Part 1 - The young man

Barry was in his early fifties. He stood about 6ft-1, and weighed nearly 300 pounds. He had brown hair going to gray, and green eyes. In his youth, he'd been considered handsome.

Barry was also very lonely. He was struggling to cope after the loss of his wife nearly five years ago. His wife of 25 years was a companion he sorely missed, both sexually and mentally. She was very open to his needs and willing to experiment. She'd even bought him a subscription to Playboy a couple of years and watched him as he was turned on by the beautiful models.

After her death, Barry hired an older woman, Consuela, come clean and cook for him. She was short, round, with ponderous breasts, and mischievous grin. She also knew he was staring at her large breasts. She was also widowed.

She caught him looking through an old Playboy, stroking himself. Barry was very embarrassed when he saw her grinning. She removed her dress and underwear and stood before him. Her breasts had saucer sized aureoles with nice big nipples. She saw the lust in his eyes.

"Let me help you with that," she said, looking at his stiff, six inch cock.

She expertly sucked him off, then stood over him, her breasts nearly hitting his face. Barry pulled one to his mouth and sucked eliciting moans from Consuela. After that, one day a week, she would clean his house naked and let him play with her breasts before sucking him off.

Consuela cleaned for Barry about a year, then informed him she was moving away to be near her grandchildren. She offered to stay the weekend and let Barry use her anyway he wanted. Barry fucked and ate her several times. She sucked him and fed him her breasts.

After that weekend, Barry was alone again.

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

Barry would occasionally sneak off to an adult bookstore when his wife still lived. He suspected she knew, but never said anything to him about it. She didn't care to suck cock and would do it, but not very enthusiastically. He found he often received fantastic blow jobs when he stuck his cock through the glory hole.

After Consuela moved, he returned to the glory holes, often several times a week. Some days, he'd spend a whole afternoon hoping to get sucked.

One afternoon, he was approached by a young man before he entered the booth. The man was nice looking and a little on the short side.

"I see you here, quite often,' he said. "I've even sucked you a few times."

He then added, "I really love sucking cock. I wondered....would you mind if I came into the booth with you and sucked you? I will pay for the movies and you could sit and watch them while I sucked your cock."

Barry shrugged, then motioned him in. he dropped his pants, sat on the edge of the bench and spread his legs. The young man handed him twenty to put in the slot. $10 would buy thirty minutes. The young man handed him another twenty. That would be nearly two hours!

He looked at Barry and said, "I hope you don't mind. You can leave at any time, but I hope you'll stay."

He then stripped and knelt taking Barry's cock into his mouth. Barry came very quickly. The young man took him all the way in and licked Barry's balls. He stopped for a minute and looked up.

"Whenever you come, grab my head and pull me tight against you, forcing me to swallow. Then I'll start all over again!' he said, then resumed bobbing up and down on his cock again.

Over the course of the next two hours, the young man's mouth rarely left Barry's cock. His tongue would lick Barry's balls every time he came.

Barry needed to go pee, but the young man said to pee in his mouth and he swallowed it all!

The time had run out and the young man was still sucking. The door opened and another man stuck his head in, watching a couple of moments then leaving.

"I'm out of money," the young man said sheepishly.

Barry pulled a ten out of his pocket and the young man smiled. Barry came several times the previous two hours, but was spent. The young man had no problem sucking on Barry's now limp cock. By the end of the third hour, he'd managed to make Barry come one last time, then left.

The next evening Barry sat back in his easy chair and stroked his cock. He played with a nipple as he relived the previous day's encounter. He remembered the young man, smooth, pale skin, the flare of his hips. Hips that begged to be gripped tightly as a cock was driven up his ass. Barry hesitated, uncomfortable with the idea of fucking another man.

That night he tossed and turned, wondering and fantasizing about the young man. The next morning he woke to find his crotch and sheets covered in cum. Embarrassed, he cleaned up and resolved never to think of the man again, even to the point of watching porn only at his computer. But each time, he found himself drawn to the gay porn sites.

Barry decided to return to the arcade and approach the young man if he encountered him again. He was prepared for rejection, but he had to try. He stood around, checking out various DVDs when he heard a familiar voice behind him.

"I haven't seen you in a while," the young man said. "How have you been?"

After a little small talk, Barry asked if he would like to suck him again. The young man smiled and followed him to the booth. Barry put twenty in the slot and the young man stripped again. Barry let him suck him a few minutes, then stopped him.

"You have a beautiful bottom," Barry commented. "I've fantasized fucking you."

The young man grinned and, "That would be nice, just not in here. We can rent a private viewing room here for a couple of hours for $50 bucks. It has a nice couch and cushions. I only ask you let me suck you after you fuck me."

Barry agreed and let the young man make the arrangements and pick the movies. The young man undressed and stood naked, encouraging Barry to strip. Barry was very self-conscious, being as heavy as he was, but the young man only smiled and ran his hands along Barry's chest.

The young man knelt and took Barry into his mouth, sucking only long enough to make him hard. He took some lube he'd bought and coated Barry's turgid member. He turned around and spread his cheeks, offering his asshole. Barry lined up his cock and pushed it in. He slid in easily, going all the way in.

"Yes! You feel good inside me!" the young man exclaimed.

Barry grabbed his hips and started thrusting rapidly, coming too soon for his, or the young man's, liking. He was disappointed with his poor performance, but the young man immediately spun around and took him into his mouth again, sucking with gusto!

"I like sucking a cock that's just been in my ass! I like my taste on it!" he said and returned sucking.

It took about fifteen minutes of vigorous sucking before Barry was again hard. The young man stood, spread his legs, and leaned against the wall. Barry stood behind him and slid his cock between the youth's ass cheeks. The young man reached behind him and guided Barry's throbbing manhood back into his asshole. He then pulled one of Barry's arms around his chest, placing the hand on a nipple, encouraging him to play with it. He pulled the other arm around and placed his hand upon his cock. Barry held him close as he thrust up into the young man. He leaned forward to nuzzle the young man's neck. The young man reached behind him and drew Barry's head close.

Barry hadn't felt this good in a very long time. He had fucked his wife this way many times, foundling her breasts and plating with her clit. This wasn't much different: he was just playing with a cock instead. He rolled a nipple between his thumb and a finger pinching slightly. The young man groaned in pleasure.

Barry thrust harder, his pelvis grinding against the young man's round bottom. The young man moaned appreciatively. He rotated his ass against Barry.

Barry managed to fuck the young man nearly twenty minutes before he gave one final hard upward thrust and filled the nice ass with his cum. He collapsed on the couch, the young man next to him. They held each other a few minutes before the young man leaned over and, once again, took Barry's cock into his warm mouth. Barry ran his fingers over the young man's smooth skin.

The young man drained him, then smiled as he dressed and left. Barry sat a few more minutes and realized he'd never asked the young man's name!

Over the next several days, Barry would sit naked, stroking his cock and reliving the encounter. He felt guilty about not learning the stranger's name, but soon lost himself in his memories.

Part 2-Todd

Barry soon began to wonder how it would feel to suck a cock. He didn't want to prowl the arcades. With few exceptions, most the men who sucked him were older men who looked quite pathetic. Barry didn't want to be remembered that way. But where to go? He researched a few clubs and picked out some likely places. One might yield some contacts.

Barry dressed nicely, wearing a sports coat and tie. He was nervous as he left his house. It had been a long, long time since he'd tried to pick up someone in a club.

The first place he entered was a seedy dive and he turned around quickly and left. The second obviously catered to a rough crowd. The third had a few desperate looking older men. He visited a couple more, neither appealing to him. He had one left: a place called "the Flagpole".

Allen was working the bar, his twin brother, Todd, seated at a table in back. Both were tall, fit men in their mid-to-late twenties, both very fit, both very handsome. Allen noticed the nicely dressed, but heavy, older man enter, look around, then proceeded to the bar. Something was different about his stranger. He looked to be new to the "Scene". Allen took his drink order. He caught Todd's attention and nodded towards the stranger. Todd nodded in return, and soon sauntered over.

"May I buy you a drink?" he asked. When the stranger nodded yes, he introduced himself. "I'm Todd."

"Barry," the stranger replied.

"I haven't seen you around before," Todd continued. "What brings you in, tonight?"

"Cruising," Barry responded.

Cruising? Todd looked more carefully at this stranger. He didn't look like a player. He seemed very nervous and unsure! Todd was intrigued.

"Care to join me? I'm about to order a sandwich. "He then walked back to his table, Barry close behind.

Over sandwiches, Barry told him about his wife and his encounter with the young man. Then he mentioned his desire to suck his first cock and was looking for someone who might be interested.

Todd was surprised, and secretly pleased! While mainly a very submissive bottom, he'd occasionally sample another bottom. And this stranger looked like he might be a willing bottom. And a virgin, no less! Allen would be jealous!

"I'd be pleased to let you suck me!" he exclaimed. "Would you like to come home with me?"

Allen stared curiously as his twin walked out the door with this stranger. He wished his brother good fortune before turning to his next customer.

In the apartment, Todd stripped and asked Barry to do the same. Nervously, Barry removed his clothes and folded them neatly. Todd checked looked him over. Barry had little body hair, and what he had was fine. Todd liked big people, and Barry was big, but not too big. Barry also had a nice six inch cock a little thicker than Todd's. Todd wouldn't mind taking it in his mouth, or his ass!

"How would you prefer me? Standing? Or sitting?" Todd asked.

"Sitting, if you don't mind," Barry replied.

Todd sat on the edge of the sofa and spread his legs wide. Barry knelt and took him in him about half his length. He closed his moistened lips around the shaft and lightly sucked as he pulled back. Todd moaned encouragingly. Barry opened his mouth slightly as he slid back down, taking a little more of Todd's cock. Soon, he was taking all of Todd's cock. The head hitting his throat caused him to gag, but he soon learned to ignore the sensation.

Todd arched his back slightly, allowing Barry to take it all. Barry's tongue dragging along the underside of his shaft felt fantastic! For a beginner, Barry was doing all the right things! He tickled Todd's balls with the tip of his tongue. He pulled back when he felt Todd's body stiffen.

Todd filled his mouth with his load. Barry thought it tasted bitter. He didn't want to swallow, but had no idea where to spit it out! The young man had always swallowed!

Todd saw Barry's expression and said, "Share it with me. Kiss me."

Todd knelt to meet Barry's mouth. He kissed him and used his tongue to take the load from Barry's mouth. He swallowed most of the load, and Barry decided to swallow the remainder. He decided to try to swallow more in the future.

"Your turn, now," Todd said, with a smile.

Todd had Barry stand with his legs spread slightly. He rapidly sucked Barry to coming. He continued sucking and Barry was soon stiff again. Todd reached between Barry's legs and fondled his balls. The moans he heard told him he was on the right track! He reached further and found Barry's asshole. He lightly fingered the rim and Barry rewarded him with another load, which he quickly swallowed.

"May I suck you again?" Barry asked.

Todd stood in front and offered his cock. Barry kissed the head and licked the slit. Todd ran his fingers through Barry's hair. He wanted to hold his head and fuck that warm, moist mouth, but he didn't want to scare the older man away. After all, Barry was doing an excellent job on his cock. He took the cock all the way and ran his tongue along the younger man's balls. Todd grabbed Barry's head and filled his mouth with another load. This time, Barry forced himself to swallow it all.

"What? You didn't save some for me?" Todd teased.

Barry was pleased with himself and promised to get together soon and do it again.

Part 3 - Todd and Allen

Later that night, Todd filled Allen in as his brother drove his thick eight inch cock deep into his ass. Allen was unusually turned on by the tale.

"Are you going to fuck him?" Allen inquired. "You're not going to let a piece of virgin ass get away from you, are you?"

"I'm taking it slow with this one," Todd replied. "I think I'll let him fuck me first."

"Do you think he'd be willing to be a threesome with us?"

"Being in the middle of two brothers fucking might be too much for him, right now. He's still new to all this."

"I want to hear every juicy detail," Allen said.

"I'll be glad to tell all......as long as your cock is deep in my ass!" Todd laughed. "Now shut up and fuck my ass off!"

Part 4 - Barry and Todd

Barry got together with Todd often over the next several weeks. He enjoyed his evenings sucking off Todd and Todd returning the favor. Todd was slowly working up to taking Barry's anal cherry.

Barry lay back on Todd's (and Allen's) bed. He had his knees bent. Todd had been slowly working a long, well-manicured finger inside Barry's asshole. Previously, he'd only ran it around the rubbery ring. Barry now accepted the finger inside and moaned. He filled Todd's mouth with his warm juices. He and Todd were now in the habit of sharing loads when they kissed.

Barry enjoyed kissing Todd. They even made out while waiting to recharge. Todd felt Barry was close. He'd make his move soon.



Barry invited Todd to his place. He planned to grill steaks and have a bottle of wine. He intended to ask Todd to let him fuck him. He worked hard to set the right mood. He didn't realize Todd had the same intentions toward him.

After the meal, Barry asked, "Do you take it up your ass? Would you be willing to let me fuck you?"

Damn! This may be easier than I hoped! And I'll get fucked, too! He thought.

"I'd like that," he replied.

In the bedroom, Barry undressed Todd, kissing him, and exploring his body with his mouth. He sucked Todd's nipples, nibbling gently. Todd held his head close, wanting Barry to chew on them, bite them hard, but Barry wasn't ready for the rough stuff. Not by a long shot! Barry moved down, licking the navel and curves and hollows of the young man's hips, before finally taking his cock into his mouth.

Todd raised his legs slightly and allowed Barry to slide his lubricated cock inside his asshole. Barry offered to use a condom, but Todd said he preferred bareback. Todd wrapped his legs around the older man's waist and pulled himself onto Barry's cock.

Todd's ass felt nice and warm on Barry's cock. Barry couldn't help himself as he thrust faster and harder. He only fucked Todd a few minutes before he stiffened and filled Todd's ass. Barry felt embarrassed, but Todd was squirming beneath him, clenching his asshole around the rapidly stiffening cock. Barry was soon thrusting again. He found his rhythm and knew he could last much longer this time.

"Your cock feels sooooo gooood inside me!" Todd declared. "Please! Ride me hard! I want you sooooo bad!"

Barry felt better than he had in a very long time. Not only was he having great sex, his partner was also having a great time. He was so captured by the moment he didn't notice the fleeting look of impatience that crossed Todd's features.

I wish he'd just hurry up and finish! Todd thought. I'm ready to fuck him! I want his cherry!

Todd put on his best 'I'm enjoying this' face as Barry continued thrusting into him. Barry felt nice, but he wasn't nearly as good as Allen. He missed Allen's big cock right now.

Barry was thrusting wildly, nearing orgasm. Todd squirmed beneath him, trying to hurry his finishing.

"Oh, Barry! Come in me! Fill me with your cum!" Todd encouraged.

Barry stiffened and dumped his second load. He rolled into his back. Todd immediately took Barry's limp cock into his mouth. He needed Barry drained before he worked on fucking him. He'd ride Barry expertly, milking that last bit of cum. Barry would have to let him fuck him then!

Todd straddled Barry's cock and sat on it hard. The older man looked surprised to be so hard so quickly! The younger man was expertly riding his cock. He could feel muscles in the younger man's ass gripping his cock as he lifted. It was almost as if he was getting a blow job from Todd's ass!

Todd had plenty of practice milking his brother's big dick with his ass. He'd been trained to be the perfect bottom. He could get the most out of any cock he rode! He could feel Barry twitch beneath him and knew the older man was about to come.

Barry grabbed Todd's hips and pulled him down hard as he emptied his last load into the younger man's talented ass. Todd rolled off and snuggled next to Barry, kissing him lightly.

"That was great," Todd said. "I really enjoyed this!"

He saw the older man was exhausted. Todd was frustrated, but knew better than to push anything right now. Maybe another time. He started to get out of bed when Barry laid a hand on his thigh.

"You could spend the night, if you like," Barry said tentatively.

Maybe all isn't lost! Todd thought. Maybe after he rests.....in the morning perhaps?

"I'd love to," he replied.

The next morning, Todd woke to the sound of the shower. When he saw Barry, he decided to join him. Barry seemed a little self- conscious this morning. He wondered how someone could be attracted to a guy his size. Todd soaped the older man's cock and started stroking it. He kissed Barry.

"Good morning," Todd purred.

Barry hesitated, then asked, "Would you like to fuck me this morning?"

Todd couldn't believe his ears! Yes!!!! He thought.

"After we finish here!" he said, then knelt to suck the now hard dick in his hands.



Todd had Barry lay face down on the bed. He proceeded to massage the older man's neck and shoulders and worked his way down his back and legs. He wanted the older man to relax and surrender to the moment.

Barry flinched a little when Todd spread his cheeks and probed his asshole with his tongue. Todd lightly licked and kissed the rim. He was also expert at this. He had plenty of practice on his brother and his very dominant older sister. He knew how to make someone feel good with his rim jobs.
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!
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.

She 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.

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."

The following week, 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 claiming 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 over thirty 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. He and his wife left the room and talked for quite a while. He was still frowning when they came back. Soon he called Caramae 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 slowly walked away. He stood a few moments at the truck door, before he reached for the handle.

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 still 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."

Epilogue

One 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.

- Angela K