tagMatureNo Regrets

No Regrets

byblueplains©

"AHH!! OHH!!"

I yelped as I felt something cold moving inside my t-shirt, shocking me awake. Jumping straight out of the deck chair, I felt the chill slide down my chest, drop into my baggy shorts and nestle right next to my nut sack.

"OOOH!! SHIT!!"

Landing on my feet with a thud, I danced wildly around our backyard patio, frantically shaking one leg, and then the other. With the last shake, I saw an ice cube dislodge itself from my boxers, pop out the bottom of my shorts and skitter across the sun-drenched wood floor of the patio. On the table next to my chair, I could see that my glass of lemonade was missing exactly one ice cube.

"I'm sorry, Michael, I couldn't resist."

In front of me, shaking with laughter, was Mrs. Martini, our next-door neighbor, my best friend's mom, and Grade A MILF. Her petite frame was doubled over as she giggled uncontrollably, and her mane of curly black hair spilled over her shoulders as she quivered in amusement. Finally, she managed to compose herself, giving me a warm smile as she shook her head at me.

"You should try those moves out on a dance floor," Mrs. Martini said, still beaming at me. Mrs. Martini's smile was perhaps her most attractive feature, and that was high praise, considering the many other facets of her beauty. She stood about 5' 4", and although her college cheerleading days were almost 20 years in the past, she still retained the trim figure and the effervescent personality of a pep squad leader. Her dark brown eyes twinkled, and although she was 40 years old, the only clue to her real age were the tiny wrinkles that formed at the corner of her eyes when she smiled, which was a lot. Otherwise, you'd swear she was 10 years younger.

"Ha, ha very funny, Mrs. Martini," I sputtered, straightening up. I stuck my tongue out at her in mock annoyance, and Mrs. Martini stuck hers out right back. Her tongue was wrapped in the red buds of her lips, which she pursed at me with theatrical effect. Then she narrowed her eyes at me and wagged a scolding finger.

"I've told you, you're not a kid, you're 18 years old, in college and an adult. You don't have to call me Mrs. Martini." She moved her lips into a pout, and my heart fluttered. "Besides," she added, "it makes me feel old."

"OK, OK. Judy."

Judy's face brightened. "Oooh, much better," she cooed in delight. She motioned to the quiet house behind me. "I tried the doorbell, but no one answered. Are you the only one home?"

"Dad's at work and Mom's out for the afternoon. I had classes this morning, but I'm done for the day. I came home to do some reading, but obviously, it wasn't very interesting...if it wasn't for that ice cube, I'd have slept till they came home." Then it occurred to me that Judy was home on Wednesday at 12:30 in the afternoon. "Shouldn't you be at work?" I said teasingly.

Judy was definitely dressed casually, in slim black Capri pants that hugged her hips and thighs, and showed off her still-supple calves, and a red polo shirt that flattered her flat stomach and pert breasts. It was easy to see why the other guys at school teased Matt about his mom being such a hottie. I never did, because I know how much it bothered Matt, and also how protective he was of her. Still, a big part of my adolescence was spent fantasizing about Judy's ass, Judy's breasts, Judy's lips...well, you get the idea.

Judy gave my arm a squeeze, and gave me a wink. Her long, black eyelashes fluttered, and she moved her head closer to mine. "It's such a beautiful Indian summer day today, maybe the last one of the year. I'm playing hooky," she murmured in a conspiratorial whisper. Then she raised her head again, laughed and gave her raven-black locks another shake. She sat down in the chair next to mine and gave me a pleading look.

"I need a favor, Michael. I'm supposed to be working from home today on a presentation. I just have to email it to the office, but the wifi at the house isn't working. I tried calling Matt on his cell phone, but he's probably off chasing girls instead of answering the phone." I could see a twinge of sadness in Judy's expressive eyes.

Matt was Judy's only child, and my best friend since the Martinis had moved in across the street five years ago, following Judy's divorce. Matt and I had graduated from high school the previous June. Matt had always been the better student, and he easily won a scholarship to a prestigious university which was four hours away, while I had to settle for Valley Community College here in town. Judy was obviously happy for Matt's success, but Mom, Dad and I could tell that sometimes it was hard on her to be all alone for the first time. As a result, we really did try to go out of our way for her and invite her over for dinner, to watch movies, or whatever. It wasn't forced; Matt and Judy felt like a part of our family, and I really adored Judy. Matt had also asked me to check in on his mom while he was away, and of course, I would do anything for Matt.

"Your IT support team is here," I said in an assured voice. "I'll have you up and playing hooky again in no time."

"Oh, Michael, you're the best!" Judy squeezed my arm again and gave me a big wet kiss on the cheek. "Come on over, and I'll make us some lunch." With that, she bounded out of her chair and disappeared around the corner of the house.

* * * * * * *

I came around the back of the Martini's house, past the swimming pool, and went up the steps of the patio to the sliding glass door that led to the kitchen. Inside, Judy was at the sink washing lettuce.

"Is chicken salad sandwiches OK?"

"That sounds great, Judy. Please, don't go to any bother for me," I said. I sat down at the kitchen table, admiring the profile of Judy's breasts, hips and ass as she bent over the sink. I tried not to be obvious, but she turned her head to me, catching me in full ogle. I felt myself go red in the face, and looked away in embarrassment.

"It's no bother at all," Judy replied, smiling. She didn't seem put out at all; in fact, she bent over the sink just a little deeper, slowly and carefully rinsing off each individual leaf of lettuce. As I stole another glance, I could see she was now gently swaying her hips, her flesh undulating seductively beneath the black fabric. Her pubic mound was pressed against the counter, and as she leaned forward, her breasts swelled out over the sink. She caught me looking again, and her brown eyes twinkled in acknowledgement of my attentions.

"Holy shit," I thought. "She knows I'm looking and she likes it!"

Judy flitted about the kitchen as she fixed our lunch. Taking a few steps to her right, she got up on her toes and stretched to read the top cabinet, which was beyond her reach.

"Michael, honey, I need that serving tray at the very top. Can you grab it for me?"

"Sure," I said, rising from my seat. Judy didn't budge, forcing me to reach over her. She was the picture of serenity as I nervously stretched over her, trying to take the tray without touching her. Her bottom was now only an inch or so away from my awakened loins, and I could smell her perfume and feel the warmth of her soft neck as I reached over her and brought the tray down. I could see Judy imperceptibly push her hips back into me, and my left thigh brushed her ass. She tensed as we made contact, then sighed deeply.

"Thank you, honey," Judy said, taking the tray from my unsteady hands. She loaded the tray with sandwiches, two glasses and a pitcher of iced tea. "Here, take this outside, and I'll be right down." She gave me a smile over her shoulder as she glided out of the kitchen and went upstairs.

I grabbed the tray and went poolside. The pool was the main reason Judy originally picked this house for herself and Matt; it was a beautiful in-ground job with an eight-foot deep end with a diving board. Judy said that having it made the other hassles of living in a fixer-upper bearable, and as I looked at the inviting, crystal waters, I had to agree. There was a big table under an umbrella with cushioned chairs on the right side of the patio, so I took the tray there and waited.

Judy came down after 10 minutes or so. She had changed into a white one-piece swimsuit, and wore a floral-print wrap around her bottom. She had put her hair into an updo, baring her graceful neck. The white swimsuit set off her olive skin and dark features well, and its plunging neckline afforded spectacular views of her décolletage.

"I wanted to change into my swim stuff," Judy explained. She gave me an imploring look. "You're going to stay for a swim, right?"

"Sure, but I don't want to swim in these," I replied, pointing to my cargo shorts. "I can run home and change, though."

"Don't bother, I'm sure I can find a pair of Matt's trunks in his room. Here, let's eat."

We talked as we munched on the sandwiches. Judy peppered me with questions about school and my part-time job in the local pizza parlor.

"So how do you like Valley Community College? Do you find it different than Southside High?"

"It's only been a month, but it's good so far. It's different than high school...you're more on your own, and I like that." I felt a little self-conscious as Judy kept her eyes on me, her eyes wandering over my lanky, muscular body.

"Have you found a girlfriend yet? Have your eyes on anyone?" Judy had a mischievous smile. "You can tell me, I promise I won't tell your mom."

I laughed and shook my head. "Not yet. It's a big place and I don't know a lot of people yet." I decided to tease Judy back. "How about you? Are you going to become a woman about town now that Matt's out of the house?"

Now it was Judy's turn to laugh. "I don't know. I really should...I get so lonely sometimes, but it's been so long, I think I've forgotten how to go about it. We'll see." I could see the sadness cloud her eyes again, and I felt bad about bringing it up.

"A beautiful woman like you should have no problem finding the right guy," I countered.

"You're sweet, but I'm feeling past my prime." She absentmindedly poked her fork at the potato salad on her plate.

"You're crazy. A man would be lucky to land a hottie like you." The emphatic way I said it made Judy perk up.

"A hottie?" Judy bit her lower lip and smiled. "You do know how to make a woman feel good, you snakecharmer, you." She winked at me and raised her glass of iced tea in a toast. "To our romantic success."

I clinked my glass against hers. "To our romantic success," I repeated.

The conversation paused for a moment. "Well, that was delicious," I said. "Why don't I take a look at your wifi problem, and then we can go for that swim."

* * * * * * *

I sat down in front of the PC in the family room, where the wifi router was connected. After checking the obvious stuff, it seemed that all I was going to have to do was refresh the settings and it would be up and running again. "Ten minutes of work," I thought to myself, "and I get to see Judy in a swimsuit!"

Judy came up behind my chair, and put a hand on my shoulder. "Oh my goodness," she cried. "You're so muscular now! What happened to that scrawny string bean of a kid who used to skateboard up and down the driveway?" She ran both her hands over the tops of my shoulders. "You sure you don't have a girlfriend yet?"

"I'm positive." I continued tapping at the keyboard, trying to ignore the rising lust in my shorts.

"You need to go around with your shirt off more," she said in a kidding tone. Her hands rested lightly on both shoulders now. She leaned over my right side to see what I was doing, and I could feel her breasts start to brush lightly on my back as she swayed back and forth. Through my t-shirt, I could feel her nipples stiffen as her perfume wafted over me.

"There," I said, as I became aroused and distracted at the same time. "That should do it."

"Let's see," Judy cried as she bounded to the living room, where her laptop was.

I stayed in my chair, afraid to betray the raging hard-on which her teasing had provoked. "Let me know if it's working," I called out. I rubbed my dick, trying to make my erection subside.

"Yay! My file just went through." Judy skipped back into the family room, and whipped off her wrap with a flourish, revealing her toned legs and flat stomach. "Let's go for a swim!"

Judy managed to find a pair of Matt's swim trunks for me to wear, and I went into the bathroom to get changed. Matt is a little smaller than me, and the fit would have been tight even without my still-prominent hard on. But Judy had me stirred my teenage hormones, and Dad's genes had blessed me with an abundant package. Thus, as I slipped into the Speedo trunks and looked in the mirror, I was horrified to see a bulging sausage straining the fabric, and threatening to pop out from under the bottom. I closed my eyes and thought about baseball, calculus, my grandmother, anything to make my hard-on go down.

"Hey, what are you doing in there?" Judy called. "The water is waiting."

I opened the bathroom door cautiously and stepped out. Maybe I could get in the water before she could see me. I hoped the pool would be on the cold side and I'd get some shrinkage.

I looked out the window, but saw no sign of Judy. Seeing my chance, I broke for the door and headed straight for the pool, diving in. I swam underwater for the length of the pool, then stroked on the surface on the way back. Crouching in the shallow end, I saw Judy come out from the house.

She had changed into a different swimsuit. While the white one was flattering, the one she had on now was unmistakably sexy. It was jet black, with a halter top and high cut sides that revealed at least half of each ass cheek. The front plunged almost to her belly button, while the scoop on the back was so low that I could see the top of her ass crack. Her hair was down now, and her dark curls tumbled over her shoulders in wild abandon.

"Do you like it?" she asked in a little-girl voice, spinning around as she modeled it for me. "I got it years ago, but never had the nerve to wear it in front of Matty."

"Umm...it's great," I stammered. I felt the blood rush to my groin, as my cock swelled even bigger than before. "Thank God I got to the pool before she did," I thought. I couldn't believe Judy was teasing me like this, but I couldn't take my eyes off her. She was even sexier than in my bedroom fantasies when I was 15 years old.

Judy walked up to the diving board and stepped out to the end. With perfect poise, she leapt up, jackknifed and plunged in headfirst, with barely a ripple. As she burst up from under the water, I held an imaginary scorecard over my head. "Ten-point-oh," I called out. She smiled and swam over to me.

"Am I a ten, or was it just the dive?" The water was too deep for Judy to stand, so she put a hand on each of my shoulders and clung to me. Her breasts pressed into my chest, and her mouth was poised right above mine. Instinctively, my hands went to her waist, and then wandered lower over her hips before settling on her backside. Her ass was incredible...it felt firm, like that of a much younger woman, but unlike the teenage girls I had been with till now, it felt full, like it was intended for a man to hold.

"God forgive me for what I'm about to do," I thought, as I spread my hands across her ass and pulled her into me. Judy wrapped her legs around me as I carried her to the edge of the pool. She closed her eyes as our lips met in a soft kiss, then another, then another. Her mouth opened slightly, and I felt our tongues meet in a languorous swirling dance. My cock was fully erect, and the head poked over the top of my trunks. As she let herself slide lower against my body, I could feel her pussy slide across my cockhead, and she murmured in satisfaction as she ground herself against my meat.

"Mmmm...we shouldn't do this, Michael," she sighed, while she tenderly bit me across my shoulders and up my neck.

"Christ, don't tell me she's having second thoughts now," I thought. My hormones were making me insane. Her fingers were buried in my hair now, and her hips swiveled up an down as she furiously pleasured herself against my manhood. I could feel the protruding tip of my cock disappearing into her furrow, only restrained by the sheer fabric of her swimsuit. I turned Judy around, facing the swim ladder. She grabbed the ladder with both hands and I swung in behind her, removing my trunks. I slid the length of my cock along her slit, and put my lips to her right ear.

"Let me prove to you how beautiful a woman you really are..."

Judy craned her head back, hungrily kissing me as I held her by the hips, slipping my shaft between her legs as she kept them tightly closed, the friction making her moan. Pulling the thin crotch of her swimsuit to one side, I felt her smooth pussy dance atop my cock. Judy purred, then raised her hips and spread her legs apart. As she lowered her head down, I positioned my tip outside her entrance and tightened up my hips to thrust.

"No! This is so wrong..." Judy jerked her head up, pulled her backside away from me, and shot up the swim ladder like she'd been fired from a cannon. "I'm sorry...I'm so sorry," she sobbed as she ran into the house and shut the door behind her. Through the open windows, I could hear Judy run up the stairs to her bedroom, and heard the slam of the door behind her.

Naked and ashamed, I stood quietly in the pool for a moment, with no sound but for the birds in the trees and the low hum of the pool filter. I stayed there, watching the sun glisten on the water as the ripples moved outward from the swim ladder, gently lapping against my body.

* * * * * * *

Judy and I avoided each other for the next week. My parents invited her over for dinner one night, but I made up a bullshit excuse and said I had to study at the college library. When I got home, Mom said Judy had looked terrible.

"Your father and I are going away for the day tomorrow, so we can't do anything. You should go over there and try to cheer her up," Mom told me in a concerned tone. "You're almost like a second son to her. Bring a movie over or something."

I made up another lame excuse and went upstairs to my room. I felt bad, but Judy was the one who started it. Or maybe I started by ogling her body in her kitchen that day. I stopped trying to figure it out, put my pillow over my head and tried to go to sleep.

The following day was Saturday, and Mom and Dad had left before I woke up to look at the autumn foliage, and to visit my Aunt Mary upstate. They said they'd be back on Sunday, so I had the whole day to myself. The weather was definitely getting colder now, and I thought I'd take my motorcycle out for one last ride before I had to put it away for the winter.

I was in the driveway, polishing my sportbike and getting ready to go when I saw Judy across the street. She was raking leaves, dressed in torn baggy jeans, an old sweatshirt and sneakers. Her eyes, which always seem to give her emotions away, just looked tired and sad. She looked up and saw me, and I could see that she was waiting to see whether I'd say hello, or just continue ignoring her. My head hung in shame, but I forced myself to meet her gaze.

"Hi, Mrs. Martini...I mean Judy." I walked down our driveway and crossed the street.

Judy straightened up, and gave me a weak smile.

"Hi, Michael. I haven't seen you in a while. Wait, I have something for you."

She ducked into the garage and came out with a small bag. Inside was my shorts and t-shirt from that day at the pool. I felt the blood rise in my cheeks, and I looked at my feet.

"Judy, I'm really sorry about the other day. It got way out of control..."

"I know, it's my fault..." she interrupted, her voice trailing off. She turned her head from me, and I could see the tears begin to well up in her eyes.

She started sobbing, and I couldn't think of anything else to do but put my arms around her. She buried her head in my chest and continued weeping.

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byblueplains© 12 comments/ 213592 views/ 61 favorites

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