The Futanari Diaries Ch. 09

"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 sister 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.