Kendra's Very Merry Christmas

In addition to having never been with a girl like Kendra before, I also had zero experience with anything anal sex related. Honestly, I was a 100% virgin all the way through, not just with transsexuals...with sex in general.

With my parents being so strictly religious, I had dated a few girls in the past, but sex was out of the question. I only dated girls that went to the same church that we did, so everybody knew everybody. I knew that if I had sex with anyone, word would spread through the church like wild fire and my parents would find out about it, in no time.

The most experience I had with anything sexual, was masturbation. I had fingered myself on a few occasions but that was it, pretty much.

Kendra must have suspected as much, because she made a remark about how tight my ass was and I took note that her cock was hard as a rock. After loosening me up a bit, she moved between my legs and lifted them up over her shoulders.

I felt myself starting to get really nervous now, knowing that the moment I had been waiting for was quickly approaching. I watched, as Kendra took hold of her slick cock, glistening in the light and guided it into my hole.

It was a bit painful at first, and I couldn't help but tense up a bit. Once the head was inside of me though, Kendra was able to easily start pushing forward and easing the rest of her monster cock into my ass.

She was so fucking big and I could feel every inch, as it worked it's way into me.

Having looked at it just moments before she started pushing into me, I had been overcome with anxiety brought on by her size and I had thought for sure, there was no way she would be able to fit the whole thing in my ass.

Once she got about halfway in, I felt myself starting to shake underneath of her. My body trembled and I bit my lip, trying not to scream; she was going to split me in half, with that thing.

"Take a deep breath," Kendra whispered in my ear.

I hadn't realized until she said it, that I had been holding my breath the entire time. My cheeks were burning and I was starting to feel a bit dizzy. I opened my mouth and exhaled, my lungs aching as I started breathing heavily.

"Relax," she encouraged me. "You're doing just fine, hon."

I moved my hands up, over my head and grabbed the pillow, gripping it tightly. Kendra waited a few moments, before she started easing the rest of her cock into me. A few more long, thick inches and she had completely bottomed out.

Her cock throbbed deep inside of me. It felt really hot, almost like it was burning my insides. Yet strangely enough, it was a pleasing sensation.

"Good lord baby, your ass is so fucking tight!"

I whimpered, holding my breath again without really meaning to for a few moments, then releasing the air.

"Fuck," I gasped, as Kendra shifted slightly and her cock slid back just a little.

"So...fucking...big!"

"Mmm, mama loves your ass baby. Do you like my big, black cock in your tight little ass?"

"Y-Yes," I groaned. I could feel sweat running down my forehead and Kendra wiped it away, kissing me on the nose.

"Brace yourself baby," she said, softly. "Here we go."

She pulled back and slammed forward, shaking the bed and causing my entire body to jump with surprise and a little bit of pain, too.

"Fuck!" I yelped.

She drew back again, slamming forward and grunting as she did. The third thrust caused me to gasp for air, knocking the wind right out of me and I swore, I could feel it in my gut.

Kendra repeated herself, drawing halfway back and slamming hard into me again and again. I was slowly starting to warm up to it, but it was taking a bit longer then I had hoped. The pain was minimal at this point and my own cock was throbbing, leaking a steady flow of pre-cum.

My balls ached and my head was spinning, as Kendra continued to plow my ass with that monster cock.

Eventually, she pulled out and turned me over onto my stomach. I buried my face in the pillow and braced myself, as I felt her probing my hole with her cock again...then she rammed it straight back into me, with such force that it once again knocked the air out of my lungs.

Now, she wasn't holding back anymore. Hands placed on either side of my head, Kendra was drilling my ass now. She was hammering away, shaking the bed underneath of us and moaning and panting in my ear.

I was grunting and panting, struggling to catch my breath as she thrust harder and harder. Each stroke seemed to have more strength behind it then the last, and I really did feel like she was trying to break me in half.

My eyes were bulging and I was having a hard time catching my breath, my asshole aching with every thrust that she delivered. I felt like I was going to cum at any second, but I didn't want to do that too soon.

"S-Stop!" I yelled out, trying desperately to control my body.

"What's the matter," Kendra asked, stopping immediately and staying perfectly still.

"Did I do something wrong?"

"God no," I replied, breathlessly. "I just...need a moment. It's all a bit overwhelming."

"Sorry baby," Kendra whispered, rubbing my back in an attempt to soothe me.

We waited a few moments until I relaxed and I felt like I had a grip, over my impending orgasm. Once I was good to go again, Kendra started thrusting...slowly at first.

Then gradually, she started to pick up the pace until she was right back to pounding my ass, like she'd been doing earlier.

The feeling of fullness was pleasing, her dick sliding in and out and moving over my prostate, hitting it at just the right angle every time she thrust into me. My cock was swollen, harder then it had ever been before and trapped between my body and the mattress.

"God, I'm gonna pump your ass with my cum!"

Kendra said, quite loudly.

"Do you want that white boy? Do you want me to fill your ass with my cum...I'm gonna knock you up!"

"D-Do it," I yelled, my voice muffled by the pillow.

Kendra grabbed a handful of my hair and yanked my head back.

"Say it again, I didn't hear you the first time!"

"I-I said, do it! Please!"

"Do it please, Mama!"

"Please Mama," I begged.

I would have said anything at this point, I just wanted to feel her cum inside of me. "Please cum in my ass!"

"One big creampie, coming right up baby boy!"

Thrusting harder and much faster now, Kendra shoved her cock as deep as it would go and I felt it start to pulsate. She started twitching and moaning, practically screaming in my ear as her cock erupted and shot her cum so deep in my ass that I thought I would be able to taste it.

I felt the warmth of her semen, pumping into me and it was honestly a very sensual feeling. Kendra reached underneath of me and wrapped her fingers around my cock, jerking it furiously as she continued thrusting, even after she had finished cumming.

It only took a matter of seconds, before I was twitching and writhing around underneath of her, moaning like a bitch. My cock gave a twitch and I exploded, roaring out in pleasure as I covered the sheets with my cum.

I collapsed, hardly able to breathe and Kendra collapsed on top of me.

Seconds later, she pulled her cock from my ass and flipped me onto my back, sitting on my chest and shoving her dick in my mouth. I gagged, as she pushed all the way into my throat and started fucking my mouth. I could taste myself on her dick, mixed with the taste of her cum.

I couldn't believe it, but she was still so fucking hard. This time though, Kendra wouldn't last quite as long as she had earlier.

A moment or two after thrusting her cock into my mouth, Kendra cried out in pleasure and her cock started to pulsate once again. She pulled it back quickly, stroking it hard and fast right in front of me and exploded.

Kendra painted my face with her warm, sticky cum. At least ten, thick ropes of cum shot from the tip of her dick. Some of it splashed across the bridge of my nose and all over my chin. One shot landed on my left eye and I just barely managed to close it, saving myself from the unfortunate discomfort that a cumshot to the eye would bring.

Opening my mouth, a few more shots landed right on my tongue and I moaned, savoring the sweet taste.

The rest of it actually shot right over my head, landing on the pillow, before Kendra flopped onto the mattress beside me, struggling to catch her breath.

"Holy fuck," she muttered. "Baby, that was the best orgasm I've had in a very long, fucking time."

"You really came a lot!"

"I sure did, didn't I?" she laughed, scooping some of her cum off of my face and tasting it for herself.

"And how did you enjoy your first cock?"

"Ha...it was...intense," I replied.

"Did you enjoy it though?"

"Oh yeah, of course! It was great...a bit painful but...it felt great, too. Does that even make any sense?"

"Ha-Ha, hardly baby. But I know what you mean. You aint the first boy to tell me that."

I looked down and noticed that Kendra's cock was starting to get hard again, already. I was incredibly impressed, by her sexual stamina...this girl looked like she could go on and on forever, if she really wanted.

I reached over, wrapping my fingers around her cock and started to stroke, as I kissed her on the lips.

"Wanna go again?" I asked, in a sexy voice.

"Oh honey, you don't got to ask me twice."

This time, I wanted to be more in control. So before Kendra could move a muscle, I rolled over on top of her and mounted her. Kendra laughed, as I leaned in close and captured her lips once again.

I started humping her, feeling her huge cock probing at my hole until it popped right into me. I sat back on her dick and started riding, bouncing up and down and moaning as I did.

Kendra moved her hands to my hips, placing her feet flat down on the bed and lifting her ass off of the mattress. As she did this, she pushed me high up and her cock so deep in my ass, that I couldn't stop myself from screaming out loud.

She started thrusting, bouncing me hard, up and down on her cock. Her ass never touched the bed as she continued throwing me up and down. I wasn't just moaning anymore, now I was screaming in pleasure...this was great. Much better then the first time, a few minutes earlier.

I grabbed my cock and started jerking off, as I continued riding her cock. Kendra finally dropped back against the mattress, pulling me down with her and shoving her tongue into my mouth.

We kissed passionately, tongues wrestling as my cock erupted and sprayed cum all over her stomach and breasts. Just moments later, she rolled me over onto my back and buried herself to the hilt in my ass.

Throbbing and pulsating, her cock spewed her third load of cum of the night, into my abused asshole. She pulled out and laid down beside me, shoving me onto my stomach and smacking my ass hard.

"Let's see that creampie," she said, still out of breath.

Kendra spread my ass cheeks and I could already feel her cum, leaking from my gaping hole. She seemed to be really aroused by the sight of it and buried her face between my ass cheeks, shoving her tongue into my hole and eating her own cum.

I shivered and moaned, the feeling of her tongue in my ass, causing my cock to swell up once again.

Then, she was slowly pushing two fingers into my hole. Her other hand moved underneath of me and once again, started stroking my cock.

Her two fingers pushed firmly against my prostate and I tensed up, eyes watering and body trembling.

A third finger was slowly and carefully inserted into my loosened hole, spreading me even wider then I already was. She fucked my ass with all three fingers, pumping them in and out of me and stroking my cock at the same time.

"Do you know how many fingers, I have in your ass Marc?"

"Th-Three?"

"Wrong," she replied, to my surprise. "I have my entire hand inside of you right now, Marc."

Was she serious? I hadn't even noticed, until she told me...it still felt like just three fingers. How wide had she spread me? I looked back over my shoulder and could just barely tell, she had her hand all the way inside of me up to the wrist.

Now that I realized she wasn't lying, the realization that her whole hand was in my ass, made me feel a bit funny. My head started to spin again and my heart was pounding in my chest, as she worked her hand in and out of my ass and kept stroking my cock with the other hand.

"I...I'm gonna...c-cum," I stammered, feeling that familiar sensation building up inside of me again.

This time though, it was the most intense that it had been all night.

I opened my mouth to scream, but nothing came out...just air. My face turned red and hot and I shuttered, as my balls filled up with cum once again and once again, I erupted like a fucking volcano. By now, the bed sheets were soaked with a mix of sweat and cum and when my orgasm subside, I sunk into the mattress and laid in a pool of my own cum.

Kendra carefully pulled her hand from my ass, the feeling a bit less pleasurable now and a little more painful. My ass was gaping and I could feel cool air blowing inside of me.

I knew I was going to be sore as hell, in the morning. Kendra laid down beside me and smiled, pulling me into her arms.

"You're a good fuck boy," she whispered to me.

"You can stay with me, for as long as you want."

I might have to take her up on that offer, I thought to myself. Not only was I in a warm bed, wrapped up in her warm arms...but god damn, I had never felt so good in my life. Christmas morning would be here soon and what a morning it was going to be, I thought.

I couldn't wait to spend the rest of the weekend with Kendra...maybe even longer then that, I hoped.