Ever since I was little, I always enjoyed dressing up in my sisters' clothes despite being a boy. This may have been because my dad left before I was born and so I had a big female influence due to my 3 elder sisters and my mum. When I was about 11, my sister Alice, 14, and my other sister Izzy, 16, decided to dress me up as a girl using all sorts of make-up, shoes, clothes and other accessories. Ever since then I have always dressed up as a girl when I was at home and wasn't near any of my friends.
Now I am 20 years old, and I go everywhere dressed in girl's clothes and people don't realise that I'm actually a boy. I sometimes even get men come and flirt with me which gives me a pleasantly warm feeling.
I had realised that I was bisexual a few years ago but I had never actually had any sexual relations with other men until recently. I was getting changed into my tight little miniskirt and my skimpy little top to go out in after work when I realised that I had needed to get a few items for shopping.
So I went out and as I was driving I saw an adult movie store. I don't usually go into these stores, but today I was feeling especially horny and I decided to go rent a movie to jerk off to.
I went in and brought a couple of gay porn movies to fantasise to and decided I'll take a quick pee whilst I was in there. As I entered, I head some strange moans coming from the stalls but thought nothing of it at the time. I went into the stall and noticed all the graffiti saying things like 'cocksucker' and 'cock whore' written on the walls. Again, I thought nothing of it and I went to piss. As I was finished I noticed a rather large hole in the wall with a voice coming through saying "Hey baby, you got a fucking nice ass".
I don't know what came over me but I replied carelessly "Thanks, but I'd bet it'd look so much better with your big cock in it"
I heard a rustling noise and after about 20 seconds a limp cock came through the hole in the wall. It must have been at least 6.5 inches and it wasn't even hard yet! "If you want my big cock in your ass you're gonna have to work for it you little whore"
I finally realised that this hole was in fact a gloryhole and I also realised the mess I had got myself into. But after a few moments of thought I had realised that I wanted to try some big cock anyway and also I was extremely horny with my own hard little 4.5 inch dick straining against my panties. "L-Let's get your big c-cock nice and hard for me" I stuttered with anxiety and excitement joined by a whimper of a smile.
I got down on my knees and put my face just millimetres away from his beautiful circumcised penis. I was extremely nervous. This was the closest my face has ever been to a penis before and the first one I have seen in person other than my own (which was now leaking pre-cum from the tip without me even touching it once.)
I gently moved forward to plant a kiss on the purple tip of unknown man's dick. I could hear my heart beat rapidly as I was closing in to abandon my oral virginity for good. My purple painted lips pressed against the equally as purple tip which had now began twitching slightly. I licked the tip slowly and started stroking the base as he began to grow too full size.
Within 10 seconds of my licking and stroking he was hard as steel and measured up to at least 10 inches, no, 11 inches long. His cock had thick, prominent veins running through it which made my mouth began to salivate as I licked my lips subconsciously.
"Hurry up and suck it, you filthy whore!" I heard faintly as I was admiring not just the length, but also the girth of this amazing cock.
I licked from the base to the tip several times and then engulfed the head in my mouth and swirled my tongue around the big head using the techniques I had heard from other crossdressing sissies I had met on the internet.
"Ahhh yeah...Is this your first time babe?"
I stopped slurping. "Yeah...Is it good?" I replied staring hungrily at his big cock.
"Yeah, it's the best head I've had in years"
I began gobbling on his penis head again but this time I put as much as I could in at once. I had been training with my 6 inch dildos for a couple of months beforehand and I managed to get in 7 inches of his thick cock down my throat! He was moaning and thrusting his cock deeper down my throat so I predicted he was going to cum soon. He shoved all 11 inches of his big, thick cock in my throat at once and pulled out. He began spraying his thick, creamy load in my mouth and his twitching cock sprayed it all over my face, hair and some even went onto my little femboy tits.
Without thinking, I began licking up all of his sperm and swallowed it with a big gulp. I had only ever tasted my cum before but this cum was so much more tasty! It was thick and creamy and tasted deliciously salty.
"Ah yeah! It's hard to find a girl these days that swallows" He said whilst regaining his breath.
I knelt there silently.
"Wait...Why are you in the boy's bathroom?" He said with sudden realisation.
After a few moments of kneeling in shock the door flung open breaking the locks.
I saw his gaze move down my feminine body and stop directly on the little bulge making a small tent in my miniskirt.
"I-I-I'm sorry! I'm really sorry!" I started crying after realising I had just done to this unsuspecting man.
He took my hand and raised me to my feet. His hot, long tongue licked up the tears flowing from my eyes.
"It's OK. I'll forgive you if I can fuck your little asspussy"
His lips reached down. I am only about 5 foot tall and he must have been about 6'2 and muscular as well. Our lips became entwined together and his tongue explored my mouth, making my tiny cock start twitching.
"P-Please be c-careful...It's my...uhh...first time"
He was silent. But his actions spoke for themselves. He rapidly took off my clothes leaving just my panties and bra on. He pinched my nipples as my (now free) hard cock twitched around leaking drips of pre-cum on the floor.
He lay me down on my back. The ground was cold and hard, but I was concentrating on his cock. It bounced around as he walked, getting into the prime position. He started licking my ass and gently poking his tongue through ever so often. I was moaning like a girl getting her pussy eaten. He slipped one finger into my tight, virgin ass.
This was a strange sensation.
I had never used a dildo in my ass because I wanted my first time to be with a real cock. I also have a major foot fetish and love watching foot worship porn and footjob porn. Using my memory, I started rubbing his cock in between my feet and toes. The warmth of his member felt great as it tickled my sensitive soles.
Eventually, he had put 3 fingers in and was fingering rapidly. He was also rock hard and leaking pre-cum on my painted toes. I wanted it. I wanted his huge member inside of my virgin asspussy. I was prepared to beg for it. And beg I did.
"Please! I want your cock! Please fuck me! I'm begging you!"
"Hehehe" He laughed menacingly. "Tell me exactly want you want me to do."
"Please! I want you to take your big, hard, thick, beautiful cock and thrust it into my virgin boypussy! I want you to fuck me with your cock and cum in my tight little ass! Please!"
He needed no more. He used his saliva on my ass and pressed the tip against my asshole. He slowly pushed. His cock slowly invaded my sissy ass. It was so warm. Eventually the whole of the tip was in. 1 inch in... 10 more to go. He pushed slowly into my ass and after thoroughly stretching my little pussy, he got all of his massive cock in.
It hurt. But the pleasure was phenomenal.
He started moving in and out slowly. My cock strained against my pre-cum soaked skimpy panties. I knew I was going to cum. I was going to shoot my biggest load ever and I haven't even touched my cock once. I'm such a perverted sissy slut. I am going to cum from sucking a stranger off and letting him rape my ass.
He was moving fast. His big balls slapped against my ass and added to the pleasure. I was high on pleasure. I was going to cum. I shot my load of hot cum all over my stomach, tits, face and some went on his chest from the twitching of my little cock.
"You little slut! Cumming from taking my cock!"
This got me hard again instantly and within another minute I came again. I was officially a cock slut. He kept pounding my ass while I was in bliss and eventually shot his load into my cum-hungry boypussy.
The pleasure of his cum hitting deep inside me sent me over the edge and my little semi-erect cock shot another load of cum all over myself which caused me to faint.
When I awoke, I was surrounded by three big, naked black men, all with huge, erect black cocks. One had my cum-soaked panties in his hand and was licking it. One was feeding me the cum off my body and face using his fingers, and the last one was licking my sensitive little toes which were still sticky from the footjob I gave.
I was in complete bliss.