After the immediate elation from losing my sissy virginity to the bricklayer Steve. Strong feelings of shame had set in. I didn’t want my family to find out about my girly side. So, in September, when I started university, I chose to bury Sissy Ami. University started well, and soon, I had struck up a romance with a girl I had met through a society called Em. Em was the first girl I had caught feelings for. Unfortunately, as with most young romances, I fell for her quickly, hard and before I knew it, Em had called it off as she had met an older guy.
This crushed me. I had lost what little confidence I had in speaking to girls. I started watching more porn again, and then the fantasies of being the girl who got to suck the big dicks of the muscular men in these videos began to come back. Before I knew it, I was spending my life back on Tumblr looking at sissy captions again and I even started watching sissy hypno videos online.
The advantage of being at university compared to being at home living with my parents was that I had a lock on the door to my bedsit entrance in my halls. Which meant I had true privacy for the first time in my life. With my student loan, I went online and bought some bits of lingerie, a few miniskirts and tops that I knew I could wear around the bedsit without being interrupted. I also started dieting so I could lose a bit of weight, and I started doing Pilates exercises to tone my body and make it look more feminine.
It got to the point where I went out one night and was asked by a group of netball girls at uni what I had done to get such a peachy ass. One of the netball girls said she had spied her boyfriend checking me out in the queue for the bar. This shocked me so much that I ran back to my halls and called it a night. God, at this stage of my life I had just lost any short-lived confidence I may have had.
I chose to keep pressing on with my alter ego behind closed doors, Sissy Ami. In addition to exercises to make me look more girly and dressing up more, I decided I wanted to get better at applying makeup to myself. I also thought that If I was going to take cross-dressing seriously, I should get a wig.
Em, the girl who had broken my heart, was blonde, so taking inspiration from her, I bought a 16-inch blonde wig. Shortly afterwards, my makeup kit arrived in the post too. I started skipping my lectures altogether, as instead I would wake up, shave myself smooth, put some girly clothing and my wig on, and then practice applying makeup. After a couple of weeks of watching YouTube tutorials and practising in the mirror, I started to look like a passable girl.
The craving of wanting to be with a real man was only growing stronger. I knew from when Steve the bricklayer had fucked me, I could take seven inches, so wanting to test myself I decided to buy a black nine-inch lifelike dildo. As soon as this arrived my mind went into overdrive. I would spend entire days in bed pretending to be the centrepiece of a blowbang practising on this dildo. Even I would fantasise that Em would watch and take the piss out of me whilst Sissy Ami got fucked in front of her by a black bull, and I would use the dildo to simulate this.
Since starting university in September, my parents had retired and were spending multiple weeklong periods not at the family home in London. In addition, my older sister had moved out of home and was now living with friends. The Easter holidays were fast approaching, and I was due to go back to London for a month. A couple of days before I got the train home my mum called me up to say my dad and her were going to South Africa on a last-minute holiday they had won for 3 weeks but were due to depart soon after I got home. As sad as it was that I wouldn’t get to see my parents much when I was home, I also thought a new opportunity had presented itself for me being able to dress up even more when I went back home to London.
The next day I started packing my suitcase to take back home. I made sure to pack all my girly bits but hid them underneath my regular boy clothes in the suitcase. The journey home was uneventful. When I got home, we had a lovely family meal with myself, both my parents and even my sister had come back for the evening. My mum mentioned how long my hair had grown and that whilst home I should get my hair cut. My dad even chimed in saying there was a new Turkish guy at the local barbershop who he had used and thought was great. The next morning my sister went back to the flat she was living in with her friends, and the day after that my parents flew off to South Africa. I was home alone for the next three weeks.
A couple of days later I decided to take my parents up on their advice to get my hair cut. I didn’t have any clean boy’s boxers, so I thought what’s the harm, reached into my girly panty stash and pulled out a bright pink string thong which was held together by a gold love heart at the back. I pulled this on and immediately felt happier. I loved the feeling of panties covering my little clitty and how thongs rode up my butt crack. They made me feel like such a naughty girl. I went to admire my ass in the mirror and was pleasantly surprised. The Pilates exercises I had done in recent months were really starting to show their progress. What topped it off for me was that this girly ass of mine was perfectly framed by this pink string thong. It was all getting a bit too much and I had to jerk myself off until I came into my hand. I licked all my semen up, then pulled my jeans on over, grabbed a t-shirt and left the house to go the barbers.
I didn’t get there until early afternoon. By then the lunchtime rush had started to dissipate. I sat in the queue and listened to the barbers chatting with their customers. There was a new man I hadn’t seen before cutting hair. I assumed this was the new Turkish barber my dad had raved about. Anyway, I got listening to the conversation he was having with his client. They were joking about the barber’s escapades from the previous weekend.
The Turk said, “Anyway, about 3 am, we entered what I thought was a normal strip club. I was quite drunk by this point and didn’t take much notice of any of the strippers in there. Eventually, one girl convinced me to go for a private lap dance with her. We went into this booth and almost immediately this hotty starts sucking on my dong. Man, she was goooood! Anyway, this stripper eventually took off her bottoms at which point I realise the stripper didn’t have a vag. Instead, where her vag was meant to be there was a minuscule penis, but it was locked away in something the stripper told me was called a chastity cage.”
The customer barged in now, “Wait you’re telling me you got your dick sucked by a guy dressed us as a girl? Did you run out of there when you found out?”
“Nah, man. It was a sissy girl,” retorted the barber, “Besides, the stripper was too good at sucking dong to leave. I let her keep slurping me, whilst I made sure to teach her who the real man was. I thought it would be funny to keep gently kicking her in her chastity cage and balls as she finished me off. Somehow, this turned my cocksucker on more. The best thing was when I came in her mouth; she said thank you and didn’t even charge me for the BJ or lap dance!”
The barber then erupted in laughter like it was the funniest thing in the world. I just sat there quietly squirming thinking what would happen if this barber found out about me.
The Turk finished up on his current client and I was next in the queue. He welcomed me to his seat giving me a look up and down as he ushered me in. I let him know my dad had been recently and had recommended him as a barber. Anyway, the Turk started trimming my hair as his colleague was finishing up on his last client. The colleague said he was quickly nipping out to grab some lunch and would be back in five minutes.
As soon as the other barber left and we were alone, the Turk put the shaver down, placed one hand on my shoulder and asked, “So how long have you been a panty wearer, sissy?”
“What? How? Why do you even say that?” I stammered out in shock.
“Come on, girl, I could spot something was wrong a mile off. When I told that story about getting my dick sucked last weekend, I could see how nervous it made you. Then when you walked over to my chair, I spotted you don’t have muscles like a real man. No chest or arms at all. All I could see was how slim you were and how juicy your ass looked. Then most importantly, as you were sitting down, I could see that bright pink thong of yours had ridden up above the jeans you were hiding them in.”
Fuck, I thought. I’ve been caught. I sat there panicking. After a second the only words I could meekly say were, “Please don’t tell my dad? Actually, please don’t tell anyone?”
“Hmmm I dunno that’s a big ask,” he responded, “What’s in it for me?”
“I’ll do whatever you want,” I came back quickly, still semi-panicked.
The Turk stood there quietly for a few seconds, “Ok here’s what we’re gonna do. Firstly, I want you to show me what you’re wearing right now, right here. Secondly, considering how good the other sissy from last weekend sucked my dong, I wanna see how good you are at it tomorrow.”
I sat there thinking, trying to work out a way from this situation I had gotten myself into. Finally, I thought let’s just do what he tells me. Besides it could be a little fun whilst I was home alone. I nodded, then stood up slowly, unbuttoned my jeans and lowered the front of them so that the Turk could see. The triangle at the front barely covered my modesty.
“Woah,” the Turk laughed, “Your puny pee pee is getting hard from this.”
I looked down. The humiliation of having to show this stranger my deepest darkest secret was turning me on.
“Now drop the rest and turn around.” He half laughed out.
I obeyed and lowered the back of my jeans to reveal my ass. I then turned around so he could inspect it. At this point, I was standing facing the window of the empty shop. I realised that any passer-by who looked in would see me in a t-shirt, pink thong and jeans around my knees. My clitty was straining behind the front of the thong now. Suddenly I heard a massive clap and then felt the pain coming from my ass cheeks as I realised what the Turk had done.
“Girl, that ass of yours is fine. So perky.” He turned me back around and then told me to pull my jeans back up and sit down.
He started back up cutting my hair just as his colleague walked back into the barbershop. I sat there in silence thinking about what had just happened, what I had just let myself in for?
Once the Turk had finished cutting my hair, he took me over to the till to pay. I let him keep the change and just as I was about to walk out, he asked, “So where am I meeting you tomorrow?”
“Oh, uh, I’m home alone for the next few days, so meet me at the corner of Well Street and Hill Avenue tomorrow at 10 am, and I’ll bring you back to mine.”
I wandered back home with my mind racing. How had I just been caught? What did the Turk want to do with me?
The next morning, I got out of bed at 6 am. I had barely slept the night before. The previous day kept on playing out in my mind. I went into the bathroom and started prepping myself. Due to the fact I had been shaving my body so regularly, it only took a few minutes. I then cleaned myself up in the shower. Towelled myself dry and then went to the bedroom to decide what I was going to wear for the day.
My favourite outfit I had bought since starting university was a black wired lace bra with white trim around the edges and a built-in neck chocker. This came with a matching thong. Finally, I found my sheer hold-up stockings and pulled them up. I grabbed my blonde wig, pulled that on and went to the bathroom to apply my makeup.
I had finished prepping myself by 9:30 am and sat there now, kind of excited thinking about what was going to happen. At 9:55 am I suddenly had the realisation I couldn’t meet the Turk on the street dressed like this. I had to put a disguise on over what I was wearing so no one on the street would see me walking about in lingerie. I pulled on some tracksuit bottoms and a top, took my wig off and pulled on a baseball cap to cover my makeup-plastered face.
I was walking to the meeting spot which was around the corner from my parents’ house equal parts excited and nervous. Finally, as I got near, I saw the Turk waiting on the corner. He greeted me, and then we started walking back to my parents’ house.
“So, you know, when I made this proposition to you yesterday, I thought you would be dressed up as a girl for me to enjoy?” he blurted out.
“Don’t worry I’ve got my best outfit on underneath this tracksuit. I just don’t want the neighbours to see me all dressed up,” I replied.
“Got you, yeah, that makes sense. God, I’m really looking forward to seeing if you can suck my dong better than that other sissy.”
“Well, you’ll have to be the judge of that.” I winked back coyly at him.
“Anyway, what should I call a slut like you?” the Turk asked.
“Anything you want, but the guy I was with before you called me Ami.”
“Hmmm, I can dig that.”
With that, we were back at my parents’ front door. I had a quick peek around to make sure none of the neighbours were looking and then let him in. Once I had locked the door behind us, I took off the tracksuit bottoms and top, then put on the blonde wig. I turned around eager to see what he thought of the outfit I had been hiding underneath. He was smiling, “Girl you look like you were born to please dick.”
He slapped my ass, which I took as a signal to lead him up to my bedroom. I was halfway up the stairs when he called out, “Ami, stop. If you’re going to dress sexy like a girl, then you need to learn to walk sexy like a girl. That means when you walk up these stairs your hips and tushy need to sway from side to side. You should be able to hypnotise me with that fine ass of yours. Now, try again.”
I restarted climbing the stairs, this time paying extra attention to sway from side to side. This extra effort was rewarded by the Turk clapping his hands in approval. As we entered my bedroom he lay down on the bed and beckoned for me to come over, so I crawled onto my bed and stopped just below his crotch.
“Open it,” the Turk ordered.
I undid his zipper and out popped a semi-hard python. For such a hairy man, he had clean-shaven his cock and balls, as I couldn’t spot a hair anywhere. It was too good-looking to wait. I started slowly licking his balls, alternating between them. Every so often his shaft would jump in excitement.
Soon enough, I stuck my tongue out and started licking the underside of his shaft, working my way up and down. I could tell he was getting more excited now as his dong was mostly erect. I then tongued the underside of his tip, trying to get him as erect as possible.
I pulled back to inspect the specimen I was working with. The Turk must have been 7 and a bit inches long, but much thicker than the previous man I had been with. I spat as much saliva as I had in my mouth onto his shaft and started working my hand up and down, while at the same time lowering my head onto his shaft. I had to try and open my mouth wide to fit him in. I kept on going up and down and soon enough I had managed to get his shaft most of the way into my mouth. I could feel him lifting his pelvis, gently thrusting to meet my mouth.
After a few more pumps, he called out, “Here, get on all fours facing me and open your mouth wide.”
I did as he instructed and waited eagerly with my tongue stuck out, I also tried arching my back so my lace-thong-covered ass would stick out more. The Turk got up, placed his glistening dong onto my tongue, then grabbed the back of my head and rammed it onto the base of his cock. I was so shocked. I could feel his dong down the back of my throat. How had he done it so quickly? Was my jaw ok? Hold on, I was struggling to breathe!
I pulled off him and caught my breath, then he went again slamming my head into the base of his shaft. This time I was better prepared for it. He started to pull out of my throat slowly and I found a quick millisecond to breathe before his dong was all the way down the bottom of my throat again. He kept slamming my head up and down his shaft. I loved the feeling of having my face mashed into his pelvic bone, whilst at the same time I could feel his man bone in my throat.
Whilst keeping the motion of fucking my face he reached over me, bent on all fours, pulled my thong to the side and shoved his finger into my ass as far as it would go. My clitty jumped at this. The sensation of my face being used as a fuck hole, whilst the Turk was ferociously ramming my ass with his finger was incredible. I would have moaned except for the fact his dong was stuffing my throat. It became too much, so I reached for my clitty and started yanking. I had barely touched it when I could feel myself exploding all onto my bed.
The Turk was not happy about this. He pulled his finger out my ass, took his dong out my throat, and before I could catch a breath whacked me across the face with his dong.
“You stupid silly sissy. Don’t you know a sissy isn’t allowed to cum until she has made everyone else cum first?!? Even then a sissy can only cum with permission from her man.”
He whacked me three or four more times across the face with his weapon, before once again impaling his shaft down my throat. He picked up the ferocity of his throat fucking. I could feel his large balls whacking against my chin. God this was hot. I could feel myself starting to get hard again when suddenly the Turk thrust with such force my jaw went numb. He held me impaled on his dong whilst he let out a gorilla-like roar and released stream after stream of his hot cum down my throat and straight into my stomach. After what felt like an age he pulled out and I gasped for air.
He wasn’t done yet. The Turk got up and marched round to my ass. I could feel him shoving his finger up my ass again. God, it felt so good being used by him. I could feel him jamming a second finger up there whilst still ferociously finger-ploughing my hole. I was intentionally resisting the urge to touch my clitty again until the Turk permitted me.
He pulled out briefly. I looked downwards and saw his fingers rolling around in the pool of my jizz that I had caused a few minutes ago. Then suddenly, I felt this massive force stretching my sissy hole wide. I looked around as best as I could and saw what looked like the Turk ramming four cum glazed fingers in and out of my sissy pussy. This was incredible. He was using my juices as lube to finger fuck my ass even more.
The Turk finally whispered, “Go on, wank your teeny sissy cock.”
It felt so emasculating being finger blasted by another man, whilst dressed as a girl, and having the man tell me when I could and couldn’t touch myself.
I did as I was told and almost instantaneously erupted an even bigger load of my jizz onto the bed. The Turk pulled all his fingers out my whole now. Grabbing me by the scruff of the neck, he used my face to mop up all the jizz I had sprayed over the bed. Some of it I managed to catch with my mouth and swallow, but most of the jizz just painted my face.
I lay on the bed face up looking at the ceiling in a daze. That was when I saw the Turk’s already hard again cock approaching my face. He put each of his knees on either side of my head and entered my mouth again. This time he was truly fucking my face. I could feel his balls now whacking my nose and even eyes, whilst at the same time I could feel his meaty shaft halfway down my throat. He kept ramming in and out and grunting. My jaw was so tired and sore from having to be open so wide. Finally, with one Herculean pump, I felt his dong let loose all his cum. He lay there with his balls resting on my eyes for 10 seconds. I could finally start to feel his dong shrinking in my throat and finally again in my mouth. As he was pulling out, I did my best to suck him clean.
“Damn, sissy. You really got me going there. You got some skills, and your mouth was great to use.”
All I could muster was a brief, “Thank you,” and smiled as jizz ran down my face.
The Turk got dressed quickly, and I went downstairs with him, still wearing the thong, bra, stockings and wig, all while I had jizz running down my face.
“You know, Ami,” he said whilst opening the door wide. “As good a sissy girl you are, you need to work on your discipline and subservience more. You should invest in a chastity cage.”
With that, he disappeared down the street. Whilst I stood with my parent’s front door wide open, looking like a semen-drenched whore. All I could think was, I must buy myself a chastity cage.
