The Futanari Diaries Ch. 09

I'll admit to feeling nerves as Mum drove me to work for my first time working with Isabella and Naomi. Though the role I was taking on wasn't exactly what I thought it was going to be meeting with Isabella for the first time, what I'd been told by the Pythia had certainly kept me awake the past couple of nights. Jade, Vanessa and Bailey did their best to wear me out and distract me, but if what I was told was correct, the future was going to be interesting, to say the least.

Mum could sense I was nervous, so eventually turned off the main road until we were parked in a quiet alley. She pulled down her panties, took off her shirt and skirt, unhooked her bra, and started lubing up her girlcock. She didn't even need to ask me, taking off my own clothes as she pushed her seat all the way back, managing to move over and straddle her lap.

"I love you, baby," she whispered, feeling the head at my rosebud, ready to accept her shaft.

"I love you too, Mum," I whispered back, pressing down and feeling the head slowly pop inside me.

We both moaned as I slowly lowered myself all the way down, wrapping an arm around the back of her neck as we made out. Once I'd bottomed out, I broke the kiss and smiled. "It's been a while, Mum. I'm sorry."

"No apologies, baby, but I do miss the feeling of being inside my little boy. You'll always be him, no matter how old you get." She looked me up and down. "There's no missing you're a man now though. With a lovely cock between your legs." I felt myself blush. "I know you had worried, sweetie. Are they gone now?"

"Yeah, I guess I was worrying about nothing."

Bouncing up and down on her, we resumed making out, using one hand to tweak her nipples that earned a few soft moans. I'd woken up horny that morning, feeling Jade's girlcock pressing into me. I'd have loved more time with her, but I had to get up for work. She woke up a little as I kissed her goodbye. Her face lit up with a smile, and I felt better knowing I'd be leaving her in a better mood. Wishing her a good day, that last kiss was something else. Bailey was fast asleep, kissing her softly, waking up enough to hear her love for me before she rolled over and was lightly snoring within seconds.

"Oh baby, you feel so good," Mum moaned.

"I love riding you, Mum."

"Caroline knew I was doing this so we didn't fuck last night. I've got a massive load for you, baby."

"God yes, I want it so much."

"Soon, baby. Just a little longer inside you now. I'm loving it."

I bounced faster and faster, loving the feeling of my mother's thick girlcock deep inside me. I kept kissing her, eager to feel her lips pressed against mine as she seemed as eager to kiss me. I'd always been close to my mother, but since adding a sexual relationship, I'd never felt close, and I think she felt the same. Just those little moments during each day we shared, she was still my mother, but there was no doubt she enjoyed the deeper, meaningful relationship created since we'd been intimate.

"Mummy," I moaned.

"I know, baby. You like Mummy's girlcock?"

"So much, Mummy," I whimpered, as I really wanted her to cum in me.

Feeling her hand on the back of my head, I lowered my mouth to kiss her again, whimpering as she seemed to start slamming her girlcock up into me, not that I'd complain. But I knew it was because she was close to finishing. So I kept kissing her, wrapping my arms around her, feeling her smile as I kissed her. I felt her hands on my arse as she started to fuck me harder, and when she finally started to cum, I think it was to the relief of us both.

"Baby," she whimpered, and I noticed the tears down her cheeks.

"Don't cry, Mummy," I whispered.

"I just feel so close to you like this, baby. I just know that as much as I love my wife, I'm also in love with my son." I kissed her softly, as I felt exactly the same way. Her hands moved up my body as she finished ejaculating. I made sure I bottomed out again before we broke apart. "You'll be late your first day."

"Don't care. You're more important, and once I tell Isabella, she won't care either. Mum, I'll make time for you. I promise."

Resting a hand on my chest, she met my eyes. "Baby, your girlfriends and sister... Never deny them. You have such a good heart. You're so special." She started to cry again. "I know how much you love me, baby. I'll never, ever think otherwise. Any time I get a moment like this is enough."

"But..."

"Sweetie, I have Caroline. She's my wife, and she makes me feel special every day. But she also understands the connection I have with you, not just as your mother. She feels that too."

"She does?" I ask softly.

"She loves you as much as Jade and I do. Do you feel the same for her?"

"I love her to bits, Mum. She's been a second mother since the day she moved in. I've told her that."

Her fingers stoked my cheek, the smile lighting up her beautiful face. "And now I love you a little more. But we'd best go, baby. You have a job, hopefully making futanari feel as special as I do right now."

"I'll always love you, Mum."

She started up the car, but I saw the tears fall down her cheek, grabbing her hand and holding it the rest of the way. We were both naked, but neither of us cared until we parked up near the townhouse. Only then did we dress. Once I had my clothes on, Mum turned to me, leaning over and kissed me again. "I'll pick you up, baby. Just let me know each day, okay?"

"Are you sure?"

"I'll get half an hour here, half an hour home with you each day. So yes, I will."

"I love you, Mum. So much."

Her lower lip trembled again before she kissed me. It was a kiss not only of passion but something else. When she pulled back, her cheeks were wet, eyes glistening. "I wish your father..."

And I understood why in that moment. She'd had a man, and he'd destroyed her at heart. Now she had another man, a man she loved unconditionally, and I was now returning that love. And it was overwhelming her. I had to get out of the car, lest I start blubbing like a baby. I kissed her softly, told her how much I loved her, and got out of the car, striding towards the door.

I didn't hear the car pull away. Pressing the doorbell, Isabella actually opened the door. She took one look at me, meeting her kind and soft eyes, and I burst into tears, feeling her pull me close. I heard the door shut as she hugged me tightly, feeling a second part of arms around me, figuring it was Naomi.

"Is it this? The role? What you were told about who you are and your future?" Isabella whispered. Shaking my head, she asked, "Your mother?"

"I think I understand a little bit more about her now," I murmured, "I think I do, and it's heart-breaking."

There was silence before Isabella asked, "Are you the only man in her life?" Nodding, I felt both hug me tightly. "Naomi, take him to his room. Just comfort him for now. Benji, your visitor for today will arrive at ten. Will you be ready?"

"Yes. I'll be fine. I think I've just learned a couple of big things that I probably wasn't meant to, at least right now."

Isabella kissed me softly, and I had a feeling she cared about me a lot already. Naomi took my hand and led me to the stairway leading upstairs, walking towards a closed door. The bedroom was decorated beautifully, no expense spared, with its own bathroom to the right. Naomi sat at the foot of the bed, taking a seat next to her. Turning towards me, she stroked my cheek.

"Big morning?"

"Feels like it. I think I understand my mother a bit more. Her depth of love for me but also the pain she keeps hidden from everyone. Just a chink but... I think I might need to ask some tough questions. She's given me the basics but there is more. Maybe only Caroline knows."

"And me?" she asked softly.

"I was attracted the moment our eyes met, Naomi."

Her face lit up in an absolute stunning grin. "Really?" she asked, seemingly surprised by what I said.

"I never lie. But surely you must have men falling over..." Her face fell, changing from joy to sadness in seconds. "You've been hurt?" I asking, keeping my voice soft.

"Too many times. I don't trust many men nowadays. But there was something about you... Isabella said there is an aura about you that we now understand, but she felt as safe with you more than anyone she knows, and you were a stranger. I felt the same thing. The moment you hugged and kissed me, I just felt this warmth inside me, that you would never hurt me, that you'd fight for me, that you'd... That you'd die for me." Raising my eyebrows at that, she added with a smile, "Those were only feelings, Benji, but they were so strong, I cried when you left on Monday. But when I got home, I was so horny, I masturbated five times before I finally fell asleep."

"Could that explain all the futanari I've met?"

"It's possible. Isabella might know more. All I know is that... I'd love that date with you, Benji."

"Despite what I'll be doing?"

"Sex is sex. It's a physical act, but you're doing something very special while you're here. When you're out with me, your focus is me, and feelings might be involved." She broke out into giggles. "Okay, I lied when I said 'might'. Feelings will definitely be involved." Taking my hand in hers, she met my eyes, "I like you already. And I'd like to know you better."

"If that's the case, you might need to get to know my girlfriends too."

"If they love you, Benji, they'd be worth knowing and meeting."

"Okay, you'll need to come to my house sooner rather than later. If that's not too soon..."

"Take me on a date, and I'll do it the day after."

"Agreed."

We sealed that agreement with a soft kiss. I sensed she wanted more, a lot more, in that moment. So did I. She was gorgeous, incredibly sweet, and she wanted me. That much was obvious. But she broke the kiss before things went too far. "You should shower and ready yourself. Your very first client will be her at ten. She's going to be very nervous because she knows exactly who you are."

"Really?"

"My grandmother wasn't incorrect. Word has spread through our networks, Benji. You'll learn more and more as you go along. You're still young and nothing major will happen yet. But your preparations must begin."

"Do I need to wear anything?"

"Nope. Just shower, put on a robe, and wait in here until there's a knock at the door. It'll either be the client, Isabella, or me."

"Okay, I'll have a shower and wait in here."

She kissed me again before skipping to the doorway, glancing back a final time and smiling, before disappearing and closing the door. Striding into the bathroom, I washed off first, particularly my butt as Mum's cum was still leaking out, before I ensured I smelled nice, looking in the mirror to see I didn't need to shave, typical, throwing on a silk robe and waiting in the bedroom. There was a small cabinet that held bottles of liquor, a fridge filled with water and soda, a small cupboard with snacks, and lube absolutely everywhere around the room.

A knock at the door almost made me jump, checking my watch to see it was just after ten. I wasn't sure what to expect. What I didn't was a beautiful but clearly nervous young futagirl, looking as fidgety as anyone about to have sex for the first time. Blonde, beautiful blue eyes, at least 6'3 if I guessed correctly, wearing a gorgeous summer dress that highlight her curves, showed off her long legs. Meeting my eyes, the smile that appeared melted me completely. If she was a virgin, god help me...

"Hi," she said softly.

"Hello. Who are you, beautiful?"

"I'm Riley."

Wondering if I should use a fake name or not, I figured it didn't matter. "I'm Benji." I kissed her cheek, noticing she blushed. Taking her hand, I felt her shake at my touch. Definitely nervous. Escorting her inside the room, I shut the door and led her to the couch. She sat down, smoothing down her dress. When I sat down next to her, she glanced at me and grinned. "Would you like a drink? Anything you want?" I paused before asking, "Are you nervous?"

"Is it that obvious?"

"I know you're a virgin and therefore it's your first time with a lover."

"Is that a problem?"

"No. Two questions. How old are you?"

"Eighteen."

"So am I." That made her smile. "Am I receiving?" She nodded eagerly. "Okay, sweetie, I can work with that. And we'll enjoy a drink first, hopefully calm those nerves."

Pouring us two fingers of some pleasant liquor, I sat next to her and asked some simple questions. The obvious was obvious. She lived at home. She had siblings. She was a recent graduate from high school. Single with no previous relationships. She was a virgin at eighteen and wanted to lose it. She'd looked on the internet and, from what she told me, the Pythia of the globe had started to spread word already.

The drink calmed her down, so by the time we kissed, she wanted to take control, and I let her. Since I only had a robe on, undressing me was easy, so I took delight in undressing her instead. She lifted her arse so I could take off her panties as I sat on my knees in front of her, looking up her naked body. Her breasts were not large, noticing the tan lines she had over her breasts and groin. That wasn't a real surprise.

What did make me grin was what was between her legs. "That's quite the girlcock for an eighteen year old. Nine?" The smile was so adorably shy, I almost wanted to just cuddle her and that be that. "Impressive, sweetheart. Would you like me to blow you first? If I make you cum, you'll last longer when we make love."

"Make love?" she asked softly.

"Of course. Your first time should be about love. I will show you everything I know and love, and trust me, my aim is to make you feel as special as I can during your first time. All I can hope is that you leave this room feeling as special as you obviously are."

"I wish all men were like you," she whispered. And, in that one sentence, I knew a young futagirl who'd had her heart broken, probably more than once. Some men did well and truly suck when it came to futanari. Thankfully, the majority liked them, and a lot of those loved them too.

Taking her thick girlcock in my mouth made her moan loudly, and I had a feeling her first blowjob wasn't going to last long. She didn't know what to do with her hands or body, which didn't bother me. I knew this was going to be awkward for her so it was important to make her feel comfortable. So I focused on making her cum, noticing her head rested back but the smile on her face. "Look at me, beautiful," I whispered, watching her head life in time to see her girlcock slide inside my mouth again.

"Oh my god," she cried, "It feels wonderful, Benji."

I didn't reply, just focused on how great her girlcock felt in my mouth. She rested a hand on the top of my head, using my hand to show her what to do. That earned another smile, before she cried she was close to orgasm already. I knew it was going to finish early, ensuring I took as much of her cum in my mouth as possible before.

Lifting myself up when she was done, I opened my mouth to show her its contents. She laughed out loud and asked if I was willing to share. Leaning forward, she kissed me softly, feeling her tongue in my mouth as we swapped her cum, only breaking once we'd swallowed it all. Standing up, I took her hand and led her over to the bed, sitting back, ensuring she followed me as I lay on my back, head propped up by pillows as we continued to kiss.

"I didn't expect this," she admitted, "I thought it would just be..."

"Isabella told me that those who wanted to visited me wanted more romance, to feel special. And that's how I feel too. Sure, I loved being fucked, but I also want to feel something. Riley, you're gorgeous, and I'm glad you're my first client."

Her face lit up. "I am?"

"You are. Now, give yourself a few minutes until you're hard again. I prepared myself earlier, so you don't need to worry about me. All you need do is slide that wonderful girlcock of yours inside me, and we'll make love. But you're not on a clock as I will only see one futagirl any day that I'm here. I reckon Isabella or Naomi will eventually knock to make sure everything is okay, but my entire focus is on you alone."

Her girlcock was hard in no time, so all I needed to do was get comfortable and guide her inside me. I watched her face as she slowly slid inside me. I actually felt honoured I was taking her virginity. I was a little sad that she was with me rather than someone she loved, but I knew it was something many young futagirls did. Life was still difficult for so many futanari out in the world, despite all the changes in recent decades.

"Oh god!" she cried, "Oh my... Oh Benji..."

Putting a hand on her chest, I said, "Go slowly, sweetie. Take your time. In and out slowly, just leave the head of your girlcock in each time, then slide back in. It'll feel wonderful for both of us." She did that, watching her face just light up again. Leaning down to kiss me, I let her take control and she figured out what felt good for her. It was going to be great for me no matter what.

When I wrapped my legs around her waist, her eyes lit up as she had a different angle to enjoy. "Fuck me, Riley," I moaned. And she did. Feeling her pump into me faster, she figured out that slow and steady would win the race, but slowly but surely certainly felt even better. I wasn't worried about an orgasm. I knew my role was about making sure the young futagirl enjoyed herself, and that she had all day to do it again and again to her hearts content.

"Oh my god," she moaned again.

"Fill me up, Riley. I'll get you hard again."

"I've never felt... Is it always like this?"

"Yes, it is. You feel wonderful. Keep going, sweetie."

"I'm close, Benji."

"Then cum in me. I hope you cum in me more than once."

That earned another of those smiles before she kissed me, feeling her pump me faster and faster before moaning into mouth, that first throb of her girlcock before she filled me with her cum. I wrapped my legs and arms around her tightly to keep her close as she spurted again and again. Once she was empty, I expected the tears. The first time was always emotional for anyone, but I'd learned for a young futagirl, it meant a whole lot more. Acceptance was just one feeling.

"You're a special young futagirl, Riley," I whispered, "I'm glad I was your first."

"Thank you, Benji."

"You're welcome, sweetie. Now, dry your eyes, then we'll relax for fifteen minutes, then... Well, what would you like?"

"You on top. I've always dreamed of a young man riding my girlcock."

"Then that's what you shall have. And when you cum again, we'll go have a shower, clean up, and we'll snuggle until the end of the day, unless..."

Her face lit up again. God, she was gorgeous. "No, that sounds wonderful, Benji."

To get her nice and hard again, I made sure she was on her back and showered her body in attention. It was obvious she'd never had that, not only focusing on her gorgeous breasts, but from the top of her head to her little toes. By the time I'd finished, I wasn't sure if she wanted to cry or orgasm, but her girlcock was almost obscenely hard and leaking pre-cum, wasting no time sliding down it and immediately riding hard and fast.

"Can I come again?"

I laughed at the double meaning. "Sweetie, you can cum again now and you can visit whenever I'm working. But try not to get attached... Well... Let's see anyway..."

"I want to actually cum in you soon."

"Sweetie, if you can cum twice, three times or ten, I won't be complaining."

I rode her hard and fast, watching her face light up as she was happy to lie there for a while, letting me do the work. I wasn't going to complain, polite enough to ask if she wanted to see me cum too. Yes, she definitely wanted to see that, so while bouncing myself, I stroked my cock and came quickly, considering I was incredibly turned on by enjoying a young futagirl enjoying her first time. She giggled as I erupted all over her, leaning down to kiss her once I was empty. Explaining what she should do next, I rested on forearms as she placed her arms on my butt cheeks and started to pump me.