Paying Mommy’s Mortgage

This story contains incest, non-censual sex, crossdressing and nylon fetish themes. If you are offended by such material do not read the story. Comments and criticism are always welcome and appreciated. All characters in this story are adults.

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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 family and we have a great family life as we are often together for festive occasions and family dinners. I have an Uncle Wally on my father's side of the family 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 child'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 kids 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 drunk at the time; I'm absolutely hopeless when I'm drunk, 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 drunk. 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 brother 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 family 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 family 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.