This story originally appeared at Reddit.com
A couple of years ago Jessica and I were ready to move out of our home. We were engaged to be married early the next year, and while I’m sure Jessica had different reasons, a large part of the motivation for me was to have somewhere we could fuck without feeling like we were doing something illegal at my parents’ houses. Jessica was fit, toned and about 5’7. She dressed for sport when she wasn’t working, usually in a thong and yoga pants that showed off her perfect ass. Being an ass man, it was supremely frustrating to me that she only rarely initiated sex and palmed it off as frequently as possible, though she made up for it in other qualities.
Unfortunately, rentals where we wanted to live were priced out of our reach, so we put out feelers for potential housemates. Peter had been one of my closest friends for years and was in a relationship with Lily. We all hung out fairly regularly but the girls barely tolerated each other. You know when two people are just going to clash, so Peter and I had given up attempting to make them friends. They were polite to each other’s faces, so we left it at that.
Peter and Lily had an… interesting relationship. They had the most dramatic and ridiculous fights over nothing and didn’t care who was watching. We weren’t spoiled for choice in the housemate department though, so we eventually found a two story townhouse fairly close to where we wanted and moved in together.
My frustrations with Jessica and my lackluster sex life were compounded by the close proximity of Lily. I had never before found her that attractive compared to Jessica, but she was starting to look pretty good. She was a bit smaller than my fiancée, probably about 5’6 with green eyes and shoulder length chestnut brown hair framing a face best described as being ‘cute’. There were frequent occasions where just the two of us were home together, doing our own thing but acutely aware of each other. She often went around the house in a short white dress that tantalizingly displayed her legs. I was in love with Jessica though, so put it out of my mind.
I was in a hurry to get up to our bedroom one morning, taking the stairs two at a time. The staircase had a bend in it, so I didn’t see Lily coming down until it was too late. We ran into each other and I ended up steadying myself by firmly gripping her waist as we both teetered on the edge of tumbling down the stairs. We managed to regain our balance, laughing a bit awkwardly. I looked at my assailant and my jaw hit the floor; Lily was wearing nothing but a matching set of mauve underwear, her panties capped with a tiny bow that mirrored the one displayed between the cups of her bra. I had never seen her in anything less than fully dressed before and she definitely knew it by the way her face was turning beet-red.
Lily swiftly pulled away and ran back up the stairs yelling “Sorry I thought you were at work!” I attempted to respond but was distracted by the sight of her panty-clad butt as it jiggled slightly every time she took a large step up. At my angle, I could just barely see her mound at certain stretches in her gait. It was over too soon with her shutting their bedroom door with a snap. “Sorry!” came the muffled and embarrassed apology from behind the door. “It’s fine,” I replied. Then I added before thinking “as if I’d complain about that.” She laughed, thankfully, and I retreated to my room.
That was the start of it, really. She was more than just Peter’s girlfriend now, or my fiancee’s frenemy. I couldn’t get her ass out of my head, or the way the smooth skin over her hips had felt when I gripped her waist. It might have been my imagination, but Lily seemed to be going out of her way to hang out with me when we were home alone as well. She usually spent most of her alone time locked up in their room, but if I was downstairs she would set up and paint her nails nearby, or share some funny cat pic she’d found on the web. I wasn’t in any danger of cheating though despite what you may think. In my head, I was stubbornly the good guy and would be loyal to Jessica no matter what happened.
Of course, I’d been doing a lot of self-servicing, usually in our bedroom or bathroom (we had a separate one to Peter and Lily). Jessica wasn’t getting any warmer to the idea of sex despite a myriad of possible solutions I had spent the time coming up with, so it was really my only option. Interestingly enough, I heard around about that time that Peter had a low sex drive too. It wasn’t difficult to do the math and realize that Lily shutting herself up in their room might be for the same reason I did.
I had to know. The concept of Jessica masturbating was so foreign that, in my head at least, Lily couldn’t possibly be spending all that time in their room touching herself. One day, when I was home alone I snuck into their room, my heart hammering in my ears as I strained to listen for any sounds indicating someone coming home. I didn’t know how long I had. Their room was tidy apart from some clothes and books and such on the floor, a stark contrast to my usual messy bedroom. I was extremely careful to place everything back where I found it, but when I found the exact same set of mauve panties Lily had been wearing weeks ago on the stairs, I had to pick them up. My hands were shaking with excitement and nerves. I’d never had an underwear fetish, but there was something incredibly sexy about knowing she had worn them. Feeling my hard on growing against the constraints of my pants, I realized I could smell pussy from them a good foot away from my face.
I put the panties back, hopefully exactly where I had found them, and continued my search. To my great surprise, I stumbled on a drawer that contained a vibrator and a dildo (along with condoms and such). As I said, Jessica found the concept of masturbating weird, so finding ‘advanced’ toys like these was pretty unexpected. The dildo hadn’t been cleaned properly after its last use and had a slight white discoloring around the end. I caught myself on the verge of picking it up, suddenly disgusted with how pathetic I was being. I left the room quickly, and such was my guilt that I didn’t even feel an urge to jack off.
That was my first and last invasion of Peter and Lily’s privacy. The situation remained the same, with both of us spending a fair amount of alone time behind closed bedroom doors, though I did listen hard whenever I passed their room for any faint buzzing sounds.
One afternoon, a couple of weeks after my espionage, I was sitting on the edge of our bed gripping my dick with one hand and trying to get off without imagining Lily at all when there was a soft knock on our door. For some reason I still can’t comprehend, I thought it would be best to respond with “yeah?” The door opened, and Lily stood there in her white dress, just a hint of cleavage on show but more than 80% of her legs displayed. For a few seconds that stretched out forever she was frozen, mouth open, wide eyes locked to the semi-hard-yet-deflating-fast cock in my fist – then she closed the door.
Shit. Shit shit shit. Why did I fucking say YES to her knock? FUCK!
I had never been so embarrassed. I quickly got dressed and went looking for Lily to apologize, but couldn’t find her.Shit! I tentatively snuck up the stairs towards Peter and Lily’s bedroom, ready to knock and apologize, but stopped when I heard something from behind the door. Moaning! I moved as close to the door as I dared, head turned to the side. I couldn’t hear much, just some soft rustling movements and – Lily groaned from the other side of the door, a long, low, fucking sexy noise from deep in her throat. I stayed and listened until the noises stopped then retreated to my bathroom where I came like a volcano into toilet paper.
I ran into Lily downstairs an hour or so later and she apologized to me for walking in on me. It turned out that Lily and Peter had another one of their arguments and she had wanted to talk with someone about it. Our whole conversation Lily was shyly looking at her knees, which were pressed tightly together. We chatted about their argument until she had vented. Apparently, Peter had been trying to get her on the pill as a way to moderate her sex drive, but she hated the pill as it did weird things to her moods. Even though Peter is a good friend, I sided with her and said, “Hey, it’s your body, right?”
She nodded, “Thanks so much for listening to me vent.”
“No problem,” I smiled at her. I picked up my car keys. It was time to pick up Jessica from work as we had dinner plans. She still didn’t have her license. As I left through the front door, I looked back at her and said laughingly “I’m really sorry for the miscommunication. I don’t know why I said ‘yes’ to your knock.” I grimaced wryly. “I don’t think I was thinking too clearly.”
Lily looked up at me, pink lips in a bow of a smile. “It’s fine. As if I’d complain about that,” she said, throwing my words back at me. I closed the door. This was getting dangerous.
After that day, whenever we were home alone together, Lily and I were on good terms, though I kept my guard up. I’d be getting married in just 6 months’ time, I couldn’t make any stupid mistakes. She would confide in me and confirmed to me that Peter had an abnormally low sex drive. She kept bringing the topic up and hinting that she found it frustrating (with strong emphasis on the word frustrating) so she completely understood my need to ‘take care of myself’. She was endearingly obvious about trying to make me feel better about her walking in on me. We were both putting the dishes away while we talked, Lily in her white dress she so often wore around the house. Every time Lily bent over or reached up, I watched as the dress slide up those thighs until I could catch a glimpse of the slight curve at the bottom of her ass.
“How often do you… touch yourself?” Despite the way the conversation had been going, Lily’s question still caught me off-guard. I answered in what I hoped was a detached manner. “A few times a week, I guess.” She continued stacking dishes under the counter, dress covering her properly at the moment. “What about you?”
She stood upright, brushing a stray hair from her eyes. My eyes snapped to hers from where they had been looking. Suddenly the few feet between us felt inadequate. “About the same,” she smiled, seeming very confident and unembarrassed for someone a few years younger. I guess she’s more embarrassed by running into me in her underwear then talking about fucking herself with a dildo. I changed the topic, and nothing else of consequence was really discussed, just a few more minutes of friendly conversation.
Something changed, though. It definitely was not my imagination that I could hear her whenever she ‘relieved herself’ as she put it. Maybe she just felt more comfortable now our maintenance habits were out in the open. I heard moans, vibrating, bed springs (though not much of those) and the occasional ‘fuuck, I’m cummming” from Peter and Lily’s bedroom. This last sound was pretty awesome. Jessica had never had an orgasm. I didn’t make any more noise myself (I blame ten years of fapping like a ninja). After a week of this, there were a couple of instances where Lily would come downstairs in her underwear then apologize and go back upstairs, saying she thought nobody was home.
The third time this occurred, Lily was wearing her mauve set with the little bows, so I couldn’t help but peek out from the room I was in to watch her retreat towards the stairs. The panties weren’t exactly a G-string but they still showed off half of her ass as she walked up the stairs. My dick was rock hard and throbbing and I felt the same shaky excitement I had felt weeks beforehand. She turned as she went up and grinned at me.
“Sorry. I understand if you need to jack off, I’ll stay upstairs for a bit,” then she disappeared around the bend up the stairs. There was something incredibly arousing about the situation, the thought of jacking off downstairs in the common area while Lily was upstairs, likely finger fucking herself to a vision of me. So I did it. I sat on one of the dining table chairs, slipping my pants to the ground and felt how swollen my cock was, stroking slowly with my eyes closed. I wasn’t going to last long; Lily’s ass as she walked up the stairs was a fresh vision behind my eyelids, her mound covered tightly by satin with creases hinting at her lips. As I neared my climax, my eyes opened and I saw Lily standing on the stairs, hand making a small bulge in her dark panties as she moved it circles. I gripped harder and stroked as hard as I could, an involuntary groan escaping my lips as I started to cum all over my hand. Still stroking, still cumming, I watched as Lily’s knees trembled and she partially collapsed against the wall.
I sat and she stood, staring at each other, chests heaving. Then I went to clean up, and she was gone when I came back.
I felt horrible for a couple of days, completely avoiding conversation with everyone in the house. Peter and Jessica joked that I was just upset my team lost (I’m an NFL fan). Lily didn’t correct them or go along with it, but let me have my space. I was getting married. I loved Jessica. What the fuck was I doing? So were my thoughts for days, until I came to the conclusion that it wasn’t cheating. I mean, we hadn’t even touched each other.
The next time I spoke with Lily alone she attempted to apologize to me for coming down, but I cut her off.
“It’s fine. I probably wouldn’t have been able to resist if I were you. And besides, I’m no saint myself.” We were in the computer room, her standing in blue shorts and a white sports top with me seated at my desk. Her dark purple sports bra was visible through the shirt.
She looked at me quizzically. Damn, she’s cute, I thought. “What do you mean?”
I felt I had to come clean at this point, she looked really apologetic. I told her about going into her room when I was curious about her masturbating, explaining that Jessica has never so much as had an orgasm and was more put off by sex than aroused by it. I expected her to be furious, but her only reaction was to blush a bit. “We’re even then?” she said with a cautious smile.
“Even,” I confirmed, returning her smile. “We’re in a tough situation, and maybe it’s not their fault, but our partners aren’t exactly meeting our needs for us. We didn’t cheat or anything.”
Lily nodded emphatically, then went and sat in her chair. “Yeah, it’s not cheating if we don’t even touch each other.”
Some time passed with us doing our own things, my dick annoyingly hard but hidden underneath my desk. She sat to my left browsing the internet when she suddenly said “I think I need to relieve myself again,” laughing. Cue chest pounding like a drum. I should have left the room to give her space or suggested she go upstairs. But it had already happened once, and it wasn’t cheating if we didn’t touch each other.
“Go ahead,” I replied, barely managing to keep my voice steady.
I couldn’t see much while pretending to continue working, but from the corner of my eye I saw one hand snake under the blue waistband of her shorts and she sighed. I stared furiously at my work, reading the same sentence over and over again, while I heard her movements gain some urgency and a wet schlock-schlock sound begin to emanate from her direction. My peripheral vision caught that she seemed to alternate between her wrist moving in small circles, presumably rubbing her clit, and steady flexes when she was penetrating her cunt or stroking up and down. It was so easy to imagine going over there, sliding my hand down beside her own and feeling how wet she was.
My cock was straining hard against my own waistband, but I managed to continue to face forward. When she was finished, she withdrew her hand from her shorts.
“Thanks,” she said, sounding pretty out of breath. “Sorry about that.”
“I am so fucking hard right now,” I replied, turning my chair to look at her and not thinking about my words until they were out. Instant regret. She blushed but smiled at me. “Maybe you should have joined me,” was all she said before turning back to her computer.
Maybe I should have.
After that, whenever Lily needed to orgasm and we were home alone, she would just do it. On the couch watching TV, I’d hear her moaning and rubbing herself furiously. Occasionally (all the time) I would walk past and ask her if she was having fun, to which she would just moan something along the lines of “fuck yesss”. It was driving me insane. I exited the computer room one day, wondering where she was until I heard moaning from the staircase. As I turned the bend, Lily’s pussy was not two stairs above and in front of me.
She was wearing her white dress, panties pulled to the side while kneeling on the stairs. She was facing the top so hadn’t seen me, but had her left hand gripping her dress while her right was back between her legs. Her middle two fingers were plunging in and out of her pussy while her lips tried to grip them. She looked really tight.
I took one step backward then stopped, taking in the sight and listening to Lily moan. Her forehead was pressed into one of the top stairs. As quietly as I could I pulled out my cock, already hard. I felt like I could cum at any second. It was good I had taken a step back from her as I felt like I could shoot several feet in my current state. It’s not cheating if we don’t even touch. I started rubbing my cock up and down, pulling the skin tight on each downstroke. Lily moaned again, turning her head to the side and looking back at me past the hand that was gripping the white skirt of her dress. She saw me. She fucked herself harder with her fingers.
I have no idea how I didn’t cum right then, but I somehow managed to hold it. I increased my pace slightly, watching her fingers disappear into that tight fuckhole with soft wet squelches. A thought came to me that it would be really hot to jerk off onto her ass though I wasn’t sure if she would be ok with it. Cum, while not technically a part of me after it leaves my body, might still be stretching the ‘not touching = not cheating’ rule. Thankfully, I remembered that she wasn’t on the pill so I would have to be extremely careful not to get any near her pussy.
I took a step closer. Her knees were only two steps above me now, and her body was angled down slightly so I could see everything perfectly. I felt my cock throb as I jacked off, unconsciously pointing it in a perfect line towards the fingers going in and out of her vagina. Her panties looked like they were soaked from the shrapnel of pussy juice.
One step closer. My cock was about six inches from her pussy and I felt close to cumming. I aimed up slightly, towards her ass, but kept my eyes glued on her fingers. I was going to cum all over her back and dress. Then she pulled her fingers out of her snatch with a pop, panties moving to half cover up her slit. I hesitated, looking at her face. She was breathing hard, still resting on a cheek on the stairs above. Her eyes looked at me for a moment, then closed and a second later she was rubbing slow, hard little circles on her clit. Her other hand hiked her dress skirt up further revealing her ass in its entirety, and she pulled her panties to one side like… like an invitation. Blood from my head rushed elsewhere. I felt like I was going to faint. We were both breathing heavily, almost gasping with how turned on we were.
My cockhead was 4 inches away from her pussy. I could feel the warmth radiating from it. What happened to angling up? A part of me wondered, but it was a small, quiet part. I could cum all over on the surface of her cunt and it wouldn’t matter. Her hand switched from circles to roughly rubbing up and down her clit with her fingertips. I thought I could see her pressing harder as I got closer, breathing more raggedly. Her vagina was soaking wet and pink and pulling taut as Lily frantically rubbed her clit just above the entrance to her tunnel. I could barely resist taking the last step up and shoving my cock in. Suddenly her butt started clenching spasmodically and I saw her vagina start to clench in orgasm. Lily let out a deep groan, and without thinking, I took the last step up, lined up my cock, and touched the tip to her still clenching cunt hole.
“FUCK!” Lily moaned, and pushed backward, impaling herself a good halfway down my cock. She felt tight, tighter than Jessica, and still clenching in orgasm around me as she froze with surprise. I had never felt a girl cum before. I groaned in primal need and pushed the rest of the way into her, forcing her face and shoulders into the stairs above. Her cunt relentlessly milked at my cock, massaging me in ways I had thought impossible. I pulled out, then fucked into her again, my own orgasm overtaking me, drowning my thoughts in waves of pleasure. Cum burst from my cock, splashing over her cervix in an amount that felt like it would fill her entire pussy. My orgasm continued for the longest time, all the while Lily making mewling noises and lightly fucking herself on the end of my dick.
Finally, I pulled out. Seeing the white cum drool out from her vagina onto the stairs would give me nightmares for the next few days, even though I bought her a morning after pill later that afternoon. “Fuck,” Lily sighed with content, still with her face pressed into the stairs awkwardly, and we both laughed a bit. What else can you do, when you’ve fucked up your life?
I felt a huge amount of guilt. Eventually, Jessica and I broke up, but not before another half a year living with Peter and Lily. That’s another story.