tagTranssexuals & CrossdressersIn Over My Head Ch. 02

In Over My Head Ch. 02


Authors note: Sorry for the lack of editing. I only had time to get a singe draft done.

I woke up in a haze the next morning. I'd hardly slept at all after my "chat" with Janie, and I was more confused then when I'd first lain down. My mind just couldn't seem to wrap around the fact that she wasn't really a she at all. Everything about her was so feminine, and she was so beautiful. The fact she had a dick was so absurd I almost had myself convinced it was some sort of nightmare.

I think I would have just gone with it being a weird dream had I not re-watched the video of our chat. I always recorded them so I could see her during those times we couldn't actually talk, and that left the truth of what happened obvious as I watched her orgasm all over again on the recording. After it finished playing all I could think about were her last words, that she would see me soon. Luckily my room mate was going to be out of town for awhile, so I at least didn't have to deal with him.

It's safe to say I was a bit manic as I attempted to re-trace my previous steps that night I first met her in the chat room. Lucky for me, it was still in my history so I was able to quickly track it down. Reading the title I saw that it didn't say LOTS as I had previously thought. Instead it was LGBT's. I knew I'd heard that term before, but I could remember what it was all about.

Having a new clue I ran a quick Google search on the acronym and found out it stood for lesbian, gay, bisexual, and transsexual. Going back to the chat room I read some of the conversations being had and it was obvious that it was a gay dating room. The fight from before, and being drunk I'm sure, had distracted me fully from where I'd entered.

It's not that I was homophobic; I just never really questioned my own orientation so the topic didn't really come across my mind most days. It was very much on my mind now though, and for the first time I realized how little I truly knew about gay people. Worse then that, I suddenly found myself questioning everything about my own sexuality. I mean it should be easy. I don't like guys so I'm not gay, right? We'll that didn't really apply in my situation.

I glanced at the clock and realized I was late for class. The thought of rushing out crossed my mind, but the urge to know more quickly over-ruled it. Page after page flashed by as I read through one site after another. The main thing I got out of it was that there were way to many terms being through around. I mean TS, TG, TV, TSTV, CS, Pre-Op, Post-op, Non-op. It's insane that they could literally try to apply so many labels to what accounted to a man that was really a woman, or maybe it was the other way around. All I knew is I was even more confused then when I started.

Before long I gave up on trying to figure out exactly what Janie was and instead I turned to porn. I know that's probably not the right answer, but that was the big question in my head. How exactly was all of this supposed to work? One of the first things I read about was how vulgar a term shemale was considered, but all the same I typed it in. The search engine was all to happy to send me millions of sites to peruse.

Just as before, I jumped from site to site and watched countless acts involving every possible combination of a transsexual and a man. The whole time I was half terrified, but another small part of me was also amazed that I had stumbled onto another world of sex I had never imagined before. My dick was a water witching stick, going up and down every few seconds. I'd get hard before things got to intense and then I'd go limp in fright as I'd watch some poor guy scream as his ass was reamed. Again, porn was probably not the right place to look for answer.

At last I gave up and turned my computer off. I was so mentally exhausted from all my twisted thoughts that I gave in and laid back down. Thankfully sleep was not so allusive this time around. I slept for what felt like minutes, but awoke to find it was already evening. Even crazier, I was fully hard and my heart was racing. My dreams were quickly fading, but I could remember Janie and her cock taking a large role in them. I rolled out of bed and thought about getting something to eat, but instead I grabbed my half empty bottle of whiskey.

As I poured my first drink my thoughts started flowing again and I found they had turned to how I felt about Janie herself. It was strange to think I still thought of her as a woman, but I did. I still wanted her to be a woman, I still wanted to lover her like one, but it was all so crazy now.

Those thoughts filled my head as I proceeded to drink myself unconscious.


The next few days flew by in a drunken haze. Before I knew it I was waking up to the day she was going to arrive. I was still no closure to having any answers, but I knew I couldn't figure it out without talking to her about it. I decided no matter how things went I would at least let her stay with me. After all, she came all the way to see me, and there was no way I'd be a jerk and leave her on the street.

Strangely enough, I found myself excited to finally meet her in person. Sexual confusion aside, I did get along with her better then anyone else I'd met in college and she had a great personality. I reasoned to myself that I'd at least found an interesting friend if nothing else. That thought gave me a sense of clarity that I'd lost over the last few days. Realizing for the first time how bad I smelled, I decided it was time to get cleaned up. I jumped in the shower and scoured every inch of myself. I came out feeling revitalized and seeing she would be arriving soon I quickly got dressed.

I was just finishing a quick cleanup when I heard a car pull-up outside the house. My heart immediately started to race and I through the broom in a corner and hurried to open the door. Looking out I saw her getting out of a small station-wagon and seeing her uncle unloading her bags I walked out to great them.

She heard my approach and turning to see me her face lit with a huge grin and she literally ran to meet me. Before I knew what was happening she was leaping through the air, and suddenly had her arms and legs wrapped around me in a tight hug. I held her against me and let myself enjoy the moment as I held her in my arms. At last she pulled back and I carefully sat her down.

She was even more beautiful then I remembered. I sat staring at her awkwardly and she just smiled back. I caught myself looking for some sign that she was actually the man I knew her to be, but there was nothing that didn't shout that she was a beautiful woman.

"So are you going to say hello or just stare at me like a creep?" She asked with a playful note to her voice.

I couldn't help but grin as I replied; " I don't mind being a creep if it means I get to stare a bit longer."

That made her smile grow, but before she could reply her aunt and uncle came walking up with her luggage.

"You must be Rob" her uncle said as he set the bags down and extended his hand towards me. I nodded in response as traded a quick handshake. His grip tightened at the last moment as he evaluated me, but then seeming to come to a decision he let go and smiled.

"We'll, she's all yours then. Be careful she doesn't tear the place down around you, she's been going crazy being cooped up in the car with us." He said as He gave Janie a shoulder hug.

"Hey, it wasn't that bad." She replied with feigned indignation. Her uncle raised his hands in mock defense before her aunt spoke up.

"You two have fun and be safe now. We'll be back in a week to pick you up Janie, but call if you need anything in the meantime." She gave her niece a warm smile and then they both said their goodbye's. Janie and I watched them go and moments later they were in the car and driving away.

"Here, let me grab those for you." I said as she started to reach for her luggage. I picked up her bags and motioned for her to follow me into the house.

After setting her luggage down in the living room we found ourselves in the kitchen as I offered her a drink and again I found myself staring at her as she leaned against the island.

Her hair was redder then I first realized, and she couldn't have been much over five and a half feet tall. Giving her body once over I figured she had to weigh close to a hundred pounds if I guess correctly. She happened to turn to face me at the worst possible time, just as I was staring at her crotch trying to see if I could make out her private parts.

I looked up to see that familiar grin on her face and I could feel my own face quickly turning red.

"Didn't ogle me enough out on the lawn?" she asked with an arched eyebrow that was made less harsh by the glee in her eyes.

"Sorry, I've just been thinking about you non-stop since we last spoke." I said with a sheepish smile.

She walked towards me and I had to look down to meet her eyes.

"Don't feel bad, I've been doing the same thing." She said as she reached towards me. The next thing I knew we were locked together and making out with an intensity that took my breath away. She was an aggressive kisser and our tongues slid together as our hands wondered over each other.

At last the frantic pace of our kissing slowed and we pulled apart. For a short while we simply looked at each other and for the second time that day I found myself forgetting about my earlier worries.

The clock on the stove happened to catch my attention and I remembered that I had a gift for her.

"Wait here for a moment, I got something for you." I said.

"You didn't have to get me anything!" she said softly, but when I made no move to leave she ushered me on, "We'll go get it!"

Smiling I went back to my desk in my bedroom and grabbed the envelope I'd left there. Returning to the kitchen I handed it to her and then explained.

"I figured for our first date together we should go all out." I said.

She opened the envelope and found the tickets to a show and dinner reservations.

"This is so amazing Rob, you seriously didn't have to do this." She said but her excitement shined through and I loved seeing it.

"I just wanted everything to be perfect." I said. For whatever reason saying that my thoughts turned back to my earlier worries, but I refused to give in. "We'll have to leave soon to make it in time for the show. I hope you don't mind waiting till dinner till afterwards, it was the only time I could get the reservation for."

In response she just smiled and quickly grabbed her bag and went of to get ready. I myself was already set to go as I'd gotten dressed up to great her, so I waited patiently in the living room. The sun was already setting and I couldn't help but get even more excited for our night as I sat there.

At last she came out, and she was wearing a red dress that made her look so beautiful it took my breath away. It was sexy without being to over the top, and it fit her like it was meant only for her.

Not wanting to have yet another awkward silence I forced myself out of my reverie and made my way over to her. Placing my hand gently on her hip I smiled as I said, "You look amazing."

She smiled in response and then reached out to feel the jacket I'd just put on as I waited for her. "You don't look to bad yourself." She replied.

Not wanting to be late, I offered her my arm and together we quickly made our way out to the car.

It wasn't a far drive, and I spent the time asking about her trip over. She'd had a good, if boring, time with her aunt and uncle, but she was clearly glad to be away from them. I in turn made small talk about my school. I'd thought about letting her know I hadn't really known about what she was, but I didn't want to ruin our night.

The show we were going to was normally an acrobatic act in Vegas, but they also traveled around the country. It was apparently a risqué version that only adults could attend. I'd bought the tickets before she'd left and I was a bit worried I'd made a bad choice, but just being with her was making everything seem less dire then it had been.

We arrived just in time and quickly made our way inside. The show had special couples seating which I'd paid extra for, and we were escorted to a small private loveseat the back that was just for the two of us. We still had a perfect view of the stage and she cuddled in me as the show began.

The lights went down and then the performers came out and began to dance and perform all sorts of crazy acrobatics. It really was an adult show though as each act had it's own naughty theme, and most of the actors were semi-naked.

A quarter of the way through the show I felt Janie's hand on my leg start to shift as she leaned over and whispered in my ear, "Can I have your jacket?"

I nodded and quietly pulled my jacket off and handed to her. She draped it across our laps and then leaned into me again. This time her hand ran all the way over my thigh and came to a rest on my quickly hardening cock.

"I don't know about you but this show is turning me on like crazy." She said as he hand definitely unzipped my pants and snaked into my underwear. I could only moan in response as she began to gently message my head and shaft.

This went on for a short while as I simply sat there and enjoyed the sensations she was giving me. Then, for no reason I could tell, I came to a decision. I decided right then I was going to figure out if I could really go through with being with her or not.

Almost as if it had a will of it's own my own hand slipped under the jacket and found it's way to her thigh. The feel of her black nylon garters turned me on even more and felt the curve of her thigh as my hand traveled down towards her panties. Reaching them I gently felt around and was confused to not find anything there to meet my hand.

Guessing my intentions she stopped playing with me for a moment and shifted, and suddenly her cock sprung up and was in my hand as she settled back down. It was already semi-hard and it filled my hand completely. I spent a moment just feeling it's length as it quickly hardened further in my hand. It was surprisingly soft and yet also firm in my grip.

I traveled down it's length and felt her hairless balls nestled at it's base. Looking at her I watched as she shivered with pleasure each time I moved my hand. Seeing the effect I was having motivated me to keep going and I slowly started to work my hand up and down her shaft.

A soft moan left her lips and her own hand sped up causing a fresh wave of pleasure to flash through me. I could feel myself getting close to cuming and I knew she must be to as pre-cum was filling my hand, making it easier to glide my fingers up and down her length.

She leaned into me and with a breathless whisper asked, "Let me know when you're close."

"I am right now." I said in an equally breathless reply.

Hearing that she gave me a grin and then suddenly she was leaning over and slight shift of the jacket was all it took for her to get my cock in her mouth. The explosion of sensation burned through me and I was cuming out of control. She never slowed down and it wasn't until I was completely finished that she quietly leaned back up.

I'd stopped stroking her as I came, but her cock was throbbing in my hand as she looked me in the eyes and then leaned in to kiss me. I was shocked to find she still had my cum in her mouth and it spilled into mine as our tongues danced together.

The taste was shocking, and not all together pleasant, but I was so turned on by what we were doing that I just went with it. Before long she pulled away, and then resting her head against my chest she moved her hips gently to remind me I still had work to do.

So much pre-cum and leaked from her dick that my hand now glided effortlessly along her length. Her hips kept moving it little thrusts as she fucked my hands and I felt my own dick start to harden again seeing the effect I was having on her. I went even faster and I knew she was going to cum any minutes, but then suddenly the show was coming to an end.

She let out a frustrated moan and leaned in to ask, "What should we do?"

"I can't walk out of here like this." She replied motioning to the large tent she was making against my jacket.

Realizing she needed to finish I quickened my pace and tried to beat the show to the end. Her moans came faster and faster and I knew I was close as my hand moved like lightening.

"Stop, I can't cum like this. If I do it'll get all over my dress and your jacket. We still have dinner after this." She said with sexual frustration clear in your voice.

Once again I realized what I needed to do, and without thinking I quickly leaned over and sliding my jacket aside I took her cock into my mouth.

She let out a startled moan, which only increased as I swirled my tongue around her head. Her pre-cum had a surprisingly sweet taste to it that drove me crazy with lust and I found myself trying to remember every thing I'd ever had a girl do for me. Her soft thrusting took on a faster pace as she began to fuck my mouth and I must have done something right because only moments later her hand was pushing my head down as she started to cum.

The first shot took me by surprise and nearly choked me as it went straight down my throat. It was followed my shot after thought of thick cum, but I was able to keep it in my mouth as she seemed to come forever. By the time she finally finished my mouth was so full I didn't know how I could pull my mouth off without spilling, so I swallowed it all. This brought another moan from Janie and I carefully milked the last few drops from her so they didn't spill onto her dress.

At last her dick started to soften in my mouth so I gently tucked it back into her panties and sat up. She gave me a giant relieved grin and then laughed softly as she wiped a bit of cum off of the corner of my mouth.

Looking around I realized the show had fully ended, but the lights were still dim as people made their way out. Luckily it didn't seem like anyone had noticed. Looking back to Janie who still had the relaxed smile on her face as she stroked my hair.

"Are you ready for dinner, or did you get full swallowing all of that?" she asked with a playful tone in her voice.

I could only smile in response.

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by Anonymous

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No, really. You Have to write more.
Okay, so, technically, you do not have to do any such thing, right. But this story series is so full of potential.
Well, after taking a moment, let me just saymore...

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