Cum and Dress for Me... Pt. 01

I saw the advert in my local paper - it just jumped out at me! Then I was surfing the internet, usual stuff, looking for something to get horny over... WHAM!! The same advert appeared within three days of seeing the advert in the paper. I'm not into that hocus pocus stuff, but it seemed weird that within three days I had seen the same advert. I felt compelled to do something about it. I tried to reason with myself about it. In the end it was like a message, a message telling me to do it. The little voice in your head that you listen to for advice was telling me to call the number.

I sat at my PC, my cock was hard. I really wanted to call the number, but I had never done anything like this before and was worried that the local porn police were going to identify me with some kind of porn radar and expose my kinky desires to everyone who knew me.

I bookmarked the website and decided to look at 'normal/ ordinary' porn. Jesus was there such a thing? Man fucks girl, girl cums in the end. I tried to get the advert out of my head. It was obsessing me, I couldn't stop thinking about it. I clicked on the advert, it came back up, it had a website link. I clicked on the link, my fantasies were answered. I looked at the pictures and read an extremely professional and very well written introduction of what the site offered. My cock was so hard; I leaned over to get my mobile phone. It was just before nine, guaranteed no one will be there this time at night. I tapped in the numbers then hesitated. Jesus, I should hide my number... But part of the excitement told me to press enter. The dial started up, the phone was ringing. 'Shit its working' I thought to myself. I heard the phone being picked up, I put the phone down, 'Jesus, Fuck' I thought to myself. Somebody actually answered the phone. I sat in the chair, for some reason my cock seemed to be even harder. Jesus, just call the fucking number I told myself. I hit re-dial, the phone rang, a girl said 'Hello'.

"Emmm... yes, I'm ringing about your advert!" I said.

"What advert is that?" said the girl.

'Oh shit, bollocks, fuck, fuck...' I thought. "The advert online!"

"What advert are you referring to? We have lots of adverts on the internet?" said the lady.

I had no choice at that point; I just knew I had to say what I wanted: "The dressing service that you offer!"

"Oh, I see...what dressing service is that?"

I could sense the lady was teasing; I was like a big kid frightened to talk to a stranger. "The crossdressing advert!" I finally said.

"Oh Darling, what are you looking for? Wedding dress, French maid, business woman?"

I couldn't believe how casual she seemed to be about it.

"Look, if you want to come and meet me, you have made the call Darling, and broke the ice! Tell me what you want?" Her straight talking just made it sound like I was ordering a new part for a car. I paused on the phone.

"Hello, are you there, Darling? Look, we offer a dressing service for people just like you...would you like to come and see us? It's so much easier if we talk it through over a coffee! Would you like that?"

I was silent sitting in my chair with a massive hard-on. "I would like that, but you are quite away from me...it would be a long way to come for a coffee, especially if I didn't want the dressing service!"

The lady laughed "Darling, you sound like you really need to put on a frock and de-stress! Am I right, darling?"

I suddenly felt really relaxed talking to her, "I can offer you a starting up dressing service...full makeup and pictures on your phone! You will get two hours for £50 and choice of one outfit! Does that sound fun?"

My hands were actually shaking.

"Yes, it does! I'm really nervous...never done this before! It's just that your website...your advert it looks so professional! I just wish I could look like the girls in your photos!" I started to relax.

"Well why don't you visit us, Darling? When do you want to come and dress for me?"

The invite really threw me; I needed to check my diary, but I was sure I could do the Thursday the following week.

"Could I visit next week? I will need a lunch time appointment so I can get home in good time!"

The lady went quiet, "I can do that! What's your female name, Darling?"

My female name? I had never thought about a female name! Jesus, this was all happening very quickly! I thought for a minute then said "Dionjade!" It was the name of a female lap dancer I had met the year before. She was very erotic - I loved her dancing for me - loved her name.

"Emmmmmmm Hun...that is a nice name! Dionjade...tell you what...if you're worried about last trains home, I can do a really good price on a B&B! You could visit us, then leave in the morning in reasonable time! How does that sound?"

I took all the details of where it was and committed to the B&B as well. Worst case scenario, I could go for a beer afterwards, get my head down and move on having done something on my tick list - the famous one hundred things to do before you die list.

My cock was really hard and the helmet was really shiny - it was such a turn on knowing that I was going to dress fully as a girl! It had been something on my mind for years, and I really wanted to crossover and see what it felt like... But, who do you share that desire with? Hardly a conversation for a girlfriend, wife, or best friend! I had always fantasised about being a woman with a pussy, but I never had the courage to do something about it! I really loved women - I loved their clothes - I loved their humour. I preferred women to men! Now the advert was like my calling - it was like I need to get this out of my system.

I booked the two days off at work, rang Jennifer at the dressing service to confirm my booking. Then, on the Thursday, got an early morning train to the dressing service. When I got to the station, I could not see any buses. I took Jennifer's advice and got a taxi to the road where she told me to go. I got out early in the road and waited until the taxi had disappeared. It was a simple, normal, road with big houses in it. I walked down the road until I found the actual house. 'Jesus!' 35 Hornby Avenue. I looked at the house - it was big, but it looked like all the other houses. I was four hours early! 'Shit! What am I going to do?'

I decided to call Jennifer. I explained that 'my train was early and maybe if possible could I drop my bag off in the B&B and come back later for the service?'

Jennifer laughed and said she 'had no one else booked, so come over early for a coffee'.

I knocked on the door. When it opened, a very pretty girl aged about 28 answered the door. She smiled straight at me. I paused and smiled back.

"You must be Dionjade! Come in, Darling...let's get you a drink!"

The house was really lovely, it had expensive furniture, it was very stylish.

"Just relax, Darling...I won't bite!"

I walked in to the large foyer; it had coat hooks and shoes neatly stacked together. I followed Jennifer into a large kitchen - it was really nice. The radio was playing quietly and I could smell toast.

"Coffee or tea, Dionjade?"

I smiled at her "White coffee please...no sugar!"

The coffee machine started up and Jennifer walked towards me. "Leave your bag, Darling...I will show you to your room in a minute, but let's have a chat first!"

We walked into a large lounge with a big log fire burning - it was a beautiful house.

"So, how do you feel Darling? Excited, nervous, apprehensive? All of the above?" she smiled at me. "Darling, you won't need much makeup...you're very pretty! Let me see...I think you're a size 16! Yes...I think you're a 16! We will have to work on getting you to a 14, won't we?"

The lady was spot on - I was a 16 - unfortunately, my frame was a guy's frame. I was not fat, but my body was of a man. I hated being so big because in my fantasies I always wanted to be the pretty skinny girl that gets fucked.

"So, tell me about what you want from today! Tell me what Dionjade wants to achieve! Tell me your kinky thoughts?"

I was really shocked with her honesty, but as we talked, it was obvious she knew exactly what buttons to press to relax me.

"OK Darling...I think you are going to look good in something bright...something that says intelligent business woman! What do you think, Dionjade? Would you like that?"

I nodded.

"Ok Darling...let's get you up to your room...bring your coffee! Let's start now, shall we? You can have a shower and freshen up before you get changed! How's that sound? I hope you shaved your legs, Darling, like I told you to. We all love IMac...all the girls love it...takes hair off your legs so easily!"

I nodded in silence. She was right, the hair simply washed off, the feeling was amazing! It felt so horny having shaved my legs. I got in the shower - it was piping hot and it was really powerful on my back - it was a really lovely shower. When I got out, I could see a pink terrycloth dressing gown on the side - I assumed it was for me. With the excitement, I had forgotten to pack a towel, so I was really grateful to dry myself off.

Jennifer shouted from downstairs, "When you're dry Darling, put on the underwear on the bed!"

I turned to the bed and saw the silver coloured satin underwear laid out on the bed - it was so fucking horny! I touched the French knickers - they were like liquid satin - they felt amazing! A matching bra, suspenders, camisole top and some tan stockings. My cock was rock hard! I slid the French knickers up my legs - my cock was just pointing outwards completely killing the sexy look. I dressed slowly hoping my hard-on would go down, but it just sat their rock hard - I had never seen it so hard before.

"Oh, Darling look at you! You look so pretty! Oh dear Dionjade...what is that in your knickers? You're a naughty horny girl, aren't you? We will have to get rid of that, won't we?"

I looked down, embarrassed at my rock-hard cock sitting in the shiny French knickers.

"Come here, Darling...let's see what I can do with that?"

I walked over to Jennifer.

"Wow...this satin really has quite an effect on you, doesn't it Darling? It's not fair, is it? That's why I run this service...so people like you can relax and be whatever they want to be!"

The bright flash really startled me. "Stand by the window, Darling...let me get a few more shots of you dressed like a horny slut!"

I put my hand up indicating I didn't want any more photos. I was ashamed of how easily I could be controlled. The material made me so high.

"Don't be so shy, Dion...you look so cute and you're obviously excited about this! Relax Darling...enjoy the moment! No one knows you're here, do they my precious? Nobody here will judge a girl having fun and relaxing in her undies! The pictures will look great, Darling...you'll see! Now, put your fingers up to your mouth...act like a complete sex kitten...enjoy that satin, Darling!"

Jennifer raised her camera again and started to get me to pose again. My cock was so hard, I wanted to wank so much, the feeling was overwhelming me... But, her voice and the satin seemed to hold me like a tortured prisoner in its spell. She really knew how to take photos; she made me pose in several sexy positions by the window. I simply couldn't stop myself; I was completely under her spell. Some of the poses were me bending over slightly; I just didn't seem to care.

Then, all of a sudden, I realised what was happening, Jennifer was taking photographs of me. Oh My God, everyone would recognise me if they saw my face, it was obvious it was me, a guy dressed in sexy lingerie. It hadn't even crossed my mind - I wasn't wearing a wig to disguise who I was. Jesus, I was so stupid allowing this to happen with a woman I didn't even know. What the hell was I doing? I turned and shouted out "No! Stop it Jennifer! I can't have these photos of me! Everyone will know it's me! I look like a sissy, a gay guy, a weirdo...please stop this..."

I started to get really upset; I was breathing heavy and shaking. Even my voice sounded like a girl in distress. Jennifer stopped taking the photos and walked over to me.

"Darling, you need to embrace what an amazing horny girl you look like! Look at the excitement it's created in you! When was the last time you were this high? When was the last time you felt so normal and so horny?"

Jennifer was right! I couldn't remember ever feeling as high as this! I really felt incredible - it felt like it was how I should dress - I felt unbelievably horny! If I had been at home feeling like this, looking like this, I would have wanked myself off into a crazy sex-fuelled fever.

"Jennifer, you're taking photos of my face! Everyone will see me! Everyone will know it's me in women's underwear!"

Jennifer lowered the camera and smiled "Darling, these are your photos! These are your memories of the moment...the moment of your beautiful day! The photos are safe with me, Dion. I wouldn't be in business if I couldn't be trusted, would I?"

She had a point, the underwear felt like a satin liquid, it just clung to my body - it was a perfect fit. What made it even sexier was there was a slight chill in the room, the underwear was just slightly cold on my skin, it really made it feel amazing on my body.

"Tell you what, Dion... I think have got the perfect look for you, Darling! Do you like leather?"

I looked up and smiled at Jennifer with a girly, nervous, look... I nodded.

"Good girl...look at these! Don't you just love them?"

I looked over in the corner of the room; draped over a pink Georgian chair was a shiny mustard coloured blouse and a tan coloured skirt - it was short and really sexy.

"Don't they look yummy, Darling?"

I stared at the chair, the clothes looked fantastic.

"Tell you what, Darling...Why don't I do your makeup and let's get you in a nice wig to top it up and finish that look? How does that sound?"

I nodded.

"Oh, let's also get you some drop dead gorgeous titties as well!" she giggled in a very girly way. "A sexy girl like you has to have a nice pair of titties to finish the look, doesn't she? Why don't you lay on the bed Darling and relax...I'm going to speak to one of the girls in the office downstairs! I think Fay will have some ideas on what to do about that monster trying to escape in your knickers. Now behave, Darling...no playing with it! I can imagine what a naughty girl you would be without me stopping you play. No playing, Dion...I will be back in a minute. Just relax, Darling...you never know it might just go down!"

I laid on the bed; it was soft and really comfortable. My breathing was really calm. I really felt sexy, I actually felt like a young, sexy, woman! I couldn't believe the feelings I was having. I kept touching the satin - it was mesmerising me. I couldn't believe the softness and horny it made me feel. I must have fallen asleep because a voice made me wake up with shock...

"Hi Dion! Oh Darling, don't jump, it's ok! My name is Fay... Jennifer said you were having a rather big problem in your knickers! It's ok, Dion... We get this all the time when guys come here and get dressed! Why wouldn't you be turned on? I'm turned on looking at you! She's right...you really are cute. I'm on my break at the moment, Dion...I haven't really got long! Jennifer suggested I pop up to see if I could help you get rid of that!"

She leaned over and put her hand on my knickers - my cock was still really hard inside the satin prison.

"Oh Dion...you need to get rid of that, Darling! Do you want me to help you..."

My eyes focused on the stunning woman in her mid-thirties; she was wearing a black skirt and a dark pink wrap round blouse that tied at the back. Her breasts were quite a feature of her overall presence.

"I had a boyfriend like you, Darling...he didn't realise the power of satin either! I really miss him! He was like you...he loved to wear my sexy underwear for me when we made love!"

She had long dark curly hair she was really pretty.

"Oh Dion...have I made that happen to you, Darling? Oh my goodness, Darling...you're getting bigger! We need to sort that out for you before you make a mess of your undies?"

I looked down and my cock was sticking straight up - it was so obvious! Fay was right - I really needed to do something about it.

"Dion, you know this service is not sexual that we offer here, don't you? Jennifer is very strict that clients know it's not a sexual dressing service that she runs here! If we did, we would be in all sorts of trouble! You understand that Dion, don't you?"

I nodded, but the overwhelming desire to shot my hot cum out was killing me, especially with a really pretty girl standing by my side of the bed.

"Look Dion, I don't normally suggest this, and if I got caught doing it, I would get into trouble, but why don't I help you with that massive hard-on?"

I couldn't believe what I was hearing; most guys would probably shoot their load at that very moment they heard those words, but for some reason it was like an enchantment. I managed to hold back.

"Let's have a look, Darling! Jesus, Dion...are you always this hard? Wow...it's quite a cock you have there, Darling! Well lucky old me...I guess this is my lucky day!" she giggled.

"Now close your eyes and relax...I want you to feel safe, darling! Close your eyes...imagine I'm your lesbian girlfriend and you are about to orgasm!"

Fay held my cock in her hand and started to wank me off. I felt so high, hearing her sweet voice talking about two girls being in each other's arms needing to cum, needing to orgasm together as one. I didn't expect what happened next. My eyes were tightly shut and I suddenly felt her silky wet red fire engine lips wrap round my cock as she started to suck me off. Her hands were everywhere on my body; one hand was massaging my shaven ball sack, she was squeezing the sack as if to ensure the cum was going to come out.

Her other hand was circling one of my nipples. The feeling that I suddenly felt...Oh My God...WHAT was happening to my body?

I felt the most amazing high as I suddenly began to orgasm - I could actually feel the cum leaving my balls as I exploded into Fay's mouth. Fay seemed to get faster as I shot my hot milky cum straight into her mouth. Fay didn't stop; she kept wanking on my balls searching for every drop of hot cum that was in my sack.

Fay finally stopped... I opened my eyes...She was still swallowing the hot creamy cum I had shot into her mouth. Standing in the corner of the room was Jennifer camera raised taking photos of us.

At that moment, I actually didn't care, it was the orgasm of my life, I don't ever remember cummin' like that.

"Oh, my God, I can't believe how much cum you just produced! Jesus, where did that cum come from, Darling? If you have a girlfriend, she's a lucky Bitch! If you haven't got a girlfriend, make it me! I'm serious...you are fucking amazing! I couldn't get enough of your cock!"

Jennifer had stopped taking photo's she was just smiling at both of us as I lay on the bed. I was still trying to catch my breath after the orgasm I had just had. Fay stood up and moved away from the bed, "Jesus Jen, where did you find him? He's fucking gorgeous!"

They both giggled. I closed my eyes; I was just totally exhausted with the sheer sexual activity. My cock felt so sensitive, I could feel every sensation in my cock, I could feel the blood still rushing through the veins, my ball sack was completely empty. Fay walked over to me and kissed me lightly on the head and left the room.

"Right, you horny Bitch! Let's get you made up! Take those knickers off... I don't want you getting them dirty or my sheets... They are both clean on today, you dirty girl!"

I opened my eyes and lifted my head, still breathing heavily.

"Come on, it's already been nearly two hours! It was only supposed to be two hours with some photos! I have got a business to run you know, and you're starting to overlap with other clients!"