A meeting with a woman who has a high heel fetish
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Living The High (heel) Life free porn video
Chapter 1
It had all started about two months previously. Chris had been at his
part time job, at the show store, and his boss, Amy, had noticed that he
was pretty ineffective when it came to dealing with female clients. Amy
had thought that maybe a better understanding of woman's footwear would
inspire Chris to sell better. So she made him an offer, if he would take
home and wear around a pair of heels for the next couple of days, then she
would give him an extra hundred dollars, betting that his increased
effectiveness would offset the money that she had given him.
Chris refused outright at first, but after thinking about the money he
said he would consider it. That night at supper, he discussed it with his
mother and sister, and they said that they would give him some help. His
mother, Diane, was a bit more skeptical. Her husband had left when Chris
was born, forcing her to raise Chris and his older sister on her meager
hairdresser's salary. Her whole life she had worried about Chris having a
lack of male figures in his life, and still at the age of 17, he had never
really filled out as a man. He was still pretty short and not very manly.
Jessica, his sister, on the other hand, was excited about this little
project. Although a year older, she and Chris had been best friends
throughout their lives. Although she was pretty enough she hadn't had
many boyfriends, and she was presently following in her mother's
footsteps. She was finishing off her high school and was planning on
studying to become a makeup artist in the coming year. Chris had chosen a
different route. His marks in school had always been very high and he was
looking forward to going to university in a couple of years. He had been
increasingly consumed by his studies so much so that he made little time
for other pursuits. He was a nice guy and although not very masculine
some of the girls at school had expressed an interest in him and so he had
been on a few dates, though never really had a full time girlfriend. He
spent the rest of his time studying and trying to make as much money as
possible to save for university at his part time job. His only other
pursuit was his on-again off-again membership in the school chess club.
So Chris had decided that he would take Amy up on her offer. The next day
after closing he chose a pair of black matte pumps, with 3 inch heels, and
then later on at night he tried them on. His first attempts at balance
were pretty ridiculous and he got Jessica to show him how to walk and
balance. After showing him for a few minutes Jessica had suggested that
he try on a skirt. It would allow him to feel a bit more comfortable and
also emphasize the femininity of the movement required. Chris accepted,
though not without much deliberation as he didn't like the idea of his
increased feminization. Jessica selected a simple black skirt which went
down to Chris' knee. Chris felt what she had been talking about, he
immediately felt much more feminine and his walking soon became much more
rhythmical. In fact he even started to enjoy it a little bit. The next
couple of days when he was supposed to wear the heels would not be so bad
after all. Maybe he could even make the best of it.
When Chris returned home the next day he found that Jessica had had more
ideas. Diane was working late, she sometimes augmented her salary by
working on movies in the area, doing hair and makeup for the actors and
actresses. Diane was going to be working late for the next while and so
Jessica and Chris were mostly home alone. Jessica had gone out this day
and bought a couple of pairs of panties. She argued that as Chris was
wearing just men's underwear under his skirt that the full experience was
still being lost. Again Chris was hesitant to the idea but Jessica
persuaded him. As she explained panties were not much different than
regular men's briefs. Also, she said, this would force him to think of
the modesty that women have to always think of. So Chris begrudgingly
accepted. When Jessica next brought out a pair of black tights for Chris,
explaining he could put them on if he was getting cold sitting around the
house, Chris said thanks but had no real intention of wearing them. But
as he was sitting around later he noticed that his legs were indeed
getting cold and so he thought that trying on the pair of tights would not
really bother him, so he decided to give them a try.
When he slipped the thick nylon up his leg, he felt shocks go through his
system. These were so comfortable and they were so sexy. Chris felt
himself getting hard in his panties and immediately went and masturbated.
These tights felt absolutely amazing to him. A few minutes later he went
to Jessica asking if he could try on different pairs. She agreed that he
could, but she said she mostly had pantyhose and that his legs would look
much better if he shaved them first. Chris thought about it for a minute,
there was no reason that shaving his legs would be bad, it was October and
there was no reason to wear shorts outside anymore. No one would notice
that his legs were shaved. So with a bit of advice from Jessica on how
shaving legs differed from shaving one's face, he went off to take a bath
and rid his legs of hairs. The next couple of days after school and work
became ones of exploration for Chris. Jessica was very close to the same
size as Chris and she didn't mind if he tried on her tights and pantyhose.
So Chris experimented with all her different types and colours. He tried
the thick wool ones, barely there black shades, ones with funky colours
and designs and so on.
It was after trying on a pair of white pantyhose that Jessica had pointed
out how sexy white pantyhose look when the toenails are painted red. By
this point Chris was no longer hesitant about any further feminization
when it came to his legs. He let Jessica pick out a deep red colour and
then paint his toenails. He rationalized this the same way that he had
before. No one would ever see his nail under his shoes and socks at
school of at work. The feminization of his legs was done. Over the next
few days Amy asked if he was going to bring back the shoes. Chris asked
if he could borrow them for a while longer. Amy agreed and told Chris
that he could borrow anything else as long as they were not the only pair
of shoes left in the store. So after looking around Chris found an extra
pair of knee high boots, some red pumps with 3 inch heels, some strappy
sandals also with 3 inch heels and some stiletto heels with 5 inch heels.
Arriving home that night, still with his mom working late nights, he found
that Jessica was a little upset. One of her friends had gotten sick and
another couldn't some over. She was supposed to have done a makeover on
either one of them for her co-op class the next day, and without them she
would fail. Chris told her that it was too bad that he couldn't stand in
for them because he would like to help. But as he mentioned it Jessica
liked the idea. She assured him that if he let her make him over that he
wouldn't look bad, she could use her skills and highlight his natural
feminine features and draw away from his masculine ones. Also she said
that she wouldn't tell her teachers about who she made over and that these
pictures would never get out. After some begging and pleading Chris
finally gave in. To get himself in the mood he first put on his skirt,
panties, pantyhose and black stilettos. Not good enough Jessica told him.
He would need to look more like a girl. So she sent him off to the
bathtub to shave the rest of the hair off of his body. She would lend him
one of her dresses. Coming out of the bathroom about a half hour later
Chris found a dress and bra on his bed. The dress was one which covered
his whole top half but was rode fairly high on his leg. He suspected that
he was going to have to wear the bra and so put in on without much
thought. As he came out of the room Jessica stood there. In her hands
she held a pair of ankle high pantyhose, which she had filled up with some
rice, to simulate some breasts for Chris.
After she positioned them for Chris, he went to sit in the hairdresser's
chair in the basement. Diane also sometimes saw her clients at home, but
as she was away at her toher work so frequently, this mainly became
Jessica's area for praticing. Jessica came in with a dark curly haired
wig and some clip-on hoop earrings. After putting them in place she
looked at Chris and noted that any need for anonymity was not required.
He already looked nothing like a guy and her makeup would only help to
hide his secret. Sitting with his legs crossed Chris settled into the
chair and after about an hour of careful makeup application Chris finally
looked at himself in the mirror. Gone was the gawky teenager. Now in
front of him was an attractive young lady, looking like she was ready to
go to her prom.
Chris was immediately very aroused. He thought of how sexy he looked and
wished he could have a woman this amazingly beautiful. But now he was
this amazingly beautiful woman. What before had been a passive adventure
now became an active one. Chris loved the way he looked and wanted to
keep it going. Now it was him who was doing the begging. He begged
Jessica to take him out in the car and go to a fast-food restaurant. He
wanted to see what guys would think of him. Jessica at this point feared
a little bit for his safety and thought that maybe she had gone too far,
but Chris reminded her that he had done a favour for her so now she owed
him a favour. Jessica agreed and told him that she would need about half
an hour to get ready, so that she wouldn't be outshone by her brother.
After about 40 minutes Jessica came back with a short skirt and some red
tights. Her makeup was immaculate and they both felt like a couple of
girls going out on the town. They went to a nearby restaurant and Chris
felt immediately more powerful than he ever had. There were a lot of guys
looking at his sister, but then there were also a lot of guys looking at
him.
Chris was now intent on trying out more and more stuff as a woman. Diane
continued to be working late and Chris took as much advantage of this as
he could. He began experimenting with all of Jessica's clothes, from
jeans to miniskirts and sweaters to tube tops. About five hundred dollars
spent on the internet returned everything else he needed. Special panties
designed to hide any appearance of his penis, a special bra like device
designed to simulate cleavage and breast forms all rounded out the
physical needs. Jessica and him made a few trips to some second hand
stores and picked out some cool clothes for him. Jessica spent all he
free time with him trying to teach him small makeup or hair tricks and the
two painted each other's nails. Also Chris worked hard to get his voice
sounding more feminine. He was not sure where he going with this but for
the time being he was happy pretending to be a woman.
Chapter 2
This coming weekend for Chris was going to be a special one. He had told
Amy everything and asked if he could come into work on Saturday dressed as
a woman. After some deliberation, and seeing Chris dressed completely and
talking like a girl she agreed, but Chris would need a new name. Without
much thought, they had come up with Christine. By now Diane was nearing
the end of her film work, but she was still going to be working for the
next weekend. Jessica had also made plans with her friends for Friday
night. After spending almost all her time with Chris in the past two
months her friends felt as though she had been ignoring them and so she
agreed to go out. And so Chris was left alone that night. Diane was
adamant that her children not have tattoos and the two of them respected
this, but the previous night they had painted some henna tattoos on each
other's lower back and a floral pattern around each other's ankles.
Jessica also pierced Chris' belly button. He was looking more and more
feminine every day.
So it came that on Friday Chris was home alone. He figured that other
that studying and acting like a girl in the past couple of months that he
had not had chance for any of his other pastimes. So after getting
completely made up he settled in front of his video game player and put in
one of his usual favourites. He had chosen to sit around in some racey
clothes. He had just bought a little black dress that he was eager to
wear around. Underneath were some thong panties with a black garter belt
and some thigh high stockings. His toenails were painted red and so were
his fake acrylic fingernails. Again he was wearing hoop earrings, though
these ones were regular earrings. He had gotten his ears pierced a couple
of weeks previously and he was still getting used to the feel of them. He
wore some sexy makeup, red lips and smokey eyes with some fake eyelashes.
Although he lacked real breasts the device he bought allowed him to make a
fairly convincing allusion. Really he looked like a girl ready to go out
for cocktails and not someone that wanted to play video games on a Friday
night. At first he realized the game play would be a bit more difficult.
He was not yet used to using nails, and the game controls were such that
even with no nails it was hard to master. So he decided to give up on
gaming and instead put in a movie.
It was not long until he fell asleep. He had been very busy recently and
not noticed how fatigued he had been. Without noticing that he had gone
to sleep, he did notice when he woke up, to the sound of a male voice
-Chris is that you?
Chris bolted upright. It was his friend Dave. He had met him a couple of
years ago in the chess club when Dave was a senior in high school and he
was still a sophomore. They had become friends and Dave came over
regularly to play video games and hang out. Dave was not a very
attractive guy. He was fairly big and awkward and had not been very good
with women as Chris had remembered. He hadn't stopped by in over a couple
of months. He was usually off at university in a nearby town, but
apparently he was home for the weekend. Chris knew that no matter how he
tried to explain this, that it would be impossible to explain it except
with the truth. So instead he chose to modify the truth.
-Yeah, hey Dave.
-What are you doing dressed like that?
Chris explained it very logically and told Dave exactly the circumstances
leading up to the transformation. But instead of happening a couple of
months ago, it happened last night and this night. Rather than liking it,
Chris explained that he was being heavily reimbursed, by Jessica, who he
said would be back soon, though really she wasn't
-Well whatever I guess. I mean it is pretty strange but as long as you
are getting something back for it. When is Jess going to be back?
-I don't know she just went out to give something to mom. She will
probably be back any minute.
-Well that's all right, this can just be our little secret. I decided to
come home at the last minute for the weekend but found out that my parents
had already made plans to be out-of-town. So I figured I would swing by
here and see if you were up to anything.
-I just fell asleep after watching a movie
-Any new video games?
-No just the old ones.
Chris was a little surprised that Dave was not very disturbed by the way
he was dressed. It had the effect of putting him a bit more at ease.
-Well do you mind if I stick around and play some? You want to play a
fighting game?
-I can't really because of my nails, I tried earlier, but couldn't quite
master it. But if you want, you can play, I will jut watch.
-OK sure thing.
Dave put in their regular fighting game and chose one of the female
characters.
-If you are going to be a woman tonight so then maybe I can too
Chris laughed a small laugh and starting watching Dave play. After a few
rounds Dave started to get a bit exasperated.
-Man it has been a while since I played I'm rusty.
-Maybe we should just watch some tv.
-Sure
Chris got up and switched on the TV
-I guess you know, seeing as you are a guy underneath there, that you look
very hot tonight.
The compliment touched Chris, but he pretended that it hadn't
-Thanks I guess.
They started watching some random action movie that was on the television.
-That's a pretty cool tattoo on your leg, is it real?
-No its temporary.
-Do you mind of I have a closer look?
-Uh sure I guess
Chris lifted up his leg for Dave to see. He was surprised when Dave
grabbed onto it. He could feel impulses run up his leg like shocks of
electricity. He got as hard as his underwear would allow.
-That's pretty cool.
Shocked and embarrassed, Chris replied thanks.
They continued to watch television for a few more awkward moments. When
the commercial break came on, Chris got up and went to the bathroom. He
didn't know what he wanted, but he knew what he needed, and that was to
orgasm right away. He was so excited it did not take long to cum. His
body shuddered with pleasure and he got himself ready to go back out.
When he got back he realized that he had not even missed any of the show
he had been so fast. After sitting for a minute Dave reached out and put
his hand on Chris' leg. Chris looked at him and saw that Dave wanted him
too. Dave leaned in to kiss Chris and as there tongues met Chris went
crazy. He moved over and straddled Dave and started grinding against him.
Chris could feel Dave getting hard through his pants. The idea of sex
with a man had never even occurred to Chris in his new womanly role, now
it was all he wanted. As they were making out Chris stopped for a minute
-Do you think you could call me Christine?
-Sure
So Christine and Dave started becoming hotter for each other. After a
couple of minutes Christine reached her hand inside of Dave pants. She
felt his warm hardness in her hands and wanted this in her mouth. She
undid his zipper and pulled down his pants. Dave was extremely well hung.
If he were better looking he would be able to have any girl. As it was
Dave's massive hardness was all hers to play with. She licked the head of
his penis and then began bobbing up and down, her long red fingernails
working his shaft where he mouth had just been. She worked her tongue
around the head of his penis and listened to him groan in pleasure. The
hair from her wig was being held back by Dave, but her hoop earrings
followed her movements back and forth and hit against her neck to give her
yet another reminder of what she was doing.
She felt Dave's legs and then ass muscles start to clench up and she knew
what was next. She tasted a little bit of pre-cum and then seconds later
her mouth was full of his semen. She looked up and smiled at him as she
swallowed. The taste was nothing like what she expected, it was not a
pleasant taste, but she swallowed anyway, eager to please.
Dave grabbed her and pulled her back up towards him. He buried his head
up her dress and pushed her thong panties aside and started to lick around
her asshole. Christine knew what would be coming next and waited
impatiently. On the couch Christine got on her hands and knees and
prepared for David to enter her. When he pulled his head from her dress
he then lifted up her dress around her waist. The initial feeling of his
hard penis against her rim felt nice, but the next part, s he pushed in
deeper, was not so nice. Christine pulled back in a bit of pain.
-Is it OK to go on?
-Yes just take it slow
-Are you sure?
-I just want you to fuck me, get on with it.
With this prodding Dave did not take it slow. Instead in one movement he
pushed inside Christine. She let out a small whelp, but now that he was
all the way inside her she knew his would be as much as she would feel,
and while there was some pain, she also enjoyed the feeling very much of
having his hardness inside of her. Dave began a rhythmical motion, and
Christine ground her hips against his perfectly to maximize the pleasure.
Christine looked down her body. She saw and felt her hair hanging and
following the swaying of her body, her red nails were on the surface of
the couch holding her up. Her eyelashes were just a little weighed down
by the feeling of her fake eyelashes and mascara. Underneath her dress
appeared to be two perfectly shaped breast, rocking back and forth as well
with their every movement. Further down, past where Dave was inside her,
she could feel her nylon stockings and she felt her high heels trying to
find a place on the couch to push back with.
After a few minutes what had seemed like Dave's hardness got much bigger
and each thrust carried a bit more pain but a lot more pleasure. As she
felt Dave tighten up again, she knew he was almost ready, and he came
inside her. She collapsed on the couch, with one of Dave's huge loads in
her ass, another one down her throat. Dave collapsed with her and settled
in beside her on the couch. He pulled her dress back down and held her in
his arms.
-Jess wasn't really coming home soon, was she?
-No she will be gone for a while still.
-You know I wanted to fuck you from the moment I walked in the door?
-I didn't know what I wanted before, but I know what I want now.
-You took my virginity tonight, Christine.
-You took mine too Dave.
As the two of them lay there and caressed each other and talked, Dave said
that he had always felt something different for Chris, now Christine.
Christine was flattered but still a little confused. After some time, she
asked if Chris could leave, but she also said that they could meet the
next night for some more fun, at Chris' house.
Christine got cleaned up. Her ass was still throbbing with pain, but she
still felt a sense of euphoria. She decided to leave Dave's cum inside
her as she slept. She went to sleep, still wearing her acrylic nails.
She would be wearing those the next day at her work.
Chapter 3
The next day at work, Christine was in a great mood. She was completely
fooling everyone. She had chosen a knee length skirt with some over the
knee boots with long heels. Underneath she wore some red tights. On top
she wore a black sweater with a plunging neckline, exposing her seemingly
real cleavage. Throughout the day she dealt with numerous customers, most
of whom, she thought, were a bit surprised at her lower than normal voice,
but she was sure she was fooling all of them. More so towards the end of
the day a guy had come in looking for shoes and he was flirting with her.
Her ass was still sore from the previous night and it affected the way she
walked. In fact she seemed to think she walked more like a woman now than
before. By mid-day her feet were killing her. Wearing these heels
required a high pain tolerance she realized. She all of a sudden had a
greater understanding of what it means to be a woman. Here she was, still
sore from last night's pleasure, yet she was expected to be well put
together. She was sure that Dave was at his home right now, not looking
anywhere as good as she was, and even though she knew she was exerting a
lot more effort, she still liked the way he made her feel, warm and
protected. She couldn't wait to see him again tonight. She was going to
go to his place after stopping by her home and expected a second round of
fun.
Amy commented half way through the day that Christine seemed to be very
happy. Amy was still a little uneasy with the whole situation. She felt
as though she had played a large role in turning Chris into Christine, and
so Christine didn't mention the real reason she was so happy ? it was
because she had lost her virginity the night before, not in a way that she
could have ever expected, even yesterday morning. While most guys who
lose their virginity feel more like men, she felt more like a woman now.
She was eager to experiment more and feel alive again.
Amy decided to close for the day and sent Christine home early. Christine
swung by her place and didn't expect to be long. She was going to just
freshen up her makeup and put on some perfume. Instead when she got home
she found Jessica there.
-How was it last night Chris? And how was your experiment at work today?
Christine debated whether to say everything, nothing or just a little.
She thought she would start by addressing her work and hope Jessica forgot
the rest.
-Work was good, Amy says that I probably fooled everybody
-Of course you did, looking like that, you want to me tell me about it?
-Well, I can't, really. I am meeting someone.
-Oh?
-Yeah Dave is in town.
-And you are going dressed like that?
-Actually he stopped by last night and caught me completely off guard.
-Oh so he saw you? Well how did that go?
-Seriously?
-Yeah of course
-You won't get mad?
-Why would I?
-Well we made out.
Jessica stepped back
-Really?
-Yeah
-Wow now you really do have to tell me everything.
-Can it wait Jess?
-I guess, but don't you think you are rushing things? I mean you are
probably pretty confused right now. I just started this with you because
I was looking to bond with you in a different way. Now you are making out
with guys. I mean I didn't want to turn you gay or anything.
-Like you said it was you that helped to put me on this path, and for now
I am just enjoying it. I feel more alive as a woman than I ever did as a
man. And I think most of all you want me to be happy right?
-Well of course, Chris. So what did you do with him? Just kiss him a bit?
-We did more than kissing.
-Oh, you didn't, like, go all the way, did you?
Chris looked away, Jessica could tell he didn't want to answer the
question. Jess was immediately taken aback, and knew the truth.
-Oh wow! I don't know what to say.
-You aren't mad?
-No, just shocked. I mean you wouldn't have done this if it weren't for
me.
-Yes, but that's a good thing Jess. Haven't you had sex with a guy
before?
Now it was Jessica that didn't want to answer. Chris knew the truth
immediately, that despite her lack of boyfriends that she had been with a
man. Finally she responded
-All right, yes I have. Johnny and I ? uh ? last year after the junior
prom.
-Was it good?
-I was a little drunk.
Christine was surprised to hear that Jessica drank at all, let alone was
drunk.
-But was it good?
-It was pretty amazing
-So why is it any different for me?
-Its just I always imagined my little brother would bring home some girl
some day.
-Your little brother brings home a girl everyday. She is a part of me
now.
-OK Chris I can understand that. Are you happy?
-I feel more alive than I ever have today, and it has to do with me being
a woman, not anything to do with me having sex last night.
Jessica moved towards Chris and gave her a deep hug.
-OK well you have my blessing then. Just let me know when you get home
later we can have a talk
-OK will do big sis
-OK little sis, have fun tonight.
Chapter 4
The previous night had been as amazing for Christine as the first one.
While the innocence of the first night had worn off, Christine and Dave
made up for it in experimentation. She had been on top, both facing him
and facing away, and also let him fuck her from behind and while she lay
and he stood. She couldn't believe that Dave could cum four times in one
night. By the end, her ass was almost numb from the pain, which really
made the experience much more pleasurable. While she was sure that she
would be very sore the next day, while he was thrusting inside her toward
the end all she could feel was pleasure. When she came home Jess was
still waiting up for her. The two talked about making love, about feeling
a man's hardness inside them and compared the feeling. While Jess knew
her's was much more of the natural biological feeling, she didn't take
anything away from Chris'. The opposite in fact, she was jealous that he
could feel so amazing in this way and not be a woman. She was also a
little jealous that her little brother had had more sex than she had
either.
Chris was willing to help her out though as much as he could. She was
going to try and stay faithful to Dave, who promised to come home as often
as he could, which would be about every three weekends. But Chris said
with her help that the two of them could go and meet guys and find a nice
guy for Jessica. The only ongoing problem would be Diane. They had as
far been successful in hiding almost everything from her. She had been a
little suspicious upon seeing Chris' pierced ears, but other than that she
had no clue what her son was wearing or what he was doing.
End part 1
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