This is a story originally posted by captjim51. It has been edited for grammar and typographical errors. If anyone feels that this story has been posted in error or misattributed, please contact me.
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Superbowl Anal Bet
Let’s just start by saying my wife, Linda, had a very busy Sunday night. Yes, she’s a Broncos fan, and made a bet with me. It wasn’t for money. You see, my little 5 feet 2 inch petite doll has the nicest ass I’ve ever seen. I love sliding my eight inches between her ass-crack. The trouble is, she only takes it up the ass about once a year. The rest of the time it’s straight vaginal sex with some fairly good blow jobs thrown in. So, our Super Bowl bet was unique, whoever’s team was ahead at half time got to pick our private half time entertainment. Linda knew that if the Broncos were behind at halftime she was in for an ass fucking.
Well, we all know what happened last Sunday night. At the two minute warning Linda went to her room and came out in her Bronco’s T shirt and nothing else!!! The jersey revealed just the bottom of her cute ass cheeks with her perky tits protruding under her shirt. I knew I’d have her ass but I didn’t want to rush things. I began by relaxing on the couch and kissing her passionately concentrating on her lips, neck and breasts; I whispered softly in her ear.
“Can I have you in that ‘special place’?”
“Yes, I’m willing to try it,” she sighed. “But PLEASE be gentle”.
I gently put her on all fours at the couch edge, so she could present me the gift of her fine small ass. I knew exactly what to do; I got some Astro-glide and lubed her ass, inserting a finger into her awaiting opening slowly and gently. I knew she was unaccustomed to things going IN her ass and she squirmed from my gentle probing. But I could see a strange feeling come over Linda as I began making and in and out motion with my fingers. I could clearly see that it began to feel pleasurable to her. Soon, I saw that the pleasure was overwhelming the slight painful feeling of the initial insertion. Linda moaned in pleasure as my finger gently worked and massaged her anus. I added a second finger, gently inserting it deeper as I got better at manipulating my wife’s fine ass. I knew I’d have to get her ready before I slid my much thicker larger cock into her now-aroused and anxious rectum.
“Go ahead,” she quietly moaned, pushing her head onto the floor. “Take my ass”.
She turned her head to one side. I saw her facial expression. It was mix of arousal, wanting more pleasure, and apprehension, but nowhere near panic. She was curious… She told me to go slow.
I slowly rubbed my cock head up and down her ass crack, then found her sphincter. I could hold back no longer. I grabbed her by the hips and slowly eased forward pushing the first inch of my cock into her awaiting ass. She squealed as my cock slowly pushed her anus open. I held still a moment, then pushed slightly further. I offered to remove my cock from her ass, but by then my cock head was past her anal opening and well inside her. She quietly murmured for me to go ahead. I could tell Linda was growing accustomed to my cock. I slowly pushed further into her, then stood still so her rectum could get used to being filled and stretched by my cock. I knew to be considerate. A vagina is very elastic and designed for taking the pounding that a penis can deliver. Linda’s ass was just a group of tight muscles that had to get used to the stretching of a cock. I saw on her face that she soon began to relax and was more at ease with the feeling of a cock partially up her ass. I slowly pushed the remaining length of my cock into her. Again, I just stood still as she got used to it. Then, I gently slid my cock back and forth in Linda’s rectum. I was very gentle as she spread her cheeks firmly, so she could more easily take my small thrusts. I saw the faint apprehension slowly leave her face, but the arousal and pain/pleasure remained. She softly moaned in pleasure, just as she did when we had regular sex. Soon, her pain faded as pleasure sensations washed over her. I watched her face as waves of different and new sensations overwhelmed her. She rocked back and forth, slowly. It seemed like her body was one with my cock as it slid in her almost-virgin ass again and again. Soon all pain and apprehension left her face. I fucked her faster as she moved her ass back and forth on my rock-hard manhood.
Linda looked intoxicated from the new feelings her body was experiencing. I angled my cock upward to rub against her “G” spot as I thrust into her, faster, harder. Then it happened. She let out a loud groan as she experienced her first anal orgasm.
“Fuck me! FUCK MY ASS!” she shouted. “Don’t you DARE STOP!”
I obliged her, keeping my rhythmic pounding up for what seemed like forever. I could hold off no more. I felt my cock swell inside her. She flinched in pain/pleasure as I squirted cum deep into her ass. The sight of my cock working in and out of her ass drove me to an earth- shattering orgasm. My cock was engorged as I felt wad after wad of sperm splash in my wife’s fine ass.
I dismounted and passionately kissed her. After I pulled my cock from her ass, out came my creamy liquid. Warm sperm mixed with lube oozed from her ass as we laid back exhausted on the couch. She told me that the sex was “different” and this time she liked it, because the idea of submitting to me totally turned her on.
“The Broncos may have lost,” she smiled and purred. “But you sure won tonight!”