Paying Mommy’s Mortgage

I half closed my eyes and mom applied my eyeliner, from the inner corner of my eyes to the outer corners, gradually thickening the line.

"Keep you eyes half closed honey ok?" she encouraged me and patted me on the knee, "just a little while longer while I do your eyeshadow."

Then she reached for the eyeshadow and selected a pale blue shade which she applied to my eyelids and then blended it with a shade of dark pink which she brushed onto the upper part of my eye sockets and right up to my eyebrows. She took the mascara brush and applied thick coatings of black mascara to my upper and lower eyelashes.

"Ok honey, have another drink and I'll do the rest ok" mom said, taking a long sip of her own.

I took another drink and then sat still while mom applied I rouge to my cheeks, defining my cheekbones. Then she applied a coating of 'skin-glow' face powder all over my face and neck. I was amazed when I looked in the mirror at the transformation that was taking place before my very eyes. Mom carefully brushed another coat of mascara onto my lower and upper eyelashes.

"Ok son, I'm going to do your lipstick next. Open your lips for me honey while I apply the base coat. Women now days like to wear long-lasting two coat lipstick like this," she explained.

"You never know what you might be doing that will cause your lipstick to wear off," she giggled.

"Mom!!! What the fuck does that mean!" I relied, a little stunned by what she had implied.

"Oh come on Mike you know mommy ain't a virgin for god's sake!" she laughed.

I realised that mom was more than a little drunk and that I was not for from drunk myself. I giggled a little myself.

"Ok mom; more info than I need ok? Just keep going with the war paint ok? I giggled back at her.

Mom took some time applying Max Factor 'Lasting Colour' lipstick to my lips. I watched intently in the mirror as she applied the base coat carefully just outside of my lip-line and my lips suddenly appeared fuller. She let the base coat set for a minute and then applied the clear topcoat over the 'Raging Ruby' lipstick.

"Purse your lips honey," mom said, imitating what she wanted me to do.

I had seen my mom and other women do this before so I pursed my lips and smacked them together to smooth the lipstick. It tasted quite pleasant. I look at myself in the mirror and am amazed at the transformation, although I still do not look like a woman; I look like a guy in makeup. I sip at my drink while mom rummages around in one of the packages.

Mom produces a brunette wig from the package and brushes it with a wig brush. I have to admire the sheen of the artificial hair; it has some highlights in it and looks quite refined.

"One of the things I went out for today Mike; and I have to tell you it was not cheap," mom explained.

She I positioned the wig on my head and adjusted it so that the fringe was straight and level with my eyebrows. She looked at me quizzically and frowned and then smiled.

"My god Mike! If I didn't know better......." she stammered, and I turned to look in the mirror.

I could have been my mother's younger sister; the resemblance was uncanny.

Mom turned to me, a serious look on her face.

"Let's get you finished and get this over with," she said and reached out for a bottle of nailpolish.

Mom painted two coats of plum red nail polish on my finger and toenails, putting my feet in her lap when she painted my toenails. She finished off her drink and stood up.

"Ok Mike; I think I can leave the rest up to you; from what I have seen in those video clips you know how to get dressed. I've laid one of my suits and a blouse out on the bed for you; just as well I'm a big girl because I think they will be your size. They'll have to be son; I've no money left to buy you skirts or dresses," she smiled wanly at me.

"There are a couple of other items that I got for you today in that bag on the bed and I have laid out some of my jewellery and some perfume on the dresser; you've seen me wear my jewellery, just do the same."

"Call down to the lounge room when you're dressed; I'll make sure the blinds are closed and the doors locked so we don't get any unexpected visitors."

"Good luck son," she said rather poignantly and kissed me gently on the lips.

The taste of my mother's lipstick mingled with mine and caused a stirring of arousal in me. I shrugged off the inappropriate response.

"Thanks Mom," I said as she picked up her glass and the bottle of Scotch and left the room.

I opened the package that mom had left on my bed. It contained breastforms. Because of all of the time I had spent on the net in crossdresser chat rooms and sex sites I knew what they were as soon as I saw them. There was also some medical adhesive tape and cosmetic gum in the package and I struggled for a while but eventually I affixed them to my shaved chest. Mom has provided me with one for her brassieres; it was white satin with lace trim and I tussled with the straps for a while but I managed to fit into it and adjusted it so that it held my breastforms in place.

I walked over to my wardrobe and removed the false panel and unlocked the concealed door and gazed at my stash of lingerie and heels.

I selected a packet of taupe sheer-to-the-waist pantyhose. Despite the graveness of the situation I did feel a small tingle of excitement as I smoothed the pantyhose up my legs and over my tummy and buttocks. I carefully arranged the toes of the hosiery around my painted toenails so that I didn't ladder them.

I sat down on the bed and pulled a pair of peach coloured satin full-cut panties up my legs and smoothed them around my buttocks and over the gusset of my pantyhose and then I stepped into a matching satin half-slip. The lace hem of the half-slip fluttered against my nylons and the scintillating feel of the lingerie on my body began to arouse me but then I remembered why I was dressing this way tonight and all of my pleasant thoughts disappear.

Mom has laid out a navy blue woman's business suit on the bed. I stepped into the skirt and noticed that it has a single pleat at the front and a split side. I buttoned myself into a peach coloured, long-sleeved, satin blouse, fumbling with the buttons because they were on the opposite side to men's shirts. I tucked the blouse into the waistband of my skirt and closed the zipper. The skirt was tight around my buttocks and thighs and the hem sat high up on my legs.

I walked back to my wardrobe and selected a pair of black high-heeled sandals and sat down at the dresser and put them on, fastening the ankle straps. My nylon encased painted toenails peeked out from the black patent shoes. I mooched amongst the jewellery that mom had left out for me and remembered what she said about wearing jewellery. I slipped a gold anklet on my right ankle and adjusted it so that it fell below the ankle-strap of my high-heeled sandal. I clipped on a pair of gold drop earrings, and put on an elegant gold ladies watch and two gold bangles on each of my wrists and a matching gold chain necklace around my neck. Mom has left a bottle of her favourite perfume, 'Poison' on the dresser so I sprayed some on my décolletage and then sprayed a modest mist of the perfume under my skirt, a trick that I leaned from my few girlfriends.

I stood up and put on the suit jacket and stared at myself in the mirror. I couldn't believe I was looking at myself. The woman in the mirror with the heavy makeup, subtly streaked shoulder-length hair, tight skirt, matching jacket and leg show looked like my mom's younger sister; her son nothing like Mike. The skirt was short and tight and the side-split exposed my nylon-encased thighs. I find that moving around my room fully dressed as a woman for the first time is exhilarating; sure I've dressed in lingerie, nylons and high heels before and I love the feelings that dressing like that evokes in me; but being fully dressed this way was totally different. The swish of my nylons against my slip; the feather-light caress of the hem of my skirt against my legs; the taste of my makeup and the smell of my perfume and the subtle stroke of my hair against my face; was so exciting and uplifting; even empowering. But most of all it was just damn hot! I felt feminine and sexy!

I made my way over to my PC and fired it up; I bought up my webcam, looking at the screen I adjusted the position and focus so that the whole of my room was in frame. I hit the record button and switched off the video monitor. With my external hard drive I can record video for over six hours; that would be easily enough time to get the goods on my freaky uncle I thought. I went over to the bedroom and door.

"Mom; I've finished dressing!" I called out.

I heard the clatter of mom's high heels as she approached my bedroom door and then saw the look of amazement on her face when she came into the room and saw me standing there.

"My god Mike you look gorgeous!" she gasped looking me up and down.

"I look like you," I answered.

"Well a younger version of me yes; but god I would never know it was you unless I got right up close. Come over here so I can do a little adjusting," she said as she sat on my bed.

I walked over to the bed and stood in front of her and she pulled me in close to her and reached under my skirt and started adjusting my slip. As he fiddled with the hem our legs touched and silky caress of our nylons rubbing together caused a wave of intense pleasure to shoot though my body. I gasped and felt mom pull her legs quickly away from mine as she realised what had happened.

"Let me get this slip adjusted Mike, the hem of your slip is showing beneath the hem of your skirt," she said in an attempt to ward off anything I might have had to say about what had just happened between us.

Her hands fiddled around under my skirt as she adjusted my slip. This just made the situation worse; as she rubbed the satin material of the slip against my nyloned thighs another intense wave of pleasure shot through me and my penis began to engorge inside my panties. This escalated the situation as my cock was now being stimulated by the slinky material of my satin panties. Every boy's worst nightmare was happening; I was becoming sexually aroused in front of my mom. It was bad enough that mom and Uncle Wally knew about my crossdressing; but getting sexually aroused while my mom was touching me was just too much. Mom was getting a little angry too.

"My god Mike; can't you control yourself!" she said; staring at the bulge tenting the front of my skirt.

"I'm sorry mom, it's just a reaction to you touching my lingerie; I don't think I can control myself, it's just so stimulating," I whimpered.

"Well Christ Mike, Uncle Wally will be here soon and I can't let him see you like this can I? He'll think that you like and accept his advances, and more importantly that's what it will look like when you record it on video" she said, the undercurrent of anger growing in her voice.

"Mike you are not going to fuck this up for us! We need to be able to blackmail that fucking Wally or else we'll be living on the streets!" she said, no longer disguising her ire.

"I'm sorry mom; I just can't control myself, this is just too stimulating for me for me. You don't know what it's like to have a raging nylon fetish and have someone fondle you; even if it's your own mother!" I cried.

"Don't you start crying now! I don't want to have to do your makeup again. Come on Mike get it together; you need to be cold and calculating when Wally gets here, not behaving like some horny transvestite!" mom spat.

"Fuck it Mike; desperate times call desperate measures!" mom said and put her fingers around my nylon and satin panty encased cock.

I gasped as waves of illicit pleasure shot though me. Mom put her other hand under my crotch and stroked my scrotum through the gusset of my pantyhose and panties while the fingers of her other hand traced the outline of my imprisoned penis and then began to stoke it forcefully through the layers of satin and nylon.

"OH god mom!" I gasped.

"Come on Mike lets get this finished with so we can get back to business," mom said whilst vigorously stroking my tumescent cock and scrotum.

"Lets not make a mess on your slip and skirt," she said and lifted up the hem of both garments with one hand while she squeezed and stroked my penis with the other.

My knees began to buckle as exquisite pleasurable sensations, the like of which I had never felt before, ran from my penis, through my groin and then to the pleasure centres of my brain. I became intensely aware of the soft caress of the satin and nylon of my lingerie and blouse against my skin. My cock began to throb as my mother's fingers gripped my iron hard member and squeezed and caressed it, her fingernails raking along the sensitive glans over the diaphanous coating of satin and nylon. I felt my orgasm begin to build and I rocked back and forth on my heels and groaned as release coursed through my body.

Mom quickly removed her hand as I began to flood my panties with hot viscous semen.

"There now; that's that problem taken care of," mom said matter-of-factly, "now hold up your skirt and slip while I change your nylons and knickers".

I was gob-smacked; I couldn't believe what my mother had just done.

"Mom!!! What the fuck was that???" I stammered, standing there holding up my skirt and slip; my panties flooded with warm semen.

"Oh shut up Mike' we don't have time for this; where do you keep your stockings and panties?" she asked, not the least bit interested in having this conversation.

I pointed to my walk-in wardrobe where the secret panel had been removed and mom went over and rummaged around coming back with an unopened package of taupe Voodoo 'Shine Naked' sheer to the waist, sheer toe pantyhose and a pair of white nylon boy-leg panties with lace trim which she dropped on my bed leaving me standing there holding up my skirt. She took a quick detour to the bathroom and came back with a wet facecloth and dropped to her knees in front of me.

"Hold still," she said and pulled down my panties and pantyhose and bunched them around the tops of my thighs.

She wiped down my genitals with the facecloth and mopped up the small pool of white semen in the crotch of my hosiery and then pulled my pantyhose and knickers all the way down to my ankles. She unclipped the gold anklet from my right ankle and then undid the ankle straps on my high heels.

"Lift," she instructed.

I lifted my feet out of my high heels one at a time, holding on to mom's shoulder with my free hand and mom removed my come stained pantyhose and knickers one leg at a time.

"Drop you skirt and sit on the bed Mike; we haven't got much time," she said anxiously looking at her watch.

I was too dazed by what was happening to argue, so I sat on the bed while mom opened the package of pantyhose and rolled up each leg and slipped them over my feet.

"Lie back sweetie," she ordered and eased the sheer shiny nylon up my thighs and around my buttocks pulling the waistband tight.

She ran her hands up each of my legs from toe to crotch removing any wrinkles and pulling the hosiery taught. Even though I had just climaxed I still got a thrill out of the feel of my mom's hands running up and down my thighs but I was too recently spent to become erect. Mom put my ankle chain back around my right ankle and then slipped on my high heels and buckled them.

"Stand up and raise your skirt and slip again Mike," she said.

I stood up again and mom, still on her knees, reached out and lifted my feet one at a time, slipping the boy-leg panties over my feet. She the material of the panties hissed against my pantyhose as my mother pulled them up my legs, pulling them tight and then smoothing them around my buttocks. The sensation was exquisite and I closed my eyes in pleasure. Then mom pulled open the waistband of my pantyhose and reached inside my knickers and arranged my limp penis so that it did not bulge. She patted the front panel of panties and slapped my hands away from my slip and skirt and adjusted them so that the hem of my slip did not peek from under my skirt. She hopped up to her feet and leaned forward and kissed me gently on the lips and patted me on the bottom.

"All ready Mike?" she said sweetly.

I now realised that my mom was not only a conniving witch who was prepared to prostitute her son in order to get her hands on the mortgage to her house; she was also crazy enough to commit incest in the process just to keep her son focussed on the prize. Had she always been this way I wondered? Probably: who knew? She was certainly drinking a lot and that seemed to be affecting her inhibitions and reasoning.

"Hmm; I don't think Mike is an appropriate name for you anymore son; from now on while you are dressed as a woman you are Michele ok?" mom said.

"Now Michele let's put some touches on your makeup before Uncle Wally comes a courting," she smiled.

"And then when we will have the bastard by the balls you will never have to do this again."

"Unless you want to of course," she smiled wickedly at me.

"What!!!" I stammered.

Mom cut me off by pulling me over to the dressing table where she touched up my mascara and lipstick and then gave my face another dusting of face powder. She turned off the overhead light and dimmed the two bedside table lamps and turned to leave the room.

"There now; you really could be my daughter. Let me go and get something for us to drink," she said on her way out.

I listened to the click-clack of her high heels as I pondered my situation and sat down on the bed. I was lost in my own reverie for a few minutes and then I heard the doorbell ring. I froze in shock and alarm as I realised who it must be. Then I heard my mom's voice and the deep baritone of Uncle Wally. I heard the approach of mom's heels and the heavy footfalls of Uncle Wally approaching my bedroom. . Mom and Wally entered my room and I stood up.

Wally is a big hairy man in his fifties; well over six feet with a heavy gut and he at stared at me in disbelief and amazement.

"Fuck me Audrey; she's absolutely gorgeous; she's just like her mom," he sniggered.

"But first things first hey?" Uncle Wally said and strode over to where my PC sat on the desk.

He turned on the monitor and looked at me mom accusingly. Then he started fiddling with the mouse and opened up another program and started clicking and typing. Mom looked at me questioningly; raising her brows silently asking me what was going on. I sat down on my bed as my knees buckled; I realised what he was doing! My god how could I have been so stupid!

Uncle Wally turned around and grinned at me and then at mom who was now sitting beside me on the bed.

"Well isn't lovely what a mother is prepared to do to help her son?" Wally said sarcastically.

"I've seen some interesting things on the net before but seeing my sister-in-law wank off her son has to be the most exciting things so far. I nearly shot my load in undies when saw you at it Audrey," he sniggered.

"My god Mike what the fuck is talking about?" Mom looked at me; her alarm evident in her eyes.

"I'm sorry mom; I just realised what I've done; when I fired up the webcam it automatically started transmitting a video stream on my website," I explained.

"Speak fucking English son; what the fuck have you done!" mom demanded.

"What he's done Audrey, is broadcast your little dress-up and stroking session out over the World Wide Web; that's what he's done!" Wally gloated.

"Lucky for you I was logged in and checked the counter; only three people logged onto Mike; err sorry, Michele's website; and I don't know how many of them were recording the video stream. Most people don't record webcams."

"I did." he finished ominously.