat on my
lap on my sofa.
I read her my tale of Sleeping Beauty as she cuddled
on my lap, and as we reached the sad part of Sleeping
Beauty's sleep, I became conscious of a wetness oozing
thru the seam of her waterproof pantie.
"Has wittle Stevie wet herself?" I interrupted the tale.
She nodded coyly.
"Then come with Mummy," I led her by the hand to the
adjacent bathroom, where I sat her in the dry bath before
pulling off her pink dress.
I could see she was very erect as she clung her arm
round my shoulder, but I turned on the taps and with the
water swelling round her bum, whisked off the pantie. I
couldn't help being attracted to her giant erection, but tried
to pretend not to have seen despite her hand digging into
my shoulder.
I switched off the tap and let the water and wee drain
away, then left her naked with a toy ship to play with as the
bath refilled. Stevie was left to play for a while, then I
helped her out onto the changing mat and poured talcum
powder all over her.
I noticed she was no longer erect but still cooing like a
little girl ought. I pulled on a fresh plastic pantie, then I put
some lovely smelling perfume on her upper body and
rubbed it well in. She liked that and smiled contentedly as I
put on the silky dress again.
Back to the nursery where I left her in the playpen with a
selection of toys to play with. She asked for a feeding doll
and fed her, softly saying the words Wittle Stevie as the
doll gulped down the toy bottle's contents.
As the doll began wetting Stevie, I could see she was
straining wee out herself too, and soon she was very
squishy indeed, sorta bouncing on the floor of the pen.
This was clearly a game she thrilled to, and I held her
hand as she bounced up and down, up and down in her
wee cuddling her doll. She kissed me, that told me she'd
finished, it was time to get her changed.
We repeated the bathing only this time I handed Stevie
her real clothes and a happy Gary said goodbye. I never
saw him again, maybe I hadn't got it quite right, in fact
looking thru my more experienced eyes, I'm sure I didn't,
but you always remember the first one.

Daniel was the shyest Sissy I ever met.
I myself was much more experienced when he came for
his first day. He did visit several times, but I'll never forget
his first visit. when I christened him Blanche.
He was small in stature, and I remember his walking
into the nursery that first morning, hands in front of his
crotch avoiding my eye contact and slipping down
nervously on the mat as though it were something
As he clutched his crotch, I whispered, "good wittle
Blanche, let Mummy get oo changed."
But though she let me remove her vest and dress her in
a sweet long lemon chiffon nightie, she kept her hands
tight to her.
"Come on wittle Blanchie, be a good girlie. Mummy
must put ore nappy on," and I looked away to reassure
her. T
hen I groped, and gently pulled her reluctant hands
away to remove her pantie. I slipped a disposable nappy
round her bum and sealed it tight.
"There, that wasn't so bad was it?" Blanche shook her
"Now let's tuck oo in ore cot," and she was light enough
for me to lift into my special cot. I tucked her in and fetched
a bottle of warmed milk which I popped into her mouth.
For the first time she looked at me, but glanced away at
once. As she sucked I sang a lullaby, and she again tried
looking at her mummy, only to glance away again at once.
I stroked her longish hair, which she seemed to like,
then kissed her cheek which she certainly liked, for she
smiled at me for the first time. But she resumed staring at
her bottle and sucked the more as I went on singing and
caressing until the bottle dropped out her mouth and she
fell asleep.
I left her peaceful until she awoke for lunch, which I had
already prepared, As she looked round, she resumed her
coy looks and I could not get her to look at me at all, she
simply turned her head aside.
"Good little Blanche wanna eat?" I asked.
No response. I asked several times, before I realised
she was a little wet.
"Mummy will clean oo after dinner," I coaxed, "just eat
ore food first, as it's weady."
She shook her head, so I turned away. She cried out to
stop me leaving.
"Oo want ore food or not?" She lay in her cot crying,
and as we hadn't agreed any punishments, I had to leave
her alone in the nursery.
From the kitchen, I heard her noise grow louder and
louder. I filled her soup into a bowl and took it in, without a
word lifting her wriggling body from the cot into the high
chair. She struggled to stay in, but I pulled down the clamp
and she was stuck there, a dicky bib tied to her neck.
"Now wittle Blanche, let's get down ore soup."
She wriggled making it clear she wanted changing, but I
threatened, "if oo don't eat it all up, ore nappy will stay on
all afternoon."
That almost did the trick and I filled the large spoon with
soup and pushed it to her mouth. She jerked away, so I
held her head and stared into her eyes. She couldn't avoid
my looks now, but she looked downwards and ashamed.
The spoon was forced in and if most of the soup went out
and down her chin, at least Mummy had won her point.
She gave in, not seeming to like any more soup
dripping off her chin and soon she was gobbling it down.
"Good wittle Blanche. Now Mummy'll fetch ore
She made a face when I tried feeding her with this, but I
was determined to win this battle of wills, and though
nearly as much ended up in the bib and on her face, some
got down and was made to stay down. As she'd been
naughty, I didn't wipe her clean, instead inserted another
bottle of warmed milk in her mouth which was held by a
clamp so I didn't have to feed such a disobedient sissy.
This she resisted too, but her head was resting on the
back of the chair, and my device forced my baby to keep
the teat in her mouth. She began sucking and clearly liked
this sweetened milk.
"Wee wee," she stuttered thru the teat, and I could hear
her squeeze more wet into her nappy.
"Like wee wee, " she repeated the wetting this time
looking at me longer than ever before.
"Good wittle girlie," I responded and filled her empty
bottle when she begged for more.
After three bottles she sighed and looked at me
imploringly. I noticed for the first time her deep brown eyes
as she held out her arms. I released the clamp and she
gripped me as I lifted her to the bathroom.
I'd become more worldly wise by now, and was ready to
strip her on the changing mat. But she resumed her coy
position after I removed her grubby dress.
"Now oo want to be clean, so be a good wittle girl and
let Mummy clean oo."
Once more I had to wrench her hand away to remove
the nappy, her hand shot down as the nappy came off. I
caught sight of only a tiny pinkie hidden there, and lifted
her into the bath for a rinse and then a proper clean. All the
time she kept her hands over her pinkie, very few of my
sissies would not be erect by now, but she wasn't in the
I washed her chest and back, I had to do the best I
could round her bottom, then her arms and hands. She
must have been waiting for me to clean her hands and the
movement stirred her at long last. I quickly continued with
her feet then up her legs, but I could see that under her
hands there was something fighting to remain hidden.
When I reached her thighs, she couldn't control any
longer and removed her hands to show me an impressive
sight. What had been as nothing only minutes earlier was
now eager.
Blanche was evidently most disappointed that I turned
away, and she cried. But she did know this was no part of
the day, and I lifted her on the mat and pointedly ignored
the erection and wrapped it all in a terry nappy which was
pinned tightly up. Then over her head another chiffon
nightie, this in lime green but with lots more frills, and I
took her to her cot.
She didn't need any more sleep, so I didn't lay any
blanket over her, but the arrangement was that I should
look after her while she played with one of my dolls. The
one she wanted was a male doll, and she began making it
drink from a toy feeding bottle, while I stroked her trying to
catch her eye. But she remained absorbed in feeding the
doll which began to drip and soon to squirt fully, at which
point Blanche did what I had never seen before, place her
mouth over the doll's pinkie to suck the liquid herself. She
went on feeding her doll, I filled the bottle anew and
stroked her forehead, as she raised her bottom and arched
it off the mattress, and I could see she was starting to grow
I had a lot of Sissies like this before, it was part of the
fun for many of them, but this turned me on too as she
sucked one pinkie that obviously couldn't grow, while
growing herself in a very obvious way.
She let out a little yell as I saw her nappy suddenly burst
with wee, the yellow stain covering it right round to her
bum. But I was more aroused myself when I saw her
moving her nappy up and down as she swilled more milk
into her doll in fierce bursts of feeding, so some trickled
over dolly's face.
She was obviously masturbating herself inside her
nappy and though this was no part of my Mummy's brief, I
admit I was wildly tempted to help her. I think she must
have wanted that, but I was a mere spectator, a very
excited spectator, as she arched even higher, throbbed
her wet nappy furiously in her gyrations, spilled milk over
dolly and with a cry was suddenly released from her
frenzy. She subsided and at last stared right into me. I held
her hand very very tight.
She looked very proud, no shyness now, as I took off
her chiffon covered with milk stains, and then with one
hand stroking her forehead, I deftly unpinned her soaking
nappy. She was back in the state she had entered the
nursery, only now with plenty of lovely cum cherishing that
sodden nappy to prove she'd had a completely fulfilling
Blanche came back several times after that, never so
shy, but always to that same routine. And I must admit that
after her every visit, that same evening I'd play with that
cummy nappy as I gave myself a bit of pleasure on my

Undoubtedly the most exhausting session I had was the
rare time when I agreed to have two Sissies to an early
evening session.
Ryan and Roger were strong hulking lads and I was
more than thankful when they arrived that they'd agreed to
handcuffs, to prevent their getting out of hand.
I also advised them I was videoing them, not for any
ulterior motive, but in case there was any funny business.
They'd agreed to these conditions as they lay in their
underwear on my changing mats.
I had a sailor type suit for each, one in dark blue for
Renee the other in pink for Rohaise, but they wore no
naval clothing down below, for each had a skirt, one a
matching dark blue satin number with lace hem, the other
a frilly pink tutu.
Once these were on, I handcuffed them, one hand to the
other one's hand and two longer chains held them on the
mat, which had a double rubber mattress underneath.
I was ready to remove their underpants, and I could see
they were keenly aroused. They didn't want nappies on,
but when one spurted a heap of wee across the other, I
warned Rohaise she'd have to wear a nappy if that was
repeated, and wiped Renee's skirt and her mat.
But Rohaise had evidently been saving herself, for no
sooner was the mess dried than she did exactly the same
This time, I swivelled Rohaise over, Renee lay on her
back in the wet as I smacked Rohaise's tutu with my bare
hand. I made it real hard and she cried a little.
Then I turned her back and shoved a black plastic
pantie to cover her erection.
But though they were tied down, Renee was most
definitely bent on retribution and when my back was turned
she leaned over and sprayed Rohaise with her wee. Some
landed on her face, most on her dress.
She cried in horror and I turned back to see their linked
hands attempting to thump each other.
I got real angry and undid the two long chains and
ordered them Stand Up. This time, standing on their mats,
they were chained to two rails on either side the room. I
warned them they'd have to remain standing until they
learned to behave.
Renee's response was to wee on her changing mat, and
she stood there her feet soaked in wee. Rohaise followed
suit, only hers filled her pantie which made her tutu bulge
I fetched out my whip and lashed them across their
backs, once, twice, and three lashes made them red. Then
I took down their skirt and tutu and Renee was whipped on
her bare bum while Rohaise's whipping crashed on her
bulging pantie.
She started laughing as I continued the ineffective
lashing and I could see she was becoming increasingly
erect as she suffered only traces of her whipping. Louder
she laughed as I turned to smacking, my hand bouncing
off her bum. By hitting real hard I could reach her bum,
though this made some wee spray out the pantie.
But now I'd got to hurting her, I couldn't stop, so cross
was I. Renee encouraged her, "go on", she cried to her
friend as I could see Rohaise burst into her pantie with the
thrill of ejaculating cum.
Renee thought it very amusing, until I started slapping
her bare behind, and her erection became stronger as I
walloped on her bottom.
"Naughty, naughty girl," I shouted, "it's not funny at all."
But both were laughing for all they were worth, my
slapping only encouraging them more. Finally Renee cried
out and landed a heap of cum, cascading into the puddle
on the mat below.
"Take my pantie off, please," begged Rohaise, and with
difficulty I stopped at least some of her wee and cum in the
pantie from floating away.
I went to discard the soaking pantie, but their next trick
fooled me. They must have placed some kinda lock on the
waste bin and it trapped my hand.
"It's locked you in for ten minutes," explained Rohaise,
you canna move it, just watch us."
I had little choice, I had to stare at these two naughty
sissies in their sailor suits as, handcuffed hands together,
they rubbed on Rohaise making her erect again and, wildly
excited, a spurt of cum was sprayed towards me, wetting
the carpet, not a foot away from myself. Then Renee was
ready to burst anew, fully erect again, and she aimed a
mighty ejaculation at me, the first load powerful enough to
land on my embarrassed face.
They apologised after that and told me the time lock on
the bin would soon free me, and I thankfully unlocked them
also and resolved that I'd never again entertain two clients

Of the girls, always gentler and less stressful, I specially
remember my very last client,
Shirley was a girl nearly as tall as me with long blonde
hair, to whom I took at once.
She even arrived in a sissy dress of frills and puffy
shoulders in an attractive light blue. She wanted to be
treated as a little sissy girl, so after wrapping her in a
woolly romper suit, feeding her and giving her the usual
bottle she stretched out in my lap and curled up to sleep. I
cradled her and I wondered what exactly she had come
for, she said she wanted just to be loved as a little baby
girl, so I decided when she awoke to allow her to suck my
Only girls I'd allowed this privilege occasionally, and
she surely had deserved that with her undemanding
nature. In fact the session proved memorable for me as
well as her.
When she awoke, I put my fingers thru her long hair and
without her asking, I unbuttoned my white blouse to reveal
my slender bosoms.
She needed no invitation, merely looked at me
thankfully, and she suckled like an infant. My fingers
stroked her hair, enjoying the sensation of her sucking,
when I suddenly felt a surge within me, and milk trickled
out my nipple and into Shirley's mouth.
She stopped surprised, and watched fascinated as
more drips fell from my breasts onto her face. She smiled
at me, then resumed suckling me, harder now for there
was reward, and soon my milk was flowing freely to my
immense pleasure, and, I could see, hers also,
What a special feeling that was and she continued her
drinking and I could feel her terry napping getting wetter
and wetter in my lap, until I had quite dried up and she was
satisfied. She expressed her eternal thanks as I kissed her
goodbye. Sadly she wanted to return this week, but I had
to disappoint her, informing her I'd retired.

One more lovely time I must tell you about. It was some
eight months before Shirley that little Alan came, a frail
looking young man, he'll look an ideal sissy I thought.
He had requested my most popular session, being a
sissy little girl, and when he lay on the mat, all soft and
unerect, I knew this was gonna be a special night.
Usually my clients are eager and erect, but Eileen as I
called her, lay back waiting for me to do, as she'd said
"whatever I should do."
It is always nice to have carte blanche, and I dressed
her in my own favourite sissy costume, thigh length, pink
of course, a shiny satin material with black hems and
ruffles, She didn't wanna wee so I merely pulled off her
pantie, oh yes there was in evidence only a very tiny
As she was so tiny, she snuggled into my lap so sweetly
and I lay aside my original idea of bathing her and tucking
her in for the night, in favour of singing to her. It was a
slushy sorta song about love that I liked, and she smiled at
me as I sung softly, so nice was her little look that I broke
my rules and what I'd never done before, unzipped my red
dress, and allowed her to see my bosom.
She politely hesitated, but I moved my nipple to her
mouth and she needed no other encouragement, but
licked it gently. Then she took my bosom in her mouth and
fondled it so lovingly I felt all warm inside.
I stroked her hair and kissed her cheek. She just
sucked me and tickled me with her tongue so that I quite
lost myself in the pleasure, I must have been enjoying it
more than Eileen!
I wanted her to do more- and I was the one in control! It
was not a thing I had ever done before, but I kissed her
firmly on the lip.
As I did so, I felt a trickle fall down my tummy, her little
pinkie had suddenly become firmer in response to my love,
and I could feel it growing as it pressed against my skin.
More than a trickle shot out and I became insanely
aroused as I felt her cum trickle further down over my clit.
Eileen, like any good girl, did not press herself, but
carried on her happy suckling. But I simply had to enjoy
more of this!
With one hand ever fondling her head, my spare hand
reached down and felt under her dress. There it was,
proud and inviting, so sticky was it. She kissed my bosom
even more as I pulled at her erect pinkie. I pulled it down
then up and she gave out a tiny squeal, I am sure it was
encouragement. Up and down. Up and down harder. I
fingered the skin and felt its hardness and made it even
firmer by my caresses. I should have let her have her
climax, but something made me stop.
But my pause was only for a second, though it seemed
longer, because what I did now was what I had never ever
done- I ripped off my tights to let her know what I desired,
yes, to feel her right up inside me.
I can tell you that I was so pleased to let her have her
way, so thrilled when I pushed myself onto her squirming
cock, and so ecstatic when she immediately shot out a
fertilising throb of hot pleasure that I could feel hungrily
pulsing and swirling all round inside me.
Eileen never came back, but she had left me her very
special legacy.
You see, very soon I'm gonna be raising up my own little
sissy baby, that's why I have to retire.


Last Post
6 posts
These lovely people support all the features in Sissy Kiss to contribute to our community! So it would help so much if you could check them out, and say your from Sissy Kiss. Some even give discounts, or free gifts by mentioning it!
Add your message here..
Hmmmm, exiting
Its all about the humiliation
Wonderful accounts, I loved it
is dare more of da stowy or is that it? me no see a "the end " at the end

 is dare more of da stowy or is that it? me no see a "the end " at the end  

hi bigbabysissy
yes, dere is more to dis tale, but I am too busy bwinging up my sissy babby to wite it down!  
Stevie Sweet

Great story.More please.x
What kind of post would you like to make?
To post certain kinds of posts, like images, audios, or videos you need to be signed in first.