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 boys 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 story 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 Man           by: Brett Lynn

 

Marilyn woke up refreshed from a nice night’s sleep. A good cum 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 step out of the bed. She stood up, tucked herself up, pulled on a T-shirt, some panties 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 father looking at her funny again. Then again, her father 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 father 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 later, OK?"

Donnie jumped back as he realized who just opened the door. As with any other teenager, he was shocked when his father walked in on him pleasuring himself. What was unusual, however, was that his father 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 breasts 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 inevitable.

"OK Dad. See ya when you get in tomorrow."

"OK."

With that, the door closed, the conversation ended and the secret was out. Donnie vaguely heard his father 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 her stereo.

"Something big just happened."

"What?"

"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 now."

He conveniently saw his father 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 dad."

"Hey son," his father replied. "Well, let’s talk. Your mother told me all the medical details about how this got started. So what do you go by when you’re like this?"

"Marilyn."

"Alright, um, Marilyn, I understand what you feel. I mean, I thought this was something you only saw on TV to grown people, but it’s different when you see it on TV."

"Thanks Dad."

"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."

"You WHAT?!"

"Don’t worry. It’s OK. I’ll let him know about your condition beforehand. Besides, I think he has some gay tendencies, you know?"

Marilyn was in utter shock and disgust when she heard the news. "Where does this asshole get off thinking I like guys now because I have boobs!" she thought to herself. Then, while her dad prattled on about details about the date, she saw her sister in the hallway listening to the proceedings and mouthing to her "don’t worry. We’ll talk after he’s finished."

"So how’s Friday night for you son, er, Marilyn."

"It’s OK, it’s OK," Marilyn said as she gave her father 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 guys 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 shirt 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 sister 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 brother 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 sister get the underwear for her, since her sister knew her sizes. Sharilynn had smartly gotten her some front-closing 38C bras, the easier for her sibling to manipulate, and some lacy panties 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 breasts and to latch the clasp in the front.

"Man, this is tight," Marilyn said, looking at her cleavage 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 panties 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 old T-shirt and shorts. The other image was something unusual. There stood a girl, with hair that needed to be combed, cleavage 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 sister shot back while getting a dress from her closet door. "Here, put this on." Sharilynn handed her sister 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 cleavage showing. Then, her sister picked a tube of coral pink lipstick and pointed her face towards the mirror.

"Pout for me please?" her sister asked.

She pouted on cue, and then her sister spread out the lipstick on her lips. She made a kiss in the air and saw that the lipstick that her sister 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."

"Thanks sis."

She sat down on the bed, pulled on the socks and laced up the sneakers.

DING-DONG!

"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 sister 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 father 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 going on.

"Marilyn!" said her sister 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 movie at Red 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 college 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 chill man!"

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 note."

"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 sister 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 sister 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 guys 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 out?"

Instead of answering, Marilyn grabbed her sister’s head and kissed her on the lips hard, slipping her tongue in the mouth. Her sister put her hands up in shock, then embraced her sister as they continued to make out, feeling her sister’s back through her dress. Marilyn pushed her sister 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 breasts 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 sucked 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 sister loved her to do in kissing all over her soft, firm tits, drooling as she salivated all over them. She grabbed her sister’s boobs and lifted the nipples to her mouth as her sister shifted her body slightly forward. Sharilynn took one nipple in her mouth as sucked 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 sister as she felt her panties get a bit uncomfortable with her hardening cock. She reached down to let her dick loose and let her breast partly smother her sister, with her sister lightly biting on her breast 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 panties and lick my pussy to get it wet!"

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 panties 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 sister 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 sister 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!"

"Huh, sis?"

"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 sister 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 breasts against her sister’s, and pumped as hard as she could inside her sister.

"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 guys 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 pussy harder and starting to twitch.

"Oh, yeah, this feels so good. Oh yeah, Mmm hmm, yeah! Your pussy felt so good squeezing on me as you came….Squeeze me tighter sis…I’m about to cum…"

Marilyn felt her sister 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 sister 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 virginity.

"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."

"OK, shoot."

"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 baby."

"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 sister a peck on the cheek. "Can I lay here like this for a while? This is a once-in-a-lifetime experience."

"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 leisurely read.

_______

Please! Send your comments my way! You know how to hit me up!

 

 

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