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But Who Am I Really? 3 7
Hugh stood outside Nordstrom's. He looked at it. It was big... and full
of women's clothing.
"OK, let's go." He bravely started towards the door, but stopped,
turned around, pretended to whistle. "This is ridiculous, let's just do
it." It was worse than the time he had tried bungee jumping. At least
there, it was pretty much out of your hands - just strap yourself in
"So here goes," he thought again, "I'll just strap myself in..." a
curious metaphor considering what he was about to be strapped into,
"... and jump!" He pushed open the door and headed towards the
information counter, which directed him to the shopper services office.
"Hi, my name's Francis N. Way, but everyone just calls me Fenway. My
goodness, it looks like you've come to the right place. And what's your
"Hi, uh, Fenway. I'm Erin. Actually, I've just come for a business
"Nonsense Erin, anyone with a figure like yours who comes to this store
with jeans and a loose shirt should realize that it is a crime against
nature and art to be dressed like that. Let's get started."
After a quick measurement, Fenway took Hugh on a complete tour of the
store. As they went through each department, Fenway kept up a constant
running interview, asking Hugh questions about his likes and dislikes,
colors, fashions, where he was from, what he had worn in the past, how
he had got to this awful state of dress.
Hugh did his best, running after Fenway, he tried to answer as many
questions using Erin's past as he could, but inevitably wove in a good
deal of his own background. He explained that he had found a new
boyfriend, and that this boyfriend was paying for the shopping spree.
She showed her a blank check that he had signed ahead of time, and some
credit cards for verification.
"Oh, don't worry about that, dear. We get wayward children here all the
time. My recommendation is that you take a deep breath and enjoy it."
Fenway snatched a blouse from the rack and held it against Hugh.
"Definitely cream with that red hair."
At this point, Fenway was snatching clothes off racks left and right.
By the time they had finished, they both had armfuls of clothing, and
Hugh had seen every single department: casual, suits, sports,
eveningwear, formal wear, coordinates, business wear, sleepwear, and
lingerie. He was exhausted at the variety and breadth of clothing he
saw - now that he had been dragged through the other 90% of the
Fenway stopped one last time. "I hate to ask. I notice you're wearing a
man's shirt. Are you wearing men's underwear, too?"
Hugh blushed beet red, and looked down at the floor.
"Oh my goodness." Fenway couldn't help but smile. "Well, these are on
the house. And we'll also be needing these, these... and these, and
your bra size?"
Hugh knew this. He had looked it up on Erin's bra before he entered the
"... and a pair of these, and let's try these on, just for fun, OK?"
They arrived at the dressing rooms where Fenway hung everything up.
"Now dear, we need to get serious. What is your upper limit? Should I
try and maintain a budget?"
Hugh thought about it. It's my money, he realized, I can spend it
however I want. And it's not like I'm doing this solely for myself,
it's really a present to Erin, for when we switch back. Hugh thought
back to Fenway's comment about "a crime against Nature and Art." He
couldn't have agreed more, since Erin's body, of which he was the
current custodian, was a masterpiece and he was sure it would look
exquisite in the right clothes.
Hugh came to a decision. He looked up at Fenway and grinned. "Sky's the
And then Hugh tried on every single piece of clothing they picked out,
for over four hours. Each time, Fenway would analyze, using subtle
suggestions to teach Hugh about color coordination, patterns, figures,
and fashions. He discovered that absolutely anything could be
fashionable and look good, as long as it was worn at the right time
with the right accessories. Hugh had always fancied himself a
connoisseur of the fine arts and art history, and he found concepts
from art interwoven with fashion in ways that he had never imagined.
For example, the way that a look has a goal, or an emotion, or an
atmosphere, and the way that all components contribute to the look, and
how things that he would have never worn in a million years could look
just right together.
Each time he came out with a new ensemble, Fenway would come back with
more to try on.
"How do you do it, Fenway? I'm exhausted just watching you!"
"Comfortable shoes," was her reply.
Each time Hugh came out of the dressing room, Erin's body, *his* body,
at least temporarily, looked better and better. Fenway was getting
closer and closer to finding Erin's ideal colors, fits, and styles.
"I can sure tell that you grew up on the farm. Look at this skin!" Hugh
looked down. He was dressed in just a silk bra and panties. He had
gotten over his embarrassment of being naked in front of Fenway over
two hours ago. "It's radiant. And you really don't know how to do your
hair up? Too busy shearing sheep?"
Fenway spent a second showing Hugh how he could pull his hair into a
business-like bun. "It can look prudish, or it can look sharp. It all
depends on how you finish it off. Here, let me show you." As she worked
Hugh's hair, she continued, "and some go all the way with a pair of
non-prescription glasses, just for the looks. Normally, I would
consider it a sin to hide those stunning green eyes, but your face is
so arresting that it might be a good idea."
Hugh was in heaven. Janice from the Bagel place had been absolutely
correct, Hugh liked feminine things. His delight, which increased
beyond measure as he tried on each ensemble, proved it beyond a doubt.
Unlike every single shopping trip he had done as a man, this one wasn't
tiring at all, but fantastically energizing. And Fenway was wonderful,
with just the right combination of critical eye, honest suggestion,
gentle cajoling, and appreciation of beauty.
And as Hugh watched his reflection in the mirror, he saw aspects of
Erin's body revealed that, at times, nearly took his breath away, and,
at other times, caused him to dissolve into giggles of delight. Like
the curve of a bare neck or shoulder, an ear highlighted with just the
right earring, a pair of pert eyebrows peaking up over her business
glasses, an incredible waist, and astonishingly long legs. But he saw
something else which he couldn't quite place a finger on. Something
about Erin that he noticed as he tried on each ensemble, starting with
casual knits, sweaters, light skirts, cool summer dresses, shocking
halter tops with bare midriffs, one-piece dresses for casual affairs,
sharp business suits, other, more casual, business clothes, more formal
dresses, and finally a stunning and expensive evening gown for a formal
Hugh nearly fainted when he saw the price of the last item: $1,800
Fenway looked down at her gasping customer. "It's a lot, I know. But
this is *it*. This is the dress that goes beyond just displaying your
best assets - of which there are many, I might add. This is the dress
which defines you as a woman."
Hugh had to agree. He didn't know exactly when he (or Erin) would be
able to wear it, but he had to have it.
And last came the bill: $4,300 dollars. And that didn't include the
$400 he spent on shoes.
- - - - - - - - - - - - - - - - - - -
The bedroom looked like it had been worked over by the FBI. Clothes
were everywhere, dr*ped over everything. Erin walked in and just stood
"What's happened here?"
Hugh jumped up, surprised. "Oh!" He had been trying on different
combinations of skirts and blouses trying to decide what went with
what. "Hi. Ummm, how was your day?"
Erin just stood there. "Hugh?"
"Well, I guess I went a little overboard. I had such a good time! I
couldn't believe it! Oh, Erin, I wish you had been there! Here, let me
Hugh went though each and every sweater, blouse, jacket, skirt, suit,
and accessory. He actually tried on most of the outfits and modeled
them, runway style, for Erin, who applauded and praised Hugh as much as
Erin was astonished. "Hugh, I suggested that you go and shop for some
clothes, but I never thought...."
"Oh I know, but Fen was so incredibly helpful..."
"Oh, my personal shopper! But wait until you see this formal gown I
bought, it's out being tailored, but when you see it you'll just die!"
Hugh stopped and saw Erin looking away.
"Erin? Are you OK?"
Hugh sat down on the bed next to Erin and hugged her. She was crying.
"Shhhhh, baby. What's the matter?"
"Oh Hugh!" Erin sobbed, "I want to shop for clothes! I want to have my
own personal shopper!"
"Oh, sweetie, you can! She assists men too! Just set up an appointment
and get a spiffy new suit, or a new tuxedo, or something."
Erin sniffed, "It's not the same."
Hugh hugged her, "I know. But maybe it will be close enough. Have you
enjoyed being a man?"
Erin looked at him, through her sniffles. "I guess so, I mean, everyone
treats me so well, I like working on contracts and doing business, I
like being president, I like it how everyone defers to my decision and
asks my opinion..."
Hugh reached down, "do you like this?" he started manipulating Erin's
penis, gently squeezing it.
"Oh, I *really* like that."
"Really? Better than when you were a female?"
"It's different. They're both good, but in different ways."
"How about this?" Hugh unzipped the pants and reached in to stroke
more seriously, through the cotton briefs.
"Mmmmm." Erin's tears had stopped and she reached forward and started
to unbutton Hugh's new silk blouse.
Hugh pushed away Erin's hands. "Not this time. You just lay back and
let me take care of you.
As Hugh continued manipulating Erin's penis, he gradually opened up and
worked her suit pants down and off her legs, and then, with a deep
breath, reached into her briefs and grasped the bare penis.
The intimate contact caused Erin to moan. She lay back just enjoying
Hugh had never been this close to a man's penis before. Of course, he
and Erin had had sex the last two nights, but it was always Erin who
had controlled things, as they had been trying to recreate the night
where they had switched, in a hope that they would switch back. So,
this was the first time that Hugh had held Erin's cock in his hand, and
the first time that his face had been within 6 inches of it.
Of course, Hugh had played and masturbated with his own cock, when he
had one, for days on end. So, he knew it intimately, and he knew
exactly what felt good and what didn't. But facing in the third person
was completely different. It felt alive in his hand as it grew, it
throbbed a bit as Erin flexed her abdominal muscles. As it grew harder,
it somehow felt more fragile, as Erin could be easily hurt if he
squeezed too hard. Of course, Hugh knew better than anyone that the
frailty was just an illusion, and he knew that rough and heavy
treatment was better.
Hugh reached down and cupped Erin's scrotal sac. First, he ran his
fingernails very lightly across the surface. This caused Erin to take
in a sharp breath of pleasure. He did this for a few seconds more,
knowing how the ultra-light teasing caused the entire surface to tingle
and come alive.
Next, he grasped them, moderately hard, and squeezed and manipulated
the balls inside, rolling them through his fingers, and squeezing each
one until it slipped out of his grasp.
"Oh Hugh! Oh my god..." Erin couldn't believe it. She had never had
testicles before, and had no idea that they were so incredible
sensitive, or that such rough manipulation could be such an incredible
Hugh knew what Erin was waiting for next. It was time for direct
Hugh looked at the penis he held in his hand. 'I'm not sure I can do
this,' he thought, hesitating. There were just some things that had
never seemed appealing. Like eating raw squid, for example, or kissing
another man's cock. Hugh leaned in for a second, opened his mouth, but
then stopped and pulled back.
Finally, Hugh took a few deep breaths, swallowed hard, and leaned
forward and kissed the glans.
It was soft and silky. This isn't so bad, he thought. It's just like
kissing anything. Hugh gradually covered the entire penis with kisses,
from the head, all the way down the shaft, then all the way back up
again, and then around the top. He smelled the musky sent of male
genitalia, especially as he kissed the base of the cock and buried his
nose in pubic hair. Hugh had, of course, smelled it plenty of times
before, and it was not an unpleasant smell. In fact, it caused his own
excitement to build, and Hugh felt just the beginnings of some wet
slipperiness between his legs.
Hesitating again, but this time not as long, Hugh reached out
tentatively and licked the underside of the cock.
It tasted just a little bit salty, from Erin's long day at work. Hugh
continued licking, light licks on the underside, just beneath the
All this time, Hugh had kept one hand glued to Erin's testicles, and
another stroking and squeezing the base of her cock. All of this
foreplay was driving Erin nuts. Her legs were stretched out, and her
hands were clenched.
Hugh knew it was time to get serious. He couldn't keep teasing Erin
forever, or she'd attack and fuck him, or worse, loose her erection.
Hugh looked at the cock head, screwing up his courage one more time to
take it fully into his mouth.
But just before he did, he saw a drop of pre-cum squeeze from the tip
and glisten there.
My god, he though, she must really be horny. Hugh knew that he better
start sucking soon, or it would be all over. But seeing the cum there,
he just couldn't! First, he wiped his finger across the tip of the
penis, causing Erin to gasp. He held up his finger and sniffed it. The
cum smelled warm and wet - like jasmine. Tentatively, he reached out a
tongue and tasted it.
'Well, that's not so bad,' he thought. It had tasted salty, of course,
but really not that salty. In fact, there was not that much taste at
all, just warm and fluid.
"Hugh! What are you doing down there?" Erin cried out, desperate.
"Just this!" Hugh called back, and then, with one more deep breath, he
covered Erin's penis with his mouth and started sucking.
Hugh was thinking hard, trying not to gag, trying not to scr*pe the
cock with his teeth, and trying to suck as hard as he could and as
deeply as he could. But after a few seconds it hit him, 'Hey!' he
thought, 'I'm enjoying this!' Hugh continued sucking, and the sensation
of the penis in his mouth, sliding in and out, rolling over his tongue,
bumping against the back of his throat, was delicious.
Hugh loved it. Of course, it helped that Erin was appreciating it so
much. She was gasping, pounding the bed, and whimpering. Hugh loved
that he could give someone else so much pleasure, he enjoyed how his
mouth could bring out such sexual excitement.
Just as he felt Erin's hands on his head, pushing down urgently, Hugh
sucked and then felt her penis ejaculating. It throbbed uncontrollably,
as she practically screamed with a very high pitched and un-masculine
wail. The semen spurt out, filling Hugh's mouth and flowing down the
shaft, over his hands, and into her pubic hair.
Hugh gagged. His mouth was full of cum and cock and saliva. He held
very still for a second, made up his mind, and then swallowed.
It was disgusting as it slid down his throat.
But somehow, the whole scene had made Hugh fantastically horny. Erin
was now wasted, she was laying on her back in bed, eyes closed,
whimpering and jerking slightly as he continued to manipulate her
So, Hugh would have to take care of himself. He reached down, pulled up
his skirt, slipped a hand into his panties, and then a finger into his
sopping wet pussy.
This was the first time that Hugh had actually touched his crotch other
than to clean it. It didn't take long to find out what to do, however,
his finger found his clitoris and started stroking it.
"Oh!" Hugh looked surprised. He hadn't realized that he was so close to
cumming. "Oh!" his hand worked faster inside his panties as Erin's cock
slipped out of his mouth. Hugh rested his head on Erin's upper thigh,
her cock just inches away. He watched the cock, thought of how it felt
in his mouth, and smelled the semen as his hand moved faster and
"Oh Jeez!" Hugh came.
Erin looked down and smiled. She had felt guilty about taking all of
the pleasure, and so was glad that Hugh had been able to take care of
"Oh! Oh! Oh!" Hugh gasped, as the orgasm flowed through his body,
peaking multiple times, eventually subsiding.
Hugh was a mess. One hand was covered in semen and saliva. A second was
covered in pussy juice. His face was slick with cum, and his hair was
matted with sweat. He leaned forward and kissed Erin's penis one last
time, and then rested for a second, his face in her wet and matted
He looked up at Erin who smiled down at him. "I'm going to have a
Erin sat up, completely sated, "and I'm going to join you!"
- - - - - - - - - - - - - - -
That night, Hugh was alone in bed as Erin worked on the details of the
contract and went through the general ledger.
Hugh thought about the amazing day. He had discovered that he liked
sucking cock and that it actually turned him on. He wondered why this
was, and had come up with several theories: he could give pleasure to
someone else - so he had that power, it seemed that he was good at it
since Erin had told him it was the most fantastic orgasm she had ever
had - male or female (a thought which caused Hugh to blush), he enjoyed
the very raw physical feeling of being so close to someone else's sex
as to have it actually inside your mouth, and finally, he realized, he
enjoyed the strange feeling of serving someone.
This last feeling was very strong, but it was so new to Hugh that he
couldn't fully grapple with it. Apparently he liked serving Erin,
helping her get over her sadness at not being female anymore and not
being able to shop for pretty clothes.
Oh, and the clothes! That was something new entirely. Even as he
thought about it in bed, he had to giggle and squirm in delight. He
grinned and pushed his face into the pillow, in a silent scream of
Trying on clothes had been the *most* fun of all. Of course, Fenway had
had a lot to do with it. She was so great! While Hugh realized that he
enjoyed serving and taking care of Erin, he also enjoyed it when
someone knowledgeable, an artist, really, was able to teach her and
show her everything she needed to know.
And the clothes were wonderful. They felt great, the looked great, and
he couldn't wait to try them out in public.
All in all a fantastic day, thought Hugh. And I owe it all to Erin. He
As he drifted off to sleep, Hugh realized what it was that he had seen
in his reflection of Erin's body in the mirror at the department store.
At the time, he couldn't quite put his finger on it, but now it came to
He had seen himself in the mirror. He was no longer a stranger to his
own reflection. Somehow, in those pretty features from the Irish
countryside, Hugh had come through and the two had blended together
End of Story