Educating Cassidy Ch 02 Postponed

See Educating Cassidy - C1 - Audition for the first part of the story. It does lay down some of the groundwork for this chapter that will help the reader understand a few things that are going on here.

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So Wednesday rolled around. I had gotten up and cleaned up after working out at the gym And was about to start grooming my crotch area when I realized that I couldn't do that if I was actually wearing the cock cage. So I decided I probably ought to wear the cage for the rest of the day. It wasn't going to be too much of an inconvenience, as my physical exertion for the day was pretty much done.

It wasn't exactly easy to get on, just the act of putting it on and what it represented for later in the day was starting to get me hot and bothered. It wasn't entirely comfortable, but it wasn't difficult to move around in either, so I was okay. At the appointed time I pulled the wine out of the refrigerator and set it up on the counter, open and with a couple glasses. I went to the bedroom and set it up the way it had been when she left, though I kept the curtain's closed and the lights on. I was wearing a pair of blue satin boxers, I'd gotten a three pack the last time I was out shopping. The cage was certainly keeping me in check, the first time I'd really felt constrained in it, since I was anticipating what was coming.

I heard the garage door opening, followed a couple minutes later by it closing again. And then footsteps coming down the hall, the carpet muffling them compared to the kitchen floor. And Gwen came into the room, wine in her hand. She was barefoot and wearing a dress. It was pretty form fitting and she really made it look good. The cage had to work hard as I pictured what was under it.

"I'm afraid things didn't work out the way I was planning. Cassidy had a mandatory meeting at the school for her spring break trip to Quebec with her French class. But I didn't feel right just canceling on you, particularly since I've got you caged. So I told my husband that I was working on a group assignment that slave driver Professor Al had stuck us with."

"Um yeah, well, about the cage. I'm not sure it is going to work out the way you were thinking. I get that you want to keep me safe, but it is likely to have the opposite effect from what you want in other respects."

"Go on... "

"Well, while it certainly prevents me from engaging with other women, or even myself, but it is going to make me overly sensitive when it is released. Not having any relief for a number of days, that first pop is going to happen awfully quickly. And I don't feel that I can really keep things clean with it in place, and I certainly can't trim any hairs."

"Valid points. But let's get you out of there and see what happens." She pulled the key out of her purse and proceeded to remove the cage. It wasn't easy as my cock was swelling as quick as it was able, mostly fueled by anticipation, but the view down the top of her dress wasn't helping any. By the time she had worked off the last ring from the tip it was at full capacity, and throbbing.

I was concentrating too hard on not over reacting to the fingers currently caressing my dick and balls to really reply. Even though I had only locked the cage in place earlier that day, the constant reminder of what was to come, as well as the non-stop stimulation it subjected me to were more than enough to prove my point. I was almost a perfect example of what I had just been talking about as I spewed in less than a minute.

"Yeah, that was pretty quick. Just thought it might be a good idea. Maybe I'll slap this on my husband and make him wear it for a few days. I did like the feeling of power it gave me, having this key. Just looking at it would get my juices flowing."

She cleaned up the mess with a combination of her tongue and a towel. Wiping her hands off she stood up on the bed over me and pulled her dress up over her head. Watching it climb up her thighs and reveal the blue panties was quite a treat. A bit further and the matching blue bra came into view. Surprisingly, I hardened up pretty quickly to the vision. Even though I wasn't fastened to the bed, I was frozen by her presence.

"See anything you like?" There actually seemed to be a question in the words, as if she wasn't sure of something. I reached up and pulled her knees toward me, causing them to fall on either side of my torso, plopping her down on me.

"Yes, and you better get a rubber on that cock before I slide it in."

She giggled and slid back a bit, grabbing a condom off the nightstand and after checking the orientation, rolling it down the shaft. Moving back up she slid down onto my cock, the warmth enveloping it with a wonderful sensation. She slowly started moving up and down the length, savoring the sensation. I enjoyed watching her breasts jiggling with the motion, but after a couple of minutes, I decided it was my turn to take charge. I rolled her over and began pistoning in and out of her. Her moans gradually raised in pitch until she was almost screaming with passion as we both reached a climax within moments of each other. I fell off to the side as I collapsed and we laid next to each other panting heavily.

"That was good, very good!," as she finally caught her breath. She rolled over onto her side and looked at me. "Would you be willing to help me fulfill a bit of a fantasy that I have? I'd have to tie you up again."

"At this point, I'd probably do anything you asked! And I do want to keep you happy!"

"Yeah, well, I'm not sure how much is you wanting me and how much is you wanting to get with Cassidy!"

"Given your presence right here and now, I'd have to say you have my complete and full attention!"

We cleaned up a bit and shared some wine before she positioned me on the bed and locked my hands into place. Then she reached into the bag. Removing some materials, she came up to my head and pushed something into my mouth. By the time I really registered what was going on, she had the ball gag firmly in place and fastened. Then she proceeded to tie my legs up, only instead of the bottom of the bed, she used the same bedposts as my hands, tightening them up so my ass was a bit up in the air and my knees were over my shoulders.

I had a pretty good idea of what was about to happen, but there was absolutely nothing I could do, or even say, about it at this point.

"I don't know whether you are going to like this or not, but I've always wanted to try it and my husband wants absolutely nothing to do with it. So this may be my one and only chance! So I hope you do like it!"

The lube hit my ass with a cold splat and she rubbed it in. She pulled out a fortunately small vibrator and slowly used it to push some of the lube further up my ass. After a couple of minutes, she turned the vibrator on and I found myself looking at my own dick growing hard.

"I think you are liking this! At least your body is reacting like it is enjoying the sensations! Okay, next step!"

She went back to her bag and pulled more things out. The first was a harness that she started strapping around her waist. Then she pulled out a dildo, a bit bigger than the vibrator she was using, but with two heads. Gwen slid it into place in the harness and then slowly buried the other half into her cunt. Adding a bit of lube to the shaft, she moved below me and slowly ran the dildo up and down my ass crack. Her eyes were closed as she slowly rocked back and forth. A flood of emotions was running through me, a bit of fear, some anticipation and a lot of lust. My hard dick was starting to take control and push all of the other thoughts away as I wanted her to pay attention to me.

After a few minutes of teasing herself, Gwen placed the head of the dildo firmly on my tight ring and began to push. I tried to relax and slowly she made progress, pushing the head a bit further into the tight channel. I could see in my mind each tiny bit of progress as with deliberate care she forced the dildo into my ass. It took a couple of minutes, but soon she had it buried fully inside me, the other half transmitting the vibrations between our bodies. After the initial pain and discomfort, it was starting to feel pretty good.

With a bit of a pull she began rocking again, only now it was in and out of my ass instead of along my ass crack. The sensation was certainly strange, but I could see the build up of excitement in her face. It matched what I had seen earlier as I had plowed her vagina. Between the pain in my butt and the pleasure I was getting by watching her face, thoughts of my own arousal had left me. When I caught a glimpse of my own erection bobbing in front of my face it was a distraction blocking my view of her pseudo penis as it pumped in and out of my ass. It took longer for her to reach her orgasm, but it was an intense one, clearly etched in her face.

Gwen screamed and shuddered before collapsing on top of me. I was struggling to breathe, the ball gag, my folded position and her weight pushing me to the very edge of consciousness before she rolled off of me, the dildo popping out of my ass in the process. It took her a few minutes, but she crawled up and unfastened my legs, allowing me to inflate my chest fully. It was a bit longer before she removed the gag and I fully caught my breath.

She pulled my face to hers and kissed me, a deep soul wracking kiss, the first time she had ever done that.

"Thank you! That was everything that I had hoped it would be. Thank you for letting me do that, I have imagined doing that since I was a teenager, maybe it's because of penis envy and wanting to know what it felt like." She reached down and discovered that I was wilted and not particularly aroused. "Hmmm, I can tell you weren't really into that much!"

"Actually, I was probably in it more than you would think, but it was less about me and really I was watching you. That really connected with you and seeing your face was a pretty incredible experience. I'm glad I could help you with your fantasy. I'm not saying I want to do it again, but I don't think I'll ever forget it!"

Her manipulation of my genitals was having an effect, as my penis started to harden up.

"I take it you aren't done with me?"

"Not yet. We're doing some things we will not be doing with Cassidy, and this may be the only opportunity we have, so I'm going to take advantage of it. Your turn!" With that she proceeded to unfasten my arms and then grabbing the ball gag, she placed it into her own mouth and strapped it into place. With a twinkle in her eyes, she proceeded to fasten one of her arms to the bedpost and then strapped the leg on the same side into place before throwing her other arm in the direction of the other side. I placed the handcuff on the wrist and checked the tightness carefully. I made some adjustments to the leg restraints before finishing the adjustments. There we were, her hair cascading around her head with her ass up in the air and me with a growing hardon between my legs.

"You sure about this?" She nodded so I continued. I pretty much did the same thing she had, used the vibrator to help lubricate the tight channel. Switching it on started to elicit some quiet moans from her. After a minute or two, I removed it and switched it off, and positioned myself to replace the mechanical device with my own penis. I pulled out a condom and actually grabbed two, rolling one over myself and the other over the vibrator. Adding some lube I slowly began to push into her tight rear channel, moving slowly as she had, not wanting to cause pain or damage. As I made my first bit of progress, I got harder, making it a bit easier to push in. It felt good, but with this position, I wasn't going to be able to bury myself in her the way my body wanted to, I slowly started pumping in and out. I didn't want to push too hard, as it might hurt her back, mine had certainly been stretched more than it should have been.

Knowing the position wasn't going to do it for me, I added to the mix. I turned on the vibrator and slowly worked it into her vagina. The vibrations could be clearly felt through the walls of her two tunnels and felt really good to me. It was only a few minutes of pumping with the added stimulus and she started the tensing up that came before her orgasms. I moved faster and a couple minutes later she went rigid. As she did, her sphincter tightened up on my cock, almost locking me in place and it took me over the edge.

I got her legs unfastened and the handcuffs off, she removed the ball gag before I got to that part. We spent a few minutes getting cleaned up and she kissed me goodbye before sliding out of the garage.

Gwen decided we would try again on Sunday afternoon with Cassidy. No problem for me, the biggest plans I normally have on a Sunday afternoon would be watching the crowds on the lake. I was in the process of laundering the sheets when I realized she hadn't even thought about putting the cock cage back on me.