THE FUTANARI DIARIES CH. 09 By UltimateSin

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 aunt... 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.

"Oh Benji!" she moaned.

"That's it, baby. Fuck me nice and hard. Fill me up again."

"You're so tight."

"Just for you, sweetie."

The smile that formed was ever so sweet. She probably knew that was bullshit, but again, it was about making her feel special. Kissing her again, she pumped me faster and faster, harder and harder. Soon enough, I was begging her to keep fucking me, and she knew that was real, making her smile again, knowing she was pleasing me so much.

"Take my big girlcock, Benji."

"God yes. Fuck me, sweetie. Keep going, long as you can."

Kissing me deeply, her tongue now exploring my mouth, the confidence was now flowing through her. Thrusting up into me faster and faster, I met her eyes and smiled, letting her know I was loving it. Moaning and groaning simply urged her on. Fuck, she felt wonderful inside me. Shame she was a client, I'd have kept her around with my girlfriend, mostly because she was just so damned sweet. Isabella had warned me, the fact I'd met some adorable young futagirls and I'd have to box away any feelings or emotions I might feel.

Damned difficult to do when my first client was just so damned cute and I knew she was falling for me already. The Pythia was right, it seemed.

When she finally came inside me again, her face lit up and I certainly smiled as I felt her fill me up again. As she slowly stopped thrusting into me, I rested down on her girlcock, ensuring I kept kissing her until she was completely relaxed. "Now that was an orgasm," she whispered, "And I'm covered in your cum too."

"That's why I have a bathroom nearby."

Sliding off her, she turned onto her side and we snuggled for a few minutes. She was just too damned cute, and I was worried she'd get attached, even though I was an entertainer. But I also didn't want to break her heart, so I let her cuddle me until I suggested we have a shower. She enjoyed that, cleaning each other up and down before stepping out, enjoying drying each other down, before we sat in a pair of silk robes on the couch, chatting about our lives. I had nothing to hide, and I learned more about her. It was obvious she was incredibly smart but almost painfully shy, but also wary of people, admitting she'd had her heart broken more than once, which is why she chose to visit me.

The knock at the door halted our conversation, Isabella poking her head in. Noticing we were sitting on the couch, she walked in and took a seat on the lone chair. "Did you enjoy your first time, Riley?"

"I loved it, Ma'am. I'd love to come again." I chuckled the double meaning behind the phrase, Riley realising and giggling too.

"Well, you're more than welcome to. I can give you his schedule, and if you wish to become a regular after today, that's more than possible. If you end up being one of his girlfriends, I'd certainly understand why you'd both make that decision. Just note that this young man is only with us temporarily."

"That's okay. But he's made me feel so special today."

Isabella smiled at me, and I think she was proud in that moment. "Well, that's what we aim to do, please our clients. Riley, would you like to stay all day or is there a time you wish to go home?"

"I don't know. Benji?"

"It's your choice, sweetie. I'll be here until around 5pm."

"Um... I really enjoyed our first time, but I also have to think about things." She took my hand in hers. "You made me feel so special, Benji. I'm already falling for you." She giggled, adding, "Typical futagirl, falling for her first lover."

"You're very special to me already too."

I could sense Riley wanted to stay longer and eventually agreed to stay for another couple of hours. We spent most of the time chatting about our lives, and I did give her one or two snippets of my conversation shared with the Pythia. She knew about them, another reason why the Church of Avignon despised futanari, the fact they still worshipped in the old ways, revered the old gods.

We also made love one more time, slow and gentle, Riley above me as I savoured the feeling her nine-inch girlcock being thrusting into me. I made her smile when moving my hips, meeting her thrusts, and by the end, she was slamming it nice and deep, her mouth on mine constantly. When she came, she almost screamed with delight before collapsing on my chest. When I felt her shake, I knew she was crying again, wrapping my limbs around her, whispering how special to me she already was.

She said she had to go home eventually, that she couldn't handle being with me any longer, otherwise it would be too hard to go. We dressed together before I escorted her downstairs. She hugged Isabella and Naomi, thanking them both for providing something as special as our few hours were.

"I'll be back soon," she whispered as she hugged me for the final time.

"I hope so, sweetie. I had a great time. Thank you for being my first."

"You too," she whispered back, hearing her catch the sob, "You made it so special for me."

"I'm glad to hear that, sweetie." Leaning back, I caressed her cheek, meeting her eyes. "Live your best life, Riley. Don't let them get you down. Okay?" She nodded to that, a small smile forming, before I kissed her again. "Hope to see you again."

"Goodbye, Benji."

"Goodbye, beautiful."

Another heart-warming smile before she opened the door, walking towards her car parked on the opposite side of the road, waving as she took off, before I closed the door. I sighed, feeling myself slump. First client and she was just far too adorable, someone I'd get attached to if I saw her again. Turning back to where Isabella and Naomi, they could almost read my mind.

"She needed you, Benji," Isabella said, "Someone as young as herself to make her feel special."

"I understand but... Damn, I loved every second but had to remind myself that, despite my role, she's not one of my girlfriends or family. She was a lover. And I stand here knowing I want to see her again."

Isabella hugged me tightly. "Just that good heart of yours, sweetie," she whispered, "You hungry?"

"I could do with a nibble."

"I know you're not here for it, but would you like to enjoy a couple of other lovers before the end of the day? Again, no payment. You're not a working man like others. You're not here for that sort of thing. But many of the futanari who visit here are lonely, looking for companionship and just that feeling of being loved, even if only for a little while."

"Actually, that sounds like I'm doing a good thing, providing a service of companionship and love. I don't see how that can be viewed negatively."

"Sex work is still looked down upon unfortunately, again, led by the Church and their moral charters. But many of my men and futagirls are providing a service for many people. Many are not here for sex. Some want nothing more than a cuddle and to feel a connection, even if only for a brief time."

Taking a seat at the kitchen counter as Naomi started making us sandwiches, I gave it some thought. "I see both points, but the problem is meeting more futagirls like Riley. I'm not sure my heart could handle it. I can close myself off as best I can, but it was her first time because..."

"She told me when I called her," Naomi said, "Unfortunately, Benji, so many of us don't have it easy. I'm sure you see the news each night, what happens to us on a daily basis."

"That's why I'm going into law," I muttered.

Finishing lunch, we enjoyed a drink in Isabella's office, noticing Naomi sat close to me on the couch. I didn't mind, our mutual attraction was obvious. She was different to most of my lovers, but there was no doubting she was a sweet futagirl. I definitely wanted to get to know her outside of work.

Close to 1pm, I headed to my room to ready myself for my next visitor. Unlike Riley, she was close to forty years old, and although friendly, she was there for one reason. She wanted a young man to fuck. Next to no 'romance', we just stripped and she wasted little time fucking me. I didn't mind, to be honest. Actually made it easier. I was just a warm, tight hole for her to slide her girlcock into, fuck nice and hard until she climaxed, got her hard again quickly, and she fucked me again until she left a second load inside me. Shower together, kiss on the cheek, then goodbye.

Explaining that to Isabella afterwards, she laughed but admitted that quite a few of her clients would probably be like that with her other workers. I retorted, stating I'd probably prefer it if I was doing something similar. Easier on heart, conscience and soul. Just keep it to the act of sex without any intimacy.

My last client of the day was much the same, to start with anyway, but was left thinking she was even older, perhaps in her fifties, and that's when I learned that, unlike women, futanari kept their figure, for want of a better word. When I politely asked her age and she told me late-fifties, I was amazed. She simply smirked at my surprise. "Another reason why they hate us," she muttered, "My tits are still up here, even after three children and breastfeeding."

"They are spectacular." No word of a lie. I wasn't good at judging how big a pair of breasts were, but even on a late fifties futanari, there was no doubting they were huge.

"Well, aren't you a sweetheart," she said, continuing to strip off, "Now, when was the last time you were fucked by an enormous cock?"

"Monday. Isabella is well endowed."

She turned around and I almost choked on my drink. She was at least as big as Isabella. I sculled my drink, placing the glass on the nightstand, before I stood up and approached her, making sure I had lube. Ensuring I lubed up her girlcock nicely, I saw apprehension on her face. "Been a while?" I asked softly.

"A few years. I've wanted to do this before but... I lost my nerve..."

"I'm young enough to be your son, maybe even grandson..."

"I was looking online and saw your profile, who you might be to my people. I didn't think you'd see someone like me, but I finally just found some courage and knocked on the door downstairs."

"I'm glad you did."

"Can we make love?"

"Whatever you wish is my desire."

It started off gentle and slow, but once she was over her nerves, she fucked me senseless. I didn't complain at all, every minute was wonderful, particularly when she came inside me and just kept on fucking me. When she had my legs over her shoulders, my arse raised, and she was just absolutely pounding me, I just wanted her to keep going the rest of the day and night, it felt so damned good.

She wore herself out it in the end, blasting inside me before she pulled out and collapsed next to me. "Fucking hell, what a workout!"

"Never enjoyed something like this with... um..."

"Someone as old as me?" she asked, chuckling to herself, "As you said, I might be old enough to be your grandmother. Though I'm still fit, my hair colour is natural and not too many wrinkles, yes?"

"Still gorgeous, far as I'm concerned."

"And that's why Isabella recommended you. Haven't felt this good in years."

After a shower, I escorted her downstairs, a cuddle and a kiss before she walked out towards her car, turning back to see Isabella and Naomi smiling at me. Walking into the kitchen, Naomi made us all a coffee as I took a seat on a stool. Isabella chuckled as I did perch myself somewhat carefully. My last client had given me one hell of a hard fuck in addition to having an enormous cock.

Mum must have been informed that I finished with my last client at 5pm as she arrived half an hour later. We sat in Isabella's office, enjoying a coffee each as we discussed what I'd been up to. Mum wasn't surprised to hear I'd enjoyed time with two other futanari, in addition to the young futagirl who had given me her virginity that morning.

"Before you go, Benji, one question. Did you enjoy it?" Isabella asked.

"I did. More than I thought I would. Each client was different."

"Good. So you'll be back when I next have someone interested?"

"Definitely."

Smiling, she stood up out of her chair, taking me in her arms and kissing me softly. Kissing her back, I melted against her firm body, feeling her thick girlcock pressing into me. "Far too adorable," she whispered, "You'd better get your cute butt out of her, otherwise I'll keep you here all night, and that'll make Naomi jealous. Give her a kiss and cuddle before you go."

"See you soon, Bella."

"I'll see you then, cutie." She paused, looking unsure before adding, "Before you go, there is one thing, Benji."

Walking around her desk, she opened her desk and took an envelope out, handing it over to me. Opening it up, I saw money. Glancing at her, she returned a shy grin. "It's not for what you did in the bedroom. I'm paying the same as Naomi. A flat daily rate on the days you're here, whether you have sex or not. That way you won't feel... You know..."

"Are you sure? I don't really need the money."

"You're officially an employee here. You'll pay tax, earn superannuation, everything will be above board and lawful."

Scratching my chin, I finally nodded. "Okay. I guess if you put it that way, it doesn't make it sound as..."

"Sordid?"

"I don't mean to offend."

Thankfully, Isabella laughed. "Benji, I know what I'm doing here, but you are different. Your role is different. You're an important young man, plus your time here will be brief. Once you're at university, the Pythia will soon reach out again." She smirked, adding, "You'll still enjoy virgins every so often, but the approach will be different."

Wishing Naomi goodbye, she stood up out of her chair, hugging me tightly. I felt her girlcock press into me from underneath her skirt, sharing a long, lingering kiss with her. No doubting we were attracted, particularly when we pulled apart and her cheeks were bright red. "I'll see you again soon, Benji," she whispered.

"If it's quiet, I'll make sure I spend some time together next time so we can talk."

The smile that formed was so sweet, I had to kiss her again. Whispering goodbye, I walked to the door, making sure I turned back one last time before I stepped outside. The house was cool as the heat almost knocked me out, making sure I was sat in the air-conditioned car as quickly as possible. I burst into laughter as Mum had her girlcock out, nice and hard, pre-cum glistening at the head of it.

"Mum, I've..."

"I was just masturbating while I was waiting, sweetie. Have a good day?"

"I enjoyed it, Mum. More than I thought. Thanks. I mean it."

"You're welcome. Want to blow me while I drive us home?"

"Long as I get a creamy load in my mouth."

"Give it five minutes. Ten at most."

She wasn't lying. It was between five and ten minutes by the time she blasted in my mouth, gulping it down before I sat back, Mum smiling widely, taking her hand in mine as she drove us the rest of the way home. She did pack away her girlcock after pulling into the driveway, heading inside to be greeted by Bailey and Vanessa, who had organised with Bailey and Jade to move in what she needed. Greeting both of us with a hug and kiss, Mum headed off for a quick shower, Caroline appearing in that time, no surprise she immediately headed upstairs to join Mum.

My girlfriends asked about my day and I hid nothing. I admitted that the young futagirl I'd been with was named Riley, she'd obviously been a virgin, and we enjoyed a few hours together, adding that there was already a depth of feeling between us. They all smiled when I told them about Riley eventually needing to leave to think about things as we already shared a deep connection.

"The futagril who works at the front desk, she's interested in me too," I admitted, "Her name is Naomi."

"When can we meet her?" Vanessa asked. Blinking at her in surprise and silence made both of them giggle. "Benji, if she likes you, then we're going to like her in return. What's she like?" When I'd explained what she looked like and how sweet she was, they started grinning again. "She sounds spectacular."

"Only known her a couple of days but there was that immediate connection. Shit, those few hours with Riley were special. I really liked her from the start."

Mum and Caroline appeared a few minutes looking rather rosy-cheeked. Mum and Bailey started to prepare dinner, Vanessa stepping in quickly to assist. Mum asked them both why, hearing replies that, until they found jobs, they'd help around the house by doing most of the chores. Mum smiled, kissing both on the cheek in thanks. Hearing the word 'chores', I wandered outside to check the pool and figured the lawns would need another mow soon enough.

After dinner, we chilled out in front of the television until Jade arrived home. Thankfully, she was in a better mood than the previous night, just tired after being on her feet for hours. Mum had left her a plate in the oven, so after she had a shower, I joined her at the table to keep her company. Sitting close as always, I ran a hand up her thigh towards her skirt, smiling when I felt no underwear.

Sighing, she stopped eating to kiss my cheek. "Good day at work, cutie?"

"It was. I've obviously explained my role to everyone, and considering I'm eighteen, Riley being an eighteen-year-old virgin wasn't a big deal, but it was a lot of pressure."

"I'm sure you made her feel special."

"She was. One other thing. Isabella's assistant, Naomi, has taken an immediate shine to me too."

"Well, I wouldn't blame her." She took my hand in her free one. "Don't worry, cutie. I get you nearly every night, and you have many of us to give attention."

Bailey and Vanessa wandered off to bed together before Jade and myself, left thinking the three would come to a decision each night who I would sleep with. Quietly asking Jade about Mum, she explained they'd already had a talk and Mum was fine with the occasional night in her bed at most, she knew the three young futagirls now in the house needed me.

Bailey and Vanessa were snuggled together when I wandered in to wish them goodnight. I then asked if they were going to fool around, intrigued if they were interested in each other. Both confessed they wouldn't have sex, but handjobs and blowjobs were better than doing it themselves. I told them to have fun and I'd see them in the morning.

Jade wanted a little bit of fun that evening, and as neither of us had to be up early the next morning, we took advantage of that fact. Having her stand up, I dropped to my knees before her, enjoying the smile on her face as gave her girlcock and balls plenty of attention, before I finally just took most of her length in my mouth, intending to make her cum quickly.

"Oh baby," she moaned, "You're far too good to me sometimes."

"Fill my mouth once, my butt the rest of the night."

Head bobbing up and down her on girlcock, running my hands up the back of her legs until I grabbed her tight little butt, her fingers caressed the back of my head as I felt her get ready to orgasm. Positioning my head correctly as always, she was polite to let me know when she was about to take off, filling my mouth with her sweet cum a few seconds later. Keeping some in my mouth, I showed her, surprised when she dropped to her knees and kissed me, her tongue in my mouth, licking up her cum.

"Hmmm. I do love my taste," she whispered, "Want a blowjob or would you rather cum while I fuck you?"

"Second thing. Definitely the second thing."

I was expecting to end up on my knees and for my aunt to just fuck me senseless for a few hours. Wouldn't have bothered me if she had done, but I ended up on my back first, my legs wide as she slid her girlcock inside me, thrusting nice and slow as she kept herself upright, taking my cock in hand and stroking me in time with her thrusts.

Fuck, it felt good, though her fingers did start to move faster and faster, my breathing getting faster as I felt my own orgasm starting to build. And as my orgasm approached, she started to fuck me faster and faster.

"Oh fuck yes," I moaned, the end now approaching.

"God yes. I'm going to fuck you all night, Benji."

"I'm close, Jade..."

What I didn't expect was her to pull out, lean down and watch her lips wrap around my cock. Half a dozen bobs of her head at most before I erupted inside her mouth. As soon as I'd finished, she lifted herself up and slid back inside me, amused when she opened her mouth to show its contents before smiling, gulping down my cum.

"I love swallowing your cum, little brother."

"Fuck me, big aunt."

Leaning forward, she rolled my lower body slightly, and she did just as her little brother wanted, her thick girlcock pumping into me faster and faster. I loved watching it happen, and we'd discussed more than once about filming our lovemaking sessions. Leaning down to kiss me hard, I whimpered into her mouth as she drove her girlcock even deeper.

Then she came, spurting deep inside me, counting at least six full loads before it started to slow down. She kept fucking me, though, my legs now over her shoulders, almost folded in half as she didn't relent for a second. And I wasn't about to ask her to either.

"I love fucking you, Benji. And I fucking love you too."

"Ditto, Jade. I'll never say no to you either."

Pulling out, she gestured so I sat on my knees, leaning forward so she could slide back inside me, only to find myself lifted to rest back against her chest, hard nipples poking into my back, feeling her thrust up into me. We'd done this position one or twice before, usually good for stroking myself as she fucked me. Feeling her hot breath in my ear sent a shudder through my body, whispers of her love and affection before she growled how much she just wanted to own me forever.

That didn't sound like a bad thing to me.

Her soft hands caressed my body, her lips kissing my cheek, down my neck and across my shoulders. I did eventually end up pushed forward, feeling her above me as she started to fuck me harder still.

"Oh god yes," I moaned, "Fill me again, Jade."

"I will soon, cutie. Then I'll need a rest."

"Me too, but I can't get enough of you anyway."

Feeling her fill me up a second time without her stopping fucking me was something new. If she'd done it before, I couldn't remember. I'm sure she wouldn't blame me for forgetting, considering I'd had a lot of sex recently. Once she was finished, I felt her pull out and lay next to me, turning onto her side as I turned to face, our first kiss soft and intimate.

We snuggled and fell asleep.

Waking up the next morning, I was spooned back against her, feeling her thick girlcock pressing into my lower back. Rubbing myself against it, I was rewarded with a giggle. Feeling her arms squeeze me lightly, nuzzling into my neck. I sighed with relief when I felt her apply lube to both of us before she slid her girlcock inside me.

"Now that's the best way to start a day," I whispered.

"Nice and slow, cutie. Want to savour this feeling for a while."

She slowly fucked me for at least half an hour, filled me nicely, then we headed for a quick shower before breakfast. We found Bailey and Vanessa outside, sipping at some juice as they enjoyed early morning sunshine, aware it would likely get rather warm by the early afternoon. Jade and I joined them, both of them giggling as they had heard us moaning softly as she'd fucked me.

"Can't get enough of him?" Bailey joked, "Sounded like you wore each other out last night."

"Oh, her cum was leaking out of me half the night," I replied.

"Any plans for today?" Vanessa wondered.

Shrugging, I admitted I wasn't sure. "I wasn't expecting to be earning any money, but Isabella said I'm going to be a salaried employee, different to anyone else who works there. I'll admit, I still feel a little... Well, dirty, taking any money as I'm doing this willingly because of what I've been told, but although I do have savings, I could also do with the money."

Both of them smiled at me. Jade gave me a cuddle. "We'd still like to contribute," Bailey said, "Your mother has already done so much for me, and opened her home for Vanessa. Contributing financially, even just a little bit, would be right. Plus, being home for two to three months might get a little dull. Sure, we can spend that entire time fucking you..."

Smirking, I retorted, "Think I'd complain about that?"

Jade snorted. Vanessa giggled. Bailey gave me a look that told me that, despite saying it, she didn't mind the idea of fucking me constantly. "Actually, that does remind me. When can Chloe and Georgie visit so they can finally no longer be virgins?" Vanessa asked.

"Trust me, Ness, I'm thinking of them too. Certainly miss both of them." That earned three grins, as I knew Vanessa and Bailey missed them too. I was amazed at how quickly Bailey had become central to our little group. "Next week, I'll take them out Tuesday and Thursday, one day each for both of them, and we'll take it from there. I also need to take Naomi out. I would just invite her here, and while I don't think anything that does happen here would shock her, I'd rather our first time be somewhat intimate before she gets involved in group activities."

"Still want that gangbang?" Jade asked.

"God yes, but I'd like to ensure I've been with all my girlfriends intimately before doing something like that."

"I'm thinking today," Vanessa announced, "That we laze by the pool, the occasional dip, and the three of us spend time fucking Benji in between the lazing about."

"Works for me," I stated.

"No clothes between now and when Mum gets home, Benji," Jade told me, "And make sure you keep yourself lubed up, and we'll keep some lube around for us. Girls, how many loads do you reckon?"

Bailey scoffed. "If we don't make a dozen between us, I'll be very disappointed."

Smiling at them, I walked inside to my bedroom, took off my clothes and lubed myself up. Walking back outside with three tubes of lube, I handed one to Jade, one to Bailey, one to Vanessa, then I grabbed a towel, placed it on the lawn, getting down on my hands and knees, wiggling my butt in their direction.

The three futagirls started out as they meant to go on. They fucked me one after the other, depositing their first loads rather quickly considering how turned on they were, then decided to fuck me a second time, not changing order. Bailey pounded me first, Vanessa filled me as soon as Bailey came, then Jade fucked me last once Vanessa deposited a load in me.

"I think we should have bet on more loads!" Bailey exclaimed, giggling to herself.

By the time Mum got home later that afternoon, Jade had left for work, finding me in the living room with Bailey in my bum, Vanessa in my mouth, being fucked hard at both ends. Mum smiled as she immediately stripped, taking a seat on the couch, lubing up and stroking her girlcock, asking if she could have me once they'd both cum.

"This will be our sixth load each," Vanessa moaned, "Jade left five in him before leaving for work."

"So my son has been well and truly fucked today?" I moaned around Vanessa's cock, nodding happily. "Want to ride me once Bailey has cum in you again?"

"His bum is very full of cum, Cathy, but I think he'd love some mother and son time," Bailey giggled.

Bailey fucked me as hard as she could in the last couple of minutes before she left load number six inside me, spinning around so Vanessa could leave her sixth load in me too. Both of them collapsed onto the floor, giggling away as it was perhaps the first day we'd ever spent just fucking and sucking nearly the entire time, only breaking for refreshments and breaks to refill their enormous balls.

Lifting myself up, I felt cum dribbling down my thighs, but I'd been feeling that half the day. Straddling Mum's lap, I kissed her first, soft but passionate, her tongue sliding into my mouth, her arms wrapping around me. When she earned that first whimper of desire from me, she gently moved my head down so I could take a nipple in my mouth, a good distraction as she pressed the head of her thick girlcock against me.

"Oh fuck yes," I moaned into her nipple, "Fuck me, Mummy."

"Okay, I love it when he's like that," Vanessa said, noticing that they'd already moved to sit either side of Mum and myself.

"Mummy has a great big girlcock that she can fuck my tight little butt with," I said, ensuring my voice was far more innocent than I was. "Fuck me, Mummy. Fuck me nice and hard."

Mum smiled before I kissed her, feeling her fingers move down my back to my arse. She asked Vanessa to move, no surprise I ended up on my back, feeling my legs spread as wide as possible, Mum wasting no time in fucking me as hard as possible. Considering I'd spent nearly all day being fucked by my aunt and two girlfriends, I simply urged Mum on to really give it to me.

That's how I ended up with my knees almost by my head, Mum ensuring she was giving me nearly all nine inches of her thick girlcock with each thrust. Feeling her hands at the back of my knees, pushing them back with each thrust, her eyes were alive with her desire, no doubt a million and one carnal thoughts passing through her mind.

"Fuck me, Mummy," I moaned softly.

"I love you, sweetie."

"I love you too, Mummy. And your big, thick, throbbing girlcock inside me!"

"That throbbing girlcock is going to leave yet another load in that tight bum of yours, Benji."

"Please, Mummy. I really need it."

"Okay, I'm really fucking hard again," Vanessa joked, "So hot watching and listening to you two make love."

Caroline arrived home while Mum was still fucking me. She took one look, burst into laughter, and returned within a couple of minutes, glass of wine in hand as she took a seat at the right angle to watch Mum's girlcock slamming into me. To all our amusement, she started to cheer Mum on.

"That's right, Cathy, you pound that little arse into submission. Fill him with your cum, then do it again!"

"You want to fuck him?"

"Benji?" Mum asked. I nodded eagerly. "Get your kit off, my love. As soon as I cum, you can slide your great thick girlcock into him. He's so sloppy inside. He's spent all day getting fucked."

"And so he should."

Mum filled me within a couple of minutes, at least half a dozen enormous spurts filling me up before she leaned down to give me a soft kiss. We were both dripping with sweat, not that it mattered, Mum releasing my legs as she carefully pulled out to inspect her work. Grunting her satisfaction, Caroline got into position, lining up her thick girlcock. "You want this, baby?" she asked softly.

"Fuck yes, Ma. Give it to me hard."

She did, sliding all ten inches into me without stopping. Earned a grunt of satisfaction before she started to thrust slowly. Once we were both comfortably, the look in her eyes changed as my legs ended up over her shoulders, and within a couple more minutes, Caroline was pounding me so hard, I knew that would be the end of my activities once she'd cum.

Caroline wanted me to eventually move, ending up on the floor with my arse in the air, Caroline mounting me and driving her cock into me hard and fast immediately. To my surprise, Vanessa lifted me up enough to she could get her mouth to my cock. I was rock hard while being fucked as always, but hadn't cum all that much during the day. As soon as I felt her lips wrap around my shaft, I couldn't help shudder.

"Fuck," I moaned.

Caroline gripped my shoulders and drove into me even faster. Bailey giggled, stating my face lit up in euphoria. Wasn't capable of speech any longer. In fact, I reckon I probably gurgled out a couple of things in addition to moaning and grunting. Definitely moaned when I exploded in Vanessa's mouth, managing to find the words in my frazzled mind to thank her, before Caroline pushed my head back down.

"Nearly there, sweetie," she moaned, "Nearly there."

Those last couple of minutes were intense before she did finally climax, leaving her cum buried as deep inside me as possible. She pulled out very carefully before I collapsed onto my side, taking a couple of minutes to just catch my breath. Feeling a damp cloth on my bum, I turned to see Mum smiling at me, my mother's eventually helping me to my feet, insisting I go shower before dinner. Bailey and Vanessa made to follow, Mum asking them to help prepare dinner.

Didn't stop Caroline following me, though she only helped wash me down, giving me more than one cuddle during. "Fun day?" she asked.

"Twenty loads of cum ended up inside me. You were twentieth and last, Ma."

She cracked up laughing. "Bloody hell, Benji. But you're young and enjoying yourself. Make the most of it! And there's nothing wrong with enjoying sex with multiple partners either. If you find a beautiful futagirl you want to have sex with, do it. Don't let others judge your lifestyle."

"I don't and I won't, Ma. Trust me on that one. I'll live life how I want but I also want to be happy, and having my girlfriends and other lovers will certainly do that."

Dinner at the table was lively as always, though I did miss Jade's presence. After only four days, though, she was already talking of changing her hours to just daytime so she'd be home in the evening. She'd make a little less money but I had a feeling she didn't mind. Just like every other night, I kept her company when she did get home.

"How many loads in the end, Benji?"

"You, Bailey and Vanessa left eighteen, Mum and Ma got it up to twenty."

She burst into giggles. "How are you feeling?"

"A little tender. No sex tonight, plus I have another young client tomorrow."

I slept with Bailey last night, happy to snuggle back against her, both of us wearing underwear so we didn't give into temptation. Mum woke me up the usual soft, her fingers caressing me before I felt her soft lips on mine. That woke me up, yawning before telling Mum I'd get up in a second. Turning around, I kissed Bailey before rolling out of bed.

Ensuring I said goodbye to everyone before I left, Mum was already behind the wheel as I slid onto the passenger seat. She'd barely left the road we lived on before she pulled the car over, lowered her panties, and lifted her skirt to reveal her erection. "Is this payment for driving me to work, Mum?" I laughed, "Not that I'm complaining. I'll blow you whenever you want."

I'd swallowed her load by the time we pulled up at work, sharing a last, lingering kiss that would have promised a lot more at any other time. Her eyes sparkled as I pulled back, and I think we had to face fact that the feelings of love were now well past anything we might have anticipated.

"Have a fun day, sweetie," she said as I got out of the car.

"I will, Mum. See you this afternoon?"

"Of course. I'll get my half an hour with my son on the way home too."

"Okay. See you then."

Waiting until Mum departed, the door to the house was already open as I walked up the short path, Naomi and Isabella waiting for me with smiles on their faces. Greeting them with a soft kiss on the lips, which only earned broader grins, I followed them inside. Another young client, a futagirl of twenty years old, had heard of my name and wanted to give me her virginity.

Naomi entered my room as I was getting ready. "Are you busy this weekend?" she asked.

"No real plans. Why?"

"Why don't we meet up for a drink? Get to know each other properly."

"Name a place and time, I'll be there."

Her face lit up. In fact, I think she got a little excited, bounding over to kiss me again. "I'll call you tonight," she whispered, "Though we can talk when you're finished." Pausing she then moved her lips to my ear, "Izzy might want to fuck you later too."

"That bother you?"

"Of course not. I'm hoping she'll let me watch her utterly nail you." Taking my hand, she placed it underneath her skirt. "I don't want to go too fast, Benji, but trust me, I want to be intimate. And I know it'll be good because your clients on Wednesday all left grinning ear to ear. If you do that for them, what would you do for someone you actually like?" Clearing her throat, the blush that appeared just made her more adorable. "Anyway, the young futagirl will be arriving around 10am and is hoping to spend the day with you. But, if she's like Riley, it might end up being too emotionally overwhelming so she might only be here for a few hours."

"No complaints from me, Naomi."

"Have a fun day."

"I'll do my best."

Kissing my cheek, she paused at the doorway and glanced back, a sweet smile, before she closed the door. I took a seat and waited for my next young futagirl, hoping she'd be as loving and wonderful as Riley had been.