How to train your virgin. (MF)

I watched the boys laying by the pool, enjoying the sunshine with tall tales and laughter. Boys, ha, my youngest son was one of them, the rest were some of his friends from college here to celebrate his 21st birthday tomorrow. My eyes found Paul, god he looked like his dad, I still missed Mike occasionally, mostly on those nights where you can feel the dark pressed against the silent walls of the house.

I turned away from the window, but their laughter brought me back. My gaze finding Charles, Paul’s oldest friend and the son of one of my own friends. Charles looked like something out of a greek myth, his lightly muscled physique suiting his height perfectly. His blonde hair was lighter than I remembered, if you looked into his bright blue eyes, you could see the intelligence in them, hiding behind a shimmering twinkle of humour.

I caught myself admiring his physique, the way a light sheen of sweat added definition. He had a soft patch of hair on his chest, I followed it as the patch narrowed and disappeared under the waistband of his shorts. I swallowed and turned away, trying ignore the ache that had started in my loins. I shouldn’t feel like this about someone 25 years my junior, admitting Charles made certain parts of me tingle wouldn’t be good.

I took my robe off and stood in front of the mirror, striking a pose I looked at myself with a critical eye. Not bad for 46 I thought, but could be better. My breasts had been perfect in my youth a full 36C, they were bigger now 38DD but softer, definitely not as perky anymore either. I turned and looked over my shoulder at my butt, that still looked good at least.

I got dressed in a black bra and panties, pulled a loose dress over my head and headed downstairs to the kitchen. I was prepping some things for dinner when Paul came inside.

“Hey Mom, we’re going to go into town for a bit, maybe catch a film or something.”

“Okay hun, let me know if you’ll be out late”

The next few minutes were filled with noise as the young men got ready, quickly fading to silence as they left me on my own. I rinsed my hands under the tap and glanced outside. My breath caught in my throat as I saw Charles had stayed behind, he was laid on a lounger playing with his phone.

My head filled with ideas, fantasies, unspoken wishes of a sexual nature. My heart beating fast, I walked outside before my brain could tell me stop, I walked over the the pool.

“Charles? What are you still doing here?” I asked.

He looked up from his phone. “Oh, hi Mrs Taylor, it’s okay me staying isn’t it? I just didn’t fancy going out.”

“You’re fine Charles, and please call me Lisa. I was just going to enjoy some sun. Do you mind?”

“It’s your house Mrs.. I mean Lisa. You can do whatever you want.”

Whatever I want, I thought, oh you sweet child, if only you knew. I moved to the next lounger and shrugged my way out of my dress. My back to him, I dropped my dress on the empty lounger between us. I ran my hands through my hair secretly hoping that he was checking out my ass. Stood there in my black thong and bra I suddenly felt stupid, what was I doing. I took a deep breath, I couldn’t run away now without looking foolish. I laid down on the lounger and closed my eyes, trying to control myself.

“Hey, uh, Lisa. Are you okay?”

I opened my eyes and found Charles looking at me. “I’m fine Charles, I was just thinking I should have worn something more appropriate. Sorry, I’m not used to having company.”

“I mean it’s your house, wear what you, uh, like, and well, you know…”

I rolled on my side and lifted myself up on one elbow, I felt my breasts shift and quickly moved my other hand to stop them falling out my bra. Charles eyes flicked down to my breasts before finding their way back to my face. I heard him swallow, I could see a blush starting to appear in his cheeks.

“What is it Charles?”

“Well, it’s just… I mean… oh man… it’s not like you’re ugly or anything”

I laughed, I couldn’t help it. His blush deepened.

“God, I’m sorry Mrs Taylor, I’m just trying to say you look good. I’m not good at talking to women,” he chuckled “but I’m sure you’d guessed that”

“Charles, I’m sure you have your pick of all the girls at college. I don’t believe you”

His blush deepened further, the red flush spreading.

“Yeah, I guess, but they’re, you know, girls. They’re not that interesting, not like you.”

I arched an eyebrow. “What do you mean?”

“I don’t know. I’m sorry, I didn’t mean anything by it, it’s just you’ve lived a life. You have… I don’t know, experiences and everything. You can have a conversation without talking about how wasted you’re getting.”

He paused for a second.

“Paul and the others, they don’t seem to mind, but I just find the girls kinda boring. That’s one reason I didn’t want to go so with them today, there’s only so many jokes about being a… know what, never mind, doesn’t matter.”

He stood and left quickly, nearly running into into the house. I stood, picking up my dress as I followed him, my thoughts racing. Had he just been about to come out to me? Thinking about what to say to Paul if I found out he’d been making obscene jokes about his friends sexuality. I went to the guest room where Charles was staying and knocked on the door. I could hear him moving around in there. I knocked again, but he didn’t answer. I felt silly standing there in my underwear, trying to think of the right thing to say.

“Charles, it’s ok. It really doesn’t matter who you are attracted to, not in this day and age. You’re still young, you’ll find someone who you can connect with. Do you want me to help you talk with your mom about being gay?”

The door flew open, he stood there, looking at me.

“Gay! I’m not gay, I’m a virgin.”

He walked away from me to sit on the edge of the bed, he put his head in his hands and stared at the floor. My thoughts were racing, could I? Should I? Would I? I closed the door behind me and sat beside him on the bed, my hand resting gently on his shoulder.

“There’s nothing wrong with that either, if you want to talk, I’m a good listener.”

He sat up, I took his hand in mine and gave him my best “it’s okay” smile. Charles took a deep breath.

“Well it’s complicated I guess. I’ve had girlfriends before and we’ve kissed and stuff, you know, made out, but I always panic before going any further. I mean, I know what to do, I just worry that I won’t be any good at it, that she’ll laugh at me. So I just stop and that’s it.”

“Charles it’s okay to be nervous, when you meet the right person, you’ll learn together. You shouldn’t worry about it.”

“Easy for you to say. I… I don’t know, I guess so, I mean like I said, I know what to do, and I’ve seen things online, it’s just the actual doing…”

“Okay, firstly don’t believe everything you see in porn. Secondly, it’s fine to be inexperienced. Tell me what’s the furthest you’ve gone with a girl?”

“Uh, I guess… technically, this” he gestured at me. “I mean, yeah, this.”

Suddenly, I was acutely aware that I was still in my underwear and there were only three items of clothing between the both of us. I felt a rush of heat in my pussy, my clit tingled as I carefully crossed my legs and cleared my throat.

“Okay, we’re setting records today. That’s good.”

I smiled and winked at him, he laughed, I saw some tension leave him as his shoulders relaxed.

“Yeah, I guess you’re right. I’m sitting here with a beautiful woman in her underwear and the world hasn’t ended.”

I paused for a second, thinking how far should I take this, had I already gone too far, could I go further?

“You’ve kissed girls before right?” I asked.

“Of course I have.”

He looked so earnest, so sincere. I smiled and leaned in pressing my lips against his. He froze for a second like he was a marble statue, before starting to kiss me back. I put my hand on the back of his neck and opened my mouth slightly letting my tongue have access to his lips, he responded in kind, letting our tongues meet and explore. My other hand found his gripping the sheets, I loosened his hand and moved it to my waist as I deepened the kiss. My fingers entwining in his hair, the heat between my legs intensifying, I moaned in pleasure as I broke the kiss.

His hand dropped from my waist, I was breathing hard and watched him stare at my breasts as they moved. I glanced down at his shorts and was pleased to see I’d had a positive effect on him.

“Now you’ve kissed a woman in her underwear, another first and everything is still okay, right?”

He finally tore his gaze away from my breasts, I smiled to let him know it was ok.

“Lisa, is this a dream?”

“If it was, what would happen next?”

His eyes flicked down again, his thoughts obvious to me, I reached behind and undid my bra. His breathing quickened as I slid first one strap then the other down my arms, leaving my bra just resting on my breasts. His knuckles were gripping the sheets like he was on a cliff edge and his life depended on it. I let my bra fall to the floor, I was feeling nervous myself, I hadn’t felt this horny in years. I could feel the eddies of his breath against my nipples, they stiffened almost immediately.

I took his hands and lifted them to my breasts, helping him cup and squeeze them, letting him fondle and explore. Every touch of his fingers on my skin was setting my nerves on fire. I gasped when he circled my nipples with his fingers, he gently squeezed them between his thumb and finger, rolling them around. I was pushing against his hands, he lifted my breasts and caressed them up and down. My clit was tingling with renewed fervour, my pussy getting wetter by the second. His fingers came back to my nipples again and he tweaked them again, harder this time, almost but not quite enough to hurt. I put my hands over his.

“Gently works best for me, you don’t need to get too firm.”

“Oh Lisa, I’m sorry. Are you ok. I knew I’d mess it up!”

“Charles, you’re doing fine, more than fine to be honest, I’m enjoying myself. Are you?”

“God, yes. I can’t believe this is happening.”

“Do you want to try for another first?”

I licked my lips in anticipation as he nodded. I moved before the doubts could set in, swinging one leg over him and straddling his lap. I could feel how hard his cock was now it was trapped between us. I held his head in my hands and brought him lower, brushing a nipple across his lips. Charles didn’t need a invitation, his lips parted and sucked my nipple in.

I let out a small main as his hands found my sides, thrusting my hips forward against him as his lips and tongue flicked and sucked my nipple. I moved his head to my other breast, he obediently started reading that nipple, one hand coming up to tease the one his mouth had just left.

Waves of pleasure were rushing down through my body, all crashing down on one place. My clit was throbbing as I ground my hips against his, rubbing my crotch against his hard cock, only two thin pieces of fabric separating us.

I pulled back slightly, slowing the bucking of hips. I lifted his head and kissed him deeply, my tongue probing into his mouth, meeting no resistance as our breath mingled. I pulled back, my chest heaving, we were close enough still that I could feel his chest hair against my nipples.

“Are you okay?” I asked. “Do you want to stop?”

His hands slid down my sides and further back as he stroked my ass cheeks. He shook his head and grinned at me.

“I don’t ever want this to end.”

I kissed him again, slipping my hand between us and lifting the waistband of his shorts I moved it slowly lower, exposing a thick patch of hair. I kept moving lower letting his cock spring free and further until his balls were resting on the waistband. His cock was huge, at least 7 inches and when I gripped it with my hand my fingers didn’t go all the way round.

He was staring down at my hand holding his cock, disbelief written clear in his face. He was uncircumcised, the foreskin sliding down as I gripped and moved my hand lower. The head of his cock glistened with moisture. I kept my grip steady and moved my hand up with a slow twist, watching as his shiny tip disappeared behind the foreskin.

His breath was ragged as I moved my hand down, up and down again. The foreskin now pinned back as he swelled even bigger. His cock felt like a rod of steel as I moved my hand steadily up and down. I could feel it throb and pulse against my grip. I knew he was close and kept my rhythm steady.

His fingers dug into the cheeks of my ass, his head rolled back as his cock gave a further massive twitch, I felt the pulse start at the base of his shaft, travel quickly under my fingers till it erupted from his tip in a huge spurt of cum. It spattered against my breasts and stomach, over his chest as well.

I pumped my hand a few more times, each one bringing another small spurt from him till my thighs and his shorts were covered. My hand dripping in his cum. I felt his dick soften slightly so I let go. I was shocked at how far I’d let this go, but I didn’t want to stop. Charles lifted his head and looked at me as I slowly licked my fingers clean of his cum.

“Another first?” I asked.

He nodded, unable to speak as he struggled to regain control of himself.

“How far do you want to take this?” I asked.

Source: reddit.com/r/Erotica/comments/pe4m2a/how_to_train_your_virgin_mf