Roommate Interrupts my Butt Play

Before this story starts, I just wanted to give a heads up that, like in my last story, there is a relatively long build up before the action starts.

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These days when everyone is mostly confined to their homes, having a roommate means that my "alone time" is severely limited. For weeks my only alone time has happened either in the dead of night when my roommate is asleep or locked in our bathroom. Both being awkward, needing to be quiet to avoid my roommate hearing. Not that I am necessarily loud, but the knowledge that I need to keep it down, is enough to make me self-conscious and ruin my ability to focus on what I am doing.

This means that I haven't been able to truly satisfy myself, leaving me horny and frustrated, so when my roommate had to go to a doctors appointment that would keep her out of the house for at least an hour, I was quick to seize the opportunity.

As soon as she left I set an alarm for 45 minutes to ensure that I would have time to finish off and get cleaned up before she returned. After that I quickly found the toys I needed for my play and got into it.

About 15 minutes after I started, I was lying naked on my belly on my bed, my legs spread and my hand working a dildo in and out of my well lubed ass, when the door to my room opened.

I had been so absorbed in my play that I had missed my roommate returning early and when I didn't respond to her call, she had come to my room to let me know she was back.

"Hey, the doctor called and..." Anna, that's my roommate's name by the way, said as she opened the door. Her voice dying down as she saw the position she had walked in on me in.

I turned to look at her, neither of us saying anything, the only sound in the room the persistent vibration from the toy still in my behind.

"Anna, I..." I started to say before she cut me off.

"Oh my god, I am so sorry. I, I...the doctor called and cancelled and I...sorry," with that she turned and fled through the door, closing it behind her.

And that is where I am now. Sitting in my bed, mortified at what Anna might think of me and embarrassed as hell. All arousal chased away, my dildo lying forgotten on the bed.

While we are close me and Anna have never really talked about sex or masturbation or anything of the sort. I know that due to her upbringing it isn't really something she is comfortable discussing and I have always done my best to respect her feelings and not push my sexuality in her face. Also, while I don't have the same hang-ups about discussing sexual matters as her, I am still a very private person when it comes to the actual acts. I know, to some, the idea of having another person within hearing distance, or even having another person watching, is a turn on, but to me it has always been a surefire way to stop my arousal dead in its tracks. The exception of course being if the other person is a partner in the act.

So what do I do now? Do I go talk to her? I have no idea how to start a conversation like that. Or do I try to just ignore it and pretend that nothing happened? Or will that make things even weirder.

I am starting to feel a bit chilled, sitting naked on my bed, still wet with sweat, and other fluids, from my earlier play. I decide that that at least is something I can do something about, so I grab my toys and a towel and head to our shared bathroom.

The layout of our house is so that our bedrooms are next to each other, with the bathroom being on the other side of a hallway. If you turn down the hallway you will either get to our front door or, if you turn the other way, end up in our living room / kitchen combo room. This means that I can pretty easily slip from my room to the bathroom without much risk of running into Anna.

Once in the bathroom I quickly clean the toys before turning on the shower and stepping under the hot flow of water.

I usually enjoy showering, the feel of the hot water against my body, sliding my soaped hands over my skin, maybe lingering a bit in certain places, but today my mind is too distracted for that.

After I dry off I quickly slip back to my room. I hate the fact that I feel like I have to sneak my naked body from the bathroom to my bedroom. While we have never spoken about sexual things, nudity has never been an issue and normally I would just walk between the rooms without given it a thought. Hell if there was something I needed in the living room or if I had something I needed to ask her, I would not have hesitated to go there in the buff, but after earlier I feel awkward and like my nudity will mean something else if she happened to see me.

In my room I slip into a short sleeved loose t-shirt and a pair of sweatpants. For a moment I consider putting on underwear, something I otherwise usually don't do when it is just the two of us home. But I worry that suddenly putting on underwear will just make things even more awkward if Anna notices, like it is an open admission that what happened earlier has changed things.

After putting my clothes on I sit on my bed.

Sitting there I start getting annoyed with myself. "Okay, stop, you are blowing this way out of proportions. So what if she walked in on you masturbating. So what if she saw me with a dildo up the behind. It is not like I was doing something wrong. I was alone in my room, thinking she was out."

But even though I know logically that makes sense, I can't seem to shake the embarrassment and, yes, fear, that somehow what happened will ruin our friendship. I haven't really realized how much our friendship means to me before now, us living together being the result of coincidence rather than intention, but over time we have grown really close.

I don't know how long I sit there spiraling in the same pointless thought patterns, but I am eventually interrupted by a knock on the door.

"Mary, do you wanna come eat with me?" I hear Anna ask through the door. Mary is my name by the way or actually it is Marilyn, but no one but my parents call me that.

The fact that Anna is asking through the door and the fact that she is asking at all is unusual. We normally always eat together and she would usually either have called me out to help cook or, if she decided to do it herself, simply have yelled "Dinner" from the kitchen to get me to come.

"It's ok if you don't want to," I hear her say, her voice sounding sad and I hear her start walking away from my door.

I quickly jump up and rush to the door, pulling it open and stumble out after her.

"Wait up! Of course I want food," I say as I catch up to her, deciding to try to act like nothing has happened.

We walk together to the table we usually eat at and sit at our normal spots. Before living with Anna i would usually eat sitting in the sofa in front of the television, balancing my plate on my knees. Anna however have insisted from day one that we eat at the dinning table and, while I was skeptical at first, I must say it has grown on me. Not the table itself, but the conversation over the dinner.

We make some small talk, her complaining that her doctor had called to reschedule her appointment while she was on her way there and me agreeing that it is totally not ok. By silent agreement neither of us mention what happened earlier, but it is clear that it is still on both of our minds and the conversation quickly dries up leaving an uncomfortable silence in its wake.

Taking a deep breath Anna breaks the silence. "Look, about earlier, I am really sorry for walking in on you like that. I...I didn't know you where doing...you know. I just got back and when you didn't answer I..." shrugging she lets her words trail off, her eyes looking down, avoiding eye contact.

"No, no, you don't have anything to be sorry about. I mean you didn't do anything wrong. You didn't even do anything. I mean we come into each other's room all the time. I am the one that should be..." I say before she interrupts me.

"Stop, you don't have anything to apologize for. I was the one..." she says before it is my turn to interrupt.

"No I mean it, you didn't.."

"Neither did you. I was the one..."

"It was me, I am so..."

Neither of us able to get a full sentence out before the other interrupts, we eventually both give up and stop talking, both sitting and looking down at our hands.

I raise my eyes and she does the same at the same time. When our eyes meet a second passes by and then we both break out into laughter.

Through her laughter she chokes out, "So we're good?"

"Yeah," I reply. "I am embarrassed as fuck, but I was never angry. I was just worried about what you would think. I know you aren't really comfortable with all that...stuff".

"I know, I am not..." She starts looking down, suddenly embarrassed again, before I interrupt her.

"No, no, it's okay. I respect how you feel."

Still looking down she whispers, in a voice so low that I can barely hear it. "It is not that I have anything against that sorta stuff. It is just, it is so embarrassing and I don't...I mean...it wasn't really something we talked about where I am from and I don't really know...you know?"

She is still looking down, so I stand up and walk around the table. Putting my arm around her shoulder I say, "No, I have no idea what you are saying. Just spit it out. It is just me and you here and nothing you say will make me think any less of you."

"I am, you know, curious, about that kind of thing. I just, I don't know how to talk about it. I don't know how to ask."

Realizing what she is saying I am momentarily stumped, realizing that I have misjudged her all this time and what I thought was prudeness was really insecurity.

"Wait, so you are saying that you want to talk about..." I almost say that stuff, in order to spare her ears, but if we are going to be able to talk about it, we have to be able to say it, "...sex stuff?"

She mutely nods her head.

"Well ok. Let us make a deal. You can say anything you want, ask anything you want, no matter how silly you think it is and I won't judge or laugh at you or...well ok, I might laugh, but you don't have to feel embarrassed if I do. I won't think any less of you."

She sits for a moment, mulling it over, before simply saying, "Okay."

"Okay, lets clean this up and go sit in the sofa and talk," I say and then, without waiting for a reply, I start gathering up our plates.

As expected her upbringing does not allow her to stay seated while I clean up, so she gets up and starts helping out.

We clean up in silence, both lost in thought and before long we are done.

I grab her hand and start tugging her to the sofa. "Okay, lets do this."

We have a large sofa that easily hold four people with room to spare and as I sit down, she sits on the opposite end of the sofa, as far from me as possible, trying to put distance between us and between her and the conversation we are about to have.

I am not going to allow that so I get up and move over to sit right next to her, putting my arm around her shoulders.

"Much better," I say. "Now start talking."

"I don't know where to start."

"Okay, how about we start by establishing how much you already know."

"Okay, I guess," she says the doubt clear in her voice.

"Alright, so, first thing first, have you ever, you know, done it? Have you ever had sex."

To my surprise she nods, "Once."

"And how was it?"

"Not that good. Neither of us knew what we were doing and he, you know, finished, real quick."

"Hmm ok, but that's pretty normal. First times are usually pretty meh. The trick is to do it again and again and again. But lets not dwell on that. What about, you know, what I was doing earlier?"

"I-I have never put anything up my..." she starts to say before I interrupt her with a giggle.

"I didn't mean that. I just mean, you know, playing with yourself. Masturbating."

"Yes. I mean, some. I sometimes touch myself down there, but nothing more than that. I've never tried, you know, with a toy or anything."

At this point her shyness seems to have somewhat faded and she is now looking at me rather than at her hands.

"So, what are you curious about?" I ask, hoping to draw her out a bit.

"That thing I saw you do. Putting something up your butt. How is...is it...nice?" She asks hesitantly, but with what I can only interpret as genuine interest.

I give her shoulder a small squeeze before replying, "Well I think so, otherwise I wouldn't be doing it. It is a different feeling than what you get from playing with your girl parts. A different kind of pleasure. For me, when I combine it by touching myself while I have something up my butt, the feeling is so much stronger than either on its own."

She sits still, subconsciously biting her bottom lip, staring out into nothingness as she digests this.

A thought strikes me and I can't help myself from asking, "Is it something you think you might want to try?"

At this she quickly turn her head towards me, looking at me as she whispers, "I...yes...maybe."

As we have been talking I have been feeling myself getting mildly aroused. I thought it was just from the subjects we were discussing, but upon hearing her admit that I feel my arousal spike and the truth that my arousal is, at least in part, because of Anna, is unescapable.

"Maybe start with something a little, simpler, than the dildo I was playing with. Maybe you could start by slipping a finger back there when you are touching yourself," as I say this I can't keep from picturing it, her lying in bed, naked, one hand stroking her between her legs and the other creeping back to gently start working at her back door. It is these images that inspires me to say, "If you want me to I can help you."

"He-help me? How?" she asks, her voice sounding kind of shaky, making me wonder if I am the only one being effected by the conversation.

"I could help show you how and help you do it the right way and answer any questions you might have and stuff like that," I say, wondering if my voice sounds as eager to her as it does to me and hoping she is too districted to notice.

"But you would have to be there while I...did stuff"

"Sure, but, I mean, I don't mind."

"I don't know. Isn't it kind of weird?"

"Who cares? It's not like anyone but us will know. So the only thing that matters is whether you want it or not. If you're curious and want to try it then I am happy to help."

Despite my words my motives are far from altruistic. The more we talk about it and the more the image flash through my mind, the more I find myself aroused by the thought. I briefly regret not wearing underwear, wondering whether or not my hard nipples are visible through the t-shirt I am wearing and whether my arousal will be visible in the crotch of my sweatpants. For the first time I know what it is like for guys, having to worry about hiding their boners.

While I have been taking a physical inventory, Anna has been contemplating my suggestion and she seems to have come to a decision.

"Okay, I guess we can try."

At that I feel parts of anatomy clench up and I know that if there wasn't a visible wet spot at the crotch of my pants before, there most certainly is now. Thinking quickly I say, "Okay, if you go to your room and get ready then I will be right there. I just need to grab a few things."

"No-now? We're going to do this now?"

"Sure, why not?" thinking quickly I take a gamble and add, "Don't even try to pretend that this conversation hasn't got you at least a little bit turned on."

I can see my words strike true as she starts to turn red and turn her head. I quickly reach out with my hand and gently put my hand on her cheek and turn her head back towards me and say, "Hey, me too. It's completely natural and nothing to be embarrassed about."

At this her eyes open wide in surprise, "Really?"

"Really," I decide that maybe letting her know how much our conversation has effected me isn't such a bad thing. I gesture towards my hard nipples. "See for yourself."

She looks down at my chest and then quickly averts her eyes before slowly moving them back.

"And if that isn't enough proof then look here," I say, standing up and grabbing my sweatpants, pulling them up tight against my crotch making sure they capture as much of my wetness as possible. This of course also has the side effect of making the fabric slide against my sensitive parts and it is all I can do to stop myself from moaning out loud.

As her eyes are inevitably drawn to the wet spot on my pants Anna lets out a gasp and clasps a hand over her mouth.

For some reason her shocked reaction is highly comical to me and I can't help but burst out laughing. Through my laughter I choke out, "See nothing to be embarrassed about."

Anna looked up at me when I started laughing, but she can't keep her eyes from straying back down to the wet spot in my pants.

She stands up and says, "O-okay, le-lets do it." and turns and almost flee to her room.

Still laughing to myself, I give her time to get to her room before I start towards mine.

Once I get to my room I find a bottle of lube. I also consider whether I should bring a small toy, but decide against it, better not push her too much the first time and, of course, if we take it slow then I have an excuse for helping her out again another time.

I stop for a moment and consider whether I am taking advantage of Anna, but after weighing my different motivations I decide that yes, I am partially driven by my own desires, but at the same time, if I can help her be more open and accepting of her sexuality then that is a good thing.

Before going to her room I make a decision and pull off my shirt and pants. If I am naked as well it might be less hard on her and also, if I am going to demonstrate anything then I might as well start out naked.

As I stand outside her room, lube in hand, I am faced with a minor dilemma. Her door is closed. Should I knock or just enter. Deciding to play it safe I bring my hand op and knock on her door.

"Co-come in," Anna calls from inside.

I open the door and enter. To my surprise Anna is sitting fully dressed on her bed.

"You're dressed!"

"You're naked!"

"Well yeah, I figured it would be less awkward for you if I was naked as well."

I walk over and crawl onto the bed sitting cross-legged facing her.

"Soooooooo?" I draw out the word and end it on a questioning note and make a gesture towards her to indicate her dressed state.

She lets out a sigh and visibly steels herself. She then grabs the edge of her shirt and pull it over her head. Not taking a break she then immediately proceeds to open her bra and slide it off, freeing her breasts to the air.

I can't help taking a closer look at her breasts than I have done previously. I have seen them plenty of times, but the different context here makes me see them in a different way and I can't help but wonder what they would feel like in my hands.

Unaware of my thoughts Anna, move to the edge of the bed and stand up to give herself space to unbutton her jeans and slide them down and off of her legs.

I am very interested in seeing whether her white panties has a wet stain on them, but unfortunately the angle she got off the bed at means that I can't see it.

She slides the panties down her legs and step out of them, leaving them on top of her jeans. Part of me really wants to go over there and take a look.

Before I can turn thought to action however, Anna crawls back onto the bed and the way she does it means that her rear end is briefly facing my way, giving me a clear view of her cute butt and down below it, her wet lower lips, and they are DEFINITELY wet.

I subconsciously lick my lips as a steady warmth spread through my body and coalesces between my legs.

Once she has made her way back to her previous spot on the bed, Anna turns around and faces me again, copying my cross-legged pose.