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Ask and Ye Shall Receive

Category: Anal Sex
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Mike’s wife laughed the first time he brought it up.

“You’re kidding, right?” She looked at him incredulously.

“No, I’m serious,” he said. He was a little miffed that she was laughing as they lie in bed after having sex. It wasn’t anything to do with what they’d just done but … still. She was laughing at something that he really wanted and had finally gotten up the courage to mention.

“I’m not gonna do that! That’s just… weird.”

Mike lapsed into silence. She looked over at him and sighed.

“I’m sorry honey, I didn’t mean to say it like that, but I don’t think I can do that for you.”

Mike smiled half-heartedly and she leaned over to kiss him before curling up to sleep. Mike decided to forget about it. It just wasn’t going to happen.


However, Mike found he couldn’t forget about it. A couple weeks later he was home alone while his wife went out Christmas shopping with some friends. He decided to spend a little quality time by himself online. He found a web site with sex stories and read a few. He had gotten a nice warm feeling and decided to browse through the discussions taking place when he noticed one that said “Strap on sex – F to M.” It had over 154 pages!

He quickly got naked and put a towel over the leather office chair so he could be comfortable. He relaxed and started reading through the thread. He put a little lube in the palm of his hand and started stroking himself slowly as he read. There were men saying how much they wanted woman to do this to them, men saying how much they enjoyed having it done to them and women saying how much they loved to do that to men.

But as he read on it got even better. More and more people started posting their experiences with it and a couple people started posting lots of pictures. He really got into it, stroking himself hard and squeezing his balls as he looked at the pictures. Women with big dildos strapped to their bodies slid into guy’s asses from every conceivable angle. Then someone started posting video clips. They were so hot! Watching a woman in a leather outfit slide a big dildo into the guy’s anus made him squirm and shoot his load. He cleaned himself off and kept reading. There were links to a couple stories specifically about this so he followed one and read it.

It was sooo hot! If only he could get his wife to look at it this way. He decided to print the story out and show it to her. He was already getting hard again. The article printed, he made a note on it of the thread address so she could look there if she wanted as well.


It took him a couple more days to get the courage up again to show her the article. He finally decided to leave it for her with a note before he left for work. Cheryl found it Tuesday morning on the counter in the kitchen.

Cheryl – Please, just give this a read. If you still don’t want to do it, I’ll understand but I think this might change your mind. – Love, Mike

Cheryl rolled her eyes. Not bloody likely. But she got a mug of coffee and sat down with the story in the living room anyway. She started to read with a feeling of duty but by the third page she was hooked. It wasn’t quite what she imagined. She had to admit, the idea of being the one in charge, giving orders sexually, did excite her a little. She just didn’t have any interest in hurting or humiliating Mike. She didn’t want to go down that road, but that wasn’t what was happening in the story. In the story, the woman’s goal was to give him an incredible orgasm by stimulating his prostate.

As she read, Cheryl felt her own anus start to tingle a little. Suddenly intensely curious, she sucked on her finger and laid down on the sofa face first. She lifted up her nightie and reached back into her panties and found her own rosebud. She started to massage around it and gasped. Mmm, that did feel good. She pulled her finger out of her panties. She wasn’t about to go any further without some major lube.

Cheryl went into the kitchen and washed her hands then headed into the computer room to fire it up and check out the web site Mike had noted down for her. She was a little shocked by the photos. The dildos were huge! She read through the posts and then found some “how to” articles. With the right precautions, it sounded like this could actually be fun. She went back to the pictures and studied the outfits the women were wearing. With a couple additions to her wardrobe, and a few toys, she could do something like that.

She scooted over to the adult toy store web site that she’d used before and looked through things, picking out a couple toys and ordered them. Then she went back to the how to articles. She was getting excited.


That night, at dinner, Mike asked her how she liked the story. She kept her eyes down and was noncommittal.

“It was okay.”

“Do you think we could do something like that?”

“I don’t know. I’m going to need some more time to think about it. I’ll let you know.” She got up and took her empty plate into the kitchen.


Two weeks later, on a Friday, Cheryl called Mike at work and suggested he come straight home after work.

“I have a little surprise for you,” she teased in her bedroom voice.

“I’ll be right there!”

Good to his word, Mike was home in twenty minutes. It may have been a new record for the drive from his office.

Cheryl met him at the door. She didn’t say a word as his key turned in the door and it swung open. letting in a blast of cold air. She simply stood there, stroking her hand up and down a purple dildo that was strapped to her crotch. She gave Mike a wicked grin. She was wearing a black leather bustier that left her tits bare and a garter belt with black lace stockings and red stiletto heals. She’d slicked her blond hair back and applied her make-up rather heavily.

Mike stopped in his tracks and forgot to breath for a minute. He exhaled on a groan as he took in the vision in front of him. He’d given up hope on this but she’d definitely been planning this for a little while. He closed the door behind him.

Cheryl crooked a finger and stepped backwards into the living room.

Mike dropped his briefcase and followed after her, shedding his overcoat as he went. He stepped into the living room and looked around. She had indeed been busy.

The heavy drapes were drawn across the windows and there was a gentle fire in the fireplace. Candles were lit on all the flat surfaces around the room. A soft, dark blue chenille spread covered the sofa. A champagne bucket stood to one side with a bottle chilling inside and a platter of chocolate covered strawberries. A cinnamon scent filled the air. Music played softly in the background.

“Honey, you are the best wife in the world, you really must be,” Mike said, looking at the soft, seductive setting she had created for him. His eyes were continually drawn back to the dildo she was wearing though.

Cheryl picked up a glass of champagne and drank it down.

“I’ve drawn a bubble bath to get you cleaned up,” she said. “Go into the bathroom and strip down. You’ll find an enema on the sink. Use it. Call me when you’re done and I’ll come supervise your bath.”

Mike grinned as he walked out of the room, already unbuttoning his cuffs.

Cheryl took one more look around the room to make sure everything she would want was laid out and poured herself another glass of champagne to sip while she waited. Finally, Mike called her into the bathroom.

“What now?” he asked with a half smile.

Cheryl smiled back and flicked the overhead light off. The only light now was from the glow of candles on the sink counter. She walked up to Mike and ran a finger down his chest. Her hand slid around his cock, giving it a little squeeze and releasing it.

“Now… you get into the tub and clean up.” She sat down on the padded toilet seat and crossed her right leg over her left. “I’ll supervise.”

Mike gamely stepped into the tub. The water was warm and sudsy as he settled into it.

“Use my body wash,” Cheryl decided suddenly. It had a nice soft, peachy smell. His soap was too crisp and clean smelling for the mood she was trying to create.

He lathered up a washcloth and scrubbed himself clean. When he thought he was finished, Mike wrung out the washcloth and hung it up.

“Not so fast,” Cheryl said, picking up a plastic glove and walking over. “Crouch down.”

“What?” Mike looked at the glove warily.

“Now,” Cheryl said, cocking an eyebrow.

Mike did as he was bid, crouching down in the sudsy water. Cheryl reached under him and slid her hand down his ass in the warm water. He jumped a little when she found his anus. She took her time, massaged it for a minute and then pushed her finger in.


“You okay?” she asked, one hand on his shoulder to steady him and one finger up his ass.

“Yeah… oh yeah.”

She slid her finger in and out, swirling it around for a minute as Mike groaned. She abruptly pulled out and he sighed.

“Okay, time to get dried off. There’s more to come out in the living room. You towel off and put on the robe.” She gestured to a black silk robe hanging on the bathroom door. “Then join me in the living room.”

Cheryl left the bathroom as Mike stood up, water cascading off his body, and stepped out of the tub. She went back to the living room and poured him a glass of champagne then sat on the sofa, nibbling on a chocolate covered strawberry. She was beginning to get used to having this dildo strapped to her crotch, particularly the way it rubbed against her clit.

Mike walked in and she gestured for him to sit next to her. When he was seated comfortably, she handed him the glass of champagne then held a strawberry up to his lips for him to take a bite.

“Mmm, lovely.” He rolled the strawberry around in his mouth, letting the chocolate soften.

“Harry and David, expensive but I figured for a special occasion like this it would be appropriate.” She leaned in and pressed a kiss to his lips. “Since I’m gonna pop your anal cherry and all.”

She giggled as Mike reached out and touched the cock strapped to her. His brow furrowed.

“That looks pretty big to go in my ass.”

“Don’t worry, we’re going to get you nice and opened up before I take this bad boy in, and it’s not even as big as yours. It’s only an inch wide and five inches long. I wouldn’t damage my property.” She winked at him and finished her strawberry.

“Your property?” he asked with a smirk.

“Yeah, your ass is gonna be mine tonight, babe.”

“Mmm, my ass has always been yours for the taking, ” he replied, leaning in to kiss her. He took her champagne glass and set them both on the table.

“And I really love this outfit.” He reached up to cup her right breast, which was encased in a supple leather that left her nipple bare. The leather was soft against his palm as he brushed his thumb across her nipple and watched it harden. He leaned down and applied the flat of his tongue to it, the hard nub sliding across his soft tongue. He blew on it and Cheryl shuddered.

“Suck it,” she hissed. He complied readily.

“Mmmm.” Mike started to pull back but Cheryl reached up and gripped his short hair to hold his head against her breast for a moment longer, asserting her control.

When she let him pull back, they were both feeling warmed up. Cheryl reached down to untie the sash on his robe and slid her hands in over his chest. She let her fingers drift down over his abdomen, lightly stroking the thick hair covering him as she went then stroked one long finger nail down the length of his semi hard cock.

Abruptly standing, Cheryl moved over to the padded hassock in front of Mike as he sat on the sofa.

“Put your feet up here,” she said, patting the hassock to either side of her. “And scooch down so your ass is on the edge of the sofa.” The hassock gave her some mobility to move forward when he was ready.

Cheryl lifted the dark blue hand towel on the tray set to the side and pulled out a set of latex gloves and a tube of lube. She pulled the gloves on with a snap and opened the tube to apply a generous dollop to both her middle finger and his anus. His anus contracted when the cool gel hit it and she smiled. She looked up at him and he smiled back. The tube set aside, she rubbed the lube up and down her finger then started to smooth the dollop over his anus.

She circled around and around then rubbed over it and circled again. Finally, she began to press in slowly. After inserting her finger about a half-inch, she met a little resistance but was easily able to push forward gently. When her finger was all the way in, Cheryl felt Mike’s anus begin to spasm a little so she waited until it stopped then began to gently rotate her finger. She looked up to see Mike’s eyes were closed and he was biting his lip.

“How does that feel?”

“It feels… ohhhh. It feels sooo good.”

Cheryl grinned. She started to roll her finger around as if she was trying to slowly enlarge a hole. She’d hold still for a few seconds then start again. After about ten minutes of this, she reached back under the cloth on the tray and pulled out a butt plug that was tapered and almost twice as wide as her finger at the largest part.

Mike groaned as she slowly drew her finger out of his ass. She quickly lubed the butt plug up and added a little more lube to his anus again then started pushing the plug in slowly. Easing it in, she encountered no real resistance and soon it was all the way in.

“How does that feel baby? Do you like it?”

“I feel so… full. It feels good. It doesn’t hurt at all. I love it.” He kept his eyes closed, enjoying the new sensations he was experiencing.

Cheryl put some more lube in her hand and took hold of his now semi-hard cock and started to stroke it, one hand at the base and the other slowly sliding simply up and down. She stopped about half way up his shaft and brought her other hand up so that she gripped him very loosely and started to turn her hands in opposite directions.

Mike groaned and opened his eyes. “Baby, you know how to touch me just right, nothing you ever do seems to be wrong.”

Cheryl smiled up at her husband and let one hand slide up to cup and polish the head of his cock in a round circular motion. He was fully erect by now.

Cheryl decided it was time to see if he could take the dildo. She lubed it thoroughly as he watched. He reached down and started stroking his own cock as she stroked the fake cock harnessed to her. She looked back up at him.

“Are you ready to try this? We don’t have to go through with it if it hurts.”

“I’m ready,” he said, staring into her beautiful blue eyes.

Cheryl reached forward and took hold of the anal plug in his ass and started to draw it out, twisting gently as she did so. Mike groaned again and closed his eyes. It slipped out faster and faster as she pulled.

Scooting the hassock forward, she quickly positioned the head of her dildo at his anus and started to push in. She moved slowly, giving him time, stopping every half inch or so for a few seconds to let him adjust. Finally, she had all five inches buried in his ass. She held still and drew her fingers up and down his thighs, teasing a little. He shuddered and opened his eyes. She cocked an eyebrow in question and he nodded.

She began to pull out then slide back in, excruciatingly slowly. Her gentleness served to heighten the sensations Mike was experiencing. It was almost too much. Beads of sweat appeared on his face and he moaned continuously.

As momentum slowly built, Cheryl reached out and started to stroke his cock again, keeping time with her thrusts into his ass. She squeezed his cock just a little on the up stroke, as if she were milking it. She slowed to a slow stroke then gave him a couple fast, alternating speed to see what felt best to him, watching his face to gauge his reaction. The rubbing against her own clit was making it a little difficult, but she struggled to concentrate on what she was doing to him for now.

“Faster,” he urged as he felt his orgasm build, his balls pulled in and the muscles throughout his body tightened. It was like nothing he’d ever experienced before. Cheryl stroked the dildo faster in and out of his ass. Mike felt his orgasm rip loose. His come spurted like a geyser into the air, landing on his chest. It felt like every part of him was shaking with pleasure. The muscles all through his body shuddered in release.

“Oh God! Yes! Yes!” The orgasm seemed to go on forever, shot after shot coming from his cock and his ass spasming deliciously. Finally, he slumped back. Cheryl released his cock and slid the dildo out of his ass. She took the cloth that was nearby and wiped him off gently. Unbuckling the harness, she stepped out of it, wrapped the dildo in the towel then curled up on the sofa next to Mike.

“Thank you baby, that was incredible,” Mike said weakly.

“You’re welcome.” Cheryl stroked her hand over Mike’s chest then leaned over to kiss him softly. “You rest and recover, I’ve got more plans for you yet tonight.”

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