The Futanari Diaries Ch. 04

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The life of a young man and his love for futanari.
9.8k words
4.83
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Part 4 of the 14 part series

Updated 08/03/2023
Created 01/08/2022
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UltimateSin
UltimateSin
5,331 Followers

I'll admit, I woke in agony the next morning. A good sort. A pleasurable sort. But agony nonetheless. It was the first time I'd been utterly dominated during an evening. It was partly loving, but it was mostly hot, sweaty, ball-busting, big girlcock pounding a tight arse type of sex, the sort where I was pretty much the submissive bitch to Miss Wilson for god only knows how long during that evening.

I enjoyed every single second of it. Miss Wilson woke me up with a soft kiss, taking me by the hand as I hobbled to the shower. She gently washed me from the top of my head to my toes, kissing me softly all the time. Leading me back to her room, she dressed first before she helped me get dressed. Downstairs, she prepared breakfast as I attempted to sit on the stool, but to be honest, it still hurt.

"Oh baby, I'm so sorry," she cried, taking me in her arms. I thought she was about to cry.

"It's a good hurt, Sandra. I think I overestimated myself though. But I loved every second. No regrets."

"Your cheeks are still a bit red too."

"It's fine. Really..."

Another soft kiss on the lips before she placed some toast and a mug of tea in front of me. We ate and chatted about the upcoming day before grabbing our things and walking to her car. I held her hand the entire way to school, just to put her mind at ease. Sitting wasn't entirely comfortable but I'd been through worse on a rugby field. Suffered more than one concussion and those sucked.

Parking up at school, I'm not sure if we were seen arriving together. Getting out, I grabbed my things, Miss Wilson looking around to see we were alone, giving me one last kiss and cuddle. "Thank you for last night, Benji."

"My pleasure, Miss Wilson."

"Would you like to do it again?"

"God yes, Miss Wilson. Name a time and place, and if I'm free, I'll be there naked, lubed and ready."

"Bad enough to make an old futagirl like me fall in love."

"Being in love won't be a problem once I've graduated, Miss Wilson."

She took a couple of seconds to comprehend what I was suggesting. "You'd like to keep going after you've graduated?"

"You really think I'd give up what we did together last night?"

With some reluctance, we shared one last kiss before heading in opposite directions. Walking around to the front of the school, my presence was eventually noticed by my friends, noticing I'd not arrived with Jade. I managed to fob them by stating I'd come in by other means. They didn't ask too many question, but they noticed I was hobbling and wincing every so often.

"Good night, Benji?" Vanessa asked.

"Like you wouldn't believe, Ness."

"We need details," Georgie demanded, albeit gently.

Glancing around, all eleven nodded their heads. "We won't be jealous, Benji. Looks like you had a good time," Bailey added.

"Okay. So... She had a massive, thick cock. And she was dominant. I mean really dominant. Had me tied to the bed last night by my wrists, whipped my arse with a riding crop something good, then just fucked the shit out of me for a few hours, spending most of the time on my knees, head buried in the pillow, sometimes blindfolded and gagged. Think we stopped early this morning. Filled my arse with so much cum, it was still leaking out of me in the shower this morning." Glancing around and down, I could see a series of erections under skirts. "I'm guessing you liked that story."

"Did you know she was like that?" Vanessa wondered.

"Not particularly. It was fun. Trust me, it was a lot fun, but also not something I think I could tolerate every time. I do prefer it being slightly more gentle and intimate than that."

"I'm intrigued as to who," Bailey murmured, earning plenty of nods.

"Maybe later. A man has to have some secrets."

Thankfully, I didn't have a class with Miss Wilson on a Thursday, so we didn't have that awkward moment during class. I did see her in the halls though, stopping long enough for her to rest a hand on my shoulder and that glance only lovers do. I would have liked to kiss her but wasn't confident enough for that sort of display.

My friends wanted nothing but my company at lunchtime, spending the entire hour sitting together, chatting about school, work, our hopes for the future. I mentioned the holiday my mother had mentioned and the fact I could invite friends. When they asked who, I insinuated my mother meant potential lovers rather than my male friends. Adding that my mother and Caroline had mentioned going to a university with a larger futanari population, I noticed many smiles in my direction, so I had a feeling many of friends might be attending the same university.

"What are you hoping to study?" Vanessa wondered.

"I'm thinking law. For a few reasons, but it will depend on my final marks."

Vanessa smiled as she had an inkling why. A couple of reasons were purely personal.

Jade picked me up from school. Taking one look at me as I sat in the passenger seat, she burst into laughter though caressed the back of my head with her fingers. "Late night, sweetie?"

"I'm still a little tender even now, Jade."

"She fucked you properly, did she?"

"I'll show you when we get home."

After completing my homework, I wandered into Jade's room, finding her hard at work with her end of year assignments for her university course. Kissing her cheek, she sighed and turned her chair to face me. Making a gesture, I turned around and dropped my shorts I'd changed into. I was expecting laugher. Instead, she disappeared for a few seconds, returning and asking me to bend over the bed.

Feeling her rub some cream on my cheeks and thighs was a relief. Miss Wilson had done the same thing the previous night once we were done, and also after the shower that morning, but I guess they still looked a little sore. I told Jade that, which headed off any criticism. "I didn't think about the rest of the day," I said, "And I couldn't very well go to Miss Wilson about it while I was at school."

She rubbed my back. "It's okay, baby," she said softly, "No sex tonight though. I think you could do with a night off."

"Yeah, I can agree to that."

Mum and Caroline noticed I was still slightly hobbling. I hadn't told Jade everything we got up to, thinking it best just to tell them at once. While they were definitely aroused, I noticed the concern in Mum's eyes. I took her hand, assured her I consented to everything. In fact, I wanted everything done to me. But even Miss Wilson was feeling guilty that morning, so I had a feeling that, although it wouldn't be a one-time thing, our next time together would be more... normal, for want of a better term.

I woke the next morning with Jade's arms wrapped around me, my head resting underneath her chin, and her hard girlcock pressed into me. Licking my hand, I gently grasped her length and started to stroke her. She woke slowly, hearing her whisper I was being naughty.

"Can I blow you, Jade?"

"My girlcock is always yours, sweetie. You know that."

Turning onto her back and spreading her legs, I sat on my knees between them, taking her girlcock in my mouth, ensuring it was a slow, sensuous blowjob. I loved my sister's girlcock and I loved making her cum. In fact, the blowjob took so long that Mum knocked on the door, letting us know it was getting late. I was busy and I don't think Jade even heard, Mum opening the door and hearing her giggle.

Feeling her hand rub my back, Jade told her how good my mouth felt. "I know, baby. He's wonderful at this now. Are you instructing him how to deepthroat this weekend?"

"Yes, Mum."

"Good. Once he does that... Damn, he's going to be even more popular." Mum leaned forward to kiss her. "Are you close, baby?"

"So close, Mum."

She was, as within a few minutes, she warned me she was about to cum, getting in the right position to ensure I tasted every single drop of what she fired into my mouth, gulping the first few spurts down before keeping enough in my mouth, looking at Mum and smiling. She smiled, leaning forward to kiss her, swapping my sister's cum.

"Mmmm. My little futagirl does taste delicious." She stood up. "Okay, take five more minutes, then you really need to get ready for school."

"Yes, Mum."

Cuddling into my sister, she wrapped an arm around me, holding me tightly. Whispering our love for each other, we shared a long, soft kiss before finally getting up. Showering together saved water, dressing quickly and heading downstairs for a quick breakfast, rushing out to the car. I arrived at school on time, my sister not getting out as she was running a little late, still sharing a steamy kiss before getting out and waving goodbye.

Vanessa and my other friends noticed I was feeling much better and there was immediate talk of who was fucking me at lunchtime. Bailey and Chloe didn't want their first time inside me to be at school, and all my other friends, too numerous to name right now, felt the same way.

It was decided Vanessa would have me at lunch, but we'd do something different. We took our blanket as far away from everyone else as possible. The other futagirls gathered in a circle as Vanessa and I stripped off. Getting on our knees, I kissed down her body before taking her girlcock in my mouth. The moan she released thankfully didn't carry with the wind.

"Wow, those are some marks, Benji," Bailey whispered, "Do they hurt?"

"Not anymore," I replied before swallowing Vanessa again.

"Definitely want to fuck that tight little arse," Georgie murmured, "Fuck, I'm so hard right now."

"Baby," Vanessa whispered, "Want to blow our friend while I fuck you?"

"Threesome! Spitroast! Totally fucking hot!" Aubrey exclaimed.

Spinning around, I felt Vanessa waste little time burying her tongue between my cheeks as Georgie got into position in front of me. Like all my lovers, she was a good four to five inches taller when standing. Her hair was currently blue, one of those futagirls who went through phases of colour, but her blue eyes were rather dark but utterly gorgeous. Like all my lovers, she was drop dead gorgeous, a pair of C-cups on her chest and at least eight inches between her legs.

Taking off her panties, I unzipped her skirt as she took off her blouse and bra. My shirt, trousers and underwear was already off, glancing to see Vanessa was naked too. Georgie's thick girlcock sprung free from her panties, licking up and down her shaft, hearing her actually choke back a sob. Glancing up, she smiled down at me. "Please, baby, I want to cum in your mouth so much," she whispered.

"This is going to get emotional," Chloe stated softly.

Futanari never left home without lube, no surprise I felt some applied to my arse and two fingers quickly slide inside me. I kept licking Georgie's girlcock and balls until I wrapped my lips around her shaft, enjoying her tasty pre-cum as I lowered my mouth further. I only stopped moving as I felt Vanessa press her thick head against me, groaning around Georgie's length as she slowly slid inside me.

"Oh fuck, it's Miss Wilson!" Chloe exclaimed.

"It's fine. Don't worry," I assured them.

Lowering my arse slightly for Vanessa's benefit, I resumed sucking Georgie as Vanessa slowly fucked me. Aside from the three of us moaning, I glanced to see some of the futagirls with girlcocks out, stroking themselves. And then I heard chuckling, glancing to see Miss Wilson standing by our circle.

"My, my, my, everyone looks like they're having fun. Are you having fun, girls?"

"Yes, Miss Wilson," most of them managed to reply.

"And you, Mister Marsh. Are you having fun?"

"God yes, Miss Wilson. Ness has a fabulous girlcock and I really want Georgie to cum in my mouth."

I know the next request surprised everyone but me. "Make room, girls. I want to watch too. Love seeing a cute young man being taken both ends."

Ignoring the presence of everyone else, I focused on the feeling of Vanessa's girlcock thrusting into me and Georgie's thick cock with my lips wrapped around it, head bobbing up and down. Her fingers were soon running though my hair, moving her hips, forcing a little more of her length into my mouth. Using a trick I'd learned since my first time, I gently fondled her balls, which made her moan.

"Benji," she moaned, "I'm close already."

"He'll swallow everything," Vanessa stated, thrusting into me faster and faster, "Just cum, sweetie. It's okay."

Vanessa buried her cock and stopped moving so I could give my full attention to Georgie. She was practically sobbing by now, not wanting to cum but also desperate to cum. Looking up into those gorgeous blue eyes pretty much guaranteed her orgasm as she would have seen the lust and desire in mine. With a squeal, that first spurt hit the back of my throat, easily swallowing each subsequent spurt with ease, savouring her taste.

Now that her friend had cum, Vanessa resumed fucking me, Georgie changing her seating position so I could rest my head on her lap, feeling her caress the back of my head. "Fuck, Benji," Vanessa moaned, "I fucking love your arse."

Chloe snorted but didn't say anything. I heard a few more moans around us, figuring other futagirls were climaxing from watching the shower. Vanessa leaned forward to mount me properly, her thick cock pounding me for a couple of minutes before she filled me with another load of cum. No doubt a little tired, she relaxed on top of me before finally pulling out, allowing me to lie down for a couple of minutes. Cuddling into each other, we shared some light kisses, caressing her cheek, before there was a cleared throat. "Everyone have fun?" Miss Wilson asked.

"Yes, Miss," we all said.

"Good. And a smart decision to come all the way over here, though I figured out why. I warned Mister Marsh about the constant use of the changing rooms for your escapades. Being this far away is almost good enough, but just be mindful of certain teachers. They even get an inkling of something like this...

"We'll be careful, Miss," Vanessa said.

Miss Wilson no doubt looked around, receiving nods that the warning was received. "Vanessa, you're a beautiful young futagirl. I'm delighted you finally got to share yourself with Benjamin. Georgie, dry your eyes. Was that your first blowjob?"

"Yes, Miss," she whispered.

"Good. Sharing something wonderful like that is sometimes even better with friends. And Benjamin, now I see why you're just so damned popular. You take a girlcock very well."

"Thank you, Miss. Vanessa has been a close friend for years. I'm glad we're finally being intimate."

"I love you, Benji," Vanessa whispered, finally confirming her true feelings.

"I love you too," I whispered back, kissing her softly before we cuddled.

"About fucking time, Ness," Chloe said, hearing plenty of giggles as everyone else agreed.

"I really don't want to bring down the mood, but you've got five minutes until lunch is over. Best you wipe yourselves down. Benjamin, I hope you'll manage to concentrate in my class during last period."

"Of course, Miss Wilson."

"Good boy. Girls, lovely to see you all too."

The three of us dressed quickly as other girlcocks were slid back behind panties and underneath skirts. The blanket was covered in cum. Vanessa brought a different one every day, so I assumed this would definitely be washed. The bell rang as we were walking back to the main building, Vanessa in my right hand, Georgie in my left. Only Georgie was in my next lesson, stopping outside the door and sharing a long kiss.

"That was wonderful, Benji," she breathed into my ear, "I can't wait until we make love soon."

"Me too, Georgie."

My last lesson on a Friday was with Miss Wilson, Vanessa to my left as always, Bailey now to my right, practically demanding the young woman who was sat there to move or else. She wisely moved, not without whispering a derogatory comment in her direction. Bailey laughed at her, sat down and held out her hand. "How are you, handsome?" she asked once I'd taken hold of the offer palm.

"Just fine now that I'm surrounded by two beautiful futagirls."

"Jesus, get a room, mate," Mark called out from the other side of the room, hearing him laughing away with Mike. I would have told them to get fucked, but classroom and all.

The lesson otherwise passed without incident. Miss Wilson didn't ask me to remain behind this time, though I was last to leave, wandering over and asking if she was okay. She sat me down on the desk and admitted she felt guilty about going overboard on Wednesday night. After shutting and locking the door, I returned and hugged her, assuring her I'd loved every minute of it. Yes, I was sore the next morning and most of the day, but that wasn't a problem.

"Miss, I'd love to stay and assure you by doing something else, but Jade is waiting for me." Stepping back, I smiled. "Tell you what, I'm going to invite a few friends over for swim tomorrow. Would you like to come?"

Her face lit up. "I'll give you my number. Text me your address and details."

Numbers exchanged, we shared a kiss and cuddle before I unlocked the door and headed out, smiling to myself as I made my way to Jade's car. Sliding into the passenger seat, she immediately asked what had me smiling. I explained what happened at lunch, then what I'd asked Miss Wilson. Jade loved the whole idea. Mum finished work early on Friday's so was already home when Jade and I walked inside.

"Mum, can I ask a favour?" I asked, wondering if I'd need to butter her up.

"What is it, sweetie?"

"Can I have some friends around tomorrow? It's meant to be hot and..."

"Male or futanari friends?"

"The latter."

"Definitely. Will I know them all?"

"You know Vanessa. She couldn't make my party, otherwise she'd have been here that day. The rest, I'm not sure." I paused before adding, "And Miss Wilson."

Mum laughed, putting my nerves to ease. "Should have known. Okay, baby, want to go shopping for a few things? We'll make it a barbecue, get some drinks in... Maybe a lot of lube too..."

"Mum," I groaned.

"Definitely a lot of lube." Kissing my cheek, she whispered, "Make sure you spend the night with your sister."

"What about you?"

"I'm important. Your sister is your life partner, Benjamin." I felt my eyes widen at the use of that term. "You can't marry her. You'll be together forever. Trust me on that one."

Glancing at Jade, I knew, in that moment, Mum was speaking the truth. "I'll send some messages and let you know who's coming. Jade, want to hang out by the pool before dinner?"

"I'll wear one of my sexy bikini's for you, Benji, though I won't tuck it."

Heading to my bedroom, I sent a few messages, hearing almost instant replies, everyone excited about the invite, and that they'd arrive in time for lunch, with a possible extension for lunch, depending on how everything went. Even Miss Wilson's reply was eager, stating she had just the sort of bikini that I'd appreciate it. Considering her curves... I knew I'd be in for a treat.

Swapping into a pair of swim shorts that were basically the same as boxer-briefs, but for swimming. After grabbing a towel, I walked through the house towards the back door, not surprise to see Mum and Jade both sitting by the pool. Jade's bikini was dark blue, covering her nipples and a little bit more of each breast, her bikini bottom straining with her thick girlcock flaccid but no longer tucked. Mum wore a white bikini, covering a bit more of her breasts but her thick girlcock was almost prominent.

Dropping my towel on the sunlounge next to them, I looked over both of them. "You are both so fucking hot," I said, "I mean, seriously. So beautiful."

Jade was up on her feet, hugging me tightly. Mum was distracted by wiping her eyes before she hugged me too. "You have no idea how much it means to hear that from you, baby," Mum whispered, I think Jade was busy crying. "Right, dry your eyes, my darling daughter. Let's get in the pool."

UltimateSin
UltimateSin
5,331 Followers