SilverHubby and Silverdrop

Wicked Wednesday – Keeping it Real…

… or not:

This challenge is to prove WHY erotica glamorizes the beast with two backs.  Write a story, or a paragraph or a note of the finest fantasy sexual encounter, and then do it again.  The second time, make is “real”: awkward, messy, stuck bra clasps, shoes with knots that can’t be undone, pauses, ouches and “did you finish?” “Wait, what are you doing?” “Should I get a towel?”

The Fantasy.

They had both been interested in pegging for several years, and this was it, Der Tag. The harness and dildo had arrived that morning and they couldn’t wait to use it. He watched her climbing into the harness and adjusting the straps, his cock hard and throbbing with excitement.

He rolled onto his belly, butt in the air, as she positioned herself between his legs. He let out a groan as the tip of the dildo touched his virgin ass, then gasped in surprise as she slid smoothly into him and started to thrust.

He buried his face into the bedding, moaning all the while as she fucked him like she’d been doing this for years. He couldn’t stop himself from pushing back against her, willing her in deeper. His aching cock leaked pre-cum over the sheet as the pressure on his prostate became unbearably wonderful.

When she grabbed his pelvis and thrust all the way in, just like when he fucked her doggy style, he was lost. With a shout, he orgasmed, hot spunk jetting out of him in several bursts over the bedding and his belly. She collapsed on top of him, smiling.

The Reality?

The harness and dildo had stayed in the delivery box for a week. There just never seemed to be enough time or energy to use it. They decided Friday night would be it, Der Tag (The Day).

He lay on the bed watching her struggle with the harness, quickly realising he would need to get up and help her with all those straps and buckles that need adjusting the first time it’s used. It took several attempts, not to mention a skin nip or two as folds got caught in the buckles. Then the dildo wouldn’t go through the ‘O’ ring, so that had to be changed.

“Lube!”, he said. How could they have forgotten that? They were playing safe and used two syringes full in his virgin ass. But he could feel it leaking out of him with all the exertion, and it felt odd, uncomfortable.

After a cuddle and some stroking, he rolled onto his belly and opened his legs. His hip joints immediately reminded him they were arthritic and were’t at all happy with this position and would he mind moving the hell onto his side, which didn’t hurt so much.

They got into position for spoon-style sex, after which it went something like this:

Her: Positions dildo between his legs. Immediately realizes that, unlike a biological cock, the dildo has no nerve endings to give her feedback. “Am I in the right place?”

HIm: Wiggles a bit. “A little lower. There, that’s it.”

Her: Pushes her hips forward a little, trying to enter him.

Him: “Ow!” The dildo skidded on the lube and hit him in the balls.

Her: “Sorry, but I can’t feel what I’m doing.”

Him: “It’s OK, let me help.” He reaches back and guides the dildo back against his anus. “Now Push gently.”

Her: Pushes forward again, the head of the dildo entering him.

Him: “Oh!”

Her: Thinks something’s wrong, stops what she’s doing. “Are you OK? Did I hurt you?”

Him: “No, I’m fine. It’s just my brain processing a new sensation. Carry on, please.”

Her: Too worried about hurting him to relax into it and enjoy it, pushes again. “Is it doing anything to your prostate?”

Him: “Not yet. Keep going.”

Her: “It’s all the way in. How do you feel?”

Him: Whimpers.

Her: Very worried by whimpering. “What’s wrong?”

Him: Muffled. “Nothing. Fuck me.”

Her: Begins thrusting. Feels him pushing back against her. Feels her male energy coming forward and starts to actively enjoy herself, feeding off his reaction to her fucking him. Realizes he’s making noises she’s never heard him make before. Is worried she’s hurting him. Stops fucking him. “Are you OK?”

Him: Gasping. “My prostate… for fuck’s sake fuck me!”

His orgasm, which triggered hers, was memorable to say the least. The bedding needed to be changed.


The second version is more or less what happened the first time we tried pegging – we got much better at it. We actually prefer the second version because it is real. What do you think?


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8 thoughts on “Wicked Wednesday – Keeping it Real…

  1. Stella

    I enjoyed both but the second one really spoke to me. It’s true about not knowing what’s going on when trying to do it the first time. I remember being so concerned I was hurting him as well. It did get better but know where near the fantasy version of it.


  2. Molly

    Yep I agree with everyone else, the second real version has that strong thread of truth about it that makes it far more intimate


  3. sabsam

    I too prefered the second version, much more interesting, better in the writing too, and so much more funny!

  4. Curvaceous Dee

    *grins* The second version is very much like my many sessions with Hylas – I love doing it, but damn it’s difficult not having that tactile knowledge of where that toy is actually going! I can always angle my fingers correctly, and I can never get a toy right, ever 🙂

    Really loved reading this.

    xx Dee

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