The Futanari Diaries Ch. 08

Story Info
The life of a young man and his love for futanari.
11.7k words
4.88
9.4k
34

Part 8 of the 14 part series

Updated 08/03/2023
Created 01/08/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
UltimateSin
UltimateSin
5,135 Followers

A/N - So, I'm sure some of you were thinking 'Where the hell is this going?' with the last chapter. Let's just say we're going into complete fantasy now, though I guess a world with futanari in it is quite fantastical as it is.

No, Benji is not going to become a man-whore. It would go against everything I've built up so far. I've insinuated a couple of things in previous chapters. Time to start laying the groundwork for something that is pure fantasy, but I also don't want this turning into a fifty-chapter story, so I'll also have to start thinking about how this will all end.

Anyway, hope you enjoy the next few chapters.

*****

Mum drove us into a residential area, eventually stopping outside what looked like your regular townhouse. It was larger than normal, but there was nothing spectacular about it. Looked totally normal, like your everyday run of the mill family lived inside.

"Ring the doorbell, tell them your name, and the rest is up to you, sweetie." Mum gently gripped my chin, leaving a soft kiss on my lips. "If at any time you feel uncomfortable, Isabella will stop the interview. She knows how old you are, how nervous you'll be. But she's a sweetheart, just like you. You'll be in good hands."

"Is she the same age as you?"

I enjoyed the smirk. "Does that idea excite you, sweetie?"

"Well, you're fucking hot, Mum, so..."

I didn't finish my sentence as I found myself kissed hard, her tongue in my mouth quickly, pulling me close as one of her hands ran down to my arse. Had me erect in seconds, running my hand down her body to her skirt, reaching under to feel her up at the same time, making her smile as she broke the kiss. "Thank you for saying I'm hot, baby, but you'd better go, otherwise I'm going to fuck you."

"And I'll complain because?"

Playfully slapping my shoulder, she told me to get out of the car. Wishing me good luck, I stood on the footpath until she'd pulled away, turning and walking up the path towards the door. Pressing the doorbell, I waited a few seconds until the door opened. A futagirl definitely appeared, perhaps mid-twenties at most, immediately smiling at me.

"Hello," she greeted me, her tone friendly, "Are you Benjamin?"

"Hello, that's me. I'm here to see Isabella."

The smile remained. "Of course. Come in." She offered her hand. "I'm Naomi."

First thought was that she had incredibly soft skin as I shook her hand then stepped inside. My second thought was that she was utterly fucking gorgeous. She had that pale, almost semi-goth look about her. White skin, hair as black as night. Bright blue eyes. She had a little colour on her cheeks and dark red lipstick. Nose ring and I think a stud in her tongue. Wore a simple black vest that showed off ample cleavage, and a couple of tattoos down her upper arms, and such a short black skirt, it would be illegal in probably fifty countries.

"Can I get you anything?" she asked, "A coffee? Tea? Drink of water?" I stammered over my response for a good number of reasons. That made her giggle, which was another dagger to the heart. She was far too sweet already. "Nervous?" she wondered.

"A little."

Taking my hand, she led me to what would have been a lounge room, telling me to sit and relax while she got us drinks. I sat in silence, looking around. Art on the wall. A bookcase full of, well, books. Plants in two corners. Music playing quietly in the background. Naomi returned with two mugs of coffee on a tray, placing it on the table in front of us as she sat next to me.

"How do you like it?"

"Two sugars, dash of milk, please."

After preparing both, she handed me mine, still that smile on her face. "You're very cute, Benjamin. Isabella is going to absolutely adore you." Definitely blushed straight away, which made her giggle again. "Oh god, our clients are going to love you even more if you're like this with them. You're not completely innocent, are you?"

"No. Mum told me she was friends with Isabella."

Naomi nodded. "I know, I've met your mother before. I sat in the meeting when she proposed her idea to Isabella."

"Oh, I didn't..."

She patted my thigh. "Isabella will no doubt discuss everything with you." She paused before asking, "If you ever want some fun..."

I looked her up and down. "You're serious?"

She smiled again. "Two things. One, you're unbelievably cute, and two, your mother was very complimentary."

"Oh..."

Sipping at my coffee, we moved onto other topics, such as how I'd just finished school, was now looking for a part-time job, and deciding on which university to study at. She seemed to be impressed by how I'd done at school and I think even further when I told her what I wanted to study. I tried not to talk about my private life, but I think she had a good idea as she'd figured out rather quickly I'd enjoyed a lot of sex recently.

Before I could misinterpret anything further, an absolute vision of beauty appeared in the doorway. Tall. Busty. Long blonde flowing locks to her shoulder and further. A short skirt that ended mid-thigh to accentuate unbelievably long legs. I drank her in, feeling my jaw drop slightly, before I finally looked at her face, pleased to see her smiling. "Benjamin?" Managing to nod and stand up, she offered her hand. "I'm Isabella. Delighted to meet you."

I was expecting just the handshake, maybe a kiss on the cheek. I didn't expect a soft kiss on the lips. Definitely blushing after that from the heat in my cheek. "Oh, you are just adorable. Your mother showed me a photo or two. Those don't do you any justice." Gripping my shoulders, she smiled. "Oooh, there is a hard little body under there. What do you think, Naomi?"

"He's far too cute, Izzy. I want him for myself. Just wrap him up and take him home."

"Maybe later, Naomi. Now, Benjamin, I'm not sure how much your mother told you. I know she would have only told you this morning. Correct?" Nodding, she continued. "That was my idea as I didn't think giving you days or weeks to overthink things was a good idea. We'll go and have a chat, I'll explain what you'll do, answer any questions you have, and we'll go from there." She caressed my cheek again, which made me smile. "Photo's definitely didn't do you justice. My god, no wonder you have so many girlfriends."

"Mum told you?"

"She suggested you are rather sexually active and have a number of lovers." Shrugging helplessly, she chuckled before taking my hand. "Follow me, sweetie. We'll go have a chat. Naomi, I might call you in later. We expecting any clients this morning?"

"It's a Monday so it's pretty quiet. I think there's one at nine, one at eleven. James will take care of them both."

"Good. I'll give you a shout if I need assistance."

"Please do, Izzy. See you later, cutie."

Following Isabella down a hallway, she glanced back and smiled. "I'm sure you're a little overwhelmed right now," she said, leading me into what looked like an office, "But you'll be fine." There was a desk with chairs either side, a bookcase, cabinets, pictures on the wall, and a couple of couches. Hearing her shut the door, I glanced back. "Take a seat on the couch, sweetie. Need something to calm the nerves?"

"Would that be okay?"

"Of course, sweetie. What do you like?"

"I usually drink beer."

"Oh no, something much more pleasant. I've got some good scotch. Ever had that before?" Shaking my head, she smiled at me. "I'll water it down a tad to take off the edge."

Preparing drinks, I watched her and felt that familiar stirring in the loins. As I've said, there is no such thing as an 'ugly' futanari. Women range from 1-10. Futanari range from 9-10. If there is an '8' out there, I haven't met her yet. Offering me a glass, she sat next to me, sipping at her drink, before turning in my direction.

"I want you to work here, Benjamin. I can say that straight away. Appearances alone, you'll be incredibly popular."

"Um, thanks."

"Can I ask some personal questions?" Nodding, she continued. "How many sexual partners have you had?"

"Um. Let me think. Jade. Mum. Caroline. Sandra. Vanessa. Bailey. Alexis. Veronica. Chantelle." Pausing, I added, "Those are the futagirls that have fucked me. I've also blown a few others but not had sex with them yet."

"How would you describe your orientation? I mean top, bottom, switch?"

"Mostly bottom. I have topped a couple of times, but I prefer to receive."

That made her smile. "Good to hear. So, with your sexual partners, is it vanilla or have you dabbled in other things?"

"Sandra is my Mistress. Well, sometimes."

That made her smile broaden. "Ah, so you've dabbled in BDSM?"

"Lightly. But I trust Sandra completely. It's fantastic at the time. Does leave me feeling a little sore afterwards, but it's worth it."

"Is there anything you wouldn't do?"

"A few things. Do I need to describe them?"

"No, I can take a good guess. Double penetration?"

"Not done it yet but I've heard it mentioned. All I'd ask is that I'm prepared correctly."

"Watersports?"

"I'd consider it. Sandra has mentioned introducing it later during our play sessions. Anything more, I'm not sure. She likes to push my limits but seems to know what they are already. As I said, I trust her completely. She won't hurt me."

"Sign of a good Mistress." She took a gulp of her drink. "Can you undress for me, please?"

I expected that question so finished my drink, my hand shaking slightly as I put it down on the coaster. She gently grabbed my wrist and stood up. "Let me, sweetie," she said softly, "No reason to be nervous with me around. I'll care for you like your own mother." She paused then leaned down to kiss me, her fingers moving to the buttons of my shirt as her tongue slid into my mouth. She was a good distraction, as before I knew it, I was standing before her naked, even taking off my shoes and socks myself without noticing.

Her hand grasped my cock, causing me to moan into her mouth. "Oh, you have a nice cock, Benjamin. Our clients will love it." She paused a moment. "Want to see me naked?"

"God yes!"

I helped undress her in return as we continued making out. She smiled as I helped off her jacket and blouse to reveal her bra. Taking that off, it freed her big tits, my hands going to feel those up as she unzipped her skirt and lowered that to the floor before removing her panties. That's when I felt her thick girlcock press against me, looking down to see it. "Holy shit," I muttered.

Taking my hand, she led me over to her desk. "Sit up on that, sweetie." Doing as she asked, she leaned forward to kiss me again, pulling me into her body, her girlcock pressing into me. It was so thick and long, I think it was even bigger than Sandra's. "Sweetie, can I ask you a question?" she breathed.

"Sure."

"Can we make love first? I don't normally do this with potential employees but..."

"Isabella, I think you're fucking gorgeous in return."

"God, you are going to break hearts working for me, sweetie. Lean back for me." I did so, resting on my elbows, as she spread my legs, getting me into the position she wanted. Dropping to her knees, feeling her tongue at my rosebud wasn't a surprise, nor the fact she enjoyed it and was good at it. Had me moaning loudly within a couple of minutes.

Grabbing lube that sat on her desk, she applied some to me and slid a couple of fingers inside me. "I'm going to need to loosen you up a lot, sweetie. I'm bigger than your mother or Caroline."

"Okay," I breathed.

"You okay, sweetie?"

"I'm turned on, Isabella, and looking forward to making love."

She leaned up to kiss me as she slowly finger-fucked me. Her kisses were surprisingly intimate, her eye contact more than I'd expect. Two fingers was moved up to three after a few minutes, liking the smile that appeared on her face when I moaned loudly. She didn't stop kissing me, though moved down to my neck, as that was always a sensitive area for me.

"Oh god," I moaned.

"One more finger, baby." I nodded, feeling a fourth finger. Moaned even louder followed by a curse or two. She kissed me deeply again. "I really want to be inside you, Benjamin."

"Benji. Call me Benji. And I want you inside me."

Removing her fingers, she kept kissing me while lubing up her girlcock. Pressing it against my rosebud, I tried to relax as I felt she was even bigger than Sandra. Taking a couple of deep breaths, I met her eyes and nodded as she pushed forward. Just the head of her cock alone had me squirming. "Fuck," I grunted, "Keep going."

Thankfully, she took her time, though the sense of relief when the head of her massive girlcock finally popped inside me was a relief. Pushing forward a little more, I moaned loudly again. I hadn't been stretched this much ever, yet at the same time, it felt absolutely fucking wonderful. "Oh god yes," I whimpered.

She kissed me again. "Thank you, sweetie," she breathed into my ear.

"Give me everything. I want to feel your entire length inside me."

Thrusting slowly, I felt more and more of her enormous girlcock slide inside me. Not sure how long it was, but there did come a time that her entire length was inside me. It was the best feeling ever. She looked down herself to see we were joined completely, looking up with a wonderful smile on her face. "Wow, sweetie. Just wow. How does it feel?"

"Please make love to me. Please..."

Caressing my cheek, she started to move slowly in and out of me. I spread my legs even wide, holding them wider with my hands inside my knees, feeling her even deeper inside me. "Oh yes, that's even better, sweetie. Fuck, I'm so deep."

"God yes. Holy shit, Isabella..."

"Izzy. My friends call me Izzy." She paused before adding, "No, call me Bella. My lovers call me Bella."

Smiling, our lips met again, the kiss incredibly passionate. I guess we liked each other already. She started to thrust a little faster, and I whimpered more than once because it just felt so damned good. Her kisses increased in intensity, her eyes wild with desire. Whenever I winced, she'd stroke my cheek, concern in her eyes. I'd nod each time. I could handle the occasional moment of discomfort.

"Fuck me," I moaned, "Fuck me and cum."

"Are you sure?" Nodding eagerly, she gripped my knees and pushed them back further, and she started to fuck me. I came hard all over myself within a minute or two. Her girlcock was almost a blur of motion at times as it slid in and out of me. Kissing stopped as she clearly focused on her orgasm, gazing into her eyes, though her large breasts jiggling with each thrust were a distraction.

"Cum in me, Bella. Fill me up."

"Oh god!" she cried. Those last couple of minutes were painful, I won't lie. A girlcock that large slamming into someone my size is always going to hurt. Totally fucking worth it though. She cried out before she buried herself and came. Her girlcock was so thick, I felt every single spurt deep inside me. It was never ending, or so it felt, almost like a fountain. Breathing deeply, her forehead glistening, she left herself inside me as she leaned forward, a soft but passionate kiss that continued for a few minutes.

Isabella proved her strength by lifting me up, ensuring my arms and legs were around her, before carrying me over to the couch, sitting down so I was on her lap. I couldn't help starting to ride her girlcock, which made her giggle. "You're insatiable."

"And you feel fantastic, Bella."

She grabbed her phone from the table next to the couch and made a call. "Naomi, come to my office."

The door opened within a few seconds, glancing to see Naomi stood in the doorway. Closing the door and locking it, she walked over to sit next to Isabella. "How is he?" she asked.

"Naomi, he's going to be the most popular man here."

"Can I..." Naomi started to ask.

"Properly, Naomi."

"Benjamin, would you..."

"Name when and where, though it's a little weird asking with Bella inside me."

Her eyebrows raised at the use of that name. "Well, Izzy has already got her claws into you too. Benjamin..."

"Benji..."

Her face lit up, no doubt aware what it meant. "Benji, I hope you do work here. You'll have fun, but I'd like to get to know you too."

"Me too," Isabella said softly, "Though I think I know you fairly well now. So the question is..."

"I guess I need to ask further details about what I'm doing here, I guess?"

"There is one more thing, Benji. It is why your mother made sure you were introduced to me." She sat in her chair and picked up the phone. "He's here now in my office. Come downstairs." Giving her a curious look, she smiled at me. "My grandmother."

"What? But she must be..."

Standing and walked around her desk, she sat down on the couch and patted the spot next to her. Naomi sat on one of the chairs as I sat next to Isabella. "Do you know your history, Benji?"

"It was one of my core subjects at school. I did rather well."

"You ever learn about Ancient Greece?" Nodding, she continued, "So I assume you might have heard of high priestesses known as the Pythia?"

"You mean Oracles?"

Both Isabella and Naomi smiled. Before they could say anything else, there was a knock at the door before someone else joined us. Standing up, I only realised I was naked when the eyes of the old futanari lit up for a second before she walked towards me. I had no idea how old she was, but I sensed she was wise beyond my own years. Offering her hand, I gently shook it.

"You're Benjamin." Nodding, she gestured for me to sit down. Isabella rested a hand on my thigh as the old futanari sat down on the chair next to where I was sitting. Taking my hand again, she met my eyes. I had no idea how old she was, but those blue eyes belonged to a woman a quarter of her age. "I'm sure you're wondering how old I am, perhaps wondering what I'm doing in a place like this. Thing is, Benjamin, your arrival here was already known to me. I know who you are in your heart and mind. I know what you're going to do in the future." She took my hand, turning it over so she could look at my palm. She smirked at my reaction. "I'm not a palm reader, Benjamin. Instead, through your hand and eyes, I gain a window into your soul. I could predict your entire future right now, but your future is something you must discover yourself. But I can let you know one or two minor things."

"Like what?"

"Your position here will not be like anything else. You won't be paid for your services. You will not be selling your body. Your good heart and kind soul is what will draw futanari here. You will entertain nervous guests, show them all the love and affection I know you are capable of. Each single futanari who visits will be a virgin. They will honour you by giving you their virginity."

"Honour me?"

"It was in the signs, Benjamin. I am not the only Pythia. There are others across the globe. We communicate regularly. And I am currently training my replacement." When she glanced away, I turned to look at Naomi, who immediately blushed. "She has the gift. All futanari do, but it is only those who choose to undertake the training that eventually rise to my position."

"So who am I? Or what do I do?"

She glanced at Isabella, noticing she returned a single nod. "You will have a child with your sister, Benjamin. A child of pure blood. She will be futanari. You will have children with your other lovers, but it is the child you have with Jade that will lead our kind to a brighter future."

"Only one child?"

"No, just your first born. You will have more children with your sister. Sons and futanari. She will be your first wife. Alongside your sister, you will lead the first wave to strike down the Church of Avignon." She leaned forward and pressed her hand against my chest. "You are of pure heart and soul, Benjamin. It is why you will work alongside Isabella. Your name has already spread, Benjamin. I'm sure you've realised that there is something special about you, that any futanari who meets you seems to fall in love."

UltimateSin
UltimateSin
5,135 Followers