My First Chatroom

I.

It was just over a year ago when I went into my first adult chat site. I was 19 at the time and had just recently moved into my first apartment alone. It was a good hour drive from all my friends at home. I wasn't really sure what to expect in the move, but I was a young woman, ready to take on the world. I had just started a new job, and while I was ready for anything, I think the stress of the move had left me exhausted. It was early a Thursday morning when I decided I needed a break and decided to take the day off work to relax.

I started the day off with my cup of coffee, I answered all my email, and chatted with a few friends online while watching TV. The reality is though, after about an hour, there really isn't anything to do. I became kinda curious about the adult chat site on my IM. I had never really gone in one, but I had seen the ads and was certainly curious. I knew my parents and friends would kill me if they ever found out I was there, so I decided I would create an alias. I picked the name "emma_mar19" and picked a city between my new apartment and my old home town. I thought there was no way I'd ever actually meet anyone, so it really didn't matter where I said I was from. I signed in, posted a kinda blurry picture in my profile, and entered the room. Right away I got quite a few Instant Messages.

HotBud23: "Hey Girl"

Wandering Around: "hi./m/56"

BigGuy24: "Welcome to the room"

HornyHubby: "Where ya from Honey"

Handsome Fellax: "over here Slut bag XXX"

Obviously the guys were crude, but i found it kinda funny. I liked the attention, although none of the guys seemed like someone I would actually ever want to talk to. I sat there, reading through the chat room. Mostly it was what seemed like guys posting their stats or spammers recruiting for webcams; hardly exciting. It was far little less sexy than I had imagined. I suppose that's what happens when you have so many little boys in one place. lol. While disenchanted, I was still interested, and kept reading through the room. After about 15 mins I kinda zoned off and began to do other things... until I got a private message that seemed a little different.

DirtyOlder52: "hi there sweet thing"

DirtyOlder52: "I know I'm older than what I'm sure you are looking for, but I thought I'd say Hi"

Something made me think he was a bit more of a man than all the boys in the room. He seemed like a genuine guy. He had a different approach. His SN was "dirtyolder52" but he obviously had a sweet disposition. Unlike calling me a slutbag, he actually just seemed like he wanted to talk, and it completely engaged me. I decided to say hi.

emma_mar19: "Hi there"

DirtyOlder52: "hows it going"

emma_mar19: "Good, and you?"

DirtyOlder52: "really good"

DirtyOlder52:"I saw that you lived just a couple of miles away and thought I'd say 'Hi'"

DirtyOlder52: "to be honest, I didn't expect that you would actually write back to me"

emma_mar19: "I have to admit you're a lot older than my type, but you seem nice, no harm in chatting"

DirtyOlder52: "well I'm glad."

There was a minute pause and I couldn't really think what to type.

DirtyOlder52: "so what you up to in these rooms?"

emma_mar19: "this is my first time, I guess i'm just looking around"

DirtyOlder52: "oh ok, welcome. I tend not to be on here too often"

emma_mar19: "thanks... I took the day off work and decided that I would check this out"

emma_mar19: "u?"

DirtyOlder52: just surfing

emma_mar19: cool.

DirtyOlder52: "I like your pic, its really cute"

DirtyOlder52:"obviously you are a little curious about me or you wouldn't say hi, want to see a pic?"

emma_mar19: "sure"

I don't really know what I was expecting when I said "sure". I suppose a picture that was a little more PG, but he sent a pic of his cock. It startled me and wasn't at all what I expected. It looked different than the couple I had seen on guys my own age, it had grey pubes and the skin looked a little tired, but something about it really turned me on. It was so huge and so hard.

DirtyOlder52: "do you like it emma?"

emma_mar19: "yes. Although I have to admit that wasn't the type of pic I was expecting"

DirtyOlder52: "Oh shit, I'm sorry"

DirtyOlder52: "I didn't mean to offend you Emma"

emma_mar19: "You didn't... I just wasn't expecting it"

He immediately took the picture down.

DirtyOlder52: "forgive me Emma, I still very much want to talk to you."

emma_mar19: "You didn't have to take it down silly."

DirtyOlder52: "would you like me to put it back up again?"

emma_mar19: "yes"

I didn't really know what else to say. I sat there looking at that picture of his hard cock and something just got the better of me. I started playing with myself. Rubbing my clit through my panties as my eyes traced the curves in his shaft.

DirtyOlder52: "I'm looking at your profile picture emma, its extremely hot"

DirtyOlder52: "does that make you nervous"

emma_mar19: "not at all, actually it makes me kinda turned on"

DirtyOlder52: "would you like me to call you sweety?"

It seemed very quick, but before I could even think about it, I posted my number. I had heard a thousand "don't post personal info on the web" lectures, but for some reason I ignored it. I wanted to hear his voice. But the second i actually pressed send, I regretted it. all I could think about was "I can't believe i just did that."

I sat there for a few minutes and nothing happened. He signed off and I didn't hear back from him. A few minutes past. I was starting to think he wasn't going to call at all and was actually pretty relieved. I felt so guilty. I had just made a huge mistake giving out personal info and the more I thought about it the more it occurred to me that this guy could be anyone! He was twice my age and we had only talked for a few minutes online... and then the phone rang.

"Hello?"

I picked up the phone. I must have sounded so nervous. Even thinking back to it I can remember I was shaking.

"Hi there girl,"

His voice was deep and raspy. It sounded old, stern, deep, but somewhat familiar.

"I want you to know that you can talk about anything with me... don't be shy..say want your thinking. nothing ever leaves me....never."

He paused for a few moments and I listened to the sound of his thick breath on the phone. I could tell he knew I was nervous.

"Have you ever been with an older man before?"

"No...."

"Come on you can tell me, have u had a relationship with an older man before.....be honest... I'm okay with what ever you say."

"Thank you for being so kind. But no, I've only dated one guy and he was my age. I've always found them cute i guess though."

"Well thats good for me. I'm glad you liked my picture, I'm sorry if it was a little indecent."

"To be honest I liked it. It was much bigger than my ex's, and it turned me on so much."

"It sounds like you have a bit of a dirty streak in you Emma, is that true?"

I couldn't really respond, I opened my mouth and all that would come out was a soft moan.

"Would it be ok with you Emma if I took out my cock and played with it a little?"

I could hear him unzip his pants. After a few moments his breathing got heavy.

"So Emma, I'm looking at your profile picture here... and i have to tell you how sexy I think you are. I keep looking at your tight little body and those thin little lips. Do you think you'd ever actually meet up with me?"

I didn't know what to say. I knew nothing about this guy. In reality I had only seen one picture of his dick. He could (and probably is) some psycho.

"Hello...? Emma?"

"Well maybe, but I don't even know your name, I've never even seen your picture."

"Well my name is James. Let me email you a face pic"

A few moments later I had a new email in my mailbox. I opened it and my jaw dropped. It was Mr.Stevenson my high school PE coach.

II.

"Emma... Emma?"

I didn't know what to say. I recognized him right away but for some reason he seemed not to recognize me. I thought about it and supposed I had only had him for a couple of months during my sophomore year and the pic was pretty blurry. It didn't seem too likely though that he'd remembered me, but I certainly remembered him. He was 6'2, overweight, and had a great big white mustache. I never found him sexually attractive, and thinking about him sexually kinda grossed me out.

"Emma, are you there?" I could still hear him stroking his cock on the phone.

"Umm... yes, Mr. Stevenson"

"Mr. Stevenson?" He laughed. "When did we get so formal?"

I contemplated not telling him who I was. The reality was, I wasn't really sexually attracted to him at all. The more I thought about it, the more I kinda wanted to get out of the whole thing altogether. It seemed like just telling him the truth would be the fastest way to end it all.

"When i was your student."

"My student? Oh Shit, I'm sorry Emma. This must be very uncomfortable for you. I've had so many students and I can't remember all of them right away."

"Its ok Mr. Stevenson, I understand that its just a misunderstanding."

There was silence. I was extremely awkward. The silence lasted for what seemed like forever. All I could do was search for the right words... for any words... but none came. All I wanted to do was hang up the phone. I heard his breathing again getting heavier. Slow soft breaths became deeper and muted. Each one seemed a little louder the one before it. and regular.

"Mr. Stevenson, are you still masturbating?!?"

"Emma... uh.... its just that I got so turned on.... I...ssshould probably go." He hung up the phone.

I sat there, feeling awkward. I didn't really know what to think about what had just happened. My panties were wet, but felt cold. I stood up and walked across the room. The computer monitor was still on and displaying the picture of Mr. Stevenson's cock... of Mr. Stevenson's old sweaty cock. Again my eyes traced the curves of his shaft, and I found my hand running over my stomach, down to my panties. At first I just held my hand over it, but I started rubbing, and finally I pulled my panties to the side so I could fully get to my clit.

I rubbed faster and faster. Feeling my pussy get so wet. my lower lip cupped under my front teeth and I began to bite down. My eyes rolled back my head and I whispered, "Oh Mr. Stevenson". I had no idea where that had come from... I picked up the phone and pressed "*69".

III.

"Emma?" Mr. Stevenson picked up the phone on the first ring.

"Yes. Mr Stevenson. I'm sorry I was so uncomfortable. I think the fact that you used to be my teacher is actually very sexy. If you'd be up for it, I'd really like to meet up with you. Can you come pick me up?"

I could tell I had taken him off guard.

"Are you sure Emma?"

"Very."

I gave him my address and we hung up. It was about a 30 min drive before he'd be here and I decided I would jump into the shower before he came. My pussy was still so wet and I wanted to clean up. I was so turned on and couldn't wait to see him. I got out of the shower, wrapped myself in a towel and opened my dresser. I picked out my black thong and matching bra. I walked over to the closet and looked for something to wear. Almost immediately something caught my eye...it was perfect... my old school uniform. It seemed just right for the occasion. I pulled on my white socks, bringing them high to my knees. I buttoned up my white shirt and tucked it into my plaid skirt. The uniform still fit surprisingly well, although tighter than it had last time I wore it. It made my breasts bulge out, but I think that made it even better. I decided to tie my hair back into a ponytail like I used to in Mr. Stevenson's class. And I waited.

After about 10 minutes of watching out the window I saw a car pull up. It stopped in front of my building and a few seconds later my phone rang.

"Emma, I'm outside. Wanna come out?"

"I was thinking Mr. Stevenson... maybe you should come up here, its apartment number 34h."

I really didn't want to come out of the house dressed in my old uniform. While I thought it would be kinda fun for Mr. Stevenson, I thought that I really didn't want the other tenets in the building to see me dressed like that. I watched him get out of the car. He looked fatter than I remembered, and certianly scruffier, but it was the same Mr. Stevenson. He walked down the path and disappeared into my building. A few moments later I heard a knock on the door.

"Hi Mr. Stevenson!" I was really excited to see him and jumped a little when I said his name.

"Wow Emma, you dressed up for me! You look amazing"

He put his hands around my waist and drew me close to him. I was pressed against his pot belly as his hands traced over me. I felt comfortable with him, secure and safe. His hand moved up to my neck. He brushed my hair to the side and ran his fingers along my neck. His lips followed close behind, bringing chills all over me. I moaned lightly.

My chest heaved in anticipation, practically busting out of my shirt. He placed his hand softly on my breasts, massaging them as my nipples became swollen and stiff.

"Emma?" he whispered into my ear.

"Yes Mr. Stevenson?"

"I have a confession..."

He paused for a moment.

"I knew when I first saw you that you were a student of mine... It really turned me on"

I stood up on my tippy toes and kissed him on the lips. Our mouths opened and I felt his tongue caressing mine. His big thick mustache rubbed against my face. He reached inside my shirt, pulled my bra to the side, and began playing with my tits. I felt like I was in extascy in his big strong hands. I pushed my pelvis into him, wanting to feel as much of him as possible touching me. I could feel his cock pressing against my crotch. He was hard against his kakais, pulling his pants tight.

I i snuck my hands under his shirt and put my hands around his waist, feeling his large belly beneath his shirt. I traced the lines of his stomach with my fingers until I got to the top button of his pants.

"Emma I want this so bad."

"Me too Mr. Stevenson"

"I want you to blow me Emma, show me how good you are."

I took off my shirt exposing my bra and got down on my knees. His cock was buldging out of his pants. The fabric was tight and it looked extremely painful. I unzipped him, freeing his hard cock, and slid the kakais to his knees. He reached behind me and unfastened my bra, tossing it to the ground.

I looked up at him, making eye contact as I gripped his cock in my hand. It was warm and hard and i slowly began stroking it back and forth. It felt so good. So hard and so warm. His eyes rolled into the back of his head and he let out a soft sigh. I closed my eyes, opened my mouth, and took his hard cock in.

"Not so fast sweet girl. Lick it first and be gentle."

I ran my tongue down the shaft of his dick to the small dropplet of cum oozing out. It tasted salty but sweet. I took him into my mouth slower this time. Tasting it as it went in and out past my lips. I loved it. He took the back of my head into his hands and pulled me deeper onto his cock. I sucked him faster and faster as he groaned.

"Suck it Emma!"

"Suck my dick like a good girl!"

"yes Emma!"

His words trailed off as all I could concentrate on was that hard dick. His dick seemed huge, trusting in and out of my mouth. I wrapped my tonuge tightly around his dick as he pushed it back into my mouth. I could tell he was getting close. All I could think about was hoping he didn't cum into my mouth. I tried to say it but it was no use with him in there. He got faster and faster. I closed my eyes tight and waited for him to blow.

He grabbed my ears as cum shot down my throat.

"Yes baby!"

I swallowed as much as I could, but there was so much that it dripped down my chin and onto my skirt. I got up, wiped my face off and thanked him.

Mr. Stevenson pulled up his pants, buttoned them, tucked his shirt in, and kissed my forehead.

"Thank you Emma. I needed that"

He shut the door behind him. I felt so slutty. used. dirty. but more turned on than I had ever been. I opened my legs and masturbated with the taste of his cum still in my mouth.