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.

To this point Cassidy has been pretty quiet, but there had been a few gasps and low moans as she watched her mother getting eaten out. I was thinking that the cushion of that chair was going to need a good cleaning!

Gwen had caught her breath and rolled off of me. “You are pretty good at that! I think the pillow being there helped!” She adjusted the stocking on my head as it was askew from her thighs rubbing against it. She looked over at her daughter and gave her a smile. “I think I can help you out a bit.”

Gwen went to her bag and pulled out the small penis shaped vibrator. She showed Cassidy the setting before sliding a towel under her bottom and placing the vibrator under her. It was a matter of moments before the soft humm of the vibrator joined the sound of boats out on the water. I was straining my neck trying to see what was happening, but the bed didn’t give me a very good view of the chair.

“Have fun, but watch what we are doing.” Gwen then proceeded to open a rubber and carefully showed Cassidy how to make sure it was oriented correctly before rolling it on. She then straddled my body in a reverse cowgirl. She used her hand to line me up and then slowly sank down on my cock. She was definitely well lubricated and I felt her bottom out with her butt cheeks hitting my pelvis. I so wanted to reach out and grab those hips, causing me to moan with frustration. As much as I wanted to thrust vigorously into that juice tunnel, the restraints kept me from doing more than a slight wiggle. Gwen moved slowly, teasing me as she went with an occasional tickle to my balls. She had a great technique, a slight rotation of her hips and the ability to tighten up her vaginal muscles to really squeeze things. Even with her amazing ability, it was a good ten minutes before I felt things really getting close to the edge.

But just before I reached a climax, Gwen gave a shudder and a slight scream as she was able to get herself off. And that seemed to trigger Cassidy, as I heard her gave a bit of a scream. I could only assume the vibrator had helped her reach an orgasm, even bound to the chair. And found myself flopping in the air as Gwen pulled up and off of me, depriving me of the last few strokes that would have let me reach my own orgasm.

I moaned in frustration, “I’m so close, don’t stop! Please!”

Gwen laughed, “I never promised you anything more than two orgasms. My only requirement was you be able to cum twice and I didn’t care about the third time. However, I’ll give you a choice. First option is we leave now and see you on Wednesday for the next session. Second option is I’ll use a hand to help you cum, and then I’ll lock you in the chastity cage until we return.”

I was a bit surprised by the choices. I had thought she had given up on the cage idea, given my valid points from earlier in the week. But, my little head was doing the thinking and an orgasm now was worth more than something days away.

“I know what you’re thinking! I’ve decided that seeing something happen quickly would be a good experience, after all, her first time with a young man is likely to experience a challenge when it comes to sensitivity and being able to control one’s self. And even if you chose the first option, I suspect you’ll be pretty excited anyway. So which do you want?”

“The cage! I’ll take the cage!” I knew I would be able to pick the lock again, so that wasn’t a problem. And my previous experience with it let me know that even a few hours in the cage would achieve the desired results when it came to sensitivity.

Gwen bounced off the bed and tossed a pillow on my face, I couldn’t see what was going on. I heard her moving around and heard something heavy being moved on the carpet. Then came the ripping sound of velcro, but my legs didn’t loosen up. Was she just going to take Cassidy and leave? Then to my relief, I felt a hand around my shaft. It squeezed and began to stroke it with a tight grip.

“I told you I would use a hand, I didn’t say it would be my hand! Besides, I can’t get the cage on you when you’re fully erect.” The thought that it was Cassidy’s hand on my cock brought me back up to full size. The tightness of the grip was slowing things down a bit.

“Is this right, mom?”

“Not so tight, dear, it is pretty sensitive.”

Just hearing the two of them talking about my cock was enough to send me over the edge. I’m not sure what the sound was that came out of my mouth, a cross between a scream and a moan and I felt my cum pooling around the base of my shaft.

“It didn’t shoot, mom, it just sort of oozed! Did I do it wrong?”

“No, no, just being the third orgasm in the last hour or so, it’s actually a wonder that anything came out! Now, let’s get the two of you cleaned up a bit so I can show you the cage and how it goes on.”

Again she used a washcloth and towel to clean me up. The pillow still blocked my view, but I could feel the metal ring being placed around the base of my shaft and balls and the cage around the wilted shaft. There was a click and I knew that lock had been secured.

“There, that will keep him out of trouble until we come back!”

“Mom, do you do that to dad?”

“No, at least not yet. I’m thinking about it though! And here, I’m giving you the key. Don’t lose it, or he’ll be in trouble! But it will remind you of what is coming in a few days!” I heard more velcro ripping. “Okay, go use the bathroom in the hallway and go to the kitchen, I’ll be out in a few minutes.”

The pillow was moved and the stocking pulled off my face. It was a bit of a relief to have things freed up, it was just a bit tight.

“You, sir, did very well! I wasn’t too surprised by your choice of the cage, I know which head was making the decisions at that point! And that was when I decided to give you a bit of a reward and let Cassidy help with things. Shall we try Wednesday evening for the next session?” She unfastened my legs and then the handcuffs. I groaned a bit as the pressure on my shoulders was relieved. I was pretty tired and there was still a residual ache in my guts from the rap on my ball.

“You’re not going to let her bust my balls, are you?”

“No! I will not allow that. Once is enough to make the point and get her to realize just how much control she can have in a situation like that.”

“Okay, Wednesday will work for me!”

Once again, I waited until they were out of the driveway, watching from behind the curtains. Once I had everything locked up tight I grabbed my lockpick set. It didn’t take as long as the first time, but I was again able to pop the lock. The thought that Cassidy was wearing the key was certainly going to weigh on my mind for the next three days. I went on with my week and waited anxiously for Wednesday.

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