Happy Trails

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Dave finds a happy ending on the trail around his home.
1.9k words
4.35
19.7k
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Part 1 of the 8 part series

Updated 06/10/2023
Created 05/01/2020
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I was getting about completely sick and tired of hearing about this virus all the time and the mass hysteria brought on by it. My sister, an RN, who worked at the local hospital had clued me in on some facts I was not seeing anywhere on the news, Facebook, and Twitter... Aptly named since it's full of twits... Anyways, I was an essential worker so I went to work, in the enforcement industry, just the same as I did every day. Problem is Sarah, my girlfriend of three years, was trapped in Tampa, Florida with her parents.

Sarah had gone to help her mother due to Judy; her mom's sister being killed in a car accident. Sarah helped her mother through the tough times, funeral arrangements, and much more since Kathy had been named executor of the will.

So almost two whole months without Sarah was taking its toll on my balls. Sarah was a sexual dynamo and kept me on the verge of wore out daily. With the possibility of having to fly back with 'sick' passengers and her job not working during the current state of things it was my idea she stay. Regardless of how blown out of proportion things were I did not want to risk her possible safety.

We talked pretty much every other day after I got home from work, Sarah had suggested phone sex. While it was nice it still was not the same. Jerking off maybe for some people is awesome but I never felt like I got it all out when I jerked, even with Sarah coaxing me on the other end.

Tonight when we talked Sarah suggested something different. "Walk the trails around the neighborhood late and jerk off at one of the benches Dave."

"Have you lost your mind? I could get arrested."

Laughing, "No you won't, there only adults in our neighborhood. Besides, go about eleven tonight, you know we never see anybody on the trails late babe."

Sarah was right, we had had sex on the trial a couple of times due to her being a little bit of an exhibitionist. "Still though," I argued.

"Oh god do it Mister Scary Cat," she said with a giggle.

"Maybe."

She fake sighed, "Too bad you aren't here we could do something really freaky."

I have no clue why it came out of my mouth but the instant it came out I felt the gates of hell ready to be unleashed by her on my. "Like your mom?"

No, I did not really mean do her mom, although she was a babe at fifty-one, I meant it as a joke. Like Yo Mama is...

Kathy was twenty-one years older than Sarah and twenty years older than me. Kathy, a platinum blond, had that trim waist and round ass like Sarah. Both just over five feet tall. Where Kathy had the upper hand on Sarah was the tits department. Sarah sported nice firm B-cups still at thirty, they were close to a C, but mom had to have D's or better.

Sarah was silent a second, me still trying to formulate how to explain it was a joke. "Well maybe next time she visits, I know she makes you hard."

"Babe it was a joke. I meant like yo mama."

"Mom knows you got a big cock," she ignored my attempt to explain, "and she knows you fuck like a beast. So does Mellissa."

Melissa is her twenty-seven-year-old younger sister who lives in Louisiana. "How the fuck!? They what? Sarah it was a joke."

"Sure babe," she said in a teasing voice.

I will not lie her sure babe made me rock hard. "Maybe someone wants me to fuck their mom... Or watch me fuck their mom."

That bedroom giggle she had that drove me crazy proceeded a, "Maybe."

I heard someone in the background, "Huh? Ok dad. Gotta go babe, time for dinner. Love you!"

"Uh... Love you to Sarah, be safe."

"I will babe, you to. Muah," and she hung up.

Great now I had a raging boner over my girlfriends mom. It wasn't the first time, but fuck it was hard as Chinese Algebra.

I had ordered sushi delivery and the doorbell was dinging. I was met on the other side of the door by cutest little Asian chic delivering it. I tipped her extra because she was cute, I have a thing for short women, and I saw her notice my erection straining at my jeans and turned red.

I found an old movie I liked on T.V. and unwrapped my bounty delivered by the little Asian goddess, hoping to forget my need to bust a nut and my throbbing go down. Food and a good movie had made me basically forget about being horny, but Sarah decided to remind me with a text.

"Mom says next time she visits."

I sat staring at my phone, surely Sarah was just fucking with me. I mean she could not possibly want me to fuck her mom. Could she? I mean Kathy was hot, that's where Sarah got all her incredible looks. Great now I was throbbing hard again and debating what to even say.

Finally I managed, "Sure babe whatever you say."

No reply, fuck I was... I was gonna do what she said. Why not? It was just after ten and people were never out anyway, surely, they would not be now. I stripped down and threw on a pair of loose shorts, baggy tee-shirt and running shoes.

Still raging hard I decided to give Sarah a bit of her own medicine before I went and tried to jerk off on the trail. I bet the excitement of being out there would make my cum harder. I sat on the couch flopping my hard cock out and snapped a picture of it.

I sent it to Sarah, "Tell mom I said hi."

I was laughing to myself stroking my pole, I realized it was harder that ever. Just the thought of something that would never happen had my cock slit oozing as I played with my cock. I had about given up or her answering when my phone beep again.

"That is a really big cock David. Sarah says next time you can send it to me directly instead."

That text nearly made my balls explode as I read what Sarah's mom had just text. Fucking A for real she showed Kathy.

I was still sitting stunned when Sarah chimed in. "I told you mom. Now I know you are hard as fuck, go do what I told you and jerk it off. Think of us when you do."

Fuck it was a group text!

Cat must have his tongue," Kathy added.

"Go babe, cum hard for us."

"Imagine cumming on my big soft tits David."

Then they stopped. My balls were aching, fuck heading to the trail. In just a few strokes later I was unloading sitting on the couch. They had my blowing cum, I felt like I had not cum that hard in years. Cum ended up on the, floor and coffee table.

Me walking around the house, cock over the band of my shorts headed to get paper towels and cleaner. Shit that was hot and I was still frigging hard.

Deciding they were not playing I jumped into the text. "You two made a great big mess."

"Oh babe that's hot."

"Really hot," Kathy added, "was it on my tits?"

I decided to wade deeper to see how serious they were, "Yes."

"Oh my god yes," Kathy sent back, "Hopefully soon."

"Mmmm babe, soon as we can," Sarah added. "Now go rest love. Night".

"Night Sexy Ladies."

"Night Handsome," Kathy sent.

I could not rest I was still hard as hell. I sat playing my still ridged cock, the trial I thought, let's give it a try so I headed out.

I found a nice quite stop, a spot Sara and I had fucked at a few times. Satisfied nobody was around I pulled my cock over the waistband and started to stroke. My mind drifted to the thought of watching my girlfriend and her mother suck my cock. I was going to enjoy this. I'd got so wrapped up in the fantasy I never heard anyone approach, till I heard a voice behind me next to my ear.

"Don't move," came whispered from a female vice behind me.

I jerked up right as an arm came over my shoulder. "I said don't move, let me."

"What?"

"Let me relieve it for you," she whispered in my ear.

I started to move, "Don't look at me. Just let me play with it."

I noticed the left hand reaching over my shoulder was a woman's. Painted nails and a wedding ring.

"But" I tried.

"If you look, I won't finish him off. Here let's do this," she said and stretched one of the mask everyone seemed to be wearing over my eyes.

I felt her sit beside me her hand wrapping almost around my cock. "Big," she whispered and started stoking me. Now both hands on it as she leaned across my lap stoking my aching cock.

"Mmmm," she'd moan now and then, and she worked it with both hands.

It was sweet bliss. She was no stranger to jerking a cock for sure. I wanted so bad to shove her face toward it, but I was afraid she'd stop. I was building another blow; her soft cool hands had become warm on my cock. The night breeze still cool in April blowing across my balls making them tighten even more.

"Fuck, I'm gonna," I moaned warning her.

Another, "Mmmm," from her and a few stokes later I was cumming. She'd pointed my cock straight up. I heard her laugh as I fired up a couple of ropes and felt it landing my me. Her hands became slippery coated with my cum as she continued her jerking.

Her slippery hand twirling on my swollen cock head. That tickling sensation that drives you insane with pleasure, then she popped just the head in her mouth, sucked and swirled her tongue till the head was clean. Tucking it back in my shorts I heard a small giggle.

I was literally panting from what this unknown woman had done to my cock. I knew then and there it was the best orgasm I had ever had in my life.

Her lips were at my ear, "leave the mask on and count to thirty. No peeking. If you are good and don't peek you can meet me here tomorrow at 10:15 P.M. and I will do it again. No need for you to be so hard all alone with Sarah gone."

I swallowed hard, "Sarah."

"Uh-huh. I won't tell if you won't. See you tomorrow and no peeking."

I heard her shoes on the paved trail, it sounded as if she was jogging. I did not count but I waited a few seconds after I quit hearing her.

Holy shit I was done for. Some random woman that knew Sarah had just jerked me off on the trail. Had Sarah set me up for this? No this woman said she would not tell Sarah. I did not recognize her voice, but then again it had been a whisper and all sexy sounding. I doubted that she sounded like that normally. Shit she's married; I remembered the ring. Great a neighbor I do not know, who is married just jerked me off on the trail and my girlfriend doesn't know.

I was not sure if Sarah and her mom were just teasing, maybe they had been drinking but I sure as hell wasn't telling her this. Nor was I coming back out here on the trail... Maybe.

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  • COMMENTS
6 Comments
WretchedMonkeyWretchedMonkeyover 2 years ago

It was okay but I'm wondering why it's in the romance category and even has romance as a tag.

OvercriticalOvercriticalalmost 4 years ago
Not Bad...

A pretty good start to something - hard to tell where it's going. Worth a 4* right now. I do wish writers would spend a few minutes proof reading their product. Two glaring errors: trial instead of trail and quite instead of quiet. Spell check isn't enough.

AnonymousAnonymousalmost 4 years ago
My 2 cents

Hmmm. No romance as of yet. I think this is part of the build up. I'm partly confused as he has a great girlfriend and the real possibility of fucking her mother. He is looking for a romance? I guess the dick has no conscience. I look forward to seeing where you go with this. Will this new woman take the place of his girlfriend or is this just mindless sex with a stranger. Thanks for your time and imagination.

KottonKhandieKottonKhandiealmost 4 years ago
Hot

Men and my husband have done that around where we live. May do it tonight. :)

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