The Ballad of Barry

When he finished licking, he kissed his way down the back of Barry's thighs, then asked him to turn over. He kissed his way back up to Barry's cock and sucked it a couple of moments before moving up to lick his navel.

Todd was glad Barry wasn't a hairy bear. He lightly caressed on of the nipples. It became aroused as he lightly rubbed it between his thumb and finger. He took it into his mouth and gently sucked it.

"Nice," he said. Todd was extremely attracted to bigger men and women. His sister was a big woman, and very sexy in his eyes.

"May I take you from behind?" he asked. "I like the feel of a bottom next to my crotch when I'm fucking. Would that be all right?"

In truth, Barry was glad the younger man suggested it. He was still too self-conscious to allow someone to fuck him face to face. He rolled over and spread his legs.

Todd kissed his bottom while he worked some lube into the older man's asshole. The rubbery ring was very tight, but soon relaxed.

Todd lined up his cock and slowly pushed into Barry's ass. Barry clenched tighter, at first, then relaxed suddenly, letting Todd push in balls deep. He waited a moment to allow Barry to get used to the feel of a cock up his ass.

Barry marveled at how good a cock in his ass felt. His wife had suggested using a strap-on on him once, but he declined the offer. Todd slowly ground against the older man's butt. His movements loosened Barry's asshole a little more. Barry's tight ass felt great. He planned to take his time riding this ass.

Todd nibbled and kissed the older man's neck as he slowly thrust into him. Barry moaned in pleasure. He regretted not letting his wife do this to him. He hadn't realized what he was missing! Todd slowly rode him for about a half hour. He could have ridden longer, lots of practice taught him self control. He didn't want to wear Barry out. There would be plenty occasions for that later.

Todd started fucking faster and soon emptied into Barry's ass. He kissed his way back down to the older man's asshole. He watched as the first bit of cum oozed out of the sphincter, then buried his face between Barry's cheeks and eagerly lapped up his juices. Barry moaned again.

Afterwards, Todd dressed to leave. He could tell Barry wanted him to stay longer, but keeping the older man anticipating the next encounter was all part of his plan.

"I have to be at work, soon," he lied. "I'll call you when I get home tonight."

Part 5 – Todd and Allen

Todd and Allen lay next to each other in their bed. Allen had finished fucking his twin and was resting a little before he started again. Todd filled him in on the previous night's activities.

"He's nice, but I don't believe he is ready for a threesome yet." Todd replied to his brother's query." He may never be ready for a threesome with us."

"Work on him. See if you can bring him along. We could use a fresh toy in our games."

Todd rolled back on his stomach, legs close together. He spread his cheeks enough for Allen to get the head of his cock inside him. Allen clamped Todd's legs between his and thrust balls deep into his brother.

Yeesssss!! This is how I want it! Hard!! Todd thought. Barry just wasn't big or powerful enough to fuck him like he craved. He needed to be fucked hard! He wanted to submit to a strong master. And Allen was that master!!

Part 6- the Mixer

Todd and Barry got together regularly for the next several weeks. Todd slowly introduced the older man to slightly rougher sex. They were fucking doggy style frequently. Todd convinced Barry to thrust harder, and to accept harder thrusts. They'd finish sucking each other off, then kiss good night.

Barry was beginning to feel uncomfortable with the younger man. Several times, Todd mentioned how much he enjoyed sucking a cock while taking one in his ass. He casually mentioned he thought Barry might like to try it sometime, maybe be the one in the middle.

Todd discussed Barry's continuing reluctance with his brother. Allen suggested they invite him to one of their mixers. He could meet more people and maybe find someone else with whom he was comfortable. Todd secretly began feeling qualms about what they wanted from the older man. Barry was too nice to play their games. But he would ask.....

"We're having some friends over next Friday. Please come over," Todd implored. "It might be nice to meet new people. You might even meet someone you like better than me!" he teased.

Barry reluctantly accepted and arrived wearing his old corduroy jacket and a pair of nice jeans and loafers. His Oxford shirt complimented the look. The other guests were dressed equally casually. Although the other guests were nice, he didn't really feel comfortable around them. He felt they were looking him over, sizing him up for the bedroom.

Todd had informed him that most of the guests would be men. There would be a couple of women and two or three transsexuals. Todd thought Barry might find them interesting and amusing. The best of both worlds! Todd had called them.

Although the other guests were friendly, none really caught his interest. He sat on a sofa and watched the others. After a few minutes, a small chocolate-skinned beauty approached and asked if she could sit. Barry was immediately drawn to her.

Her name was Caramae. She was petite, maybe 5ft-2, with long curly hair and beautiful brown eyes. Her smile melted Barry's heart.

She sat at the far end of the sofa, her legs tucked up under her skirt. Barry wondered if she might be one of the transsexuals. He really couldn't tell! They made a little small talk. She looked as uncomfortable as he.

She looked around, then told Barry she was going home. She didn't like the party very much. Barry offered her a ride. Caramae smiled and said she lived in the apartments across the street. She added he could walk her home, though.

Caramae didn't say much on the walk, but slipped her arm through his and laid her head against his arm. At her apartment, she stood on her toes to kiss his cheek when her roommate came out.

Her roommate saw Barry and smiled. She turned and smiled at Caramae.

"I'm off to work. Susan is at her mother's tonight. Oh....don't forget your share of the rent is due next week! Bye." And off she went.

Caramae looked crestfallen. Suddenly, Barry thought her very young and vulnerable.

"I'm about $100 short," she replied to his look. "That's why I went to the party. Sometimes, at these parties, I would go off with the other guests. They would leave me a gift when they were through using me. I chickened out: this bunch looked to like the rough stuff too much. I guess I'll call my folks tomorrow and ask for a loan."

Caramae went to fix some coffee. Barry waited until she was out of sight and took $100 from his wallet. He laid it on the bar. Unfortunately, she saw it from the corner of her eye. With a sad smile, she unfastened her blouse. Barry stopped her before she went farther.

"You don't need to do anything for this," he said. "I didn't want to see you cry. I really like your smile."

"Thank you," she smiled and hugged him tight. "And thank you for not........."

Barry kissed the top of her head and left.

Barry thought a lot about Caramae the next few days. He would have asked for her number, but he had a daughter older than her! It wouldn't be right! But, visions of her lovely smile and her chocolate skin danced before him, though. He found himself stroking his cock, fantasizing about her!

Barry started declining invitations from Todd. Todd wasn't really disappointed: he liked Barry and wished him well. Barry wouldn't have liked the BDSM scene he and Allen were into, anyway!

Barry was having coffee one afternoon at a new shop. The waitress was Caramae! It was a slow afternoon, so she came and sat with him. Barry was pleased to see her again. But he needed to know more about this woman child.

Caramae laughed and replied to his query, "I'm nineteen, almost twenty! I'm in my second year at the community college!"

"That night.....Do you often sell yourself?" he asked, afraid of the answer.

She looked down and quietly replied, "Only a couple of times. I wish I hadn't now. I feel cheap when you look at me."

She started to rise, tears forming in her eyes. Barry laid his hand on her arm.

"Please, don't go. I'm sorry I asked."

Barry asked if she'd like to have supper with him.

"I get off at seven," she smiled.

Barry was waiting when she left the shop. He suggested a couple of places, but she offered to cook at her place. Her roommates wouldn't be home till late.

Over bacon and eggs, Caramae told her life story. Her parents were very supporting when, at the age of thirteen, she declared herself to be a woman. She started hormone therapy at fourteen and changed her name to Caramae. Since she'd been home schooled, she hadn't had a rough time in high school. She'd had a few boyfriends and slept with a couple. But boys tended to look at her as a plaything, not a real woman. And others got angry to find out she had a cock.

Barry told her of his wife and how he came to be with Todd. Caramae listened better than even his wife did when she still lived! He finally blurted out how beautiful the young woman was.

Embarrassed, he started to leave, but Caramae pulled him back. She crawled onto his lap and kissed him.

They kissed for quite a while before she excused herself. She returned with her phone and asked her roommates to sleep elsewhere that night.

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. And, most importantly, 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 fingertips, 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 days 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 herself 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!