Bob and Sheila lived next door to my parents and me. They were all great social friends, constantly inviting them over for beer and wine and a soak in the hot tub. They didn’t know I knew, but I once nearly walked in on them in the middle of a full partner swap after ditching my senior homecoming date early.
I was taking a gap year post-high school graduation, honestly unsure of what to do with the rest of my life. Between shifts at the sports bar, I’d often pick up odds and ends gigs around the neighborhood like babysitting or house sitting.
Bob and Sheila asked me to house sit for a long 3-day weekend while they and my parents slipped away for a “golf outing and wine tasting getaway” up North, where undoubtedly they’d make a side quest to the White Lotus Hot Springs swingers resort. I was more than happy to watch TV and dog sit for the weekend for a few hundred bucks.
“Jason may pop in from college” Sheila called as they were leaving, both couples piling into my Dad’s silver Suburban. “I left some cash in the kitchen drawer in case you guys want to go out for a movie or something.”
Jason and I were roughly the same age, classmates in several classes in high school including computer science and AP US History. He was once put on suspension after being caught peeping into the girl’s locker room and again after hacking the 12th-grade Biology teacher’s email to send a staff-wide message about how the earth was flat.
I last saw Jason before he left for college. He was slightly overweight with hair long enough to pull into a small ponytail. He wore a steady rotation of Anime shirts and spent time gambling money on options and cryptocurrency. He had a reputation for being an awkward duck subsisting on a diet of Doritos and microwave pizza, with a complexion that reflected these substandard choices.
Last summer my girlfriends and I ran into him at Tina McCory’s party. Despite not being particularly popular or outstandingly attractive, he found ways to make himself indispensable at parties by procuring copious amounts of beer and booze through his “connections.” Random older women who often drove him around town. He often used the cash he made to solicit blowjobs and other favors from some of our classmates. As far as I knew, no one ever obliged.
However, we did occasionally spend some time together socially. After all, he wasn’t a complete creep. As kids of the notorious swinger couples on the cul-de-sac, it made sense for us to escape these hot tub hook-up nights by going to a movie or party. I got to know him a bit better in those instances. We had similar interests in action movies, geeky sci-fi literature, and a shared celebrity crush on Margot Robbie.
Rex, Bob and Sheila’s 6-year-old Doberman, nuzzled my leg and shook his head towards the front door. I grabbed his leash, laced up my shoes and we took off for a quick afternoon walk.
An hour later I returned to find Jason’s car in the driveway. A touch temperature check of the hood indicated he had just recently arrived.
“Get over here Rex!” A familiar voice called from inside the house.
I opened the door, dropped Rex’s leash, and he went flying to the arms of his master, tippy tapping along the laminate floor.
I looked up, expecting to see the same nerdy guy but was pleasantly surprised to find he had been replaced by an absolute stud.
Jason’s first year of college came with a glow-up. He was a few inches taller than I last remembered and a few pounds slimmer too. His hair no longer in an unruly ponytail, but shorter and styled like late 90s Leonardo DiCaprio. He was wearing an open white button-down, closefitting undershirt, and jeans that showed off his new muscular pecs and biceps. His nipples just peeking through that fruit of the loom.
“Long time no see,” I said, reaching in for a hug and a reason to cop a feel. I teasingly smacked his butt and felt his glute tighten underneath.
“Hey Jenn” he responded, “Nice to see you.”
We spent a few minutes exchanging pleasantries, me asking about his experience in the dorms and what he was up to now.
“I was dating this girl who was a theatre major” he started. “She volunteered me to move these heavy set pieces around all the time. I started going to the gym regularly and improved on my crappy diet. I ended up joining intramural weight lifting and got in shape. Next thing I knew, girls started paying attention to me.”
“So are you still dating here or…” I asked.
Jason shook his head.
“Nah. Don’t get me wrong, that ass of hers was straight cake, but I just couldn’t deal with the emotional strings attached anymore.” He remarked.
“So what are you doing home this weekend?” I implored.
“Well, funny you should ask.” He started, “I could actually use your help with something.”
Jason explained that while he still YOLO’d stocks and traded options, he found another lucrative side gig as an XXX video performer. Ladies and gents alike would bid for an hour or so of his company where he’d perform acts of masturbation for the favor of his patrons.
“I figured I’d save some cash this week by doing it from here instead of renting a hotel room,” he commented. “I’ve got a booking in an hour. I’ll make it worth your time if you wouldn’t mind being my camera crew today.”
I was a little taken aback by his straightforwardness, but to be honest, I wanted to get a glimpse of his body under those clothes. Gone were the pizza-faced teenage acne and diet soda belly that I remembered. Plus money. Money is always good.
As he rearranged furniture, hung lights, and dressed his set, I caught a glimpse of his bulge underneath his jeans. His new fitness lifestyle really did a lot to maximize his potential. The Glow Up was real.
“Ok, so here’s the camera,” he said, handing me a monopod with a webcam mounted to the top. “Just follow me around the room as you see fit. My client may chime in with some direction as well.”
“Ok…” I hesitated. “So can you give me some examples of what to expect?”
Jason took off his white shirt and reclined on the couch. He rubbed a handful of baby oil across his tanned chest, abs, and arms. The glimmer of oil accentuating every curve of his lean and built body. A tuft of pubic hair was peeking through the waistband of his underwear underneath his low-hanging slim-cut jeans.
“Yeah, we got some time before the show.” He said. “So start by standing here.”
He pointed to a spot about 3 feet in front of him. I took a step and planted myself on the spot he indicated, but he placed his hands on my waist to nudge me just a half step closer. A tingle ran thru my tits at his unexpectedly electric touch.
“Yeah right there,” he said. “You can look at that monitor there to double-check the camera feed as needed.”
The picture on the monitor was squarely focused on the bulge of his crotch. I watched as he slowly placed his hands down his front, undoing the fly of his jeans with excruciating patience. Slowly he started stroking himself through his boxers, his not so little soldier standing at attention while making quiet sounds of pleasure.
I could feel my cheeks start to blush and as the heat of excitement between my legs began to smolder. I watched as he slowly stroked his cock up and down through the elastic cloth as if tempting me to come closer for a look. I found myself instinctively reaching out to touch it.
I grasped the full width of it with my hand over his boxers, my thumb finding the notch below the head. Without realizing it, I dropped the equipment and lunged forward for a better look.
Our lips met as he grabbed a palm-full of my hair, interlacing it in his fingers as he pulled me on top of him. With his other hand, he reached underneath my shirt, unbuckling the back of my bra, and massaging my breast, my tits rock hard like ice.
Our clothes came flying off in a fury. He guided the tip of his cock to my pussy. The warm juice of arousal easing its passage inside me. My tightness giving way. He held my waist as he guided my journey, easing me slowly onto his member. Down I sank on his lap, further until I thought I had enveloped him totally, the further down still, his extensive length catching me off guard. I moaned feeling myself being penetrated deeper than any before. Even without seeing it fully in the flesh, I knew he had an above-average-sized cock. No wonder strangers were willing to pay!
I rode him like a porcelain pony on a merry-go-round, soaking his groin with my juicy pussy. I felt him scoop his hands around my lower back as he lifted and lay me down across the couch. His hands pressing my knees apart, allowing a full unobstructed view of my cunt. He lowered his head at my groin, inserting his middle and index finger inside me. His tongue lapped at my pussy, exploring its walls and sides, working his way up to my clitoris, which he kissed and licked and sucked delicately.
He sat up, pressing my knees even further apart.
“I’m going to penetrate you slowly.” He said, looking me deeply in the eyes. “I want you to feel every last bit of me.”
I drew in a deep breath and nodded in eagerness as his head entered me. He pumped his hips shallow and slowly, going ever slightly deeper with each push. I moaned with delight, savoring his tease as I took more and more of him with each sway of his body. He pressed himself with his entirety, and I exhaled with breathy delight, enjoying the abundance of flesh within me. Expertly, he gyrated his pelvis against mine, allowing his cleanly shaved skin to rub up against my trimmed bush.
“I’m going to ruin you for anyone who comes after.” He alleged. “Your tight pussy will never be the same after I’m through with you.”
“Yes!” I urged, placing my hands on his glutes, urging him deeper to me. “Oh god, yes! I want your huge cock. Stretch me with your huge cock!”
I felt myself build towards climax as he rammed his member repeatedly against my insides. It didn’t take long for me to reach the promised land, animalistic cries escaping my lips. As my pussy began to quiver around his member, he held fast, maintaining his momentum against me. I felt myself building inside again, my face growing flush, the bottom of my feet tingling with fire as I felt an unexpected explosion of warmth forth from deep within.
I lay on my back, catching my breath as he exits himself and stands alongside me. His soaking member, coated with my bodily dressing, standing inches from my face. I turn to my side, placing a hand at the base of his cock. I taste him. I taste myself on him, luxuriating this product of lust we made together. I swallow, as much of him as I can. His fullness unable to fit in my mouth without choking and gags.
I adjust my position, laying at an angle that offers both my breast and my mouth to his cock. I squeeze my boobs together as he slides his dick between them, the tip and upper shaft grazing my lips with each full thrust. Back and forth he rocks, working his way towards the finish. I see his eyes roll back and his body tense as he nears. I close my eyes and open my mouth, ready and waiting.
Warm ropes of cum shoot forth from the tip like a fishing net cast into the water. I taste his seed as he sprays my mouth and breasts. I opened my eyes as he kneels beside me, our foreheads touching tenderly. I breathe in as he exhales, our hearts pounding as we catch our breath, our sweaty bodies co-mingling in the byproduct of our mutual desire.
“I’m glad we caught up.” He finally said as we giggled.
“It’s no wonder,” I started, pushing the words out between breaths. “That my mom digs your dad so much. Must run in the family”
“Actually,” he raised an eyebrow at me. “I’m pretty sure it’s your dad that keeps coming back for more.”