The Ballad of Barry

Part 7 – Caramae

Caramae had been going to “parties” like Todd’s at her friend’s insistence. Gina told her that some of the gentleman were nice and left “gifts” for those who gave them a good time. Meaning open your mouth and spread your legs, and you'll get paid. Only desperation led her to go to a couple of the parties. Although she was no novice to what was expected by her dates, she really didn’t like selling herself. She told herself, she’d never do it again once she found a good job.

Caramae purposely chose to ingratiate herself with what appeared to be a nice, but lost, looking older man. Although she couldn’t put her finger on it,  but something told her this man wasn’t part of the “scene”. He was visibly uncomfortable around the other guests. She was pleased when he offered to drive her home. She wasn’t a Daddy’s Girl by any stretch of the imagination, but she felt safe around this fatherly older man.

She was embarrassed when her roommate reminded her about the rent. She was slightly disappointed when she saw the money on the bar. She was confused when he refused her “gratitude”.

After he left, Caramae sat and thought about this man. He was very kind. He treated her respectfully, something her boyfriends seldom did. She thought she might enjoy going out with him, but all she knew was his first name: Barry. She didn’t even get his phone number, and he hadn’t asked for hers!

She was surprised, pleased, and somewhat nervous when he showed up at the coffee house. She was hurt when he asked about her sleeping around for money, but he seemed genuinely concerned when he realized he’d hurt her.

When he offered to buy her dinner, she hadn’t planned to take him home. But as she waited for her shift to end, she wanted to go home to a more relaxed setting. He listened to her talk about herself and was open about his deceased wife and his fling with Todd. He hadn’t made any overt sexual advances towards her.

After she’d kissed him a few minutes, Caramae decide to take the plunge. She called her roommates and asked them to find other accommodations that night.

Barry had mixed feelings as this gorgeous young transsexual woman calmly undressed before him. She had pert small breasts, nice hips and ass, and a small cock. Her skin was the color of milk chocolate. Her curly hair fell to just pass her shoulders. But her smile…..oh, her smile! When she smiled at him, he forgot he had a daughter several years older than her. All he could think about was making love to this beautiful young woman!

Caramae often felt naked under the appraising stares of her other lovers: however, this older man looked appreciative of the gift she was offering. Rather than grabbing for her, he drank her in with his eyes. Rather than groping her, he lightly caressed her with his finger tips, tracing sensual outlines on her skin. It was as if he didn’t believe she was real! He was treating her like a delicate flower.

Barry couldn’t believe his eyes. He certainly couldn’t believe his feelings. Here was someone like him, someone who wanted more than just a ship in the night. Someone who didn’t want a plaything, or to be a plaything. Although he didn’t know it, he was already falling in love. Falling in love with a girl he’d only known a few hours at most!

Barry had to bend over to kiss her. Caramae went to the kitchen and brought back a small footstool. She could now kiss him and put her arms around his neck.

This is wonderful, she thought, I could spend hours kissing him!

Caramae unbuttoned his shirt and slid it off his shoulders. She traced outlines over his chest. It was obvious he was uncomfortable being naked around her. She leaned into him and hugged him tightly. He slowly returned the embrace and soon relaxed. She kicked the stool aside and unfastened his pants while she kissed his chest.

She was pleased to see his six inch cock spring free, already erect. She could easily take it in both her mouth and her ass. Too many of the men she dated had very large cocks and used them as tools to dominate her. They never seemed concerned with her pleasure.

Barry closed his eyes and reveled in the sensation of this moist, warm mouth engulfing his cock. She lightly caressed his shaft with her lips as she finished removing his pants. Her sucking was enough to make him feel good, but not enough to make him come. Caramae wanted him to have a nice long blow job and then still be able to fuck her.

Caramae led him to her small bed. It would be tight with both of them on it, but the closeness, and the intimacy felt right to her. Barry slowly explored her body with his mouth. His warm breath on her skin raised goosebumps all over. Her nipples stiffened as he flicked his tongue across them. He lightly fondled her breasts before moving down her body. He left no patch of flesh unkissed as he slowly traveled lower.

Caramae was ticklish and squirmed beneath him. Barry was pleased to hear her giggle when he kissed a particularly sensitive spot. She gasped when he reached the hollows of her hips.

“Please, kiss there a little longer,” she pleaded when he started to move on.

When he took her now erect cock into his mouth, she gasped with delight. None of her previous lovers had done this! Her roommates would occasionally suck her, but no man ever had. Barry had her at his mercy. She’d do anything he asked. His tongue tickled her balls. She filled his mouth with her cream. He surprised her again by swallowing it all!

Barry looked up and saw the brightest smile he’d ever seen.

“Would you like me to do it again?” he asked.

“Maybe later,” she replied. “Please, I want you to fuck me first!”

Caramae lifted her hips, but Barry asked her to roll onto her stomach. She hid her disappointment, thinking he was just going to use her as a cum dump. She was saddened because Barry didn’t seem to be that type. She gasped in amazement when she felt his warm breath on her asshole followed by his tongue probing her delicate flower.

No one had ever licked her there before! Usually, the men stuck a lubed finger in her right before pushing their stiff cocks inside. Barry was no stranger to analingus: his wife loved him to lick her ass almost as much as she loved him eating her pussy. He also liked it the times Todd did the same to him. He was pleased at the response he elicited from the young tranny. He licked her for a quarter of an hour then rolled her onto her back.

Caramae gave him a shy smile and asked, “Would you do that some more? That felt wonderful!”

Barry smiled and said later. The young tranny pouted a little, then smiled as she raised her arms and lifted her hips. Barry lubed himself and positioned his cock against her rubbery ring. Caramae was tight, her ass not used enough to loosen it. He eased into her as she arched her back to accept him. He held himself up to avoid crushing her. She wrapped her legs around his and arched to meet his thrusts.

Caramae had never been fucked so gently. Most her lovers were rough with her. Barry was gentle to the point of caution. She was tiny next to him. Although he was fat, she could tell there was muscle underneath. 

Barry‘s thrusts felt wonderful. She could feel his cock as he traveled the length of her channel. He didn’t quite hit the end, but the petite tranny felt pleasantly filled. Barry fucked her with a measured pace that would let him enjoy her ass for a long time. He feared this would be the only chance to have her, and he wanted it to last as long as possible.

Caramae only knew Wham Bam, Thank You, Ma’am! Few rode her longer than a few minutes before they were done with her. She didn’t know a man could fuck so long! Although he fucked her for a half an hour, she wasn’t ready for him to pull out when he came.

She wanted to suck him hard again, but he gave her a tired smile and said he needed to rest. He surprised her again by asking her to sit on his face so he could lick her again. 

Caramae felt deliciously wicked as the older man slid his tongue past her rubbery ring and sucked his juices from her. He held her bottom as he guide her asshole to his mouth. She stroked her cock as that magical tongue probed her hole. Barry chuckled to himself when he felt he felt her cream hit his chest. The young tranny started to roll off and get a towel. She was clearly embarrassed by her actions, but Barry held her hips and kept eating her ass. 

Caramae relaxed. She was overwhelmed by all the feelings the older man elicited. His charm and consideration was something she’d never experienced. He was rapidly ruining her for boys her own age.

Caramae surprised herself and asked Barry to stay the night. She'd never done that before, but it seemed right. She was pleased and relieved when he smiled and pulled her close.

Caramae snuggled against Barry as he drifted off to sleep. She traced outlines on his chest as she watched it rise fall. He was fat, but she could feel muscle underneath. She laid her head on his chest and drifted off to sleep.

She woke the next morning to see Barry quietly dressing. He kissed her cheek thinking she was still sleeping. She smiled then stretched. Barry still had a hard time believing his good fortune. The young tranny was beautiful in the morning light.

“I don’t have any classes today and I don’t to work till five,” she whispered. “Would you……?”

He smiled, then returned to bed. She sucked him hard enough to allow him to enter her. She straddled him, guiding his cock into her ass. She was a little tender, but soon forgot her pain as she rocked on his cock. Barry reached up and gently kneaded her small breasts while she played with her cock. Barry enjoyed being ridden by this tiny woman. The contrast of her dark skin against his pale flesh mesmerized him.

Caramae was pleased the older man still desired her. She hardly knew him, but he stirred feelings new to her. She didn’t know how to describe what she felt. She only knew she wanted the feelings to last forever!

The cock rubbing her ass walls felt even better than it had the night before! Her eyes glazed over and her breathing got shallower. She’d stopped playing with her self a few minutes earlier and rested her hands on Barry’s waist. Barry watched the young tranny as she lost herself in her pleasure. Her cock was pointing up and away from her. Suddenly, cum shot out of her cock as she experienced the most intense orgasm of her life!.

Caramae rode the older man a few minutes longer, then collapsed on his chest. Barry stroked her hair as she lay there lost in the warm afterglow.

Caramae felt Barry’s heartbeat against her as she traced patterns on his skin. She wanted to stay like this all day. Barry, too, wanted this to last. While he enjoyed the sex with other men, he wasn’t ever completely comfortable. Especially with the direction Todd had been pushing him. He really wanted something like he currently had with Caramae.

Caramae suddenly realized Barry hadn’t come! He didn’t say anything, though, hadn’t insisted she finish him. Hadn’t acted like she owed him. She appreciated that. Because of that, she was more than willing to do whatever it took to satisfy him.

Barry smiled when the young woman turned around and took him into her mouth. She was sucking him like a vacuum cleaner trying to get him off. He admired her little anal pucker and moistened a finger. He lightly teased her opening as she sucked enthusiastically.

Caramae moaned in delight. The older man was still interested in seeing to her pleasure! She’d suck him all day, if she could. She tickled his balls as she worked him ever closed to coming. He stiffened beneath her and filled her mouth with his warm, sticky fluids.

They snuggled together for much of the morning. Everything about this felt right about this. Neither wanted this time to end.

“May I see you again?” Barry nervously asked.

“I’d like that very much!” she replied, relieved he’d asked.

As Barry dressed and left, Caramae anticipated their next meeting. After he’d been gone awhile, she realized they hadn’t swapped numbers!

Caramae felt dejected when she arrived at the coffee shop. She had no idea how to reach Barry. She didn’t even know his last name! And she hadn’t given hers to him! She wanted to just hide and cry.

Her manager came and told her there was a delivery for her on a table near the back. On it, she saw a beautiful vase full of roses. With them were two notes. One was marked *Read Me First!*

Dearest Caramae,

(May I call you that?)

Thank you for such the wonderful gift you gave me. You are much more than I ever imagined. I hope you meant what you said about me calling you. I was so excited, I forgot to ask your number. Here is mine. I hope you'll call. – Barry

Caramae teared slightly. Of course I’ll call!!!!

The second note contained a receipt and some cash. Caramae's heart fell. She didn't want to be a ‘kept’ woman. But her spirits rose again as she read the note.

Please don’t be angry. I thought about your rent troubles and paid for two months for you and your roommates. This should give you a breathing space. This cash is to use however you need or wish. 

You didn't ask for this, and I don't want you to think you earned it by sleeping with me. I just wanted to help you out. You don't owe me anything. If anything, I owe you more than I could ever repay.

If you’re uncomfortable with this gift, consider it a loan. You can repay me when you are rich and famous.

Barry

Caramae cried. Barry had upended her world and had her head spinning. Everything seemed to move too fast! She needs time to think.

A week later she called him.

------ To Be Coninued -----