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Author's Notes

"Welcome to Side Jobs, a series about the sexual adventures of a handsome, well hung and horny part-time handyman."

Some jobs are very simple. People hire me to do them when they could easily do it themselves. Occasionally a job is just an excuse to have some company, lonely folks who want someone to share a cup of tea… or more.

This was one of those jobs…

*****

The condo complex had the visitor parking clearly marked and fortunately, there was a space open when I arrived. The building was large, at least ten stories, and the signage by the entrance displayed '55+' next to the exterior door I passed through. I typed in the number she had given, 906, and heard the loud click as the interior door unlocked.

The elevator ride was uneventful, quick and quiet with no stops, and I was quickly at her door. I knocked and the door opened, a small hand gesturing for me to enter.

“Come in, come in, young man,” the cheery voice invited.

Joan was a petite woman, very short and slender. She smiled as she looked up at me.

“Well, you are a big fellow,” she announced. “Much bigger than my Howard was.”

“Hi, Joan. I’m J.”

“Well, of course you are,” she replied with a smile. “I don’t have any other men coming over.”

She giggled at her joke and winked before going into the kitchen.

“Come, have a cup of tea and we will chat,” she invited.

I slipped off my shoes and put my tool pouch on the floor, moved to the table and sat on the chair she gestured to. She placed a cup of tea in front of me and took the seat across.

“Cream and sugar?” she asked.

“No, thank you,” I answered.

“To each his own,” she shrugged as she put a little of each in her cup. “I appreciate you coming on such short notice, especially on a Sunday.”

“Well, I had no plans and you made it sound like it required immediate attention.”

“Oh, did I?” she mused with a coy smile.

“Yes.”

“Well, it was on my mind and I wanted to call before it slipped away,” she explained.

She sipped her tea and I waited for her to continue, taking in the open-concept design of the condo and noticing the balcony overlooking the golf course beside the river.

“Nice place you have here,” I commented.

“Yes, I like it,” she replied with a smile. “After Howard passed the house was too big, so I found this place.”

“Have you been here long?”

“A few years. It’s small, but so am I,” she giggled. “It suits me well.”

“It looks fairly new and well maintained.”

“Well,” she sighed. “I should be honest with you. I don’t need anything repaired.”

“No?”

“No,” she admitted shyly before taking another sip.

We sat quietly for a moment as she chewed on her lower lip and gathered her thoughts.

“I got your number from my friend, Marilyn. You did her kitchen.”

I smiled at the mention of Marilyn.

“Well, at Bingo she was always talking about her kitchen and how much she enjoyed your company, so at church today I asked how she could afford such a renovation on her budget. She told me about your arrangement and your… equipment…”

I smiled and nodded as she continued.

“As you can see, I am a small woman. I have a very small vagina. My husband, Howard, fortunately, had a small penis, but even then intercourse was difficult and painful.”

I sipped my tea, wondering where this was headed. She put her cup down and leaned forward, resting her forearms on the table as her small hands encircled the cup.

“We did other things,” she continued. “With our mouths and hands. My favourite was to tease him while I watched him masturbate.”

Her eyes brightened and her smile widened as she continued.

“He would stroke his penis and say dirty things, and make me say dirty things while I watched. Sometimes I would tease him and please myself while he did it,” she admitted.

“Sounds like fun,” I teased.

“Well, after Marilyn told me about your penis…” her face flushed and she looked down as she paused. “I can’t stop thinking about it. I… I‘ve never seen a big penis. Just pictures and a few dirty movies. I want to watch you masturbate.”

Not what I was expecting, but I never refuse a woman’s request for my physical company.

“Sure, we can do that,” I replied with a smile.

“Oh goodie!” she exclaimed, clapping her hands quietly and jumping up from the chair.

She began pacing the room, mumbling to herself as she wrung her hands together. I stood up and removed my shirt, placing it on the chair, and put my hands on my hips.

“Where would you like to do this?” I asked.

She turned and looked at me, her eyes widened and her mouth agape. Slowly she stepped close and reached her hands out, putting them on my chest and running them over my shoulders, arms and torso.

“Oh my,” she mused. “Like the statues at the museum, all muscular and hard.”

“Thank you. I try to keep in shape.”

Her hands roamed my chest and stomach, stopping at my waist above the edge of my jeans. They were soft and warm, and her touch had its effect on my now-swelling cock. Her eyes fell to the growing bulge level with her chin.

“Oh my… oh, the bedroom. Yes, on the bed. That’s what Howard liked the best.”

I followed her to the bedroom, stopping at the foot of the bed to remove my jeans and socks as she watched intently. Her eyes widened and she smiled brightly as my hardening cock swung free.

“Oh my!” she gasped. “You are huge! Just as Marilyn described!”

I smiled and stroked myself a few times before climbing on the bed. I lay on my back and patted the bed next to me. She slowly crawled on and sat on her heels next to my hip, staring intently at my engorged cock as I stroked slowly.

“Talk to me, like you talked to Howard,” I suggested. “You can take your clothes off as well.”

“Oh, no,” she giggled. “I’m not comfortable being naked with you.”

“Up to you,” I smiled. “At least unbutton your top for me.”

She smiled coyly and slowly undid the buttons, her small breasts partly hidden under the white lacy bra underneath.

“Ooh, I feel so naughty,” she giggled.

I put my thumb and finger around the base of my cock and squeezed gently, the thick shaft and head swelling to the max as she stared at it. My other hand stroked slowly, gliding from base to tip and back again as she stared hungrily.

“You can touch it,” I assured her.

She reached out tentatively, her fingers trembling as the tips grazed the fat swollen head. Her other hand moved to the shaft, her fingers gently tracing the pulsing veins as she gently rubbed around the tip.

“It’s beautiful,” she praised quietly. “So hard, so big. Howard had a nice little penis… I liked his penis.”

She wrapped her little hands around me and slowly stroked the length of my cock, making it throb and twitch.

“This,” she announced with a smile. “This is a big cock.”

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I took my hand away and put my arms behind my head, pulling a pillow underneath as she stroked and squeezed.

“Talk to me, Joan. Like you did with Howard.”

“Your cock is huge! I never said that before!” she giggled. “I did tell Howard his cock was big sometimes, though.”

“Did he like that?”

I was hard as steel, my cock throbbing and pulsing as she expertly stroked and teased. She knew exactly where to squeeze, how hard and when to slow down. Her little hands worked my cock like an instrument that she had played numerous times.

“Oh yes,” she replied. “He liked it when I talked about big cocks.”

“Oh?” I moaned.

“Yes,” she giggled. “I would tell him about playing with big cocks while he watched.”

She suddenly moved between my legs, shrugged her shirt off and removed her bra. Her small breasts hung freely, the little strawberry nipples hard as she leaned forward and grabbed my cock again.

“He would get very excited as I described them, big fat cocks like this, while I played with him.”

I moaned as she rubbed her thumbs up and down along the underside of my shaft, just below the tip. She had a slight smile on her face as she teased one finger over the fat head, circling and twirling it while the other stroked slowly.

“We both liked it. He would get so excited when I described it, stroking and teasing another man’s big cock until it burst. I would play with him and pretend, making up stories about other men’s cocks I played with. That I stroked them hard, licked them and made them cum for me.”

Her finger swirled over the tip, picking up the liquid that was starting to seep out, and ran it over her pert nipple. She moaned quietly as she made it glisten and then repeated it with the other. My cock was aching, near the bursting point as she teased and rubbed.

“Big, thick cocks with my hands on them. Throbbing, swelling and exploding while he watched.”

She leaned forward and flicked her tongue out, lashing the underside of my shaft with sudden fury. I writhed and moaned as her tongue teased, moving around and stopping at just the right times. It swirled over the throbbing tip, licking up everything seeping out as she slowly pumped the shaft.

“Ooh, it’s time!” she exclaimed gleefully. “Your turn!”

She took her hands away and sat back as I grabbed my cock and pumped furiously.

“Oh yes, do it!” she urged excitedly.

The first spurt shot high in the air, a long, thick rope that rained down on my thigh and waist.

“Oh my!”

I pumped my fist and groaned as streams of cum splattered across my chest and stomach, little rivers of cum ending in a puddle. I squeezed my cock, milking out the last drops as the massive orgasm subsided.

“So much!” she gasped.

I let go of my cock and relaxed, watching as her fingers ran through the streams and puddles, spreading the cum across my torso.

“How did Marilyn swallow all that?” she mused as she brought her finger to her mouth and slurped off the creamy glob.

I laughed and she smiled at me.

“Just wondering,” she giggled. “There’s a lot.”

“Maybe you should try sometime?” I teased.

“Oh, no,” she giggled. “It won’t fit in my mouth!”

We laughed as her fingers ran over my cock. The gentle touch caused it to twitch and swell slightly.

“Besides,” she admitted. “I like to watch the finish.”

My cock swelled more and began hardening as she slowly teased me back to life.

“Keep that up and you can watch again,” I said with a smile.

“Really?”

“Sure, I just need a few minutes.”

I found this little lady exciting and she had given me one of the best hand jobs I have ever had. I wanted another.

“Hmm, how about a cup of tea first?”

“Why don’t you please yourself while I watch?” I suggested. “I like to watch, too.”

I stroked my cock and she watched it harden again, slowly swelling as she considered my suggestion.

“Did Howard watch you?”

She nodded slowly and smiled.

“Did you enjoy it?”

“Yes,” she admitted. “He’s the only man to see me naked, though.”

“I would like to see you naked,” I assured her. “You turn me on and get my cock hard. See?”

She eyed my hard cock as I squeezed it, the fat tip swollen and purplish again. She moved to my side, lay on her back, and slipped her slacks off. After a pause, she hooked her thumbs in the lacy white panties and pulled them off, lay back and put her hand between her legs. I got on my knees beside her, my cock dangling over her pert little tits, and stroked myself.

“Oh, Howard used to do that,” she sighed.

“You can watch me cum for you while you please yourself.”

“Oh, I would love that! Your cock is so big… so long and thick!”

I watched her fingers as they stroked the little patch of grey hair, flitting about as if playing the keys on a piano, while I pumped my cock slowly.

“Oh my, Howard would have loved to have watched this,” she giggled. “A huge cock jerking off on me…”

I slipped my hand to her thigh and moved my fingers to hers, feeling the heat and slickness of her pussy.

“Oh my…” she moaned as she took her hand away.

I played with her folds, sliding my finger up and down the juicy crevice before rubbing her little pleasure button. Her hand joined mine on my cock, stroking and squeezing while I teased her. Little moans and groans filled the room as we teased each other, and she gasped loudly when I slipped my finger inside. Her tiny pussy was tight around my finger and soaking wet. I gently fingered her for a few moments before slipping it out and rubbing her clit as she writhed and wriggled.

“Oh my, I am so close,” she panted. “Are you close?”

“Yes,” I admitted. “Cum for me, Joan. I want to watch you cum for me.”

“Oh yes, Howard!” she moaned loudly as she climaxed.

She clamped her slender thighs together as she shook, locking my hand in place as she writhed and gripped my cock tightly. Her eyes flashed open and she looked at me hungrily as she began pumping my cock rapidly.

My cock exploded, cum spraying across her chest and neck as she jerked me and I groaned loudly.

“Oh yes!” she gasped. “All over me!”

I grabbed my cock and pumped my fist furiously, squeezing out the remaining spurts and droplets onto her cum-covered tits as she grinned up at me. Her thighs relaxed and I slipped my hand out, putting it on her chest and rubbing my cum into her skin while the orgasm subsided.

“Oh my,” she sighed. “That was fun.”

“Yes, it was,” I agreed. “You are a very sexy woman, Joan.”

“Howard would call me his little slut,” she giggled.

“You are a little slut,” I replied with a smile.

“I like to pretend to be,” she admitted with a chuckle. “I guess I am one now. Howard would like that.”

“Howard was a lucky man.”

She sat up and gave me a gentle kiss before climbing off the bed, covering herself with her clothes and dashing to the washroom. I lay down and rested, my energy sapped by the two massive orgasms this little old lady had given me. She returned dressed and freshened up, a big smile on her face as she stood beside the bed and looked at me.

“So, about that cup of tea…”

Published 
Written by 1meanjean
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