Kelly's Diary 019 - My First Time With a Married Man - Cover

Kelly's Diary 019 - My First Time With a Married Man

Copyright© 2024 by Kelly85

Chapter 1: Teasing Don

Coming of Age Sex Story: Chapter 1: Teasing Don - I was only fifteen and while I'd been having sex for about a year, so far I'd only been with boys around my age. This was the first time I gave myself to an older man and little did I know at the time what an appetite I had for older married men!

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/ft   Heterosexual   True Story   Cheating   Exhibitionism   Masturbation   Oral Sex  

Don was a forty-five year-old manager at my dad’s law firm. He’d been working there for over ten years and so had watched me grow up during my periodic visits to the office. It was summer vacation before my sophomore year of high school and my dad was letting me work part time - more for something to do than anything else since he always gave me whatever money I asked for anyway. The only other women there were a receptionist, secretary and an accountant who were your typical middle-aged frumpy housewife types.

While I may have been young my figure was beginning to finally develop nicely. I enjoyed wearing clothes that teased the men at the office even though they were almost all married and over forty. My dad didn’t seem to care so long as it was all innocent fun. I enjoyed the looks (and in some cases the bulge that betrayed their thoughts) and I’m sure they didn’t mind a bit having a young high school girl half their age prancing around for them to enjoy. I didn’t dress TOO wild, at least not by my standards - just jeans maybe a size or two too small, tight blouses with maybe one too many buttons undone, short skirts with sexy underwear ... well you get the picture.

Don (the men all preferred I call them by their first name) certainly appreciated my efforts to raise office morale (among other things) and he would often lean over my shoulder when I was at my desk to ask me something. I always made sure he was rewarded with a nice view of my small breasts - something made easier by the fact I rarely wore a bra to work. I liked to tease him in the hall or at his desk by rubbing up against him and was usually treated to a noticeable swelling in his pants by the time I left.

Between working for my dad and being married with children Don was cautious not to respond in any real way. Of course this only encouraged me to be even more daring. I started “forgetting” to pull my skirt down when I sat in his office and slowly crossed my legs to show off my tanned legs. Then I’d spread my legs just enough to hint that I might not be wearing any panties. Needless to say he never protested and I think he considered my flirting just innocent fun by a teenage girl. Even so, I would get hot thinking that he might be masturbating at night dreaming about what he wanted to do to me if he was a teenage boy again.

One day I overheard my dad talking to my mom about work and the subject changed to Don and his family. My dad was telling my mom that Don’s marriage had not been all that great lately and he was worried about his performance at work. I knew from office parties and other functions that while Don kept himself in great shape his wife had really let herself go over the years. It seems she just got heavier with the birth of each of their three children.

Once I overheard Don joking with the guys that he had twice the woman he had married except he wasn’t laughing when he said it. I thought about my mom and how she looked fantastic in her skimpy bikini. She loved it when people mistook her for my older sister. I just don’t understand why women think that once they have a man trapped in marriage that they can gain a hundred pounds and still expect their husband to want to have sex with them. In my opinion if their hubby gets frustrated and seeks out sexual satisfaction from someone else then she has only herself to blame.

A few days later I was in Don’s office helping him file some paperwork when I remembered what my dad had said about him. For whatever reason I was feeling especially daring at the time so I struck up a conversation. Moving over to his desk I picked up a picture of him and his wife and looked at it for a few seconds and then turned to him.

“So Don, what’s your secret to staying married for so long?”

Don didn’t even look up from his work to respond. “It’s really not that hard once you’re married as long as I’ve been. Things become routine, you know your roles and responsibilities, obligations that have to be met, kids to be raised. I guess it becomes more of a partnership after a while.”

“Gee, that doesn’t sound very romantic. Seems more like something you HAVE to do than WANT to do.”

Don sighed and his pen down. He looked up me with this distant look on his face. “Well Kelly, if you really wanted to know, most guys like me have no choice. I’ve actually got a pretty good life right now and a divorce would ruin me financially. There’s this huge mortgage, car loans, credit cards, not to mention two kids in college and a third not too far in the future.”

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