We had been lovers for at least six months. I loved his demanding passion, and he clearly loved my neediness. We usually fell into each others arms the moment he walked through the door, and most of the time we were screwing long before we made it to the bedroom. The sofa and chairs in the living room, the floor in every room, kitchen table, washing machine, shower, bathroom sink...we landed on whatever was closest.

He likes to fuck hard, and he has great stamina, so we go for hours sometimes. I love the way he pounds my pussy until it hurts. I love that every time I move for the next few days, I still feel him between my legs. We usually go through two or three positions in the location where we land before we come. Afterwards, we wander into the bedroom and lay wrapped in each others arms, and usually end up fucking again before falling asleep.

I absolutely love sucking cock, which he realized pretty quickly. If he put his cock anywhere near my lips, I was salivating. He was more than happy to stick his dick in my mouth almost every time we were together, and he loved to stare into my eyes while I sucked his prick and his balls.

He finger fucks me like no other man ever has, and while he doesn't do it every time, he does sometimes like to cum on my body, my face, and in my mouth. I love that, too. It is so incredibly erotic to watch him start to spurt and to feel his creamy, sticky load coat my skin or fill my mouth.

However, there was one thing that he wanted that I simply could not seem to manage. He wanted to (in his words) "fuck me in the booty." He put his finger in my tight asshole frequently, and while it did hurt at first, he knew exactly how to distract me by tweaking my nipples or slamming his dick into my cunt really hard and deep. I loved the idea of him filling my ass and pussy at the same time, and I soon learned to love feeling his finger inside me that way.

He tried repeatedly to stick his dick in the same way with little success. As much as I wanted to please him, I was really afraid. He tried to be gentle. He lubricated himself well and placed the tip of his cock against my asshole, and worked it gently, stretching me a little at a time. He tried to be a more assertive, lubing it and telling me to relax while he tried to just push his way in. That might have worked if he had been less considerate, but he wanted me to like it, and each time he tried it like that, I panicked. He bent me over the bed and when that did not work out, over a chair. He laid me down and put my legs in the air, and when that was unsuccessful, put me on my hands and knees doggy style. He tried to make me feel more in control of the situation by sitting down and having me sit on his dick as if I were sitting in his lap. Pain again, and panic.

He was wonderful through all the attempts, patient and gentle and reassuring. He insisted that I just needed to relax to enjoy it. I tried to relax, but as most people realize, when you "try" to relax, you do not. I was frustrated and annoyed with myself. I wanted to do this because it was clearly important to him. However, I am a wimp when it comes to pain, so the whole situation seemed to be a catch twenty two.
Most nights, he sleeps on his back, and he always pulls me over to lay my head on his chest, then wraps his arm around me, and we usually stay positioned that way. We usually wake up sometime during the night, entangled, and fuck again before falling back asleep. Then, in the morning, when we wake up wrapped around each other again, by the time we stretch and move around a little, he is hard again and I'm all wet, so we end up fucking one more time to start a new day.

One night, after another failed attempt at the booty, I woke up entangled with him as usual, but this time, we were laying on our left sides spooned together sensuously. I started to adjust myself a little to get more comfortable, and as is his habit, although asleep, when he felt me move, he immediately tightened his arms around me and pulled me closer. He likes having me tight against his body, and I love when he holds me that way because I feel confined and protected. Due to the sleep position being unusual for us, I was a little confused when I felt his dick against my ass. He was still mostly asleep, so although I could feel movement against my butt, as if he were slightly aroused, he was not fully erect. He was pressed into the crevice, and I could feel the length of him with the head an inch or so away from my pussy.

It felt pleasant, and I started to wriggle slightly, adjusting myself against him. His dick began to stiffen, and I started to kind of grind myself against him gently with a slow, steady rhythm. It felt sexy and sensual, but very relaxed, the feeling of his dick so close to my pussy, his body so close to mine, and his arms holding me so tightly. Neither of us was fully awake. We were groggy still, and content from the prior night's lovemaking.

I felt his cock stiffen as he matched my rhythm and pressed more tightly against me. He stroked me absentmindedly, softly and gently with his fingers. It was very erotic to me - the contrast of his gentle, endearing touch, so different from the demanding, rough pulls and grips of the night before. He slipped his fingers down to my pubic mound and continued his soft gentle strokes, no pressure at all, just light, feathery brushes across my skin.

I felt a twinge between my legs. Deep in my cunt, I felt the start of that familiar ache. I jutted my ass back against him, attempting to position my pussy against the head of his cock. He responded by pressing himself into me closer, and moving his fingers to my labia. He continued the soft feathery strokes around the folds of my pussy lips. He teased his way up and down, strumming and brushing his fingers against me slowly, never parting the lips, never moving to my clit, and it was deliciously maddening.

I could feel myself melting, liquid starting to flow from my yearning cunt. I pushed myself against him and tried to wiggle my pussy onto his now stiff dick. He remained still, letting his pulsing, hard cock rest between my ass cheeks, and moved his other hand to my swollen, puffy nipples. I have big tits, 38DD, and fat, rose-colored nipples that are extremely sensitive. I can come just from having my nipples touched, and he knows exactly how to turn me into a writhing, begging little slut by playing with them.

He moved both hands to my tits and began brushing the palms of his hands, then his fingertips, across my nipple tips. As I began to grind my ass against his cock, he took my nipples between his thumbs and forefingers and began rolling them gently. As I started to squirm even more, he began to pull and tug on them softly, allowing them to pop loose and kind of bounce free every few minutes. He alternated the plucking and pulling with flicking his fingers against the sides of each nipple rapidly but lightly.

The feelings that coursed through my body were exquisite, but the ache in my cunt had become an intense craving, and as the muscles inside tightened and squeezed involuntarily, the churning sensation made me squirm. His cock had hardened and I could feel it against me stiff and pulsing. I wanted to feel it inside me instead, plunging and filling me full. I arched my back, and reached my arms back over my head to wrap my hands around his neck. He nuzzled against me, breathing into my ear, alternately blowing lightly and running just the tip of his tongue around the orifice.

He also had started to alternate the gentle flicks against my nipples with periodic pinches, jarring my senses and making me moan. I pushed my body against him desperately, needing to feel him in me. He spread my pussy lips with his fingers and dipped just the tips of his fingers into the edge of my twat. He pressed there, just inside the edge of the opening, teasing in and out from the swollen, wet inner walls to the puffy, outer lips, wiggling his fingers just enough for me to feel the motion.

My body was on fire and aching for cock. I needed to feel his thick hard dick in me. I wanted him, and he knew he was making me crazy. As I moved against him, he continued to toy with my body, flicking and brushing my nipples, circling just inside my pussy with his fingertips only and licking and kissing my neck and shoulders. He started to press his cock against me, and I responded by grinding my body against him.

He worked his cock against the lips of my pussy from the rear, dipping slightly into my wet, dripping cunt, then suddenly plunged his fingers into it from the front instead. I didn't care how he did it, I was just grateful to feel something filling the emptiness between my legs. Just as quickly as he had pushed his fingers deep, he pulled them back out and began to play them around my clit. I felt like screaming in frustration.

However, he began dipping the head of his cock into my wet pussy and then sliding it back to my ass. It made my body quiver. I pressed against him, wanting his dick inside, needing to feel him in me. The head of dick was coated with the wetness from my pussy, and as my cream had oozed out, he had used his fingers and cock to smear the slippery natural lubricant around on my inner thighs and the crack of ass. He pressed his wet, throbbing dickhead against my tight asshole, and continued to stroke and rub softly against the lips of my pussy and my shaved pubic mound.

He did not increase the speed at all, even though he could feel me straining frantically against him. He continued to finger me slowly and gently, teasing my body mercilessly, and although I was aware of his cock pressing against my asshole, my attention was focused on the feelings flooding through my nipples, clit, and cunt. Even though the movements of his fingers were slight and measured, my erect nipples and distended clit throbbed and pulsed. He continued pressing his dick into my ass with the same slow steady rhythm.

I was beyond any thought other than fucking. I had become his little bitch in heat, wiggling, twisting, and writhing to get his dick inside. Position was irrelevant, I just needed cock. He inched his cock into my ass, pressing steadily but slowly and continued to finger softly around my clit. As he further penetrated my virgin ass, I stiffened as I became aware of the pain as his thick dick stretched me open. He immediately thrust his fingers into my creamy cunt and continued pushing his stiff meat further into my tight tunnel.

His fingers made me crazy. He knows that when I get really wet, I love the way he finger fucks me. He shoves three fingers in me deep and hard and thrusts and plunges in a way that makes me feel almost like I'm being fucked with a cock. He held my pussy cupped in one hand, thumb pressed close to my clit, fingers digging relentlessly into my dripping wet cunt. The muscles in my pussy squeezed and contracted with pleasure as he shoved his fingers in and spread them slightly, then withdrew to the tips only to ram them in deep again.

As he fucked my sopping wet twat with his fingers, he continued to work his rigid cock into my asshole. I felt the intrusion, but his fingers, which he was now alternately using to thrust into my wet, gaping cunt and brush and pluck my fat swollen nipples, had me so excited and stimulated that it was simply a subconscious awareness somewhere in my mind.

The distraction worked exactly as he intended, focusing all my energy to that burning ache between my legs deep in my pussy. I gyrated and pumped my throbbing hot box against his fingers frantically and purposefully, completely relaxing my ass and offering no resistance as he pushed his dick in completely.

Suddenly, I realized that he had buried his cock to the hilt in my ass. He had played with my tight puckered asshole with the head of his dick which was wet and slippery from the cream oozing from my cunt. He had teased me that way creating a pleasant, interesting sensation that was new to me. And as he stimulated my tits and twat to the point that I was excited almost to delirium, he had slipped his thick dick all the way into my virgin asshole. I was amazed, pleased, confused, and enthralled all at the same time.

Thoughts and sensations flooded through my mind. I concentrated on how his cock felt deep inside where no other man had ever touched me. I loved the fullness and the depth. He was still inside me, so I could feel his cock throbbing, and I loved the thickness and stiffness of him. My ass was tight and snug around his meat, slightly uncomfortable, I remember thinking, but the idea of him inside me that way distracted me from the minor discomfort.

He remained motionless for several minutes, allowing my body to adjust, and I suppose, savoring his conquest. I felt stuffed, his cock was thick and pulsing, and he continued churning his fingers slowly in my wet cunt and gently brushing his fingers across the tips of my nipples. Every nerve ending in my body seemed to be alive, with every stroke of his fingers, I felt jolts. I was keenly aware of the connectivity of my body parts because it seemed like a continual flood of electrical currents coursed from one nerve to the next with every touch.

I liked the feeling of him being in my ass and my cunt at the same time, and as I turned to look at him, he thrust his tongue into my mouth probing, then sucking. I felt like I could simply melt away in ecstasy. He began to move his cock very slowly, kind of grinding into me, but not backing out at all, and increased the speed and motion of his fingers in my pussy and on my nipples.

As he intensified the stimulation between my legs and on my tits, he began to pull his cock back slightly, and made gentle, short thrusts into my ass. It felt unlike anything I had ever experienced, his body seemed melded to mine. He began to work his fingers on my pussy and tits again, and moved his tongue from my mouth to my neck, one minute fucking my mouth with it, the next licking the hollow of my neck with rapid flicks. He then began sucking the same spot until I felt a twinge of pain, and quickly moved to suck my tongue as I tried to draw away from his.

He knows my body well, and he teased and plucked my nipples and began to ram his fingers into my wet pussy, pushing me toward release. My body responded just as he knew it would, sensations raging, cunt aching, and I moaned and pummeled my cunt against his fingers wildly. As I tried to ride his fingers, my ass swivelled and gyrated on his thick fat dick.

He knew I was flooded with desire, desperate to cum, and in that ridiculous place of need that encompasses all else. Nothing mattered to me except that insane insatiability. I wanted him slamming into me, ramming me full, forcing my body to respond. He pulled his fingers out of my quivering pussy and grabbed my nipples and held them between his thumbs and forefingers as he began to fuck my newly penetrated ass.

I felt the length of his cock slide about half way out, and then felt him push back to the place he had been. It was not painful, but it was not comfortable either. It felt intrusive. He pulled my nipples as if he were milking my tits and pulled his dick about three quarters of the way out at the same time. I moaned as he continued milking my fat nipples, and felt him shove his cock back to the original place deep inside, then start to pump in and out of my ass.

It did not hurt really, but I was conscious of being full in a way I never had been, and the sensation was very different from his cock in my cunt. I felt my insides tugging against his meat, and as he pulled out, it felt his dick was scraping the walls of my asshole. I guess he knew that my ass was tight, and that it would be somewhat painful, because when he pulled the length of his cock almost all the way out again, he shoved his fingers right back into my empty, wet, aching cunt.

He then moved them to the spot close to my clit that he knows will make me cum every time, and began to work on me. As I became hot and frantic again, he began to fuck me in the ass. He pulled almost all the way out, then shoved his pole back in deeply. He had my nipples and my cunt on fire again, and although I was aware of pain as he started to give me my first fuck in the ass, I was again beyond caring because it was minor compared to the pleasure also coursing through my body.

He pumped in and out slowly and gently at first, periodically grinding and sort of rocking his cock, I guess to loosen and stretch my muscles some. As my body adjusted, he began to increase his speed and movement. He pulled most of the way out, then plunged back in a few times, then settled into a rhythmic, steady stroke. This was the moment when I really knew and accepted that not only had he put his dick all the way up my ass, he was really, actually fucking me in the ass. I could feel my asshole tugging against his pole with every beat.

He was clearly enjoying the tight grip and pull on his hard, swollen rod, because he increased his tempo again. As he masturbated me toward climax, he fucked my ass deep and hard. He seemed to want to make sure that my first time taking it up the ass was one I would never forget, because he kept changing from one type stroke to another. He fucked with short, quick jabs, deep, long penetrating strokes, grinding gyrations and rapid, hard pumps.

As he felt me close to cumming, he began to hammer his cock into my ass the same way he pounds my pussy. He withdrew his dick to the head and the plunged it back in deeply in rapid fire motion, fucking my ass with the same demand I have felt in my pussy so often. Shockwaves of pain from the unexpected assault on my senses fought with waves of ecstasy exploding in my body while I came all over the fingers he had thrust back into my cunt.

As my body spasmed with pleasure, he rammed his thick heavy cock into my asshole with complete abandon - rutting...slamming his meat harder and harder into my tight ass. Maybe he wanted to make sure he broke my virgin ass in completely, maybe he wanted to make sure I understood how it could feel when he pounded me instead of making love to me gently. Whatever the case, I realized that his timing was perfect and intentional. I guess that he knew that while I was cumming, the elation would distract me. Within seconds after I came, he exploded, letting his load fill my ass. In addition to the strange sensation of his jism flooding my ass, I felt a sudden, intense burning sensation from the salty cream. My ass was raw and sore, but I had not realized until it until that moment.

He pulled out quicky, leaving me empty and sore but satiated. We wrapped around each other again, and he held me close and tight, basking in that feeling of complete satisfaction and oblivion that comes after really great sex. The first time I took it up the ass may not be my last.