Thelma and Me Summer of 65 part 2
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The Dress, Part 2 Of A Series free porn video
The Dress II (A shopping date)
by Diann
First, please allow me to recap a bit from the last part. I'm a thirty-year-
old transvestite (living with my mother, helping her cope with severe
arthritis) who found a magical dress in a second hand shop. The magic
changes whoever wears it into a beautiful woman when they put it on, and
the change reverses once the person is totally naked. After taking a few
minutes to get used to the new me, I went to the nearby mall and made a
couple of acquaintances, Joan (who works at the mall's concierge desk)
and Jim (a stranger I befriended, or who befriended me depending on the
point of view). Anyway, goings on go on, and I have made a date for
tonight with Joan, who invited me to a mall "Employee Sale Night" and
she has something else on her mind as well, even though she hasn't said
as much.
Now, here I am on a Saturday afternoon, doing the same old routine. I
just got done with the weekend chores (all the heavy stuff my mom can't
do). And mom is bugging me to go out and do something for the
evening, which I plan to do. Too bad she wouldn't understand what I'll
be up to, mostly because I haven't told her about my newest acquisition.
Since it would be suicidal to make the change in the house while she's
home and awake, I pack a few of my femme things into a backpack
(panties, bra, garter, stockings, shoes, my purse and of course my dress)
and I put it in the trunk of my car.
I tell mom that I'm going out to the mall for a while, and that I'll be back
for dinner. A short few minutes later I'm walking up to the concierge's
desk, eyeing Joan sitting there paying me almost no notice as an
overweight, tall man among the many who walk past her post every day.
After a minute or two of looking at the brochures arrayed around the
circular booth, she asks me if I needed any help with a well-practiced
semi-interest. I have to admit she was different toward the guys than she
was to the girl I had been a short couple of days ago. I politely say no and
she goes back to what she was doing ... she had a business card on the
counter top in front of her, and she brought a cell phone out of her purse.
She dials a number and a few seconds later she's leaving a voice mail
message checking about tonight ... and I catch my name before she hangs
up, meaning it was for me. Just then my pager goes off, and the display
reads that I have a voice mail message. Of course since I heard the
message, I just shut down the pager and ask her where the rest rooms are.
She points me toward the men's room. I notice the women's room is
across the food court from the men's, and a plan forms in my mind. I
make my rounds of the shops I usually go to as a guy, namely the
bookstore, a games store, and a tobacco shop. I leave the mall with a few
women's magazines, an 'adults only' game and a couple cigars to add to
my collection at home.
I drive back to the house with a smile on my face, thinking about the
evening's activities. I call Joan's cell phone as a "co-worker of Miss
Sean's" since she's 'indisposed in a meeting' I said I was asked to get any
information about the shopping trip for tonight. I write down when and
where I should meet her, tying it all in with my plan for changing at the
mall. She wants me to meet her in front of one of the lingerie shops, on
the level above the food court at ten.
I look at the clock, since I have a few hours I decided to take a nap before
I go. I set my alarm and masturbate myself into a relaxed mood, where I
can nod off into dreamland. I wake up to the alarm refreshed and ready to
go. Before I leave the house I add a bottle of perfume to my backpack,
grab my keys as well as the pack and head out the door, telling mom that
I'm going over to a friend's for the evening.
I get into the car and speed over to the mall a half-hour early. The mall is
almost deserted aside from a little activity at the movie theatres, which are
right by the bathrooms Joan pointed me too earlier. The entryway to the
ladies' bathroom tempts me, and I walk slowly toward the opening. As I
close the distance, trying to look like I'm studying the menus of the food
court restaurants as I'm walking, I keep my ears listening for sounds
coming from the powder room. Luckily for me I don't hear anything, so I
take a quick glance in the direction of the entry. A small amount of the
mirror is visible from my vantage and he reflection shows a vacant stall
just by the far wall. I took a last quick look around me to see if anybody
is watching, then I sprint into the 'forbidden zone' and into the last stall,
where I close and lock the door quickly.
I look around and see this was the handicapped use stall almost at once. I
noticed it was bigger, the door opened outward, and the giveaway for it
were the metal rails that let people brace themselves. I hung my backpack
on the back of the door and proceeded to undress myself. The "paranoid
crossdresser" part of my brain was screaming for me to hurry, as security
cameras might have caught me sneaking in. Since I wouldn't presume to
argue with myself, I went as fast as reasonably possible. In a minute or
two I was naked in the stall.
I opened my backpack and pulled out a handful of the soft fabric that I
packed inside, all rolled up inside the dress to keep it compacted. I
reached back in and grabbed my purse and set it on the hook in the back of
the door. I opened the purse and took out my ladies' style watch and
managed to squeeze it around my wrist. Then I took my clip earrings,
small golden colored hoop types, and fastened them to my ear lobes.
Finally I unrolled my dress to reveal my bra, full slip, pantyhose and heels
that I had secreted in the dress. I put on the bra, figuring I didn't need
anything more than basic padding (which I could use the bathroom tissue
for) and sat on the toilet to put on my hose. Then I slipped my feet into
my comfortable heels (of course after eight to ten hours or so they'll be
killing my feet, but that's too far off to think about) before I stood and
lifted the slip over my head. I took a few moments to gather my
masculine clothing and rolled them into a ball before stuffing them into my
pack. Then I turned my attention back to my dress and took it gently into
my hands. I stepped into it and zipped it up, thus triggering my
transformation. I looked down to see my 'natural' breasts filling up my
bra cups, and I could feel the toilet paper under them pushing my feminine
globes upward slightly to form more cleavage, but it was uncomfortable,
so I decided to get it out. I unzipped the dress and let it fall, then I reached
in and removed the improvised stuffing.
While I was un-padding my bra (how many women actually had to do
THAT, especially in a public bathroom???) I heard the clicking of heels as
someone entered the rest room. I quickly finished up and put my dress
back on. I grabbed the finishing touch out of my purse before exiting, my
gold cross on its twenty-four inch chain. In my first transformation it had
shrunk in proportion to my body size, but now I pulled it over my head
and it lay perfectly in my d?colletage. I closed my purse and put it over
my shoulder, then grabbed my pack and opened the door.
I walk out of the stall and over to the mirror, where I stare at the gorgeous
woman that I've become. As the flush of a toilet in the stall snaps me out
of my reverie, I set my bag down and opened my purse. I reach in and
grab the tube of lipstick I carry in there and start applying it carefully. The
stall behind me opens and a young woman in a nice olive green pantsuit
walks up next to me. She notices my makeup and comments that she just
loves that color lipstick, so I shrug and give it to her after I'm done with it
(what the heck, I was feeling generous as a woman). As a way of saying
thanks, she says that if I was up for it, she works in one of the department
stores and they're doing free makeovers for the entire weekend. Even
though the store is closed for the night to the general public, she could
give me a makeover. I told her that I'm meeting a girlfriend who works in
the mall for some shopping and that maybe later we'll stop by. As she
leaves, the young lady says she'll be expecting us.
I check my watch and figure I have just enough time to stash my backpack
in my car before I have to meet Joan for our shopping spree. I grab my
car keys out of my purse and dash out to the car as fast as three inch heels
can carry me. I walk through the door just as Joan is getting out of her
position at the concierge's desk. She comes over to me with a huge smile
on her face and her arms beckoning me into her embrace. As we hug, she
kisses me as I did with my ex-girlfriend at the height of our romance. Her
tongue parts my lips and she explores my womanly mouth and I do the
same. We separate from the kiss before anybody around us notices
anything too much out of the norm, but with a silent promise from Joan
that there's more to come.
We walk through the mall with our hands intertwined like young lovers as
she takes me to the lingerie store that overlooks the food court. We go in
and she starts picking out lovely things for me to wear. I ask with mock-
innocence where I would be wearing them. She smiles and walks up to
whisper in my ear that I'm to wear them to her place if I wanted to.
Before she goes back to picking out items for me, she pats my round
bottom lovingly.
We finally settle on a cute pink camisole and tap panty set with a scalloped
edge hem and a matching satin robe. Then Joan asks me if I wanted
anything else from the store, I jokingly say half a dozen of everything and
we laugh. She then seemed to make up her mind about something, and
she tells me to stay where I was (which was just outside the dressing
rooms, and I was still somewhat stunned to find out I'm a size 5 instead
of my normal 28 as a male). She came back a few moments later carrying
a sexy black teddy with four garters dangling from it. She presents it and
motions toward the fitting rooms with her free hand. I take the padded
hangar from her and she follows me into the stall, unzipping my dress,
and helping me out of it. She made sure to stroke my breasts, sending
flashes of electricity to my womanly loins.
We left the store about a half hour later carrying a couple of large bags
filled with lots of sexy lingerie, a robe, some hosiery and even a sexy new
dress. The interesting part about all of it was that Joan paid for
everything, even though I had tried pulling the money out of my purse.
Joan absolutely refused my cash saying that she'll get payment by having
her new girlfriend playing dress-up for her. That made me flush with
embarrassment as well as excitement from being complimented in such a
sexy manner.
Our next stop was one of the many shoe stores in the mall. This one had
more what might be termed as 'fetish' footwear, including hosiery. Joan
pointed to a particularly tantalizing pair of 5-inch stiletto heeled thigh-high
boots displayed in the window of the store. She practically tears my arm
out of joint as she rushed in to ask about it. Ten minutes later we were
carrying another box with the boots in my arms, again a gift from my
girlfriend.
The next two hours were spent looking in one store after another. With
Joan buying me little trinkets from each, whether it was a pair of earrings
or a new dress it didn't matter. Apparently Joan was very well off and
was able to spoil her lovers with gifts. At first I objected to it, stating that
I should buy within MY means, in this regard she ignored me and just
kept her shopping spree going.
By the time we were done, I think she spent over a thousand dollars, most
of it on a very sexy strapless evening gown in a shimmering dark blue
satin that cascaded elegantly to my ankles. While I was in the dressing
room trying to get into the gown, Joan almost scared me out of my panties
when she burst in on me again and she started groping at my chest while
fastening me into the bodice of the gown. A few minutes later, not to
mention some smudged makeup later, I was securely fitted into the gown.
I modeled it for the saleslady, who gushed about how it brought out the
blue of my eyes and that it was already paid for if I wanted to wear it
home. I politely declined, but as I turned to go back into the changing
room I grabbed Joan's hand, indicating that I wanted her assistance in
removing it. We had another little make-out session as she disrobed me.
She whispered in my ear that she wanted to do this at her place later, but
she's happy to get what she can. I whispered back that there's always
another dress she can help me in and out of later, to which she kissed me
lovingly in agreement.
Our whirlwind shopping adventure finally concluded, we haul our,
correction -- my packages to my car and manage to stuff them all into the
trunk, then we drove to an intimate little caf? for some light refreshments.
As I sip on some iced tea, she is drinking a cup of the house-specialty-
flavored coffee. We made some small talk about our past and she listened
in rapt attention as I highlight the few interesting points of my life. I
didn't try to change any of the facts of my gender, figuring that those few
obviously 'boyish' parts I was telling Joan about, that she would just
assume I grew up as a female. Like I mentioned to her that I went to my
girlfriend's senior prom as a 'second choice' because she broke up with
her boyfriend a week beforehand. Joan said that I was a very generous
and caring person to help her in such a pressing situation. She continued
by saying that I'm the most beautiful woman she's encountered, and that
she wants to take our relationship to the next stage. I responded by saying
we should take things slowly, but also that we should definitely get to
know each other a lot better before becoming intimate.
Joan kept attempting to seduce me over our light meal, rubbing her feet
against my legs, our stockings creating a sensuous friction and causing the
heat in my loins to rise again. I finally succumbed to the titillation of my
new lover and agreed to drive back to her place, which happened to be
only a mile or so from my place, but in the opposite direction from the
mall.
We arrive at her home, or should I call it a small mansion. It was in a little
golf community complex, showing the wealth and exclusivity of the area.
All the lawns were perfectly manicured to match the golf course that
surrounded the isolated villas, the houses themselves looked alike, maybe
about 4 or 5 basic exterior designs, though most likely with slightly
differing floor plans for inside. As we pulled up to her particular unit, I
noticed it was one of the larger exteriors, with tastefully feminine
individualization of the facade. We walked in and I was almost
overwhelmed by the beauty of her home.
Joan gently took my hand in hers and led me on a quick tour of the place,
ending it when we reached her bedroom upstairs. Once there, she turned
to look me straight in the eyes, the next thing I know we're writhing on
the plush carpet in an almost primal passionate kiss. Her hands caressed
my flesh while mine did the same, I was gently kneading her breasts
through her blouse as she was unzipping my dress and with an expert
flick of her fingers unfastened my bra.
I was naked but for my garter and stockings in almost no time. Joan's
dainty finger traced the seam of my stocking as it traveled from my slim
and shapely ankle to the terminal end of the stocking, where she slowly
traced her nail along my inner thigh toward my virginal womanhood.
Once her fingertip brushed my labia, I felt a jolt as the nerves of that area
sent an electric sensation directly to the pleasure centers of my brain. I
think I let out a gasp as she then took that finger and inserted it into my
vagina. It was so wonderful I couldn't remember anything but the
sensation, but she looked at me suddenly, understanding immediately that
she was my first lover, male or female. She whispers loving thanks for
letting her have the honors of de-flowering me.
With a nod I acknowledge her compliment and Joan went back to
massaging my womanly lips, getting my juices flowing with expert
fingers, sending me into a heavenly euphoria as I start building toward my
second climax as a woman. As my womanly lubricants started flowing
freely, and I was nearing nirvana, she added her tongue to her finger play,
pushing me over the edge and into the spiral of orgasm. The waves of
pleasure washed over me with visible effects, as if I were in the throes of
a seizure of pleasure I writhed about uncontrollably, wrapping my silk-
clad legs around Joan's body while moans of pleasure escaped my lips,
reverberating in the halls of her home.
As the pleasing ecstasy became less overwhelming and I regained my
senses, I saw that Joan was looking at me with a smile on her face. She
slides upward on my perspiration coated body and kisses my sensuous
lips, smearing my lipstick with the passion that moves us in our union. I
whisper to her in a somewhat husky voice that I should repay her in kind.
She suggests a shower together -- perhaps as hot and steamy as I am she
says, caressing my breasts with her fingernails, bringing my nipples back
to attention and sending me shuddering back into heaven for a few
moments as I start to build toward yet another orgasm. She pulls away so
I can come back to rationality, then she offers me a hand up so we can
shower, which I graciously accept.
I'm a little wobbly as I walk to her bathroom, the last pleasing spasms of
my orgasm slowly fading away. With my arm wrapped around Joan's
slender waist, we make our way to her bathroom. I strip off the last of
my clothing, making sure to leave on my earrings lest I change back and
scare my lover. She steps into the shower stall and starts the water
running before beckoning me to join her with a curling red-tipped finger
motioning me forward. I enter the shower and she pulls me into her
moistened embrace. Our breasts squeezing together as we turn around
beneath the gentle spray of her shower, she coos again that she loves me.
At this point I feel like telling her my secret, just so we can go off
somewhere and get married. After a moment's hesitation I decide to wait
till another time because at the moment I'm focussing on just loving Joan
as she did to me. I start by kissing her all over her face. And then I
slowly work my kissing downward, stopping at the base of her neck, the
sexy nipples standing erect on her pert globes of womanhood, then her
flat stomach (allowing my tongue to probe her navel sends a shiver down
her spine). Finally I reach my objective, where the moisture of the
shower blends with the moisture dripping from her warm, well-lubricated
orifice. My hands cup her firm buttocks and I decide to be naughty ... I
take one of my fingers and slowly start to insert it into her other lower
orifice. I'm satisfied by a gasp escaping Joan's lips as my pink-lacquered
nail penetrates her sphincter, while my other hand starts to play with her
labia.
I start to slowly pump my finger in and out of Joan's anus while I gently
blow across the engorged pink opening to her womanly canal. As I bring
my face closer to her femininity, Joan reaches her first climax. I can tell
that because aside from the moaning and shaking, I almost get my probing
anal finger stuck as her muscle clenched. I keep going with the clittoral
massage and I add my tonguing to the action. I taste her sweet ambrosia
as my tongue teases her womanhood while I move my teasing finger into
her warm vagina, where I start a rhythm counter to the one I established
with her rectal area. She soon climaxes several times in rapid succession.
I finally cease my ministrations and start washing her down with the body
wash and netting sponge, starting at her dainty feet and gently scrubbing
my way upward. In a few minutes she's covered head to toe and she in
turn does the same to me. She titillates me as she scrubs my womanhood,
but she manages to control herself enough to finish soaping me up. Then
we squirmed together, feeling ourselves sliding against each other as we
slowly rinsed under the showerhead.
We stepped out of the stall hand in hand and started to dry each other off.
I gather up my clothes and go to the guest bedroom to dress. I pull out
some of my new lingerie -- sexy soft pink garter belt, bra and panty set,
and a pair of powder blue stockings and matching full slip. I feel so sexy
as I drape them about my body.
I keep my dress lying flat on the bed, while I sashay back into the master
(or is it mistress' in this instance) bedroom. I stand and pose as
seductively as I can imagine in the doorway, which brings a catcall from
Joan. She comes over to wrap me in her embrace, but I playfully slap her
hand away. I slowly make my way to the clear area at the foot of the bed,
where I pirouette, letting the skirt of my slip billow outward. Joan douses
the lights in the room, leaving me momentarily disoriented. Then her
bedside reading lamp clicks on, blinding me momentarily in its
illumination. I mimicked an escapee caught in the police searchlights
before I relaxed and slowly stripped down to just my garter and stockings.
As I exited the bedroom I heard her catcall again as well as some applause.
I took my bows and re-dressed myself. I could see her unasked invitation
to stay in her facial expression. I told her that I live with, and help care for
my aging mother and I should go home. I promised her that I will stay
overnight on another occasion, when I know someone can watch over
her. She says I'm a sweet young lady for helping out like I do. I start
dressing and I comment that there are tons of things she doesn't know
about me. Before I leave her place, Joan says she looks forward to
finding out all there is to know about me.
I drive home in a pleasant, euphoric haze. I have to make three trips to
bring in all my packages from the car, but I manage to do it without
waking up mom. I quickly strip and complete my change back into the
old, familiar me. I'm emotionally and physically exhausted from my
evening's activities. I collapse onto my bed and fall into a deep, dreamy
sleep.
Fin.
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