Darren's Girl?

I'm Darren. I live in downtown Memphis. I head the IT Department in one of the corporate buildings on Second St. I don't consider myself to be the most attractive guy in the world but I don't have any trouble with the ladies. You know, I work out four times a week and run everyday but Sunday. I'm very lean but well defined. My hair is dark brown and cut short. I usually put gel in it. I was told once that I look a lot like Randy Orton, whoever that is. I think he is a wrestler. I'm about 6'3 so I'm fairly tall. The last girlfriend I had was a bit of a bitch but was great in the sack. To be honest the sex was the only thing that kept us together as long as we were. I have to admit it was real cool to start with but things just went to shit.

I usually spend the days working on computers and printer networks and defragging older CPU's. I don't really like my job, but I don't hate it either. It pays the bills and pays them well. I have a nice apartment in Harbor Town on Mud Island. I drive a Civic and I have a Suzuki GXR that I like to ride around occasionally. After work I used to spend the evenings at home with my girl. With my current situation I tend sit at home with my dog Gator and watch CSI reruns. My dog rarely gives me any trouble. He always wants attention, but doesn't break things or chew on things to get it. The only problems I've had are when guy friends of mine come over for the first few times. He'll bark and growl until I put him up.

I do get out on the weekends. I spend Thursday, Friday, and Saturday at the clubs and bars around town. Once I was single again I would sometimes meet girls at the club and bring them back to my place. My dog never cared he would come up to them and wag his tail. Like I said he always wants attention. Gator just loves the ladies. Wile I was with Kathy I forgot how much fun being single was. I spend every night on the weekends with a different girl. If the girl was worth fucking again I get their number or sleep with them again the next night. It's definitely the life to have in my opinion.

This mentality completely vanished the day I met Arial. I got a call from the main office suite that one of the computers was on the fritz and needed someone to take a look at it. All my workers were busy doing other jobs, and it needed to be fixed ASAP so I couldn't wait on one of them to get back. I got on the elevator and hit the top floor button. Twelve floors from the top the doors opened and a woman I hadn't seen before was standing there. This wasn't extremely odd considering the number of people that where employed in the building I wouldn't expect to recognize everyone. I knew that I would recognize her in the future because the woman was gorgeous. She had raven black hair and creamy looking skin. She was wearing a maroon suit and a black blouse. She had skin colored stockings and black heels. Even in her high heels she was only about 5'7". Her chest was large, her waist was thin, and her hips were nicely curved. She had a breathtaking figure. As she stepped into the elevator she smiled at me. Her smile lit up her already beautiful face. I was taken aback that a woman as amazing looking as her existed.

"Going up?"

"Yes ma'am," I replied. "What floor?"

"All the way to the Top," she answered as the doors closed and the elevator started up.

"Me too. What's up there for you?" I asked. "If you don't mind me asking." I added quickly realizing that might be taken as rude

"I don't. My desk is up there."

"Really? You're Ms. Sorenstien?" I asked knowing there was only one female exec in the building.

She laughed and smiled, "No I'm Mr. Floren's Personal assistant. I started Tuesday." Her laugh made my heart race. I felt like a little kid with a crush. "What's taking you up there? You don't look like any of the old men that run this place."

"I'm going to Mr. Floren's office to fix his computer." The doors opened and the elevator chimed. A heavy set man in a suit got on at the 24th floor. On the 25th floor the elevator opened and chimed again. We all got off. The heavy man went to the left and the woman and I went to the right

"Do you know where his office is?" She asked. "I can show you if you don't."

"Yes please." I responded. I knew where it was, but I wanted to follow her so I could get a view of her backside. She led the way. Her ass swished in her maroon skirt as she walked down that hall.

"Here it is," she said as she sat down at her desk in front of his office. She pushed a button on her phone and spoke into it. "Mr....What's your name?"

"Darren Blaney."

"Mr. Blaney from IT is here to fix your computer Mr. Floren," she finished and let go of the button.

"Send him in." a deep voice came through the speaker.

"You can go on in."

"Thank you...Ms. Donovan," I said looking at the name plate on her desk. Her name was Arial Donovan and I was head over heels for this woman and I didn't even know her.

I spent twenty minutes working out the bug that Mr. Floren had managed to pick up looking at porn. All I could think about was her the whole time when I walked out she was gone. She must have run a file to another floor or something. I got this knot in my stomach. I had been trying to get rid of that virus as quick as I could so I could come back out and talk to her some more. I got down to my office and sat down. I thought about calling her and asking her out Friday night for dinner at a nice restaurant. I finally worked up the balls and was reaching for the phone when it rang. I sighed and took a deep breath. I still had a job to do and needed to sound professional.

"Darren Blaney, IT Department what can I do for you?"

"Yeah I'm not sure what I did but I got the blue screen of death and restarted and now it won't start back up again. I knew that voice it was her. It felt like she was calling me to get me up there so we could talk. I remained calm and pretended that I didn't know it was her.

"What's your name and company ID number?"

"Arial Donavan and my ID number is 34726814."

"Ok I'll run you through some steps that may help." After I talked her through several steps that I knew wouldn't help her she asked if I could come look at it.

I quickly walked to the elevator and hit the up button. The doors opened and I got on. I hit the 25th and began my ascent. The elevator stopped on almost every floor to let people on and off. It was like God didn't want me to get there. On the 25th floor I got out and headed to her desk calmly so as not to seem like I was in a rush to get to her. When I got there she greeted me and let me sit down at her desk. I talked to her for about an hour while I ran scans and tests that I knew would take a while and leave me no positive results. After I finally restarted the computer so that it would work properly she thanked me.

I stood up and let her sit back down and I asked, "Would you like to have dinner with me tomorrow night?" She looked at me in a kind of I'm sorry way and then a grin slowly grew to a smile on her face.

"That would be great. I just moved here a last week for this position and I don't really know what to do on the weekends."

My face lit up with a smile and I said, "Great I'll pick you up at your place tomorrow night at seven?" I said wanting approval.

"That'll be great," she said as she wrote down her address and phone number on a piece of paper. "You can call me tonight if your not busy I don't really have any friends yet."

"Ok. I'll talk to you later then. I walked off feeling good and headed back to my office.

The rest of the day seemed to drag on as I watched the clock. I answered a few phone calls, and sent my people all over the building to do work. I even did a few more jobs in the building myself. At the end of the day I headed to the garage and got in my car. I headed home and sat down with Gator to watch some TV. Around eight o'clock I pulled the sheet of paper that Arial had given me out of my pocket and looked at the number. I pulled out my cell and called her.

"Hello?" her soft and sexy voice answered.

"Is this Arial?" I asked. Again I recognized her voice, but I wanted to play dumb.

"Yes."

"This is Darren from work."

"Oh hi, I'm glad you called. I've been sitting here at home doing nothing."

"Oh yeah, me too. I've been watching TV with my dog, Gator."

We started a conversation that started another one and so on and so. We talked for a few hours about what we liked doing, what foods we liked, what relationships have been like, taste in music. Overall it was like all the conversations I had had in high school when I liked a girl and talked with them for the first time. The only difference was the connection I felt with this amazing woman. I found out that we have a lot in common like we both like the same music and listen to the same radio station. We also like a lot of the same movies. The commonalities seemed to be endless. I had talked to this girl for only a few hours and seen her twice at work and I felt like I was in love.

The next day was a blur. I don't remember anything I did as far as work goes. I remember around noon I called my favorite fancy restaurant and made a reservation for eight o'clock. At five I grabbed my things and headed for my apartment. I got up from the couch and started getting ready. You know, shower and shave, brush my teeth the regular things. I put on what I thought made me look the best. At six thirty I left for her place.

Just before seven I pulled up in front of her place. It was a relatively small house, probably a two bedroom. I got out of my car and walked up to the door and rang the bell. I heard some moving around and a young boy opened the door. The kid couldn't have been more than three.

"Julian, come back here." Arial's voice called. Arial came to the door she was drop dead gorgeous. She was wearing a dark purple haltered evening gown and had a little matching handbag. "I'm sorry Darren this is Julian."

I squatted down and looked in his eyes, "Hey there little guy." I didn't care that she had a kid. It was a bit of a surprise, but I like kids so what ever. "How old is your son?"

"My son?...Oh no no this is my nephew my sister and I live together. This is her son. He's almost four."

"Oh ok that's cool. She here?"

"No I'm looking after him. Its ok if he comes right?"

"...Uh sure I jus..."

She started laughing. "I'm just kidding she is in the back room watching TV he's staying here." I laughed nervously. I was kind of embarrassed.

"Well are you ready then?" I asked.

"Yeah lets get outa here." She turned her head back in and yelled, "Later sis see ya later."

We walked to my car, "You look stunning Arial."

"Thanks you look pretty good yourself."

I opened the car door and let her sit down and get in before I closed the door. I went around to my side and headed to the restaurant.

"Did I scare you with the kid?" she asked sympathetically.

"Not when he answered the door, but you caught me off guard when you asked if he could come along."

"Yeah I thought it was kinda funny."

"It was. Looking back it's a lot funnier now than I thought it was then."

We chit chatted about different things on the way there. I pulled up at the restaurant before eight. We went in and they sat us. We had a big fancy dinner with wine and finished off the best dinner date I had ever had with a desert that we split. We talked all through dinner. When we finished dinner we sat there and talked some more.

"Arial, I know that I barely know you but I have never felt this way about anyone before. There is just something about you that just feels good. I hear your voice and see your smile and I feel all warm and fuzzy. I know that sounds lame and cheesy, but it's true."

"That's not lame. That's the sweetest thing any guy has ever said to me. And I just want you to know that I feel like that about you. I just feel good around you."

We kept talking a little longer and finished off the bottle of wine. We left the restaurant and walked down the street to the club. Neither of us was fit to drive so we decided to go dancing for a bit. We got into the club and walked out onto the dance floor. I wasn't really paying attention to the music but it was fun to dance to. Arial stood in front of me and rubbed her sexy ass on my crotch as we danced. Dancing with her made me hard. We danced until around two. Arial told me she was getting tired and needed to get home.

I felt sober by the time we got to my car. I drove her home. When we got to her house I walked her to the door.

"I had a great evening," she said as she jingled the keys in her hand. I leaned forward slowly as she moved toward me. We kissed softly for a few seconds. Her lips were soft and wet. When I backed up I opened my eyes and noticed her eyes were still shut. She slowly opened them.

"Wow!" she said. "That was amazing."

"Yeah, that was intense. Can I call you tomorrow?"

"Oh yeah absolutely," The speech between us had become a bit awkward. She could tell that I wanted to sleep with her, and I could tell that she didn't want to sleep with me, at least not on the first date.

"Well I'm gonna head back to my place and I'll call you tomorrow."

"Ok that'll be great." We kissed again and I headed to my car as she opened the door and went in. When I got to my place I went to bed. Around four my phone rang. It was Arial.

"Hey beautiful," I answered with a groggy voice.

"Hey there, I couldn't sleep. I was laying here thinking about our date and how much fun I had. I didn't want to wake you but..."

"No no it's cool. What's on your mind?"

"Here's the thing I really like you, and I really wanted to spend the night with you but there is something you should know before we go any farther...that is if there is an any farther."

"What are you talking about?" I asked with a concerned tone.

"It's better if I tell you in person. Can I come over?"

"Yeah sure"

I gave her my address and told her the best route to get here. About twenty minutes later there was a knock at the door. Gator jumped and ran. He was all over the door jumping and barking.

"Hold on a sec I'm gonna put Gator in his room he's acting all funny." That should have been a hint as to what was to come but I thought nothing of it. I put Gator in the second bed room and closed the door. "Ok here I come." I opened the door to see Arial standing there in a spaghetti strap tank and some flannel PJ pants. She looked great.

"Hey," she said softly. She reached out and stepped in to hug me. I embraced her and held her close. Her tits pressed against me. I could tell that they were fake but they looked nice anyway.

"Hey beautiful, what's the deal?"

"Can we sit down?"

"Sure." We walked over to the couch and sat down.

"Ok, this is going to be a shock, and I can leave after I tell you if you want me to." The suspense was killing me.

"Ok what is it?"

"I'm a transsexual." I almost started laughing. I thought it was her idea of a joke, but when I looked into her eyes I could see that it was true.

"A what?"

"A transsexual...I have a penis." I sat there for a second without saying anything. It was sinking in. The idea that I had kissed a guy, a very good looking guy pretending to be a woman, but still a guy was bothering me a little. Not to mention the fact that I wanted desperately to sleep with this guy...well before I found out it was a guy. "Are you ok? Do I need to leave?" she asked.

"No. Hold on. So how long have you been a woman?" I asked

"I have felt like I was in the wrong body almost my whole life, but I was only able to afford the hormonal treatment and breast implants a couple of years ago. I was hoping to get a sex change operation as soon as I got the money. So that I could be the woman that I know I was meant to be."

"Good for you," I said trying to sound sympathetic.

"I just thought it wouldn't be fair to you if I kept this from you. I really like you and I feel good when I'm with you."

"I felt the same way about you, but I just don't know what to think right now. I mean this is a bit of a bombshell."

"I understand. I think I'll just head home and let you think about it." She started to get up.

"Wait, don't leave. Stay the night with me." She smiled. "We can sleep in separate beds if you want."

"No no one bed is fine." We got up and went to the bedroom. We laid down and cuddled up against one another and went to sleep.

I woke up the next morning with my rock hard boner pressed against her ass. I knew that if she was awake she would feel through my boxers and her pajamas.

"Morning beautiful," I said. I had forgotten that she was a tranny and it hit me when I spoke.

"Hey there you, didn't figure I would be feeling that on my ass yet." I pulled back so it wasn't touching her anymore.

"Sorry, didn't realize it was there."

"It's ok it kinda turns me on." She rolled over and looked at me in the eyes. We kissed again. It was a soft, passionate kiss that made every other kiss I had experienced seem like a peck on the cheek. I felt like I was in love. As we kissed again I felt my cock grow even harder. I felt a hand reaching through the hole in the front to pull out my hard member. Her hands were soft and gentle. She stroked my dick slowly. A little pre-cum oozed out.

Without thinking about it my hand was on her hip sliding up her little shirt. I grabbed one of her large, firm tits in my hand and massaged the flesh in my palm. I ran my fingers over the nipple and lightly pinched. A light moan escaped her lips. We continued kissing as she stroked my cock a little faster. My hand remained on her breast softly squeezing the large mound.

"Let me get a little more comfortable," she said as she rolled off the bed to her feet. She slowly peeled her top off revealing the large double D's. Her tits sat high and perky on her chest. The doctor that put those in was an artist. They were flawless. She then turned around and slid her pants down so that I could see her sexy ass in a red thong. After she took off the pants she looked at me and asked, "Are you ready?"

"As ready as I can be." She slid down her thong revealing a little hairless penis it was probably two or three inches long. She had either waxed her pubic hair or gotten the laser removal because there was no stubble. I was surprised to find that it didn't ruin my mood. I was still hard and still horny.

"Do you want to touch it?" she asked. I was a little hesitant to say I did because I felt a little gay but I still wanted to. I reached out and grabbed it. It wasn't hard as I stroked it a little it stiffened up a bit growing in my hand. It only grew another inch or so. Arial climbed up on top of me straddling my face and inhaled my cock. It caught me by surprise that she got it all. I didn't hear her gag at all. As she sucked my cock her little penis bobbed up and down in front of my face. I wondered if I could do her too. Without thinking about it anymore I sucked it into my mouth and began sucking on her little dick. I heard her begin to moan with a full mouth. I sucked on her until I felt her body start to tremble. I knew what was coming. I let her cum in my mouth. Her white cream was sweet but the texture was a bit strange. I swallowed and rolled her over to her back. I reached into my side table and grabbed the lube. I squirted some on to my dick and rubbed it all over.

"Oh are you gonna fuck me big boy?" she asked in a sexy and seductive voice.

I looked into her eyes as I slid my cock in to her little hole as she stroked on her own. In and out, in and out, I drove my shaft deeper with each thrust she moaned in ecstasy. As I stuffed her tight ass with my dick she continued to scream louder with pleasure. I continued driving in and out as she started cumming. Her semen sprayed onto her stomach as her penis began to get smaller. I was still going strong. Her ass was tighter than anything I had ever been in. I felt my cock trembling