How I Met Rachel
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How Rachel Came To Be free porn video
The night I proposed to my girlfriend and she said yes I made a sudden
realization; I had two choices: tell her that there was another side of
me she didn't know about, a side I called Rachel, who enjoyed wearing
skin tight mini dresses, nylons, lace lingerie, 4" heels, dramatic make-
up, and an assortment of long wigs or somehow figure out how I could
once and for all quit being Rachel for good.
When I was 12 years old, I found myself in my sisters room one night
when the rest of my family was away. Before I knew it I was pulling one
of her dresses, a pair of her tights, her shoes, and preening in the
mirror. Pretty soon I was stealing underwear and pantyhose regularly
from my mom and my sister, sleeping in nighties borrowed from their
closets. The first time I ever masturbated I was wearing a black lace
nighties, black thigh highs and a pair of my sister's kitten heels,
while flipping through a Victoria's Secret catalogue. Unlike other boys
my age looking at the same images, I was wishing I could be those girls
instead of wishing I could have sex with them.
In high school, anytime I had the house to myself, I'd borrow a dress
from my mom or my sister's closet, roll on a pair of pantyhose--which
was always one of the most sensual parts of getting dressed--straighten
and style my long wavy brown hard, do my make up and sit around the
house drinking my mom's white wine, admiring the marks my lipstick left
on the glass's rim.
This was all before the internet, however, so I assumed for a long time
that no one else did this. Every night ended the same, I'd eventually
jerk off to pictures of women in sophisticated dresses wearing pantyhose
and high heels, and I'd immediately feel guilty, shameful, empty. I
tried to quit toward the end of high school. This just made me develop a
nylon fetish, insisting that my high school girlfriends wear short
skirts and nylons whenever we were together, getting irrationally angry
if they refused, wishing I was them while we made out or while they gave
me blow jobs.
When I got to college there was no way I was going to be able to dress,
not with a strange roommate. I assumed those days were over. One thing
that college did bring, for the first time in my life, was unfettered
access to high speed internet, and with it a whole new world opened. Not
only was I not the only crossdresser in the world, there were thousands,
and hundreds of websites dedicated to them. So while I wasn't dressing,
I was creating carefully thought out personas of sexy, submissive
sissies, stealing photos from other websites, passing them off as
myself, and chatting late into the night with dominant males who would
call me their "sissy cumslut" or their "prancing little fag." Every
humiliating name turned me on more and more. I learned to address them
as "sir."
Still, in reality I was a fairly masculine guy. Tall and broad
shouldered, I could grow a fairly impressive beard in just over week and
as I got older I found myself with more chest hair and back hair than I
ever wanted. Every time I ended a night of chat sessions, I felt the
same emptiness and shame I'd felt earlier in life.
My junior year in college, I'd gone three years without wearing any
women's clothing (even if I dreamed and fantasized about it constantly),
and found myself dating an amazingly attractive girl I'd met in one of
my engineering classes. Best of all, she loved wearing short skirts and
nylons, often paired with ripped band t-shirts or oversized flannel
shirt, combat boots or Doc Martens. One night, we'd come back to her
apartment, both of us drunk. We'd been making out the whole way back.
Walking a block while groping each other, stopping to make out against a
light post. When we got back we were both undressing each other when she
suddenly stopped and looked at me and suddenly burst out laughing.
"What?" I said curiously.
"Nothing... It's just... Nevermind."
"No, seriously, what were you thinking? I want to know."
"It's just, well...listen, you're going to think this is crazy, and
you'll totally never be up for it."
I looked over her ridiculously smooth, toned, olive-skinned body, her
perfect breasts, round ass, and long legs, and realized I would do
absolutely anything she asked. "Just tell me, I promise it won't like
weird me out or anything."
"All right. Well, I've always had this fantasy...no...I can't do it.
Nevermind."
"Oh come on. Just tell me."
"Okay, okay, okay. Well, I've sort of always had this fantasy of
dressing a guy up in my clothes, and then having sex with him. Like
putting him in one of my shortest skirts, pantyhose, heels, make up,
doing his hair. Like the whole thing."
I hoped she wouldn't notice the fact that my cock had gotten harder and
longer than either of us had ever seen it while she was talking. I tried
to play it cool, when inside I was dying with excitement. "Um...that's
not that weird, what's the big deal? I mean if it's something you've
always wanted to do, why not?"
She beamed an enormous smile my way, "So you'll do it?!?!"
"Yeah, sure why not?"
She pulled me into her and gave me a deep, passionate kiss, while
stroking my now rigid cock. Then suddenly she pulled away, grabbed my
hand and pulled me into the bathroom.
"Here, put this on," she said handing me a pink robe. She grabbed a pink
razor from her medicine cabinet and a bottle of shave gel and started
running the shower. "Come here, put your legs under the shower. This
will be way easier if we wash your legs first."
Next thing I know she is shaving my legs, my ass, then my chest, my
back, my arms, and my shoulders. I find myself in a daze, thinking that
I should be protesting, trying not to make it evident that her fantasy
is also making my biggest fantasy come true. Wondering if I should just
tell here, but then doubting myself, assuming that she'll think that I'm
gay or that it will suddenly make it weird. So I just go along with it.
So then I'm sitting perfectly hairless in her room, it's at least three
in the morning, she has rollers in my hair and she's doing my make up.
She's a part time beautician at the make-up counter at the local mall.
She's caking on foundation and then smoothing it out, adding rouge, then
eyeliner, eye shadow, highlighter, powder, lipstick. She's reassuring me
the entire time, "Oh my god you are going to look so good. Thank you so
much for doing this. You don't know how much this means to me." She's
occasionally stroking my cock. At one point when she sees that, despite
my excitement, I'm starting to lose a little steam, she gets down on her
knees and starts giving me a blow job. She stops just short of me
cumming.
While she brushes my hair out, she tells me to put on a pair of panties
and a bra. She fills a pair of thigh highs with rice from the kitchen,
ties them off and tells me to put them in the bra. I suddenly wonder why
I'd never thought of that. She hands me a pair of sheer black nylons and
instructs me to roll them before putting them on, I pretend like I
haven't done this hundreds of time before.
"So this is kind of the weird part. I, um, well I sort of bought clothes
for you for this because I was worried mine wouldn't fit and I knew my
heels wouldn't fit."
I was wondering how the bra and the panties fit so well. She hands me a
bag and I open it to find a leopard print sleeveless mini dress with a
turtleneck. My cock instantly hardens at the sight of it. Then she sets
down a pair of 4", patent leather, black heels in front of me. I pull
the dress on, adjusting my "breasts" and step into the heels. She pulls
out a pair of big hoop clip on earrings and a matching silver necklace,
which she puts around my neck, pulling my hair up and clasping behind
me. Then she pulls me over to a mirror.
My mouth drops and I'm surprised to the mouth of the beautiful, if
slightly masculine looking, woman in the mirror do the same.
"You like?" she asks.
"Um, yeah...I mean, um, do you like."
She's just been wearing her bra and panties the whole time, with a black
robe over them. She drops the black robe to the floor and pulls me over
to her. Her hand is working it's way up my silky smooth, nylon covered
thigh, while she pulls me down and starts kissing me. It's the most
intense kiss we've ever had. Her hands work their way up to my breasts
and she bring my hands to the front of her panties, starts to work my
fingers across her clit. She is wetter than I have ever felt. Suddenly
she pushed me down to my knees. "Lick my clit you little bitch," she
says with a smile. And I start to lick as sensuously as I can, imagining
myself as a hot lipstick lesbian. I catch our reflection in the mirror
and almost cum right there.
Her hand is running through my hair as she forces her pussy into my
face. She's moaning louder and louder. I find myself moaning
uncontrollably, in a much higher pitch than usual.
"Come here, Rachel," she says. And while the name throws me for a
second, I go with it. She pulls me up to my feet and starts kissing me
again, even more passionately than before somehow. She is pulling my
skirt up and my pantyhose down and pulling my cock out and climbing on
top of me as she pushes me down onto her bed. She slides herself onto my
cock and starts thrusting her hips as she bounces on me.
"Oh fuck yes, Rachel. Fuck me you pretty little bitch," she screams in
between moaning. It doesn't take long before I'm cumming like I've never
cum before and she is too. Suddenly she is lying on me, both of us
breathing heavily. "I love you Rachel," she says softly as she closes
her eyes and falls asleep.
The next morning, I wake up feeling an odd weight on my chest, I hear
her in the bathroom. She comes out and smiles at me. "You might want to
change before my parents get here. Remember, we're supposed to have
lunch with them today."
"Oh shit," as I jump up, looking at myself in the mirror, my hair still
bigger than usual, but a mess, my lipstick smeared across my face.
"There's make up remover in my medicine cabinet."
She never brings up this fantasy again. I just assume that some day when
we're really drunk it will happen again, afraid to bring it up myself.
Three weeks later, she breaks up with me, out of nowhere. She drops off
a bag at my apartment. It's the clothes, the heels, some make-up, the
stockings filled with rice, a couple of pairs of panties, and couple of
bras and a few pairs of pantyhose, some stockings, some tights, a little
black dress in addition to the leopard print one. There's a note:
"Seemed like you enjoyed it as much as I did that night. Thought you
might like there."
A month after that, I hear from a mutual friend that she's dating a girl
named Rachel.
A year goes by and for the most part those clothes stay in a bag in the
back of my closet. Occasionally when my roommate is out, I'll put on the
panties or a pair of stockings and chat with some doms online. I ask
them to call me Rachel. I tell them how much I love being their pretty
little bitch.
It's my senior year and the second week of October. I'm seeing another
girl. She's not quite as pretty as Meghan, but she's smart and the sex
is pretty great. We get invited to a pimps and ho's themed Halloween
party at a fraternity that her little brother is in. She says she thinks
it would be hilarious if I went as the ho and she went as the pimp.
Suddenly, I find myself trying to see how much weight I can lose in two
weeks. I order a corset online, some more make up, 5" heels. She asks me
if I need any help with clothes, and I just tell her I have it covered.
I'm watching make-up tutorials online, I blow $100 on silicone breast
inserts. I find myself tweezing my eyebrows into an androgynous arch.
The day before I buy two bottles of Nair, some girly bubble bath,
perfume, women's deodorant, shampoo, and body wash. I take a bubble
bath the afternoon before the party, thankful that my roommate, Matt, is
over at his girlfriend's house. I apply the nair on all of my body, just
as it starts to burn I wash it all off, watching all of my hair come
with it, feeling my smooth hairless skin. On a whim, I pull out the hair
bleaching kit I bought at the drugstore and after two hours, I find
myself blowdrying my now platinum blonde shoulder length hair. Because
my hair is so curly, it usually barely comes past my ears, but now
straightened, it is skimming the top of my back, just past my shoulders.
I put in barrettes as I do my make-up. I overdo it on purpose, trying to
look like a total slut. I practice my best come-hither look in the
mirror as I finish, looking at the clock realizing I have just enough
time to finish getting dressed. The jiggle of the silicone inserts in my
40DD lace bra feels amazing. My cock is so hard I jerk off while staring
at myself in the mirror in just panties, a bra, stockings and my heels.
Now limp, I tuck it back and pull in my testicles as I've read about on
line. I pull on the leopard print dress, touch up my make up and put all
of my things in a handbag I bought at a thrift store. I pose in the
mirror, waiting for Katie, and suddenly it hits me. I've gone way too
far. How did I not realize it. I hear her knock on the door and I
panick. "Oh fuck, what have I done?" I think. The sound of my heels
clicking on the hardwood, my hips swaying uncontrollably in the tight
dress, only makes it that much clearer. I pause before opening the door
and when I do, I see Katie there in a cheap purple pimp suit costume she
probably bought for $20 at Walmart. Her mouth drops.
"Um, Mark?" she says, stunned. "Is that you?"
I just give her a weak and nervous smile.
"Wow. Um...wow," she says. "Um, is the the first time . . . um, you know
what never mind. We should get going." She leans up and gives me an
awkward kiss on the cheek. And in that moment, I make my decision. I
just have to go with it, and if anything I should enjoy it.
The walk there is amazing. The feel of the cool air against my nylon
covered legs. The sound of my heels clacking on the pavement. The looks
I get from the guys as we walk down the street, the catcalls and even
the pats on the ass. I can tell Katie is annoyed and confused, because
she can see how much I'm smiling.
Once we get to the party, she almost immediately leaves me to talk with
some of her other friends. Over and over again, I find guys hitting on
me before realizing I'm a guy as soon as I start to talk. Over the
course of the night, the more I drink, the more I work on my girl voice
and the more I find myself flirting back. Pretty soon, I'm on the dance
floor grinding against some giant football player, he has his hand on my
ass and I'm staring up into his eyes. Suddenly, I feel a hand on mine
and I'm being pulled into the next room. It's Katie.
"What the fuck are you doing Mark?"
"Nothing, I'm just having fun, call me Rachel," I say, finding myself
stuck in my new breathy girl voice, slurring my words from the far too
many cups of punch I've had. I lean forward to kiss her. I take her
hands and put them on my ass. I start to moan like a girl, as I drop to
my knees, rubbing my hand against the front of her cheezy, purple
polyester pants. I start to pull her pants down, but she pulls them up
and pushes me back as she steps back.
"What the fuck Mark? What is this?" she says looking me up and down. "I
bet you were hoping there'd be a cock in my pants weren't you, you
fucking little fag." And with that she storms out of the room and out of
the party.
The empty feeling, the shame, the embarrassment all comes back. The
football player tries to stop me, but I grab my handbag and start to
leave. I take mostly back alleys back to my apartment to avoid the
crowds, but still end up hearing catcalls, feeling guys eyes all over
me. Feeling like an idiot the whole time.
I walk into my apartment and stop cold in my tracks when I see Matt
drinking a beer by himself in the kitchen. His eyes open wide, as he
looks my legs and my ass up and down. "Holy shit! Mark, is that you?"
"Yeah, I'm just going to go change. It's been a weird night."
"Wait, wait. Don't do that. Come have a beer with me."
He's in some sort of Hercules costume: bare-chested, with leather loin
cloth or something, matching boots, a long blonde wig. Sometimes I
forget how much he works out.
"Where's Katie?" he asks.
"I think that's over. Melissa?"
"Yeah, um. I fucked up and ended up with some freshman in a slutty
police woman costume. She found me."
"Cheers?" I say and lift my beer. I find myself leaning back and
automatically crossing my legs, brushing my hair out of my face.
"Fuck man, you look good," he says as he eyes my legs and my breasts.
"Really?" I ask with a slight smile.
"Um, yeah. If you were a real girl I would be all over you right now."
"Oh really," I say, finding myself slipping into my Rachel voice. "And
what would happen then?"
He looks surprised, but he plays along, "I think you know what would
happen. But, you know what, I don't even know your name, miss."
Staring intently at his hard chest, I slip one of my heels off under the
table, and as I start to rub my manicured foot against the front of his
loin cloth, I say in my breathiest, girliest voice, "It's Rachel."
I see him bite his lip as his eyes roll back. Breathing heavy, in a low
voice, he says, "Why don't you come over here and sit on my lap you
pretty little slut."
I mince my way over to him, hips swaying, and bend over rubbing both of
my hands against his hard chest as I sit on his lap, my legs straddling
him. He puts his hand on the back on my neck, the other on my ass
squeezing it as he pulls me in and kisses me. I find myself loving the
feel of his stubble against my smooth face, the smell of his musky
cologne mixing with my sweet perfume. My hands make my way under his
loin cloth, stroking his already hard cock, grinding against him as I
feel his tongue wildly explore my mouth.
He pulls back and pushes down on my shoulders, "Suck it you little
bitch."
I kiss his chest and his stomach, his pubic hair even, as I make my way
down to his cock. I lick it and stroke it. I take his balls in my mouth,
loving the feeling of his pubic hair against my lips and chin. I start
to take his cock in my mouth, when suddenly his hand is on the back of
my head, forcing it all the way down my throat. I gag. My eyes start to
tear up, but I do my best to take it. I try to moan like I've seen the
girls do in the videos I've watched. I grab his ass and pull him into
me, making a mental note about working on my gag reflex. But then he is
pulling me up again. He pulls out a condom from the drawer and a bottle
of lube and hands them both to me. I stroke his cock while pulling the
condom on, he smiles as me leaning in to kiss my neck. I rub the lube on
his cock while kissing him. Then he turns me around and instead of
pulling my pantyhose down, I hear him rip a hole in them. And suddenly I
can feel his cock against my ass, and before I can even wonder if I'm
actually ready for this, he is entering me and at first my vision is
filled with stars as the pain radiates throughout my whole body, but
then he slows and I start to relax and while it still hurts, I find
myself enjoying it. I'm thrusting my hips in time with his, I'm moaning
loudly. I feel him speed up, his thrusts are more intense and then I
feel him spasm and breathing heavily, and then he picks up speed as he
moans louder, pumping right through his orgasm. I start to breathe more
heavily and moan louder and find myself suddenly feeling like I might
cum too, and as he pushed in one last time, I feel my panties fill with
warm wetness, and I sight as he pulls out.
"Oh god, that was so fucking good," he sighs as he sits back down. And
he smiles up at me and I wonder, what the hell just happened?
Eisley
- 22.08.2021
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