This story is actually a really long one so I’ll split it up into parts.. I’ll leave some kind of cliffhanger at the end. If you want to hear more, please let me know <3
So about 6-7 years ago I start a new job at a family owned mechanic business, there was just myself, the 2 owners and 1 Milf of a receptionist (for the story sake, I’ll refer to her as Jess).Jess was about 5″6, brunette with a E bust and tiny waist so as you’d imagine, my eyes were always glued to her gorgeous looks.
Jess worked 2 days a week as she would take care of the business bookkeeping but every time she came in she’d always come straight up to me and start a conversation that was what I’d call semi-flirtatious. She’d comment on my hair, tattoos on my arm and even throw in a few “stud” claims towards me. I didn’t think much of it, mainly because she was almost the same age as my parents so I shrug it off.
Months go by, the same conversations ensue and the days go by. Until she drops the bomb that she left her husband (who for the record, was a massive fuckwit). Suddenly, her advances become a more and more obvious.
This one day in particular, we were both asked by our boss to go upstairs and organise some new stock. Jess and I began talking about girls and relationships, even sex when she asked me “Surely you’ve been seeing someone”, I told her I had recently broken up with my girlfriend and we had a huge blowout the weekend prior. Jess’s eyes somewhat lit up but in such a specific way, It made me really confused in the moment, She then shrugged and said “maybe you’d find someone else soon”, I kind of just ignored the comment. As we were leaving the upstairs area, Jess turns out the lights with the door still shut in front of us. She turns around and without any hesitation, she grabs my cock and pulls me in. I was so thrown by the situation I didn’t know how to react. Jess starts passionately making out with me till I gave in and together we ran our hands up and down each others bodies. It was the single hottest moment of my life at the time, my cock was throbbing at this point BUT, in true cougar nature he left me hanging. She stopped the kissing, she looked at me with this SEXY grin, let me go then left the room… you better believe that moment got saved straight to the wank bank…
A few weeks later at work, Jess and I were talking about music and I mentioned that I was a guitarist in a band and have been playing guitar for years. Jess got really excited and asked If I’d teach her which I agreed to immediately.
“Do you think you’ll be free tonight” she asked.
“yeah for sure, I’ve got nothing planned, where do you want to do it?”
“We should go to the beach tonight and do it there”… she started to exhibit a very similar grin I was far too familiar with from weeks before.
“It’s a date” I replied, whilst trying to hide my boner.
9pm rolls around and Jess has just driven to my house, I grab my acoustic guitar and meet her. I hop in the car and she greets me with a comforting hug which was the first time ever, immediately I knew I was in for a good night. We arrive at the beach and surely enough, It’s dark and no one is there but us. The beach was at the base of a big hill so there was a 5m concrete wall backing up to the carpark so naturally we walk across the sand and up to the wall and sit with out backs against it. I naively proceeded to teach her chords and finger placement on the fretboard, after about 20 minutes Jess starts to struggle.
“Can I come and sit between your legs so you can correct my hands?”
“Oh yeah of course”, Instantly my cock becomes erect.
Jess shuffles over the sand and sits between my legs and this is where it got awkward.. my boner is poking her in the back.. Waiting for her to mention something but she completely ignores it and keeps trying to play. She struggling so much she askes me to correct her hand on the fretboard, I lean forward to see what was going on and then It happened… Jess turns her head and proceeds to kiss me just like last time but this time, I reacted naturally. We’re passionately making out, my left hand is lightly holding her cheek whilst my right hand caresses her breasts. Her hand slowly moves up my leg and begins to rub my bulge. It finally hits me, HOLY SHIT IM ON A DATE WITH A MILF!!!!. This is the hottest thing ever. We continuously make out for about 30 minutes until she offered to go back to the car. We both get up holding hands this time and she leads we to her car. Jess is walking in front of me purposely swaying her hips as she walks up the stairs… WHAT a TEASE!…
Let me know if you want to read more!
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