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.