Sunday, December 4, 2011

#748 - Sissy Story 17 - My first time was with an old man

I'm addicted by first time's tales..
because i'm virgin, of course.. but not only for this reason..
in addition, mature men are my favorite target..
I think they are able to put real passion with a young gurl..
and to make you feel.. truly safe and appreciated!
I think with an old man.. i could really become a total devoted sissy slave!
so I love mature men.. and this story is dedicated to all of you.. old sweet porks! ;))
enjoy the sissy story number 17! ;))

Anna Malice

My first time was with an old man

As a young boy growing up I always had a fetish for dressing up like a girl. When I was 20yo I had my first experience with an older man, Tony a man in his 70s. I met him through a phone chat line and we seemed to hit it off right away. He told me that he would buy me some clothes and lingerie to wear for him when we met. So after a couple weeks of phone chat I mustarded up enough courage to meet him face to face.
When I arrived at Tony’s house he greeted me with a warm hug and kiss. Tony was a very handsome man, stood about 6’ tall and clearly looked like he took good care of his body. He held my hand and led me into the house. We walked into the living room and there it laid my new wardrobe. I was shocked to find that he had bought a very nice selection of lingerie and some dresses and short skirts. He picked out a very sexy black bustier with garters and g-string and as a surprise he pulled out a pair of 5” stiletto heels. He told me to go get dressed in the bathroom.
I came out dressed up in my new lingerie. Tony walked up and began to kiss me. I felt his eager tongue in my mouth searching and probing. He then pushed me firmly up against the wall, pinning my arms on each side. He continued to kiss me deeply on the mouth, then moving down to my neck. I can hear him whispering to me “You’re my little slut now and I’m going to have my way with you whether you like it or not.” I knew he liked to be dominant from out phone conversation. I played along and pretended to resist, I can tell this was making him more and more turned on. I can feel his cock getting harder and harder as he pressed up against me. By this point I can feel my little boy clit getting wet.
“Now go get in my bedroom and wait for me there” he ordered.

I waited eagerly on his bed. He came back wearing nothing but a cock ring. He had a nice cock, about 6” semi erect. He walked past me to open his bedside drawer. He pulled out some lube and studded collar and leash. Tony walked back to me and slapped the collar on me. “Get on your knees and crawl, bitch!!”
I got on all fours and he yanked on the leash, motioning me to crawl off the bed. He walked me to the end of the bed then chained me to the bed post. By now I’m feeling like a complete little Asian whore serving her White master.
“Get up on your knees bitch!!” Like a good little slut, I obeyed. “Now open your mouth.” He took a step closer then grabbed his cock and fed it to me. By now he’s pretty much fully erect, about 7”. I began to slowly suck his cock, tasting his yummy precum. I can feel his hands on the back of my head pushing his cock deeper down my throat. This was the biggest dick I’ve ever sucked until this point. I tried to pull back a little but he wouldn’t allow it. “Swallow it you little slut”, he barked.
I reached up and grabbed the base of his cock and began to bob up and down on his big manly tool. Then I ran my tongue down his shaft to his nicely shaved balls, slowly sucking on his balls. The sound of his moaning only made me hornier.
While sucking on his balls, I can feel him un-chaining the leash. He pulled me up and told me to lean against the bedpost. He then began to kiss me and running his down my chest toward my little hard clit. I felt his warm tongue licking my neck then down my chest, stopping at my perky nipples and gently biting them. While sucking on my little tits he reached into my g-string and began to stroke my erect clitty. He looks up at me and says “Looks like my baby slut has a little something extra for daddy.” He then pulls my g-string aside and knelt down to lick my clit. He started out slow then harder and harder then swallowing my clit whole. I let a soft moan which seemed to make him more excited. He spread my legs wider by put one of my feet up on the bed. He then reached under to caress my hairless balls and pussy, probing gently around the pussy. By now I have both my hands reached up over my head holding the bedpost, rocking back and forth in his mouth.
Slowly he stood up and threw my face down on the bed. He followed behind my started to rub his face on my firm little bum. Then he spread my cheeks apart to get a taste of my pussy. “Spread that cunt whore,” he demand “I wanna get a good look you.” I reached behind me and grabbed both cheeks to show off my clean shaved pussy. He immediately drove in and began to lick my eagerly awaiting pussy, probing it, digging his tongue further inside. It felt so good that I start to let out little screams of ecstasy.
“Oh ya daddy, lick my pussy. I need it sooooo bad.” I moaned.
The more I moaned the deeper his tongue went inside me. Then I felt his hand reach under to stoke my clit while the other hand rubbing on my pussy as he ate it out. As he’s rubbing on my pussy I felt his finger go in, then 2. “I’m going to stretch that cunt a little so I can fuck it good.” He told me.
After a few minutes of finger fucking me, he told me to get on all fours and keeps my legs spread. He then reached over to grab the lube and squirted some down my bum crack. The cold lube gave me a tingling sensation that sent shivers right through me. I knew it would be only a few seconds before his hard, throbbing cock would be inside me.
He squirted some lube on his hard cock then began rimming the outside of my pussy. “Daddy’s going to pound that slutty cunt of yours.” He then slapped my bum and began to push his way in. Back then I have never had my pussy fucked by anything but fingers and dildos.
“Not to fast daddy, it hurts a little.” I said. Which seem to only make him push in a little harder.
“You’re going to take it one way or another, bitch!.” With that being said he pushed all the way in as I let out a small scream of pain.
“Scream all you want whore. Daddy is going to own your cunt”
He reached forward to grab the leash that’s laying beside me and began to ride me like a dog. He pulled on the leash a little hard, choking me slightly but not enough to cut off any air circulation. He then began to pound me harder and harder.
“Mmmmm I love little Asian whores. You’re such a little good fuck toy.” He snickers.
We continued to fuck doggy style for about 10mins then he laid down on his back and told me to squat on his cock. He continued to hold the leash as I bounced up and down on his cock. I could feel that he was going to cum soon, so I started to stoke myself. Couple more minutes later I was ready to cum.
“I’m going to cum soon daddy.” I moaned.
Almost as soon as the words left my lips, I shot a big load of cream all over his stomach and chest. Then he quickly pushed me off and stood up over me.
“Open your mouth bitch, daddy has a nice load for you.”
He stood there as I choked down his throbbing cock. Then without warning I felt a hot load of cum shoot into my mouth. I swallowed a big load but more was still coming out. I felt streams of cum oozing out of my mouth as I kept sucking him till he was completely dry.


  1. Really good story, like her i'm beginner in féminization and virgin and i need to be used step by step and the story is well done to show us where is the good way

  2. giggles...
    sooo. i had just finished posting my own deflowering story, when i came here to check out your new posts... and i found this.
    Very. Hot.
    thanks now my clitty is stiff again.. whatever shall i do?


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