Changing Sides Ch. 02

Story Info
Jackson and Tommy continue to explore each other.
3.2k words
4.69
4.4k
4

Part 2 of the 2 part series

Updated 06/10/2023
Created 10/22/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jackson rolled over and blinked stupidly as the Sunday morning sunlight streamed into his bedroom. He smelled the aroma of dried sweat and sex. The rumpled and stained bedclothes jogged his memory of the previous night's encounter. His nostrils detected the faintest odor of Tommy's perfume...

Tommy! He was gone. Jackson quickly glanced around, checking if anything of value was missing, then he stopped himself and jumped out of bed angrily, chiding himself for the thought.

Did this really happen? Was it all a dream? Then he saw the neatly folded paper under his phone.

Jackson rolled over and blinked stupidly as the Sunday morning sunlight streamed into his bedroom. He smelled the aroma of dried sweat and sex. The rumpled and stained bedclothes jogged his memory of the previous night's encounter. His nostrils detected the faintest odor of Tommy's perfume...

Tommy! He was gone. Jackson quickly glanced around, checking if anything of value was missing, then he stopped himself and jumped out of bed angrily, chiding himself for the thought.

Did this really happen? Was it all a dream? Then he saw the neatly folded paper under his phone.

'Dear Jackson,

Thanks for the wonderful evening. I really enjoyed it. I wanted to stay longer but thought it better to not be there when you woke, just in case you wanted to write this off as a one time thing. You may feel somewhat confused right now and I don't want there to be any awkwardness.

I have to admit that I am attracted to you, but I understand if the feeling may not be mutual. You have my promise that I won't share this with anyone else, ever. So you can return to your life and me to mine if that is what you want. Hopefully you'll still come by the shop for coffee sometimes (you are a great tipper! )

Tommi

P.S. Here's my number, just in case. XOXO.'

Jackson stared at the note for a few minutes before folding it carefully and slipping it back under his phone. He took a long shower, images of the previous night bombarding his brain whenever he closed his eyes. He grinned ruefully as he realized he was getting an erection! "Not bad for an old man."

As he dried himself off and got dressed his eyes kept wandering to the note. He really wanted to call. He had some toast and coffee and read the paper as he tried to get a handle on his jumbled emotions. He just had a night of hot sex with a guy. Was he GAY??? Was it just a "thing" that happened because he was lonely? Should he just walk away?

Tommy saw the message pop up on his phone and his heart leapt. He didn't recognize the number but he knew who it was!

Can we meet? I really want to see you. I NEED to see you.

When Jackson walked into the downtown chain restaurant 2 hours later Tommy was already sitting at a booth. He slid into the seat alongside the young femme and as their hands touched Tommy slipped his hand into Jackson's and squeezed gently before letting go. They smiled at each other somewhat diffidently and didn't try to speak to each other until the waiter had taken their orders for drinks.

"Hi, Jackson", Tommy's voice was a sultry whisper. "I'm really happy you came."

The older man grinned mischievously as he winked at his companion knowingly.

"Me too Tommy. Twice! Thanks to you."

Tommy's cheeks turned bright red as he blushed, then they both broke down laughing. Jackson resisted the urge to plant a kiss on those pouty tempting lips.

They made small talk over lunch. Both enjoying the other's proximity but keeping the conversation light.

"Jackson, what's happening here?" Tommy's face was suddenly serious, his blue eyes piercing.

The older man lay down his fork deliberately and dabbed his mouth with his napkin before responding.

"I don't know for sure Tommy." He paused before continuing," I'm definitely attracted to you. I keep enumerating the reasons why it won't work but I can't shake the emotions that I'm experiencing."

"You're gay, I'm straight. Although after last night I'm not sure what I am. You're very young, I'm older than your own father I bet. You're white, I'm black. That being said, I know that right now I don't want this date to end."

They stared into each other's eyes for a long minute and Tommy started to speak when they were interrupted by the waiter. Had they decided on dessert?

Tommy smiled knowingly at Jackson, his eyes sparkling and dancing in the low light. He grasped his new lover's hand as he replied, "Could we just have one large slice of cheesecake please. Two forks, to go. Cherry topping on the side."

As the waiter retreated Tommy leaned close, "I'm hoping this gorgeous man will have me over at his place for dessert!"

Impulsively, Jackson leaned in and kissed Tommy gently on the lips. "You're definitely the sweet thing I want to devour!"

The drive back to Jackson's condo was like torture for him as he struggled manfully to keep his attention on the road. Tommy spent the journey with his head resting on Jackson's right shoulder as he ran his brightly painted fingernails along Jackson's inner thigh, occasionally making contact with his burgeoning erection.

When he mercifully pulled into the underground garage he swept the sexy waif into his arms, kissing him deeply and hungrily. When their lips finally parted they stared into each other's eyes both panting slightly. A slow impish grin came to Tommy's face and he suddenly leaned forward, his slender fingers deftly loosening Jackson's belt and pulling down his underwear to expose the throbbing erection beneath.

Jackson moaned as Tommy's soft lips engulfed him and his tongue licked at his pulsating shaft. Tommy moved into a kneeling position as he continued to suck and lick Jackson's cock with a steady rhythm. Jackson's left hand lightly tousled Tommy's hair as his right stroked the younger man's back and down to his denim encased buttocks. Every time Jackson's fingers probed the younger man's asscrack Tommy moaned loudly around the cock in his mouth and his body shuddered.

Almost reluctantly, Tommy released Jackson's throbbing cock from his mouth and looked into his eyes, "Jackson, honey, please take me upstairs. You don't know what you're doing to me!"

Jackson pulled him into another deep soulful kiss, then gingerly zipped his pants over his erection. They got out of the car and walked hand in hand to the elevator. The lovers shared tender kisses as the elevator ascended to the 6th floor. Jackson fumbled briefly with the lock as he pulled Tommy eagerly into his condo. Their lips locked hungrily as Jackson pinned Tommy against the door. Fingers fumbled with buckles and buttons as they stumbled into the bedroom and fell naked and giggling onto the bed. Jackson lightly pulled on one of Tommy's nipple rings,eliciting a soft moan as his slender fingers stroked the older man's cock. Tommy kneeled beside Jackson and hungrily resumed sucking and licking his cock. Jackson's hand found the back of the blonde's head as he moaned in appreciation. He traced his fingers down the younger man's spine until he was gently squeezing and kneading those sexy, tight asscheeks. Tommy moaned around Jackson's cock as he felt a finger probe his anus. He shuddered as he felt Jackson's fingers caress his hairless scrotum and stroke his small slender cock.

Tommy squealed in surprise as he felt himself being lifted in the air and then set down with his knees astride the older man's head. He gasped as he felt Jackson's warm breath on his scrotum followed by the older man's tongue and lips. Tommy resumed sucking Jackson's throbbing erection as he felt his actions being reciprocated.

For several minutes the lovers stayed in the 69 position, the only sounds heard were the slurping and sucking sounds punctuated by the occasional moan. Tommy finally came up for air, grinning mischievously as he raised his upper body on his outstretched upper arms his hands resting on Jackson's muscular thighs.Tommy's cock slipped out of Jackson's mouth with a loud pop and he found himself looking at Tommy's pink puckered anus.

"Don't stop baby," Jackson's cock throbbed as Tommy's super sultry voice penetrated through the trance-like fog. "I love your tongue. Lick my hot little asspussy. Make me nice and wet. You know you want to!" He gently glided his scrotum back and forth across Jackson's lips until he could once again feel his breath on his perineum and anus.

Jackson ran his tongue roughly along the ridge between Tommy's ball sac and anus then he slowly circled the puckered orifice. He licked and teased and sucked, pausing on occasion to let the tip on his tongue partially penetrate the opening. Tommy moaned and squirmed sensually, grinding his pelvis against Jackson's mouth.

"Please Jackson honey, don't tease me! Eat my ass! Fuck me with that hot tongue! Then you can fuck me for real!"

He felt his cheeks parted by strong hands and he held his breath as he felt the desired tongue slither easily into his rectum. Jackson started working his tongue deeper and deeper inside while his lips firmly pressed against the muscular ring of Tommy's anus. The younger man now sat upright, bouncing up and down on Jackson's face, his head thrown back in ecstasy as his left hand stroked his cock as he felt himself brought to the verge of orgasm. Sensing the frantic need of his lover Jackson withdrew his tongue and quickly replaced it with his thumb. The pad of his digit finding and massaging Tommy's now aching prostate.

"Jackson!" Tommy screamed as he came. His anus gripped Jackson's invading finger tightly as he shot rope after rope of semen onto Jackson's chest and belly. He collapsed onto the bed beside Jackson panting.

Jackson slowly became aware of the sticky deposit on his torso. He dipped his index finger in the translucent goo and slowly brought it to his face. No odor he could discern. He licked and then sucked his fingertip clean. He wasn't sure if he liked it but he quickly tried some more. He realized suddenly that he had almost consumed all of the cum when he saw that Tommy was watching him with those ice blue eyes.

"Next time you can drink straight from the source if you like stud!" The beautiful smile lit up Tommy's face as he saw the goofy grin on Jackson's face. He eased into his lover's embrace as they kissed passionately.

Tommy paused to lick his lips dramatically, "Mmm! I taste delicious." Jackson playfully smacked his ass as they laughed. Tommy wriggled closer, "Careful honey, you start doing that and things may get a bit kinky!"

Not waiting for a response, Tommy grasped Jackson's still impressive erection and started slowly stroking it. He thumb flicked over the glans and he was rewarded with a throaty moan from the older man.

"Jackson," Tommy's tone was suddenly more serious, "I want you to make love to me. Now."

A hungry look came into Jackson's eyes as he pushed Tommy onto his back kneeling between the youth's slender thighs as he leaned in and kissed him on the lips, then trailed a wet path to the angle of the jaw, pausing to nip gently at the earlobe and pulling on the golden hoop therein. Tommy squirmed and moaned as he broke out in goosebumps.

"Oh yes baby, love me. Please!" Tommy begged as Jackson hooked his forearms under Tommy's knees and raised them towards his chest laying him open before Jackson's lustful gaze. Tommy hooked his heels on Jackson's broad shoulders as he looked between their bodies at Jackson's bobbing chocolate brown cock.

Jackson was almost trembling with desire, and something else he couldn't describe. He grasped his cock and slowly rubbed the head against Tommy's moist pucker. The younger man arched his hips, trying to impale himself on the object of his desire. Jackson slid slowly forward, They moaned almost in unison as Jackson slowly penetrated Tommy's anus and sank into the warm receptive rectum. Jackson didn't realize that he had been holding his breath until he felt his scrotum gently slap against Tommy's silky buttocks. He drew in a deep breath, revelling in the exquisite sensations. He glanced down at Tommy's gorgeous face, the sexy blonde's eyes were half-closed and his mouth hung slightly open. His eyes flew open as he felt Jackson's lips on his again. He eagerly accepted the insistently probing tongue into his mouth as Jackson's pelvis began to move against his, slowly pistoning his fat cock in and out of Tommy's ass. Slowly and gently at first, then with increasing frequency Tommy felt Jackson's hardness fill him.

The room reverberated with the moans and groans of pleasure and the slapping of sweat-slicked skin against skin.

"Oh god Jackson, I love what you do to me. Don't stop, stay here forever! So good!" Tommy was almost incoherent. Jackson now rested on his outstretched hands, his glistening torso suspended as he moved his hips faster and harder.

"You make me so crazy sweet Tommy. I hope this never ends." Jackson gritted his teeth as he felt his orgasm rising in his loins.

"It doesn't have to, sexy. Come inside me! Make me yours!" Tommy's cry was plaintive.

Jackson felt his cock throb as he bottomed out in Tommy's ass and he collapsed on top of his lover as his come exploded into Tommy's hot rectum.

The older man flopped over onto his back panting as his still somewhat turgid cock slid out of Tommy's gaping hole. Tommy lowered his legs as he groaned at the sudden feeling of emptiness. He smiled contentedly as he felt some of Jackson's semen leaking out of his ass. He draped an arm and leg across Jackson's body as he snuggled close. The sounds he made reminded Jackson of a cat's contented purr.

When Jackson woke the room was dark. The clock on the nightstand read 10:17 pm. Tommy wasn't there, He was suddenly overcome with a sharp sense of loss. Alone. Again.

The bedroom door opened and Tommy padded softly into the room. He paused when he saw Jackson had moved. "Oh good, you're awake."

Jackson grunted inarticulately and switched on his reading light. Tommy was still gloriously naked. He was carrying a small tray and 2 glasses of milk. He saw Jackson's quizzical look and smiled slyly.

"I went to clean up and then I remembered the cheesecake." They both laughed as he set the tray on the bed between them. They talked quietly as they partook, Tommy insisting on feeding Jackson.

"When I woke up alone, I thought you had gone." Jackson's voice was soft. Tommy's eyes looked searchingly into his.

"Did that upset you?"

"Yes. It did."

Tommy's eyes glistened as he gently traced Jackson's thick lips with his index finger.

"Do you want me to stay the night, Jackson?"

Jackson didn't reply immediately. He captured Tommy's digit gently between his teeth and sucked on the tip while he nodded his head in an affirmative manner.

"Stay as long as you want,baby."

Tommy beamed as he leaned in to kiss him.

Tommy was suddenly dragging Jackson by the hand into the bathroom.

"Let's shower. I'm so sticky!" Tommy giggled playfully. Jackson followed without comment his gaze fixed on Tommy's sexy undulating ass cheeks. He felt his cock starting to throb.

Tommy turned the rainwater shower to a thin steamy mist and stepped in. He grabbed the body wash and started lathering his blonde locks and smooth skin. Jackson stood transfixed as he took in the erotic scene. He was vaguely aware of the stirring in his groin as he watched water and soap cascade down Tommy's nubile form.

He was suddenly yanked from his reverie by a soggy loofah mitt smacking against his chest.

"I can see you're enjoying the show, stud. But I was hoping to get some help with those hard to reach areas!" Tommy was standing under the spray hands on his hips with an impucent smile on his pouty lips.

Jackson smiled broadly then hopped into the shower and swept the younger man into an embrace and kissed him hard. Tommy finally broke the kiss, panting.

"Wow Jackson, I could get used to this!" Jackson's only response was to pick up the loofah and start to massage the soapy lather into Tommy's skin. Starting at the neck then down to the shoulders and chest. Tommy moaned and trembled slightly as it glided over his pierced nipples. The moans became louder as the loofah moved to his flat belly and brushed lightly over his bobbing erection. Jackson let the loofah drop to she shower floor as he gripped the soapy member and began to stroke it slowly. Tommy's body trembled as his skin tingled under the spray.

"Oh god Jackson! You're driving me crazy!" Tommy's word came out in a half moan half scream as the older man teased him. Jackson switched the shower off as he eased the younger man against the steamed up glass enclosure. He continued to

stroke Tommy's cock as he kissed him hard then slowly kissed and licked his way down his neck, chest and belly as he slowly dropped to his knees at the feet of this gorgeous blond creature. He cupped Tommy's balls and rolled them gently in one palm as his other hand milked his swollen pink member. After every few strokes he would run his thumb across the pee slit, wiping away droplets of pre seminal fluid.

Tommy squirmed and moaned under his black lover's touch. Jackson pushed Tommy's small penis up against his belly and he took his scrotum into his warm mouth. He slid his tongue around and between his testicles, pausing at times to pull and nip at the wrinkled sac. Tommy's hands gripped the back of Jackson's head tightly as he thrust his hips against the mouth giving him so much pleasure. Jackson let his lips trail up the underside of Tommy's cock before locking his lips around the head.

"Please Jackson baby, don't stop! Your mouth feels like heaven!"

Jackson's brown eyes locked with Tommy's baby blues as he started to suck in earnest. Working his lips up and down the 5 inch shaft as his tongue flicked out and around.

''Oh Jackson, I'm so close...! I'm going to..! Please!"

Tommy was babbling as he felt his orgasm explode. Jackson felt Tommy's cock start to throb and pulsate as he felt his mouth fill with the salty ejaculate. To Tommy's and his own amazement he swallowed every drop.

Tommy's legs felt like rubber as he started to slide down the glass barely conscious of being in Jackson's arms as the older man wrapped him in a giant fluffy towel and carried him back to bed. He toweled them both dry. He carefully wrapped the sleeping youth in one of Linda's silk kimonos (no idea why he kept it), put on his flannel sleeping pants and fell asleep with Tommy in his arms.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
MarriedWhiteSissyMarriedWhiteSissyover 1 year ago

Absolutely phenomenal story and really romantic!!

AnonymousAnonymousover 3 years ago
More

Would really like more of this story.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Best Friend's Older Brother The surprise night of my life.in Gay Male
My Father's Best Friend A young man falls in love with an older man.in Gay Male
Surfstruck Young principal dancer performs for a new lover.in Gay Male
Becoming His Sissy Pt. 01 Straight guy discovers the pleasures of being a sissy.in Gay Male
Luke's Big Butt Changes Ch. 01 Baseball jock's big butt undergoes some strange changes.in Gay Male
More Stories