After a few months of debating with himself, Tom Wilson finally decided to jump off the fence and visit an escort. It was now over two years since his wife died. He was 57 and in OK shape. He wasn’t really that interested in women his age, and the feeling seemed to be mutual. He was OK with that. Yet still, for some reason, he was suddenly horny as hell and most importantly, he was tired of dating the Palm sisters.
Tom created a pseudonym, “Jack Jones,” a Twitter account under that name and acquired a separate “burner” phone for which he paid cash. The “nom de sex,” as he called it, wasn’t very imaginative but provided sufficient distance from his real life. He didn’t want this new lifestyle choice to be connected to his life.
He’d researched a bit on Escort Forums to figure out what the best practices were and gain more insight into this strange world. He had “shopped” a few escort sites and finally settled on Paris at Dream Girls. The agency webpage described her as: “This tempting treat is erotic, sensual, intelligent, sweet and ready to please! She is 29, works out daily and has the body to prove it! With her tight bottom, long legs and pert natural bust, you’re in good hands. Paris is well versed in the art of seduction. Her confidence and playfulness will leave you craving more.” He thought she might work and crafted his first message to her via Twitter
“Hi, Paris. This is actually my first encounter with an escort. I’ll be brief. Might you be open to entertaining gents in their late 50s suffering from LOH? What’s LOH, you ask? Late-Onset Horniness. Not fatal, and I’m hopeful that it can be well-managed thanks to beautiful women like yourself who might be open to providing the necessary therapy. OK, hope you got the kidding part. Can you provide the therapy? Would like to know either way. Cheers. Jack”
Here goes nothing, he thought and pressed send.
Silence.
Two days later, Jack’s phone buzzed: New Text Message. “Hi, Jack. You made me laugh. Of course, I’d love to meet you. Age is a number. Check my schedule and book through the agency. Hope to meet you sometime. Paris.”
Jack held off for a few days before responding. Then he texted back: “Paris. Thanks for the response. You sure you’re up to seeing gentlemen like me?
A few hours later, Paris responded, “Sure. I love dads. In fact, I’ve got a bit of a fetish for them. The great thing about older dudes is they can fuck long, and they love pussy. Let’s meet. Sorry for my cheeky talk. Book at my agency if you are interested. I’ll rock your socks off – promise! Teehee! LOL”
And Jack did precisely that. Booked her for noon the following week. He was hard as a rock and more excited than he’d ever been in a very long time.
A week later, he was hanging out at a coffee shop near the location he received earlier. He was waiting for a text that would send him to his first encounter. He was trying to be inconspicuous.
The text message buzzed: “She’s ready. The door code is 2304. Take the left corridor, past the concierge desk, turn right at the mail center, Take the elevator to PH. Turn left. The door will be open; please don’t knock. Just enter. You have 1 minute to reach the elevator and select the floor; otherwise, you might need to sign in at Security. If that happens, don’t stress; tell them you are visiting Bob Jones in PH14.”
Jack left the coffee shop and headed to the condo. His head was swirling with the instructions, and he was now sweating.
The building was a new part of the new ghetto of young urbanites in Toronto. He punched the code on the screen 3204. An Asian voice answered. He apologized, “Wrong Number.”
Dude. Take a breath, his inner voice said.
Jack punched the code again, 2304, the door buzzed, Jack rushed for the handle.
As he traversed the lobby, he thought he could feel the concierge’s eyes on him. He pretended to confidently negotiate the large lobby hall in the direction he thought was toward the elevators. Was it right-left or left-right? FUCK!
No matter, he arrived at the elevator lobby, which was now packed with five or six residents. FML! All the elevators were inching down from the upper floors. Jack glanced at his cell phone, trying to look casual and not as an older sex-starved maniac. He’d started a timer at the door. 34, 33, 32…
Ding. The elevator finally arrived and disgorged what seemed liked 20 folks; it wasn’t. Everyone then poured on punching their destination floors: 2, 17, 18, 22 and finally, Jack tapped PH. He glanced at his timer. 25,24. Phew. And off they whisked.
From the corner of his eye, Jack noticed a woman at the back smiling at him. Did she see he was aroused? Did she know something about his destination floor? Jack dropped his hand in front of his groin to cover his rising tumescence.
Ding. Ding. Ding. Ding. The passengers left one by one at each stop. The woman who smiled at him earlier caught his eye and seemed to wink as she left the elevator. Finally, the Penthouse level arrived. Jack was very grateful to be alone in the car. Exiting the elevator, he scanned for PH14. There.
The instructions had read: Don’t knock, just enter. Jack tentatively tested the handle – it moved. He opened the door and entered his first den of iniquity. A quick scan revealed that the condo was modestly decorated but tidy. The hall opened on a living room and then an island kitchen counter.
“Hello?” he asked.
Almost immediately from around the corner, he heard the slow, gentle tap of heels. Then he was greeted with the very essence of his imagination costumed as he requested.
“Hello Jack”
“Sweet Jesus! You’re gorgeous,” he stammered.
“Thank you, Jack. Welcome,” she beckoned with her finger, “let’s get to know one another better.
EARLIER THAT DAY
Paris woke earlier than usual, and for some reason, she was horny as hell. It was all she could do not to finger herself in the shower. She got the call from the agency mid-morning. Jack and a few other appointments were confirmed. Jack had requested she wore a business suit with a skirt. Paris was totally into that. She wondered what office slut she might channel; sweet and innocent intern or a dominant and demanding boss.
Her intuition told her there was something about this Jack fellow. It wasn’t necessarily bad. She couldn’t quite put her finger on it, but she hoped he would.
11:55 AM
As instructed by the agency, Paris monitored the lobby door on TV. This was her main chance to accept or decline a client. She’d learned that clients came in all shapes and sizes. She’d never needed to reject one yet. They were primarily sweet, lonely, awkward guys with a few awesome studs now and then.
Jack’s phone buzzed. “She’s ready. The door code is 2304.”
He left the coffee shop and headed to the condo across the street.
Paris checked the time. It was 12:02. A man entered and keyed in the code. His first attempt didn’t seem successful. He looked directly at the camera as he fumbled with his phone.
“OMG,” she thought, “Is that Mr. Wilson!?” Tom Wilson was her best friend’s dad. WTF!
The unit’s door request rung again. “OMG, breathe, breathe,” she thought. She realized she had just a few heartbeats to decide. She saw that Jack was flustered. The number rang again.
“Fuck it,” and buzzed him in. Minutes later, the condo door opened. Paris heard the tentative “Hello.”
The door closed. Paris took a deep breath. Should she reveal now or later? Her pussy was already flooded; this was so naughty.
Showtime.
She stepped forward and recognized him immediately. It was Mr. Wilson!
Paris wore a fitted black skirt and white blouse that highlighted her full, firm breasts and slim figure.
“Jack. So nice to meet you finally. Do you like the outfit?” as she did a little twirl. She stepped in and embraced Jack firmly. Her lips touched his, and she moaned into his mouth. The kiss melted into a full-on teenage tongue wrestle. He kissed her lips again, pulling her tightly against him. She reciprocated.
Jack thought, “I just want to melt into this woman and never come back.” Jack moved his soft kisses along her jaw and down her neck. She tasted delicious, fresh. He nuzzled into her neck, breathing in her aroma deeply. Lavender and citrus and sweet notes swirled about.
Paris moaned appreciatively, thinking -“OK, this guy is pretty good at this. And he doesn’t seem to remember me.”
They both rubbed each other’s backs and ass cheeks, pressed heads and pelvises together, and moaned into each other’s mouths. It was a moment that seemed like hours, but it was only a few seconds. They broke apart, smiling and gazing into one another’s eyes; her’s deep green, his deep blue.
“Fuck me!” Jack blurted.
Paris giggled and smirked. She had made up her mind. “I probably will, but first, here’s a towel, the soaps in the shower. Freshen up, and we’ll continue when you get back. Would you like something to drink?
“Just a glass of water,” he said as he turned to the shower.
“Oh Jack, the donation? Please just leave it on the counter. When you’re done, join me in the bedroom.” One thing Paris learned. Always get the donation upfront.
Jack fumbled in his pockets, placed the envelope on the counter, and then made his way to the bathroom.
In the shower, he fiddled with the knobs to get the temperature right. He squirted generous gobs of soap on his hands and rubbed all the crucial bits thoroughly. He knew that hygiene was absolutely essential to having a successful experience with an escort from his research. Though rinsed and towelled dry, he still smelled like a poster child for man-scented soap products.
Jack emerged from the shower, his cock straining at full mast. He couldn’t believe he was actually going to fuck this beautiful woman. The towel just wrapped around him and headed to the bedroom.
“I hope you don’t mind; I thought I’d slip into something more comfortable.”
Paris stood before him in a gorgeous light blue lingerie set. His eyes were drawn to the gap in her thighs and how the sheer lace had moulded firmly to her labia.
“You know it’s impolite to stare,” she giggled; “I know what you’re looking at, mister.”
She closed in on him and kissed him full on the lips. He returned the kiss again, savouring her perfume and her sweet breath. His kisses moved along her jaw. She moaned and opened her neck to him. He moved slowly, alternating soft kisses with licks and gentle bites. She sighed approvingly, guiding his head.
Truth be told, Jack would have been fine if the whole session was just like this.
He moved down to her breasts which he had been not so gently massaging, drawing his fingers over her now hard nipples.
“Here. Why don’t I take this off?” Paris sprung her bra and let it slide off her shoulders, releasing her girls. Her firm, perfect C breasts bounced in front of Jack. His cock got firmer.
“Sit back, mister,” and pushed him on the bed, “Let’s see what’s behind the curtain, shall we?” With that, she peeled away Jack’s towel.
“Oh my! Someone is happy to see me,” she leaned in and devilishly flicked her tongue on his deep purple glans.
Jack’s cock pointed skyward, and he gazed down her both expectantly and a wee bit anxious; his breath was short.
“Jazz, Jack. Relax. It’s just a blow job. How long since you had one?”
“Thirty years.”
“Oh, dear. I’m sorry. Very sorry. Well, we’re gonna make up for that today, aren’t we? Oops, just me. And, Jack, just so you know: I’m an epic cock sucker – you’re in great hands and lips.” Paris giggled.
With that, she took Jack’s penis in hand and gently stroked it and at the same time looking directly into his eyes. “You have a lovely cock, by the way. It’s so hot and hard.” Jack’s glans were deep purple. “I love the colour – it goes with my lipstick, don’t you think?” She licked her deep red lips and kissed his cock, ever so gently. “Oh look, precum,” Her tongue lashed out. She swirled it about his glans and then slurped up the residue. “Hmmm. Delicious.”
Jack gazed down as this gorgeous woman took his entire length in her mouth. Briefly, he felt guilty having someone so young sucking his cock, and then he gave in; he couldn’t care less.
Paris slowly slid her lips up and down his thick pole. It felt alive in her mouth. The salty taste of his cock contrasted perfectly with the tangy flavour of his precum. The feel of his engorged shaft in her mouth caused her cunt to tingle. She knew she had him in her control when he grasped her head.
Truth be told, Paris had been sucking cocks since her senior year in high school. This was power. They thought they were in control, but Paris knew she controlled them. She remembered the party in her senior year celebrating the football team’s city championship. She and a couple of her cheerleader mates fucked the entire first string.
She still got wet just thinking about wrapping her lips around a man’s cock. Other than the money, it was one of the reasons she decided to become an escort.
As she reflected, Paris continued to bob up and down on Jack’s hardon. She fondly teased his scrotum and taint with strokes of her fingers. Every few passes, Paris swirled her tongue over and about his gorgeous glans. She knew from experience no man could resist this multilevel assault for very long.
Jack groaned loudly, and his legs began to spasm. He closed his eyes, breaking their intense mutual gaze.
Paris smiled.
“That’s it, Jack, gimme that sweet cum,” as she pumped his rod, and she fluttered her tongue one more time delicately against his cock head.
“Fuckkkkkkk,” and then Jack felt his pulsating shaft erupt in her mouth and deliver his huge load. She took it all but reserved a mouthful for play.
“Hmmm. So. Jack, have you tried cum swapping,” she said, expertly holding his cum in her mouth.
“Huh?” Jack was still recovering.
“A cum kiss after you’ve come in someone’s mouth. Have you ever tasted your own cum?” She didn’t wait for an answer and pounced on his lips with a cum filled kiss. Their tongues intertwined once again in a moist battle of ecstasy. Jack again was stunned but didn’t resist, and then they broke.
“OMG. I just ate my own cum.”
Paris giggled and smiled mischievously. “Are you thirsty for more?”
Paris’s cunt was awash with lust – she needed to be fucked. But now was the time to come clean.
“Yep, you see what a world-class cock sucker I am, Mr. Wilson?” she giggled and held onto his cock, licking the rim. She now remembered what her first boss in this realm taught her: If you control his cock, you contain the man. Always have a hand on his cock.
Jack instantly froze. His erection started to subside.
“What? Wait, you know me?” He looked at her now intently. Nothing registered.
“It’s me, Anne Simmons, your daughter’s high school best friend.”
Jack gazed at her incredulously. It was at least 10 years since he’d last seen her. She’d changed considerably. Bigger boobs, tighter ass, hair.
“I had some work done,” Paris presented her pert boobs, “had the girls upgraded. Just to a C.. My fine ass and fitness are from four years of college volleyball. My hair – blonde was so boring, red hair is sexy as hell – it’s also why I shave my pussy. Ya got the have the collars match yer cuffs.”
“Anne. I’m mortified, embarrassed. I have to…I can’t do this.”
“What! Don’t know why. You came here to fuck a horny young woman. Sorry ’bout the surprise. Mr. Wilson, but you can’t leave. I let you in. You owe me at least one orgasm. And I know you want this sweet cunt.”
He made to move, but she pressed back and straddled his chest, pinning his arms. She could control him; she was fitter. She was also horny as hell, and she really wanted to fuck him.
“Awe, jeez, don’t you remember that tiny white bikini I wore at the graduation pool party Amanda held when your wife was out of town. I knew the whole thing became transparent and clung to every contour of my pussy when wet. I could feel your eyes on me all night. Your daughter knew too. We were both in on the tease. I’d have fucked you in a minute. Amanda would have too.”
“Shit. She’s my daughter. I’d never have dreamed.”
“Don’t get all gruff. Yea, she’s your daughter, but she’s a woman. I’m a woman. A very horny woman, by the way. Remember those other pool visits when I was around, and your wife was away, and we’d suddenly jump into the pool and pretend to be talking in the deep end. We were fingering each other and imagining that big boner you were trying to hide. Then we’d dive underwater when we climaxed to suppress the screams.”
“I can’t do this.” Jack moved to escape again. Feebly.
“Yea, you can, and you will. I just gave you a fantastic blow job, let you come in my mouth and swallowed your sweet load. Besides, you’re as hard as stone again, which I know is rare for you older dudes. You owe me an orgasm. You at least have to eat me out. You owe me.”
With that, she shuffled forward, positioning her now dripping cunt just over Jack’s face. She hadn’t been this excited about fucking a client or anyone since forever.
“Eat me!”
Jack’s mind spun. Truth be told, it was a fantastic blow job. He knew she was his daughter’s age. His dick was straining for relief again, and her cunt was so beautiful.
“Fuck it! You win.” Jack pulled her down on his face.
OH, YEA!
He ran his tongue between her lips, running it up and around her clit, giving it the smallest of flicks before moving on. She responded by pushing herself against him and grinding her cunt from jaw to nose.
“Fuck, Jack, stop teasing. EAT ME!”
In response, Jack moved his tongue down to her fuck hole with his tongue flicking in and out, alternating in circles which cause Paris to moan louder.
“I need to cum, please, please….Daddy,” Paris begged,
The “daddy” hit him. Jack was happy to comply. He focused on her clit and ran his tongue in circles around the base. Then he slurped the whole of her into his mouth and sucked unmercifully hard.
His efforts were met with louder moans. Paris started fucking against his face in earnest. Grinding her cunt on his mouth.
“Oh. Fuck Oh my god,. Oh. Daddy, I’m cumming”
He continued flicking her labia and driving his tongue into her dripping quim.
Suddenly she screamed and then exploded on Jack’s face. She held his head firmly against her streaming pussy. Girl cum filled his mouth and dribbled over his beard. Her thighs throbbed out of control, and eventually, she collapsed, gasping.
He froze for a second, overcome with the emotion of the moment. Then he licked Paris’s quim clean, cherishing her flavour.
She made her way to his face. She was beaming, kissing him in joy.
“OH MY FUCKING GOD, I have never come so hard. Shit Jack, I’m sorry, I made a mess. She tried to clean him up, licking up her juices. Let me get a towel.”
Jack said, gripping her arm: “Wait, can we just hold each other and kiss.”
“Sure, of course,” She continued to kiss and lick him tenderly. She snuggled next to his ear, “Jack…em… I hope you didn’t mind me calling you Daddy. It’s just pretending.”
Jack’s cock started to get hard again.
“Sure. What do I call you? Anne?”
She looked at him directly. “Sorry Jack, No. Here I’m, Paris. And you are Jack. Do you understand?” Jack nodded. “Good. Glad you understand. And now Paris needs to be fucked. Hard. OK, Daddy?
She grabbed his head and pressed her lips to his lips, kissing him passionately, then she grabbed his cock firmly, “Let’s strap a condom on that bad boy and fuck. OK?”
Jack groaned approval as Paris attended to the business. Jack’s girth required a Magnum. She squirted some lube on his cock.
“You ready for the fuck of your life? Are you?” She straddled his waist, guiding his pole to her hungry pussy.
“Yes.” Jack breathed.
“Seriously, Mr. Wilson, I’ve wanted to feel your fuckstick in my cunt forever. Fuck me, Daddy. Fuck me hard. OK?.”
She grabbed his shaft, rubbing its glans up and down between her slick outer lips. Then she placed the head against her opening and sat down, pushing her hips down and engulfing it in her smouldering pussy. Jack’s cock slid into her like a hot poker into butter.
“Fuck! Your pussy is so hot and wet and tight.”
“Fuck me, Mister.”
“Uhu,” Paris braced herself with her hands on his chest, concentrating on her pleasure. She closed her eyes and settled into a slow grinding motion with her hips pumping his shaft. Every few rotations, she would push down, driving his thick member deep into her sopping cunt.
She giggled at each stroke and tossed her head back with a smile on her face. “Sweet Jesus Jack, your cock feels amazing.
She sat back, bracing herself now with her hands behind her on top of his thighs. Then began grinding her tight pussy up and down faster. Her nipples were hard and erect. Jack pinched them. Hard. Paris squealed with delight and gripped him harder with her pussy.
“This isn’t gonna take long,” she said breathlessly, the motions of her hips increasing, “I’m gonna cum all over your cock and then feel you cumming inside my pussy!”
She now drove her pussy faster up and down the length of his cock. Jack roughly grasped her breasts.
Paris’s breath came faster, and her hips sped up a little more as her excitement and arousal increased.
“Gimme that cock! I wanna feel your cum inside me!” she moaned, grinding her hips faster and harder on his rod.
Jack pulled hard on her nipples and now drove his cock upward in response.
“Fuck yessss. “Paris moaned loudly, slamming her hips down onto him, her eyes squeezed closed, and her mouth hung open as she gasped for breath.
He took one of his hands from her tits and moved it down to her pubic mound, laying his hand flat and pressing her clit with his thumb. Paris cried out loudly, and her hips moved even faster. “Fuck Yes! Yes! Yes!” she gasped as he circled her clit with his thumb. “I’m gonna cum, I’m gonna cum, oh my God, I’m gonna cum!” she cried through gritted teeth.
Her pussy was now a hot wet blaze around his shaft. Her slick juices were pouring down across his balls. One more flick of his thumb on her clit finally pushed her over the edge.
“FAAAAAACKINHELLLLL” she screamed. “I’m cumming, daddy!!”
Paris’s orgasm exploded and took control of her. Her eyes rolled back. Her face was locked in a beautiful cum grimace as she gasped for breath. Then her whole body was locked in a spasm as she continued to drive her pussy up and down on Jack’s cock. It was all she could do but to hang on as wave after wave of pleasure rocked her body, shaking her down to her core.
Jack held onto her hips, amplifying her pounding. His balls tightened as he felt his cock swelling inside her and his orgasm hit hard in response to hers. Jack closed his eyes and groaned like a beast through clenched teeth as his cock shot stream after stream of hot, thick streams of his jazz shot into Paris’s clutching, gripping pussy. Jack came so hard he thought he might have torn something loose.
Paris felt his cock pumping inside her and opened her eyes, grinning as she looked at him. Another satisfied customer.
Paris carefully dismounted Jack. The condom held, but they were both drenched with sweat and sundry other fluids. They held each other briefly. Basking in that afterglow that comes after a good fucking.
“Well, I better freshen up,” Jack said as he bounded off the bed and headed for the shower. As he washed up, the sum of the experience came home: This was just sex. Not love. On the one hand, he got to fuck a gorgeous woman. On the other; well, there was no other hand, that was it.
Jack dressed and emerged from the bathroom. Paris had donned a lovely wrap.
“Jack. Thanks. I had an amazing time. You’re a champ pussy eater, by the way.”
Jack chuckled. “Thanks, em, Anne, er Paris. Listen, can I see you again? Sometime?”
“Sure, Jack, I’d love to see you again,” she kissed him full on the lips and hugged him warmly. “Now you get out of here, you sexy man before I have you fuck me again.”
“Thanks, Paris”
“Back at ya Mr. Jones.
The door closed.
Both Tom Wilson and Anne Simmons knew they would never see each other again. At least in that realm.