Paying Mommy’s Mortgage

"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 forced 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 forced 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 family as a person who commits crossdressed incest 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 forced 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 forced 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 animal, 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 forced 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 animal 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 scrape 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 forced 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 forced 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 forced 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 forced 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 rape 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...