Part 8 – Barry and Caramae

Caramae and Barry took it slow, going out and having long talks at the coffee house. She didn't sleep with him often. It was difficult to find times when the roommates would be out. Barry never pushed her. He never asked! Caramae always made the first move.

They'd been seeing each other for a couple of months. Barry asked her to meet him at the coffee shop on her day off. She arrived to see him talking with a blonde in her thirties. She was holding his hand and laughing. She started to leave, tears forming. Barry saw her and rose, smiling as he called her over.

The woman rose and smiled as she approached the table. Caramae’s heart was in her throat. Barry  took her hand and kissed her.

“Cara, I want you to meet my daughter, Cynthia!”

The blonde took her hand and kissed her cheek

“Dad! She's gorgeous! You old dog, you!”

The three made small talk, then Barry excused himself. Cynthia took Caramae’s hands in hers, smiling sweetly. The young tranny was warming to this woman.

“Dad has told me so much about you! He talks about you all the time! I haven’t seen him this happy since Mom died!”

“It doesn’t bother you that I'm so young? Or that I'm…………….” Caramae trailed off.

“I think he loves you. I'm okay with that!” Cynthia replied. "I know he hasn't brought you to the house, but that's because I moved home……. He needs to have you over.”

A couple of weeks later Barry called and asked her over for dinner with him and Cynthia. Caramae picked her best dress. She wanted to make a good impression.

Barry offered to pick her up, but she borrowed her mother’s old VW and made the drive over. She was pleased to see a simple, small house. She was afraid Barry's place would be huge and expensive. Barry forgot to mention he had a pool. She eyed the pool with longing, but she didn't have her bathing suit.

“That’s okay,” Cynthia said. “Mom kept all my old clothes, I'm sure I can find one that will look nice on you.”

Barry's eyes widened when Caramae came out in a white bikini. He wanted this woman child so badly he'd fuck her now, if Cynthia hadn't been there.

Caramae dove gracefully into the pool and Barry splashed in after her. Cynthia watched as the two splashed around playfully. The years seemed to melt off her father. Soon the play became more intimate as the couple embraced and kissed. Barry held Caramae, her legs wrapped around his waist. Soon, they were just kissing, not moving at all.

Barry watched the young tranny as she climbed from the pool. He wanted to grab the small bottom and bury his tongue in her hole. He could barely stand it as she ran her fingers through her curly hair.

Cynthia could see desire for her father in the young woman's eyes. Young woman!  Cynthia wasn't sure about this budding romance, especially her father fucking a boy pretending to be a woman. However, she couldn't help but think of the transsexual as a woman. A woman with a penis! But as she watched the couple, she could see the love for each other in their eyes.

“Go on, take him to bed,” she whispered as Caramae passed. .”I'll call you when dinner is ready.”

The young woman smiled her gratitude.

She took the older man's hand and said, “Come dry me off.”

Barry looked over his shoulder, but his daughter just mouthed, “Go on!”

Barry toweled the young woman, kissing the areas he'd just dried. Caramae gasped when he took a nipple in his mouth and lightly bit it. He moved lower until his mouth was level with her cock. She ran her fingers through his hair as he sucked her. He held her hips with his hands, guiding her to fuck his face. She wasn't sure about fucking him like that, but he continued guiding her hips. She thrust slowly, afraid she might hurt him. But his tongue dragging along underneath the shaft made her feel so good! She couldn't help herself and thrust faster, her balls slapping his chin. She was too excited and rapidly emptied her load into his mouth.

Caramae leaned over to kiss Barry. They’d taken to sharing each other’s cream in a kiss. To her, it was about as intimate a kiss two lovers could have!

She knelt upon the bed, pulling her knees close to her chest, offering him her raised ass. Barry grabbed her hips and proceeded to lick her crack. She purred quietly. Caramae had grown to love the time the older man spent licking her ass. He made her feel special every time he did it. Barry probed her sphincter with his tongue, twirling it around inside her asshole.

Barry applied a little lube to her asshole and slowly slid his cock balls deep. Caramae rolled her hips trying to take even more. She gripped the sheets as Barry fucked her with steady powerful strokes. Once he found she wasn't fragile, he fucked her harder. Caramae discovered she enjoyed him taking her hard. She was surprised that often made her come when he fucked her. Barry thrust one final time and filled her ass.

He pulled out and watched as some of his fluids leaked out. He really didn’t care for the taste, but the young tranny really loved having him eat her ass after he fucked her.

A text message told the couple dinner was ready. They came out to find a candlelit dinner with a couple of glasses of wine. Caramae was just barely twenty, but she'd occasionally sneak a drink from her parents’ bar. Barry didn't drink around her, out of respect and courtesy.

A note on the table read “I’m spending the night elsewhere. Have fun. Cara, wear my father out! See you around Noon!”


Barry and Caramae sat on the patio and watched the moon rise over the hills. Neither said anything, content to hold each other close. The young tranny looked at the older man’s face. He used to weigh nearly 300 pounds, but went on a diet and exercised when they started dating. Barry had lost nearly thirty pounds and had promised to lose even more! She was beginning to see the handsome man he once was.

Caramae made the next move. ”Barry, do you love me?”

She nearly bit her lips. She’d meant to say she loved him. What was I thinking? Why won’t he say something?”

Barry smiled, but continued to hold her hand as he searched for the right words. He could see the distress building in her eyes.

“Cara, when I lost my wife, I couldn’t see how I would ever love anyone else. I never expected to meet someone like you…..someone very special…..someone who could teach me to love again.”

Caramae wasn’t quite sure what he was saying. She wanted to tell him how much she loved him, but now, she was afraid of his answer.

“Caramae Daniela Whitaker, I love you more than you can possibly imagine.” Barry blurted out.

Caramae held him close and said, “I love you so very much, Barry.”

Back in bed, Caramae snuggled close to her lover.  He’d managed to fuck her almost an hour before he wore himself out. She finished him with her mouth. She was caressing his cock. If he stiffened, she’d ride him again. 

“Barry? Doesn’t it concern you that I’m thirty five years younger than you?........I mean……I’m almost ten years younger than your daughter! And you are older than my father! My parents think I should stop seeing you!”

“Cara, dear, I want you in my life forever. But I want what’s best for you, too! Don’t throw away your family for me. I’m not worth it!”

“Yes, my love, you are so very much worth it.”


The next morning, Barry asked her to stay the weekend.

“I have to take Mom’s car home,” she said. Then with a wicked grin added, “But, you can come get me!”

Caramae left ahead of Barry. Traffic slowed him enough that he found a very angry looking man on the front porch. He was shaking his finger at a very contrite Caramae while her mother looked on. Barry was nervous as he exited his truck. Mr. Whitaker was much taller than him and very muscular. He looked like he could easily break Barry in half.

“So you’re the son-of-a-bitch that’s been screwing my son…….er, daughter!” (Caramae had kicked him in the shin at the word “son".)

“I don’t like the idea of a fat old pervert using my daughter!.....Owww!”

Caramae had kicked him again. “HE’S NOT A PERVERT! He’s a good, decent, kind, loving man!.....JUST LIKE YOU!” She said as she stomped her foot.

Mrs. Whitaker invited him in. They sat at the table as Mr. Whitaker mercilessly grilled Barry. Inwardly, Barry liked this gruff man. A man who loved his transgendered daughter deeply. Caramae held his hand and yelled at her father when he said something about Barry she didn’t like.

“YOUNG LADY! GO TO YOUR ROOM AND STAY THERE!” he finally yelled. A sullen, but contrite young lady went to her room.

“She obviously loves you,” he said grumpily. “She’s just a child, and………well…. Frankly you’re too damned old for her!”

“My daughter, who’s thirty, says Caramae’s way to young. But she likes your daughter. And likes to see us together. Cara and I have discussed the age difference several times. But I will respect and honor your decision if you refuse to let her see me again.”

Mr. Whitaker frowned, but sat quietly. Soon he called Caramae back. He and his wife left the room and talked for quite a while. He was still frowning when they came back.

“You’re a nice fellow, and you obviously care for her….But I don’t want you to see her anymore!”

“DADDY!!!!” the young tranny screamed and fell to her knees sobbing.

The look in Mr. Whitaker’s eyes stopped Barry from going to her. Mrs. Whitaker touched her husband’s arm and he nodded, letting Barry pass.

Barry held the sobbing Caramae and stroked her hair. She leaned into him as he kissed her goodbye. He felt as dead inside as he had when his wife had passed away. Dejected he walked away. As he reached for the truck door, a huge black paw held it shut. He turned and looked up into Mr. Whitaker’s face. He features had softened and he looked to have aged many years.

“Please, take care of my baby,” he quietly said as he turned away, shoulders slumped.

As he held Caramae, he said, “I trust you, and I love you.”

Caramae went to Barry and hugged him tight. She kissed his cheek then returned to her family. Barry smiled sadly, then drove home. He knew she was doing the right thing, but it hurt. He wished her well.

Cynthia was home when he returned. She held her father as he wept and told her of the day’s event. As they were cleaning up the supper dishes, they heard a VW pull into the driveway. Barry rushed to answer the knock at the door. Caramae stood there with a backpack and a suitcase.

Smiling she said, “I hope you have room in your closet for my clothes.”



A year later, Todd smiled as he read the local Free Press. He saw the wedding announcement for Barry and Caramae.

Good for them!! He thought!


Walt finished reading my story and snorted.

“I didn’t know you believed in Fairy Tales”, he commented.

“Oh….I believe in 'fairy tails'…. And…happy endings!” I replied as I wiggled my ass in his face.

He groaned at my lousy pun, then chased me to bed.

- Angie K.


Angie K


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