Pleasure and Pain

My sweet-but-strict wife, Mistress Jennifer, had not allowed me to orgasm in five days. On the fifth day, she called me at work and told me to be prepared for the night ahead, because I was in for a “learning experience.”

I pondered that with a mixture of excitement and dread. Every time she used that phrase, I usually ended up with a bruised bottom, but I had to admit I always enjoyed it.

When I arrived home from work that afternoon, the lights were off downstairs and there was a note on the door that instructed me to go up to our bedroom and take off all my clothes except my underwear. I walked upstairs quietly, listening for sounds to figure out where Jen was. I heard nothing. I walked into our bedroom and found a variety of toys laid out: Two paddles, a flogger, some nipple clamps and a rather large anal plug. There were several candles burning all around the room. The only light spilled from under the shade of our bedside lamp. There were padded restraints attached to all four corner bedposts.

Finally, I heard water running in our bathroom, and I assumed Jen was showering. I smiled, looking around at the scene she had set up for me.

I did as I was instructed and took off everything I had on except my white briefs. The note had not specified what I needed to do, so I sat on the edge of the bed and waited on Jen.

Momentarily, she emerged from the bathroom. She had on a white teddy, and nothing else. Her hair spilled down over her neck, almost to her shoulders. She smiled a seductive smile at me and kissed me.

“Welcome home,” she said.

“Thank you.” I smiled at her and shivered a bit as I admired her body and the sexy outfit she had chosen. My cock stirred, bouncing to life, ready at a moment’s notice after five days of denial.

“So what’s my learning experience?” I asked.

“Well, Honey, tonight I’m going to help you associate pain with pleasure,” she said. “I’ve been reading about it in a great sexual domination book I found last week in the bookstore.”

I looked at her with a quizzical look.

“Jason, you know when I spank or paddle you really hard, sometimes you lose your erection or arousal, right?”

I nodded.

“Well, I know you enjoy your spankings, even when it’s hard, but I want you to really associate spanking with sexual release. Enough explanation, Honey. Let’s just get started. I want you on your back, right now, and spread your legs and arms out so I can tie you.”

I did as she asked, my erection bulging in my underwear as her breasts swung against me while she fastened my arms and legs to the bed. She finished and lay beside me, her mouth near my neck. She began to rub my erection through my briefs and whisper into my ear.

“You haven’t come in a while, have you Baby?”

I moaned no in response.

“You want to, don’t you?”

“Yes, Ma’am,” I said in a breathy voice.

“It feels good when I rub your cock, doesn’t it? It makes you want to come. I’ll bet you could come right now, couldn’t you?”

I nodded, turning my head toward her.

She quickly pulled her hand away from my cock and slapped my face, hard.

“Well, you’re not going to, for a while, anyway,” she said firmly.

My face flushed and my cock throbbed. She put her hand back on my cock and just left it there, without rubbing, feeling it throbbing beneath her hand. With her other hand, she grabbed my right nipple and twisted it, hard, making it erect. In one smooth motion, she grabbed a nipple clip and fastened it to my erect nipple.

It HURT. I moaned and writhed as far as my restraints allowed me to. The pinch began to really sting on my nipple. It hurt so badly that my cock began to get soft, as all I could think of was the biting sting on my nipple.

She watched all this, calculating. She felt my cock grow soft under her hand. When she was satisfied my erection was gone, she took the clip off and kissed my nipple. She began to rub again, stroking me.

As the pain subsided, the warm feelings came back as I enjoyed her mouth on my nipple and her hand on my cock. I began to harden again, my cock bouncing as it did so.

She stroked me harder this time, feeling the shape of my cock and whispering dirty things into my ear, things she knew turned me on. She whispered to me to tell her when I was close to coming.

“Don’t you dare come, Jason,” she warned. “Tell me before you lose control.”

Finally, I moaned to her that I was close, almost there.

Sure enough, she repeated the nipple torture on the left nipple, the twist and the clamp doing the same thing to my arousal as before.

She revived me again, taking the clamp off and rubbing me back to life.

It was sweet, submissive torture.

After I regained my erection after the left nipple got its treatment, she pulled my underwear down as far as the restraints would go. She straddled me, took my cock in her hand and rubbed it on her wet pussy. Again, she told me to tell her when I got close.

“It’ll be worse, Jason, if you lose control and come,” she said. “I won’t let you come for two weeks. You better tell me when you’re close.”

I moaned, wanting to tell her, to obey, but dying to let it go and get the sweet release my aching cock and balls were begging for.

I chose to obey, and told her I was close.

This time, she got off me, unfastened the restraints and told me to get on my knees.

She pulled my underwear off and began to smack my ass hard with her hand. As usual, this just turned me on more, and she reached underneath me to see if I was still hard. I was.

She grabbed our oval, oak paddle and placed it against my ass. I felt it leave, and with a loud crack, I felt it strike me. I collapsed on the bed, off my knees, the sting more than I expected.


“Get back on your knees, NOW,” she said. I quickly complied.

She put the paddle back against my ass, rubbing it from side to side. Again, with almost all her force, she paddled me. The crack reverberated through the room and it hurt so sharply I cried out again.

Rapidly, barely pausing between smacks, she gave me 10 more. My bottom ached and I felt the heat spread over my skin.

She reached underneath me, and my cock was still semi-erect. She swapped the oval paddle for a larger, heavier, sorority type.

“Ok, a few more. Back on your knees, please.”

I did as I was told, elevating my ass, submitting it to the paddle.

From previous experience, I knew when I felt the next smack it was as hard as she could deliver. I moaned, very loudly, and felt tears sting the corners of my eyes. Four more just like that one followed. All I could think of was the burning and aching in my ass.

She reached underneath me again, and felt me flaccid.

“Turn over, Jason. On your back.”

I did as I was told, the cool sheets feeling good against my burning skin.

This time, she took my soft penis in her mouth and caressed it. I sprang to life, my cock getting hard in seconds, as the sudden shift from pain to pleasure made me dizzy.

She bobbed on my cock, in smooth, fast strokes, then abruptly stopped.

“Tell me, Jason, when you’re close. Don’t you DARE come.”

She resumed her mouth action, but I quickly stopped her.

“I’m about to come, Mistress. I can’t help it. I’m so very close.”

She stopped.

“Back on your knees, Jason.”

I groaned as I flipped over and presented my ass again.

It was the same process again…hard smacks, a quick feel of my dripping, throbbing, semi-erection, then more hard smacks, then some killer-hard smacks to finish the deal.

Finally, mercifully, she told me to roll over. I had tears in my eyes as I did so.

My balls ached. They were heavy and achy and sore. Even rubbing them hurt a little, but sure enough, she stroked me back to a rock-hard erection.

She stopped again, and paddled me again, my ass cherry-red and really burning.

Then the same process…I rolled back over and she kissed me all over, touching me and arousing me.

The next time I told her I was close, she told me to bend over some pillows. I heard her grab the lube and rub it all over the plug. I groaned when I felt its tip against my anus, and I moaned as she quickly inserted it.

The pressure was intense, and I gasped for breath as she fucked me with it, pushing it in and out. She felt my cock as she did so, feeling it eventually get soft from the intense pressure, the pain from the fullness of the plug in my ass.

Again, she stopped, and stroked me back to the brink of orgasm.

I lost track of the cycle. Once, she straddled my hips and put my cock in her pussy. It took all my control not to come. After that came the flogger, as she used it to created stinging explosions on my bottom.

Finally, after an hour or two, she told me my learning experience was over and told me if I begged enough, she would give me release.

I wasted no time, begging her earnestly to please let me finish and come.

She leaned back against the pillows.

“Ok, if you want to do it, do it. I’m just going to watch. I want to watch you stroke your own cock for me and come on yourself.”

I did as I was told, furiously stroking before she could change her mind.

Mere seconds later, I erupted, come shooting on my stomach and chest. The release after the five days of denial and two hours of torture was immense.

She just watched me and smiled. I knew enough to savor this orgasm, because there wasn’t any telling when she would allow me to have another one.

© ~*lilith*~ 1997-2009, except where noted