tagTranssexuals & CrossdressersIn Over My Head Ch. 01

In Over My Head Ch. 01

byready2play85©

It's funny how you can never know where life will take you. I was on the verge of turning 22 and it seemed like I had it all figured out. I'd find Finish College and get job that would make me a fortune, and hopefully I'd find a girl to marry along the way.

Three changes to my major, and a string of bitter relationships later, and I found myself not really sure what I was doing. All I knew is I was miserable in my current studies and the thought of hooking up with one more local girl had my skin crawling. The funniest part is it had only been a year since I thought I new it all, and in another year I'd probably look back and realize I still didn't know anything.

That's how I found myself up late board out of my mind wondering what to do with myself. My roommates had all gone out looking to get laid, but as I said that didn't sound so appealing at the moment. Usually when I sat home it was because I had a good book, or a game worth playing, but tonight I had nothing.

I started drinking then, and that was where it all started. After my third glass I was feeling decidedly tipsy when a nostalgic urge hit me and I found myself looking up Internet chat rooms. It had been years, my teenage years, since I'd last been in a chat room. I didn't even know if there were still such a thing, or if the world had turned fully to Facebook and twitter. As it turns out they were still out there. Lots of them.

I had no idea what I was looking at, and it wasn't just the whiskey. Sure I was technical, but there was a whole culture on the Internet that was alien to me. Acronyms flowed everywhere and pretty soon I gave up on choosing something specific and just started clicking on random ones.

Reading people chatting was boring to say the least. At least until I got into the lots room and found one hell of a fight going on. Some pretty nasty insults were being traded back and forth between two groups and amidst them all were a few please for them to leave Ready2Play alone. My own handle was SomeGuy1234. I know creative.

I watched the chat war gone on for a bit and even I was compelled to tell the assholes to leave Ready2Play alone. At that point I had no idea who they were or what the fight was about, but you didn't get called things like that and not feel hurt. At last Ready2Play left and the fight petered out. I lost interest and left the chat room. I was about to call it a night when I noticed one board only had 1 person on it.

I don't know what it was that compelled me to enter the chat room. Maybe I was lonely, or maybe I was just drunk, but I hadn't said a word to anyone all night and I felt the need to say something.

To my surprise it was Ready2Play. I wasn't sure what they were doing in that board, or even what the name of it was, but I thought what the hell I could say hello. My fingers typed the words without any thought on my part.

"You ok?" I asked.

"Who are you?" they asked in reply?

"I saw the fight on the other board. That was brutal" I said.

There was no response for awhile so I took the chance to look at their profile. It turned out Ready2Play was a 21 year old woman and her picture was smoking hot. Just one more reason I was confused why those other people were being so harsh to her.

"Are you here to yell at me to?" she asked

"No of course not. Those guys were just assholes. I just wondered in here and when I saw you I thought you could use a friend." I know it sounded corny, but I did feel bad for the girl.

From there our conversation opened up and pretty soon she was comfortable enough to give me her regular chat account so we could talk privately without the public forum. I found her real name was Janie and she was going to cosmetology school. We talked all through that night until I was completely sober and ready to pass out. It's strange to think two people could fall in love at first words, but I think that's what we did.

We became inseparable. At least, in so far as how much two people can be when they are limited to long distant communication. We called each other after a few times chatting and had long conversations that way to. Eventually we even got web cams so we could see each other as we talked.

It took a month before things turned sexual, but I was more then happy when they did. It started out with a strange question. At least, it was strange to me at the time. It was during a late night video chat.

"So can I ask you something?" She asked with a catlike look on her face.

"Sure." I said trying to sound casual. I was hoping to have some sort of web cam sex if I'm being honest. I hadn't even seen her naked yet and I was going crazy!

"When you picture us together, are you top or bottom?" She asked.

I had no idea what she was talking about, but I wasn't about to let that ruin what seemed to be a sexual innuendo.

"I'm whatever makes you happy." I said with a seductive glance. I loved the smile she gave me for that, and meant what I said all the more for it.

"That's good, that's how I look at it to. I just didn't know. When we do phone sex you never mention anything other then my pussy." She said still smiling.

I panicked. Had she gotten the idea that I was just into it for the sex?

"No it's nothing like that. I love all of you Janie. I've just never done anything like this before." I said.

"You've never been with anyone?" She asked with a confused look?

"No, just never anyone like you. Just plane boring girls and nothing long-distance like this. You're just so much more to me." That brought the playful smile back for me and my heart finally slowed down. It sped right up again with you next question though.

"Have you ever played with ass before?" she asked teasingly. She laughed as my jaw dropped and then continued, "Don't act like you haven't thought of it. You wouldn't be with a girl like me if you hadn't."

I guess I had thought about it, but I didn't know what that had to do with her. She was being playful though and I really was young and open minded so I ran with it.

"Sure I guess I have. I mean I've seen road-trip. I just haven't ever found a person that wanted to try it with me"

She grinned as I spoke.

"We'll you've officially found someone." Her eyes narrowed as she spoke and in a whisper she asked, "In fact, why don't you put on a show for me?"

My heart was racing. Sure I'd pictured doing naughty things over the webcam with her, but nothing like this! Still, I was so horny for her, and hadn't gotten laid in awhile so I thought what the hell.

"Ok, but you have to tell me what to do. I'm a virgin to all this." I said laughing.

She was so excited she actually clapped her hands together and her beautiful auburn hair danced around her face leaned forward quickly.

"ok, what do you have that's long and narrow, but really smooth?" she asked.

I looked around the room and my eyes landed on the new hair brush I'd bought that morning. It had a long polished handle. The only thing is it wasn't all that narrow. I held it up for her and here eyes lit instantly.

"You really want to start that big?" she asked and I knew right then I couldn't say no.

"I think I can take it." I said with a feigned manly bravado that was nowhere near real.

"That's good, because that brush has nothing on me." She said and the predatory look in her eyes made me nervous to say the least.

"Ok. I want you to take your pants off and kneel on your chair with your hot ass facing me." She said in a sultry tone. I'd heard it before during phone sex, but this was a whole new scenario.

"Wait a second, if I'm doing this what are you doing for me?" I asked with a smile.

"I'm already playing with myself if you haven't' noticed, and here," she stopped for a moment and pulled her top off. Her tits were amazing and looked so perfect in every single way. Maybe not huge, but just perfect. "There is that better?" she asked

I couldn't' even response. I just assumed the position and looked back over my shoulder waiting.

Looking back I saw for the first time that she really was playing with herself, and from the way her arm was going up and down she must have been rubbing something along her clit.

"OK, we need it to be good and wet so it slips in. Why don't you suck on it?" she said as she continued to play with herself. I was a bit nervous but I went for it all the same.

I started sucking on the handle the same way girls had done to me and I would be lying to say I didn't get into it. I must have been pretty convincing because pretty soon I heard a moan. Looking back her arm was moving even faster and lust was painted across your face.

"Oh my god that is so hot. You have to put it in now before I finish. Just go nice and slow and work it around your opening." She said panting.

Leaning farther forward I gave her a full shot of my ass and did as I said. I felt self-conscience at first, but her increased moans motivated me to go on.

My cock was rock hard, and while only 7 inches I thought it was enough to be proud of. I mean it was somewhat thick and perfectly shaped in my mind. I was glad to finally show it off to her.

I brought the brush handle back at last and rubbed it around my asshole and in a strange way I found it very much a turn on and I suddenly had enough playing around. I lined the brush up and pushed it in.

It hurt! I mean it really hurt! I pulled it out really fast and waited a moment for the stinging to go away.

"Oh was that to much baby. Can't you take it?" she asked with playful mocking in her voice. Looking back I gave her a determined look and tried again.

This time I took it slow and let it work itself in. It took me a good 5 minutes to be honest before I was really able to open up and let it start to slide it. Her moans only increased as I did it and that drove me on all the faster.

Pretty soon I had the brush all the way in and after a short break I pulled it back out before working it back in. I repeated this for a short while before I felt really open and ready for it and suddenly my cock was rock hard again and ready to explode. I almost forgot Janie if I'm being honest, until she chimed in again.

"That's so fucking hot. Fuck your tight ass with that brush." Her moans were getting frantic and I could tell she was getting close. Crazy as it seems, I was holding back myself.

"That's it, take it all. Pretend it me, pretend I'm fucking you and about to cum deep inside you." She said completely overcome by her need to orgasm.

Suddenly my own orgasm raced through me and I was moaning even louder then her as cum poured out of me. I pull the brush out and turned around to see how she reacted to my finally and saw she was there herself.

"You came without even touching yourself. Fuck that's it, I can't hold back anymore. You're so fucking sexy you little slut!" her arm was a blur as she neared her peak. "You want to see it don't you. You want to finally see me come don't you. Jus pretend you on your knees waiting for me!" She said and then everything went crazy.

She carefully stood up, never taking her hand away from her cock and stepped back so I could see all of her.

You heard that right. Her cock. This beautiful woman I had fallen in love and lust with had a cock just like mine. Even more surreal is it was bigger then mine! Maybe not a monster from a porno but on her petite frame it seemed huge!

She worked it like a pro as I sat there transfixed. Suddenly a major moan went through her and she was coming all over the place. It shot out like it would never stop and every blast seemed to send a shockwave of pleasure through her. It lasted at least twice as long as my own orgasm and left her totally drained as she collapsed back into her chair.

I was still standing there mute with mouth open wide in shock. Her eyes opened again and she gave me a huge satisfied, but sleepy, grin.

"That was so fucking good. Oh my god I can't wait till I get there next week. After this I don't even know what to think us being together in person is going to be like." She said breathlessly before continuing, "I see you like it too, I'm surprised your hard already." She said with that sultry look in her eyes again.

I looked down in shock and saw she was true to her word. I was hard a rock again and pre-cum was literally leaking out of me.

Looking back up I still couldn't figure out what to say or do so I sat down and couldn't help but give her a sheepish grin in reply.

"Ok baby, I have to get cleaned up and I'm sure you do to. Just remember that I wont' be one for a few days, but I'll be there before you know it and then the real fun will start!"

With that she blew me a kiss and turned the camera off.

I sat like that for some time before my brain turned back on. At last it all came rushing back to me and I was in a panicky all over again. I mean what did this mean and what did it make me? More then that though, all I could really think about was the fact that my girlfriend had a large cock, and she was going to be in sitting with me in person in a matter of days. To top it off, I had no way to get through to her in the meantime because her phone had been turned off and she was driving with her aunt and uncle who loved rustic bed and breakfasts.

All I knew was that I was in trouble.

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