tagTranssexuals & CrossdressersImportant Business Comes Up Ch. 04

Important Business Comes Up Ch. 04

byEmmcee20©

I recommend that you read Chapters 1-3 before this entry so that the characters and background are established. Enjoy! Thanks to those who voted on earlier chapters and a special thanks to those who left comments or sent feedback. Much appreciated. Hopefully Chapter 5 won't be too far away.

Following on from their earlier adventures, Dana was now testing Jason to see how far she could goad him into cross-dressing at work. Was the promise of sex with this gorgeous man-eater too much?


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It was Monday afternoon and Dana had arrived at the appointed time in my office. Alison, my personal assistant, showed her in and I told her not to disturb us. Again she gave me an unusual look as if she were suspicious of something. Dana locked the door and came across the room.

"Show me!" she demanded, the fire in her eyes betrayed her arousal rather than establishing her control.

Wow! I stood up and went around the desk. I undid my belt to show Dana her own red satin underwear that I was wearing together with matching stockings. I explained that I hadn't washed them so I could still smell her juices.

She smiled a little smile and said, "Is this really all that adventurous? Where's the risk. You even wore socks over the stockings because of the colour. What about suspenders or a bra? You said you have them. I suppose it is good enough for you to be allowed to finger fuck me until I come."

And that is what she let me do, leaving me feeling my cock under my desk when Alison came in with a message after Dana had gone. Alison was barely in the room before she stopped and sniffed the air. Dana's sexual scent was probably still quite noticeable but Alison didn't say anything. She went about her business while I did my best to hide my agonising discomfort.

The next day I was more daring - I had to move this along some how. I wore the suspenders. When I sat down the clips were clearly visible against the material of my pants. Dana was impressed, so much so that we sat together on the couch and just as I thought I would get lucky she leaned over and opened the office door to call in Alison. My mouth fell open. Alison came to the door and Dana asked for coffee for us both. Alison looked at me and I nodded and she went. I was about to get up when Dana held me back and said, "Don't you dare move. This is the risk. This is what makes it sexy – the chance to get caught!"

Soon Alison was back and brought in the tray. She put it down on the coffee table in front of us and it was unmistakable. She saw the clips outlined in my trousers. She hesitated briefly and then stood up, looked me straight in the eyes and asked, "Is there anything else I can get you Mr Meadows?

I mumbled an embarrassed no and she left, closing the door behind her.

"Did she see do you think?" Dana asked excitedly, clearly aroused by the scene, her fingers already up her skirt.

"I'm not sure. I don't think so," I lied, wondering what the hell was I doing.

Then she said, "Get it out so I can suck you."

And she did.

That afternoon we had a brief meeting in the boardroom and Dana made a point of sitting next to me. Bob asked her what she thought of the prospects for this lingerie account. She said she thought it was very promising and that she would keep working closely with me on it to ensure that it went ahead. In fact I was almost ready to have the contracts written up for signing by Sue and Andrea. All through this meeting she kept stroking my leg being sure to brush the suspender clips and, on one occasion, she managed to lift and snap the suspender against my leg while covering the noise with a cough. I was a nervous wreck.

Over several days I declined to take any more risks and she would just brazenly lift her split skirt to show me her cunt and say, "You'll never get to where you want to be with that attitude!" and left.

At last I built up enough courage, or was it horny stupidity, to take another step. I wore a dark lace trimmed camisole under my shirt, under my jacket. She was impressed but to show me she wanted more she called Alison in and, before she arrived, spilt coffee on my jacket. Alison fussed over me and insisted I take it off to have it cleaned immediately. She took it off me despite my protests that it didn't matter, stopped and looked closely at my shirt before saying, "I think you may have spilt some on your shirt too sir." Then she hurried from the office. Dana laughed while I panicked. It wasn't fair to bring Alison into this, this way. Dana then caressed my chest and the camisole satin felt wonderful. She said I deserved a treat and that I was to come to her house that night at six.

The afternoon flew by and I wisely removed the cami top to avoid any more obvious distractions if anyone came in. I got to Dana's and she was in a very good mood. "Come in, have a seat. Wine?"

We did and it was lovely. We sat a chatted for a while as she dug information out of me about where I was up to with the Close to You account. I guess she was covering her tracks in case she got asked anything as we hadn't really spoken about the account at all in our meetings. They'd had a rather different agenda. Then she changed the topic as she said how she enjoyed hearing my exploits with Sarah and Jody.

"Would you like to do something like that with me?" she queried enticingly.

I agreed without hesitation.

"Good. That's what tonight will be for you - a night without any hesitation. Take off your clothes and meet me upstairs."

I did as she demanded, leaving my clothes in a pile on the lounge as I went in search of the pussy I wanted so badly. I went up the wide staircase. I could hear the sounds of movement in one of the rooms and so I entered a vast bedroom that was centred by a huge antique metal framed bed. There was Dana standing facing me as I entered, wearing a skimpy almost transparent teddy. She was stunning, her formidable frame encased in the gossamer material.

"First a bath to sooth you."

We went into the huge en suite and the spa tub was filled already and it produced a most aromatic alure. The soft lighting and incredible opulence of the luxury was overwhelming.

"Stop. First I must shampoo your hair."

She'd brought a chair to the sink and I sat back to have my hair washed and scalp massaged. She was very attentive.

"Feel free to fondle and caress if you wish. You were daring today so you earned it."

Shortly after she said that I had two fingers probing her pussy and her moaning as she did my hair. I was able, at my leisure, to explore her heated core and stroke her downy pussy hair. She finished the shampooing and then she said, "I want this to be a very sensual experience so you must wear a blindfold."

I agreed and she put it on me and then she steered me to the side of the hot tub and helped me get in. After a while she turned on the spa jets and the warm water bubbled and frothed. She had her hands roaming all over my body massaging and stroking every single nook and cranny, steering me at her will so that she could caress and massage every inch of my body, although she avoided any contact with my head. My foreskin was peeled back and forth and my balls vigorously rubbed. My arse crack was explored and a finger dipped in. My nipples were pulled and stroked and finally my face was massaged. My cock was fully erect and waiting impatiently for what was to follow.

After an intense fifteen minutes of this close attention, I couldn't wait to jump her and I was sure that's what she wanted. The blindfold did increase the sensuality of not knowing what was coming next. Then she ordered me from the spa and into the shower. She climbed in with me and the hot water tingled on my skin under the harsh spray of the hand held shower head that she expertly directed across my body to tingle and keep me aroused while she was rubbing her body on mine. The tantalising sting of the water jets caressed my body and, as she drew the water up my legs, the spray engulfed my scrotum like a hot mouth. I gasped at the sensation - every nerve ending of my skin seemed super-sensitive.

After I was completely washed and my hair was rinsed of the suds, she got me out of the shower and patted me dry with a towel before she took off the blindfold. There in the still water of the spa floated a mat of dark hair. I looked at my body – even in this dim light I could see that I was bald everywhere except my head; even the early days of a moustache had gone.

"There, isn't that better? I put a hair removal cream in the spa. The blindfold saved your eyebrows and the shampoo saved your head. You don't need any other hair and now you will really feel the satin or silk. Now come to bed and let's fuck."

I was stunned but also rather intrigued and titillated. Again she turned and walked away and I saw that wonderful set of hips that I was about to get into sway as she went back into teh bedroom. I followed eagerly, feeling the gentle caress of air movement across my whole body. With raging hard on in hand I chased her and caught up just as she reached the bed. She side-stepped me and pushed me onto the bed. I fell and was surprised by her speed and agility. Then she leaned over me and grabbed my hand and thrust it to her breast and I stopped moving to concentrate on fondling her tit. Then she pulled it again and I felt the sharp knock on my right wrist as the handcuff went on and was squeezed tightly closed.

"Don't even think of struggling and it will go much easier for you. Now shift your arse over here. Banana? Ha! I'll give you something better than that."

I watched while Dana slipped out of the teddy and walked naked across the room to her dresser. She opened a drawer and withdrew something about the size of a shoebox only flatter.

"Now this will be fun," she said as she dropped it on the bed and took off the lid. The dildo was about ten inches long with imitation veins - a very angry looking hard on for anyone although not particularly thick, in fact not as thick as my own still rampant cock. Then out came the harness and I knew for sure what she meant when she said, 'Let's fuck'; I knew who was going to give the fucking and who was going to receive it. I lay back on the bed to await the inevitable.

She left me with just one hand cuffed so that I could move to meet her demands. She told me to turn around, roll over and move my face to the edge of the bed. She then went to the dresser and brought the chair to the edge of the bed in front of my face. Oh well at least I'd get some of her juice first I figured. Then she strode to the wardrobe, there was real purpose in her every movement, and she returned with a black three-foot long riding crop. The real thing, just like jockeys use. She sat on the chair, allowing the crop to dangle from its wrist loop so that it swayed menacingly in my vision with its silver cap and black binding. She spread her legs wide and swung one over my head and onto the bed beside me. Her pussy was a matter of inches from my chin.

"Now listen my little slut, first you are going to eat me until I come. Any time I feel your heart isn't in it you'll get this," and with that she swung the crop hard onto my buttocks. I felt it imprint its shape into my buttock and it stung like Hell.

"Then, when I decide I'm ready, I am going to fuck you. Got it?" her intimidatory tone would brook no argument. If I had even a hint of what was good for me, I would obey. I nodded.

"Good. Let's eat," she said with a wicked smile and shoved her cunt forward and into my face.

She lay back a little and spread her lips for me as I only had one hand free. She was really juiced up. This power trip was really getting her off. I was practically in mid air too with the hard on that I had. The cracks on the backside were actually fairly rare – I must have been eating well. When they came they stung but invigorated and they made me lunge forward to escape them, shoving me deeper into her pussy folds. The pressure that kept building in my raging hard on needed to be got rid of somehow.

Dana's moans and groans were increasing and the crushing pressure of her thighs on either side of my head made breathing difficult. The musty aroma of her pussy seemed everywhere. She started to thrust her hips into my face in a rhythmic pattern, bumping her pubic bone against my nose.

It took a while but she finally let out a low growl that increased in volume and intensity until she was grunting as I burrowed my tongue deep inside the wet flesh, trying to spear her as far onto my tongue as I could. Forceful thrusts into my face were accompanied by guttural roars as, like a Derby runner, she lashed my backside to get us both to the winner's post. She sprayed my face as her orgasm enveloped her being. After she had come long and loud, she said I had done a good job and, seeing I was obviously enjoying the whip, judging by my cock, she would reward me.

She made me lay flat and started belting the daylights out of my bum with the whip. She was a remarkably good shot and by whipping the soft flesh of my inner thigh she made me reflexively spread my legs wide to avoid another contact only to give her a great angle on my balls, cock and arsehole. They were red raw by the time she let up but the heat in them only made me ache to come even more. It was amazingly stimulating! I'd never experienced this type of pleasurable pain. Then she put on the harness and held the strap on cock forebodingly in her hand. It looked scary.

Dana walked back to the chair and sat as she had before. She sat inches from my face and then put her feet up on either side of my head so that I had an exquisite close up of her open wet folds. Again she spread her legs and then smiled at me as she slowly slipped the huge dildo into her cunt. Gasping in the pleasurable feel, she stroked it several times before slowly extracting it. I had a great view of how it pulled at the flesh of her womanhood and was smeared with her juices. Finally the tip slipped out and she arranged the harness and snapped the cock into place.

"Now worship the cock you are about to feel," she demanded.

Automatically obeying her, I opened my mouth and took as much in as I could. I was pleased to feel that it was quite soft in my mouth and pliable but it was still so long. She shifted back and forth, fucking my face quite gently and I tried to get it all in. I was leaking all over the bed. She decided I was ready so she climbed on the bed behind me and told me to roll on my back and lift my butt in the air. Then she shoved pillows under me. She was going to do me while facing me. I'd never even thought of this position before. I'd always thought of anal sex as in the doggy position. Momentarily thinking about it, there were some clear advantages to this arrangement.

"I want you to see it as well as feel it. You'll know who is boss then, won't you?"

"Yes ma'am," I replied.

"It's MADAM or Mistress Dana to you, slut; got it?" And again the riding crop swished through the air.

"Yes Mistress Dana. My apologies."

My cock was going to detonate; I was so turned on. Dana grabbed my ankles and lifted them high above her head to expose my backdoor fully and then she held them wide apart and told me to keep them there. With only one hand free I had to just use my stomach muscles for the task but I knew that the first intrusion of my bum would make that difficult to maintain.

She spread some sort of lubricant on her shaft and proceeded to penetrate me. Having not had more than a finger or two ever pass through those muscles until the banana incident I'd told her about, there was a lot of resistance to something going in the out door. Dana pushed firmly once she had aligned her cock with my dark entrance and slowly my sphincter spread to allow access. It stretched and burned until the lube kicked in and then it was quite smooth.

She started into a steady rhythm that took about 6 or 7 inches of the cock out of me and then slid it back in. She gave me exquisite relief by grabbing my ankles for her leverage and allowing me to release the tension in my lower muscles so that she could slip deeper inside me. She leaned forward to penetrate me and my legs were pinioned by her breasts and over her shoulders as she reached for my nipple and tweaked it.

She snaked her other hand down between us and was soon painfully squeezing my balls to hold off my orgasm as long as possible. My cock stretched to its full length up between us. She had neatly managed to encircle the top of my scrotum with a thumb and forefinger so that she could squeeze the full, tight and sensitive testicles with her other fingers. Her thighs were neatly nestled below mine so that her loins crushed against mine on her inward stroke. If she could penetrate me with all of this ten-inch cock, her pubic bone would bang against my balls. I was practically praying for a deep shafting as I became delightfully accustomed to the feel of the intrusion, an inner warmth building as my prostate was being thoroughly stimulated. While all of this was going on, she spoke to me.

"Tomorrow you will wear a bra as well as your panties, suspenders and stockings. You will make sure that your mousy little secretary gets a look – a cleavage view would be good. You will be bending over the desk when you call her in while I am there. She is going to know your secret tomorrow. Do you understand? You will have to figure out what you will do about it. If this works out well and you do as you are told, you can fuck me in the cunt right there in your office."

That was the last straw as I visualised the scene – squeezing my balls wasn't going to stop me coming now. She had released them and was now pumping into my backdoor and the first time her pubes belted against my balls, I erupted with long strings of cum spraying my torso and up near my aching tits. Dana thrust the cock in and out at a more rapid pace hammering my arsehole as she pulled on my nipples; she came also I think from the pressure on her clit but possibly also from the power of the situation. She wanted me to know who was in control.

To make sure she was right she left me locked to the bed. The sexual tension and completely exhausting orgasm allowed me to nod off to sleep soon after she had slipped her cock from me and left the room. I slept. It seemed like minutes later that I felt the all consuming warmth in my groin and woke to find Dana had engulfed my cock in her red lips as she seductively mouthed me to an orgasm. The best wake up call in the universe!

She undid the manacle and gently led me to the bathroom. It all seemed so civilised after the wonderful torture of the night before. She enjoyed running her hands over my now hairless body, then she led me to the shower where she directed as I pampered her. She kept me naked while I assisted in dressing her. The other bedroom, where she had obviously spent the night, had her beautiful lingerie waiting laid out on the bed. I was aroused again as I slipped her suspender belt around her trim waist, my cheek against her full breast while I connected the three hooks and eyes, feeling the swell of her breast with each breath. Then she sat on the edge of the bed to allow me to draw her seamed stockings up her legs and attach the three clasps to each stocking. The sensual hiss of the material as it moved over her skin only served to remind me of what it would feel like the next time I had the chance to wear my own stockings only now on my over-sensitised hairless skin - it just wasn't the same as shaving. Once both were on she splayed her legs wide to expose her open and wet inner sanctum and then languidly stretched each leg in a high arc until it was vertical above her head.

"Are my seams straight?"

I fussed to make them so while luxuriating in her aroma and the sensation of the silken material as I stroked her calves into perfect alignment. My cock was fit to burst as it pointed to her clearly wet opening only inches from where I stood but it got no attention. She lowered her legs and sat up, nodding to the bra. I moved to her, holding the arm straps agape for her to slip into and then I scooped her glorious breasts into her satin blue bra and reached around her firm bosom and attached the hooks behind her. She remained seated and I could feel my cock grazing against her stocking-clad leg and I was certain I was smearing my pre-cum juices along her thigh. Not a word was spoken as I stood up to see the clear fluid sticking in strings to her stocking tops.

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