Paying Mommy’s Mortgage

As long as I can remember I have had a penchant for wearing nylons and lingerie: pantyhose; stockings; silk, satin or nylon panties (not those horrible cotton things or G-strings that are like candyfloss in your arse crack -- I mean, full cut panties, cami-knickers, or boy leg panties); garter-belts; slips -- both half and full; basques and corsets.............I can go on but you get the picture.

I also have a fetish for high heel shoes: sandals, pumps, courts, stiletto heels, kitten heels, stacked heels, Cuban heels, platforms, open-toe, "Pilipino bar girl fuck-me shoes"; you name the high heels -- I love them!

Now this might not seem unusual if I was a sophisticated woman (or Pilipino bar girl) but I am a male; a young adult male who lives at home with his mom.

Mom and I have lived alone in a comfortable three bedroom house with a two car garage and a small in-ground pool since my dad died when I was only three years old. I don't remember him and don't care about him to be honest. I have three uncles and aunts on my mother's side of the f****y and we have a great f****y life as we are often together for festive occasions and f****y dinners. I have an Uncle Wally on my father's side of the f****y who occasionally visits mom but really has nothing much to with us and we never visit him.

Now back to my fetish; I have read about it extensively on the internet and I have a good understanding of my proclivity for women's underwear, hosiery and shoes. From my research; my fetish is best explained as follows:

"Most of the material on fetishism is in reference to heterosexual men, with most of the objects fetishised being high-femme items such as lingerie, hosiery, and heels a specific object or type of object, dating from an experience during the period where the mother gradually pulls back as an immediate provider of satisfaction of the c***d's desires, persists as a characteristic in adult sexual life."

So I understand that my fetishism is somehow linked to my mom; I certainly have fond memories of her dressed only in her lingerie snuggling and hugging me when I was younger and remember the soft silky feel of her slips and nylons against my skin but I don't remember any sexual excitement; just a feeling of and reassurance. I certainly had no sexual feelings for my mother. We love and respect each other of course; but that is as far is it goes.

That said; at sometime I developed sexual feelings for her lingerie and footwear. I can't remember when I first started dressing in mom's nylons and heels but I know I knew I shouldn't be doing it and soon realised I would get caught if I kept dressing in her clothes. Initially I took some silly risks and stole some hosiery, panties and slips them from my aunts washing baskets or from neighbourhood clothes lines; this was also risky, so once I had a few items I stopped doing this and just took whatever mom or my aunties threw out in the trash.

Once I was old enough to earn my own money I stopped taking anything at all and purchased my own lingerie, hosiery and shoes. Pantyhose were easy to buy; I just threw them in with the weekly groceries when it was my turn to do the shopping; the cashier just naturally assumed they are for my mom. Likewise I learnt that if I approached the attendants at the various lingerie shops I could ask them to assist me to purchase lingerie and shoes "for my girlfriend". When I was a too young to be buying lingerie or shoes for a girlfriend they were for "for my mom for mother's day -- birthday -- Christmas"; you get the picture. By the time I had reached adulthood I had a very extensive collection of lingerie, hosiery and shoes.

Now a little about my mom, Audrey. My mom has always been what society likes to call 'a big girl'; she is not particularly fat but she has a large frame. Mom has never complained about this; unlike my aunts who always lamented they were too fat. Mom likes to dress nice; business suits for work, skirts and blouses after work and on the weekends. She always wears hosiery, heels, jewellery and makeup; her hair was always coiffured and she always wears perfume. My aunts and mom's friends sometimes mock her about the way she dresses saying it is 'old-fashioned' and 'too much' but mom ignores them god bless her. Mom is very much focussed and goal oriented and is not really concerned about other people's opinions of her anyway.

I like the way my mom dresses and when I was still in the habit of borrowing her lingerie I particularly liked that she had such a nice assortment of underwear and shoes for me to borrow. You could say that mom's style of dressing became mine; at least as far as my fetish went. I am not the only one that likes the way my mom dresses; she had her fair share of suitors. Mind you she is not a slut and I have never seen her do anything untoward in my presence nor does she allow her gentlemen friends to stay overnight in our house. Mom has occasionally stayed out all night but as I got older I was not naïve enough to think my mom was not having sex.

Now a little about me, Mike; besides my fetish that is. I am a slim, moderately handsome, adult heterosexual male. Sure I live with my mom but that is more for the convenience rather than any 'mommy's boy' issues. I might as well admit that my job sucks and that I don't earn a very good wage, so staying at home, rent-free, makes perfect sense ok! I have had the occasional girlfriend but I am awkward around women. I'm no virgin but I don't get a lot of sex.

Now a little more about my fetish. Obviously I keep it totally secret; I'm sure that mom might have suspected something during my younger days when I used to borrow her lingerie and hosiery but most young k**s experiment with that sort of thing; you know, playing dress-up. Now I am obsessive about not being caught.

I do keep my body fully shaved; but hey it's the era of the metrosexual and all the guys are getting 'back, crack and sack' wax-jobs and getting their chests waxed and legs shaved. I'm not that hairy anyway and with my nice tan, I must say that my slim body looks quite good. The real reason I remove my body hair though is so that I can fully appreciate the feel of sheer silk, satin, and nylon against my bare skin. The only real blemish on my body is a small tattoo of a reclining lady (dressed in lingerie and high heels of course) on my right calf. I regret getting it but I was d***k at the time; I'm absolutely hopeless when I'm d***k, I'll do anything!

I keep all of my fetish clothing and associated pornography behind lock and key in my room and my computer is password protected. I keep my room locked at all times and when I'm exercising my sexual predilections, I keep the blinds drawn and hang a 'do not disturb' sign on the door. To appease my demands for privacy, my mom understands I am studying for a degree part time that will hopefully lead me to a better job. So she is used to me demanding solitude and staying up late in my room. To be fair; I do spend a lot of time on the weekends and weekday nights locked in my room studying; but I spend a lot more time in there dressed in hosiery, lingerie and high heels masturbating to pornography on the internet.

I like to strip naked, shower and then slide into a nice pair of sheer pantyhose or stockings; my panties go over my pantyhose or over the suspenders of my garter belt if I'm wearing stockings. I then put on a nice slip, usually a full-slip and finally a pair of nice sexy high heels. I like to pose in front of my full-length mirror or look at pictures in my extensive pornography collection of women being fucked in lingerie; but mostly I end up in front of the PC surfing the net and masturbating.

I am a member of numerous websites where guys have similar interests to me and I recently discovered the joys of web-camming and set up my own webcam site; I like to show off my lingerie clad body (never my face) and sometimes I jack off on camera as well. I never accept webcam streams from other guys; I'm not gay or interested in men, but I get a kick out of knowing that anyone can watch me on my webcam site. This peccadillo for displaying myself on the web dressed in lingerie was to cause my downfall.

It started couple of weeks ago when my uncle Wally can around to make one his rare visits. He and mom were in the lounge room for quite some time when I heard him and mom arguing; not just quarrelling but out and out ranting and screaming at each other. Mom was yelling,

"No way! No fucking way Wally; that is never going to happen!!!"

And then Uncle Wally was screaming back at her.

"It's the only way it's going to happen Audrey; you know you don't have the money!!!"

They kept on like this for quite a while; I went into the lounge room to investigate but when mom saw me at the door she slammed it shut and all I could hear were her and Wally hissing at each other so that I couldn't overhear them. Eventually Uncle Wally slammed the door and left; as he went out the door he yelled back at mom.

"You know what you have to do Audrey; it ain't like he's even paying his way is he?"

"I'll see you both tomorrow night!"

This last statement puzzled me but when I looked at mom with an inquiring gaze she gave me an angry look.

"Why don't you just go to your room and lock the door and do what you do in there!" she hissed at me.

Now I was really puzzled; mom seldom got this mad with me, so Uncle Wally must have really pissed her off somehow. I decided to retreat to my room and do some long overdue study. About two hours later there was a soft rapping on the door. It was mom.

"Mike, can I talk to you honey; I'm sorry I yelled at you; come and talk to me please," she begged.

"Let's go sit in the lounge room and talk ok?"

I unlocked my bedroom door and went into the lounge room. She was sitting on the couch and was obviously d***k. Her makeup had run down her cheeks, her hair was dishevelled and her skirt had ridden up exposing the darker band of her control-top pantyhose on the top of her thighs. She saw me looking and straightened her skirt and smoothed her fingers through her hair.

"Sit next to Mike; we have to talk," she said patting the space beside her on the couch.

I sat next to her and she poured me a large scotch from the half-full bottle on the coffee table. She topped off her own drink and turned to me with her glass raised.

"Take a drink Mike; you're going to need it son," she said and took a large gulp of her drink.

I took a sip of mine and looked at my mother searchingly.

"What's the matter mom? What has Uncle Wally said to upset you?" I asked.

"I don't know how to tell you this, so it's probably best that I just show you the filth that Wally bought into our house today," she responded.

I looked at her quizzically again but she just pointed with her chin at the television set and hit the play button on VCR remote.

"Look," she said in a sad, heart-rending voice.

I was shocked at the scene playing on our TV screen in livid colour. It was recorded video of a person sitting on a chair in front of a camera. The person, dressed in a white satin full-slip, sheer taupe pantyhose, white nylon full-cut panties and black patent leather high heels was only visible from toe to neck. You would think that the person was a woman except for the fact that the person was holding down the front of her panties with one hand and stroking an engorged penis with the other. The person was a man. The person was me.

I could try to deny it of course; except that the room in the background of the video was obviously my bedroom and also, on the man's right calf, visible through the sheer nylon of his pantyhose, was a small tattoo of a reclining lady dressed in lingerie and high heels.

My bedroom and my tattoo were as evident to my mom as they were to me. I gulped down the rest of my drink and reached for the bottle as mom hit stop on the VCR remote.

"I had my suspicions of what you got up to locked in that room for hours at time Mike; but I never dreamed of anything like this!" mom whispered.

"And to display yourself for the world to see; my god!!!"

"I'm sorry you had to see that mom," I apologised, "I'm really sorry,"

"Well Mike the issue is no longer that you like to dress up like that and masturbate; it's that uncle Wally knows about it and he has plenty of video footage of you doing it," she replied.

"Pour us both another round Mike; I need to tell you something and it's going to take a while," she went on.

"When your father died, he left us with nothing Mike. Your uncle Wally has been paying the mortgage on this house since then."

"He promised me that he would keep up the payments and then give me the deeds to the house one it was paid off; it was the least he could do for the widow of his b*****r he said."

"Now the time has come; the house is paid for but there is one hitch. The bastard won't transfer the deed to my name unless I give him something that I hold precious," she said looking at me intently.

"What is it mom?" I asked.

"You Mike," she answered.

"That's what Wally and I were arguing about!"

"He told me that he is some sort of admirer of crossdresser and has always wanted to be with one. I told him that I was not interested in his disgusting sexual deviances; but then he showed me that revolting video."

"I recognised that it was you of course from the tattoo; and then I realised that it was video of you taken in your room. Wally told me about the webcam thing and how he had found you online and that he has recorded you on a number of occasions."

"He's blackmailing us Mike!!!"

"If you don't do what he wants he's going to show the video to all of the f****y and post it on Internet sites along with your details!" she sobbed.

I was stunned.

"He can't be serious mom," I implored.

"He is serious Mike. We have no money to give him for the house and he's threatened to evict us if we don't do what he wants!" she answered.

"What are we going to do mom?" I cried.

"We're going to play along that's what," she answered coldly.

"I'm going to swallow my pride and so are you! We're going to pretend to give the sick fuck what he wants; and then we're going to turn the tables on him!" she went on.

"You're going to dress up for your uncle Wally and let him come into your room. You get him naked and let him do some stuff with you; nothing extreme; and you film it on your webcam and we blackmail him back!"

"You only need to record video of him touching you inappropriately; so long as we can clearly see his face; that will be enough to blackmail him. I don't expect you to commit any sex acts," she finished.

"Like fuck!!!" I shrieked, "I'm not letting that pervert anywhere near me!"

"Well what are we going to then Mike? Where will we live?" mom snapped back.

"And what about the video of you that he already has? What are we going to do about that? Do you want the world to know that you're a pervert?"

Mom calling me a pervert bought me down to earth with a thud; I realised that there was nothing I could do but go ahead with mom's plan to ensnare Uncle Wally with his own trap.

"Ok mom I'll do it," I said reluctantly.

"But only so far as to get the goods on Uncle Wally attempting to interfere with me; then we spring the trap before it gets any further ok?"

"Ok son; but there is one other thing that uncle Wally wants; he wants you fully dressed as a woman Mike; makeup, hair, shirt blouse; the whole caboodle," she explained.

"Well what the fuck mom? I'm going to let my uncle act in appropriately with me dressed in women's underwear; I would actually prefer to have on some clothes on. In for a penny in for a pound I guess." I capitulated.

"Ok Mike; we have to be ready to act tomorrow night; that's when he's coming back." Mom said, and drained off her drink.

We finished off the bottle of scotch and planned and schemed into the early hours of the morning. I woke late the next day with a hangover and the memories of last night came flooding back. I didn't want to do what mom and I had planned but I knew no other way out of the situation. Both mom and I were broke, so there was no way that we could pay my uncle the outstanding mortgage bill and he had the webcam video footage of me which he had threatened to show to mom's f****y and post online. I was trapped I had to go along with mom's plan.

I spent most of the day locked in my room in trepidation of what the evening would bring. About six o'clock there was a tap on my door and I got and let mom in to my room. I lay back down on my bed sulking and she came and sat down on the edge of my bed.

She was dressed immaculately as always; skirt, blouse, hose, heels, makeup and hair perfect. I cast a critical eye over her. She was quite attractive for a woman of her age, even though she was a large woman. Her legs were her best assets and she was not afraid to show them off with short skirts and sheer hosiery. Her face was pretty; framed by a blonde bob and heavily made-up with lashing of eye makeup and lipstick. I hadn't really noticed how flat out sexy my mother was before tonight.

"Mike; go and have a shave and shower ok? I'll get the rest of the things we need for tonight," she said.

"Come on honey let's get this over with."

She leaned forward and kissed me on the cheek; the scent of her perfume lingered when she stood up and left; her heels clicking on the wooden floor.

I went to the bathroom and used the toilet and then shaved myself very closely. I brushed my teeth and showered, returning to my room clad only in towel around my waist. Mom was sitting next to my dressing table on a chair that she had bought to my room. Mom had pulled my chair next to hers alongside the dressing table in anticipation of my return. The were a number of packages piled on my dressing table and I realised that this is it; I'm going to dress as a woman to entrap my uncle Wally and blackmail him into not blackmailing me. The whole idea was preposterous but I was going along with it; without an alternative plan I had no choice.

"Sit down Mike," mom sat patting the chair beside her adjacent to the dressing table.

"I went out today and got a couple of things we; well that is you, are going to need."

I noticed a fresh bottle of scotch was opened on the dresser and two doubles had been poured. As I sat down besides mom she handed me one and took one herself. She chinked her glass against mine and said,

"Hair of the dog," and drank down her drink in one long gulp.

I followed suit and mom topped off our glasses again. Mom had bought in a vanity case and she busied herself sorting though the cosmetics and then she turned to me.

"Ready honey?" she smiled at me.

"Ok mom," I answered.

Mom applied foundation to my face explaining how she had picked a shade that closely matched my skin colour. I Then she liberally coated my face and neck with face powder, one shade darker than my foundation. Mom turned my face towards the mirror.

"Now I have the blank canvas on which to apply the rest of the makeup Mike; take another drink if you want because we're going to be busy for a little while making you look pretty," she smiled.

I took along pull on my drink and then relaxed and let mom do her job. I was actually intrigued by what she was doing to me and concentrated on watching her do my makeup. The smell of the foundation and powder was quite appealing and bought back memories of me as a young boy sitting next to mom as she made herself up before going out.

"Mike I want you to half close your eyes for me ok?" she said.

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 d***k and that I was not for from d***k 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 s****r; 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 s****r; 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 f***efully 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 i****t 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 s****r-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.
"So forget your little plan to film me and Michele 'in flagrante delicto' and blackmail me with it. I now have a better video to blackmail both of you with." Wally went on.

"What will everyone think of a mother who dresses up her son in ladies clothing and wanks him off; or of the son who willingly participates? I don't think we want to find out do we?"

"Nah! Let's just go back to our original agreement shall we?" Wally gloated.

"See you Aud; lock the door on the way out will you?" Uncle Wally grinned evilly at me and mom.

Mom slowly raised herself off the bed and turned to look at me; shoulders slumped and defeat in her eyes.

"I'm sorry son," she said and then turned to Wally.

"Don't you hurt him!" she spat vehemently.

"Fuck off Aud; don't let the door slam you in the arse on the way out," Wally laughed as mom left the room and the door slowly closed with an ominous click as it locked.

"Now Michele honey; such a lovely name your mommy picked for you...............get your arse over here; come to Uncle Wally," he chuckled.

I stood up and walked over to my Uncle Wally. I knew that mom and I had been defeated and that I had no choice but to comply with Uncle Wally's demands. I was determined to get this degradation with over as quickly and painlessly as possible.

"God your just fucking beautiful, Michele" he whispered and put his arms out to me.

Uncle Wally stepped forward and embraced me, locking his strong arms around me. His faced moved forward and I sensed he was about to kiss me. I f***ed myself to stay still as his lips came down on mine. It was the strangest feeling, I could feel the slight rasp of afternoon shadow on his face, smell the faint scent of his aftershave and the press of his thick lips against mine. He pushed his tongue into my mouth and I could taste my lipstick mingled with his mouthwash. His tongue started to explore my mouth and he pulled me even closer.

I f***ed myself not to back away, rather, I became limp. I knew there was no way out of my current predicament so I tried to clear my head and just endure what was happening.

Wally kissed me passionately, his lips pressed hard against mine, his tongue exploring under mine then working its way slowly around my mouth, flicking and probing. His body was hard-up against me and I felt a hand slide down my back and come to rest on my buttock. He rubbed his hand there, the material of my dress and slip whispered against the smooth nylon of my panties and hose.

"Mmmm," Wally whimpered, his lips still against mine.

He lifted his face and looked at me again. I realised that in his own mind Uncle Wally was not looking at his nephew, but at a gorgeous woman wearing heavy makeup with the rouged cheeks and red painted lips of a whore.

Wally began to kissing me passionately and I felt his other hand slide down and take both of my buttocks in his grip. He lifted the hem of my skirt and caressed the material of my slip. His hands worked in a circular motion in time with his tongue, rubbing the silky slip against my pantied buttocks. I was so shocked that it took me a while to realise that he was also gyrating his hips against mine; pulling my lower half hard against him as his passion intensified.

I commanded myself not to move, to just take what was coming; it couldn't be worse than being exposed to my friends and f****y as a person who commits crossdressed i****t with his own mom.

Then I felt it, I went from being a limp rag doll and tensed up, almost pulling myself away. Using the utmost self-control I f***ed myself to go limp again in his arms and allow him to ply my body against his. What I felt was a thick hard bar that could only be his erection pushing against my stomach. I could feel it though the material of his slacks and my skirt.

Wally gyrated against me now, his tongue working feverishly in my mouth, his lips crushing mine. His hands gripped my buttocks and pushed my lower body harder against him. He was 'dry humping' me I realised; pushing his erect member against me through our clothes. I felt a deep humming from his deep in his throat and he was breathing heavily in and out of his nose as he continued to kiss me deeply.

He suddenly stopped pushing on my buttocks and I felt his hand leave my bottom, glide across my hip then move between us. He fumbled there, his hand between my navy blue skirt and his loose linen pants. My god I knew what he was doing! And then I felt his erect member spring from the confines of his trousers and slap against my thigh.

Wally's erect penis was like a hard iron bar between us. His hand flew back to my bottom and he again rucked up my skirt and used both hands to caress my buttocks through the slip as he pulled me back against him.

He ground himself against me, rubbing his cock hard against my lower abdomen. I could feel the girth of it though the layers of skirt, slip, panties and pantyhose. I concentrated harder on not panicking and just allowing him to do as he wanted; surely this would be over soon.

Wally's kisses had now become a hard insistent invasion of my mouth; every few seconds he had to break to take a breath, panting and gasping.

"Yes! Oh yes Michele! So good! So good!!!"

Wally again removed his hand from my bottom and fumbled around down there between us. This time I felt him lift my skirt up completely so that it was rucked up around my waist. He lifted me up and f***ed me on to my toes, my heels left the floor and I fell against him, my face now level with his as I balanced awkwardly in my high heels. Wally struggled with his erection and I felt him push it down then release it so it sprag forward whilst at the same time he pushed our lower extremities together.

His cock was now wedged between my legs, hard against my crotch, encased in the silky sheer material of my half-slip.

"Oh my god!" Wally groaned and began his hard circular humping against me yet again.

He got into rhythm, dry fucking me in time to his feverish kisses; slowly circling his trapped manhood between our bodies. Wally struggled with the hem of my slip and eventually bunched it up around my waist with my skirt. Now I could feel his turgid penis trapped between my panty crotch and my gossamer clad thighs. Wally was pushing up now as he thrusted, fucking the silken trap made by my pantyhose thighs and panty crotch. I could feel the head of his penis rubbing itself against mine through my panties.

I felt Wally quicken his pace and his cock begin to throb. He pushed against me harder and he held me so tight I though he would squeeze the breath out of me. His tongue was now a wild wet a****l, thrashing in my mouth, fluttering and exploring every crevice.

Both his hands gripped my buttocks squeezing them roughly through the gauzy nylon panties and pushing me forward and back to the rhythm of his thrusts. Then he groaned and gripped my ass so tight that I thought my panties would tear. He f***ed me against him as hard as could and I felt his penis begin to pulse and throb.

Then he suddenly pushed me away so violently that I tottered backwards on my high heels and fell onto my bed. Wally was red faced and groaning; his tumescent penis sticking out of his flies, bobbing in front of him, a string of clear pre-seminal fluid dribbled from his glans.

"Wow that was close Michele; nearly came then; don't want a premature ejaculation to spoil my fun now do we?" he sniggered and started closing in on the bed.

I didn't know what he intended to do to me but a number of disgusting scenarios raced through my mind. I decided the best way to deal with the situation was to be compliant and go along with him and hope that he took whatever he wanted from me quickly.

Wally kicked off his shoes and trousers; dressed only in shorts, socks and shirt he looked at me with a****l lust, tucking his slowly deflating penis away into his shorts. He reached down and lifted my legs onto the bed and then he dropped onto the bed besides me. His tongue invaded my mouth in a passionate kiss.

Wally's hand went straight to my legs and he stroked my pantyhose thighs. He obviously liked the feeling because he started to grunt as he continued to kiss me. He pushed me back on the bed and straddled me, all the time keeping his lips locked on mine as he grunted and snuffled like a pig. Wally was now running his hand up and down my nylon legs working his way from my ankles up to my thigh as he pulled my legs up and bent my knees so that my high heels were flat on the bed pulled up close to my buttocks.

Wally ran his hand over the front panel of my panties and then reached inside the gusset of my pantyhose and found my flaccid penis tucked away. He pulled it free and rubbed his hand over it through the gossamer nylon. I shuddered.

He took my hand and bought it up to his shorts and I felt the heated bulge of his package. I suddenly had a plan! Maybe if I masturbate him I can make him climax and prevent him from being capable of any other sex acts!

I dragged my fingers over the bulge so that my fingernails dragged agonisingly slow over his tumescent erection. Then I feathered my fingers back down his member, softly fluttering them against the rigid pole. Wally groaned and broke the kiss so that he could look down at my painted red fingernails running up and down across his sac and his rampant member which was straining against the light material of his shorts.

I reached into Wally's shorts and gently stroked his scrotum using my fingernails to lightly sc**** against the sensitive skin. Wally groaned and began to kiss me passionately again and with my free hand I stroked his face and ran my fingers through his hair. I circled the girth of his erect member and started a slow feathery stroking motion up and down the shaft; as my fingers slipped over his glans I flicked my fingertips over the spongy mass.

Wally adjusted his position on top of me so that he could shuck off his shirt and pull down his jockey shorts and discard them. He was now naked except for his socks and he stretched his body over me, his rampant penis sticking out proudly from his hard hairy beer-belly. He lowered himself down on me, pushing my legs down so that I was suppliant; lying beneath him with my legs splayed apart, my skirt stretched taunt.

Wally lifted himself up on his elbows and gazed along my body. He took in the shiny black high-heeled open-toe sandals on my feet, the glittering sandal-toe hosiery highlighted my painted toenails. He caught a glint of light off the gold chain on my ankle and ran a hand under my legs and stroked his hand all the way along my nylons from my calf to my thighs. His hand slid across my sheer boy leg panties and he gently stroked my still flaccid penis.

He stroked my cheek as looked into my heavily made-up face, he pushed a finger into my mouth and I sucked on it seductively. Wally stroked my hair following the mane of my wig to where it caressed my shoulders, the highlights in my hair enhanced by my mascaraed and eye-shadowed eyes and ruby red lipstick lips.

"Oh my fucking God you are beautiful Michele!" Wally whispered and lowered his lips to mine.

I tried to push my hand between us to arouse him further but he was rubbing his cock against my nyloned thighs and I couldn't get my fingers to it. I pushed back against him, encouraging him, responding to his kisses with false passion, hoping I could make him ejaculate against me.

He moved on top of me again and to my horror I felt his strong hands pull my calves up again, bending my knees so that he was between my legs with my heels flat on the bed. I tried to push myself down into the bed but he f***ed his hands under my buttocks and lifted my buttocks clear of the bed. In a swift movement he grabbed two of my pillows and positioned them under the small of my back. I knew what was coming next as he reached down to my stockinged calves and pushed them upward so that my knees came up almost under my chin.

I was terrified about what was to happen but concentrated on trying to get my Uncle Wally to climax before he could go any further. I kissed Wally deeply, my arms locked around his back. I felt his hard cock punching at my thin gauzy panties and pantyhose gusset; those garments were my last line of defence between Wally's erection and my puckered anus. I broke the kiss and reached down to try to masturbate him in desperate attempt to ward off this attack. If I could just make him come before he went any further!

He slapped my hand away and reached between our bodies and inside my panties and with his calloused stubby fingers he took a handful of the fine material of my sheer to the waist pantyhose and tore a small hole in the gusset exposing my sphincter.

"Please, don't Uncle Wally" I pleaded.

"I'm sorry Michele, your mother has given you to me; it's time to make a mortgage payment," he sniggered, indifferent to my pleas.

With that Wally clamped his lips over mine again and his tongue assaulted my mouth. I felt his grip tighten on my legs, pushing them hard against my body exposing my bottom, still clad in my boy-leg panties, supported by the pillows under the arch of my back. He pushed the gusset of my panties aside and thrust forward with his rock hard cock and I felt it slam against my sphincter.

I wanted to scream but he clamped his mouth tightly against mine, kissing me hard but keeping his tongue out of my mouth for fear of me biting it. Wally started to push hard against my puckered ring, gripping my legs even tighter. I felt my sphincter stretch as Wally's glans began to invade my anus; the slight lubrication from his pre-seminal easing the passage only slightly. I felt a pain that was almost unbearable as Wally continued to push against me. He was still kissing me but grunting at the same time; his breath exploding in little gusts between my lips.

The head of Wally's penis was now just inside the entrance of my back passage and my sphincter clamped tight around his shaft. He pushed slowly into me, forcing his engorged member deeper. The pain was excruciating and I began to cry. I couldn't help it. The fear, the humiliation, the pain; it was too much. Large tears ran down my cheeks leaving trails of mascara as I began to sob in earnest.

He continued pushing into me showing no sympathy for my pain. I knew now that all I was going to get was more pain unless I relented and helped Wally get this over with. Passive compliance was doing nothing but causing me agony. I concentrated and f***ed myself to try and relax the muscles in my anus that were resisting the intrusion of Uncle Wally's cock as it slowly slipped deeper inside me. It was hard to do but I was able to make my anal muscles relax and suddenly Wally's cock slid about four inches inside me.

There was more pain now as the thicker part of his member f***ed itself even deeper into me. Wally was panting now and was supporting his weight on his forearms while locking my thighs open and pressed back against my body. He was looked down to watch at his penis disappear through the hole in the gusset of my pantyhose as he buried himself into me. Then he looked at my face, my makeup running from my tears.

"Oh yeah, this is so good!" he groaned and gave a mighty thrust.

I felt the thrust coming and f***ed myself to relax as Wally's hard cock thrust all the way in, deep into my bowels. His scrotum bounced against the soft nylon covering my arse cheeks and as he ground his cock inside me and rubbed his balls against my buttocks.

I screamed; the pain was the most incredible thing I had ever felt. I tried to stop, but one long agonising scream escaped me.

I heard Mom knocking frantically on my bedroom door.

"What are you doing to my son you bastard!" she screamed through the door.

Wally lifted a hand and I knew he was going to belt me unless I capitulated.

"Tell her it's alright!" he hissed into my ear.

"It's Ok mom; don't worry about me. Every thing is fine!" I lied, shouting back at the door from where I lay crushed under my Uncle Wally.

"Go away mom; we'll be out in a minute!" I called, and heard her clatter off down the hall.

"Good girl Michele," Wally grinned, his face inches from mine.

I knew now that I had to get this torture over with. I did the only thing I could. I raised my legs up and wrapped them around my Uncle Wally, locking them around his waist, my shiny black high heels pointing up at the ceiling.

I pulled his lips down to mine and thrust up to meet him and slid my tongue into his mouth. I started to fuck my Uncle Wally! At first the pain was so bad that I was sobbing into his mouth as we copulated. Eventually though, enough of his pre-seminal fluid had leaked into me that it began to lubricate my anus. Although it felt immensely uncomfortable I was able to bear the pain and concentrate on trying to get the **** over and done with.

I bucked against Wally matching his thrusts and getting into his rhythm; I scrunched my bottom against his scrotum as he slammed his cock home inside me and rubbed my stocking legs along his back to excite him further. My arms were locked around his back and we both kissed passionately gasping for breath as we rutted.

I felt Wally quicken his pace and he plunged harder and faster, I worked hard to keep up with his rhythm and held his face in my hands and kissed him as my legs remained locked around his back. I eased my legs down slightly and dug my high heels into his sides to further stimulate him; I just wanted this to be over.

Wally was moaning and running his hands up and down my stockinged legs; I guessed he was approaching his orgasm. Then a strange thing happened; I began to feel a warm pleasant sensation deep inside me. My penis was beginning to stir in my panties, encouraged by the pressure of Wally's body against mine as he fucked me. What the fuck was happening? Then I realised what was happening, I had read about this somewhere, Uncle Wally's penis was stimulating my prostate gland.

'I am not enjoying this! I am not enjoying this!!' I tried to convince myself in my head.

Wally gave a huge lunge and pushed his cock deep inside me right up to the hilt; he ground his balls against the silky fabric of my panties and madly stroked my stockinged thighs. He clamped his lips hard against mine and I felt him ejaculate his hot seed inside me. His cock convulsed and shuddered as he moaned in the throes of orgasm.

I couldn't control myself; the pleasure centre of my brain kicked in. My high heels drummed on Wally's back as I lifted my bottom up off the pillows and pushed as hard as I could up against him. My tongue lashed around wildly in his mouth. My sphincter spasmed and my anus convulsed around Wally's ejaculating penis. My prostate released spasms of pleasure causing concentric waves of delight to surge through my body. Wally's thrusting trapped my penis between our two bodies forcing the diaphanous material of my panties to caress my cock. I ejaculated into my panties. I wasn't even erect and I was climaxing!

We lay locked together for what seemed like an eternity as our mutual orgasms subsided, gradually relaxing our fierce grip on each other and our hot wet kisses slowly softened to delicate lip brushing.

Wally eased himself out of me; but my anal muscles remained relaxed and my sphincter dilated. I felt Wally's semen flow out of me and slowly run down the crevice between my buttocks and pool in my panties. Wally sat on the edge of the bed his member slowly deflating. He reached out and caressed my cheek with the back of his hand and then bent down and kissed me tenderly. He pulled down the hem of my slip and my skirt and helped me up to a sitting position.

"That was lovely Michele," he whispered.

"Now let's get your mother in here and really have some fun!" he spat with malevolence.

To be continued...
100% (28/0)
 
Categories: AnalShemalesTaboo
Posted by sparkyking
9 months ago    Views: 5,745
Comments (10)
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3 months ago
great story
6 months ago
part 2 please, and hurry. think Mom can do anal too?
7 months ago
hot story had me hard as a rock wish I had a hot thing like that uder my power cannot wait for part two
8 months ago
Oh my !
Awesome story, very well written, so erotic & exciting
Cant wait for the next chapter
:D
9 months ago
will be fun for all when Mom joins in !!!
9 months ago
Great story, keep up the good work:)
9 months ago
Fantastic writing,,,I was hoping there would be mom involed somewhere and seems like there will be,,,can't wait.
9 months ago
One of the best orgasms ever!!!
9 months ago
Great story sparky!
9 months ago
Fantastic! I dont believe ive ever been aroused by cross dressing or man on man sex before, certainly not to orgasm. I look forward to more, more with mom if possible.