Sissy Stepson 10 Stepmother s Sissy
- 4 years ago
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Becoming The Sissy Girl I’d Always Longed To Be free porn video
I wanted to thank him for all he done for me in the last couple months, all the times he’d taken me out to dinner when I was broke and the money he loaned me for rent after I got ripped off. I was such a shy k** back then and it was nice to have someone around that take the lead and anticipated my needs. I was in a tough spot and I appreciated the fact that i didn’t have to ask for his help at every turn. He just lent it. Now here we were back at his place after a busy morning of running errands around town. I wasn’t sure if he was gay, or if I was for that matter, but I had a feeling he might be. The hugs goodbye were warm and comfortable and lasted a maybe little longer than they might with a platonic friends. On a couple of occasions, his hand had wandered a little lower down my back and there seemed to be some intention when it brushed against my butt. The sensation of the touch of his fingertip against the back pocket of my blue jeans had stayed with me long after I’d left that other night.
He sat next to me fairly close on the sofa as we watched our sitcom and I looked over at his leg and began to form and idea of what I wanted to do. My heart beat faster through the commercials and segments and then it happened, almost involuntarily. I scooched in a little bit and slid my hand onto his thigh. My fingers felt a little clammy and nervous, but I left them there and he didn’t seem to mind or even acknowledge the move. Another sit-com started and I began to move my hand back and forth, up and down slowly on his thigh. He leg was so much firmer and more muscular than mine. He got up to get a bag of chips from the kitchen and I thought that might be the end of it. But when he returned he sat a little closer to me, and, after a moment, he took me hand and gently placed it back where it had been. I fumbled up and down a little more and found myself heading for his fly, and enjoying the weight and gravitas of what lie beneath. I could feel his pulse through his jeans and the shape beginning to change. He put his armed around me, and I calmed a little and cozied up to his chest.
Now I was looking down at what I was doing and thinking about what should happen next. I need to unbutton those jeans to make room for his expanding needs. My other hand entered the picture and I unbuttoned and then unzipped. I watched as my left hand reached across and it darted into his underpants, found his cock and helped the phalus out of its confines. He began to rub his fingers through my hair and I stared at the penis pointing up at me. I’d never really looked at anyone else’s penis up close before. This one was definitely larger than mine but not so big as to be intimidating. Admittedly, my mouth began to water, but I wasn’t ready to indulge just yet. I sat up and watched the rest of Seinfeld and gently stroked his shaft as I did so, and contemplated sucking my first cock.
My own organ was getting hard as I thought about tasting that cock and my breathing was getting quicker too. As the evening news started, he walked his hand up my neck, cupped the back of my head and gently guided me down to his shaft. Tugging his jeans out of the way as I teased his sack with my tongue, I gave a wet kiss or three underneath his scrotum, then two or three just above his sack at the base of his dick. My lips followed the vain up to the top and I circle his head with the tip of my tongue. When I got all the way around I moved up the part on the underside of his dick head, pursed my lips and placed a warm wet kiss right on top and then took it like a pussy. I just closed my eyes and took it in. What a rush! What a mouthful, so meaty, so firm, and so reassuring. My eyes began to tear up, just a little, as gorged myself on his man meat. I was crouched sideways on the couch like a little squirrel or bunny and he was feeling my ass, paying special attention to the divide. Then with his other hand he reached beneath me and undid my jeans and I was freed from my masculine trappings. I paused to throw off my shirt, so that my only clothing was d****d around my knees. Somehow I maneuvered my self off of the sofa on my knees, cock in mouth and leaned in closer.
I heard the sports reported start reading scores and turned around, out of habit, to see them. That whenI really lost control of the evening. He gripped me around the waist with his hands and turned my body towards the television screen, then worked his firm paws up my ribs to so that they were just under my shoulders, the whole time pushing me forward, until I was bent over the coffee table. Next he placed his open palm between my should blades and applied a little pressure, lowering my chest until my bare chest was pressing against the glass tabletop and my but was up in the air and exposed. He began exploring the small of my back with his fingertips and the part down to my anus, licked his finger and plied his way in. Once his middle finger was all the way in, as far as it would go, he lifted his hand from my upper back and gave me firm spankings on the side of my ass that made my anus grip the finger and release. The finger was rough against the inner walls, but I have to admit, I enjoyed it nonetheless. With each spank, I sucked in a little air through teeth, squinched my eyed shut and reared my hips in to the air to meet that finger.
He whispered, “stay right here,” as he paused to fetch some lubricant. I welcomed his warm body as he returned and once again embraced my back side, this time sitting back and gently rubbing me down with scented oils. He suddenly returned to fingering me, fast this time, spanking me a little harder as he went, and I squirmed and recoiled and made weird noises under my breath, my ass shaking side to side and up and down. When he finally inserted his manhood, I welcomed the slower pace of entry and the smoother texture, but winced at it’s girth. I opened my lips wide, telegraphing my ass to do the same and let a long slow moan. He arrived at a place were everything felt comfortable, and I was warm and squishy inside, then slowly pulled back and proceeded to do it again. It must have been about the fourth or fifth time that he jabbed in quick and surprised me, straightening my spine until I could feel his hairy chest against my back. He embraced me and expertly directed me down to the rug, so that he could really go to work. He placed a couch cushion under my chin, which I bit with my teeth as I stared down at the tweed. As he had his way with me, I closed my eyes and found myself dreaming of lacey panties, smooth legs, berets, makeup, lipstick, painted toenails, heels, bras and breast forms, cooking dinner for him and meeting him at the door in a little apron with gentle kisses, one leg raised in the air as he cupped my bottom. My strange reverie was interrupted and began to rut ever harder and grunt and slap my ass. Wham, wham, wham! He was gushing like a volcano all up in my ass and all over my back. He must have saved that up for a week! I collapsed on the floor and he collapse on top of me too for a moment and then wandered off the shower.
Five minutes must have went by before I peeled my self off of the ground and stumbled in to join him. Still in a dreamlike state, I pulled back the curtain just enough to slip into the warm shower. I lathered him up and stroked my cock with his semi-hard parts against my back. I fell to my knees and let the warm sudsy water run down my face as the head of his dick bumped into my face, finally finding it’s way back into my mouth. I took deep breathes, closed my eyes and felt it become hard and throb against my tongue. I thought about all the subtle advances he’d made towards me as our friendship developed: The way he opened doors for me, insisted on paying for dinner or drinks, the warm hugs goodbye that lasted a little too long. I was a little embarrassed and ashamed but also aroused as I realized that everyone at church already thought of me as his boyfriend. He was definitely wearing the pants in this situation. My eyes teared up again as his cum hit the back of my mouth and I felt it ooze down my throat.
He turned off the water, helped me to my feet and gently wrapped me in a towel, as though it was a dress. Then he looked into eyes and held me in his arms as though I was a woman. Gentle kisses followed and I enjoyed his warm, tender embrace. The whole experience should have felt foreign to me, but it didn’t. It was somehow familiar and right and my shame was beginning to be replaced by relief that I was finally being treated the way I had secretly longed to be. As I looked back on the last couple of weeks I realized that I had u*********sly been changing my behavior all along. Wearing a little more form fitting clothes, lingering a little longer and a little later at his place each evening, waiting at the door for his gentle hugs and letting them last a little longer. Looking back as I walking away to make sure that he was checking me out. Now as he held me in his arms and cupped my ass through the terry cloth towel, I wished I was wearing women’s underwear; red satin panties that covered my whole ass. My nipples were cold in the damp towel and I wished they were covered with a matching bra. I wished that my legs were shaved smooth to the touch for him and that I could stand up tall and sexy as I kissed him in a pair of high heels. I couldn’t tell him any of this just yet. I couldn’t really even admit it to my self. For now I just had to enjoy his warm embrace and feel my asshole pucker in anticipation. He took my hand and led me to his bedroom. I lay down on my tummy on his king sized bed and closed my eyes. I felt him lift the towel, and then a couple of spanks and kisses on my bum. Slowly he spread my cheeks with his strong hands and began to lick my anus and the tender skin around it. His tongue darted in and out and then his thumb and middle finger, with a little warming massage oil. I was in heaven and my semi hard cock pumped semen onto the towel as I panted in delight. He removed the towel and lay down and top of me, his curly chest hairs brushing against my back. His hard cock was set perfectly across the crack of my ass and I could feel his pulse throbbing rhythm on my sphincter. Sawing up and down slowly at first, as he massaged my shoulders, this big hulk of a man began to swing into motion. More lube was applied as he vigorously slid and sawed. Oh god! I wished I was wearing sexy black fishnets and a matching silk slip. All that friction was beginning to heat things up down there and the piston pumped faster and faster and then it stuck in my hole and he reared back and drove it home. I arched my back and grabbed my tits with his hands and bit the back of my sideways like a cat. After a few thrusts, I let go and collapsed on the bed, overpowered. I was covered in manhood and contained beneath him as he pounded away and squeezed me ever tighter. I heard the cries of a women and realized the women was me. That was the sound of letting go and taking what i deserved. That was the beginning of me becoming the sissy girl I’d always longed to be.
He sat next to me fairly close on the sofa as we watched our sitcom and I looked over at his leg and began to form and idea of what I wanted to do. My heart beat faster through the commercials and segments and then it happened, almost involuntarily. I scooched in a little bit and slid my hand onto his thigh. My fingers felt a little clammy and nervous, but I left them there and he didn’t seem to mind or even acknowledge the move. Another sit-com started and I began to move my hand back and forth, up and down slowly on his thigh. He leg was so much firmer and more muscular than mine. He got up to get a bag of chips from the kitchen and I thought that might be the end of it. But when he returned he sat a little closer to me, and, after a moment, he took me hand and gently placed it back where it had been. I fumbled up and down a little more and found myself heading for his fly, and enjoying the weight and gravitas of what lie beneath. I could feel his pulse through his jeans and the shape beginning to change. He put his armed around me, and I calmed a little and cozied up to his chest.
Now I was looking down at what I was doing and thinking about what should happen next. I need to unbutton those jeans to make room for his expanding needs. My other hand entered the picture and I unbuttoned and then unzipped. I watched as my left hand reached across and it darted into his underpants, found his cock and helped the phalus out of its confines. He began to rub his fingers through my hair and I stared at the penis pointing up at me. I’d never really looked at anyone else’s penis up close before. This one was definitely larger than mine but not so big as to be intimidating. Admittedly, my mouth began to water, but I wasn’t ready to indulge just yet. I sat up and watched the rest of Seinfeld and gently stroked his shaft as I did so, and contemplated sucking my first cock.
My own organ was getting hard as I thought about tasting that cock and my breathing was getting quicker too. As the evening news started, he walked his hand up my neck, cupped the back of my head and gently guided me down to his shaft. Tugging his jeans out of the way as I teased his sack with my tongue, I gave a wet kiss or three underneath his scrotum, then two or three just above his sack at the base of his dick. My lips followed the vain up to the top and I circle his head with the tip of my tongue. When I got all the way around I moved up the part on the underside of his dick head, pursed my lips and placed a warm wet kiss right on top and then took it like a pussy. I just closed my eyes and took it in. What a rush! What a mouthful, so meaty, so firm, and so reassuring. My eyes began to tear up, just a little, as gorged myself on his man meat. I was crouched sideways on the couch like a little squirrel or bunny and he was feeling my ass, paying special attention to the divide. Then with his other hand he reached beneath me and undid my jeans and I was freed from my masculine trappings. I paused to throw off my shirt, so that my only clothing was d****d around my knees. Somehow I maneuvered my self off of the sofa on my knees, cock in mouth and leaned in closer.
I heard the sports reported start reading scores and turned around, out of habit, to see them. That whenI really lost control of the evening. He gripped me around the waist with his hands and turned my body towards the television screen, then worked his firm paws up my ribs to so that they were just under my shoulders, the whole time pushing me forward, until I was bent over the coffee table. Next he placed his open palm between my should blades and applied a little pressure, lowering my chest until my bare chest was pressing against the glass tabletop and my but was up in the air and exposed. He began exploring the small of my back with his fingertips and the part down to my anus, licked his finger and plied his way in. Once his middle finger was all the way in, as far as it would go, he lifted his hand from my upper back and gave me firm spankings on the side of my ass that made my anus grip the finger and release. The finger was rough against the inner walls, but I have to admit, I enjoyed it nonetheless. With each spank, I sucked in a little air through teeth, squinched my eyed shut and reared my hips in to the air to meet that finger.
He whispered, “stay right here,” as he paused to fetch some lubricant. I welcomed his warm body as he returned and once again embraced my back side, this time sitting back and gently rubbing me down with scented oils. He suddenly returned to fingering me, fast this time, spanking me a little harder as he went, and I squirmed and recoiled and made weird noises under my breath, my ass shaking side to side and up and down. When he finally inserted his manhood, I welcomed the slower pace of entry and the smoother texture, but winced at it’s girth. I opened my lips wide, telegraphing my ass to do the same and let a long slow moan. He arrived at a place were everything felt comfortable, and I was warm and squishy inside, then slowly pulled back and proceeded to do it again. It must have been about the fourth or fifth time that he jabbed in quick and surprised me, straightening my spine until I could feel his hairy chest against my back. He embraced me and expertly directed me down to the rug, so that he could really go to work. He placed a couch cushion under my chin, which I bit with my teeth as I stared down at the tweed. As he had his way with me, I closed my eyes and found myself dreaming of lacey panties, smooth legs, berets, makeup, lipstick, painted toenails, heels, bras and breast forms, cooking dinner for him and meeting him at the door in a little apron with gentle kisses, one leg raised in the air as he cupped my bottom. My strange reverie was interrupted and began to rut ever harder and grunt and slap my ass. Wham, wham, wham! He was gushing like a volcano all up in my ass and all over my back. He must have saved that up for a week! I collapsed on the floor and he collapse on top of me too for a moment and then wandered off the shower.
Five minutes must have went by before I peeled my self off of the ground and stumbled in to join him. Still in a dreamlike state, I pulled back the curtain just enough to slip into the warm shower. I lathered him up and stroked my cock with his semi-hard parts against my back. I fell to my knees and let the warm sudsy water run down my face as the head of his dick bumped into my face, finally finding it’s way back into my mouth. I took deep breathes, closed my eyes and felt it become hard and throb against my tongue. I thought about all the subtle advances he’d made towards me as our friendship developed: The way he opened doors for me, insisted on paying for dinner or drinks, the warm hugs goodbye that lasted a little too long. I was a little embarrassed and ashamed but also aroused as I realized that everyone at church already thought of me as his boyfriend. He was definitely wearing the pants in this situation. My eyes teared up again as his cum hit the back of my mouth and I felt it ooze down my throat.
He turned off the water, helped me to my feet and gently wrapped me in a towel, as though it was a dress. Then he looked into eyes and held me in his arms as though I was a woman. Gentle kisses followed and I enjoyed his warm, tender embrace. The whole experience should have felt foreign to me, but it didn’t. It was somehow familiar and right and my shame was beginning to be replaced by relief that I was finally being treated the way I had secretly longed to be. As I looked back on the last couple of weeks I realized that I had u*********sly been changing my behavior all along. Wearing a little more form fitting clothes, lingering a little longer and a little later at his place each evening, waiting at the door for his gentle hugs and letting them last a little longer. Looking back as I walking away to make sure that he was checking me out. Now as he held me in his arms and cupped my ass through the terry cloth towel, I wished I was wearing women’s underwear; red satin panties that covered my whole ass. My nipples were cold in the damp towel and I wished they were covered with a matching bra. I wished that my legs were shaved smooth to the touch for him and that I could stand up tall and sexy as I kissed him in a pair of high heels. I couldn’t tell him any of this just yet. I couldn’t really even admit it to my self. For now I just had to enjoy his warm embrace and feel my asshole pucker in anticipation. He took my hand and led me to his bedroom. I lay down on my tummy on his king sized bed and closed my eyes. I felt him lift the towel, and then a couple of spanks and kisses on my bum. Slowly he spread my cheeks with his strong hands and began to lick my anus and the tender skin around it. His tongue darted in and out and then his thumb and middle finger, with a little warming massage oil. I was in heaven and my semi hard cock pumped semen onto the towel as I panted in delight. He removed the towel and lay down and top of me, his curly chest hairs brushing against my back. His hard cock was set perfectly across the crack of my ass and I could feel his pulse throbbing rhythm on my sphincter. Sawing up and down slowly at first, as he massaged my shoulders, this big hulk of a man began to swing into motion. More lube was applied as he vigorously slid and sawed. Oh god! I wished I was wearing sexy black fishnets and a matching silk slip. All that friction was beginning to heat things up down there and the piston pumped faster and faster and then it stuck in my hole and he reared back and drove it home. I arched my back and grabbed my tits with his hands and bit the back of my sideways like a cat. After a few thrusts, I let go and collapsed on the bed, overpowered. I was covered in manhood and contained beneath him as he pounded away and squeezed me ever tighter. I heard the cries of a women and realized the women was me. That was the sound of letting go and taking what i deserved. That was the beginning of me becoming the sissy girl I’d always longed to be.
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