Man! I Feel Like A Woman! free porn video

It all started when I went to college. I met a woman in a class during my
freshman year. Her name was Karen -- a communications major. Karen and I
started dating and things rapidly progressed. By my junior year, we shared
an apartment together.

She was always a little on the kinky side. She liked things like a little
minor bondage -- being restrained while making love and the like. I was a
naive k** from the Midwest; however, I was open minded and wanted to please
her -- so I picked up on these skills and rapidly adapted. On more than
one occasion she even had shared with me that she wondered what it would be
like to be with a woman.

On Halloween, we used to go to this Kareoke bar that offered $500 dollars
prize for a best costume. It was a well known local event. When you are a
poor k** from the Midwest -- $500 is a very large sum of money. I used to
dress up and try to win. I went my first year as Elvira, the buxom movie
time hostess. I came in second and won $100. Karen and I would go
together. She enjoyed dressing me up and making me look good.

The following year she helped me dress as Cher in her video -- `If I Could
Turn Back Time'. She did wonders -- I looked great. The look was very real
-- complete with a tattoo on my ass that she drew on with a marker. I had
all sorts of guys hitting on me and several even grabbed my ass. We didn't
have to buy a single drink that night. She was all giggly about it --
thinking it was incredible that I looked so passable. I lip sank the Cher
song and took first place. She was thrilled. When we got home, we were
barely in the door before she was all over me. I went with it pretending
to be a woman. I have never seen her so responsive. Her hands were
everywhere especially on my breasts. When she went to the bathroom, I ran
into the bedroom and slipped into one of her sexy little teddies. When she
came back and saw me she was thrilled. She led me to bed and I did
everything that I could think of that a woman would do to please another
woman -- going down on her, using my hands and mouth all over her. She had
many orgasms that night. I hid my erection until the very end of our love
making session. I enjoyed the evening as did she.

>From that point forward she started to occasionally want to dress me as a
woman. I would typically decline, but once in a while I would oblige her
especially if I had a few drinks in me. I was somewhat concerned that she
seemed to be into it that much. However, I was interested in pleasing her
and I didn't mind that much. Besides, I have to admit, the feeling of
satin panties against my penis, the smoothness of my hose covered legs, the
look of my face when made up like a woman was arousing to me.

For the following year's Halloween party, she dressed me as Monica Lewinski
-- little black dress and all. I have to admit she did another masterful
job. She even gave me a blow job and put some of my cum on the dress.
Guys once again were all over me. Most asking if I would blow them --

"Hey, wanna step into my oval office?"

She thought this was great. We didn't win -- there were other people
dressed as Monica Lewinski and we took second place. Once again, we went
home and I made love to her dressed as a woman. I would buy her lingerie
as gifts occasionally. I had gone to Victoria's Secrets for no special
reason some months earlier and purchased a black lace corset with matching
panties and nylons. When we got home and I saw it laid out -- I have to
admit -- I was starting to enjoy being dressed as a woman. When I came out
of the bedroom dressed in that with a short little black silk robe I had
purchase a year or so prior the look on her face was one of -- I don't know
-- absolute lust. I have never seen her like that with me when I was
dressed as myself.
I pleased her as I had never done in the past. Part way through the
session she produced a strap on dildo and asked me to just take the act a
little further and oblige her by wearing it. I did so. I have never seen
her so responsive. She bucked and screamed as I had never seen her in the
past. Again, we both had a wonderful time that night.

After that point, she started to want me to dress even more. I was
reluctant. She asked me

"Didn't you enjoy it Halloween night?"

I really did enjoy it. I wanted to desperately to please her and I would
agree to dressing perhaps once a every week or two. On occasion, we would
go out in public. Shopping, trying on outfits in women's stores, sometimes
dinner, sometimes a movie, etc... The first few times I was petrified.
This was not like Halloween. She reassured me that I was a better looking
`woman' than most of the real women out in public.

She would buy me things to wear that she could wear also. She had
impeccable taste and always made me look great. I was even getting
somewhat skilled at dressing myself. I have to admit I did get aroused by
seeing myself dressed, going out in public and passing as a woman. She
would rub my swollen cock keeping me erect almost the whole night long and
when we go home I would make love to her dressed as a woman. She always
enjoyed these nights out as did I. I started wondering who enjoyed it more
-- me or her.

On of the best times we had was Christmas shopping. We took an overnight
trip. We left Saturday with me dressed. I didn't get into my normal
clothing `til we returned late on Sunday night. The whole weekend being
dressed was wonderful. Breakfast in the hotel lounge. Shopping. Trying
on outfits. Walking through the malls. Shopping for lingerie together.
Dinner out. Out clubbing. Guys buying us drinks. Making love to her as a
woman. It was all truly wonderful.

She had classmates that were lesbians -- one in particular -- Mary that was
a little on the outspoken side. Mary never passed an opportunity to male
bash. She didn't like me -- one, because I was a man and two, because she
felt that I forced Karen into the sexual activities that we took part in
together (bondage, oral sex, etc) -- male oppressing the female and all
that. If only she really new who was doing things to please who in Karen
and my relationship. Karen never told her of my dressing as a woman for
her, or at least I never thought she did.

On more than one occasion we had somewhat heated discussions about sex,
women pleasing male partners and about how women are made to feel. During
one of these discussions Mary got very loud and angry perhaps due to the
drinks we had, perhaps not. The conversation was about women giving men
blow jobs. I was of the opinion that wanting to please your partner was a
good thing as long as both people were adults and not hurting anyone else.
Mary was very adamant that it was degrading to women and wouldn't have any
of it. Karen started to side with Mary. I was surprised. Karen was
always quite the good little cock sucker and she seemed to enjoy it. Mary
said

"Maybe all men should swallow a little cum to see what it is like"

To which Karen quickly added

"Yeah! Perhaps you should see what it is like to give a blow job and to
swallow!".

Well, I quickly calmed the conversation realizing that it was too heated
and this was not good for Karen and my relationship.

>From that point forward Karen seemed less interested in performing blow
jobs and least of all swallowing. I didn't force the issue. She would
occasionally ask

"Would you like to see what it is like to swallow some cum?"

She wanted to blow me and take my cum into her mouth and then feed it back
to me. She actually tried to do it with once without my knowing and I got
upset with her. This caused a very large riff in our relationship and for
several days we didn't talk to each other.

Later in an effort to make up, I tried to appease her one night. I decided
to surprise her. I came home and got dressed using all my acquired skills
to make me look as best as I could. I put on a black strapless bra,
breastforms, black high cut lace and satin panties, sheer to waist black
hose and a slinky black dress that she had purchased for a wedding we had
gone to. Black, shiny, spaghetti straps, very high slit up the side --
very elegant and sexy. I put on her fake diamond earrings, necklace and
spikey heels. I have to admit that I did a very good job. This was almost
as good as Karen would do. I prepared for a romantic dinner and had it
waiting when she got home.

When Karen came home, the door opened she entered with Mary and another
woman I had never seen before. I was floored. Mary's jaw dropped open.
Karen quickly introduced me as `Jamie', a girl friend of hers from out of
town. My real name is James, but I was used to some, Karen included,
calling me Jamie. I saw her make a subtle motion to Mary not to let on.
Mary came over and shook my hand pretending not to know who I was. I
greeted the other woman as well.

We sat around had a couple of drinks and chatted. Mary asked

"So Jamie, why are you all dressed up?"

and gave me a sly smile knowing that she was putting me on the spot. Karen
quickly answered --

"She is in town and having a friend over for dinner."

and shot Mary a dirty look. Mary wouldn't let it go. Mary asked

"Friend for dinner, hmmm... What is he like? Must be special to dress
like that? Is he handsome? When is he getting here? Maybe we could stay
and meet him?"

and gave me a sly smile and a knowing look. Karen said

"Yes, she does have to get going and I have to get changed. So you'll have
to excuse us."

Karen gave Mary another dirty look and as they were leaving said something
to Mary.

The door closed and she turned, came gave me a huge hug and a long deep wet
kiss. She lit the candles, killed the lights and threw me on the coach. I
felt as though she was r****g me. I let her have her way. I wanted to
please her. Later, after dinner, I agreed to let her wear the strap on
dildo while I went down on her as a woman. I proceeded to perform a blow
job on her as though I were a woman and she a man. She coached me through
it and was very gentle -- not forcing it down my throat when I started to
gag. She seemed to enjoy it immensely. Later we laid in each others arms
for a long time and talked. She assured me that she told Mary to keep her
yap shut or she would kick her ass. She basically told me that what Mary
was saying is accurate and that she thinks that every man should know what
woman are made to feel like. In a very loving tone she said

"Maybe some day you will know what it feels like to be a woman".

She asked if I wanted to see what it was like to swallow cum and I told her
no. She let it go.

After that things seemed okay for a while in our relationship, but
eventually she wanted me to dress pretty much full time at home, laying
things out for me all the time. I told her that this had to stop
progressing along this path and she got upset with me. We had a blow out
argument where we both said things we regretted. Needless to say, this was
the end of our relationship. I moved out several days later.

Both her and I were very deeply hurt. I missed her. I missed our love
making, both not dressed and dressed. She and I would run into each other
on campus and be very cordial to one another. I saw her with Mary quite a
bit and often wondered if she was now a lesbian. I truly just wanted her
to be happy. Mary never said anything about the seeing me dressed as a
woman.

I received a call from Karen at the beginning of the following October -
our senior year. She told me that she wanted to get together and talk. We
met at a local coffee place and talked.
It was great to talk to her. I always enjoyed my conversations and time
spent with her. We caught up on everything and truly enjoyed the moment.
As it turned out -- she wasn't seeing anyone nor was I. I was getting
ready to go when she said to me

"Are you going to enter the Halloween contest this year???"

I told her that I was, but I hadn't given it much thought what to go as
because I had just been too busy. Perhaps Elvira again I told her. She
shook her head no and mentioned that she had a great idea for a costume for
me and that she thought that I would love it. She went on to mentioned
that the prize for first place had been upped to $1000 this year. That
certainly got my attention. Not sharing rent with someone was much harder
financially.

She said that if I won we could split the prize. She told me that she
couldn't guarantee that I would win, but she did think that this would be
one of the best costumes that she could think of. I asked her what it was.
She didn't answer and just added that she thought it would `put the Cher
costume to shame'. She peaked my interest. She reassured me that she had
no interest in getting back together with me -- however, she would like it
if I spent the night at hers that night -- for old times sake. To which
she added --

"Who knows, maybe there will be a blow job or two in it for you"

and smiled. This got my attention even more -- I loved to get blow jobs
from her.

I asked her again what the costume was and she wouldn't tell me -- she just
kept on saying that

"I would love it".

I asked her to tell me if I would be dressed as a woman. She said
absolutely. She leaned over at that point and said

"You really will love this."

At this point I agreed it was a deal. She said great. She got ready to
leave and mentioned she had a few things to get to prepare for it, but she
had most everything already. I left wondering what it could be and was
intrigued by the idea -- and aroused

Halloween was a few days off when she called and asked if I could come over
about one in the afternoon the day of the contest to get ready. I thought
that this sounded like a lot of time to get ready and she agreed and told
me that I had to have my nails done so we needed the time. I agreed. I
enjoyed spending time with her anyway.

Halloween came and I went to Karen's around 12:30 -- I was certainly eager
to see what this costume was. I got there and her friend Mary was just
leaving. She shot me a dirty look and said

"Well, the both of you enjoy tonight"

and then she looked back at Karen with what looked like a sly smile and
then at me and just smiled. That was the most civil I ever recalled her
being.

I apologized to Karen for chasing Mary off. Karen closed the door and said
she was just leaving anyway. Right away she ushered me into her bedroom.
She told me that we had to hurry because my `appointment' was for 2:30. I
said

"Appointment???".

She explained it was to get my nails done. I told her that I wasn't going
to do it. She said

"Look -- trust me. I know what I am doing. You want to win the thousand
dollars don't you?"

in a very reassuring tone. I looked at her for a moment -- and I said

"Okay".

I asked

"What is this costume anyway?".

She told me just a bit longer and I would know. She looked at me and said
in an excited tone

"You are going to love it!"

Now I was aroused. I enjoyed dressing as a woman. She came up to me
rubbed my crotch and said

"And there will likely be many blow jobs during the night for you".

I had a raging erection now. Still she didn't tell me what the costume
was.

She ordered me to strip. She led me into the bathroom where she proceed to
smear hair removal cream all over me from my neck down. She applied some
special cream to my face. I told her that I had shaved earlier and that it
wasn't necessary. She said

"One thousand dollars!"

and again -- I agreed. After a short while she had me get into the shower
and clean up. I came out hairless with the exception of my head. Baby
smooth from face to toe.

She brought out some breastforms that we used when I dressed for her when
we were together and applied them with some adhesive adjusting them very
carefully for position. She gave me a matching white strapless satin bra
and matching high cut panty and told me to put them on. It had been a
while since I had done this and I was starting to remember the feelings of
arousal. After this she gave me some sheer nude panty hose to put on. Next
came a white camisole and half slip. She sat me at her dressing table as I
had done so many times before. Looking down and seeing my beautiful long
hosed legs protruding from the lace trim of the slip made my erection even
worse. She made me up very conservatively -- kind of a soft demure look.
I was wondering what the costume was going to be like. She told me that
this was not how I would look this evening and that it was just for going
out in public. She fitted me with a shoulder length auburn wig to complete
the look. She handed me a white silk blouse and slim black skirt and I put
them on familiarly. I slipped into a pair of black heels I had worn so
many times in the past and she put a small pair of pearl earrings on me and
a matching necklace.

I was getting very aroused now. I was starting to fondly remember what it
was like to dress. You could see a bulge clearly in my crotch because of
the tight fit of the skirt. She saw this and said

"The first of many blow jobs in your day".

She dropped to her knees without hesitation, raised my skirt and pulled
down my panty hose and panties and proceeded to give me a blow job. All
the time I saw a profile view of this in the full length mirror on the
closet doors. A gorgeous leggy woman with another woman with her face in
her crotch. The long lovely legs, the look of the lace of the slip against
the legs, the curves of the body, the red lips -- this image was all too
much for me to handle for long. I came in what seemed like a minute and I
came hard. My knees buckled. I stumbled and practically fell. She got
up, licking her lips, smiling and said

"I guess you liked that?"

I was breathless.

I had to sit down at the dressing table. She came over she spritzed me
with some Tommy Girl. She grabbed her jacket and bag. She handed me a
purse to put my cigarettes, wallet, keys, cell phone in along with a
jacket. We headed out. I was still a little light headed from the blow
job. I made it down to the apartment parking lot. I heard her tell me
that we should take my car. I looked back and saw her videoing me. I
found my keys in my purse and quickly got in the car. She got in and I
asked her what was with the video.

"I thought you might like to see yourself."

I have to admit, the thought did have me interested. In all of our
occasions dressing me, we rarely took pictures and never video. She had
experience with video equipment from her communications course work for her
degree.

We headed out to the nail salon. When we arrived we went to the front desk
and were told we would have to wait a minute or two. Shortly thereafter we
were taken right in. I turned a few heads which made me nervous, but when
I saw myself in the mirrors on the wall I knew they were just looking at a
beautiful leggy woman not a man dressed as a woman. I sat down and the
girl introduced herself and got started. She asked some simple questions
to which Karen answered them all including the color of polish to use. I
would see Karen video it occasionally. The girl asked if it was for
Halloween -- to which I answered yes. I would occasionally say something
and practice my `woman's' voice. By the end of the appointment, I was
becoming comfortable with talking in small sentences. I received a full
set of beautiful nails with deep red polish expertly applied. They really
added to the look. On the way out, the cashier apparently told Karen

"Your friend is very pretty. Is she a model?"

Karen told her

"Yes. How did you know?"

Karen was loving this as I was. I was feeling much more at ease that I was
very passable as a woman.

We left the salon and instead of returning to the car in the parking lot
Karen took my hand and lead me in the opposite direction. We walked down
the sidewalk past all the little shops. I could see my reflection in the
storefront windows. We were just two woman walking down the street. We
looked like two women out window shopping. We walked for a few blocks
passing people on the street. Most didn't give us a second look, except an
occasional man that would check me and Karen out. I actually saw one man
from his reflection in the store window checking me out after he passed me
looking at my ass I believe. Karen would occasionally stop while I walked
ahead a bit. The sound of the heels on the sidewalk, the guy checking me
out were enough to keep me aroused. The cool feeling of the air on my
beautiful hosed legs was wonderful. I was enjoying this outing very much.
I had forgotten what it was like.

Karen stopped in front of a storefront doorway and looked at me and said

"Surprise!".

I looked up to see that it was a bridal shop. She opened the door and said

"You ready?"

I immediately became nervous. We entered and were immediately greeted by
the sales woman. Karen introduced us. The woman asked Karen for her size
to which she replied

"Oh, I am sorry. Not me -- my friend Jamie. She is a perfect eight".

I immediately got another raging hard on. Oh my god, I was going to try on
a wedding gown?!?! I never shared this with Karen, but I always secretly
wondered what it would be like to wear a wedding dress to see what it felt
like. Some women look absolutely spectacularly beautiful in a wedding
gown.
The anticipation of how I would look was incredible. I was fumbling with
the excitement of what it would be like.

We were escorted to some racks where the sales woman made some
recommendations after asking some questions -- long or short sleeves,
modern or traditional, length of the train. Karen and I picked out not
one, but several. I loved them all. I was in heaven. We took the dresses
and went into the dressing room telling the saleswoman that we needed no
help. She said

"Just ask it you need anything"

and headed back to the front of the store. Once in the dressing room, I
had to strip to my bra, hose and panties. I had been in many dressing
rooms before, but this dressing room was different - very large and open
with mirrors everywhere. The stalls were large and open as well. Karen
quickly helped me into the crinoline slip to hide my erection. She
produced a pair of white heels from her bag. Karen had apparently planned
for this little excursion.

Then the first dress. It was an elegant simple white dress with a tight
fitted bodice. I looked in the mirror and could not believe my eyes.
There before me in the mirror was a beautiful looking woman in a wedding
dress. Karen asked --

"Well? You like it?"

I absolutely loved it! I raised the skirt to see my legs. Oh my god! The
image was awesome! After a short while of swishing around -- posing this
way and that. She helped me out of that and into the next dress. My
erection was rock hard now.

The next dress came -- a more traditional off the shoulder long sleeve with
a cathedral train, beading all over the bodice and lace. It was very
ornate. It took a while to get me into it. Karen wouldn't let me look
until she got a veil on me. The only thing I could do was look down to see
my breasts, arms and the front of the skirt poofed out in front of me. The
anticipation of seeing myself was incredible. When she did allowed me to
look and I turned and looked.

When I finally looked, my jaw dropped. I was just stunningly beautiful. I
looked like one of those spectacularly gorgeous brides! I moved toward the
mirror to see myself more closely. As I move, the gorgeous bride in the
mirror moved too. The sound and the feel as I moved -- I almost came right
then and there in my panties. I put my hands on my waist and ran my hands
over the bodice -- the painted nails, the breasts, narrow waist of the
beaded bodice, full skirt, the long train. The look was fabulous. I
looked back to Karen and she had her video camera going again and was
beaming from ear to ear. I explained that I thought I might cum if I got
much more aroused. She shut the camera off. Came over and asked to see me
legs. Oh my god the image was indescribable! She immediately dropped to
her knees, lifted the crinoline slip, pulled down my hose and panties and
started to blow me right there. The whole thing - the image -- the
beautiful bride, tight bodice displaying my feminine curves with all the
beading and lace, the beautiful face framed by the veil, the painted nails
holding up the skirt with the long legs peeking out from under the lace of
the hem of the dress, the rustling sound of the gown and slip, the feel of
the slip against my legs, doing this in public -- I literally came in just
seconds this time.

The next dress wasn't as nice. It was kind of anticlimactic too. Karen at
this point seemed bored or something. So I got changed into my street
clothes and we made our exit and excuses. The sales woman handed me a
card. We left and headed back to the car. I thanked Karen and told her
about my secret desire which she fulfilled. She just smiled and said

"I told you to trust me."

I felt so wonderful and satiated.

Next we went to the mall. We went to the food court where we grabbed a
bite to eat. We talked a bit. I asked her what prompted her to plan all
this. She just smiled and said

"A thousand bucks and maybe you spending the night for old times sake".

We strolled around the mall just like old times -- I was on a high. The
sound of the heels clicking was through the mall was awesome. We tried on
some outfits, shoes, sniffed perfumes, went to the ladies room. It was
good to see her smile and enjoy my company, even though it was while I was
dressed as woman.

Before we left the mall. She said we just had to get one thing - some hose
for my costume. We went to Victoria's Secrets and the hosiery displays she
proceeded to pick out some off black lace top stockings and a lace and
satin black thong. She smiled at me and just said

"You are going to absolutely love tonight!"

I just knew that she was going to be right. Again, I was getting aroused
and could hardly wait any longer. While she was looking for hose, I went
to a rack and was looking at a slinky looking sparkly mini dress marked for
clearance. She saw this and asked if I wanted to try it on. I didn't
reply. She took it from the rack and handed it to me just smiling.

Here I was trying on clothes in Victoria's Secrets! When I came out of the
dressing room, I looked in the mirrors immediately. There were other woman
about, but I was to interested in seeing myself to worry about if they saw
something that made them think I was a man dressed as woman. I was hot
looking, I loved the dress. Karen appeared and told me

"Your legs are one of your best assets and that dress really shows them
off, Jamie."

There was a sales woman near by working on a display -- she agreed with
Karen and mentioned that she saw a customer's boyfriend checking out my
`assets' while I was looking at myself in the mirror. She looked at her
watch and said

"Oh geez, we better get going!"

It was now like 6:30. I got changed out of the dress. When I came out,
the sales woman handed me the hose and panties Karen had picked out and
told me that Karen told her to tell me to check out. While I waited in
line, I looked at some sales displays -- I actually purchase some satin
panties for myself because of the outing and remembering what it was like
to wear panties. We made a hasty exit and got back to her apartment.

Again, she was videoing me going up the stairs and to the door of her
apartment. While I waited for her at the door one of her neighbors came
out. She introduced me as a friend. He noted the bag and said

"Ah, Victoria's Secrets"

and smiled at me. He asked us what our plans were for the evening and I
replied. She and I said goodbye and entered the apartment. I couldn't
believe how comfortable I was feeling passing as a woman -- the voice, the
look, everything.

She had me strip immediately and told me to take off the wig and to go wash
my face. I did as I was told. I was getting aroused again because of the
long awaited anticipation of the secret costume. When I re-entered the
room, she had the mirror on dressing table turned so I could not see my
face as she worked. She said that she wanted it to be total a surprise.
She told me to get into the black strapless bra, thong and stockings that
were laid out for me and to put on the short black silk robe laid out as
well. She asked

"What didn't you like my choice for underwear?"

and held up the additional satin panties that I had bought at Victoria's
Secrets. I was embarrassed. I explained that they were for me. She
smiled and said

"That's okay. If you want something to go with it, just ask."

I sat down at the dressing table and she did her magic. It seemed like a
good half hour or so. She produced and brunette wig already done up into a
bun and secured it with some sort of tape to my scalp. She finished.

She stood back to admire her work for a second and then gave me permission
to look. First I adjusted the dressing table mirror to see my face. Oh
wow!!!! Was that really me??? I had to see what I looked like in the full
length mirror. As I stood and took a look at the results. My mouth
dropped open. When I saw the woman in the mirror whose mouth dropped open
at the same time and whose every movement mirrored mine - I knew this was
not someone else -- it was me! I have never looked this -- well -- hot.
Yes, I was a hot looking woman! The sultry look, the pert breasts, the
beautiful nails, the long legs topped with the lace tops of the stockings
protruding from under the short little robe. I could not believe my eyes!
I had this sultry, seductive almost slutty look. Dark makeup around the
eyes and lots of it. Deep red lips. Blush that gave me a high cheek bone
look. The woman, or rather I, looked somewhat familiar, but couldn't
figure out where I had seen this woman. While I stood there admiring
myself, she told me to spritz some more perfume on and to put on the
earrings that were on the dressing table. I did as she asked. The
earrings were simple black elegant and sparkly.

I turned to see my image in the full length mirror again. Oh my god! I
looked so hot. I ran my hands up over the stockings and adjusted the lace
tops. The image was heavenly and I felt very excited. She was busy
getting her outfit together (a Hooters girl) when she told me to open the
closet and to retrieve the box in the bottom. I did so, putting it on the
bed and opened it eagerly. There was top hat with a tiny veil, long satin
gloves with a kind of fringe, a choaker again with a beaded fringe, a short
slinky stretch satin mini dress with a tube top, a black corset and
above-the-knee black leather boots with about 4 inch heels. I was very
eager to get dressed now. I simply couldn't wait any longer.

She was almost done getting herself ready and asked --

"Well, what do you think of your costume???"

I was speechless and to thrilled to finally be getting into my outfit for
the night. She came over and started to help me get dressed. I wanted to
do it myself. I started to put on the corset when she stopped me and told
me to put the dress on first saying

"Trust me"

I did as she asked and slipped into the dress. I managed to get the corset
on but needed help lacing. She had me grab the door jamb as she cinched
the corset. She really had it tight. She told me to catch my breath and
breath out as deeply as I could. She cinched it tighter yet. I could only
breath in short shallow breaths. The whole process took about five minutes,
but when she was done. Wow! I had a bosom! I had breast bursting out of
the top of the corset! Cleavage even! She was absolutely right. I was
loving this!

Putting on the leather boots took a bit. I could barely bend over and had
some trouble getting my foot into the bottom past the ankle of the boot. I
did eventually manage though. I had a slight bit of trouble standing on
them at first due to the size of the heels, but quickly got used to it.
Short sure steps. Next the choaker which she had to help with. Then
gloves -- I thought that it was odd that I had gloves -- why the nails
then. Finally the top hat to complete the look. OH MY GOD!!!!

She was absolutely right. I did love it! There looking back at me in the
mirror was Shania Twain! She made me up like Shania Twain from her video
`Man! I feel like a woman!'

If we were going to a Shania Twain look alike contest -- I had no doubt we
would win -- I remember thinking that Shania Twain herself might even loose
to me in a contest. Perhaps that was an exaggeration, but I did look
awesome. She did a masterful job, I really looked like Shania Twain. I
told her she did an awesome job. Tall, leggy, sultry. I was looking
totally hot!

I practically starting cumming right then when I looked in the mirror.
What a hot looking honey she had transformed me into. I just stared at the
image in the mirror. I couldn't get enough of looking at myself. I
turned, walked, looked this way and that. Oh, I was in heaven! She came
over, gentle brushed the erection in my groin when she again dropped to her
knees an proceeded to give me another blow job. Again, the profile image
of me with the slutty sultry look, the exposed lace from thigh high hose,
the waspy waist with the breasts bursting from the top of the corset, it
was all too much to handle for long. This time she barely got my cock into
her mouth when I exploded. I grabbed her head and pumped everything I had
down her throat.

She got up smiling and said

"One of many.."

to which I completed

"Blow jobs in my night"

She just smiled from ear to ear --

"Yep, that's the plan, Stan!"

She seemed to be enjoying this way too much, but I was on an indescribable
high and couldn't see straight if I had to.

She put on a video tape of the Shania Twain music video in her living room
VCR as she finished getting ready. I poured some drinks and had a
cigarette while I studied the video. I could easily do this. We were going
to win $1000!!! I kept looking in the living room mirror -- practicing the
video and just admiring my look. I was really loving this. I was so happy
that she talked me into this.

It was now 8:30 and the night was getting on. She told me to sit at the
dressing table and recoat my lip stain that she had used. I did and loaded
up the purse again -- wallet (oops needed to stop at the ATM for some
cash), keys, cell phone, cigarettes to which she added -- blush, eye liner,
mascara, lip stain, perfume.

I asked her about her video camera, `cause I definitely wanted to see this.
She said not to worry that she wouldn't disappoint me and that I would get

"More than I would ever wanted".

She handed me a short little waist coat and my purse. She grabbed her bag
and out the door we went. As she locked her apartment door -- her neighbor
came out when he heard the voices. He looked at Karen, smiled, told her
she looked hot. Then he looked at me, he was starring. First his eyes
went to my chest and cleavage. Then he looked me up and down. He was
checking me out! All he said was

"Wow! You look very, VERY hot Jamie!"

He apologized to Karen that he was slighting her for me. Wished us luck
and fun and we headed out.

That was too cool. Passing as a woman and a guy thinking that I was `hot'.
I was loving this already. As I walked down the hall, I stopped and
glanced back and indeed, she had her video camera going. I looked down and
saw these long sexy legs making their way down the stairs. They were
mine!!! I was loving everything about this. Tonight was going to be
great!

She wanted to take her car this time. I agreed. As I climbed into the car
my skirt hiked up, the look of the legs with the lace top stockings peeking
out from under the skirt was indescribable. We hit the bank so I could go
to the ATM. Walking into the glass booth I saw my reflection in the glass
-- I was getting another hardon again. Coming out of the bank. A couple
of men coming up the walk toward me -- hooting, whistling, cat calling as I
passed them,

"Hey, baby I'll make you feel like a woman".

I was on an indescribable high. I got back to the car and Karen was
absolutely enjoying it all too -- she was proud of her work -- just
beaming. She went down on me right there in front of the bank. Her head
in my crotch, right here in front of the bank, seeing the long legs with
the lace top nylons exposed -- I came in seconds again. I could never
recall ever having been able to cum so many times in such a short period
ever before.

We got to the bar and couldn't park anywhere near the place. Downtown was
really crowded. The closest we could park was about three blocks away in a
parking garage. We passed all sorts of people along the way -- some in
costume, most not. Almost everyone did a double take when they saw us.
The walk to the bar went past a whole series of small restaurants and bars
on the street. I could see my image in the windows as we walked past.
Men's heads were turning. One of the restaurants had tables in the front
window. When I walked past, one man gawked so badly his girlfriend or wife
said something to him and she appeared to kick him under their table. Too
funny! The entire walk to the bar. More whistles, cat calls and guys
hitting on me. This was really great! This was the most I enjoyed being
dressed yet. I couldn't tell you whether I enjoyed dressing in the one
wedding gown more or this. I was thrilled that I had gotten to do both.

Karen hung back and videoed me walking down the street with all of the men
giving me looks and hitting on me. I got to the entrance to the bar and
waited her. We entered together. Heads were turning. People pointing and
commenting. We were creating quite a commotion. The person running the
kareoke saw me and threw a light on me and said

"Ladies and gentlemen -- Miss Shania Twain!"

The place erupted with applause, whistling, etc.. I made my way through
the crowd to the bar. All the way, more guys hitting on me, women
commenting how great I looked, etc.. I finally made it to the bar to get
Karen and I drinks when the bartender told me that two guys on the other
side of the bar wanted to buy us drinks. I wasn't into it, but Karen
looked at them and seem like she wanted to meet them so I accepted.

We went over and joined them. We talked for a while. After a drink or
two, the guy on my side of the table kept on putting his hand on my thigh.
The other guy kept on grabbing Karen. She seemed annoyed so we thanked
them and said goodbye. They gave us their numbers and I told them

"We will call."

As we left them Karen said to me --

"You lying little tramp!"

and we chuckled together.

During the night, we sang along with the songs, drank (always drinks
waiting for us at the bar from guys) and talked to people. I was getting a
lot of attention as was Karen. When I finally had to go to the bathroom, I
went to Karen and asked her

"What do I do? The bathroom is really crowded."

The place was packed and it wasn't like in the mall. She told me --

"Just like all us girls -- we go together."

She led me to the ladies room. We waited in line a while -- something I
pity women for. We finally entered the ladies room. Certainly much
cleaner than the men's room. There were two woman just leaving. I had to
wait in line a short while for the stall to open up. All the time I was
waiting there, I was able to see my image in the mirror past the women
adjusting and primping themselves at the sinks. Finally, a stall was
availible. I entered the stall the woman had just vacated, lifted my
skirt, pulled down my panties and did what I came there to do. While I was
in the stall, I heard some girls come in and they were talking about who
they felt had the best costume. All but one thought

"The girl dressed like Shania Twain"

I heard another voice say

"The one dressed like Shania was just using sex to win. It is supposed to
be best costume -- not sluttiest outfit. All of the guys are like drooling
over her, even Timmy - that bitch!"

I finished. Pulled on my panties, adjusted my stockings and skirt and left
the stall. When I came out -- the conversation went silent. Karen was just
standing there with a knowing smile and shot me a sly look. I went to the
mirror and looked at my hair, touched up my lip stain, adjusted my breasts
slightly and turned to the girl that apparently called me a bitch and said

"Honey, I am not interested in your boyfriend. I am just here to win a
thousand bucks."

I turned and walked out. Karen immediately came up to me, kissed me on the
cheek and said

"Welcome to the more catty side of women. Promise me, though -- No cat
fights tonight."

We both laughed. Gosh, I was having fun with her.

As the night progressed -- I got up and I sang `Man! I feel like a woman!'
and I got a standing ovation. More drinks. Hugs from guys. Yes, again --
some guy tried to grab my ass. I guess I was finding out what it was like
to feel like a woman. Karen was videoing things.

Needless to say -- I, or rather, we won the $1000 first prize. On the way
out, Karen mentioned she had met someone who told her about an after hours
and invited us. I was feeling no pain and neither was Karen. She said she
would like to go just for an hour or so. Karen had been so wonderful all
day. So I agreed. We got back to the car and she helped me touch up my
makeup.

We got there, it turned out to be a fraternity at another school. I was
somewhat uneasy about this, but I could fake it for an hour or so for
Karen. Especially after everything I had been through today. When we
entered, it was your typical after hours. People, music, drinks, pot
smoking. Many of the guys were looking at us as we came in. No sooner did
we get in the door and Karen whispered in my ear

"Your bulge again".

She escorted me upstairs and walked down a hallway that headed toward a
bathroom into a vacant bedroom. We entered and she closed the door behind
us.

I asked

"What are you doing? Here?"

She told me to trust her as she sat me on the bed and rubbed my crotch. It
had been hours since my last blow job and I was eager. She produced a
blindfold from her bag, put it on me, whispering

"Have I disappointed you yet? Trust me"

as she tied it. Once blindfolded, she rubbed my crotch again. Next thing
-- I heard an unusual noise and she did something to my ankles. I felt her
take me wrists and guide them down between my legs. All of the sudden I
heard this clicking sound and felt something on my wrists. I could only
sit up partly. My wrist were secured some how. Next she started to give
me a deep French kiss, she stopped momentarily. As I groped for her tongue
and lips with mine, I received something in my mouth and I felt her pull
something tight behind my head. I thought -- What the heck??? I felt her
go between my legs, go under my skirt and pull down my panties and started
to blow me yet again. Again I came quickly. However, without the visuals
-- it wasn't as exciting.

I could feel her replace my panties adjusting my cock. She pulled back
down and adjusted my skirt. I think she got up and did something in the
room for a minute. I could hear occasional noises and I started to wonder
what was going on. Why wasn't she undoing the restraints? Did she pass out
or something? Did she have that much to drink??? I tried to talk, but
could only produce muffled groaning sounds with whatever was in my mouth.
Finally she came back and removed the blindfold. I looked and discovered I
was directly across from a bureau with a mirror. What the??. What was
this?? There I was ankles handcuffed together with a bar separating them
and my wrists hand cuffed to that by a chain. I recognized this -- we used
this gear a year or so ago during one of her bondage sessions. In my mouth
was a big red ball secured by a strap around my head. I shot her a
quizzical look.

She then took more things from her bag. What the hell was going on??? Why
isn't she undoing this stuff??? Out came red ribbon or sash like a beauty
queen in a pageant would wear. She held it up so I could see -- it read
`Happy Birthday' in large glittery letters. I immediately thought -- who's
birthday? My birthday was in the spring and hers was in January. Again I
gave her a puzzled look. She fastened the sash around me and said nothing
as she carefully adjusted it. I struggled with the cuffs to no avail. She
looked at me and told me that I might as well not even try as it was very
secure. Besides, if I made too much noise people would come look what was
going on. She looked at me and said

"Perhaps tonight you learned a little what it is like to feel like a woman.
Well, Jamie, now you are really going to get a good taste (-giggle-) of
what it is like to feel like a woman."

I started to feel very vulnerable and frightened. She wasn't sounding like
this was some kinky game of hers. Next, she pulled out what looked like a
greeting card from her bag, opened it and started to read.

"Happy Birthday Nick! I know I haven't been in touch with you lately, but
I wouldn't forget your birthday. I had a friend hire a hooker for your
birthday present. She is paid for an hour. She will blow you and as many
of your friends as you can fit into an hour. She takes a while to warm up,
but she can swallow as much as you can feed her. Again, Happy Birthday --
Jake"

I was getting scared now. She knelt down looked me straight in the eyes and
said

"Jamie - uh, I mean Shania (-giggle-). I promised you many blow jobs in
your night. This is totally true. What I didn't tell you was that you
would be giving the majority of the blow jobs!"

Terror rushed over me. I started to struggle and tried to yell. It was
fruitless.

She told me that she recommended that I do a good job or they might think
something is up. If they were to reach under my skirt they would discover
my little `secret' and might not take to kindly to some `gay' guy duping
them like this and would probably beat the crap out of me. She told me to
think back on what I learned during my little dildo sucking lesson and to
`Practice, practice, practice'.

She bent over and whispered in my ear

"Shania dear (-giggle-), Man! Are you gonna feel like a woman!"

and she started to laugh loudly. With that she tucked the card into my
bosom and exited leaving the door wide open.

Oh my god! What had she done? This couldn't be happening. Looking in the
mirror just brought me back to reality. Seeing as the bathroom was at the
end of the hallway it would only be a matter of minutes before Nick's
birthday present was found. I was about to become a fraternity house boy
toy unless I did something quick.

I franticly studied the shackles. They were locked and very secure -- this
was not some cheap piece of crap -- these were real handcuffs and very
solid. The chain to my wrist was some how wrapped around the leg of the
bed. Maybe if I got that free I could do something. I tried. I stood and
lifted the bed. When I did the chain to the wrists lifted as well. Damn!
Try it again! More carefully. I looked and struggled in vain. Nothing --
It wasn't even close to coming off the leg of the bed. Even if it did.
What then?

Oh my god, I could hear voices coming now! The voices stopped. I looked
and struggled again. Where was the damn key!?!? I heard one of the voices
again! Closer still! NOOOO!

A tall skinny guy walked past the open doorway, did a double take and for a
brief second I thought he would walk right by and then he stopped came back
and stepped into the doorway.

"Hello there Shania honey! I saw you come in. Looks like you made
yourself right at home. Happy Birthday, huh?"

He took the card that was tucked into the top of my dress, studied it for a
second then he yelled down the hallway

"Hey guys come take a look at this! Hey, someone get Nick!"

My heart sunk. I was about to learn to be a woman.

In the matter of seconds, the doorway filled and then they started flowing
into the room. There were at least a good dozen that I counted. Then I
heard someone say

"Hey, here comes Nick!"

He entered with Karen's friend Mary at his side. I thought -- was she in
on it too? She took one look at me and just started smirking. She
definitely recognized me. It looked as though she was trying to keep from
laughing and she looked away. I could tell she wanted badly to laugh, but
she contained herself. Oh please, let this be a bad joke that Mary ends
right here!

The tall skinny guy gave Nick card and explained how he discovered me.
Nick opened the card and read. A smile grew across his face.

"Hey guys! Listen!"

and he proceeded to read it out load for everyone. At the end he announced
--

"Blow jobs for everyone!"

My heart sank. Panic swept over me.

The group of guys cheered, hooted and hollered. Nick made some comment
like

"Jake is one hell of a brother, man!"

Mary suggested

"Hey, why don't you wake up all the guys. Might as well get Jake his
moneys worth."

She looked at me and smiled. Oh great! There weren't enough here
already!!!! She made a comment like

"Well, I don't need to hang around for this. Happy Birthday Nick"

and pecked him on his cheek. She headed toward the door, stopped and said

"Hey, why don't you give her a real `Trick or Treat' and pop her up the
ass!
What is she going to do? Tell the Dean? Well, you boys enjoy your NIGHT
FULL OF BLOW JOBS."

Hearing that let me know she was DEFINITELY in on it -- those were the
exact words Karen had used. She said good night and started to leave. On
her way out she looked back, made a blow job motion pretending she was
pumping a cock into her mouth and bulging her cheek with her tongue,
stopped and blew me a kiss, winked and smiled -- walking away shaking her
head and chuckling. No one saw anything though. They were all gawking at
me. Drooling! Eager to have the sultry slutty looking hooker dressed like
Shania Twain blow them.

They started to converse amongst themselves what to do and how to do it.
Everyone agreed Nick should be first. He came over examined the ball in my
mouth and removed just the ball leaving behind something that held my mouth
wide open. I felt terror rushing over me. Oh my god -- I am going to be
forced to suck a guys dick. I shook my head and tried to say something.
Nick pulled back and looked at me puzzled for a second. He dropped his
pants and underwear and there I was -- face to face with a partially erect
man's penis. He told someone to hand him the card he placed on the bureau.
He produced a key from it that apparently had been taped to it. Oh please
Lord -- let him just turn me loose and let me leave. He leaned down and
said

"I'm gonna undo your hands here. If you do a good job, we might loosen
more of them."

With that he undid my hands from the chain that tied them to the bar
between my feet. My hands were still cuffed together as were my feet, but
I could use my hands at least.

He came toward me again. This time I put up my hands to push him away. As
he push toward my mouth with his cock, I reach out and accidentally gently
grabbed his cock -- it was fully erect now. He didn't hesitate. He came
right at me and started to guided it into my mouth. No! Please No!

I have never sucked another mans dick before. He pushed forward and
entered my open mouth. I could feel the warm head of it in my mouth. He
groaned slightly. He pushed harder. His cock slid into my mouth further
still. The warmth and velvet skin as it slide over my tongue was strangely
-- I don't know - pleasant. He pushed forward as his cock slid further
down my throat. He stopped and pulled out till the head was all that
remained in my mouth. He groaned. Back in a again.

"Oooh, baby your mouth feels great."

I heard the voices of the others

"Yeah!" "That's it" "Take it all"

Out again. I looked up. He stopped and reached behind my head and removed
the ring that held my mouth open.

"Can't suck too well like that can you???"

Before I knew it he was in my mouth again.

I didn't know what to do. He commented that I didn't seem to `interested
in my work'. I thought that I better do something -- I better start
pleasing him. I grabbed his sac and started to fondle his balls.

"Ooooh!"

When he pulled out I grabbed his cock and held it as the head was in my
mouth. I started to lick the head with my tongue like I had learned in the
dildo sucking session with Karen.

"Oh baby!"

He rapidly slid it in, then out again.

"Oh yeah!"

In and out. The pace got faster. I started to focus on the head licking
all around it and sucking. The motion of his hips combined with my sucking
and they seemed to synchronize with one another. It was as though I was
bobbing up and down on his dick! I began putting a little motion into it.
I WAS bobbing up and down on it!!! I was like some porn star in a skin
flick!! He gently grabbed the back of my head and kept pumping into my
mouth.

I felt him begin to tense and heard him moan deeply. I felt his cock
twitch and I realized that he was going to cum. Panic flooded into my
head. I was going to receive a mouthful of cum if I didn't do something
quickly. I stopped sucking and began to try to push him from my mouth.
His grip held me tightly and after a few deep thrusts he started cumming in
my mouth. In a fraction of a second, his cum filled my mouth. Warm,
slippery, sticky, salty cum. He kept pumping. I couldn't keep up with it.
He kept pumping as his cock twitched again. I didn't know what to do. I
bobbed and sucked. It started to leak from my mouth. I swallowed and
swallowed hard as he pumped. Then the slurping, sucking noises from my
mouth. His pace slowed. The taste of his cum filled every corner of my
mouth. Salty, slightly bitter and warm. I have never tasted anything like
this. His pumping slowed as did his twitching of his cock. I gently
licked him clean. He retreated. The guys were all going

"Yeah!", "Oh man!", "Oooh, she is warming up!"

Oh my god, I just sucked a cock!!!! AND I SWALLOWED HIS CUM!!!! I was too
mortified with the whole thing. All sorts of thoughts rushed through my
head. My mouth felt kinda funny -- never tasted anything like that --
kinda salty and metallic almost. It didn't taste as bad as I thought it
might, but I had enough. I wanted this to end. I wanted to wake up and for
this to be a bad dream. I looked up and they were all eager to be next. I
heard someone say

"That took like five minutes. There are like fifteen of us, we better
speed this up."

Oh my god -- I thought -- FIFTEEN! Someone jumped to the front and put
their dick in my face. I looked up to see the skinny guy. I reached out
with my hands, mouth open. As he pushed forward my tongue greeted the base
of the tip of his cock as he slid into my mouth. He took like two seconds
before he was fully erect and grabbed the back of my head and started to
fuck my face. I wasn't doing much work. He was literally fucking my
face!! I applied some sucking and greeted the underside of his dick in my
mouth with my tongue every time he entered. The slurping, slorking,
sucking sounds again. I looked up at him and he down at me. Moments later
he blew his load. I sucked and swallowed so hard and yet it wasn't enough
it. It started to dribble from the corner of my mouth. I heard someone
say

"This is taking to long. She won't be able to get to all of us."

Too bad I thought.

"Undo her hands so she can work on someone else cock while she sucks one".

I was on another planet. It was too much for me to handle. Being called
`she' -- a prostitute no less, sucking not one cock, but now two.
Swallowing their cum.

Next thing my hands were undone and my gloves pulled off. I worked the
next guy with my mouth and one hand while the next in line placed my hand
on his cock and started to stroke it. I looked up and the audience was
captivated and aroused. I occasionally could catch a glimpse of myself in
the mirror when the view wasn't obstructed by the person skull fucking me.
The red lips, sultry slutty looking eyes, my bosom, red painted nails. I
was watching what looked like Shania Twain giving a blow job to one while
stroking another. I was terrorized with what was going on, but at the same
time captivated with the image.

There was one strange looking k** standing there stroking his own cock.
Right then the one in my mouth started to cum. Then I heard the one I was
stroking say

"Oh, I'm going to cum"

He stepped forward and tried to get into my mouth, but I was late removing
the first from my mouth and he blew his first two jets on my face before I
finally got him into my mouth to receive the remainder of his cum. My
mouth and throat were totally flooded with the two men's cum.

The strange looking k** came up and blew his load on my chin and breasts.
When I finished with the one in my mouth, I reached down, wiped it up with
a swipe of my fingers and licked them as they watched. They seemed to love
it. I similarly cleaned the cum from my cheek and chin lapped it up
without hesitation.

"Oh baby! You love swallowing cum don't you?"

someone said.

One after another, I sucked, stroked and swallowed. One guy the others
called `Big Hank' - he was a big guy, a football player type. When he
opened his pants and I saw that -- I couldn't believe it. It looked to be
about nine inches long and as thick as a beer bottle. I remember thinking
to myself, I CAN'T DO THAT! Initially, I had trouble just getting it in my
mouth. I just sucked the head. He started pushing and I did manage to get
it about half way down. He held my head and moved me to his needs fucking
my mouth slowly then fast all the time getting deeper. I was making a
sound like someone plunging a toilet now. Finally when he started to cum,
he just buried his cock down my throat. I could feel his jets of cum
hitting the back of my throat. I almost gagged but relaxed my throat and
just tried to swallow. As I swallowed, I realized I was actually using my
throat muscles to stroke his cock! I was becoming an accomplished little
blow job artist. I looked up to see him looking down at me and felt as
though he was feeding me his cum. He pulled out as I caught my breath.

The next guy had ordered me hold all his cum in my mouth, I didn't swallow,
I just sucked it and gathered it into my mouth. I had trouble keeping it
all in my mouth and it dribbled from the corners of my mouth. He pulled
out, told me to open my mouth and show it to him. He rubbed his dick
around my mouth smearing his cum all over and shooting one last jet in my
nose. All of the guys giggled at this. He told me to swallow it and clean
him. I did. I was a whore.

This went on seemingly forever. I lost count. The thought of my release
had left my mind. My mind was elsewhere. I was strictly concerned with
`doing a good job' in hopes of gaining my freedom and so that they wouldn't
think that anything was up. I found myself studying what seemed to turn
them on the most. And I `practiced, practiced, practiced'.

We were thankfully nearing the end when Nick came back and told everyone to
leave. I don't know what the final count must have been -- maybe fifteen
like someone had said. He closed the door and gave me a towel to clean up
a little. He asked me my name and I told him in as feminine a voice as I
could manage with my throat having been fucked and painted with cum. I was
hoping that he was going to set me free and that the hour was up.

"Well, one more time Jamie and you are done".

I nodded in consent. I started slowly and gently looking at him. I was
even talking

"Oh baby, Ooooo yeah"

as I kissed and caressed and stroked his cock. I had been working him for
several minutes. He was very erect now and I could feel and taste his
precum. I had gotten pretty good at getting them to cum pretty quickly and
I felt that I would be swallowing his load in several minutes when all of
the sudden he pulled out. He helped me up from to my feet, unfastened the
bar between my feet from the bed post. With that he threw me down on the
bed rolling me on my stomach.

"Jamie, time for a little Trick or Treat lik