I worked at a pharmacy while in college because where else could I make $15/hour part time with paid benefits. I was the youngest employee and 1 of 3 guys who worked there. Most of the staff were friendly and sarcastic but married or otherwise not interested in anything more than counting pills & billing insurances. Susan was similar but every now and then would flirt when it was just a few of us working and usually when the pharmacist wasn’t around. She was also 36, married with 2 kids, tan skin, a healthy rack and some great curves for a 5’4” brunette.
I joked along most of the time and didn’t think anything of it until 1 day about 18 months in to the job we were working on a prescription and the insurance billing wasn’t processing correctly. Complex request for a customer and after we’ve prepared the medicine we can’t get the system to process it through the insurance. Pharmacist works at it to no avail. Susan, the resident insurance billing expert, can’t figure it out. It’s becoming an ordeal and the customer is waiting to get their medicine and be on their way. I offer to take a crack at it despite previously unsuccessful attempts by more veteran staff. As I’m working my way through insurance screens Susan’s soft sultry voice whispers in my ear, “I’ll bet you a blow job it won’t work.” While I heard her clearly I also thought…haha. Ok. But that’s an empty wager.
Click, click, type, type, change a few codes & voila insurance accepts the prescription, spits out a copay for the patient & all this with Susan hovering over my shoulder waiting for resolution.
As a young military guy & virgin, the rest of my shift is spent with a) a healthy erection & b) endless scenarios attempting to calculate how to cash in that sexy wager. A few days later as I’m working on college homework, I spy Susan is online via MSN messenger. It’s past her kids bedtime so I shoot over a casual hey & resume typing a paper or researching. We trade a few pleasantries and I decide now is a great time to validate how serious that bj wager was. She doesn’t even flinch and engages in some erotic chatting about when, where & how it could go down. Around thanksgiving she will have a near empty house & that would be a convenient time for her to pay up. We finish chatting and I don’t see her at work for the next 3 days.
When Susan & I finally have a shift together it’s an early morning and pretty slow day so we spend some time restocking pharmacy shelves and catching up on paperwork. A few aisles have obstructed views which offers some privacy & being 2 feet wide, its usually 1 person in an aisle at a time. Susan is sending fax requests while I’m restocking pill bottles. As I near the aisle with our fax machine & limited counter space I notice she’s at the end of the aisle making notes. When she sees I need to put stuff away she attempts to shift her body closer to the counter (a la airplane row seat style navigating) so I can slide by. With her ass toward me I slide behind her in a non-sexual manner to carry out my work. Just as I’m positioned directly behind Susan she sticks her ass out & into my crotch to grind against me. So I don’t fall backward and knock over shelves of drugs I’m forced to grind back in to her pretty strongly. She takes this opportunity to wrap her left arm around my waist and further assist my grinding while ensuring it lasts more than 5-10 seconds. Cue near instant boner. The next 10 days is filled with these “accidental” grindings as we still any moments possible for shameless flirting and horny clothes physical contact. The online chatting has equally escalated and formal plans are confirmed for the Tuesday before Turkey day.
The Monday before our scheduled rendezvous we work together and engage in excessive amounts of copping feels and bumping & grinding sessions. As we get off work at the same time I walk her out to her car in anticipation of the next 24 hours. She climbs in the front seat of her F150 and her rack is virtually in my face with her legs conveniently spread wide open for me to further fondle over her jeans. Even this brief petting session is causing a wet spot in her pants and she has no way to fully enjoy the moment nor reciprocate.
To prevent any further temptation she starts her truck and heads home.
All day Tuesday at college is consumed with thoughts of what is about to happen later that night….Susan blowing me to pay off her lost bet. I leave school, grab a quick bite and head towards her house for our 8pm meetup. I park in her neighborhood and text to make sure we are still on. Her kids haven’t fully gone to sleep so I’m asked to wait outside in my car. Once I get the all clear text I head to her house & am trying to conceal a very health erection. Cue surprise of all plot twists. She opens the door in a spaghetti strap tank top, no bra & polka dot bikini panties. That’s all folks! My mind has just gone supersonic as I enter her dimly lit living room & have no clue what is about to unfold. We sit on her couch in candlelight and make chit chat to break the ice. Finally she decides it’s time to head to her room & I’m happy to follow like a little puppy as her ass jiggles out of the room & down the hall. We enter her room, all lights are on & she asks me to close the door. She hops on her bed, kneels in the middle and tells me to take my clothes off.
I obediently shed everything and await further details. She invites me over to the bed and I climb in, laying atop her cheetah patterned throw blanket flat on my back. Without even a word, she straddles my rock solid cock & slides me inside her soaked wet pussy. Welcome to heaven…enjoy the ride. She proceeds to ride & grind me while I alternate between fondling her tits under her shirt & grabbing her by the waist to further bury myself inside her. She’s a wet as can be & i’m rapidly nearing orgasm as she throws her hair back and plants her hands firmly on my chest for balance. Houston we have liftoff!!! I explode inside her, sans condom & it’s amazing. She’s enjoying this just as much and is moaning in rhythm with each thrust.
Once I’ve finished she rolls off me & on to her stomach beside me pleasantly satisfied but also victorious in getting me off. Thanks to my youth & inexperience I’m ready for round 2 in no time, but she is content to stay in her current cozy position and let me explore. I oblige and proceed to enter her from behind doggy style and she happily responds with an incredible combination of grinding back in to my thrusting and intense kegels. Sooner than the 1st round I realize I’ve hit the point of no return. She shoots a sly grin over her right shoulder as I’m hovering over her sexy curves and heavily breathing in her ear I’m again about to cum. She times it perfectly and executes another series of death grip kegels which seem to extract every ounce of me into her wet juicy pussy.
No sooner have we finished her youngest knocks at her door sending me darting in to her bathroom. I hide behind the door for a few minutes while she shuffled the little one back to bed. Without moving she signals for me to return and engage in round 3 except this time she’s staying put while offering up her ass as my next source of heavenly release. Knowing I’m still covered in her moist juices she grips my cock and slowly guides it into her ass & I experience and even tighter hole than my previous forays. As we synchronize the rhythm our bodies this round is a bit slower and more intense as I can tell she’s really getting off to my fucking her ass. She’s again grinding herself backward in to me while clenching her ass cheeks around my cock. It’s otherworldly and before too long I’m already unleashing load 3 into her gorgeous cougar frame.
I collapse on her back utterly drained and relaxed while she reaches back to run her fingers through my hair. Her sultry giggle and thanks for several good rounds still ring in my ears. I finally pull myself out of her and climb off and head for my clothes. She hops out of bed, slides her panties back on, and walks me to the door. We still worked together for a few months after our encounter, still flirting and grinding like before. Whenever possible the dirty sex talk at work increased and sparked some more feeling each other up. Unfortunately late December I had to leave working there & we never had another encounter like our Tuesday night romp.
To this day I can still feel the softness of that cheetah blanket & picture that gorgeous MILF figure greeting me at the door. She’s relocated not too far away, but we haven’t seen each other since we last worked together.
Source: reddit.com/r/gonewildstories/comments/csus5d/blowjob_bet_becomes_more_fun_with_older_coworker
Well I mean, she never did actually pay off the bet. :P She still owes you a blowjob
She never gave you that blowjob….
Such a hot read. I especially loved the teasing and grinding part of it
Did she know it was your first time