tagTranssexuals & CrossdressersA New Year to Remember

A New Year to Remember

byAngelaK©

Samantha looked at herself in the mirror: while not considered beautiful, she was still attractive. If asked, most people would say she was pretty.

Samantha (or Sam, as she liked to be called) stood 5ft-9: tall as women went. Her shoulder-length brown hair and twinkling brown eyes gave her the appearance of being younger than her thirty-eight years. She still had full, firm breasts, though smaller than many men liked: 33D. Her narrow waist gave way to thirty-six inch hips.

However, Sam had something else that turned most men off: a penis. She was transgendered, and had been since she was fifteen. Her penis was small, but it was enough to turn off most men. And the men who did go out with her were only interested in her ass. Few men asked her out more than once.

"What's wrong with me?" she asked herself. "I'm witty. I like a lot of different things. I'm easy to get along with. I like sex!"

Sam had been living with Randy for almost five years. They seemed to hit it off from the start. Randy was considerate of her, though he tended to be a little domineering at times. He was good in bed, and occasionally made her come. It didn't hurt that he was extremely handsome. Other women more attractive than her often followed him with their eyes. Randy seemed oblivious to their desire.

Sam worked for an insurance office, while Randy tended bar most evenings. He would get home around three in the morning. Sam would go to bed early and wake up around the time he came in so they could have time together. The arrangement allowed them more time than they would have otherwise had. He was usually leaving for work an hour after she arrived home in the evening.

Randy came home one morning and didn't seem to be interested in sex, claiming he'd had a rough night and was exhausted. One of his co-workers didn't show. This happened again the following week. And the week after. Randy would kiss Sam and then go straight to bed.

Sam decided to take off early the next time it happened. She would wake him early and convince him to go in a little later. She stopped at a little lingerie boutique and bought a black teddy that she wore home under her dress. Randy liked seeing her in a teddy: maybe this would perk him up!

Sam was excited, anticipating his pleased expression when she crawled into bed next to him. She was crushed with what she found!

Randy was in bed with two women!

Sam knew both of them: they were waitresses at the bar where he worked. And they were both transsexuals! Both were short blondes with big breasts!

Sam watched in stunned silence as Randy pulled his cock out of one's ass and put it in the other's mouth, then back again. She watched as they did this for several minutes. Her jaw dropped when Randy stood on the floor and one took his cock in her mouth and the other knelt behind him, spread his cheeks, then stuck her tongue in his ass. After a few minutes, the women switched places.

Tears flowing down her face, Sam watched them do the things she'd refused to do. She wouldn't lick his ass and wouldn't participate in a threesome, no matter the gender.

Sam quietly slipped out the door and walked around a while before settling on a park bench. It had been a couple of hours: the girls were probably gone by now. He'd have them out before she came home. She decided to call him.

"I saw," was all she said.

"Huh?" he relied. "Saw what?"

"You...Tina...Carol", she said flatly. "Tell me, whose tongue felt better in your ass? Tina's? She licked you the longest!"

Randy tried to make excuses, promising it wouldn't happen again, but Sam knew better. There had been the previous weeks when things didn't seem quite right after she came home. Smells were off, the bed tidier than normal for him. And then there were those mornings when he came in just in time to see her off to work.

"I'm staying with the Myers tonight. Have all your things out of my apartment when I get home tomorrow evening. I don't want to see you there: I don't want to talk to you. I want you to leave, and never come back!"

Sam would be safe with the Myers: Mr. Myers was a SWAT officer. Randy was slightly afraid of him anyway.

Sam cried as she looked in the mirror. She was convinced it would be harder to find someone new the older she became. Men seemed to want the younger women: Tina was twenty-two, and Carol might have been twenty-one!

Younger men hit on her frequently, but, she felt they thought older women were desperate for sex and would be easy lays. Sam wasn't interested in a life of one-night stands that grew fewer as her looks faded with age.

Sarah, a friend from the office, tried to get her to go clubbing with her. It only took a few times before Sam discovered she didn't like the type of men she met. It was the same story: men her age wanted someone younger, and younger men were only looking for an easy fuck.

Sarah tried a different tack: she, and her boyfriend hosted several parties and invited Sam, hoping she might meet someone she could like. Sam liked most the men she met, but none seemed more than casually interested in her. Sam kept coming, though: she liked the company and the distraction from her loneliness.

Sarah invited Sam over for Thanksgiving dinner with her family: she had a couple of cousins to introduce. Sam took a liking to Scott, the older one. He was funny and charming: pleasant company.

However, she was drawn to Tom, the younger cousin. He was in his twenties: young by Sam's standards. He seemed sad, and a little withdrawn, and that caught Sam's attention.

Tom and Sam were seated next to each other during the meal. Sam had the impression Sarah was trying to fix her up with him. He was pleasant, but quiet. He smiled shyly whenever Sam talked to him, but, he didn't say much in response to her questions.

Later in the evening, Sam was outside, looking at the night sky, when Tom joined her. He draped his coat over her shoulders when she shivered from the chill night air.

As the dinner ended, Tom walked her to her car, then kissed her cheek, surprising her.

"I'm...I'm sorry," he said quietly. "I shouldn't have done that!"

"That's okay. I liked it," she replied.

Tom then asked if she would like to go for a drink the next night and suggested a quiet bar close to where she lived. Sam agreed and they set a time to meet.

Over the next several weeks, Sam and Tom met regularly for a drink. As she learned more about him, Sam realized he was very mature for his age. He was also very courteous: helping her with her coat, holding doors for her, holding her seat as she sat, letting her enter a room first. Their ten year age difference didn't seem to mean anything to him.

As they became close friends, Tom talked about his past girlfriends, and she talked about Randy.

"My last girlfriend left me for a man with a bigger bank account," Tom lamented.

"Ouch!" Sam replied.

Tom laughed and said, "Yeah, but, at least it's growing now, and not shrinking anymore!"

They laughed together, but Tom couldn't help but notice the sadness in Sam's eyes. He reached across the table to take her hand.

"What happened?"

"I found Randy in bed with two younger transsexuals who worked with him."

Sam noticed the funny look in Tom's eyes as he thought about she'd just said. A light seemed to come on in his head as he realized the implications of her words.

Expecting him to pull back, she lowered her eyes and whispered, "Yes, I'm transsexual, too."

She looked up when she realized he still held her hand. He seemed to be studying her closely.

"He was an idiot!" Tom declared. "You're very lovely!"

"You really think so?"

Tom smiled and nodded. They kissed goodnight when he walked her to her car.

"What are you doing for New Year's?" Tom asked.

"Sarah invited me to her party, but I don't want to go. I would just feel lonely at midnight."

"She invited me, too"' he replied. "Would you like to go to dinner, instead, and maybe a movie? We could watch the fireworks at midnight."

"That would be nice."

Sam went through her closet: she didn't own any sexy dresses, and her work outfits wouldn't be appropriate. She found a black dress crammed in the back. She ironed it and stood before the mirror as she checked it out. It was a little tighter than she remembered, and a little shorter!

Tom stared admiringly at Sam. Her hair was up exposing her neck. He could see the swell of the top of her breasts. Her dress came to mid-thigh: Sam had very shapely legs. Tom was having a difficult time believing she was transgendered.

Tom took her to a nice restaurant by the bay: It was expensive, but the look on her face when they arrived was worth every penny! The place even had a dance floor! Sam was enjoying every moment as Tom swept her off her feet!

When Tom suggested a movie, Sam invited him to her place, instead.

"We can watch old movies on TV, and I have some Champagne chilling, if you like.

Tom sat next to Sam on the couch as they watched a Marx Brothers comedy, "Animal Crackers". Both laughed at all the puns and gags. He placed his arm around her shoulders and drew her closer. She pulled his hand to her breasts.

Soon they had forgotten all about the movie as they embraced in a long, deep kiss. Sam was pleased at how well Tom kissed: he seemed to enjoy kissing as much as she! His hand caressed her legs. His light touch was arousing her.

"Undress me," she whispered as she straddled his lap. "Please!"

Tom continued kissing her while he worked her zipper down. He lightly stroked up her back till he reached her bra and unclasped it. He slid the dress and bra off her shoulders as he kissed her neck. He slid the dress lower until her breasts were exposed.

Sam tossed her bra aside and raised herself up and presented a nipple to Tom's mouth. It was soon erect from his kissing and nibbling. She held his face closer, encouraging him to suck harder. Tom raised her dress enough to be able to slide her panties off her bottom. He squeezed both checks as he continued sucking.

Tom asked Sam to sit on the couch: her dress was around her waist. He unfasten the strap to her shoe, removed it, and began kissing her foot. He slowly nibbled and kissed his way up the inside of her thigh. When he reached her balls, he kissed and sucked them through the thin fabric of her panties.

Sam gasped with delight! No previous lover had ever done this! She shivered as he moved to the other leg and started all over. When he reached her panties the second time, she raised her hips slightly as he slid them off her bottom and down her legs.

She gasped again when he took her cock into his mouth and began bobbing up and down the shaft, taking all of her small cock. When his face was in her crotch, he ran his tongue across her balls. He pulled back, he sucked harder and dragged his tongue underneath her shaft. She soon filled his mouth with her cream.

Tom raised himself to her face and asked, "I've never done this before: did I do it right?"

Sam pulled his face to hers and kissed him deeply. She could taste herself faintly on his lips.

"Did you ever!!"

Sam stood and led Tom to her bedroom. She sat on the edge of her bed and unzipped his pants. She reached in to his shorts and pulled out...

The biggest cock she'd ever seen!!

Most of her previous lovers had cocks around six inches long: most were average thickness, but a couple were slightly longer, and a few thicker. She was able to take them easily.

However, Tom was almost three of her hand's width long! Sam had long fingers, but she couldn't close her fingers around him!

"Your girlfriend left THIS for a bigger bank account? Was she nuts?" she asked.

Sam was sure this would be a tight fit in her mouth, and an ever tighter fit in her ass, but she was going to try!

As she stroked his length, she managed to get nearly three inches inside her mouth. It wasn't as difficult as she first imagined and soon had half his length inside. Tom's groans warned her of his impending ejaculation: she pulled back until only his head was inside. She kept stroking until he began pumping his large load into her mouth. She could barely swallow it all: some ran out along the sides of her mouth and down her chin. She used her fingers to clean her face.

"Wow! It must have been a long time since you last came!"

He looked down sheepishly as he replied, "Actually, it's only been a day: I've been stroking myself and fantasizing about you ever since I first met you."

Sam was floored at his confession! But she had to admit she'd fantasized about him a few times, too!

She reached into her nightstand and pulled out a jar of lubricant, handing it to Him. She rolled over onto her stomach and spread her legs.

"I need you to use your fingers to open me up. Please, go slowly."

Tom started tracing her rim with one finger. He applied a little of the oil and slowly worked one finger inside. A few minutes later, he worked a second finger inside, then a third, followed by the forth. He twisted his hand and varied the pace as he pushed his fingers in and out.

"Yeesssss! Just like that! It feels so goooood!" she moaned.

Tom gently kissed her bottom as her fucked her with his fingers. She had such a lovely bottom: he could spend hours admiring it!

"I'm ready, now," she said.

"Please! Go slowly!" she begged.

It was all she could do to keep from screaming as he worked the head into her tight sphincter. She'd never felt this much pain: not even the first time someone fucked her! The head slid past with a pop. Tom stopped and waited until her breathing calmed.

He slowly slid in, stopping every inch to let her rest until his head touched the end of her channel. He was only three quarters of the way in. He slowly pulled back, then slowly slid in again. As Sam relaxed, he increased his tempo.

He'd been holding his weight off Sam, but, now he wanted to feel her skin next to his. He nibbled her ears as his hips ground against her perfect bottom. Even though he came a few minutes ago, her tightness excited him: he was close.

Suddenly he felt her channel contracting and relaxing repeatedly. He couldn't help himself: he came again, his load pushing out around his cock.

Sam had wanted him to stop at first, but his huge cock travelling back and forth in her channel soon had her feeling wonderful. She could feel her neck and chest growing warmer. Her breathing grew shallow and rapid. Her cock felt harder than it had ever felt! She felt the pressure building and then she creamed the space between her stomach and the bed.

Sam seldom had an orgasm just from someone fucking her: she usually used her fingers to finish herself. Most of the time, just having someone in her channel was good enough, even if she didn't have an orgasm herself.

Tom rolled off and she quickly turned over and grabbed his head, covering his face with quick, passionate kisses. He knew she was pleased, and that made him feel better about the pain he first caused her.

As they lay their resting, they heard the fireworks going off announcing the New Year. Both started laughing uncontrollably.

"I guess we made our own fire works!" Tom said.

Sam groaned then began kissing him anew.

"Stay the night? Please?" she implored.

Tom smiled, and kissed her long.

"I can stay as long as you want!"

Sam smiled contentedly as Tom snuggled intertwined with her as they fell asleep.

Sam woke the next morning to find Tom watching her as he traced outlines on her stomach down to her crotch.

"Happy New Year, sleepyhead!" he teased.

"Yes! It is!" she replied. "Want to make it even better?" she asked.

She rolled onto her stomach and spread her cheeks, but Tom rolled her back.

"I want to look at you when I fuck you this time," he said. "I want you to hold me and kiss me."

Sam smiled brightly and held her arms out to him.

"I'd like that very much! But, I may need more lubrication."

Tom lay between her legs and began working his fingers into her ass again. He took her cock into his mouth and began sucking as he finger fucked her. As he massaged her ass walls, she felt the warmth arise in her again, then filled his mouth with her cream.

Tom crawled up and placed his cock against her ring. She gasped a little as he pushed in, but it didn't hurt like it had the previous night. His mouth covered hers as he slid deeper into her. She held his face close to kiss him and wrapped her legs around his hips. She arched to meet his thrusts. He fucked her with long, deep strokes, taking his time and savoring the feel of her ass along his cock.

He moved from kissing her mouth to nibbling her neck. She responded by raking her nails along his back. Tom had known several women, but none had responded to his touch the way this lovely transgendered woman had. None had made him feel like he'd pleased them the way Sam had. And, none had cared about pleasing him as much as she had!

Sam came twice while he thrust into her. She asked if she could ride him. Tom lay on her back as she slid down his shaft. He marveled as she fought to take his entire length inside her. He played with her breasts and stroked her cock as she rode him, rocking back and forth on him. After he came she rode him a couple of minutes longer then shot her cream all over his stomach.

She lay on him, her head on his chest. Tom had been the best lover she'd ever known! She didn't want the night to end.

They rested, then fucked again. They explored each other thoroughly and tried any position that came to mind. Both were saddened when Monday afternoon rolled around and Tom had to leave. Each promised to call often.

Sam was off to work the next morning and opened her door to see Tom standing there with a bouquet of roses. He informed her he'd quit his old job so he could be closer to her. He asked if he could stay with her until her found a new job and a place to stay.

Sam pulled him inside and told him he'd already found a place, then kissed him deeply.

Sam called in sick that day, and the next.

Report Story

byAngelaK© 6 comments/ 10726 views/ 20 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heart87118711, 300bowler300 and 18 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by DianeRedfern04/12/17

So sweet, lovely and hot!

Great writing makes for a great read. The story was winning, well-told, and believable. The descriptions were vivid. The situations were compelling. You sucked me all the way in and it led to greatmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by jasmine196601/07/17

greet

What a story is there another chapter

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by BrendaNW01/06/17

wonderful, more please

more...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by cdmartine01/05/17

Great

An excellent story a great ending looking forward to the next chapter.

Made me very hard
Thank you
Martine

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by griffin5701/05/17

Very Nice

Very romantic. Kinda odd coming from a guy, but I am a sucker for a happy ending. Sam sounds like a wonderful woman. Yes, I believe that Transwomen are women.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 6 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel