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2026-01-25
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I'd love to try a lady

Summary:

Phil experiments with a woman. Dan watches.

Notes:

Prompt by an anon on @phornythoughts on tumblr: Hey guysss remember when phil said he “would love to try a lady” on the pod. yeah. no sfw thoughts here. i’m sure dan would be okay with him exploring his sexuality (and vice versa. dan has likely done the same in his self discovery process) but my main takeaway is that i want to put dan in the cuck chair and make him watch phil’s first time with a woman. without being able to touch himself (the lady is a lesbian who is also trying something, a little awkward and funny) (bracket added by my fiance who helped me pick a prompt)

Work Text:

 

“Did you mean anything by that? About trying a lady?” Dan asks, “you know you could, right? I mean, if you wanted to, I wouldn't stop you.”

 

Phil is slightly taken aback by this sudden revisitation of a conversation they had in passing. “What do you mean, you wouldn't stop me?”

 

“I just mean, I don't want to deny you any experiences. It's normal you’d want to try something new after sixteen years.”

 

“I'm - I'm not sure if I actually meant anything by it. Anyway, it would feel weird, having sex with someone else. Especially a woman. But I'd be lying if I said I wasn't curious, at least.”

 

“So, you are curious, then?” 

 

“I mean, yeah. Kind of. I've always wondered what it would feel like to - you know?” Phil licks his lips nervously. It's not like this is entirely new. They had this conversation a few years back, when Dan was once again questioning his sexuality. Back then, he was the one who wanted to have sex with a woman at least once, now Phil finds himself in this position, and he's not entirely sure how they got here. 

 

“I'm saying you could find out. If you wanted to,” Dan says.

 

“I don't know, Dan, you know I'm such an experience-sharer, I wouldn't want to experience something like this without you, if that makes sense?”

 

Dan's face softens for a moment, and then lights up in an amused grin. “Well, I could be there,” he says.

 

Phil shakes his head in confusion, “you mean, like a threesome?”

 

“No, I've had my female experience, and it wasn't for me. But I could, you know, watch.”

 

Something stirs inside Phil. This is getting him interested now. Having sex with a woman while Dan is watching him? Fuck, this could be actually hot. He lets himself consider the scenario seriously for the first time. And immediately runs into an obstacle. “How would we even find someone?” 

 

Dan's brow furrows into his thinking face. Then he seems to have an idea. “You know, our friend Effie has been saying she is kind of in the same situation?”

 

“Effie? Isn't she a lesbian?”

 

“Yes, and you're gay, babe. That's the point. At Sam's party the other day, she said she wants to have sex with a man. She was quite drunk, but I think she was serious about that. Although we'd have to check with her if she's fine with me watching, obviously. As well as check with her about all of this, I mean.”

 

“Sure, I mean, if I'm going to sleep with a lady, Effie is a good choice. I like her and stuff.”

 

__________



They are actually doing this. They asked Effie (which was kind of an awkward situation at first) and she was into the idea, and now they are actually doing this. 

 

And Phil is nervous. It feels like a first date, something he hasn't done for the better part of two decades, and all of this is new, and what if he does something wrong?

 

But he is so glad Dan will be with him all the way. Dan, who exudes a calm confidence and who will help calm him down as he always does. They talked about this in the days leading up to the event, the two of them, sometimes also with Effie. 

 

They all know the rules. It's quite simple, really: Phil and Effie are going to have sex. They purposely didn't define it further, whatever happens, happens. Dan will watch them from a chair next to the bed. He will not participate in any way, and he is not allowed to touch himself. This was Phil's idea. He likes the thought of Dan, his Dan, getting turned on by him having sex with someone else, but not being able to do anything about it. Maybe they can have some fun when Effie is gone again. He loves getting Dan riled up.

 

When the doorbell rings, Phil actually jumps. He gets up quickly and almost runs to the door. Dan just chuckles at his partner's eagerness and follows him at a more leisurely pace. By the time he makes it to the bottom of the stairs, Phil has flung open the door and embraced Effie, who has tumbled in with a rush of cold air. 

 

They exchange greetings and pleasantries, but don't linger too long before moving their activities to the bedroom. This is also something they had talked about. No unnecessary preambles. They end up in their assigned positions, Dan in his armchair, Phil and Effie on the edge of the bed, facing him. 

 

Phil throws one last reassuring glance at Dan, one last question for permission. Dan nods almost imperceptibly, and Phil takes Effie’s hand shyly. 

 

“You ready for this?” he asks her.

 

“Let's do this,” she says, and leans in to kiss him. 

 

It has been so long since Phil has kissed anyone but Dan, who's lips are always a bit chapped. Effie's are softer, and taste faintly of mint. The kiss stays chaste only for a few moments, then Phil slips his tongue into her mouth and plays with her tongue. 

 

Effie moans into the kiss, and places her hand on Phil's thigh, rubbing small gentle circles. He puts his hand on her back, petting it, feeling a little awkward. Her form is so different from Dan's, and he can't shake the acute awareness that Dan is also right there, watching them. 

 

Effie seems to sense his thoughts wandering, and breaks from the kiss. She looks into his face searchingly. Phil dodges her gaze, and looks over at Dan, who seems a bit flushed already but gives him an encouraging nod. This is the reassurance Phil needs, and he dives back into kissing Effie. 

 

She takes his hand, that is still stroking her back helplessly, and gently puts it on her chest. Phil gasps into her mouth. He likes breasts, in an appreciative way. He now discovers he also likes the feeling of one in his hand. Carefully, he squeezes a bit, feels around, moves over to the other one. 

 

Then Phil remembers he has two hands, actually, and can touch both of Effies's boobs at the same time, so he does. Effie pulls away from the kiss again and giggles lightly. “You can grab them a bit, don't be scared,” she says.

 

Phil also chuckles. “It's just, they are so soft, I don't want to hurt you,” he says.

 

“You won't. I'll take my shirt off now, yeah?” Effie asks. 

 

Phil nods, and she pulls her shirt over her head, revealing a black sports bra. While Effie is occupied, Phil looks over at Dan again, who is watching her intently and doesn't notice Phil looking. Phil thinks he is very cute in his singular concentration. 

 

Then Effie starts kissing him again, and he can no longer look at his boyfriend. She slips her hands under his shirt and, after a few moments of roaming, finds his nipples. Phil lets out a surprised moan, and then mirrors her, putting his hands on her boobs again, playing with her nipples through the thin fabric. 

 

She helps him out of his shirt and then blinks up at him innocently. “Help me with this?” gesturing at her bra, “I wore one without clasps just for you.”

 

Phil can't help but be touched at her consideration. He was in fact a bit intimidated by trying to get a bra off her, but Effie has made it easy for him. In a joint effort, they manage to get the tight fabric up and over her head, not without some fumbling and giggles. 

 

Phil stares at her now exposed boobs. Then he notices he is staring, fixes his eyes back on Effie's face, a blush rising in his face. “Sorry,” he murmurs. 

 

“It's okay,” Effie laughs, “you can look. They are one of my best attributes. So can you, by the way,” she throws over at Dan, who seems caught off guard, but was, in any case, not waiting for permission to stare.

 

“Can I - do you want me to - kiss them?” Phil asks.

 

“Yes. I'll lay down now, yeah?” Effie replies and, and lies back on the pillows. 

 

Phil follows her, cupping her breasts again, kissing her mouth, and then working his way down along her jaw, her neck - she lets out a gasp just like Dan does when Phil kisses his neck - her collarbone, and down to her boobs. He licks her nipples, sucks them into his mouth, gently grazes them with his teeth. Effie makes soft moaning sounds to let him know she is enjoying his ministrations. 

 

He glances over at Dan again, whose eyes are trained on Phil's face where it is buried in Effie's chest. Dan smiles at him when he catches Phil's gaze, asking him a silent question, and suddenly Phil feels weird about all this. He sits up, earning puzzled looks from both Dan and Effie. “This is weird,” he says. 

 

“Do you want to stop?” Dan asks. 

 

Phil considers this for a moment. “No, I don't think so. It's just - weird,” he replies. “Are you both still okay with this?” 

 

“I am more than okay,” says Dan, “quite enjoying the show, to be honest.”

 

Phil's eyes flick down and oh - Dan is growing hard in his jeans. Phil licks his lips. Suddenly, the fact that Dan is turned on by this comforts him, and turns him on too. 

 

“Me too,” Effie says, “I agree that it is weird though. But I don't want to stop, if you want to continue too.”

 

“Yes, sorry,” Phil says.

 

“No need to be sorry, sweetheart,” Effie smiles and pulls him back down and into a kiss. 

 

They make out for a few minutes before Effie's hands wander to Phil's ass and slowly make their way into his jeans. Phil is not unaffected by all of this himself, and he can feel his erection start to fill out. 

 

“Let's take these off, yeah?” Effie says. 

 

Phil nods and, without further ado, wriggles out of his trousers and underwear, before helping Effie out of hers. They are now both completely naked, and he can hear Dan's breathing become heavier. 

 

He allows himself to look up and down Effies's soft curvy body. She does the same with his. Phil can't honestly say that he is really turned on by the sight, but he sure is fascinated by her form, the fact that she is smaller and somehow rounder than Dan is, the freckles in unfamiliar places, the mess of curly hair between her legs. 

 

Phil takes a deep breath and looks into Effie’s eyes again, smiling at her. She smiles back at him, and for the first time, he detects something like insecurity in her eyes. 

 

“So, what do we do now?” Phil asks, wanting to give her another opportunity to back out.

 

“Can I -  touch you? And you tell me what feels good? Because you know, I've never -”

 

“Yeah, yeah, ‘course,” he says.

 

Effie crawls up to him and, with some difficulty, flips them over, so she is on top of Phil and straddles his legs. She roams her hand all over his chest again, steadily making her way down and scooting further down his legs in the process. Phil scoots around a bit when her weight squeezes his shins uncomfortably, almost making Effie fall off him and the bed. He grabs her hips to steady her and she moans.

 

“Oh, you like that?” Phil asks and Effie nods. “I'll remember that.”

 

Effie has worked up the courage to touch his dick, carefully cradling his balls and stroking the shaft, making Phil groan. Her hands are smaller than Dan's, but it feels good. Phil has closed his eyes, and so startles when he feels something wet at his tip. He looks down to see Effie tentatively licking the head of his dick. 

 

“Is this okay?” she asks.

 

He lets his head fall back to the pillow. “More than okay.”

 

“But you'll tell me if I'm doing something wrong, alright?”

 

“Yes, I will.”

 

Effie continues licking his dick, and, after a while, carefully takes the tip in her mouth. She is not as confident with this as Dan is - Phil immediately feels guilty for the thought, because he shouldn't compare them, and also, how could she be? Dan has sixteen years of experience sucking his cock, and Effie has none and - Dan. Phil's eyes blink open and he turns his head to look at his boyfriend. 

 

Dan is breathing heavily, and palming his erection through his trousers. Which is not allowed.

 

“Hey, no touching!” Phil says, and both Dan and Effie startle and look at him.

 

“Not you,” he says to Effie, “you're doing great, but this one -” he points at Dan, “is breaking his own rules.”

 

Dan stops touching himself, but looks at Phil through his eyelashes seductively. “Well, you're gonna have to punish me later,” he says. 

 

“Oh, I will,” Phil smiles, his dick twitching at the thought of what he will do to Dan. But now he has to focus on the present situation. “Keep going?” he suggests in Effie's direction. 

 

“No,” she says with a wicked smile, “my turn.”

 

Phil swallows thickly. Suddenly he's nervous again, and his hands are shaking slightly as Effie climbs off him and lies down next to him. 

 

Effie notices and gives him an encouraging nod. “It's okay,” she says, “you can't do as bad as I just did.”

 

“Hey! Don't say that, you didn't do bad at all. But you also tell me if I do something wrong, yeah?” 

 

“Okay,” Effie says and settles down in the pillows, lightly spreading her legs for him. 

 

Phil takes another deep breath, and begins kissing her neck, since he got such a positive response for that earlier. It works again, and, feeling encouraged, he kisses his way down.

 

He makes his way to between her legs, and gently licks her there and - she is wet. To be honest, Phil kind of forgot that this is something vaginas can do naturally, without lube. Well, this is very convenient. He uses his fingers to spread the wetness around, carefully monitoring Effie's reactions to make sure she is enjoying this. But she has her eyes closed and lets out small moans, so Phil gains courage and begins licking all up and down her slit. 

 

One way he prepared for this - he knows this is ridiculous - was by looking at diagrams of vulvas on the internet. So he knows where the clitoris is - theoretically. No one told him that real vulvas look different from diagrams, so it isn't easy. 

 

“A little bit further up,” Effie decides to help him out, and, when he gets it, moans louder, “yes, right there.”

 

Phil gently sucks on her bundle of nerves and, feeling reassured by her reactions, carefully pushes one finger inside her. It slips in so much easier than with a man, and for a moment he has the silly thought that this is natural. All sex is natural, he admonishes himself, but he can't help but be amazed at her wetness and wonder what it will feel like around his dick. 

 

He continues to finger her open while licking her clit, until Effie gently pushes his head away. “I think I'm ready for the next step,” she says, slightly out of breath.

 

Phil nods, and looks around at Dan again. Dan is watching them with ravishing attention, his dick fully hard now, but he is not touching it. Good boy. 

 

“Condom?” he says to Dan, pulling him back to reality. Dan shakes his head confusedly, then seems to realise what Phil wants from him and leans over to the table next to him, where they deposited the box of condoms they bought just for tonight. The two of them haven't used condoms in years, but with other sexual partners that is a must. Especially if said partners could get pregnant otherwise. 

 

Dan takes a condom out of the box, fumbling slightly, and deposits it in Phil's outstretched hand. Phil tears open the packaging and rolls the condom over his hard dick. 

 

“You sure about this?” he asks Effie again. She nods, and glancing at Dan, he sees him nod as well. 

 

Phil lines himself up with her entrance, and her wetness makes him slip in easily. Still, he makes sure not to push in too much at once, and instead pulls back slightly before pressing deeper, to give her time to get adjusted to his girth. He gauges her reaction carefully all the time, and as far as he can tell, Effie seems to enjoy it. And, thinking about it, so does he. It is definitely unfamiliar and different, especially since he rarely tops, but it feels good. So soft and warm and seemingly pulling him in deeper. 

 

Finally, he bottoms out and pauses again, looking at the woman underneath him. A woman. Insane concept, really. When he doesn't move, Effie opens her eyes and smiles. “You feel so good,” she whispers, “fuck me, please.”

 

Phil doesn’t need to be told twice, he begins to thrust inside her, moving slowly at first, but gaining force at her enthusiastic moans. Somewhere in the back of his mind he is still aware of the strangeness of the situation, he is still aware of Dan, who sits in his armchair and whose hands are straining against his thighs in an effort not to touch his throbbing erection. But an animalistic instinct in Phil has taken over now, and he just wants to fuck, to claim, to be deep inside that tight wet heat.

 

He leans down to kiss Effie again, and they both swallow each other's moans. On an impulse, because Dan likes it, he lets his hands wander over her throat to her face and pushes two fingers into her mouth. Effie also seems to like this, sucking on his fingers greedily, mimicking the same sensation he feels below. 

 

All the while, his thrusts never let up, and slowly, Phil can feel himself getting closer to orgasm. He thinks about what he would be doing at this point if he was inside Dan instead. Stroke his cock, probably. Then he remembers he should probably do the equivalent here, and he reaches down between their bodies to touch Effie's clit. It takes some effort to find it again, but he manages, he thinks. 

 

Effie makes adorable little uh, uh, uh sounds, and fuck, Phil really is getting close. He thinks he should probably warn her, so he says “Effie, I - I'm gonna -”

 

“Yes, Phil,” she moans, “give it to me”

 

He turns his head to Dan again then, and Dan is flushed and moaning, it takes visible effort for him not to touch, and this is what sends Phil over the edge. He thrusts frantically a few more times and then buries himself as deep as he can and spills into the condom.

 

Phil carefully slips out of Effie and immediately makes sure she is okay by asking a little clumsily “Are you - I mean, do you need me to - ?” 

 

Effie smiles up at him. “No, but that's okay. I have a hard time coming, especially with a new partner. Come kiss me?”

 

Phil gladly obliges, kissing her sloppily, and flopping down next to her. After a few minutes of this, he gets uncomfortable, so he takes off the condom and mindlessly hands it to Dan, who goes to dispose of it. Phil wraps his arm around Effie and watches as Dan comes back, still hard and looking flustered. But he will have to hold on a little while longer. 

 

“Do you need anything?” he asks Effie. 

 

“Just some cuddles,” she says. And that, Phil can give to her. That is one thing he is very sure he is good at, even with a woman. He lets her put her head on his shoulder and feels her melt into his arms. 

 

“You're a good cuddler,” she says. 

 

“I know,” says Phil, “what about the rest of it though? How was that for you?”

 

“I liked it, it felt good, even though it was weird,” Effie says, “let's never do it again.”

 

Phil laughs at that. “Agreed,” he says. 

 

“How did you like it?” she returns the question.

 

“I mean, don't get me wrong, it was great, but I'm pretty sure I'm gay,” he says.

 

“Me too,” Effie sighs. “But now we have the experience.”

 

“How about you, Dan?” Phil asks. Effie turns so she can look at Dan too.

 

“I kind of forgot you were there,” she admits.

 

“I didn't,” says Phil.

 

“Fuck, that was hot,” says Dan. He seems to have calmed down a bit, though. 

 

Phil smiles at him. 



__________



Later, after Effie has gone, Dan and Phil find themselves in their bedroom again. 

 

“You still all hot and bothered from earlier?” Phil asks.

 

“Yeah, that was really hot. Like my own personal porn video. If I watched straight porn. But getting to see you have sex from an outside perspective - I don't know, it did something to me. And don't get me wrong, I love Effie, but I was watching you the whole time.”

 

“You better have,” Phil grins, “but for real, do you need some relief? I don't think I can go again, I'm not twenty anymore, but I could still help you get off?”

 

Dan just nods, and that is all the confirmation Phil needs to pull his boxers down to reveal his already half-hard cock. 

 

Phil begins stroking it lazily, until Dan's moans grow desperate. He scoots down the bed and takes Dan's hard dick into his mouth, swirling his tongue around and swallowing him down. This feels easy and familiar. As exciting as new experiences are, Phil knows he will always prefer the comfort and safety that is Dan. 

 

Dan has apparently really been on edge since earlier, and it doesn’t take long at all before he's writhing underneath him, moaning and desperately pushing Phil's head down. He knows exactly how much Phil can handle and that he doesn’t mind being pushed around a little. With each other, they don't have to tiptoe around anything. They know each other so well. As Dan reaches his orgasm, he is also filled with a wave of overwhelming love for his boyfriend. 

 

Phil looks up at him with adoration, swallowing one last time and pulls off him. When he is face to face with him again, Dan smiles fondly, musses Phil's hair and kisses him. 

 

“I love you,” Dan whispers.

 

“Love you too,” Phil replies sleepily, “more than anything.”