The three of us were crammed into a tiny den off the living room and the inside of the house was dark except for a couple of lights nearby. My mom had just finished explaining to Jennifer about the three spankings I was soon to receive: laying over her lap in nothing but underpants, bending over the back of a chair with undies pulled down in back, and finally sprawling across her lap completely naked.
Acknowledging my presence for the first time, she ordered me to remove my robe and lay across her lap in my undies. I removed my robe but then hesitated a moment too long, at which point she grabbed my arm, put a strong hand on the back of my thigh, and pulled me over her rather roughly.
It didn't take long to get the first one over with. She was all business on this one. "One"..... "Two"..... "Three"..... she counted loudly as she delivered her smacks. My stomach tightened and my ass stung as I took the hard blows. Before I stood up, she held a mirror behind me and commanded me to examine my ass in the mirror as she gloated over her accuracy: no paddle hole marks anywhere but on my undies. (I dared not point out there were a few marks from the edge of the paddle on my thighs.) As required, I stood up and apologized for what I had done to deserve this punishment.
Moving toward the big leather chair, I was conscious that the room was impossibly small with three people in it. Jennifer was practically right on top of me and I had to pass very close to reach the chair, which added to my discomfort...and the sexual tension. This wasn't like an observer standing way across the room; it was up close and personal. I could feel her gaze as I stood on my tiptoes and bent myself over the back of the chair.
When I was in position, mom held my waistband with both hands and peeled it down to the tops of my thighs, leaving my butt totally exposed. While I waited in that awkward position, she spoke in hushed tones to Jennifer about why naughty little boys should "feel a hard paddle against their bare ass skin." As she talked, she made little slaps and squeezes on my ass cheeks. I'm not sure what that was for, but it made my 'boner' (speaking as the little boy I felt like) stiffer. My stomach knotting up in anticipation of each stroke. With Jennifer now in charge of keeping the count, I hung there helplessly, my feet barely touching the floor, as my bare ass absorbed ten smacks.
Standing up to apologize, I must have been quite a sight for Jennifer, with underpants pulled down below my ass and my hard shaft stretching the fabric out crazily in the front. I could see a huge wet circle, maybe 3 times the diameter of my penis head. Jennifer would be aware of that, too. What must she be thinking of me!
For the final humiliation, I stood beside my mom's lap while she explained to Jennifer that naughty little boys should get their last spanking "completely bare" so they can feel the shame of what they did and never do it again. I couldn't help thinking this was more for my benefit than Jennifer's. Even at eighteen, I felt the helplessness and the shame of being spanked just like I had as a little boy. Only now, with a raging hard on that everyone was about to see, the situation had gotten infinitely more humiliating. Mom instructed Jennifer to come around to the other side of her, so that we were now -- incredibly and impossibly -- facing each other across her lap. This playing field was far from level! Jennifer was fully clothed in her cute dress and black tights, and I was about to be completely naked over my mom's lap for a spanking. I was at a huge psychological disadvantage!
"Okay Jack, now I want you to pull down your underpants and take them all the way off. Then you are going to lay over mommy's lap, just like a naughty little boy does for his spankings. And if I see there's a stiffy in your penis, there will be extra consequences later for that!" I knew she only said the last part for effect, but couldn't she have spared me THAT embarrassment with Jennifer three feet away looking me up and down? Daring a brief eye contact I glanced at Jennifer, wondering whether I would see compassion, interest, disgust. I didn't catch her eye. As I pulled my underpants down and stepped out of them, I am SURE she was staring straight at my penis. I felt a quivering go through me.
Whenever I laid over naked and erect, I had the choice of how to position my penis. There seemed to be a tacit understanding about this ever since puberty when I began manifesting obvious arousal: I could let it flop over her thigh and lay on top of it, or I could move so that it went down the side of her leg. The second way offered less risk of accidentally cumming and making a mess that she would have to clean up and for which she would make me feel even more humiliated. Secretly, I liked the first way but with Jennifer watching closely, I could not chance it. I could just hear my mother telling Jennifer what a bad boy I was as she wiped the sticky mess from her lap. There was another factor, too: If I came during the spanking, I would miss going up to my room, still naked and erect, and shamelessly beating off for as long as I wanted. Using just a slight touch that I hoped Jennifer would not see, I guided my erect penis down the side of my mom's leg as I positioned my body over her lap. Jennifer kept the count again, this time with a noticeable tremble in her voice.
When the count reached ten and the last of the punishment had been meted out and taken, I laid there gathering my wits and then stood up. I uttered my apology with a brief glance in Jennifer's direction and quickly exited the room, reaching down to pick up my underpants and robe but not bothering to put them on. Tiptoeing up the stairs and down the hall, I entered my room and shut the door.
After a few long, shaky breaths in an effort to collect myself, I recounted what had just happened. As always, I stood in front of the mirror enjoying the sight of my erect penis, then turned my backside to the mirror, looking over my shoulder to evaluate the damages. I bent over to look at my ass from that angle and imagine it bring spanked ... and seen. Feeling terribly hurt, shamed and humiliated from the experience, masturbation was how I would soothe those feelings whilst savouring the awkward sexiness of it all.
Taking a few steps to my bed, I piled two pillows and laid over them with my burning raw ass sticking up in the cool night air and my hard dick sandwiched between pillows and sheet.
Ahhh, it felt good! This moment was for picturing the whole scene through Jennifer's eyes. What could she see? How did it look to her? How did she feel about it? I really had no idea, but loved pouring over these matters in detail. As I humped the pillows slowly, the feelings in my stomach persuaded me to stand up and beat off.
Retrieving the bottle of lube from my dresser drawer and applying a few drops each to my hand and penis, I admitted with a flushed face that my mom must have a pretty good idea of what I do in my room after spankings. Jennifer, however, wouldn't have a clue.
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