[MF] When I was 18 my 56F boss gave me a blowjob in her car the week before her wedding day.

18 year old me, 6’5″ 220lbs, fit tennis player, working at a pizza restaurant, horny all the time. My boss was a fairly good looking cougar of 56 years old. Blonde hair, medium build curvy body with nice DD tits.
 

I worked the closing shift on the weekends quite a lot during the school year, then during that summer I began working the closing shift 5 nights a week, 3 of those nights with the store manager “Jan”.
 

Jan began obviously flirting with me at times when we were alone in the back of the store. It started by her brushing up against my back as she edged past me in the tight space by the sink area. I would feel her large tits press against my back and drag across me as she passed by slowly stepping sideways behind me to get to the stockroom area.

On one of these occasions I pressed back against her and trapped her against the wall behind us. She let out a sudden moan that could have only been pleasure and then pinched my side just above my belt line, causing me to move and she moved on as well, no words spoken.

 

Later, she was eating her “lunch” as we worked the closing shift. Her lunch was a salad and some long frenched carrot sticks, about 5″ long each. I stood at the sink washing pizza pans as she sat to my right on a stack of stocked goods in one gallon cans. I watched out of the corner of my eye as her tits strained against her blouse, which was a button down, dress shirt with small pinstripes. The curve of the pinstripes over her tits was amazing and the blouse was gapping between the buttons as her breasts pressed against the fabric, threatening to pop open a button or two. When she would turn just right I could see the lacy fabric of her sheer white bra through the gaps.

 

I looked over at her… more honestly, at her breasts and then realized she had caught me openly staring. She smiled at me, said nothing, then opened the top three buttons of her blouse, revealing her ample cleavage to my gaze.

She then took one of the carrot sticks in her fingers and slowly slid her mouth down over it, her lips caressing it as if it were a small thin cock she was enjoying.

 

I had lost my virginity at 14 and had quite a bit of sex in the 4 years between. I also had my stash of porn magazines, so I knew what she was doing, there was no mistaking it at all. My favorite reading material at the time were stories printed in the magazines I hoarded under my mattress, and this was beginning to play out like one of those amazing stories!

 

I decided to be bold… a bit against my character with her up until that time, but what did I have to loose besides my job. Something told me I was not about to loose anything. I smiled back at her and said, “you know, if you need something bigger to suck on, I can probably find something for you”.

 

She was visibly shaken when I said that. I watched as she closed her eyes for a moment, with a soft gasp. Could it be that Jan just came when I mentioned her sucking something bigger?

When her eyes opened, there was fire in them and she asked, “how big are we talking here Rick?”

Continuing to be bold, I grinned and admitted that I had never measured myself to know. She laughed and said , “If you are going to tease a woman Mr, you should know what you are talking about”. She then stood and squeezed past me, her tits against me once again, and then walked out.
 

I figured that I had blown it, as she just walked out the back door, probably to take her smoke break I figured. However, a few moments later, she came back inside and walked over to me with a sewing type tape measure dangling from her fingers. With a serious tone, she handed the measuring tape to me and said, “anything over six inches and I’m a happy woman.”

I looked at her, likely with a look of shock on my face. As I tried to gather my wits once again, I heard her say “Do you want me to do it for you?”

It was my turn to gasp in surprise, and I quickly walked to the bathroom. No need to work on gaining a hard on, as I was already throbbing by the time I shut the door. Oh fuck! I thought. And I proceeded to measure my length after dropping my pants and briefs. With the tape at the base of my cock, against my balls, I measured 7.5″ to the large mushroom tip. I remembered her saying that anything over six inches was going to make her happy, and I couldn’t help but stroke myself a bit.

 

A knock on the bathroom door woke me from my self pleasuring and I quickly put my hard cock away and fastened my pants back. Emerging from the bathroom, handing her the tape, which she immediately put to her nose for a long inhaling breath. She asked what the results were, and I told her, to which she simply shook her head and walked away giggling.

 

She was quiet the rest of the hour as we cleaned and closed things down for the night, and I was not sure what to think of it. When I was about to leave, she called me over to where she was finishing up going over the accounting for the day. She asked me If I would mind going with her to make the night deposit because she didn’t want to make such a large deposit alone. I thought nothing of it and agreed to go with her.

 

We walked out to her car after locking up the restaurant, where she handed me the keys and asked me to drive. As we pulled out onto the street, toward the bank, she sighed and her hand fell to my knee, her fingers squeezing and caressing my knee and thigh with silence in the car.

A few blocks later I pulled up to the bank where she got out of the car to make the deposit, but not before leaning over and kissing me on the lips suddenly. A short but decidedly wanton and wet kiss. She then made the deposit and got back in the car. This time she sat slightly sideways in the seat facing me, and asked me to find a place where we could park alone.

I knew just the spot, and drove there quickly. A place I had been just the week before with a sweet girl I was dating off and on. We pulled up and I parked in the shadows. She then leaned over and kissed me again, pushing her tongue into my mouth as her hands quickly found my pants and pulled them open, freeing my very hard cock.

 

Jan wasted no time and went down on me, taking me fully into her hot mouth in one long smooth sucking draw of her mouth over me until I was lodged in her throat. I felt her throat clench me as she swallowed and began to mover her mouth up and down over me, her tongue swirling around my head, her hand stroking me with each long suck and retreat she made. I lost all track of proper time, and was soon on the brink of cumming, warning her of it. She simply moaned over my cock, then used her lips to squeeze my head tightly, the blood rushing from it, staying my orgasm.

This she did over and over again, bringing me to the edge four or five times over what I would guess was an hour of her mouth and hands enjoying and pleasuring my young hard cock. She then looked up at me and said that she was ready and it was okay to cum in her mouth. She asked me not to tell anyone, especially her soon to be husband that she was going to make vows to in just a week.

I promised my silence, (which I kept for years after) and she lowered her mouth to me, sucking me in a way I had not felt yet, and I was very quick to cum so fucking hard and long. Shooting stream after stream of my juice into her hot mouth, hearing her swallow and slightly gag once, as I flooded her with my cum.

She sucked me dry and clean, swallowing it all, then kissed me once again, (the first time I tasted my own cum). I tucked myself back into my pants and leaned over to begin playing with her tits. She pushed me back, and said that she just couldn’t because she was getting married soon.
 
And that was that. We drove back to the store, went home, and she never flirted with me again. A week later I was there as she walked down the Isle to get married. She looked at me as she passed and winked.

Source: reddit.com/r/gonewildstories/comments/59sczt/mf_when_i_was_18_my_56f_boss_gave_me_a_blowjob_in