Plenty O'toole Stories

63,274 results
Orientation
Length
Source
Infinite Scroll

John's First Time

by paul697 on Oct 15, 2017
First Time

This is based on part true experience this was back in 1990 my first story too so be kind. It was Johns dads 40th birthday John was dressed smart in a dark grey suit. It was a surprise party in a hired bar plenty of drink music was playing lots of family and friends. John was 19 at the time and a shy virgin. There was a family friend in attendance Denise...

Dear Dora (Pickup)

by Dear_Dora on Sep 1, 2017
Humor & Satire

Dear Dora, I work with a guy named Don. Don had to go on a two-day business trip earlier this month, and he asked me if I would mind taking his wife, Carol to and from work each day, as he would have their only car. I said I would be glad to. The first day was last Thursday. After I dropped her off at work in the morning, it started to snow, and my the tim...

My Dream Job

by slutslave201 on Sep 13, 2017
BDSM

I'd been working at dKteck for 5 years. First hired as a web designer, I'd worked my way up the ladder until I was appointed the IT director. It's a wonderful job: intellectual challenging, plenty of perks, plenty of power, plenty of cash. Even so, there was one job I truly lusted after. Though it meant significantly less money and significantly more hours (...

From Beyond

by Damon Wildeve on Dec 26, 2015
Science Fiction

Banished. Banished to the void. An instant? An eternity? Surrounded by oblivion, it's hard to tell. No frame of reference, nothing to mark the passage of time. Only the memory of your last moments in the mortal realms. You were something of a general in the Wars of Creation, a leader of your people. You kept a hundred mortal wives and sired countless magic-b...

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My New Plaything

by tzman2 on Sep 30, 2010
Cheating Spouses

You were invited to a party for a friend, at a trendy new bistro. that had opened in a major city hotel. Your wife had died about 10 months earlier you decided to go as it was a good way to start meeting new people. It was a good meal and plenty off wine was consumed, most people were quite merry. The host was someone who you wouldn't pick for a friend, she...

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Going to the Bar

by fnchristie81 on Aug 7, 2018
Loving Wives

I was enjoying a lazy day at home when my husband called me up. He asked if I was up to going out to the bar that night, and maybe spending the night. Since both of us had been working an insane amount for the last year almost, I jumped at the chance. Late in the afternoon, I started driving towards the town we were going to spend the night in. I was dress...

Team Effort

by spoonerism on Sep 13, 2017
Group Sex

Author's Notes: This is my second story. The first one was well received but got a lot of conflicting feedback (some people wanted bigger cocks, others thought it was unrealistically big, etc). I ignored most of that and just wrote a new fun story that came to me. Hopefully you'll enjoy. Sequel to "Family Friends" is also in development. It would probably...

Educating Alan

by Britease on Sep 17, 2017
Loving Wives

I should warn you that this is a short, but pretty intellectually stimulating treatise on the deep understanding that can exist between a loving couple after several years of marriage. ------------------------ "Hey Alan, can you give me a hand in the kitchen for a minute?" "Sure Mac," I replied, following him, expecting to help carry another crate of...

My Adventure As A...

by ARGEE on Sep 17, 2017
Loving Wives

My Adventure As A Public Relations Manager! When I married Mike just two years ago I thought I had really hit the jackpot! I have very good looks - I have been told by plenty of people I am beautiful but I am too modest to claim that myself! I am quite tall - 5'9" and I have a very attractive figure which is enhanced by my wonderful breasts. My tits are com...

Eighteen Ch. 01

by SelenaKing on Sep 13, 2017
First Time

I woke up horny. And for the first time in my life, that was totally okay. I wanted to lay there and enjoy the early morning sunlight. I also wanted to leap out of bed and dance around my room. I opted for a middle ground, slowly sliding the blanket off of my naked body and swinging my feet over the edge of the bed. My breath nearly caught in my throat. It...