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The Deeper End

"A woman treats her boyfriend to some fun with a friend."

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Author's Notes

"The Deep End was initially intended as a standalone story, but it received such a positive reaction that I’ve written this sequel. To understand the context, it is recommended to read the original story first."

A few days after I introduced Aidan to Matt, I was still embarrassed about a little faux pas.

Whenever I was naked with Matt in the changing room and nobody else was around, I would lean in and joke, ‘Nice penis,’ in a theatrical whisper.

He would roll back his foreskin to reveal his small purple head and say, ‘Thanks, I grew it myself.’

Then I absentmindedly said it while we were drying off with Matt. The moment it was out of my mouth, I realised what I’d done. As usual, he rolled the skin and delivered his line, adding context about his transition for Aidan. ‘You’d better not put this in your stand-up routine,’ he jokingly added.

Aidan seemed amused rather than upset. ‘Don’t worry,’ he replied. ‘Some stories are for personal use only.’ I didn’t know what he meant by that. Was he making a joke? Was he really turned on by the display? I was trying to think of the right way to ask when a group of loud guys entered the room, making further conversation difficult. It seemed no damage was done, so I tried to let it go.

Meanwhile, Aidan and I had been experimenting with anal sex and found a way that worked for both of us. When he pulled out after our first successful attempt, I took the opportunity to ask light-heartedly whether Matt was his type. Aidan would typically answer my questions openly and honestly, but he clammed up with this one and changed the subject.

Offstage, he was never extroverted to the same extent as onstage, but he was definitely acting more distant than usual. I tried a few different ways to find out what was wrong, even asking directly whether it was down to my in-joke with Matt. He eventually explained.

‘When I was nineteen, I went out with a guy who was about four years older, if I recall right. What he would do was ask if I liked some guy – it might be someone I knew, or he knew, or someone on TV – and if I didn’t answer or said no, he would push and push until he got one. And if I said yes just to keep him quiet, he would throw an absolute strop and start screaming about how I wasn’t committed to him, then he wouldn’t talk to me until I apologised.’

‘Until YOU apologised? Oh my goodness. I’m so sorry for asking you. I had no idea about that.’

‘It’s not your fault. It’s just… when you’re that age, things stick with you and that just brought all that up. He was a psycho.’

‘You don’t still speak to him?’

‘He broke up with me. Never heard from him again.’

‘Okay, that’s good.’ But I couldn’t just leave it there. ‘Look, I know what you said, but is he your type? If you answer, I promise one hundred percent I won’t go mad. I just saw how you boys looked at each other and… I was curious.’

He took a deep breath. ‘Please don’t fly off the handle, because I don’t think I could go through that again.’

‘One hundred thousand percent.’

‘Yes,’ he stuttered, ‘I think he’s… I would go for him – if I wasn’t with you, obviously, but I’ve never been with a guy who wasn’t… Who didn’t have a… you know.’

‘A whacking great dick?’

‘I was trying to be polite.’

‘No need. That’s exactly how he would put it.’

By this time, a significant pool of semen was running out of me. I moved to the bathroom to clean up, trying not to let any more drip onto the sheets. As I wiped, I wondered: now I knew there was at least an attraction on my boyfriend’s part, was there a way to indulge my fantasy of watching them together? It was a risk, but I was almost certain he and Matt would enjoy themselves if I gave my full permission.

It was Aidan’s birthday the following month and that seemed like the ideal time. Considering how close I was to Matt, I initially thought it would be simple to open the conversation. We’d routinely talk about the attractive guys in the changing room and what we’d theoretically do to them, even if our tastes rarely overlapped. But that was a world away from asking him to actually do something erotic with my boyfriend. I didn’t even have a solid idea about what they could do or how to arrange it.

On top of that, it was increasingly difficult to speak to Matt alone these days. Whenever she wasn’t on reception, Dawn had fallen into the habit of taking her swims at the same time as us. What’s more, whenever we’d planned something else for afterwards, she would invite herself along, forever dominating the conversation. We didn’t dislike the woman entirely, but we craved some time without her company.

Just three days before the birthday, I finally summoned the courage to speak to Matt. As it was so warm, we took a trip to the beach with ice-creams and coffees, far from the prying ears of Dawn. I rambled for a bit about my half-formed idea until Matt slowly raised his hand to stop me.

‘Okay, okay, so what you’re saying is: it’s Aidan’s birthday and you’d like to give him – for want of a better term – a happy ending? And you,’ he paused for a second, ‘would like me to help you do it?’

‘Yes. That’s what I’m saying. I mean, I don’t actually know what form this would take yet, so if you don’t want to, no worries if not, it was just a suggestion but I’m all ears if you have ideas.’

He paused again and looked briefly deep in thought. Just when I thought it was going to be a flat refusal, he brightened up.

‘So you’re saying I can have sex with your boyfriend?’

‘No, not sex, just a bit of a tease.’

‘I promise I’d use a condom. Come on, I haven’t had it for months now. Too busy working.’

‘I’m putting my foot down. No dick in the dock.’ Matt still had a functioning vagina, but he’d told me a lot of trans men don’t like the word, so they typically use an alternative. His preferred term was dock. ‘I mean, he might not even be your type. We don’t have much time either. Just until the end of the week. If that’s a problem, we can just forget the whole idea.’

‘Stop back-pedalling. I think it’s a terrific idea, and I have a wide range of types, thank you very much.’

‘As long as he’s hairy and muscular and well-hung.’

He turned thoughtful once more. ‘I still think you should let us dock, but if I can’t persuade you, then I have a suggestion. Three days is a bit of a squeeze, but not impossible.’

‘I’m all ears.’

He told me his plan in some detail. The more he talked, the more I agreed to it. I suspected it was already an existing fantasy and he’d simply adapted it. On the topic of boundaries, I was happy for the boys to kiss and touch each other, and I was persuaded to allow oral sex as well.

The only trouble now was setting up the scenario on the day itself.

I’d invited Aidan around to my house-share for an unspecified ‘birthday surprise’ after work. Half an hour before his arrival, I was expecting Matt to come over and hide in a vacant room. One of my housemates was away for the weekend and gave permission to use it. Meanwhile, I would cook a quick dinner then start the fun part.

That’s what was supposed to happen, but there was nothing else to do after buying the ingredients for dinner, so I went to the pool. This was a mistake. I initially thought I’d be safe from Dawn because she was on reception, but by the time I’d dried off, her shift had finished. I’d repeatedly told her I was preparing something special and I needed time alone to do it. She said she would walk me to the door, which would have been fine, but then invited herself in.

I excused myself long enough to type out a brief message to Matt explaining the situation. I gave Dawn the TV remote, which distracted her for five minutes while I let him into the house. She kept talking the whole time, largely to herself and finally left after giving Aidan a tuneless performance of Happy Birthday.

Once I was sure she was down the street. I brought him into my bedroom, closing the door.

‘I’m sorry I haven’t had a chance to start dinner yet,’ I told him. ‘Not with her wanting attention.’

‘Don’t worry about it. Why don’t you start off and I can help out?’

I was conscious of our friend secretly waiting for us. ‘No,’ I said, more forcefully than I intended. ‘We can eat later on.’

‘All right.’

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I turned off the main light and switched on a lamp. I’d also prepared some music, but there was a long awkward pause between me pressing Play and it actually starting.

I kissed him, then we started to undress each other as if preparing for sex. He had an intense erection, but before he could take me to the bed, I pulled out my desk chair and placed it as near to the middle of the small room as I could.

‘What’s going on here?’ he asked.

‘Never mind that. It’s part of your little treat, so just go with it.’

‘Okay,’ he said slowly.

I pulled out a blindfold from my bottom drawer. ‘And you need to wear this.’

He let me put it on but asked, ‘There aren’t going to be handcuffs, are there?’

‘Not today.’ In truth, I simply hadn’t thought about them. ‘You’ll have full use of your hands.’

Once I was sure the blindfold was in place, I waved my fingers in front of his eyes a few times to make sure he didn’t flinch.

Now my acting skills would come into play. ‘Oh, I’ve forgotten the lube. Two seconds while I grab it. Now, the door is open so don’t even think of peeking, but feel free to keep yourself hard.’

‘Do you not keep it in your bedroom?’

I realised I hadn’t fully thought out my excuse. It was in the same drawer as the blindfold. I simply gave a whispered, ‘Shh,’ as I opened the door. He was already stroking himself.

As quietly as possible, I brought Matt from the other room. We both swiftly moved back into my bedroom, and he quickly removed his T-shirt and boxer shorts. I made a big deal of closing the door noisily to signal my return.

‘You got it?’

‘Yes. Now the fun begins.’

Matt and I had to work together. I would sit nearby and take care of any talking while he went to town on Aidan.

His first move was to kiss Aidan on his neck before working up to his mouth and kissing him with tongues. At the same time, he gently took Aidan’s penis in his hand and matched the stroking rhythm. He worked carefully down to his nipples, which weren’t very sensitive in my experience but it looked enjoyable. He moved incredibly slowly, making sure to spend a lot of time in each area for maximum pleasure.

I moved my face right next to Matt’s face and waited until his mouth wasn’t full of some part of my boyfriend. I whispered, ‘Are you having fun?’

‘Yes,’ he whispered back.

Matt took this as a cue to move lower on Aidan, kissing him down the stomach, still incredibly slowly. By this time, the boys must have been going for a good ten minutes and I was becoming wetter and wetter as this scene unfolded. I found myself gently masturbating at the sight.

I again moved my face right next to Matt and waited until his mouth was empty. ‘Still having fun?’

‘Yes,’ he whispered again.

Matt started to cup Aidan’s testicles. Without altering his stroke in any way, he placed his lips on the very top of the head, which made Aidan groan a little. In fact, it soon looked as though he was on course to shoot into Matt’s mouth, and the big reveal hadn’t even started.

I tapped Matt on the shoulder and signalled for him to slow down. He stopped stroking with his hand and instead moved his mouth gently up and down over the entire head. While Matt was occupied, I whispered into Aidan’s ear. ‘Are you still enjoying that?’

It took him a second to realise that if I was talking, my mouth couldn’t have been on him.

He reached up to the blindfold. ‘Who is that?’

‘Keep it on,’ I said, ‘don’t spoil the surprise.’

Matt removed his mouth and stood up. He took hold of Aidan’s hand and guided it towards his genitals, letting him feel the wetness of his dock. He then gently bent back Aidan’s first two fingers and squatted slightly so they slotted inside him.

‘It’s Dawn, isn’t it? Are you Dawn? But how did you get back in the house?’

‘Do you think she’d be able to shut up for this long?’ I whispered.

Matt leaned in to stroke my boyfriend’s penis again, all the time still allowing him to gently thrust his fingers in and out of his dock. Before either boy could say anything else, he leaned in for a kiss with tongues. I was rubbing my clit ever faster and I was close to finishing.

When the kiss broke, Aidan simply said, ‘Matt.’

‘Finally,’ said Matt, ‘I can speak again.’

Aidan turned to me. ‘How did you arrange this? How did he get in?’

‘I’ll explain later,’ I whispered. ‘First of all, he sucked you, and I’d like to see you return the favour.’

Matt let go of Aidan’s penis and lifted off the blindfold. He removed Aidan’s fingers from his dock and licked them slowly. At the same time, he stood as close as possible to Aidan, who placed his mouth over the self-grown penis. I’d never seen it hard before and I thought it was cute how it still pointed downwards rather than upwards. Aidan moved his lips back and forth over the little purple head. Matt gave a rather feminine moan, which amused me.

I’d now watched each of the boys suck the other and I needed a release, so I increased my speed until my orgasm hit. I pinched my nipples and made some noise so they both knew exactly what was happening. After my orgasm, Matt stepped back and I let my boyfriend lick my fingers.

Matt held Aidan’s penis again, which was rock hard and likely ready to blow. ‘I’m afraid your girlfriend won’t allow that inside me. If she had, I would have done this.’ Without letting go, he turned to face away from him. ‘And then I would have done this.’ He squatted down until there was very nearly forbidden penetration. This was too much. This birthday treat had gone better than I could have hoped for and after a few seconds of thought, I decided to relax the rules. But just before I could tell them, Matt stood up abruptly. ‘Unfortunately, that’s off the cards, so we’ll need to work around that. Get on the bed face up and I’ll show you.’

I dismissed my thoughts of moving the goalposts and enjoyed the unfolding scene. Matt asked for the bottle of lube and spread some on Aidan’s penis and shaft. He then lay on top of him and placed his own against Aidan’s, rubbed it up the entire length until the two purple heads met, then rubbed it all the way back down again. He repeated this motion again and again, making it shorter and faster every time until the two heads were rubbing together constantly.

Matt caught my attention. ‘See? Not docking. Still within the rules.’ But still very close. I continued to bite my tongue and take pleasure at the sight of the dry humping. He added, ‘You can join in if you like.’

I didn’t need to be asked twice. I lay beside Aidan and offered one of my nipples to suck, letting him put his fingers into my vagina while I started to masturbate again. His other arm was already around our friend’s back.

It didn’t take too long before I heard both boys starting to breathe more loudly and their humping becoming more urgent. Matt’s orgasm hit just as my boyfriend’s semen shot all over his stomach. Both their penises were twitching in the aftermath. Matt leaned in to give him a long kiss. When the kiss finally broke, he scooped up a little semen, held it in front of his little purple head and asked, ‘Can we pretend I’m the one who made that mess?’

‘Mmm, yes.’ I didn’t mean to let that slip out, but I was still masturbating and seriously turned on.

 ‘Are you going for another orgasm?’ asked Matt.

‘Definitely,’ was all I could say.

‘Let’s finish ourselves off together.’

I stayed on the bed beside Aidan, who had found a tissue and started to clear up his mess. Matt climbed off the bed to sit on the chair. Although we weren’t attracted to each other, I found myself watching as his second orgasm built up. His style was to wrap a finger around his little head and pull the foreskin rapidly back and forth, just like Aidan but on a smaller scale. He also placed two fingers from his other hand in his dock.

I couldn’t hold back any longer. I squeezed my nipples and closed my eyes and let my orgasm happen. When I opened them, Matt’s penis was twitching again and he was licking the fluid off his fingers.

‘Well, that was nice,’ he said. ‘How was your little surprise, Aidan?’

‘That was… something else.’ He had finished wiping up and had been watching us both orgasm.

‘Can we do this again?’ said Matt and I at the same time.

‘Wow,’ I said, ‘looks like we’re on the same page.’ I stood up to find my dressing gown. ‘I’d better make a start on dinner.’

‘Let’s just get a takeaway,’ said Aidan. ‘We need to relax after all that.’

‘I agree,’ nodded Matt. ‘I’m in the mood for pizza. Veggie, though. I’ve had enough meat for one day.’

Published 
Written by JennaSide
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