So Much Like Your Mother

Dedication: I wrote this one for an intimate friend. I hope you all enjoy. Everyone in the story is over 18.

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This is my confession. Some of you may read this and think that I am beyond redemption, others will realize the emotions involved and perhaps give me a pass. Either way I need to get this off my chest.

I was lying in bed, in the dark, stroking my cock and riding the edge of an orgasm. OK, so far nothing too out of the ordinary for a 19 year old, skinny effeminate boy. Not even the fact that I as wearing a pair of my Mom's thigh high stockings over my shaved legs and a pair of her sexy satin panties as I pleasured myself would be all that out of the ordinary. I had been more or less dressing in my Mom's clothes every chance I got since as far back as I could remember. I'd long since gotten over my guilt about it. Mom had even known when she was alive.

And that, my dear readers is what will make people take notice and perhaps call me a sick fuck. My Mom had died of cancer nearly eight months ago. Prior to that she was sick a long time, so long it seems like most of my life she was sick, but I know that isn't true. I remember her being young and healthy.

I certainly wouldn't want my Dad to find out that I wore Mom's things; he'd lose his mind way more than he already had. That's why I instantly froze and pretended to be asleep when my door creaked open and I saw his bulky frame in the doorway. I could tell by the way he swayed that he was drunk again. I closed my eyes most of the way so it would look like I was sleeping. My hard cock throbbed in my hand, begging me to finish. I dared not move as he came in and loomed over me.

"So sweet, my sweet, sweet Alex." He said his voice full of emotion but quiet so as not to wake me.

"You'll never know how much she loved you, or how much I loved her."

"So much like your mother... so much like her..." he said as he brushed the back of his fingers along my cheek before turning to leave.

God help me I couldn't stop. My cock exploded and my body shuddered as soon as he turned his back. It was all I could do not to cry out in ecstasy and my orgasm wracked my body. By the time my Dad shut the door my sheets and my belly were covered in cum. In the midst of all that biological commotion, my brain somehow managed to connect some dots that I really wish it hadn't.

Instantly I knew why my Dad was so emotional around me. I look nearly exactly like my Mom looked when she was healthy. I had the same blue eyes, dark curly hair, thick lips and long eye lashes that she did. My Mom was a small framed and small breasted woman. I had always known that I looked a lot like my Mom, so no revelation there. What struck me for the first time was how a grieving widower might react to seeing a near mirror image reminder of his dead wife in his teenage son. It was this realization that made me cum so hard it felt like I got hit by a bus.

After I came, I changed into boy pajamas and went to bed and cried myself to sleep. The crying had become less and less lately, but it was still an open wound. I loved my Mom more than anything in the world. I also wept for Dad's sadness. It is just awful losing someone you love so much. In my Mom's case I always loved her so much I wanted to be just like her. That had been our secret, one she took with her to her grave, that her son was a sissy.

To make things clear, I don't think my Dad was attracted to me. I was just a constant reminder. My Dad and I were never close before Mom got sick. I was too feminine for a boy in his eyes and I knew it, still he never treated me badly. When Mom got sick all that changed and we pulled together for her. Now that she was gone, I loved my Dad very much, I just wished he'd not get sad every time he looked in my general direction.

Nor was I attracted to my Dad. He was a big, older man, which did match my general taste in men (I'm bisexual, though still a virgin and very inexperienced). I did watch porn and enjoyed looking at older men fucking young girls. I always fantasized that I was the girl. Still he was my Dad and so not something I thought about a lot.

After the incident in my bedroom, my Dad was all I could think about. I wanted to make him feel better, if just for a while because I loved him. For the first time I also tentatively asked myself if I was attracted to him. I didn't know. I knew I was attracted to my Mom, I wished I could be just like her, but my Dad? I just didn't feel it the same way.

My head was full of these kinds of thoughts when Friday came around. I got back from school and hanging out with friends a bit late. Dad was already hitting the sauce while watching a football game. I made us diner and made sure he ate. It wasn't long before he was passed out sitting up on the couch.

I watched him in his troubled sleep for a while. My did, while always a big man, had really let himself go. He had gained probably forty pounds since Mom died. He used to be a very sober and clean cut guy. He always wore a nicely trimmed beard, now it was getting longer and scraggly. Still it was easy to see what Mom saw in him, despite all that he was a good looking man.

As I watched him he started to move. He was mumbling my Mom's name. Then his eyes fluttered open and he looked at me in an unfocused way.

"uhhhgh Hellen...?"

I didn't respond, just stood there watching.

"Hellen baby I could use some love." he mumbled almost incoherently.

His hand moved back and forth a bit in his lap and I looked down. My Dad had a raging hardon in his sweat pants; I could clearly see the shape of it as his hand rubbed it drunkenly. I was fascinated instantly. He was big, but not outrageously so, definitely bigger than me. I was somewhat surprised to find myself getting excited at the sight. That's when the thought hit me. I can help.

I tip toed out of the room, not wanting to disturb him further and ran up to the spare room where all of my Mom's stuff was in boxes. I knew exactly the outfit I wanted from experience, a tight black leather skirt and a low cut white blouse, with thigh high stockings and tall stiletto heels.

I quickly striped down and put on a favorite pair of Mom's black lacey panties and bra. My Mom was a small breasted woman and only wore a bra for looks and I suppose to keep her nipples under control. As such I didn't even need padding. In panties and bra I took down one of the wigs my Mom had from when she lost her hair do to chemo. I sat down at her vanity and got to work. I forced myself to not rush, to do a good job. My Dad wasn't going anywhere.

About 45 minutes later I had my makeup just about perfect. I chose a smoky eye shadow, dark red lipstick and just a bit of rouge in my cheeks. I put on the blouse, skirt and shoes. I looked at myself in the full length mirror in the corner and almost broke down crying right there. My Mom stared back at me. Fanning my eyes to dry the tearing I turned away and walked with confidence back down stairs.

My Dad was stirring again when I walked in. The clicking of my heels on the floor must have woken something deep in his stupor. He woke up and looked at me through hazy eyes, then drifted off again mumbling over and over "Hellen, Hellen."

I felt a surge of confidence. He had softened since I had left, but watching him his cock grew hard again. I knelt down between his legs and brought my face close to his cock. I kissed it tentatively through his pants and he groaned but didn't otherwise move.

Then I got bold and my hands went up to his waistband and began pulling his pants down. To my surprise he grumbled but helped me, still completely out of it. After a bit of struggle his pants were around his ankles, his rigid cock sticking up from the nest of his pubic hair. I looked at it and swallowed the nervous lump in my throat.

I reached forward and gingerly took his cock between my thumb and forefinger. He immediately let out a long low groan and pushed his hips up, thrusting and grumbling. His cock was about six inches long and pretty thick. It was very hard under the soft skin and the purple head looked angry and ready to explode. I started to feel my own somewhat smaller cock strain against the lace panties I had on.

Taking his cock in a firmer grip I started to stroke it up and down. My Dad settled down a bit, moaning and insistently thrusting it into my hand. My mouth started to water. I took the plunge, leaning forward I took the head between my lips and let him thrust into my soft warm mouth. I couldn't believe it I was actually sucking cock, and my own Dad's cock at that. I moved my head up and down a little, trying to match his thrusts and letting him in deeper, my tongue bathing the head in hot saliva.

He was really groaning now as I worked my lips further and further down his hard throbbing cock. As I took more of him the more excited I got, I was really loving this. Soon my head was bobbing up and down on my Dad's cock as he was thrusting deeper and deeper. I still couldn't quite take him all.

Then I felt his hand on the back of my head "Hellen, yes, oh Hellen" he was moaning drunkenly. He pushed me down further until the whole thing was sliding in and out between my soft wet lips. When I started this I kind of expected him to cum quickly. I don't know if it was the alcohol or what but he didn't cum right away and I was a little worried now that he would come to his senses soon. We were really going at it between his thrusts and my head bobbing up and down.

My cock was crying out for attention and I used my spare hand to rub it through my skirt. His movements started to get more frantic, less smooth, which messed up my timing and made me choke a bit. We both just kept going though. I knew he was going to cum soon. He started grunting.

"fuck."

"So good."

"fuck Helen."

"so fucking good."

"You're gonna make me cum."

He moaned and grunted over and over. I started pumping my hand and mouth up and down on his rigid dick. I couldn't tell if he was lucid or not, my entire focus on pleasing his cock.

Then his body shuddered and he cried out in a way that startled me. My mouth was filling with hot warm liquid and in my focused state it took me a second to realize he was cumming. I was filled with an odd kind of pride. I tried to swallow as fast as I could, working my throat with a mouth full of cock and cum. Cum poured out of my lips and down his cock and over my chin. I licked and sucked it greedily.

While I was cleaning him up, he lifted my head in his big hands. I looked up at him, scared of what I would find. His eyes struggled to focus on my cum covered face and apparently couldn't. He closed his eyes and leaned his head back and let out a heavy sigh.

"You look so much like your Mother." He said.