Carissa at Camp
- 2 years ago
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Carissa's Journey free porn video
The light filled the room slowly, filling the room with a soft glow. It
wasn't even fully out when 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 his 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 male underwear, and wears panties
daily. He would dress more, but having roommates has limited his
dressing time. That fact makes this weekend 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
masters and mistresses. Once a month he attended a sissy social night at
a local caf?. There were several sissies that would show up, some
regulars, some first timers. 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 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 it. 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 fit from playing sports. She was going to on the 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. It was also the time when having a computer
with internet was popping up. So they spent hours talking on ICQ all
night, which turned into texting once he got his first cell phone. 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. The first time like many was done
and over quickly, but there were many of times after that. Tim and Jenna
had dated for over a year now and were coming close to the end of their
senior year. They talked about college, and staying together, they loved
each other. 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.
His dressing hadn't been going on of late, since he was busy with
school, track, work and his girlfriend. He was feeling frustrated and
mostly took it out on Jenna in the bed room, but knowing he had weekend
to dress, made him excited. He got dressed up on 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 as 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 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. This
filled his head off and on, he would date girls in college, even fall in
love again. It didn't work out, not like how Jenna fell apart, but just
normal relationship differences. After his second year the desire to
dress was too much to push down.
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 he was enjoying it. 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 it
was here for the first time, did Tim notice the hole in the wall. 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.
This went on during the rest of his college years, he even started
meeting up men at their houses to dress for them and play. Over the next
few years, he would dress up and play, then get guilty and stop. It
would cycle, he would try to move on and forget about it, but the desire
always came back. This brings us back to where we are, Tim had been
dressing more and wanted to be the slut he was in college.
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, unable to
relief himself, the horniness just grew. After his tinkle, he turns on
the water in the tub. As the tub filled up, he pours in some perfume and
bubble bath, 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.
The water was released and he dried off, applying some lotion and stood
in front 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. 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 as 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 set 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 blinked 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,
and her 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. This goes on for about an hour,
every so often she is checking her normal cam site for her Mistress. A
few months back, Carissa came across two girls on a cam site 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 who pops up. After continuing and finding nothing with the cam
models, he switches over to milovana and finds a nice anal sissy tease
to follow. He does everything that is said and really pounds his hole
along the way, having fun and feeling like a total slut. There's just
something missing, that real human touch isn't there, and Carissa knows
it.
She switches back to the cam site, since it's the most personal he has
found online. He needs a real person to play with. He searches sissy
once more, this time he notices a girl he hasn't seen before. He clicks
on her link to check out the show and her stats. The screen comes on, he
scrolls down to her stats. It says in the about me section 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. The question
about her first incident seems to come up. 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. It
wasn't tell a few later a sorority sister of mine showed me how fun
sissies could be." Jenna continued. Carissa became increasingly hornier.
He had found is true love from so long ago, she had turned out to be
everything he was looking for in a women. He checked her prices, 3.99 a
minute seemed like a good price.
He 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.
Also you can call me Carissa, though my real name is Tim and I use to be
that boyfriend of yours." He saw her eyes light up as she smiled from
ear to ear. "Oh My God, TI I mean Carissa, I can't believe it's you,
let's go private, I want to see you. Carissa clicked the go private
button. She then allowed access to her cam. The session started, he
waived to the cam. "Tim, I can't believe that'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, 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 can, and I have a black
boyfriend with quite the cock. That's so hot, your making me wet." Jenna
responded, "Take that cock, damn." He slammed his 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 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
again, he would be able to see her in person, but could he 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, nice
yeah I'll stay in touch." Jenna said and logged off. Tim's world was a
bit upside down.
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