A Lesson Learned

"This is a butt plug, Andy. Guess where it's going? she asked as she twirled the toy inches in front of my face.

"Nnng oooh!, I screamed. That was not going in my ass. Nothing was.

Jenny took the lube and the plug, and got up on the bed between my tethered legs.

"This is soooo hot." she said.

Jenny unscrewed the cap to the lube, and holding my sac out of the way, dripped a generous amount into the crack of my ass. She coated her index finger and then spread the lube she had dripped across my sphincter. I jumped as she tapped her finger on the little rosebud.

"Melissa says that all guys love getting their ass done by their woman once they get over themselves. She said you have to relax. If you don't, it will hurt."

Her slippery finger began to exert pressure on my sphincter. I could tell right away, it was going to give in. It was a battle that I couldn't win. The pressure on it increased. I think I whimpered as her finger finally entered me. Jenny held her finger still for a moment, as I tried to come to grips with the weird sensation. She pulled it out, and coated more lube on the finger, and pushed it right back in. There was no battle this time. It slid in a little deeper than the last. Jenny alternated holding her finger still, then gently pushing, pulling, and wiggling. I had to admit after a few minutes that it actually was beginning to feel good. The lube was warming up, amplifying the empty feeling each time she pulled her finger out to add more lube.

Jenny gave a push, and her finger was now deep inside me. She was moving it around, almost as though she was searching for something.

"Ooooonnggg", I cried out through the ringed gag as her finger rubbed against something that sent jolts of pleasure through my to cock.

"Aha, I just found your prostate, Hun. We are going to have a whole lot of fun with that today." she whispered huskily. Jenny then pulled her finger from my ass, and picked up the butt plug.

She coated huge amounts of lube on it and put the narrowest point against my sphincter.

"I think you're ready for this now."

Jenny began pushing on the rubber butt plug. At first it went in easily, but then it began to widen, and become uncomfortable. Jenny sensed this and stopped. She pulled it out, and added more of the evil warming lubricant that by now had my ass aglow. She began pushing again. This time, it went in much deeper. But it was stretching me too far. It was really starting to hurt. She stopped again, and pulled it out, adding more lube. Again it entered me. It was almost in. Jenny was not stopping this time. She increased the pressure. I thought that my ass was going to split. I remembered her advice about relaxing, and seriously tried to let my sphincter go and relax around the intruder. It hadn't looked all that big in front of my face, but it felt huge. I thought that it was surely going to injure me. And then suddenly my sphincter contracted. It was a jolt of pleasure and relief all mixed together as the pain disappeared, and the plug seated itself in my ass. It was in. My sphincter was firmly gripped around the narrow piece between the plug and the base.

"Oooooo, Baby, that is sooooo hot", Jenny dripped. She tapped the butt plug sending wicked sensations through my ass.

She then climbed off of the end of the bed, and pulled up two more straps that seemed to be attached to the footboard. She attached them to the cuffs on my ankles, and undid the straps holding my feet up by my head. My legs thankfully dropped back to the bed. She then began tightening the new straps. This had the effect of trapping me in a spread eagle form on the bed. How on earth did I not notice the straps already attached to the bed? With my legs down, the pressure of the plug in my ass increased. I was very, very full of rubber. And I was very aware of the heat surrounding the plug.

She made her way back to the purse beside the bed and proceeded to pull out two very small rubber spatulas. I was reminded of licking icing off the ones my mother used when she made birthday cakes when I was young. She placed them beside my head. I was beginning to understand her game. I was being forced to watch her prepare whatever was coming next. Jenny then placed a controller of some sort next to it. It was white plastic, very cheaply made, with a round dial. There was a wire coming from the controller that ended in what looked like a small headphone jack.

"We are starting your punishment now. You really made me mad last night, and I am going to make you think twice about ever pulling that crap again." Jenny said in a very matter of fact manner.

I had no idea of what was coming, but I was certain that I didn't want to know.

"Nnnng ooooorr eeee!" I tried to apologize through the gag, which was making swallowing very difficult.

"It is 10:55. I am going to tease you until 11:55, and then you can cum. Let me rephrase that. Then you will cum." Jenny said.

She grabbed the controller and hopped back up on the bed between my legs. The spatulas remained beside my head. She knelt between my legs, and took the wire from the controller, and pushed it against the butt plug. I felt a tiny click as the tiny jack locked home. She turned the dial on the controller, and stared at my face to watch my reaction as the plug came to life. The demonic thing was a vibrator! Her finger on my prostate was nothing compared to this. She turned the speed way up for just a second or two, before turning it back down to a gentle hum. When she turned it up, I felt my eyes roll up in my head. I had never felt anything like this before.

Jenny leaned forward and took my cock in her mouth. It was so hard, her mouth so warm and wet. She gently and slowly took it in and out, in and out, teasing me with her tongue. Her long blond hair was tickling my thighs. With the vibration in my anus and her free hand rubbing my balls, I knew I wouldn't last long. As I got closer and closer, she stopped.

"Not yet, Baby." she laughed. "It hasn't been an hour yet, it's only been a few minutes."

I pleaded through the gag to cum, but it was not to be. Once I had sufficiently backed off, she turned the vibrating plug up, and began pushing on a spot between my ass and my balls. The feeling was intense. She was forcing my prostate to rest more tightly against the vibrating plug in my ass. She then began stroking my cock at a maddeningly slow pace. It felt so good, but I needed more to cum.

"Melissa says this is called edging." Jenny turned the vibration up some more, and took my cock back in her mouth, swirling her tongue around the head. As she sucked on it, knew I could cum, just one more stroke and I was there. The vibration stopped, and so did the blowjob.

I screamed in frustration as Jenny burst out laughing.

"Not yet big boy!"

My cock felt like it was going to burst beyond its six and a half inches it was so hard and ready. I did not like edging. Jenny took me to the edge no fewer than six times in that hour. I really needed to cum. Mercifully for the last fifteen minutes, the vibrator had been at a very low setting.

At 11:55, Jenny looked at the clock and said "that was fun. Now it's time to make you cum. Did you know that both edging and prostate stimulation will greatly increase how much ejaculate you expel?"

Ejaculate? Expel? Why the hell was she talking like that?

Jenny took my cock in her mouth and began slowly caressing it, in and out. As my excitement began to rise, her other hand took the controller, and turned the dial slowly all the way up. The vibrating plug whirred to a fury inside me. She then began pressing on that spot between my ass and balls. Her mouth increased suction and speed. There very loud strange noise in the room that I realized was me screaming through my gag. I was cumming, and cumming harder than I ever had in my life. Jet after jet of cum raced from my cock into her mouth. As my orgasm subsided, Jenny turned off the vibration in my ass. I was hyperventilating and seeing stars. Jenny began moving up my body. The things my wife could make me feel. This had been weird, but amazing. I was so in love with her. Jenny was still moving upward. I figured she was just going to cuddle me. This was something else. She was now on her knees. Once again, I felt the leather of those boots on my ears as she trapped my head between her legs. She squeezed my head tightly, and picked up the spatulas, resting one on each thigh, the wooden handle of each tucked into the top of each boot.

I looked into her eyes and saw the same look the sly lioness has when it sees that its prey has realized its impending fate. It suddenly dawned on me.

She still had my cum in her mouth.

I tried to turn my head, but her legs had me trapped. She grabbed my hair and held me immobile. I watched in horror, cursing this open gag that had my mouth forced wide open. She was smiling as she slowly let the cum drip from her lips. A huge long strand stretched from her mouth all the way to mine. I felt it touch my tongue. We were joined by a strand of my cum. She pushed more out of her mouth, and it quickly followed along the first strand. When the strand broke, she giggled, mouth still full, and leaned closer, letting a huge amount drop into my mouth. I wanted to gag. She spit even more into my waiting helpless mouth.

Now I had a huge amount of my own cum and her saliva to deal with. I lay there not sure what to do. This was so gross. I was still trapped between her legs, but at least now she had let go of my hair. I could move my head up and down.

"Swallow." she said, staring into my eyes.

With my new limited movement, I leaned my head forward, and using my tongue, tried pushing the cum up and out of the gag. It dripped out past the gag, and down my chin. If only I could do that a few more times. Jenny picked up one of the rubber spatulas, and calmly scraped the cum off of my face and deposited it right back in through the gag. This wasn't going to work.

"Swallow" she said. "We can do this all day. The longer you wait, the more you will have to swallow. Your body knows that there is something yummy in your mouth, and is pouring saliva in there to help you eat it. Swallow."

She was right. I could feel my own saliva seeping into my mouth, ever increasing the volume. I realized that it was the thought of what I was being forced to do that was making me gag. The taste was neither good nor bad. I think I was actually beginning to come to terms with my situation. But just as I was about to try to swallow with this damn gag, a challenge on its own, Jenny stuck her finger in my mouth and began wiping cum across my teeth. She was trying to make it harder to get. I swallowed. And then again. And again. Thank God it was over.

"I enjoyed that sweetie. Are you ready to go again? "

My cock was rock hard. What was wrong with me? I could never get hard so quickly.

"You are ready. The Viagra I crushed in your OJ this morning seems to be working well. That's good, because we have a big day planned for you. Melissa will be here soon, and she's bringing some of her really good toys." Jenny chuckled.

Melissa, my assistant was coming here, today, with me like this? What had I gotten myself into?

To be continued...