tagTransgender & CrossdressersEmily and Steve Ch. 01

Emily and Steve Ch. 01


As I pulled my cock out of Emily's ass and shot my load onto her flat stomach, where my cum mixed with the load the beautiful blonde cross-dresser had just shot from her throbbing cock a moment before, I thought to myself that work was suddenly going to be a lot more fun.

My name is Steve and I work as an accounts payable clerk at an office supply company. Basically, my job is pretty dull -- sitting around and trying to reconcile our purchases with our vendor invoices, but that's not why you're reading this story, so that's enough of that.

I work in a department of five people plus my boss. In addition to myself there are three women who I can't stand. All they do is gossip all day long, especially about each other behind the others' backs. Whenever possible I avoid speaking to them. My boss spends most of his time sitting in his office, planning unnecessary business trips for himself and his "executive assistant" and playing Free Cell.

The only other person in the department is Mike, who isn't much of a conversationalist either, at least not with me. I'm a pretty big dude who is into sports, working out and cars, and Mike is a small guy who doesn't watch sports, hasn't lifted a dumbbell in his life and rides to work on a bicycle. Add to that the fact that Mike is one of the shyest people I know, and any conversations we've had have been over almost before they start. Usually I'll say hi to Mike, who will stare at his feet and mumble something, strands from his blond hair escaping out of the ponytail he keeps it in to fall in front of his face and cover his eyes completely.

It's fine that I don't talk to the folks at work, though. In fact, I don't have many friends in the city at all. I moved here from another state after finishing college, and haven't bothered to make many friends. But it's okay for me, because it saves me having to explain why I would keep showing up to their dinner parties and potlucks without a girlfriend. I don't think that the chatty-Cathys in the office would understand if I brought who I wanted to date to their next pool party. I like shemales and cross-dressers.

Mostly on weeknights I go home and watch some good shemale porn, waiting for Thursday night to roll around. On Thursday, Friday and Saturday nights, some of the local clubs hold their transgendered nights, which is my opportunity to get out and meet some of the lovely t-girls in the city. I keep hoping to find a nice girl to date, but mostly I just run into girls who are "working" to make a little extra cash.

Last Thursday I got dressed up in a nice, button down shirt, a pair of dark slacks and a highly polished pair of black shoes, and headed out to the OUTside Club's Thursday night transgendered night. I arrived around 11 o'clock at night, which is about when the party gets started. I walked in and surveyed the scene. Mostly it was the same crowd as usual, a few really good looking t-girls who I know were professionals, a few cross-dressers with bad wigs who I could tell were just starting their transformations, and a bunch of guys hanging around and ogling the girls. It looked like it was going to be another sorry night.

Then I saw her, standing by the bar sipping a vodka cooler, a beautiful, blonde slim t-girl wearing a short skirt and spaghetti strap top. She was about 5 feet 6 inches tall, with a few extra inches added by her tall heels. She had blonde, shoulder-length hair with a slight wave in it, which bounced as she laughed. Her body was very slim, and though she appeared to not have any breasts, her legs were amazing and her skin was creamy white and looked smooth.

I started to move towards her, and soon she looked up and caught my eye. For a moment, her blue eyes sparkled as we connected, but then I saw a strange look cross her face. She quickly grabbed her purse and taking a wide berth around me, ran towards the door. I turned to call out after her, but then my brain kicked in and I suddenly realized what I had just seen. The beautiful, vivacious blonde I had just seen was actually Mike, from the office! Or, at least, inhabiting the same body as Mike from the office, because in the few moments of observing the woman at the bar, she definitely showed a different personality than the mousy, accounts payable clerk to works a couple cubicles over from me.

I stuck around at the club for a little while, but I couldn't get the amazing blonde out of my head, so I headed home and tried to fall asleep, for the first time in months looking forward to going into work the next day.

Friday morning I showed up at the office early, the first time that has ever happened, but just sat at my desk without working. I waited, my heart pounding, for Mike to appear, but come 9 o'clock he still hadn't come in. Mike had never been late before, and I was starting to get worried that I might have scared him away from work for good, but then about 9:30 he showed up.

For the next half day I tried to get Mike alone to speak with him, but he was very adept at avoiding me, always rushing off to a meeting or to the mail room whenever I approached. Finally, after lunch I had my opportunity, catching Mike walking down a hallway towards me, and knowing that there was no way for him to reverse his direction. Staring down, he tried to move around me, but I blocked the hall.

"Hey Mike," I said, trying to sound cheerful and nonchalant, "how you doing?"

Mike, staring at his feed, mumbled something I couldn't even hear. I plunged forwards.

"So, last night I was out at this club, the OUTside. I don't know if you know it, anyways, there was this amazingly hot blonde there. She was so attractive, but I didn't get an opportunity to speak with her before she left. I really wish I could have spoken with her." I paused, but Mike didn't make any move, just continued to stare down.

"So," I continued, "I'm heading out to this club tonight called Blo on Smith Street. It'd be great if I got an opportunity to meet the amazing woman I saw last night. If you know her, maybe you could pass on a message for me."

Mike nodded and spoke very softly, "Umm, okay." I expected him to push past me right away, but he kept staring down. I looked down, and realized what he was looking at. I had a rock solid hard-on that was straining against the fabric of my slacks. Normally I'd be mortified to be walking around with a boner at work, but given Mike's interest, I decided to play it up. I put my thumb through my front belt loop, and stroked my cock through my pants with my fingers.

"Anyway, let the blonde know that I'd really love to see her tonight," I concluded. With that, I turned and let Mike pass me.

Mike disappeared from the office for the rest of the afternoon, my boss told me that he had asked for the afternoon off to run some personal errands. I was a little depressed, because it made me think that perhaps Mike's beautiful, blonde alter-ego was going to avoid the Blo club tonight. I tried to keep my spirits high after work as I got ready to go out, but I couldn't help but feel like I wasn't going to get my wish.

I arrived at Blo earlier than I usually do, showing up at 9:30 pm. I scanned the mostly empty room, no signs of the blonde. I grabbed a beer and stood at the bar, hoping that she would show up. I stared at the entrance, my hope rising each time I saw a shadow in the entrance way, but depressed each time someone other than the blonde turned the corner and entered the club. I took a swig of beer, and sighed. Just then, I felt a tap on my shoulder. "My friend Mike tells me you are looking for me," a soft voice said.

I turned around, and there she was. She was standing close to me, and the odor of strawberries came from her shoulder length blonde hair. She was wearing a thigh-high, bare shoulder gold and black dress. I looked directly into her blue eyes, and a big smile came across my face. "I didn't see you come in," I said.

"I was in the powder room, fixing my makeup. I'm Emily," she introduced herself.

"I'm Steve," I replied back, and stood frozen not sure what to do next.

"Don't I get a hug?" Emily asked, her eyes sparkling and a sly smile coming across her face. I grabbed her and held her tight, and I know she couldn't help buy notice that my cock was already hard and pressing against her stomach.

I bought Emily a drink, and we chatted for a bit. She was confident and funny, always looking me in the eye, nothing like her alter-ego Mike from work. Emily exuded a passion and sexual energy, and was generous with her physical touches, constantly touching my arm or chest when telling me a story. After we finished our drinks, we hit the dance floor, and soon Emily was in my arms facing away from me, her ass pressing up and grinding against my groin. I let my hands drift down her body, past the hem line of her skirt and across the smooth skin of her thighs. I buried my nose in her blonde hair, inhaling deeply, and then moving her hair to the side so I could kiss the nape of her neck.

We continued to dance, our bodies sliding against each other until I was ready to explode. I would have taken Emily right there, in the bathroom of the Blo club, I was so horny, but I decided a slightly more refined approach was called for.

"Emily, my apartment is only a few blocks away. Would you care to come over for a drink?" I asked. She smiled, grabbed my hand and without a word led me out of the club.

The four block walk to my apartment was one of the most torturous events of my life. I just wanted to be upstairs in my apartment with Emily in my arms, but the walk seemed like it took forever. Finally we arrived at my building, and took the elevator to the 12th floor. Just as the doors open, Emily turned around, pressed me against the back of the elevator, and gave me an amazingly passionate kiss. My knees buckled and the blood drained from my head. I felt like I'd just run a marathon. Emily turned and strutted out of the elevator, asking me "what apartment number?"

"1214," I called out weakly, still steadying myself against the back wall of the elevator. I probably would have stood their all night if the doors starting to close hadn't jarred me back to reality. I dashed out of the elevator just ahead of the closing doors.

Emily was walking down the hall, about 10 feet ahead of me. She reached up to her shoulders, and moved the straps of her dress off down her arms. The dress fell to the floor, and Emily stepped out of it. She walked down the hallway wearing nothing but her black heels and a black thong showing off her amazing tight ass. "Can you get that for me," she asked, gesturing back towards the dress lying on the floor.

I was turned on and terrified at the same time. I so wanted Emily, but was scared that one of my neighbors might exit their apartment and see a beautiful woman wandering down the hall with nothing but a thong on. I had no idea how I would explain that.

Emily reached my door, and turned around, pressing her back against the door and sliding her arms up to the top of the doorway. As I approached, I could see Emily's cock straining against the front of her little black thong. That would be even harder to explain to the neighbors. I reached the door, and Emily wrapped her arms around, pulling me close in to kiss her. She parted her lips, and I soon found her tongue exploring the inside of my mouth. I let my right hand run down her back and over her precious ass as I fumbled with my keys in my left hand, trying to unlock the door and get us inside before the neighbors saw us.

Finally, as nervous sweat poured down my brow, I unlocked and opened the door and got us inside. I breathed a sigh of relief, but Emily just laughed. "You seem a little nervous," she said, walking into my kitchen, "let's see if we can't find something to cut your nerves." She opened the fridge and pulled out a bottle of white wine I had chilling, as I collapsed onto the couch. I watched her move around my kitchen, finding wine glasses and an opener, opening the wine and pouring it, all the while wearing nothing but a black thong.

She walked towards me, and I finally relaxed enough to take an opportunity to really check out her body. She had a beautiful face, with her blue eyes, button nose and red lips. Her long neck led down to a slim body. Emily had no breasts, but her nipples were large and already hard. She had a flat stomach, a slender waist and long, thin legs. And, as I have already pointed out, I could see the outline of a beautiful cock inside her tiny black thong.

Emily sat beside me, and handed me one of the glasses of wine. "I guess I got you a little riled up," she said, running her hand down my chest and along my leg. "I hope you don't mind, but I am a little forward when it comes to sex."

"No, I don't mind at all. I was just a little, umm, unprepared for such an incredible display. I really enjoyed it though."

She stood up, and through a sly smile said, "then perhaps you'll also enjoy this." She walked over to my stereo, and turned it on. She started to dance to the music, erotic and sexy, occasionally coming close enough to place a kiss on my lips, but mostly staying tantalizing just out of reach. I stroked myself through my pants. Finally, as the song ended, she walked over to the couch, and straddled me, pushing me back. She kissed me hard again, her tongue again playing with mine.

As she kissed me, her hands went to work, undoing my shirt buttons, my belt and unzipping my pants. I raised myself off the couch just a little, and she slid my pants down past my knees and around my ankles. I kicked my pants off and wrestled myself out of my shirt, all without ever breaking our lip lock, and soon I was sitting on the couch in nothing but a pair of boxer briefs and Emily, still wearing just her heels and thong, continue to straddle me.

Emily finally broke our kiss and stood up. She looked at me for a moment, and then ran her hands over my stomach. I don't want to brag, but I have a pretty rock hard set of abs, and Emily seemed to really appreciate them. Soon she was kissing and running her tongue along my stomach, slowly working her way downwards. She reached the elastic of my boxer briefs, and ran her tongue along and inside my underwear. I moaned and threw my head back, and Emily took the opportunity to grab my underwear with both hands and yank them off. My cock sprang free, and Emily took it quickly in her mouth.

Emily sucked my cock as I stroked her beautiful blonde hair. She was very good, sucking me, as well as adding in elements like licking the shaft, sucking on my balls and flirting with the tip of my cock with her tongue. I was close to coming, and told her so.

"If you come now," she asked, "will you be able to come again later?"

"Yes, for sure," I replied.

"Good," she said, and lunged upon my cock with her mouth, deep throating it. I pushed up against her face, and soon launched a wad of cum into her mouth. Once I had shot my load, Emily looked up at me, opened her mouth and showed me the cum inside it. She smiled, closed her lips and then swallowed down my load.

After that, we moved to the bedroom where we lay on the bed and kissed as I recuperated my strength. After 20 minutes, I was ready to go again, and I finally got a chance to see Emily's cock. Moving into position to sixty-nine each other, I pulled her thong off. She had a nice 6 inch long circumcised member, hard and almost bright red in color. The tip of the cock was covered with gooey pre-cum, which I gladly sucked up before getting her whole cock in my mouth. We continued to sixty-nine, but it was hard to concentrate with Emily doing such an excellent blow job.

After 10 minutes of sucking, Emily said he wanted me to fuck her. Emily lay on her back, and put her legs in the air. I grabbed her legs, and pulled her ass up to my cock. I entered her, and started pushing inside her. Emily grabbed her cock and started to stroke herself as I plunged deep inside her ass.

And that is where this story started. Emily soon shot her load onto her stomach, and when I was close, I pulled out of her and shot my load onto her as well. I cleaned up Emily's cock and stomach with my tongue, lapping up our combined loads in my mouth and swallowing them down. Then we kissed some more, and soon fell asleep in each other's arms.

As an aside, I know that sounds romantic, but I woke up an hour later and my arm was completely numb! After my arm woke up, though, we had an excellent weekend together, and I dropped Emily off at her place on Sunday evening. "I hope to see you again soon," I said.

"Me too," she said. "We can probably communicate through our mutual friend Mike. Just let him know when you want to see me, and I'll do the same. I'm sure we will be able to arrange many more meetings."

On Monday I trudged into work, depressed about the week ahead as usual and pining for my excellent weekend again. Mike came in, blond hair back in a ponytail and head down as usual. He walked by my desk without saying a word, but after my computer booted up, I got an IM from an Emily69 saying how much she enjoyed our weekend. I replied back that I enjoyed it too, and heard the ping of an incoming IM from Mike's cube.

Not much has changed at work since meeting Emily. Mike is still pretty non-communicative; though now we usually eat lunch together, though mostly we don't say much. But every once in a while, Mike will say something funny or sassy, and look up at me, and I'll see sparkling blue eyes and know that Emily has joined us for just a moment, and I'll start looking forward to our next meeting.

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