When I was in my late 20's I met a young nurse who worked at the community Crisis Center. I volunteered there one night a week, after my regular day job. We dated for a while and got along well enough. Neither of us was in a relationship at the time, so the arrangement was very convenient. She ended up moving out of her parents' house and getting her own apartment, which worked out great. I started staying at her place a few nights a week, and eventually our friendship turned sexual, as sometimes happens when two young adults end up naked and sharing the same bed together.
Things seemed to be progressing fairly smoothly, although I don't think either one of us was actually in love with the other one, although we both admired each other. It was pretty much a "friends with benefits" type of deal. But when it came to sex, things were a little complex. She had a religious conflict about the topic, and it seemed like her parents were constantly in her head as well. She refused to go on the pill, because both her religion and her parents frowned on premarital sex, and using birth control was forbidden. She was torn between maintaining her "good girl" image and satisfying her natural sexual needs. But she didn't want to put herself at risk of getting pregnant, so she compromised: If we were to engage in sinful intercourse, at least I would have to agree to wear a condom. And as an extra layer of protection, she would use anti-spermicidal foam as well. (Porn Stories)
I must admit, the idea didn't excite me, but I figured it was better than nothing. When we first started out trying her method, it was a nightmare, to be honest. We would kiss and caress and fondle and do all the things necessary to achieve arousal. It wasn't all that easy when you factor in the realization that we really weren't all that into each other in the first place. But we soldiered on, and when it came time to perform, we separated and attempted to do our individual parts and then put it all together in a well-timed, grand performance.
Only, it didn't quite work out that way: as I located the condom on the dresser in the dark room, tore open the package with my teeth and began unrolling the contents onto my erection, I could hear her reach for her can of foam, shake it up and apply some to her hand and then down between her legs. Usually, by the time we were prepared, I would climb on top of her (our repertoire mainly consisted of the missionary position), and by then my sagging manhood could barely support the condom. No penetration: game over. Other times when our preparatory efforts were quick and well synchronized, I would mount her successfully and pound away repetitively for fear of losing my hard-on yet again. Only this "success" was short-lived because of the awful, putrid smell caused by the friction and subsequent heat that would result from my synthetic rubber condom repeatedly coming into contact with her foam. The ensuing odor was just overpowering and reminded me of burning tires.
So, it was one turn-off after another for us. On top of that, I truly believe she willed herself to prevent having an orgasm. I think she felt guilty and unworthy and could not allow herself to feel any pleasurable sexual payoff from our rare triumphs. She wasn't supposed to be having sex at all, she reasoned, so she damn sure didn't deserve to enjoy an orgasm; perish the thought. Hell, one time after a particularly frustrating encounter, I suggested perhaps we could try anal sex, thereby avoiding the whole protection thing altogether. She shot flaming daggers from her eyes that penetrated my very soul; like I had told her she should have sex with Satan himself. End of discussion: we will not only forget that I even mentioned anal sex, but we will heretofore refrain from even considering such a filthy, dirty, heinous act now and in the future. How dare I??
She abruptly turned away from me and that was that. I lie awake for a while longer, silently seething as I heard her gentle snoring begin: she passed out almost immediately, and that pissed me off even more. Feeling defeated and a bit defiant, I rolled over on my side and faced the back of her body. We usually spooned each other and I didn't see any reason to deny myself the sensual pleasure of pressing up against her naked body on this night. I had to give her credit: at least she always went to bed in the nude. I had read that only 4% of women actually did that on a regular basis. Even though I was rather frustrated and discontent, I began caressing her hip and leg, up her side, and her shoulder. She was so soft and smooth, I found myself getting aroused just from touching her bare skin. I leaned in and took a deep breath, inhaling the sweet scent of her hair.
Perhaps because of our sharp disagreement earlier, my attention gradually focused on her ass. It felt so nice and tight and round and firm under my fingertips, and I noticed she didn't budge at all, despite my caressing and gentle squeezing. Emboldened, I began running my finger ever so delicately up and down her crack: still no reaction from her, other than a more pronounced snore here and there. I was intrigued. At that point I reasoned that I really didn't have much to lose, so I went a little further. I tried parting her ass cheeks ever so slightly with my thumb and finger. No resistance. I opened them a little wider and I was amazed that she didn't seem to notice at all. Instinctively, my index finger zeroed in on her forbidden entrance. I gently twirled it around the outer area and I was kind of surprised to find it a bit slick to the touch. Finally, I went for it, thinking 'risk/reward' all the way, and I entered her anus with the very tip of my finger. It met with little resistance. There was no tightness, no clenching. I figured it was because she was so out of it; she was totally oblivious. Again, I was surprised that her rectum was so moist that my fingertip was able to slide in so easily. Then again, we did just try to have sex earlier, so it wasn't a complete mystery that she was moist and damp between her legs.
By now, my cock was raging hard, which was a welcome realization after experiencing so much limpness of late. I moved my finger in and out ever so slightly, not wanting to tempt fate at this point. It felt so hot inside her ass, like it was on fire in there! Finally, I reluctantly slid my finger out and rolled over onto my back. My manhood stood straight up and I couldn't help but wrap my hand around it and pump it like mad. I didn't care if she was aware or not, but I decided to beat my cock until I came. The only thing that surprised me was how I turned onto my side just as I erupted, and I aimed it at her ass. By the time my sexual contractions subsided, my semen was running down her ass, and I frantically directed it to her ass crack, lest some of it seeped down and somehow got into her vagina. I rubbed it all over her ass and used my finger to make sure some of it got into her rectum. I rolled over and nodded off, satisfied and excited about the future.
The next morning, I awoke to the sound of the shower. She started her job earlier that I did, so she always had her shower done even before I got up. I thought of what had happened the night before, and it hit me that I had never cleaned her up before I passed out. I panicked a little and waited to see if she had any reaction. I hopped out of bed, put my robe on and got the coffee going just as the shower stopped. I poured us each a cup and sat at the table waiting for her appearance. She exchanged 'good mornings' but little else. She seemed to be in a chipper enough mood, so I just remained rather quiet as I looked for any sign from her. Nothing. Next thing I knew she was dressed and ready for work. She kissed me on the forehead and disappeared out the door. So I finally exhaled while I pondered our situation.
Sex had become so unsuccessful between us that we didn't even try all that often. Some nights we just spooned and cuddled, which I didn't really mind, to be honest. But the night after I had stealthily penetrated her virginal rosebud, I could hardly contain my enthusiasm as we climbed into bed. It didn't take long before she was out, as evidenced by her soft snoring. I waited for a reasonable amount of time, content to just caress her smooth curves as I lie next to her. But as I became more and more convinced that she was in a deep slumber, I zoned in on her ass once again. I will admit I had devised something of a plan: anticipating that she might not be so damp down there this time, I had procured our sex lube beforehand, and smuggled it under my pillow.
After several minutes of gently playing with her ass and teasing her crack, I retrieved the lube and squirted some on my finger. I spread her cheeks with my other hand and started applying the slick gel around her most vulnerable opening. My fingertip slid in up to the first knuckle with ease. I kept it still for a minute or two to make sure she was completely out: she didn't move a muscle, nor did her calm breathing pattern change in the least. Finally, I slowly pushed my finger deeper inside her hot, dark tunnel, stopping at the second knuckle. My heart pounded with lust and thoughts of forbidden pleasure. My head ached and my cock throbbed in anticipation.
I started fucking her ass with my index finger, gently but firmly. I couldn't believe she didn't move, or make some sound, or actually wake up while I violated her body. Finally, I buried the entire length of my finger up her tender rectum, as far as it would go. Wow, was she hot in there! Of course, I was getting more and more aroused and brazen as well. I pulled my index finger out and replaced it with my middle finger. Her naughty passageway was downright slippery by now, and my middle finger immediately penetrated her to the hilt. I finger fucked her with some authority for as long as I could stand it. But I couldn't hold back much longer. I removed my finger and pressed my hips in close enough so that my screaming prick rode her crack up and down, contacting the slick lube with each pass.
I would have liked to have continued the motion for hours, but my cock was near explosion. This time, instead of cumming all over her ass, I made sure the head of my dick was nestled in between her ass cheeks, and I pumped her crack full with my hot offering. I couldn't remember ever having such an intense orgasm in my life, and I hadn't even actually fucked her. So, while I busied myself with pushing as much cum as deeply into her rectum as possible, I wondered why this particular climax had felt so good. I supposed it was a combination of things: her obvious disdain for anal sex which she had made very clear; the fact that I was guilty of taking advantage of her, obviously without her consent; the feeling of justification I got from exacting some type of revenge for her insisting on her fateful combination of birth control methods; but mostly it was just so naughty and so taboo and so fucking hot…
Once again, I didn't attempt to clean her up. I wanted to know if she would notice anything in the morning, after not mentioning anything last time. But again, she took her shower without incident, and she said nothing about it to me. She was as sweet as could be, and she actually seemed more agreeable and satisfied with our relationship of late.
After she left for work, I felt a certain smugness about the situation. I couldn't wait for our next opportunity. I went to work and fantasized about the next steps I would take with her. I couldn't wait to be next to her in bed again. Things felt almost too good to be true. Maybe ours wasn't the best example of successful sexual relations, but it was secretive, exciting and ultimately rewarding, at least for me: I got to play with her unmentionable sexual orifice and ultimately achieve tremendously satisfying orgasms, while she really didn't have to go out of her way at all. And it's not like I was denying her any pleasure, seeing as how she never climaxed anyway.
So you could say that I was feeling confident, if not complacent as well. At bed time we did our kiss goodnight routine and she promptly rolled over on her side, once again presenting her ass for me to take advantage of. I wasted no time with my preparation ritual: cuddle, caress, gentle touches as I awaited that familiar first snore which signaled her meeting with the Sandman. As usual, I directed my attention to her young exposed bottom. Just rubbing it got me aroused immediately. As I began my finger teasing, I realized that I forget about the lube, stupid ass that I was. I didn't want to risk waking her by getting out of bed, so I came up with a brilliant Plan B. It was something I had been thinking about doing anyway, but it felt riskier than anything I had tried so far: I scooted down ever so slyly until my face was even with her sexy ass. I was immediately crazed with lust. Just the thought of licking her most intimate area got me so worked up I thought I might faint. But I managed to persevere.
Slowly I spread her cheeks wider and wider with both hands until I had enough room to get my tongue in there. I gave her tender knot one quick lick and waited for a response. She didn't move. She just kept snoring peacefully, so I licked her some more. Soon enough, I was pushing the tip of my tongue through her opening. I tongue-fucked her and sucked on her asshole until I couldn't go any longer, but I made sure her entire area was sufficiently covered with my saliva before I crawled up to my usual spot behind her. I started my finger action, switching back and forth between my index finger and middle finger, getting them both wet enough for my newest intrusion. I monitored her for any signs of waking, but she remained dead to the world. The only thing I detected was what might have been a slight change in her position: she seemed to have pulled her legs up against her chest tighter than usual. But I figured it may have just been wishful thinking on my part.
Nevertheless, I proceeded cautiously: as I continued to switch fingers, I slowed down enough to see if I could squeeze both of my fingers into her anus at one time. I went as slowly and as gingerly as possible, but it really wasn't all that difficult. Again, no resistance at all. By the time I had managed to push them in tandem as far as they would go, I thought the head of my cock might explode, I was so excited. I guess my rampant enthusiasm cleared the way for me to start ramming my two fingers into her as hard and as fast as I could, leading up the my final act of ejaculation. I reluctantly pulled my fingers out and spread her ass cheeks as I pushed forward and started working my shaft up and down her crack. I was moments away from ecstasy, oblivious to my surroundings and confident in my expectations, when all of a sudden I felt the blankets flying off the bed in one motion, and heard those unexpected words I had dreaded:
Oh my god, I thought: busted!
I believe my heart stopped momentarily, and I couldn't breathe. I was in shock. I hadn't seen this coming at all. I was immediately drenched in sweat and I could feel the color drain from my face. Everything was a blur amid the flurry of activity that ensued. When I my eyes finally cleared, I looked over to see her perched in the middle of the bed. She was up on her knees with her ass pointing towards the ceiling. Her head was on the bed, covered by her pillow. She said nothing else, but I could see that her arms pointed back and she had an ass cheek in each of her hands, spreading herself as widely as possible. If ever there was an easy interpretation of body language, this was it. I took my place in silence, kneeling between her open legs. I rubbed my trembling shaft up and down her exposed crack a few times, but she shook her ass at me in defiance:
"FUCK ME NOW! JUST PUT IT IN ME AND FUCK MY ASS!"
She wiggled it as if she wanted to make sure I knew what she was referring to. I was happy to oblige, even though I hadn't quite overcome the initial shock of it all. As I prepared to mount her ass for the first time, and apparently with her permission as well, I couldn't help but wonder how much she actually knew about my recent activities. She may have known what I was up to all along. I'm sure she would fill me in later, but for now, it was time for me to fill her up.
I pushed my cock past her sphincter muscle with surprising ease. No longer silent, she oohed and aahed my every move, inhaling sharply one second, and then exhaling with the same intensity. When I finally managed to get most of my cock buried in her ass, she pulled each of my hands from her hips and positioned them on either side of her ass crack. Once I got the message to take over for her, I eagerly spread her as wide as possible and began to fuck her ass hard and deep and with unabashed fervor. I noticed that one of her hands slipped under her head that remained hidden by her pillow, while her other hand reached down between her legs: the better to finger her quivering cunt.
It was the first time I had ever seen her touch herself sexually. Obviously, it was a sinful practice too, but this time she had other ideas. Seeing her make an attempt to derive pleasure from our sexual encounter for the first time got me even more excited. I pulled out of her in midstroke, causing a cry of disappointment from her until I stood up on the bed and straddled her hips. I re-entered her gaping anal canal and buried my entire shaft until it completely disappeared inside her lithe, shuddering body. I continually banged down into her and my strokes got rougher and more pronounced with each new thrust.
"OH MY GOD, OH CHRIST, OH JESUS AND THE TWELVE APOSTLES!"
Her religious litany spewed out of her mouth in rapid fire.
'FUCK ME! FUCK ME! OH FUCK YES; FUCK MY FUCKIN' ASS!"
Her filthy dirty exclamations served to rile me up even more, and I redoubled my efforts, pounding her totally exposed anus into oblivion. I was pleased with my staying power; maybe I was trying to prove a point, I don't know, but I could tell that I was getting close, and I wouldn't be able to hold off much longer. And then, she provided me the distraction I needed to continue for a little longer:
"OH YES! OH MY GOD YES! I'M CUMMMMMMIIIIIING!"
Her entire body shook like crazy as she fingered herself to frenzy. All I could do was hang on for dear life and try to keep up my end of the bargain for as long as possible. As she finished, she collapsed flat onto the bed with my cock still inside her ass and her hand still between her legs. It was my turn now:
"HERE I GO TOO, ARE YOU READY?"
Just as I was about to pump her ass full of my cum, she surprised me again:
Somehow she managed to break free of my cock and spin around to face me in one swift maneuver:
"Cum in my mouth! I want to taste your cock!"
I didn't need to be told twice.