tagTransgender & CrossdressersHer New Girlfriend Ch. 02

Her New Girlfriend Ch. 02


Chapter 2: Transition

I stayed awake all night thinking of what transpired the day before. My girlfriend Cheryl secretly recorded a DVD and caught me dressing in her lingerie and masturbating with her vibrator deep up my ass.

After the grand viewing, she dressed me up in some of her lingerie again, put one of her wigs on me and fucked my ass with her double headed rubber dildo until we both came.

This morning, my hard on strained against the flimsy material of her panties she made me wear to bed last night.

Cheryl finally stirred awake.

"Hello girlfriend." She said as she reached under the baby doll she also made me wear. Her fingers found my already hard nipple and tweeked the agressively. My cock jumped.

Cheryl slid her hand down my tummy and between my legs to find me hard as rock.

"Well that will never do." She said. Cheryl threw her vibrator at me.

I looked at the vibrator then at Cheryl. She returned an affirmative stare at me. I knew what I had to do. I pulled my panties down to my knees and rolled up onto my knees. I switched on the vibrator and placed the tip against my bunghole. The vibrations immediately sent shivers through my body.

I started to jerk off.

"Good girl!" I heard Cheryl say. "That's so hot!"

It wasn't take long before I started spurting my cum on the sheets beneath me. I remained on my knees; my face buried in my pillow; my body convulsing ever so slightly with the vibrator still sticking out of my ass.

Finally, I rolled onto my back. My prick was still as hard as ever.

"Hmmph!" Cheryl expressed. "Again!"

"But ..... I can't!" I cried. "It's too sensitive."

"Do it or I'll do it for you." Cheryl ordered.

I tentatively wrapped my hand around my stiff and slowly moved my hand up and down. The sensitivity of my cock ran through my entire body.

"Put your ass on top of the wet spot, just like you make me after you come."

I moved my ass on top of it; my hot cum had since grown into a cold pool. Cheryl knelt between my legs and put them on her shoulders. My panties were still strung across my knees. Cheryl took the vibrator and fucked my ass as I jerked off.

As she shoved it deep inside me, I shot my second load onto my chest and belly. My body was involuntary jerking in response to the overload of sensations. My dick finally started to get limp in my hand.

"Have a shower and clean yourself up. We have a lot to do today." Cheryl then added, "Unless I approve, you will not be allowed to have an erection in my presence. Do you understand?"

I nodded my head up and down.

I had to wait until Cheryl was finished with the bathroom before I was able to shower. Not wanting to get into trouble again, I laid in bed, my ass soaked in my own cum and my last load crusted on my belly.

I emerged from my shower to find Cheryl dressed and ready to leave. She held out a short trench coat. "Put this on and let's go!"

"...but I'm naked!" I started to protest.

"I don't want you wearing my things and since you don't have any proper clothes of your own..."

I put on the coat. It was so short, the hem only came down to my mid thigh. At least she let me wear my own shoes.

We got into her Miata convertible and I found it difficult to keep covered with the short coat on. Fortunately it was a short drive to our destination. But it wasn't a cloth store. It was a spa!

I got out of the low car as carefully as I could but was unable keep anything hidden and ended up flashing my nakedness to some females passing by. They pointed and giggled at me as they scurried away.

I guess I looked confused as I followed Cheryl into the store.

"Well we can't have my new girlfriend looking like that when we go shopping." She told me.

Jacklyn, Cheryl's friend and owner of the spa greeted us.

"So who's your new girlfriend Cheryl?" Jacklyn asked.

"This is.." Cheryl paused to think. "Gina. She's here for the works."

"Well let's see what we have to do. Take your coat off Gina."

I looked around. Even though it was still early, there were a couple of women clients around as well as some of the female staff.

"Gina!" Cheryl looked at me sternly.

I slowly undid my coat. One of the staff took my coat from me and gasped to find me naked underneath. The other spectators pointed and giggled. Fortunately I was too embarrassed to get hard.

"The works!" Cheryl and Jacklyn agreed in unison.

I was lead into a room where I was scrubbed down. Every hair on my body was then removed. Fortunately, for a male I had very fine blond body hair, but getting my waxed was still extremely painful.

Both Cheryl and Jacklyn watched and were amused as the sexy female technician manipulated my cock and ball to remove any stray hairs and inspected her work as I tried hard not to get hard.

I was told to go into "Down Dog" position to get my ass done. That really hurt. Then the cute technician applied some lotion to ease the pain paying special attention to my asshole. I felt her finger massage my backside entrance before she started to push it inside. She pumped it in and while stroking my prostrate. Even with that I was able to maintain a limp cock thanks to masturbating earlier. I later found out that Cheryl signaled her to do finger fuck me and try to get me hard just so I would have to jerk off in front of them.

Then I was given a wonderful facial and body wrap, manicure and pedicure, nail extensions paint a bright red and heavy make up to hide any remaining masculine traits.

Finally they affixed a strawberry coloured wig to my head. It was shoulder length with full, soft curls.

"Gina, get your coat." Cheryl ordered. "We've got another stop to make."

She turned to Jacklyn and said "Great job Jacks. See you tonight!"

I put on my short coat and looked at myself in the mirror. I thought I looked pretty hot.

Then I thought "Huh? Tonight!?"

As we drove in the Miata, I didn't even bother trying to cover myself up.

In fact, at one red light, a trucker pulled up beside the car. My coat had fallen open and showed my crotch. I had tucked myself between my legs and from a distance it looked like a shave pussy. The trucker gave me a long wolf whistle as we drove away.

"Oh you do like being slutty." Cheryl noted. I smiled back proudly.

We arrived at our next destination without further episodes. I got out of the car and flashed some older gentleman walking by. He looked at me and smiled.

We walked into the store; a kind of "Frederick's of Hollywood." Immediately a clerk came up to aid us.

"I am Pierre. May I help you?" There was definitely something feminine to his voice.

"Yes, we need a couple of things for her." Cheryl replied and referred to me.

Pierre looked at me and smiled recognizing I was in drag.

Cheryl and Pierre had me try on a number of different lingerie and things including bustiers, garters with stockings, and panties and bras. Pierre was very helpful assisting me with the outfits.

"Something is missing Pierre. I think she needs some help upstairs." Cheryl said referring to my lack of boobs. "Can you help her grow to a size C?"

Pierre left and came back with some skin toned silicon falsies. They fit perfectly and kind of sucked on to my chest like they were actually mine. With skin tone colouring, you couldn't tell they weren't real.

The last piece I tried on was a pretty lacy pink bra and matching crotchless panties. They were open in the back end for you know; and the front had two ties keeping the front closed.

Pierre knelt in front of me, held the panties open as I stepped into them, then he pulled them over my hips. As he reached around to make sure they were in the correct fit, his face "accidentally" rubbed against my noticeable hard on.

"These panties have these cute bows which untie for access." Pierre said stating the obvious. "See?"

Pierre tugged on the lace bow. My hard cock popped out and hit Pierre in the face.

"Oh my!" Pierre said excitedly. Still holding my hips, he opened his mouth and took me in. With a practiced mouth he sucked my cock until I exploded inside his mouth; then placed my cock back inside and ties my panties closed.

I looked over at Cheryl who had played with herself and also just cum from watch Pierre and me.

"That's perfect Pierre. We'll take that and these things too." Cheryl told him. "But that coat won't do. We need something she can where outside."

The both of them opted for a tight white blouse opened to expose my new deep cleavage. The buttons strained to keep my "tits" contained inside.

Next was a short demin skirt with white knee-high stockings and black strappy 4-inch heels. I was use to wearing Cheryl's heels so this wasn't a problem.

"Pierre, please personally deliver these things to my place at 8.30 tonight." Cheryl said. "We're having a Gina fashion show and she'll also need you to help her with her outfits."

"Of course. I should not have any problems." Pierre answered.

We left the store and stopped at an outdoor café. I sat facing Cheryl and the street. The short skirt rode up my thighs and back side as I sat on the patio chair.

I tried to keep my legs together, but the short skirt made sure it difficult to keep things lady like.

As we have some coffee, Cheryl made a number of phone calls. Meantime, the surrounding tables were all occupied by men trying to eye inside my blouse and under my skirt. Inside my panties, I could feel my hard cock leak precum. I dared not let Cheryl know in case she made me "fix" myself there in the open.

"Come on Gina." Cheryl ordered. "Time for home and get ready for tonight."

"Tonight!?" I said to myself. "What's tonight?"

I was to find out soon enough.

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by Anonymous

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by LisaBrooks09/04/18

The Take Charge Wife!

I'm not to surprised Cheryl needed to buy Gina new clothes! It was an added surprise, to me, that Pierre was able to suck Gina's cock! Now that's a woman that I need to take charge at the salon.... themore...

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