Thangaiku Theriyaamal Amma Magalai Oothen
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Carissa's Journey-the Beginning free porn video
The light filled the room slowly, creating a soft glow. It hadn't fully
risen before the alarm on Tim's phone went off, waking him from his
slumber. With a stretch of his arm, the alarm went silent. He smiled from
ear to ear, for today his weekend adventure begins. He flipped the covers
off his body, exposing a mostly naked male, only having a pair of pink
panties on. You see, Tim isn't like most men, he has been a cross dresser
since a little boy, and it has only grown over the years. He now owns
more panties than boxers, and wears them 24/7. He would love to dress
more, but having roommates has limited his dressing time. This weekend is
a special one, because both roommates are gone and he can dress up like
Carissa for two whole days. Carissa, was the name he used to express his
fem side. Over the years he has been Carissa in a digital form, having
accounts on various sites, and having several sissy friends. He had
videos and photos posted online to share with others. He even had regular
cam sessions with various Dommes. Once a month he attended a sissy social
night at a local caf?. There were several sissies that would show up.
They discussed various sissy subjects and ideals. It was hosted by a
local Mistress, who was very passionate about sissies. Tim had developed
a crush on her, but felt way to out of her league. Over the past year, he
had become more and more of a sissy, more and more of the people in his
regular life knew he dressed, or were catching on. It might have
something to do with all the sissy hypno videos, but Carissa was pushing
out more and more. He even began to meet with a counselor once a week to
talk about his sissy side, trying to come to terms with it all. Let's
look back at how Tim got here.
Tim grew up in a small country town, were everything was painted black
and white, boys were boys, and girls were girls. You had to be manly, go
to church 3 times a week, and save one self for marriage. He was raised
in a strict conservative house, so all the dressing he did as a child and
teenager brought on guilt and shame. At an early age, he would just wear
his mother's clothing, dance around and such. It was harmless, but he
felt guilt. He tried playing with his sisters dolls and would get yelled
at. Kids at school made fun of the boys that didn't play sports. He
caught on, and knew he had to hide his desires, had to fit in to survive.
Outside he was a normal popular boy, but when he could he would dress up.
Once in junior high, he learned about sex and started having wet dreams.
His dressing became more sexual, but was still about dressing, he wasn't
attracted to boys. He started dating and was like most high school boys
looking to hook up. It was his junior year of high school when he met
Jenna. She had just transferred in, and was quite the looker. She was a
bit taller at 5'8, and very athletic. She transferred in to be on the
state winning softball team. She had long red hair and put every other
girl's body to shame. Tim feel in love instantly.
She sat next to him in history, and they hit it off from the start.
Having similar movie and music interest. Before long they were dating,
hanging out all the time. Tim was still a virgin, and was hoping Jenna
would be his first, they had made out several times, and were taking
things slow. After a month of dating, they talked about having sex, and
planned a date out to the local make out spot. The date went well and Tim
found himself naked in the bed of his truck with this beauty. He was hard
before his pants were even off. He slowly took off her shirt and began to
kiss her neck. She moaned as he fumbled with her bra, his nerves getting
to him. It finally came loose and as her bare breast sprang forward Tim
took her breast into her mouth. He was licking and sucking while undoing
her paints. His hand slide into her pants, and he felt he lace of her
panties, his excitement was showing as his cock twitched. Jenna couldn't
take much more and her aggressiveness took over, she pushed Tim over onto
his back and pulled her pants off. She climbed on top of him and began to
passionately kiss him. "You ready for this baby." She asked before
blowing in his ear, the excitement of her lace panties rubbing against
his cock and the blowing in the air, sent Tim over the edge and he came
right there. "I'm so sorry babe, I've I've.."
"No worries, let's just keep kissing you'll get back up in a bit. It was
no time at all before he was hard again and a new condom was put on.
Jenna mounted him and began to ride him. Tim was in heaven and lasted a
whole 10 minutes. They became quite the couple as they became seniors
and were finishing up school. They talked about college, and staying
together, they loved each other. Jenna had a scholarship to play
softball, and Tim had the grades to follow her. The weekend after
graduation, Tim's parents were going out of town with his brother and
sister. He was going to have the place to himself.
He had been looking forward to this weekend for months, since he hadn't
been able to dress all that much with everything going on. As the weekend
approached he started acting sick, so he could play off not being able to
go out with Jenna that weekend. It had worked, he called her Friday night
and explained that he was going to rest all weekend, feeling like he had
the flu or something. He got dressed up that Saturday and logged online
to chat with others. He was talking with another cross dresser and
masturbating when his front door opened and in walked Jenna. Tim was
totally caught with panties around his ankles, his skirt hiked up, and
stroking his cock. "Oh my God, Tim what are you doing, what the Hell, are
you a FAGGOT." She took off, Tim rushed to the door, but didn't go out
being dressed. He changed and called her "Jenna, I can explain, please
where are you?" He drove to her house, she wasn't there, he drove to
their favorite hang out spot and found her crying. "Jenna, I'm so sorry,
I just, it's just a thing I don't know I've done it since I was like 5
and I don't know." He said trying to hug her. She pushes him away. "Are
you gay?" Tears running down her face, "I loved you, what the fuck is
wrong with you? Fucking Fag, I don't want to talk to you again." Tim
didn't say anything, just looked down as she left. They never spoke
again.
Tim went off to college, but was different. He didn't feel the same
confidence he once had, he was confused and didn't know what to think. He
stopped dressing and threw his sissy things away, started drinking and
became a bigger asshole. He started watching porn more and more, the
thoughts of being gay filled his head. He had never looked at a guy, or
fantasied about one, but dressing up like a girl, did that make him gay.
These ideals and thoughts filled his head off and on. He didn't have
anyone to talk to or knew anyone that would understand. College had its
ups and downs. There was happiness and sadness, he dated a few girls and
some got serious. His dressing was almost a distance memory until his
senior year. He came home late one night and walked in on his roommate
and his girlfriend. "Sorry, didn't know you guys were here." He said and
waited in the hallway. Not long after they finished and came out and
took off to the concert they were supposed to be at. Tim entered the room
and changed into a pair of shorts before lying on the couch to watch tv.
He shifted on the couch and felt something soft and lacy. He reached
behind him and he was holding a sheer pink pair of panties, they much be
Holly's, her and Justin must have been in a hurry when they got dressed.
Just holding them flooded Tim's mind with his dressing, his cock became
rock hard. He brought the panties to his nose and inhaled her scent. "Oh
God." He moaned as he slide off his shorts and wrapped the panties around
his cock, it only took 5 pumps before his stomach and chest was covered
in cum. His desire to dress started to grow and grow it did.
He got online and ordered some clothes on ebay, he built his collection
back up. It was even trickier dressing up in a college dorm room, having
to hide things and be careful when to dress. It was also around this
time, he discovered that many adult video stores, have private viewing
rooms. He found one that was near his college and packed a bag of girl
clothes and took off. He parked around the corner from the place and
looked around before entering, not wanted to be seen by anyone he knew.
He was nervous, not about being in the store, but about paying to enter
the arcade section. He gave the cashier a twenty and got some tokens and
headed to the back.
He pushed his way past the beads and entered the darkness, it took a few
seconds for his eyes to adjust. There were two hallways, one said theater
the other said booths. He walked down the booth isle, and found a room
that had a green light on above it, signaling it was free. He entered and
placed a few tokens in the machine, and TV turned on. It was a gay
station, as the images of small white guy getting pounded by a big black
man. Tim was caught off guard, but was turned on, the moans from the tv
filled the small room, and the musky smell of the place filled his nose.
It was all new, and felt so dirty, but so exciting. He took off his
shirt, exposing the black bra he was wearing, then slide off his jeans,
exposing the red panties and stockings. He took a dress out of his
backpack and slide it on. He sat in the chair and watched the monitor,
his cock began to grow. He was rubbing it through the dress, when he
heard a cough. It was the person in the booth next to him, at that point
Tim noticed a hole in the wall. It was a hole to the next booth. He
looked at the other wall and also noticed a hole. He could see into
either booth, being embarrassed he was watching gay porn he changed the
channel. After flipping through about 8 gay stations he found a video of
a young girl getting double teamed. As he watched and played with
himself, the desire to look through the hole became stronger, he would
try to peak without being too obvious. Once he found the best angle, he
was able to see the stranger, stoking his cock, pumping it. Tim was too
focused to realize the stranger had turned towards the hole and was
stoking towards him. The man stood and Tim, shot up and started at the
TV, then he saw it out of the corner of his eye, the cock came through
the hole. Tim turned and looked at it, not sure what to do. His mouth
began to water, strangely. As if on auto-pilot, he reached out and took
it in his hand, feeling the texture and weight, it was heavier and
thicker than his own. He stroked it and before long found himself on his
knees, bring it to his mouth. He slowly wrapped his lips around it and
started to bob. The stranger moaned, "Oh yeah baby, take daddies cock.
That's good slut." Tim lost himself and just sucked and licked the cock,
it would enter his throat and he would gag. "Oh you slut, yeah take that
cock." Before long the cock tightened up and shot a load into the back
his throat, he had no choice but to swallow. Most of it went down some
spilled out onto his chin, the stranger withdrew his cock. "Thanks
sweetheart, here's my number." He slide a card through the hole, Tim
leaned back against the wall, trying figure out what just happened. The
taste of semen filling his mouth, his cock was leaking pre-cum through
the skirt. As he started to get up, he noticed a cock coming through the
other hole. "That looked hot, you still hungry, slut?" The other stranger
said, Tim got back to his knees, and took the cock right in. He didn't
even think, just took the cock until it exploded in his mouth. He took
three more cocks that night, before filling full and messy. He walked
out, having cum drying on his chin, sweaty and dirty. He got back to the
dorms and was even more confused. That night he dreamt about cocks, and
it wouldn't be the last.
That final year college brought on a lot of sex, most of which found Tim
dressed up like Carissa and being used by men. He had a created a second
life that continued after college. Now back to present day. Tim got out
of bed and heads to the bathroom. He slips his panties off and sits down
to pee, being in chastity and all. He has been planning this weekend for
a month, he bought a new dildo, set up a few cam sessions, and bought a
new outfit. The chastity cage was put on a week ago, and his horniness
level was pretty high. All week building up to this weekend, he spend 2
hours a day watching sissy porn, no chance of release, just frustration.
After his tinkle, he turns on the water in the tub. As the tub filled up,
he pours in some various oils and scents, creating bubbles, the room
filled up with the smell of jasmine. Once the bubbles climbed to the top
of the tub, Tim slips in, soaking in the warm water, softening his skin.
As he laid there, the thoughts and anticipation grew for what the day was
going to bring. He couldn't wait to fuck his boi pussy with his new toy,
to be a dirty slut for his online Mistress. His mind was so focused on
being a slut, he just wanted to be used. He couldn't get enough of his
dildos. The water begin to cool down, and Tim wanted to get the day going
and got out of the tub. He dried off, applied some lotion standing in
front of the mirror. He turned back and forth and tried to imagine a more
girly figure, and was jealous he didn't have the curves. He sighed it
off, and got out his make-up.
Once all the make-up was out on the table, he began with some foundation,
and smoothed out his skin, added some blush and bronzer to bring out his
cheeks make his nose smaller. The most important aspect were the eyes, he
decided to go dark and smoky, using silver and blues, after getting it
on, next came the fake lashes. Carissa was becoming more present, the
final touch was some sparkly lip gloss, and he blew himself a kiss and
pulled out his phone. He was posing and taking selfies, just like any
girl getting ready. Once back in his room he pulled out his new outfit
which included: a black dress, thigh high stocking, pink panties and bra,
and pink heels. He got his wig out and made sure it was in place. He then
started to dress, first just in under garments. He set up a tri-pod and
camera. Got his computer set up and put on some music. He found a station
that was titled slutty dance music, and turned up the volume. He was
dancing around his room and snapping photos, bending over, licking his
lips, posing like a slut. Letting Carissa come to life. He finally got
fully dressed and plugged in his web cam. He made sure to have all his
toys close by to play with. Before turning on the cam, he went to the
kitchen, his heels clicking on the floor, making him even giddier. He
poured a glass of wine and headed back to the room, where he rolled a
joint and sat in front of his computer. He logged into skype, and also
pulled up fictionmania.tv, imagefap.com, xtube.com, and milovana.com. He
was ready to play, he wasn't on for ten minutes before a message popped
up on skype. It was from a guy, Carissa chatted with normally.
MASTERSMITH: Hello, are you ready to serve me slut?
Carissa didn't send a message back, just turned on the cam and waited for
him to accept. He was watching, Carissa looked into the cam. "Hello, Sir.
I am here to serve you, what would you like to start with?" She pouted
her lips and batted her eyes, trying to come off as a shy little girl.
MASTERSMITH: Get your dildo out and suck on it like it was my cock, we
need it nice a ready for that pussy of yours.
"Yes, Sir." She grabs her dildo, it's about 8 inches long and pretty
thick, she licks her lips and with one thrust it's all the way in. The
balls resting on her chin, she holds it for a second, pulls out and slams
it back. She picks up speed and fucks her mouth. Saliva pouring down her
chin and onto her dress, her eyes begin to tear.
MASTERSMITH: That's a good slut, now I want you to fuck yourself.
Carissa gets up and bends over exposing her ass, she lifts the skirt and
pulls her panties down a bit. She had already lubed up her ass, so she
knew the dildo would go right in. She slowly started to push it in, and
picked up speed. Ramming the cock deep in her ass. "OH GOD Yesss, fuck
me. Thank you daddy for making me your slut. OHH GODD YESS." Carissa
cried out, while she fucked herself.
MASTERSMITH: Good slut, I'm about to cum, better take that cock back in
your mouth.
Carissa turns around and slams the cock back into throat and fucks
herself, gagging and swallowing her ass juice.
MASTERSMITH: Oh yeah, that's it. Thanks slut.
He signs out and Tim falls over, her cock straining against its cage,
breathing heavy. She takes a swig of her wine and fixes her clothes. She
lights the joint and takes a few drags and puts it out. She heads back
into the bathroom, seeing the mess she has made of her make-up and fixes
it up, before returning to the computer.
She starts to watch various sissy videos and looks at pictures, while
slowly sliding the dildo inside her. Every so often a video would pick up
and she slammed away at her hole. A hour of playing passed by, during
which she checked a cam site for her Mistress a few times. A few months
back, Carissa came across two girls on cammodels.com and they all hit it
off really well. The girls were quite pleased with Carissa's dildo
skills. Now Carissa was addicted to showing off for them. No sign of
them, he begins looking at other models. Search's the word sissy and sees
which models were on. Nothing really caught her eye, so she switches over
to milovana and finds a nice anal sissy tease to follow. She follows the
instruction to the letter, giving her hole a god pounding, she was having
fun and feeling like a total slut. There's just something missing,
Carissa could use that dildo for hours and still didn't hit that spot she
wanted. The only way to hit that spot was to be fucked by another person.
She switches back to the cam site, wanting to find someone to play with,
someone real. She searches sissy once more, this time noticing a new
model. She clicks on her link to check out the show and read her profile.
The screen comes on, before watching she scrolls to the bio section. It
said she loves cam2cam, exploring role playing and has a soft spot for
sissy boys. What turns her on are sissies, cuckold roleplay, sph, and
joi. He then scrolls back up to watch the show. The girl is talking about
being in the scene for some years. Answering other's questions. Some
asked how she got started, why her bio mentioned sissies so much. Carissa
can't see the question, but guesses off the girl's response. "Hmm my
first sissy encounter. It had to be in high school, I went to meet my
boyfriend at the time and walked in on him dressed up jerking off online.
I totally freaked out and left him." Carissa's heart stopped as he
realized that it was Jenna on cam. His first love was now doing cam
shows. "It's a bit sad, because we never talked again, I just didn't
understand it." As she lit a cigarette. "It wasn't until a few years
later a sorority sister of mine showed me how much fun sissies could be."
Jenna continued, exhaling smoke. Carissa became increasingly hornier. She
had found her true love from so long ago, Jenna had turned out to be
everything she was looking for in a women.
She began to type. "Hello Mistress, I quite enjoyed your story. I am a
sissy and totally understand what your ex was going through." She
responded quickly, "Hello sissy, I'm glad you liked, I would love to see
what you were wearing today." "Yes Mistress, I would love to show you."
Carissa started to stream her cam. "Also you can call me Carissa, though
my real name is Tim and I use to be that boyfriend of yours." She winked
and blew a kiss to the cam. She saw Jenna's eyes light up as she smiled
from ear to ear. "Oh My God, Ti.. I mean Carissa, I can't believe it's
you, you look so cute. I'm so sorry for what happened, but it looks like
we both made it out okay." Carissa responded back, "Yes it's true, I've
been on quite the journey, and I only wish you were there to share it."
Jenna giggled, "So do I, so what have you learned? Can you show me a
thing or two." Carissa pulled her dildo out and didn't even respond, she
just opened her mouth and took the whole thing in. She started to fuck
her throat for Jenna. " Oh WOW, you take that cock better than I do, I
can take it deep with little cocks like yours, but now I have a black
boyfriend with quite the cock. That's so hot, your making me wet." Jenna
responded, "Take that cock, damn." She slammed her throat for a good five
minutes. "Okay go ahead and stop slut." Carissa took the cock out and
swallowed hard. "I don't even know what to say, running into you like
this." Carissa typed away. "I know, so where are you living? What are
doing with your life? Well other than being a slut online haha." Jenna
said with a laugh. "I'm living up in San Francisco, have a basic day job
and such, haha." Tim typed back. "Shut up, I live over in Oakland with my
boyfriend Rodger. We defiantly have to meet up." Tim's heart stopped, he
would be able to see her in person, but the doubt crept in how could he
after having degraded himself as such. "What's your email, I'll send you
a message and we can figure things out?" Jenna asked. Tim wanted to stop,
and disconnect, but typed his email in and sent the message. "Okay,
awesome. I can't wait to see this in person." Jenna said and logged off.
Tim took his wig off and looked at the ceiling, not sure of what had just
happened and his mid raced with the possibilities.
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