tagTransgender & CrossdressersHer New Girlfriend Ch. 04

Her New Girlfriend Ch. 04


4 - Overtime

So let me recap the events leading up to now.

My girlfriend Cheryl video-ed me in her lingerie and masturbating. She fucked my ass until we both came. She first transformed me into a very attractive female by giving me the full spa treatment including a total body hair removal, facial, manicure, pedicure, wig and makeup. Cheryl also gave me a more fitting name, Gina. Then she took me to a sexy lingerie store where I was outfitted in various sexy bras, bustiers, garters, stockings and panties. We were more than ably assisted by the feminine Pierre who gave me my first male blowjob.

While we prepared for a fashion show featuring me for Cheryl's other girlfriends, I gave my first blowjob to some rough delivery guy.

That evening, I dressed in my outfits for the girls. The night was ended with me given my first anal fuck from a male, well sort of, it was Pierre. Who would have thought he possessed such a big, beautiful cock.

Well that was a lot of firsts for me in such a short time. My head was spinning with excitement.

The rest of that weekend, Cheryl made me stay in drag which pleased me to no end. I think it turned her on too. She must have fucked my ass with her strap-on at least a dozen times. I had a lot of difficulty sitting down after that.

Monday, I got up for work. Showered, shit and shaved. I went to get dressed only to find all my male underwear gone.

"Hi girlfriend." Cheryl often called me that rather than the name she gave me for some reason, but I really liked it when called me her "girlfriend."

"Where's my stuff?" I asked.

"You will only wear your new undies when ever you go out." She replied. "But I'll let you wear your normal clothes on top."

I giggled with excitement. "Okay." I replied in kind of a girly voice.

Cheryl helped me select my undergarments: sheer black panties, black garters with a small, red bow in the front and black stockings. On top, I slipped on a matching sheer black cami.

I looked in the mirror and could not believe how hot I looked or how hard I was.

Cheryl just stared at me angrily. I looked back at her apologetically and started jerking off abiding by her rule of no erections in her presents.

I stood in the middle of our bedroom then pushed my panties down to my knee. I firmly gripped myself and started moving my hand in the traditional manner, but it felt totally different... erotic, sexy, hot. I'm not sure how to describe it. It was euphoric.

Cheryl stood there and watched. I could see that hunger in her eyes which only made me want to please her more.

I was close to cuming when she said. "Don't cum on the floor! I'm tired of seeing your stains all over the place."

I felt the surge coming. There was no stopping it. I had no other option I could think of but to cum in my free hand.

"Aa.g.g.h!" I groaned as my sperm shot into my palm. I came so hard my knees were about to buckle.

I looked at my handful of cum and it was about to spill over. I couldn't run to wash my hand since my panties were still around my knees and I didn't want to soil them by pulling them up. I looked at Cheryl. She only stood there and looked back at me.

"What am I going to do?" I started to cry to myself. I slowly brought my hand of cum to my mouth and looked at Cheryl again. She nodded.

I tentatively started to lick my own sperm. The taste was like nectar so I lapped my hand clean trying to drink every drop.

Satisfied, Cheryl let me finish dressing and off to work I went.

Work was great. The sexy undergarments felt great rubbing against my skin. It made things hard, especially in my panties. I was almost disappointed that Cheryl wasn't there to see my erection and make me jerk off again.

Over the next couple of weeks, my wardrobe of under things grew. So did my outerwear; short skirts, tight tops and high heel CFM's.

Cheryl even took me out on a girl's night with some of the others who were here for my fashion show.

The first time out, some guy tried to pick me up at the bar. He placed his hand on the small of my back and let it slide down until it was caressing my ass. I probably would have sucked him off, but Cheryl and the other girls saved me.

I got more daring each day at work. I wore a very light underwired satin half slip under a very opaque women's blouse hidden under my suit jacket and tie. Under my pant I wore the matching white satin boy shorts with garters and white stockings.

Of course I looked incredibly hot. Of course I got hard. And of course Cheryl was there to watch me jerk off and drink my own cum. All of which I really enjoyed.

I finally made it to the office. It was warm but I kept my jacket on all day regardless. But near the end of the day, my manager Katherine asked me to help her get some boxes from the storage room.

Katherine is a tall 5' 10" beauty with long, straight, thick, dark nugget brown hair and intense green eyes. She has fair, smooth skin, large C breasts on top of a well toned, shapely body and long legs. Many of the other girls called her a "dyke" because she was often aloof with many of them and had an aura of superiority about her.

As a manager, she always was impeccably dressed. Today she was wearing white slip under the jacket of a red business suit. The skirt was knee length and had a slit half way up her right thigh. Her makeup was subtle and perfect.

We went to the back and she showed me which boxes she wanted down. I started to reach for the first box when Katherine said "Better take off your jacket or it will get dirty."

Without thinking, I removed my jacket. Katherine stared at me. Well not me but my attire. I was so comfortable I forgot what I was wearing underneath.

Katherine didn't say anything. I got the boxes, put my jacket back on and moved the boxes to where she wanted them.

"Please come to my office." Katherine asked softly but firmly. I followed her to her office not knowing what was going to happen. I took a seat as she shut the door and sat behind her desk.

"First, I have no problems with your private life or your office attire." She stated. "We all have secrets and I want to let you know, what I saw is no one else's business."

"Thank you Katherine." I gave a big sigh of relief. "That's really understanding of you."

She continued. "Does Cheryl know?"

I had forgotten they had met at company functions.

"Yes. She approves actually." I informed her further. "In fact, she helps me pick out my wardrobe." Maybe that was too much information.

"May I see more?" Katherine asked. "Take off your jacket." It was more of an order than a request. Her voice was so commanding I had to obey. I stood up and removed my jacket then placed it on the chair behind me. I began to shake nervously.

"Very pretty." Katherine complimented. "Anything else?"

I could only nod.

"Show me."

I removed my shoes and socks first. Katherine immediately noticed my stocking feet.

"M.m.m.m." She moaned.

I unbuckled my belt then loosened my pants and let them drop around my ankles. I stood in front of Katherine in my satin undergarments! My stiff cock made a huge tent form in the light material of my boy panties.

"What is your name?" Katherine asked.

"Huh?" I looked at her in a quizzical manner. "You know my name."

"No, your name."

Then it donned on me. "Gina." I said sheepishly.

"Well Gina. I 'm pretty sure Cheryl wouldn't allow that." Katherine was referring to my boner. "What does she make you do to fix it?"

I was kind of stunned. My boss was essentially telling me to masturbate in front of her.

"Perhaps you need a little incentive." Katherine offered. She stood up and removed her jacket and pulled her slip over her head. She was wearing a red demi bra that cradled her massive orbs. Her red nipples were pointing directly at me.

Katherine took licked her fingers and pinched each one of her cherries, but I stood the unmoving. My cock was jumping inside of my panties.

"Not enough?" She asked.

She reached behind and unzipped her skirt letting it drop to the floor. Her slip followed. She wore tiny, tight, red lacy panties with stockings held up by a satin garter. She pulled her panties down and exposed an 8-inch uncut penis.

"Inside I'm a woman but I didn't have the courage to cut it off." Katherine explained. "I laugh at the upper execs when they say I don't have the balls to go any higher in the company."

Katherine's tool made mine look like a toy by comparison. I stared in amazement as I pushed my panties down around my knee like I've done for Cheryl so many times before. I started to fist myself while still staring at Katherine. I knew I'd come pretty quickly.

Katherine stepped out of the pile of clothes about her ankles and walked around her desk to in front of me. She stopped my hand from jerking off and replaced it with hers. Her hand felt so soft as she started sliding it along my shaft. For my part, I stood there motionless.

Katherine then fell to her knees. Her hands reached around and grabbed handfuls of my ass cheeks. Her mouth closed around my dick as she pulled me into her face.

Her nose pressed into my body as I was totally inside her mouth. It was unlike anything I felt before; completely different from the blowjobs I received from Cheryl or Pierre. Her head was almost motionless as her throat seemed to be sucking me.

"A..a..a.....h!" I moaned as I started firing my load directly into her belly. Even after I was empty, she continued to suck me, ensuring every last drop of semen was drained from me.

"Good girl Gina!" Katherine praised as she licked her lips. "See? Now you'll be able to please Cheryl by not wrecking your beautiful clothes she picked out for you."

I was totally spent. I couldn't get a stiff even if my life depended on it.

"But now I have the same problem." Katherine said as she stood up and referred to her tent pole.

I was about to drop to my knees and return the favour, but Katherine quickly grabbed me and pushed me face first over a chair and held me there.

"But...What are you...?" I knew what was coming next. I wanted it. I needed it. But what if Cheryl found out. Was I was turning into some sort of office slut?

Katherine spit into my ass. I felt the knob of her cock rub it into my winking hole. She placed it onto the opening and paused.

"Gina, you can be whatever Cheryl wants at home, but at work you're mine."

Katherine increased the force pushing her fat knob into my tight ring. I was use to being "fucked" by Cheryl, so Katherine's cock slid into me easily.

"Oh! Yes! Fuck!" I grunted.

"Gina likes that doesn't she?" Katherine was pleased. "Hmmm. Mine hasn't been the first in your tight ass has it?"

I shook my head "no" And groaned as she drove all of her inside me.

Her rhythm increased, smashing her hips into my ass. I sensed it was only a couple of seconds until....

"I'm c..u..m..m..ing!" Katherine screamed as she shot her load deep into my bowls.

I felt spurt after spurt of her seed ejaculate in my ass. I did not realize that I to had ejaculated again.

Kathleen pulled out of me leaving me bent over the chair with my ass in the air. Cum was leaking out of my asshole and dripping from my own dick. Katherine then grabbed my panties and pulled the over up over my hips; then smeared all the cum the inside.

"What am I going to tell Cheryl?" I fretted.

"I expect you to be mine as I wish at the office if you don't want to be humiliated." Katherine warned me. "And don't even think of quitting."

I silently nodded in agreement. I loved getting corn holed by Katherine, but what to do about Cheryl?

I got dressed and took the transit home; cum was still leaking out of my ass. I could smell it permeate the air in crowded bus. I didn't realize how big the load inside me was. By the time I got home, it stopped, but my beautiful panties were still soaked.

"Hello girlfriend!" Cheryl greeted me at the door.

"Hi." I tried to be nonchalant. I bent over to untie my dress shoes, when Cheryl came up and rubbed her hand on my ass.

"Why are you so wet there?" She demanded but didn't wait for an answer. "Take off your clothes!"

With great trepidation, I started stripping. When I removed my pants, Cheryl immediately saw my sperm soiled panty.

"What have you done?" Cheryl shouted at me. I was about to open my mouth. "Don't lie to me." Cheryl didn't wait for me to say anything. I looked at Cheryl cowering and ashamed.

"You fucked Katherine, that slut boss of yours, didn't you?

I was amazed Cheryl would remember her. I nodded "yes" in confession staring at the floor.

"Good girl!" I heard. "Telling the truth is much better than telling me a lie." Cheryl said. "Don't you think so Katherine?"

I looked up and saw Cheryl and Katherine standing beside each other. "Yes, we are VERY good friends." explained Cheryl. "I needed to have someone watch you at work."

I stood there in awe of what was happening. "From now on, you will be Gina permanently." I looked at Cheryl with a puzzled look.

"You will be Gina my executive assistant at the office." Stated Katherine. "With emphasis on the 'ass' part." they both chuckled.

"And at home, you will be my girlfriend." Said Cheryl.

I was so happy I started to cry like the girl I am.

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by LisaBrooks09/04/18

Gina Hit The Mother Load!

Wow! If I wasn't retired I'd like to have Cheryl as my girl friend and Katherine as my boss! I don't have a penis like I use to (6") because of the hormone replacement therapy medications! It more or lessmore...

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