The Boat Show 2 Cherie
- 3 years ago
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Letter From Mistress Cherie free porn video
It's really hard when you spend your life doing things you enjoy with
your partner and then, all of a sudden, they are gone. You see, I had
lost my wife of many years to a drunk driver. I have gotten over my loss
as best as anyone could but I so missed the opportunity to indulge in
those enjoyable times we shared. No, I don't mean golfing or going out
dancing. My wife and I enjoyed a very kinky life involving leather and
BDSM and especially my being a crossdressed sissy in her service. Even
with friends in the local West Coast kink community, I could never find
the intimacy I was looking for there.
Some day when the lawyers finish their work I will be able to retire and
relax. It has been 3 years since and I am tired of working so I hope it
is completed soon.
So I gave up on dating and started to look for a partner online. Maybe I
could just start over somewhere else. Or not. I might as well look and
see whats out there. About a year ago I met a wonderful woman from France
online. Having also lost a spouse we had many common events in our lives
and we shared similar kinks on so many levels. We chatted regularly on
Fetlife and Skype and really clicked. I am 10 years older than Ms Cherie
but that never appeared to be an issue. We loved playing online but
always seemed to have issues with the time zones between us. Either she
was at work or I was.
We did manage to find our time together and played sexy games on cam with
each other. She really got off on having me as her sissy and seemed to
know just what buttons to push to get me hot. She loved that I was
totally hairless below my head and that I had pierced nipples, a navel
piercing and some genital piercings as well. Some nights she would have
me paddle my ass while she pleasured herself, some nights she would love
to see me dressed and fucking my sissy ass. At times she would have me
doing cbt, abusing my cock until it was too sore to touch. These scenes
seemed to really turn her on the most. There were even times I had to
sleep in a baby diaper to please her. I loved watching her orgasms on cam
and could only dream of being there to lick her and serve her in person.
We connected on many other levels as well and my years of business
experience have helped her in her daily life as well. It wasn't just
about the kink. We both shared a variety of interests including the
theater and ballet, concerts and cooking and travel. It seemed like I
might have found love for a second time in my life. I asked Ms Cherie if
she would consider accepting me as her property. My heart skipped a bit
when she said yes.
One day after a long Skype session involving some cbt play she told me to
stroke my sissy clitty for her. She wanted me to cum for her but, I had
to use sandpaper to do it or I couldn't squirt. After about 8 minutes my
already sore penis couldn't take much more. I begged her to let me stop.
She said that I couldn't squirt if I didn't use the sandpaper and said I
could stop if I get out my CB3000. I had mentioned I had one to her
previously but had said that it had not been used for many years. I got
it out and cleaned it up a bit. She told me to put it on and lock it. She
watched intently as I placed the ring and cage over my "clit" and locked
it shut. She asked me to show her the keys. I held up the 2 keys for her
and she told me to put them in an envelope, seal it up and mail them to
her.
I told her that I was unsure if that was safe to not have a key
available. She told me it was safe as long as she had the keys to her
property so I had better obey. After I addressed the envelope she
reminded me that it was I who complained that it was too sore to touch.
Now I wouldn't have to worry for a while about touching it. Hard to argue
with that logic. She promised that she would send one key back so that I
would be unlocked within two weeks. Hope the mailman doesn't lose the
letter.
We continued our chats over the next week or so. More and more I was
having to use dildos and plugs on my sissy pussy, and in my mouth as
well. Being locked I was told these were my only options. With clamps on
my nipples I would spend and hour or so learning to deep throat a dildo
for her amusement. When I used them in my bottom she enjoyed watching my
clitty drip its juices as my prostate was stimulated. On other occasions
she would have me diapered firmly and made to eat multiple containers of
baby food prunes or other yucky tasting stuff and drink from a bottle for
her. My sissy clit longed for attention and would cause me pain form
getting hard. Which was every time I thought of Cherie.
One Thursday I got home from running errands and there was a letter from
France in the mail box. I could feel the key in the envelope. Yea, I
could get unlocked now. I tore the letter open on the way into my house.
I started reading:
Dear sissy baby
Here is your key for the chastity. You will Skype me tonight and we will
release you. You will have a wash basin and cloth handy at that time.
Once released you will clean your clitty and put the chastity and its
parts in the water to put away later. I have ordered a more secure
chastity for you. It will arrive by post in 6 days. Here is what will
happen between now and then.
When you are clean we will make your little clitty squirt. But you will
squirt in a zip lock bag and then place it in the freezer.
As it is morning for you now, you will squirt into the bag again tonight.
You will continue to squirt 2 times a day for the next 4 days. More if
you can.
At the end of the 5 days we will measure how much cum you have produced.
Believe me when I tell you not to miss an opportunity to add to your
little cum bag. The more you produce the happier you will be.
Love and Kisses
Your Mistress Cherie.
Well I skyped Mistress and thanked her for the key. I definitely needed a
good cleaning. After removing the chastity and cleaning up it didn't take
long for me to squirt. It looked like a lot of cum to me but apparently
not to Mistress. She kinda laughed at me and said I better hope that I
can produce more next time or I may not like it.
Reminding me of the letter she signed off. I did not hear from her until
after the 5th day
That night I worked my self up to another orgasm and added that to the
bag. I did my twice a day and it certainly didn't look like all that much
in the bag. I did 3 a day the last 2 days and it seemed that the bag held
a fair amount of frozen cum.
The next afternoon I returned from work to find a package in my mailbox.
It was from France and must be the new chastity. It was heavy for the
size. I went inside and opened it. On top was a note from Cherie that
said read before opening bag. I guess the black cloth bag held the new
cage. The note said:
Sissy baby:
I hope you filled your bag for me. And it better all be real cum because
if not I can tell by looking at it. When you get this you will bring to
your desk a clear measuring cup and the new chastity, and a good
attitude. You have had a lot of time to play with your clitty but that is
going to change for a while I'm afraid.
We are going to measure your sissy squirts. If you are fortunate enough
to have stored 7 ounces or more away you will receive 2 weeks in chastity
and one week out.
7-8 you will get 3 weeks locked and one week out.
6-7 will cost you a month in and a week out but we will add the spike
ring to it as well.
4-5 ounces will put you at 6 weeks in and 4 days out with the spike ring.
3-4 ounces, (I hope you got more than this) will also be 6 weeks but the
front shield with the internal spikes will be added.
Under 3 ounces. You are in real trouble if you cant top that babygirl.
You will be locked up until you come to France and have your cage removed
by me.
You will also need to fill a tall glass bottle half way with water and
freeze it. Have this ready as well. Skype me at 3am Paris time.
Love
Mistress Cherie
Holy shit. I run to the freezer and look at my frozen bag of cum. Its
hard to tell but I think there must be 4 ounces in it at least. I quickly
jerk into it again and put it back in the freezer with the requested
bottle of water.
At 7pm everything is in place and I call Mistress Cherie. She tells me to
get the baggie of cum and the bottle and return and strip naked. I show
her the frozen bag of cum and she laughs and says it doesn't look like
much to her. I am told to sit and put it between my legs until it is all
melted so we can measure it. It is really cold and causes my clittie to
shrink rapidly. We chat about our past few days and some news items as it
melts.
I am told to open the bag with the new chastity. I looks like a cb3000
but made of stainless steel. There is the regular ring that goes behind
the cock and ball. A second ring that goes over the cock but in front of
the balls with 4 sharp (yes I do mean sharp) spikes in it. There is
another curved metal plate with a slot that would fit inside the front of
the metal cage with numerous little metal spikes on it. There is a weird
little nut and bolt, an odd looking little screwdriver, and a tube of
super glue. The head of the bolt is round and smooth except for 4 tiny
holes in a weird pattern. Apparently they match the odd screwdriver.
She asks if the bag has fully melted and I tell her yes. She tells me to
pour it all into the measuring cup. I follow her directions and I almost
cry at the results. It shows no more than 2.7 ounces. I try desperately
to squeeze more out of the bag but its no use. There's no way that I can
get another .3 ounces out of it. I am royally screwed. Mistress is
laughing while watching me and I cant blame her. She tells me she was
hoping for more but is still pleased with the results telling me that
maybe I should have tits instead of a sissy clit if that's all it can
produce. I tell her its not fair because I was never a heavy cummer. She
said I had plenty of time to produce more and should have worked harder
at it.
She asked me when I would be able to visit and I told her it would not be
before 6 months. She told me it would please her so much to have me
locked that long.. I was told to check the fit of the spiked plate and
then to spread the glue on the front of it and fit it in place. Next I
was made to put the two rings on and then attach the cage. The nut was to
inserted into its notch and then the bolt was tightened into place with
the special driver. I was told to put the screwdriver back in the box and
mail it back to her in the morning.
Not wanting to waste the cum, Mistress had me take my fat plug and dip it
into the measuring cup and then lick it clean for her. As mistress was
enjoying her vibrator she had me dip it again and then push it in my
sissy ass. I continued this first in the mouth and then in my ass until I
had eaten half and filled my pussy with the remainder. She loved that I
was wincing in pain from the spikes all the time this was happening.
She told me that the chastity had more openings to be able to keep my
self clean than my other so I should not have a problem in that area.
After she had a major orgasm watching me she said she needed to go to
bed. I was told I would not need the bottle of ice. And since I was
sending the key back maybe I should empty it and start saving my pennies
in it for a plane ticket to France. Although I hadn't told her I sure
hoped my lawsuit money would come through soon so I wouldn't have to stay
locked so long.
Spring had arrived and I had been locked for the past 2 weeks. The head
of my sissy clit felt like a pin cushion from the spikes in the end of
the chastity. Every time I got excited they would remind me of my place.
The spiked ring at the base insured that I could not pull out of the
tube. Mistress Cherie and I talked a couple times a week. It wasn't
always sexy stuff. Often we just talked about life and got to know each
other better. She would always check to make sure the chastity was in
place though. Some days she would have me hold a vibrator against it just
to make me squirm. I was falling deeper and deeper in love with her and
deeper under her control as well.
Not much changed until about 10 weeks into my chastity regimen. I got a
call at work from my lawyers. We finally were going to settle my suit. I
left work early and met with them. I would be getting about $6 million
after taxes. A bit less than I wanted but I was pleased. I signed the
papers and would have the check in 2-3 weeks. I went back to work and
told them I was going to be retiring in a couple weeks. After 15 years I
had made many friends there but I was certainly ready to move on and they
were saddened to hear I was leaving. I would receive a nice severance
package and other perks I had coming to me.
I went home and started searching plane fares to Paris. I emailed
Mistress Cherie and told her I was ready to plan the trip over to meet
her. She wrote back to call her on skype that evening. I spent some time
checking my passport and insurance other personal things and made sure
they were all up to date. I made a checklist of things that I would have
to do before I traveled. If nothing else happened on the trip I would at
least be getting unlocked.
Mistress was elated at me finally retiring and traveling to meet her. I
had not yet told her of my coming windfall. We looked at dates on the
calendar The best time for me to fly would be early June. Cherie said
that she would be at the beach in Nice for most of June and I should meet
her there. We could spend the time enjoying the beach and the
Mediterranean before returning to Paris.
We played for a couple hours on cam that night. Mistress had me sitting
on my largest plug while she pleasured herself to 3 strong orgasms. I was
in pain at both ends watching her and listening to her telling me all the
things she wanted to do with her sissy. How she was so hot to have me
serving her in person. Learning to please her properly.
Time couldn't pass quick enough after that. As soon as I had my severance
from the company I booked my flight to Nice, flying through Barcelona. I
arranged for a friend to watch the house when I was gone and took care of
all those loose ends you need to do before traveling. I met with my
financial adviser and we worked out a plan for my funds to be invested
and banked.
Finally June 4th I was heading to LAX. My bags were packed according to
Mistresses instructions. No male clothing. I was wearing a womens dark
blue business suit with pants not a skirt. Unless you looked closely you
would think it was a mans suit. My shoes looked like wingtips but had a 1
? " heel. I wore my long straight hair down. I had a touch of mascara on
and a very pale pink lip gloss. The flight was mostly uneventful and I
slept for much of it. Well, uneventful is you don't count trying to get
through security with a steel chastity on. The TSA made me actually go
into a closed booth and show them the chastity. And of course the saw my
blue lacy panty as well. They cleared me to fly and as I left their area
I heard one of them comment " another fucking sissy". What as asshole, I
thought. And then there was the flight attendant that spent too much time
telling me how "pretty" my suit was and how she would bet I would look
really pretty with a nice hairstyle.
Finally arriving in Nice I got my baggage and headed to customs. No
problems there thank goodness and as I exited out into the terminal and
there was Mistress Cherie. She looked so hot I couldn't believe it. Twice
as pretty in person and taller too. She was dressed as a vacationer to
the beach would be in shorts and a tank-top. A little bit of make up but
not too much. She came over and gave me a huge hug and warm long kiss.
She gave my chastity a grab as we broke our embrace. We finally said
hello and she pointed to the floor and I knelt down right there in the
terminal and kissed her feet. I didn't notice or care if anyone was
watching. We chatted about the flight as we headed for her car, a very
new Puegot sport sedan. It was late morning and she said that we would go
to her beach house and I could change before we went to lunch.
She had rented a nice 2 bedroom home on the beach. What a spectacular
view. Of her ant the sea. Lol
I changed into some shorts and top and we walked down the beach to a
small restaurant. Over lunch she told me we would have a great time at
the beach for a couple more weeks before returning to Paris.
She also said that she wanted me to be Briana while I was here. No more
Brad for a while. We had a lovely lunch and walked along the beach for a
while. I said I would love to go for a swim and reminded Mistress that
she had not told me to pack a swimsuit. She decided we should go into
town and do some shopping. She asked me my sizes and converted them to
European sizes so we would know what to get.
First stop was a dress shop where she picked out a couple new outfits for
me. I tried them on and when she was happy we paid and moved on to a shoe
store. Some beach sandals, a platform pump a pair of sneakers and a new
pair of 4" heels in blood red.
We stopped in a hair salon that she frequented and she talked to the
stylist for a bit. Cherie said she would continue shopping and get me a
couple swimsuits and lingerie while Ms Claire did my hair and nails. I
was treated like a queen at the salon, A pretty pedicure with sissy baby
written on my bright pink big toe nails. My manicure left me with nails
almost a half inch long in a matching pink. Ms Claire shampooed my hair
and began styling it. I asked what she was going to do with it but she
did not speak English and although getting better my French is not that
strong yet. I hoped I would still be able to tie it back in a ponytail to
look a bit more manly if needed. She she finished and turned me to the
mirror I saw a head of beautifully styled hair, wave after wave cascading
to my shoulders. No way this would ever look male.
We moved to a more private area in the back and I laid on a massage table
while she waxed my brows. She plucked a few strays and handed me a
mirror. My brows were now in a very feminine but not too severe arch. I
could live with that. I guess I will have to until they grow back. She
had me remove my top and the bra I was wearing. I am glad I had no hair
because I didn't want the pain of the wax on my breasts. My pierced
nipples didn't seem to phase her at all. She did notice some hair under
my arms and had me raise them up and she waxed both sides. Pleased that
the hair was gone she took a small jar of sweet smelling cream and rubbed
a bunch into my breasts. She massaged them until it disappeared into my
skin and smiled to herself. She handed me my shirt, and then handed me 4
jars of the cream and I think she told me to rub it in 3 times a day. It
was about 4pm when Cherie returned for me and her wide smile told me she
liked my new look. We made one last stop on the way back to the beach. A
small jewelry boutique where she picked a piece for my naval, a dangle of
bright pink crystals and had another hole added to each of my ears with
matching crystal posts put in them.
Brad was quickly fading into the background as Briana appeared. I just
wanted to get back to the house and have my chastity unlocked. We did
finally make it back to the house and unpacked my suitcases and the new
purchases making sure everything was properly put away. Mistress Cherie
then told me to strip and stand in the center of the room and remain
motionless. I could feel her warm breath on my neck as she stood close
behind me. Whispering in my ear. "Slut", "My own sissy baby", "You belong
to be now baby", "You will serve me and obey me in every way I command",
"You are MY sissy" "my property", " My bitch", "My babygirl", "I will
use you and abuse you" " You will crave my touch", "You will love me more
everyday because of it" , "You will beg for it"
I heard the woosh and felt the crop land on my ass. I was startled and
jumped. "Back into place she demanded. 10 extra for moving. She proceeded
to rain strokes down on my ass. I remained motionless, as if frozen in
place by my Mistress. My ass was on fire when she finished and my poor
clit was pushing hard into the spikes. "Thank you Mistress was all I
could say." Mistress told me to get her some wine and cheese and bring it
to her in the bedroom. I did as told and found milady relaxed on the bed.
I set the tray nearby and stood quietly as she sipped it. I decided to
ask about the ever present chastity and when she would remove it. She
replied that she had left the key at her home in Paris and would see how
well I behaved over the next 10 days before we returned there. If I was a
good girl I would be unlocked as soon as we got there. I was of course
disappointed that I would remain locked for another 10 days but was in no
position to argue the point.
Mistress then told me to take off her shorts and panties. I eagerly and
tenderly removed them and with an aching clit admired the beauty of her
feminine form. I was instructed to pleasure her and to pay attention to
her instructions in how she liked it. She made a point of informing me
that she did not like to explain things twice. I eagerly went at my task.
Following her instruction and adding some of my own technique. Gumming
her clit, running my tongue inside the clit hood. I soon had her moaning
with pleasure and had her orgasm wildly beneath my mouth. I gently licked
up all her juices as she came back to earth.
She rolled over and motioned me to her ass. I needed no extra
encouragement and kissed he beautiful cheeks, slowly making my way to her
rosebud. I gently kissed and sucked on it and when I drove my tongue
deep into her I could hear her moans. I fucked her beautiful ass with my
tongue, in deep, sucking her as I did. I slid my hand under her and
touched her clit as I sucked and she exploded in another orgasm. We
snuggled for a bit and must have fallen asleep. It was getting dark as we
awoke for our nap and we could see a beautiful moon rising over the sea.
Cherie said we should go for a night swim before its totally dark and
watch the moon rise. She handed me a silver maillot bathing suit and put
on her bikini and we headed down the walk to the beach. I mentioned that
the chastity looked a bit funny under it. She said no one would notice in
the failing light and she had a skirt to cover me during the day. The
water was warm and relaxing but really stung on my crop striped bottom.
There were only a handful of people out this night and I doubt anyone
thought we weren't 2 women out for a swim.
We made our way back to the house and as jet lag was taking its toll on
me. We showered and were getting ready for bed when Mistress reminded me
to get my breast cream and apply it before bed. She then pulled out a
beautiful diaphanous pink babydoll for me to wear as she slept in the
nude. I'm sure I was asleep in 5 minutes.
We slept until 11 am, at least I did. Mistress woke me with a kiss and
said breakfast was on the table. I totally didn't expect her to do that.
We had a light breakfast and I did the dishes before showering. As I was
drying off Mistress Cherie came in the bathroom dressed in a tiny black 2
piece swimsuit that showed off her spectacular body, and a jar of the
breast cream and began rubbing it into my chest. Damn that made the
chastity hurt. I asked what was in the cream and she told me it was an
old French formula that women have used there for years to promote breast
growth. I told her it tingled a bit and she said that that was a good
sign that it was working
She said I was too pale and we are going to spend the day at the beach. I
mentioned that I couldn't wear the maillot suit to the beach. She
responded "Of course silly sissy. Your chastity would show right through
it. I have something more modest for you." She led me into the bedroom
and handed me a 2 piece pink bathing suit. The top had straps that
crossed in the back and the bikini had an attached skirt. "See baby, the
skirt will cover your chastity and all you need to do is act like a girl
and no one will care. You will see there are a lot of gays at this beach
and no one will notice you.." she laughed.
"But I " and she cut me off. "If you want to be unlocked you will have to
learn to behave sissy, now lets put some lotion on and get to the beach."
She handed me a bottle and I spread it on her already tanned body. She
used a different lotion on me. I could tell by the scent. I told he I
needed a lot of protection or I would have tan lines. Mistress told me "
that's why she was using that lotion." She handed me a coverup and put
one on herself and having no choice it was off to the beach, blanket and
towels in hand. The beach was semi private but still fairly full. We set
out our blanket and sat back to people watch and enjoy the sights.
We were getting a few stares from passerby but Cherie said not to worry
as they were probably looking at her not me. I couldn't argue with that
logic. We went for a quick swim in the clear Mediterranean waters. We
sunned some more before Mistress sent me to the beach cafe and to fetch
some wine coolers and fruit. I refreshed my lips and headed the hundred
yards or so through the beach-goers to get them. I was glad the bikini
had the skirt attached. I was getting a few looks so I started to flow
with it and walked as sexy as I could through the crowd. I think the
bartender/server was hitting on me when he took my order but I couldn't
understand him. When I paid he gave me a card with a phone # on it.
I told Mistress about my experience and showed her the card. "Oh that's
Henri, he is a drag performer at one of the gay bars in town, He's very
talented. Maybe he can get us in to the club. Its a great show." She put
is card in the bag. In the sun the coolers hit me harder than I thought
as I rarely drink at all and never in the daytime. Mistress put more
lotion on me and I think I nodded off for a while. I awoke on my belly as
M'lady tickled my foot. "Cant let you lay there and burn baby, lets go
for a dip." we swam a bit more and headed back to the house.
Mistress showered as I stood by with a towel. After drying her off she
removed my bikini with a big smile. I had tanned nicely but had the
obvious lines of the bikini. "I though the lotion would prevent that
Mistress?" " Not what I said sissy, you need to listen more clearly.
Maybe it is my poor English she joked. And it does make you breasts look
bigger. She rubbed more cream into my breasts and said to put on the
clothes on the bed. She was back in shorts and a braless cami. On the
bed I found a lavish pink maids outfit that she must have gotten for me,
and the 3 ? " black patent heels I had brought along. There was a pink
underbust corset that she laced snugly around my middle after having me
pull on the matching pink stockings. Panties and a garter belt and some
makeup and I was directed to start cleaning.
I spent a good 2 hours cleaning the kitchen as Mistress sat on the porch
and read while enjoying some wine and cheese. She called me out to her
and said there was a menu on the fridge and I was to prepare it for
dinner. Everything I needed would be found in the kitchen. I enjoyed
cooking and had no problem preparing a mushroom and chicken dish over
rice with fresh sauteed asparagus. Mistress allowed me to dine with her
and after dinner we took a stroll around the local neighborhood back to
the house.
Mistress relaxed in the living room and told me to freshen my make up and
return to her. I did as told and went to her immediately dropping to my
knees. She had removed her shorts and told me to get busy pleasing her. I
needed no additional encouragement and gladly pleasured her. I was so
happy to be pleasing her at that moment that the pain in my locked up
clit was . I know its hard for some of you reading this to fully
comprehend, but I felt that the pain in my clit was like a gift from
Mistress for bringing her pleasure and it was no longer pain to me.
Mistress was so hot and my face was coated with her juices when she
pulled me up to her face, fully sated, she kissed me deeply tasting he
sweet juices on my tongue. She then turned over and allowed me to worship
her ass for a while before we retired to the bedroom.
Mikayla
- 04.05.2020
- 29
- 0
