50 Shades of A Bookseller

*Crossdress Story*

So, I finally got a "proper" job and managed to move out of my parent's house.
It was a damn good job too, as my crossdressing was becoming increasingly difficult to keep secret. Numerous times my Mum would try to talk to me through my bedroom door, whilst also slowly creeping it open to talk face to face; why she does this I have no idea, but it's usually at a time when i'm either half dressed in a skirt and bra, with my cock hanging out or when i'm posing for timed photo's on my mobile phone (probably with my ass cheeks spread and my puckered hole pointing at the camera).

Anyway, so a new flat and a new job, perfect.
Money is a huge problem though, but i'm happy and getting to dress when I like is a massive bonus.
My job is at a bookshop in the main town (I won't name it, but let's just say it's pretty much the last bookshop chain in the UK). It's an awesome job, pays well and has some really fun people to hang around with and chat to. Hell, even the manager's nice.
You do get some lovely customers, but you also get some really wierd ones; like the two stinky b*****rs that come in and just shout and leave their pissy aroma wherever they waddle, the old main in the long coat and the poker
visor that sniffs books and the lady who mumbles to herself and takes an armful of books from the shelf and just stacks them on the floor.
One day, one of the girls I work with sidled over to me and whispered; "This guy's creepy, can you deal with him?", I didn't mind, so if it made her feel safer, of course I'd deal with him.
I approached the desk where he was waiting and did the usual "Good afternoon" thing and all that jargon, when I realised that he was actually very normal looking, to be honest he was surprisingly fit.
Medium length dark hair, swept back, probably early thirties with a nice friendly and handsome face, dark eyes, quite tall (well, much taller than me) and from first glance, pretty in shape.
We talked for a minute about what book he was looking for and I got on the computer to look it up. He seemed a little distracted and nervous, but some people are like that, I know I can be pretty shy for no good reason sometimes. Anyway, I found that we had the book in stock and offered to show him where it was. So off we went towards the other side of the shop.
We reached the fiction section and I found his book and handed it to him, but he didn't take it. He instead asked in a very low voice if we had an erotic fiction section, I said yes and it's really not so taboo to ask,
but he shook his head and asked if we dealt with "non-traditional" stories.
I said I'd never really looked at what we had, but there definately was some bondage and hardcore type stories.

"No, no..." He continued, "I dunno, like gay stories...or, no, not gay...you know, like shemale, type stuff?"

I smiled, now I totally understand why he was so nervous, if only he knew he was talking to a crossdressing, slut wannabe.
So I made him follow me over to the erotic fiction area and told him to browse the sci-fi section opposite while I looked for what he wanted. But we started talking (guess he felt a little relieved or maybe just knew I wasn't judging him) and as there was no othe customers in the area, we just had a bit of a laugh over the awful covers these books had.
After about twenty or thirty minutes I found him two books on shemales and sissy maids and told him i'd do the transaction for him so he didnt have to be embarrassed at the main tillpoint.
Before I started to walk off he asked me a question completely out of the blue;
"You ever read or looked at this sort of thing online?"
It was easy to lie and so simple, but I couldn't, so I told him I was actually a crossdresser and i WAS online.
The look he gave me was quite funny, like I was some kind of celebrity and started to ask me all kinds of questions like how I got into it, what I wore first time and all that sort of stuff.
I told him truthfully (from what I could remember!) and think i got a bit caught up in the moment, going off on a tangeant and telling him the first webcam show I did and the praise from the viewers made me carry on.
This was when I noticed the bulge, sticking out at the corner of the crotch of his jeans. He was getting turned on by my story...which turned me on as well!
As my tale got more and more fictional, his hardon became more and more obvious.
He began to breathe through his mouth now too, not heavily, just had his mouth open. And I wanted those jeans open.
As he hung on my every word, I stepped forward, closer and closer until I was facing his chest.
Reaching my hand to his jeans, he backed off in shock for a moment, but then stayed put. My fingers brushed over the lump in his trousers, and again...and again.
I knew I couldn't rip his cock out in the shop, even if no one was around, but that didn't stop me from grabbing a fistful and rubbing furiously.
Through the denim I could just about feel his helmet, but my grip was totally hindred by those pesky pants. From left to right, I rubbed him off...over and over, faster and faster until judging by his quickening breath; my index finger knuckle rubbed madly on the underside of the cockhead as an explosion of warmth radiated from the area.
I saw his knees give way a little and suggested he sat down at the reading area.
As he took a seat, I wrote out my mobile number and gave it to him as I had to get back to work as i was due on the tills.
When I returned an hour later, he was gone, but the books i'd picked for him were on the table.

I didn't hear from him for at least two weeks, I half expected him to never get in touch, which made me a little sad as I found him very attractive. But when he did get in touch it was a little more than I expected. It was a text message and it read;

"Hey m8. Was thnkng of u. Wanna meet up? Hve a buddy intrstd 2. Can u dress?"

This had me a little panicked, as i'd never been with two people before, plus the fact i'd never met the guy. I mulled it over and decided to reply (only live once right?), and he responded immediately with time and the place, provided I was available which as luck would have it, I was.

The day crept up fairly fast and it was a scorcher. As a side note, I hate hot weather! I'd much rather cold, rainy days over hot sunny ones...I guess that's the goth in me ;P
I decided to wear my tight, white crop top. A black sports bra. A rather fancy pink thong with gold metal at the back (very classy - ill post some pics). Black tights with some pink sport socks, the kind that are baggy and go over your boots/trainers. And finally a pair of VERY short denim hotpants with a belt with dangly metal stars on a chain.

Jack picked me up (I discovered that was his name during a few dirty texts) not long after I got ready and we drove down a few streets while listening to some awesome 80's rock...if only i had a chance to be fucked by Billy Idol!
Proabably took about forty minutes to reach his house, all the while he was rubbing my leg and trying to find a way under my tight shorts.
When we got out of the car I met Terry, the friend. A very big chap. Looked a lot like a body builder that hadn't worked out for a while; huge arms, wide chest and thick legs. He had a bald head and now I think about it i'm sure his sunglasses were permanent fixtures to his face. Again though, very friendly and a great sense of humour...and extremely perverted.
As we walked towards the door, Jack unlocked it and allowed me to go first, as I did they both grabbed a buttcheek each, making the usual macho noises.

The house was huge and Jack was apparently a f****y man; a wife and a son, he told me she too was into the idea of having sex with a crossdresser or shemale but she was in America on holiday with her father. Terry slammed down onto the couch in the living room and un-buckled his belt and jeans and switched the music channel on the television on, a giant grin planted on his face.
Jack told me to get comfortable and he went to get some drinks.
Terry and I spoke for some time and we quickly got onto the subject of what he wanted to do to me, detailing it all with his hand down his pants. Jack had come back durig this and was listening eagerly, he'd told Terry what happened in the bookshop.

We drank a little and relaxed with each other, as the thumping music made it's way to my hips and I started to dance a little for them. As my hips gyrated around Terry's face, he pulled down his pants and flopped out the biggest cock I'd ever seen in real life. It made me stop.

"You wanna blow it, bitch?" Terry yelled excitedly.

It sounds dumb, but I instantly fell to my knees and took hold of his floppy, giant cock in both hands and began to caress it.
Jack whipped his dick out too and stood next to me, rubbing it near my face. The smell of cock is intoxicating.
I ran my hands all over Terry's huge dong, feeling it getting fatter between my fingers while Jacks cock jabbed me lightly in the face.
I gave Jack a little lick as I pulled on Terry.

"Fuck this, man." Terry said, "My cock needs more lovin' than yours."

He stood up and directed me to lie down face-up on the couch as he stepped over me with one leg, his arse was a few centimetres from my chest...and his cock was speeding towards my face.
He began slapping my cheeks with his giant cock, leaving silvery strands of precum with each hit before shuffling nearer and resting his ballsack
over my mouth.
His balls both reached each corner of my mouth and his member rested on my forehead, the giant shiny helmet leaking that sweet, sticky precum into my hair.

"Open." He commanded.

I did.
As my mouth opened, I eagerly anticipated those man-eggs to fill my yap-hole, as he fed them to me, my eyes widened as I realised how smooth and salty they were.
I began to roll them gently with my tongue, caressing and gently tugging. He moaned and stroked my hair, a sharp intake of breath occassionally when I pulled a little too much.
After a few minutes, he took hold of that masterpiece cock, which had become veiney and eager for conquest. He rubbed it up and down, masterbating as I sucked and swirled his balls, saliva was pouring out the corners of my mouth and that's when he decided my mouth was ready to become a fuck-hole.
With a pop his ballsack was free, drenched in spit and pink from sucking, he rubbed a new globe of precum that had formed from the slit of his penis all around my face before taking aim and plunging it down my eager throat.
Jack, who had been jacking off and enjoying the view, was now at the other end of the couch and putting his head between my legs, unbuttoned my shorts and finally pulling them down my thighs.
Once they were off, he tore my tights and revealed my freshly waxed ass and testicles. He proceeded to hold my legs apart and delve his tongue in between my ass cheeks; his nose nestled amoung my soft, hanging balls.
His wet, warm tongue licked and rolled up and down the limited space he had, as I was still firmly planted and trapped underneath Terry, but Jack had now lifted my right leg and Terry had grabbed hold,
hooking it under his armpit, they did this to my left leg too, so I was fully exposed; My ass ready, legs well up and out of the way, my little cock dangling helpless and my mouth and throat about to be ravaged by a huge,
throbbing cock.
Terry's knob didn't disappoint; he worked his hips and slid it in and out of my mouth, my tongue trying to gain purchase and keep it in so i could suckle on it, get some of that sweet precum.
His balls swung into my chin as he swooped in sometimes, those beautiful, heavy testes, teasing me.
Jack slurped at my asshole, and it drove me fucking mental. His tongue trying had to poke in, then swirling around my anus, saliva oozing down my crack. Every now and then he licked from the bottom all the way up, passed my hole and to the base of my ballsack.
After a few minutes, Jack spat and worked his finger around, slipping in a out, untill he teased me even more and began to rub my asshole like a woman strums her pussy. His fingers working in a furious circle, rubbing around
and around, every time his fingers went from top to bottom then bottom to top, his middle finger would slip into me briefly, causing my ass to clench, popping his finger out - yet i desperately wanted to fill that hole so badly now.
Terry was getting into an aggresive rhythm now too, almost throwing his massive dick down my throat, he wasn't pulling out anymore, always keeping at least that lovely helmet inside my mouth, rubbling itself against my tongue and sometimes stretching the inside of my cheek when i squirmed.
Just as I thought I wanted Terry to blow his load, he withdrew, saliva dribbled and poured from his member as he flicked it at my face, my mouth open and tongue lolling out, like a dog wanting a treat, I was panting heavily.

"Jack, let me fuck this whore!" He said and Jack stood up and stepped over slightly, i could see him now and his prick was upright, a long slender one, with a really pink helmet.

Terry let go of my legs and got up, walked around to my legs and bent down, nudging my side he motioned for me to turn over. I did, and got to my knees.

"No, lay flat, slut." He yelled.

I obeyed, letting my knees slide down.

"I want you to try to keep me out..." He whispered. "You can't use your hands, just your ass muscles. Try and keep my cock out." He giggled as he said this and it excited me.

"Fuck me" I responded.

"Oi!" Terry yelled again. "Jack, teach this fucking whore a lesson, teach her mouth not to swear."

Suddenly the skinny dick was in my face, poking me in the eye and rubbing along my cheeks, leaving a wet trail where it'd been. It found my lips but it recieved no resistance from them. His cock slid in, I sucked with all my
might and Jack gasped, he was trying to pull it out until i ran out of breath and had to let it go, but it came right back in again.
Meanwhile, my asscheeks were clamped together but Terry had been wiping his saliva soaked cock up and down the crack, like a hot dog sausage outside the bun, I could imagine what he was doing as he lifted off for a second, then came plunging
down, trying to break my ass apart.
He used his right hand to slowly work his thick cock in, I could feel it sliding off then back on traget.

"C'mon baby...open for daddy." He said.

Suddenly, it was between my cheeks and against my fuckhole, that big head banging on the door to the warm home inside. It didnt take him long to slide a little within, but his cock was very big and my ass hadn't been stretched to
accomodate. To be honest, it didn't put him off, I tried to scream as that massive dick went inside me, but Jacks cock was almost down my neck and my lips were sticky with drool and clamped to his balls.
Terry's Helmet slid fully into my asspussy, I felt it swell slighty with anticipation, the shaft was slowly sliding in too, but saliva dries out fast and now he was diving in pretty much raw.
Pain and pleasure are so close and marry so well, It hurt like fuck but I was so turned on by having two cocks inside me, one gagging me so I couldn't cry out and the other dominating me and keeping me in place.
Jack was watching Terrys thick prick going in my tiny ass and was beginning to hold my face as he thrusted his hips, making his penis bounce to the back of my throat as my lips continued to taste his balls.
Terry was now over halfway in, gritting his teeth as it became a challenge to push it further inside me, after a minute or two, he spat in his hand;

"Fuck this, I just wanna cum in her now!" And rubbed his spit around his exposed cock, trying harder to thrust it in.

"Oh God yeah!" Jack said, high pitched, as he became faster in his own thrust.
Jacks cock was leaking precum at such a rate, I thought he'd already ejaculated, until he stopped, leaving his cock on my tongue.

"Suck it, really hard. Suck it now."

I did as I was told, I sucked as hard as i could, like i was trying to suck up a really thick milkshake, and on about the fourth time, a warm, thick wash spread all around my mouth, I stopped sucking and a shot of cum sprayed across the roof of my mouth, I sucked hard again, Jack moaned as more cum engulfed my mouth, flowing freely over my teeth and coating the inside of my cheeks.
This is where I nearly bit down on him because terry had almost jumped and f***ed his fat cock in me, my mouth flew open and i screamed; cum dribbled everywhere, ran all over my chin and dangled like thick drool, which started to sway as Terry began to plow me.
I've never been fucked so hard and so fast, my ass felt like it was on fire, in and out, burying deep inside me. He reached his hands under each side of my hips, lifting me onto me knees.

"You know what to use, bitch."

Between pants and painful grunts I managed to make a noise which meant I didnt understand.

"Wipe that cum on your ass!" He shouted. "Fucking do it!"

My left hand shot to my mouth and wiped my chin with the palm. Reaching under, between my legs I smeared it under my stretching asshole, feeling that mammoth dick speeding in and out, ravaging it. It turned me on even more, I gathered the
cum that dribbled onto the carpet and spat any more that was in my mouth into my hand, reached back and this time grabbed his cock as it withdrew from it's temporary home.
This time, as it thrust back inside me, I realised his cock was never fully in, but now, aided with super lubricting semen, it powered through, almost lifting me off my knees as Terry's hips banged into my asscheeks, sending a clap
echoing through the room. Again.
Again. Another massive clap.
Another huge thrust and a grunting Terry.
As he pulled back for another thrust, Terry whimpered, his cock plopped out of my ass and shot a giant stream of creamy white cum across my back, as it hit the back of my neck I moaned and arched my back, lifting my ass which was now gaping
like a cave entrace and Terry burried his penis in deep, spurting his seed and coating my insides with cummy yoghurt. I felt the powerful climaxes, his spasms, his swells and his offshoots, hitting my anus walls.
My upper half collapsed, cummy dribble oozed from my mouth onto a pillow and my knees began to slide backwards until my ass lowered, once again making Terry's cock pop out.
As my cock rested on the couch, my gaping ass began to clench and return to normal size, causing Terry's man juice to slowly trickle out and down onto my balls.
Terry and Jack then both leaned down and kissed my asscheeks.

"Cheers Kit." Terry said as he wiped his cock along my leg.

"Fuckin' star." Said Jack, stroking my hair. "Stay as long as you need. There's a shower upstairs."

I smiled at him, too weak to say anything.
But I knew...
I was going to stay the night at least.

=^.^= Kit x
100% (27/0)
Categories: Shemales
Posted by KitsuneTV
2 years ago    Views: 1,048
Comments (11)
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14 days ago
Great job! You made me feel the passion building through out my body & made love to my mind & just thank you.
1 year ago
wow thats hot
2 years ago
best story ive ever read on here! id love to meet up with u someday xx
2 years ago
Awesome story. That is one of my favorite fantasy.
2 years ago
It made dream of a white (cum) christmas! :-)
2 years ago
That was quite the horny lil ditty. Cheers.
2 years ago
I love your nasty story sister slut
2 years ago
fucking crazy story! it made me so hard
2 years ago
Fuckin amazing babe :D
2 years ago
Nice story.
2 years ago
Great story! good work!