Mrs Goodwin
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My Very Good Friend free porn video
My Very Good Friend
By Wendi Robertson
My good friend, Charles Dumont, caught me cross-dressed the other
evening. I was so embarrassed! You see, Charles is a very handsome man
and very intelligent. In fact, he is a psychiatrist.
Charles and I are both successful men in our early 40s. We are both
married. Charles wife is a beautiful, sexually-charged woman who really
knows how to dress and strut her stuff, so to speak (I have always
envied that lovely woman so!) My wife is sweet, pretty, and quite
naive. In fact, she was a virgin when we married or she would have
never accepted my small penis and propensity to prematurely ejaculate
after only two minutes, or so, of sexual intercourse.
When Charles caught me I was alone, or so I thought. My wife Mary and
Charles' wife Jennifer were on an overnight trip to attend a seminar.
Charles was supposed to be tied up at the hospital with some visiting
physicians. It was a perfect time, so it seemed, for me to engage in
full makeup and dress-up, and goodness knows how I needed to release
too many months of built-up sexual and emotional tension from being
unable to really cross-dress properly. Oh, there had been my usual
quick panty sessions and some private intimacies with Mr. Dildo, while
reading transvestite erotica, but not the rush of going "all the way"
into womanhood.
Charles, Jennifer, Mary and I were such good friends we had keys to
each others' homes. Charles' hospital session had unexpectedly ended
quite early and he figured since we were both alone he would surprise
me with a visit for cocktails and a dinner out. That is the how and why
of his catching me with my panties up, so to speak.
Charles made me sit down with him and discuss the matter. I requested
that I first remove my makeup and change back into my male clothing.
Charles insisted that I sit beside him and remain fully made up and
cross-dressed. A discussion ensued about my transvestism and my sexual
desires. I was so embarrassed and quite uncomfortable as Charles
treated me like his new patient rather than his life-long friend.
Charles, "Well, my dear Wendell, at what age did you first cross-
dress?" (He called me "dear?" My goodness, did he intend to say that!?)
Blushing intensely, I replied softly, "At age 13 when I wore my
sister's sexy one-piece swim suit."
"Did you masturbate while dressed in her swim suit?" he asked in a
probing manner.
I looked down and softly replied, "Yes, Charles, I did."
Did you think of being with a man as his girl-like lover at that time,
Wendell?"
"Oh, no, Charles, such thoughts did not enter my mind at all!"
"Did you think of screwing a woman as you ejaculated that first time
wearing her swim suit?"
"No, Charles, I only focused on how good it felt to first be naked,
then wearing only a woman's swim suit as I had my orgasm."
At what age did you first do makeup, lingerie, panties, padded bra,
nylon hose, slip, and the dress, my dear Wendell?"
(Oh my goodness, he is calling me his "dear" again!)
"At age 19 Charles, and it felt so good and so natural, yet I also felt
I was a pervert of sorts."
"What was your sexual fantasy when you masturbated at age 19 in full
drag, my dear?"
I looked down, flush with embarrassment and humiliation. My
embarrassment was intensified as I looked down at my pretty skirt, and
sheer nylon stockings jutting out from beneath my skirt, my sexy high
heel shoes on my feet, my painted false finger nails, and my woman's
rings on my fingers. I suddenly became acutely aware of my throbbing
hard little erection tightly constrained by my pink satin panties and
tight-fitting panty girdle.
"Look at me, Wendell, look me directly in the eyes and answer my
question!"
I looked up at him, and at that moment I felt so feminine and womanly
and I was overwhelmed with romantic feelings and love for Charles, and
wanted so to be his submissive lover! I softly replied, "Back then,
Charles, as I beat off with my panties taut about my knees, and my
buttocks squirming on the sheets, I suddenly wanted more than anything
to have a loving, sexually aroused male atop me, crushing me into the
mattress with his primal thrusts! As I ejaculated I could feel his
fantasy penis ejaculating inside my nonexistent vagina; I would cried
out, 'Oh, fuck, I want so to be a woman! Oh fuck, I need a man so very
much!'" I hastened to add, "But as I came down from that orgasm I knew
it was a lustful perversion; that I really desired a woman sexually."
"I see, Wendell. That is quite understandable. Did this become a
pattern; that is, cross-dressing followed by masturbation 'en femme,'
with progressing feelings of wanting a man mounted to your womanly
self, and with that plaintive cry of wanting to be a woman at the
moment of orgasm, followed by post-orgasmic denial?"
"Oh, Charles, I am so embarrassed?but yes, exactly."
Charles then noticed I was hiding something behind me. He grabbed
behind me and wrestled the items away from me: a very realistic rubber
penis, a tube of KY Jelly, a gay magazine with many close ups of erect
penises, some ejaculating; and a transvestite pornographic magazine
with many photos of effeminate transvestite in various sexual
encounters with naked men. And, finally, a cuckold magazine showing
real men having sexual intercourse with wives of transvestites, the
transvestites assisting while dressed in sissified maid's uniforms.
Charles spent several minutes looking all of this over with great
interest and care as I sat pulling my skirt down again and again, flush
with embarrassment and thoroughly mortified and humiliated.
Presently, Charles commented, "Well, Wendell, the combination of all
these items is pretty apparent. You obviously are sexually aroused not
only by your cross-dressing but by your very strong desires to be as a
woman with a commanding man. That is the case, is it not, Wendell?'
Yes, Charles?yes, it quite certainly is?" I could almost feel his eyes
burning through my skirt and blouse directly to my vagina and supple
breasts!
"How do you use this artificial penis, Wendell? And, do you get great
pleasure from it? Is it exciting to use and look at?"
I responded, "Oh Charles, those are such intimate, probing questions.
But, I can't hide any of this from you, my best friend. Charles, I kiss
the dildo, I rub it up and down my nylon-clad legs, I press it against
my face and false breasts, I perform felleto on it, and I even apply KY
to it and screw my vaginal anus with it. Sometimes, when I screw my
anus with it I ejaculate without even touching my small, rigid penis?so
there?now you know!"
Soon, Charles diagnosed me as being a submissive, effeminate homosexual
with a proclivity towards graceful passivity and with a strong feminine
orientation. He characterized my condition as the state, in an informal
sense, of that of being a male woman. That sounded both so incongruous
and, yet, so exciting!
This was surprisingly followed by Charles taking me in his arms and
full-mouth kissing me! Before I knew what was happening he had one arm
around me and one hand going up my skirt! Oh, this really was good!
I broke away briefly and said, "But, Charles, you are straight and love
your beautiful Jennifer so."
He hugged me and said, "Yes I love her, but I've always wanted you,
Wendell. I've had a homosexual crush on you since high school dear boy!
Now, that I know you are a homosexual, submissive transvestite I find
you absolutely irresistible. Jenny can never thrill me like this,
honey! Seeing my homosexual fantasy boy dressed wonderfully in women's
clothing and so sweetly made up makes you hotter than Jenny ever could
be, my dear transvestite pussy boy!"
I couldn't believe it! Charles led me by the hand to the bedroom. I
awkwardly walked in my spiked high heel shoes trying to keep up with
him. He deftly pulled down the bed covers making the bed ready for
lovemaking! He gently forced me to lie on my back on the bed.
He felt me up all over, and he particularly played with my false breast
by unbuttoning my sexy silk blouse and cupping my satin bra cups with
his hands. As he discovered that I was wearing expensive, supple
silicon breast pads glued to my chest, he smiled and softly said, "Nice
tits, baby, really nice transvestite tits."
Before I knew it my skirt and slip were up, Charles deftly removed my
panties and panty girdle and he was fingering my anus with a lot of KY!
He gently forced me on my back and he took off his pants and underwear,
exposing to my wide eyes a handsome, very erect, very many penis! I
swooned with girlish moans. Oh, the indescribably erotic and sensual
feelings I felt the first time I got to see a real man's penis that was
urgently erect for me!
He instructed me, "Place your legs over my shoulders, Wendell honey.
There, there, now don't cry baby. We both need this so, and I will be
so gentle honey. With this he slowly pressed his rigid cock head
against my anus and I tried to relax as I had done many times with my
dildo. I thought my little erection would just spurt right then and
there as he slowly entered my anus, inch by inch until his manly balls
were resting atop my little sissy balls! I looked him in the eyes and
said, "Oh Charles am I your woman now?"
He responded with lust in his voice, "Oh yes, yes, Wendell baby! You
are my boy woman, the desire of my life! Oh, fuck, Wendell, you are so
tight and feel so fucking good! I've wanted you like this always,
darling sissy boy! My fondest fantasies never had you all dressed in
satin and lace and so pretty and feminine!"
He started small thrusts of his manly cock, so slowly at first, almost
like he was teasing me! I whimpered and from out of nowhere I
exclaimed, "Oh Charles, darling, I am your satin-panty sissy boy!" I
couldn't believe how wonderful his hard penis felt deep inside me!
Years of dreaming and fantasy were now our shared reality, and more
erotic and fulfilling than I could have ever, ever imagined!
Charles started thrusting inside my vaginal anus a bit faster, "Oh
Wendell, oh baby, yes! You are my satin-panty sissy pussy boy! Oh,
honey, your boy pussy feels so much better than Jenny's hot pussy!"
I started crying with joy as my Charles told me his thrusting penis was
mine, not Jenny's! I also thought about my Mary, and how she needed so
a real man to fulfill her just as her homosexual sissy-boy husband was
being fulfilled! Oh, the complex erotica of it all, thinking of
Jennifer and Mary being fucked and then thinking of Charles and me
coupled as man and woman! It was all so exciting!
My small, thin sissy-boy penis was harder than it had ever been before.
Charles strong, muscular stomach rubbed against it with each of his
sensual thrusts deep inside my girlie boy vagina! I knew I would sissy-
cum soon. I tried to hold it back; I cried out, "Fuck me deeper and
faster Charles darling!"
With this he became a primal man responding to his urgent instincts to
deposit his seed in his effeminate lover! There was no gentleness now;
rather I was being pounded into the mattress with rapid, deep thrusts
of his rock-hard cock! The sounds of intercourse filled every nook and
cranny of the bedroom: my sissy, high-pitched moans of delight; his
guttural manly grunts; flesh slapping against flesh, the bedsprings
"singing" that wonderful song of sex!
I squirmed my buttocks on the bed sheets, and I instinctively thrust
back at my virile man. He cried out, "Oh Wendell, oh fuck baby, that is
so hot!" He knocked off my wig and began to rub my bald head as he was
obviously approaching orgasm. He cried out, "Oh my hot sissy boy is my
transvestite piece of hot, hot ass! Take it pussy boy! Take my cum!!
Ahhhhh!"
I could feel his cock pulsate and discharge copious amounts of semen
deep inside my anal pussy! I could feel a very effeminate climax deep
inside my anus as my little dick spurted all over Charles' stomach and
my tummy! I held tightly onto Charles; I wanted him atop me and his
penis inside of me always!
As Charles came down from his orgasmic high, he remained hard, but
still, within my vaginal anus. We hugged and kissed for a few moments,
then he looked directly in my eyes and said, "I love you, sissy baby."
I replied, "Oh Charles, I love you so, too. I guess I always have since
we were boys. Do you suppose I became a transvestite because of a
secret need to please you?"
"That could be, Wendell honey. Then again, you probably needed to be a
male woman in any case, because you are such a vaginal, effeminate
sissy boy. And, I mean that as the ultimate compliment, my sweet cross-
dressing girlie boy! I love seeing you cross-dressed my sweet boy
woman. You turn me on so not because you can 'pass,' which you can't,
but you turn me on so because you can't pass, nor should you ever try
to pass. You should look like what you are, my dear: a very sexy boy
woman in women's clothes and makeup!"
"Oh Charles can I be your 'Wendi' instead of your 'Wendell' when we are
along together?
"I'll think that over, little one," he softly replied." I then teased
him by clamping my anal muscles on his penis and alternately squeezing
and letting go, like really hot women do with their vaginas! As I did
this, I whimpered, "Oh please, pretty please!" He breathlessly replied,
"Oh baby, you are really good?yes, my Wendi?you are one hot boy cunt!"
I loved being coupled to my manly Charles as we lie quietly kissing,
hugging, and having romantic pillow talk. I could feel that my small
penis was stuck to his manly stomach because of my dried jizz.
As wonderful as all this was, I realized that my femmie butt was sore
from our hot session of intercourse. I whined and complained a bit, "Oh
Charles, I want you in me but my sissy butt-pussy is sore."
He placed his finger over my mouth and softly said, "Quiet, little one.
That is to be expected. You will grow to accept me with no soreness at
all. As we grow together in the coming days and weeks as a couple,
honey, your butt-pussy will adjust fully to having my penis where it
belongs; where we both want it to be, right my little sex pot?"
"Oh, Charles, I know you are right. I must learn to stop being such a
whining girl and act like a grown male woman." The thought of what he
had just said was so erotic and romantic. That, with the feeling of his
still hard penis quiet inside me caused me to reach down and gently
caress his manly balls. He softly moaned and, in turn, he gently
fondled my little sissy balls and rubbed my little penis, freeing it
from the sticky jizz. He then cupped and gently squeezed my little
penis and I could feel him grow harder inside my anal vagina.
Charles began to breathe harder again and, oh my gosh, he started
screwing me for a second time. Faster and faster until the sounds of
sexual intercourse once again filled the bedroom! I thrust my ass back
at him with more finesse than my virginal first attempt at being his
transvestite girlfriend! We were truly a sexual team now, man and boy-
woman truly and thoroughly coupled and locked together in, by far, the
best sexual intercourse that bed had ever seen! (Before it had only
been my wife Mary and me!)
This time his hands cupped my buttocks as he repeatedly and rapidly
drove his hard penis home deep inside me. The feeling of his strong
hands kneading my ass as he gave me the hard, fast dick caused me to
once again orgasm from my small penis and deep inside my vaginal anus.
I swooned and cried out, "I am so glad we found each other, Charles! I
am so glad I love to wear women's clothes and sexy lingerie!"
***
Elle
- 17.08.2021
- 7
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