The Futanari Diaries Ch. 03

Swallowing, I asked quietly, "How long?"

Grinning as she pulled away from the lights, she replied with one word. "Eleven."

"Holy shit!"

Turning to me for a moment, she smiled. "As I said, I'll be gentle, but I'm going to watch all eleven slide inside you, sweetheart, and you're going to love every single inch. Can you deepthroat?" Shaking my head, she smiled. "Okay, I won't do that to you. Your sister going to show you?"

"This weekend. I know the theory but she's going to train me."

Continuing to stroke her girlcock, she shuddered slightly. "Just your hot breath and soft lips on my length will make me cum, sweetie." At the next set of lights, she leaned over to give me one hell of a kiss. "Part of me thinks this is so wrong..."

"And that's why it'll feel so good, Miss. Trust me, I'm here more than willing to do anything with you."

Her eyes lit up. "Careful what you promise, young man, lest you find yourself handcuffed to my bed." When my eyes lit up at the prospect, she giggled. "Well, no wonder you're so popular."

Her house was in a suburb quite a distance from my home and school. Not a real surprise as I figured most teachers didn't want to run into their students too often out of school. It was a small townhouse, following her inside to a decorated living room, modern kitchen and an upstairs where she explained there was a large bedroom and bathroom. There was another room as a study, and she had a small backyard.

"Can I ask a question, Miss?" I asked as she poured us a glass of wine each.

"We're home now. Call me Sandra."

"Well, I'm Benji then. Those who I'm close with..." She immediately rested her hand on mine, her face lighting up. "Well, if we're going to be doing what I think..."

"Definitely doing," she almost growled at me, before smiling, "What's the question?"

"Um... is there a Mister or... I don't know... um..."

"You're adorable when flustered, Benji. To put any concerns out of your mind, I'm single. I've been single for a while."

"How? You're fucking gorgeous. And smart."

I wasn't kissed for that. I was cuddled, finding my head resting on top of two large breasts. Wrapping my arms around her, she sighed contentedly. "There was someone special, a long time ago. A woman. I know, I know, most don't like us but she was different, until she was slowly indoctrinated, and her love turned to... well, our relationship ended badly."

"Sorry. I didn't know..."

"It was an innocent question, Benji. You're young, curious, full of questions."

"Well, her loss, Sandra. I think you're wonderful."

"Benji, you can stop with the compliments. I'm going to fuck you."

"Just being honest, Sandra."

Pulling back, she met my eyes before kissing my cheek. "I'm your year co-ordinator. Last interviews are next month. Will your mother be coming? I'd love to see her again, tell her how well her son is doing."

"I think she's already got the evening free, but I'll remind her when I get home."

Taking my hand, I followed her outside, glass in hand, as we took in the decking. There wasn't a pool, but there was a hot tub. The weather was already warm as we approached summer, but she bent over to flick a switch and bubbles started to form. "Want to get naked in there?" she asked.

"God yes. Um... can I see you, Sandra?"

"You first. Get in the tub and I'll put on a little show."

No show from myself. I just took off my clothes, my cock hard and pointing out. She took it in hand, giving it a gentle stroke, before gesturing to the hot tub. Getting in, the water was already warm, watching as she sculled the wine, disappearing inside for a moment with the bottle. Placing that and the glass down, she started by undoing her blouse, shucking it off to reveal a white lacey bra. Her black skirt was next to reveal a long girlcock, partially erect but, as I stared at it, I noticed it filling up nicely. Glancing back up her body, she slowly took off her bra to reveal a large pair of breasts, nipples obviously hard. Kicking off her heels, she slowly approached and stepped down into the tub.

"Do you think I'm beautiful?" she asked, surprised to hear some nerves.

I slid across to where she was sitting, straddling her lap and probably surprising her with one hell of a kiss. Feeling her fingers in my back, I smiled to myself when she released a light moan, and definitely smiled when I felt her enormous cock now resting behind me. "How's that for an answer, Sandra?"

"I always keep water based lube nearby," she whispered, "I have lovers on occasion, just none as young as you."

"You're forty-eight, Sandra. Do you have any idea how fucking hot it is that an older futagirl like you wants to be with me?"

She kissed me hungrily, her tongue in my mouth this time, though she eventually moved to my cheek and down my neck, making me shudder as I felt her teeth gently nibble at my skin. The tub of lube was nearby, reaching across to open it, preparing myself as we continued to make out. I asked if she wanted my mouth, but the look in her eyes told me she wanted only one thing from me. "We'll make love out here than adjourn to the bedroom later," she said, before she paused.

"What is it?" I wondered.

"Stay the night," she whispered.

"I'll call Jade, ask her to bring me some clothes for tomorrow."

Readying herself in no time at all, I lifted myself as she grabbed the base of her girlcock, lowering myself to the head and I paused as it felt far larger than anything I'd taken before. Realising I was nervous, she kissed me softly, caressing my back with her other hand, as I slowly but surely allowed the enormous head slip inside me.

"Oh my fucking god," I groaned, resting my head on her shoulder.

"Okay, baby?" she asked, hearing concern.

"So fucking big, Sandra. But, my god... I know I'm going to love it in a minute."

"Take your time, baby. We have all night."

She didn't move, allowing me to completely control my descent down her enormous length. With every inch that filled me, I'm sure my face lit up with an even broader smile. Never had I been stretched so wide. Never had I had something so long inside me. I didn't think I'd fit the entire length inside me, but after a few minutes, I felt my cheeks press against her thigh. I met her eyes and she returned the smile on my face, kissing me softly.

Taking a couple of minutes just to enjoy such a large girlcock inside me, I started to slowly lift myself up and down her length. She held my hips at the same time as I rested my hands on her shoulders, never taking my eyes off hers. The sheer delight I could see, the near constant smile, I'd never seen her look so happy in the time I'd known her.

"So tight, baby," she whispered.

"Because you're fucking huge, Sandra!"

"I'm not going to last long. It's been a while, Benji. And, just a warning, I cum a fucking lot."

"Good. Fill me up all night."

She kissed me softly before whispering, "Definitely going to fuck you at school for the last couple of months. Friday afternoon, after last lesson. I'll figure out something and drive you home afterwards."

"Think I'll say no after tonight, Sandra?"

I had no idea if I'd cum riding her without stroking myself so I figured I'd just cum later. I wanted to feel her blast inside me though. Gritting my teeth, I started to bounce faster and faster. No matter what I did, that was always going to cause at least a dull ache. Sandra's hands moved from my hips to my arse, feeling her move only slightly, judging her body reactions for how close she was.

"What a tight little butt you have," she murmured, "Can't wait to cum in it."

"How long?"

"Oh, very soon, sweetie."

She wasn't wrong as I felt her cock throb within a couple of minutes and it felt like a gunshot deep inside me. Spurt after spurt, losing count as I kept on bouncing away, before she finally gripped my hips so I stopped moving. A dreamy smile was on her face before she kissed me softly. Making sure I remained on her lap, she grabbed our glasses and poured us each a wine, sitting back enough so I could fondle her tits while I sipped at my wine.

"You love sneaking peeks at me, don't you?" Nodding, a little embarrassed, she giggled. "Trust me, I appreciate it. Nothing feels better than feeling sexy in front of a young man like yourself. Honestly thought I was too old to turn on someone your age."

We only moved once we'd finished our glass of wine, lifting myself up off her cock and feeling her cum immediately start to leak out of me. Taking my hand, she led me into the conservatory, where she kept towels for us to wipe ourselves down. Or, she wiped herself down, then had a lot of fun doing it to me. "Make love upstairs, call your sister, dinner then more fun?" she wondered.

"Sounds good to me."

Finding myself dragged upstairs had me chuckling away. Thankfully, the room was cool thanks to central air, Sandra gently pushing me back onto the bed. Shuffling back so I was comfortable, she grabbed lube from off the nighstand, crawling towards me once she'd lubed herself up, lifting me up and sliding two fingers inside me to get me ready again.

Hands under my knees, she pushed them as far back as possible, commenting on my flexibility, as she pressed the head of her girlcock against me.

"Fuck me, Miss Wilson," I moaned as the head of her cock slid inside me again.

"Want me to stay dressed when we do it at school?" she asked after another few inches slid inside me.

"God yes. And leave your glasses on. You look so sexy when you chew on them when thinking."

Once she was buried, she leaned down to give me a soft kiss. "Thank you, Benji. I haven't felt this beautiful in a long time," she whispered, "Up for a hard fuck now?"

"I'll tell you if I'm hurting."

Amazed at the positions I found myself in, she pushed my knees back until they almost touched the bed, watching as her entire length pistoned in and out of me. I was left wondering if I'd ever feel anything as deep inside me again, her large breasts jiggling with each thrust. The sound of her skin slapping against my arse echoed around the otherwise empty house.

"Oh my god," I moaned, "Oh god, please don't stop... I love you girlcock, Miss Wilson."

"Well, she loves your tight little arse, Benji. Graduate top of your year, and I'll give you the fucking of a lifetime."

"Yes, Miss Wilson. Anything to feel this again."

I'd felt euphoria before. I don't know how to describe what I was experiencing as her enormous cock plunged the depths of my arse. Hell, I almost felt on the verge of crying, not due to pain, but due to overwhelming... something. Closing my eyes, digging my fingers into her back, I felt her fingers wipe my cheek. I assured her I wasn't sore, but she seemed to know what I was feeling.

Starting to pump into me harder and faster caused my eyes to finally shoot open. "Fuck!" I cried, "Oh fuck me."

"Okay?" she asked between pumps.

I actually started to laugh "Oh fuck yes, Miss Wilson. Just pound my little butt."

She practically had me in a ball by now, her massive cock now slamming me. Was it hurting? God yes, but I wasn't going to complain. With the pain came overwhelming pleasure, and I loved watching her face and body, the sheer delight and pleasure she was taking from fucking me in return. She warned me when she was getting close. Part of me felt relief, part of me wanted her to just fuck me all night into the next morning.

"I'm close, baby," she finally moaned, "So close."

"Fill me, Miss Wilson."

"Arse or mouth?"

"Arse, Miss Wilson. I'll suck you at school and take a load."

"You're a naughty little boy, Benjamin."

"Your naught little boy, Miss Wilson."

That made her smile before she filled my arse again. I counted them. Eight! Eight full spurts of cum filled my bum. Then she collapsed on me, releasing my legs so I could wrap them around her, thankful that although taller, like all my lovers, she wasn't too heavy. Plus, feeling her breasts pressing into me was rather soothing.

Lifting herself up after a couple of minutes, she kissed me softly before pulling out, grabbing a nearby towel she'd brought in as I was leaking a lot immediately. Helping me up, I followed her into the bathroom, where I watched her have a pee. Not something I'd ever done before, then we had a quick shower together as, despite the air-conditioning, we'd built up quite a sweat, and I did need a slight clean up too as cum was going to leak all night otherwise.

Following her back downstairs, she asked what I wanted for dinner. I assured her that, in addition to whatever she wanted, I'd try and help. Whenever I offered Mum and Caroline, they declined, insisting they could do it. First, I needed to call my sister. Pressing speed dial on my phone, she answered within two rings.

"Okay, tell me. How was it?"

Looking at Miss Wilson, I smiled. "She was a fantastic lover, Jade. I loved every second."

Miss Wilson smiled at me. In fact, I think she verged on crying too. "Do you need picking up?"

"Actually, I'm kind of... going to stay here. Is that okay?"

Hearing her laugh, I didn't hear a reply before I heard her say, "Mum, Benji's at Miss Wilson's and he's staying the night. Is that okay?" There was another pause. "Mum says that's fine, Benji. Do you want me to bring over some clothes for tomorrow?"

"Yes, please. Is that okay?"

"Give me her address and I'll bring something over right now."

Passing my phone to Miss Wilson, she gave my sister the address before she no doubt was asked a question about me. She met my eyes and smiled. "He was wonderful, Jade. He's made an old futanari feel beautiful once again... I'll see you soon... Yes... Yes... Okay. Bye for now." Hanging up, she passed my phone back. "I remember you sister. Pretty little thing she was." She paused before adding, "And she's always been in love with you. She asked me for advice. I told her she just needed to wait, her time would come."

"Worth the wait, to be honest."

"Good. Now, dinner. How about some pasta? Something simple."

"Okay."

"Good. Then all you need do is plonk that cute little butt of yours on the stool opposite, ensure my wine glass isn't empty, and talk to me. Once we've eaten, we'll wait for your sister to arrive, then we're heading upstairs to make love the rest of the night."

"Fantasy fulfilled, Miss Wilson."

Jade arrived after we'd eaten dinner. To my slight consternation, Mum and Caroline were with her. When Miss Wilson opened the door and I saw them, I almost groaned, though was thankful I was at least partly dressed. She invited them in, Jade handing me a bag of clothes, Miss Wilson offering a drink, gesturing to the empty couch. I sat on the other two-seater, Miss Wilson returning quickly with wine for the parents, a soda for my sister, as she was driving.

Taking my hand once she sat next to me, my family smiled at me. "How was he?" Mum asked.

"Wonderful," Miss Wilson replied, "No wonder Jade loves him so much. But he was also very... well, I've had few lovers who can take my entire length without a single complaint."

"How big?" Caroline wondered.

"Eleven. And thick. Very thick."

Caroline glanced at me, that predatory look I'd grown accustomed to. "Good to know as I have plans for him too."

"What will the school say?" Mum wondered, "I don't want either of you in trouble."

"We'll be smart, Mum," I replied, squeezing Miss Wilson's hand, "But we really like each other and I don't want this to be the only time. I've discovered a few things since my birthday. I have a lot of love to give, and want to be loved in return."

Miss Wilson kissed my cheek. "Thank you, baby," she breathed into my ear.

Jade turned to Mum. "I don't think you could stop this anyway. If they want to be together..."

"I don't want to stop them, I just don't want them in trouble or hurt. But, Benjamin, if you're confident and you this won't affect your graduation, I'm not going to stop you. All it will do is force you away from us, and I'm not having that for a second."

I think Miss Wilson and I both breathed a sigh of relief. Making chit-chat until everyone finished their drinks, Mum and Caroline hugged me goodnight, Jade kissed me passionately as always, waving at them as the car disappeared. Miss Wilson hugged me from behind. "Ready to make love the rest of the night?" she wondered.

"Want to utterly nail me from behind, Miss Wilson?"

"Oooh, you are a very naughty boy, Benji. We're going to have such a goodnight."

Back inside, she ordered me up to the bedroom, told me to strip, and wait on the bed on my hands and knees. Doing as she asked, I waited a few minutes before appeared, wearing a black leather corset, stockings and suspenders, garter, black leather boots, and a black leather mask across her eyes, her emerald green orbs alive in the gaps.

And she had a riding crop in her hands. Along with one or two other things I recognised.

"Baby, we are in for one hell of a night," she said, "I'm going to make sure you hobble into school tomorrow morning."