Educating Cassidy Ch. 03 – Observe by AlbericGrunnion,AlbericGrunnion

See Educating Cassidy – C1 – Audition and Ch2 Observe for the first parts of the story. They do lay down some of the groundwork for this chapter that will help the reader understand a few things that are going on here.


Gwen and Cassidy arrived pretty much as expected. I had laid out the wine and set up the bedroom the way it had been for the audition. The blinds were staggered to block out most of the light but still allowed for light and even a bit of a view of the lake. It was a pretty nice view and I would normally have been out on the deck reading or grading papers while enjoying a cold beer and watching the boaters. I tried to avoid boating on the weekends, the traffic and weekend warriors out for their skiing fix were too much of a risk. I had moved the nice reading chair to a position in the corner near the foot of the bed, I figured it would provide Cassidy a better view of what was going on.

Gwen came in and after looking over the room she smiled. I was wearing the red shorts today. She was once again wearing a pair of tight leggings and this time a sports bra, her midriff bare. I don’t care what the situation was, that ass in those leggings would have commanded my full attention anywhere.

“Okay, this is going to be a bit of a shock to Cassidy, but here we go!”

“Why a shock, you mean you haven’t told her?”

“Oh, I explained everything, but I left a few things out. It’s just a matter that she wasn’t sure who you are, and I don’t think she will be expecting you to be safely restrained. I’ve decided that I should probably restrain her as well. That way she won’t get in the way. And I thought about another thing you mentioned. We can work to keep this a bit more anonymous.”

“And just how do you plan on doing that?”

“Very easily!” She proceeded to fasten the restraints on me and then brought out a black stocking. Rather than putting it on, she rolled it over the top of my head. With a few adjustments, she had the thicker top part covering my hair and ears, while a thinner double layer covered my eyes. I found I could see pretty well through the layer of material, but it totally covered the top half of my face and my hair, even my ears, while leaving my mouth exposed and not blocking my nostrils.

“There, that gives you some aura of anonymity. If you can keep anything you say to a whisper, it will help. I have decided to gag you to start with, but we know that isn’t going to stay in place all afternoon. Anything else before I gag you and bring her in?”

“How about a pillow under my head, so I can see a bit better?”

Gwen took a pillow and made sure it was properly placed. She placed the ball gag in my mouth and securely fastened it. She then teased my cock with her fingernails for a minute or two, just to make sure it was fully erect, not a problem as I was anticipating what was to come. “Okay, it’s showtime!”

I heard two sets of footsteps coming back a minute later. I could see that Cassidy was wearing pretty much the same outfit her mother was. She was a bit smaller than her mother, but a very similar build. She was a soccer player and her legs and butt showed it. Her hair was longer and pulled into a loose ponytail. She was staring at me tied to the bed as Gwen sat her down in the chair and I heard the familiar velcro rip.

“I want you to focus on what is happening and not be distracted. Now hold still while I get your arms.” I could turn my head, but my own arm was blocking some of the view. Cassidy’s arms were fastened to the arms of the chair, based on the sounds, her feet probably were as well.

“Geez, mom! This is really making me uncomfortable!” Her voice was pretty similar to Gwen’s, but a bit softer and slightly higher pitch. Gwen’s had a sultry timbre to it that I liked.

“Uncomfortable as in emotionally scarring or is your body reacting to the stimulus?”

“Well, I’m getting pretty excited!” as she wiggled in the chair.

“Okay, that is perfectly natural. So let’s get to it! The first thing to realize is that it is pretty easy to tell whether a man is sexually excited. They have a very difficult time trying to conceal it. I’m sure you’ve noticed some of the boys in your classes waiting until the room has emptied before they go to leave, and are holding their backpack in front of them rather than throwing it over their shoulder. See what I mean?” I was serving as a good example, my cock was at full size, creating a tent in the boxers. I was at full extent, each beat of my heart causing it to jiggle with excitement. A few more beats and it was going to pop right through the fly and into the open air.

Gwen flicked it lightly with her finger, just hard enough to cause me to yelp into the gag and my cock to slide out of the satin confines.

“I would say this is slightly larger than average, at least from my experience. And a guy doesn’t have a lot of control over his erections, something as simple as seeing the curve of a girl’s butt when she bends over a bit this is enough to get the younger set hard. Older guys are a little bit more jaded and don’t get unexpected hard ons as often. This is the sort of view you are likely to get from a first time with someone. You can see that it is hard and it is difficult to hide it, and it makes it difficult to walk. Guys often have to shift things around especially if it has gotten hard while in an awkward position, such as pointing down their leg.”

She moved my cock around as she demonstrated, which elicited a couple of good moans from me, partially because of the roughness in which she handled it and because any attention was good attention. She pulled my balls out of the fly into the air and proceeded to explain various aspects, such as their extreme sensitivity and how even a relatively light hit could cause a painful reaction that could put a stop to amourous activities. And then Gwen flicked my left nut really hard. I screamed as the pain rolled through my body, the gag hardly containing my howl. Any trace of a hard on that I had was gone in a matter of seconds.

“So if a guy won’t take no for an answer, this is one way of slowing things way down.” I was trying to catch my breath and avoid puking as my guts continued to reverberate as the pain slowly subsided. “So if this happens accidentally, you can help him by rubbing his lower stomach. After a few minutes you can gently massage his balls.” She matched her actions to her words and the pain started to go away, but a dull ache continued to exist for a long time. And the attention to my ball sack was starting to return my cock to its previous state of full erection. With this distraction going on, she unfastened my one leg and worked it up through my boxers so it could be slid down out of the way, before refastening my leg securely.

Gwen proceeded to walk through a pretty standard hand job from that point on. She showed the location of the various parts and where I was most sensitive, using her nails to gently run up and down my shaft. She demonstrated how to tell when an ejaculation was getting close, the balls pulling up tight to the base of the shaft. She also explained that while she had helped me clean up a lot of the excess hair around my penis, that I had been keeping it nicely groomed and that a good partner would do that.

Then she began stroking, holding the skin in place so that her hand wasn’t actually rubbing across the skin and explained that if there wasn’t any lubrication, this was a good way to avoid rubbing the penis raw. Once she had gotten me warmed up, she showed Cassidy the drop of pre-cum that was forming at the tip. And how to rub it around the head as it was slippery. And warned her that even though it was called pre-cum, it could contain viable sperm and that she needed to be careful in handling it. And called her attention to the fact that she was still fully clothed.

Then Gwen got the lube out and proceeded to jack me off with one hand while gently playing with my balls with the other. No doubt her hand felt really good, even though I still had an ache.

Once I got to the point of no return, she allowed my orgasm to shoot up my belly and some even hit my chin.

A wet washcloth and a towel were applied and used to clean me up. Then Gwen did a bit of a strip tease. Not that there was a whole lot to take off, the sports bra went first and her breasts bobbed as she moved, the dark red nipples starting to harden in the cooler air.

“Now, I would never recommend hitting a man in the gonads like I did, even though it was relatively lightly, you saw what pain it caused. That was the main reason for the ball gag, it was a given that he would scream. And he did not have any warning about that happening.” Turning her head to look me square in the eyes she continued, “And it will not happen again! I promise!”

She smiled as she then reached over and removed the ball gag. “Open wide!” and she sprayed something into my mouth. I’d guess it was a breath freshener from the tingle a burn, it had a minty taste to it and it made my mouth feel better after the ball gag. “It is always a good idea to take care of someone in a vulnerable position. This will help remove the taste of the gag and help get things lubricated. You have to be careful when they are on their back as well, because if they can’t swallow, they can choke on their own saliva.”

She slowly settled onto my face, her voice was now muffled a bit by her calves being so close to my ears. This was more like it! I dove in with gusto and was a bit harder on her, biting at her outer lips and clitoris. I wasn’t going to let her off lightly, but wasn’t going to go too far, as that might shut everything down. And I realized that there was no way for Cassidy to see exactly what was going on. It seemed to stimulate Gwen as her moans were definitely louder than normal, or perhaps it was the idea that her own daughter was watching her get off that increased her excitement. And with that thought I was fully erect again, Gwen’s breath tickling the short hair around my balls and shaft. With a scream she tensed up and shuddered, before collapsing on me, one of her breasts pressing into my crotch, stimulating me even more as she took huge gasps of air into her lungs.

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