Sim Sissy I
Posted: Mon Sep 09, 2024 2:52 pm
01. The Start.
When I turned eighteen I started my own little free-lance IT-Company so I could also do IT work for companies instead of only cleaning up viruses on computers or replacing hard-drives. I didn’t earn super much but now I don’t need to work in a retail store or work in cafes or restaurants like other people with the same education need to do. And yes, I study IT, at the moment super boring but I NEED the diploma so I can go to work at a graphics designer or gaming company, at least that’s what my parents keep telling me. They hold a draconic watch on my bank-account and for every euro I earn they transfer 70 percent to a savings account I’m not allowed to touch,even though I’m an adult. The other 30 percent I can use to pay for my own expenses and whatever I need. But they allowed me to buy my own car as soon as I turned eighteen. I got my driving license at the first try at seventeen.
Well, enough about me, let me tell you more about me. I’m nineteen years old and this summer I’ll enter the glorious twenties. I’m a skinny kid, I weigh about 56 kilo’s and I’m 172 cm tall. I have never been a big pain in the ass for my parents, the only rebelling against them was not going to the barber or cleaning up my room. And because my mom got tired of collecting my clothes from my room, one day she said I had to do my own laundry. She wouldn’t touch my clothes any more so I learned how to do the laundry all by myself.
Because I stayed inside my room a lot, didn’t have many friends, my parents pushed me, no they ordered me to join the scouts so I became a junior scout leader. I’m the one with all the crazy ideas for the games and summer camps, like pirates and treasure chests full of gold and jewels.
02. Starting the Sims.
Since my parents control my official income and also make me hand over any money I make when going over to someone for virus removal or disk replacements, I have another side job. At my school a lot of students still play the Sims or other games and I have a real talent for manipulating game-data. I can manipulate everything in games like the Sims. Clothing, faces, body parts, families, the whole woohoo’s, so beside creating skins for games like the Sims, Fortnight and so many more, I also develop save-games with Sim-Families as requested. Hand me a picture of your family and I’ll create a similar family in the Sims for you to play with.
I’m the most proud of one I did for a girl who walked up to me in the cantina at school. A standard request about recreating her family in the Sims. She wanted the house and garden in the Sims to match her own house and garden. Of course the same went for her pets and family tree. I was able to do it and 25 euros were earned. She actually should have paid more but she was gorgeous and when I had created the save, I also had my fun in equipping every adult with genitalia and orchestrating a huge gang-bang in the game. But her copy was of course without the genitalia-mod present.
I liked playing and manipulating the Sims, I could be anybody but I preferred playing as a female character. They were so much nicer to look at and the sex was way easier. It sometimes took a couple of days, but in the end my Sim character had fucked every male and if possible also did the woohoo with every female in the game.
03. Exploring myself.
With the right add-ons in the sims, I had my character walk around with a cum-covered slut-face and that turned me on so much, letting her kneel down, slobber on some cock, get a facial and take the next one. Just as in the pornos I liked to watch.
I preferred to only see the dicks from the guys, if it was attached to a tranny, I okay-ed watching that body also. But I loved seeing a girl bob on a cock, sucking and guzzling down the cum. I saved it in my mind and somehow, I kept fantasizing about wanting to do it myself, suck a cock, feel the cum shoot into my mouth. But I’m a guy and honestly, when I look at other guys I ain't thinking, fuck he’s hot, so I know I’m not gay.
An idea came to my mind. I would try to suck myself. For camp I had gathered a lot of jewels for our treasure-chest, my mom, and friends of hers, had helped and donated a lot of cheap or plastic jewelry, all shiny. Clip on earrings, necklaces, diadems, you name it. What if I would dress up and then pump my mouth with a load of cum.
Luckily my parents went on frequent weekend-trips, they considered me a responsible adult, so when they left Friday-evening, I showered, shaved my face, (I'm lucky to have very little body hair), massaged my whole body with some body-cream and took out my treasure chest.
On my desk I had a make-up mirror I used for putting in my contact-lenses and I started putting on stuff. I ended up with a fake-ruby encrusted diadem, clip-on earrings with plastic jades set in gold and about four necklaces with fake pearls and beads. Between the jewelry there was also a nice make-up kit and, while watching some tutorials online (thank you Nikki), I was surprised at how good I looked.
Next, dressing up, I had some older shirts that were a tight fit, they made me look more girly, next some panties, I had bought a simple four-pack in a shop in the city pretending I was running an errand for my mom. Luckily I also had a simple skirt. I had bought it last year for carnival, everyone dressed up like they wanted and I had bought it together with some other costumes, I had never worn it.
I put everything on and I watched myself in the mirror. But a girl was looking back at me, flat-chested but still a girl. I was a flat-chested rosy-pink girl with glimmering earrings, necklaces and a tiara in my hair. I took out my phone and made a duck-face at myself in the mirror. I had a separate work account on it with my secret accounts for snap-chat, TikTok and other applications, so any picture I would take would not be visible in my normal account.
And even my normal account was really well protected. I snapped and edited some pictures, put on filters and they looked extremely good to me. I kept looking at myself and I was horny, fuck, the only thing my girly face was missing was indeed a load of cum.
I put my digital camera on a tripod, fixed the focus and sat on my knees with my mouth at cock-sucking height. I would then later add some shots of myself with my dick out and align it so the result would look like a girl was sucking my dick. Hot! I did various shots and decided the bed was next.
The camera turned onto my pillow, I laid down and started jerking my dick. I laid on my back on my bed, put my legs against the slanted ceiling above my bed. As if I walked forward against the ceiling, my penis crept closer and closer to my face, my back more and more arched, and then I started jerking it, but it wasn't easy.
I was used to masturbating while lying on my stomach having my hands between my stomach and penis, until I finally would come, I had never really jerked off in the classic way. Now I had to get used to jerking, while I kept my penis aimed at my face. I had to stop several times, stretch and then ‘backtrack’ aiming my penis to my face.
But finally I hit the nerve in stroking my cock, I came and my cum splattered in my face, my eye, hair, pillow, earrings, diadem, everything.
It was thrilling but also kinda painful when I finally slowly relaxed my back. I felt the cum trickle down and I stood up, relaxing my back some more, walked towards the mirror and saw the mess, also felt the mess in my eye, while having had my orgasm, my post-nut clarity kicked in.
I felt extremely ashamed, picked up my clothes and walked into the bathroom and cleaned everything and took a shower. When everything was returned to normal my feeling began to return and the shame dissipated slowly. It had been hot and I had been a good gurl. I liked it. I would do it again, I knew for sure. I looked at the footage and felt the urge to delete it all.
But I never did.
04. Practice makes perfect.
The rest of the weekend I tried again, dressed up, sucked my cock and collected my cum in my mouth and swallowed. Practice makes perfect and so I was finally able to get the head of my penis completely in my mouth so I didn’t miss a drop at all. I enjoyed it immensely. After every session I looked at myself in my big mirror. I was dressed up as a girl and had a face or mouth full of cum.
But I also really enjoyed dressing up, putting on the jewelry, make-up, taking pictures and videos of myself. I somehow got the urge to share it. So I started visiting cross-dressing boards and forums. I also started buying clothes; I bought various clothes online and I browsed a lot of thrift-shops. Sometimes I got some glances but then I mumbled something about studying for a play.
But also Vinted, an online site where people, mainly girls, sold their old clothes. You could easily ask a seller to check some measurements. So, Vinted was a perfect way to score clothing. There were a lot of nice clothes and it was simple to get those packages delivered to a shop with a pickup point. My parents kept going on their frequent city-trips and they even bought a timeshare in a so-called chalet together with my aunt and uncle. When they were away, I could easily do whatever I wanted.
My clothes with cum or makeup stains on them were washed, dried and stored back in my closet before they returned home. I had also collected a small set of lingerie and some fillers for the bra’s. I just love cheap online shops like Shein and AliExpress.
Since I decided I wanted to share myself with the rest of the world, I had thought about how, just posting a shot of myself with my face visible, no way, a face blurred, also kinda lame. So I decided to open Sims and manipulate the character until we were twins. Then I would post a picture with both me and the sim together. The first sets were pretty conservative, but I kept going and going on with my fantasies. I received a lot of positive comments so I kept on doing it.
Besides my own collection, I of course also had a nice collection of beauties I loved looking at, and since I was a guy dressing up as a girl, it mostly contained trans, fem-boy and of course sissies. I had them only because I needed tips for dressing up, I wasn’t a sissy or fem boy, I was only cross-dressing. But I loved the fact that I could look so feminine myself.
I had made a lot of contacts and online friends and told some of them about the dress-ups I did and the sim-characters I had created. So I posted a nice set I had made. I had struck a pose like my sim, wore the same type of clothes, I had even incorporated the logo on the shirt in the sim's clothing. It was fun, but all of a sudden, my post went viral on the board. I also received notice that it also traversed to other boards. Luckily the people on the boards only roughly knew my location (the Netherlands), but oh wow, this was empowering, hot.
I was glad I had blurred and masked my face, though my Sim’s face wasn't blurred and yes, it did kinda look like me but it wasn’t me. I posted some other sets and they also went viral.
I received all kinds of messages, some wanted to woohoo me, gave me sim-tasks to do, like read a book, sit on the couch, play games, weed the garden, take a shower, go pee, and of course a lot of sexual related tasks. I was flattered and I tried to do more of these poses.
Some people sent me a screenshot of their sim in clothes and asked me to copy it, but not having those clothes IRL was difficult. I always masked and blurred my face enough so I remained incognito.
When I turned eighteen I started my own little free-lance IT-Company so I could also do IT work for companies instead of only cleaning up viruses on computers or replacing hard-drives. I didn’t earn super much but now I don’t need to work in a retail store or work in cafes or restaurants like other people with the same education need to do. And yes, I study IT, at the moment super boring but I NEED the diploma so I can go to work at a graphics designer or gaming company, at least that’s what my parents keep telling me. They hold a draconic watch on my bank-account and for every euro I earn they transfer 70 percent to a savings account I’m not allowed to touch,even though I’m an adult. The other 30 percent I can use to pay for my own expenses and whatever I need. But they allowed me to buy my own car as soon as I turned eighteen. I got my driving license at the first try at seventeen.
Well, enough about me, let me tell you more about me. I’m nineteen years old and this summer I’ll enter the glorious twenties. I’m a skinny kid, I weigh about 56 kilo’s and I’m 172 cm tall. I have never been a big pain in the ass for my parents, the only rebelling against them was not going to the barber or cleaning up my room. And because my mom got tired of collecting my clothes from my room, one day she said I had to do my own laundry. She wouldn’t touch my clothes any more so I learned how to do the laundry all by myself.
Because I stayed inside my room a lot, didn’t have many friends, my parents pushed me, no they ordered me to join the scouts so I became a junior scout leader. I’m the one with all the crazy ideas for the games and summer camps, like pirates and treasure chests full of gold and jewels.
02. Starting the Sims.
Since my parents control my official income and also make me hand over any money I make when going over to someone for virus removal or disk replacements, I have another side job. At my school a lot of students still play the Sims or other games and I have a real talent for manipulating game-data. I can manipulate everything in games like the Sims. Clothing, faces, body parts, families, the whole woohoo’s, so beside creating skins for games like the Sims, Fortnight and so many more, I also develop save-games with Sim-Families as requested. Hand me a picture of your family and I’ll create a similar family in the Sims for you to play with.
I’m the most proud of one I did for a girl who walked up to me in the cantina at school. A standard request about recreating her family in the Sims. She wanted the house and garden in the Sims to match her own house and garden. Of course the same went for her pets and family tree. I was able to do it and 25 euros were earned. She actually should have paid more but she was gorgeous and when I had created the save, I also had my fun in equipping every adult with genitalia and orchestrating a huge gang-bang in the game. But her copy was of course without the genitalia-mod present.
I liked playing and manipulating the Sims, I could be anybody but I preferred playing as a female character. They were so much nicer to look at and the sex was way easier. It sometimes took a couple of days, but in the end my Sim character had fucked every male and if possible also did the woohoo with every female in the game.
03. Exploring myself.
With the right add-ons in the sims, I had my character walk around with a cum-covered slut-face and that turned me on so much, letting her kneel down, slobber on some cock, get a facial and take the next one. Just as in the pornos I liked to watch.
I preferred to only see the dicks from the guys, if it was attached to a tranny, I okay-ed watching that body also. But I loved seeing a girl bob on a cock, sucking and guzzling down the cum. I saved it in my mind and somehow, I kept fantasizing about wanting to do it myself, suck a cock, feel the cum shoot into my mouth. But I’m a guy and honestly, when I look at other guys I ain't thinking, fuck he’s hot, so I know I’m not gay.
An idea came to my mind. I would try to suck myself. For camp I had gathered a lot of jewels for our treasure-chest, my mom, and friends of hers, had helped and donated a lot of cheap or plastic jewelry, all shiny. Clip on earrings, necklaces, diadems, you name it. What if I would dress up and then pump my mouth with a load of cum.
Luckily my parents went on frequent weekend-trips, they considered me a responsible adult, so when they left Friday-evening, I showered, shaved my face, (I'm lucky to have very little body hair), massaged my whole body with some body-cream and took out my treasure chest.
On my desk I had a make-up mirror I used for putting in my contact-lenses and I started putting on stuff. I ended up with a fake-ruby encrusted diadem, clip-on earrings with plastic jades set in gold and about four necklaces with fake pearls and beads. Between the jewelry there was also a nice make-up kit and, while watching some tutorials online (thank you Nikki), I was surprised at how good I looked.
Next, dressing up, I had some older shirts that were a tight fit, they made me look more girly, next some panties, I had bought a simple four-pack in a shop in the city pretending I was running an errand for my mom. Luckily I also had a simple skirt. I had bought it last year for carnival, everyone dressed up like they wanted and I had bought it together with some other costumes, I had never worn it.
I put everything on and I watched myself in the mirror. But a girl was looking back at me, flat-chested but still a girl. I was a flat-chested rosy-pink girl with glimmering earrings, necklaces and a tiara in my hair. I took out my phone and made a duck-face at myself in the mirror. I had a separate work account on it with my secret accounts for snap-chat, TikTok and other applications, so any picture I would take would not be visible in my normal account.
And even my normal account was really well protected. I snapped and edited some pictures, put on filters and they looked extremely good to me. I kept looking at myself and I was horny, fuck, the only thing my girly face was missing was indeed a load of cum.
I put my digital camera on a tripod, fixed the focus and sat on my knees with my mouth at cock-sucking height. I would then later add some shots of myself with my dick out and align it so the result would look like a girl was sucking my dick. Hot! I did various shots and decided the bed was next.
The camera turned onto my pillow, I laid down and started jerking my dick. I laid on my back on my bed, put my legs against the slanted ceiling above my bed. As if I walked forward against the ceiling, my penis crept closer and closer to my face, my back more and more arched, and then I started jerking it, but it wasn't easy.
I was used to masturbating while lying on my stomach having my hands between my stomach and penis, until I finally would come, I had never really jerked off in the classic way. Now I had to get used to jerking, while I kept my penis aimed at my face. I had to stop several times, stretch and then ‘backtrack’ aiming my penis to my face.
But finally I hit the nerve in stroking my cock, I came and my cum splattered in my face, my eye, hair, pillow, earrings, diadem, everything.
It was thrilling but also kinda painful when I finally slowly relaxed my back. I felt the cum trickle down and I stood up, relaxing my back some more, walked towards the mirror and saw the mess, also felt the mess in my eye, while having had my orgasm, my post-nut clarity kicked in.
I felt extremely ashamed, picked up my clothes and walked into the bathroom and cleaned everything and took a shower. When everything was returned to normal my feeling began to return and the shame dissipated slowly. It had been hot and I had been a good gurl. I liked it. I would do it again, I knew for sure. I looked at the footage and felt the urge to delete it all.
But I never did.
04. Practice makes perfect.
The rest of the weekend I tried again, dressed up, sucked my cock and collected my cum in my mouth and swallowed. Practice makes perfect and so I was finally able to get the head of my penis completely in my mouth so I didn’t miss a drop at all. I enjoyed it immensely. After every session I looked at myself in my big mirror. I was dressed up as a girl and had a face or mouth full of cum.
But I also really enjoyed dressing up, putting on the jewelry, make-up, taking pictures and videos of myself. I somehow got the urge to share it. So I started visiting cross-dressing boards and forums. I also started buying clothes; I bought various clothes online and I browsed a lot of thrift-shops. Sometimes I got some glances but then I mumbled something about studying for a play.
But also Vinted, an online site where people, mainly girls, sold their old clothes. You could easily ask a seller to check some measurements. So, Vinted was a perfect way to score clothing. There were a lot of nice clothes and it was simple to get those packages delivered to a shop with a pickup point. My parents kept going on their frequent city-trips and they even bought a timeshare in a so-called chalet together with my aunt and uncle. When they were away, I could easily do whatever I wanted.
My clothes with cum or makeup stains on them were washed, dried and stored back in my closet before they returned home. I had also collected a small set of lingerie and some fillers for the bra’s. I just love cheap online shops like Shein and AliExpress.
Since I decided I wanted to share myself with the rest of the world, I had thought about how, just posting a shot of myself with my face visible, no way, a face blurred, also kinda lame. So I decided to open Sims and manipulate the character until we were twins. Then I would post a picture with both me and the sim together. The first sets were pretty conservative, but I kept going and going on with my fantasies. I received a lot of positive comments so I kept on doing it.
Besides my own collection, I of course also had a nice collection of beauties I loved looking at, and since I was a guy dressing up as a girl, it mostly contained trans, fem-boy and of course sissies. I had them only because I needed tips for dressing up, I wasn’t a sissy or fem boy, I was only cross-dressing. But I loved the fact that I could look so feminine myself.
I had made a lot of contacts and online friends and told some of them about the dress-ups I did and the sim-characters I had created. So I posted a nice set I had made. I had struck a pose like my sim, wore the same type of clothes, I had even incorporated the logo on the shirt in the sim's clothing. It was fun, but all of a sudden, my post went viral on the board. I also received notice that it also traversed to other boards. Luckily the people on the boards only roughly knew my location (the Netherlands), but oh wow, this was empowering, hot.
I was glad I had blurred and masked my face, though my Sim’s face wasn't blurred and yes, it did kinda look like me but it wasn’t me. I posted some other sets and they also went viral.
I received all kinds of messages, some wanted to woohoo me, gave me sim-tasks to do, like read a book, sit on the couch, play games, weed the garden, take a shower, go pee, and of course a lot of sexual related tasks. I was flattered and I tried to do more of these poses.
Some people sent me a screenshot of their sim in clothes and asked me to copy it, but not having those clothes IRL was difficult. I always masked and blurred my face enough so I remained incognito.