The Ballad of Barry

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 free 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 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 mowing 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 actually 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 mans 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 hurried 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 testing 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. He soon was comfortable. The other guests were nice, but he felt they were looking him over, sizing him up for the bedroom.

Todd had informed him that most of the guests were men. There were 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 the other guests 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. Her siblings accepted her decision. 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. 

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.

------ To Be Continued ------