Category: Mature Stories

A Handyman's Memoir Ch. 20

by riverboy©

"Oh, you are handsome!" a woman's voice said from the sidewalk as I was stowing away tools in my truck.

I had just finished a job at another of the 'big money' houses a few blocks from Lindsey's place.

"So how old of a woman do you service?" she asked.

She was silver haired, walking a small dog, and looking at me with that 'I hope he likes me' look you usually see on a teenager. I'd guess she was around sixty, and very attractive.

"I have customers of all ages," I said with a little smirk. "Do you have something that needs working on?" I asked, playing her little game.

"My name's Connie. I'm Barb's neighbor," she said, extending a hand laden with rings.

"I'm Steve. Pleasure to meet you Connie. Always nice to meet a friend of a friend. Barb's a sweetheart," I said.

"She speaks very highly of you too Steve. You seem to have helped her, ah, over a hump, so to speak. She has a nice new gentleman friend, the first in many years. She's had quite a re-awakening, judging from the noises coming from her bedroom window," Connie said with a sly smile.

"Well good for her. I was wondering why she hadn't called me lately. Perhaps he's good with the tools?" I said, playing the role of the witty sophisticate.

"Yes," she said with a smile, "but I doubt he works to your high standards. I've heard you're very highly skilled. I'm wondering though — do you mind working on older places that need some . . . rejuvenation?"

"Mind? Heck no," I said, looking Connie over from head to toe. "I've got the afternoon free if you'd like me to take a look at it."

"Well! This is exciting! I'd like a complete renovation please!" she said with a delightful laugh.

"That may take some time," I said with a wink.

"I'm well past the hot flash age," she said as she fanned her face, "but . . .wow, that was a doozie!" After a moment she added, "I should have listened to Barb and called you weeks ago."

"Would you like a ride, or shall I meet you there?" I asked.

"No, I'll walk. I've got Inky," she said, referring to the little black dog. "I'll meet you there in ten minutes. I'm right next to Barb, with the green door."

"You know there's a classic x-rated movie called 'Behind The Green Door.' Pretty hot stuff," I said.

"Whoa! Another hot flash," she said quietly, tugging the front of her blouse out repeatedly to pump cooling air under it. "Behind The Green Door huh?" she said, looking me in the eye and laughing a little. She shook her head and said, "And I thought Barb was exaggerating your seductive charms..."

Connie walked off down the street with Inky. She was wearing an expensive looking waist length black leather jacket and a pair of well-tailored blue jeans that showed off a lower body that looked much younger than her years. Her haircut continued the youthful illusion — it was very short and highly styled. 'Give me the Jamie Lee Curtis,' I could imagine her saying as she walked into the salon. She even had a youthful wiggle in her walk as she made her way down the sidewalk — if it wasn't for the silver hair you'd never guess her age from behind.

I sat in my truck for a few minutes checking messages on my phone and contemplating Connie. If my guess of her age was correct she would be the oldest woman I had been with, assuming I was going to 'be with' her, of course. I was thirty, and this new line of work I was in had led me into the beds of some wonderful older women, something that I hadn't experienced before. My life was better for it, that was for sure. I started my truck and headed over to see what was behind Connie's green door.


Connie's house was typical of the neighborhood—huge and expensive, with a stone facade, perfectly manicured landscaping, and a big circular driveway that led to a three car garage with climbing roses on the front of it. A classy place for sure.

"Welcome Steve," Connie said from the front steps as I walked up. "I hope you haven't had second thoughts and decided you'd rather work on something that isn't this old."

"Not at all," I said. "By the time I'd watched you walk down the street I knew I was very interested in the working with you."

"Okay then," she said, smiling and eyes twinkling, and she pumped on her blouse again to cool another flush of heat from her body.

"It's a beautiful home. Have you lived here long?" I asked as we walked inside.

"Yes, my husband and I were among the first in the neighborhood," she said. "We moved in thirty years ago. I'm afraid it's gotten a bit run-down though. My husband suffered from a long illness—I cared for him for almost ten years—and very little got done on the house in that time. He's been gone now for three years, and I think I finally have my head on straight again. Time to spruce up and take another stab at life."

"Good for you Connie," I said. "I can tell by those sparkling eyes of yours you won't have any trouble with that."

"Now I know why all the women fall for you," she said softly, shaking her head. "So, let me show you around and we'll see what projects we can find for you. I can probably keep you busy all winter."

After a tour of the big house we decided I'd start on the screened porch, before the weather got too much colder. A thorough paint job and a new ceiling fan would take care of things out there, and have it ready for spring when it rolled around. Connie helped me move the furniture into the house and I started right in on the scraping and sanding, prepping the space for a nice paint job.

"Tomorrow morning we can go to the home center and pick out some paint," I said when Connie came in to have a look at the progress.

"Oh, this is exciting. I never dreamed this would be happening when I woke up this morning," she said with a big smile. "Can you stay for a light supper Steve? I'd love to have some company."

"I'd love to Connie. I didn't bring any clean clothes with me though," I said.

"Oh, you won't be needing those," she said, and then she blushed bright red, looking shocked at what she had said. "I mean . . . we're . . . we're casual around here." She turned and left in a hurry, clearly embarrassed, and I smiled to myself, thinking how cute she was.

A little later, when I had finished for the day, I followed my nose into the kitchen. Connie, freshly showered and dressed in a form-fitting casual dress, was stirring a ridiculously great smelling pasta sauce, made with tomatoes, garlic, wine, olives, capers and anchovies.

"Wow! I don't know if I've ever smelled anything this wonderful," I said. I walked up behind her and barely brushed my lips against her neck, inhaling her perfume. "Intoxicating."

She dropped the spoon in the pan and turned to me. "Oh Steve, it's been so long since I've felt a man's touch. I may not survive this."

She tipped her head back and our lips met, softly and tenderly. She moaned quietly as our mouths opened, and the tips of our tongues barely touched.

"I hope you don't mind if I drink some wine. I'm nervous as hell," she said as our first kiss ended and I held her in my arms. I could feel her trembling a little. "I was thinking about it when I was in the shower—it's been fifteen years..."

"We can slow down Connie. Get to know each other better," I said.

"No . . . I want you . . . tonight if you'll have me," she said with a hopeful look in her eyes. "I'm worried though—I have no idea if I have anything left to give."

"Well if that first kiss was any indication," I said, "it's gonna to be a magical evening."

"God Lord, where did you come from," she said, smiling and shaking her head.

We ate her fabulous pasta and a salad, drank more than enough wine to relax her, and she led me upstairs.

"After my husband passed I had this room fixed up and moved in here," she said as we entered her bedroom. "I needed a fresh start." The room was light yellow, with big windows overlooking the backyard gardens.

"It suits you—cheerful and bright and beautiful," I said.

"I've laid here many a night wondering if I'd ever have a man in here to help me christen the new room. I guess it's not so new anymore..." she said.

"Better late than never. I'm honored to be the one to christen it with you. Would you like me to splash my fluids over your bow?" I said with a wink.

She looked shocked for a second, and then burst into laughter. Suddenly the laughter stopped and she threw herself into my arms and we kissed hard, the floodgates of passion opened wide. I unzipped the back of her dress as we kissed, and her hand found the swelling crotch of my jeans. I quickly shed my t-shirt, and she moaned as her hands moved over the muscles of my stomach and chest. I pulled her dress forward over her shoulders, and she let it drop to the floor revealing a lovely matched set of lingerie—black and lacy, small and sheer. Not exactly what you'd expect on a woman of her age, but oh my, did it ever look good on her well kept figure.

"Wow!" I said, much to her delight.

She unzipped my jeans and pulled them down, ending up in a kneeling position in front of me.

"Oh my!" she said as she saw my eight inch erection through my tight boxer-briefs. She ran her hands over the thin fabric and moaned. Then she pealed my briefs down slowly, revealing me inch by inch, until I sprung up and nearly hit her in the face. "Okay, now it's my turn to say wow," she said quietly, with her eyes locked on my throbbing cock. "I think I may have gotten in over my head here," she said, looking up at me a bit apprehensively.

"That's just the way Barb felt Connie," I said, pulling her up on her feet and embracing her. "Don't worry, we'll take things at your pace."

"I've never done anything . . . oral," she said tentatively. "I'm rather old fashioned I guess."

"Did your husband ever pleasure you that way?" I asked.

"No, never," she said.

"Well I'd like to, if it's all right with you," I said quietly in her ear.

"Yes," she said even quieter.

I reached behind her and unclasped her pretty bra and ran my hands around her sides, palming her tits. "Oh Steve!" she whispered. Her breathing was getting short and ragged. I slipped the straps from her shoulders and she shrugged it off and let it drop to the floor.

"You look beautiful Connie," I said as I kissed my way down the center of her chest. Her tits were quite lovely, full and surprisingly firm, with lovely dark nipples that were hard and sensitive. She let out a long, deep moan when I sucked one into my mouth and tongued it against my teeth.

I continued kissing my way down her stomach until I was on my knees. I slowly pulled down her lacy panties revealing a wispy grey bush around her pussy, the first I had seen with grey hair.

"How beautiful!" I said, looking up at her. "I love it when the carpet matches the drapes." She laughed and all the tension seemed to drain out of her.

"Just kiss it you fool!" she said through her laughter. "I'm dying to know what it feels like."

I dove in and sent my tongue as deep into her as I could, and then licked up through her folds to her clit.

"Oh God in heaven!" she exclaimed softly, and her knees went weak. I supported her with my hands under her ass and gave her my best tongue lashing. She didn't speak again, just moans and chirps and much ragged heavy breathing.

"I need you inside me," she finally managed to say, and she pulled me up. I kissed her and let her taste herself, and she hugged me tight, her tongue trying to snake down my throat.

Connie reclined on the bed and I quickly shed my shoes and kicked off my jeans.

"On your back young man," she said forcefully. She straddled me and didn't waste any time lining me up and taking the first inch or two.

"This may not be easy," she said. "I've got an ancient tube of lube if we need it. How did Barb do with this monster of yours?" She gasped as she took another inch.

"She was a bit overwhelmed, but she loved the end result. So did I," I said. "God you feel good Connie."

"Oh Fuck!" she said, halfway on with four inches to go. She leaned forward and started rocking back onto me, fucking the first half of me. Gradually I started to fill her—a half inch, then a half inch more, until she slowed and sat up, and with a big moan realized I was all the way in. Her hands went to her crotch and she started slowly grinding her hips fore and aft. "Oh my God!" she said as her head tipped back, and a guttural scream that sound like it came all the way through her from her toes bounced off the ceiling into my ears. She was grinding hard on me, like a woman possessed, and her head flipped forward, staring me in the eye with a piercing gaze. "Fuck me Steve! Fuck me!" she groaned in a deep voice.

She leaned forward and lifted her hips and I started thrusting up into her.

"Harder! Oh fuck me god damn it!" she groaned.

I gave it all I had, and she took it with great loud groans and moans. Just about the time I was going to have to back down and re-group she came with a shudder, her head thrown back, and she screamed a series of wordless sounds at the ceiling. I was slowing down, nearly spent of all my energy but still thrusting up into her, when she collapsed onto my chest. If she wasn't breathing so hard I would have thought she was dead, she collapsed so totally and completely. Like a rag doll she lay on me, gasping for breath.

"Are you okay sweetheart?" I asked softly.

"Better than okay," she whispered, barely able to get the words out.

Connie didn't move a muscle for many minutes, and as her breathing slowed to normal she seemed to fall asleep on top of me. My cock was still mostly hard and deep inside her. After a few minutes she woke.

"So it wasn't a dream," she said as she turned her head to look at me.

"It felt like one, didn't it?" I said. "You're quite a woman Connie."

"You're still inside me?" she asked, sounding surprised. "You didn't . . . finish?"

"No. There's plenty of time for that. We're far from done," I said.

"Are you serious?" she said. "You could put an old lady in the hospital you know."

"Not you sweetheart, you're built for this," I said.

"Ha! You think so huh?" she said. "Let's see, my husband, who I loved dearly, had a tiny little penis, lasted about two minutes in missionary position, I've never been with anybody else, never had or given oral sex . . . I could go on."

"You've got the body of a forty-year old—and a sexy one at that, your ass wiggles beautifully when you walk, you love receiving oral sex, you clearly love to fuck and you have amazing, beautiful orgasms . . . I could go on," I said with a smirk.

Her warm, luscious pussy was keeping me mostly hard and I gave her a thrust that took her breath away just as she was about to answer me. She giggled.

"I guess you've made your po...oint," as I bottomed out in her again. "God that thing is huge. I feel like my whole gut is full of you." She paused and moaned a few times. "So, I don't want this to sound to clinical," she said, "but I'm kind of fascinated by the oral thing. Do you think I could try it?"

"Do I think you could try it?" I laughed. "That is a bit clinical. Try saying it this way—I want your cock in my mouth Steve, and I want you to cum on my tits."

Her eyes got big and darted back and forth between mine, and her mouth curled up seductively. "I want your cock in my mouth Steve . . . and I want you to . . . cum on my tits." She looked shocked and amazed and thrilled at the words that came out of her mouth.

"No man could resist that look on your face Connie," I said, and I kissed her as I slid my cock out of her wonderful feeling pussy.

"Oh . . . my!" she whispered as I slipped out.

"Would you like me to wash it clean for you?" I asked.

"That's not the normal way is it?" she asked. "I mean that would sort of break the flow of things, wouldn't it?"

"I thought maybe for your first time, you might enjoy it more," I said. "But yeah, usually it's a little more down and dirty. I woman tasting herself on a hard cock can be a big turn on."

Connie's breathing started to get short and ragged again, and I could feel her heart pump faster against my chest. "Oh my, this is an education, isn't it!" she exclaimed quietly.

She pushed herself up off my chest and onto her knees between my legs. She wrapped her hand around the base of my sticky cock, lowered her head, and took the swollen purple tip into her mouth. She held on tight and licked the four or five inches protruding from her hand like a popsicle.

"I've always wondered what it felt like to be a dirty girl," she said between breathy moans, her nostrils flaring as carnal lust overtook her.

"Help me," she grunted out lustily between licks. "Tell me what to do."

I wanted to be able to 'splash my fluids on her bow', so I got up and stood and Connie sat on the side of the bed. I showed her how to take me in her mouth and stroke me at the same time, and she took to it like a natural. She clearly enjoyed it, and when I started gently thrusting into her mouth her moaning increased to a fever pitch, as did mine.

"Oh Connie!" I said, and I grabbed my cock just in the nick of time and splashed hot cum on her neck and chest, the last spurt a bullseye on one of her dark nipples.

"Oh my God!" she exclaimed in a near whisper.

I moved closer to her and she took me back into her mouth and ravenously sucked me clean.

"God Connie! You're a natural!" I said as I regained my breath. She finally slowed and then stopped her hungry sucking, let my cock slip from her mouth, and looked up into my eyes. Semen was running down her heaving chest, and dripping off her tit onto her thigh.

"You're well and truly christened now sweetheart," I said.


Connie wasn't kidding when she said she wanted a complete renovation — she kept me busy all winter working on her big house, and we whipped it into shape room by room. Lot's of painting, floor re-finishing, and new light fixtures. Two bathroom re-models, new kitchen cabinets — lots of good work that made my meager bank account swell nicely.

As for Connie's personal rejuvenation, she became a wonderfully sexual person for the first time in her life. She kept the local Victoria's Secret store in business virtually single-handedly with all her lingerie purchases, she took up yoga, and she even bought a Kama Sutra book of sexual positions that we had lots of fun with. I was a little worried though—she had gotten very attached to me, and she never spoke of any men in her life, even though she often went out in the evening to charity events and concerts with her friends. I finally told her about my concerns.

"Oh, don't worry about me," she said. "I've got my eye on a few men. When the house is done and you're not around so much . . . I'll be fine don't worry. I'm planning on fucking their brains out—they won't know what hit them," she laughed. "For the time being I'm going to enjoy you to the fullest. You're sweet to worry about me," she said, and she kissed me. Her eyes misted up with tears. "Do you have any idea how much you've changed my life?" she said.


One beautiful winter morning Connie stopped me as I was bringing my tools in from the truck. We were in the middle of a warm 'January thaw' and the sun was shining brightly. "No work today," she said. "Let's go for a drive—I want to show you something."

Connie drove us away from the city in her car. "I never told you about my husband John's fishing, did I? It was his favorite thing to do, the only thing that got his mind off his big business worries. I swear the stress from running that company is what killed him..." she said, with a sad shake of the head. "I finally persuaded him to buy a small place on the water, not far from home. Something he could get to easily in the evenings if he wanted too."

She turned down a long dirt driveway that was badly overgrown. Halfway down I had to get out and pull away a large branch that had fallen. It looked like it had been there for a long time.

Category: Mature Stories