THE FUTANARI DIARIES CH. 05 By UltimateSin

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 Aunt?"

"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 Aunt 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

'Study group in session. Please do not disturb' was written on it.

"Please stick that to the door, then close and lock it please. I'm going to get ready in the supply closet." She stood up, gently gripped my chin and kissed me. Her eyes sparkled with mischief. "I so wanted to just bend you over your desk all lesson," she said quietly. Turning me around, she patted my butt to do what she asked.

With the door locked and closed, I glanced to see my eleven girlfriends. Females hated that futanari used the term 'girlfriend'. In fact, they hated them for the simple use of feminine pronouns. Then again, futanari had proven to be far more feminine recently. No wonder the incidence of male/futanari relationships had exploded in the past hundred years after centuries of oppression.

The door to the supply closet opened and an absolute vision walked out. On her feet were stiletto's, at least six inches, so she now towered over all of us. Black stockings and suspenders. No panties so her glorious girlcock swung with each stride. She wore a black bustier top that just about covered her large breasts. Long black leather gloves that reached her elbows. She'd put on make-up, her lips a vibrant red, dark eyeshadow around her eyes. Her red hair flowed down to her shoulders.

She was utterly fucking beautiful. A futanari goddess.

"You're beautiful," Vanessa said, noticing I'd been left speechless. There was plenty of agreement to that statement.

Miss Wilson walked towards me, looking me up and down. "Strip!" she ordered.

My clothes went everywhere in my desperation to get naked for her. Once I was, she stepped closer to me, running a hand down my body to my hard cock. "I want it soft!"

"What?"

That earned me a grab of the shoulders, bent over the desk and a hard slap on my arse. "Don't 'what' me, young man! What am I called when I wear this?"

"Mistress!"

"Correct, and you do what I say, and I want your cock soft. Soft! I want it soft!"

"Yes, Mistress. I'll do my best."

"Oh my god," I heard a few of my girlfriends' whisper.

I closed my eyes and willed my cock to go down. I thought of the most awful and gruesome things possible that would kill my libido, at least for a few seconds. To my relief, I did feel my cock finally go down. "Vanessa, in the closet is a box on the floor, waiting for now. Please get it for me. Benjamin, eyes closed."

"Yes, Mistress."

Hearing Vanessa placed the box on the desk next to me, I was gently hauled to my feet, keeping my eyes closed. I didn't expect what came next. I felt something placed around the base of my balls, knowing what that was. I then felt something placed over my cock, a click or two afterwards. "Your cock is now caged, and you are not to cum until I say so. Understand?"

"Yes, Mistress," I whispered.

"Open your eyes."

I blinked a couple of times, noticing Miss Wilson stand before me. Reaching into the box, she grabbed the ball-gag I remembered she used last time, putting that in place, making sure I was comfortable. Meeting my eyes as she held the blindfold, she whispered, "Remember what to do if you want to stop?" Nodding, she kissed my forehead, probably the last sweet gesture for the next hour or two. Probably...

Once blindfolded, I was bent over her desk. Hearing a metallic clink, I felt a cuff placed over my left wrist, pulled behind my back and a click over my right wrist. At least she made sure I was comfortable, feeling her covered nails dig into my back, all the way down to my cheeks.

"Next time, I'll make sure you wear a butt plug all day so I can fuck you immediately. A big one, just for you."

I couldn't reply, considering the gag and all. Feeling her spread my legs, her tongue was a slight relief as she admitted to enjoying eating my little butt before having sex. She didn't do it for all that long before I felt lube applied and two fingers slide inside me. She wasn't gentle, one hand on the back of my neck as she finger-fucked me. A third was added after a couple of minutes, and she was fingering me in a such way to cause me a little discomfort considering the cage.

Adding a fourth made me moan louder as she was really fucking me, and I did wonder... "I could fist you right now, Benjamin, and there's nothing you can do about it. All the way up to my elbow. I bet you'd love it, you little slut."

Miss Wilson had promised that would be the only time she'd ever use language like that with me. We were both characters, in a way. "But why fist you when I have a massive girlcock that belongs in you instead."

Feeling her fingers disappear, I felt the thick head of her girlcock at my rear entrance and she wasn't gentle when sliding it in. I grunted as I felt all eleven inches slide in within the space of a few seconds. She did wait a few more seconds as I tried to get comfortable, difficult with hands handcuffed and a thick girlcock up my bum.

With her heels making her taller, I sensed her presence over me, her breath in my ear. "I'm going to utterly fucking destroy you now with your little girlfriends watching. I'm going to make you my permanent slut, keep you on a dog dollar to serve me whenever I want." She thrust into me hard, earning a grunt. "I bet you'd love it too. Pass you around so my friends can enjoy my little slut." Another hard thrust. "Constant double and triple penetrations. No end of fisting. You'll drink our piss." Another hard thrust. "Whatever deviant thing comes to mind, we'll do to you." Another hard thrust. "And I'd bet you love every second, your only desire to please Mistress and her friends. The perfect little slut for our enjoyment." She paused for a moment. "Please take your girlcocks out and enjoy yourselves. My little slut here will clean up any messes."

"Fucking hell," one voice said.

"Damn, he's done this before?" another wondered.

"Not to this degree," Miss Wilson replied, "But this little slut will do anything I demand of him."

The time for talking ended as she started to thrust hard but slow into me. Earned more grunts than any moans, feeling her lower body press into my back and I could feel her breath near my head. Slowly but surely, her thrusts got harder and faster until it felt like she was ramming a log up my bum each time. The pleasure was overwhelming. Sure, there was an ache but, my god, I'd never even considered something like this could bring such pleasure.

Feeling her move back, she grabbed the chain linking the cuffs and pulled me back, straining my shoulders. And then, if possible, she fucked me even harder. The sound of her skin slapping against mine echoed around the room. It wasn't silent, my girlfriends clearly masturbating and moaning at the same time. Miss Wilson slapped my arse constantly with each hard thrust, left thinking my arse was going to be bright red.

Grunting and groaning, I'm not sure how I actually endured it, but I wasn't going to give in. Plus, I was enjoying it far too much. "You little slut, you should be begging me to stop right now," Miss Wilson growled. When I actually pushed back a few times, she really rammed her cock into me, making me squeal. "Oh, the little slut wants more, does he?"

When she pulled out suddenly, I moaned with disappointment. Hearing giggles, I was wondering what she was doing. Then I felt a slap on my left cheek. "I'm going to paddle you something fierce, slut. Girls, count off each one!"

She stopped at thirty, fifteen on each cheek. Sliding her cock back inside me, I almost cried with relief to just feel her girlcock back inside me. Hearing me whimper, she stopped for a moment, wondering if I was crying, but when I pushed back, desperate to feel her fuck me again, I knew her mind was reassured. "Time to fill your arse, my little butt slut."

Anything before was merely an entrée. She'd never been as rough with me until then, feeling her lift me flat up on the desk and she quite clearly joining me, driving her cock as deep as possible, now earning a grunt with each thrust of her cock. I was now desperate for her to cum as I was worn out.

"Miss, you're hurting him." That was Bailey, and I could hear she was upset.

"My little slut is just fine. Trust me, Bailey, you'll see in a minute. But my little slut needs an injection of my hot cum in his arse."

Thankfully, that injection came a couple of minutes later. She'd never filled my arse as much as that time, hearing her breathing deeply above me once she was finished. Feeling her pull out, I was left alone for a moment before the handcuffs were gently taken off my wrists. The ball-gag was taken off next, moving my jaw as it was a little sore, before she removed the blindfold, blinking as I adjusted to the light. The last thing she removed was the cage off my cock and the clasp around my balls.

Miss Wilson sat in front of me, her eyes showing a little concern. "Are you okay, sweetie?"

Managing to nod, she helped me sit up, which made me wince, wrapping my legs around her as carried me to her comfortable chair, ensuring I straddled her lap. Resting against her, she caressed my back. "See, Bailey, he's okay. But I'm sorry if that shocked you."

"It was a little intense. But I think I understand, Miss."

"Never thought a young man, only eighteen, would enjoy it," Miss Wilson stated.

"I love you," I whispered. I truly did. I had for a while now. My crush for her had blown up into something far greater after we'd made love.

She squeezed me tighter. "I love you too. I shouldn't. I really shouldn't... But I do love you too. I can't help it. I haven't felt like this in years."

"Am I cleaning up the floor, Mistress?"

"Hush now. No more of that. And no, that was just something to turn on your friends. Did you make a mess, girls?"

There was a lot of giggling, suggestions that an ocean of cum was now residing on the tiled floor. Miss Wilson explained that some rags were in the box and if they minded cleaning up. My girlfriends were more than willing to do so, Miss Wilson continuing to cuddle me. I knew why, she called it aftercare for such an event. To be honest, I needed it, and I felt safe in her arms.

"We won't do that again for a while unless you want to. That was intense," she said, "But I'm so proud of you, sweetie."

"Did you mean anything that you said?"

"We can discuss it later, if you want. As I said, I won't do anything you don't want to do."

Finally lifting myself up, I met her eyes and kissed her. Earning a smile, I slid off her lap and almost collapsed. My legs were jelly and I could feel cum leaking down my legs. Bent over the desk, Miss Wilson helped clean me up then rubbed cream onto my bum, giggling that she had left it quite red, but the paddle was better than the whip for my soft skin.

Helping me get dressed, she could see I was almost useless. After my girlfriends all hugged and kissed me goodbye, with promises to text them later, Miss Wilson quickly changed into her other clothes, grabbed her handbag and almost carried me to her car, barely able to walk next to her. She didn't even both putting me in the passenger seat, opening the rear door and insisting I just lie down.

Arriving at home, she helped me off the rear-seat, Mum opening the door and noticing my dishevelled appearance. "Enough of that guilty look, Sandra. Did he want it?"

"God yes, Mum," I replied, "It was a lot of fun. But I'm done in."

Mum kissed her cheek. "Take him to the bathroom and enjoy a bath together. Something sweet to do after what was obviously some intense sex."

Miss Wilson stopped by my mother. "I love him," she whispered.

"I know, Sandra. And I know he loves you, so it's fine with me. Scoot. Bathroom. Bath. Now. And you're staying for dinner."

"Thank you, Cathy."

I fell asleep while leaning back against Miss Wilson while we bathed. I only woke up because I heard her soft cries. Turning to look at her, she wrapped her arms around me, quietly told me she was happy. Happier than she could remember. She just never thought someone my age would ever find her desirable.

Mum brought her a robe to wear while I staggered to my bedroom. Jade had obviously been told, coming to give me a warm hug. Gathering around the table for dinner, Jade looked at Miss Wilson. "Was it fun, Miss?" she asked.

"Your brother is an absolute delight, Jade. So open-minded and willing to please, almost putting ours above his."

"Bollocks," I muttered, "I derive an equal amount of pleasure from anything I do with anyone. Trust me, Miss... er, Sandra, I enjoyed every second of what we did in that classroom." I paused before adding, "Okay, the one thing I really need is to cum."

Miss Wilson offered her hand, helping to my feet, as she fell to her knees. "Sorry, sweetie, in trying to clean up and... I'm sorry. Forgive me?" she asked before swallowing my swelling cock.

"The only reason I mention is that I'm a little sore, you know, blue balls..." Her eyes sparkled as she sucked my cock. God, she was pretty fucking good at it. Caressing her face softened her eyes even more. "Love you even more now," I said softly.

I didn't last long, Miss Wilson swallowing my load before I helped her up and cuddled her. "Okay, Sandra, consider yourself invited whenever you want to come around," Mum said, echoing the invitation from the previous weekend, "Have fun with the youngsters though I guess Caroline and I are more age appropriate..."

"If you're inviting me to your room, Cathy, though only dependent on your wife, of course."

"We'll double team her," Caroline said, amused when I noticed Mum's eyes light up.

Miss Wilson looked at me. "Would it bother you..."

"Of course not, Miss. In fact, I'm finding the idea a turn on."

Caroline winked at me. "Live show or film it for you?"

"Both," I replied, smirking away.

Miss Wilson stayed to enjoy a drink outside as the sun started to set. Everyone gave her a hug before I escorted her down to her car. That last kiss we shared was an expression of the feelings we clearly shared. I was left believing she wanted to invite me back to her place, but after stroking my cheek, she wished me goodnight. I stood there until she'd drive out of view.

Jade cuddled me once we were in bed that night. In fact, it was a sedate weekend, giving myself a Saturday off as I was still sore. Didn't mean I couldn't use my mouth, Mum, Jade and Caroline finding themselves blown throughout the day, swallowing down their cum each time. Vanessa dropped by for an afternoon study session, blowing her while we took a break, ending our study session with a swim and make-out session in the pool.

Sitting under the shade afterwards, I asked, "How upset was Bailey?"

"She was crying, Benji. She'd never seen anything like it before. She thought it was really hurting you."

"Don't get me wrong, there's a little pain, but the pleasure is overwhelming. Think it's to do with endorphins or something. I'm not sure, not read up about it yet. Certainly don't like hearing she was upset though. I'll give her a call tonight, put her mind at ease again."

I went further, calling her and inviting her around for the Sunday. We shared a couple of classes, so could study, but I'd take the time to chat. I was starting to get to know her but I figured a private conversation. I told Mum and Jade, both just smiling, admitting they thought Bailey was very sweet from the time she'd visited.

"In fact, from the sounds of it, all of your girlfriends are adorable," Mum said, "Beautiful. Sexy. Confident. But definitely adorable too."

Jade was waiting for me in bed that night, naked with her thick girlcock waiting for me. Stripping off after shutting the door, I joined her on the bed, kissing her softly before her tongue slid into my mouth, her fingers caressing my body and cock. Moving down to her sensitive neck earned a couple of moans before moving down to her spectacular breasts.

"Lick your Aunts' nipples, little brother," she murmured, "Suck them. Nibble them. Enjoy them. Yours, whenever you want, baby."

I lavished her breasts with attention as I gently stroked her girlcock at the same time, feeling her pre-cum leaking out onto my hand, rubbing it into her breasts to taste her at the same time. It earned a giggle, before I finally moved down her body, a trail of soft kisses over her naturally toned body, before I ran my tongue along her shaft.

Ignoring her cock, I ran my tongue over her smooth ballsack, taking each large one in my mouth, ensuring I didn't hurt her, before running my tongue down her perineum. She seemed to sense what I was doing. "Are you sure, baby?" she asked softly. Nodding, she lifted her legs and arse as I delved into that space between her firm cheeks. "Oh baby, that's good," she moaned as I tongued her little rosebud. She didn't want to be fucked but no reason I couldn't give her that sort of attention.

She loved it, but she wanted my mouth somewhere else, licking back up to her girlcock and swallowing most of it in one movement of my head. Desperate for release, I didn't waste time deepthroating her, enjoying her cry of delight as I had my head bobbing up and down quickly, eager for her cum.

Feeling her fingers grab my hair, she started to thrust at the same time, a sign I knew well that she was getting close. "Oh fuck yes, Benji. Suck my fat girlcock. You love it, don't you?" I looked up and met her eyes, winking at her. It earned a giggle. "That's right, you want your Aunts delicious cum now. You've earned it. I'll give you my cum whenever you want." She was almost fucking my face by then, gently, but still doing it. I let her control me as I enjoyed it as much as she did. "Oh god yes, here it comes, Benji. All my cum for you. Swallow it all down."

She erupted in my mouth, greedily gulping down each thick load. By the time she was empty, barely a dribble, she relaxed on the bed as I continued to bob up and down until she whispered it was a little sensitive. Ensuring she was at least clean, I lay on my side and cuddled into her, feeling her arm wrap around me as she covered us in a sheet. We were both fast asleep within a couple of minutes.

Waking up horny the next morning, as it was a little unusual to go an entire day without having a girlcock inside my bum for over twenty-four hours, I walked into the dining room naked, my arse already lubed. Mum and Caroline glanced at me as I looked at them, smiled, then walked back to the living room, bending over the arm of the couch.

Mum was inside my arse within thirty seconds. "Morning, baby," she whispered, thrusting into me slowly.

"Morning, Mum. I woke up horny, Jade looked far too peaceful asleep, but I needed a girlcock inside me."

Caroline sat on her knees in front of me, offering hers to suck, so I found myself spitroasted by my mothers, taking a load in each end after around fifteen minutes. It worked up an appetite, both kissing my cheek, telling me to sit down and they'd prepare me breakfast. Jade walked in as it was being served up, noticing the three of us smiling, Mum humming a tune to herself.

"Okay, who fucked him?" Jade asked, laughing away.

"I fucked him, he sucked her," Mum replied, gesturing at Caroline with the spatula.

"I didn't want to wake you, Jade. You looked so beautiful..." That earned a soft kiss on the cheek. "Guess I wore you out last night?"

"That was one hell of an orgasm, Benji. My entire body was tingling afterwards."

"Our boy is getting better?" Mum asked as she placed a plate of bacon, eggs, sausage and trimmings in front of Jade and myself.

"I'm still learning, Mum. It will take lots of practice to become a great lover. Or at least better at blowjobs. And I could probably become a better kisser."

"Oh, no complaints from me there, sweetie," Caroline said, "Then again, you have good teachers."

"What time is Bailey getting here?" Mum asked as she sat down to eat.

"Around lunchtime. We'll study this afternoon, plus we need to have a chat about Friday afternoon, and also our own relationship."

"Sex?" Jade wondered.

"I'm not sure. She wants to. I want to. But we want it to feel right in the moment."

"You really like her!" Caroline exclaimed.

Feeling myself blush, I nodded immediately. "I've noticed her for years, same as her with me, but we were just never in the same group of friends. But she made her intentions clear to me recently and, since then, we've grown closer."

I actually spent the rest of the morning playing my games console, just chilling out for once. Jade was busy with her own university studies, in her final weeks before her semester ended. I was on the verge of my final exams, two more weeks of classes, a final week of study, then the exam period finished. Then it would be two weeks to Christmas.

Bailey arrived at lunchtime, Mum offering to make us some sandwiches. Both of us thanking her, I grabbed some cans of soda, taking our food and cans back to my room. Shutting the door, we sat back on my bed to eat. "My mother would freak if I shut the door with company. Typical woman," she muttered.

"Oh, your mother..."

"Mother is female, father is male. Let me tell you, the fact I'm futanari... Run away more than once. It's only Dad who comes looking for me."

Wrapping an arm around her, she leaned against me. "I'm sorry. That sounds awful."

"I have good friends. Their parents will help me when they can. Dad then gets me, my parents argue. Mum's... You know, one of 'those'. I know she'll kick me out as soon as I finish school. I thought she would do it as soon as I turned eighteen, but I think Dad protected me from that."

Finishing our food, we grabbed our workbooks and got to work, bouncing ideas off each other. Time passed quickly, realising it was late afternoon before either of us checked the time again. Placing our books on the floor, there was that moment which happens when your eyes just meet. Next thing you know, your lips are locked together and the passion is increasing with everyone second.

"What do you want?" I had to ask.

"I want you, Benji. For so long, I watched you. With Vanessa. With Chloe. With Georgie. I was jealous, but coming from my family, I didn't understand. My auntie, the only other futanari, so naturally estranged, found me online and coached me through what I'd feel and how things truly are for my kind in relation to males like you. That day I sat next to you in class with Miss Wilson..."

"I'm glad you did, Bailey. So, I ask again, what do you want?"

"I want to make love. I want to make love with you, Benji." Tears started to fall from her beautiful blue eyes. "My god, I've never wanted anything more."

"Want to do anything else first?"

"Later. We have all the time in the world for that."

"Know what to do?"

It was her turn to blush. "Only what I've read and seen on the internet."

"Want me to lead?" Nodding, I added softly, "I can't wait until you're inside me, Bailey."

She hugged me tightly. "Me too, Benji."

Bailey was tall as we stood up, stating she was 6'2. Good thing I loved futanari and my partners being taller than myself. She wore a simple t-shirt, helping that off to reveal a white, relatively normal bra, which I expertly took off with one hand, earning a giggle, admitting I was getting used to taking off bras. Like most futanari, she constantly wore skirts and dresses, so that was next to go, kicking off her sandals before she rolled off her panties, her thick eight inch cock standing out proud, pre-cum dripping from the head of her cock.

After helping me strip off, we made out, lubing up each other before we gently stroked each other. She shuddered every few seconds and I knew was extra excited. "Bailey," I whispered, meeting her eyes, "Let me blow you, enjoy your load, and you'll last longer when we make love." Taking her hand, I sat her on the edge of my bed, sitting down on my knees between her legs. "Nervous?"

Biting her bottom lip, she nodded. I knew confidence came later for many futanari. Like any virgin, with no experience, they were full of nerves the first couple of times. Just running my tongue up her shaft caused her to moan loudly, feeling her girlcock throb, and I knew she wasn't going to last long. I knew she might also be embarrassed, sitting up to kiss her again, using similar techniques to what I used on others, focusing on the rest of her body and not her girlcock.

When I did finally arrive at it, she was lying back on the bed, groaning loudly when I wrapped my lips around her thick shaft, pre-cum leaking from the head of her girlcock, moaning as I enjoyed her taste.

"Oh my god!" she shouted. Well, the rest of the family knew what we were doing, but with the door shut, no-one would come looking. That was the rule. With family, come on in. With a visitor, knock and only enter if summoned.

Wrapping my hands around her thighs, my head was quickly bobbing up and down her member as I knew she needed a release. Her fingers ran through my hair, looking up into her eyes, her cheeks already wet. I had a feeling this was going to me an emotional afternoon for her. I think she was someone who needed to be loved.

"Oh fuck," she cried, feeling her started to throb in my mouth, "Oh god, Benji, I'm gonna..."

Savouring that first spurt, I moaned loudly as I eagerly awaited each subsequent spurt, swallowing her delicious cum as she collapsed back on the bed, watching her chest rise and fall. Releasing her legs, I quickly cleaned up her cock before I kissed back up her body until I was resting on her lap, looking down at her beautiful face, amused that her black hair was stuck to her forehead and cheeks.

"I had no idea," she muttered, "No idea at all."

Suggesting she turn so she could lie down comfortably on the bed, after a quick shuffle, I grabbed my lube and prepared myself for her, lubing up her girlcock again, though I wasn't in any rush, giving her time to just relax. We spent a few minutes making out and cuddling, and I think that meant the most to her. Just a little affection meant the world.

"Stay the night," I suggested, "You're not much taller than Jade, same height at Caroline, I think. You can borrow..."

"I brought a change of clothes," she whispered, noticing the blush, "I didn't want to go home tonight."

I sent a quick text to Mum, letting her know we'd have a guest for dinner and she was staying the night. I also let Jade know, as I knew she loved having me sleep with her whenever possible. Mum returned a message, stating all was fine. Jade sent a smiley face and a love heart. I sighed with relief that she was fine with it.

Sensing Bailey was ready, I positioned myself, grabbing the base of her shaft and pressed it against my rosebud. She gasped as the head slipped inside me. It was starting to get slightly easier. Considering all the sex I was having, I wasn't really surprised, though stories of incredibly loose arseholes and whatnot were nothing but old wives' tales.

Sliding down her length nice and slow, Bailey's face was one of shock before a broad smile formed, her eyes lighting up as she soon felt her entire length buried inside me. "How does it feel?" I wondered.

"So tight and warm. I feel... connected to you."

"Well, you are, Bailey. In more ways than one though."

Slowly starting to ride her, I grabbed her wrists and put her hands at my hips, adding that she could also grab my butt, if she wished. And if she wanted to fuck me, all I needed to do was lean forward and she could take control, if she wished. Otherwise, I loved riding girlcock and assured her that she was going to fill my bum.

"What about you?" she asked.

"I'll stroke myself. Want a load on you?"

"God yes. I want to see you cum, Benji."

Starting to stroke my cock at the same time as bouncing up on her girlcock had both of us feeling rather excited, leaning down to give her breasts some more attention before leaning up to kiss her again, driving my tight butt down on her cock each time, making her moan, while I felt my orgasm fast approaching. I sat back in time to spurt all over Bailey, the first firing at far as her chin, smiling as she erupted in giggles, the next couple landing on her breasts before I left a little puddle on her chest.

"Fucking hell," I groaned, stopping for a moment with her girlcock sat inside me still, "And your girlcock feels absolutely fucking sensational buried in me, Bailey."

"Can we roll over, Benji?" she asked softly.

A few seconds later, I was on my back with legs spread, Bailey sliding her girlcock back inside me, slowly thrusting away again, her eyes gazing into mine before I leaned up to kiss her again. She whimpered into my mouth, sensing her desperation to cum inside me but she wanted the moment to last. Resting on her forearms to either side of me, I pulled my legs back further, feeling her even deeper inside me. Moving faster, I knew she was on the way to orgasm.

Her kisses became more urgent but increasingly passionate, eventually breaking apart to rest her forehead against mine. She was incapable of words, only moans and whimpers escaping her. "Cum in me, beautiful. Cum in me. It's okay, we have tonight too."

"And after?" she manged to ask.

"Of course. I'm not one and done with any lovers, Bailey. You're all special to me."

She wasn't quite when reaching orgasm, crying out as I felt that familiar warm sensation when an enormous girlcock thrust and then spurted her seed inside me. She pumped me hard those last couple of minutes, losing herself in the sensation of my tight arse and her orgasm. She kept pumping well after she was done, not wanting to stop until she simply couldn't go any longer. Wrapping my legs around her, I ran my fingers up her cheek and through her hair, gently dragging her down to kiss me.

"I'm not dreaming, am I?" she asked softly. Giving her a gentle pinch on her shoulder earned a sweet sounding giggle. "Okay, now I'm sure."

Feeling her pull out brought its usual momentary disappointment, smiling to myself at the fact I was already a little addicted to the feeling. Lying on our sides facing each other, we conversed quietly, interspersed with some hot and heavy making out, enough to get her hard again within a fifteen minutes. "Again?" she wondered, loving the eager tone to her voice.

Seconds later, I was on my knees, head resting on a pillow, Bailey figured it all out rather quickly. She remained rather slow and gentle until I turned back to look at her. "This position, sweetie, is to fuck me. Trust me on this, you're not going to hurt me, and we'll both love it."

Taking further advice, leaning forward to grab my shoulders, I lowered my arse enough to be comfortable, and she gained more confidence as she started to fuck me harder and faster. When I urged her on even more, she started to giggle as her skin slapped against mine. Making a further suggestion, she mounted me properly, a position I'd grown to absolutely adore when being fucked, her thick girlcock now driving deep inside me.

"Oh fuck... Benji..."

"I know, gorgeous. You feel fucking wonderful."

"I love you," she whispered into my ear, "I have... as long as Vanessa... but always from afar..."

"I'm glad you sat next to me that day in class." I turned to kiss her. "I've fallen in love with you too."

"I'm going to cum then I need another cuddle."

"Can't wait until you blast in me again. Love the feeling."

Her next orgasm was even better than her first two, I think, really driving her girlcock into me until she just about collapsed. Carefully extricating myself from underneath her, she was half asleep so I stayed on my side as she rested on her front, lightly caressing her back. She smiled often, but there was often a little fire lacking in her eyes. The smile on her face, the look in her eyes as she lay next to me, this was a futagirl as content as could be.

After a quick shower, we put on swimwear and headed out to join the family. It was getting dark so it would only be a quick dip. As soon as we were in the water, Mum asked, "First time, Bailey?" She blushed but nodded, hugging me tightly. "Was it good?"

"Is it always that good?"

"Even better once you've done it a few times." She swam over and kissed her cheek. "I'm glad my son put that smile on your face. You love him?" She nodded again. "I hope to see a lot more of you here. You're more than welcome."

"Thank you, Miss..."

"None of that. I'm Cathy, my wife is Caroline. No need for formality or titles in this household."

Jade swam over and hugged Bailey as well, whispering something incredibly sweet in her ear, enough to cause a couple more tears. Jade then looked at me. "Don't you break her heart or I'll kick your butt, I don't care how cute it is."

"Yes, ma'am."

After dinner, Bailey and I tried to concentrate on more studying but it was pointless. She liked to game, so we played a couple of co-op games on my games console before we agreed to go to bed. No sex was had, just a lot of cuddling and quiet talking, Bailey pleased to see that I had a comfortable home life, something she'd lacked for a long time now.

"I sleep with Jade nearly every night. If you ever need a bed..." Her bottom lip started to tremble at my kindness. "Bailey, trust me, I know what it can be like for futanari out there at times. Things have come a long way, but a lot of people of a certain... biology, let's call it, still have issues, even centuries later."

"Will your mothers mind?"

"They'd insist you stay here if you told them what I know. I want you safe. More importantly, I want you in a home where you're loved unconditionally. You'll have that here."

She hugged me tightly, whispering that she'd think about it. For the first time I could remember, I was the big spoon as she snuggled against me, ensuring I held her tightly in my arms. She felt wonderful in my arms, pleased she drifted off rather quickly.

I knew I'd have to sit down and have a heart to heart with my Mum very soon