See Educating Cassidy Chapters 1, 2, 3 and 4 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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The Coach
Following the normal process, the two women arrived as expected. Gwen came back first and arranged the stocking mask over my head. She didn’t put the blindfold in place like the last visit, and I wasn’t going to remind her. After she was satisfied with the stocking she went and got Cassidy. When they came into the room together Gwen walked Cassidy through the process of fastening me securely to the bed.
Cassidy really surprised me. She had dyed her hair a bright blue that really did a nice job of pulling out the blue of her eyes. It was really the first time I had gotten to see her naked and it was a sight to behold. There was a lot to be said for her looking like her mother. Obviously younger, her breasts had less of a sag to them, I was no expert, but they were probably around a 34 B, with nice pink nipples which were at full attention. They were big enough to be really attractive.
She had also shaved since our previous session, her mound was clean and bare, there was just a bit of her vaginal lips pouting out of the crease between her legs. Her ass was smooth and curved around perfectly. Her mother’s, while just as shapely, did have the dimples of cellulitis scattered around them, not that I minded! I was drinking in her body and our eyes met. She gave me a wink with a bit of a grin that gave me some pause. What was she up to?
“Some men like to be confined, and it is a relatively simple kink to accommodate without being dangerous. But you need to be sure that you aren’t cutting off blood circulation or causing bruising. If you squeeze the cuffs too tightly they can really hurt. If you go too far you have to use the key and open it to relieve the pressure. Velcro bands like the ones on his ankles are easy to use and surprisingly strong. If you use rope directly on the skin, you want to make sure it is soft, and not the hard nylon stuff that can chaff and cut, unless the guy is into that sort of thing.”
Once I was in place, Gwen moved over to the chair and sat down. To my surprise, I heard velcro again. “Cassidy, come fasten my hands in place. I can observe and watch, but won’t be able to interfere in anything, even though I may want to.”
Cassidy made her mother stand up and moved the chair to the foot of the bed, rather than the side where it was. As she started fastening her mother into place, I was still focussed on Cassidy’s body as she bent over her mother to put the fasteners on. My primary thought was on how I wanted to kiss that delectable ass that was pointed at me and bury my tongue into the folds of her pussy. Once she had completed her task and her mother was in place, Cassidy went back to the bag. She removed the ball gag and I wondered what I was in for. Only she went over and forced it into her mother’s mouth! I was definitely surprised, but decided that I needed to be careful, we were entering unknown territory.
“Now, xxxx, you’re going to behave, aren’t you?” She was looking me straight in the eyes and I nodded, afraid to say anything. “Trust me, you will like all of this!” Going back to the bag, some more constraints were brought out. She replace the handcuffs on my arms with longer rope and velcro fasteners and refastened my arms to the same headposts. I had a lot of room to move my arms, but she had me walk my butt down the bed as far as I could and removed my leg fasteners. I sort of slid off the bottom of the bed, my arms stretched out now. Cassidy reworked the leg ties to basically have me on my knees with my back arched over the end of the bed. My cock was pointing straight out at her mother at this point, whose eyes were wide as she watched her daughter’s manipulations.
I wasn’t sure where this was all headed. I found it extremely tantalizing, a number of scenarios running through my mind. But I wasn’t ready for what happened next. Cassidy proceed to place a condom on my shaft, nothing unexpected there. But then she turned her back to me and slid down my body, lodging my cock right into her pussy. It took some wiggling on her part, but it didn’t take too long and I was completely buried in that tight tunnel, obviously not the first time something had been in there. Gwen was trying to yell into her gag, but everything that came out was muffled and sounded more of a whimper than anything.
Cassidy then bent forward and buried her face in her mother’s pussy. If her mother had been trying to scream before, her efforts were doubled at this point, but it only succeeded in constricting her air flow to the point she passed out. Gwen’s head rolled onto her shoulder and her entire body went limp. Cassidy didn’t panic, but loosened the gag and made sure she was breathing properly before turning her attention back to her mother’s vagina, the place where she had come into the world. It was only a few licks and Gwen was back with us, her eyes slowly coming into focus. Meanwhile, with each little lick, Cassidy would rock back on my cock, building up a rhythm as she slowly fucked back into me. Those gorgeous ass cheeks were sensuously bouncing against my crotch, her tight tunnel rubbing the length of my shaft. I was glad there was a layer of latex there, or I would have been shooting my load a lot sooner.
There was little Gwen or I could do, Cassidy was in complete control. But the view of her head slowly circling her mother’s mound was enough to make it really hard for me to keep control.
With a moan I declared, “Cassidy, I’m not going to last much longer! This is just too good!”
She giggled and reached back with her hand and grabbed my balls. A quick squeeze and a tug, nothing too drastic, was enough to slow things down for me. She raised her head out of its valley and said, “Keep talking to me and I’ll keep reigning you back in. I don’t want you coming before I’m ready!”
With that she returned her attention back to her mother. Every minute or so she would remind me who was in charge with a tug on my balls, which were threatening to release a pretty significant load fairly quickly. When not tugging she was fingering herself, rubbing her clitoris as she continued working on her mother. Another five minutes and Gwen was shuddering with an orgasm provided by her daughter’s talented tongue. With that, Cassidy slid off the end of my shaft and turned around. She quickly remounted me, her tits bouncing in front of my face. She didn’t even acknowledge the fact that I let loose a load within a minute of her remount. The cum leaking out of the bottom of the condom did nothing to slow her down from riding me to her own orgasm.
After a couple of aftershocks, Cassidy let my softening tool slip out of her. “Well, this stuff is toxic, so I better take care of it.” She patted off to the bathroom and I heard the bidet being used. She returned with a couple of washcloths and proceeded to apply one to her mother’s face and then used the other to clean up my groin and remove the messy condom.
“Okay, coach, I’m going to remove your gag, but I don’t want any negative comments about what just happened. Constructive criticism only! And I have to figure out what I’m going to do next, I didn’t really get past this scenario in my mind. But it was good, right? You enjoyed yourself?”
With that Cassidy removed the ball gag and stepped back. Gwen worked her jaws to give some relief to her face muscles. There was silence as the two of them stared at each other. If there was going to be an explosion, I was going to be at ground zero, so I hoped that things were going to remain civil. The scene was tense enough that I wasn’t really aware that my back was hurting from the position, and my knees were a bit raw.
The silence was finally broken, “Please unfasten me.” Gwen said it softly and without any trace of anger. Cassidy looked at her for a moment and then nodded and started taking off the leg restraints. Once she got the arms loosened, Gwen stood up and rubbed her wrists for a few moments, before moving over to me.
“He’s been restricted in this position too long. His back has got to be hurting and I hope you haven’t caused him any permanent damage.” She unfastened my arms and pulled me upright so my back was at least straight. Then the two of them removed the leg ties. I was able to pull myself up to my feet by leaning on the bed. I didn’t say a word, afraid anything I said might start an avalanche of yelling.
The two looked at each other again, intently staring at their eyes. Gwen finally moved. She walked over to Cassidy, and with a gentle, but firm, push, forced her back on the bed. And then dropped to her knees and proceeded to bury her face in her daughter’s crotch. Cassidy gasped when the tongue made contact. I sat in the recently vacated, and soaked, chair and watched. Despite having just had one of the most intense orgasms of my life, I found my cock raising to attention in response to the view in front of me. Within moments I was at full length.
It didn’t take a lot of thought about what was going to happen next. Even though my knees were getting rubbed raw, I placed them between Gwen’s knees and aimed my shaft at her pussy. I slid in easily and her groans, muffled by the thighs of her daughter, let me know I was meeting her needs as well as my own. I hadn’t thought about putting a condom on, but it was too late for that now. The three of us worked our way to a nice rhythm, my thrusts pushing Gwen’s face into Cassidy’s crotch and the back and forth motions lasted a lot longer than I would have expected. It was almost ten minutes before the chain reaction started, my fingers were stroking Gwen’s mound with one hand and the other was playing with her breasts as they rocked back and forth with our motion. Cassidy was clutching the back of her mother’s head as the tongue was applied with the love of a mother. Gwen shuddered to orgasm, the tremors in her body transmitting to Cassidy and setting off her own climax. Their screams of pleasure triggered my own rather feeble climax, it wasn’t nearly the volume of my previous one, but was very satisfying, nonetheless.
I helped Gwen to her feet and laid her next to her daughter on the bed. My turn to get some warm wash clothes. After a few minutes Gwen got to her feet and grabbed each of us by a hand and pulled us into the bathroom. A couple of directing pushes and we were all three in the oversized shower stall, the multiple shower heads cascading warm water over our bodies. Even with all the events of the past month, it was the most sensuous experience and the one he remembered most vividly in the future. None of them said a word as the three of them slowly soaping each other up and rubbing their bodies together as they let the water flow. The after glow as they washed each other’s backs and then dried each other off was memorable.
As the two women combed and brushed out their hair, I went to work stripping the bed. It was a bit strange to have the two of them there, fully naked and me not being tied up. I had the first load of towels in the washing machine and started to get myself dressed as they did the same. I pulled a t-shirt out of the drawer, not paying a lot of attention to what it was. Cassidy immediately came over and started going through the drawer, looking at the logos and events they commemorated. Eventually she pulled out one from a concert I had attended in college and pulled it on over her sports bra. A quick twist and she had knotted it to show off her belly button.
“There, now I have a souvenir to help me with these memories! And, if I ever show up at your door wearing it, I’ll expect you to let me into the house and proceed to fuck my brains out!”
Afterwards
Even after Cassidy headed off to school, it was difficult to maintain my composure when I was around Gwen in social situations. Pretty much anything she would wear would remind me of at least one of our sessions, but I managed to keep in control. That isn’t to say we avoided each other. On a rare occasion she would send an email and ask if I might have a few minutes for her. Unless I was really busy and couldn’t change my schedule, I always said yes. Oh, and she did get an A in my class.
I would see Cassidy once in a while when she was home from school. She would always greet me with a big smile and a hug and we would chat for a few minutes. I’d ask about her classes and tease her about boyfriends. And watched that amazing ass as she walked away, trying not to be too obvious. And on three separate occasions before she graduated college, she actually showed up on my doorstep, wearing that t-shirt.