Plain Jane Ch. 02

Insignificant fact that nobody cares about but me: this is my 100th story on Literotica. Thanks to all my followers, readers, and commenters (good & bad) for reading my stories and helping to make me a better writer.

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The foursome I had with Tom and his roommates made me do some serious self-reflection. Don't get me wrong, it was fun, a lot of fun but it also got me worried that I couldn't control myself. I wondered if I was becoming a sex addict or a nymphomaniac. I settled down for a little while as I convinced myself that I didn't have to do everything Tom wanted me to do. I told myself I wasn't out of control, I could quit having random sex with him any time I wanted.

Looking back at that time in my life, I realize that I sounded like a typical drug addict who thought they could quit drugs whenever they wanted. My problem was that my drug was the cutest, most charming hunk of a guy that I had ever been with. Not only was he cute but I couldn't resist him. I knew he was bad for me but I was having the time of my life. Every time I thought about Tom or his roommates, my pussy got damp. Whenever I Jilled off, I was thinking about all the nasty things I did with Tom and his friends.

Maybe I was making up for lost time after being a social outcast in high school and not having many friends. I was an average girl in every way. I wasn't the first kid who went off to college and got a little wild at their first taste of freedom. I won't be the last either.

I was never going to be the prettiest girl in the room but at least I was real. I had seen a lot of girls that looked gorgeous with a lot of makeup on but if you saw them when they weren't all dolled up, it could be quite scary. My big boobs were real and my ass might have been a little on the curvy side but I was genuine.

I stayed clear from Tom for a little while but always ran into him at the library where I also worked. It was impossible to avoid him. He would continuously try to convince me to go upstairs with him so I could blow or fuck him in the corner of the library but I resisted. He asked me to hang out with him a couple of times but I told him I was busy.

After a couple of weeks, I ran into Tom in the student union and he asked, "Is there something wrong between us? Are you mad at me or something?"

"No, I've just been busy."

I tried not to look at his deep blue eyes or that dimpled smile of his that I found irresistible. I tried not to check out his broad shoulders, muscled arms, and chest in his tight T-shirt. I could only avoid eye contact for so long and it was like I was hypnotized. I fell victim to his charms again. I hadn't had any sex in over two weeks either so that didn't help. My pussy was itching for attention.

"I've missed you, babe. I thought we had something special going on."

Fuck, his charm was working on me but I did my best to resist.

"I'm just worried that you just want me for, you know, sex."

"Oh baby, you know that's not true. I'm just so busy with football that it's hard to have a relationship. You know I care about you."

That son of a bitch was doing it to me again, "Yeah, I know but it's hard sometimes."

"I'm sorry, Jane. You know I find you irresistible. You're the sexiest girl around. Fuck, you drive me wild," he said while touching my shoulder.

That's it, he had me. Tom made me feel pretty, sexy, and desirable.

"I'm sorry, Tom. I should know how you feel by now."

The fucker had me apologizing to him but I wanted him.

"Hey, do you wanna go up to your room and you know, kind of makeup?"

"I don't know, my roommate is going to be back pretty soon."

"Come on, we've got time."

I hesitated and thought about it for about ten seconds before I replied, "Okay."

And we were off to my dorm room where we had our clothes off in a matter of seconds. God, I missed fucking him. I dropped to my knees and stuffed that familiar banana-shaped dick into my mouth and began to blow him. His dick felt so good in my mouth.

"That's it, baby, suck my dick. Oh man, I've missed your blow jobs. You're the best."

He then led me to my bed where I spread my legs for my lover. I moaned as he entered me and started to pound my pussy. We were kissing and he was playing with my tits as he was fucking me. I was so horny it didn't take me long to cum on the curved dick of his that I missed so much.

Just then, my roommate Danielle came into the room. I think she was more shocked than we were. Tom never stopped drilling my pussy.

"Oh my god, I'm sorry. I didn't know. You should warn me next time," she said as she closed the door but not before taking a good long look at us in the throes of having sex.

Shortly thereafter, Tom came inside me. He had me lick him clean as usual before he got dressed and quickly left.

As he was walking out the door, he said, "Thanks babe, I'll be in touch."

When Danielle returned, the first thing she said to me was, "I can't believe you're fucking Tom, the quarterback of the football team. How long has that been going on?"

I smiled because for the first time in my life, a girl was envious of me and I replied, "Oh, it's been going on for a while."

"You're one lucky girl. Half the girls on campus want to fuck him. Damn, he has a nice body. That ass is to die for."

"It sure is. He's a stud in bed too."

Danielle and I never got along. She was a typical princess type of girl who expected people to cater to her. She always looked down on me like I wasn't worthy of being her friend. It didn't bother me because the popular girls treated me like that for four years in high school so I was used to it. After that day, she was acting like my best friend but I wasn't falling for it.

I felt like Tom had used me for sex once again but to me, it was worth it if it made girls like Danielle jealous of me. Fucking Tom was giving me sort of revenge on the stuck-up girls that shunned me in the past. It made me want him even more. I was more addicted to his charms because it elevated my status for the first time in my life.

Now that Tom had brought me back into his sphere of influence, he made the most of it. When I would see him in the library, he would easily convince me to go up to the remote second level so I could blow him or fuck him. I wasn't doing it every time we were there; I still had a job to do but if it was slow and he was there, we'd have some fun. I'm sure it was a status symbol for him too because I'm positive he was bragging to his teammates that he was getting a quick blow job or fuck from me.

He even convinced me to suck off his roommates Mike and Steve once in a while. I figured "What the fuck," I had already blown them before and they fucked and sodomized me too. Tom obviously didn't mind because he was the one who suggested our rendezvous.

Things were going along smoothly for me. Tom and I would hang out and "watch a movie" and we'd get together for a quickie in my dorm room or the library. I was having fun and getting a lot of sexual satisfaction. I still wished Tom would take me on a real date but I never pressed him on that.

One day right at closing time, after I had just gotten done blowing Tom, my supervisor at work called me into his office. Mr. Diamond was an older man in his late fifties or older, very overweight, and kind of a slob. He seemed to stare at the girls around campus which made them uneasy.

I thought he was going to talk to me about my schedule or to ask me to fill in for someone. I knew something was up when he asked me to close the door to his office.

"I need to talk to you about something, Jane. I don't know how to bring this up so I decided to show it to you."

"Sure, Mr. D."

I had no idea what was going on. He was doing something on his computer and then turned his monitor around. My heart sank with what I saw.

"You obviously didn't know that there are surveillance cameras throughout the library. I noticed you going upstairs several times with men following you moments later so I checked the cameras. I was shocked at what I saw."

My heart sank as I was watching myself on the monitor sucking Tom's dick. Mr. D fast-forwarded the video to Tom playing with my bare breasts and cumming in my mouth. Tears started rolling down my cheeks. I was worried about getting fired and everyone knowing what I was doing on the second floor.

"This was from this evening so I looked back and saw some very shocking things, Jane. You surprised me. I thought you were a shy, reserved girl and found out you love to have sex."

"I'm sorry, Mr. D., I promise it will never happen again. I swear to god, I won't do it again. Please don't fire me."

"I don't think I can trust you not to act like a slut again. I mean, look at what you've been doing," he said as he went to a video of me fucking Tom laying back on a table with my legs spread wide and even zooming in on his dick plunging into my cunt while I was moaning and begging for more.

I wanted to die from embarrassment. I was just waiting for him to say I was fired but he seemed to take pleasure in watching me suffer.

"So now what? Am I fired?"

"I don't know what I'm going to do, Jane. I guess that depends on you."

I was confused but he was leering at me. I was wearing a short skirt and a V-neck T-shirt that showed my cleavage. I put my hand near the bottom of my skirt to make sure Mr. D. couldn't see my panties.

I then asked, "What do you mean, Mr. D.?"

I was pretty sure where this conversation was going.

"Well Jane, I see that we have two options. I could fire you and I'd have to explain to the work-study program why I was letting you go which may include letting them see the evidence. They may even end your funding or kick you out of school for breaking our code of conduct. The other option is that you seem like a fun-loving girl. I just want to sample some of that fun, if you know what I mean."

A million thoughts were flashing through my mind. I was humiliated beyond belief but Mr. D. seemed to be holding all the cards. I didn't see any other options.

"If I choose the second option, will you delete the videos?"

"Of course I will, Jane. I promise," as he smiled at me with this disgusting smug grin on his face.

I wanted to punch him in his fucking face but he was getting his jollies knowing he had me backed into a corner.

"Okay, now what? I asked.

"Well, you can start by slowly taking off your clothes."

I reluctantly stood up, took a deep breath to help me gather up my courage, and slowly pulled my shirt over my head. I was standing before him in my white lace brace with the areola of my nipples showing through. Mr. D. was glaring at me. He nodded for me to continue.

I reached behind to unzip my skirt, wiggled to get it past my wide hips, and let it fall to the floor. I picked it up and placed it on a chair with my top. My thong matched my white lace bra. He made a circular gesture with his hand and finger so I slowly turned around. I could feel his lecherous eyes on my scantily clad body. I was humiliated beyond belief but found my pussy getting damp and my nipples harden. I found it difficult to believe my body was reacting this way and tried to fight it but to no avail.

"My, my, my, you have an outstanding body, Jane. I like a woman with a nice big butt. Now take off the bra."

I reached behind my back to unhook my bra and tossed it aside. My big tits were now on display for this dirty old man.

"Come here, Jane, let me feel those beauties."

Having no other choice, I stepped closer as Mr. D. reached up from his chair and began to roughly fondle my tits and tweak my nipples.

"You have a nice pair of tits, Jane. They are better than I imagined, even after seeing them on my monitor. Now continue."

As I peeled my thong down my legs, Mr. D. said, "Hand it to me," as he held out his hand.

I gave him my thong and he immediately held it up to his nose and said, "Um, you smell divine."

I thought that was pretty disgusting but began to blush when he said, "What's this, Jane? They feel a little damp. Are you enjoying this more than you are letting on? Get closer and let's find out."

I was ashamed because I knew my pussy was wet but I did as instructed and stood right in front of Mr. D. He sucked on my tits while he grabbed and played with my ass cheeks. He then slid one of his hands around and up my thighs. I moved to part my legs because I knew that's what he wanted. Deep down, I think I wanted him to touch me too.

"Now that's a good girl, Jane. I see we have an understanding.," he said as I quivered when I felt his fingers brushing against my pussy lips.

I wanted to slap him across the face but stood there in silence as he continued his assault on my naked body. I audibly gasped when he shoved his finger into my pussy and began to fuck me with it.

Mr. D. got a shit-eating grin on his face and said, "Well, well, well, Miss Jane, it appears you're enjoying our little talk."

"I hate it and I hate you," I replied but wondered if I just hated the fact that he was exposing the fact that I didn't mind his advances.

He then used his thumb to stimulate my clit. My knees almost buckled from the pleasure I was receiving. Truth be told, in a strange way, I was enjoying being dominated and being made to strip naked so Mr. D. could fondle and probe my young teen body.

"Your pussy is telling me a different story, missy."

Mr. D. kept rubbing my clit as I was holding back my moans of pleasure. The fact was that I was on the verge of orgasm and he knew it. I closed my eyes, lightly bit my lower lip, and my legs began to shake. I let out muffled moans and as much as I didn't want to, I started to cum.

"That's it dear, cum for me. You're nothing more than a little tramp."

He was right, maybe I was nothing more than a tramp.

When I was done cumming, I wanted to submit to the creepy old man in his office. I didn't care that he was old, fat, and ugly. He deeply desired to have me and at that moment, I wanted to get fucked. Mr. D. stood up and began to run his hands all over my body. He tried to kiss me but I turned my head to avoid his lips.

He then ordered me to, "Get on your knees, darling. You know what to do next. You know, just like you've done for the guys."

I got on my knees and unbuckled his belt, unzipped his pants, and pulled them down. I noticed a large lump in his briefs and was shocked when I pulled his underwear down. Mr. D. had the biggest and thickest dick I'd seen in my young life. I wondered if I'd be able to swallow it all but I was also curious to find out what it would feel like in my pussy. He was a creepy old man but he was well-hung.

I began by stroking him while staring at the big cock in my face and he said, "Go ahead and suck it for Mr. D."

I decided I'd give him the best blow job he ever had in hopes of making him cum sooner and ending my nightmare. I licked and tongued the shaft, working my way up to the head. I licked under the ridge and swirled my tongue around the head. I squeezed his dick and licked the precum that was oozing out of it. My lips then engulfed his dick as my head started to bob.

"Oh, that's it, baby, suck Mr.D's dick real nice for him."

I found it difficult to deep-throat him but I kept trying. With each downward bob of my head, I'd try and take more of him into my throat, gagging a few times in the process. Mr. D. even held the back of my head while forcing more of his big fat cock into my mouth. I closed my eyes and pretended it was someone else I was blowing so I could enjoy it more and believe me, I was enjoying it. When I got his entire dick into my mouth, I felt a sense of accomplishment and pride.

"Oh, you're a good little cocksucker, darling. You're the only one who's been able to take me deep like that. Do you like sucking my dick?"

I stopped sucking him long enough to reply, "Oh yes, I love sucking your dick."

"Call me 'sir' when you talk to me."

"Yes sir. I love sucking your dick, sir."

When he stopped me from blowing him and ordered me to lay back on his desk, I knew what was about to happen. By that time, I wanted to feel that big dick inside me. I spread my legs without Mr. D. asking me much to his surprise.

I encouraged him further by saying, "Come on and fuck me, sir. I want to feel Mr.D's dick inside me."

I did want him to fuck me but I also wanted to make him cum faster so I played along with his fantasy.

Mr. D. rubbed his dick along my wet, waiting pussy and said, "Here, take my dick you little slut."

My eyes rolled back into my head and I let out a loud moan as I felt Mr. D's dick stretch my pussy like never before. I was disgusted when I'd look into his face and found it hard to believe I was enjoying having him fucking me. He started out thrusting slowly but picked up the pace the longer he went on. He tried to kiss me again but I wouldn't let him. He then started to suck on my nipples and even left a hickey on my right breast. It was like he was marking his territory.

"Do you like my dick inside you, deary? Huh, do you?"

"Oh yes sir, I love your dick in me. It's so big. It feels so good. Fuck me, sir. Fuck me," I replied as I orgasmed.

Finally, after fifteen or twenty minutes, Mr. D. filled my pussy with his cum. He made the strangest sounds and weird faces as he came deep inside me. My torturous pleasure was now over. I felt so slutty when we were done. He used me for his carnal desires but that's also what made it so erotic.

"You're a great piece of ass, Jane. Let me know if you want to do this again sometime."

"That ain't happening, Mr. D. We had an agreement, now delete the videos, please."

To be honest, I expected him to renege on our deal but he went to his computer and I watched as he deleted the file. I was relieved, to say the least. I made a huge mistake by fucking and sucking guys at work and I paid a price for that mistake.

As I was leaving, Mr. D. told me. "You know where to find this big dick if you want it again."

I rolled my eyes in disgust but didn't say anything and closed the door. I rushed back to the dorm because all I wanted to do was to take a shower and wash off Mr. D's filth and cum from my body. When I looked in the mirror I saw the hickey he left on my tit. It would serve as a reminder of what I did with him for around a week but the memory will last forever. The mixture of disgust and pleasure I felt along with his dominance and my submission would also last forever.

In the ensuing days and weeks, I quit having sex in the library while fully expecting Mr. D. to call me into his office and show me another surveillance video that he didn't delete so he could have sex with me, however, that never happened. I did think about his massive dick at times though and was tempted to go to him at closing time so he could fuck me again but I thought better of it. Then one day, I heard that he was retiring and would be leaving in a week.

My slutty desires got the best of me and I decided to give him a special retirement present. I wanted to feel his big dick inside me again and figured it was safe because I'd never see him again.

The day before his retirement luncheon, we were working together at closing time when I went into his office. I was wearing a V-neck T-shirt and a short skirt just like the first time we were together. I removed my panties before I went in. He was curious as to why I came to see him.

"What brings you in here, Jane?"

"I just wanted to thank you for deleting those videos and never telling anyone."

"I'm a man of my word, Jane. A deal is a deal. I got what I wanted and you got what you wanted."

"I came here to express my appreciation for being a man of your word," I said as I opened my legs to show him I wasn't wearing panties and crossed my legs.