tagTransgender & CrossdressersEmily and Steve Ch. 09

Emily and Steve Ch. 09


Over the next few weeks things really started to settle in at work. Emily was being more than accepted, she was being lauded. Emily, feeling much more comfortable as a woman, started being a much better worker. The quality of work that Emily was producing was far superior to Mike's work. She was featured on the company's intranet site as an inspiring story.

But while things were going well at work, things seemed to be getting worse at home. The first few nights after Emily started living full time as a woman we had amazing sex, but quickly our interested started to diverge.

I wanted to stay in and have a nice dinner, maybe getting cosy on the couch with Emily and watching a video. If we went out, I wanted to go out to a nice restaurant, maybe to a lounge for a couple of drinks and then head home to bed.

Emily, now living as a woman, wanted to go out and party. She wanted to get out party, dancing and drinking. I would come home from the gym and find her circle of friends hanging around in the apartment, already drunk and stoned. I would beg Emily to stay in, but in the end I would always get dragged out to the club.

The worst thing, though, was that I noticed that Emily started liking attention from other men. At the club, she was out on the dance floor while I was fuming by the bar. Soon her pretty little blonde body would draw the attention of the skirt chasers at the club. She would be surrounded by dudes. I couldn't watch, it made me sick to my stomach.

Emily would always tell me afterwards that it didn't mean anything. She was just having fun. She loved me, and was only going home with me. I believed her, but I stopped going out with her to the clubs, it was just too hard for me to watch.

Things came to a head a few weeks after Emily's change. Tessa, her friend from the country came down for the weekend to celebrate the change. We were sitting around on Friday night drinking a few glasses of wine and chatting.

"So," Tessa said, "when are you going to start the drafting course?"

Emily turned red, and looked down. I raised my eyebrows, confused. "What drafting course?" I asked.

Tessa stammered, "I'm sorry, I thought you had told him. I shouldn't have said anything."

Emily looked up, "no, it's okay Tessa. Steve, I am taking a night course this semester at school. It starts next week on Tuesday and Thursday nights. With it, I'll have the prerequisites to apply to go to university and get a degree with industrial design."

I shook my head. "What? You want to go back to school?"

Emily nodded. "Yes. I don't think accounting is for me. Accounting was something to keep a low profile when I was Mike. Now I am Emily, I want to do something else. Are you mad?"

I shook my head. "No, not mad. I just don't understand why you didn't say anything to me. I would have thought that's the kind of thing that we would share. But, whatever, that's okay. Don't worry about. So, tell me, where do you want to go to school?"

"Virginia tech has a really good program," she said. My jaw dropped. Tessa quietly picked up her glass of wine and walked into the kitchen. Emily just looked at me, waiting for me to say something.

It took me a minute to compose my thoughts, and I really wish I had handled this next bit calmly, but I didn't. Instead, I said, "Virginia fucking Tech? That's two thousand fucking miles from here! You just up and decide to move to Virginia without even talking to me?"

Emily tried to grab my hands to reassure me, but I just pulled away. I stood up and paced.

"Please, Steve," she said. "I haven't decided anything. We can talk about it, but let's talk about it later, okay?"

"No," I screamed. "Not okay. Nothing is okay any more. Recently, you seem to be off in your own little world, and I'm getting left behind all the time. How can you even think of moving to Virginia, when we are making a life for ourselves here?"

"I don't understand what is going on here, Steve," Emily said, tears welling up in her eyes. "You were so supportive of me becoming Emily full time before. Now as I continue to grow as a woman, you suddenly revert to this Goddamn caveman? It is my life to direct, Steve, not yours!"

I stopped pacing and walked right up to Emily. "Not mine? Not mine? I made you. Remember, you said that. You would never have done this without me. I made you, and now you just want to chuck me aside. Not acceptable. Not acceptable."

Emily stood up, and pushed me aside. Tears were streaming down her cheeks. "You know what, fuck you. Tessa and I are going out, and I think we'll stay in a hotel tonight. You can sleep alone in your kingdom, your fucking highness."

With that Emily stormed out, slamming the door behind her. I picked up a dining room chair and hurled it across the room. It crashed against the wall, and fell limp to the floor. Just then, Tessa walked out of the kitchen, sheepishly.

"Oh shit, sorry Tessa. I didn't realize you were there."

Tessa picked up her bag, and started walking towards the door. I called after her. "Tessa, please, try and talk to her. I do support her, but I just want to be included in the decisions she makes. We are a couple, she can't just go off and live her life like a single person."

Tessa looked back sympathetically. "Steve, Emily appreciates what you have done for her, she really does. But you've given her wings now. She's going to want to fly, to experiment. She's made one change, now you have to be prepared that she is going to want to make a whole host of changes. If you love her, either you'll find a way to support her, or you'll let her go."

With that, Tessa walked out the door. I collapsed on the couch and started to cry.

* * *

Tessa and Emily didn't come home that night. The next day I talked to Emily on the phone. She was going to spend another couple nights at the hotel with Tessa, because she wanted to think things through. I pleaded with her to come home.

"No, Steve, I need to figure out where my head is at. You need to do the same. We'll talk on Monday after work, okay."

I sat around thinking all day Saturday about what I wanted. The more I thought, the more it was clear to me. I wanted Emily in my life. I needed a plan to get her back. As luck would have it, Frisco called the apartment asking after Emily.

"Oh, she's not in right now," I said. "She's out with her friend Tessa. Are you meeting up with them later?"

"Yes, at Foo Bar," Frisco said. "Are you coming?"

"Maybe," I said, but I knew I was.

I had a shower and got dressed up and then headed out to Foo Bar, by the time I got there the line up was already around the block. I tried to get past the doorman in the VIP lounge, but without the hot blonde on my arm, no such luck. Instead I stood in line like all the rest of the suckers.

After 30 minutes, the line up barely moved. "What's going on," I asked the person in front of me.

"DJ Ank Kar is playing tonight," the guy said in between sucks on a pacifier.

"Who is that?"

The guy looked at me like I was an idiot. "Only the hottest DJ from Eastern Europe right now." The guy rolled his eyes, and went back to sucking on his pacifier. I shook my head, and continued to wait in the line.

Two hours later, and I had moved forward about 10 feet. Only another 50 feet to go. At this rate, I figured I would get into the bar sometime around noon on Monday. I was trying to think of another plan when I spotted Emily walking out of the bar with two guys. I jumped out of line and started to follow them.

They had a good head start on me, so I nearly lost them when they ducked into the alley behind the Chinese food restaurant, but just as I was running by I saw movement out of the corner of my eye, so I turned down the alley.

There, at the dead end of the alley was Emily, passionately kissing one of the guys as the other guy rubbed her ass and kissed the back of her neck. Part of me wanted to scream out, but a larger part of me wanted to see what would happen, so I hid behind a dumpster and watched.

The guy kissing the back of her neck pulled away and said, "Oh, Todd, you should feel this chick's ass. It is rock solid." His hands continued to squeeze Emily's ass.

The guy kissing Emily's mouth, who I suppose was named Todd, broke away from Emily's lips long enough to say, "you think her ass is nice, you should try feeling her tongue in your mouth. She is a goer for sure, Rich."

I sat in the darkness and watched as Rich and Todd continued to grope my girlfriend. Emily's hands ran down Rich's chest, and came to rest on his groin. She pulled away from the lip lock and said, "I want to see that cock of yours."

Rich looked around. "Are you sure, baby, that you want to do both of us, in this alley?"

Emily nodded, "yes, I am. I am sick of my boyfriend telling me how to live. I am a young, beautiful woman, and I should be able to act how I want, right?"

Todd, undoing his pants, said, "fuck yeah!"

Emily dropped to her knees, and started to blow Todd's hard cock. Rich shrugged his shoulders, and whipped out his dick as well. Emily grabbed Rich's dick and started to stroke it as she blew Todd. Both the boys had average size, uncut cocks, and both were hard as rock already.

Emily sucked off Todd for a few minutes, and then switched, sucking Rich while stroking Todd. I sat there watching. I saw the pleasure on the boys' faces. Watched the way their eyes fluttered shut and the way their mouths involuntarily quivered and opened with let out muffled noises of pleasure. I watched as their backs arched and toes curled as Emily's expert mouth worked on their dicks. Mostly I watched those cocks, sliding in and out of Emily's mouth. I could see the coating of saliva on their shafts glistening in the light in the alley, and the occasionally bead of spit roll down Emily's chin and fly free for a second until it hit the ground.

I closed my eyes, trying not to see it, but then I heard it. The boys' gasps and moans, their occasionally expressions of disbelief at the pleasure, they brief thank yous to the gods above for delivering Emily onto the end of their cocks. And I could here Emily's mouth moving up and down on the shafts, the sound of her gulping and breathing, the sound of spit building up and being released, the licking and lapping of her tongue.

I opened my eyes again, and watched. The boys were close to cumming. Todd, currently getting the hand job, pulled his cock away from her hand. "If I am going to cum, I want to cum either in that mouth or in your pussy, baby. I don't want a damn hand job."

Emily kept her mouth working on Rich as she raised her ass in the air, pulled up her skirt and moved her underwear out of the way. Only then did she break off Rich's dick to say, "forget my pussy, come in my ass!"

Todd smiled and moved close. Emily grabbed his cock and started to guide him towards her awaiting hole. Todd though, reached down and grabbed at Emily's crotch. He pulled back suddenly.

"Oh shit, dude, this chick has a cock. She's a guy!" he exclaimed.

Rich stiffened, his cock still hard in Emily's mouth. He seemed to waiver for a moment, but then shook his head. "Whatever, this mouth is so good, I don't give a shit. Keep sucking my cock, you little faggot. Todd, if I were you I would fuck this faggot whore's ass."

Emily broke off from Rich's cock and exclaimed, "Just fuck my ass, Todd," before hungrily gulping Rich's dick back down again.

Todd stood for a moment, and then shrugged his shouldered and pushed himself in. I heard him moan as his dick entered Emily, and Emily squealed briefly before continuing to hungrily suck Rich off.

I couldn't watch anymore, so I ran from the alley. As I was leaving, I heard Rich declare that he was shooting his load down Emily's throat. "She is swallowing it all down like a fucking cumdump!" he screamed. I covered my ears and ran.

I wandered aimless for hours, finally ending up in a park I used to come to back before I met Emily. On the north side of the park, along a darken stretch of the road is where the transsexual hookers work at nights. I used to cruise along here on nights when I was really lonely, looking for a quick fuck.

I don't know what drew me there. I think I just wanted to feel someone, to know that I could feel something. I didn't even feel like having sex. No, I felt like being punished. I picked the biggest, most manly looking tranny I could find, and approached him. He was at least 6 foot 4 inches tall, and despite his best efforts at makeup was let down by his square jaw and five o'clock shadow.

"Hey, I want you to fuck me," I said.

"Do you have a car?" he asked, looking around.

"Not tonight. Just take me over in the bushes there, tear my pants down and rape my ass. I want you to punish me. Make me hurt," I said.

The guy looked at me funnily, but then said he'd do it for one hundred. I pulled out five twenty dollars bills and gave it to him as I started to wander over to the bushes.

Before the tranny had even followed me into the bushes, I had my pants around my ankles, and was bent over against a tree. I spread my ass cheeks and ordered him to fuck me hard and fast.

The tranny stood behind me and hiked up his skirt. I could hear him playing with himself as he took a condom out of its packet. Once he was hard enough and had the condom on, he entered my ass.

He was big, much bigger than Emily had been, and not at all gentle. He pushed in me, and I shuddered with pain. That was fine though, for it was pain I wanted to feel. The tranny started pushing into me hard and fast. I started to relax, and the pain started to turn to just discomfort, and then surprisingly to pleasure. I opened up, and soon shivers of pleasure were pulsing from my ass. It was causing my cock to stand up at attention. I soon found myself reaching down and jacking myself off as the tranny continued to pound away at my tight asshole.

"Do you like that?" he asked me.

"Yes," I whimpered. I did. I suddenly felt an intense desire to have more of this. I wanted more cocks in my ass. I had never felt that way before. The feeling welled up in me, and I found myself spurting my load against the tree and the tranny pounded hard and fast. Once I was done, the tranny took off the condom, tucked away his cock, pulled down his dress and walked away.

I was left in the bushes, my pants around my ankles, feeling both strangely satisfied but at the same time empty.

* * *

On Monday evening, I thought it would be best to clear the air between Emily and I. My plan was to lay everything out on the table and see how we can make it work. I went to the gym first to work off any nervous energy and anger, and so when I arrived home, Emily was already sitting on the couch. I walked over and sat down.

"Can we talk now?" I asked. She nodded.

I started, confessing to Emily that I had cheated on her on Saturday night, without getting into too much of the details. I concluded by saying, "I wanted to tell you that, so we have no secrets. I want to make us work, and I hope you do as well."

Emily took my hand, and told me she forgave me. It felt good to hear those words. Next I expected that she would admit to cheating on me, but instead she didn't. Instead, she said, "I want to go to Virginia, Steve. I want to live my life, now. I have been living someone else's life for so long. It's finally my chance to live my life. And while I know it is selfish, I need to make my own decisions. I can't have you as part of that, because then I am just living someone else's life again."

I was stunned. "Emily, I thought you wanted this. I thought you loved me."

"I do love you, Steve, but what we have here, that is your creation. You are the one that is looking for a partner, a lover, a wife. You are the one that wants someone to stay home with and cook dinners and watch videos. Maybe some day I'll want that, but right now I want to be a young, vibrant girl. I want to experience the world, and sow my wild oats. I need to go out dancing and drinking. I need to take courses to learn new things. I need to... ummm." Emily was stuck for another example.

With nothing but venom in my heart, I said the following words, "you need to have two guys double-team you in an alley."

Emily looked at me. I stared at her, my hardest, coldest stare. She wasn't ashamed, as I had hoped. Instead she was angry. "What the fuck, Steve, are you following me around now? Stalking me? Jesus Christ, Steve, that is the problem here. You rushed me into this, this whole exclusivity thing. I made a mistake agreeing to it, but you were so nice and so supportive, it felt like the right thing to do. Now, it just feels wrong."

Emily stood up, and walked towards the door. "I'm sorry, Steve, this has got to end. I do love you, though you might not be able to see that now, but I can't stay with you." Emily opened the closest by the door, and pulled out two large suitcases. She walked towards the door.

It hit me then. She was leaving. She had always planned to leave tonight. That's why the suitcases were there already. She had already packed.

I feel to my knees, trying to beg her, but instead just sobs came out of my mouth as tears rolled down my face.

Emily started crying as well, she opened the door, and gave one look back. "I am sorry, Steve, I love you, but I have to do this. Goodbye."

The door shut behind her. I crumpled on the floor.

* * *

Emily wasn't in at work on Tuesday. Rita came by to tell me that Emily had given Glen her resignation letter, effective immediately, on Monday after work. She had left a forwarding address for her final pay cheque to Tessa's place in the country.

I fell apart after that, as you do after relationships end. I went through the usual stages. Drinking and crying, drinking and seeing hookers, drinking and cursing Emily, drinking and trying to call her late at night, and finally just drinking.

Time has passed, and I think things are better now. I ran into Tessa last week. After a few awkward words, I asked about Emily. Tessa just said that things were going well, and she was going to be starting at Virginia Tech in the fall for industrial design.

I smiled. "Great to hear. Tell her I said hi, and wish her luck with her studies for me, okay?" Tessa promised she would, and then she walked away.

As for me, I still work at the same company in the same boring job. I still go home and whack off to tranny porn most weeknights, and go out crusing the tranny bars on weekends. I keep hoping that I will meet another girl. A girl like Emily, but this time one that wants to settle down, to make a life with me. There's been a couple how have been potentials, but nothing has stuck yet. But I haven't given up hope. She's out there, I know it. I just have to keep searching.

In the meantime, I always have my memories of the glorious time I spent with that special girl named Emily.


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