Jennie Goes to New York City

"Yes Master, if it pleases you Master, please clamp my nipples Master," she pleaded with her voice still cracking. At this point, I couldn't tell if Jennie was playing the game for my pleasure, of if she was actually finding pleasure in her sub-space. I was so hoping it was the later, but we'd discuss that at another time. Right now, all that mattered was taking Jennie up to her limit, then making her cum. I only hoped that she was enjoying this as much as I was.

"OOOOWWW", she screamed as the first clamp compressed hard onto her left nipple.

"I know it hurts Jennie, but just relax, breathe deeply, and concentrate on my thumb as it circles your clit," Jamie said, as his thumb once again worked in circles on my pussy. The clamp hurt a lot at first, but as he continued the ministrations of my clitoris, the pain slowly morphed into a minor dull throb that seemed to serve as background music to the strumming of my clit. "OK Jenn, you seem good, so now it is time for the second clamp," Jamie warned. Once again, he abandoned my clit to begin working on my right nipple. And while the teasing of my breast felt terrific, I knew the stinging bite of the clamp would soon follow.

"AAAAAAHHHHH FUCK!!!!" This one hurt twice as bad as the other, and really got my blood pumping and my body near convulsing. "Relax and breath, Jennie," Jaime counseled. "Nice and deep breaths, and focus on your pussy" he again cooed, as his thumb found it was back to my clit and resumed the pleasure half of the experience.

"How do you feel Jenn," Jamie asked in that caring, but firm, monotone of his.

"I'm good Master", I replied. "It hurts, but as long as you keep stroking me Master, it's also very enjoyable as well", I continued.

"Good Jennie. I'm so happy to hear that you are enjoying this, because your Master is enjoying this immensely, Jennie. You'll be happy to know I'm going to fuck you soon." he added. "And we're both going to cum like crazy Jennie. Are you ready to cum Jeannie?" I asked, continuing with the monotone. Would you like to cum Jenn? Tell me how bad you want to cum Jennie," I asked finally.

"Oh yes Master," she responded. "Please fuck me Master, and make us both cum," she pleaded. Cum on my face, Master, cum in my mouth, or my cunt Master, just please make us cum, PLEASE," she said pleading for relief.

"Just lie back and relax Jennie," I gently scolded her. "We'll both cum soon enough," I promised as I got off the bed. "I have one final test for my slave to experience before we complete your challenges this evening. Can you handle one more test for me Jennie", I asked her?

"Yes Master, I'll do anything you ask Master, but I am so close to cumming Master, and I need to cum so badly," she responded.

She was desperate, and we both knew it, so I needed to be careful. I wanted to add to her pleasure, but I did not want the momentum to totally crash. "Jennie, you look so beautiful here tonight, but I am a little disappointed that your ass seems to be lonely. Is your ass lonely Jennie? Does your ass want some attention, Jennie? Do you like having your ass played with Jennie," I questioned hoping to get her to the finish line without fucking the whole thing up.

"Yes Jaime!! Fuck me Jaime, Fuck me in my ass Jamie, FUCK ME ANYWHERE, just please let me cum Jamie, PLEASE MAKE ME CUM!!!!"

With my thumb once again circling her clit, my index finger penetrated her ass in preparation for the vibrator. "I am going to put this vibrator in your ass slave, and it will feel very, very, good. But you are not allowed to cum until I say it is OK. Do you understand slave?"

"Yes Master, I understand Master. I will not cum until you say Master," she added like the perfect slave girl.

"Excellent Jennie", I praised her. I am going to untie your legs now, so that your Master can better access your ass, Jennie. Will you allow me to access your ass slave," I asked.

"Oh, Yes Master, my ass is your ass," Jennie replied, once again as the perfect slave girl. After un-securing her legs, I turned on the vibrator and the initial buzzing startled Jennie into more thrashing and moaning. "Oh Master, please Master, make me cum," she begged again.

"You will cum soon my Love, you will cum soon", I promised. "Now I want you to hold still".

"Oooohhhhhhh Master, fuck my ass," I screamed, as the vibrator was slid fully into my ass in a single stroke. "AAAAAHHHHHHHH FUCK!!!" I wailed as vibrations reverberated throughout my entire body. "Oh, my fucking-God!" I continued wailing. The buzzing, coupled with the clit stimulation was almost overwhelming. "Master, may I cum Master?"

You will not to cum yet slave," Jamie commanded, in conjunction with a slap to my thigh to get me refocused. "I have one more thing to do before we both cum," he advised. I was crazy with the need to cum, and there was no way that I was going to be able to hold off for very long with that vibrator buzzing in my ass.

"Smile Jennie," Jamie commanded condescendingly. At first, I couldn't grasp what he was talking about. Then it dawned on me that his fingers were no longer teasing my clit. "You look beautiful my love, and I want some photos to help us remember this evening together" Ch-chit/flash. Ch-chit. flash. "Lift your ass Jennie," Jamie commanded, "Show me that vibrator in your butt". He took about a dozen photos of me posed in various stages of spread eagle, ass up, legs overhead, face in my cunt, etc., and then mounted the camera on a tripod. "Now for relief my dear", he said, as he, and his hard cock, crawled into bed with me.

I put the camera on video mode, then mounted it to the tripod, and got into bed with the most beautiful woman I have ever known. "Jennie, I love you" I confessed to her.

"I love you too Jamie! Please fuck me now Jamie, please fuck me hard Jamie, FUCK ME HARD JAMIE," she desperately pleaded. So, with the clamps on her nipples, her asshole buzzing with the vibrator, and her whole body virtually shaking in despair, I positioned myself between her legs, with the "Come Fuck Me Shoes," up over my shoulders, and slid my rock hard 7" cock into her pussy. "Oh, Fuck Me Jamie, FUCK ME HARD PLEASE", she begged.

I fucked her in and out, and in and out, as deeply as my dick would go for what seemed like a long time, but I'm certain it was only a minute or two. Between her beauty, the "Come Fuck Me Shoes", the vibrator buzzing through her anal wall, and the fact that we were both so worked up, it could not possibly have lasted very long. "Come now Jennie, come with me now Jennie, I allowed her. FUCKING Jennie I'm coming, Jennie I'm coming Jennie, COME WITH ME NOW JENNIE.... FUCKKKKKKKK!!!!

We both simultaneously exploded in spit, and sweat, and spasms, and convulsions that lasted a long time. It was fucking-glorious!! The eruption was so powerful, I virtually lost track of Jennie. Thankfully, she and her orgasm were equally lost, in a time-space continuum of her own. It was an un-fucking-believable end, to an un-fucking-believable day, that rocked us both to the core. My only hope is that Jennie enjoyed it somewhere near as much as I did. But I would worry about that, and other details tomorrow.

Tonight, all I had left was energy enough to unbind Jennie, remove her heels, get us both into the shower, then jump back into the clean bed with the woman I've loved for over thirty years. Holding her tight all night long was a true pleasure, especially knowing that we'd be fucking again in the morning. I don't know how it could possibly be as good as today, but I knew with Jennie it would be wonderful.

Stay tuned for episode 2, featuring the trip to Madison Square Garden, Broadway, and maybe, and maybe a little bit more...