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Nancy's Tale free porn video
Nancy's Tale ? by: NancyCD
Like most crossdressers, I too began as far back as I can remember. At
age 6 a distant cousin and I would play the hero and heroine roles in
an Indiana Jones type adventure in my great grandmothers basement
during the holiday gatherings. The heroine would put on stockings that
on an adult woman would come to the high calf level but on a six year
old were thigh highs, and some old skirt hanging in the closet.
I don't remember if we ever got caught. Due to divorces we stopped
attending those gatherings and thoughts of dressing didn't cross my
mind again until I was 12. Then of course I would raid my mom's drawers
and the bags of old clothes in the closet. I did this daily after
school while she was still at work. I still remember a 'sick' day when
my grandparents showed up to drop something off. I ran upstairs before
they got in the house and, fortunately, since they didn't know I was
home, they quickly left. When I think back my mom must have noticed but
nothing was ever said.
Once in college it was a bit more difficult to wear more than panties
and pantyhose in the dorm and that was very infrequent at best. I
fortunately found a few pair of panties in the dorm laundry that let me
fulfill my hidden desires. In my third year I had a shared apartment so
I was able to buy a few things but was still limited by two male
roommates, one of who never seemed to go out. I would stay over spring
break and other long weekends when they would leave and absolutely love
the time to spend a few days dressed.
For my last two years, I was on the five-year plan; I was fortunate
enough to share a third floor two-bedroom apartment with a girl friend
of mine, Claire. We had a strictly platonic relationship and since I am
a bit of a neat freak it worked out very well. It was much better than
living with any of my male friends who typically were slobs. Of course
she knew nothing of my hobby and I was not ready to announce it.
Claire was a very stylish dresser and I would try on the things she
would leave thrown about her room but never disturbed her clean things.
This includes a number of plaid skirts and sweaters that were adorable.
The real advantage came in that she lived only an hour and half from
campus and would go home for weekends at least once a month. This gave
me the opportunity to buy some clothes. This included a pair of heels,
a black skirt, a purple turtleneck above the knee sweater dress, and
some lingerie including a white corset with thigh highs and garters.
I would spend those weekends dressed and began to experiment with her
makeup. My hair was not all that long but not a typical short male
cut either that gave me the chance to play with it a bit. My typical
weekend involved going out on the balcony to smoke a cigarette, with
the lights out of course, and just lounging around the apartment with
the blinds fully closed. I never thought of going out since I knew way
to many people in town. I was not passable except to people walking
on the ground who saw a shadowed figure of a woman smoking in the dark.
My life completely changed one fall weekend when Claire had a test on
Monday and decided to come home on Saturday night. I had gone to the
balcony to smoke as usual in my dress and shoes with my best/only
lingerie underneath and I didn't notice when Claire walked into the
apartment since I had closed the curtain behind me. She must have
headed to her room right away because as I came in, shut the slider and
curtain, I turned around to see her walk around the corner from the
hallway towards the bedroom. My jaw must have just dropped.
I thought of 20 excuses in a second the best of which was I was
practicing for my acting class but I knew none of them were plausible.
Her response was better than expected in that she didn't scream and
yell although she wasn't thrilled about the sharing makeup she told me
later. Her mouth popped open and her hands went to her face as she
burst out laughing. She then proceeded to jump around very excitedly
just cackling. I ran to my room and tried to shut the door but she was
right behind me keeping me from closing it fully to lock it.
She somewhat apologized and with a straight face said, "So what's new?"
as she busted a gut once more. Fortunately her laughter began to rub
off on me considering she saw me dressed but with unshaven legs and a
sad excuse for makeup. I then fessed up to my sorted history and she
asked some questions. The typical questions were "Are you gay?", "How
long have you done it?", "How often?" and "Does anyone else know?" At
this point the internet was new and foreign to me so as far as I knew,
I was one of very few crossdressers in the world. My knowledge was
limited to books I found in the school library. I knew she was opened
minded in general but was scared to death she would tell our mutual
friends. With a little begging she promised she wouldn't tell anyone.
Her next statement came as a big surprise when she said my makeup
needed some real work and led me to her vanity.
There she wiped off what little was on and began working on what she
described as "our" project. I had recently shaved my face so she began
with a foundation, followed by a number of products I didn't even
recognize, spending quite a bit of time with my eyes. She then styled
my hair in no time much better than I could have ever done. Even though
I was able to watch her progress until I stepped back and took a quick
look in her full-length mirror, which I was very familiar with, I
didn't realize how much she had accomplished.
The next step was somewhat difficult as she handed me her hair remover
and said the leg hair had to go. I would be classified as hairy and the
hair suddenly missing would be noticed. Claire pointed out it was fall
and I would be wearing pants for the next 5 months. She also asked me
to let her tell a friend, and after she said it would be their secret,
I reluctantly agreed.
I disappeared into the bathroom and with a few inches of water in the
tub removed all of my leg hair promptly stopping up the drain. I then
got re-dressed while Claire banged on the door every minute asking if I
was ready. I could not believe the sensation the thigh highs on me
freshly shaven legs. When I walked out and into her room the sliding of
the dress on my legs immediately caught my attention. When I looked
into the mirror I was nearly in tears. Claire kept praising how great I
looked, not a homecoming queen but much better than my wildest dreams.
I spent so long looking in the mirror that I didn't notice her getting
to pull some of her clothes out of the closet. "These are the things I
never wear so you can have them," she added that I could keep them in
her closet but I could only wear the approved items. They were all
wonderful. A pink turtleneck sweater, a green and red plaid skirt, a
short black dress, a denim jumper, and a few tops.
She then demanded a fashion show and insisted I take off my dress. She
had not seen the lingerie prior to me pulling the dress off. The
combination of her watching and seeing myself in the mirror immediately
began to tent my panties, something that was not lost on Claire as much
as I tried to hide it. She then handed me the sweater, a slip, and the
plaid skirt. The slip rubbing my panty covered erection only made
matters worse. As I modeled in the mirror she came over and tried to
flatten the bulge in the skirt.
Claire patting down the front of the skirt was nearly too much to
handle. "You need to take care of that before we go on to the next
outfit." When I turned to go toward the bathroom she grabbed my arm and
said, "No, take care of that right here." She handed me some tissues as
I slid off the skirt and slip fully exposing my moistened panties to
her. Again she gave it a quick rub to help me along. I tried to
volunteer her but she said she'd rather just watch.
I slid my panties to the side and proceeded to gently stroke myself.
Given the situation and her watching I came in a matter of seconds.
Once I cleaned up and pulled the panties back the fashion show
continued for a few hours including some clothes I was forbidden to
wear again. At four in the morning we were both exhausted and called it
a night. She gave me a peck on the lips and big hug saying my secret
was safe with her. Needless to say I had quite a bit of trouble getting
to sleep that night.
I continued to dress when the opportunity presented itself but not too
often since we had infrequent visitors that would just drop by. Claire
bought me some makeup and I became quite proficient at doing it myself.
After the first few times neither of us was uncomfortable and the
fashion shows ended, as it became more of a routine when I had a late
class the next day. Finally the week of Thanksgiving came and we were
both going home for the week but not leaving until Sunday while nearly
everyone else bugged out on Friday if not Thursday.
It was that Saturday that I was dressed watching television when she
tossed me a purse and said, "Let's go." My stomach dropped and I said
there was no way I was going out like this. She explained that everyone
we knew was gone and that any acquaintances would never recognize me.
It wasn't like I was going to go chat with people, she simply had to go
by the ATM, get gas for her trip, and stop by the bookstore. She swore
I could stay in the car and I gave in.
The sound of my heels on the steps and sidewalk caused my heart to beat
quicker and almost run but Claire touched my arm and slowed me to a
nice walk. I joined her at the ATM and my confidence was built when a
number of people passed by. Claire looked better than I did which meant
guys would stair at her but at least notice me. She insisted that a man
should pump the gas and made me do it. I got a nice rush when an older
man pulled up on the other side of the pump and said hello. The
bookstore was another story.
I was not ready for direct contact in a well-lit environment so Claire
left me in the car. She claimed she forgot cigarettes and made me go in
to get them after pointing out the store was empty except for the one
counter person, a middle aged non-threatening woman. I entered the
store money in hand so I would not rummage through the purse and I
picked up the cigarettes without incident. The entire ride home Claire
was bragging about how passable I was.
We then promised to arrive back the Saturday after Thanksgiving and
have another adventure together. With Claire I felt safe and I knew she
would gladly run interference if necessary. Of all the ways to be
brought out of the closet this was by far better than imagined.
When I arrived back from Thanksgiving at 1:00 pm Claire was not there
yet. I unpacked, showered and dressed in the black dress, black
pantyhose, and a cardigan sweater. I was sitting on the couch when
Claire walked in followed by her good friend Jessica. Claire introduced
me as Nancy, a friend of her roommates, and disappeared into her
bedroom leaving me sitting there with Jessica. I had met Jessica
briefly which scared me to death but Jessica just tried to make small
talk and asked what I was watching and in my most feminine voice I told
her it was a Night Court re-run.
She then asked a few more questions looking me in the eye the entire
time. After a few minutes I excused myself and went to my room. Claire
knocked and came into my room apologizing. She claimed she didn't think
I'd be back and ready this early in the afternoon. Jessica lived near
her so she had driven Jessica back from home and was just getting some
notes to swap before taking her back to her apartment. Jessica didn't
seem to know it was me but I was still upset. The event seemed to pass
without any problem when I saw Jessica on campus a week or so later and
she said she met Nancy and she seemed nice and that we would make a
good couple. Talk about an ego boost.
As Christmas break approached I was looking forward to another
adventure with Claire. We had discussed stopping by a few places I
would be comfortable at like the ATM, gas station, and then take the
next step of going into a few stores together. Mostly large department
stores where we could walk through largely unnoticed. We both finished
our exams that morning and we met for lunch that afternoon.
Claire then said she had a surprise and took me shopping for a new
dress of my own. She was tired of seeing me in the same old outfits. I
was still in my male attire so she acted as if the dress was for her as
we walked through the department store. We ended up with a dark green
turtleneck sweater and a black pleated skirt. The skirt settled about
three inches above the knee. Not overly short but with the normal
movement of walking, climbing stairs, and getting into cars would show
a bit more leg than I usually did and would swish nicely on my legs.
Claire also said she would lend me a red thigh length coat of hers that
would accent the outfit nicely given the Christmas season. On the
entire drive home I was really looking forward to the nights adventure,
no matter how boring it sounded.
Once we got home and relaxed for an hour or so cleaning up from exam
cramming she helped me with my hair and makeup as promised since I
never quite got it as good as she had done it those first few times. It
seemed she was looking forward to tonight as much as I was. Claire said
she was going to go get ready and we would leave about 7:00. I thought
it was weird she needed time to get ready to go to the store but
thought as long as she looked better than me I would be better off. I
put on a matching pair of pink panties and padded bra, my new outfit,
my two inch black cluncky heels, and a pair of black control top
pantyhose to help keep me in place.
It turns out that Claire wasn't as good at keeping secrets as I had
hoped. She didn't tell any of our mutual friends but apparently in a
drunken state told her girl friends with whom I had a passing
acquaintance. No pun intended. These four girls were regular visitors
to our apartment so at least knew their names and majors. One of course
was Jessica. The others were Carolyn, Jennifer, and Stephanie.
All were attractive co-eds in their second and third years. A few
minutes to seven the doorbell rang and I ran back to my bedroom. Claire
happily came out of her room looking much too nice for a trip to the
store and said, "I wonder who that could be?" I was in my room with the
door partially open to hear what was going on at the door. It became
clear that I had been set up when all four came into the apartment and
started talking. They asked if Nancy was ready and that they couldn't
wait to meet me after all the nice things Claire and Jessica had said
about her.
I shut the door and locked it but Claire had the key we kept on the
door molding in case we accidentally locked our doors and she walked
right in. She said she had a surprise and we were all going to go out
dancing. With that the rest of the group walked in. All of them were
very nice about it and explained how Claire had spilled the beans. They
thought it was terrible that I was limited to the balcony and the
quarterly trips to the ATM. They had decided to take me out on the town
and take me under their collective wing. We were going to a dance club
thirty minutes away in the next town where a small college was located.
Since nearly everyone had headed home they knew it would not be very
crowded and very few from our school would make the trek down there
since most were just thrilled exams were over and would get drunk at
home. Needless to say I was scared to death but by going with a group
they pledged they would stay with me. In my opinion I was the fifth
worst looking of the six so I doubted anyone would be interested in me
as long as the group stayed together.
We took two cars and the two beers I had on the way loosened me up a
bit. Since the club allowed underage dancers I wouldn't need to show
ID, just accept not being able to drink once we were inside. The car
ride was uneventful, Claire drove while I road shotgun and Jennifer
was in the back seat. Jennifer was very complimentary the entire way so
my confidence was built up as much as it could be given the situation.
She said Jessica knew it was me since Claire had already spilled the
beans but was just amazed at how good I looked and how feminine I had
acted. Jessica said she had to stare at my eyes to keep from gawking at
the rest of me and giving the secret away.
The five of us arrived about 8:30 so the place was fairly empty
although it seemed some had started celebrating the end of the semester
a bit early and were already on their way to hitting the floor. I
entered without any glances and we checked our coats and purses. The
five of us starting dancing together and my confidence was higher than
ever being with the group. The club really never got completely full
but was somewhat crowded considering how deserted the town was.
There were a few groups of guys that would dance with the group and
flirt with Claire and Stephanie, the hotties of the bunch. They
rebuffed their attempts as best they could but there always seemed to
be a guy or two dancing within our group. Of course the obligatory slow
song came on and Claire and Stephanie agreed to dance with the two guys
in our group at the time. With that three of their friends came over to
dance with the rest of us. Since they were one guy short I thought I
could get out of it but was surprised when asked. I thought I would
decline but I didn't have much choice as the others said that 'we'
would love to dance.
It turns out that my partner, Eric, had been celebrating most of the
day so the fact he was drunk worried me to some degree but I knew I
would pass and could rebuff any advances. Eric was about my height, a
little more muscular, and went to my school, as did all of his friends.
He was wearing a pair of jeans and an oversized sweatshirt over a tee
shirt with our school's logo on it. It was awkward putting my arms up
around his neck as his went around my waist. I put my head down on his
shoulder as he pulled me tight. I kept my head down, as it was obvious
he was trying to get my head up so he could kiss me.
He did get the hint but then went to gradually rubbing his hands lower
on my backside and along my outer thigh. I let him grope a little since
I was more concerned about making a scene. This clearly got him a bit
aroused that began to rub off on me. Fortunately with the pantyhose
holding me down it was not noticeable. The dance ended and the couples
parted and began to dance as a big group again. I was very relieved
yet thrilled at the effect I had on a guy.
A half hour later I saw a few of the guys talking to Claire and her
nodding in agreement. It turns out the group was leaving to another
party but Claire agreed to give Eric a ride home since we had room for
one more and he was not interested in leaving. I hoped this wasn't
because of me but secretly wished I had something to do with it. We
stayed another hour and danced uneventfully while Eric mostly drank to
the point he slurred quite a bit and became the typical college drunk
guy everyone despises. He would dance his way through the five of us
and put his arm around us at which point we would make some turning
action to get his groping hands away. Since he was hitting on everyone
I figured he didn't stay just for me. This put me at rest considering
we would be in the same car for the 30-minute drive home.
We all grabbed our coats and purses and made our way to car while Jim
made a pit stop between a few parked cars. Jennifer quickly called
shotgun and ran to the front passenger side door leaving me in the back
with drunken Eric. He was at the point were he would not stop talking.
He tried to slide next to me but I told him I had a boyfriend and
although I enjoyed the dance I wasn't interested. He kept saying how
beautiful I looked and touching my hair and shoulders, as he would put
his arm on the back of the seat. The comments were nice but getting
annoying to all of us. At this point he said, "So which one of you is
going to hook up with me? You know I'm going to tell all of my friends
I got laid anyway so you might as well get some pleasure out of it."
We let this comment slide but he just kept on talking about how good he
was and started to undo his pants pulling out his partially erect cock.
At this point Jennifer, looking over the front seat, let out a laugh
and said she couldn't believe he did that considering how average he
was. Claire looked over the seat and let out a chuckle. This did not
phase Eric one bit as he began to fondle himself and try to rub my neck
at the same time still talking about his prowless.
I had never been this close to another guy's dick except in the showers
of high school gym class. The showers had no effect on me but watching
him stroke him now fully erect cock did peak my curiosity. It was
similar in size to mine and I couldn't take my eyes off it. Claire
noticed this in the rear view mirror and said I should do something
about it just to shut him up. She asked him if I gave him a hand job
would he not say another word the rest of the trip or be risked getting
left on the side of the road. He reluctantly agreed to the hand job as
Claire and Jennifer egged me on.
I slowly reached over and wrapped my hand around his shaft and slowly
began to stroke him. It felt very much like mine except for feeling the
twitching of his cock was much different than when it is your own. I
looked at his face as I changed from stoking him to palming the head
and rubbing my finger just under the head. He got a slight smile as he
laid his head back on the head rest continuing to massage my neck and
shoulder. I then undid my seatbelt and reached over with my other hand
and began to fondle his balls. I'm not sure what he enjoyed most but my
two-hand job was having the desired effect.
Of course using two hands leaning over in a car my face was now less
than two feet away from his cock. I looked him in the eye and licked my
lips, which caused an immediate twitch. I was overwhelmed by the
feeling of power I had. I had this young man literally by the balls and
wanting me to do something that we both knew he would never forget. He
would always remember the one night stand blowjob he got after exams
that one year in college.
I slowly lowered myself while continuing to rub his balls and stroke
the base of his cock. I looked at his face while I licked his head like
a blow pop. The pre-cum had a slight salty taste that I got use to very
quickly. I licked a few more times and then lowered my mouth onto him
until I felt the head hitting the back of my throat. At this point I
stopped looking at his response and just closed my eyes to enjoy the
moment. I knew just how great it felt when your dick was fully into
someone's mouth so I slowly began to bob up and down re-positioning my
head each time to get him a little deeper into my throat.
After a few bobs I took him all the way in and he started to moan with
delight. Claire said he would have to be quiet for a whole week since
we only promised a hand job. Jennifer and Claire were giggling and
making comments but I was not paying much attention to them at this
point. I began to slide up and down working his head with my tongue
every time I pulled off. At this point he removed his hand from the
back of my neck and began rubbing the back of my pantyhose clad thigh
working his way up to my ass. I was in a bent over position so I knew
there was no way he could get close to my surprise.
I was in ecstasy, a cock in my mouth and my legs and ass being rubbed
the way I had always dreamed when dressed in the apartment. I could
tell he was close to coming and I took him all the way in and began
using my tongue to lick and apply pressure to his full length as he
began to cum into my mouth. I had to pull off and swallow letting some
run down the base of his cock. I made sure to lick his cock thoroughly
to clean him off, as I knew he would want. I slowly raised myself and
leaned in to give a kiss.
He quickly put his tongue in my mouth and I responded in kind. This
lasted a brief time while he still stroked what was my now the front of
my thighs since I was kneeling on the edge of the seat. Since he was
getting too close I quickly moved back to seat and said he should put
that thing away. He gave a satisfied drunken grin and pulled his pants
back up.
The timing was perfect; we had just pulled into his apartment complex.
He tried to talk as he got out but Claire cut him off and said he had
to keep his promise. As he closed the door she quickly took off out of
the parking lot laughing hysterically. Jennifer said that had made her
very horny and joked of climbing into the back seat to see if I was as
good on girls as I was with guys. I was very open to that considering
how horny I was but it was played off as a joke.
I said the offer was open ended. She said she would think about it but
it was played off as a joke. Claire said I was her bitch and Jennifer
should find her own. Claire dropped Jennifer off and we made our way
back home. As we got into our apartment she had a smirk on her face and
said she was impressed with how good I was and thought I did I great
job of 'acting' to enjoy it. She said she couldn't wait for the next
time we could do a group outing but it would probably be a few months.
I did pass Eric on campus a few weeks later but he had no idea who I
was. He had seen Claire and asked about Nancy but she said I was really
only in town for that weekend so he wouldn't see me again.
Alessandra
- 03.01.2021
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