*This isn’t the first story I’ve written, but first I’ve ever posted anywhere. Feedback is welcome. It’s a bit longer than typical posts on here but I sometimes find them too short for my taste. Enjoy!*
The past three Friday night I had ended up at The Fiddler. With big windows, brick walls, candles on each table, and a cobblestone patio out back, the pub had a familiar charm while serving craft beer and cocktails to the downtown crowd. A friend had invited me to after-work happy hour with her coworkers there three weeks ago, and I had such a great time meeting her colleagues that I kept coming back. This team worked together at a tech start-up in a post-and-beam converted warehouse office next to the bar. They did something to innovate the printing industry, I never got a full explanation. Clearly, they were all good friends, as their happy hours often turned into drunken late nights together.
I loved meeting this new group, I relished being the new person in the crowd. And of course, there was one person who kept me coming back. Tony was an Account Manager. I’d describe him as confident, well established, and strikingly handsome. He also happened to be in his mid-40’s and I was 26. I normally wouldn’t even have thought twice about him, but he oozed sex appeal in the most compelling, mature way I’d ever experienced. His trim beard had a sultry salt and pepper look that gave him an aura of wisdom. He was tall, muscular, had glowing olive skin and honey eyes, with a smile reminiscent of Jeff Goldblum’s wide and inviting mouth. He wore savvy button-down shirts and fitted chinos that clung to his toned thighs, unlike the boxy suits I was used to other men of his age wearing. He blended right in with the start-up crowd. What I noticed most, though, was how he spoke openly about being a bachelor.
I quickly grew enamored with him. Being a new addition to the group, he often sat next to me to make me feel welcome. We soon discovered our mutual love for photography. I wondered if he felt the same electricity I did when our legs grazed each others’ under the table. He clearly knew the effect he had on women. I had witnessed him giving compliments to servers that made them blush and lighting cigarettes for the ladies who smoked out on the patio. He never missed a chance to refill my glass when it was empty with beer from his pitcher.
That evening, as the loud bar roared with liquor-fueled conversations and toasts around us, we ended up in a deep conversation just between the two of us about dogs. He scrolled through his phone’s camera roll for me, proudly showing off adorable pictures of his border collie, Akita. I leaned into him to get a closer look, unavoidably pressing my breasts into his bicep and cupping the back of his hand in my petite palm to angle the phone towards me. He accidentally swiped one image too far and I caught a glimpse of the last thing I expected – a nude selfie angled down to show off his enormous erect penis. The lighting was actually flattering and made his junk look appealing as it stood tall against his firm bare abs. Turns out he was a good photographer. He let me ogle the photo for one moment too long before black screening his phone.
“Oops, you weren’t supposed to see that,” he mumbled so that only I could hear. He cracked a wide, cheeky smile at me while I was still leaning up against his body. I didn’t believe him.
By the time I got home that night after midnight, I was aching for Tony’s body. We had tipsily walked part of the way home together. It was a cool summer night, and the moonlight was utterly romantic. I secretly hoped he would give me a signal to follow him, I would have gone home with him in a heartbeat. He lived in a quiet old neighbourhood west of downtown and I lived south, over a bridge.
In my bedroom I opened up my laptop and found Tony on Facebook. I scrolled through some old pictures of him from years earlier – oddly, he wasn’t as dashing without his deep smile creases and silvery hair. I didn’t dare add him as a friend. I was completely aroused, but these pictures wouldn’t do it, so I closed the laptop and let my mind wander. Luckily, I had a visual aid in my mind, having had a glimpse of Tony’s impressive manhood to help get me started.
I barely managed to unbutton my short sleeve blouse before slipping a hand down my bra, more aggressively than usual. Tightly pinching my hard nipples, I crawled onto my bed on my knees. I pulled on the front of my underwear, forcing the fabric to rub against my impatient clit, giving it its first attention of the night. I slid one hand down under the fabric and felt my warmth. I spread my legs open on my bed and rubbed my pearl gently, back and forth, gaining speed and pressure. I felt tingles through my body, my heart was racing and I made a quiet involuntary moan.
I was just getting into a good rhythm and feeling shocks of pleasure when I made myself stop. I took a pause and slid fully out of my underwear and skirt, and unhooked my bra so I was fully nude. I took a few seconds to lie on my back on my bed, savoring the calm night and beautiful man in my head.
I imagined what we’d be doing if he was here now. I’d sit on his lap and hold his face against my chest, soaking in sucks and kisses from his juicy lips. I’d be feeling in-between his legs to find out if the outline of his cock through his pants was as big as it looked in that picture. I’d strip him naked and lube myself up to fit his manhood inside of me as I fucked him thoroughly from on top. I knew from his flirty demeanour that he was an experienced lover. He’d be able to teach me things and make me feel ways I’d never felt before.
I lay my head back on my pillow and let my fingers come back to my swollen clit again. This time I let myself go wild, using one hand to hold open the lips while the other used every finger to rub and pinch and pry at myself. I was normally so modest and vanilla when I pleasured myself, but soon I was shoving three fingers inside my steaming hot cunt, pumping as hard and fast as I could. I played on the edge of pain and pleasure. I stroked my clit until I arched my back in bliss, and then flicked it with the back of my nails and clamped it cruelly between my fingers. I liked this new game, but mostly I knew a light cum wouldn’t be enough for how turned on I was tonight. I was bringing myself up to a new level of pleasure. My pussy was so wet that I could hear a squish as I pumped my fingers in and out.
I bucked my hips in the air when I finally gave into a shock wave orgasm. I gasped loudly as this new level of euphoria washed over me. I kicked out my legs and shook through my whole body. I brought the hand that had been inside me up to my chest and I rubbed the sweet juice all over my breasts, making them delightfully shiny. I took an extra moment to enjoy my own supple tits that I rarely take the time to appreciate. My other hand soothed my quivering clit with a feather touch as it recovered, I couldn’t stop touching myself. I fell into a deep sleep on top of my damp duvet.
The next morning, I went for a much-needed run to blow off some steam. I had woken up early miraculously without a hangover, bursting with energy. I was a few kilometres in, back over the bridge and heading towards the beach, when I spotted a familiar dog. It was Akita. Tony spotted me running on the sidewalk and followed Akita’s pull towards me. He was fresh faced, glowing in the morning light in his casual weekend skinny jeans and crisp floral button down. “*How dare he be so put together before 9am on a Saturday?”*, I thought to myself, almost annoyed at how appealing he looked. I was glad that I’d shaved my legs and combed my hair that morning, so I didn’t look like a total slob in front of him.
“There’s a familiar face,” greeted Tony as we made eye-contact. I approached Akita first, petting her under the chin and letting her greet my freckled legs with a sniff.
“I feel like I’m meeting a celebrity pup!” I exclaimed, mostly speaking to Akita and trying to ignore Tony. I would take any distraction that would help me to simmer down my excitement at seeing him in broad daylight. “What a good girl! Hi Tony, how was the rest of your night?”
“So eventful, I hit up an after-hours club and two orgies,” responded Tony sarcastically, now petting Akita too so our hands brushed past each others’. I giggled at his joke flirtatiously, unable to act cool in his presence. My voice broke in a dry crack and I coughed seriously to bring myself back to reality.
“Gorgeous day, isn’t it?”
“It is, not that I have a choice. We go out rain or shine.”
“Where do you walk?”
“Around the neighbourhood, but I’m just on my way to get a coffee. Want to join me?”
“I was going to get one anyways,” I lied, trying not to sound too excited. We wandered into a hip café and Tony asked what I like to drink. “Americanos in the morning,” I informed him, and before I knew it, he ordered two. With our coffees in hand we wandered down the tree-lined residential streets, past colourful century homes and neighbourhood parks. After a few blocks, without warning, Tony turned towards a 1950’s low-rise modernist apartment with ivy climbing up the side and gold numbers to mark the street address.
“Why don’t you come in for a second, I wanted to show you my newest Nikon lens,” offered Tony, indicating that this was his building. I couldn’t have said no if I wanted to at this point. The next thing I knew we at his back-corner unit. As soon as he opened the door I was in shock of his abode. For a single man’s apartment, it was meticulously organized and styled. We left our shoes at the door and I wandered barefoot inside.
“Make yourself at home,” Tony mentioned over his shoulder as he immediately tended to feeding Akita. I strolled through the space, taking in the pleasant symmetry of his mid-century Scandinavian teak furniture set. He boasted several healthy, lush palms in sunny spots through the room. The apartment was fitted with original hardwood floors in the living room covered by an intricate Turkish rug. He had real art on his walls, which I especially admired knowing that my walls were adorned with band posters. I slyly peaked into his open bedroom door, spotting a neatly made bed with crisp linen sheets. I took a seat in a luxurious, high-backed vintage loveseat freshly upholstered in deep blue crushed velvet. I felt a light tickle on my exposed arms from the velvet that turned me on in an unexpected way.
Tony had moved to his credenza; he was pulling out his camera gear as he spotted me taking a seat in the corner of his eye. He placed the camera down and turned towards me, I stood back up quickly.
“Don’t worry, make yourself comfortable anywhere you’d like,” Tony assured me with a deep, low voice. I took a step towards him, pretending I was interested in flipping through his record collection, but I clumsily walked right into his body, which was now leaning against the low cabinet. I wasn’t dressed for air conditioning in my light running clothes. My skin formed goosebumps and my nipples were so hard they poked out of my athletic wear in the cool apartment. Tony didn’t hide the fact that he noticed.
“Are you cold?” he asked with a small laugh, shifting his gaze to my protruding nipples.
“I’m alright, it was warmer outside though.”
Tony placed his broad hands over my arms and rubbed them to warm me up. He was holding my small frame in his grip. I tilted my head up to him and we locked eyes for a second before we both leaned in for a kiss. The sexual tension broke as a kiss turned into making out which turned into Tony caressing me down my neck and chest.
“I was tempted to do this last night,” managed Tony between kisses.
“I wish you had, but now’s good.”
“Do you want me to warm these up?” he offered, in reference to my chilly nipples.
“Please,” I begged. A new expression crossed his face, he was mentally planning what he was going to do to my body.
I ran my hands over his firm torso as he placed his manly hands over my sports bra with a light squeeze. I lifted my hands in the air to signal that I wanted him to take my shirt off. Tony flashed a pleasantly surprised smile as he pulled my top and sports bra off over my head, before taking both of my perked-up tits in his hands. One at a time he took the stiff nipples softly between his lips and sucked lightly while tonguing them. I had never been so turned on, and I leaned back as he held me up with one sturdy arm. I unbuttoned and pulled off his shirt to reveal his irresistibly smooth chest. Our fronts rubbed together as we made out topless, still leaning against his sideboard. As we tongued and nibbled each others’ lips, I felt the outline of Tony’s stiffening cock appear in his pants as he pressed against me, just as I’d imagined it the night before.
“Did you have plans today?” inquired Tony with raised eyebrows.
“Yeah… doing you,” I replied naughtily.
Tony squatted down for a second and picked me up around the hips, letting my tits bounce freely as I was hoisted up. I straddled his body, allowing my pussy to rub up against his abs through my thin shorts. I salivated between my legs from the stimulation. He carried me to the loveseat and sat me down. Tony knelt down in front of me, grabbed the waistband of my shorts and underwear, and in one fell swoop pulled them to my feet. Earlier that morning in the shower I had shaved my bikini area, so the skin around my pussy was as fresh and smooth as it would ever be, a real treat for Tony. He leaned over my naked body and planted a kiss on my mouth.
Tony traced a line with his finger down my torso to my mound. He followed the line with a string of kisses, stopping right below my navel. He certainly would have tasted the sweat from my run earlier, but that didn’t concern me. He settled into a comfortable spot, placing my legs one at a time over the arm rests of the loveseat, fully spreading my lower lips open for him.
“*So, this is what a comfortable seat like this is for, a pleasure throne,”* I thought to myself. He gripped his strong hands around my ass and pulled me towards his face. I felt his breath tickle and warm my clit. He paused for a second, his nose just barely grazing my most sensitive bits. When Tony finally gave my pussy a broad lick, I moaned and thought I would melt into a puddle. But then he gave another, and another, lapping it up with enthusiasm.
“Oh my GOD, Tony!” I screamed. He worked me up right away until I was about to cum from his relentless licks, and then he stopped. He switched styles to using a stiff tongue, concentrating in on one small area at a time, taunting me by not letting me rupture already.
“You didn’t think I’d let you get off that fast, did you?” he teased.
He dragged the pressure point through every region of my crevice, eventually moving down and entering me with his tongue. Tony used his thumb to rub circles between my folds while he fucked me with his tongue. I sank deep into the chair and enjoyed every second of being treated like a queen. This was certainly more of a stress relief than a run.
Eventually Tony came back up and put his full focus into bringing me over the edge. He gingerly mouthed my pink pearl, simultaneously sucking and flicking it with his tongue. This was an advanced move I’d never felt before until he’d done it to my nipples a few minutes earlier. It brought me to a sharp orgasm in seconds. I shook uncontrollably as Tony held me by the waist, head still buried between my legs as I felt my cream drip down my thigh. Tony lapped it up with long drags of his tongue down the back of my thigh. His beard was sticky with my sweet juices, he looked up at me satisfied. I could tell that he was turned on by making me cum, exactly as he should be.
“How was that?” inquired Tony as he got off his knees and stood up, towering over me. His bare chest glowed as the morning sunlight bathed it through the window.
I needed a minute to sit in the chair, I was motionless as I recovered from the intense surge of pleasure.
“I need you inside of me, but I need a second,” I panted.
When I was ready, I held my hands up and Tony picked me up and walked me over to his bed, placing me on my back. I had regained my strength and I sat up as he stood in front of me, so my head was at crotch level with him. He was still wearing his pants, but I massaged his thighs, working upwards. I wasn’t even at his groin yet when I heard him make a low moan under his breath.
“Pants off, please,” I coquettishly demanded, as I leaned back propping myself up with my arms behind me. I admired his firm body. Clearly, he took good care of himself – and me.
Tony undid his fly and stepped out of his jeans in an instant. I slipped my hands under his boxers to grip his substantial manhood. It was nice to feel its power in my hands, knowing that it would destroy my pussy that morning.
I joked, “Can’t wait to see that piece again. It’s a work of art,” reminding Tony of the dick pick incident.
“Oh, I knew you’d like it,” he confidently responded. My suspicion that that photo didn’t show up by accident was confirmed.
I stretched the waistband of his boxers, letting his shaft spring free. I was too short sitting on the end of his bed to properly perform a blowjob, but that didn’t stop me from playing with his package, rolling it between my palms and tickling it with the tips of my fingers. It was as hefty and stately as the picture had shown. I pulled the rest of his undergarment down to the floor, and as he stepped out. I stood up and guided Tony onto his bed on his back, crawling over his body. I straddled his stomach, rubbing my still wet clit against his toned abs.
I reached behind me and felt his throbbing cock again, indicating that I wasn’t done playing with it, I had just needed a repositioning. I crawled back down below his waist, leaving a trail of my nectar down his stomach until I had nothing left to straddle and was back on my knees at the end of the bed. I approached his shaft with my mouth for the first time, hungry for his meaty erection.
It was too big to fit entirely in my mouth and I wasn’t adept with deep throating. But I wrapped my lips firmly around the tip and bobbed down as far as I could go. I felt Tony tense, a lightning bolt of sensation shocked down his legs. I bobbed up and down, only really reaching three quarters of the way down his mast, using both hands to stroke the base. Tony breathed sighs of relief and pleasure as I attended to his hard on, working him up. I knew I might not be able to make him cum like this, but I tasted his pre-cum mix with my saliva and knew he was enjoying the ride.
After a few minutes, I paused to take a breather. Tony decided enough was enough, no more foreplay. Until now, he had only guided me with gentle leads. But suddenly, he authoritatively got up, tossed me on my back, and pinned me down against the bed with his body between my spread legs, holding my wrists down against the covers. He transitioned from this dominating commander to gentle lover for a second, caressing my neck with a few soft kisses, before tightening his grip on my wrists again. I was into this dual personality bit he had going.
His shaft hovered between us and I could see his entire muscular body as he knelt on the bed over me. He lowered his hips to my level, sliding his tip down over my clit sending tickles through my body. We were both so wet that he eased into me with no resistance. Two, four, six, eight inches. I felt him fill me up, just as I had desperately wanted the night before. With my wrists still locked down by his hands and bodyweight, he leveraged himself to pump in and out of me, both of us letting out moans. He brought our fucking up to speed, so intense that the entire bed bounced under us.
Tony let one of my wrists go and opted to grab me by the back of the thigh instead, pushing my open and using it as balance as he athletically boned me from on top. I wrapped my free arm around his shoulder, feeling him move as he used his core strength to thrust his body into mine over and over and over. I was already overwhelmed with stimulation when he took his other hand to my clit, giving it a delicate caress that juxtaposed with the hard cock ramming I was receiving from him simultaneously. This heightened my senses to a new level, and I knew I couldn’t last much longer.
My voice cracked as I screamed, “Fuuuuck! Tony!,” convulsing into a climax that added more cum to the already drenched situation. My back arched as I reached the peak of my orgasm, making my tits bounce, the sight of which impossibly turned both of us on even more. I squirmed under him as I pulsed with orgasmic waves, Tony still gripping my thigh possessively. He took his hand off my pearl, but never stopped thrusting.
His hands found my wrists again and pinned them back down, I knew he was close. I panted and moaned as he pushed my body past its usual limit. I tried to free one hand to wipe sweat off his brow, but he wouldn’t let go. In fact, he liked when I tried to escape, he grabbed even tighter. That pushed him over the edge, he let out a roaring orgasmic scream. His grip loosened as he lost control of his body. I watched him buck as released his load into me. His thrusts slowed down and then stopped altogether.
Tony lay his torso and head down next to me, still inside of me. I was turned on again at the sight of Tony reaching his sexual peak, but I knew I didn’t have another fuck in me, so I let my fingers lazily wander over my tits for a small, pleasant stimulation. Tony gazed at me tenderly as I lay facing him on his bed, tracing the outline of my rose coloured nipples with one fingertip. We didn’t say a word.
20 minutes later I sat out on Tony’s patio wrapped only in a plush towel, warming up in the sun again after a quick cold shower. Dense bamboo plants created a privacy wall, forming an intimate urban oasis. Tony joined me, wrapped in a towel that sat right below his waistline, exposing his deep V-line. Although it was a massive turn-on, I was satisfied for now, but I drank in the image and stored it mentally for later. He brought over a small wooden box where he stashed his weed. He rolled a joint and we shared a few puffs together in silence, occasionally making eye contact and giggling. I knew that Tony had secrets that he hadn’t let me in on yet. But this was a perfect moment and I decided to enjoy it, not wonder when we would meet again and what he had in store for me next.
Source: reddit.com/r/eroticliterature/comments/hc369f/tonys_place_part_i_mf_age_gap_multiple_orgasm