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Author's Notes

"Like everything in the Masturbating with my Classmates series, this is a work of fiction. This is especially true of the part where one woman squirts into the other's vagina using a funnel. I don't sleep with women, so I genuinely don't know whether this is possible and I can't find any other examples online. I'm interested to hear from any ladies who have done or tried this."

Fiona and I had moved into our own place, and we'd invited the rest of our masturbation group to the housewarming. The previous night had been the most raucous session yet, with threesomes, strap-ons, and spankings. We'd all tired ourselves out and gone to bed early.

But in the morning, we were up and masturbating again, and Tiff wanted to make the most of her time. She asked if it would be all right to borrow Steven and Thomas for a threesome, as she didn't see them very often. Besides, we'd all recently agreed they could finish inside her without a condom and she wanted to feel what it was like. They moved to my bed. Her fiancée Samantha had no objections and continued to masturbate as the three decided how they would arrange themselves.

Fiona and I were employed at the same bar, and we were due to work the same shift that afternoon, so we had our second orgasms almost at the same time, then changed into our work uniforms. Our friends all had trains to catch, so they too were watching the time.

When we were nearly ready, Samantha said, 'There was one more thing I wanted to mention, but there hasn't really been a right time to say it.'

'Go on, then,' I said.

'I didn’t want to spoil the mood. It's about Jack.'

On hearing the name, Steven turned around. 'What's he done now?' He was inside Tiff, still moving slowly back and forward.

'No, it's nothing like that. It's just, we've made some good progress with him. Fiona, just for context, this is my brother. He used to be in this group, then he fell in with some wasters, but I think we've turned a corner. He's seen them for what they really are. I don't want to get into it but they basically robbed him.'

'Serves him right. Sorry, I know he's your brother, but I really can't...' His words trailed off as he continued to thrust into Tiff.

'I know, he's a piece of work. But like I say, I think we've turned a corner and he wants to make something of his life. I was wondering if we could let him join us again, just for some structure.'

'No, absolutely not.'

'He really has changed, Steven. I wouldn't say it if he hadn't.'

Steven increased his thrusts. 'Remember what he did. He broke up with... hang on.' He thrust even faster, then stopped as he ejaculated into Tiff. 'He broke up with me, just out of the blue, at the station, remember?'

He withdrew and stood up, his erection slowly subsiding. Behind him, Thomas took his place and kissed her as he entered her.

'I know what he did, but I'm trying to help him.'

'He didn't even admit we were boyfriends for months. So no, there's no way he's coming back and that's that.'

After a pause, I tried to lighten the mood. 'How did it feel spunking inside a lesbian?'

'Ninety percent lesbian,' said Tiff.

'It still counts.'

Steven didn't answer the question. ‘I’ve heard enough.’ He dressed himself and closed his bag. When Thomas and Tiff finished, everyone headed their separate ways. The atmosphere was becoming ever more tense, and Steven in particular wasn’t interested in saying anything but curt goodbyes.

Fiona was never particularly extroverted, but during the shift, I noticed she seemed more withdrawn than usual. I was desperate to ask her about it, but there was no private time at work with customers and other staff about. The shift didn't finish until 11 PM, so I decided to wait until we were back home.

I first asked if everything was all right. She said it was, but something was definitely up, so I gently coaxed her. The story slowly started to fit together.

'It's about... coming inside, you know.'

We all had a clean bill of sexual health in the group, and I had a contraceptive implant. However, Fiona hadn't yet found a method that worked without side effects, so that was the only time any of us used condoms.

'Ooh. Did you find something that works?'

'No, not yet. Okay, this is going to sound weird, probably.’

'You're not pregnant, are you?'

'God, no. Like I say, it's going to sound weird, but I wondered if maybe...'

'Yes?'

'Well, you know how you squirt. Maybe I could... maybe you could... somehow squirt in me, just so I can see how it feels and of course you can't knock me up, having the same bits.'

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I struggled to imagine what she was describing, but I was intrigued.

'How... how would that work?'

'Basically, I always lie on my front, as you know, so I would touch myself that way, but have a funnel inside me. Then you could come behind and when you squirt, aim it into the funnel and your... stuff would go inside me.' She added quickly, 'I just want to try it, see how it feels, just once.'

I didn't know what to tell her at first, but she’d clearly thought this through. I was curious by this point how it would feel. 'I'll think about it,' I told her.

The next morning, I agreed to have a couple of orgasms with her to see how it went, on condition, there was no kissing or unnecessary touching. By this time, 24 hours had passed since my last ejaculation so I was ready to go. Fiona and I undressed and she lay naked on her bed, face down on a towel. She’d taken a small funnel from the kitchen and gently inserted the pointed end into herself. Holding it in place with one hand, she lowered her clit onto her vibrator.

Meanwhile, I kneeled behind her and figured out the logistics. I could feel the vibration and it was nice, but it wasn't enough to get me off as well. I used my own vibrator on my clit, and inserted two fingers into myself, leaning as close to the funnel as possible.

I found I wasn't particularly turned on by this situation, so when I found the sweet spot inside me, I relied on my fantasies instead. I often thought back to my upper high school days, when the girls and boys would tease and masturbate after games class. But I liked to change it, imagining I was the only female and that they’d invited me in the male locker room so I wouldn’t be on my own, and I would end up showering, teasing, and playing with them.

Fiona didn't take long to reach her first orgasm. She moved off the vibrator as she finished, then straight back onto it. I finally felt myself start to build up and I moved into position, as close to her vagina as possible.

At the climax, I removed my fingers and ejaculated into the funnel. I loved the sensation of my liquid going straight inside someone else, and I finally had an insight into how our boyfriends must have felt.

A lot of wetness hit the towel, but the few drops that dripped inside Fiona made her say, 'Wow, I felt that.'

Just then, I heard a new message arrive on my phone, but I ignored it in favour of a second orgasm, which didn’t take nearly so long.

Second squirts are never as heavy as the first, but I managed to direct more of it inside her this time, quickly pushing my vagina right against the funnel. This time, almost all my liquid went inside, and Fiona told me she was about to get off again from the feeling of it. For just a moment, in a weird sort of way, I felt like a jock finally scoring with a cheerleader, even though I wasn't attracted to my flatmate.

I called a halt at that point, but I asked, 'Do you want to do that again some other time?'

I'd never heard her say, 'Hell yeah,' before, so she must have really enjoyed it. With a guy, I'd normally kiss him, but I offered a high-five instead.

I cleaned up some excess juice and picked up my phone. 'It's Thomas. He says he and Steven have agreed to speak to Jack about him rejoining the group, but,' I paraphrased, 'they're not promising anything.'

'Did Samantha say he was her... brother? I'm not imagining that?'

'Yes, he is. They're total opposites, though; he thinks a lot of himself, not like her. I'll tell you the whole story some other time. Oh, speaking of brothers, did I mention Ryan was coming over in a couple of weeks?'

'Oh,' she said, 'that's nice.'

That sweet and innocent comment hid a lot of history. The first time he’d met her at the student union, he wouldn't stop flirting with her, even though he was only seventeen and she was nineteen, and she kept returning his advances. At the end of the night, they went back to her room, and that was far from the last time they had sex.

'I just thought I'd mention it,’ I said. ‘In case you wanted your fill again.'

Published 
Written by JennaSide
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