| Keywords: tg/f, inc, oralPart: 3 of 4Author: Brett LynnTitle: Marilyn's
Beginnings: Marilyn Becomes A
OK, welcome to the next installment of my erotic tale. Sorry about the
formatting problems from the last edition. This one is supposed to be a
bit of a climax (no pun intended) to the prequel series. This will also
hopefully be very different from every piece of transgendered erotica that
you’ve ever read. You’ll see why when you read this. Ah, what fun it is
to have such a twisted mind. Thank God that the only way this will be
traced to me is by search warrant. I know America’s so loving and
understanding when it comes to alternative sexualities. That’s why the
Internet is filled with HNG’s looking for shemales to fuck on one hand,
while they get drunk with the and beat the crap out of ‘sissies’ in
the other. What a wonderful world! ;-) Now for the most erotic part (or
at least I hope it isn’t) of this tale…the disclaimer.
This work of fiction is for the non-commercial use of its readers.
Permission to copy and distribute through electronic media for
non-commercial purposes is granted. All commercial and non-electronic
rights are reserved by me, the author. Please do not read this if
you are offended by adult material, reading this material is illegal in
your legal jurisdiction or, if in the United States, under the age of 18.
It ain't like this disclaimer is going to stop the determined, but I gotta
try. So without further ado, on with the story.
MARILYN’S BEGINNINGS 3: MARILYN BECOMES A By Brett Lynn
Marilyn woke up refreshed from a nice night’s sleep. A good can do
that to you, with the release from your muscles and the endorphins swimming
around in her bloodstream. She sat up, stretched her arms, threw off the
covers and stepped out of the bed. She stood up, tucked herself up, pulled
on a T-shirt, some and shorts and walked downstairs to get
something to eat for breakfast.
When she walked into the kitchen to pour herself some cereal, she ran
into her father, sitting down drinking some coffee and reading the paper
after a hard night as a senior system administrator. His head and face
were covered with the salt and pepper hair that betrayed his age. He had a
stocky build that was padded with some fat that came with a slower
metabolism. However, when he stood up to his full 6’2” height, he did
impose a commanding, respected form.
“Hey Dad. How was work?”
“Hey child of mine. Same ol’, same ol’. Nothing unusual.”
“Cool. Can I see the sports section after you’re finished?”
“Sure, son. No problem.”
Marilyn pulled the milk out of the fridge and poured it onto her Frosted
Flakes. As she replaced the milk, got her spoon and sat down to eat, she
noticed her looking at her funny again. Then again, her always managed to do that. After all, he wasn’t exactly very accepting of
the changes that his only son went through. Fathers often expect their
sons to follow in their footsteps, especially socially speaking. The last
thing most fathers expect from their sons is for them to become female
before their very eyes.
“So, son, what are your plans for today?”
“Oh, nothing much really. Might go out to Queens to see Kat, hang out
and stuff you know?”
“Cool. Hope you enjoy yourself.”
That got Marilyn thinking back a while, to a time when her didn’t
react so benignly to her new look…
It was towards the end of her sophomore year at Queens Lutheran High.
Things were going decently for Donnie/Marilyn. Donnie was starting to
identify himself more as Marilyn these days. After all, one look at
himself as he took a shower on a Saturday afternoon gave him all the reason
he needed. Playing to the genes he carries from his mother, the hormones
coursing through his system gave him nice sized boobs. When he measured
his chest out of curiosity of the developments on it, he measured himself
as a 40C in the bra department. Actually, as measured, he would be a bit
on the tight side in a C cup bra, but loose in a D cup. However, the legs
and especially the arms seemed to go the other way on the gender continuum.
From working out during the basketball season, her arms got bigger and more
cut, vaguely resembling something on a body builder. His legs weren’t as
defined, especially in the thighs, but they were somewhat big and muscular
nonetheless. However, his legs seemed vaguely feminine enough, especially
since they were shaved, that it contributed to his new feminine body image.
The ever- lengthening cornrows finished off the gender conundrum that was
his body. In fact, when they were let loose occasionally, his hair looked
like the wavy hair of a woman than of a man.
As she stepped out of the shower and started drying himself, Marilyn saw
the one thing that was definitely all-male. His dick seemed to grow bigger
and bigger, seemingly in a rebellion against the subtle and not-so-subtle
feminization of his body. In the past several months, another two inches
had been added to his erect length, bringing the total length to about 11
inches. On top of that, it had become thicker to the point that he could
barely wrap his fingers around it when it was hard. Speaking of hardness,
it was starting to get that way as the terry cloth tickled his tip as he
dried it off. He decided to indulge himself in a little bit of
masturbation, not enough for a release, but just enough to give him a nice
little tingle. He let the towel go limp in his right hand while he gently
stroked himself with his left.
“Whoa! S-so sorry…I’ll be right back. Uh, we’ll speak about this
Donnie jumped back as he realized who just opened the door. As with any
other teenager, he was shocked when his walked in on him pleasuring
himself. What was unusual, however, was that his was scanning his
body. See, Donnie’s dad had never seen him en femme before, and he was
looking at the somewhat rounded hips and sizable of what he thought
was his son. After all, the person before him did have a penis, and there
could be only one other person with a penis fresh out of the shower in this
house. Donnie had taken care to avoid walking around as Marilyn when his
dad was in the house. After all, he didn’t know how he was going to take
it. He took care to wear sports bras when his mammary endowments became
too large to hide in baggy shirts, and he always took care to be modest
around his father. Now, though, he was going to have to face up to the
“OK Dad. See ya when you get in tomorrow.”
With that, the door closed, the conversation ended and the secret was
out. Donnie vaguely heard his calling for his mother. “Well, I
presume that ends that secret,” he thought to himself. With that, he
pulled his T-shirt over his head, pulled on his briefs and shorts and
walked out of the bathroom over to his sister’s room.
“Sis, we gotta talk”
“What’s up Marilyn?” answered Sharilynn as she sat up from listening to
“Something big just happened.”
“You know Dad? Well, he just met Marilyn.”
“Huh? How is that possible? I know he came back to get something he
left in the living room…”
“…But apparently he needed to go to the bathroom. I was just getting
out of the shower when he opened the door.”
“I wonder how he’s gonna react. I hope he doesn’t take the wrong
meaning out of his discovery.”
“He probably is. I know he tries to be helpful, but he’s so damn
meddling at times. Could you braid my hair now please?”
“Sure, sis,” Sharilynn replied as she rolled over to get her comb and
hair grease from her night stand drawer. “You know, with your hair, you
could probably get it done nice if you ever wanted to live full-time as
Marilyn,” she said as she started to comb out her unusual brother’s hair.
“You’re probably right. The thing I’m afraid of is that knowing Dad,
‘ever’ is coming real soon.”
THE NEXT DAY
Donnie walked into the living room around 11 that morning looking to
catch the Sunday morning edition of SportsCenter. He was tired and missed
a lot of the previous night’s sports action on TV. Then again, the reason
he was tired contributed to the reason he missed the previous night’s
games; a couple of blowjobs plus a marathon masturbation session where he
came so hard that he passed out has the ability to drain someone like that,
both physically and mentally. He was dressed in a “Lutheran Basketball”
T-shirt he found laying around in his room and some shorts. He didn’t
bother with any briefs because of how sore he was, and he didn’t bother
with the sports bra because, he thought to himself, “ain’t no use hiding it
He conveniently saw his sitting down watching SportsCenter on the
couch. “Look like the Yankees are on a bit of a tear,” Mr. Walker said to
no one in particular. “After the way they’ve been running through the
league, they seem to be a World Series lock.”
“Hey son,” his replied. “Well, let’s talk. Your told me
all the medical details about how this got started. So what do you go by
when you’re like this?”
“Alright, um, Marilyn, I understand what you feel. I mean, I thought
this was something you only saw on to grown people, but it’s different
when you see it on TV.”
“Anyway, I understand it must be hard for someone like you to be a
teenager and like this, especially with dates and stuff. So I decided to
fix you up on a date with my friend’s son.”
“Don’t worry. It’s OK. I’ll let him know about your condition
beforehand. Besides, I think he has some tendencies, you know?”
Marilyn was in utter shock and disgust when she heard the news. “Where
does this asshole get off thinking I like now because I have boobs!”
she thought to herself. Then, while her dad prattled on about details
about the date, she saw her in the hallway listening to the
proceedings and mouthing to her “don’t worry. We’ll talk after he’s
“So how’s Friday night for you son, er, Marilyn.”
“It’s OK, it’s OK,” Marilyn said as she gave her the brush-off
and went into the hallway with her sis. “Told you that was gonna happen,
Shari. Now what?!”
“Relax, relax. Look, I’ll let you borrow one of my dresses. Even
though you are taller than me, you aren’t as filled out in the chest or the
butt. And I’ll take you shopping for some more feminine underwear,
alright? Besides, you need something to hold yourself in besides some
sports bras. Aren’t they a bit uncomfortable?”
“True. Besides, while I don’t wanna be jiggling all over the place, I
don’t want to be squashed either.”
“And one last thing…I know you say you’re straight and all, but you
gotta give a fair shot before you say you don’t like them. Come on,
do it for me. If you don’t like it, I’ll make it worth your while,”
Sharilynn said with a wink.
“Aw, alright sis. Let’s go to your room and look through some dresses…”
THE FOLLOWING FRIDAY…
“C’mon Marilyn! Let’s get a move on!”
“Ah man. I dunno why we have to go through this.”
“Look,” Sharilynn said, lightly tugging on her brother’s hand to get him
into her bedroom, “you gotta go through this to get ready. At least you
have your braids loose. It’s a start.”
Sharilynn sat her sibling on her bed to get her ready to her date. Of
course, Marilyn was still going to school as Donnie, and she still wore her
usual baggy polo and jeans. However, in advance of the impending
date, Sharilynn convinced her sibling to allow her to put some texturizer
in his hair before getting it braided. Sharilynn smiles as the combined
effects of the braiding and the texturizing solution gave her something to
work with hair wise. “Thank God for small favors,” she thought to herself.
“At least I can comb it to look right.”
“Now take off your clothes…all of them.”
“Oh, alright sis,” Donnie reluctantly complied and shucked off his
boots, jeans, shirt, underwear and sports bra. When he bent down to take
off his socks, he looked at his and said, “I’m ready. Let’s get
this over with.”
“Come on, Marilyn,” replied Sharilynn, looking at her feminine brother.
“Cheer up! You’ll do fine.” She then gave her a peck on the cheek
and got the Victoria’s Secret bag that she had laying in the corner.
Pulling out a white set of bra and panties, she said, “here. Wear this.
It’ll look nice on you.”
Taking the lacy underwear from her sister, she held them out in front of
her face and said, “you’re right. Let me put this on.”
Marilyn remembered trying on the underwear earlier in the week. Since
the siblings knew that there would be no way he could go into any lingerie
store in her normal attire asking for a bra, she had let her get the
underwear for her, since her knew her sizes. Sharilynn had smartly
gotten her some front-closing 38C bras, the easier for her sibling to
manipulate, and some lacy substantial enough to hold in her
sibling’s lower endowments in white, black and red. Marilyn pulled on the
bra like a vest, then struggled to pull the cups around her and to
latch the clasp in the front.
“Man, this is tight,” Marilyn said, looking at her practically
pouring out of the bra.
“I know. If I remember your measurements correctly, you are between cup
sizes. It’s better to be too tight that too loose. It looks better. Now
tuck yourself up and pull on your panties, and let’s look at the whole
package, if you pardon the pun.”
Marilyn spread his legs slightly, grasped her dick at the base with one
hand and pulled the tip straight down with the other. Then the hand that
was at the base of her cock pulled it back and into the crack of her ass.
“Ouch, that hurts,” he said to himself. Then he took the panties, put his
feet through them and pulled them up her legs.
“Don’t sweat it, my sis o’ mine. The pull will loosen it self up
throughout the night, plus the will help to hold yourself in as
well. Now let’s take a look at yourself in the mirror.”
The siblings walked over to the mirror behind the dresser and saw an
interesting sight. On one hand, there was Sharilynn, dressed in an T-shirt and shorts. The other image was something unusual. There stood a
girl, with hair that needed to be combed, popping and curves
curving. Even the broad shoulders, big arms and lack of makeup didn’t
detract from the beautiful sight in the mirror. “Damn,” Marilyn said to
her sis while looking in the mirror, “I look fine! So what’s next?”
“Stop being so vain,” her shot back while getting a dress from
her closet door. “Here, put this on.” Sharilynn handed her a navy
blue sundress with a flower print on it. Marilyn pulled the dress over her
head. She then buttoned up the bodice from her waist, leaving a small
amount of showing. Then, her picked a tube of coral pink
lipstick and pointed her face towards the mirror.
“Pout for me please?” her asked.
She pouted on cue, and then her spread out the lipstick on her
lips. She made a kiss in the air and saw that the lipstick that her put on came out perfectly.
“Oh, by the way, I got you some all-white walking sneakers and some
cute-looking white socks. I knew we didn’t have the time to get you any
heels or anything.”
She sat down on the bed, pulled on the socks and laced up the sneakers.
“Right on cue. Well, sis, I wish all the luck in the world. Enjoy your
date!” Sharilynn said.
“Alright, sis,” Marilyn said before she gave her a kiss on the
cheek. “I’ll let you know how it works out.” She then bounded out her
sister’s room into the living room to see her and her date. She saw
her dad chattering away about some religion she didn’t half understand when
her dad noticed she had walked into the room.
“Oh, there you are. Marilyn, meet your date,” Mr. Walker said.
“Hi! I’m William Dixon, your date for the evening,” the caramel skinned
guy on the couch said to her. He then stood up, took Marilyn’s hand in his
and kissed it. “Pleasure to meet your acquaintance.” Then he hugged
Marilyn tight and gave her a kiss on the cheek. Marilyn shuddered for a
bit, uncomfortable with the feel of a guy against her, especially trying to
kiss her. However, she took a deep breath and responded coolly, “well,
it’s a pleasure to meet you to.”
“Look, we need to get going. I gonna take us to get something to eat,
then we’ll go out to a movie. Sounds fine by you?”
“Yeah, it sounds OK,” Marilyn replied, trying her best to like what was
“Marilyn!” said her as she ran in, “here’s a purse with your
wallet in it. Now enjoy yourself!”
“We will,” responded William. He took Marilyn’s hand and took both of
them out of the door to his car. “See you later, guys!”
The dinner before the at Lobster was simple enough. The only
thing out of the ordinary was that Marilyn was constantly checking around
for people she knew, afraid that she would be found out. Of course, there
was the simple conversation. William was a graduating senior in high
school from Harlem. He was on his way to at SUNY-Albany and, as
was par for the course with anyone connected with her father, was a bit of
a hippie interested in all kinds of weird religions and stuff. “Well, at
least I’m getting free food out the deal”, Marilyn thought to herself.
Mercifully, dinner was over, for Marilyn was at least, and the dating
couple was off to the movies. They had gone to see the remake of the great
Hitchcock classic “Psycho.” “It was a decent movie, but the colorization
took some of the edge off of it,” Marilyn thought to herself. While
Marilyn was playing Siskel and Ebert in her own mind, William was playing
with something much closer to home for Marilyn. First, she felt William
stroke her hair with her fingers. Then, William’s fingers led his arm
around her shoulder for a nice, tight one-armed hug.
“Are you OK with this movie?” William whispered in her ear.
“Yes, I’m OK,” Marilyn responded coldly.
Then William pursed his lips close to his date’s ear and blew in it.
With his free hand, he touched her knee, then slid his hand halfway up her
thigh. “Are you sure?” he asked again just before giving his date another
kiss on the cheek. “Yes,” Marilyn responded with gritted teeth, “now let’s
just watch the movie.”
Thankfully, Marilyn’s date didn’t get fresh with her the rest of the
movie. The ride home was pretty uneventful, if not downright quiet.
However, when they ended up pulled in front of Marilyn’s house, William
decided to get a bit more amorous. Staring in her cleavage, her date said
to her, “you know you’re a beautiful girl, and, you know, I like you a lot.
I just wanna show you how I feel."” With that, William leaned towards
Marilyn in the passenger seat to nibble on her neck. In response, she held
onto his shoulder and said with an edge in her voice, “Look! Won’t you
Then she thought to herself what could get herself out of this
situation. “You know what? I really appreciated your company this
evening,” she said as she started to lean her head towards the guy’s
slack-clad crotch. “You know what? I’m going to give you a thank you
“What kind of thank you notes are you thinking about,” William said with
a leer in his voice and a smirk on his face.
“This one,” Marilyn curtly said with her mouth poised above the boy’s
crotch. Then she opened her mouth and bit down hard on her companion’s
dick through the slacks.
“You bi…” Before he could get the words out of his mouth, Marilyn’s fist
and some blood from her lips was it in. “Don’t you dare try anything like
that again, you got that? And if you didn’t try to play me out, you would
have gotten your thank you ‘note’…C sharp!” With that, she opened the door,
pulled out her purse, angrily stepped to the front door and ran the bell.
When Sharilynn answered the door, she took one look at Marilyn’s face and
let her in without a word. She placed her arm around her and walked
into her room.
As they sat down on the bed, Sharilynn asked “what happened? I heard a
commotion out there.”
“My date, in a word sucked. I didn’t like being touched by the guy!
Yuck! Even worse, the guy tried to…well, touch me, you know?” Marilyn said
to her in a dour mood.
“Yeah, I know,” Sharilynn replied. Then, she wrapped her arm around her
sister, placing her hand on her sister’s breast. “Sorry that that had to
happen. I at least wanted you to give a shot, but I see it didn’t
work out,” she continued on as she kissed her sisters forehead and rubbed
and palmed her sister’s breast. “Remember I promised to give you to give
you something to make this whole night worth your while if it didn’t work
Instead of answering, Marilyn grabbed her sister’s head and kissed her
on the lips hard, slipping her tongue in the mouth. Her put her
hands up in shock, then embraced her as they continued to make out,
feeling her sister’s back through her dress. Marilyn pushed her back onto the bed, putting her full weight on her sister’s body as her
sister pulled up her skirt to caress her panty-clad ass. She moved up her
sister’s body, pressing Sharilynn’s head to nibble on her neck as their
breasts rubbed past each other. When she felt her sister’s lips kiss down
her collar bone, Marilyn reached up to unbutton the top button of her
dress. In response, Sharilynn nearly ripped off the top of her sister’s
dress in trying to unbutton the rest of the dress, greedily looking at her
sister’s bra-covered breasts. Feeling how urgent her sister’s hands were,
she reached up to her bra and, after a bit of struggle, unclasped the front
of her bra, allowing her constricted to go free.
“Mmmm, you look delicious! I could just eat you!” said Sharilynn in
enthusiasm, and it seemed that would do just that as she on her
sister’s skin. Slowly, she tried to kiss and suck and lick a trail down to
her former brother’s breasts, enjoying the mildly sweet taste her sister’s
skin had. Then, she started to do what she knew her loved her to do
in kissing all over her soft, firm tits, drooling as she salivated all over
them. She grabbed her sister’s and lifted the nipples to her mouth
as her shifted her body slightly forward. Sharilynn took one nipple
in her mouth as on it hard, then flicked her tongue over the tip of
it. When she switched her treatment to the other nipple, Marilyn balanced
herself with one arm and grabbed her sister’s head with the other.
“Yeah, sis, suck on my nipples! Ooh, that feels so good!” Marilyn said
to her as she felt her get a bit uncomfortable with her
hardening cock. She reached down to let her dick loose and let her partly smother her sister, with her lightly biting on her and
lashing her tongue on her areola. As her tip brushed against her sister’s
T-shirt, her nipples and areolas were slobbered over by her sister’s tongue
while she enjoyed the feel of her sister’s cooling saliva on her tits.
“Ma-ri-lyn! I feel your dick hanging down on me. Do you want something
special? Then pull off my jeans and and lick my to get it
Marilyn slid off to one side such that she was even with her sister’s
body. She then reached down, unbuttoned her sister’s jeans and pulled off
her sister’s jeans and with one powerful tug. She then stopped a
second to look at her sister’s newly shaven pussy.
“I told you I would make it worth your while! Now get me hot!”
Sharilynn barked out in lust. Marilyn went between her sister’s legs,
spread them wide enough for her shoulders and began to lick her in
long, strong, powerful strokes. She then flicked her tongue gently along
her sister’s labia as she held onto her sister’s hips. Then, realizing
that she wasn’t trying to make her cum, she licked a couple of quick
circles around her sister’s clit, then slid her tongue into her sister’s
slit. She took the time to lick inside her sister’s lips, slobbering the
inner lips and starting to taste her sister’s wetness. She licked back and
forth in her sister’s sweet sex, sticking her tongue deeper and deeper with
each pass. Finally, she reached the point where she pushed her tongue into
her sister’s sugar walls. Sharilynn pulled her up by her hair, looked into
her eyes and said “Fuck me!”
“I said fuck me now! I need your hard dick right now!”
Just then, it began to sink in. Marilyn was going to loose her
virginity to her sister, and she could not believe her luck. She gathered
herself mentally, then crawled up her sister’s body to line up her dick
with her sister’s pussy.
“Do it dammit!”
Marilyn lined up her dick with her sister’s pussy, grabbed her butt and
slowly pushed himself in. When she felt her sister’s walls close around
her hard cock, she felt like she was in heaven. After she finally bottomed
out, she grabbed on tight to her sister’s hips and started pumping them
half out of instinct and half out of what she saw in porno movies. Still
mentally trying to get used to the feeling of actually fucking, she almost
didn’t notice her bucking under her, almost to the point of orgasm.
“Oh, you feel sooooo good inside of me! Fuck me harder! Hi-hi-I’m
about to cum…oh yeah…”
On hearing this, she wrapped her arms around her sister’s back, pressing
her against her sister’s, and pumped as hard as she could inside
“Oh yes, oh yes, Oh yea….”
Sharilynn lost the ability to speak as her most intense orgasm of her
life gripped her body, made her shake and took her seemingly to another
planet. Of course she had fucked some before, but it was never like
this. It could have been her sister’s endowments that took her so high,
but it was her deep love of her sibling and the fact that she was doing
such a big favor for his by taking her virginity, especially in the rough
spot she was in. As she glided back down to Earth, she started to realize
the consequences of her action. She and Marilyn were now lovers, and with
that needed to come some ground rules. After all, as much as she had for
Marilyn, she didn’t want her to be her everything. Slowly, everything came
into focus for Sharilynn again as she felt the huge cock pumping her harder and starting to twitch.
“Oh, yeah, this feels so good. Oh yeah, Mmm hmm, yeah! Your felt
so good squeezing on me as you came….Squeeze me tighter sis…I’m about to
Marilyn felt her squeeze her whole body around her, from her legs
wrapping around her back to her sugar walls collapsing on her member.
“Ooo, ooooooooooooooooooh YESSSSS!”
Marilyn slowed down the pumping of her hips and squeezed her tight as she nutted for the first time inside of a woman. She held tight
as her release came and went through her cock and her being. She then
collapsed on top of her sister, huffing and puffing after losing her
“That was great, Marilyn,” Sharilynn said as she looked at her sister,
“but if you want to do this again, we have to establish some ground rules.”
“First of all, this is the last time you’ll be fucking my pussy. I
wanted to give you the gift of making you a man. However, I don’t want to
be pregnant right now, plus there are the risks of having an incestuous
“You got a point there. So what do you want me to do?”
“I want you to fuck my ass. Don’t worry about that. Even though it’s
harder for me to get you up there, and for you to learn how to do it right,
we’ll work on it. Besides, I liked anal sex the one thing I tried it, and
it’s fun for the guy and, in your case, girl.”
“Gotcha sis. One thing though,” Marilyn said before giving her a
peck on the cheek. “Can I lay here like this for a while? This is a
“Sure sis. Just hold me in your arms.”
Marilyn came out of her nostalgia trip to find her bowl of cereal
completely devoid of cereal and that she was spooning milk to her mouth.
She looked up at the time, then looked at her dad.
“Dad, can I see the paper? I wanna read it before I go upstairs and get
ready to visit my friend.”
“OK, son. Here you go, since I’m finished.”
“See ya later!” Marilyn said as she pulled away from the table, stood
up, grabbed the paper and walked into the living room, ready for a
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