Jackson's New Man

"And in this image, we can clearly see the difference in performance when..."

Oh god who cares Jackson thought to himself. It was day 2 of a 3 day conference on Diversity, Equity, and Inclusion in the tech sphere and Jackson had found himself out of fucks to give somewhere on the morning of Day 1. His boss had assigned him this conference as a "perk" (as well as wanting to send the only Latinx person in the office) but - aside from the open bar party last night - there hadn't been a lot to hold his interest.

Jackson glanced at his watch and took one more look at the dais. Mr. Ogilvy-McCoy was still talking about performance variables in diverse hiring practices, gesturing in little, controlled movements at god knows what figures on his slide deck.

"Fuck it" he mumbled, flipping his notebook closed as he quietly made for the exit. Lunch was in 20 minutes and Jackson was going to be damned if he was going to wait in that line again. Fast-walking, he made it to the bathroom and made for the farthest urinal in the corner. Tucking in, Jackson opened the fly of his slacks to reveal the cute, baby-blue panties he'd chosen for the day. Jackson had been a sissy for years and loved to express himself more when travelling, choosing often to pack only women's underwear and a sex-toy or two in his carry-on. Smiling to himself, he pulled his little shaved cock out and let his flow start with a sigh as he closed his eyes and rested a free hand on the wall.

"Long Day?" said a sonorous deep voice.

"The fuck?!?" Jackson jumped, dribbling a little urine on the floor before catching himself. A barrel chested hairy man of ~45 years in age had appeared at the urinal next to him. "Oh shit, sorry...yeah long day..."

The man laughed to himself, smiling, his gaze clearly wandering the full length of Jackson's 5'7'' frame.

"Very pretty panties as well...baby blue suits your skin tone..."

Jackson had made a point to always use the urinal while wearing women's underwear, hoping for just such an encounter, but had never really made a plan for what such an encounter might bring when it arrived. He stammered oddly, not sure how to answer while fumbling to slip himself back into the little soft undies.

"It's ok to be shy" the thick man said softly, looking around the room to ensure their privacy before sliding his hand into Jackson's waist and gently taking the slim boy's cock in has hand. Jackson took a peek down and could see the thick, meaty shaft in the bigger man's hand start to swell as well. Mr Dad-Bod smiled again, a mischievous twinkle in his eye. He leaned in and whispered "Family restroom, 3 minutes." then quickly washed his hands and left. Jackson stood as still as a ghost, his stiff cock twitching in his pants. His brain clearly wasn't working so his dick made the choice as he finally got his pants zipped and hurried outside.

The family restroom was right across the hall and had a red-occupied tag. Jackson stepped across quickly, knocking at the door. It opened, thankfully revealing the swarthy dad and not an angry mother and child.

He quickly pulled Jackson inside and locked the door. "I don't have long before my next session but I can't resist a slutty little sissy. Pants off cutie."

Jackson mumbled and stammered again, clearly perplexed as to why language had abandoned him in this crucial moment.

"Oh good, you're dumb too" the older man smiled. "Pants off, panties on..." he spoke slowly as his hands undid Jackson's belt and pushed his jeans to the floor, revealing the cute bikini cut undies fully.

"So cute! Now on your knees, lets see how you do" Jackson's eye popped as he looked down and noticed a fat, cut 8 inches of cock hanging out of the thick man's slacks.

Finally language made it out of Jackson's mouth "Whoa hey, I didn't...I mean...I"

"Oh stop. No one is hear to see you, I don't know your name, and I won't see you past tomorrow. We all know what's going to happen to my dick in the next few minutes, so let's not lie to ourselves ok?"

That shut Jackson up quickly. He kicked his pants and shoes off the rest of the way and squatted in front the big alpha, kissing, suckling, and teasing his cock into full hardness.

"Mmm, attaboy. Good job, show me how a sissy handles a real man's cock"

Jackson swooned at the lewd praise, drooling on the thick cock as he started to pump it into his mouth. Soon the room filled with the wet, sucking and grunting noises of intense oral as the femboy serviced the alpha to the best of his ability. Jackson wrapped his fist tight around the base of the shaft, moaned, and began pumping a fast, twisting wet rhythm in and out of his mouth, his eyes glazing over in lust.

In short order, the big mans balls tightened and he yanked Jackson to his feet.

"Pull your panties open" he grunted. Jackson obeyed, pulling his little undies open to his expose his stiff dicklet. He grunted heavily, placing his thick head into Jackson's undies and grunting once, causing his dick to squirt rope after rope of thick, sticky batter into the waiting panties. After a moment, he sighed and wiped his cock off on the waistband before tucking himself into his boxers.

"There, now you'll remember me for the rest of the day. Keep that man-fluid in your panties all day, sissy." He smiled and tucked a room key into Jackson's waistband as well.

"But clean yourself up before you come over. 3207, midnight"

And he was gone. Jackson panted for a second, considered cleaning himself up and decided to go ahead and embrace this. Fuck it...strangers for the win. He slipped his khakis back on and checked to make sure no fluids were visible but spent the next two hours squirming and uncomfortably horny, fiddling with the room key in his pocket and not paying any attention to his afternoon courses. What the hell was going to happen tonight...

Jackson hurried down the hall of the 32^nd floor, his heart racing. He wore a simple tee shirt and fitted jeans with strappy pink bikini panties under. Originally, he had worn a delicate lacy pair of briefs from La Perla but decided sacrificing them to Daddy's particular fetish wasn't worth it. Like it or not, these panties weren't likely to survive the night.

It had taken some will power, but Jackson finally knocked on the door of room 3207, right at midnight. The man opened it quickly, shirtless but wearing low slung pajama pants, a tumbler of whiskey and ice in his hand.

"Excellent, right on time. There's an outfit in the bathroom, go change, then make yourself a drink. I'll be in the lounge."

Nice baller-suite flex Jackson laughed to himself, before sliding off his shoes and padding into the bathroom in stocking feet. The outfit, such as it was, was laid out on the counter. It consisted of a matching set of stockings and garters, a pair of transparent lacy briefs, and soft, pretty teddy on top, all in a beautiful soft shade of sunny yellow. Jackson eagerly dressed, returning to the lounge and presenting himself for inspection.

"Lovely...just lovely. And to think you hide all this with ugly boy-clothes all day. Turn around"

Jackson spun obediently, showing off the pleasing thickness he'd built up in his behind through careful gym routines.

"Excellent. You really are a very sexy little sissy aren't you?" The man sighed contently. "Now go freshen our drinks and then come sit with me."

Jackson walked softly to the bar, intensely aware of how feminine and different it all felt. He'd been with plenty of partners, some even in girl-mode, but none had ever had him quite believing as hard as he was today.

He walked nervously to the sofa, handing over the drink and settling onto the sofa, a little far from the man but close enough to smell his familiar cologne.

"Don't be silly, I don't bite." He took a swallow from his drink then pulled Jackson in tight, his arm strong around the young sissy's slim waist.

"You make a lovely girl, and you're going to be my girl tonight..." he said softly, his thumb caressing Jackson's chin and pulling him in for a kiss.

Drinks soon forgotten, the lovers made-out passionately, Jackson straddling Daddy's lap as his strong hands ran up and down the slender little sissy, exploring and caressing. Their tongues danced as they moaned softly, enjoying each other. They kissed heavily for a moment more before the older man broke away, pulling Jackson to his feet and admiring him, grabbing a firm handful of his ass and giving it a spank.

Jackson yelped pleasingly, enjoying the tingle when he was suddenly surprised by the warm breath on his butt cheeks. Daddy clearly was taking what he wanted and Jackson felt no cause for complaint, pushing back and presenting himself slightly as a pair of strong hands slid his panties to his knees. Soft kisses spread across the sissies behind but were quickly replaced by a wet tongue probing the young mans tight hole. A finger, then two soon followed as Jackson moaned at the familiar feeling of a man warming him up.

The man's swarthy voice groaned, heavy with lust "You ready sweetheart..."

"Fuck me daddy" Jackson managed to purr back before he felt the insistent hammer of a big cock probing its way into his bussy. Daddy entered slowly and firmly, burying himself deep before starting an insistent driving rhythm in and out of his eager little plaything. They moaned together, their bodies in sync for minutes of sex until Daddy finally pulled out and flopped onto the sofa, his cock wobbling and moist in the air.

"Go for a ride sissy" he ordered. Jackson eagerly obliged, stepping out of his panties and mounting his alpha's twitching meat, moaning as it filled his bussy with pleasure. Soon his hand found his own genitals and Jackson started stroking himself in time with each thrust

Each party could feel something building but it was Jackson who popped first as he dropped onto Daddy's lap, cock buried deep inside while his body spasmed heavily from a full body orgasm that left a cummy mess between the two sweaty lovers.

Thankfully Daddy had been close as well and they twitching, quivering mess in his lap had been enough to push him over, his meaty cock filling the little sissy bussy with an obscene amount of cum.

As the last of their orgasms drained, they clung together tightly in a mass of sweat and stickiness, panting until their breath returned. Finally separating, they flopped exhausted on the sofa.

Daddy grunted, satisfied, and scratched his sticky cock. "I'm going to shower. Be in there in 5 minutes in case I need one more ball draining." and he walked off, not even looking back. Jackson was momentarily appalled but quickly peeled off the sticky sex clothes and rushed into the steamy bathroom.

The shower was bigger than Jackson's apartment and equipped with multiple heads. Cautiously he slipped into the steam, curious what was next.

"Hey cutie" he was greeted with a spank on the butt. "I'm good actually. Get cleaned up"

Jackson started to object but it came out as a whimper and he was left alone in the shower, his thoughts full of panties, cum, and long, hard cocks.

He came out naked, wrapped in a towel and was shocked to find his new friend fully dressed, his suitcase behind him.

"I uh...what?" Jackson mumbled.

"Suite's paid up till Friday but I have to get back. Enjoy yourself cutie." He smiled warmly.

"Oh, I'm in Orlando next week for HR ROCKS. Meet me there." And he handed over a card.

Jamison Michaels

COO, Stopgap Inc

And he was gone. Jackson gasped to the empty room. No wonder he looked familiar. StopGap Inc was the worldwide leader in office HR solutions, meaning Daddy was quite likely a billionaire once or twice over.

Jackson grabbed his phone and starting checking Orlando flights...