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Introduction:

Anna-Brooks fascination with an older man leads her farther down the rabbit hole than she ever thought she’d go, as Mike Robert’s introduces her to the BDSM lifestyle
Hello! This time I thought it would be fun to see where the Roberts Boys got it from. If you are not sure what I am referring to, please click my profile. Of the 12 multi-chapter stories written so far, 10 are about the Roberts boys and their sexual hi-jinks/adventures, so it’s high-time I wrote something about their Dad. This one incorporates a young lass’s introduction into BDSM, hope you enjoy it!)



The temperature was humid, the air thick, and the sun bright, which only made my mood worse. There are things about Florida I loved, but the heat was not among them, and I cursed under my breath, because the babysitter had just canceled on me.



Who am I? I’m Mike Roberts, father of Johnathan and David (about whom I have written several stories already). Yeah, I’m getting close to 60, but I’m still enjoying being a ‘power-player’ in law & business related to the panhandle part of my state. Swimming and Biking have become a thing, along with a trainer to keep this “old” man in shape, and at 6ft. 4” I sport a body & lifestyle much more athletic than men younger than myself. Heck, I still have most of my hair!



I have family in this week, as her father David & his partner Brandi (See my 4 part series, DAVID’S GAME) were out of town, but I also had a philanthropic function I was to attend this eve. Even though the function was casual, Maddie, my grand-daughter was just too young. I had hinged at least one if not two deals on getting to hob knob & politicize, and now the damn babysitter had cancelled on me.



My younger son David Roberts certainly made a cute little girl that I of course doted heavily upon. I checked my Rolex and saw that I needed a babysitter in the next 4 hours, & on a Saturday night to boot. Damn kids these days. I sighed and decided to ask the one person I knew, knowing what the answer was probably going to be. I stepped outside and made my way to my neighbors, knocking on our door.



A moment later, Anna-Brooks Cowan was standing before me.



"Hi, Mr. Mike!" She said brightly.



Anna-Brooks Cowan was 19, and was a very pretty woman. She stood about 5ft. 5 , & yes, she carried a bit of weight in the hips, combined with a small chest that made many boys her age pay her no attention, which was a shame. Anna-Brooks had that ‘thicc’ body, with wide hips and a sexy round, buoyant rear end. Her body was voluptuous, with smaller-yet-plump-looking breasts on her chest. In the last year plus, she had become a very attractive woman, and it wouldn’t be long before the boys took serious note.



Anna-Brooks’s skin was pale, milky almost, which made her sweet brown eyes and brown-brunette hair seem even more vibrant. Her smile was large and beaming; enough to light up any room. She was maxing-out the girl-next-door thing, right down to some powerfully cute freckles, but she had a certain ‘needy’ vibe going, and that got this ‘old man’s’ mind spinning, but she WS a neighbor, after all, so at least for the moment, I tucked it away.



Currently, she was in a gray t-shirt and yoga pants, with the front of her shirt being loose enough for me to see the budding outline of her breasts, but I kept my gaze professional. I explained the situation to her and offered her a generous amount. I felt silly and I wasn't going to judge her at all when she said no.



"Sure!" Anna-Brooks said. It was not the answer I thought he would receive. "My boyfriend is working night shift this time of year, and I'd rather have something to do so I'm not all alone at night." Yeah, one boy had noticed but he was at best a poor excuse for a boyfriend. Her father even called the young man “Curb,” because he was sure his daughter would wake up soon enough and drop him there.



Before I could thank her, Anna-Brooks's smile grew even more luminous. Her cat, Muffin (oddly-aptly named), had just walked by. She turned and bent over to grab me, and I found myself in an awkward position. As Anna-Brooks was bent over at the waist struggling to pick up her squirmy cat, the stretched material of her yoga pants was being lit up by the sun and had turned completely see-through. Not only was her bubble butt being presented right to me, but he could also see the bright pink lacy thong she was wearing. Were I shorter, I could have gotten a glance at her back-camel-toe. I got a goo-oo-od look, And I could not look away. Hmmm…what the Hell? Time to test.



Anna-Brooks wrangled the cat and turned around. I shot my eyes back to hers and I made small-talk, mentioning it was nice to pet her Muffin. When I did Anna-Brooks got a wry smile. I thanked Anna-Brooks for agreeing to babysit, handing her a portion of the agreed amount. She glanced down and took the money, and I saw her eyebrows twitch. It was when I walked home I realized I was semi-erect. She must have noticed that. I found myself picturing her ass in that thong, and I realized that the test was a success



***



When Anna-Brooks came to my door later, both she and I were momentarily surprised. I was taken aback by how...casual yet sexy her attire was. Her black skirt was rather short, sitting just a couple inches above the knee. The blue blouse she was wearing was tight, and I could not help but notice the two buttons on top weren’t buttoned. " Wow Anna-Brooks, You look...(Fuckable)...nice, that color really suits you" I said. My boner was instantly back.



Anna-Brooks seemed taken aback by how cleaned up I was, which was not my norm since becoming a widower. My usually shaggy hair and unkempt beard had been groomed, and I was wearing a nice button-down and slacks showed that my body was actually well defined. She hadn't ever noticed how big my arms were, or how piercing my gaze was. She shook the thoughts off and returned the compliment. "Well don’t you look... (Fuckable)...you're ready for a fun night!"



I laughed, and I when I mentioned I’d almost rather spend it with her, she again got that wry smile. As I turned I could hear her mutter something about ‘wishing I would’, & I thanked her one more time before heading out the door. As I made my way to my car, I was totally getting the vibe that she was into me, a man three times her age! I thought about how fun it would be to lift that skirt, then pushed it out of my head, at least for the moment. Afterall, I had business to attend to. “She did ‘pass the test’ “, I told myself, & with that, I started the car and drove off.



--



It was just past 11:30 P.M. when Anna-Brooks heard a car pull-up. She'd been half-asleep watching TV on the couch. She smoothed out her clothes and got to her feet as I came in. I smiled warmly at her, and I’m sure she could immediately tell I wasn't exactly sober. "Hey, Anna-Brooks! I took an Uber back home. Got a little carried away at the bar..." I told her sheepishly.



"You're an adult, Mr. Mike. You can do what you want, especially on a Saturday night. " She looked me in the eye as she said it – was she also doing a bit of testing?



"How was she?" I asked, making my way to the kitchen. Anna-Brooks told me about how quiet the night had been, just playing games and drawing. I listened as I took a pair of beers out of the fridge. "You wouldn't want to have a night-cap with an old man, would ya?"



Anna-Brooks laughed and shrugged. "Sure. And you're not old. You're actually in pretty good shape…and then some."



“watch those comments young lady,” I bantered back, “I’d hate to have to teach you a bit of….” Then stopped.



Anna-Brooks had put on some low music and lit a candle. She was turned, showing some serious leg. Turning she said, “Had too much to finish your sentences?”



I glanced down & noticed how far up her skirt had ridden. Both her thighs were practically entirely out. “Let’s just say something caught my eye.”



Anna-Brooks’s first instinct should've been to immediately sit up and pull the skirt back down. But she didn't move. She liked the attention, the flirting, & Anna-Brooks Cowan realized she actually liked that this handsome older man was looking at her legs. There was a buzzing warmth growing inside of her. The practical side of Anna-Brooks knew she should stop, but she was having fun.



“Is that all you noticed?” She asked, as brought up one hand to undo two more buttons on her blouse. The effect was immediate. Mike could now see the full top-halves of her breasts, and Anna-Brooks noticed that his cock began to stir. It was clearly filling out his pants more than a minute ago. Anna-Brooks realized that this was starting to make her wet.



The beer was finished, the music was nice, and the candle added to the ambiance. Time to see how willing she was. "Thanks for coming over and helping out, Anna-Brooks." I said and bit my lip, mostly because she was staring at my bulging crotch



"No problem……Mike. I had a nice time talking to you."



"Anna-Brooks, you should go home, because if you stay..." I said, motioning towards my bulging dick.



Anna-Brooks had turned as though she were headed toward the front door. She put her hand on my knee & smiled softly. "If you need someone to babysit, clean up around the house, suck your cock, water the plants, just let me know..."



I sat frozen for a moment, and took it in, then took her hand just before she got up.



"What did you say?" My voice was low.



Anna-Brooks looked deliberately at my bulging crotch, then directly into my eyes. "Water your plants?" She asked, the mischief in her eyes betraying her innocent tone.



I smiled as I stared at her. It appeared we each had our catch
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