My name is Jack, I'm a 17 year old male raised in Staffordshire, England. This is my story. I had always considered myself 100% straight. However at a young age I developed fetishes which may lead some to question how straight I really was. When browsing through porn I would always get seek out the blowjob and anal videos. It seemed strange at the time but I sometimes imagined myself not as the man, but the woman.
Hi guys my first attempt at a story, leave any feedback in the comments section. Enjoy!
My name is Jack, I'm a 17 year old male raised in Staffordshire, England. This is my story.
I had always considered myself 100% straight. However at a young age I developed fetishes which may lead some to question how straight I really was. When browsing through porn I would always get seek out the blowjob and anal videos. It seemed strange at the time but I sometimes imagined myself not as the man, but the woman. I'd fantasize about sucking on a long thick cock, then bending over and taking the whole thing in my tight asshole. However as soon as I was done masturbating I'd lose all sense of these desires and whilst I enjoyed them at the time I would never have dreamed of acting upon these fantasies.
It was around this time that I first snuck into my older sister’s room. I wasn't sure what I was searching for the first time, I was just snooping around I guess. As I was looking around my eyes drifted towards her desk draws. The top draw was open and in it where several organised lines of crisp ironed panties. My sister always was very tidy. As I stood looking at them neatly laid out I recalled my love of porn videos with the girls wearing cute tight panties. I loved the panties snug fit and the way they caressed the ass perfectly. What I did next may very well have changed my life; I reached into her draw and took out the top pair. They were white boxer briefs with a slightly frilly edge. I was in love. The house was empty so I wasted no time. After grabbing my phone off my desk I rushed to the bathroom. I threw off my jeans, t-shirt, socks and boxers and slipped on my sister's panties. They fit perfectly, the smooth cotton felt like heaven on my bare skin and my fully erect cock was in a level of bliss I had never experienced before. I opened my phone and navigated to my porn folder, I selected my favourite video. It featured a beautiful woman taking two large dicks, at first she had one in her mouth and one in her ass but soon she was on all fours taking both in her ass, at the same time. I was so turned on, I got down on all fours mimicking the woman in the video, and grasping my bulging cock I rocked back and forth imagining taking those clocks myself. Before long I reached climax and shot my load all over the bathroom floor.
This became a regular occurrence; I slipped on my sister panties and jerked off at least three times a week. Before long I needed more so I began to wear panties under my boxers around the house. I loved the snug feeling and struggled to hold back an erection for most of the day. I also became more ambitious with my masturbating, instead of restricting myself to my bathroom I spread out. One of my favourite spots was my schools bathroom; I would slip in at lunch then lock myself in a cubicle. I fantasized about someone walking in on me and exposing me for what I was becoming, a dirty little sissy boy. I imagined them opening the cubicle door and upon seeing me forcing me onto my knees and making me beg for their cock. Unfortunately this never happened and I had to make do with my fantasies and whatever suitable porn I could find. Whilst searching for sissy porn I stumbled upon tumblr, it was a new fountain of sissy porn, hypno and basically everything to do with being the perfect sissy. I made contact with a man; he was a tall tanned man aged 28 with a nice long cock. He often sent me pictures of his dick which I would jerk off over. After a few weeks of contact he asked if he could send me clothes to wear, on the condition that I sent him photos after. I couldn't have them delivered to my home in case my parents intercepted the package. To get around this I had him send it to an amazon locker in town and I went to collect it, luckily I didn't bump into anyone I knew in the way. I was very excited to see what it was that he had bought me!
I got home to an empty house, perfect. I ran upstairs put the parcel on my bed and ripped it open. It was perfect! He had bought me a full schoolgirl outfit. Sleek black panties, with silky white stockings and a matching garter belt. There was also a short black pleated skirt and a white shirt. I just knew the outfit would look great, I couldn't try it on at home though in case someone came back. I decided to go out into the woods behind my house, I loaded all the clothes into a backpack, packed a blanket and my camera with a tripod then set off.
After 10 minutes I arrived. I had found a secluded opening in the forest, it was very well hidden and I'd never seen anyone around this area. I placed the blanket on the ground and got to work. First I removed my boy clothes and folded them neatly on the forest floor. Then I took out the panties and glided them over my now shaven legs, they fit perfectly. I then fooled the garter belt out and put it on before pulling out the stockings and sliding them onto my legs. I clipped them to the garter belt then shimmied into the gorgeous black skirt. I finished off the look by buttoning up the shirt and tucking it into my skirt. Feeling fully feminine I set up my camera and tripod and began to pose. I spent half an hour taking photos stopping only to jerk until close to orgasm then stopping. It was incredible.
I was so preoccupied with looking sexy and taking cute photos and videos for my sugar daddy that I didn't notice a small group of guys creep into the clearing. That was until I was grabbed from behind and pulled onto the floor onto my blanket. As I was forced onto my back I looked up at my three male attackers. They must have been my age if not a little younger, they were quite skinny. Honestly if I had wanted to I could have thrown them off me, but that wasn't what I wanted. I wanted them to have their way with me, treat me like a piece of meat, use me as a fucktoy. They seemed to pick up on my cooperation as they silently began to undress. They didn't take long and all of a sudden I found three cocks dangling in front of my face. I picked myself off the floor and kneeled down as they created a circle around me. I stopped for a moment to study these boys’ young hard cocks. The guy who I assumed was the leader had the most impressive package; easily seven inches with a slight upwards curve. The other two were of similar size, closer to five inches however slightly thicker than the longest, all of them were uncut and all of them were standing to attention. My silence seemed to worry the boys as they looked anxious, maybe they thought I didn't want this. I'd show them. I grabbed the largest cock with both hands, marvelling at how smooth it felt. I gave it a few strokes before taking the tip into my mouth. It felt fantastic. I worked my way further down his shaft until I had maybe two thirds of his member in my mouth. Trying to replicate the porn videos I'd seen I began to slurp on his cock thrusting my mouth back and forwards savouring his wonderful taste. After a few minutes of this his friends got bored of waiting and moved closer behind me. One of them began to fondle my ass underneath my skirt whilst the other guided my free hand onto his own erect cock. I eagerly responded and stroked his full length whilst my face was being impaled with the first boys long cock. It didn't take long for him to become ambitious with my mouth and he began matching my thrusts pushing his dick deeper and deeper into my throat. I began to choke and spit but he wouldn't stop, I could feel his cock begin to bulge and knew what was coming next. I tried to relax my throat as much as possible as he sprayed his young salty semen into my sissy mouth. As he pulled out he instructed me to swallow his whole load, eagerly I did as instructed. It tasted delicious. They were most certainly not done with me yet and the boys cycled round so a new one was in front, he pushed his cock towards my face and I obliged by taking it into my mouth. Behind me the largest boy began to get adventurous and lifted up my skirt to reveal my tight black panties. He tore them off me and threw them onto the forest floor. The third boy who hadn't had a chance to get in on the action yet spat on my asshole and began to finger fuck my virgin hole. I was in ecstasy, taking a cock from one boy whilst another fingered my ass all whilst in the middle of a forest clearing. It didn't take long for the second boy to finish in my mouth and again I swallowed as instructed. The third boy removed his fingers from my ass and made his way up front to use my mouth. For the third time today I was servicing a young hare cock. The boy who had the first go at my mouth was hard once again, I felt him rubbing my asshole with his wet fingers. He pushed me down so I was on all fours and I felt a larger object at the entrance to my hole. I moaned around the cock in my mouth as the second cock was slowly guided into my virgin ass. It burned at first as my ass stretched to accommodate this foreign object. It didn't take long before the pain started to turn into pleasure as I increased the frequency of my moans he began to increase the speed of his thrusts and I matched them with movements of my own. As I was paying so much attention to the pleasure from behind I failed to notice the cock in my mouth bulging and was surprised by a mouth full of hot sticky semen. With all boys finished up front more attention was turned to the first boy, who by now was now almost violent in his thrusting. His cock began to bulge and instead of finishing inside my ass he pulled out and sprayed his second load of semen all over my schoolgirl uniform. As soon as he was done the boys wiped any remaining cum left on their dicks onto my shirt, put there clothes back on and left.