• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Rory & Marigold: A Love Story

Rory & Marigold: A Love Story

Marigold was a young, twenty-two year old, good-looking, intelligent woman who got hit on all the time by men. She loved the attention she got, and always wore sexy clothes to make sure she got the attention. She had a closet full of mini-skirts, halter tops, fishnet stockings, and high-heeled shoes and boots. She always wore the latest Victoria's Secret panties under her clothes, just incase the right man came along.

Even though Marigold got attention from men, she didn't have much sexual experience. This was because Marigold wasn't an ordinary girl. She was born a man.

She knew all her life that she was different. She was born Thomas, a skinny nerdy boy who was picked on all the time growing up. She hated the body she was in, so when she graduated high school, she started her hormone therapy, and a few months later went to Thailand to have her sex change surgery. She loves her new body. She had gotten big 32C breast implants, and loved her new vagina. She had never had sex with her new womanly body. She had just had a few sexual encounters in high school. The first time was with a girl; they just made out and got naked. Another encounter was with his (now her) best friend John. The two boys had experimented a few times, masturbating together, and had tried oral sex a few times. But she was ready to have real sex as a woman. She wanted to know what a penis would feel like in her vagina. She always wanted to have the feeling of a man inside her, and now she could.

Marigold went online to try and find a man who would want to be with her. She joined all sorts of dating sites, and posted her pictures. She talked to a few men she was interested in, so she could get to know them. She stopped talking to most of the men, because she knew they wouldn't accept her being a transgendered woman. But there was one guy, Rory, who she felt a connection with. They had talked for a few weeks and she was building the courage to tell him she was transgendered.

One night, she and Rory were talking, and she was feeling so happy because of the strong connection she felt with him. She decided she was going to start bringing up the topic of transgendered people. Marigold nervously brought the topic up:

Marigold4U: What do you think of transgendered people?

SexxiRory82: I feel sorry for them. Being confused and in the wrong body.

Marigold4U: I know, I hate how they're always discriminated against, and made fun of... even more so then gay people.

SexxiRory82: That's so true. I think its harder to be transgendered then gay.

Marigold4U: Would you ever be friends with a transgendered person? Or date one?

SexxiRory82: I would definitely be friends with someone transgendered. I never thought of dating one though.

Marigold4U: Well, I have to tell you something. I feel so connected to you, but I have a secret. I'm transgendered. I was born a male.

SexxiRory82: OMG, really? I don't know what to say...

Marigold thought it was all over. She started crying. She knew Rory would never want to date her after finding out her truth.

Marigold4U: :'( I guess you don't want to talk to me anymore! That's fine, I didn't expect you to want to date a tranny. It was nice knowing you.

SexxiRory82: Wait! I never said that! I'm just shocked. I feel a connection to you, I want to meet you. Can we meet up tonight? Say, 9pm?

Marigold4U: OMG! OMG! I'm so shocked... and excited! You really want to meet me still? You're sure about this? I'm at 736 Queen Street on the south side. I'll be ready and waiting. I can't wait to meet you and talk to you in person!

SexxiRory82: I'm so excited to meet you too! I'm going to get ready and leave soon... I'm SO excited!

They both logged off. Marigold ran into her boudoir. She had to find the perfect outfit to make a good first impression with Rory. She wanted something that was cute and friendly, but at the same time sexy. But not too sexy, she didn't want Rory to think she was an easy slut. She put on black lace Victoria's Secret panties and bra. She looked in the mirror and made sure her breasts looks good and perky. She turned around and looked at her ass in her panties. She loved her womanly body, and thought "This is what I always wanted! I feel right and happy in this body!" She slipped on a black pin-stripe miniskirt, and some thigh-high black stockings. She put on a silky white blouse, and some black stilettos. She wore her long brown hair down. While she was putting on make-up, she heard a knock on the door. She looked at the clock and it was 9:04pm. It must be Rory.

She ran to the door in anticipation. Her heart was racing so fast, she thought she would pass out. She looked though the peep hole, and saw a tall, dark, good-looking man in his early 30's standing there. He was wearing a leather jacket and jeans, and had black hair and had scruff on his face. It was Rory. She thought he looked so much better then in the pictures he had sent her. She was so nervous. She slowly started to open the door.

Rory looked at Marigold and was in awe. He thought she was gorgeous. She had such a beautiful, feminine body. He stared at her big breasts, wondering how this beauty could have ever been a male.

"You look absolutely stunning!"

"Thank-you!" Marigold blushed.

"You look great too. You look so much better in person."

"Thanks. I can't believe you were born a man! Did you... did you have your surgery yet? I mean... I hope I'm not offending you. I'm sorry... you don't have to answer!" Rory stuttered.

He was so nervous and was trying not to say the wrong thing.

"It's okay! Don't be nervous! You can ask me anything, I don't mind. Yes, I had my sex change done in Thailand. It's so beautiful there! Please, come in, sit down. Do you want anything to drink? How about some wine?"

"Sure, I'll have a glass" Rory replied as they walked into the apartment. Rory went to sit down on the couch while Marigold went into the kitchen to get a bottle of red wine and glasses. She also brought out a box of chocolates.

Marigold poured a glass of wine for Rory, then herself. She was so nervous. She wanted this night to go perfect. She was hoping that she wouldn't say or do anything to make Rory run off.

"Let's toast", said Marigold, "To a new friendship. Hopefully our connection will grow stronger and last forever, best friends for life!"

The two clicked glasses and took a sip. They started to small talk, discussing basic details of their lives. Rory came from a small family and works at the bank as a manager. Marigold explained how her and her family weren't very close, except for her mother who was the only one who accepted her. Her father hated her, and was disgusted with what his son had become, so they stopped talking. "I'm sorry to hear that, that's so sad" Rory said.

Rory was nervous, and was already on his forth glass of wine in 40 minutes. Marigold had had three. They were both loosening up and their discussion started to turn to more personal topics.

"How many men have you been with? I mean... as a woman..." asked Rory.

"Um... to be honest... none" Marigold said shyly.

"What?! A beauty like you, and you haven't been with a man yet? That's... that's a shame! You could probably have any man you wanted! You're gorgeous, you're better looking then most natural born women!"

Marigold blushed, "Thank-you, you're too kind, but I'm scared. I don't want to hide my past, and I'm scared that when I tell men I was born a male, they won't understand, or be disgusted".

"I'm not disgusted at all, I think you're very sexy". Rory moved closer to Marigold, lightly rubbing her arm. He then moved in for a kiss.

The two shared a very passionate kiss. Their tongues met each other. Marigold was in heaven. She couldn't believe she was making out with a man like Rory. This was her dream come true. Things were moving faster then Marigold had wanted, but she wasn't about to turn down this sexy man who wants her, even after knowing her past. She slipped her hand into Rory's pants.

She felt his hard erection. This made Rory moan out, and he started kissing all over her neck and chest. She unbuttoned Rory's pants, and his cock sprang out. He wasn't wearing any underwear. They stopped what they were doing so Rory could take off his pants and shirt.

He stood in front of Marigold, naked. Marigold was eyeing this naked muscular man in front of her. She was getting very horny. She couldn't believe this was happening. She stared at his broad chest, down to his abs, and then to his long, thick cock. She couldn't believe how big and thick it was. She was dying to have that inside of her virgin vagina.

She slipped off her miniskirt and was in her black panties, bra, and thigh high stockings. She then kneeled down in front of Rory, and took the tip of his penis into her hungry mouth.

Rory's cock was the hardest it had ever been. He was so turned on seeing this beautiful woman licking and sucking his cock head. "This feels so good" he whispered.

Marigold was sucking and licking up and down Rory's shaft. She tried to take as much as she could in her mouth. She managed to take all of it, and gagged as she moved off of his big cock.

"Oh my god, this feels amazing" Rory moaned in pure pleasure.

"This is so hot, I love your big cock, it tastes so good!" Marigold said while taking a breather from orally pleasing Rory. She sucked Rory's cock for 10 minutes, deep-throating him, licking and kissing the tip, sucking it. Rory couldn't hold back any longer.

"I'm going to cum!" yelled Rory. Marigold opened her mouth wide, wanting to get every drop of Rory's man juice. Rory's cock squirt out 5 big shots of cum, and Marigold got every drop in her mouth.

"That tastes so good" Marigold said while swallowing Rory's big load. She rubbed his still hard cock on her lips, smearing every last drop. She felt so womanly having had pleased this man, bringing him to pleasure, and swallowing ever drop of his semen.

"That was amazing! But now it's your turn. Get naked, and let's go to the bed" demanded Rory.

Marigold took off her bra, revealing her breasts to Rory for the first time. Rory stared at them, and couldn't believe how perky and supple they were. Marigold continued undressing, taking her stockings off, and finally, slowly, slipping off her panties.

Rory stared at her round ass, and then, Marigold climbed on the bed, and spread her legs, revealing her vagina.

Rory climbed in between Marigold's legs, laying on his stomach so that he could get a good look – and taste – of Marigold's vagina.

He slowly started to part her pussy lips, rubbing her clitoris and teasing her with his finger lightly pressing into her vagina.

Marigold moaned out. These feelings were all new to her. She had never had a man rub her clitoris, feeling on the vagina that she had always wanted.

Rory took his right index finger and put it into his mouth, getting it nice and slippery. He then inserted his finger into her pussy.

"Are you ready for this?" Rory asked.

"Oh my god, yes! Yes Rory, this feels so good" Marigold said in anticipation.

Rory started to thrust his finger in and out of Marigold's pussy, and started to kiss on her clitoris. He then stuck his tongue out, and started to lick her clitoris. He did this for a few minutes, then took his finger out and replaced it with his tongue. He stuck his tongue in and out of her vagina, licking and slobbering all over it, making Marigold moan loudly. Rory loved the taste of her pussy. Rory continued eating Mari out, and made her scream out when she had an orgasm.

"That... that was... it felt.. sooo good! Oh my god" Marigold uttered, out of breath.

"That was nothing. We aren't done yet. Do you have any lube?"

"There's some in the drawer over there."

Rory got up to go to the dresser drawer Marigold had pointed to. In there he saw the bottle of KY lube, and saw a few other treasures. There was a pink vibrator, a butt plug, and a big double ended dildo. Rory picked up all these and threw them on the bed.

"We're going to have so much fun!" Rory exclaimed.

He put a big glob of lube on his index and middle fingers, and spread it all over Mari's vagina, making sure her new pussy was well lubricated and ready for anything. Rory slipped his fingers in and out, getting Mari's pussy warmed up and stretched out. He had 3 fingers slipped in, and after a few minutes, was able to slip 4 fingers in. Marigold was getting so aroused and horny. "Stick something in me!" she demanded.

Rory picked up the pink vibrator. It slipped right into her vagina with ease. He turned it on to the highest setting. Marigold was moaning very loud in pleasure. Rory thrust the vibrator in and out of her vagina.

"Hold onto this" Rory told Marigold. She took control of the vibrator, as he reached for the double ended marital aid. He lubed it up and started to stick one end of it into Mari's vagina while she still had the vibrator in. The double ended dildo started to stretch her vagina, with her moaning in both pain and ecstasy.

Rory was jacking off while slipping more and more of the double ended dildo into Mari's pussy, all the while she's still wiggling the vibrator in her.

"I'm so horny! Please, please fuck me!" Marigold yelled to Rory. Rory pulled the double ended dildo out of her pussy, which was half in her, and she pulled out the vibrator. Marigold got into the doggy-style position, waiting for Rory's cock.

Rory lubed up his cock, and slowly started to insert the tip. Marigold was honry and anxious and just thrust herself onto Rory's cock.

Rory wasn't expecting that, and came inside of Mari. "Oh my god, your pussy feels so good. I couldn't help it" whispered Rory.

Marigold turned around and pushed Rory face-up onto the bed. She then climbed on top of him and put his dick into her. With all the lube and cum, Marigold was able to ride Rory very hard. She was screaming in ecstasy, and Rory was yelling in pure pleasure. Rory came again and again, and Marigold had multiple orgasms.

Marigold collapsed on top of Rory. They both laid there for several minutes, catching their breath and resting.

"We didn't get to use the butt plug" Rory laughed.

"Turn around and bend over" demanded Marigold.

"What? Why?"

"Just do it" Marigold said with a wink.

Reluctantly, Rory turned around and waited on his hand and knees. Marigold got the bottle of lube and put some on her finger. She put some on Rory's ass hole, and moved her finger around and around, teasing his anus.

"Oh my god, that actually feels good" Rory said.

Marigold then started to press her finger into Rory's rectum, making sure to use a lot of lube and to go slow. She was able to get her whole index finger into Rory.

"How does it feel?" Marigold asked.

"It feels... okay... it's pleasurable."

"Are you ready for the buttplug?"

"I..I don't know, I guess" Rory said nervously.

Marigold lubed up the buttplug, and started to put it into Rory's boy hole, replacing her finger.

The buttplug was much thicker then Mari's finger, but Rory was able to take the whole thing into his rectum.

Marigold then laid on her back under Rory, and started to suck his cock while playing with the buttplug inside of Rory.

Rory was in pure bliss. He had never experienced anything like this before. Having a buttplug in his anus, pressing on his prostate was sending shivers up his spin, and Marigold sucking his cock vigorously was sending him over the edge.

Rory shot his load right down Marigold's throat. She swallowed and smiled.

"I guess that was good?"

"Yeah, it was real good" Rory replied.

The two then went to shower, where they couldn't keep their hands off of each other. Rory was caressing Marigold's implants, kissing and sucking on her nipples. The two started to make out, kissing all over each other's bodies.

Marigold was up against the wall, with her back towards Rory. Rory was as hard as he was when they first started their sexcapades, and he stuck his huge member into Marigold's waiting pussy. They fucked for thirty minutes, until Rory ejaculated into Marigold again.

Marigold stuck her fingers into her vagina and got some of Rory's cum on them, and licked it up. She rubbed her clitoris and fingered herself, and came within a minute.

"You're an amazing lover. You made my first time, as a woman, feel so wonderful" Marigold whispered into Rory's ear.

"You're amazing. Your vagina feels amazing, your breasts are immaculate. You opened my eyes to new things, I would have never thought something in my ass would feel so good" Rory replied back.

"I hope we can do this again" Marigold said, as she stepped out of the shower to dry herself off.

"Of course! Marigold, I want you to be my girlfriend. You're an amazing woman and an excellent lover. I want to be with you." Rory exclaimed.

Marigold broke down into tears. She was not expecting to hear that from Rory. She excitedly replied, "Yes! Oh Rory! You're my dream come true! I always wished to find a man like you!"

It was now 4am. The two got into bed and cuddled under the covers. Marigold was so ecstatic. She was thinking to herself, "I found him. I found my perfect man. A man who accepts me. A man who finds me attractive. A great lover. I hope we get married! Imagine that, a TV walking down the aisle in a gorgeous wedding gown! This is too good to be true!"

............

............

It was too good to be true. Marigold woke up in a hospital bed three days later out of a coma.

"She's awake! Ma'am, do you remember what happened?" one of the doctors in the room asked.

"A man... Rory... came over... and we... oh.. I can't remember!" Marigold tried to explain.

"The man you invited to your house, he beat you unconscious, and robbed your place. You're lucky to be alive" a police officer told Marigold, "he also vandalized the place, wrote FAG, TRANNY, HE-SHE all over the walls. He took all your valuables. We found you naked and with a banana stuck in your vagina. He didn't rape you, but sexually assaulted you."

Marigold was crying hysterically. She couldn't believe that she dreamed all that, and that Rory really beat her unconscious and stuck a fruit up her vagina. She was beyond embarrassed.

Marigold would have to stay in the hospital for a few days to recover. Her vagina was sore from the rough insertion of the banana. She was dreading going home. She just cried herself to sleep, trying to forget the whole situation.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Rory & Marigold: A Love Story

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 162 milliseconds