Plain Jane Ch. 02

Mr. D. got that disgusting grin on his round, unshaven face and replied, "Just how much do you appreciate me keeping my word?"

"Oh, I don't know. I appreciate it a lot, sir" I said as I uncrossed my legs and left them open.

He smugly replied, "I knew you'd be back, Jane," as he began to rub his crotch. He went on to say, "Come on over here and sit on Mr. D's lap and show him how much you appreciate him."

"Yes sir."

Before I walked over to Mr. D., I took off my bra without removing my T-shirt. My nipples were poking out and my areola could be seen through the white cotton material. He had an even bigger grin on his face as I raised my skirt, giving him a quick peek at my pussy, and straddled his lap. I let him kiss me for a short time but it was a gross, sloppy kiss and I could only do that for a little while.

Mr. D.'s hands were on my breasts in a flash and quickly raised my shirt so he could suck on them while fondling my ass. He had me strip off the rest of my clothing and told me to lay back on his desk while he undressed. I didn't need to see his fat stomach hanging down and his extremely hairy chest and back but I concentrated on the big fat dick of his. He was already hard so I thought he was going to give me a quick fuck but he got down on his knees and began to lick my pussy.

I knew what he wanted from me so I told him, "Oh, that's it, sir, eat my pussy. Your tongue feels so good on my cunt."

"Your pussy is so sweet, Jane. I should have tasted it the last time."

Mr. D. was pretty good at oral sex and brought me to orgasm within a few minutes. He then had me get on my knees for him to return the favor. I gladly stuffed his dick in my mouth and eventually got it all into my throat like last time.

"Oh Jane, you're such a good cocksucker. There aren't too many women who have been experienced enough to deep-throat me. That's it, baby, suck Mr. D's cock real nice. Yeah, just like that."

I sucked his dick for several minutes while telling me what a good cocksucker I was. He then had me bend over his desk this time so he could play with my butt cheeks while fucking me. I truly missed his big dick. I had never felt anything like it before.

I told him, "I've missed your cock, sir. Oh, it feels so good. Fill me up, sir."

"I knew you would want to fuck me again, honey. I could tell by the way you squirmed last time. You've got such a nice hot pussy. Mr. D. missed you too."

Mr. D. kept playing with my ass cheeks, squeezing and pulling them apart and spanking me a little too.

"I've been such a bad girl, sir. Spank me, sir, spank me."

"You've got a nice big fuckable ass, honey. Mr. D. likes your ass. He's gonna fuck your ass, Jane. What do you have to say about that?"

"I don't know, sir. I'm afraid you're too big and it will hurt too much."

"If it hurts too much, I'll pull out, Jane. I promise. You know you can trust me."

I thought about it briefly and told him, "I guess we could try, sir."

Mr. D. pulled out of my pussy and went to his desk drawer and pulled out some lube. I thought it was an odd thing to keep in his desk. He used to either fuck other girls or jerk off. By the looks of him, I figured he was jerking off more than having sex with anyone. I must have been a real treat for him especially now that I agreed to let him fuck my ass.

I was very concerned about taking Mr. D.'s dick in my ass. I wasn't sure something that big would fit up there but I already agreed to let him try. Tom had butt fucked me a couple of times since our foursome with his roommates but he was nowhere near the size of Mr. D.

Mr. D. fingered my asshole first with one finger, then two before he thought I was ready. I tried to relax but that was difficult under the circumstances. He greased up his cock and I spread my cheeks for him. He placed one hand on my back and held his dick steady with the other. I swallowed hard and braced myself when I felt him press up against my anus.

"Go slow, sir."

He didn't reply and gave his dick one hard push and I felt the head of his dick plunge into me. It hurt like hell. I thought he was going to split me in half.

"Stop, it hurts, sir."

He ignored me and pushed in a little further. It hurt even more.

"Please, stop. Let me get used to your dick in my ass. It hurts, sir."

My pleas were still ignored as he pushed in even further. A tear rolled down my cheek as Mr. D. started to fuck my ass. I clutched the edges of his desk and winced in pain. He stopped long enough to put more lube on his shaft then continued his assault on my ass.

I begged him to stop but he told me, "I'm sorry, Jane but no other woman has had the courage even to try and get my dick up her ass. I can't stop now. I'll never get this chance again."

He continued sawing in and out of my asshole. There was nothing I could do about it at that point either. The strange thing was the longer he sodomized me, the more I began to enjoy the competing sensations of pain and pleasure. It didn't hurt as much as when he first penetrated my backside but it still hurt.

Oddly enough, I found pleasure in giving him the ultimate gratification of fucking a young girl's ass at his advanced age. I was taking his anal sex virginity too. It was also another show of his dominance over me and my submission to him. He was using me like a slut and it got me excited.

I reached between my legs and began to play with my clit and when I began to cum, I told him, "Fuck my ass, sir. I want you to cum in my ass."

"That's a good girl, Jane. Your ass is so nice and tight. I've never felt anything so good before. Mr. D. loves your ass," and he spanked me.

I felt so dirty and slutty but that's why I was there. I didn't plan on being ass fucked but I was willingly giving my body to him to use for his sexual pleasure. I was also using his dick as my toy.

When Mr. D. came in my ass he was breathing so hard and began to wheeze a little too. I was hoping he wasn't having a heart attack or something. How the fuck would I explain that. After he was done cumming, it took him a while to catch his breath and withdraw.

As we were getting dressed, Mr. D. told me, "Thank you, Jane. That was the best sex I've ever had. A guy that looks like me doesn't have that many opportunities if you know what I mean."

I kind of felt sorry for him and was glad I let him fuck me twice.

All I told him was, "You're welcome, Mr. D. Good luck in your retirement."

He fucked my ass raw that evening. I was walking funny on the way back to the dorm because it still felt like he was up my ass.

They had a retirement luncheon for Mr. D. the next day and before he left he came up behind me and squeezed my ass through my black leggings, and whispered in my ear, "I'll never forget this luscious ass, honey."

"I'll never forget you either, sir."

I never heard from Mr. D. after the luncheon but he did add another element to my sexual awakening.

In the meantime, I finally realized that Tom and I were never going to be involved romantically so I began to hang out with other people and date other men. However, I would still answer Tom's calls or text messages when I was in the mood for some wilder sex. We would be each other's "booty call." Sex was more interesting and pleasurable with Tom so I didn't want to stop seeing him altogether.

I would go to his place where I knew I could let loose and be his slut. Sometimes I would just fuck him and other times, we'd include one of his roommates. I felt I could better express my sexuality with Tom whereas I was afraid to reveal my inner slut to other guys I dated or slept with out of fear they would judge me. No other guy satisfied me quite like Tom did besides, he was such a fucking hunk. The other guys I was dating couldn't compare to Tom with his boyish grin, charm, physique, or dimpled smile.

My second semester as a freshman away from home was coming to an end with final exams approaching and the anxiety that came with them. I wanted to do well in school and focus on my term papers and exams for the final three weeks. However, when those pressures were finally done, I had some pent-up energy and an intense need to get laid.

My nineteenth birthday was coming up soon and Tom said he wanted to throw a little party for me. I was a bit leary of what he had in mind but I was so fucking horny, I agreed to it. I figured it would be with Mike and Steve again which wasn't a bad thing. He told me to dress exceptionally sexy because he had a surprise for me which got my juices flowing.

I didn't have much of a wardrobe seeing I was a poor college student but I had picked up a hot pink backless mini slip dress at a secondhand store. It had spaghetti straps with a deep V-neck so I could show plenty of braless cleavage. I wore tan-heeled four-inch sandals. I put on more makeup than I normally wear but didn't overdo it. My finger and toenails were painted to match my dress and lipstick. I felt sexy being all dolled up. I don't do it often but I knew this would be a special night. It was so special that I decided to go commando and leave my panties in my drawer.

My roommate even commented, "Looks like somebody is out to get laid tonight."

"With any luck, that's the plan."

As I was walking to Tom's apartment, I was getting plenty of stares, catcalls, and comments from a lot of guys who were also looking to party on the last couple of days before the semester ended. Any of them would have gladly fucked me that night. I was hot and knew it.

I was proud and felt sexy as my nipples pointed the way through my dress while my breasts were jiggling freely. The back of my dress swayed back and forth across my wiggling ass as I strutted my stuff. I had come a long way in my first year of college. I went from a shy, self-doubting, insecure teen to a confident person who was enjoying her sexual awakening. I was a nineteen-year-old woman out on a mission to have some fun and enjoy my birthday celebration with Tom.

When I got to his apartment, I knocked on the door and when Tom saw me, he commented, "Wow, you look fantastic. That's a fucking sexy dress, Jane. Happy birthday."

"Thank you, Tom. I can't wait to relax tonight. It's been a tough few weeks."

"Well babe, we'll make sure you relax and I hope you enjoy your surprise."

"Umm, I'm sure I will."

As I entered the apartment, there were birthday banners hung up and a big cake. I knew there'd be plenty to drink and smoke too. I was ready to party. It didn't surprise me to see Mike and Steve there so I figured there would be a repeat of our foursome which was more than fine with me. I was feeling so sexy and horny, I was actually hoping they'd be there.

Steve and Mike also complimented me on my sexy dress and I did a twirl for them. As my dress flared, it was obvious that I wasn't wearing any underwear. They grinned as I advertised my readiness to have some fun with the three roommates. Tom told his smart speaker device to play some soft music to help set the mood.

Tom quickly handed me a beer and we sat down to share some bong hits. Within thirty minutes of my arrival, I was already high and working on my second beer. All three fellas were staring at my legs and breasts. I made sure to lean over several times to tease them by flashing more of my breasts for them. I would cross and uncross my legs to highlight the fact I wasn't wearing panties either.

There was a definite, intentional sexual tension building in the room when I heard a knock on the door. Tom went to the door and let in two of his teammates on the football team, Bill and Pat. I was confused by the additional guests but thought that maybe they were just stopping by for a beer before leaving us to our business. I knew them from the library and they were offensive linemen on the team who were just as big as Steve. They must have been at least six foot five and close to three hundred pounds. They weren't as handsome as Tom and his roommates but their muscles were just as big if not bigger.

Bill and Pat took some bong hits and had a beer as we sat around making small talk about school and the football team. I could feel their eyes watching every move I made. I began to wonder if the additional guests were part of Tom's surprise. I wasn't sure I was ready to take on five big guys. However, after a couple more bong hits and a third beer, I wasn't going to rule out the possibility of fucking them all. The more they undressed me with their eyes, the more I wondered what it would be like to fuck them all.

I declined a fourth beer but offered to help Tom get more for everyone else. I followed him into the kitchen so I could ask him in private what he had in mind for the evening.

"So, uh, what are Bill and Pat doing here?"

"Oh, they just stopped by to have a drink with you on your birthday."

"Is that all?"

"Yeah, that's all, unless you, uh, want them to stay."

I was getting a distinct feeling that I was being set up again and said, "Are they my surprise because if they are, you accomplished your goal."

"They sort of are. They know about what you've done in the library with me, Steve, and Mike. Heck, they were there when we'd sneak off. Mike spilled the beans on what the four of us did that one time."

"So you brought them here to fuck me."

"Only if you want to, babe. I thought you'd like it. You're such a hot woman. I thought it might be fun. So, uh, what do you say? Are you down for it or not?"

"I don't know, Tom. I mean, they are hunks and all but I'm not sure. Let me think about it."

"No problem, babe. You don't have to do anything you don't want to."

We rejoined the others but I was looking at them differently and they were looking at me like they were wild animals ready to pounce. My pussy was getting damp thinking about the possibility of having all of these gorgeous athletes in bed pleasuring me. I still wasn't sure I could go through with it though. Five guys on one girl is a lot.

Before I could sit down again, Tom said to me, "Why don't you show off that sexy dress of yours? It's hard to appreciate it when you're sitting down."

I knew what he was up to but decided to play along. I went to the center of the room, surrounded by the five men, and began to strut around for them. I could feel their eyes glaring at me. I made sure I walked differently to make my breasts bounce more and gave my ass an exaggerated shake like a runway model on the catwalk. The more they glared at me, the sexier I felt.

Bill commented, "I love that sexy dress," to which Pat replied, "I like that sexy woman underneath the dress."

Tom playfully lifted the back of my dress to reveal my ass to his friends and I jokingly scolded him and slapped his hand away. I loved being the center of attention and the guys knew it. Fuck, I couldn't hide it if I wanted to. I can understand why women become strippers other than needing the money. I was getting so hot knowing I had five men lusting for me.

It became a game for the guys to try and lift my dress to catch a glimpse of my pussy or ass while I pretended to object. Things were heating up but no one wanted to go much further until I gave them the okay, even after I leaned over and shook my hanging tits for them. They began to touch my ass or breasts whenever I got close to them. I would taunt them by getting close while giggling but quickly moving away purposely losing at that game at times and allowing them to cop a quick feel. I was enjoying being a cocktease.

However, I wasn't quite ready to take that next step but I knew I was just postponing the inevitable at that point. I have five hot horny guys just waiting for the word that I was ready to fuck them. I just had to make sure I was 100% sure that's what I wanted to do.

When Tom went into the kitchen to get more beers, I followed him again so we could talk.

"Okay, I'll do it."

"Do what?"

"I'll fuck all you guys."

"Are you sure, Jane?"

I took his hand and brought it to my dripping pussy and said, "I'm positive."

He smiled at me, kissed me on the lips, and said, "Happy Birthday, babe. I have an idea that I think you'll love."

"Oh yeah, what's that?"

"Come with me."

Tom led me to Steve's bedroom where I saw several towels, a package of wipes, and lube. It was proof that I was being set up to fuck all five of them.

Tom then said, "Take off your dress."

"Why?"

"You'll see. Trust me, you'll love it."

I just laughed and began to take off my dress wondering if I was doing the right thing. When I was naked, Tom put a blindfold on me and tied my hands behind my back.

"I'm not sure about this, Tom."

"I guarantee you'll love this."

"I hope so."

Tom took hold of my arm and led me out to the living room to join his friends and announced, "May I present Jane, the birthday girl in her traditional birthday suit."

I heard someone shout out, "Hell yeah, now we're talking."

"Oh shit, look at those titties."

"I want some of that big ass."

Tom then presented me to each of his friends individually so they could kiss me, grope and suck on my tits, finger me, or grab my ass. Talk about feeling like a slut, it was like I was Tom's slave girl that he was giving to his friends. He was right, I loved it.

Being blindfolded heightened my other senses, I could hear the guys shuffling around when it was their turn to fondle me, and I could smell the different colognes, some of their touches were soft and gentle while others were rougher. I could smell alcohol and the aroma of the burning weed we were smoking. I could hear them making comments on my naked body. Mike and Steve were bragging about my sexual prowess in bed. It was quite sensuous.

Tom then said, "Okay guys, seeing it's Jane's birthday, we have to give her the traditional birthday spankings for good luck. We wouldn't want her to have bad luck all year now would we?"

"Oh no, we want Jane to have good luck all year," Mike said.

"I think we're the ones getting lucky tonight," Pat added.

Tom led me to a chair as I heard his friends move into place. He pulled me over his knee and locked me in place with his leg over mine. I played along with their game and made some feeble attempts to escape without success.

I told them, "I'm not sure I like this."

Tom laughed and replied, "Well, it doesn't seem like you're in a very good negotiating position now are you?"

He was right about that. I was bent over his knee with my ass sticking up in a prone position. I could feel the air in the room against my exposed asshole. I sensed the four other men around me looking on. Talk about feeling vulnerable. However, I was getting hotter at being dominated and "forced" to submit.

Suddenly, I felt Tom's hand come down with a loud cracking sound of his palm striking my cheeks. I instinctively tensed up my butt cheeks but then loosened them. That's when he struck me again. I cried out in exaggerated pain so he rubbed my ass before spanking me again. I was counting so I knew when my birthday spanking would be over.

Tom then said, "Who's next?"

I didn't hear anything but Tom was now holding me down with two hands. I began to worry because there were three huge linemen with massive hands that were going to spank me. One of them was next. I felt this big hand come down on my ass which made my butt cheeks ripple like waves in the ocean. He rubbed and squeezed my ass before giving me two quick slaps in succession. I heard shuffling around as the next person in line took their position.

I heard Steve say, "Don't worry, baby, I won't spank you too hard."

True to his word, Steve's big hand came down on my ass but not as bad as the others. He also rubbed my cheeks between slaps.

When he was done, Steve stuck his finger into my pussy, moved it around, and announced, "Her pussy is nice and juicy. I think she likes this."