For several years after Jim's wife died he wallowed in his own misery until his three daughters convinced him to move into a retirement community with people his own age.
That led him to three high school classmates he hadn't seen in years. Anita is a hippie at heart who still smokes pot, doesn't wear panties or a bra and will sleep with almost anyone if she likes them. Janice is as fit and trim as the day she graduated from high school. She has perfect perky breasts with stiff nipples and a tight body and looks real good in spandex. Helen is the beautiful social butterfly who oozes sex with every move. She likes the leather and rubber side of sex.
After his wife died Jim didn't have an orgasm for nearly two years. He was lucky if he even got an erection. That is, until his daughters told him to get a life and started fucking him. They took turns fucking fucking their father once or twice a week. It wasn't long before he was masturbating between visits from his daughters. When he moved into the retirement community and started having sex with Anita, Janice and Helen his dick was getting hard two or three times a day. Even his morning woody's were returning.
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It was a long flight from Orlando to Seattle and they were all glad to get settled in. Their suite had two bedrooms with a king size bed in each. "Guess I'll have to share a bed with someone," Jim said.
"You can count on it," said Janice, grabbing his crotch.
Jim woke in the morning sandwiched between Helen and Anita. His morning woody's were not as "woody" as they used to be, but this morning's was hard enough to find its way between Helen's legs.
When he pulled his cock out from between her legs she stirred. He said, "Sorry, I have to pee."
"Don't go, you feel good up next to my pussy." She reached down between her legs and grabbed his penis so he wouldn't leave and sleepily mumbled, "Just pee on me. House cleaning changes the sheets every day."
When he got up to relieve the pressure in his bladder he heard Helen say, dreamily, "Oh, that feels warm." He looked down and saw a small wet spot under Helen. And it was growing larger. He wondered if she liked to pee on herself.
After emptying his bladder he saw Janice in the common area doing Yoga or Thai Chi in the buff. His dick twitched and started to stiffen again. She was facing away from him and bending over touching her head to her knees giving him a direct view of the puffiest naked camel-toe he had ever seen.
But what really caught his attention her puckered anus. It was only inches from the tip of his cock. It would be a simple thing to push it in her asshole instead of her pussy.
"You don't happen to have a condom with you, do you?" he asked Janice.
"No, but I'm way past worrying if I'll get pregnant if that's what you're worried about." Janice leaned over the back of the couch and spread her legs so Jim could get his cock up close to her pussy.
Jim didn't say anything. He just walked up behind her and stuck his forefinger in her wet pussy as far as it would go then pulled it out and pushed it in her puckered ass.
"Oh, I wasn't expecting that!" she exclaimed. But she didn't pull way. Instead she pushed back forcing Jim's finger farther up her ass.
With his forefinger buried in her ass Jim slid his hard cock into her wet pussy. He was still sliding his cock in and out of her pussy and his finger in and out of her asshole when she muffled her mouth on her forearm and climaxed. With one last thrust Jim buried his cock Janice's cunt and shot his cum as deep as he could.
They were washing up in the bathroom when Janice asked, "I guess you wanted a condom so you could fuck me in the ass?"
"I've never fucked a woman in the ass and yours was just staring at me and my cock was only inches away," Jim said. "I did my roommate in college a few times but never a woman."
