Late Night First Time Anal

I began rocking her up and down on my tongue, slowly running it from her asshole, up between her soaking wet pussy lips to her clit, and then back down again. I could taste how delicious she was and couldn't wait any longer to dive in and taste her. There is nothing on earth I enjoy more than eating a woman's pussy. I buried my face between her thighs kissing her entire pussy with my lips, and alternating between sliding my tongue inside of her and kissing and flicking my tongue against her clit. I reached up and put my middle finger in her mouth and she immediately began sucking on it, making it nice and lubricated.

"Ask me nicely to put my finger in your ass" I said.

"PLEASE put your finger in my ass" she replied.

I was going to toy with her a little bit more; saying something like "say it like you mean it" but when she said "PLEASE put your finger in my ass", it was so convincing. There was sheer lust in her voice and I knew that she couldn't wait to feel her backdoor get penetrated. As I pressed my middle finger against her eager, but impossibly tight sphincter, I got as far as the first knuckle when the thought occurred to me that I honestly wasn't sure if I was going to fit. Her anus squeezed around my finger like an elastic band when you wrap it around four times, but was almost sucking me in deeper. I began making a come hither motion with my finger, as my lips and tongue were locked onto her pussy and her clit, devouring her delectable womanhood. The wiggling motion I was making with my finger loosened her up just enough to slide my finger in a little bit deeper, up to the second knuckle, and her breathing became labored and she gasped as my second knuckle passed her asshole and was inside of her.

She began moaning as I finger fucked her butt. I would pull it out as far as my first knuckle before sliding it back in as deep as it would go. I could feel her body begin to tighten up and her breathing became more shallow. She was sucking in short breaths and began arching her back up, pressing her ass back down against me whenever she knew I was sliding my finger back into her butt, making sure that she got every last millimeter inside of her. I felt her asshole begin to pulsate all around my finger as her hips bucked and I held my tongue against her clit for dear life. Her blissful moans echoed through the darkness, making me somehow even harder. I refused to allow her to stop cumming and after what was easily a 2 minute long orgasm, she couldn't take any more and pushed my face away, completely breathless and unable to speak. I looked up at her alluring green eyes, smiled, and said "thank you."

She uttered the sexiest laugh I have ever heard to this day and breathlessly said "thank ME?! Oh my God, thank YOU! That was... That was... oh my God."

Her body was still having aftershocks as I began sucking her tits again on the way up to her lips. She sucked her own cum from my lips as we made out again, and my hand again found its way to her butt, but this time my finger slid inside. She bit my bottom lip as I began sliding my finger in and out of her puckered little butthole and she again began pushing back against me, making sure I knew how much she was enjoying it.

We moved into a 69 position and as she put her perfect ass and pussy in my face, she began kissing my stomach and rubbing my erection through my boxer briefs. She pulled them down and finally released me from the constricting fabric. One of my favorite things about having a big dick is the initial reaction I get when a woman sees it for the first time. As I grabbed her ass cheeks nice and hard and was again massaging her asshole with my tongue, I heard her say "holy shit!"

I smiled as she wrapped her hand around my now pulsating shaft and felt her lips kissing my swollen head. I began sliding my tongue in and out of her pussy as I applied Astroglide to my middle and ring fingers. I slowly slid them both inside of her, preparing her for the main event. She immediately shoved as much of my cock as she could down her throat to keep from calling out at this increased intrusion. She was hungrily sucking and slurping at my thick, 8.5 inches as I slid 2 well lubed fingers in and out of her anus while my tongue was rapidly bringing her to her second orgasm. Her entire body began to shudder again and I could feel the vibrations of her lips on my shaft as she moaned. There was no way I was going to let her make me cum without taking her anal virginity.

"Kiss me", I said, and she immediately dismounted my face, straddled me, and kissed me, deeply and passionately, while sneakily trying to get my rock hard cock into her pussy. I smiled at her and said "nice try. I promised you if you came all over my face like a good girl I'd let you have it in your ass. Are you ready?"

"Yes?" she nodded "go easy on me" and I told her to get on all fours. I applied an obnoxious amount of lube to her still impossibly tight hole and had her watch me lube up my still throbbing hard cock. I could see in her eyes she was equal parts curious, nervous, and enthusiastic. I had read that cowgirl was a really good position for beginners as she would be able to control the depth and speed of penetration so I told her to straddle me again and she obediently mounted up.

I reached around behind her, grabbing my slippery cock and guiding it toward her rear hole. After some requisite "higher, lower, right there, lower", my fat, swollen head was pressing against her asshole. I began pushing as she began pushing back and just as she looked into my eyes and said "it's not going to work", my bulbous head slid inside of her, eliciting a huge gasp, an initial tensing, and then a smile. She was more surprised than anything else. I prompted her to relax and to kind of push out, and she began working my impressive length further and further inside of her, achingly slowly.

I loved maintaining eye contact with her, watching her bite her lip and watching her eyes roll into the back of her head. Centimeter by centimeter, I could feel her asshole clenched around my shaft, trying to suck me in deeper. Every so often, I would lift her back off, so that she could feel it sliding back out. She began to smile as she got used to it and I could see the hottest mix of pleasure, surprise, and an almost smug "I'm taking this like a champ right now". I asked her if she was ok and she nodded.

"Is it all the way in?" she asked.

When I said "it's about halfway" she gave me a look as if to say "seriously?" and said "Jesus, you're fucking huge."

My initial reaction had been that she was asking because she couldn't take any more and I was prepared to fuck her like that without going any deeper, so I said "do you want me to go deeper?"

Without hesitation she replied "oh, absolutely." I loved that she was relishing the challenge and that she was almost giddy that she got to have more. It sounds funny to say, but I was impressed. She was taking it like a champ. This girl I had lusted after, this girl who I thought would forever be off-limits, this girl who (until tonight) I had never even kissed was taking my long, thick cock up her ass. It took at least 5 full minutes before, at last, I was balls deep inside of her. When I let her know, she smiled and said "it's about time" like a little smart ass, and then began moving her hips, causing me to slide out. I could feel the chilly night air on my exposed shaft and on my balls and lifted my hips, thrusting back into her just as she pushed her hips back to again impale herself on me. The contrast of the cool air and the warmth, bordering on heat, of being inside her was mind blowing. She didn't waste a single inch, grinding back all the way each time, making sure she could feel me deep in her rectum. She began moving more and more quickly until she was riding me as though I was in her now absolutely dripping pussy. Her perky tits were in my face and I reached behind her, pulling her hair to make her arch her back and I began sucking and biting on her nipples as she ass fucked herself on my huge cock. I, or course, began talking shit:

"You like that don't you?"

"Aren't you so happy this guy broke into your house in the middle of the night?"

"Can you believe you have that big cock balls deep in your ass right now?"

"I thought you said it wasn't going to work?"

She was rendered completely unable to speak. She just looked at me with alternating looks of sheer lust, smiles, and looks that almost said "oooooo...if your dick wasn't in my butt right now, I'd kick your ass".

"Your ass is way too perfect for me to not bend you over" I said, and just like every other thing I asked her to do that night, she trusted me implicitly, and immediately put her face down in the pillow, ass up in the air. I reapplied a generous amount of lube to myself and to her, and paused to enjoy the sight of her on all fours, her freshly fucked asshole inviting me to resume my apparently very pleasurable assault, and took in the breathtaking sight of her toned ass cheeks and her glisteningly wet pussy. She looked over her shoulder and said "kiss me". I leaned down, my heavily lubed erection poking her in her right cheek as we hungrily sucked at each other's lips.

I placed my head just outside what I had heard her proclaim as "exit only" on several occasions and penetrated her from behind. It was much easier this time as she had already been fucking herself nice and deep, and impressively quickly while she was on top, but I still took my time to make sure she was comfortable in this new position. Her already work of art ass looked even more mind-blowing with my cock disappearing in and out of it. She soon began pushing back against me on each thrust, her cheeks slapping against my pelvis. I told her to spread her cheeks so she could feel every last millimeter and she promptly reached back, spreading her cheeks while making primal, guttural moans that were beginning to coax my cum to the surface.

She reached down between her legs and began to rub her clit as I fucked her ass with long, deep thrusts. I felt her asshole begin to tighten around my shaft as she was clearly about to explode in her most intense orgasm of the night, and I couldn't hold out any longer. She began to almost scream as her orgasm overtook her, making her even tighter and making me start to empty my balls into her rectum. I shot wave after wave of my warm sticky cum deep into her butt for what felt like more than a minute. I collapsed on top of her, still inside of her, and teasingly kept sliding in and out a little bit as my erection began to subside. She giggled yet again and managed, through her still panting breaths, to say "holy fucking shit. That was absolutely incredible." I slid out of her and watched some of my creamy seed drip from her freshly fucked asshole, which immediately made me hard again, but my half-assed comment about round 2 was met with a "you have to be kidding me" as it was easily 3:30 AM at this point and she had already surpassed my wildest expectations.

I rolled onto my side next to her and we looked into each other's eyes, making each other laugh, making out and softly caressing each other's bodies until we fell asleep. We went out for breakfast in the morning before I left to drive back home and we unanimously and enthusiastically agreed that it was one of those very rare times in life when the reality actually surpasses the fantasy. Our anticipation had reached a fever pitch and the experience had still been everything we had both hoped for. My theory about women with small, perky tits was still very much intact.