I was 22 and had just graduated college. My job in New York City didn't start for about another month so I headed back to the dreaded Midwestern suburb that I grew up in to pass the time. I was really not looking forward to living with my parents again, doing household chores, awkward run-ins with former high school classmates or the incessant boredom that necessarily came with Midwestern suburbia, even if it was for only one month.
When I had left for college, I was shy, awkward and somewhat nerdy. But after four years at a preppy private school in the Northeast, all that had changed. I had filled out my previously slim frame through countless hours at the gym, invested in expensive, preppy clothing, and had learned how to drink, party and fuck by socializing with the rich, northeast elite that attended my school. I wanted to be in New York, making money and going to parties, not bumming around my house in the suburbs.
With so much free time on my hands at home, I quickly found myself frequenting the nearby gym. Since it was so close to many rich, suburban neighborhoods, I realized that it was a hotspot for housewives. Most of them, with about as much to do as myself, went to the gym a lot and were in great shape. Between strategically timed visits to the hot tub and playing dumb about the gym's layout (I was new after all) I pleasantly found myself flirting with many hot moms.
One weekday morning, as I was wearing a cutoff that exposed my muscular biceps and was loose enough to show off my abs as well, I maxed out on the bench press in conspicuous view of a petite blonde on the treadmill. But as I set the barbell down, I heard a surprised, familiar voice.
"Brandon!?" the high pitched voice called out.
I turned around and there in a tight, blue, athletic tank top and yoga pants was Mrs. Juliana Fasano. She had lived down the street from me for years and her two boys, Tony and Jack, had been buddies of mine all through school. The Fasano's had had me over at least once a week to swim in their pool and then enjoy a huge Italian meal. The only thing better than Mrs. Fasano's cooking was her incredible body. She was short, maybe 5'2-5'3, and her legs and arms were always perfectly toned and tan, and she had a small, tight ass. Her hair, usually light brown that she occasional dyed a dirty blonde fell in beautiful, soft curls just past her shoulders. And when she smiled at you...well, it was nearly impossible not to smile back. She would flash perfectly white teeth and her light blue eyes would shimmer. But whenever you talked to Mrs. Fasano, it was usually pretty hard to pay attention to her smile or eyes. She always seemed to be in a tight or low cut outfit that showed off her magnificent breasts. They were either large C's or on the smaller end of D's, but either way they looked amazing on her petite frame. I still remember the first time the Fasano's invited me over to swim one summer. I was maybe 13 and will never forget when Mrs. Fasano waded into the pool in her red bikini. It was so small that her boobs were oozing out of the sides as they hung there, soft and supple off her chest. Ever since that moment I had made it a point to stay close friends with Tony and Jack.
But, as it happens in life, after I graduated from high school, I drifted away from their whole family. Tony had gone off to a small school not far from town while Jack had started working for his father's construction business. Steve Fasano, Tony and Jack's dad and the lucky husband of Juliana, was a big guy. Not very tall, but stocky with a bit of a gut and with thick black hair and a mustache, he was about as stereotypically Italian as it came. He was gruff but hardworking and provided a very good living for his family Where Mrs. Fasano was light, conversational and extremely outgoing and personable, Mr. Fasano was sullen and intimating. I never exactly understood how the marriage worked. I hadn't seen any of the family since I had graduated four years ago.
I was suddenly jerked out of my reflections on my first glimpse of Mrs. Fasano in a bikini by the same voice calling out again.
"Brandon Jackson? Is that really you?" she asked as she approached me.
"Mrs. Fasano!" I gleefully replied as I became happily subsumed in the outstretched arms of her hug. With my muscular arms I wrapped her into a tight hug and relished the feeling of her boobs pressed against my chest, a sensation I hadn't enjoyed in many years. Despite those years, she looked exactly the same. The same milf I had enjoyed seeing through all of my childhood.
"Wow, you've changed a lot." She mused, feeling my chest through the light fabric of my cutoff. "You were a shy, skinny boy the last time I saw you and now look at you, a muscular young man."
"Thanks Mrs. Fasano." I said, blushing ever so slightly. "You look incredible! You must come to the gym every day, how have I not seen you here before?" I asked her.
"I do come everyday!" she replied emphatically. "Steve and I were just visiting Tony at college. He didn't do so well early on, so he's taking summer classes to try and graduate soon."
"Well, that happens." I said.
"Tony was never that good at school. Not like you. He could never have gotten into that good private school you went to. I'm sure you graduated on time." She said.
I gave a conversational laugh, "Yep, just last week. With highest honors too. I start my job at an investment bank in New York in a month."
She shook her head in amazement. "What can't you do?" she asked "Great school, top honors, a high paying job in New York plus all these muscles. Not only has Tony not done too well in school, but he's put on a lot of weight, and not in the good way like you have. He looks like a younger version of his dad."
I laughed a little nervously and tried to deflect the flattering comparison. "How is Mr. Fasano?" I asked.
It was her turn to laugh, "He's alright, I guess. Same old same old. Still pouring concrete, still refusing to shave that mustache, and still eating too much of my food."
"Oh my God." I responded, strategically lifting my shirt to show off my abs while rubbing my stomach. "I have missed your food so much. In four years of going to school near New York, your Italian food is still the best I've ever had!"
"Well, what're you doing this afternoon?" she asked "It's supposed to get pretty hot, so why don't you come over for a swim and a meal like old times. I'll cook up all your favorites."
"Oh my God, Mrs. Fasano, that sounds amazing. I'm already drooling thinking about it."
"Great!" She replied. "Come over around 1. Bring your swimsuit and your appetite!"
Though I was drooling about the thought of her food, the thing I was drooling over the most was the thought of seeing her in a bikini again. I showered and hurried home, agonizing about what I was going to wear. I eventually decided on a pair of short, salmon colored swim trunks that went about halfway down my thigh, and a light blue oxford shirt. I only buttoned a few of the middle buttons, leaving plenty of my abs and chest exposed. I brushed my light brown hair over in a slight imitation of Jack Kennedy, donned my boat shoes and sunglasses, and headed down the street with all the confidence in the world.
I rang the doorbell and immediately felt the blood rush to my cock when Mrs. Fasano answered. She had a long, white sarong tied around her waist and the same, small red bikini top from ten years ago.
"Brandon!" she squealed. "I'm so happy you came! You look so handsome." And she came in for another hug. Instead of going around my neck, her hands slipped in under my loosely buttoned shirt and wrapped around my waist while my hands felt all the way up her exposed back to where her bikini strings were tied at the nape of her neck.
She took my hand and led me back into the house and out onto the patio by the pool while I stared at her ass the whole way. Italian sausages were grilling slowly and she turned them over quickly with stainless steel tongs. Then she moved to the poolside glass table where there was a margarita pitcher.
"I didn't know what you like to drink, and I know it's not Italian, but it is summery so I figured it would work fine." She poured us each a glass and handed me mine. She was about 6-7 inches shorter than me and as her big blue eyes looked up at mine, I struggled to meet them and not wander off into the great view I had of her cleavage. She raised her glass to mine:
