Cindys First Threesome
- 2 years ago
- 18
- 0
Cindy's First Time free porn video
My girlfriend got a new job where she would travel a lot, so I had the house to myself for days at a time. It was the perfect opportunity to explore my feminine side and start dressing up in the same sexy lingerie I would buy for her. No sooner would she hit the road and I would be in her dresser fishing out sexy outfits. I had a gym bag in the trunk of my car where I kept a wig, otherwise I'd use her heels and make up and do myself up until I was a sexy little cross dresser. Semi passable too if I do say so myself, although despite how I looked on the outside I was all sissy girl on the inside.
I would go total fem and cam online with horny guys, jerking off for them, showing off my sexy panty-clad ass for them, puckering my lips at them. I'd do anything they asked and it got to the point where I was ready to have the real thing. I'd yet to really have full on sex with men as a gurly boy. Oh I'd cruised for cock here and there but those casual hook ups were usually over as soon as they began and like I said I'd never done it fully "dressed". The sissy inside of me was just aching for a man's touch and I'd been training my pussy asshole with one of my girlfriend's dildo's for months, so I was more than ready to take a big hard cock.
I conducted my search online for the right guy, and before long I came across an older man in his sixties. An average looking guy, silver haired, kinda blue collar, but seemingly normal. My preferences weren't too specific, but I'd grown accustom to watching porn of older men fucking young sissy traps like myself, so my guy needed to have a high sex drive and be wild enough to go for a cross dresser.
His name was Hank and he was probably the sweetest man I could've hoped to meet. I asked him to call me Cindy and sent him a couple full body pics of myself, which I took with my webcam, dressed in a hot little, black baby doll negligee, fishnet stocking and heels. I wore my brunette wig and bright red lipstick. I took one pic from the front and one from the back so he could see my sweet ass beneath the skirt. In both pics I sucked on my finger and gave him a pouty look.
Best part was, I described my feelings, and how badly I wanted to be a sissy slut and how I was ready to try out the real thing with a true sex daddy, in the flesh, and he knew exactly where I was coming from. He said, "Cindy, I am going to treat you right, and take good care of your steaming hot wet pussy, so that when I'm done with you you'll be a true cock slut sissy gurl." To say he hit the spot would be an understatement and my only reply was my address and an invitation to come over that same night whenever he wanted. An hour later he was at my door.
I braced myself, took one last look in the mirror to fix my hair and check my lipstick then I took a deep breath and let him in. He was barely in the door before he was manhandling me, pawing and grabbing at my ass while kissing me passionately on the mouth. I was a little off guard, this being my first time in a private setting. He was more aggressive than I thought he would be, so I tried my best to go with the flow. I pressed my hands against his chest and let him slide his tongue into my mouth. He grabbed my cute little ass in both hands and I melted into him, collapsing my body against his. I instinctively reached down and groped his crotch which seemed to calm him down a little.
"Oh, daddy," I gasped between tongue lashes, "mmm, I'm so horny."
"Me too, baby," he whispered, "I've been dreaming about you." Then we kissed more as he pushed back against the wall of the hallway where we made out for a few more minutes. "You are so sexy, god I love your hot little outfit!" He looked me over while he fondled me.
"Want to take me to bed?" I asked him. "I want to suck daddy's cock."
Without a word, and without taking me up on my offer to go to the bedroom right away, he unzipped his pants and whipped out his giant uncut piece of meat, which had been steadily growing in his pants beneath my hand. I dropped right down to my knees and took hold of his beautiful cock and immediately began to lick and kiss it all over. I massaged his hairy balls, looked up into his eyes and sucked on the head of his cock.
"Like this, daddy?" I whispered up to him, "if this how you want me?"
"Yesssss," he hissed staring into my eyes lustfully," that's perfect baby, suck daddy's dick, make daddy feel good, baby girl." He held my cheek in his hand as I took him in my mouth, over my tongue and down the back of my throat. I rubbed my own cock through my silk panties as I squatted there on the floor sucking him. Finally he took me by the hand and I stood up. He kissed me again on the lips and said, "The bed, let's go."
Then he followed me upstairs to the bedroom. On the way up I made sure he got a good look at my panties from behind until he began reaching up through my legs. At one point I thought he may knock me down and have me right there on the stairs but we eventually made it to the bed where I crawled across until my ass was sticking up in the air. I watched him over my shoulder as he undressed, and his cock was still rock hard. He climbed up on the bed behind me and wrapped his manly arms around my waist while resting his prick between my ass cheeks.
"Oooo," I whimpered, "fuck me through my panties daddy...make me feel like a little bitch." Then he spit on his hand, reached beneath my panties and smeared my asshole until it was wet. "Yeah, daddy, use my pussy, put that big hard cock inside me. I want to feel your raw cock deep in my wet cunt." Without any further encouragement he pushed his cock into my ass until he was balls deep inside of me. I lay on my stomach, legs spread, as he gently rocked back and forth loosening me up more and more until I was fully primed. Then I began to push back into him, arching my back and flexing my asshole until I was hungrily taking him as deep as he could go. He grabbed my hips and began to seriously fuck me.
"If this what you want, Cindy?" he said.
"Yes, daddy! Oh god yesssss."
"You want to be fucked like a girl." He growled, "You want daddy dick up your fucking pussy all day don't you?"
"Oh god yes daddy I do, I want it all the time."
"You feel like a sissy slut don't you, in panties and lipstick...you want daddy to keep fucking you until he cums inside you don't you?" he asked.
"Oh fuck! Yes, daddy, that's what I want, I want it so bad, I want to be fucked and I want your hot cum so bad."
"Where? Where do you want it, Cindy, up your sweet cunt?" he asked.
Then I looked back at him, my ass burning while he thrust in and out of me, my mind swirling with filthy thoughts as my fantasy was literally being fulfilled and I said, "Cum all over my fucking face. I want your hot cum all over me... make me your sissy slut!"
I got up on all fours and broke a sweat as he pounded away at my ass like no one had ever done before. I kept telling him how good he was, and how amazing he made me feel, and he kept talking dirty back to me until he was finally ready to explode. He withdrew his cock and I spun around and sucked on his throbbing shaft.
"I'm gonna cum," he said as I held my mouth open sticking my tongue out. "Oh fuck!" he exclaimed as he blasted my face with hot gobs of cum. He pumped load after load into my mouth and all over my face until I was covered in it warm luscious sperm. Then he stuffed his wet prick into my mouth and I sucked his cum-covered cock clean. I scooped his load off my face and ate every drop as I laid back on the bed beside him. I kept stroking his cock as I rested my body against his. We were both sweaty and out of breath but we kept kissing and caressing all the same.
"Oh my god," I whispered as I fondled his cock and balls, "that was so fucking hot, daddy."
"Want me to go now?" he asked.
"What?" I said looking him in the eye, "no, I want you to stay." Then I kissed him passionately on the lips. He held me close, grabbing my entire sweet little ass in one hand as I threw one leg over his torso. I finally broke our kiss and said, "I want you to fuck me again when you're ready."
"If you want me to," he said.
"Will you please cum in my ass this time? I want to feel you pump a load into my pussy. Besides," I said, "my little clit is hard now too." Then I leaned back, spread my legs and showed him my boner sticking up out of the top of my panties. "Aren't you going to kiss it for me, daddy?"
"Oh, honey, yes I am." Then he leaned down until his head was in my lap and he engulfed my cock in his mouth. He sucked me while he began to finger my pussy, which was still gapping and wet. He used two fingers on me and after a few minutes of sucking my cock, he flipped me over on my stomach and pulled my panties down unit they were over my ass cheeks. Then he buried his tongue in my hole and began to eat me out. I reached back and grabbed his head, holding him in place while he ferociously ate my pussy.
"Mmmm," I moaned at him, "oooo, daddy, yeah eat my pussy for me. Lick my hole! Oh fuck that feels so sexy! Nobody has ever done that to me before, no one has ever licked my pussy asshole before daddy, oooo fuck me." I reached under myself and grabbed my hard on. I gripped my cock and prayed I wouldn't cum yet, not until his big daddy dick was back inside of me. I looked back over my shoulder and saw he was using one hand to stroke himself back to erection while the other hand was beginning to pry open my pussy again. Before long he had three fingers up my ass while he lapped up my wet cunt hole. "Oh fuck," I growled, "I need that big daddy dick again, fuck me, daddy, please fuck me with that huge cock."
Then he knelt behind me and with ease fit his cock back inside of me. I went to all fours again and we found our stride as I pushed back into every thrust he gave me. He fucked me like I was his bitch and I loved it. I shouted and yelled with ecstasy as he did it to me, and I could swear he was even harder than before.
"Oh fuck," I yelled," yeah, daddy, fuckmefuckmefuckmefuckmefuckme!"
"Aw yeah," he shouted, "take that big dick, baby, take daddy's big fat cock up that sweet pussy cunt!" We became animalistic in our fucking and I kept looking back over my shoulder into his eyes. He gritted his teeth and glared at me while holding my hips in both hands. Just when my body began to go numb he finally said, "I am going to fucking cum! I'm going to cum right up your sweet fucking cunt hole!"
"Oh fuck," I said nearly bursting into tears, "I'm going to cum too daddy, let's both cum at the same time. I want to feel your hard cock throb in my pussy when I cum." He was balls deep inside of me when he finally came, and I could feel his fat cock unload into me. I could feel his cum gushing into me. I could feel his sweat rolling off his body and down my crack. And finally I came too, and fell face first into the pillows as my own cock spasmed beneath me. My lover collapsed onto of me and with his cock still lodged in my boy pussy, he kissed my neck and shoulders. I smiled as we laid there in a pile of spent sexual pleasure and cum. I reached behind me and caressed his naked body.
He said, "Now do you want me to leave?"
"No," I said, "I want you to spend the night." Then I managed to roll over as he pulled out of me. I wrapped my arms around his neck and my legs around his waist and held him in place. I pulled him down onto of me so we could kiss. With his sweaty, naked body against mine I said, "I'm not done with you yet."
I would go total fem and cam online with horny guys, jerking off for them, showing off my sexy panty-clad ass for them, puckering my lips at them. I'd do anything they asked and it got to the point where I was ready to have the real thing. I'd yet to really have full on sex with men as a gurly boy. Oh I'd cruised for cock here and there but those casual hook ups were usually over as soon as they began and like I said I'd never done it fully "dressed". The sissy inside of me was just aching for a man's touch and I'd been training my pussy asshole with one of my girlfriend's dildo's for months, so I was more than ready to take a big hard cock.
I conducted my search online for the right guy, and before long I came across an older man in his sixties. An average looking guy, silver haired, kinda blue collar, but seemingly normal. My preferences weren't too specific, but I'd grown accustom to watching porn of older men fucking young sissy traps like myself, so my guy needed to have a high sex drive and be wild enough to go for a cross dresser.
His name was Hank and he was probably the sweetest man I could've hoped to meet. I asked him to call me Cindy and sent him a couple full body pics of myself, which I took with my webcam, dressed in a hot little, black baby doll negligee, fishnet stocking and heels. I wore my brunette wig and bright red lipstick. I took one pic from the front and one from the back so he could see my sweet ass beneath the skirt. In both pics I sucked on my finger and gave him a pouty look.
Best part was, I described my feelings, and how badly I wanted to be a sissy slut and how I was ready to try out the real thing with a true sex daddy, in the flesh, and he knew exactly where I was coming from. He said, "Cindy, I am going to treat you right, and take good care of your steaming hot wet pussy, so that when I'm done with you you'll be a true cock slut sissy gurl." To say he hit the spot would be an understatement and my only reply was my address and an invitation to come over that same night whenever he wanted. An hour later he was at my door.
I braced myself, took one last look in the mirror to fix my hair and check my lipstick then I took a deep breath and let him in. He was barely in the door before he was manhandling me, pawing and grabbing at my ass while kissing me passionately on the mouth. I was a little off guard, this being my first time in a private setting. He was more aggressive than I thought he would be, so I tried my best to go with the flow. I pressed my hands against his chest and let him slide his tongue into my mouth. He grabbed my cute little ass in both hands and I melted into him, collapsing my body against his. I instinctively reached down and groped his crotch which seemed to calm him down a little.
"Oh, daddy," I gasped between tongue lashes, "mmm, I'm so horny."
"Me too, baby," he whispered, "I've been dreaming about you." Then we kissed more as he pushed back against the wall of the hallway where we made out for a few more minutes. "You are so sexy, god I love your hot little outfit!" He looked me over while he fondled me.
"Want to take me to bed?" I asked him. "I want to suck daddy's cock."
Without a word, and without taking me up on my offer to go to the bedroom right away, he unzipped his pants and whipped out his giant uncut piece of meat, which had been steadily growing in his pants beneath my hand. I dropped right down to my knees and took hold of his beautiful cock and immediately began to lick and kiss it all over. I massaged his hairy balls, looked up into his eyes and sucked on the head of his cock.
"Like this, daddy?" I whispered up to him, "if this how you want me?"
"Yesssss," he hissed staring into my eyes lustfully," that's perfect baby, suck daddy's dick, make daddy feel good, baby girl." He held my cheek in his hand as I took him in my mouth, over my tongue and down the back of my throat. I rubbed my own cock through my silk panties as I squatted there on the floor sucking him. Finally he took me by the hand and I stood up. He kissed me again on the lips and said, "The bed, let's go."
Then he followed me upstairs to the bedroom. On the way up I made sure he got a good look at my panties from behind until he began reaching up through my legs. At one point I thought he may knock me down and have me right there on the stairs but we eventually made it to the bed where I crawled across until my ass was sticking up in the air. I watched him over my shoulder as he undressed, and his cock was still rock hard. He climbed up on the bed behind me and wrapped his manly arms around my waist while resting his prick between my ass cheeks.
"Oooo," I whimpered, "fuck me through my panties daddy...make me feel like a little bitch." Then he spit on his hand, reached beneath my panties and smeared my asshole until it was wet. "Yeah, daddy, use my pussy, put that big hard cock inside me. I want to feel your raw cock deep in my wet cunt." Without any further encouragement he pushed his cock into my ass until he was balls deep inside of me. I lay on my stomach, legs spread, as he gently rocked back and forth loosening me up more and more until I was fully primed. Then I began to push back into him, arching my back and flexing my asshole until I was hungrily taking him as deep as he could go. He grabbed my hips and began to seriously fuck me.
"If this what you want, Cindy?" he said.
"Yes, daddy! Oh god yesssss."
"You want to be fucked like a girl." He growled, "You want daddy dick up your fucking pussy all day don't you?"
"Oh god yes daddy I do, I want it all the time."
"You feel like a sissy slut don't you, in panties and lipstick...you want daddy to keep fucking you until he cums inside you don't you?" he asked.
"Oh fuck! Yes, daddy, that's what I want, I want it so bad, I want to be fucked and I want your hot cum so bad."
"Where? Where do you want it, Cindy, up your sweet cunt?" he asked.
Then I looked back at him, my ass burning while he thrust in and out of me, my mind swirling with filthy thoughts as my fantasy was literally being fulfilled and I said, "Cum all over my fucking face. I want your hot cum all over me... make me your sissy slut!"
I got up on all fours and broke a sweat as he pounded away at my ass like no one had ever done before. I kept telling him how good he was, and how amazing he made me feel, and he kept talking dirty back to me until he was finally ready to explode. He withdrew his cock and I spun around and sucked on his throbbing shaft.
"I'm gonna cum," he said as I held my mouth open sticking my tongue out. "Oh fuck!" he exclaimed as he blasted my face with hot gobs of cum. He pumped load after load into my mouth and all over my face until I was covered in it warm luscious sperm. Then he stuffed his wet prick into my mouth and I sucked his cum-covered cock clean. I scooped his load off my face and ate every drop as I laid back on the bed beside him. I kept stroking his cock as I rested my body against his. We were both sweaty and out of breath but we kept kissing and caressing all the same.
"Oh my god," I whispered as I fondled his cock and balls, "that was so fucking hot, daddy."
"Want me to go now?" he asked.
"What?" I said looking him in the eye, "no, I want you to stay." Then I kissed him passionately on the lips. He held me close, grabbing my entire sweet little ass in one hand as I threw one leg over his torso. I finally broke our kiss and said, "I want you to fuck me again when you're ready."
"If you want me to," he said.
"Will you please cum in my ass this time? I want to feel you pump a load into my pussy. Besides," I said, "my little clit is hard now too." Then I leaned back, spread my legs and showed him my boner sticking up out of the top of my panties. "Aren't you going to kiss it for me, daddy?"
"Oh, honey, yes I am." Then he leaned down until his head was in my lap and he engulfed my cock in his mouth. He sucked me while he began to finger my pussy, which was still gapping and wet. He used two fingers on me and after a few minutes of sucking my cock, he flipped me over on my stomach and pulled my panties down unit they were over my ass cheeks. Then he buried his tongue in my hole and began to eat me out. I reached back and grabbed his head, holding him in place while he ferociously ate my pussy.
"Mmmm," I moaned at him, "oooo, daddy, yeah eat my pussy for me. Lick my hole! Oh fuck that feels so sexy! Nobody has ever done that to me before, no one has ever licked my pussy asshole before daddy, oooo fuck me." I reached under myself and grabbed my hard on. I gripped my cock and prayed I wouldn't cum yet, not until his big daddy dick was back inside of me. I looked back over my shoulder and saw he was using one hand to stroke himself back to erection while the other hand was beginning to pry open my pussy again. Before long he had three fingers up my ass while he lapped up my wet cunt hole. "Oh fuck," I growled, "I need that big daddy dick again, fuck me, daddy, please fuck me with that huge cock."
Then he knelt behind me and with ease fit his cock back inside of me. I went to all fours again and we found our stride as I pushed back into every thrust he gave me. He fucked me like I was his bitch and I loved it. I shouted and yelled with ecstasy as he did it to me, and I could swear he was even harder than before.
"Oh fuck," I yelled," yeah, daddy, fuckmefuckmefuckmefuckmefuckme!"
"Aw yeah," he shouted, "take that big dick, baby, take daddy's big fat cock up that sweet pussy cunt!" We became animalistic in our fucking and I kept looking back over my shoulder into his eyes. He gritted his teeth and glared at me while holding my hips in both hands. Just when my body began to go numb he finally said, "I am going to fucking cum! I'm going to cum right up your sweet fucking cunt hole!"
"Oh fuck," I said nearly bursting into tears, "I'm going to cum too daddy, let's both cum at the same time. I want to feel your hard cock throb in my pussy when I cum." He was balls deep inside of me when he finally came, and I could feel his fat cock unload into me. I could feel his cum gushing into me. I could feel his sweat rolling off his body and down my crack. And finally I came too, and fell face first into the pillows as my own cock spasmed beneath me. My lover collapsed onto of me and with his cock still lodged in my boy pussy, he kissed my neck and shoulders. I smiled as we laid there in a pile of spent sexual pleasure and cum. I reached behind me and caressed his naked body.
He said, "Now do you want me to leave?"
"No," I said, "I want you to spend the night." Then I managed to roll over as he pulled out of me. I wrapped my arms around his neck and my legs around his waist and held him in place. I pulled him down onto of me so we could kiss. With his sweaty, naked body against mine I said, "I'm not done with you yet."
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