Businessman is Forcibily Transformed Into a Sissy
- 3 years ago
- 26
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Many Firsts For Sissy free porn video
I have always had a desire for dressing femme and having submissive thoughts ever since I can remember. I started like many other gurls by trying on my mother's lingerie and loving it. Things gradually escalated to shaving (thankfully I am blonde and not very hairy naturally), experimenting with make-up, and inevitably sucking cock at the park toward the end of my college days. I was on my way to being a true sissy gurl now that I reflect on it. Everything I did was subconsciously geared toward looking and feeling more effeminate like keeping my body fit, tan and smooth; buying and hiding my sexy lingerie; allotting time to privately sneak away to suck random men at the park. But it seems every sissy has a moment of reckoning, and this very, very little fabricated story was mine...
Call it vanity or whatever, but I've always been drawn to the idea of being watched or pictures taken of me dressed sexy and with a hot guy. There was just something so taboo and risky that made it a top fantasy. So when I ran across an online posting for a mature man wanting to film a younger man sucking his cock in my area, I was fascinated. I must have read the ad a dozen times before I responded. I explained that I was a crossdresser and he immediately replied that the idea of being with a CD would be more than welcome. He also told me that he was in his mid-fifties. That made me hesitate as being in my twenties, I wasn't really interested in sexual contact with an older guy. He said there didn't need to be any sexual contact; he just wanted to film me. Even to my surprise, I agreed.
So when the day came to meet, I showered clean and shaved smooth. I normally don't apply heavy makeup, but today I wanted to use it to conceal my identity a bit, so I went heavier on the eyes. With my little Justin Bieber highlighted haircut, which was long for a boy, but short for a girl, it was difficult to tell which sex I was. I picked out a matching cream colored with floral design bra and panty set. My jewelry consisted of a necklace, toe ring, and anklet. I threw some shorts, t-shirt, and flip-flops on and headed to the heavily wooded park to be displayed as a sissy on film. It was so nerve-racking, but incredibly exciting.
I arrived a little early and grabbed my blanket that I brought and started to head down the path into the woods, carefully following his predetermined directions. My concern of doing this outside and getting caught was soon alleviated because it was so remote and hidden. I went across the wooden bridge and veered on to a lesser traveled path, over a couple small hills and saw the perfect spot to spread out my blanket. I stripped down to bra and panties and layed down to wait. It was summer and very humid even though it wasn't even noon yet but thankfully I was under complete shade from the trees.
As I was waiting, a million nervous thoughts were running through my head. Plus, I didn't even know if he would show up. With so much uncertainty, I almost left, but in peering up, I saw someone coming down the path. I froze. Over the two hills he came and got closer. I could see he was carrying a small, hand-held camera (this was before cell phone video capability). And I also immediately noticed he wasn't a very attractive man. He looked at least 60 to me. He was dressed in a white tank top and shorts with sandals. And he was super hairy. I mean hairy arms that carried all the way to his shoulders and hair poking out of his tank top on his chest. In addition, he had a pretty good sized gut. Right then I was so glad he agreed that there would be no sexual contact between us.
He couldn't see me as he approached because it was so secluded so he did our prearranged sign which was to clap twice. In my head, I thought this was it. Now or never. I was shaking from nervous excitement. But I knew I'd regret it if I didn't go through with my fantasy. I clapped twice back and he turned my direction. See saw me and immediately raised his camera to start filming me. No greeting, no talking, just action because the camera was rolling. My first time being filmed.
I immediately started posing and touching and rubbing myself to put on a sexy little show. Why not because I'd officially been recorded in sissy lingerie and makeup for all to see. His reaction to me and my appearance turned me on even more. He was commenting how hot I looked and he started to play with himself. One hand on the camera and the other stroking his cock through his shorts. He eventually dropped his shorts and boxers to play with his now hard bare cock. All the while I was rolling around and spreading and teasing him. Needless to say, I liked showing off as much as he liked filming me.
Occasionally he would order me in sexy poses and to perform certain acts. He got bold and reached into his shorts pocket and pulled out a tube of lubricant and tossed it to me. I figured he wanted me to jack off with it so I pulled my panties off my clitty and began to lube it up. He corrected me and said he wanted me to finger fuck myself. Well, okay, I've done that many times before so I pulled the thing strap out of my pussy ass and slowly, seductively began to insert a finger into my tight little boi pussy. It felt good. Really good as I started to freely fuck myself drawing tiny moans and coos from me. He was getting excited watching this show and probably couldn't wait to get home and replay it and stroke off to it.
But then he told me to do it doggy style. Okay I thought; anything for the director and the sake of a hot film. But I don't know if you've ever tried to finger yourself in doggy, but it's really hard and you can't get great penetration. He saw this struggle and asked me if I wanted help. I paused, but whether pure horniness or maybe starting to build trust with him, I said okay. He set the camera down on the edge of the blanket but made sure it was the right angle to keep filming me. He pulled off his tank top. Then he squirted a big glob of lube on my pussy ass and drove a finger deep into me. The suddenness shocked me a bit. He fingered me roughly which was a direct contrast to my seductive fingerbanging. Soon he added a second digit. I moaned due to the discomfort but accepted his manipulations.
I could feel his hard cock touching my left leg as he opened up my pussy. It felt okay, but I was wondering when it was going to be over. My answer came quite soon when he pulled his fingers out and split my legs and climbed in between. I thought oh my god he's going to try to fuck me. Immediately I said no. I always knew I would eventually get fucked, but I pictured my first being with a hot guy in a nice hotel or something; not here in the woods and certainly not with this guy. Even though I was saying no, he kept trying to slide himself inside me. Finally, he gave up and he told me that I needed to loosen up a bit. He told me to stay right where I was at while he dug back into his pocket. This time he pulled out a little brown bottle. I had no idea what it was. He came around and kneeled in front of me and he uncapped the bottle and sniffed it twice deeply. Whatever it was, it seemed to please him. He offered it to me and I rejected it because of being unsure of the contents. He explained that it was poppers and it would help me loosen up. I was skeptical so I took a small sniff of it as he held it under my nose. It smelled very chemically and powerful. He again corrected me and said to exhale all my air then breath it in and hold it. Nervously, I exhaled as he plugged one of my nostrils and I breathed it in and held it. He told me to let it go. When I did, oh my. My temples were throbbing. A wave of heat and euphoria came over me. I was dizzy. And most of all, super horny. Like hornier than I'd ever been. I also remember that all I wanted was touch. Whether it was him touching me or me touching him. Body contact was now so erotic.
Losing my balance a bit, I fell forward so my head was on his big stomach. I wrapped my right arm around his leg for balance and just to touch him. He was talking about how good it feels and how I was such a good little slut. All the while pushing my head slowly down his hairy tummy. Eventually my right cheek brushed his raging-hard cock. I don't know what came over me, but I automatically turned my head and accepted his cock into my mouth. I began sucking desperately like it was the last cock I'd ever get to suck. He moaned his appreciation and kept a hand on the back of my head. I wasn't going anywhere though.
With his cock still in my mouth, he put the poppers under my nose again and instructed me to inhale. I did and it started the spin cycle all over again. But this time he abruptly pulled his cock away from me, much to my disappointment. He kept a hand on me and told me to stay there as he maneuvered himself behind me again. He again split my legs and pulled the thong strap to the side. He opened up my pussy ass and began sliding his cock up and down my crack. I didn't care this time as long as I was getting touched. Then I felt him adjust down slightly and felt the pressure of his greasy cock on my virgin pussy. He asked me if I was ready but didn't really intend on waiting for a response. His meat started to open me up again and I was helpless to stop him, nor did I want to because this was the ultimate touch. He slid halfway in and locked his hands on my hips giving me little baby humps to get me used to his invading cock. He asked me if I liked it and I just turned over my shoulder and said "Fuck me!" With that he buried himself into me, making me his bitch.
I thought getting my first cock would hurt, but whether I was loosened up by the fingerbanging or a lot of lube or the poppers relaxing my hole, it didn't hurt. I just felt full. Just deliciously full. He continued to fuck me and I discovered that I am not a quiet fuck. I couldn't help but to moan and encourage him so the exquisite feeling wouldn't stop. He reached over the top of me and I could feel his hairy, now sweaty, chest on my back and he had me breath in the poppers again. This time two hits. I was euphoric. But after he did that, he buried himself deep in me and began gradually pivoting me around 180 degrees. I didn't know why; I just went with it as long as that cock stayed in me. Then I saw the camera on the edge of the blanket and realized that not only was I captured on film as a sissy, I had sucked cock and was getting my first fuck all recorded. What could I do? I wasn't going to stop so I just let my slutty humiliation be documented.
Soon after he made sure to get my face on camera getting plowed, he again abruptly pulled out. He smacked my butt and said to sit up. I turned to him and propped myself up on my hands. He said he needed a break and I could see why because he as working me over hard and it was hot out. He was glistening in sweat. He took the opportunity to pour a lot of lube on his cock so it was dripping wet. I just sat there admiring him. Still high and wanting touch, I began rubbing his hairy arms and shoulders and eventually worked my way to the thick, sweaty hair on his chest. It was amazing to me that what disgusted me just 20 minutes ago was now such a huge attraction. I thought to myself that this is what a team man looks like.
After a minute break he told me to hand him the poppers. I did and he uncapped and inhaled deeply twice. He gave it a second then did it twice more. He had that wild glazed look in his eyes. He offered them to me so I leaned forward and expertly inhaled twice. So high. So horny. So perfect. Then he said to hit it again. I didn't need more, but I wasn't going to disobey so I loaded up again. I leaned on my hands and looked up. The trees were spinning so I had to close my eyes. When I did, he scooped under my legs indicating that he wanted me to lay back flat. I went down to the blanket and it felt like I was on a cloud. I just extended my arms above my head and opeed my legs as a girl should He moved up to mount me. Instinctively, I drew my knees up and open so he could have easy access to my sex. He guided his head in and I moaned almost in relief as the rest of him entered me. He moved up to fully mount his bitch. With his arms under mine and that chest I now loved firmly planted on top of my bra-covered tittie, I wrapped my arms around his neck and back to accept his cock plunging in and out of me.
Whwn I finally opened my eyes, I realized his mouth was inches away from me. He hadn't tried to kiss me yet, but I so badly wanted him to. I decided to take a chance and I reached up and kissed him. This may have surprised him a bit, but he responded by burying his mouth into mine. Much like everything he did, he was rough and aggressive. His tongue probed my mouth deeply. I just kept moaning and whimpering around his tongue as his cock took over my body. He broke the kiss and asked me if I wanted him to cum in my mouth or my ass. I didn't say anything. What I wanted was for him to continue fucking me so I wrapped my legs around him and hooked my ankles together. He took that as the green light to creampie me. Immediately he began breathing hard and almost growling as he dumped his seeds into me. I didn't know what to do. What I do know is that I didn't tell him to stop. Nor did I unhook my ankles or try to push him away. I just let him breed me like a cumdump bitch. When he was done, he collapsed on top of me and I just held him there, rubbing his back. All the lingerie and makeup in the world couldn't have made me feel more femme then he did at that moment.
After about only ten seconds in the post-breeding position, he climbed off and withdrew from my spent pussy. He simply went over to shut the camera off then got dressed. He gave me the poppers as my "reward" and simply thanked me and left. The abruptness of his departure was probably an indicator of how guys tend to treat sissy sluts and I'd likely have to get used to it. As far as the video, whenever I search sissy porn, I keep waiting to see my face out there in the woods being exposed like a total slut. Hasn't happened yet, but I know it's out there.
Call it vanity or whatever, but I've always been drawn to the idea of being watched or pictures taken of me dressed sexy and with a hot guy. There was just something so taboo and risky that made it a top fantasy. So when I ran across an online posting for a mature man wanting to film a younger man sucking his cock in my area, I was fascinated. I must have read the ad a dozen times before I responded. I explained that I was a crossdresser and he immediately replied that the idea of being with a CD would be more than welcome. He also told me that he was in his mid-fifties. That made me hesitate as being in my twenties, I wasn't really interested in sexual contact with an older guy. He said there didn't need to be any sexual contact; he just wanted to film me. Even to my surprise, I agreed.
So when the day came to meet, I showered clean and shaved smooth. I normally don't apply heavy makeup, but today I wanted to use it to conceal my identity a bit, so I went heavier on the eyes. With my little Justin Bieber highlighted haircut, which was long for a boy, but short for a girl, it was difficult to tell which sex I was. I picked out a matching cream colored with floral design bra and panty set. My jewelry consisted of a necklace, toe ring, and anklet. I threw some shorts, t-shirt, and flip-flops on and headed to the heavily wooded park to be displayed as a sissy on film. It was so nerve-racking, but incredibly exciting.
I arrived a little early and grabbed my blanket that I brought and started to head down the path into the woods, carefully following his predetermined directions. My concern of doing this outside and getting caught was soon alleviated because it was so remote and hidden. I went across the wooden bridge and veered on to a lesser traveled path, over a couple small hills and saw the perfect spot to spread out my blanket. I stripped down to bra and panties and layed down to wait. It was summer and very humid even though it wasn't even noon yet but thankfully I was under complete shade from the trees.
As I was waiting, a million nervous thoughts were running through my head. Plus, I didn't even know if he would show up. With so much uncertainty, I almost left, but in peering up, I saw someone coming down the path. I froze. Over the two hills he came and got closer. I could see he was carrying a small, hand-held camera (this was before cell phone video capability). And I also immediately noticed he wasn't a very attractive man. He looked at least 60 to me. He was dressed in a white tank top and shorts with sandals. And he was super hairy. I mean hairy arms that carried all the way to his shoulders and hair poking out of his tank top on his chest. In addition, he had a pretty good sized gut. Right then I was so glad he agreed that there would be no sexual contact between us.
He couldn't see me as he approached because it was so secluded so he did our prearranged sign which was to clap twice. In my head, I thought this was it. Now or never. I was shaking from nervous excitement. But I knew I'd regret it if I didn't go through with my fantasy. I clapped twice back and he turned my direction. See saw me and immediately raised his camera to start filming me. No greeting, no talking, just action because the camera was rolling. My first time being filmed.
I immediately started posing and touching and rubbing myself to put on a sexy little show. Why not because I'd officially been recorded in sissy lingerie and makeup for all to see. His reaction to me and my appearance turned me on even more. He was commenting how hot I looked and he started to play with himself. One hand on the camera and the other stroking his cock through his shorts. He eventually dropped his shorts and boxers to play with his now hard bare cock. All the while I was rolling around and spreading and teasing him. Needless to say, I liked showing off as much as he liked filming me.
Occasionally he would order me in sexy poses and to perform certain acts. He got bold and reached into his shorts pocket and pulled out a tube of lubricant and tossed it to me. I figured he wanted me to jack off with it so I pulled my panties off my clitty and began to lube it up. He corrected me and said he wanted me to finger fuck myself. Well, okay, I've done that many times before so I pulled the thing strap out of my pussy ass and slowly, seductively began to insert a finger into my tight little boi pussy. It felt good. Really good as I started to freely fuck myself drawing tiny moans and coos from me. He was getting excited watching this show and probably couldn't wait to get home and replay it and stroke off to it.
But then he told me to do it doggy style. Okay I thought; anything for the director and the sake of a hot film. But I don't know if you've ever tried to finger yourself in doggy, but it's really hard and you can't get great penetration. He saw this struggle and asked me if I wanted help. I paused, but whether pure horniness or maybe starting to build trust with him, I said okay. He set the camera down on the edge of the blanket but made sure it was the right angle to keep filming me. He pulled off his tank top. Then he squirted a big glob of lube on my pussy ass and drove a finger deep into me. The suddenness shocked me a bit. He fingered me roughly which was a direct contrast to my seductive fingerbanging. Soon he added a second digit. I moaned due to the discomfort but accepted his manipulations.
I could feel his hard cock touching my left leg as he opened up my pussy. It felt okay, but I was wondering when it was going to be over. My answer came quite soon when he pulled his fingers out and split my legs and climbed in between. I thought oh my god he's going to try to fuck me. Immediately I said no. I always knew I would eventually get fucked, but I pictured my first being with a hot guy in a nice hotel or something; not here in the woods and certainly not with this guy. Even though I was saying no, he kept trying to slide himself inside me. Finally, he gave up and he told me that I needed to loosen up a bit. He told me to stay right where I was at while he dug back into his pocket. This time he pulled out a little brown bottle. I had no idea what it was. He came around and kneeled in front of me and he uncapped the bottle and sniffed it twice deeply. Whatever it was, it seemed to please him. He offered it to me and I rejected it because of being unsure of the contents. He explained that it was poppers and it would help me loosen up. I was skeptical so I took a small sniff of it as he held it under my nose. It smelled very chemically and powerful. He again corrected me and said to exhale all my air then breath it in and hold it. Nervously, I exhaled as he plugged one of my nostrils and I breathed it in and held it. He told me to let it go. When I did, oh my. My temples were throbbing. A wave of heat and euphoria came over me. I was dizzy. And most of all, super horny. Like hornier than I'd ever been. I also remember that all I wanted was touch. Whether it was him touching me or me touching him. Body contact was now so erotic.
Losing my balance a bit, I fell forward so my head was on his big stomach. I wrapped my right arm around his leg for balance and just to touch him. He was talking about how good it feels and how I was such a good little slut. All the while pushing my head slowly down his hairy tummy. Eventually my right cheek brushed his raging-hard cock. I don't know what came over me, but I automatically turned my head and accepted his cock into my mouth. I began sucking desperately like it was the last cock I'd ever get to suck. He moaned his appreciation and kept a hand on the back of my head. I wasn't going anywhere though.
With his cock still in my mouth, he put the poppers under my nose again and instructed me to inhale. I did and it started the spin cycle all over again. But this time he abruptly pulled his cock away from me, much to my disappointment. He kept a hand on me and told me to stay there as he maneuvered himself behind me again. He again split my legs and pulled the thong strap to the side. He opened up my pussy ass and began sliding his cock up and down my crack. I didn't care this time as long as I was getting touched. Then I felt him adjust down slightly and felt the pressure of his greasy cock on my virgin pussy. He asked me if I was ready but didn't really intend on waiting for a response. His meat started to open me up again and I was helpless to stop him, nor did I want to because this was the ultimate touch. He slid halfway in and locked his hands on my hips giving me little baby humps to get me used to his invading cock. He asked me if I liked it and I just turned over my shoulder and said "Fuck me!" With that he buried himself into me, making me his bitch.
I thought getting my first cock would hurt, but whether I was loosened up by the fingerbanging or a lot of lube or the poppers relaxing my hole, it didn't hurt. I just felt full. Just deliciously full. He continued to fuck me and I discovered that I am not a quiet fuck. I couldn't help but to moan and encourage him so the exquisite feeling wouldn't stop. He reached over the top of me and I could feel his hairy, now sweaty, chest on my back and he had me breath in the poppers again. This time two hits. I was euphoric. But after he did that, he buried himself deep in me and began gradually pivoting me around 180 degrees. I didn't know why; I just went with it as long as that cock stayed in me. Then I saw the camera on the edge of the blanket and realized that not only was I captured on film as a sissy, I had sucked cock and was getting my first fuck all recorded. What could I do? I wasn't going to stop so I just let my slutty humiliation be documented.
Soon after he made sure to get my face on camera getting plowed, he again abruptly pulled out. He smacked my butt and said to sit up. I turned to him and propped myself up on my hands. He said he needed a break and I could see why because he as working me over hard and it was hot out. He was glistening in sweat. He took the opportunity to pour a lot of lube on his cock so it was dripping wet. I just sat there admiring him. Still high and wanting touch, I began rubbing his hairy arms and shoulders and eventually worked my way to the thick, sweaty hair on his chest. It was amazing to me that what disgusted me just 20 minutes ago was now such a huge attraction. I thought to myself that this is what a team man looks like.
After a minute break he told me to hand him the poppers. I did and he uncapped and inhaled deeply twice. He gave it a second then did it twice more. He had that wild glazed look in his eyes. He offered them to me so I leaned forward and expertly inhaled twice. So high. So horny. So perfect. Then he said to hit it again. I didn't need more, but I wasn't going to disobey so I loaded up again. I leaned on my hands and looked up. The trees were spinning so I had to close my eyes. When I did, he scooped under my legs indicating that he wanted me to lay back flat. I went down to the blanket and it felt like I was on a cloud. I just extended my arms above my head and opeed my legs as a girl should He moved up to mount me. Instinctively, I drew my knees up and open so he could have easy access to my sex. He guided his head in and I moaned almost in relief as the rest of him entered me. He moved up to fully mount his bitch. With his arms under mine and that chest I now loved firmly planted on top of my bra-covered tittie, I wrapped my arms around his neck and back to accept his cock plunging in and out of me.
Whwn I finally opened my eyes, I realized his mouth was inches away from me. He hadn't tried to kiss me yet, but I so badly wanted him to. I decided to take a chance and I reached up and kissed him. This may have surprised him a bit, but he responded by burying his mouth into mine. Much like everything he did, he was rough and aggressive. His tongue probed my mouth deeply. I just kept moaning and whimpering around his tongue as his cock took over my body. He broke the kiss and asked me if I wanted him to cum in my mouth or my ass. I didn't say anything. What I wanted was for him to continue fucking me so I wrapped my legs around him and hooked my ankles together. He took that as the green light to creampie me. Immediately he began breathing hard and almost growling as he dumped his seeds into me. I didn't know what to do. What I do know is that I didn't tell him to stop. Nor did I unhook my ankles or try to push him away. I just let him breed me like a cumdump bitch. When he was done, he collapsed on top of me and I just held him there, rubbing his back. All the lingerie and makeup in the world couldn't have made me feel more femme then he did at that moment.
After about only ten seconds in the post-breeding position, he climbed off and withdrew from my spent pussy. He simply went over to shut the camera off then got dressed. He gave me the poppers as my "reward" and simply thanked me and left. The abruptness of his departure was probably an indicator of how guys tend to treat sissy sluts and I'd likely have to get used to it. As far as the video, whenever I search sissy porn, I keep waiting to see my face out there in the woods being exposed like a total slut. Hasn't happened yet, but I know it's out there.
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