LIVE-IN SISSY MAID
This story is protected under U.S. and international copyright law
and may not be reprinted, reposted, or otherwise reproduced
without express written permission. This story may be posted to
appropriate USENET newsgroups as long as it remains entirely
intact and unmodified, including copyright message.
Copyright http://www.RealSissySchool.com/story/wimp.html
Tom was a nice guy. Sweet. Kind. Considerate. A
great friend. But he wasn't sexually exciting. Nothing.
Not a turn-on.
He was totally in love with me. And, yes, I love
back, just not in "that way".
We were good friends. I could trust him. We even
shared an apartment (separate rooms, of course).
And he was a great housemate. He did all of the
household chores. The cleaning, the laundry, the
vacuuming, even the cooking. And he was a hell of a
good cook. It worked out great.
One day I came home early and discovered him in my
clothes! He was frantically attempting to get out of my
lingerie. He was standing there leaned over, pulling
down a pair of my panties, with one of my brassieres
still attached around his chest and a pair of my
stockings still held up by one of my garter belts. He
froze, his face the brightest red I've ever seen.
I was furious. How could he violate my trust and our
friendship by wearing my most intimate underthings?
And I became even more angry when I realized that
was why my undergarments kept coming out of the laundry
too big to wear. The jerk had been stretching them out.
After a flurry of rants, I finally told him to go
ahead and pull the panties back on. He'd already ruined
them and I really had no interest in seeing his tiny
little cock. Cover himself up.
I made clear to him that he had to buy his own
clothes. I didn't care how he dressed in the privacy of
his own room, but he couldn't keep ruining my clothes.
He whined that he couldn't afford women's clothes,
as he'd recently been laid off from his job and he
wasn't even sure if he could come up with his share of
the next rent payment.
That's when I got the idea of hiring him as a
live-in sissy maid.
I was an up-and-coming professional with a clear
path to success as a business executive. I could afford
to keep him as my personal maid and servant. And I liked
his company.
He agreed, excited as a puppy. His little penis was
an erect tent in my panties. "That's disgusting. I
don't want to see that. Go take care of yourself and
then we'll go shopping for your new clothes."
I insisted that he shave his body completely. All of
the hair was shaved off his legs, arms, back, chest, and
underarms. All that was left was a neatly trimmed little
pubic patch.
He was terribly embarassed shopping at the mall. We
picked out a few dozen panties, bras, and other
feminine undergarments to get him started. The sales
woman complimented Tom on actually shopping for
lingerie for his girlfriend. Tom became especially
embarassed when I explained to the sales woman that the
feminine undies were for him, not me.
As soon as we completed the purchase, paid with my
credit card, I told him to go into the men's room and
put on a pretty pink lace set of brassiere, panties,
and garter belt, along with black fishnet rear seam
stockings.
When he came out, I burst into laughter. You could
clearly see the pink outline of the bra under his
t-shirt. And you could see the black fishnet stockings
between his pants leg opening and his shoes. He wanted
to ruch back in and take it off, but I insisted that he
either wear it or move out. He wore it.
People giggled and laughed and pointed at him as we
walked in the mall.
At the next store, the sales woman didn't even need
to ask who the clothing was for. We picked out several
ultra-short skirts and frilly, lacy tops. The sales
woman and I had a lot of fun having poor Tom try on
different outfits, while other customers snickered and
giggled.
When we left the store, Tom was dressed in a very
short black leather micro-mini skirt and a delicate
see-through white lace blouse. His black fishnet
stockings displayed his freshly shaven legs. The pink
lace bra wasn't nearly as bright as his embarassed face.
And the miniskirt kept riding up his hips and
revealing his pink lace panties. He struggled pulling
the skirt back down over and over, juggling the growing
collection of shopping bags filled with feminine clothes.
The next stop was a shoe store, where I purchased
him several pairs of high heels. The sales woman and I
laughed as Tom stumbled while trying on various high
heeled shoes. Tom was still shakey trying to walk in
the six inch white leather heels as we left the shoe
store.
Tom was almost grateful when we picked out a long
curly blonde wig to cover up his short masculine hair.
He almost looked like a woman. His features were
naturally delicate.
Our final stop of the day was at a beauty parlor. In
addition to having his wig styled in ultra-feminine
little girlish curls, his fingernails and toenails were
painted with very feminine bright pink nail polish and
his face was made up with foundation, blush, eye liner,
eye shadow, and lip stick.
Upon returning home, I had him bundle up all of his
masculine clothes and take them out to the trash,
before putting away his new feminine clothes.
In the morning he served me breakfast in bed and
thanked me for making him my sissy maid.
When I returned from work, I discovered him in his
bedroom jerking off in his new women's clothing. Ew!
Yuck!
And his bed sheets were covered with cum stains.
He'd been masturbating all day! Disgusting!
I insisted that he had to be cleaner than that in my
place. The obvious solution was for him to masturbate
with inflatable dolls. After he finished, he could
carry the doll to the bathroom and clean up his mess
without leaving behind disgusting stains.
We went to an adult book store to purchase a doll
for him. He was terribly embarassed by the leering
glances and comments of the rather shady clientele. A
couple of them thought he was a she-male hooker and
offered him money for sex!
He picked out the Alexa's Essensual Elements
Vibrating Love Doll, the Letha Weapons Doll, and the
Chasey Lain Inflatable Fantasy Playmate. A blonde,
brunette, and red head. Those were all expensive dolls.
I picked out a couple of cheap dolls for him. The Island
Babe Love Doll, the Submissive Fantasy Doll, and the
French Maid Love Doll.
Back home, I told him that the expensive dolls were
special treats that he had to earn. He could hold onto
the cheap dolls and use them anytime he got the urge to
masturbate.
I locked up the expensive dolls and I would decide
when he was to be rewarded. He worked really hard to
please me so that I'd let him have a date with one of
the deluxe dolls.
I custom ordered real French maid's outfits,
complete with lacy white sissy panties, white lace
apron, and little white satin maid's cap. It took more
than a month to get them, but he looked fabulous in
them. Well worth the money.
***********************
Of course, once Tom started dressing in maid's
uniforms, it didn't make any sense to keep calling him
by a masculine name. I started calling him "Fifi". It
took my live-in she-male sissy maid a while to adjust
to her new name.
Things were progressing well. I got a promotion.
Fifi took care of the household chores, freeing me up
with time to date. Fifi would sometimes pout when I
went out on a date, but whenever she did that, she was
stuck using a cheap inflatable doll for masturbation.
That straightened her out in a hurry.
After several men, I really hit it off with Harry.
Harry was a great guy. Very masculine. A bit wild. And
hung like a horse.
On our third date, I confided with Harry that I had
a live-in sissy maid. At first Harry was horrified, but
the twinkle in his eye revealed that he was more than a
little curious.
We returned to my place and Fifi was decked out in
skimpy black satin French maid's outfit, white lace
apron, black fishnet stockings, six inch white high
heels, black satin sissy maid panties trimmed in rows
of white lace, and full make up. She looked so
incredibly cute.
Fifi was sullen, but she did serve Harry and I
drinks and snacks. Harry kept calling for Fifi and
sending her back and forth to the kitchen. Harry was
turned on by embarassing the cute she-male maid,
particularly enjoying watching Fifi's sexy exaggerated
feminine walk and watching Fifi bend over to pick
things up.
We retired to my bedroom, where Harry fucked me late
into the night. Between orgasms, I heard Fifi weeping in
his room. Sissy maids can be so emotional.
Harry spent several more nights before Fifi finally
adjusted to Harry's presence and stopped her silly
sulking.. Her housework improved, and she performed all
kinds of small romantic gestures that made my life more
pleasant. I rewarded Fifi's better attitude with
permission to use her deluxe dolls.
Harry and Fifi actually got along pretty well, even
watching sports on tv together. Of course, Fifi had to
make all the runs to the kitchen for beer and snacks.
Fifi referred to Harry as "Master Harold", which was
kind of funny, because not even his mom called him
Harold.
One lazy afternoon, Harry asked if I would mind if
Fifi gave him a blow job. I said that was Fifi's
decision, not mine, but I encouraged Fifi to do it
because I really didn't enjoy going down on a guy. How
much easier it would be on me if Fifi would take over
that womanly duty.
Fifi was very hesitant, at first refusing, but after
a few days Fifi consented.
Harry suggested that I have Fifi perform oral sex on
me. Harry insisted that Fifi was great at it.
I was reluctant. Fifi didn't turn me on and I'd
never had sex with Fifi. Fifi had never even seen me
naked.
Harry came up with the idea of blindfolding Fifi for
the act. That way, I could try Fifi out for oral sex
without the wimp actually seeing me naked.
Well, it turned out that Fifi was good at oral sex.
I blindfolded Fifi several times a week for her pussy
licking sessions.
In fact, that became something of a problem. It
became obvious that Harry was more into Fifi than he
was into me.
Soon Harry was demanding four or five blow jobs a
day from poor little Fifi. It became obvious that Harry
was more into Fifi than he was into me, so I broke off
the relationship.
Fifi seemed much happier not having to perform blow
jobs all the time. She re-doubled her efforts at
pampering me. And the mind-blowing cunnilingus helped
tie me over until my next lover.
That was Ramone. A handsome, muscular Black man with
his own business.
Ramone liked the idea of a dominant, successful
woman with her own live-in sissy maid.
Ramone liked the easy access to blow jobs any time
he wanted one, day or night. And Ramone was
particularly turned on by blindfolding Fifi after
Ramone and I had sex and watching poor little Fifi eat
all of Ramone's cum out of my cunt.
As much as Ramone enjoyed Fifi's blow jobs, he
wanted more. Ramone wanted to fuck her tight virgin
sissy ass. It took a couple of weeks to talk Fifi into
it, but eventually Ramone popped Fifi's anal cherry.
Ramone and Fifi and I are very happy with our
relationship, and soon Ramone and I will be getting
married. Fifi is going to be my maid of honor and is
taking care of all of the wedding arrangements.
I strongly recommend that all of you women out there
turn your sweet, shy male friends into your own personal
live-in sissy maid.
STORY EXPANDED AND CONTINUED AT WEB SITE.
FROM: http://www.RealSissySchool.com/story/wimp.html
Other sissy stories on the web site.
This story is protected under U.S. and international copyright law
and may not be reprinted, reposted, or otherwise reproduced
without express written permission. This story may be posted to
appropriate USENET newsgroups as long as it remains entirely
intact and unmodified, including copyright message.
STORY: Live-in Sissy Maid
Copyright http://www.RealSissySchool.com
|
|