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This work is copyrighted to the author © 2009.  Please
don't remove the author information or make any changes
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Nighty Night
by Anonymous (address withheld)

***

A guy is talked into cross-dressing so he can attend an 
"all girls" sleepover. (MF, cd)

***

"Reeeyullly, Jack," she said, drawing out the "really" 
like the Valley Girl that still lived inside her 
slender but reeyully-thirty-something body, "You can't 
stay for the lingerie party. Go bowling with the boys 
or something...Naughty Nightie parties are for girls 
only."

"C'mon," I protested, "I've been working every night 
this week, and I really wanted to just spend an evening 
relaxing at home... reeyully."

"Really Jack," she said, easing off on the Valley 
intonation now, "How could you relax with a bunch of 
giggling, tittering women in the next room, even if you 
could stay here?"

"Tittering? Now that does sound interesting" I teased. 
"Isn't that at least half, or more precisely, two-
thirds of what naughty nighties are all about? And what 
makes you think I'd want to stay in the next room 
watching the tube, when I could join the tittering, 
watching the boobs?"

"Bad puns will get you nowhere," she said, and 
countered with what she was sure was a one-hundred 
percent airtight put-off: "The only way you're going to 
stay for this party is if you're decked out like the 
Queen Mary."

I paused as if I reeyully had to think this one over, 
looked stage left and stage right as if seeking counsel 
from two invisible advisors, and then let it go: "Okay, 
you're on," I said, waiting for the reaction.

Whenever I think I've tricked Carol into conceding an 
argument by agreeing to something I'm sure she never 
thought I'd agree to, it always turns out that SHE set 
ME up. I could tell by the look in her eye that she'd 
done it again.

"Gotcha!" she popped, revealing that she'd planned it 
this way from the start.

"HumnaHumnaHumna," I muttered, slapping my forehead and 
rolling my eyes skyward like Ralph Cramden and "the 
Meathead" combined.

"Cut the bad impressions," said Carol. "The real sitcom 
is about to begin. Haul your buns out of that chair, go 
and shave really close, and get into the shower. You've 
got to get ready to get 'into character' for the 
show... and don't forget to shave those hairy legs."

"B-b-but!" I pretended to protest, as she pushed me 
toward the bathroom.

"And I'll be there in a while to help you shave 
whatever else needs shaving, unless you're smart enough 
to figure out what that might be."

Feigning reluctance, I shuffled off to the shower. Not 
being a total dummy, after shaving my face and neck, 
AND my legs, I shaved down my chest a bit, so that no 
chest hairs would show in an ordinary neckline. "Not 
nearly enough," said Carol, stepping into the shower 
with me. 

"Armpits, guy... we girls don't walk around with those 
grody clumps of hair under our arms... here, I'll do 
it," she said, taking the razor from me. I thought it 
would be tricky shaving my armpits, but in no time at 
all those "grody clumps" were gone... and all the rest 
of my chest hair, too. "Let's see how you did with 
those legs," she said, letting her soapy breasts brush 
against my now-erect cock as she crouched down in front 
of me and wrapped her arms around me.

"Wait a minute, you're shaving my buns," I complained. 
"Who's going to see THEM?"

"Don't complain," she said. "How can you get 'in 
character' if you don't feel entirely feminine? And we 
can't have this thing sticking out once you're 'in 
character'," she observed, looking my erect cock in the 
eye. "We'll have to take measures to keep this down for 
a while...at least until you're in costume," she said, 
wrapping her lips around its head, making it MUCH 
bigger, before it got much smaller. How could I 
complain?

I don't know how she did it, but while I was in the 
paroxysms of ecstasy, she'd managed to trim my bush so 
that it looked just like hers... well, almost. Talk 
about sneaky feminine wiles. Me and my now-hairless 
balls would have to show her a thing or two...or had 
she ALREADY seen a thing or two? Oh well, I'll get her 
later, I thought.

A quick blast of cold water suddenly hit me, making my 
depleted cock and balls shrink still further. "Here, 
dry off," she said, handing me a towel. "You've got to 
be dry before we can moisturize."

"Huh?" I responded to that bit of feminine illogic, as 
she rubbed me down with whatever fragrant stuff it was 
that made her even tastier. Not so oddly, I was looking 
forward to being just as tasty as she was. And getting 
into the mood of things, I took the bottle of 
moisturizer and started rubbing the fragrant liquid on 
her breasts, saying "Yes deah, we rahlly must 
moisturize, mustn't we?"

"Later for that," she said, leading me into the bedroom 
by my handle, which was now barely large enough to get 
a grip on.

"Easy on that," I complained, "I may need this thing 
again."

"You will," she agreed, "but much later in the evening. 
Until then we've got to keep it as invisible as 
possible. "Let me see now..." she said as she went 
rummaging through one of those dresser drawers filled 
with indescribables. 

"This should do it!" she said as she retrieved a pair 
of those little skin-colored adhesive half-bra cups 
that are made for the ultimate plunging neckline. 
Seeing that I was obviously puzzled, Carol explained, 
"Not for your boobs, dummy! Spread your legs a bit." 

She applied extra spirit gum to the bra cups, and then 
stuck the two of them together along their top edges. 
Glued together like that, they bore an amazing 
resemblance to a shaved pussy.

"Looks like a pussy," I observed brightly.

"Up yours," she countered, pushing my balls up out of 
sight with my cock pulled back over them. In the middle 
of my amazement over how easily it could all be tucked 
away, she capped my diminished essentials with the 
glued-together pair of bra cups. It was, in a manner of 
speaking, a master stroke. It stuck fast and held 
neatly. Looking down at myself, it looked to ME like 
I'd suddenly become female. Carol held a hand-mirror so 
that I could have a better look, like a hairdresser 
showing me my new "do". 

"With a little makeup, it'll be perfect!" she said. I 
couldn't believe it: I was about to get my crotch made 
up. What a make-over!

I was really getting into this, as she glued a pair of 
reeyully convincing breasts to my chest. "Where did you 
get these?" I asked, "They can't be yours...you've 
never needed them."

"They were. I was late to develop, and really self-
conscious about it. But I don't need them anymore, and 
they're yours now."

Except for the very edges, they looked like the genuine 
article(s). They bounced nicely (I couldn't resist 
jiggling "my" tits), they matched my skin color, and 
they had such nice rosy nipples. I couldn't resist 
pinching them...I almost felt the squeeze!

"Don't worry about the edges," she said, "A little 
Dermablend will cover that nicely." And it did. They 
really looked real, reeyully! My very own boobs!

"On the bed, on your back, knees up" Carol directed.

"What is this, a gynecological exam?" I clowned.

"When I'm done, you may be able to pass one," she said, 
applying more Dermablend and makeup color to my 
"pussy". "How's this?" she asked, holding the hand 
mirror so I could see the finished work.

"Incredible!" I said, "It looks good enough to eat!"

"I was thinking the same thing," she said, "but 
layyyyyter. Now it's time to pick out your wardrobe," 
she said, turning to the dresser filled with all those 
delectable little underthings.

"Since you're a new woman, I think we'll go with 
virginal white, although you may not qualify by the 
time the evening's up," she said, handing me a pair of 
lacey white nylon bikini panties. "Here, step into 
these. Don't worry about the makeup smearing... it's 
waterproof, hypoallergenic, AND it has a great 
fragrance, too."

"But how does it taste?" I wisecracked as I pulled the 
panties up my smooth legs. I loved the feel of the cool 
white nylon sliding over my equally smooth buns. I 
could see why women liked wearing these things, and I 
began to consider the possibility of wearing them all 
the time, not just tonight. I even liked the lace trim 
around the leg openings and the ruffled stretch lace 
waistband... and the little pink bows at the hips, too. 
Being feminine is really nice, I decided... reeyully.

"We have a bra to match," she said, as she threaded my 
arms through the straps of an absolutely stunning 
little front-hook push-up number whose half-cups were 
topped by wispy lace that barely concealed "my" 
nipples. I had been so enthralled putting on my panties 
that I hadn't noticed that Carol had already put on 
panties and bra that matched the ones I was wearing.

I couldn't resist comparing notes: "My boobs are just 
as nice as yours," I said, "but don't you think you 
should show a little less nipple? We're beginning to 
look like sisters, and I'm beginning to feel a bit 
protective."

"Your the one that's going to need to be protected," 
she said, "and remember, there are only going to be 
girls at the naughty nightie party, so be a good girl. 
You haven't met Laura, the woman who sells the 
lingerie, but some of the girls you've met from my 
office will be here, so you've reeyully got to make 
sure they don't recognize you. 'Jack' is out bowling 
tonight, and you're his twin sister Jackie, who's 
visiting us from down South... got that?"

"Got it," I said, as she fastened a white lace garter 
belt around my waist - it was a great match for the 
panties and bra I was wearing.

"Let's stick with a neutral beige for the nylons," she 
said, "Here, watch how I put them on so that you won't 
snag them... and keep those seams straight."

I watched carefully, especially since this was 
something I always enjoyed watching. Even though I'd 
never done it before, I knew EXACTLY how to put them 
on... I just hadn't imagined how great it would feel to 
have my legs hugged by those long silky stockings. It 
was a delight that they were long enough to completely 
cover my thighs. Carol adjusted the straps on my garter 
belt so that they'd stay up snugly. What a wonderful 
feeling it was, especially to be able to slide one 
smooth leg against the other! How do women get through 
a day without getting excited about how feminine they 
are?

Carol could tell what I was thinking from the dreamy 
look in my eyes: "I know how wonderful it feels," she 
said, "and I always wanted you to be able to share it 
with me. I just KNEW you'd love it!"

"What can I say," I sang, "I enjoy... being a girl!"

"Good," said Carol, "but we'll have to work on your 
voice. Remember that little Southern twang that Dustin 
Hoffman used for 'Tootsie'? That will probably be easy 
for you to do, and more convincing than anything else 
we can manage in just a couple of hours. Try to 
practice speaking that way while we finish dressing."

"Sho 'nuff, honey," I mimicked.

"Careful now," Carol said, "you may wind up sounding 
more like Flip Wilson's 'Geraldine', and we don't want 
to offend any of the black girls who are going to be at 
the party."

"You wouldn't have a Tina Turner wig for me, would 
you?" I asked, only half kidding. I've always thought 
that Tina Turner is one great lady, and I was beginning 
to feel jealous of her legs.

"Not exactly, but it will be bouffant though...after 
all, Jackie, y'all are from the South where big hair is 
still big. Actually, it's one of my wigs from the 
Seventies...and I think that a nice bright stretch 
Lycra mini-dress would be just the thing to go with 
it... also one of my relics from the Seventies!"

I remembered her in that dress from when we were first 
dating, and dropping into my best "Tootsie", I drawled, 
"Would thayut be the shahny rayud dress, honey? Ayyund 
was thayut a weeyug y'all was wearin'? Ah thawt Ah took 
awf evathin' y'all was wearin' thayut naht."

"Evathin' but thayut," Carol replied, picking up the 
drawl, "Thayut weeyugg held on REAL good!"

"A-mazin'," I said, "Ah nevah woulda thawt it!"

Sure enough, she produced that dress out of a garment 
bag in the walk-in closet. I thought it had long ago 
made the trip to the Goodwill box, but it still looked 
like new. I was really glad to see it again.

"I became a woman with that dress, Jackie," said Carol, 
"and so will you. Put on this little half-slip, and 
then slip into the dress so that we can do your 
makeup."

I hate to admit that although my fanny's cute and 
nicely rounded from going to Jazzercise classes with 
Carol, my hips aren't nearly as well- rounded as hers, 
despite all those leg lifts. To think that I used to 
worry that those exercises were making me shaped like a 
woman! But the stretchy red dress did show off my buns 
nicely, and I just loved that lacy little half-slip 
tickling my legs.

Carol picked out a pair of red patent leather shoes 
with 2-1/2" heels to go with the dress. "Try these," 
she said, "I'd love to give you higher heels, but you 
shouldn't be too much taller than me, and 4" heels are 
the tallest I've got for myself. If your shoes are too 
tight we'll use a little shoe stretch on them."

Although the nylons made it easy to slide into the 
shoes, they were a bit tight, so Carol wet them with a 
bit of the shoe stretch solution, and I could feel the 
shoes become more comfortable in just a few seconds. 

"Walk around in them while I select makeup for you," 
said Carol, "it will help them stretch enough. We don't 
want your feet to spoil the evening for you." If they'd 
been higher heels, I might have had difficulty, but 
this was EASY. I pranced around, wiggling my little ass 
for all it was worth. This was really FUN. Carol broke 
into a broad grin: "You're going to LOVE this night, I 
can see that. But as good as you look, you still need 
makeup, the wig, and some jewelry."

I'd never sat at Carol's makeup mirror before, but it 
all seemed completely natural now. The last traces of 
masculinity vanished under a subtle cover of Dermablend 
with just the right accents of blush and shadow. I 
blushed... my true femininity was being revealed.

"Remember those green-tinted contact lenses you bought 
as a joke?" said Carol, "I'll bet they'd look perfect 
now." I had to agree, and tottered off to get them. I'd 
only kept them as a spare pair, but when I put them on 
and looked in the mirror, I was amazed... I was one 
sultry broad! "Ready for the eyeshadow!" I called out.

"Eyelashes first," said Carol, "You Southern girls like 
lots of eyelash."

"Just don't overdo it," I said, sitting back down in 
front of the mirror. "I don't want to look like a 
hooker. Jack would be embarrassed if his sister looked 
tacky."

"Don't worry, Jackie dear," said Carol, "I'll get it 
just right." And sure enough she did - just the right 
emphasis on the eyelashes, just the right amount of 
mascara, just the right tint of green and silver 
eyeshadow - the woman was truly an artist. I was 
jealous! but I would learn.

False fingernails were next, and I was equally amazed 
by how easily they went on, and how with the right 
silvery red polish, they became MINE, like I'd been 
taking care of them for months. Carol then returned to 
my face, finishing her work with a luminous pale red 
lip gloss, and lowered the bouffant auburn wig over my 
head. God, I was lovely! "Is it possible that I have 
the hots for myself?" I asked Carol.

"Could be," she said. "I know I do! but later for that 
- we still have your debut ahead of us," she said as 
she spiked my earlobes and put in a pair of glittery 
pendant earrings.

"Ouch.... and ouch!" I complained.

"Don't worry", Carol said, they're all sterilized, and 
you'll forget the sting in about a minute. And if you 
don't want to keep them, the holes will heal up 
overnight if we don't put studs in to keep them open.

"Don't want to keep them?" I said. "I think they're 
great."

"Okay, finishing touch," said Carol. "How's this 
necklace?" she asked, looping a long dangly creation 
around my neck and clasping it behind.

"I love it! It's perfect!" I said.

"Okay," she said, "Just remember to keep it from 
falling into your cleavage...that never looks good."

Cleavage! I'd been so involved with the way my face was 
evolving, I hadn't even realized that I had a nicely 
exposed decolletage. Wow! They were lovely - they 
looked so REAL. I couldn't resist cupping them in my 
hands.

"You're getting preoccupied with yourself," Carol 
cautioned. It wasn't until then that I realized that 
while tending to me, she'd also managed to get herself 
completely dressed, in an electric-blue dress similar 
to the one I was wearing. It was easy for her, of 
course, but she was stunning! Were we ever an eye-
popping pair of dolls!

"Woman's work is never done," Carol admonished. "You've 
got to help me get the place ready...Laura will be here 
any moment, and the girls will start arriving soon. 
Moving some furniture in heels should be good 
practice."

I'd always ducked these party preparations before, but 
this time I really pitched in. I was eagerly 
anticipating the evening to come, and I wanted 
everything to be just right. We knew that there would 
be a model to show how the lingerie looked on (I was 
certainly looking forward to THAT), so we removed the 
coffee table from the living room and replaced it with 
a low carpeted platform that we usually used for sit-
ups and other exercises - it would be perfect as a 
runway for the model! 

Carol, who thinks of everything, replaced all the white 
light bulbs in the living room with rose-tinted ones, 
and dimmed the lights down. "Not just for the 
atmosphere," she explained, "You're going to be in 
close contact with about a dozen women, and if they 
look too closely, they'll think you're wearing too much 
makeup. You wouldn't want them to think you were 
overdoing it, would you?" 

I had to agree with her, and I was grateful that she'd 
expressed it that way... with no offense to my 
femininity.

We'd barely finished setting out the wine and cheese 
when the doorbell rang. "Don't forget that sweet 
Southern accent," said Carol, "and don't overdo it 
either." I cleared my throat, and breathed, "Hi, y'all" 
a few times until it sounded right... or do I mean 
"raht?"

Ah was bayerly satisfahd wiyeth mah voice when Carol 
opened the door to let in Laura, a tall, raven-haired 
beauty with a gay smile - and two enormous traveling 
cases. Carol introduced me as her sister-in-law, 
"Jackie", and I breathed a too-sexy "Puleezed to 
meetcha all", as I took one of the cases - expressing 
the proper degree of exertion - and led Laura into the 
living room.  

We set down the cases, and I poured a glass of Chablis 
for each of us. Looking straight into Laura's eyes as I 
handed her the glass, I could see that I'd easily 
passed the first test: Laura was still smiling at me, 
but the smile had hardened, and I could tell that she 
viewed me as competition. 

"Interesting..." I thought - at a gathering with no 
men. Could she be jealous of my being there with Carol?

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 65