Join the best erotica focused adult social network now
Login

Author's Notes

"After a gap of two years, here’s a surprise 25th chapter of the Masturbating with My Classmates series. I recommend reading over at least the previous chapter to provide some context for this story."

Although we were in a five-star hotel, the honeymoon suite was still only set up for a couple, and I was willing to bet it had never hosted a masturbation group before. I immediately spotted the only two chairs.

‘Right, Fiona and I are having these. Sorry, boys, but you’re on the floor.’ I felt I should stop calling them boys as they were now all in their twenties, yet men or lads didn’t feel right either.

‘How’s that fair?’ asked my brother.

‘Oh sorry, Ryan. I didn’t realise you’d been in high heels all day as well.’ I kicked mine off and Fiona followed suit.

‘There’s no need to be sarcastic,’ he muttered.

‘You don’t see them complaining.’ Steven, Thomas and Jack had already started to kiss and undress each other.

‘Fine,’ he said, clearly not fine. He sat beside them but, as the only straight boy, he didn’t join in the kissing.

‘The brides,’ I added, ‘are of course allowed to have that massive bed.’

We’d drawn up ambitious plans for our one night together, but we hadn’t accounted for the tiring day.

‘I am dead,’ said Samantha, lying face-up on top of the covers, still in her white dress. ‘Next wedding, I demand someone follows us with chairs at all actual times.’

‘Next wedding?’ Tiff was stripping naked. ‘Why would we do this again?’

‘I meant someone else’s wedding, but good point. What if one of us has a midlife crisis when we’re forty and runs off and marries someone half our age with massive knockers?’

‘Well,’ said Tiff, now joining her new wife, ‘let’s hope that doesn’t happen.’

Our masturbation sessions typically began with each of the ladies enjoying an initial orgasm while the boys kept themselves hard for later. Given the significance of the day, the brides were granted the privilege of finishing first. While it had started as a jokey suggestion, they’d also requested everyone should use only their hands rather than toys to symbolise taking each other’s hand in marriage.

Tiff had been growing her clit for a long time with pumps and hormones. It had reached the point where she used her thumb and two fingers to pull the pierced hood rapidly up and down, much like the boys. She even called it her foreskin. Samantha had only lifted the bottom of her dress and slipped her hand into her panties.

‘I know I should be the last person to say this,’ said Jack to Samantha, ‘but I’m pretty sure the others want to see your lady bits.’ As Tiff turned to Samantha and helped to remove the rest of her clothes, he continued, ‘Do you know it’s been two years since we did it at the gym?’

‘The gym you pretended to run?’ added Thomas.

‘For God’s sake,’ Jack slammed his non-masturbating hand onto the floor, ‘how many times do I have to apologise for that?’

‘I’m not asking for an apology. I’m just pointing out the compulsive lying.’

‘That’s all in the past.’

Samantha, now naked, gently interrupted. ‘I’ll vouch for that. You’ve done a lot of work on yourself since then, so just let it go and don’t spoil the night.’

As the newlyweds masturbated, their moans went slightly in and out of sync with each other, one making a noise and the other echoing it a second later. They looked into each other’s eyes but kept their hands to themselves as they gauged how long it would take the other one to finish.

With this unspoken co-ordination, the moans started to fall into sync as they both closed their eyes and orgasmed. Through the screams and moans, we could see both their vaginas contracting at the same time. Everyone whooped a little at the couple as we continued masturbating.

Fiona had a strong preference for lying face-down, but she’d learnt how to stroke in other positions. As such, we both sat in our chairs while watching each other. I felt my own orgasm starting to build up, at which point I realised the funnel was still in my bag.

Using my other hand, I found it just in time. I shuffled a little closer, gently placed the narrow end a little way into Fiona and I squirted into the wide end. Fiona gasped as most of it landed inside her, although a few stray drops ended up on the floor. She had her orgasm quickly after that, still with the funnel inside her.

‘I see that’s the funnel free,’ said Tiff as I handed it to her, ‘so why don’t we skip to the part we’ve all been waiting for?’ Just then, there was a faint knock at the door. ‘Bang on cue. Come in.’

Our wedding planners entered and shut the door behind them.

‘Hi,’ said Katherine, ‘we came as quick as we could. That’s the caterer and the florist paid.’

‘Not the DJ. He’s wandered off somewhere,’ added Mike. ‘We’ll chase him up tomorrow.’

‘As I say, bang on cue. We’re about to give Samantha her gift, so take your clothes off.’

They both started to undress, but Kathrine added, ‘Yes, about that. I want to… We both want to… It’s just the…’ She tailed off.

‘I think what Katherine’s trying to say,’ said Mike, ‘is we still need to decide about helping you, much as we want to. Maybe it would help to go through it again.’

Tiff nodded. ‘So basically, I’ll have sex with each of the boys. They cum in me, then the five-second rule applies, so it becomes my sperm, then I put that into Sam so I can make her pregnant. I’m on the pill, obviously.’

‘And obviously I’m her brother so I won’t be doing it,’ said Jack. ‘Mine’s reserved for one of these guys.’ He kissed Thomas and Steven in turn.

‘Well, yes,’ said Katherine. ‘Mike and I are cousins, and we don’t want children together, but we’ve spoken at length about your… request, and there’s a certain appeal in helping you out. Just… not in that way.’

‘Don’t feel under any pressure,’ added Tiff.

‘No, we don’t feel any pressure. It’s just… Is there no way he can just funnel his sperm straight into you instead of having sex? I don’t know why it makes a difference; it just does.’

She shrugged. ‘It would be less fun, but it would do the job.’

Katherine paused. ‘Well, that’s the way we want to do it. Is that all right, Mike?’

‘That’s all right.’ I could tell he was pretending not to be disheartened.

‘Like I say, don’t feel under any pressure, but let’s start the ball rolling. Ha,’ she laughed at her own joke, ‘ball! Who wants to be first?’ The boys looked at each other without answering. ‘Fine, I’ll pick someone. Thomas, are you ready?’

‘Always.’

The cousins were now as naked as everyone else. They started their masturbation as the rest of us resumed ours. We watched Tiff and Thomas kissing a little, but they were both so turned on that any foreplay would be minimal.

It didn’t take long before the two were having sex. I’m sure she would have preferred to be on top, but we all knew the spunk had to be contained.

While this was going on, I’d noticed Jack was already thrusting into Steven, who was lying on his front.

It used to be the case that Thomas would take ages to finish, but this time it was over in a matter of minutes. He climbed off Tiff, who kept his sperm inside her with a hand and produced the funnel with the other. Placing the pointed end into Samantha, she moved herself over the funnel and released the fluid inside.

‘How does my sperm feel?’ she asked Samantha.

‘I don’t really have the words. Just not a texture I’m used to. Not unpleasant, though.’

‘Well, just let it sink in,’ said Tiff as we all watched Jack unload into Steven. ‘It looks like Steven’s free already. Everyone’s going off on a hair trigger today.’

Steven and Thomas kissed on the lips as they swapped places and Tiff lay on her back again.

While awaiting his turn, Ryan had joined me, and we enjoyed a deep kiss together. ‘I could do with another orgasm,’ I whispered to him. ‘Do you want to help a girl out?’

One of the earliest sexual activities I taught him was how to make a woman orgasm with his fingers. I couldn’t speak for his other ladies, but he was excellent at knowing my sweet spots. He stood beside my chair and kissed my neck, allowing his other hand to fall to my clit.

With Ryan’s hand in just the right place and a good view of Steven thrusting into Tiff, I soon orgasmed again. I squirted only a little that time and let it land on the floor.

‘So, Ryan. You still not had your gay awakening yet? You don’t fancy a little kiss, just to find out?’

‘All right, then,’ said Ryan, to everyone’s amazement. It was probably his horniness talking. ‘If you’re so confident, let’s find out.’ His hand was still on my clit.

Jack didn’t wait. He leaned forward and gave my brother an open-mouthed kiss on the lips. From my observations and reports from the boys, Jack wasn’t good at kissing. Most people grow out of the vacuum-cleaner approach with lots of tongue, but not him. After a few seconds, I could see Ryan struggling to remove himself. When he succeeded, he said, ‘Not for me.’

ValentynaGuzman
Online Now!
Lush Cams
ValentynaGuzman

‘Maybe it’s just the wrong guy,’ said Thomas. ‘Why don’t you and me try it?’

Ryan hesitated at first before nodding, his hand still rubbing away on me. Thomas approached him much more gently, starting on his cheek and working his way down to the mouth. It seemed like they were both having a better time. The kiss ended naturally, yet he still said, ‘No, definitely not for me.’

‘Maybe you just need some anal,’ said Jack. ‘We can arrange that no problem.’

It was time to step in. ‘The boy gave you a firm answer, so let’s leave it there, thanks. Anyway, that’s Steven finished now.’

‘Let me unload my sperm,’ said Tiff. ‘How are our wedding planners doing?’

Katherine kept masturbating but briefly removed her other hand from her nipple to give the thumbs-up. There was a wet patch on the carpet where she’d squirted a couple of times; I’d forgotten she did it as well. Mike looked as though he was trying to stop himself from shooting too soon.

Ryan didn’t manage to make me orgasm before it was his turn with Tiff, so I masturbated myself.

‘I wish we could do it the other way around,’ said Fiona suddenly.

‘Do what?’ I asked. I noticed she was looking at the wet patch in front of Katherine.

‘The funnels. I know we’ve tried it a few times, but you manage it on every orgasm and I’m lucky if it happens one in ten times. I didn’t manage it today and I’ve been holding off for three days.’ She sounded more disheartened as she added, ‘I just want to squirt inside you, the same as you do with me.’

‘It took me a long time to manage it even half the time, never mind every time.’

‘I try, I really do, but then I’ve got my fingers in the right place and I think it’s going to happen and then it doesn’t. There’s no consistency.’

‘Keep at it, and I promise you’ll see results. Watch Ryan and Tiff, maybe that’ll help.’

I loved watching my little brother having sex. It was a combination of factors: because it was so taboo, because he’d lost his virginity to me, and because we considered ourselves to be girlfriend and boyfriend as much as any other couple.

But unlike Steven and Thomas, he was taking a long time. Five minutes went by, then ten, and there was still no sign of finishing. Tiff looked like she was enjoying every moment, but I could tell he’d been turned off by kissing the boys. It was time to help out.

Fiona and I lay at either side of Tiff. We stopped touching ourselves for the moment and placed our focus on Ryan. We stroked each side of his chest in unison, then kissed either side of his neck. It was challenging because he was still thrusting in and out of Tiff, but we soon helped him to shoot his load into her.

With ruthless efficiency, the funnel was produced, the sperm was poured into Samantha, and she was asked how she was feeling.

‘A bit fuller now. How do you non-lesbians manage to take one load, never mind three?’

‘And we’ve still got one more to go,’ said Tiff, pointing out our wedding planners. Ryan vacated his spot while Tiff took the funnel and inserted the narrow end into her own vagina. ‘Mike, how’s the erection doing?’

The cousins exchanged a few whispered words and a kiss before Mike stood up and took his place in front of the funnel.

‘When you’re ready,’ said Tiff, ‘just wank into there. I hope you don’t mind if I do it as well.’

‘Of course not,’ he said.

Tiff and Mike settled into a rhythm, watching each other pulling their foreskins in near-unison. With most of our energy depleted, a certain lull had descended across the suite. Steven and Thomas were cuddled up together, while Ryan was sitting on my lap. A few drops had escaped from Samantha, leaving a tiny pool of white on the bed.

When Fiona and I took our seats again, she placed her hand on her clit and said, ‘I’m doing it again. I’ve got to try.’

I looked up at Ryan. ‘Do you want to help me out again?’

With barely a word, he stood up. I’d expected him to use his hand, but he instead placed his mouth over my genitals and gave me oral. I knew from the start it wouldn’t be good enough for an orgasm, but it still felt pleasant.

I took the time to savour the view of Mike and Tiff masturbating together. ‘Katherine,’ asked Tiff without stopping, ‘can I kiss him?’

‘Sure.’

She immediately brought him down for a deep kiss. He looked surprised at the sudden gesture and it seemed to put him off his stroke somewhat.

I heard a faint moan from Fiona, signalling she was close. I switched my attention to her as she brought herself to another orgasm. She didn’t shoot any fluids and shook her head in my direction.

‘It’s all right,’ I said reasonably quietly, ‘try again. Just remember what I said about keeping going. Sometimes when you’re not aiming for it, it happens’

‘One more shot.’

‘You know,’ said Katherine unexpectedly, ‘I’ve changed my mind.’ She was still masturbating furiously with one hand and gripping a nipple with the other.

‘Oh,’ said Mike. ‘I’ll stop.’ He pulled away from Tiff but kept masturbating.

‘Sorry, sorry. I mean changed my mind about the funnel. You can just go inside if you want. I don’t mind.’

Ryan stopped pleasuring me to take in the situation. I took over with my own hand.

‘Inside?’ he asked cautiously. ‘As in, no funnel?’

‘Only if you want. I thought it would be weird to watch, but it’s not actually. If that’s okay, Tiff. No worries if not.’

‘Ha! Absolutely no worries. Your husband can shag me any day.’ She dramatically removed the funnel from herself. It slipped out of her hand and fell on the floor.

‘Not any day,’ said Katherine, ‘this is a one-off.’

“I know, I know, I’m kidding. But I’m looking forward to this.’ Mike looked for reassurance from his wife. She nodded enthusiastically.

I assumed it had been a long time since he’d had sex with anyone but Katherine, as he had some difficulty finding the right spot. Tiff opened her vagina with two fingers and guided him in with the other hand, which helped him enormously.

Once he was inside, his thrusting started like there was no tomorrow, possibly knowing this might be his only chance to be with another woman. Tiff also hadn’t orgasmed by that point, but she brought herself to one shortly after he entered.

It appeared Samantha had fallen asleep despite the movement on the bed. The rest of us waited for the inevitable to happen, not least Katherine, who kept her eyes glued to them both as she continued her self-pleasure.

We didn’t have to wait long. The thrusting stopped and Mike’s sperm became Tiff’s sperm as they kissed for a final time.

‘Hang on,’ he said, ‘I’ll find the funnel.’ He removed himself from the bed and handed it to her. Placing the pointed end into Samantha didn’t wake her up, nor did the sizeable load of fluid that was released into it.

While all this was happening, Fiona was bringing herself to another orgasm. ‘Funnel,’ she said urgently. ‘Give it to Rebecca.’

Tiff handed it over straight away and I inserted the narrow end into my vagina, taking an educated guess about what was about to happen. The bottom of the funnel still had traces of Mike’s sperm that dripped into me, but the cousins were too preoccupied with cleaning up to notice, so I took it as a little bonus. I moved my chair as close as I could to Fiona as her faint moans built up again.

‘Same motion,’ I said, ‘work through it.’

As soon as I said those words, she slid down further in the chair. For someone who didn’t ejaculate regularly, there was so much fluid, as much as my first load, and almost all of it was transferred from her vagina to mine. We’d tried this a few times before but this was the most she’d managed to fill me up. I had some idea how Samantha would be feeling.

Fiona looked utterly delighted with herself. She couldn’t stop giggling and saying, ‘I did it, I did it.’

‘Well, it’s been fun,’ said Tiff, ‘and I’m sorry to bring this breeding session to an abrupt end, but the wife’s exhausted and so am I and I’m sure everyone else is too.’

‘And if it doesn’t work out,’ added Jack, ‘you’ll just need to get all the boys back in.’

‘Such a shame.’

‘I just want to do the squirting again,’ added Fiona, not particularly paying attention.

‘I saw that,’ said Steven, ‘well done.’

‘So,’ continued Tiff, ‘if you’d like to start to begin to consider thinking about making your...

To continue reading this story you must be a member.

Join Now
Published 
Written by JennaSide
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors

Comments