The White Sissy Slave Society A Walk into Sissyhood
- 3 years ago
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Continued Sissy Date free porn video
Before James arrived, I checked myself in the mirror; to make sure I looked great for him. My girlfriend Ann taught me well how to apply my shade and I styled my hair long and curly, so it just d****d over my shoulders, my short grey dress stretched tightly over my chubby frame and looked great against my light chocolate skin tone. I painted my toes so when they poked out the 3-inch mule they would be very pleasing. A little lip gloss and finally a dab of my favorite perfume behind each ear. After a few more poses I asked myself “Does this dress my butt look big?” then chuckled to myself remembering James said he likes a gurl with nice bubble butt. OMG I was getting more girly by the minute! Once again, I was a bit nervous knowing what was going to happen tonight, but a shot of Skyy Volka helped with that temporarily. The fact kept hitting me that there is a huge difference between my toys, and having a real man eager to “break me in.” And from our first session, I knew he would he would have to be slow taking me.
Just as I was putting on my necklace, the buzzer rang, and I thought this is it. A few minutes later there was a knock at the door, and my guy was there in my doorway was a bottle of wine. It was fun to see the grin on his face. Even in my heels, I had to stretch on my tippy-toes to kiss him. His scruffy beard felt so manly against my soft skin. Once again he gave me an enormous hug where his shoulders felt like they engulfed my entire body. But this hug was different, his hands went from the small of my back down to my chunky ass. We kissed as his strong hands groped each cheek and palmed them like basketballs. As he tonged me I also felt his bulge inflate. After we broke our kiss I gave a playful “Whew” and laughingly fanned my face. I loved the sparkle of his green eyes looking me over again.
“Wow, you look stunning”, I think this time he could actually see me blush! We sat back down on the sofa, the scene of the crime from earlier in the day, and talked a bit as we enjoyed a couple of glasses of wine. We talked about so many subjects as the wine flowed. Then he asked, “Is this really your first time?” “Yes” I replied. Telling him I recently started to accept who I am and what I want. “That was first real blowjob I gave you” “You, all of this is new to me, but my female friends knew” “They helped me learn how to dress, walk, act, do makeup, you name it.” James smiled, brushed my hair back and gave me a long passionate kiss. Something inside of me pushed flicked on, wanting to give him all of me, and I returned his passionate kiss. When was broke from our kiss the second time, James looked down to see the small lump under my dress. I looked at him and looked down, then inexplicably apologized. I thought I had that little thing tucked away. He gave a quick chuckle, kissed me on the forehead and said everything is fine. Now it was my turn to lunge into James was a passionate kiss. Our tongues slid over, around our mouths as I unbuckled his belt. James, being a man of experience, knew how to strike when the iron was hot. He popped off his shoes, just in time for me to slip off his pants. Next, to go was his knit shirt revealing his brawny chest. It was not musclebound or rippling with muscles like in the magazines, but it was perfect for me. He also did not have 6-pack abs but I could tell he kept himself in shape for a man his age.
I rubbed my hands over his massive back as James removed his socks. He was almost completely naked except for his tenting blue boxers. With a devilish smile, I helped free his beautifully thick, uncircumcised cock from its confinement. As, I started to remove my dress, he quickly grabbed my hand and shook his head. Noticing my confusion, he said “Let everything on, I want you just this this.” I nodded my head in agreement not wanting to spoil the mood. Everything stayed on, including my shoes. My attentions turned back to his thick white cock, still growing in my hand. Stroking his cock made it harder and bigger. James rubbing tweaking my nipples under my dress was so turning me on, I was almost at the point of begging him to just take it! I think that was his plan all along and it was working.
We got back comfortable on the couch again, James slumped to bring his cock to the perfect sucking position, and I complied curling up in a ball over his and taking the head of his cock in my mouth. James gave a moan of satisfaction as my tongue gently rolled over the slit of his cockhead, again exploring real flesh. I thought how lucky it must be to be so well-endowed, his cock was twice the size of mine in girth and length. In an old life, I would have been so envious; now I had mixed feelings. I wanted nothing more than to please him, and I absolutely loved hearing him grunt and moan as my mouth and soft hands made him erupt in my mouth on our first date. This was a 8-inch cock I was sucking on, and I was barely managing to get 70% of it down my throat. What the hell is going to happen when this thing is knocking at the door of little brown rosebud?!
James huffing “Good girl” snapped me back. One of his hands was on the back of my head trying to slowly inch is cock down my throat. When I was not paying attention, his other hand had pulled up my slinky grey over my ample bottom and was rubbing my cheeks under my lacy panties. I was glad I took the time to make sure every inch of me was absolutely smooth. In real life, it made me feel more feminine, I even went the extra step to powder and perfume down there. It felt like the woman in me was coming out, and when the time, I wanted James to fuck my ass like a cunt.
It felt so good as he felt me up. I was bobbing my head up and down on his now fully inflated manhood. James started to grind his hips to meet the rhythm of my mouth. My panties were being gradually lowered until he got them down to my knees. Then he played my ass like an instrument. Rubbing my thick chucky ass up and over, moving from one cheek to the next. I got hot, and raise my ass when James placed his hand between my ass cheeks and started to thump my sissy hole with his middle fingers, I think it was his way of say…this is next. After a few minutes of his thumping and my sucking, he whispered “Let’s head to the bedroom.”
We stood up, I completely removed my panties, took his hand and led him back to my room. It was fascinating to glance behind me and see James’ rock hard cock bounce up and down as he walked. And I hoped he liked the view in front of him; of my thick round ass, pushing the backside of my dress outlining the evening’s menu. Smooth, light chocolate shapely legs and my dark brown high heels.
The bedroom lights were turned off, but the candles I had lit on the dresser and night stands provided enough light to enhance the mood. I stood in front of the bed and shyly pushed a few strands of hair behind my ear. A kiss planted on the back of my neck and hands from behind rubbing my sissy breast increased the heat of the moment. Feeling James’s against 6’4” almost football player like body behind me, walking me to the bed took away all chances to turn back. This was the point of no return. James took my hand and cupped it around his heavy hairy balls. “Remember these?” I nodded my head yes, “It’s time” “First I want to taste what’s under that beautiful dress” I went to the edge of the bed on my knees as my heels hung over the side of my bed. Once there, I looked back and gave James my most seductive look with a devilish grin. James returned my action by making his pale, veiny uncut cock jump. Peeling my dress back to my waist, he now had full view and access to smooth shaven backside.
The sensation of having a man, a big strong dominant man behind me as I was on my bed, ass in the air, in dress and heels was so different. I felt like such a vulnerable sissy. The last steps of my femininity were almost complete. I had fantasied about a man taking and owning my ass for what seemed like such a long time, but having James behind me with this swing cock, licking my puckering star had my little clitty leaking. I was moaning so loud as James pried my ass cheeks apart and eat my little asshole like it was his last meal. His wet tongue darted in and out, then licked around my hole. Next, I hear him spit directly on my sissy cunt. I listened and obeyed everything he said to me. “Wiggle your ass” “Tell me how much you like it” “Wink it” a few times his tongue went from inside my hot little cunt to the base of my smooth sissy balls. I was in heaven! The rough feel of his scruffy beard as it scrapped across my sensitive virgin ass was something I never imagined. “Daddy!” blurted out my mouth when his tongue ran over my balls and the length of my clitty. I instinctively arched my back high, wanting him not to miss an inch. My toes curled, and chocolate chunky ass melted with each lick.
My ass was totally wet, from the top of my crack to my tightened sissy sack. As James’ tongue came out of my asshole for the last time, I wanted him to fuck me soooooo bad. I was going to do everything in my power to take his thick pale meat in my ass cunt. I pointed to the tube of gel on the nightstand next to the candle and as James reached over, I felt his meat smack against my ass cheek, another odd sensation. I captured the moment of everything. The sound of the tube being cracked opened, how cool the lube felt oozing down my crack as James drizzled it over my ass, the contrasting warmth of his strong hand separating my cheeks and my thoughts of me, giving my virginity to a man I met less than 12 hours ago on a gay porn website. The sound of James applying lube on this rock-hard cock made my asshole pucker. I guess I would call it nervous anticipation. Knowing that he was breaking in new ass, he inserted one finger to see my reaction, then another. “It’s okay daddy” I gasped. I knew James want to fuck my virgin brown ass after a fingering me. Getting off the bed, he grabbed me by the hips and pulled me back so my knees were at the edge of the bed and spread my legs wider. He paused, and I heard him re-lube his cock, then I felt my asshole stretch like it had never be stretched before. I couldn’t help moaning as the mix of pain and pleasure as his big mushroom head bullied it way through my no longer virgin asshole. The pressure made my catch my breath as it overwhelmed me. James hiked up my dress a bit more to have a better grip on my waist as he slowly, inch by inch invaded my tight cunt. “Relax” I heard as he firmly pulled me back and I pulled away. “Wait…, wait…, wait baby” I managed to get out as I reached back to stop him. James stopped, but did not pull out. That was okay, I just need to give my ass a few seconds.
“It’s okay baby, you are doing fine” he encouraged. I took a deep breath and clutched two handfuls of the bed sheets. The further James sank in my ass, the louder I got. “OOOOWWWW” “DADDY” I kept saying in my soft feminine voice. “It’s almost in, be a good girl…” he responded each time I whimpered daddy. The pain was intense, but I did my best to relax as he broke me in. I thought his cock would never stop entering me until I felt balls tap my ass. I DID IT!!!! I knew James would start having his fun now, it was his reward for showing patience. Less than 30 seconds after taking my virginity did he start plowing my newly opened cunt. I braced the bed as the deep pumping started. James’ cock felt like it was digging a hole, each thrust was met with a groan. I was getting what I dreamt, to have a real man fuck me and to be dominated. I could tell James was enjoying my super-tight ass cunt. We both were sweating and moaning, after a few minutes I felt tiny drops of his sweat hit my back as he impaled me. His rhythm was getting faster as he made every attempt to go deeper.
As he laid pipe on my sore sissy cunt and pushed his full weight in me, he reached around and started jacking my little erect 4-inch clit. His thrusts were hard and each and I dripped precum with each stroke. I could tell his was about to his moaning and swearing. I felt the throbbing of his cock in me, but I came first. My jets of jizz streamed on the sheets and I knew soaked down to the mattress. Soon after I felt his warm man cum in my cunt. It must have been at least 5 or 6 spurts of raw baby juice seeding me. The feeling of being stretched to the limit and not being able to close, then warm goo being shot in was so strange, but I liked it.
He collapsed on top of me and we both laid there (me on the wet spot) for a few moments. “Well, how was it?” he asked. Still in a fog from having my ass turned inside out, and trying to catch my thoughts, the only thing I said with a wincing smile was “Thank you.” He laughed and kissed me on the neck. His cock was finally limp enough for my asscunt to release it and the juices flowed. Ever being the gentleman he went to the bathroom and cleaned himself the told me to raise up as he cleaned wiped my sticky wet asshole, balls and inner thighs with a warm face towel. God, that felt so damn pleasant. ‘I think your dress is ruined” he chuckled. “I got more” I said as slowly got off the bed and looked at the damage in the mirror.
We kissed and said our goodbyes as he finished getting dressed and headed for the door. James asked before he walked out the door “What are you doing Saturday?” Playfully looking at his crotch, I replied “You are taking me shopping in the morning, so be here before 9.” “Okay, we will.” With that he kissed me on the forehead and left.
Just as I was putting on my necklace, the buzzer rang, and I thought this is it. A few minutes later there was a knock at the door, and my guy was there in my doorway was a bottle of wine. It was fun to see the grin on his face. Even in my heels, I had to stretch on my tippy-toes to kiss him. His scruffy beard felt so manly against my soft skin. Once again he gave me an enormous hug where his shoulders felt like they engulfed my entire body. But this hug was different, his hands went from the small of my back down to my chunky ass. We kissed as his strong hands groped each cheek and palmed them like basketballs. As he tonged me I also felt his bulge inflate. After we broke our kiss I gave a playful “Whew” and laughingly fanned my face. I loved the sparkle of his green eyes looking me over again.
“Wow, you look stunning”, I think this time he could actually see me blush! We sat back down on the sofa, the scene of the crime from earlier in the day, and talked a bit as we enjoyed a couple of glasses of wine. We talked about so many subjects as the wine flowed. Then he asked, “Is this really your first time?” “Yes” I replied. Telling him I recently started to accept who I am and what I want. “That was first real blowjob I gave you” “You, all of this is new to me, but my female friends knew” “They helped me learn how to dress, walk, act, do makeup, you name it.” James smiled, brushed my hair back and gave me a long passionate kiss. Something inside of me pushed flicked on, wanting to give him all of me, and I returned his passionate kiss. When was broke from our kiss the second time, James looked down to see the small lump under my dress. I looked at him and looked down, then inexplicably apologized. I thought I had that little thing tucked away. He gave a quick chuckle, kissed me on the forehead and said everything is fine. Now it was my turn to lunge into James was a passionate kiss. Our tongues slid over, around our mouths as I unbuckled his belt. James, being a man of experience, knew how to strike when the iron was hot. He popped off his shoes, just in time for me to slip off his pants. Next, to go was his knit shirt revealing his brawny chest. It was not musclebound or rippling with muscles like in the magazines, but it was perfect for me. He also did not have 6-pack abs but I could tell he kept himself in shape for a man his age.
I rubbed my hands over his massive back as James removed his socks. He was almost completely naked except for his tenting blue boxers. With a devilish smile, I helped free his beautifully thick, uncircumcised cock from its confinement. As, I started to remove my dress, he quickly grabbed my hand and shook his head. Noticing my confusion, he said “Let everything on, I want you just this this.” I nodded my head in agreement not wanting to spoil the mood. Everything stayed on, including my shoes. My attentions turned back to his thick white cock, still growing in my hand. Stroking his cock made it harder and bigger. James rubbing tweaking my nipples under my dress was so turning me on, I was almost at the point of begging him to just take it! I think that was his plan all along and it was working.
We got back comfortable on the couch again, James slumped to bring his cock to the perfect sucking position, and I complied curling up in a ball over his and taking the head of his cock in my mouth. James gave a moan of satisfaction as my tongue gently rolled over the slit of his cockhead, again exploring real flesh. I thought how lucky it must be to be so well-endowed, his cock was twice the size of mine in girth and length. In an old life, I would have been so envious; now I had mixed feelings. I wanted nothing more than to please him, and I absolutely loved hearing him grunt and moan as my mouth and soft hands made him erupt in my mouth on our first date. This was a 8-inch cock I was sucking on, and I was barely managing to get 70% of it down my throat. What the hell is going to happen when this thing is knocking at the door of little brown rosebud?!
James huffing “Good girl” snapped me back. One of his hands was on the back of my head trying to slowly inch is cock down my throat. When I was not paying attention, his other hand had pulled up my slinky grey over my ample bottom and was rubbing my cheeks under my lacy panties. I was glad I took the time to make sure every inch of me was absolutely smooth. In real life, it made me feel more feminine, I even went the extra step to powder and perfume down there. It felt like the woman in me was coming out, and when the time, I wanted James to fuck my ass like a cunt.
It felt so good as he felt me up. I was bobbing my head up and down on his now fully inflated manhood. James started to grind his hips to meet the rhythm of my mouth. My panties were being gradually lowered until he got them down to my knees. Then he played my ass like an instrument. Rubbing my thick chucky ass up and over, moving from one cheek to the next. I got hot, and raise my ass when James placed his hand between my ass cheeks and started to thump my sissy hole with his middle fingers, I think it was his way of say…this is next. After a few minutes of his thumping and my sucking, he whispered “Let’s head to the bedroom.”
We stood up, I completely removed my panties, took his hand and led him back to my room. It was fascinating to glance behind me and see James’ rock hard cock bounce up and down as he walked. And I hoped he liked the view in front of him; of my thick round ass, pushing the backside of my dress outlining the evening’s menu. Smooth, light chocolate shapely legs and my dark brown high heels.
The bedroom lights were turned off, but the candles I had lit on the dresser and night stands provided enough light to enhance the mood. I stood in front of the bed and shyly pushed a few strands of hair behind my ear. A kiss planted on the back of my neck and hands from behind rubbing my sissy breast increased the heat of the moment. Feeling James’s against 6’4” almost football player like body behind me, walking me to the bed took away all chances to turn back. This was the point of no return. James took my hand and cupped it around his heavy hairy balls. “Remember these?” I nodded my head yes, “It’s time” “First I want to taste what’s under that beautiful dress” I went to the edge of the bed on my knees as my heels hung over the side of my bed. Once there, I looked back and gave James my most seductive look with a devilish grin. James returned my action by making his pale, veiny uncut cock jump. Peeling my dress back to my waist, he now had full view and access to smooth shaven backside.
The sensation of having a man, a big strong dominant man behind me as I was on my bed, ass in the air, in dress and heels was so different. I felt like such a vulnerable sissy. The last steps of my femininity were almost complete. I had fantasied about a man taking and owning my ass for what seemed like such a long time, but having James behind me with this swing cock, licking my puckering star had my little clitty leaking. I was moaning so loud as James pried my ass cheeks apart and eat my little asshole like it was his last meal. His wet tongue darted in and out, then licked around my hole. Next, I hear him spit directly on my sissy cunt. I listened and obeyed everything he said to me. “Wiggle your ass” “Tell me how much you like it” “Wink it” a few times his tongue went from inside my hot little cunt to the base of my smooth sissy balls. I was in heaven! The rough feel of his scruffy beard as it scrapped across my sensitive virgin ass was something I never imagined. “Daddy!” blurted out my mouth when his tongue ran over my balls and the length of my clitty. I instinctively arched my back high, wanting him not to miss an inch. My toes curled, and chocolate chunky ass melted with each lick.
My ass was totally wet, from the top of my crack to my tightened sissy sack. As James’ tongue came out of my asshole for the last time, I wanted him to fuck me soooooo bad. I was going to do everything in my power to take his thick pale meat in my ass cunt. I pointed to the tube of gel on the nightstand next to the candle and as James reached over, I felt his meat smack against my ass cheek, another odd sensation. I captured the moment of everything. The sound of the tube being cracked opened, how cool the lube felt oozing down my crack as James drizzled it over my ass, the contrasting warmth of his strong hand separating my cheeks and my thoughts of me, giving my virginity to a man I met less than 12 hours ago on a gay porn website. The sound of James applying lube on this rock-hard cock made my asshole pucker. I guess I would call it nervous anticipation. Knowing that he was breaking in new ass, he inserted one finger to see my reaction, then another. “It’s okay daddy” I gasped. I knew James want to fuck my virgin brown ass after a fingering me. Getting off the bed, he grabbed me by the hips and pulled me back so my knees were at the edge of the bed and spread my legs wider. He paused, and I heard him re-lube his cock, then I felt my asshole stretch like it had never be stretched before. I couldn’t help moaning as the mix of pain and pleasure as his big mushroom head bullied it way through my no longer virgin asshole. The pressure made my catch my breath as it overwhelmed me. James hiked up my dress a bit more to have a better grip on my waist as he slowly, inch by inch invaded my tight cunt. “Relax” I heard as he firmly pulled me back and I pulled away. “Wait…, wait…, wait baby” I managed to get out as I reached back to stop him. James stopped, but did not pull out. That was okay, I just need to give my ass a few seconds.
“It’s okay baby, you are doing fine” he encouraged. I took a deep breath and clutched two handfuls of the bed sheets. The further James sank in my ass, the louder I got. “OOOOWWWW” “DADDY” I kept saying in my soft feminine voice. “It’s almost in, be a good girl…” he responded each time I whimpered daddy. The pain was intense, but I did my best to relax as he broke me in. I thought his cock would never stop entering me until I felt balls tap my ass. I DID IT!!!! I knew James would start having his fun now, it was his reward for showing patience. Less than 30 seconds after taking my virginity did he start plowing my newly opened cunt. I braced the bed as the deep pumping started. James’ cock felt like it was digging a hole, each thrust was met with a groan. I was getting what I dreamt, to have a real man fuck me and to be dominated. I could tell James was enjoying my super-tight ass cunt. We both were sweating and moaning, after a few minutes I felt tiny drops of his sweat hit my back as he impaled me. His rhythm was getting faster as he made every attempt to go deeper.
As he laid pipe on my sore sissy cunt and pushed his full weight in me, he reached around and started jacking my little erect 4-inch clit. His thrusts were hard and each and I dripped precum with each stroke. I could tell his was about to his moaning and swearing. I felt the throbbing of his cock in me, but I came first. My jets of jizz streamed on the sheets and I knew soaked down to the mattress. Soon after I felt his warm man cum in my cunt. It must have been at least 5 or 6 spurts of raw baby juice seeding me. The feeling of being stretched to the limit and not being able to close, then warm goo being shot in was so strange, but I liked it.
He collapsed on top of me and we both laid there (me on the wet spot) for a few moments. “Well, how was it?” he asked. Still in a fog from having my ass turned inside out, and trying to catch my thoughts, the only thing I said with a wincing smile was “Thank you.” He laughed and kissed me on the neck. His cock was finally limp enough for my asscunt to release it and the juices flowed. Ever being the gentleman he went to the bathroom and cleaned himself the told me to raise up as he cleaned wiped my sticky wet asshole, balls and inner thighs with a warm face towel. God, that felt so damn pleasant. ‘I think your dress is ruined” he chuckled. “I got more” I said as slowly got off the bed and looked at the damage in the mirror.
We kissed and said our goodbyes as he finished getting dressed and headed for the door. James asked before he walked out the door “What are you doing Saturday?” Playfully looking at his crotch, I replied “You are taking me shopping in the morning, so be here before 9.” “Okay, we will.” With that he kissed me on the forehead and left.
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