My Bestfriend
- 3 years ago
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New Friend free porn video
The wonderful thing about falling apart
quietly is that you can start over.
Part 1 The beginning
First, let me tell you I'm old. No, not "mature," but OLD, past 65 in
fact. I've been a closet CD for most of my life, going through secret
purchases and purges for years. I married and had a conventional life,
work and kids. But I always dressed in private when I got a chance, then
felt the shame and repressed it for extended periods. Many years ago I
confessed my secret to my wife, or at least the CD part of my secret.
What I didn't confess was my strong fantasies about being submissive to a
dominant male that I had when dressed. She took it pretty well and even
purchased a few items for me, but was never really enthusiastic. We also
had a conventional sex life, which I enjoyed along with my secret fantasy
life. When we had children, she told me I had to stop while they were in
the house growing up, and I did, but the desire never left. When they
were grown and out of the house, I carefully broached the subject of
dressing up again. She was kind and understanding, but said it made her
uncomfortable and simply did not want to be involved or even know about
anything "like that." The subject was never mentioned again.
I'd given up on ever fulfilling my fantasies. I knew I was not going to
be able to be a sexy "gurl" of my dreams, the kind in all the story
postings that transforms into a beautiful girl, let alone find someone to
help me act out the more submissive parts of my dreams. Too old by far.
Yet the desire burned bright. Until a wonderful unexpected turn.
I met Sam awhile ago at a old car show. We were both looking at an old
Mercedes and we started talking about the car. It turned out we had a
shared interest. We exchanged names and decided to meet for lunch. That
was the start of our friendship and we met many times. He was around my
age and had been widowed a few years, living at home alone, with his kids
on the other side of the country. One day at lunch he mentioned he had
recorded a vintage car race and invited me over to watch. A few days
later I drove to his home and he welcome me with a beer and we sat down
to watch the race.
A number of beers later, I had to make a pit-stop myself, and when I came
back in I accidentally knocked over a bookshelf. Sam got up and started
to quickly cover and pickup the fallen books and magazines, but not
before I saw that some of them where rather explicit and a bit kinky! He
was very embarrassed and said he hoped it wouldn't end out friendship. I
told him I understood and certainly wasn't judging him. He said that a
combination of being lon0ely and "certain long held" secrets was making
him unhappy. I told him that we were on the same boat and that he could
talk to me about anything. He said don't be so sure as his secret
thoughts were really pretty twisted. I knew he didn't have a clue as to
my secret desires, but just said that anything he told me would never be
revealed to anyone.
And the floodgates opened. He said he always liked the idea of being
totally in charge, ordering a girl to please him in every way, dress sexy
and be punished if she failed. But he was a responsible guy and would
never, ever treat a real girl that way. His wife was always plain
vanilla when it came to sex and never did anything remotely kinky and he
had spent his whole life wishing he had been able to play out his
fantasies. And now, that he was alone, he had succumbed to reading and
watching porn. Maybe I had had a few beers too many, but I said Sam I
really appreciate your honesty and I'm now going to be honest with you.
I shared with him some of my secret desires and said it looks like our
secret selves where both very unconventional but did not mesh very n
well. He wanted to be in charge and dominate a girl and I was submissive
when dressed, and I was a guy, but he had said his fantasies involved a
girl, not a gurl.
He suddenly started laughing. I asked why he was laughing after we just
had revealed so much intimate information about ourselves. He said I
have something else to show you. He led me into the den and went to a
closed cabinet. Inside was a pile of DVDs and magazines. The magazines
were all about transvestites being dominated! Bound in Silk, Male Maids,
Submissive Sissy. He said it looks like are interests are not just
similar, but complimentary. I didn't know whet to say, we were both
pretty out in the open about something that was a great secret all our
lives. He said lets talk about where we go from here. I told him I was
afraid that if we acted on our desires things would get awkward and
uncomfortable for us both. And then he said a few things that were
incredibly reassuring. Sam said I know we've both been living with these
fantasies for most of our lives and the thought of actually living them
is scary for both of us. What if we setup some ground rules that will
allow us to have some harmless, but intense fun, that lets us both live
out are dreams and not intrude on our normal, conventional lives. So we
both started tossing around some ideas and came up with these shared
rules:
1) our playtime scenes would have a specific starting point and end -
nothing we did would be mentioned or exist outside this specific time.
2) when not doing our scene, we would be equals - playtime did not exist.
3) no mention or even hint of these activities would be shared with
anyone under any circumstance.
4) while living a conventional life, we both tended to be pretty proper
in our talking, but admitted that when thinking about sex we liked "dirty
talking." We agreed that anything goes when we were playing
5) only minor "sexy" pain was allowed, nothing intense that would leave
a mark that I couldn't explain to my wife.
6) no talk of making this a "lifestyle" or blackmail, even in jest or
play.
7) a safe word - while domination and force were important parts of both
of our dream worlds I needed an absolute ability to stop. But we also
agreed that testing my limits was also very important. and it would not
be used lightly
8) if this did not turn out to be fun, either of us could simply stop
having playtime and hope that our friendship could be sustained.
There were a few other details. Sam said that since he lived alone he
would get and store the "stuff" we needed. We were both retired and,
while not rich, pretty comfortable. I asked him what "stuff" and he said
just use your imagination. He said part of the fun for him was selecting
what clothing, and equipment we would use to turn him on. H said he
needed a couple of weeks to get ready. We decided on a date.
On that fateful day I said goodbye to my wife and said I was going over
to Sam's to help him with some work on his car and would be gone all day.
I felt a mixture of unbelievable excitement and fear. Did I trust Sam
enough? How would our roles play out. What "stuff" had Sam purchased?
Would reality destroy my fantasies. Yet I hoped.
I rang the bell and heard Sam say the door was open, come on in to the
living room. I went in, not knowing what to expect, and sat down on the
sofa. Sam came in, wearing shorts and a tee shirt. He seemed a bit
nervous, but not nearly as much a I was. He said he had been giving it a
lot of thought and had made a few decisions. First, he had decided that
he had the perfect way to clearly mark the beginning and end of our
little sessions. He took out from behind his back a beautiful lace
choker with SISSY embroider in large letters. He said that when he put
that (or any other choker, collar or necklace) on me our session would
start and not end until he removed it. Only he had the authority to do
so. And secondly, because while he was be a stern master, he was going
to go slow as he trained me to be his obedient sissy.
The first stage of my training would be begin immediately if I offered my
neck to receive the choker. I stood up and he placed the choker around
my neck. He said you are now my sissy slut. I nodded my head, and he
said, no you have to be absolutely clear. I said I'm your sissy slut.
No, no he said, you must be more explicit. Deeply humiliated I said I'm
your sissy slut and will do anything to please my master, for his
pleasure was my sole concern. He had me face a mirror and said tell me
what's wrong with this picture? I'll tell you what's wrong, slut. Look
at what your wearing, look at your hair, your face. Your are wearing
shorts and a tee shirt, like a master. But, look at your choker, you are
just a submissive sissy, aren't you. Yes, I said. He got angry and said
you really are a slow learner. You should know how to respond to your
master. I said, I'm a sissy girl and should be dressed as a sexy girl to
please my master. He said that was better, but I had earned several
demerits that he would have to punished me for a bit later.
Since I told you we would start slow, I think it's time for you to dress
for me. I told him I had never dressed in front of a man before. He
said I'm not just a man, but your master and I have many ideas on how you
must dress and perform to please me. For today I've chosen a somewhat
conservative look. Your going to change as we talk about each item of
clothing. Including how you are accepting your new role. He then led me
to the spare bedroom. Laid out on the bed was a Vintage White Exquisite
Form Long-line Bullet Bra, Vintage Pantry Girdle and Vintage Cocktail
Halter Dress. All in my size.
He said to me, sissy this is your look for today, you are a 50's
housewife. You are just a sissy and you will be much more comfortable
and relaxed when you are dressed correctly. Now get out of those silly
male clothes and put on your new finery. NOW!! I want you to tell me
about each article as you put them on. I undressed, feeling helpless and
embarrassed and stood there naked. He said you don't have much to show
as a man, but you will look great as a women. I don't get hard anymore
but the sexual thrill made my soft clitty feel incredible. I picked up
the beautiful long-line bullet bra (there were substantial falsies in
the cup, and put it on. Tell me what you are doing Sam ordered. I'm
putting on my bra master. Why are you doing that, he demanded. To look
pretty and sexy for my master. But why do you need a bra? My sensitive
tits have to look attractive for my man, I heard myself say! Now I
picked up the panty girdle. I need a panty girdle to hold my clit I
said. Then I attached the white stockings that were also on the bed and
attached them to the girdle straps. I then put the 50s Housewife Style
Swing Dress. There was also a page boy wig which I affixed to my head.
Now I (and Sam) knew I didn't look like a girl, but I was beginning to
feel the excitement of finally doing something I had dreamed about for
years and I could see on Sam's face he was also getting into it. Now
slut, walk around, stick out your tits, get use to your new position.
Yes daddy, your sissy loves her new look. He said now we are going to
watch some training videos.
We went into the den. I sat down on the couch. He said what we were
going to see were advanced ideas for future sessions, and I should pay
careful attention, because if I failed in my training consequences would
be severe. But, he would proceed slowly, letting me adjust to my new
position as his sissy slut. Sam put on a DVD and sat down close to me, I
could feel his heat through my dress. The DVD had scene after scene of
cds giving blowjobs and having their sissy asses being used. Sam was
clearly getting aroused and so was I in my sissy way. Sam says this is
all so hot that even though I said we would go very slowly, I've decided
I want some action. He told me to get up and remove my dress, leaving me
in my bullet bra, panty girdle and stockings. Walk around and model your
outfit girl, show your man the goods.
I walked around and turned, feeling humiliated but excited. Now sit
down next to your master, slut. I did and he reached over and gave me a
kiss on my lips. I had dreamed about this moment, but had never thought
it would happen. He kissed me harder and harder and his tongue parted my
lips and entered my mouth. It was the most exciting kis I'd ever had, I
felt his control over me. .His hand reached up and started to rub my
tits through my bra. Did I mention my breasts were incredibly sensitive?
He then reached under the bra to rub and pull directly on my breasts. I
don't get hard, but my clitty was tingling with pleasure. Then he told
me if a girl gets her man that hot, she has to take care of him. The
"things" we had seen on the videos would wait for another day, but for
now his slut would take care of him another way.
He took my hand and put it on his throbbing erection. I had never kissed
a man and now I was touching his cock through his shorts. I n hadn't
even had my own erection for years and now I was touching his. He said
tale it out of my shorts, get a good look at whats in store for you cunt.
I took it out and started to stroke him. It was the most wonderful thing
I had ever touched, hard but soft. He was breathing heavily in an few
minutes he started to cum all over my hand. I was a good slut, I had
made my man cum! He said now get a wash cloth and clean us both up, in
the future you will be my wash cloth, but not today. From the make out
session and giving the hand job, I had a bit of that sissy orgasm I had
read about.
The shame that set in when I masturbated alone set in, and I started to
take off my sissy outfit. Sam yelled and said cunt, what are you doing.
I said he had cum and so had I, so that playtime is over. Get yourself
over to the mirror whore and tell me what you see. I see a sissy in
underwear, I said. Look at your neck. I saw me sissy choker. He said
our session is over when In remove your collar, not before. Now come
here and get over my lap with your ass up. I went to him and laid across
his lap. He said he would not punish me too harshly, because I was new
and a bit slow, but some punishment was in order. He started to spank
me, alternating between cheeks and hard enough to sting.
After finishing he said what do you have to say for yourself. Thank you
daddy for correcting me as I deserved. Sissy will do better in the
future. Sam says I want you to hang around, dressed like the sissy you
are until I think you've adjusted to your new role, horny or not. I
spent the next hour tidying up the house. When I had secretly dressed
up in private I would immediately remove any female attire after
masturbating, feeling ashamed. Now I had to stay dressed in full view of
a man. The shame was there, but so was a delicious humiliation. Then
Sam walked up behind me, reached around and grabbed my tits for a few
minutes and rubbed my ass! He took off the collar and told me to change
back. I went into the bedroom, took off my sissy outfit and put on my
male clothes. Sam said I hope you had a good time, I certainly did, but
no more talk of our "hobby" until next time. We chatted about "normal"
stuff for about 1/2 hour as though nothing had happened, and I left.
Haven
- 12.12.2020
- 18
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