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Note, this a true story, some of the names have been changed, but
certainly not the events of the days!, this is taken right from my
diary entry of the time.
My (email) name is Joyce Devries and it was a real life adventure
I will never forget, my first adventure, working as a French Maid. I
am 5'2", TV, live near Toronto, Ont., Canada, pass quite well as a
woman and have done tons of "real life" things as a woman, but never
anything like this.
I will forgo the long and detailed story of how this came to
happen, but what I will tell is that I had an admirer contact me and
we started to date. Some of the dates were very cordial and nice,
while others were very steamy and hot, he was a very sexy and handsome
man, about 10 years my senior. He like to see me dress in everything
from short skirts to long and formal dresses. His only request at all
times was that I NEVER wore pantyhose, only stockings and a garter
belt, along with high heels. However, only once did I find myself on
me knees very briefly kissing his "Prince", his nickname for me was
Princess and I called his lovely 8" member "Prince".
He eventually found out I LOVED role playing and that I have a
very large collection of costumes to play a variety of roles,
everything from a nurse to a flight attendant to a cheerleader, and
yes a French maid. He loved the idea of the French maid and we came up
with the pet name of "Angela" as the character. We talked for hours
about how he would love to stroke her lovely stocking covered thighs
and watch her walk about his new apartment and clean in her 4" black
patent heels, eventually servicing his most personal needs. He
eventually asked if "Angela" was willing to come over for an afternoon
and I agreed.
He then sent me this actual email, and here is exactly what it
said:
Would you please tell Angela I will need her services very soon. She
should arrive before me and prepare herself. I would need her to come
over to my apartment, clean up and prepare a light dinner for me. I
would arrive while she was busy working and I would ask that she wear
only stockings and high heels with her uniform so that I can glimpse
her stocking tops.
I will let Angela know that she has a job opportunity and that she is
required to satisfy her employers needs totally and that she must be
prepared to bring a spare lipstick in case she runs out with the one
she has, her lips must always be 100% perfect.
You are very correct to make sure Angela has her lipstick ready, as I
will insist her lips are bright red at all times, especially when she
is servicing her employers personnel needs. Hopefully she knows how
to take her time and bring her employer to full arousal and then to
drink back the reward of her efforts. As well her stockings must be
always properly exposed so that her employer enjoys her legs and
increases his desire to have Angela please him. I have been spoiled
in the past by former servants and require someone with skill to
complete their tasks and give me complete fulfillment. If I am
disappointed I may have to discipline her, which of course will then
make my desire very strong.
If possible Angela should arrive in the early afternoon and pick up a
key from the concierge for the apartment. She will let herself in and
put on her uniform ready for work, remembering to have her stocking
tops very exposed. I will call to confirm that she is busy at work
and preparing the apartment for me. I will arrive home at 3:00PM and
expect to be greeted as follows, Good to meet you Mr. *** Sir, and
then as Sir for the rest of the afternoon. If I am pleased with her
appearance I will reward her with the ability to touch me and see if I
am aroused. I will expect a few kisses to show that she has the
proper credentials to perform her duties later that evening. I as
well will provide her with some new stockings in case hers get runs in
them from being on her knees later on.
Next at 4:00 PM I would expect a small supper prepared for me. The
ingredients would be on hand. I would expect her to prepare my bath
while I was eating. After supper at 5:00PM I would expect her to
clean up the kitchen, help me with my bath and then join me on the
couch so that I can properly caress her legs and give her the
opportunity to thank me for allowing her to train under my direction.
I would expect her to carefully but sensuously take my hard cock and
give it a complete massage before taking it into her mouth and make it
explode inside her.
If she failed to do bring me to a complete orgasm I might have to
restrain her and discipline her bottom so that she knows of my
displeasure. At 6:00 PM I would retire for a nap and Angela could
change for her trip home.
The date was set for a Friday afternoon in late March, we talked
back and forth a length on how I would arrive and the details of how
"Angela" would get into the apartment and leave. Once all the details
were set, the days leading up to the big trip were exciting. Angela's
employer name was Bob, of course for Angela it was just "sir". The
arrangements were set and all I had to do was pack and figure out how
to get to Bob's house and prepare for the exciting day. I decided that
I would be dressing rather androgynously on the way to Bob's house as
it was the next city over, and I would have to present myself as
Angela when I picked up the key for the apartment.
There was last phone conversation between Bob and I and it
was on the Thursday night, and he basically told me that "Angela" was
in for a little surprise. That is all he said and as I went to bed
that night, I could help but wonder what was "the surprise", but I was
soon to find out.
So the packing began, I backed several pairs of ultra sheer
black stockings, my 4 1/2" black patent heels, my uniform of course,
my favorite long curly black wig and all of the makeup I would need.
As well, an extra lipstick of Bob's favorite colour, as well as
Obsession perfume, Bob's favorite.
The day of the adventure came and I was on pins and needles,
I packed the car with the bag containing all that I would need and
changed into a pair of ladies jeans, nylons and low black heels. I
chose a white sweater and applied only a little makeup, some eyeshadow
and light pink lipstick. I looked at myself in the mirror, and even
with my rather short hair, I looked like a "butch" type of woman and
if I got stopped by the police, I am sure they would not say a thing.
I got in my car and I was off to the nearby city and to be a maid
for real!, I left at about 12:30, figuring that would give me enough
time to drive there and then get dressed and ready for the 3pm call by
Bob. I arrived at his downtown apartment and parking in the private
parking lot, and the apartment building was really posh, and as I
parked and got out of my vehicle, and was surprised by a security
guard!. At first I was taken back and was scared, but he was just
inquiring as to who I was visiting and in my feminine voice told him,
and asked how long I was staying and told him until around 7pm, and he
showed me the way to the lobby. Once in the lobby I introduced myself
as Angela and was handed a key and was told Mr. XXX was expecting me,
and informed me of his apartment number.
I headed up to his apartment on the 15th floor, and found that it
was not an apartment at!, but a rather large condo!, with huge windows
and a great view of the city of Toronto. Bob already told me were the
bathroom was and after picking up a wine cooler from the fridge that
he left for me, headed to the bathroom to change, the timing was
perfect as it was a little after 1pm. The bathroom was massive with
chrome and brass everywhere!.
Since I had already shaved all over baby clean before I arrived,
it was time to get dressed. I unpacked my bag and started into my long
curly wig, and then lingerie. First things first, I put on my laytex
vagina, squeezing my own member, well under, when I was done, it
looked like I had a real pussy. Then, a lacy black bra, girdle, garter
belt and very carefully rolled up a pair of very, very sheer black
lace stockings and snapped them into place. With my "clit" carefully
tucked away, I was ready for my uniform. I slipped it on and zipped it
up, added my white satin apron and white satin cap, finally my frilly
little "sissy pants", and I was ready. A quick glance in the mirror
and noted that my stocking tops were clearly visible under the tiny
little poufed out skirt.
My makeup application was detailed, but I knew exactly what I
wanted. Firstly, the eyeliner was applied dark and thick, like for a
formal night out. Eyeshadow was a dark lavender colour, and finally a
thick coat of mascara to give my eyes a "dark and sultry look". Blush
was applied to be just visible, but not too much. Finally a thick coat
of the lipstick Bob loved the taste of so much, and I took the
lipstick and shoved it into my bra for easy access later. Final bit of
makeup was applying a matching coat of nail polish, that matched the
lipstick.
After admiring my makeup job, and waiting for my nails to dry, I
took out the Obsession perfume and applied a healthy coat everywhere,
wrists, ankles, neck, and even behind my earlobes. The crowing touch
was some small diamond earrings and then I slipped into my 4 1/2"
black patent heels and was ready to go to work as a maid.
First order of business was to clean up my own mess and pack it
away which I did, then headed out of the bathroom to the large condo,
the time was 1:40pm, perfect. As I walked around the condo I noticed
that a number of books had been left on the floor, scattered about,
and I realized it had probably been done on purpose so that Bob could
get a good glimpse of my stockings and garters as I bent over!.
Shortly after the phone rang, and I answered it, and it was Bob
making sure I was dressed and busy at work. I asked if there was
anything specific he would like me to clean and directed me to the
kitchen and bedroom to clean, which I did. The bedroom was HUGE, and
featured a large king sized brass bed, the bed was not made, so I
proceeded to make sure that was take care of first. Then I cleaned up
some of the clothes that were lying on the floor and took them to the
laundry room. I was walking back from that, and then it happened!, it
was 1:50pm and the door to Bob's apartment opened.
At first I thought it was Bob coming home and the place was still
a mess, but to my surprise I was caught standing there in horror as a
woman walked in the door!, I knew Bob had a girlfriend, but she was
out of town!. I froze in horror as she spun around from closing the
door and saw me, and then simply walked towards me, holding out her
hand, and saying, "Hi, you must be Angela, my name is Brenda, Bob has
told me all about you, and oh yes, 'surprise!!'".
I shook her hand and stood there in disbelief, did she know who
or what I was?, I simply answered back in my feminine voice, "nice to
meet you mam". She spent the next 5 minutes talking with me as she
stood there with her briefcase and coat on, making comments like, "Bob
said you were good looking, but you are as 'cute as a button'", and
"so you are the 'full service maid'", she walked all around me looking
me up and down, and finally coming in front of me and then staring me
in the eyes and said, "well Angela?", making motions to her coat and
briefcase. I quickly helped her off with her coat and hung it in the
front closet and then walked behind her carrying her briefcase. She
sat down on the large sofa in the living room and I handed her the
briefcase. "Thank you Angela, that will be all for now", I curtsied
her and continued to clean up around the house.
Brenda was an attractive 46 year old looking woman, nothing
spectacular, but had large breasts and was dressed typically as any
business woman in the downtown Toronto core. Red silk blouse, knee
length black skirt, matching blazer, black hose and around 3" strappy
black heels. Her makeup was the most striking thing about her, done to
perfection, and she wore a very floral smelling perfume.
I could hear her making business phone calls and such as I was
cleaning up little messes here and there. I was then walking through
the living room and she was staring at me as she talked on the phone.
She covered the receiver and asked, "Angela, please get me a glass of
wine, and wine is in the fridge". I got her the wine and brought it to
her, standing in front of her, waiting to be dismissed.
She hung up the phone and made the comment about how I could walk
for as long as I have in the heels I was wearing. I explained it was
part of the job and it did not bother me. She told me her feet were
killing her and that would like me to remove her heels and massage her
feet. I quickly complied and dropped to my knees and slid her feet out
her heels and slowly started massaging her stocking covered feet. She
kept telling me how good that felt and starting asking me questions
and commenting on who did my makeup, and how nice it was. I answered
her and as she relaxed and I massaged her feet, the next request came,
"you can appreciate how my calves must feel wearing heels all day,
please massage them now".
I was not looking up at her, but I could feel her eyes burning
through the back of my head as massaged her calves. After about 5
minutes, the next comment came, "My thigh muscles also ache, can you
please take care of them now?". I looked up at her and started moving
my hands up her skirt towards her thighs, in doing so was pushing her
skirt higher and higher up her thighs, she just smiled back and sipped
more on her wine. A few minutes later, still staring at me she softly
said, "higher", I did as I was told and eventually was at her crotch,
her skirt was completely around her waist by now. She then reached
down and guided my right hand to her crotch and looked at me and said,
"Angela, find it and massage it", I looked back and asked, "it mam?",
she grinned and uttered, "your a woman, your should know what 'it'
is".
My thumb explored her crotch and found her "it", and starting
massaging her swollen clit. I could smell her musty scent and hear her
groan as I went back and forth and around. After a minute or so, she
stopped and asked me to sit with her on the couch, telling me not to
stop rubbing her clit through her pantyhose. She then made a comment
about how sweet I smelled and wanting to taste the lipstick Bob talked
about so much and proceeded to kiss me hard on the lips. Her kissing
was passionate, our tongues danced together and I continue to rub her
clit through her pantyhose. She then stopped all of a sudden and
declared, "I cannot take this anymore!, let's see how 'full service
you really are', come with me".
She grabbed my hand and practically dragged me into the bedroom,
once in the bedroom, I pulled out my lipstick and applied another
coat, as per Bob's instructions. Brenda commented, "that's right my
dear Angela, lips always perfect and red, now undress me". I removed
her jacket and blouse, and finally her skirt, hanging them all up
neatly. I caressed her breasts gently outside of her bra before
removing it. When I did her huge tits flopped out, 38DD's at least, I
did not touch them, but proceed to kneel down and remove her
pantyhose. Once those were off, Brenda was just dressed in a plain
pair of white cotton panties, which I slowly removed. She kicked them
off as I slid them down and found myself staring at a 40 year old
woman's shaved pussy with a clit at least an 3/4" long, it was huge.
She asked me to remain on my knees and as she lay back on the
bed, ordered me to lick her. I started licking fast and furiously,
making sure to hit all of the sensitive spots. Before I know it she
was bucking wildly with an orgasm, then another, then another, I must
have licked for 15 minutes before she finally stopped me. I remained
on my knees as I could see her starting to calm down, "Angela, you
have other work to do before Bob gets home, I suggest you get it done"
is what she uttered.
I picked myself up and headed straight to the bathroom were I
fixed up my makeup and applied another coat of lipstick. I was done
straightening up and started to go about the house, picking up papers
and such and tidying up, it was 5 minutes before 3pm.
I was in the kitchen finishing the last of the dishes when I
heard the front door open, I quickly made my way to it and there was
Bob, dressed from work and looking handsome. I took his coat and hung
it up and curtsied him. He moved towards me and gave me a long and
inviting kiss, caressing me all over my body, enjoying the lovely lacy
panties I was wearing. Then he reached around and grabbed my hand and
placed it on his crotch, I felt his cock straining through his pants.
He broke our kiss and with my hand still on his crotch, he told me
that was for later and that I should get back to work.
I curtsied him and then headed back to the last job I was doing
to finish up. I heard Bob and Brenda talking as I worked and knew they
where probably talking about Brenda seducing me. I walked through the
living room from the kitchen for the first time, and there was Brenda
in a silky cream coloured nightgown lounging on the couch, with Bob
sitting next to her. Bob asked me to come close to him and turn
around, he slowly caressed my legs and then a second pair of hands
caressed me right from my stocking tops to my heels. I just stood
there and Bob was making comments about how silky smooth my legs were
and how pretty of a maid I was. Bob then asked me to turn around and
as I did he got up off the couch when he did, both Brenda and I
noticed the bulge straining in his pants, and Brenda instinctively
grabbed for it. Bob quickly told her, "No Brenda, that is Angela's,
that is her reward for a job well done". Brenda looked a little
miffed, but stood up and announced she was heading for a shower and
that he should have fun with his "new toy", and Bob responded back
that he will.
With that Bob kissed me deeply and caressed me all over, I
responded back, and checked the bulge in his pants and I could feel
that there was some wetness coming through. The time was almost 3:45
and Bob made a note of that and said I should get started on dinner. I
retired to the kitchen and started to prepare the meal Bob had
requested, and every once in a while he would come in to the kitchen
for more wine. As he did he would caress me all over and expect
another nice long kiss of my always freshly painted lips, and expect
me to check his pants.
When dinner was finally ready, I found Bob and Brenda sitting at
the dining room table, Bob still in his suit and Brenda in her long
cream colored robe. I served dinner, nearly tripping a couple of
times, but once they were set eating what I had prepared, I went to
the bathroom and started to run Bob's bath as requested. Once that was
done I went back to the dining room and stood next to Bob as requested
and my legs were being caressed by him, as he finished up his meal.
When they were both done, Brenda retired to the living room and Bob
asked me to follow him to the bathroom, which I did. Once in the
bathroom, Bob asked me to strip him for his bath, and hang up his
clothes in neatly in the bedroom. He brought my face to his and as we
passionately kissed I started to take his jacket and tie off, along
with unbuttoning his shirt. Once he was naked from the waist up, I
moved to my knees again and started with the belt of his pants and
could see the bulge seem to grow as I unbuttoned his pants and slowly
lowered them.
Eventually, I was staring directly at a large tent, and as I
lowered his boxer shorts, there was my "Prince", standing proudly with
the tip covered in pre-cum. "Give it a little kiss Angela", was his
request, I gave the head a kiss, leaving a lipstick mark, and I stuck
my tongue out and licked a little pre-cum. "Cannot wait to give you
your 'payment' my dear", was his words as he slipped into the tub,
"now hang up my clothes, clean the kitchen then return to help me, I
will save the best part for you to clean.
I got up off my knees and hung up his suit and tie and then
returned with a soft white robe and left it in the bathroom as I went
back to the kitchen. I walked through the living room, I walked past
Brenda, who was lounging in a comfortable chair sipping on a glass of
wine listening to soft music, she made the comment as I walked by, "I
cannot believe you are still on your feet in those 'stilts' Angela?".
I responded "no problems mam", and headed into the kitchen to do the
dishes. Thank heavens for dishwashers and in no time the kitchen was
clean.
I returned to the bathroom, and Bob commented that he was glad
that it was so quick as he was almost done, and that he saved the best
for last. He handed me the soap and a washcloth and told me that I
should make sure my Prince is nice and clean. I knelt beside the tub
and used both hands to soap up Bob's now erect member and balls. I
stroked up and down with the washcloth, to clean up the soap and Bob
just sat back and moaned. When I was done, Bob got out of the tub, I
dried him off quickly and handed him his Robe. There was definite lust
in Bob's eyes as he took my hand and lead me to the living room and
sat me on the couch and then him beside me.
Bob then announced, "care for a show Brenda?", Brenda just smiled
and opened her robe and spread her legs and started to play with
herself. Bob then looked at me and said, "Angela, a job well done, now
let me really enjoy those legs, you may play with your Prince and when
I am ready, I will let you know, and you my Princess, can go and
properly take care of him". With that Bob swung my legs over his and
started kissing me with intense passion, his hands caressing from the
tips of my heels to the tops of the stockings and the garter straps as
well. I on the other hand, used both of my hands to gently massage his
balls and paying close attention to the now very wet tip of his cock.
The kissing and caressing went on for about 15 minutes, and with my
back to her, I could here Angela moaning as she masturbated. Finally
Bob could take no more and broke our kiss and looked at me and moaned,
"Angela, my princess, meet your Prince".
With that I stood up, looked over at Angela and very slowly
applied a thick coat of lipstick, Brenda just softly said, as she
stared at me, "you go girl". I turned around to find Bob gently
stroking his cock and I lowered myself in front on him, he moved his
hand from his cock and to the back of my head pushing me into his
cock. I started pleasing him, first by licking and sucking his balls,
he jumped at every touch of my lips and tongue. I licked from the base
of his shaft to the top like a lollypop, always pausing at the top to
wrap my lips around and lick up what pre-cum had formed. I carried
this on for some time, but finally, one time when I was teasing the
head of his cock, he grabbed either side of my head and started to
pump his hips up and down while holding my head still. I took the
queue and then started a rhythmic pumping up and down with my lips
firmly wrapped around his shaft. I am not sure how long I was pumping,
but finally I could hear his breathing getting quicker, and then
Brenda, moaned out, "get ready for a mouthful Angela", then about two
strokes later it happened. He blew like a volcano, I wrapped my lips
tight and slowed my strokes as he shot about six or eight good loads
of cum into down my throat, and I swallowed and swallowed, and thought
he was never going to stop.
Finally, his cock went limp in my mouth and I let it free, and
made sure he was all clean, by licking his now very sensitive balls. I
stood up and I knew my lipstick was a mess and applied another coat,
staring and smiling at Bob now all sweaty and exhausted. "Good to the
last drop?, now dear Angela, finish me off", cooed Brenda, I turned
and Brenda was motioning me to her, by this point my jaw was aching,
but I obeyed and made my way to the front of her chair. She too,
pushed my head to her swollen and very wet pussy and I began to take
care and lick and suck her large and swollen clit. She had her hands
on the back of my head and was groaning wildly, "stick a finger in",
which I certainly complied. I thrust it in and out, I could hear her
moans getting louder and louder, then she started shaking
uncontrollably as she came, almost like the first time, over and over
again. Finally she calmed and stopped and ordered me to my feet, which
I did, and again, quickly adjusted my lipstick. I looked over and saw
that Bob enjoyed the show as he was semi-erect and slowly playing with
himself.
Brenda got up out of the chair and walked over to Bob and gave
him a long lingering kiss, leaving me standing by the chair she just
got up out of which smelled musty from her juices. Brenda looked over
at my while still embraced with Bob and asked Bob, "so, did you enjoy
your little toy?", Bob just smiled and told her of course he did.
Brenda then said, "well, I want something bigger than a finger in my
pussy tonight", as she grabbed Bob's semi erect cock. Bob then stood
up and took Brenda by the hand and they walked towards the bedroom, as
they walked past me, Bob said, "come along dear Angela, you have one
last duty to perform".
I followed them into the large bedroom and as Angela laid back
removing her robe so she was naked. Bob then kissed me long and hard,
which would turn out to be our last kiss. He then broke the kiss and
said, "I need your mouth to get me hard so I can put your Prince in
Brenda's pussy". He then pressed down on my shoulder and I went to my
knees and took his semi erect cock in my mouth and started to do my
best to suck on it. It took a little while, but before long he was
hard and I could taste pre-cum starting to ooze out as I pumped up and
down. He put his hand on my shoulder and told me to stop, he told me
to give Brenda a goodbye kiss and then my duties were done and I could
leave. I got up and went over to the bed and gave Brenda a long and
probing kiss, as we were kissing, I could feel the bed moving as Bob
was moving to enter Brenda. We broke our kiss as Brenda gasped as Bob
entered her and started pumping hard.
I looked back as I closed the door to the bedroom, seeing Brenda
making love with Bob. I retired to the bathroom, and not wanting them
to see me, quickly got out of my uniform, washed my face, applied the
same makeup I had on when I came in the afternoon. The worst part was
taking off my girdle and latex vagina, my own clit was absolutely
aching, so hard it hurt, but I decided I would have to wait till I got
home to take care of it. I changed, made sure everything was cleaned
up and grabbed my bag and quietly left the bathroom, the bedroom door
was closed, but I heard no sounds.
I left the condo, got back in my car and all the way home thought
about how lovely the evening was, and I was shocked when I looked at
the clock to see that it was almost 9pm!, time does fly when you are
having fun. I got back home, took a long and welcome shower, slipped
into my favorite negligee and took care of the ache in my clit.
Needless to say it was an early night for bed.
Epilogue:
Bob sent me an email the next day telling me how well I had done
and that he and Brenda fell asleep until morning and they never heard
me leave. They saved the panties that Brenda was wearing when she
first got home as it had smears of my lipstick on them.
I never heard from them again, but think about that day every
much and often, and hope one day it will happen again.
certainly not the events of the days!, this is taken right from my
diary entry of the time.
My (email) name is Joyce Devries and it was a real life adventure
I will never forget, my first adventure, working as a French Maid. I
am 5'2", TV, live near Toronto, Ont., Canada, pass quite well as a
woman and have done tons of "real life" things as a woman, but never
anything like this.
I will forgo the long and detailed story of how this came to
happen, but what I will tell is that I had an admirer contact me and
we started to date. Some of the dates were very cordial and nice,
while others were very steamy and hot, he was a very sexy and handsome
man, about 10 years my senior. He like to see me dress in everything
from short skirts to long and formal dresses. His only request at all
times was that I NEVER wore pantyhose, only stockings and a garter
belt, along with high heels. However, only once did I find myself on
me knees very briefly kissing his "Prince", his nickname for me was
Princess and I called his lovely 8" member "Prince".
He eventually found out I LOVED role playing and that I have a
very large collection of costumes to play a variety of roles,
everything from a nurse to a flight attendant to a cheerleader, and
yes a French maid. He loved the idea of the French maid and we came up
with the pet name of "Angela" as the character. We talked for hours
about how he would love to stroke her lovely stocking covered thighs
and watch her walk about his new apartment and clean in her 4" black
patent heels, eventually servicing his most personal needs. He
eventually asked if "Angela" was willing to come over for an afternoon
and I agreed.
He then sent me this actual email, and here is exactly what it
said:
Would you please tell Angela I will need her services very soon. She
should arrive before me and prepare herself. I would need her to come
over to my apartment, clean up and prepare a light dinner for me. I
would arrive while she was busy working and I would ask that she wear
only stockings and high heels with her uniform so that I can glimpse
her stocking tops.
I will let Angela know that she has a job opportunity and that she is
required to satisfy her employers needs totally and that she must be
prepared to bring a spare lipstick in case she runs out with the one
she has, her lips must always be 100% perfect.
You are very correct to make sure Angela has her lipstick ready, as I
will insist her lips are bright red at all times, especially when she
is servicing her employers personnel needs. Hopefully she knows how
to take her time and bring her employer to full arousal and then to
drink back the reward of her efforts. As well her stockings must be
always properly exposed so that her employer enjoys her legs and
increases his desire to have Angela please him. I have been spoiled
in the past by former servants and require someone with skill to
complete their tasks and give me complete fulfillment. If I am
disappointed I may have to discipline her, which of course will then
make my desire very strong.
If possible Angela should arrive in the early afternoon and pick up a
key from the concierge for the apartment. She will let herself in and
put on her uniform ready for work, remembering to have her stocking
tops very exposed. I will call to confirm that she is busy at work
and preparing the apartment for me. I will arrive home at 3:00PM and
expect to be greeted as follows, Good to meet you Mr. *** Sir, and
then as Sir for the rest of the afternoon. If I am pleased with her
appearance I will reward her with the ability to touch me and see if I
am aroused. I will expect a few kisses to show that she has the
proper credentials to perform her duties later that evening. I as
well will provide her with some new stockings in case hers get runs in
them from being on her knees later on.
Next at 4:00 PM I would expect a small supper prepared for me. The
ingredients would be on hand. I would expect her to prepare my bath
while I was eating. After supper at 5:00PM I would expect her to
clean up the kitchen, help me with my bath and then join me on the
couch so that I can properly caress her legs and give her the
opportunity to thank me for allowing her to train under my direction.
I would expect her to carefully but sensuously take my hard cock and
give it a complete massage before taking it into her mouth and make it
explode inside her.
If she failed to do bring me to a complete orgasm I might have to
restrain her and discipline her bottom so that she knows of my
displeasure. At 6:00 PM I would retire for a nap and Angela could
change for her trip home.
The date was set for a Friday afternoon in late March, we talked
back and forth a length on how I would arrive and the details of how
"Angela" would get into the apartment and leave. Once all the details
were set, the days leading up to the big trip were exciting. Angela's
employer name was Bob, of course for Angela it was just "sir". The
arrangements were set and all I had to do was pack and figure out how
to get to Bob's house and prepare for the exciting day. I decided that
I would be dressing rather androgynously on the way to Bob's house as
it was the next city over, and I would have to present myself as
Angela when I picked up the key for the apartment.
There was last phone conversation between Bob and I and it
was on the Thursday night, and he basically told me that "Angela" was
in for a little surprise. That is all he said and as I went to bed
that night, I could help but wonder what was "the surprise", but I was
soon to find out.
So the packing began, I backed several pairs of ultra sheer
black stockings, my 4 1/2" black patent heels, my uniform of course,
my favorite long curly black wig and all of the makeup I would need.
As well, an extra lipstick of Bob's favorite colour, as well as
Obsession perfume, Bob's favorite.
The day of the adventure came and I was on pins and needles,
I packed the car with the bag containing all that I would need and
changed into a pair of ladies jeans, nylons and low black heels. I
chose a white sweater and applied only a little makeup, some eyeshadow
and light pink lipstick. I looked at myself in the mirror, and even
with my rather short hair, I looked like a "butch" type of woman and
if I got stopped by the police, I am sure they would not say a thing.
I got in my car and I was off to the nearby city and to be a maid
for real!, I left at about 12:30, figuring that would give me enough
time to drive there and then get dressed and ready for the 3pm call by
Bob. I arrived at his downtown apartment and parking in the private
parking lot, and the apartment building was really posh, and as I
parked and got out of my vehicle, and was surprised by a security
guard!. At first I was taken back and was scared, but he was just
inquiring as to who I was visiting and in my feminine voice told him,
and asked how long I was staying and told him until around 7pm, and he
showed me the way to the lobby. Once in the lobby I introduced myself
as Angela and was handed a key and was told Mr. XXX was expecting me,
and informed me of his apartment number.
I headed up to his apartment on the 15th floor, and found that it
was not an apartment at!, but a rather large condo!, with huge windows
and a great view of the city of Toronto. Bob already told me were the
bathroom was and after picking up a wine cooler from the fridge that
he left for me, headed to the bathroom to change, the timing was
perfect as it was a little after 1pm. The bathroom was massive with
chrome and brass everywhere!.
Since I had already shaved all over baby clean before I arrived,
it was time to get dressed. I unpacked my bag and started into my long
curly wig, and then lingerie. First things first, I put on my laytex
vagina, squeezing my own member, well under, when I was done, it
looked like I had a real pussy. Then, a lacy black bra, girdle, garter
belt and very carefully rolled up a pair of very, very sheer black
lace stockings and snapped them into place. With my "clit" carefully
tucked away, I was ready for my uniform. I slipped it on and zipped it
up, added my white satin apron and white satin cap, finally my frilly
little "sissy pants", and I was ready. A quick glance in the mirror
and noted that my stocking tops were clearly visible under the tiny
little poufed out skirt.
My makeup application was detailed, but I knew exactly what I
wanted. Firstly, the eyeliner was applied dark and thick, like for a
formal night out. Eyeshadow was a dark lavender colour, and finally a
thick coat of mascara to give my eyes a "dark and sultry look". Blush
was applied to be just visible, but not too much. Finally a thick coat
of the lipstick Bob loved the taste of so much, and I took the
lipstick and shoved it into my bra for easy access later. Final bit of
makeup was applying a matching coat of nail polish, that matched the
lipstick.
After admiring my makeup job, and waiting for my nails to dry, I
took out the Obsession perfume and applied a healthy coat everywhere,
wrists, ankles, neck, and even behind my earlobes. The crowing touch
was some small diamond earrings and then I slipped into my 4 1/2"
black patent heels and was ready to go to work as a maid.
First order of business was to clean up my own mess and pack it
away which I did, then headed out of the bathroom to the large condo,
the time was 1:40pm, perfect. As I walked around the condo I noticed
that a number of books had been left on the floor, scattered about,
and I realized it had probably been done on purpose so that Bob could
get a good glimpse of my stockings and garters as I bent over!.
Shortly after the phone rang, and I answered it, and it was Bob
making sure I was dressed and busy at work. I asked if there was
anything specific he would like me to clean and directed me to the
kitchen and bedroom to clean, which I did. The bedroom was HUGE, and
featured a large king sized brass bed, the bed was not made, so I
proceeded to make sure that was take care of first. Then I cleaned up
some of the clothes that were lying on the floor and took them to the
laundry room. I was walking back from that, and then it happened!, it
was 1:50pm and the door to Bob's apartment opened.
At first I thought it was Bob coming home and the place was still
a mess, but to my surprise I was caught standing there in horror as a
woman walked in the door!, I knew Bob had a girlfriend, but she was
out of town!. I froze in horror as she spun around from closing the
door and saw me, and then simply walked towards me, holding out her
hand, and saying, "Hi, you must be Angela, my name is Brenda, Bob has
told me all about you, and oh yes, 'surprise!!'".
I shook her hand and stood there in disbelief, did she know who
or what I was?, I simply answered back in my feminine voice, "nice to
meet you mam". She spent the next 5 minutes talking with me as she
stood there with her briefcase and coat on, making comments like, "Bob
said you were good looking, but you are as 'cute as a button'", and
"so you are the 'full service maid'", she walked all around me looking
me up and down, and finally coming in front of me and then staring me
in the eyes and said, "well Angela?", making motions to her coat and
briefcase. I quickly helped her off with her coat and hung it in the
front closet and then walked behind her carrying her briefcase. She
sat down on the large sofa in the living room and I handed her the
briefcase. "Thank you Angela, that will be all for now", I curtsied
her and continued to clean up around the house.
Brenda was an attractive 46 year old looking woman, nothing
spectacular, but had large breasts and was dressed typically as any
business woman in the downtown Toronto core. Red silk blouse, knee
length black skirt, matching blazer, black hose and around 3" strappy
black heels. Her makeup was the most striking thing about her, done to
perfection, and she wore a very floral smelling perfume.
I could hear her making business phone calls and such as I was
cleaning up little messes here and there. I was then walking through
the living room and she was staring at me as she talked on the phone.
She covered the receiver and asked, "Angela, please get me a glass of
wine, and wine is in the fridge". I got her the wine and brought it to
her, standing in front of her, waiting to be dismissed.
She hung up the phone and made the comment about how I could walk
for as long as I have in the heels I was wearing. I explained it was
part of the job and it did not bother me. She told me her feet were
killing her and that would like me to remove her heels and massage her
feet. I quickly complied and dropped to my knees and slid her feet out
her heels and slowly started massaging her stocking covered feet. She
kept telling me how good that felt and starting asking me questions
and commenting on who did my makeup, and how nice it was. I answered
her and as she relaxed and I massaged her feet, the next request came,
"you can appreciate how my calves must feel wearing heels all day,
please massage them now".
I was not looking up at her, but I could feel her eyes burning
through the back of my head as massaged her calves. After about 5
minutes, the next comment came, "My thigh muscles also ache, can you
please take care of them now?". I looked up at her and started moving
my hands up her skirt towards her thighs, in doing so was pushing her
skirt higher and higher up her thighs, she just smiled back and sipped
more on her wine. A few minutes later, still staring at me she softly
said, "higher", I did as I was told and eventually was at her crotch,
her skirt was completely around her waist by now. She then reached
down and guided my right hand to her crotch and looked at me and said,
"Angela, find it and massage it", I looked back and asked, "it mam?",
she grinned and uttered, "your a woman, your should know what 'it'
is".
My thumb explored her crotch and found her "it", and starting
massaging her swollen clit. I could smell her musty scent and hear her
groan as I went back and forth and around. After a minute or so, she
stopped and asked me to sit with her on the couch, telling me not to
stop rubbing her clit through her pantyhose. She then made a comment
about how sweet I smelled and wanting to taste the lipstick Bob talked
about so much and proceeded to kiss me hard on the lips. Her kissing
was passionate, our tongues danced together and I continue to rub her
clit through her pantyhose. She then stopped all of a sudden and
declared, "I cannot take this anymore!, let's see how 'full service
you really are', come with me".
She grabbed my hand and practically dragged me into the bedroom,
once in the bedroom, I pulled out my lipstick and applied another
coat, as per Bob's instructions. Brenda commented, "that's right my
dear Angela, lips always perfect and red, now undress me". I removed
her jacket and blouse, and finally her skirt, hanging them all up
neatly. I caressed her breasts gently outside of her bra before
removing it. When I did her huge tits flopped out, 38DD's at least, I
did not touch them, but proceed to kneel down and remove her
pantyhose. Once those were off, Brenda was just dressed in a plain
pair of white cotton panties, which I slowly removed. She kicked them
off as I slid them down and found myself staring at a 40 year old
woman's shaved pussy with a clit at least an 3/4" long, it was huge.
She asked me to remain on my knees and as she lay back on the
bed, ordered me to lick her. I started licking fast and furiously,
making sure to hit all of the sensitive spots. Before I know it she
was bucking wildly with an orgasm, then another, then another, I must
have licked for 15 minutes before she finally stopped me. I remained
on my knees as I could see her starting to calm down, "Angela, you
have other work to do before Bob gets home, I suggest you get it done"
is what she uttered.
I picked myself up and headed straight to the bathroom were I
fixed up my makeup and applied another coat of lipstick. I was done
straightening up and started to go about the house, picking up papers
and such and tidying up, it was 5 minutes before 3pm.
I was in the kitchen finishing the last of the dishes when I
heard the front door open, I quickly made my way to it and there was
Bob, dressed from work and looking handsome. I took his coat and hung
it up and curtsied him. He moved towards me and gave me a long and
inviting kiss, caressing me all over my body, enjoying the lovely lacy
panties I was wearing. Then he reached around and grabbed my hand and
placed it on his crotch, I felt his cock straining through his pants.
He broke our kiss and with my hand still on his crotch, he told me
that was for later and that I should get back to work.
I curtsied him and then headed back to the last job I was doing
to finish up. I heard Bob and Brenda talking as I worked and knew they
where probably talking about Brenda seducing me. I walked through the
living room from the kitchen for the first time, and there was Brenda
in a silky cream coloured nightgown lounging on the couch, with Bob
sitting next to her. Bob asked me to come close to him and turn
around, he slowly caressed my legs and then a second pair of hands
caressed me right from my stocking tops to my heels. I just stood
there and Bob was making comments about how silky smooth my legs were
and how pretty of a maid I was. Bob then asked me to turn around and
as I did he got up off the couch when he did, both Brenda and I
noticed the bulge straining in his pants, and Brenda instinctively
grabbed for it. Bob quickly told her, "No Brenda, that is Angela's,
that is her reward for a job well done". Brenda looked a little
miffed, but stood up and announced she was heading for a shower and
that he should have fun with his "new toy", and Bob responded back
that he will.
With that Bob kissed me deeply and caressed me all over, I
responded back, and checked the bulge in his pants and I could feel
that there was some wetness coming through. The time was almost 3:45
and Bob made a note of that and said I should get started on dinner. I
retired to the kitchen and started to prepare the meal Bob had
requested, and every once in a while he would come in to the kitchen
for more wine. As he did he would caress me all over and expect
another nice long kiss of my always freshly painted lips, and expect
me to check his pants.
When dinner was finally ready, I found Bob and Brenda sitting at
the dining room table, Bob still in his suit and Brenda in her long
cream colored robe. I served dinner, nearly tripping a couple of
times, but once they were set eating what I had prepared, I went to
the bathroom and started to run Bob's bath as requested. Once that was
done I went back to the dining room and stood next to Bob as requested
and my legs were being caressed by him, as he finished up his meal.
When they were both done, Brenda retired to the living room and Bob
asked me to follow him to the bathroom, which I did. Once in the
bathroom, Bob asked me to strip him for his bath, and hang up his
clothes in neatly in the bedroom. He brought my face to his and as we
passionately kissed I started to take his jacket and tie off, along
with unbuttoning his shirt. Once he was naked from the waist up, I
moved to my knees again and started with the belt of his pants and
could see the bulge seem to grow as I unbuttoned his pants and slowly
lowered them.
Eventually, I was staring directly at a large tent, and as I
lowered his boxer shorts, there was my "Prince", standing proudly with
the tip covered in pre-cum. "Give it a little kiss Angela", was his
request, I gave the head a kiss, leaving a lipstick mark, and I stuck
my tongue out and licked a little pre-cum. "Cannot wait to give you
your 'payment' my dear", was his words as he slipped into the tub,
"now hang up my clothes, clean the kitchen then return to help me, I
will save the best part for you to clean.
I got up off my knees and hung up his suit and tie and then
returned with a soft white robe and left it in the bathroom as I went
back to the kitchen. I walked through the living room, I walked past
Brenda, who was lounging in a comfortable chair sipping on a glass of
wine listening to soft music, she made the comment as I walked by, "I
cannot believe you are still on your feet in those 'stilts' Angela?".
I responded "no problems mam", and headed into the kitchen to do the
dishes. Thank heavens for dishwashers and in no time the kitchen was
clean.
I returned to the bathroom, and Bob commented that he was glad
that it was so quick as he was almost done, and that he saved the best
for last. He handed me the soap and a washcloth and told me that I
should make sure my Prince is nice and clean. I knelt beside the tub
and used both hands to soap up Bob's now erect member and balls. I
stroked up and down with the washcloth, to clean up the soap and Bob
just sat back and moaned. When I was done, Bob got out of the tub, I
dried him off quickly and handed him his Robe. There was definite lust
in Bob's eyes as he took my hand and lead me to the living room and
sat me on the couch and then him beside me.
Bob then announced, "care for a show Brenda?", Brenda just smiled
and opened her robe and spread her legs and started to play with
herself. Bob then looked at me and said, "Angela, a job well done, now
let me really enjoy those legs, you may play with your Prince and when
I am ready, I will let you know, and you my Princess, can go and
properly take care of him". With that Bob swung my legs over his and
started kissing me with intense passion, his hands caressing from the
tips of my heels to the tops of the stockings and the garter straps as
well. I on the other hand, used both of my hands to gently massage his
balls and paying close attention to the now very wet tip of his cock.
The kissing and caressing went on for about 15 minutes, and with my
back to her, I could here Angela moaning as she masturbated. Finally
Bob could take no more and broke our kiss and looked at me and moaned,
"Angela, my princess, meet your Prince".
With that I stood up, looked over at Angela and very slowly
applied a thick coat of lipstick, Brenda just softly said, as she
stared at me, "you go girl". I turned around to find Bob gently
stroking his cock and I lowered myself in front on him, he moved his
hand from his cock and to the back of my head pushing me into his
cock. I started pleasing him, first by licking and sucking his balls,
he jumped at every touch of my lips and tongue. I licked from the base
of his shaft to the top like a lollypop, always pausing at the top to
wrap my lips around and lick up what pre-cum had formed. I carried
this on for some time, but finally, one time when I was teasing the
head of his cock, he grabbed either side of my head and started to
pump his hips up and down while holding my head still. I took the
queue and then started a rhythmic pumping up and down with my lips
firmly wrapped around his shaft. I am not sure how long I was pumping,
but finally I could hear his breathing getting quicker, and then
Brenda, moaned out, "get ready for a mouthful Angela", then about two
strokes later it happened. He blew like a volcano, I wrapped my lips
tight and slowed my strokes as he shot about six or eight good loads
of cum into down my throat, and I swallowed and swallowed, and thought
he was never going to stop.
Finally, his cock went limp in my mouth and I let it free, and
made sure he was all clean, by licking his now very sensitive balls. I
stood up and I knew my lipstick was a mess and applied another coat,
staring and smiling at Bob now all sweaty and exhausted. "Good to the
last drop?, now dear Angela, finish me off", cooed Brenda, I turned
and Brenda was motioning me to her, by this point my jaw was aching,
but I obeyed and made my way to the front of her chair. She too,
pushed my head to her swollen and very wet pussy and I began to take
care and lick and suck her large and swollen clit. She had her hands
on the back of my head and was groaning wildly, "stick a finger in",
which I certainly complied. I thrust it in and out, I could hear her
moans getting louder and louder, then she started shaking
uncontrollably as she came, almost like the first time, over and over
again. Finally she calmed and stopped and ordered me to my feet, which
I did, and again, quickly adjusted my lipstick. I looked over and saw
that Bob enjoyed the show as he was semi-erect and slowly playing with
himself.
Brenda got up out of the chair and walked over to Bob and gave
him a long lingering kiss, leaving me standing by the chair she just
got up out of which smelled musty from her juices. Brenda looked over
at my while still embraced with Bob and asked Bob, "so, did you enjoy
your little toy?", Bob just smiled and told her of course he did.
Brenda then said, "well, I want something bigger than a finger in my
pussy tonight", as she grabbed Bob's semi erect cock. Bob then stood
up and took Brenda by the hand and they walked towards the bedroom, as
they walked past me, Bob said, "come along dear Angela, you have one
last duty to perform".
I followed them into the large bedroom and as Angela laid back
removing her robe so she was naked. Bob then kissed me long and hard,
which would turn out to be our last kiss. He then broke the kiss and
said, "I need your mouth to get me hard so I can put your Prince in
Brenda's pussy". He then pressed down on my shoulder and I went to my
knees and took his semi erect cock in my mouth and started to do my
best to suck on it. It took a little while, but before long he was
hard and I could taste pre-cum starting to ooze out as I pumped up and
down. He put his hand on my shoulder and told me to stop, he told me
to give Brenda a goodbye kiss and then my duties were done and I could
leave. I got up and went over to the bed and gave Brenda a long and
probing kiss, as we were kissing, I could feel the bed moving as Bob
was moving to enter Brenda. We broke our kiss as Brenda gasped as Bob
entered her and started pumping hard.
I looked back as I closed the door to the bedroom, seeing Brenda
making love with Bob. I retired to the bathroom, and not wanting them
to see me, quickly got out of my uniform, washed my face, applied the
same makeup I had on when I came in the afternoon. The worst part was
taking off my girdle and latex vagina, my own clit was absolutely
aching, so hard it hurt, but I decided I would have to wait till I got
home to take care of it. I changed, made sure everything was cleaned
up and grabbed my bag and quietly left the bathroom, the bedroom door
was closed, but I heard no sounds.
I left the condo, got back in my car and all the way home thought
about how lovely the evening was, and I was shocked when I looked at
the clock to see that it was almost 9pm!, time does fly when you are
having fun. I got back home, took a long and welcome shower, slipped
into my favorite negligee and took care of the ache in my clit.
Needless to say it was an early night for bed.
Epilogue:
Bob sent me an email the next day telling me how well I had done
and that he and Brenda fell asleep until morning and they never heard
me leave. They saved the panties that Brenda was wearing when she
first got home as it had smears of my lipstick on them.
I never heard from them again, but think about that day every
much and often, and hope one day it will happen again.
