Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here
When he stirred and said 'good morning' I felt like I had waited a lifetime and so my response was not exactly typical.
"I want you to fuck my ass. I mean, if you want to... if you'd like that I..."
He did. He wanted to. He liked it. A girl can sense these things when a man is cumming in her ass.
He was amazing, truly, teasing me with his mouth, forcing his tongue inside me, helping me along with warm and wet fingers. As he gently filled my ass with his hard cock, my hand drifted to my sopping wet pussy and I came instantly. We both groaned in pain as my clenching naughtyhole squeezed him almost too tightly.
I was able to relax as he settled into a gentle rocking rhythm. Soon I felt so open and full of cock that my second orgasm must have been more comfortable for him because when I clenched he moaned, growled actually, and pumped his load into my most forbidden fuckhole.
Anal is a rare urge for me but Jack was special. The moment it occured to me that anal sex would probably be a unique slice of 'life after Caroline' for my darling Jack was the moment I began to want him in my ass.
There was no awkwardness afterwards but after a night and a morning like that it seemed OK that separate showers felt right to both if us. As we dressed and drank a ridiculous amount of water, Jack asked the important question. It was important because I needed him to hear the answer.
"So... Katy... what happens now?"
I was more than a bit nervous but my darling Jack had not been rescued yet. I knew he needed more than Bliss could give him and I prayed my terms for the future of our relationship would be accepted.
I told him I wanted him to get out of his house, out from under the dark cloud he'd become so used to, and meet the world head-on, meet women, and date. I told him that I thought a fuckbuddy that looked exactly like Caroline was probably the last thing he needed.
I kissed his cheek I hugged as tightly as I could.
I told him that I'd meet him in the bar in exactly 364 days. If he could honestly say he had done what I had asked and was still single then we would use the reservation for two I had already made. I told him the truth. I had already made our reservations, one night a year, every year, and that I would only cancel them after he had found someone else. This one night a year would be my gift to him until he found a living and breathing reason to back out in me.
He nodded and took a moment, letting the full meaning of my terms sink in. Then he smiled and kissed my forehead. That last hug wasn't a sexy one but there was love in it, fondness and caring, gratitude and concern. The kind of feelings people have when they can truly see eachother.
We used the reservations three times and each evening was unique and incredible in it's own way. Jack is a bit of a perv now, actually, but it isn't entirely his fault.
He wants to bring his new friend here so I can meet her : ). We agreed that the anniversary of his first marriage (and our adventures together) wouldn't be the right time so earlier today I cancelled our reservation for next Saturday night and like I said...
...I couldn't be happier!
I'm in love with how antsy I get writing in this journal but it fucks with my plans. I was going to go to the gym but now I have to spend some quality time with Little Jack and his friends. All of my toys have names but Little Jack is the only butt plug I own ; )
