One Possibility Pt. 04

She felt so strange and empowered, she began laughing to herself. She turned to look at his face and suddenly he looked ridiculous to her. He sensed it too and he began laughing at himself. They were both laughing at how crazy fast they both had escalated things.

"I lost control," she said. "I've never let myself do that during sex."

"I absolutely adored all of it," he said. "You did look crazed," and he laughed again. She feigned annoyance then began laughing herself. She was slowly palming his smooth, recently beaten and bruised balls, gently squeezing, rubbing, and fingering them.

"Why do you like being humiliated?" she asked.

He wanted to tell her the truth, but he was worried this would be something she would judge him harshly for.

"My mom walked in on me. I was wearing her panties. I thought I was home alone, no pun intended, and I was on my bed with my legs spread wide. I was rubbing the underside of the tip of my cock against the satin fabric of her Vanity Fair bloomers. That's how I used to masturbate, before I read how to really do it in The Joy of Sex."

"Wait, what?? I don't believe you," she challenged him.

"Which part?" he asked.

"That your mom walked in on you," she said. "That you were wearing her panties," she added. "And that you didn't know how to masturbate," she paused for effect. And then added, "so, I guess all of it," then she laughed.

"Ok, I'll start with the masturbation part," he could feel her rubbing his balls, it was like she was coaxing all of it out of him. "I had no idea what masturbation was. I didn't know it existed. I knew my penis would get hard, and I knew it felt good sometimes. But, I didn't know it could feel so good that it would shoot out sperm, I didn't even know what sperm was," he laughed out loud at how naive he was back then.

He was looking at her pink thong and he could see her wet pussy lips pressed against the satin material. He lazily let his hand fall in he lap and he mimicked her hand's contact that she was applying to his balls by applying the same touch to her. He rubbed her pussy through the thin material.

"I'd learned that I could rub the underside of my cock against the inside of my hairless thigh and that would make me feel good. Like so good, that I would rub it for long stretches feeling the tingling sensations, but then after a long time rubbing it, I began to feel something was wrong and the tingling sensations changed into a burning sensation. I always stopped myself before anything happened. I remembered that something warm and wet would come out of the tip of my penis and lay streaks across the inside of my thigh, and that would frighten me as well. I didn't know what it was so I tasted it. It tasted sweet, but it scared me nonetheless, I thought I was doing something bad."

"Damn, I thought girls had it rough," she empathized. "I guess it would be strange if you really had no idea about any of this."

"Yeah, it was. But, as I said, I hadn't found my parents' copy of the "Joy of Sex" yet. A couple more days and I would have known a lot more about masturbation. As it happened, a week after this encounter, I was going through my parents' room again, looking for more panties and I found their copy in the bedside table, under a stack of Cosmo magazines. Until then, I'd found my mom's panties and the feeling of the satin material against my penis was very enticing."

"I understand your fetish for panties, I love women's lingerie," she said. "But I still don't understand how you masturbated in them."

"They were very big on me, but the elastic waistband fastened neatly around my waist, and the satin or nylon material of the actual panty hung loosely on me, like my ass, penis, and balls were swimming in satin," he said.

She laughed at his vivid description. "That explains a lot," she smiled. "So you what, swirled your penis on the satin?"

"You gotta remember, I was still hairless, the first time putting on those....my mom's Vanity Fair panties, I was doomed."

"Why doomed? I thought you like this," and she spread her arms around the room, indicating the feminine lingerie, the makeup, the wig, the heels, everything indicated how much he adored this theatre.

"I wouldn't trade it or wish it away, but there are times I wonder what it's like to be dominant. I have been dominant in the past. But it always felt like I was doing it because that's how porn portrays sex. I didn't ever feel powerful or masculine as a result of playing the more dominant role. I felt power and intensity most when helping my partner orgasm. And that didn't happen until I was 25. Once I learned how to listen and respond in bed, how to be in every moment, to be with my partner completely, then I realized it wasn't about "hard fuckin" it was being present and in service to her. I would become like a sex toy, always in service of my partner. If that led to hard dominant fucking, then I did that, if it led to servicing her with my mouth after fucking her so she could orgasm too, then I did that. That's when I discovered how god-damned sexy and how much women love a good foot massage."

They both laughed. "So you've told me, and yet I remain sceptical," she said laying back, perpendicular to his body, her hot ass just resting against his side torso, and then putting both her naked and smooth feet flat onto his chest. She felt his strong hands, silky smooth begin fast work on the soles and arches of both her feet at the same time.

He stopped rubbing her pussy and picked up her feet in his hands. Something he'd masturbated to a thousand times imagining. He began his ritual, starting on the arches of both feet, one in each hand.

"You haven't finished telling me about your masturbation technique," she said pointing to her feet, as if to say, don't stop massaging.

"Yes, so my mom's Vanity Fairs were sexy the first time I laid eyes on them. She had a full top drawer dedicated to panties, slips, bras, stockings, and gowns. I just grabbed the silkiest looking pair and as soon as the elastic bands around the legs grazed my ankles, slipped up my hairless legs, and then pressed up against my hairless balls I had been fundamentally changed forever.

"I would walk around, look at myself in the full-length mirror in their bedroom. I twisted and moved in a way that made my reflection feminine-looking. In this movement, I felt this incredibly sensuous feeling each time the underside of the tip of my penis would touch the silky fabric. I began swishing my penis so contact between these two scintillating forces would occur more frequently. Soon, believing no one was home, I ran to my room and flopped down on the bed. I found that by spreading my legs wide open that the front panel of the silky panties would stretch, and then tighten and press my penis flat against my stomach seeming to encase the underside of my shaft from root to tip. Naturally, I started humping. This created this silky and feathery sensation that made my penis hot and angry. I'd never ejaculated, masturbated, hell, I literally had no idea what sex even was. My penis kept getting hotter and harder, I kept humping and humping, and I guess I was making enough noise that I heard my mom ask from nowhere if everything was alright. I open my eyes and with my penis literally ready to burst she walks in and sees me like this."

She is staring at him in disbelief. "You're lying, you're making this up from some fantasy."

"No, but because I was so hot, hard, and seemingly on fire down there, I was past the point of no return, past the point I'd ever let myself get to alone. You have to realize, I had no idea what was about to happen, not when or how or why, nothing, I had zero clue orgasm was something in the universe. So, when the heat started to catch fire, I was ill-prepared. With my mom standing over me I finished mid-hump and after what seemed like an eternity, I felt my penis explode. My mom ran out of the room yelling at me to make sure no one's home next time and I ejaculated five or six more times and by the time I'd finished my penis was a shrunken pea."

"Wow, just abso-fucking-lutely wow!!!" She was stunned.

"I lay there humiliated, completely limp, and yet, I felt arousal," he paused. He kissed her toes as he held both feet, gripping her around the arched part of her feet, his thumbs pressing into each arch at varied pressure and location, pushing up into the balls of her feet and making small circular movements with his strong thumbs. She had her eyes closed and was listening to him describe his first orgasm.

"I looked down at my penis, soaked in sperm. It was warm, and the feeling of warm, slippery sperm, mind you, I didn't even know what it was, that it was even called sperm, mixed with the warm nylon gossamer Vanity Fair panties, I began to feel aroused again. I dipped my fingertips in and tasted it. I rubbed it around on my now stiffening erection, I rubbed my balls with the wet material and then I took off my mom's panties and licked them. It aroused me so much that I started to suck on them."

"Wow, everything, well so much of who you have become as a sexual person stems from this moment," she said. She kept her eyes closed and moved her feet to his servicing hands. She pointed the toes and rubbed them together. She let him kiss each toe as he rubbed her feet like a masseuse. She felt his warm wet tongue testing her limits, she'd told him in letters that she'd never had a "foot job" as he called them. She wasn't convinced by him, but she was beginning to understand that he took this challenge seriously. He was treating her feet like priceless stones, with utmost care and deliberation. He licked across the pads of each toe, slipping his wet warm tongue between them, always remembering to use his strong hands to squeeze, rub, and press on her arches, the balls of her feet, and along her Achilles tendon.

"So, do you fantasize about being with your mom?" She asked.

"No," he laughed. "I do however fantasize about being with "a" mom. Like I want to be with my mom, just not my real mom."

He wasn't sure she understood. He felt her rubbing his balls and he opened his legs and let them fall wide open and lazily to the bed. He was sucking each toe into his mouth. He moved slowly with intent. He used his hands to manipulate her. He knew how good a foot rub is and he knew what felt good. The Achilles tendon, he pinched it tenderly in the little hollow and slid up and down her ankle from heel to calf and he felt her flex her toes and point them straight up. He put her whole foot into his mouth.

"Suck my cock," she said. She pointed her toes and pushed them into his open mouth. "Do you feel better honey?" She said it in the same way she would talk to her sons (but not her sons) if she was putting a bandage on a boo-boo. "Suck on mommy's cock," she said. She felt his cock twitch and her whole foot up to her arch was down his throat.

She pushed it further, she wanted to see how much he could take. He opened his mouth, and when she called herself mommy he took her down to the arch of her foot.