tagLetters & TranscriptsMy Diary Pg. 107

My Diary Pg. 107


My junior year of college I had this roommate, Justin, who was a complete screw up. Now, don't get me wrong, I like to party and I got more than my share of partying done while I was in school, but Justin never seemed to come up for air. He was always the last person to leave a party, assuming he didn't drink himself unconscious and wind up crashed out on some strangers couch.

Before I moved in with Justin, I thought he was cool. We had the same friends, went to the same parties, and he usually left with some sorority girl or hot foreign exchange student. The semester I met him, we were both looking for new roommates and it didn't take long to convince myself that this guy was as good a prospect as any other. When he showed up at the end of the week with half the rent in cash, I didn't bother to look for any other potential roommates.

It wasn't long though, before I started to realize what I'd gotten myself into. Justin was a good roommate in that he paid his rent on time, kept the house clean enough to bring girls over, and shared his weed whenever he was able to score some. Justin was a terrible student though. His professors, his parents, and even some school administrators would leave angry messages on our answering machine for him. People he owed money to would quiz me to make sure I wasn't him when I took his phone messages. Finally, there were all the women.

Justin was the kind of guy who would go back to some girl's place on Friday night, and stay with her until Monday morning if her or one of her roommates didn't force him to leave. Justin also had a habit of snatching panties and hanging them over his headboard. On one hand, it kept him from bringing these chicks home and having them know where we lived but on the other hand, it made it harder for me to get any play on campus because people knew he was my roommate. On top of that, with all the bridges he was burning by sleeping with everything that moved, even my friends were keeping their distance from me so as not be associated with him.

Midway through the semester, I was trying to figure out the best way to deal with Justin. Even though he hadn't been a jerk to me, there was no question that my roommate was an asshole, so much of an asshole that I was having a hard time avoiding the splash back every time the shit hit the fan. What was making this particular bit of afternoon brainstorming more difficult is that I was smoking a joint he'd rolled for me before vanishing on one of his three-day dates.

Between the haze of bitter smoke clouding the living room and my thoughts, I was having a tough time thinking of Justin as an asshole. True, I had firsthand accounts of girls he'd gotten drunk and slept with, some of whom had boyfriends or even girlfriends that now wanted to kick Justin's ass, but I don't really consider someone who cheats as the victim in that scenario. Still, Justin could have avoided a lot of that bullshit by, if not keeping his dick in his pants, at least by being a little more selective about where he put it. I couldn't exactly sympathize with the guy for what he was going through either.

Around that time, the weed had started to kick in and I was leaning more towards the opinion that everyone should just leave me out of it and that I, in return, should take a nap on the sofa. I realized that wasn't exactly a solution to my problem, but at the time, it really did seem like the best idea out of all the ones I'd come up with. It probably would have been the one I went with if the phone hadn't started to ring.

Justin thanked me when I picked up the phone, but he should have thanked the weed. At about this time, I was as prone to let the answering machine pick up the phone as he was. I had a cell phone if anyone wanted to reach me. Anyone calling the house phone was usually someone pissed off at Justin.

"Hey man," I said.

"Hey yourself dude. You smokin' that joint I left you?"

"Yeah. It's good shit."

"Fuckin-a right it's good shit man. You know I don't fuck with no bullshit weed."

I just laughed because there really wasn't a response to that statement. Justin's highest compliment was that this or that person 'didn't fuck with no bullshit' and once given, it really wasn't up for debate from that point forward.

"I am aware of the quality of your weed. In fact, right now I am acutely aware of it."

"You smokin' it now?"

"Yeah. Takin' a study break," I said. Actually, I didn't study as frequently as Justin thought, but that was his explanation to himself as to why his roommate wouldn't want to party all night on a perfectly good Tuesday. When I tried to explain the concept of a 'weekend' to him, I was met with a blank stare so I just let him think I studied a lot.

"Cool man. Well when you're done, just spray the living room down. My mom's coming into town tonight."

"No problem man. What time's she coming?"

"I don't know. Late probably."

I asked Justin where he was and I got the abridged version of last night's threesome. I congratulated him on his latest conquest and promised to spray the room after I finished my joint. When I hung up the phone, we were both in agreement that his weed was not bullshit, and I was under the impression that I'd have plenty of time to finish my smoke and air the apartment out before his mom showed up.

Four minutes later, the door buzzer went off.

I was pretty high by this point so I checked the caller ID to make sure that I hadn't simply spaced out and let a couple of hours sneak past me. Nope, Justin's carelessness had struck again and now it was going to embarrass me. I could already see how this would play out, with Justin the hardworking college student and me the forgetful pothead who wasn't giving Justin his messages from mommy and daddy. My earlier reluctance to label my roommate an asshole vanished when the buzzer rang a second time.

Holding down the nozzle on the can of air freshener we kept in the living room for just such an emergency, I unleashed a cloud of perfume as I walked to the door and pressed the intercom button.

"Who is it?"

I kept the can hissing through the response, but there was no mistaking the voice on the other end when Justin's mom told me she was here to see him. I pressed the buzzer to open the door, gave the room a few more seconds of air freshener, and chucked the can back in the wicker basket next to the TV. Either I was caught, or the thick cloud of flower-scented chemicals hovering in the air was just enough to cover the smell of marijuana while being subtle enough to keep anyone from getting suspicious.

In other words, I was caught.

I snatched off my sweatshirt and tossed it through the doorway into my bedroom as light footsteps ascended the stairs to our apartment. I had a buddy who always took his shirt off before smoking. I remember laughing at him and saying he looked like a typical stoner. His response was, "at least I don't smell like one". Funny the things you remember in times of stress.

I opened the door to our apartment just as Justins' mom reached the top of the stairs. We surprised each other when we first laid eyes on each other. I was surprised that the gorgeous woman with fiery red hair, green eyes, and a swell in her sweater big enough to make it hard to look her in the eye was my roommate's mother. She was probably just surprised to see me standing there without a shirt on.

Smiling, I introduced myself and shook her hand. She introduced herself as Bailey and took a seat on the sofa, directly in front of the ashtray with one half-smoked and one freshly-rolled joint sitting in it.

"Um, am I interrupting something?"

"About that. I didn't know you were going to be here until about five minutes ago."

It wasn't an answer to her question. It wasn't even much of an excuse, but it was all I had on short notice. My hope was that having Justin as a son might have conditioned her to look the other way when "boys will be boys". It wasn't much, but you play the cards you're dealt.

"And that," she asked, pointing at my bare chest. She was smiling, but she didn't seem to be on the verge of laughter. My hopes that she would remember this situation as 'amusing' vanished when she pulled her cell phone out of her purse. She dialed while I explained.

"I was just...you know. You don't want your clothes to smell so..."

"Hello," she said, cutting me off. "You can go now, I'm settled."

Outside, a cab pulled away from the curb and drove off down the street. It was then that I noticed the little electronic bud in her ear.

"So," I said, unsure of how to go forward. "Is there anything I can get you while we wait on Justin?"

"Sure," she said, taking the joint I'd rolled and putting it between her teeth. "You got a lighter and a beer?"

Relieved, I pulled my lighter out of my pocket and tossed it to her as I turned toward the kitchen. Between me and Justin, there was plenty of beer to go around. I grabbed her one of Justins' beers assuming that it was her brand and I grabbed one for myself. Walking back through the apartment toward the living room, I asked if she drank his brand and she shouted back that it was her favorite.

"You know, I'm glad that you're cool about the smokin'. You never really know how someone's parents are going to act when..."

I trailed off. Justin's mom had been wearing a lavender sweater when I invited her inside. I remember it because I found it difficult to pull my eyes level with her own when she first walked through the door. Now, she was wearing a lacy black and red bra, her huge breasts sitting comfortably on her chest. I could also see that she was wearing a belt with a big rodeo buckle on it. The belt was undone, her pants slightly unzipped, the lacy tops of her panties, also red and black, just visible at her waist.

"You can call me Bailey."


"I was thinking that you're right about not wanting to smell like smoke afterward."

"Yeah," I said. I was thinking about the way her red hair fell over her creamy white shoulders. I was looking at the spray of freckles across her cleavage. I was looking everywhere and the fact that she was smiling back at me while I finished undressing her with my eyes hadn't gone unnoticed.

Bailey lit the end of the joint I'd already been smoking and took a deep drag. She offered it to me and I took a hit that was just as deep. Forgetting that I was already pretty high to begin with however, I ended up coughing most of it back out.

"Sure you've done this before," Bailey asked. She flashed me a smile and swayed back and forth, playfully making her breasts swing just under my nose. I took another drag, this time I didn't try to be a hero and my ears were pleasantly ringing when I handed the smoldering roach back to her.

"This is good shit," Bailey said, flicking ashes into the ashtray before carefully pinching the last of the joint between her nails and lighting it. This time I made her cough when I said, "This weed ain't no bullshit."

"Oh my god, that is dead on," she laughed, rolling into me, pressing her breasts against my chest and giggling until she stopped. Then she simply leaned her chin on my chest and sighed softly while putting the last burning flecks of paper and hot ash in the ashtray.

"So," Bailey said, her fingernails lightly tapping my stomach. "How long do you think before Justin comes home?"

"There's really no way of knowing," I said.

"Then I guess we'll have to be quick," she said, reaching down into my pants and wrapping her hand around my cock.

I gasped as she slid her body against mine to wrap her lips around the end of my dick. She kissed it playfully, squeezing me just behind the head and rolling her tongue over the crease in the tip of my cock until my eyes watered. I groaned helplessly when she ran her tongue down the vein in my cock to suck my balls.

Bailey reached behind her back and leaned forward, swallowing my cock until I could feel the back of her throat tighten with every breath. She quickly undid her bra and let it fall to the floor. Looking up at me, her green eyes flashing out from under that red mane, she gripped my cock in her hand and began to stroke me up and down while she twirled her tongue around the head of my shaft.

Sucking the head of my cock, her head bobbing up and down gently with every kiss, Bailey looked gorgeous with the sun going down right outside the window, lighting her hair on fire. Leaning back, I gripped the back of her neck and slid my cock down her throat until she made a gurgling sound.

Pulling back before she coughed, I was surprised when she grabbed my hips and pulled me back in her mouth, taking my cock in the back of her throat.

Whimpering and wheezing, Bailey slipped a hand down her pants and started rubbing herself. Looking down her back, just over the rise of her ass, I could see her toes curling and uncurling as she moaned, her hot mouth never once leaving my cock. She pushed her pants down until I could see the red tangle of bush covering her pussy. I could smell how wet she was from where I was on the sofa.

"Goddamn you smell good."

She smiled at me with her eyes as she rubbed herself faster, making her toes clench and her feet patter against the floor. I was about to grab the sides of her head and push myself down her throat one more time when she licked the tip of my cock, turned around, and dug in her purse. A moment later, she turned to my cock with a condom in her hand, a corner of it's wrapper dangling from the corner of her mouth.

"Are you sure about this?"

"Oh yeah," Bailey said. A moment later, she had pulled the condom all the way down to my balls and was sucking the tip again, forming the condom to the shape of my dick. "I'm sure," she said as she straddled me. I could feel the heat from her cunt tickling the end of my dick right before she pushed down and enveloped me in her tightness.

All the air rushed out of me as she groaned and swayed on the end of my dick. She wrapped her arms around my shoulders, and encircled my waist with her hips as she purred in my ear. I found my air and it was my turn to moan as she hooked her heels into my back and ground her hips down into me. She yelped my name as she hooked her nails into my back and started to roll her hips against mine.

I gripped Bailey by the waist and guided her as she rode my cock, rocking back and forth, sliding up and down on it. She moaned and tried to keep from making sounds as I lifted her up and down on my throbbing dick. Again, I was just about to explode when she gripped my shoulders and eased herself off me.

"Oh....oh god," she said as, trembling, she raised her leg and rolled off of me.

"Did I hurt you," I asked, briefly considering how I'd explain to my roommate how I injured his mother before I was flush with pride at the thought that I might have moved something that hadn't been moved before.

"No," she said, crawling on her hands and knees to the end of the sofa and collapsing over the arm of it. "I want you to fuck me from behind." She then looked back at me over her shoulder and spread her legs, allowing me to see her glistening cunt. I was prodding her pussy lips open with the end of my cock when she placed a hand on my thigh to stop me.

"Not there," she said, her voice was thick and deep with lust and my cock was already heavy with having almost come twice already. When she guided the end of my cock to the tight little knot of her asshole, I only hesitated for a moment before pushing inside her.

"Oh yes," she moaned as I slid my dick into her asshole. I moved slowly, feeling her slowly loosen herself for me, allowing me deeper inside. She was hot, tight, and as I slid into her, I felt certain that the next movement would end it for me, but she kept urging me in deeper and by this time my body was on autopilot. When she gripped the arm of the sofa hard enough to rip the upholstery and ordered me to fuck her, all I could do was watch as I started sawing my dick in and out of her.

"Ungh...yessssss." Bailey's ass bobbed up and down on the end of my dick, her wet thighs sliding against mine. She turned her head to look back at me, but her eyes were squeezed tight. With my hands on her ass, I pulled her down onto my cock, probing the bottom of her stomach with it. Soon, her pale skin was flushed with heat, her sweat-streaked body taking on a coppery glow in the light of the setting sun.

"Oh god, I'm going to cum," she said as she started to push herself against me, snapping her hips faster than I could keep up with. I gripped her waist to hold on, but there was no controlling her. A moan started in the back of her throat and soon became a wail. Just as her orgasm started, I could feel my balls swell to the point of no return and my cock thicken with cum.

"Goddamn it Bailey. Ride that dick," I said before arching my back and exploding inside her ass. She was clenched so tight around my cock that my cum spurted back out of the condom, dribbling down her asshole and staining the sofa.

She writhed and wiggled on my shaft for several minutes, twisting her body, and moaning as I rubbed up against some new place deep inside her. By the time she gingerly eased my cock out of her asshole, it was numb from having cum so hard. I was only aware of it when it slapped, limp and dripping, against my thigh.

Justin's mom pulled her pants back up and picked her bra off the floor before sitting next to me on the sofa. I lit the other, freshly rolled, joint and offered it to her. She took a hit and passed it back to me while she swung her tits, oiled with sweat and heaving with every breath, back into the cups.

The two of us smoked until we got hungry and I took her down to the campus cafeteria to get something to eat. That's where Justin found us. He thanked me for keeping him mom busy for the afternoon and even paid for our food. Just as he was walking away with his mom, he came over to me and leaned in close to whisper something in my ear.

"Hey man, can you do me another favor?"

"No problem."

"I'm gonna leave my mom at the apartment tonight. I've got a pair of Korean exchange students I wanna show a good time if you catch my meaning."

"Same ol' Justin."

"You know it. Anyway, the old girl will probably be asleep by ten o'clock, but if you could take her to a movie or something, show her around downtown maybe..."

"Basically, keep her amused while you're off learning about foreign cultures."

"Ha! You know me too well."

While Justin slipped a hand into his pocket to produce a small baggie of weed, his standard payment for a favor given, I looked over his shoulder and caught Bailey, his mother, looking back at the two of us and smiling. Pocketing the weed after he pressed it into my palm, I gave Justin a slap on the back and watched as he explained to his mother that he had a test to study for. She looked disappointed for a moment, but when he turned and pointed to me, she gave her son a warm, understanding smile and a big hug before he walked out of the cafeteria.

I walked over to Justin's mom after Justin left and offered her my arm in a gesture of mock chivalry.

"Wanna head back to my place?"

"Lead the way."

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