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Copyright Oggbashan March 2016
The author asserts the moral right to be identified as the author of this work.
This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.
This story includes f/m anal.
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"Ow!" I squeaked through the inadequate cleave gag. "That hurt. Be gentle, please."
"Shut up, Harry, or I'll gag you properly. You shouldn't be a sore loser. I won the bet fair and square."
"I'll be a really sore loser if you carry on like that, Donna. I won't be able to sit down for a week. Remember, I'm an ass virgin."
Donna had tied me face down to the bed with my arms and legs spread. She was wearing a strap-on that she was trying to push into my backside. Although she had used lube, I wasn't sure I could take all she wanted to give me, even though it was her smallest strap-on.
Earlier this evening we had been watching a snooker match on television. The champion was several frames in the lead and I bet Donna that he would win.
"What are the stakes?" she asked. I should have stopped there. Donna doesn't usually bet on anything. She was sitting on the settee with my head on her lap, looking up at her breasts when I wasn't watching the snooker.
"How about we try something new together? Your choice if you win, mine if I win."
"What sort of something new?" Donna asked.
"Some new sexual activity. Just the two of us, no threesomes or going to swingers parties. Something we haven't done, that you or I would like to try."
"It's a bet, Harry. If I win, I choose. If the champion wins and you win, you choose."
The champion lost. So did I. Now I'm lashed to our bed as Donna attempts to penetrate my ass with her strap-on. I hadn't realised how painful that could be, nor how nervous I would be about it. Perhaps that was the problem. I was apprehensive and my sphincter wasn't relaxed.
Donna sighed as she pulled back. She squeezed some more lube on to her fingers and applied it gently around and inside. I could take her finger easily. Her fingers were slim and elegant with short, trimmed nails so that she could use a keyboard easily. Her strap-on dildo wasn't as thick as my penis, nor as long, but too wide for me so far.
"What do you want me to do, Harry? Rape you with a ballpoint pen? Or a slim carrot? You put far more into me. Do I object or squeal?"
It was a rhetorical question. When we made love normally she usually squealed for 'More!' and 'Harder!'. But we had been making love together for many years, and she had produced three babies. Our youngest was away for a week on a school geography trip. The other two had left home. We had the opportunity to do things together without an audience. But being fucked in the ass wasn't one of the things I had expected.