The Retirement Home
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The Retirement Village free porn video
Part I The Retirement Village Not all tags apply to all chapters
First, just a little about me. I was widowed several years ago and was
living alone in a large, suburban house. As I got older the time and
effort to maintain the house became too much of an effort, so I started
looking for the alternative. I don't want to move to an apartment for
several reasons, but the major one was privacy. I was always interested
and attracted to cross dressing, but only had been able to do so a
furtive few times in all my 60+ years. My wife and I had a satisfying
sex life early on, but as I got older I no longer could get an erection.
Unfortunately my health, a heart condition, prevented me from taking the
"blue pill." Now that she had passed I could indulge my interests even
though my sexual excitement was limited. It is true that sex is mostly
in the mind. But even with that, I just would put on panties on a very
occasional basis - I guess guilt from a lifetime was simply too much to
overcome. But I did want privacy when I did dress infrequently in my
own home. I found the perfect compromise. A retirement complex that
had small attached cottages. Almost the privacy of a single family home
and all the troubles of maintaining the property left to others. I
moved in as soon as I could.
I turned out that the unit attached to me was owned by a very pretty
women a few years younger than me. She had been widowed for around 5
years and, like me, she wanted a place that was easy to maintain. Did I
say she was attractive? Well she wasn't a 20 year old model or even a
40 one, though years ago she certainly could have been. Jet black hair
and looking very fit.
I had just moved into the unit when I heard a knocking on my door.
There was Patricia, my new neighbor, with a cake. She introduced
herself and welcomed me, saying I'm sure we will be great neighbors. I
asked her in and made some coffee. We started talking and we seemed to
really hit it off, She was easy to talk to and had a bright smile and
laughed easily. We talked for hours, about our life histories, movies
and politics and we both were immediately at ease with one another. Did
I mention I found her extremely attractive? One really negative thing.,
Given my "little" physical problem (little being the operative word), I
knew that friendship was the most that could happen. At this stage of
my life, I both hoped for and would settle for friendship,
And that was what is was for several months. We would go to each others
homes for dinner or go out. I felt we could talk about anything, well
almost anything. We exchanged keys, just in case. One evening she came
over to watch a movie. We shared a couple of bottles of wine - the
advantage of being in adjacent units, no driving. I was sitting on the
couch when she returned from a bathroom break and sat down very close to
me. She smelled wonderful. When she put her glass down her hand
brushed my thigh. It felt like an electric shock and I just tensed up.
She said Glen, don't you like me? We seemed to hit it off so well and
frankly we are not spring chickens, so why haven't you made a move?
Between the wine, her presence and the literally years since my last
sexual encounter I was overwhelmed. Should I be honest with her? I
really like, even more than like, Pat. But if I was honest with her I
would be so embarrassed that I would have to move. But the very
thoughts that I was feeling overwhelmed my fear of -embarrassment and
consequences.
I decided, against my better judgment, to be honest. Pat, I said, I
have a confession to make. I know that it will end our friendship but I
just have to get it out of my system or I will burst. I am rather small
and impotent, there is no way I can please you. And, to top it off, I
like to wear panties. I find you incredibly attractive but my issues
make any further relationship impossible. I prepared my self for the
disgust and laughter that was about to happen, but I was only half
right.
Pat got this little smile on her face that soon became real laughter. I
wanted to crawl away and die. She saw the terrified look on my face and
she stopped laughing. She said, "You poor boy, you misunderstood my
laughter. You and I have never shared anything about our intimate lives
with our prior spouses, but I'd like to now. Jim and I, like you, had a
conventional sex life for many years. But when the kids were off to
college after a few years we were board and we started experimenting a
bit. Jim started out wanting to play some domination and submission
games. With Jim the dom. This did not work for me at all! I had been
a professional my whole work life. I saw women being disrespected all
the time. I wasn't about to be submissive to a man, even in play. I
told him if hw wanted to try domination and submission I would, but only
if I were in charge. Even though we were a bit older, our only exposure
to that kind of activity was the occasional story and movie in the
regular press. Neither of us was a frequenter of porn sites and we were
a bit naive. So like any subject we researched and found there was a
whole Femdom world. And we started experimenting. Jim tried on a pair
of my panties (just like you) and I ordered him around. We both like
it, and we expanded our repertoire the next few months. Also, like you,
we were very private. This was part time fun and Jims role outside the
bedroom remained the same. And then Jim had a heart attach and died
suddenly. We were married a long time and I loved him dearly. After
months of being depressed, I decided to, like you, to move. The kids
have their own lives across the country and I see them only on holidays.
Now for years I never even thought of sexual activity, but after I met
you that changed. But my interest in Femdom was also in my way. I
didn't want intercourse, but the thoughts I had when Jim and I started
playing were very strong.
She asked me if I thought the Femdom fitted in with my desire to wear
panties. Was there anything else? I hesitated a little and she said
wait, don't tell me now. I think we should meet again in a few days
over at my place. A few days time will give us both a chance to think
about all this. We can relax and see where this is heading. I readily
agreed. We finished the movie in silence and I walked her to the door.
She turned and gave me a quick kiss on the cheek and was gone.
The next few days were a haze. Was thus actually going to go somewhere.
Had I chanced into meeting a compatible spirit? On Thursday I took a
bottle wine and and nervously knocked on here door. She looked
gorgeous, 10 years younger than here age. Pat said "hi Glen, I am
really happy that you decided to come over." She said I looked a bit
like a deer in the headlights and laughed. She said try to relax and
let me handle how this goes. I'm in charge, so just do as you're told.
She took the wine and invited me into the living room where I sat on the
couch. Pat brought in some glasses for the wine and pored each of us a
large glass. I said I was afraid that my issues were a deal breaker and
that she would simply tell me this was a bad idea. She said silly girl
(girl!) where did you get that idea. I said my "equipment failure"
means I couldn't satisfy you. She said I told you I no longer want to
be penetrated. She asked me if I had hands, mouth tongue, ass (ass!) I
was taken aback with how frank she was. I said yes, of course. Then
I'm sure I'll be satisfied.
With that, she told me to go into the bedroom, she had a surprise for
me. When you get back lets continue our discussion. As I went I I
heard her say, "Put on what's on the bed and came right out."
On the bed were the prettiest panties I'd ever seen! Bright red with
lots of lace and bow ties. Could I actually wear these with someone
else around? My desire was more powerful than my shame. I undressed
and put on the panties. They fit perfectly and felt so extraordinarily
good. I heard Pat say "don't keep me waiting." I quickly put my
clothes on over the panties and, with much trepidation, went to the
living room. In a very stern to tone she said "I didn't tell say you
should put back your male clothes, Your getting one demerit and go back
immediately and come back in just your panties, Sissy."
I was so taken aback that I didn't even register the sissy part. I went
back, removed my clothes and returned
"Much better sissy, now walk around a bit and twill so I can have a
better view." Greatly embarrassed I followed her command. She told me
to sit on the couch and then sat down beside me. Somehow her being
fully dressed just added to my excitement. I could not help but put my
arm around her. She slapped it away and said keep you hands on your
sides, don't dare move them. She took her hand and started to rub the
panties right over my cock. It was though I had been hit by lightning!
She then started rubbing my chest and sort of pinch my nipples. It was
so intense that I could almost not stand it. Then she said "if this is
going to work you must now be totally honest with. I'm going to ask you
some questions and if you don't answer truthfully and completely I will
end this new adventure immediately." And she began the questioning.
Again, I felt deeply embarrassed and shameful, but I knew this was my
first and only chance to share all my secret fantasies with a willing
and nonjudgmental partner. I vowed to myself to take the leap of faith
and actually be honest with her (and myself) and hope for the best.
Question: I know that you like panties, but do you ever think about
more gillie types of clothes? Remembering my requirement to be honest
and complete or we end this right now.
I could not believe what I was about to say. Even as I felt terrible
shame, I told her of my deepest desires.
Answer: "Yes I want to wear all sorts of pretty clothes from Bras,
Panties & Lingerie to dresses. The more frilly, lacy and girlie the
better. I also like 50's style longline bras with bullet shape and
control girdles. Corsets are incredibly sexy.
Question: How about costumes and fantasy clothes?
Answer: Yes I replied, everything from maids outfits to playboy bunny.
I could not believe that I was saying these things out loud!!
Pat said before we continue I need to do a few improvement on you, and
she left the room. A moment later she came back with a matching red
bra, also frilly and lacy with some built in inserts to give it shape.
'Turn around Glenda and let me put this on you.' She fastened the bra
in back and then took my tits and fit them in the bra giving me a bit of
cleavage. I must of looked perplexed so she explained. "When we are
having our special fun time, your name is Glenda since looking at you
Glen is clearly inappropriate sissy. As to the bra, don't even think of
protesting. I like the way ot looks on you and I could tell that you,
like all girls, like to have their tits played with. Don't you agree?
I could only shake my head in agreement. Now let's continue the
interrogation."
Question: How open and frank do you like to talk when we are playing."
Answer: I admitted that the thought of verbal humiliation and graphic
sex talk was a strong turn-on for me. "So telling my sissy fagot to eat
my pussy is a turn on for you." I just nodded yes.
Question; How about pain?
Answer: I did not want any real pain or damage, but if I needed to be
punished, I would understand if I needed to be spanked.
Question: Bondage
Answer: If I need to restrained for your pleasure.
Question: I'm pretty good with cosmetics and I think I can work wonders
on you,how do you feel about makeup
Answer: I especially like the thought of lipstick, but full makeup might
be exciting.
Question: Jewelry?
Answer: I could never get my ears pierced, but the thought of dangling
earrings is very intriguing. Chokers and necklaces, especially if it
they said embarrassing things might be very nice.
This questioning went on for some time. I. in just a bra and panties
and Pat (mistress) fully clothed added to my humiliation. But I was
never so turned on in my life!!!
Tell me how you feel, she said. I said I felt a mixture of intense
excitement and shame to be dressed in my (?) bright red bra and panties
in front of you. She sat in a chair opposite the couch, pulled her
dress up and told me to crawl directly in front of her. "This is just a
taste of what's in store for you slut, now get your mouth and tongue
working to worship your mistresses pussy" Her pussy was magnificent.
Light curls of hair outlining her mystery. I tentatively took a couple
of licks and she grabbed the back of my head and told me to show more
enthusiasm, you just have earned another demerit for your hesitancy. I
worked the harder using my mouth to pleasure her, her scent driving me
wild. After about 15 minutes she tensed up and moaned in pleasure.
Now get up sissy and thank your mistress for dressing you up, getting
you to admit your true thoughts and desires and allowing you to please
me. "Thank you mistress for all you have done for me." With that she
dismissed me and told me to change back into my male clothes and go
home. Which I did.
The next morning my doorbell rang about 7:30. It was Pat. I thought it
was to talk about last night, but all she said was don't you remember a
few days ago (it seemed like forever ago) you promised to take me out
for breakfast today? With all that had happened, I'd forgotten. I
asked about about last night. She said I will only say this once:
Playtime is playtime. All other times we are just two seniors who enjoy
each others company. A feeling of happiness filed me. Here was a
beautiful, interesting women and we were entering into a relationship
that satisfied all our needs for companionship and excitement. She said
she had to make some important purchases, and would let me know when we
could have our next playtime. Le's not discus it any more and just
enjoy the day. And we did have a great day.
For the next few days we only saw each other for a few minutes at a
time. I was starting to believe that I had imagined the whole thing.
One day in the afternoon I got a phone call from Pat. Glenda, come over
in ? hour. Wear your regular clothing. I was a bit disappointed that
she hadn't told me to wear my new bra and panties, but she had called me
Glenda, so I hoped for the best as I rang her bell.
She opened he door. God,she was beautiful. "I have something special
and elaborate for us today. Are you still sure you want to continue on
this path?" Yes, I said. Oh Glend you just earned another demerit.
Now answer the question as befits our relationship. Yes mistress,
please continue to train me to please you. That's better. Now, I have
a some treats for you and me. Now go to the spare bedroom and strip. I
was naked in the room for about 30 minutes when she came in - wearing
men;'s clothes! She said today I'm your husband and your my 50's wife.
I think a 50's wife would try to greet her husband properly dressed and
in makeup, hoping to be ravished. With that, she opened a draw and
took out a Vintage Style Long Line Satin White Bra and matching panties
and wide garterbelt. We are going to start with these, so put them on
NOW I did as I was told, still not believing I was doing this in front
of my friend, now stern mistress. When I had them on she took at a pair
of share stockings and rolled them up my legs and attached them to the
garter belt. She said I hope you are getting comfortable in your new
role sissy, now walk around and show me how sexy you can be. Tell me
how much you appreciate me for bringing out your true self. After a few
minutes, she opened the closet and took out what she called a Vintage
Red Tulle Cupcake Swing Dress. It was beautiful. She put it over my
head and zipped the back. Now take a look in the mirror. I stood there
mesmerized looking my image in the dress. She said what's wrong with
this picture? I said I loved it. Silly, silly girl. You won't get
your husband into bed looking like that. Now sit down at the makeup
table and I will help you out. I sat down and she proceeded to apply
foundation and then mascara to my eye lashes and then eye liner. She
then added some blush and started to contour my face paying attention to
my cheek bones and then finished my make up with some bright red
lipstick. A brunette pageboy wig completed the transformation. Looking
like you do now, your husband will have a hard time waiting to fuck you.
Now let's have dinner.
Dinner was some prepared cold cuts. My husband (Pat) sat down and I
served him like a good wife. When we finished I started to clean up.
Pat said you really are a dumb bimbo. You will dirty you nice new
dress. There a apron in the closet. I went to the closet and there was
this extremely frilly pink apron which I put on. She watched me clenup
and then we went to the living room. She said I got a vew DVD's that I
think we should watch. She sat on the couch and patted the couch next
to her and told me to sit down next to her. The movies were all Femdom!
I was dressed as a housewife, all made up with a wig, but I still
thought pretty conventionally so what I saw shocked me. In one scene a
CD was being spanked by his (her) mistrees. Pat said see what happens
if you get too many demerits Sissy. Another scene showed the CD giving
oral service to his mistress. Pat said, I told you that you would be
able to satisfy me if you have a mouth and tongue. And yet another
scene showed the CD on her back with his mistress on top fucking his ass
with a dildo!! Pat said I was not joking when I said mouth tongue and
ASS when you made your confession to me. I told you I did not want to
be penetrated, but that does not mean that I don't like penetrating. I
expect you to be a good sissy wife and enthusiastically do your wifely
duties. Failure to accept your role will be met with server discipline.
Remember the spanking. And you already have several demerits. I am
giving you once last chance to change your mind. You can change out of
your girlie clothing, clean off the makeup, remove the wig and
underwear. Get dressed in your old clothing., We can still be friends
and I will never, ever mention these events. I said I feel happier and
more at peace than I have ever felt in my life, mistress. For almost
the next 2 years we maintained this arrangement. Sometimes I was her
wife, sometimes a fully dressed maid. There were days where I was told
to dress in just my bra and panties for hours while Pat and I watched
TV. And days were I had to be a totally submissive slut, begging to eat
her pussy and beg her to suck her strapon and use my ass. But like all
things in life, change was inevitable.
Lianne
- 14.07.2022
- 9
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