Cum and Dress for Me... Pt. 01

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Jen was smiling as she walked towards another part of the room? I sat up, I felt dizzy. I looked at my swollen cock, it was still really hard.

"Don't worry about that, it will go down in a minute... I have got something you can wear that will help! Come on, get up, lazy...come over here!"

I sat up, took my knickers off, and walked towards Jen who was sitting on a chair near a dressing table. Jen pointed to another chair with a towel on it.

"Sit there...I don't want you leaking everywhere!"

I sat down on a soft pink drying towel. "Now, let's get you finished!"

Jen started to rub cream on my face; it was cold, as she expertly covered my face. She was really quick, as she started to add powder to certain parts of my face, then she was brushing my eyes with eyeliner, mascara, and more make up on my eyelids. Jen was very precise, she didn't talk. I didn't speak either.

Jen then got a lipstick pencil and started to etch out over my lips, then she finished it off with a roll-on lipstick. It had probably taken less than 20 minutes. After what had happened, the silence felt really strange. Jen got up and started to take some photos from different angles, I didn't question her this time. I could see the time she took to take the shot and the angle she seemed to get said she had been trained.

"Can I ask you a question, Jen? Have you studied photography?"

Jen held the camera down and smiled "Well, just for the record, I am a fashion photographer... That's how I got in to doing this! I sell erotic art pictures... Mainly in black and white I have a few studios in London and New York where I sell them... It pays the rent and I really enjoy doing it! I love the shadows and the angles... I really enjoy capturing desire in the faces of the girls I take photos of."

I was amazed at her answer, it completely threw me. A professional photographer? Well it explained the beautiful house she had! Photography obviously pays well!

"So, I have to ask...who is Fay?" Jen burst out laughing.

"You like her do you? Well Fay is my PA! I would not sell my pictures if I didn't have Fay! She is brilliant... She's a real star... I love her dearly! Put your hand out!"

I put my hand out and Jen started to rub an emery board over my nails. Then she buffed them up a bit and started to paint them in a bright red fire engine colour. The varnish went on in thick strokes and completely changed the look of my hands. She was quick, then she started on the second hand. Before I knew it, my nails were painted.

"Stand up...let's sort your problem out! Here, put this on!"

It was like a g-string with a cock shape at the front.

"Put him in there for me and slide them up your legs for me!"

I put it on and rolled them up; Jen grabbed the front and yanked it downwards. Before I could complain, she pulled it between my legs and hooked it behind my arse.

"See...it's gone now! You look just like a girl!" she smiled. "Put your knickers back on...sit down, Darling!" she walked away went to a cupboard and returned with a wig. "Let's finish the look, Darling!"

I sat perfectly still as Jen eased the wig over my head. She pulled it down a few times. It felt really sexy, it felt divine. Then she went to a draw.

"Now for the final part, Darling!" She held up two false breasts. She quickly put some clear tape on them and inserted them on to my chest. They felt fucking awesome!! I actually felt like I had breasts.

"Ok darling, try these on?"

She handed me the tan leather skirt - it was so soft, the smell was amazing... it really looked special. I pulled it up to my hips, then I put the mustard coloured wrap round blouse on - it felt really silky. I felt like I was in heaven.

"Ok Hun, let's get some shots of you dressed to kill!"

Jen got me to stand and then walked round me taking photos, moving my hands, tipping my head backwards. I felt like a model! I felt like I was on fire! I no longer felt like a guy - I wanted to be a model in her pictures in the gallery.

"Do you want to see what you look like?" I was so obsessed with the camera I hadn't even seen what I looked like. "Close your eyes...put your hand out!" Jen grabbed my hand and led me along a short distance then stopped. "OK Hun, open your eyes...look at how amazing you look!"

I opened my eyes - I couldn't believe the girl standing in front of me. Jesus, this couldn't be me? Surely, it wasn't me? Jesus, I looked stunning! If I saw me, I would want to fuck me as well. I couldn't believe what she had done! I looked like Katy Perry, it was just unreal.

"Follow me, Darling...let's see what Fay thinks of you?"

We walked out the bedroom and down some stairs, past the kitchen and lounge. Another door appeared. Jen opened the door and walked in to an office - three women with headphones were sitting at desks talking. Jen put her finger to her lips and indicated that I should be quiet as we walked past them. Another part of the office had an inner office; Fay was sitting at a desk typing.

We walked in; Fay looked up "Oh my God, Jen...this can't be her! She's a master piece! It's fucking Katy Perry! Jesus, Jen...is this the same girl as?"

Jen looked at Fay and nodded yes.

"Jen, do you realise how fucking hot she is?"

Jen was smiling. "Do you like your new boyfriend?"

"Oh, FUCK YESSSSSSSSSS... She is so fucking horny!" She walked towards me and kissed me on the lips. I could feel her lipstick sticky against mine, she smelt amazing. "God, I want to fuck you so much, Darling! I want to feel that giant sissy cock deep inside me...deep inside my clit!"

I was really embarrassed; I could feel myself going red.

"Oh yes...Jen, just to let you know, your 5pm has cancelled...said he's really sorry...agreed to pay the full fee no problems! I have rebooked him, ok?

Which means you're free to go out with us tonight! Can I take her with us, please? She will have guys falling at her feet! I bet she would love to come out on a girl's night with us?"

They both looked directly at me and smiled.

"No, I'm not going out dressed...Jesus! No way...I will get beaten up! No, I'm sorry...you have made me look incredible, but I'm not going out dressed in women's clothes...no way!"

Jen smiled "What are we going to call you? You have to have a name, Darling! If we are going out with the girls, we need to call you something!"

My heart was thumping, I was getting really nervous "Look...you go out have a nice night...I have had an unbelievable day! Please, I would shit myself if I went out dressed like this!"

They both laughed out loud "You don't get it do you? We will be with you! You look unreal...nobody will have a clue...nobody will know! We will go out, have a few glasses of champagne, and then we can bring you back to your room... Besides, I want to show off my new boyfriend!" Kay burst out laughing. "Let me introduce you to the girls outside!"

She grabbed my hand and led me outside. The room was quiet, none of them were talking.

"Ladies, meet my new girlfriend Julia!"

All the women were smiling; they were all mid to late forties, all really well dressed, perfect makeup, very presentable for their ages.

"Julia is coming out on our girl's night tonight, aren't you?"

A phone rang, one of the girls answered in a posh voice, she said "Hello...who is this? Oh I see! Who gave you permission to wear that, you dirty slut?"

I couldn't believe my ears, did she just say dirty slut?

Jen leaned over and whispered "I own a sex chat line as well..." she burst out laughing. "Sit with the girls...it will be fun!" she pulled a chair over and pushed me down into it. "I'm going to do some paperwork! Get to know the girls...they won't bite!"

Jen walked off with Fay into the office and started to read some paperwork. The phone rang again, the next woman took the call "Mistress Latex here...who is this? Steven? That's not a slave name is it? What you wearing, slave? A PVC what? Oh that sounds nice! So slave, tell me what do you want Mistress to do for you tonight? Really, slave? I think you need my knickers in your mouth! Would you like that?"

It was fascinating watching these pretty ladies talking dirty to guys on the phone. I understood now what they meant about doing love scenes in a film - they are not sexy with everyone watching you.

"Oh, you want to know what I'm wearing, do you slave? Well, let's see...PVC stocking's, matching knickers and bra... Oh! My nipples are pushing through! They are so hard talking to you! Black knee length boots with 6 inch heels! Oh you think so, do you slave? You would struggle slave if I walked on your back, wouldn't you?"

The woman was actually wearing a smart black trouser suit; she had blonde hair in a bun and looked like she was about to do the school run. I couldn't believe what I was hearing. I sat there fascinated, listening to the women talk dirty to men about their fantasies. I started to smile after a while because it was actually funny listening in on what they were saying. The girls were really good, they were sexual, but they did it to draw the guys in even more. What made it funny was watching them talk dirty and sipping there coffee as they listened to the guys trying to wank.

I didn't realise how long I had been sitting with the girls; I didn't have a watch. The day was just running away from me. Jen came over to me and smiled.

"So you met the girls have you? You look like you're having fun listening in! Let's get you upstairs, Darling...you need some shoes, jewellery, coat and a handbag. Come on, Julia...let's go out with your girlfriends!"

12
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8 Comments
Doc333Doc333over 4 years ago
please continue

excellent story i enjoyed it very much.Would love to see chapter 2

contactsteph77contactsteph77almost 6 years ago
Hi

Het dearest you just never disappoint

AnonymousAnonymousabout 6 years ago
Cum and dress for me.... comment

Wow, what a really sexy story! It is one of the best I have read on literotica. I really loved the idea of the crossdressing service and how they handle the client. I see it is part one, hopefully Jen and faye will dress him again in different outfits. I thought the ending would have taken him to the B&B since he did not want to go out and there they spend the night with him convincing to do it all over again in different outfits.

From lacysliplover

AnonymousAnonymousabout 6 years ago
Nicely done

Very nice story, cant wait for pt 2 and so on. Would love to be that guy. Dressed to the max, looking like a real woman, and with women that know what there are doing dressing him. Lucky bastard.

TWOSPERITSTWOSPERITSabout 6 years ago
Supper great

I loved i. I truly hope you keep the story going. I would love to here when the part comes.

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