Handyman's Perfect Timing Ch. 02

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Handyman has more sexual encounters with guests.
1.5k words
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Part 16 of the 18 part series

Updated 06/09/2023
Created 07/10/2019
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Today has been a day of perfect timing! I had sex with my bride. About an hour later I kissed and titty fucked my short, thick, incredibly top-heavy black coworker, finishing just in time to greet the next guest to our pool party. The next guest was our older, nympho-cougar, neighbor, Dorothy (with whom I've had several recent steamy sexual encounters)!

I greeted Dorothy with our standard kiss and introduced her to Naomi, who was now in the pool. Naomi offered to climb out but Dorothy told her to stay put. Dorothy then dropped her towel and swim wrap on a nearby pool chair and plunged in to the pool. Dorothy does not know a stranger. She swam over to Naomi and gave her a big hug and a kiss. Seeing their massive breasts briefly mash together was very hot!

Dorothy spun around, raised her eyebrows, and then winked directly at me. Did she find Naomi attractive? Did she get a taste of my cum from her kiss? Had she actually arrived earlier and caught us in the outdoor shower? All were intriguing scenarios to contemplate!

More neighbors and guests filed-in and the party was soon in full force. There was plenty of food, beverages, and music, and everyone seemed to be having much fun.

As the night progressed and the sun set, a few folks left but there were still many enjoying themselves. I mingled enjoying pleasant conversations, and yes, a little flirting.

I noted an empty place in the corner seat of our L-shaped outdoor couch, so I squeezed-in to join the guests there. To my right was Randi, the adorable, strawberry blonde, late 20s daughter of some neighbors who were out of town. Side note, I observed her blowing another of our neighbors in a corner of my pool house early this evening. I'm fairly sure she didnt see me. Regardless, it was hot and will undoubtedly fuel some of my future masturbation sessions!

To my left, were our friends, Gary and Nan. They were late 40s, hard working, and fun. She was sitting on his lap and her positioning gave me a delicious eyeful of her cleavage through her low cut, loose fitting top. Nan had good sized, perky, well-tanned tits. Nan was pretty well known for her flirting and flashing. She once gave me a long, full view of her perky breasts one night at another party and has, on several occasions, playfully grabbed my ass and patted my crotch. I confess, I've had many fantasies about sliding my cock into her perfect dick sucking lips!

Directly in front of me were a series of lounge chairs occupied by some guests relaxing while patiently waiting for massages from Dorothy. In addition to being a retired pharmacist, Dorothy was also a self-taught, semi-professional masseuse, which always made this matronly, minx of a MILF very popular everywhere she went. Our party was no exception.

Her previous guest had been facing me, allowing me to occasionally catch glimpses of her heaving breasts as Dorothy worked her magic. Next-up was my busty coworker, Naomi, whom elected to face the opposite way. From where I was seated, I had an excellent view of her parted legs. I soon saw a wet spot forming between Naomi's legs and I'm fairly sure I may have heard the muffled sounds of her stifling a small orgasm as Dorothy expertly massaged her. When finished, Naomi came over to hug and kiss me explaining she had to go back home. I enjoyed her pillowy breasts inches from my face. I asked if she was glad she came? She said she was and then leaned-in to whisper she actually came twice! I gave her a knowing wink and said that she's welcome to cum more often!

When Naomi left, Randi popped-up announcing she was going to get another drink. I told her to get one for me as well and gave her a playful pat on the ass as she walked away. Oblivious to all of us, Gary and Nan began making out. Affection is always welcomed and encouraged at our home. This corner was fairly dark and more private. My position allowed me to observe Gary slipping his hand inside Nan's top to cup her full breasts. I tried to be subtle as I observed their intimate affections. The spot to my right was soon filled by two bisexual neighbor women who also decided the dark corner provided an excellent place to make out. I was getting quite aroused. One of those women, Tari stealthily traipsed her hand along my thigh, eventually grasping and groping my growing cock through my swim trunks.

While sandwiched between the frolicking foursome, I observed that Dorothy's next recipient of next her massage was none other than my buxom bride, who appeared to be rather drunk.

Randi returned with drinks. After realizing she had lost her seat, Randi just squirmed her taut, round bottom onto my crotch as she climbed up to sit on my lap. I was already semi-hard from Tari's tawdry touches so, it did not take long before this nubile, young hottie had me hard as a brick. Randi slowly squirmed and adjusted herself explaining she was just trying to get comfortable, though I'm quite certain she was, in fact, slowly dry humping herself to a small orgasm. Since the surrounding couples paid us no mind, I decided to follow suit by assertively grabbing a handful of Randi's perky tits with one hand while I deftly snaked my other hand into the top of her small bikini bottoms. She responded instantly to my mature hands.

She buried her face into my neck as her breathing grew more ragged. She was sopping wet as I enthusiastically frigged her clit. I couldn't fuck her from where I sat, but I successfully gifted her with several juicy orgasms.

My pleasure was fueled by my unibstructed view of Dorothy's subtle but sensuously massage of my bride. Her tantalizing touches of my wife's upper and inner thighs eventually produced a large wet spot around her crotch and the unmistakable small shaking of a series of orgasms. That truly appealed to the voyuer in me and was incredibly hot!

After a while, I excused myself to use the restroom. Dorothy grabbed me as I passed by and whispered she could use my help pouring my bride into bed as she was nearly asleep (presumably from the booze and the sweet orgasm she just had). I readily agreed. Dorothy helped me walk her to the master bedroom, strip her of her swimsuit, and dress her in a fresh set of panties and night shirt. I fetched her standard night time medicines, sleeping pill, and added some Tylenol for good measure. Once my bride was down and tucked in, she sleeps hard for the remainder of the night. Dorothy sat along side her, gently carressing her temples, scalp, and neck until she was fast asleep. To my joy and arousal, Dorothy then leaned in to kiss her lips before gradually planting a series of light kisses trailing down her neck and upper chest. My bride never stirred so Dorothy slowly raised her night shirt up to pepper her large breasts and nipples with several light, passionate kisses before lowering her shirt and pulling the covers lovingly up around her neck. My bride never flinched so I knew it'd be fine to rejoin the party.

As we closed the bedroom door behind us, I gave Dorothy a deep kiss and grabbed one of her huge breasts with one hand while finding her pussy with the other. I fingered her pressing her against the hallway wall to two gushing orgasms. I find it so exhilarating that Dorothy is a gusher! I began to lower my trunks to fuck her right there but she whispered a stern, "no"! She kissed me and seductively whispered she had a present for me in the garage.

I kissed her back and then made my way to the garage where, there to my surprise, stood Nan and young Randi making out and fondling each other. "Perfect timing, you got the message", Randi cooed! I had seen Dorothy, Randi, and Nan chatting earlier, and figured they were up to something naughty, but truly had no idea it'd be this!

Dorothy snuck in behind me and all three sexy ladies whisked me into my nearby workshop, closing the door behind us. Once inside, Randi and Nan dropped to their knees side by side, yanked down my trunks and tag-teamed blowing my thick cock. Dorothy stood in front of us, filming us with her smart phone. When I announced I was going to cum, Randi enthusiastically jerked me off onto Nan's large, waiting tits. When I finally finished erupting, Nan leaned in and sucked me clean while Randi kissed and licked her tits clean of my cum. We had just finished adjusting our clothing when Nan's husband Gary walked in.

"Perfect timing", I told him with a smile. "The ladies were just helping me grab more hard stuff for our guests", I said pointing to a few cases of liquor on my bench!

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1 Comments
fishgetterfishgetterabout 2 years ago

A hurry up story. Could have been a good one, but.......

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