The Futanari Diaries Ch. 05

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The life of a young man and his love for futanari.
9.8k words
4.79
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Part 5 of the 14 part series

Updated 08/03/2023
Created 01/08/2022
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UltimateSin
UltimateSin
5,319 Followers

Jade needed to wake me up the next morning as I was still fast asleep by mid-morning. She woke me up in a nice way, her soft lips pressing against mine. It made me smile, hearing her delightful giggle, opening my eyes to see her blue eyes gazing at me with adoration. "It's nearly ten," she whispered, "Don't want to spend all day in bed, do you?"

"Maybe if you're with me, I do."

Kissing me again, her smile broadened. "Sounds lovely, but I have studying, and Caroline needs you today. Between you and me, I think she might have been feeling a little left out. You've got a lot of lovers, Benji, but you haven't been with her yet." My face fell, Jade immediately cuddling me. "Not your fault. Definitely not your fault. It's new and exciting, and you almost have too much choice. She understands and is patient. But like Mum says about me, your two mothers are just as important."

"No-one but Ma today, Jade."

"Good boy. Just love her like you've always done, now you're just adding sex."

Walking downstairs, Mum and Caroline took one look at me and giggled. After making myself some toast and drinking a glass of juice, I joined Caroline on the two seater, sitting close enough our thighs were touching. Wrapping an arm around me, I cuddled into her side. No surprise she was wearing a skirt, and seeing the tent appear, I figured she wasn't wearing underwear.

"How are you feeling?" she asked.

"Oh, I'm fine. Good night's sleep does wonders."

"Are you sore?"

"Not really. Guess I'm getting used to being fucked a lot."

"Want to make love now?"

"Mum, I'm taking your wife upstairs for some fun."

"Okay. Lunch will be around 1pm. Caroline, try not to wear my son out before school tomorrow." And, with that, she turned her attention back to the book she was reading.

I'd found Caroline incredibly attractive since the moment Mum had introduced her. All my male friends had the hots for her, a definite object of desire. And as none knew my parents were futanari, they had no problem going on about the fact they were lesbians and what they did to each other. Little did they know, as I hadn't told Mike, Mark or Nathan the truth about them. Not their business unless Mum and Caroline chose to tell them.

Sitting down on the bed next to Caroline, I made a confession as I took her hand in mine. "I've found you attractive for a long time, Ma. After what Dad did to her, I just hoped she'd meet someone who loved her like she deserved. Thing is, I've seen you as my second mother since almost the day you moved in, and I've pretty much adored you since the day Mum introduced you to us. Always there to help, give advice, make me feel better, show me love. I'd never even consider calling you my step-mother. I just didn't know what to call you instead of Mum. But I've always loved you as much as Mum."

I made her cry. Good tears, she murmured, hugging me tightly. "I don't care what the paperwork says, you'll always be my son. And now I want to make love to him."

"Want a blowjob first?"

"Why not together? I'd love to taste you too. You go on top as you're smaller." She leaned back slightly. "Are you still disappointed or lacking confidence because you're not as tall..."

Smiling, I shook my head first. "No. I've come to like the fact. All my lovers are bigger than me, sure, but it seems you all seem to like the fact I'm this size. So I find no reason to complain."

As soon as she laid down, I finally got a chance to kiss her properly, then attack her large breasts. She laughed out loud as I sucked and nibbled at them, her nipples standing out proud. Caressing the back of my head, she whispered, "I never had the chance to have children of my own." Pausing, she asked, "Want to fuck my tits?"

"What?"

She smiled at me. "Want to stick your dick between your tits and fuck them until you cum?"

"Um, okay!"

Needed a little spit and lube for the job, but once she had her breasts wrapped around my cock, and I was thrusting between them, it was a somewhat bizarre but wonderful feeling. Caroline urged me on, shouting at me to fuck her tits, and cum all over her face once I was done, because she promised once I was, my arse was getting properly fucked.

Mum appeared in the doorway, watching me fuck her wife's tits. She urged me on too, and I was soon pumping that tight little gap she'd made. "My handsome son is fucking my tits. Never though it would happen. Go on, shoot all over me! Cum on my face!"

Mum wandered over, lubed up my bum, then stuck two fingers up me. Finger fucking me hard and fast, it was no surprise to anyone that I erupted within a couple of minutes, needing to lean forward and resting on my hands, as I released a couple of large doses of cum on Caroline's face. She giggled away, immediately using a finger to wipe up the mess to taste me.

Catching my breath, Mum applied more lube to me before gently pushing me back, feeling Caroline's girlcock poking at my rear entrance. "Slowly, baby," she whispered, "Nice and slow. Caroline, be gentle with him today. He was fucked pretty hard yesterday."

"We're making love all day, my love. Don't worry."

Mum kissed my cheek and wandered back downstairs, I assume keeping Jade company, if she stayed home. Caroline let me take control as I slid down her thick ten inch girlcock. Not quite like Miss Wilson, her girlcock was just insane, but a reminder of Alexis. Thinking of Alexis caused a brief grin. I'd known her as this confident futanari, but there was a shy side, realising how intense her feelings were. Shaking my head, I cleared my thoughts and focused on Caroline, how she felt inside me in that moment.

"Fucking hell, you've got a tight little arse," Caroline moaned.

"And it loves your long thick girlcock, Ma," I moaned back.

Once I bottomed out, we gazed at each other, grinning like fools. Grasping my wrists, she placed my hands back on her breasts and asked me to start riding her, assuring me that she was going to fill me up, no matter what. I was hard again already, my cock flopping between my body and hers, savouring the feeling of her thick shaft spreading me nicely each time I moved down on it.

It was a hot day outside, and despite the central air, I was soon perspiring. Caroline also glistened with sweat, moving up and down her shaft faster and faster. I finally just leaned forward, hands to either side of her. She knew what I wanted, running her fingers up and down my back a few times before she grabbed my butt.

"You sure?" she whispered.

"Please fuck me," I replied softly.

Caroline fucked me, her thick girlcock plunging my depths. The sound I made was whimpering as it was just so fucking good. Her cock must have been a blur at how fast it was thrusting into me. I eventually rested on her, one of her hands still on my butt, the other caressing my back.

"Good boy," she murmured, "Good boy. Take my big girlcock deep."

"So fucking deep," I whimpered, "Don't stop!"

"I won't, baby. Even after I cum, as long as you want."

The next kiss we shared was pretty intense. Full of all the feelings we naturally had for each other. Passionate, lustful, dripping with matching desire for each other, but also full of love. She was naturally the aggressor, the more dominant, but I made her smile as our tongues played together. I was still learning how to kiss, in all honesty. Still learning about everything. I just had a lot of good teachers.

Caroline warned me she was getting close, both hands now holding a cheek each, really driving her cock up into me. That had me grunting instead of whimpering, resting my forehead on her shoulder, begging her not to stop until she'd at least cum inside me.

"Oh fuck, baby, oh fuck..."

"Cum for me, beautiful. Fill up my bum!"

There was that usual throb of a thick girlcock up inside me as she started to cum, feeling her fingers dig into each cheek, hearing her cry out as she erupted. My god, what an orgasm she enjoyed, just firing again and again deep inside me. I actually started to giggle, figuring if I had been female, I'd definitely be pregnant by now.

Moving her hands up to my back and grabbing me tightly, she rolled me onto my back, moving my legs so they were wide and resting against her upper arms, immediately starting to thrust into me again, this time nice and slow.

"Fuck..." I moaned, "Fill me again."

"I will, but it'll be a while."

"I don't mind. Fuck me for as long as you want."

She laughed out loud. "You're insatiable. What have we created?!?!"

"I waited a long time for all of this," I said softly, "Going to take advantage of it now."

She laughed again. "Lots of different girlcocks?" A look must have passed my face as she stopped, buried inside me. "Benji, sweetheart, it's perfectly natural and okay to have fun. It's only a certain section of society that expects and almost demands monogamy. Our kind never demands. Sex is something to be savoured and enjoyed, and if you want to experience it with numerous people, it's even better. Is the sex we're having different to when you're with your sister?"

"Your girlcock is different, for starters. Your aura is different too. That make sense?"

She leaned down to kiss me. "Exactly. That's why men who are with futanari can marry more than one, and trust me on this one, sweetie, you're going to have plenty of futawives."

Caroline resumed moving her hips, her delightful girlcock thrusting into me again. God, she felt wonderful, though I was thinking it was actually good to wait a little bit. The smile on her face never wavered, her eyes sparkling with joy and her love for me in return. Releasing my legs, I wrapped them around her waist, feeling the angle change which caused me to moan loudly, earning a delightful giggle from her.

No idea how long we made love for until she was ready to cum again. She'd barely changed tempo and I simply didn't want her to stop. But when she murmured she was getting close, I told her to push my knees back as far as she could and just nail me so she could cum. Kissing me softly, she did what I suggested and started to pound my little butt.

"Oh fuck, Benji!" she cried out.

"Keep fucking him, lovely," Mum said, glancing to see her in the doorway, stroking her thick girlcock.

"Come fill his mouth until I fill his arse, my love."

Mum sat on her knees next to me, offering her girlcock for me to suck as Caroline laid assault to my arse. Caressing my cheek, Mum said she wasn't going to cum but she was a good distraction. "Oh fuck, oh fuck... Cathy, your son..."

"Best fuck except for my pussy?"

"God yes. He's so fucking tight. So warm. And his tight little body. Fuck, I'm so hard all the time nowadays."

Moaning around Mum's shaft, I couldn't say nor do anything else. Caroline completely owned my body, hearing her cry out as she finally started to fill my arse again. Mum started to fuck my mouth, and I guessed she'd been standing in the doorway long than I knew, as I was rather surprised when she filled my mouth at almost the same time.

Releasing my legs, Caroline collapsed on top of me, almost passing out, as I wrapped my arms and legs around her again, Mum withdrawing her shaft and lying down next to us. I'd never been filled at both ends at the same time, a little of Mum's cum having dribbled down my chin and cheek.

Feeling Caroline want to pull out, I tightened my legs, earning a soft giggle. "I need a rest, Benji," she whispered.

"You both need a wash," Mum insisted, "Go take a bath together. I'll go run it and let you know when it's ready."

Caroline turned onto her side next to me, making sure I was spooned back against her, almost cocooned by her larger body, cuddling me nice and tight. "That was wonderful, Benji. Thank you for making an old futagirl happy."

"Please, you're not that old. Shit, if I was out for one night and saw you in a pub or something, I'd hit on you. Badly, but I'd try."

"Futanari my age would eat you alive, Benji. But, fuck, you'd have the time of your life."

After enjoying a relaxing bath together, we joined Mum downstairs for lunch. Wondering where Jade was, Mum shook her head. "She's not jealous, but because it's still rather new, she can't handle hearing it yet. Give it time and she'll be like me, wanting to watch you and join in at times."

"Should I stop?"

Mum took my hand and squeezed. "God no. As Jade said, you will have many wives. The only thing that breaks her heart is she can't be one, can't get that certificate that makes it official. But that will never matter. She will be by your side, until death do you part."

"Maybe we should just have an unofficial wedding?"

I meant it but thought nothing more of it. Mum loved the idea, so did Caroline, but I asked them not to mention anything. I didn't have a job, stopping working until I'd graduated, so was living off some slowly diminishing savings from my previous job. I did odd jobs here and there but Mum had always insisted my studies were more important.

Caroline told me after lunch that she was happy, but if I was still interested in more, to just grab her hand and squeeze, and we'd head back upstairs. But we were happy to have finally made love, so the three of us headed to the pool to relax from the heat. Jade returned mid-afternoon. Joining us in the pool, she swam straight for me, hugging me tightly.

"Did you have fun?"

"I did, Jade. But I don't want to upset you."

She leaned back to meet my eyes. "Not upset and will never be jealous. But I'm not at that point where I can listen to you making love to someone else, even our parents. I'll get there soon and I'll smile. I can smile about it when not here, but in the house..."

"I don't want to hurt you," I whispered. The thought alone nearly broke me. She hugged me tightly against, assuring me I wasn't and never would.

The rest of the afternoon and evening was spent relaxing, Mum ordering in dinner again, stating it was simply too hot to turn on the oven or stove, but she did order in something vaguely healthy. I hadn't been going to the gym recently so wanted to watch my weight too. Jade suggested that, until my exams were over, we should go for a jog in the afternoon, just to keep fit. Adding that she'd run in front of me so I could watch her arse was very convincing.

With the countdown to the last month before final exams, the next week was what I'd call quiet. Not a return to normal, but quiet in the sense that I had regular sex but it was 'normal'. Jade still drove me to school each morning, only departing after a steamy kiss that was starting to draw a regular audience. My days would be spent with nearly all the futanari in my year group now flirting with me, or at least being incredibly friendly. They'd been friendly before, I certainly had more futanari friends than male, but it was something else entirely now.

Only had sex at lunchtime twice during the week, both times with Vanessa. Bailey, Chloe and Georgie were almost desperate to make love, but we agreed to wait until after final exams. We would have the summer break into the new year before we would head to university. Though I did plan on getting a part-time job to make a little cash, I hoped to spend some time lazing about too.

Thursday night told me the end of the week was going to be different though. Miss Wilson sent a message to me, but also to all my friends. Futanari, not male.

'Study session. Friday afternoon after final class. Please come to my classroom at the end of the day. Those already there will remain. See you tomorrow.'

Showing the message to Mum, she laughed out loud. "Looks like my little boy is going to be having some fun tomorrow."

Telling Jade in bed later that night, she simply cuddled me tighter, feeling her erection press into my stomach. "You like her, don't you?"

"Always though she was beautiful. Knew she was futanari. Could always tell with her, though I've gotten better at figuring it our over the years. Except for my family, at least. Can't believe I went eighteen years without figuring it out. It's embarrassing."

"It was done with love, Benji. You know that, right?"

"I know. No complaints any longer. I was a little hurt to start with but I now understand why."

Mum and Caroline were up early the next day and I knew exactly why. Standing at the door as Jade and I walked to her car, I heard them both shout, "Have a great day. Don't come home too late!"

Groaning, I slid onto the passenger seat, my sister giggling away as she backed out of the driveway. Holding my hand as always, she remained in the car when arriving, leaning over to share the usual passionate morning kiss. "Call me if you need a lift, but I'm assuming Miss Wilson will drive you home?"

"Probably. I'll let you know."

Getting out of the car, I was greeted by my friends as always. Vanessa asked what I was doing during the weekend. Letting her know I was probably going to spend some time with Mark, Mike and Nathan, though not sure what we'd be doing, her face lit up. "Think they'd mind if some of us joined in?"

"I don't think so. I'll let them know. Might put their nose out a bit as I haven't spent much time with them lately." Glancing around, I added, "Not that I have any reason to complain."

Vanessa took my hand as we walked into school. "Did you get the message from Miss Wilson?" Nodding that I had, she added, "I can only assume what it's about then."

"Someone's getting fucked," Chloe sang next to me.

"Wonder if it'll be a repeat of your last study session?" Aubrey asked.

That was a good question. I wouldn't mind if it was, but I did worry about how they would all react. It wasn't anything hardcore, at least what I thought was. However, I was left thinking that Miss Wilson might be wanting to put on a little bit of a show with me. That didn't bother me at all. Though, if my girlfriends were watching, I was left thinking the floor was going to be left absolutely soaked in cum.

Miss Wilson did send a private text just before lunchtime, warning me not to have any sex nor cum, so that told me what to expect after school. I was rather excited by the last lesson of the day and week, Miss Wilson looking delectable as always. Keeping us busy, she walked up and down the aisles between our desks, resting her hand on my shoulder as she passed before turning, leaning down to my ear.

"You're mine, Benjamin," she breathed, biting my earlobe for good measure. Sent a shudder through my body as I felt her hot breath on my neck, "And your girlfriends are going to watch me fuck you senseless."

"Fuck," I muttered.

I noticed her glance around before she reached down between my legs, gently grasping my cock. "So handsome," she whispered, "I've masturbated constantly all week, thinking about what we did last Wednesday then making love on the weekend."

Glancing right, Bailey was fondling her girlcock underneath her skirt. She met my eyes and smirked, seeming to know exactly what Miss Wilson was whispering into my ear. She blew me a kiss before I turned away, trying to focus on my work. "Do you want my girlcock inside you?" Miss Wilson whispered.

"God yes," I murmured, "So much..."

Releasing my cock, she stood up and remained at the back of the room until the end of the lesson. When the bell rang, she wished everyone else good weekend, students hurrying out of the room except for Bailey, Vanessa and myself. Miss Wilson walked by me, leaving a soft kiss on my cheek first, before she waited by the door. No surprise all my girlfriends arrived within five minutes, excited about what was going to happen. I hadn't moved, feeling my heart beating away due to my own excitement.

"Take a seat, girls. Benjamin, front and centre."

Rising to my feet, I walked past my girlfriends, all of them kissing my cheek as I passed, as I stood before Miss Wilson, sitting in her chair. Opening her desk, she passed me a piece of paper.

UltimateSin
UltimateSin
5,319 Followers