Roommate Interrupts my Butt Play

"So what now?" she asks, in a seemingly calm voice, but knowing her as well as I do I can hear the nervousness she is trying to hide.

"Well I guess that is up to you. You could lie down and start by just touching yourself like you usually would and then, once you're good and ready, I help you get started with a finger back there. Alternatively if you need some help to get comfortable I could also give you a massage. Or of course if you would rather, then I could also give you a more practical demonstration."

"A practical demonstration?"

"Yeah, I could show you." I say, taking my hand and letting my fingers trail a path from my neck down between my breasts, down to my belly button and then letting it slide down and to the side to my thigh and around onto my butt cheek. I then let my hand fall back down to resting on the bed.

She swallows visibly, her eyes glued to my hand, "N-No I don't think I could handle that."

"Okay then, how about we start with a simple massage and then once you're comfortable you can decide where we go next."

"Okay," she says and then she leans forward and lies down on her belly on the bed.

I consider straddling her legs, but decide that the feeling of my wetness pressed against her might be a bit more than she is ready for, so I instead kneel next to her upper body and lean over her.

I start by gently sliding my hands over her back, just making paths from her lower back and up to her shoulders and back down.

Despite the fact that my current touch is relatively innocent, the feel of her smooth soft skin under my hands still send shivers through my body. Of course the view of her butt and the unobstructed chance to stare at it does nothing to calm me down.

After sliding my hands over her back a couple of more times, I move them to the top of her shoulders and begin to actually massage her rather than just stroking her.

As I start massaging her for real, she lets out a small sigh and her body visibly starts to relax. Her muscles loosens and her breathing starts becoming deep and steady.

I work my way down over her shoulders and massage my way down her back. Not rushing, but also not taking too much time.

When I reach her lower back I can't help repositioning myself to give me a better view between her legs. Unfortunately her legs are relatively close together, meaning it is limited how much I can see of her lady bits, but I have a pretty good view of her ass, her asshole peeking at me from between her cheeks.

During the massage I have felt my arousal slowly building and have felt myself steadily grow wetter to the point where I could easily see myself leaving a wet mark behind when I move from my current spot on the bed.

I continue massaging her lower back for a minute or so, but I can feel the need for us to move on to something else growing and I am unsure how long I will be able to help myself.

I decide to try and push us onward while I am still in complete control of my actions. I lie down next to her, stroking my hand up over her body to the back of her neck and onto her cheek.

"Hey honey, I think you're ready to move on now."

"Okay, what should I do?" she asks in low, almost sleepy voice.

"Well you could just lift yourself a bit and put a hand down between your legs. That way I can continue massaging you if you want me to."

Instead of answering she does as I suggested, lifting her body up and repositioning it so that she can slide a hand underneath herself and reach down to her crotch. As her fingers make contact she gives a small gasp.

I crawl down between her legs and gently push them further apart, both to give me a better view of her hand moving over her wet folds, but also to give me room to position myself between them.

I take a moment to just admire the view of her fingers sliding over her clit and listen to her start to moan.

A moment is all I can manage however and I lean forwards and gently place my hands on her ass cheeks, one hand on each cheek.

I was half expecting her to protest, or at least ask me what I am doing, but instead she just lets out a louder moan and I see her fingers start to work faster.

My new position has brought me closer to her crotch and I have an even better view of her fingers working her their magic. Being closer also means I can hear it as well. The wet sound somehow making it even more erotic.

A large part of me wants to let go of her and move one of my hands between my legs to start giving my own wetness some attention, but I manage keep my eyes on the goal.

I start stroking my hands over her butt cheeks, not really massaging as much as simply groping. I slide my hands down to her inner thigh and stroke her there and then back up to her butt. Grasping her cheeks a bit firmer I pull them apart, spreading her open and stretching her asshole. At this she gives a slight whimper in between her moans.

I am gripped by a desire to lean down and start licking her tiny opening, which surprises me as I have never really thought of the idea of licking someone's ass as something arousing before. I have imagined having someone do it to me, but never the other way around.

I manage to contain myself, however, sure that if I followed through on the desire it would be too much for Anna. Instead I lean down and gently blow on her asshole. This makes her give another whimper and as I continue blowing on her the whimpering starts to rise in volume.

I stop for a moment and ask her, "Do you think you are ready to try something more back here?"

My answer is a half gasped, "Yes," followed by more loud moaning.

I reach out and grab the lube I had brought with me. It is the kind with a pump dispenser at the end and I place it right above her asshole. Using my other hand to hold her cheeks apart, I pumps a generous helping of lube directly onto her asshole.

As the lube makes contact with her she makes a loud sound, somewhere between a moan and a scream and the muscles in and around her asshole contracts, temporarily squeezing her cheeks together and hiding her asshole.

After a few seconds however, she relaxes and I am able to spread her cheeks again, giving me a view of her asshole, now covered in lube.

Looking at her lubed asshole I find myself really wanting to touch her back there, just gently slide my finger over her opening and then slowly slide it inside her. At the same time I know that the point of this whole thing is making her comfortable touching herself back there, not for me to satisfy my own urges.

"Give me your free hand," I say, taking her hand when she reaches it back.

I place her hand on her lower back, just above the cleft of her ass. "Okay, slide your fingers down between your ass cheeks until you touch your asshole."

I use both my hands to hold her ass cheeks open. If I can't touch her, then I can at least make sure I get a good view of the action.

Her hand slowly starts sliding down between her cheeks. Her index finger making the lightest contact with her skin. As it slides onto her lube covered asshole, she lets out a moan that is deeper than her previous ones and I see her entire body shiver.

"Now gently push against it. You don't have to push your finger inside yet, but you have to feel it pushing against your opening."

As she does, I become aware that the sound of her hand working between her legs have speed up, moving over her clit at a hectic speed. The sound of her moaning has risen in pitch and I can tell that she is close to coming.

"That's it honey, push the finger against your pretty little asshole and come for me," I say, urging her on.

At my words her body starts shaking and her asshole starts tensing and relaxing as an orgasm starts flowing through her. The finger on her asshole is still pressed against it, but it has yet to move inside, lingering instead at the trembling opening.

I briefly consider physically pushing her finger inside her, but decide to let her enjoy her orgasms instead. We may not have made as much progress as I had expected, but her coming while touching her asshole is a good start and, I remind myself again, slow progress means more chances for me to help her out.

I watch her fingers continue working her clit and watch as her vaginal opening pulses. I can't help wondering what it would feel like if I slipped my finger inside her, having her vaginal walls grab onto my finger as her orgasm continues.

I also listen to her moans, which have gone almost quiet now, as the orgasm is running its course.

I see the fingers on her clit start to slow down, the finger on her asshole slide away and her breathing start to return to normal.

I release her ass cheeks, which I have been holding apart throughout it all, and lie down next to her. I snuggle up next to her, putting my arm around her and gently kiss her cheek.

I am keenly aware that my chest is pushed against her arm, one of my hard nipples resting against her soft skin. Part of me really wants to also move the lower half of my body up against her. The thought of putting one of my legs over hers, putting her thigh between my legs, against my wetness, is enough to make my breathing hitch and make my lower parts clench, sending a wave of pleasure through my body.

I am however still wary of doing something that will push her too far and I am determined that this is about her and making her comfortable with her body. So, taking a deep breath and planting another soft kiss on her cheek, I roll away from her and prepare to go to back to my room and take care of myself in there.

Until now she has been lying still after her orgasm, her eyes closed, making me believe that she might have fallen asleep, but when I look back at her she has rolled onto her back and propped up her upper body and is looking at me.

"Where are you going?" She asks.

"I was just going to go to my room and take care of myself. I am not gonna lie, all of this has got me pretty horny and I need some relief."

She bites her lip, looking pensive for a moment, before whispering in an almost inaudible voice, "You don't have to go."

"What?" I ask, not sure if I heard her right or if my lustful mind was simply hearing what I wanted to hear.

"I said, you don't have to go. I mean, you were here while I did it and, well, I-I-I wouldn't mind if you did it here too," she says, her words uncertain as if she isn't really sure she can get the words out.

"Are you sure?" I ask, though it is mostly for show, as I am already moving back onto the bed.

"Yes, I..." she says, before stopping and biting her lip briefly before continuing, "I want to watch."

At this I feel a wave of pleasure shoot through my body and I know that I won't be putting on much of a show for her, probably coming the second I touch myself.

"How..." I have to stop and swallow before being able to get the rest of the words out. "How would you like me to lie?"

The thought of her directing my masturbation excites me to the point where I feel my entire body start shaking.

At my question her eyes open wide in surprise, but it doesn't last long, before a look of concentration mixed with excitement takes it place.

"Maybe on your knees? That way I can...see," her voice breaks on the last word as if not really believing that she would say such a thing.

In my aroused state I don't hesitate for an instant, immediately rolling onto my knees, with my lower parts facing her. I spread my legs apart to give her as good a view as possible, and lower my upper body down to the mattress.

"What would you like me to do?" I ask. The only problem with this position is that I can't see her reaction to my words, but I hear her move on the bed and feel it dipping down behind me as she moves closer.

I feel her hot breath against my wet pussy, showing just how close of an examination she is making. The breath hitting me, causes my vaginal muscles to contract and a loud moan to escape my lips.

The knowledge that she would have been able to see my vagina moving, combined with her continued breathing against my wet folds is almost enough to send me over the edge without even having touched myself, but I am determined to hold on and give her what she wants.

"Touch yourself," she whispers. I can feel the air of each word hit me, sending waves of pleasure through me.

Part of me had been hoping for more detailed instructions, but given her lack of experience her simple request is completely understandable and I don't waste any time complying.

My right hand flies between my legs, moving so fast that when it reaches the wetness between my legs it hits with a slapping sound and I give a loud yelp as a stab of pleasure mixed with pain hits me.

I don't let that stop me however, quickly plunging two fingers inside me and angling them so that they press against just the right part of my inner walls. At the same time, my palm is pushing against my clit, adding to the pleasure coursing through me.

I start moving the hand fast, the fingers and palm both moving against their pleasure zones in a frantic way, all control having been pushed from my mind by the all enveloping need to cum.

I start moaning loudly, doing nothing to keep my volume down.

My excitement is rising rapidly, my orgasm quickly approaching as wave after wave of pleasure crashes through me, but before I can reach the top, I feel a hand on my left butt cheek, pulling my cheeks apart and hear a voice ask, "Can you touch yourself back here too?"

At the words I feel my orgasm starting, but not wanting to disappoint the voice, I put my free hand back there and push my middle and index fingers against my tight asshole. The fingers don't slide inside, as there isn't any lube to allow easy entrance, but the touch still sends another shockwave of pleasure through me, pushing my orgasm to new heights.

The touch of my fingers against my asshole, pushes the pitch of my moans up making them more akin to screams and I feel my vaginal muscles continuously contract and release my fingers. I also feel my asshole pulse against the fingers pushing against the opening, still not letting them slide inside, but letting them tease the entrance.

Through all of this I am still keenly aware of the hand on my butt cheek, which has now started making gently circles, caressing my skin.

The pleasure continues rising until eventually my mind drowns in it, making the rest of the world disappear, the pleasure the only thing that exists.

I don't know how long my mind spends in that blank space of pleasure, but it feels like way too short. When eventually I start becoming aware of my surroundings again, I feel something that almost makes up for the loss of that pure pleasure state.

At some point I have turned onto my side and I feel a soft body up against me, holding me tightly against it.

Unlike when I held her, Anna hasn't kept back, completely entangling our bodies. Aside from her arms around me, I also feel her breasts pressed against my own and one of her legs is between mine, her thigh pressed against my wet pussy, just as I previously imagined. Our position also means that my own thigh is between her legs, her soft wetness pushed against it.

If I wasn't just coming down from one of the best orgasms in my life I am sure that my current position would be an instant turn on, but as it is all I feel is a nice warmth spreading through my body and a deep feeling of contentment settling over me.

I open my eyes and immediately meet Anna's eyes, her face right in front of mine.

"Hi," she says, a smile lighting up her face. "Can we do this again some time?"

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This story is relatively heavy in dialogue. As I believe I mentioned previously I am not really comfortable writing dialogue, so I decided to push through it and write a story with a lot of it. Some of the dialogue in this story is a bit (or actually a lot) awkward, but that is largely intentional, trying to portray the awkwardness of the characters. Hopefully this shines through. I would really appreciate feedback on the dialogue. Does it work? Do you guys like it? Is there anything that could be better?

You might have noticed that this story ends in a way that leaves a lot of room open for further developments. This is done on purpose, as I am considering continuing this story with another one and possibly even more after that. That will however depend on how this one is received, so if you like this story and want more, then please leave a comment letting me know.

Thank you for reading and I hope you enjoyed the story.