Changing Sides Ch. 01


Jackson Young sat in the coffee shop that early Saturday evening contemplating life. He had moved to Orlando a month ago to start over. He smiled ruefully into his cup as he thought about the events of the last year and a half.

He absently rubbed the deep indentation on his left ring finger. He had worn the ring every day for 26 years, and now…

Linda got sick 18 months ago. Cancer. They went through everything, surgery, radiation, chemo but to no avail. He buried her on a rainy spring day exactly 9 months later. Their two sons were there of course, and they did offer to have him stay with them in California, but they both had young families of their own. He put on a brave face and told them he would be fine. Liar.

New York held too many memories. The house, the streets, the people. When the CEO at his biomedical firm told him about the new office opening in Central Florida he took it.

Hey, it worked for Tom Hanks in “Sleepless in Seattle” right?

The move was difficult. Linda had been the planner. She was the organizer. Everything he would normally have left to her he now had to muddle through…alone.

Alone. His eyes burned with unshed tears as the word stabbed him in the heart. This was NOT the plan. They were both going to retire at 55. Travel the world, visit the grandkids, grow old and fat together.

Now here he was, in a new town. He had just turned fifty-one in December. He looked at his reflection in the shop storefront. He was a middle aged black man. Six foot tall in his bare feet. He had a medium build and kept in pretty good shape. But he did have a little more beef around the middle than he liked. He kept his head and face shaved to hide his receding hairline and the gray. He knew he looked young for his age. His wife had always liked his caramel colored skin and his hazel brown eyes (compliments of his Irish grandmother).

He was finally getting back into a semblance of a routine. Work was going well. It was always challenging starting up but he had a good team and they seemed to respect and maybe even like him. They seem to have been briefed about his personal issues so were understanding about his somewhat distant manner. He gently but firmly resisted any attempts to invite him to their after hours gatherings, knowing that he wasn’t ready to socialize yet. He wasn’t going to be a wet blanket.

He joined a gym and worked out most evenings and on the weekend he would take an evening walk and then stop at the coffee shop around the corner from his high rise. He sat at his usual corner booth reading the Sun-Sentinel on his tablet in a desultory fashion while his half-eaten croissant and steaming cup of black Jamaican coffee sat half ignored.

“Excuse me , sir. Your server had a family crisis, so I’m covering her tables. Is there anything else I can do for you?”

The server spoke softly, even hesitantly. Jackson glanced up, his mouth already opening to dismiss the intrusion when he froze. He was staring into the most piercing blue eyes he had ever seen. His eyes took in the honey-blonde hair held back in a ponytail, the high cheekbones the thin slightly upturned nose. The lips were full and inviting…


Jackson blinked, quickly closed his gaping mouth and then mumbled inarticulately.

“Ummm, could I have another croissant please?”

The eyes sparkled and twinkled and the lips parted to reveal (of course) perfect teeth. The smile was still registering on his retina when he heard the response.

“Coming up!”

He watched the retreating figure for a few seconds, then he started to breathe again. Alarm surged through him. He hadn’t had a reaction like this to another person since the night he first met Linda! But this wasn’t possible. He shook his head and took a long gulp of his coffee, cursing as he burnt his tongue.

Jackson’s heart was pounding and he felt a sudden urge to flee. His server was returning with his croissant. He looked at the name tag affixed to the apron.


The blue-eyed blonde was a guy!

Tommy was petite and effeminate. He was clearly gay, but wasn’t flaunting his sexuality. He was young, no more than 25 Jackson guessed. He stood no taller than 5’6″ in his baby blue Vans skate shoes. He was slender and lithe. The white t-shirt showed his hairless arms. His fingers were thin and elegant and the nails were bubblegum pink. The black super skinny jeans clung to his hips like a second skin.

The smile was slightly mischievous as Tommy placed the croissant and a slice of cherry cheesecake in front of him.

“I know. You didn’t order this, but…” Tommy bit his lower lip.

“I thought you could use something sweet.” A blush crept slowly up Tommy’s neck and cheeks as his eyes held Jackson’s. “On the house.”

Jackson gave Tommy what Linda used to call his ‘thousand-watt smile’. It had been a while since he had reason to smile like that.

Jackson took a small forkful and tasted it. He nodded appreciatively,

“Delicious.” gaziantep escort

Tommy smiled and then placed his bill alongside his plate and retreated toward the kitchen. Jackson had more cheesecake as his eyes lingered far too long on Tommy’s prominent ass encased in those too tight jeans. There was enough cleavage there so that each cheek appeared to be cupped separately by the denim…


His inner voice bellowed in his ear.

“Stop that shit right now!. This is a fucking GUY. A WHITE GUY! A GAY WHITE GUY!!”

Jackson picked up the bill and dug into his pocket. He needed to get out of here. Right now. As he looked down he smiled despite himself.

At the bottom of the tab was written: “Please come again! Tommi.” Of course, the ‘i’ was dotted with a smiley face emoji.

He dropped some bills on the table, leaving a huge tip. He hadn’t finished but he knew he had to get out of there.

That night, Jackson stepped out of the shower, toweled himself off and padded into his bedroom naked. He was horny and he knew why. He booted up his laptop and sat on his king bed. He had resorted to porn occasionally since Linda’s death so he started clicking through various sites. He started stroking his cock as he watched a pretty brunette suck a large black cock. By the time she took a faceful of cum he had a raging erection. He wasn’t porn-star big but he had never had any complaints about his moderately thick circumcised cock. His face clouded briefly, Linda had called it her chocolate caramel fuckstick. They had enjoyed an active sex life until…

He clicked on the next video …an innocent-looking young blonde was eagerly swallowing another fat dick. Her blue eyes looked straight at the camera while she bobbed eagerly up and down. She stopped after a couple of minutes and knelt on the nearby bed wiggling her tight ass at the screen as she looked over her shoulder.

“Please fuck my tight ass, Daddy! I need your cock so bad!”

Jackson’s cock exploded as he realized how much she looked like Tommy!

He tossed in his bed that night. His dreams were filled with blue eyes, blonde hair, sexy lips and tight asses. Then suddenly Linda was there, smiling sweetly.

“Baby, I had no idea you were GAY!”

He woke up in a sweat, his heart racing and interestingly with a rock hard erection! His hand brushed against his cock and he shot rope after rope of thick cum onto his hairy chest and belly.

“Jackson, pull yourself together man!” His admonition sounded hollow and unconvincing in the empty room.

For the next month he did just that. He immersed himself in his work, getting in early and working late. He avoided the coffee shop. Jackson even went on a date. Elaine was a thirty-something divorcee and a rep for a vendor company. She was a tall curvy black woman. She had flirted with him on the most recent of her weekly sales calls and he asked her to dinner.

Dinner had been pleasant. Great food and conversation, but no spark. He took her home later, politely declined her offer of a nightcap and took the short drive back to his condo. It was still early and for some reason Jackson was still restless. It was a cool Central Florida night and he was wearing black Levi’s and a white long-sleeved shirt with the top two buttons undone to reveal his hairy salt and pepper chest and the single gold chain from which his wedding ring now dangled. He slipped his hands into the pockets of his stylish leather jacket and decided to take a walk. Before too long he found himself in front of the coffee shop.

He had not been back since that day. The place looked empty. He saw Tommy cleaning up a table. He was wearing his usual skin tight jeans, t-shirt and apron. Jackson’s mouth was dry as he pushed the door and sat at his usual booth.

He heard quiet footsteps and then Jackson was looking into those blue eyes again. Tommy smiled.

“Hi there! I haven’t seen you around for a while. My don’t we clean up nice!”

Jackson saw Tommy’s approving gaze and his cheeks burned.

“I’m sorry but I was just about to close up. The kitchen is closed but I can get you coffee, tea or …”

He paused dramatically, right hand on his hip,

“Or dessert!”

Jackson was speechless for a second before he swallowed the lump in his throat.

“I’d really just like something sweet, please, Tommy.”

Their eyes held for several heartbeats before Tommy wheeled and headed for the front door. He locked the door and turned the sign to the closed position. Then Jackson heard rattling of dishes before he saw Tommy emerge from the kitchen with a tray. When he lay the tray on the table Jackson saw it held a large slice of cheesecake, two forks and two tall glasses of milk.

“I hope you don’t mind if I join you?” Tommy raised a perfectly plucked eyebrow speculatively.

“Not at all. Dessert is always better with company.” Jackson smiled. “What the hell”, he thought to himself.

The cheesecake was again delicious and went down well with the ice cold milk. They finally introduced themselves and chatted casually while they ate. Jackson learned that Tommy was actually 22 and on semester break from a local college where he was studying graphic design. He was gay and had left his home in Kansas 4 years ago after coming out to his family. He had just broken up with his boyfriend 2 months ago (an older guy apparently).

Though he couldn’t explain it, Jackson felt like talking. He told this kid his life story. It was like a catharsis. He hadn’t bared his feelings like this since Linda died. Not even to the grief counsellor the boys made him see. Tommy just listened. He could feel the pain and loneliness of the older man. He wanted desperately to say something but he wisely held his tongue.

Finally Jackson finished his tale. He sat back in his chair and polished off his milk. He watched Tommy do the same. Jackson grinned as Tommy put his glass down. He had a classic milk mustache which, coupled with the stray lock of blond hair dangling down his forehead made him look …ADORABLE.

“What is it, Jackson? What’s so funny?”

“Got milk?” Jackson responded cryptically.

Tommy looked at his reflection in the mirrored surface of the stainless steel napkin holder and giggled. He slowly licked the milk from his top lip, managing to look cute and sexy at the same time.

“Jackson? Why did you come in here tonight?”

Jackson remained silent, refusing to meet those soft blue eyes.

“I’ve really enjoyed your company Jackson, but I know you’re straight as an arrow and you know that I’m gay. If I didn’t know better I’d think that you were attracted to me.”

Jackson didn’t even try to deny it. He finally looked into Tommy’s eyes again.

“The thing is Jackson, I’m definitely attracted to you.”

Tommy smiled as he reached across the table and took Jackson’s much larger hand in his and squeezed gently.

Jackson suddenly felt warm all over. He shook his head as if coming out of a trance and he smiled. He wrapped Tommy’s hand in both of his and pulled the trapped appendage to his lips. Tommy stifled a moan as he felt goosebumps run up and down his arm.

Jackson finally found his voice, no more than a husky whisper.

“The answer is yes, Tommy I find you attractive. I know I’m supposed to be straight, but I think you’re the most beautiful creature I’ve ever seen,”

He paused as a blush crept up Tommy’s neck and face.

“I’ve hardly been able to think about anything else since I first saw you. The trouble is that I’m in unknown territory here. I’m not sure where to go from here.”

Tommy smiled coyly.

“Jackson, we’re just two people that feel something for each other. Just do what comes naturally,okay?”

Jackson said nothing for a minute. Suddenly he released Tommy’s hand from his grasp and stood up. Tommy’s face fell, thinking the older man was leaving. Instead, Jackson proceeded to sit next to him in the booth. He took the youth’s smooth chin in his hand and tilted his head up while leaning in closer. Jackson firmly pressed his lips softly against Tommy’s marveling at how soft they felt. Tommy moaned softly as he closed his eyes and let his lips part slightly. Jackson accepted the implicit invitation and his tongue slid out against Tommy’s teeth and then into his mouth. Their tongues touched and dueled briefly before Jackson pulled back.

He realized Tommy’s fingers were digging into his shoulders and they were both panting.

“Well? Any regrets Jackson?” Tommy cocked his head to the side and slid his hands appreciatively up and down the bigger man’s well muscled arms.

“Yes. One regret. That it took so long for me to do that!”

Tommy squealed as Jackson pulled him onto his lap and kissed him again. This time their tongues entwined hungrily. Jackson nibbled on Tommy’s ear and neck, causing him to wriggle in Jackson’s lap. The effect of the tight firm ass grinding on his crotch was immediate. Tommy felt the obvious bulge against his buttocks.

Tommy looked into his eyes, “Is this for me?”

Jackson didn’t hesitate, “Yes. Yes it is!”

“Jackson, if you’re sure about this then maybe we should go somewhere a little more private!”

They quickly disentangled and stood. Tommy quickly lost the apron and finished closing up. They started the short walk to Jackson’s condo in silence, both lost in thought. Their hands brushed and Tommy quickly slipped his hand into Jackson’s. He smiled contentedly as Jackson squeezed firmly and made no effort to let go.

Tommy gaped open mouthed at the ultramodern building as Jackson led him by the hand into the spacious lobby. They stepped into the sleek elevator and Jackson pressed the button for the 12th floor. As soon as the doors closed Tommy was in Jackson’s arms, lips hungrily seeking the older man’s. He moaned as he felt hands cupping and squeezing his tight ass cheeks as his own trembling fingers stroked Jackson’s burgeoning hardness through his jeans. The elevator came to a smooth stop and they pulled apart panting.

Jackson glanced nervously at Tommy as he opened his front door.

“Am I really doing this?” He thought apprehensively.” What should I do?”

He quickly ushered Tommy inside and flipped on a light as he latched the door. He hung up his leather jacket and Tommy’s hoodie.

“Would you like a drink or some-“, Jackson began when Tommy grabbed his hand and quickly led him over to the plush leather loveseat in the living area.

“I have everything I want right now”, the petite blonde said sultrily as he kissed Jackson passionately. Then he stepped back and he started to unbutton Jackson’s shirt. He ran his fingers over the older man’s hairy chest as he licked his lips. His fingertips lightly touched Jackson’s nipples and they both moaned. Tommy stripped the shirt off and leaned forward to take the right nipple into his hot mouth as he dropped his hands to Jackson’s belt.

Jackson moaned loudly as Tommy’s talented tongue flicked sucked and licked first the right then the left nipple. Tommy was delighted to feel them harden in his mouth. He loosened Jackson’s belt and unbuttoned his jeans. Tommy’s blue eyes mirrored the lust in Jackson’s as he fell to his knees while tugging at the slacks and boxer briefs beneath them. Jackson kicked off his shoes and then helped Tommy complete undressing him.

Tommy remained on his knees, his hands resting lightly on Jackson’s hairy brown thighs. His eyes flicked from the older man’s face to his throbbing cock. He licked his lips unconsciously.

“God, Jackson, your cock is beautiful.”

Jackson shuddered as he felt Tommy’s warm breath on his circumcised glans. He moaned as delicate white fingers encircled the engorged shaft. Tommy extended his tongue and caught a pearlescent droplet of precum that oozed from the slit. He closed his eyes briefly as he savored the essence then he looked into Jackson’s brown eyes as his lips closed on the tip of his cock.

Jackson moaned loudly and fought the urge to plunge into Tommy’s mouth to the hilt. He watched as the younger man moved his head slowly around as he sucked on Jackson’s cock. His tongue flicked back and forth across the smooth helmet as he stroked his hand up and down the thick shaft. Tommy’s other hand ran across Jackson’s lower belly and through his thickly curled pubic hair then down to cup his heavy balls.

Tommy started to fellate Jackson in earnest, as he took more of the cock into his mouth, his tongue flicking back and forth and his cheeks hollowing as he sucked hard when pulling back on the shaft. Jackson saw his cock glistening with saliva as the cool air hit it before once again being engulfed in the warmth of Tommy’s mouth. He ran his fingers gently through Tommy’s blonde locks as his hips undulated involuntarily from Tommy’s talented ministrations.

“Tommy, that feels too fucking good! I’m going to cum very soon if you don’t slow down!”

The blonde’s response was to increase his tempo, deep throating Jackson on each downstroke, his tongue flicking out to lick the older man’s scrotum. His hands clutched Jackson’s clenched butt cheeks as he kept up his torrid pace.

“Oh fuck, here it comes!” Jackson threw back his head and bellowed his release as Tommy felt the twitching and throbbing in his mouth that signaled Jackson’s orgasm. He pulled back so his lips covered only the head as warm spunk poured from Jackson’s cock. Tommy let his mouth fill with the warm goo, ensuring that he had caught every drop, then sitting back on his haunches looking into his new lover’s eyes and swallowing it all down.

Suddenly weak kneed Jackson flopped back onto the loveseat, his breathing labored, but a contented smile on his face.

Tommy crawled over to kneel in front of him. Tommy felt a pang of anxiety. He wondered if Jackson, having gotten his rocks off might be having second thoughts.

“Do you want me to leave? I understand if you don’t want to go any further.” Tommy’s voice was almost a whisper and he avoided looking into Jackson’s eyes.

Jackson smiled. He stood languidly, his eyes twinkling as he held his hand out. Tommy beamed as he took the proffered hand and let Jackson pull him to his feet. He trembled as the older man pulled him into his arms and kissed his pouty lips, gentle pecks at first, then with more passion as Tommy surrendered his mouth with a moan.

“You’re overdressed, sexy.”

Tommy blushed red as he giggled at the contrast, standing fully clothed in front of this gorgeous naked black man. He kicked off his sneakers and pulled his t-shirt off and let it fall to the floor.

The light glinted off of the small gold hoops through Tommy’s large, pink nipples. Jackson felt blood start to surge through his flaccid cock as he gazed at the younger man’s smooth chest and flat belly. Tommy smiled seductively as he turned his back and slowly peeled off his skin tight jeans as he bent at the waist. Jackson’s breath caught as he saw Tommy’s perfectly girlish ass was revealed.