9 to 5 Pt. 05

"I've got a little housewarming gift for you." Stacy said, handing me a gift-wrapped box, "I hope you like it."

I tore the wrapping paper off the box to reveal a 6-inch vibrator. "What the fuck, Stacy?"

"For those lonely nights in your new flat." Stacy mused.

I could not help but blush.

Part 5

I was nearing the end of my first month at Jackson and Wright, and I had ramped up to my full ability and surpassed all my colleagues in bringing in the highest revenue from my trades. This was starting to get to my so-called mentor, Greg Lowmax. I was generating at least 10% more revenue than him, and though he tried to play it off as a result of his great training, the truth was he was getting stressed out by it.

I had also received the keys to my new flat in Hanwell, though I had no furniture. I had ordered a load of items from Ikea, so I hoped that my flat could be habitable soon. Stacy helped me paint the flat during the evenings after work. And after Ikea delivered my furniture, we had a fun evening of assembling flat-pack furniture and red wine.

It was with a heavy heart that I moved out of Stacy's home.

I had a tear in my eye as I hugged her. I told her, "Thank you for everything you have done. I'm hoping to fully discover who the new me is soon, but you have helped me on my way."

"You soppy old mare." She teased me, "All I did was see an opportunity to help you get a job; I never contemplated what effects it would have on you. I feel bad that I might have made you into a sissy."

I held her hand to my heart and said, "Don't be sorry; I was lost when I was fired, but living these past months as Brenda has made me realise that I was more lost than I knew. Now I'm seeing my life with a renewed optimism that I did not know was possible."

That set Stacy off crying, "Oh Brenda, I wish you nothing but happiness, no matter how far down this rabbit hole you go. I will always be here for you."

All too soon, I was sitting alone in my flat, alone for the first time in weeks. It felt strange, but also liberating.

I soon settled into my new home; I had joined the local gym, and I divided my time between my flat, the gym, and work. I guess I was trying to avoid socialising, mainly to avoid facing the real prospect that I might be starting to be attracted to men.

The girls at work tried to invite me out a few times, but I made some excuse not to go.

I was out having dinner with Stacy a few weeks after I had moved out, just catching up.

"So, I've heard you have turned down some nights out with your office girlfriends?" Stacy asked me.

I took a sip of my wine, trying to delay answering, but it was no use. "I'm too scared to go out; what if I meet another guy? Part of me is excited to see where it goes, but the other half is shit scared because I'm not a real woman. I might get the shit kicked out of me."

Stacy shook her head and said, "Look, there are ways to dip your toe without that kind of rejection."

"How?" I asked her.

"There are tranny-friendly bars you could go to; the men there are looking for girls like you." She informed me.

I let her words sink in before replying, "So when do we go?"

She put down her fork and said, "Whoa, Missy, do you want me to go there with you?"

"I can't go alone; I'd need a wing girl." I reasoned with her, "And besides, you made me this way."

"Touche." She said flatly, "Ok, let's do this."

We made plans to go to one of these clubs this coming Saturday night. I now had a nervous excitement about what possibilities this could lead to. It would finally answer if I was attracted to men or if it was a drunken mistake that had led to me snogging a guy the last time I went out.

That night, back in my flat, I had just finished getting ready for bed. I had butterflies in my tummy with a mixture of fear and excitement for the upcoming night out. I replayed the last time I went clubbing with the girls in Camden--the feeling of being desired by my mystery man.

The memory of his hands on my butt as his tongue explored my mouth started to get me horny. My cock started to tent my satin nightgown as my arousal built. I imagined what my mystery lover would look like naked--was his cock as big as mine? Would his seed taste as good as my own?

I reached for my nightstand and slid open the drawer. Staring back at me, still in its packaging, was the dildo Stacy brought me as a housewarming gift. Taking it out of the draw, I tore it out of the box and examined the 6" faux cock. It felt heavier than I expected as I gently stroked it like I had my own so many times.

I brought it to my nose and sniffed it, and it had no odor. Reaching out with my tongue, I swirled it around the head of the fake phallus in front of me. Closing my eyes, I imagined it was my lover's cock at my lips, before parting and willingly taking the head into my mouth.

It was cold at first, but the warmth of my mouth soon warmed it up. I let out an uncharacteristic moan, and I pushed the silicon cock deeper into my mouth. My free hand reached under my nightie, my own cock leaking badly. I rubbed my fingers around my head, getting them slick with my own juices. I felt the fake cock at the back of my throat. I paused for a moment before sliding it back out. I imagined the moans of pleasure from the imaginary man I was pleasing.

I moved my slick fingers past my balls and rubbed my index finger at the entrance to my boy pussy. I pushed the cock back into my mouth as my finger pushed past my last shred of masculinity as it entered my arse. I whimpered as the finger invaded my virgin hole. Memories of the whore finger fucking me came flooding back as the sensation of pleasure overwhelmed me.

The hand holding the dildo was now stationary, but I was unknowingly bobbing my head up and down on it, blowing it like a cheap hooker.

Soon, one finger was not enough, and I pushed a second past my forbidden threshold. I had tears in my eyes as I pumped the fingers in my butt, and blew the fake cock. I was not sure when I inserted a third finger, but my hips were bucking to meet the invading digits. But I still needed more.

I withdrew my fingers from my arse, suddenly feeling empty. I removed the dildo slick with my saliva from my mouth. And without thinking, in a frenzied desire for satisfaction, I pushed the head of the fake cock into my boy pussy. I stretched more than I thought was possible; the pain was excruciating, but deeper I went.

I needed the connection with the man in my mind. I started to pump the dildo within me; it had hit my G-spot, and the floodgates opened. Both my eyes and cock were streaming their juices, and the front of my gown was soaked. With my free hand, I cupped my breast and rolled my thumb around the nipple.

"FUCK!" I screamed as my cock exploded my man juice over my nightie and belly.

It was the heaviest orgasm I had ever had. The feeling was so intense that I could not slow down the assault on my body. The feeling of the orgasm had barely subsided when I let out another scream as I creamed my nightie for a second time without touching my cock.

I managed to will myself to remove the dildo from my arse. I was panting heavily as I fought to keep up with the oxygen demand that my body now screamed for after such a release.

I instinctively scooped up the mess under my nightie and brought it to my mouth; the taste was divine. At this moment, I knew I wanted more; it was wrong of me to willingly want this, but I was fast getting to the point where I did not care. If the limited sexual exploration had yielded me so much pleasure, then I would willingly go further down this rabbit hole.

The true test would be on Saturday, when I'm faced with an actual man. Would I chicken out, would I be turned on by the reality of acting like a woman to please a man, or is this just a wild fantasy? Time would tell, but for now, I had to put a fresh nightgown on before I drifted off into a lovely post-orgasmic sleep.

The following few days flew by at work. I was quickly becoming the star trader in my department, and I could tell I was starting to be noticed by the department head.

Though I was enjoying work, I was glad to get out of there on Friday night to start my weekend of discovery. I'd either return to work as a straight guy masquerading as a woman or as a fully-fledged sissy cock loving tranny.

I had now started to follow my new evening routine. After dinner, I'd dress in some sexy lingerie and then fuck myself with my dildo until I came. I never wasted any of my spent issue, and lapped it up eagerly.

My dreams were like segments for porn videos, and I was the girl getting pounded by a hunk of a man. At the beginning of this journey, I was scared the shift to living as a female would turn me queer, but I was bordering on obsession to explore my newfound feminity. 

I was almost as giddy as a schoolgirl as I left my flat to meet up with Stacy. I told myself to calm down and temper my excitement; after all, I might still bottle it. I wore a very short figure-hugging black dress, hold-up stockings, black 4-inch heels, and a matching handbag. I went for a more formal than slutty makeup job, but my head was styled into a sexy tousle.

I was getting more than my fair share of male attention on the tube, and I loved it. I met Stacy at Piccadilly Circus station.

"You look fantastic." Stacy complimented me as we greeted each other.

"Why thank you? I feel fantastic." I replied.

We took another train to Limehouse and headed to the Way-Out Club. It was a surreal experience. There were plenty of T-girls on show, some like me who could pass, and some who looked like blokes in dresses. No one seemed to care, and there was a lively atmosphere, and Stacy and I were soon set up at a table with a couple of drinks, taking in the ambience.

Stacy excused herself to head to the ladies while I kept watch over our seats. A guy in his early 40s approached me. I had been observing him most of the evening; he had been slowly working his way through the room, being rejected by one girl after another. Great, I thought, my turn.

"Hello, darling, can I buy you a drink?" He asked; he was clearly not the man of my fantasies.

Fearing I would only attract this type of "admirer," I replied, "No, thank you; I'm here with a friend."

Several hours passed, and though I was having a great time, I feared that the night would be a bust in finding a man to scratch my new itch. What made matters worse was that Stacy got hit on several times.

I was thinking of calling it a night when a group of young people walked in. Unlike most of the groups, this was a mixture of guys and girls, and they took up a table near ours.

Observing from afar, it looked like one of the group members was a t-girl like me, and the rest were her supportive friends. One of the lads was a fit-looking guy, early to mid-20s, with dirty blond hair. It was almost like looking into my past; he was the same type of guy I used to be.

I must have been staring, because he turned and our eyes met. He smiled at me, and I smiled back, but quickly turned away from him, suddenly feeling very shy.

Stacy had noticed this interaction: "Someone has a crush."

"Shut up." I snapped back, then I caught the guy walking over to us out of the corner of my eye. "Shit, he is coming over."

"Hi, I'm Dave." The handsome stranger said this, holding out his hand.

On autopilot, I took his hand and replied, "Brenda, nice to meet you."

"May I join you?" Dave asked.

"Oh, please do, Dave." Stacy said, pointing to the empty seat next to me. As Dave sat down, she stood up and said, "If you two will excuse me, I'm going for a little dance."

Dave looked a little nervous as he asked me, "So, are you a T-girl?"

I laughed. "Yes, I am. I'm assuming that is OK with you."

"Yes, yes." He said, stuttering over his words, "If you were not in this type of club, I would never have guessed you were not a real woman, ah, not that you are not a real woman, of course."

"Relax, Dave; I'm not that easily offended." I said, before putting my hand on top of his reassuringly, "Don't worry, this is my first time here as well."

This seemed to put him more at ease, and I felt the tension in his hand relax. He went on to explain that he was here to support a friend of his who had recently started their own transition. After his friend came out, he said he had become a little obsessed with girls like us.

He was 22 years old, so slightly younger than me, and was doing a postgraduate course at Kings College. I gave him the Cliff Notes version of my life, but with a few little white lies about why I had started to transition.

I felt relaxed chatting with him, and I was enjoying his company. Was I attracted to him? If I had to honestly answer, I'd have to say yes. Did this mean I had a type of man I was attracted to? I guess so. I'd have to freely confess that since we entered this club, I have exclusively been checked the guys out.

It looks like I am turning queer, or the best thing to say is that I was already queer deep down; I just did not know it. There must be so many men and women whose nurture had suppressed their nature that they live happy hetro lives.

Dave asked me to dance, and I accepted his invitation, and he led me to the dance floor. The music was already into the slow numbers, and he put his hands on my hips like I was a hot potato.

I slid his hands around to my lower back before wrapping my arms around his neck. "Relax; I don't bite; it is just a dance."

He smiled, and we started to move together in time with the music. With my heels on, I was roughly the same height as Dave, and I was starting to get lost in his eyes.

He whispered to me, "You really are beautiful."

I blushed and replied, "You're not too hard on the eye yourself."

Then it happened: he leaned into me, and our lips met. Just a quick peck to see if the coast was clear, and when I smiled back, he came back in for seconds. This time I could not blame it on the booze; I was kissing him because I wanted to.

In his newfound boldness, his hands slipped from my lower back and onto my arse. I let out a girly moan, and he squeezed my flesh. I had no pretense of what I wanted; my cock had answered for me as it stiffened and tried to break free of its tucked hideaway.

This was it--a full embrace of my newfound womanhood--and she was in heat. My groin rubbed against his, and he too was rising to the occasion. This only turned me on more.

I whispered into his ear, "Do you want to get out of here?"

His face was a little panicked. "I've never been with a girl like you before."

I took his face in my hands and said, "I've never been with a boy before; let us explore this together."

I kissed him, and he nodded at me. We left the dance floor, and he said goodbye to his friends as I found Stacy.

"I'm off now." I said to her, She was with a small group of T-girls she had befriended. "I'll let you know how I get on."

Stacy said, "Girls, little Brenda here is about to pop her cherry."

The other girls all whooped and cheered.

Stacy brought her head close to mine and said, "In all seriousness, please be careful, and don't let him do anything you are not comfortable with."

I hugged and replied, "No worries; he might be a hunk, but I could still kick his ass."

Dave came over to us and said, "Ready to go?"

"Abso-fucking-lutly." I said, wrapping my arm around his as we left the club.