Anna's Diary Ch. 04

I started dating Anna about six months ago and she moved in with me last month. Last weekend she took her kids to visit their grandfather on the other side of the state so I once again had the house to myself. While rearranging our bedroom closet I found a box full of old diaries and decided to read them. I was completely shocked. Of course we've talked about our past but not even in her most inebriated state did she mention most of the exploits I read.

Anna is a short girl of five foot one inches. I've seen photos of her when she was young and although Anna was never a thin girl she held a lot of her excess weight in the best place possible, her ample chest. She's always had very long hair and while in her late teens and early twenties it hung down clear past her ass it's now only a little past the middle of her back. Her hair is dirty blonde and although I've never seen her with a bush I have no doubt that her hair color is natural.

Anna went to Western for only two semesters but apparently during that short stay she had quite an adventurous time. I have collected the best of them for your entertainment.

The only form of editing I've done is choosing which entries to submit and which to not. These are all her stories in her own words.

October 26 2013

What an uncomfortable yet exciting night I had. Brad went home this weekend so I took the opportunity to catch up on some school work. Although Jamila practically begged me to go out I insisted I stay in. Right around midnight I called it a night and went to bed. I don't know what time it was but I was woken up by the shaking of the bed once again. This time there were both distinctive male and female moans emanating from above me. It was blatantly obvious Jamila had a man in her bed.

I was a little angry at first. How could she disregard my feelings like that? She had to know I would wake up. I wanted to say something, I wanted to end their fun right then, punish her for being so inconsiderate. The fact was though I would have been just as embarrassed if they found out I knew. I quickly realized I was going to have to just lay still and keep quiet.

Reminiscent of the time Jamila masturbated while I listened I started to enjoy the sounds of their heavy breathing and soft grunting. Before too long I was touching myself. The man had a deep gravelly voice that I knew but couldn't quite place. Part of the difficulty was that he wasn't saying much. Every so often I'd hear him say Jemila's name or "yeah, take it all," or "you like my big cock fillin' you, don't you, you little slut." I was taken aback by his crass language. I felt like he was being disrespectful at first but soon I began to enjoy hearing it also. It wasn't disrespectful at all, was it, it was being straightforward and truthful. I've come to know my roommate pretty well and she enjoyed being promiscuous. She would often say that college was for opening one's mind to new ideas and experiences and that included sex.

About ten minutes into their play time I heard Jamila say, "we're gonna wake up my roommate. Let's move this down to the floor."

I was petrified, I was going to have to pretend I was sleeping. The worst thing about it though was I was gonna have to stop touching myself. The guy came down the ladder first. With each step I saw his manhood bounce up-and-down. I had never seen a black man's penis before in real life but that wasn't what shocked me. The guy was huge. Probably the biggest I've ever seen anywhere. Definitely the biggest I have witnessed in person, maybe bigger than I've even seen on the net. I was mesmerized by his endowment as it bobbed in front of my eyes. The darkness prevented me from making out too much detail but I could tell he was definitely circumcised. At that moment I envied my roommate. I wanted to know what it was like to be fucked by such a monstrous cock. The fact of the matter is it would most likely hurt me, maybe even damage me. I'm pretty inexperienced and a penis that size would probably split me in half.

I had gone to bed wearing only a pair of panties, as I often do, and for a brief moment I thought about pulling the covers down just enough to expose my breasts but I chickened out. Lost in thought I almost forgot to close my eyes before he descended completely. I wasn't able to see his face yet so I still didn't know who he was. When Jamila reached the floor I heard her whisper, "we gotta be quiet so no dirty talk."

"Now how are you going to be quiet with my cock in your ass," the man asked. The tone of his voice told me he had a shitting grin strewn across his face.

Jamila giggled and responded with,"what did I just say. Now behave or we won't be doing anything."

That was the first time I heard anything about anal coming from my roommate. She's obviously done that before and it sounded like she was going to do it right in front of me tonight. Of course she didn't know I was awake, but still. I've never done anal and to be honest I don't think I ever will. The idea doesn't appeal to me at all.

The next thing I heard was them kissing. I figured it was safe so I took a peak. He was facing away from me and bent down low to reach Jamila's face. It finally came to me, the guy was probably her friend Dwayne, the basketball player. He was extremely tall and thin. He had a tiny little ass that barely stuck out from his body. His shoulders were broad and his back was muscular. His dark skin glistened in the soft glow of the streetlamp shining just outside our window.

After a couple moments of kissing, Dwayne stood straight up while Jamilia bent slightly and presumably took his girth into her mouth. My fingers instinctively went back to rubbing my clit as I heard her moan and gag while she tried to conquer that beast that hung between his legs. Although his breathing increased I didn't hear him moan as my roommate pleasured him orally. I on the other hand was struggling immensely to keep my moans quiet. I was really enjoying this live sex show and found myself getting closer and closer to an orgasm. I knew there was no way I could keep quiet if I brought myself to completion so I backed off forcing myself to calm down.

Suddenly Jamila moved and I had to slam my eyes shut and lie completely still. A few minutes went by before I gained enough courage to peek again. Jamila faced away from me as she sat in her desk chair with her legs spread wide across the armrests. Dwayne was kneeling in front of her, thrusting himself in-and-out of my roommate slowly and methodically. With his head cocked back Dwayne moaned in pleasure uncontrollably. Jamila too moaned and with each thrust she seemed to be getting slightly louder.

Dwayne steadily increased the speed of his hips until he was pounding her unmercilessly. They both must have been caught up in the moment because the idea of being quiet was completely forgotten. He grunted with each drive of his pelvis while she moaned and gasped with uninhibited gratification. I wasn't being stealthy anymore either. My fingers were back between my thighs as I watched the show being put on just for me, even if it was unintentional.

Dwayne swooped his arms down and picked her up seemingly with no effort. His biceps bulged, skyrocketing my lust. With her legs wrapped firmly around his waist Jamila vigorously bounced on Dwayne's manhood.

My sight line was fixated on the rhythmic dance Jamila's plump backside was displaying so when I glanced up and saw Dwayne looking directly at me I was taken completely by surprise. Instinctively I shut my eyes and halted masturbating but I knew it was too late. I had been caught and there wasn't any mistaking what I was doing. Opening my eyes slowly I found Dwayne smiling as he stared at me. I smiled back and just watched them for a moment. I didn't even realize I had started fondling myself again until his eyes darted from my face down to where my hand was moving under the blanket. The whole experience emboldened me enough to pull the blanket down just enough to expose my breasts for him. He smiled even wider as he drew his tongue across his lips.

Jamila's moans grew louder as her gasps for air became more sporadic. Tell-tale signs she was getting close to an orgasm. I too was close and decided I would join her in ecstasy. In barely stifled shouts praising God and Jesus both Jamila exploded in euphoric delight. Thankfully she continued to moan loudly as my orgasm hit me. Hushed moans escaped my lips as I tried to subdue my shaking body. I don't know if Dwayne heard me but I'm sure he enjoyed watching me quiver in pure fulfillment.

Moments passed by while Jamila and I both came down from our highs before she finally realized how loud she must have been. "Oh my God, Anna I'm sorry," she said as she swung her head around. I had already shut my eyes and was pretending to be asleep. I didn't have time though to cover my bare chest so my breasts were still on display. "My God she must be a deep sleeper," she giggled.

"I guess so," Dwayne said with a mocked shocked tone in his voice.

"She didn't open her eyes at all?"

"Not that I noticed," Dwayne lied.

"But I bet you did notice her tits, huh?" I then felt Jada delicately pull at my blanket. I pretend to be slightly disturbed and let her cover me up.

"She really didn't wake up?"

"Not that I seen't," Dwayne lied again.

"Damn that girl musta been tired."

"Or passed out drunk," Dwayne added.

"Yeah, maybe." I heard kissing begin once again and knew I had fooled her.

After a short time Dwayne quite bluntly asked, "now it's my turn, right?"

"Of course baby," Jamila responded without hesitation, "let me go pee and then I'll get the lube."

After a moment I heard the familiar sounds of a woman peeing and opened my eyes once again. There at the edge of my bed was Dwayne stroking his enormous cock not three feet away from me. "Like what you saw," he whispered.

"Shh," I said, "I don't want her to find out."

"And you don't want it to end either, right?"

"Shut up," I giggled.

"Do you want to touch it," he asked me while looking down at himself.

Of course I wanted to feel such a massive example of a male member in my hand, "What, what about Jamila?"

"We'll hear the toilet flush before she comes back out."

"No," I said, trying to do the right thing, "I don't want to help you cheat on her."

"Cheat on her," he laughed, "her and I ain't got no commitments to each other. Besides, didn't you two go to a party at Stan's last weekend, and play strip poker?"

"Oh yeah," I said sounding dumb. I reached my hand out and rested my fingertips on the head of his humongous cock. Grasping it in my hand I couldn't believe how thick it was. My fingers didn't quite touch as I gripped it. When Dwayne released his grip I felt the entire weight of it. I hadn't even considered how heavy that mass of meat would be. That, I wasn't expecting. I only got in about two strokes before we heard the toilet flush. I abruptly let go and put my head back down on my pillow. Dwayne on the other hand didn't move. He simply went back to stroking himself again. I was amazed by his boldness. He was surely going to get caught by Jamila if he didn't back off right now. My eyes darted back and forth from his engorged member to his never flinching face.

"What are you doing," my eyes slammed shut when I heard my roommate's voice, "is she awake?"

"No."

"Then what are you doing?" Her attitude had changed slightly. The playfulness began to leave being replaced by concern.

"I don't know. You went to the bathroom."

"And?"

"And I just walked over here."

"To do what?"

"I don't know."

I was starting to think that Dwayne was going to crack. He was going to have to come up with something quick or out me. Thankfully Jamila did it for him, "you were trying to get a glance at those titties again weren't you?"

"I don't know, maybe," he was cornered, grasping for straws and actually scaring me. I really thought I was going to have to admit that I've been awake and heard, not to mention saw, everything. Thinking about it now I shouldn't have worried. They were the ones who woke me up with their sex, he was the one who presented his manhood to me, I only did what any curious girl would do, right? With no doubt in my mind I know Jamila would have done the same if the situation was reversed. In that moment though I felt like I had done something wrong and I was petrified.

Again Jamila diffused the tension, "you dirty little dog. Am I not enough for you, you want my roommate too?" The tone in her voice was obviously playful again but her next words took me by complete surprise, "maybe next time." Was she serious? I've had all night to think about it and I still don't know what I would say if she presented that scenario to me. I mean, he's definitely cute but is Jamila planning on being part of it? I have no problem being naked with her but I've never thought about being intimate with her, or any woman for that matter. Besides that I don't know if my little kitty can handle Dwayne's massive cock. I guess I'll just decide if the situation ever presents itself. If I'm being completely honest though, with a couple of drinks in me I'm guessing I'd say yes.

With my eyes still closed I heard them start kissing again. Jamila was making cute little soft moans as if she was eating something that tasted very good. I opened one eye ever so slightly to get a glimpse. Dwayne faced away from me and was bent over down to meet Jamila's lips. His tight little butt was about four feet away and if I was brave enough I would have reached out and squeezed it. Of course I wasn't and didn't. Instead I opened my eyes a little more. Dwayne's legs were separated and I could see a silhouette of his testicles hanging between them. They swung to-and-fro which told me that my roommate was probably stroking him. The tantalizing thought engaged my desire and soon my fingers were back between my thighs teasing myself again.

I shut my eyes almost all the way as she broke away from the kiss. Through barely opened eyes I saw Jamila lube up her fingers and skim them between her ass cheeks. Adding more lube to her hand she coated Dwayne's mega prick thoroughly and then bent over her desk presenting herself to him. I couldn't believe I was about to witness my roommate allow this giant of a man to force the biggest dick I've ever seen into the tightest hole on her body. Slowly stroking himself Dwayne guided the head of his penis to the entrance, or exit, or whatever, of her butt hole. I was frozen with anticipation. Only my eyes darting back and forth from Dwayne's cock and Jamila's face and the movement of two of my fingers gently caressing my clitoris beneath the blanket would have given me away.

She gasped when Dwayne entered her though not as much as I would have figured. This was obviously not her first time. From what she said earlier I'm sure this wasn't even the first time with him. He slowly pumped his hips and with every stroke Dwayne's thick cock disappeared more and more. One of Jamila's hands had made its way between her legs. Her moans steadily increased as she grew accustomed to how much her back door was being stretched. I could see her face tighten every time he entered her but the sounds emanating from her mouth told me the pleasure definitely surpassed the pain.

Suddenly Dwayne looked straight at me. He smiled like a cat who had a mouse beneath its claws. I knew he knew I was masturbating and I didn't care. I wasn't on full display or anything but that was the first time I had a man watch me do that. The whole situation was exhilarating. My heart pounded in my chest, all my senses seemed to be heightened as the sights, sounds and smells of sex wafted throughout the room. My fingers felt like they were producing electricity, sparking volts of pleasure into my clitoris which made me tingle all over.

Slowly I pulled down the blanket once again exposing my breasts for Jamila's man to enjoy. His smile grew even larger. He reached under Jamila grasping, then kneading one of her ample breasts. I felt like Dwayne was pretending it was mine he was enjoying which inspired me to squeeze my own in unison. My fingers moved from rubbing my pussy to entering it. Emulating the thickness of Dwayne's cock I plunged three fingers deep inside me and began relentlessly fucking my sopping wet hole.

Since her boy-toy entered her my roommate had been rubbing her own clit. Her efforts seemed to be paying off because the moans and gasps for air told me that she was getting close to an orgasm again. Dwayne was gasping for breath also as his thrusts quickened. Keeping pace with him I mimicked his speed with my fingers. "I'm coming," Dwayne announced.

"So am I," Jamila responded.

"So am I," I mouthed to Dwayne who was still watching me.

"Fill me with your cum baby," she begged in between moans of pleasure.

With a deep thrust and a grunt Dwayne erupted inside my roommate's ass. "Ahhhh fuck yeah," his voice was nearly a yell, "God damn girl," he said as he slammed himself repeatedly into her.

"Give it all to me baby," Jamila pleaded while her fingers buzzed across her clit, "don't stop, don't stop."

Witnessing that sent me over the edge. Slight whimpers came out of my mouth before I was able to cover it up with my free hand. Thankfully Jamila was in the thralls of her own orgasm and didn't notice me. There was no time to bask in my euphoric state of mind. Not if I didn't want to get caught. I quickly regained my composure and went back to pretending I was asleep. Lying still I just listened intently. Their breathing slowed and I heard Jamila say, "you can have the bathroom first," and then a moment later the door closed. I could hear the sink running for a little bit, then about a minute after it stopped the toilet flushed. The door opened and Dwayne nonchalantly said, "your turn babe," and then I heard the bathroom door shut once again.

Waiting a few moments I cracked one of my eyelids open just enough to notice that Dwayne was kneeling at the edge of my bed. Opening them entirely I caught an eye full of his oversized schlong. Even on his knees his waist stood above my bed. He methodically stroked his manhood for my pleasure. The monster that hung between his legs was growing again. "Did you enjoy the show," he whispered.

I could feel the blood rush to my cheeks. I was too embarrassed to speak so I said nothing, I just nodded my head slightly.

I couldn't stop staring at him fondling his member. "Do you want to touch it again," he asked as calmly as if he were asking me to pass the milk.

"No," I said playfully while at the same time reaching out and wrapping my hand around his huge meat. It was already more than three-quarter hard again. I began slowly stroking him, feeling it pulsating beneath my grip. I was completely enthralled in that moment by my roommate's sexual partner. The sound of the toilet flushing ended the experience abruptly again.

As Dwayne rose and stepped away from me I repositioned myself and again pretended I was asleep. Moments later I heard Jamila say, "is she still asleep?"

"Yeah, I think so," Dwayne lied again.

"Maybe she did have a little too much wine. I can't believe she slept through all that." I could almost feel them both staring at me. "You like watching her sleep, don't you?"

"Yeah, I guess I do." It was nice to hear him say that.

"I bet you'd like it more if her tits were still exposed," Jamila said jokingly.

"Well yeah," he responded. I had to stifle my own laugh as they both giggled.

"That thing looks like it's ready for action again. You didn't pull the blanket down to see those boobies again did you?"

"Of course not," he said, obviously offended, ''what kind of guy do you think I am?"

"Easy big fella, I'm just kidding." Jamila almost sounded nervous, like she had gone too far.