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                 K R I S T E N' S    C O L L E C T I O N
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Melissa's Sissy Boifriend
by Masterrr15 (masterrr15@hotmail.com)

***

A college freshman hooks up with the meanest girl in 
high school. He quickly is dominated by her and turned 
into her personal sissy-slave porn-star. (Fdom/M-teens, 
1st-gay-expr, trans, bd, drugs)

***

The week before my state college's winter break I was 
eating in our lunch hall reading one of my magazines 
when a loud and commanding female voice asked, "Is 
anyone sitting here?" I quickly looked up and my heart 
rate skyrocketed upwards when I realized that it was 
Melissa the meanest girl from my high school. To say 
that this girl is mean is in my mind at least, an 
understatement. 

I can still remember the first week she came to our 
small Northern Virginia high school from NY, she beat 
up any guy or girl who got in her way. During one very 
bad fight several of the resident mean girls jumped her 
after school, Melissa not only beat the crap out of the 
other ice princesses, but also the first couple of 
teachers who tried to break up the fight. 

No one messed with her after that! Not long after she 
had exerted her dominance at our high school, we 
quickly learned that she could hit you with her words, 
just as hard as she could with her fists. I have been 
interested in femdom since high school so she was in 
many of my high school fantasies.

"Hello?! I am talking to your dumbass!" She barked and 
handed me a napkin and told me to wipe her a clean area 
on the table. "I would like for you to help me with my 
stupid calculus class, you somehow understand that 
crap," Melissa said as she sat down. 

"M-my last class is at 4pm today and I can be at your 
place soon after," I stammered. 

"Come over around 6pm, and what the hell are you 
eating?! You are not in good enough shape for pizza, 
god men are such morons!" She picked up my entire tray 
and threw my food in the trash. "Go get a salad, and do 
not use any other dressing other than oil and vinegar." 

Right at six o clock I was at her door. We studied late 
into the night. The next day she came over to my dorm 
room, and started to look around. "Uh yah, this needs 
to go," she said as she started to rip my Sports 
Illustrated swimsuit model posters off the wall. "Don't 
worry I will bring over some tasteful posters."

She then started to go through my drawers and my heart 
rate leapt into my throat as she pulled out my pairs of 
flowery panties. She glared at me, "What are you gay or 
something?" I explained that I wasn't gay and just 
liked to wear panties sometimes to get a thrill from 
knowing that other students didn't know what naughty 
undergarments I was wearing under my trousers. 

"Interesting, very interesting," was all she said as 
she went back to digging through my drawers finding 
more panties, bras, and pantyhose. 

"Um," I said not wanting to interrupt, "I-I have to go 
to my history class." 

"Great, I can't make that class today, this room needs 
some serious work. Take very good notes for me or I 
will beat the crap out of you," she barked. 

I instantly started to get a stiffy from her verbal 
abuse. Melissa looked at my crotch and laughed, "Yup, I 
figured you liked that stuff, otherwise you would have 
run the other way the second you saw me, correct? You 
better get to class now!!" She said with even more 
authority than before. 

All through history class I struggled to pay attention. 
I couldn't help thinking about what could be my 
greatest dream come true. I just hoped that I could 
handle actually being a subservient in a dominant 
relationship. Would I chicken out, would it be too 
much? The bell rang and it was time for me to go back 
to my room. When I entered my dorm room, my jaw fell 
open. 

Melissa was not there, but all of my bikini posters had 
been replaced by pictures of hot guys in tight thong 
speedos. A small package with a note attached sat on my 
bed. As my eyes moved to the package, I notice that she 
had replaced my plain white comforter, to a white 
comforter with small flowers all over it, pretty much 
in the same pattern as my Victoria's Secret panties 
Melissa found earlier in the day. 

I read her note, she wanted me to take a shower, wash 
my hair and body with a strong flowery scent, then dry 
off, moisturize my body from head to foot with the 
enclosed nice smelling moisturizer, put on my new pair 
of matching panties and a bra (both pink with little 
hearts on them), a dress with a floral print from 
Victoria's Secret, and to finish up my new outfit with 
makeup and a blond wig with pigtails, each pigtail tied 
with a bright pink ribbon. 

Melissa also had found one of my many pictures of me in 
drag, she circled the picture and stated that she had 
no idea how I created the cleavage in the picture, but 
wanted me to duplicate whatever I did for tonight's 
meeting. The last thing the note said, was to spray 
myself with the enclosed bottle of Beautiful perfume 
and then to head over to Melissa's dorm room ASAP.

After preparing for our date, I peered out my door. I 
have a small frame, but my current outfit was going to 
get a lot of attention. My floral dress wasn't very 
long and let a lot of my fake cleavage show. I figured 
I would just have to suck it up and go. I counted to 
ten and pushed myself to go outside. I quickly headed 
out toward Melissa's dorm almost on the opposite side 
of our campus. Luckily the path is quite dark until I 
got near my destination. 

So far so good, I thought to myself, I pushed myself to 
walk as fast as I could without falling over. Just 
before I reached Melissa's room two large basketball 
players passed by me. "Good evening Miss, I hope you 
don't mind if I say your outfit is wonderful. Its nice 
to see that there are a few women still out there that 
don't dress like a bunch of femi-nazi dykes in loose 
black jeans and shit." 

It was Jeb, our most popular player, of course he was a 
hit with all of the ladies. "Thank you," I said 
quickly, "but I am late to meet my boyfriend." 

"Shit," he replied, "I should have known a chic like 
you would be already spoken for, ha, ha, well you know 
where to find me if something falls through." 

I thanked him and hurried on. 

Finally I reached Melissa's door. When the door opened, 
Melissa was standing there in the doorway. "Get inside 
now bitch, fucking whore. I saw you flirting with those 
two guys."

She pulled me inside and pushed my face into her bed, 
so my butt was sticking up in the air. She started 
whipping my butt with a belt. After about twenty or so 
hard hits to my now tender rear end she stopped. Tears 
were now streaming down my face as Melissa sat down 
beside me on her bed. "God dammit, now your mascara is 
running down your face," she growled. Melissa rested a 
bit and I basically just whimpered and rubbed my sore 
butt. 

"So you really want a bitchy dominant girlfriend, 
right?!" Melissa asked, already knowing the likely 
answer. I looked into her beautiful crystal blue eyes 
and had to admit that femdom was about the only thing 
that excited me. 

"Well," she said, "I used to think that I was a 
lesbian, but now I know that I want a sissy boy." She 
leaned over and whispered and gently blew in my ear, 
"You want to be my little sissy girl don't you, admit 
it bitch."

"Oh god yes, please let me worship you mistress," I 
pleaded. 

Melissa smiled and said, "Do you like your pretty pink 
panties, slut." As she said this she started to pull my 
panties down. "You wanted to suck those hot guys on the 
walkway didn't you, you little faggot sissy slut." 

I stammered that she was wrong, I wasn't gay. 

"No!" she yelled as she started pulling my panties back 
up. "Let me make this clear to you sissy, admit you are 
a cock sucking slut and panties slip off and I will let 
you put your little clit inside me, or be an idiot and 
deny it, then your panties go up and you can walk home 
with blue balls. Got it bitch!? Admit you are a sissy 
faggot and panties go down, or be a damn pain in the 
ass liar and it is blue ball city, simple enough for 
you dumbass?!" Melissa shouted. 

My horniness took over and so I said that I wanted to 
suck the jocks hard dicks. "Umm, yes I thought so she 
laughed. Will you drink their cum for me, please lil' 
sissy girl, right kitten?!" Again my reason was 
overcome by my growing need to get off. "YES!!" I 
proclaimed loudly in a pleading voice yeaning for 
Mistress Melissa's attention. 

She pulled my panties off and quickly removed both of 
our clothes. Melissa smiled as she got on top of me and 
guided my cock into her love channel. At first my penis 
missed its mark and slid past her opening and instead 
when up along her leg. "Oh, you know you want this, 
right kitten?" Melissa teased. 

I gave her a confused look, then quickly said, "Uuhhh, 
yes!" 

"Uh, you don't know if you want pussy? You sound unsure 
there little girl. Oh my god, are you a virgin? I mean 
it is OK if you are I just want the truth." Melissa 
continued her tormenting. 

I again looked into her eyes and admitted that I was 
still a virgin after all these years. "Wow, cool!" she 
laughed. Then in a mocking voice she stared to sing the 
Red Hot Chili Peppers song, "Breaking the girl," just 
to humiliate me further. 

My new mistress reached back and grabbed my little 
sissy dick, then grinned like a Chester cat as she 
guided my cock inside of her. It was amazing to feel my 
cock push through her opening and slide into her hot 
wet cunt. Melissa slid up and down on my cock a few 
times then slowly leaned forward so we were face to 
face with her fucking me. 

"So what kind of nasty fantasies does my little sissy 
kitten stroke herself to when you have your little 
girly hand wrapped around your tiny dick, humm bitch, 
and you better not fucking lie to me, tell me bitch! 
Don't hold back and don't you dare lie. As a matter of 
fact, I fucking command you to tell me your secrets, I 
know you don't want to reveal some things, but it will 
come out eventually and I will be very fucking pissed 
if you lie to me, got it you fucking little shit!" 

She grabbed my hair under my wig and said, "Come on, 
speak, tell me what I want to know, you know you have 
to confess to mistress Melissa, right whore?!"

In a moment of amazing horniness with her warm wet cunt 
gripping my cock and her warm juices dripping onto my 
balls I lost all resistence and told Melissa that I 
masturbated primarily to cuckolding, humiliation, and 
also got off on latex fetish pictures and stories. 

Melissa smiled, "God, we were made for each other." 

Tears sprang to my eyes I was so happy she liked what I 
wanted and wanted my fantasies to come true. At the 
same time I was a bit worried that I wouldn't be able 
to handle one of my stroke stories from jumping from a 
harmless story online to reality, but it was a little 
late to put the cat back in the back in the bag if it 
was too much. 

Melissa started moaning and started chanting, "My own 
little cuckold sissy slut, oh god yes, yes!" 

I could feel her vaginal muscles tightening around my 
cock as I felt my own orgasm building. My cock swelled 
inside of Melissa as I climaxed inside of my mistress. 
Jets of sperm shooting inside of her sent her over the 
edge and she started screaming as she climaxed at 
almost the same time.

***

During the winter break from classes, Melissa and I 
spent the days talking and having sex many times each 
day. I was amazed at how sexual she was. She constantly 
told me about her previous boyfriends and compared my 
dick to theirs. I couldn't get enough of her 
humiliating me on my inadequate pecker. On the Friday 
of our first week off, we were in the lunch hall again, 
this time Melissa's long term friend Jenni joined us. 

I sat down with my new usual meal of a salad, ice tea 
with no sweetener, and some vitamins Melissa wanted me 
to take. "So," Jenni started, "Melissa tells me that 
you are her sex slave and you like to be dominated by a 
beautiful bossy women." 

I couldn't believe that Melissa had told her about our 
situation. My reddening face told her that what Melissa 
had told her was indeed true. As Melissa sat down at 
the table, she commanded, "Well answer my friend slut!" 
I admitted that I loved Melissa's humiliation and I was 
totally in love with my mistress.

Jenni laughed and added that Melissa told her about my 
small cock and how I liked to wear panties. My face was 
bright red and mistress commanded me to show Jenni my 
panties. Jenni broke out laughing when she saw my pink 
panties. "Well, Ok, Jenni said, "Whatever makes you 
happy." 

She continued to debase me by adding, "Melissa is 
right, all I can see is a tiny bump in your panties, 
without that tiny bump no one would mistake you for a 
man." 

Melissa turned to Jenni and they talked about how they 
loved to dress up in provocative outfits and drive guys 
nuts. We should do that tonight, Jenni and added, "I 
would love to tease boys plus if I find a real man," 
Melissa turned to look me right in the face and added, 
"I could fuck his brains out." 

Still looking at me my mistress added, "You want me to 
have real dick, right? Plus if you're good I could let 
you watch, you know you might learn something." 

I was totally humiliated, but I wanted to see my 
princess happy even if it hurt me. I was jealous but 
excited by the idea of Melissa making love to another 
man. The idea made me very excited, but for some reason 
my cock remained soft. After our dinner we want to 
Melissa's dorm room and prepared for our night out on 
the town.
     
Melissa had me wear the same outfit I had originally 
met her in on our first "date" except now she added a 
white garter belt and white fishnet stocking. "Ouch" I 
said as my bra rubbed past my nipple, "Man my chest is 
sensitive all of a sudden." 

Jenni spoke up, "That's probably a side effect of the 
female hormones." 

Melissa shot a pissed off look at Jenni, and said, "I 
was going to tell him about that later." 

"Oh crap, I am so sorry Melissa!" Jenni pleaded. 

"Well, we better let this little bitch on to what is 
really gong on. I have been giving you female hormones 
telling you that they are vitamins and the moisturizer 
you have been rubbing into your body from head to foot 
is from a transformation website and is packed with the 
maximum amount of estrogen possible. 

"I figured that you wouldn't mind being a bit more 
feminine plus, it might make what I have to tell you a 
bit less jealous if you don't have all that nasty 
testosterone going through your veins. This week my old 
boyfriend called me. He is an older gentleman but, he 
has a nice big fat cock and is very experienced. I love 
fucking him and we are going to meet him tonight."

It was almost too much to process at one time. I was 
angry, jealous, nervous about the effects of the female 
hormones, and horny all mixed together, basically a 
cocktail of emotions. 

I kept thing about Melissa with her old boyfriend the 
entire way to the clubs around D.C. At a bar in 
Georgetown we met up with the infamous Bill. He was an 
older guy, and I could tell why Melissa liked him, he 
was clean cut, sophisticated, and very confident. You 
know, basically everything I wasn't. I noticed that the 
bar we were in, was a mixed bar with straight and gay 
sections. 

Jenni grabbed my hand as Bill and Melissa went to a 
booth and stared making out. "Come on!! Let's leave 
them alone, plus I want to check out all the hot gay 
guys, maybe I can convert one of them," she laughed. We 
sat down at the bar and Jenni told me to turn sideways 
and push my chest out. As I did, she mentioned how my 
breasts were already starting to grow. Your breasts 
should be about one cup smaller than your sister's."

I gave her a panicked look and told her that my sister 
was a double D. 

"Well you should have some big hooters soon," she 
stated while laughing. A guy sitting next to us broke 
in, "I am sorry but I couldn't help but over hear some 
of your conversation. Are you a she-male? Before I 
could say anything Jenni answered for me. 

"Chrissy is already on female hormones, but isn't sure 
how far she will take things right now." 

He exclaimed, "That is so cool! We get a lot of drag 
queens in Dupont Circle, but not too many people are 
willing to take the extra step and start getting 
permanent things like breasts. Let me buy you girls a 
drink," he said in a nonchalant tone. 

He got Jenni and I a Manhattan, then turned to his 
friends and told them about me. After two drinks he 
asked me to go out on the dance floor. Jenni wouldn't 
let me answer no. "Melissa wants you to have some fun 
too, girl," she grinned wildly as she said this. 

I went out on the dance floor with a third drink as 
Melissa joined Jenni at the gay section of the bar. As 
I danced with my "date" I watched Bill openly fingering 
Melissa at the bar. I was getting turned on by my 
"date" constantly telling me how pretty I was and 
grinding his hard cock into my softening feminine butt. 

Melissa brought Bill out onto the dance floor and she 
gave me another drink as she passed by. She then 
started to passionately french-kiss Bill and I could 
see his hands rooming over her body. I was somewhat 
jealous, but amazed how aggressive and brazen Bill was 
in public. 

Bill looked at me and told Melissa he could see why she 
still needed him, "You are pretty much a sissy boy 
aren't you, god you almost look like a woman, ha, ha." 
He added insult to injury and continued his humiliation 
of me, "Do you want to see a real man fuck your 
girlfriend? My face was burning with humiliation.

Melissa spoke up, "Go on sissy slave show Bill your 
small dick," as she said this, she laughed and pressed 
Bills pants tight around his impressive cock. "Slave 
tell him that you have a small girly cock and would 
like for your mistress to enjoy a real man for a 
change," she commanded. 

My face turned several shades of red as I followed my 
mistress's orders and stated, "I have a small cock and 
would like for Melissa to enjoy a real man's cock." 
Melissa smiled as Bill pushed her down to his crotch. 
She took Bill's cock out and said that I should follow 
along with my boyfriend. The guy I was dancing with got 
a huge smile on his face and pushed me down onto my 
knees. 

I am not sure if it was the drinks of the humiliation 
but I didn't want to displease my mistress. I pulled 
out his cock, and followed Melissa's lead. I watched as 
Melissa sucked up and down on Bill' hard member, every 
once in a while she would stop to concentrate on the 
head of his cock and run her tongue around the head of 
his fuck-stick. 

My new friend pushed his hard cock down my throat and I 
felt someone pushing my panties down. I wanted to see 
who was behind me, but all I could see was the man's 
cock I was sucking. God what a slut, Melissa said as 
she decided to take things a bit further with Bill. She 
stopped sucking his cock and told him to fuck her and 
to not pull out until he had shot a nice load of cum in 
her cunt. I felt a cock slipping into my ass as I 
continued to suck the cock in front of me. Melissa 
pretty much kept pace with me until Bill started to 
moan. 

Melissa turned and laughed at me, "You're so pretty my 
little cuckold slut." I hope you enjoy watching your 
girlfriend getting knocked up by a real man. I looked 
quizzically at her as she said this. "This is your last 
test, plus you have been the one taking all my birth 
control pills to femininize you. I could only look on 
with amazement as I watched Bill cum in my mistress' 
pussy, shooting his fertile seed deep into my 
unprotected mistress's uterus. 

As Bill climaxed my boyfriend shot his load into my 
mouth, and my apparent second "friend" came in my sissy 
pussy. I came with my worthless cuckold sperm shooting 
onto the dance floor. Billed looked over at me and said 
that my sissy sperm belonged on the floor and not 
inside of a women. Bill, Jenni, and Melissa all laughed 
as Jenni added, "No, babies for the sissy faggot, like 
any women would want sissy faggot genes."

After that night Bill let Melissa and myself move into 
his large vacation house, located on a private beach in 
Hawaii. Melissa continued my feminization and my new 
boyfriend introduced me to my new job as a she-male 
porn star, of course taking all the profits and sharing 
them with Bill and Melissa. He had videotaped the 
entire dance floor sex scene with me taking on two men 
at once, and then he made the video available on all of 
his numerous gay porn websites. 

Once word got around that I was a feminized she-male 
starring in my own porn video, my old life was pretty 
much over with. Knowing that there wasn't too much hope 
of me finding gainful employment outside of the porn 
industry, I resigned myself to my fate and spent my 
days starring in she-male porn videos and my nights 
serving mistress Melissa and her many lovers. Life is 
good ;)

END

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
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