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How It Could Have Been free porn video
HOW IT COULD HAVE BEEN
By Miss Wendi Robertson
This is a fictional account of how it could have?most likely would
have?been had Jack and William met as young men of similar age.
The period would be the late 1950s or early 1960s when
transvestites and their admirers were still very private people. The
setting is a lovely small college somewhere in America. William is
age 22 and Jack is 23. William is a freshman and Jack is a
sophomore. They are both taking Accounting 101.
One warm, sunny day, just after class, Jack approached William and
said, ?Hi, I?m Jack. I enjoy your intelligent discourses with the
professor in our account class.?
?Thank you, Jack. I am very glad to meet you, too,? replied
William.
Jack then asked, ?Do you work part-time William??
?Yes, I do Jack, I teach flying at the local airport,? replied William.
?Wow, that sounds interesting. Maybe you could take me flying
someday,? Jack stated. He quickly added, ?Since it?s lunch time
would you like to join me at Harry?s Coffee Shop for a sandwich??
William said, ?That sounds great Jack, I was thinking of driving
over there anyway. Let?s take my Chevy, it is right over there,?
William pointing to his ?56 Tutone Bel Aire.
The two young men drove in William?s car to the school?s most
popular burger joint. They had a great conversation over lunch and
soon learned that they were very comfortable with each other and
seemed to share many mutual interests. They also both commented
on some really hot girls in the eatery, and grinned about how they
would like to ?make? those tightly skirted, voluptuous sweater girls.
William commented quietly, ?Jack, notice the cute blonde with that
very tight purple skirt. She has to be wearing a hot girdle.?
Jack replied, ?Why do you say that, William? How can you tell??
?Well, Jack,? said William, ?Notice how her supple buttocks don?t
jiggle when she walks and notice how flat her groin is.?
Jack smiled, ?I guess I am not that observant, but I sure do notice
what a hot body she has! But, I do admit the thought of her wearing
an open-bottom girdle, with garters and nylons, is a real turn on.?
William couldn?t help blushing just a bit, thinking of his own
transvestite?s open-bottom girdle, which he had worn just the past
weekend, along with a hot outfit as nice as the blondes? and even
with a sexy wig and makeup. But, he immediately suppressed the
thought, thinking how completely inappropriate it was to even think
of his transvestite proclivities, sitting here with a normal young man
and around all these beautiful, charming young women.
Soon, the delightful lunch was over and the two young men were
driving back to school. Suddenly, the right rear tire of William?s
Chevy blew out. He carefully controlled the car and pulled safety to
the side of the road.
Jack said, ?I hope you have a spare, William.?
?Oh, I certainly do, Jack, everything is in order.
Jack said, ?I am pretty good at changing tires, let me work the jack
and you get out the new tire.?
The two young men proceeded to go to work. William had to move
his Air Force duffel bag to get at the tire. He thought about what it
contained?his very complete wardrobe of women?s clothes from
two girdles, several pairs of very feminine panties, and nylon
stockings, three bras, two slips, three skirts, four blouses, an evening
dress, and two wigs. It was chock full when you added in the
makeup and jewelry kits, the two purses, and two pairs of high heel
shoes. William blushed thinking about his little ?habit,? being here
with a young man who obviously was the object of admiration of all
those hot young women at school and the burger joint, unlike
William.
As work continued on the tire, Jack said, ?I need a screwdriver to
get this hubcap off.?
William replied, ?There is a little tool kit in the trunk, Jack.?
Jack went back to the trunk while William sat on the curb. Jack
noticed the very full duffel bag, and saw a bit of something pink
sticking out. He looked to see that William wasn?t looking, and he
quietly opened the duffel bag. Jack was amazed at what he saw,
from panties to parts of a slip to a skirt, a wig, high heel shoes, and
oh yes, a girdle that made Jack?s penis stir. He thought, ?William
must be a transvestite. I can?t believe it; I have met a nice young
man who wears women?s clothes. Oh, that is so hot, so erotic!? Jack
could feel passion and lust rise up in his loins and in his heart he felt
love and affection for this obviously weak, effeminate, new young
male friend of his.
Jack carefully closed the duffel bag. The two young men finished
the task at hand, and then both sat on the curb.
Jack said, ?That girl in the purple skirt was so hot, William, and I
noticed you really were looking her over.?
?Right, Jack, she is one hot chick,? replied William.
Jack said, ?I bet you look hotter than she does when you dress up
with the hot stuff you have in that duffel bag.?
William was shocked and scared. He was speechless! Found out!
Oh dear! Panic time! They were parked by an orange grove.
William ran off into the grove to hide and began crying.
Jack chased him down and said, ?William, there, there, don?t fret
my dear friend. Your special secret is safe with me.?
William was trembling and replied, ?Oh Jack, I am so embarrassed.
I simply must wear those clothes at times, it seems so right for me.?
Jack took William in his arms in the seclusion of the heavily
forested grove, ?It is right for you, my sweet girl, I am sure it is.?
?Oh Jack, I am mortified, you are making fun of me by calling me a
girl.?
Jack said, Oh, William, quite to the contrary, I think it is wonderful.
I have dreamed for years of having a transvestite boy be my very
secret girl friend.?
William replied, ?You don?t date real girls, Jack??
Jack replied, ?Oh, William, I date them all the time. They fall to
my feet. I love them all, at least the hot ones. But, they couldn?t
possibly excite me like I think you could; that is, if you are female-
like when you dress and you want a man to love you like that.? Jack
went on, ?How many girls have you had sex with, William??
William stammered, ?Oh really, Jack?such a probing question.?
Jack gently hugged William and kissed him lightly on the cheek and
whispered, ?How many William, you can tell your Jack.?
William softly responded, ?I have only had sex with a woman once,
and that was at age 16 with a whore in Mexico. I can get dates with
girls but they never will let me go all the way with them.?
Jack softly replied, ?Do you date often, William??
?Well, not hardly since high school. I just find more comfort in my
cross dressing.? William quickly added, ?But, I am not queer, I love
women.?
?Of course not, William?of course not. I imagine you beat off
when dressed though, don?t you??
William was beet red, lowered his head, and softly said, ?Always,
Jack?always. I cannot even begin to put on my panties without
getting so hard.?
Jack said, ?This really turns me on. Now my sweet transvestite
friend, be honest with me, do you think of being?. well, like a girl
with her boyfriend when beating off wearing your hot clothes??
William protested, ?I am not queer, I like women, Jack.?
Jack pressed it, ?You didn?t answer my question, William, I know
you like women, but do you like them so much you want to
experience what they get to experience when they are in bed with
their boyfriend??
?Oh Jack, you are going to turn me in and get me expelled from
school.?
?Look me directly in the eyes, William,? Jack replied, ?Young lady,
I find you very special and very, very sexy and hot, much hotter than
the girl in the tight purple skirt. I want to share your secret side
with you, to help you be a female boy, my darling William.?
William shook, and softly said, ?I dream of being a bride when
dressed. Sometimes I lie in bed with my legs wrapped around my
duffel bag and pretend it is my husband and me having sexual
intercourse as if I were a real woman!?
With this the handsome, virile Jack kissed William full on the
mouth like a real man would kiss his new girlfriend, and he pressed
his groin tightly against William?s. Jack?s hands grabbed William?s
ass and he ground his hard penis through his pants against William.
?Let?s make both our dreams come true, my wonderful boy woman!?
William?s heart was pounding as he leaned his head on Jack?s
shoulder and felt Jack?s hand unzip his fly and fondle his penis.
?My, my, you do have a small penis, my sweet boy girl?this is so
wonderful? so expected, and utterly perfect!? Jack continued,
?You obviously are going to be my girl, my special boy woman, and
you are going to love it. For it is where you belong, William, and it
is where I belong--guiding you, instructing you, loving you and, in
return, although you are male, you will be my college pretend wife.?
Oh Jack?.gee?.oh Jack?this is so sudden?ohhh?? William
trailed off.
Jack said, ?No one but us will know. We will both continue to date
girls. I will find girls that will accept you and we can double date.
But, in addition to us having our perfect girls, we will be very
special, very secret lovers when you dress as a woman, and I become
your strong, loving man who understands you like no one else can,
and who will love you more than most men love ordinary girls.?
With this, Jack unzipped his fly and pulled out his very hard penis.
He rubbed it against William?s much smaller erection, and they
kissed again.
Jack looked William directly in the eyes and said, ?What is your girl
name, honey, surely you have a very sweet female name.?
William couldn?t look Jack directly in the eyes. He blushed, with
his head down and softly said, in slightly higher octave than his
normal voice, ?Jack, I am ?Wendi? as a girl.?
?Oh that is a wonderful name, honey. It is so feminine and so
demure, just like you, my sweet sissy babe.?
William said, ?Oh Jack, to be my Wendi self right, now please let
me go to the car for a moment and get some things for a bit of
transformation?is that okay??
?Of course it is Wendi,? Jack said with such commanding
confidence and gentle control and admiration for his wonderful,
obviously weak and fascinating male girlfriend, William/Wendi.
William ran back through the grove to his Chevy. He was so excited
he nervously fumbled for his keys, finally getting the car trunk open.
He opened his duffel bag and found his very favorite open bottom
girdle, the black one with the little pink ribbon on the front, the
matching black satin bra, the wonderful black satin panties with the
pink rose on the front, a pair of sheer, seamed nylon stockings, and
a pair of rubber falsies. The sissy also grabbed a tube of hot pink
lipstick.
William placed these delectable items of naughty lingerie in a sack,
closed the trunk lid, and ran back into the deep, secret grove to his
waiting lover. There was his darling Jack standing naked with a
raging erection. William rapidly stripped naked in front of a real
man for the first time. William slid the girdle up his legs and
worked his ass and groin into the tight-fitting garment?a garment
manufactured and sold only for a real woman to wear! He then put
the bra on backwards, so he could easily close the clasps, turned it
around, and slipped his arms deftly through the straps. As he put
the falsies in the bra cups, he came alive as Miss Wendi, Jack?s new
girlfriend! He then sat on a nearby rock and expertly rolled the
nylon stockings up his recently shaved legs, one at a time, carefully
aligning the seams before he attached each stocking to the girdle?s
garters.
Jack was thrilled by what he was seeing. ?Wow!? Jack thought,
?This is so exciting! William is really Wendi, isn?t she? Look how
she knows how to put on those nylons. Look at how hard her cute
little female penis is jutting out beneath that lovely open bottom
girdle!? Jack then watched his feminine girl-boy slip those very
sexy satin panties up his/her supple, shapely legs to his/her knees.
Finally, the sissy deftly applied the hot pink lipstick to his/her
pouting lips.
Instinctively, William dropped to his knees and kissed all over
Jack?s erect penis. As he/she did this, he opened his legs until the
pretty black panties were taut around his/her knees. His/her cute
little female penis was so hard, sticking straight out beneath the sexy
girdle.
Jack softly said, ?Do as you must Wendi, do it darling!? William,
now Wendi, wonderfully sucked his first dick! It was so thrilling for
both of these wonderful young men.
William instinctively began to beat off as his new manly friend
fucked his sissy mouth. Yes! William knew now that not only was
he a transvestite, he wished so to be this wonderful man?s sissy male
woman! He/she squirmed his girdle buttocks and made soft sissy
moans as he/she took Jack?s manly mouth fucking like an
experienced slut! As the sweet panty sissy?s mind was rushing with
many womanly, wonderful thoughts, and his/her body felt those
wonderful womanly feelings that were so familiar, he ejaculated into
his/her panties and, at the same moment, Jack ejaculated into his
lovely new male girlfriend?s cunted mouth!
Jack cried out, ?Oh fucker, baby, my sweet boy woman, take my cum
baby!? As Jack?s rigid penis ejaculated into Wendi?s mouth, he/she
felt so womanly and feminine and knew that his/her years of
dressing and homosexual masturbatory passions had now been
utterly and completely confirmed and validated.
William?Wendi?truly felt like a female boy and was so proud to
be Jack?s very secret male girlfriend!
Jack pulled out of Miss Wendi?s cunted mouth and he pumped and
sprayed copious amount of his manly semen onto the sissy?s neck
and bra. Jack could see the sissy boy?s rigid little penis in post
orgasmic spasms, with a bit of dainty semen still spurting from it
into those sexy panties.
Miss Wendi cried out softly in a high-pitch voice, ?Oh Jack darling,
I am a woman! I am your woman!?
?Yes you are, baby,? Jack responded, rubbing the young sissy?s
premature balding head, ?Yes, you indeed are my very special male
woman!?
That night the two new friends went to bed together as man and
wife. Jack was the attentive, thoughtful new husband in love with
his male wife, and William/Wendi was completely made over in full
drag as a lovely young male woman. Jack told the sweet sissy that
he/she looked ?womanlier? and was hotter and sexier than the hot
girl they had seen in the tight purple skirt at lunch. Jack reminded
the eager sissy of this, time and again, as they made love in bed,
leading to the consummation of full male-female-like sexual
intercourse. The sissy fell deeply in love with his/her new husband
at that moment of moments when his/her anus became so female-
like and vaginal, receiving a thorough and loving fucking with the
rigid, thrusting penis the little queer had so much longed for
constantly since age 16 or so!
He/she cried out during intercourse, ?Oh yes, oh yes, I am as a
woman in sexual intercourse! Oh yes, this is it! I am a male
woman! I love you Jack, fuck me like the slut I am!?
This excited both manly Jack and his sissy male wife so. They were
hotter and more sexual than any mere man and woman having hot
sexual intercourse!
Jack, too, had found that very special love he had been lusting for so
secretly since a teen boy. ?Yes,? he thought, ?I do love women so,
but this sweet male woman is the girl of my fondest dreams! Not
only is he a girl, he is a weak transvestite sissy that loves cross-
dressing and submitting to my superior, manly direction and
guidance. This is perfect!?
With this, he kissed his sissy lover and said, ?William, my Wendi
girl, I love you!?
The sweet drag sissy looked intensely into ?her? lover?s eyes and
replied, in a high-pitched voice, ?Oh Jack, I am so deeply in love
with you?I love being your new wife!?
They cuddled, and Jack said, ?We will be two young men friends to
the world and man and wife in our home at night! When we date
real woman, they are never to know about this very secret, intimate
bonding of you and I, my darling transvestite wife!?
?Yes, Jack, my darling husband, no one will know, especially our
hot girlfriends. They must never know,? the womanly-attired sissy
cooed.
Before the loving couple went to sleep they freshened up. Jack put
on a pair of handsome men?s pajamas. His sissy boy wife, Wendi,
took off his/her women?s clothes and wig and removed his/her
makeup, except for lipstick. He/she then put on a lovely baby-doll
nightgown in a powder blue color. The front top was embroidered
in lace and feminine patterns with a cute little ribbon. The sissy also
put on royal blue satin full-brief panties and thigh high nylon
stockings. They went fast to sleep in each other?s arms.
During the night, William woke up and wondered for a brief
moment?then felt those wonderful satin panties and nylons? ?oh
yes, I am a male woman?oh, yes, I am in my pretty baby doll
nightgown and in bed with my real man! ?.oh, yes, yes, YES! My
wonderful man Jack is here in bed with me, and I am his girl! I am
finally really Wendi rather than William?YES!?
The sissy boy thought about the events of the day before, with the
supreme conclusion of the night before, when he truly became a
homosexual male girl in the arms of his/her thrusting manly lover!
His/her mind was full of girlish thoughts and desires as he/she lay
there in the middle of the night: thoughts of being a college girl, in
an angora sweater with perky breasts, a pretty pleated skirt over
his/her full slip and girdle, and cute saddle shoes on his/her feet
with little lacy socks. And, delightful thoughts of he/she walking
along the campus along side Jack, with her notebook clasped to her
chests, the words ?I love Jack? blazing in feminine handwriting on
the cover of the notebook.
These thoughts caused Wendi?s female penis to become throbbing
hard inside his/her satin panties. He/she squirmed her ass on the
mattress. Jack awoke and detected this. He, too, remembered the
wonderful events of the day and evening before, and that he was still
with his sissy male girl! Without a word being exchanged, the
young lovers knew what they had to do in those very early morning
hours. Jack?s hard penis was soon sticking out of his pajamas as he
knelt on the bed beside his new sissy boy wife. He placed his penis
on the cross dressed, very womanly queer?s painted lips and Wendi
instinctively kissed the tip then began to whimper with joy as the
raging hard penis of his/her real man lover invaded his/her very
willing mouth. Jack began to stroke William?s?Wendi?s?very
hard female penis inside those wonderful panties as he fucked the
sissy?s cunted mouth! Soon, they were ejaculating together as man
and homosexual male wife! Semen was everywhere: all over the
male girl?s face and nightgown, and his/her panties were soaked
with his/her very own homosexual ejaculate!
They fell back asleep. Morning came, and the sissy, now a
confirmed effeminate homosexual, arose and admired him/herself in
the mirror, and swooned at seeing all the caked, dried semen on
his/her nightgown and panties. William knew he was a weak, sissy
faggot, who loved being a male woman, and was so in love with
his/her new, very manly, wonderfully understanding husband, Jack!
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