When I had just turned 18 whenever I was home alone, I would get dressed in whatever I could find in my older sister’s room that I thought looked pretty, run into the bathroom to admire myself, and then wank to my reflection in the mirror. Sometimes if I was feeling extra naughty, I would lick up my cum afterward, but most of the time I washed it away. I remember once finding a dildo hidden under my sister’s bed. The next couple of weeks any chance I would get I would wear one of her thongs and a bra, pretend to be a girl, and fuck myself with the dildo. It made me so horny pretending to be a girl getting fucked by a proper man.
This continued for a while until one day my dad asked to speak to me. He told me that he had been putting some things in my wardrobe and discovered the stolen dildo in the back of the wardrobe. He said he had thrown it in the trash and asked if I knew about it, which I denied claiming someone else must have hidden it there. In hindsight, he must have seen straight through the lie, but he dropped it, and ever since then we have never spoken about the matter.
I had just finished school and had a part-time summer job before going to uni, which enabled me to have a little spending money. The summer heat was making me extra horny. I would stay up most nights until 3 am, looking at sissy captions on Tumblr, whilst fingering my ass pussy and wanking myself off.
One Saturday evening I came across a caption where you had to calculate your sissy score depending on all the girly things you had done. I had done most of the tasks that could be completed individually, except for wearing a butt plug. There were other tasks in the story then got onto things I hadn’t done, such as meeting up with someone from Craigslist, sucking a real dick, eating another man’s cum and getting fucked by a man. This post got me so horny about the idea of acting like a slutty girl that I came into some stripy tanga panties I had borrowed from my sister’s bedroom. I lay there thinking about how exciting it would be to meet a real man whilst I was dressed up as a sissy girl.
The next morning, I went online and bought myself a butt plug with a jiggle ball inside, some razors, and cheap makeup. I then went on the Craigslist website to see how it worked. From what I could see people put up adverts with a few pictures of themselves, what they wanted to do, and the best way to get in contact.
Over the next few days when I was home alone, I did a few photo shoots in my bedroom. One time dressed in my sister’s yellow triangle bikini; I paired this with some of her cute cotton gym shorts that I rolled up to accentuate my peachy bum. I did another shoot where I found my sister’s matching pink cotton thong and halter neck bra; on top of this I wore a denim mini skirt and a cute crop top. Finally, I did a quick shoot of myself completely naked. I wanted to show off my slim body, erect tiny clitty and girly-looking bum. I was almost done when I had the idea to get on all fours and finger my virgin asshole whilst trying to get a good photo of the action. I managed to get some snaps so put my phone down. It felt so good having my fingers up there, so I kept shoving my fingers in and out of my hole. I could feel my clitty starting to leak now. Suddenly I heard the front door open and my mum call upstairs. I yanked my fingers out my sissy hole, swiftly put on some trackies and headed downstairs to say hi. Thankfully I had got away without my mum finding out.
The next week passed by with parcels arriving for me every few days and by Thursday morning, everything had arrived.
That afternoon I put up my advert on Craigslist with the photos I had taken, along with the caption ’18-year-old virgin sissy looking for a real man to take my cherry’.
Almost immediately I started receiving emails in from men keen to meet up. Most emails were men just sending through photos of their penis asking if I wanted to suck it. There were a few better ones. Then finally I had an email in from a man called Steve, who worked on a building site as a bricklayer. He called me beautiful and effeminate, saying he had previous experience with another sissy a while back and was keen to try another one. He sent a photo of himself fully clothed. He had a nice face and a little bit of stubble. He was wearing a t-shirt where his arms were stretching the sleeves. There was also another photo of his body naked, he had nice pecs and thick muscular thighs. His body was hairy, but not too much. Finally, my eyes found the centre of the picture where I could see his raging uncut hard-on. It was a good size, and I could feel myself starting to salivate. My clitty had gotten rock hard staring at the photo of Steve’s boner. I started to rub one out staring at it and must have only lasted ten seconds before I came.
Steve and I immediately hit it off. He told me he lived alone in a block of flats right by Uxbridge tube station. He also mentioned that he had Saturday afternoon off and was finishing up at the building site by midday. We agreed that I would come over that Saturday from 3pm and we go from there.
On Saturday morning I woke up late and hopped into the bathroom with the razor I had bought the previous week, proceeding to shave my entire body from the eyebrows down completely hairless. It took an age, but when I was done and looked into the mirror and was impressed by my handiwork. I then got into the shower and gave myself a deep body scrub with my sister’s loohaf sponge, making sure to properly scrub clean my sissy pussy and my clitty. The hot shower on my hairless skin felt amazing, I was standing in the shower with my eyes closed thinking about Steve’s big arms and chest, when I heard a bang on the bathroom door and my sister shouting at me to get out the shower so she could get ready for her work and was running late. I quickly towelled myself off. Just before I walked out the door, I spotted her moisturiser, which I tucked under the towel and walked back to my bedroom.
I finished drying myself in my bedroom and them applied my sister’s moisturiser all over my body, paying particular attention to my ass. I was slowly inserting the tip of my index finger into my pussy and got lost in the moment. I was rudely brought back to reality when I heard my sister running down the stairs, shouting she was off to work and wouldn’t be back until late, followed by a loud bang from the front door closing. I slowly pulled my finger out my ass and found the butt plug I had bought last week. I bent over slightly and put my knee on a chair and slowly inserted the bulbous head of the plug. After 30 seconds of gently pressing at the butt plug, it popped all the way in. I snuck across the hallway and into my sister’s bedroom, opening her underwear drawer I saw the pink thong and halter neck bra I had done the photo shoot in, pulled it out thinking I would want to wear that later for Steve. I also found a pair of frilly blue panties I thought would look great on my freshly shaven body. So, I stepped into them and continued the search of what to wear for Steve in my sister’s wardrobe. After another minute of ruffling around I found the same denim mini skirt and crop top I had tried on a week ago and grabbed them. I tiptoed back across the hallway to my bedroom carrying my outfit for later dressed in nothing but the blue frilly panties to hide the jiggle ball butt plug.
I then packed the outfit and my makeup into my rucksack, then pulled my boy jeans over the blue panties I was wearing and pulled on a jumper and t-shirt. I then went downstairs and joined both my parents for a late brunch. They were talking about how they were just about to hit the road to spend the night over at my uncle’s and asked if I was getting up to anything this weekend. I responded saying I was going over to a friend’s place this afternoon to hang out. We sat and chatted for over an hour, before eventually realising we all had to get going.
I grabbed my rucksack double checking I had my goodies for later, then stepped out and walked down the hill to my nearest tube station. I could feel the jiggle ball within the butt plug wobbling about. This excitement meant I could now feel my hard clitty straining against the mesh of the frilly panties I was wearing underneath. I kept walking past passers-by wondering if they knew I had a butt plug inside me and I was wearing girly panties in public. This only caused me to get more aroused.
I eventually reached my tube station, went through the ticket barriers and down to the train. When the train got moving it rocked back and forth, causing the jiggle ball to wobble inside the butt plug. I eventually had to cross my legs to hide my excitement from all the other passengers on the train. About halfway through the journey, I started to get nervous. What if I got there and Steve was a catfish? What if he didn’t exist at all? What would happen if I didn’t like being with a man?
I spent the next few minutes stressing about hypothetical things that could go wrong until the intercom on the train announced we were pulling into Uxbridge tube station. I got off the train and thought well here I am. I should at least try to follow through with meeting Steve. Once I got out the station, I gave Steve a call from my mobile saying I was outside his block of flats. He came down a few minutes later, looking like he was fresh out the shower with still half-soggy hair, came over and gave me a hug to say hi. When he wrapped both his big arms around me and pressed me into his hard firm body, I became a lot more reassured about my decision to meet up with him.
Steve took me in the lift up to his flat and showed me round. His flat looked out on the high street, and you could see people on the pavement going about their lives. Steve sat me down and offered me a glass of white wine for the nerves. We sat there talking a bit more about our backstories, things we had done, other things we hadn’t but wanted to try, and what neither of us liked to do. Steve poured me another glass of white wine. Steve asked if I wanted to be called anything in particular, and I said I had always thought Ami was a pretty name. He laughed out loud as apparently the previous crossdresser he had been with also went by the name of Ami. So that’s how the name stuck. Eventually, Steve suggested I go into the bathroom and change into Ami.
I got in there and immediately stripped down to the frilly blue panties I was wearing. By now they were soaked in my pre-cum. I took them off and strained some of my juices out of them and into my mouth to taste. Next, I grabbed the pink cotton thong out of my rucksack and slowly pulled it up my hairless legs. I could feel the back seam of the thong pressing against the butt plug still in my ass. Next, I pulled on the matching pink halter neck bra, followed by the denim mini skirt and finally the crop top to complete the outfit. I pulled the makeup bag out of the rucksack and went over to the mirror. I caught a glimpse of myself and thought who was that hot girl looking back at me? Next, I applied some foundation, blusher, eye shadow, mascara, and finally a neon pink lipstick.
I meekly walked out the bathroom towards Steve, nervous as no one else had ever seen me dressed up as Ami. When our eyes connected his jaw dropped, “Ami you look incredible, so much hotter in real life than in the photos.
“Awe thanks, Steve! You really mean that?” I said as I was eyeing up the bulge in his trousers.
“Of course, darling. Now come over here so I can get a better look at you.”
I eagerly came over to him and he twirled me around so he could see me from every direction. He then slapped my peachy ass and gave it a manly squeeze for good measure. He must have felt the plug as the next words out his mouth were “Have you got something inside of you already Ami?”
A little embarrassedly I responded, “Uhhhh yeah, would you like me to show you?”
Steve nodded, with that whilst still standing up I bent over and put my hands on the floor. Steve knelt down behind me and pulled my thong down to my ankles revealing the butt plug that had been in there for the last couple of hours.
“Oh my God that’s so hot!” he exclaimed. Steve slowly started pulling out the plug and I could feel my anus closing behind it. He went back and forth shoving it in and out until he could see my clitty starting to leak some juices. At which point he promptly pulled the plug out saying, “We can’t have you having all the fun. Come kneel over here Ami. I’ve got something to show you.”
I got on all fours and crawled as seductively as I could to him, maintaining eye contact. He pulled the crop top I was wearing off, revealing the pink halter-neck bra I was wearing. Steve then undid his trousers and let them drop. In line with my eyes flopped out Steve’s rock hard slightly hairy cock. “Oh, wow how big is it?” I said thinking it was easily twice as large as my clitty.
“Errrr, I think around the seven-inch mark. Do you wanna give it a taste, Ami?”
Just staring at his cock was making me salivate. I nodded slowly and moved to wrap my lips around his uncut foreskin. It tasted slightly salty and just a little bit sweaty. The texture was way different to the dildo my dad had previously found. Steve’s foreskin was way softer and juicier than I had anticipated. I pushed my head down a little further onto his shaft and that was rock solid. Slowly I started bobbing my head up and down, which Steve seemed to like as he groaned a little. I kept going a while longer until I needed some breath. As I pulled my mouth off his shaft a drool of spit clung on between his bell end and my lips. “Ami my balls are feeling a little left out, why don’t you pay them some attention.”
With that command I moved down a little further, putting one of his balls in my mouth. I tried sucking it like a gobstopper, whilst at the same time slowly wanking off his cock. Steve really seemed to like that. I kept doing this until he looked down at me and smiled, “You know Ami, I don’t think you can really claim to have properly sucked a dick until you have deepthroated the whole thing. Do you want me to help you with that?”
I nodded up at him still with his testicle in my mouth and nodded appreciatively. Steve pulled my mouth away from his balls and told me to grab some breath before we continued. Next, he started lowering my mouth onto his shaft again, this time I was going faster and trying to take more and more of him into my mouth. I could feel him already hitting the back on my mouth, and I could still see more of his cock in front of me. How was I going to hit the rest of him into my mouth? With that, I felt his hands on the back of my head pressing me closer and closer to him.
We kept going like this until I was finally bottoming out on his cock. My nose was pressed into his pubic hair above his cock. He was pressing his cock down my throat. He held me there for what felt like an eternity, until I started gargling on his rod as I needed breath.
Steve finally released me and exclaimed, “Woah you’re a natural born cock sucking sissy slut!”
I looked at the mess I had caused on his cock and there was slobber everywhere. I could even feel it coming off my chin.
“Bend over. I need to get you ready to become a woman,” he told me.
I obediently climbed onto the sofa sticking my naked ass into the air and lying my head on the seat all the while looking back at Steve. The mini skirt I was still wearing had now fallen higher onto my chest properly revealing my virgin sissy hole and clitty. Steve got his lube out and slowly put a finger inside of me. It felt incredible, and it was almost impossible not to shoot my load in that instant. He put in another finger, and I could feel my hole stretching to make room. Steve was now pounding my ass with his two fingers, and it felt like pure bliss.
Once my ass had become properly accustomed to his fingers he pulled out, got up and walked out of the room. He came back almost immediately with a condom. Steve quickly put this on and then applied a generous amount of lube to his weapon and my semi-loosened hole. I could feel the tip of his cock pressing against my sphincter.
“Ami, you need to breathe and relax, otherwise this isn’t going to go in.”
I tried to do as Steve had told me and slowly but surely, I could feel his cock pushing into my ass. Initially, it hurt a little and I pushed back a bit until the pain subsided. Steve worked slowly in and out of me for the next few minutes. Each time I got used to feeling him inside of me he pushed in further until finally I could feel his hips clapping into my cheeks.
Steve was now going full throttle in and out of my sissy ass. It had started to feel good by now and I was gently letting out squeals of pleasure.
“You like that, you slut? How does my cock feel in your virgin ass?”
“It’s amazing, Steve! Please don’t stop,” was all I could breathe.
He kept going back and forth, then suddenly I felt him pulling at the mini skirt now wrapping around my chest. He yanked it clean off. I was now only wearing the pink halter neck bra. Then all the while his pole was still inside me, picked me up in his big arms.
“Come here, Ami, I want to show you the view.”
He walked over to the window with me still in his arms and him still impaling my sissy pussy and then started fucking me with my face pressed against the window. I could look down on the street and see the passers-by going about their normal lives. I hoped to God no one looked up. But if they did all they would have seen is what looked like a girl having the time of her life.
Steve then reached around and found my clitty. He was massaging it at the same pace he was fucking my sissy ass. The pleasure of getting fucked like a sissy and the excitement of people in the street potentially seeing me became too much. I screamed out in pleasure and came and squirted all over the window Steve was fucking me against. I don’t think I had ever come that hard in my life.
My body went limp for a moment and Steve noticed the mess I had made on the window. “Look what you’ve done to my window, you slut. Ami, a good sissy always cleans up her mess.”
He pressed me down only my knees all the while still ploughing my ass. “Now lick it all up. I don’t want to see any marks left on my window by the time you’re done.”
Steve shoved my head where moments ago I had just cum. I stuck my tongue out and lapped up my own juices. They tasted so good. The idea of me slurping up my own cum whilst getting ploughed by such an alpha male had my clitty starting to get hard again.
“Good girl”, Steve purred, “Now come here and take a real man’s load.”
He spun me round, and before I knew it, he had pulled off the condom, shoved his cock into my mouth and started erupting. It felt like I had gallons of his silky seed in my mouth. I finally managed to swallow all of it. “Good girl. We’ll make a cumslut out of you yet”.
I smiled at him as I lay on the floor for a minute catching my breath and thinking about everything I had done with Steve this afternoon. A fortnight ago, I had only ever fantasised about things like this. Had I just entered a new phase of my life?
