I put a couple of logs in the fireplace and turned on the gas. Tons of things were going through my mind, not the least of which was trying to determine how far this would go.
A back-rub was innocent enough. But was I actually going to try and put the moves on my mom? And would she be receptive to that? Instead of a scheme that had to play out, everything was sort of out in the open. Mom had caught us, my sister and I, laying in bed exhausted after just having finished an oral exchange.
Caught, Jill then laid out her plan, and mom seemed to take it in stride. Now that I went back over the talk in my mind, she had not consented to anything sexual, but neither had she denied it outright which one might expect. In fact she seemed to have side-stepped around it. Or was that just wishful thinking, that she might actually play along?
The wood started to crackle as the fire caught. I closed the fireplace screen and turned on the stereo to light music. Then I turned down the overhead lights to a dim setting.
Just then Jill came in with drinks. She had a bottle of wine with two wine glasses already filled. Plus a bottle of whiskey and two shot glasses. I looked at her and she back at me. "Just in case anyone needs something stronger," she said lightly. "Liquid encouragement."
Mom came in wearing her bath robe. She looked at the tray with drinks, noticing pairs. "Seems like you're short a glass."
Jill answered, "Well, I thought this would be enough for the two of you."
"This is your plan," mom replied. "I expect service from you too," she said as she took a glass of wine and took a long pull, eventually finishing in quick order.
"From me?" Jill questioned.
"While Jack gives me a back-massage," she now dis-robed, revealing a nightie underneath. "You can start on my feet." She offered the empty glass which Jill now refilled. Mom took it and sat down on the sofa, then put her feet up on the coffee table.
I downed a shot of whiskey. Jill re-filled it, then took the other and took her own shot. I walked around behind the sofa. Jill sat on the low table, next to mom's feet. We looked at each other. The room was warm from the fire. The ambience was soft and romantic, light music played and firelight flickered on the far wall.
There was a moment of silence, of anticipation, of what might happen.
I looked down from above and behind her, this lovely woman with a slender body in her night-gown, waiting for me. My mom was waiting for me to give her a massage. I gently placed my hands and began to work her neck and shoulders. Her chest exhaled; she must have been holding her breath too.
It could have been a simple backrub, but it was so much more than that. It was erotic and romantic. Time might have slowed, or I was just caught up in it. It wasn't just that I was touching her skin. I was feeling her essence with my fingers, my hands. I kneaded her shoulders and upper back, to occasional oohs and aahs while Jill worked on her feet and toes.
After about 15 minutes, I leaned over and looked down, noticing the tops of her breasts from my vantage point. I could see her hard nipples pointing out against the sheer fabric of the nightie. I imagined caressing them and squeezing her soft breasts, maybe even while putting her nipple in my mouth, gently biting...
"See something you like," mom asked. I was caught staring at her chest! Had she seen the look of lust on my face?
But instead of pressing the issue, she changed the topic. "That was lovely, but it's time for a different position." She stood, taking another drink from her glass of wine. Then she removed her arms out of the nightie, but still held the fabric to her chest. She laid face-down on the sofa, her bare back exposed. She crossed her arms under her head and rested on them.
"You may resume now," she instructed.
I walked around the sofa, stopping to take another shot. I leaned down to touch her back. I couldn't get much pressure and the angle wasn't right. Mom noticed the dilemma I was trying to solve.
"You can straddle my hips, if the weight is evenly distributed it won't be too much."
I gently placed my leg over and sat down on her, with only the sheer nightie between us. I thought I felt her squeeze her buns, and a tingle went through me. But I sure if that was intentional or just a response to my weight.
I tried to focus, so I leaned in and massaged her shoulders again, working on her upper back. "Mmmmm, that's nice, your hands are so warm," she cooed. After some time, she gave me more direction. "You can reach my lower back nicely in this position too."
I worked my hands down and in circular patterns. Occasionally I would gently then firmly use my knuckles to need into her, as I worked into the middle and then lower back.
I got as low on her back as I could, nearly at my own legs. Any more and I would be touching her butt directly. That's when I thought about it - I was sitting on her, and my groin was the sensory input sending information to my head about her soft, warm ass. I tried to block it out, but that only made me think about it more. I shifted my hips and the feeling of her bum under me made me excited.
I continued the lower back massage, but I was obsessing with her bottom now. Periodically I would move enough to put pressure on her, to angle into her, to rub against her. And periodically she would push back in response. After a few minutes of this, I risked more, and shifted my hips so my penis lined up between her ass cheeks. I leaned in, presumably to reach her shoulders, resulting in me pressing my manhood into her bum through my shorts.
She squeezed her buns again -- it was unmistakable this time. And my cock was hard enough to be recognized for what it was. I imagined what it would be like to slide it into her warm pussy, to move in with long strokes, with her ass against my groin. Would it be heaven as I imagined it.
"Seems like someone is enjoying this a little too much," she replied with a wicked smile. But did she mean her or me? "That's a different kind of massage," she said as her body shifted and I lifted up, not sure if I had gone too far. She raised to finish her third glass of wine, then laid back down.
"You may use your hands."
Did she mean just use my hands on her back? Or did she just give permission for me to massage her bum as long as I only used my hands? I was clearly grinding on her, so it seemed vague -- was she side stepping the issue, or was it wishful thinking again?
I had to test the theory. I scooted back slightly, off her bottom and sat on her legs, then resumed. She stretched out and I could feel her body relax underneath me. I worked her lower back in a circular pattern. On each pass, I went a couple inches lower. Eventually I was touching her bum, and I decided to stop trying to be accidental about it entirely. Either she would stop it and the massage would be over, or she enjoyed it and I could proceed.
