My High Price Paid to Write Erotica
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Sissy Erotica free porn video
The following is a fantasy sissy erotica
Chapter one: Entering sissyhood
This is a story about my first few experiences as a bottom sissy slut. I am now 21, my name is Alyssa and a dedicated slut for my daddy. I'm 5"9, very slender & smooth, feminine and i have long blonde hair. Ever since i was in my early teens i had been interested in trying to take a mans penis in my ass. At some point i decided to try playing with my butthole. I loved it right away. I would take a bath, get nice and clean and finger my then very tight hole. Over the next 5 or 6 years i frequently would finger or toy my ass in secret. By the time i was 19 i was still a virgin and i was hornier than ever. It was around then that i got into watching porn and discovered sissy porn. I was hooked. I would go through phases of staying up all night toying my ass with homemade toys. I realized that all these years i was just preparing my pussy for some lucky daddy. I managed to get my hands on some sexy clothes and some makeup and i would watch sissy hypno while all dolled up and toy my ass for hours. By age 21 I was a total fem slut. I eventually decided i wanted to feel a real penis so i started looking online. I browsed a few sites before finding craigslist. I had discovered that i had a huge amount of lust for older dominant daddy type men so i created an account using a discreet email and made my first post. "Young first time sissy in search of daddy." I couldn't believe how many older men were eager to pop my boy cherry. It was actually kind of overwhelming at first. I also got a reply from another sissy who lived somewhat close by who was also into older guys AND a virgin. I decided to reply to her. Her name was Heather and she was 19, very girly looking and she claimed to be very smooth. I was interested in meeting with her because I was nervous about going to an older strangers house alone with no experience. Turns out Heather was just as interested in me. We discussed sissy things like favourite outfits and lipstick and even shared sissy porn all through email. I had recently started renting a small suite in a private area and I lived alone, so i asked her if she wanted to come over sometime. She ecstatically replied saying "Yes I'm so excited to do this! I'm glad you can host. How's saturday night work for you?" I of course agreed to host on saturday and I asked her to bring all of her "sissy accessories." I was soooo excited i was leaking pre cum just thinking about it. All i did for the next 3 days was think about and prepare for meeting with heather. Finally it was saturday so before she arrived i took a bath, shaved my entire body and thoroughly cleaned my sissy pussy. I was so horny waiting for her to show up. I had this amazing tingling feeling deep inside of me. Around 8pm the door rang and i quickly went to open it. We had agreed to meet in "boy mode" so that we could dress up and become girls together. I opened the door and there stood a beautifully androgynous human. She was about 5"6, slender, medium length dark brown hair, pale skin that was very smooth and already girly looking face. I greeted her warmly and invited her in. There was sexual tension right away. It was obvious we were both nervous but both wanted this so bad. I took her into my living room where i had lay out large mattress and had a laptop set up on a side table and a couch with all my sissy clothes and some lube. Heather had a big smile on her face when she saw this and she set down her backpack on the couch. We sat on the bed and talked for a bit until we were comfortable and then we gave each other a small kiss. For the first time i felt like i was kissing someone as a girl and i think heather felt the same. There we were, a couple of virgin sissy sluts ready to be made into girls. We decided to get dressed. "Want to see what i have in my bag Alyssa?" I of course was eager and said yes. She pulled out her clothes, which were very slutty and a few toys. I gasped because i had never used a real dildo only homemade ones. She giggled at my reaction to her collection of anal toys. She had brought 2 buttplugs, 3 dildoes each bigger than the last and a very long double ended dildo. The thickest of the dildoes was almost as thick as a can of beer. It frightened me a little even though i wanted it in me. She could tell i was looking at it and explained she had just ordered the toys online and she could only take the smallest of the dildoes so far. She asked me if i would be interested in training our pussies together and i blushed and lovingly agreed. We decided to dress up and each went into separate rooms. I put on pink heels, fishnets leggings that strapped to my pink thong and a pink and purple crop top. I also straightened and tied my long blonde hair into pigtails with a pink hair tie. Then i slipped on a denim mini skirt and did my makeup. Hot pink lipstick. Can you tell my favourite colour? Hehe. I even used eye shadow and mascara. I looked like a passable sissy girl. I walked back into the living room to find Heather in a very sexy outfit. She wore a short purple and white frilly dress with black and white leggings and little ugg boots. She also had on full make up and she even had on a long black wig. Her lipstick was a dark purple. We had a moment of just staring at each other in amazement. That's when our voices and even the way we moved became VERY feminine. We both sat on the bed tingling with excitement. Heather reached into her bag and pulled put two chastity devices. I had never used one but i was definitely interested in trying! Then she said something that kind of surprised me. She asked me if i would like to have one but if i accept then i will have to agree to enter a sissy hood with her. She explained that there are sissy rules. Some of the rules were quite a commitment - we are only allowed to cum by stimulating our pussies and we must always wear a cage while having sex. Basically we would become total sex sluts designed to pleasure real men and we would become this together. I was wide eyed at the idea of this and surprised by the amount of trust she had considering we had just met. I don't know if it was from watching all the sissy hypno or if i'm just meant for this but i decided to accept her proposition. We both blushed and hugged. Heather had a naughty look in her eyes as she handed me my chastity device. She said that she wanted us to wear our cage for one week without taking it off. This seemed like a lot for my first time but rules are rules and now i was committed. I pulled down my thong exposing my limp clitty - heather looked very turned on by this. I slipped on my cage for the first time and it fit perfectly!!! She then lifted my totally shaven and smooth clitty and balls to inspect how it fit before locking it on with a tiny lock and putting the key in her bag. She did the same to herself. Seeing her small shaven sissy clitty started to make me hard but my new cage would not let me which forced the arousal to my prostate or "sissy g-spot." I had never felt this feminine. She also placed her key in her bag and explained she would return me mine in a week. We then lay back next to each other and each took one of the small butt plugs. After lubing our pussies we held hands, put our legs up in the air and slowly inserted our plugs. Heathers hand gripped mine tighter as we started to moan and pant. My caged clitty hanging useless, dressed like a total slut with another sissy and with buttplug inside of me. I was in heaven. Once my pussy had totally adjusted to the plug I stood up and did a girly spin to show Heather my body. I then walked over to the laptop and turned on a sissy trainer video then i got onto the bed in doggy style position and put my ass in the air for heather. My thong barely covered the plug that was in me and my mini skirt covered half my ass. Heather then knelt above me, moved my skirt out of the way and pulled my thong to the side. Finally someone else was going to enjoy my pussy. I moaned as she slowly pulled out the plug and exposed my pink winking pussy. It felt so warm and wet that i felt something leak out from my clitty as she pulled it out. I could tell she was really enjoying this because she was panting. She put her girly little hands on my hips at both sides of my ass and spread me. I put all my effort into winking my bumhole to make sure she knew i wanted it. She kissed my pussy cheek leaving a purple mark shaped like slutty lips. Then i felt something that put me into ecstasy. She drove her warm tongue as deep into my pussy as she could and started eating me out. Feeling her tongue writhing around inside me tickling my g-spot made me leak sissy juice again. She finished licking me with a kiss right on my butthole. It was obvious i had been leaking and Heather noticed. She then took my precum from the mattress and lubed my ass with it. We gave each other a naughty look. I then stood up and lay Heather down on her back and told her to spread her pussy. Her dress was pulled up and it d****d across her stomach, her caged clitty hung to the side and she had her legs up in the air with her knees together. She looked so cute spreading her plugged pussy with her ugg boots on and the little cotton balls hanging down. I slowly pulled out her plug and suddenly it popped out revealing a perfect hole that stayed slightly open for a few seconds. I was so turned on. I went crazy on her pussy with my mouth. I droves my tongue as deep as i could and she tasted so sweet. Holding her clit out of the way i licked from her butthole up the little line to her girly balls. She liked when i did that. After a while we both stood up, turned off the sissy hypno and kissed. By now we really were in a state of hypnosis and our pussies were hungry for more. I gestured at the double ended dildo and heather rose an eyebrow. "Think we could take that?" I giggled. "Want to find out?" Heather agreed but first reached into her bag and pulled out a joint. She asked if i smoked and i said i had a few times. We decided to go outside the back of my place and get high. Going back inside i remember feeling like such a slut. We sat on the bad facing each other with our legs out. We moved closer until our clitties were touching then we both lay back into a scissoring position. After lubing our holes heather positioned the long dildo with a head on each of our pussies, sliding the head halfway in so that it would stay there. Even that felt big but i was ready for more. We both put our hands on the bed behind us and slowly moved our pussies closer together. Oh my god it felt good to feel my pussy being stimulated with a twin sissy feeling exactly what i felt. We moaned together, sliding deeper. The dildo was 12" in total and soon we each had the full six inches inside of us and our little taints with grinding against each other. That's when we went crazy and starting grinding hard and fast, thrashing around trying to fuck our toy as hard as we could. Girly sex noises filled my house. Our clitty cages were hitting together and i could see our sissy juices leaking out and mixing before being ground in the space between our bumholes and our balls. After 10 minutes of scissoring we slid out the toy and touched each others holes to admire what we had done, both noticing they were quite a bit looser. We were both very satisfied and sat up. Still high we decided to check the time. It was after midnight already and we were shocked and getting tired. Heather surprised me again and asked if she could stay over, i said yes. We cuddled up in the bed and kept most of our slutty clothes on and of course leaving our cages and reinserting our plugs for the night. We slept until morning with our legs entangled together and holding hands. In the morning Heather had to leave around 9 and we made plans for her to stay over again in two nights from now. She changed back into her normal clothes but i noticed she had on her cage, some panties and her plug still in as she slipped put the door. After she left, the experience dawned on me and i was filled with happiness. I was now on track to becoming a real sissy girl.
Chapter one: Entering sissyhood
This is a story about my first few experiences as a bottom sissy slut. I am now 21, my name is Alyssa and a dedicated slut for my daddy. I'm 5"9, very slender & smooth, feminine and i have long blonde hair. Ever since i was in my early teens i had been interested in trying to take a mans penis in my ass. At some point i decided to try playing with my butthole. I loved it right away. I would take a bath, get nice and clean and finger my then very tight hole. Over the next 5 or 6 years i frequently would finger or toy my ass in secret. By the time i was 19 i was still a virgin and i was hornier than ever. It was around then that i got into watching porn and discovered sissy porn. I was hooked. I would go through phases of staying up all night toying my ass with homemade toys. I realized that all these years i was just preparing my pussy for some lucky daddy. I managed to get my hands on some sexy clothes and some makeup and i would watch sissy hypno while all dolled up and toy my ass for hours. By age 21 I was a total fem slut. I eventually decided i wanted to feel a real penis so i started looking online. I browsed a few sites before finding craigslist. I had discovered that i had a huge amount of lust for older dominant daddy type men so i created an account using a discreet email and made my first post. "Young first time sissy in search of daddy." I couldn't believe how many older men were eager to pop my boy cherry. It was actually kind of overwhelming at first. I also got a reply from another sissy who lived somewhat close by who was also into older guys AND a virgin. I decided to reply to her. Her name was Heather and she was 19, very girly looking and she claimed to be very smooth. I was interested in meeting with her because I was nervous about going to an older strangers house alone with no experience. Turns out Heather was just as interested in me. We discussed sissy things like favourite outfits and lipstick and even shared sissy porn all through email. I had recently started renting a small suite in a private area and I lived alone, so i asked her if she wanted to come over sometime. She ecstatically replied saying "Yes I'm so excited to do this! I'm glad you can host. How's saturday night work for you?" I of course agreed to host on saturday and I asked her to bring all of her "sissy accessories." I was soooo excited i was leaking pre cum just thinking about it. All i did for the next 3 days was think about and prepare for meeting with heather. Finally it was saturday so before she arrived i took a bath, shaved my entire body and thoroughly cleaned my sissy pussy. I was so horny waiting for her to show up. I had this amazing tingling feeling deep inside of me. Around 8pm the door rang and i quickly went to open it. We had agreed to meet in "boy mode" so that we could dress up and become girls together. I opened the door and there stood a beautifully androgynous human. She was about 5"6, slender, medium length dark brown hair, pale skin that was very smooth and already girly looking face. I greeted her warmly and invited her in. There was sexual tension right away. It was obvious we were both nervous but both wanted this so bad. I took her into my living room where i had lay out large mattress and had a laptop set up on a side table and a couch with all my sissy clothes and some lube. Heather had a big smile on her face when she saw this and she set down her backpack on the couch. We sat on the bed and talked for a bit until we were comfortable and then we gave each other a small kiss. For the first time i felt like i was kissing someone as a girl and i think heather felt the same. There we were, a couple of virgin sissy sluts ready to be made into girls. We decided to get dressed. "Want to see what i have in my bag Alyssa?" I of course was eager and said yes. She pulled out her clothes, which were very slutty and a few toys. I gasped because i had never used a real dildo only homemade ones. She giggled at my reaction to her collection of anal toys. She had brought 2 buttplugs, 3 dildoes each bigger than the last and a very long double ended dildo. The thickest of the dildoes was almost as thick as a can of beer. It frightened me a little even though i wanted it in me. She could tell i was looking at it and explained she had just ordered the toys online and she could only take the smallest of the dildoes so far. She asked me if i would be interested in training our pussies together and i blushed and lovingly agreed. We decided to dress up and each went into separate rooms. I put on pink heels, fishnets leggings that strapped to my pink thong and a pink and purple crop top. I also straightened and tied my long blonde hair into pigtails with a pink hair tie. Then i slipped on a denim mini skirt and did my makeup. Hot pink lipstick. Can you tell my favourite colour? Hehe. I even used eye shadow and mascara. I looked like a passable sissy girl. I walked back into the living room to find Heather in a very sexy outfit. She wore a short purple and white frilly dress with black and white leggings and little ugg boots. She also had on full make up and she even had on a long black wig. Her lipstick was a dark purple. We had a moment of just staring at each other in amazement. That's when our voices and even the way we moved became VERY feminine. We both sat on the bed tingling with excitement. Heather reached into her bag and pulled put two chastity devices. I had never used one but i was definitely interested in trying! Then she said something that kind of surprised me. She asked me if i would like to have one but if i accept then i will have to agree to enter a sissy hood with her. She explained that there are sissy rules. Some of the rules were quite a commitment - we are only allowed to cum by stimulating our pussies and we must always wear a cage while having sex. Basically we would become total sex sluts designed to pleasure real men and we would become this together. I was wide eyed at the idea of this and surprised by the amount of trust she had considering we had just met. I don't know if it was from watching all the sissy hypno or if i'm just meant for this but i decided to accept her proposition. We both blushed and hugged. Heather had a naughty look in her eyes as she handed me my chastity device. She said that she wanted us to wear our cage for one week without taking it off. This seemed like a lot for my first time but rules are rules and now i was committed. I pulled down my thong exposing my limp clitty - heather looked very turned on by this. I slipped on my cage for the first time and it fit perfectly!!! She then lifted my totally shaven and smooth clitty and balls to inspect how it fit before locking it on with a tiny lock and putting the key in her bag. She did the same to herself. Seeing her small shaven sissy clitty started to make me hard but my new cage would not let me which forced the arousal to my prostate or "sissy g-spot." I had never felt this feminine. She also placed her key in her bag and explained she would return me mine in a week. We then lay back next to each other and each took one of the small butt plugs. After lubing our pussies we held hands, put our legs up in the air and slowly inserted our plugs. Heathers hand gripped mine tighter as we started to moan and pant. My caged clitty hanging useless, dressed like a total slut with another sissy and with buttplug inside of me. I was in heaven. Once my pussy had totally adjusted to the plug I stood up and did a girly spin to show Heather my body. I then walked over to the laptop and turned on a sissy trainer video then i got onto the bed in doggy style position and put my ass in the air for heather. My thong barely covered the plug that was in me and my mini skirt covered half my ass. Heather then knelt above me, moved my skirt out of the way and pulled my thong to the side. Finally someone else was going to enjoy my pussy. I moaned as she slowly pulled out the plug and exposed my pink winking pussy. It felt so warm and wet that i felt something leak out from my clitty as she pulled it out. I could tell she was really enjoying this because she was panting. She put her girly little hands on my hips at both sides of my ass and spread me. I put all my effort into winking my bumhole to make sure she knew i wanted it. She kissed my pussy cheek leaving a purple mark shaped like slutty lips. Then i felt something that put me into ecstasy. She drove her warm tongue as deep into my pussy as she could and started eating me out. Feeling her tongue writhing around inside me tickling my g-spot made me leak sissy juice again. She finished licking me with a kiss right on my butthole. It was obvious i had been leaking and Heather noticed. She then took my precum from the mattress and lubed my ass with it. We gave each other a naughty look. I then stood up and lay Heather down on her back and told her to spread her pussy. Her dress was pulled up and it d****d across her stomach, her caged clitty hung to the side and she had her legs up in the air with her knees together. She looked so cute spreading her plugged pussy with her ugg boots on and the little cotton balls hanging down. I slowly pulled out her plug and suddenly it popped out revealing a perfect hole that stayed slightly open for a few seconds. I was so turned on. I went crazy on her pussy with my mouth. I droves my tongue as deep as i could and she tasted so sweet. Holding her clit out of the way i licked from her butthole up the little line to her girly balls. She liked when i did that. After a while we both stood up, turned off the sissy hypno and kissed. By now we really were in a state of hypnosis and our pussies were hungry for more. I gestured at the double ended dildo and heather rose an eyebrow. "Think we could take that?" I giggled. "Want to find out?" Heather agreed but first reached into her bag and pulled out a joint. She asked if i smoked and i said i had a few times. We decided to go outside the back of my place and get high. Going back inside i remember feeling like such a slut. We sat on the bad facing each other with our legs out. We moved closer until our clitties were touching then we both lay back into a scissoring position. After lubing our holes heather positioned the long dildo with a head on each of our pussies, sliding the head halfway in so that it would stay there. Even that felt big but i was ready for more. We both put our hands on the bed behind us and slowly moved our pussies closer together. Oh my god it felt good to feel my pussy being stimulated with a twin sissy feeling exactly what i felt. We moaned together, sliding deeper. The dildo was 12" in total and soon we each had the full six inches inside of us and our little taints with grinding against each other. That's when we went crazy and starting grinding hard and fast, thrashing around trying to fuck our toy as hard as we could. Girly sex noises filled my house. Our clitty cages were hitting together and i could see our sissy juices leaking out and mixing before being ground in the space between our bumholes and our balls. After 10 minutes of scissoring we slid out the toy and touched each others holes to admire what we had done, both noticing they were quite a bit looser. We were both very satisfied and sat up. Still high we decided to check the time. It was after midnight already and we were shocked and getting tired. Heather surprised me again and asked if she could stay over, i said yes. We cuddled up in the bed and kept most of our slutty clothes on and of course leaving our cages and reinserting our plugs for the night. We slept until morning with our legs entangled together and holding hands. In the morning Heather had to leave around 9 and we made plans for her to stay over again in two nights from now. She changed back into her normal clothes but i noticed she had on her cage, some panties and her plug still in as she slipped put the door. After she left, the experience dawned on me and i was filled with happiness. I was now on track to becoming a real sissy girl.
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