My names Peter and I am a sissy. I had gone from chasing skirt to being a cross dresser gay bitch. Once I hooked up with a transsexual called Daniela, things changed. Maybe she only opened a door that I didn't know was there, and I walked through it. I frequenting gay bars, and pimped out by pimp called Max. I love dressing as a woman, make-up and all.
* I went to work Monday as per usually, but I had developed a slight stutter with my walk. Putting it all down to my sore back, until one of the girls pulled up to me; at the coffee machine.
I thought she was going to flirt with me, when she adjust my shirt and circled a button on my shirt. "Petey honey, are you gay?" She asked out of the blue, smiling. I said nothing for awhile, I just stood there like a stunned mullet. "Why-why and what you asking Sheryl." I stuttered.
"It's the way you're walking lately; it's got a swagger like a girl who had been fucked hard, recently." She giggled. I was a little embarrassed. "Don't threat, it's the 21st century after all." She sipped her coffee and snicker off. I sat back down stunned, was it that obvious?
The next two weeks I kept a low profile and stayed home. By the third Friday I couldn't help it and I went back to the gay bar; but not as a TV but dressed in a tee and jeans.
The bar tender, made mention of me not being around lately. I smiled and ordered a red wine. After my second, I take a pee and on my return; Jerry the bar tender was waiting for me.
"Another?" I nod yes. "How would you like a part-time job here, on Saturday nights?" he asks. "Sure, what doing?" I ask. "Bar tending and clearing tables, plus wearing some clothes that I'll organise." I licked my lips, at this. "Tell me more." I said, sipping my wine. "You'll be wearing a tank top, leather shorts; show your bare ass and no knickers." I was thinking about, what he said.
"Oh and wear some of those sexy boots you have and your some make-up." I finally pictured it, and I was tossing up about it. "Come by Wednesday if interested and I'll show you, and I'll organise your new work clothes." He said. He poured me another wine on the house. "No obligations, if you're not interested; tell me then." Jerry said.
I looked around and it looked like a quiet night here, as I looked around at the talent; one more time. Once I finished my drink, I went home.
* On Wednesday I showed up and he showed me the ropes of my duties, he handed me a tight tank top tee; with the venues logo on it.
At about 8pm a local leather dude turned up and took measurements; of my inner and outer thighs and my waist. He gave me a demo pair of shorts to try on. "Take your knickers of before you put them on." He said, and gawked at my cock; as I did so.
The shorts were tight but flexible enough for me to wriggle into it, before I did up the laces around the belt. It was cut from 2'inches under the belt band to 2"inches from the bottom of the shorts, so basically the back of the shorts was missing.
The ass was cut out allowing flexible movement; enough for me to take a dump without taking them off but not too pee. My cock was enclosed but restrained if I grew a hard-on, I could touch my balls from the rear; from behind if I knelt or bent down.
They fit snug inside the front half of my new gear. I decided to wear the gear I was given, for the remainder of my shift. I felt naughty, all night. I grew hard but all you could notice was a bulge. Jerry told me that on Saturday, my gear will be ready. I didn't bother to change after my shift, and I walked outside with a bag of my clothes. As I wondered to my car, my heels poking my ass in the air; making and the night breeze drifted up my naked butt and against my balls.
I wanted to jerk off as I drove home, but I could even slip a hand done my shorts.
When I finally got home, my neighbour saw me and looked disgusted. I didn't care, and stripped off when I got inside and jerked off; as I waited for my bath to fill. * Friday I stayed home and on Saturday, I took a bag with me; and went to Jerry's bar. It was packed but not full, when I went behind the bar; dressed like I was. One guy made mention of my different look, I just smiled. Over the cause of the next 2 hours, I was slapped and wolf called; until about midnight when Jerry gave me a 15 minute smoke break.
I took and went out the side door and light up, in the alley. Leaning against the cold brick wall, I lifted one foot of the ground and against the wall too; smoking a ciggie. I soon realised I wasn't alone in the alley; two guys were making out and had their hands inside each other's pants.
Blowing smoke, I didn't move or make a sound. One of the guys noticed my smoke, and stopped kissing; he recognized me from inside. I winked at him, he whispered to his beau and then; they both walked up to me. "You feel like a fuck?" He asked, smelling of beer. "What about your friend?" I asked puzzled. "We're both want to fuck, and not into getting fucked." He slurred. They both had their cocks out now and were stroking them slowly. "Turn around let me see your ass." He mate said. I threw my cigarette down and turned around.
My cock was hard and the bulge could be seen stretching my red leather shorts. "We just want to fuck, and then go back for a drink inside." The first guy said. They parted my legs and pried my ass cheeks apart, then the turned me around; and gave me both cocks to play and decide with. Both were 7"inches and coated with precum, I spat on my hands and coated them even more.
"Ok, but I need to be back inside in ten minutes." I said and turned around and braced my hands against the wall and lent down. They spread my legs into position and one of them, started fingering my hole. These shorts weren't only good to have a dump in, but were good to be fucked in the ass with too. They were both silent and eager as they readied themselves. I had two fingers in my ass buried to the knuckle, fucking me and causing me to swivel my hips.
"It's ready. You first and stretch that ass hole wide for me." He said to his mate.
His mate spat on my butt then, slowly inched it in my sissy hole. Even with all the manipulation, it still hurt as it slid inside my tight little hole. "Ow, Ow, Ow, ouch." I said, and then grunted as he bottomed out inside me.
I was shushed. "Quiet and take it like the sissy bitch you are." I was told. He then pulled all the way out and spat on his cock, before forcing it back inside; he did this 3-4 times. He slapped my ass and started to fuck me hard, I could feel his ball sacks slapping near my own balls; I was so hard now but I could relieve my cock from my leather shorts.
I had to bit my lip to stop from screaming out, as he both hurt and turned me on; at the same time. "That's it, make the bitch want it." He mate, urged. His mate was grunting as he fucked me good and hard, and now I could stay quiet. "Fuck yeah, yeah, oh fuck yeah." I screamed out, as he fucked me hard and deep. He grunted out and I felt his cock explode in me, and coat my ass with his warm cum. I gasped and he did too, as he slowly slid out and a sound similar to a fart left my sissy hole; I felt cum trickle down my inner thighs and inside my leather shorts and coating my balls.
I felt sticky, in my shorts. "Ok, ok, my turn." He said in an eager voice, pushed his mate away. "Hmmm, nice cum lube you left me." He praised his mate, as he slid his cock in my hole.
God his cock felt thick as it slid deep inside, making me moan. "Oh god you feel good." I let out.
I felt him slide out then back in, chuckling to himself. "Ok bitch, time to fuck." He slurred out. I screamed in pain as he fucked me hard and fast. "If you can't take it, don't offer it, bitch." He belittled me. The pain was intense as he ploughed in, I had to grit my teeth; not letting him know it hurt. I think he knew thought, as I went silent.
He was thicker than his mate but slightly small, but effective. I felt tingling in my balls, as he rode me. His cock made noises as it slid in and out of my sissy hole.
Now his buddy was hard again and jacking off near me. I felt a twitch in my ass but it wasn't from his cock, it was my ass muscles twitching. I was feeling stimulated, and alive out being fucked in the dark open cool air.
I moaned and moaned, as a wave of electricity jolted through my body; the inside of my leather shorts felt even stickier. I was tingling all over, but he still fucked me; as I moaned with wobbly legs. He laughed at me moaning. "Yeah, I know you like it." He goaded me. His cock soon exploded as he thrust in deep one last time, grunting.
I took and had to wait for him to soften before he left my sissy cum hole.
When he pulled out, some cum juices trickled out also; from within my asshole. I collapsed to my knees, as my legs felt jelly-like.
Then his mate presented me with his cock as it blew on my face and opened mouth. I then sucked on it for a little while, still on jelly legs. Then I cleaned my ass off the other guy's softened cock. "Thanks." He said, as his mate had already gone back inside.
I felt awkward and stickiness within my shorts. Trying to clean up as best I could and stumble to my feet again, as I did so; Jerry came out telling me to get my ass back inside. * The remainder of my shift was interesting; cum was clearly visible from my rear. The odd patrons commented on my used ass.
The odd one would attempt to finger my ass hole as I gathered used glasses, onto a tray. I felt so embarrassed, but also so horny. Each time Jerry gave me a smoko break, I would also get fucked some more; after my smoke.
Sometimes I would only get two drags out before I was bent over a bin or against the brick wall and fucked. Jerry would have to stick his head out the side door to get me back, too work.
By 3.30am I had been fucked by 5 guys, some were well hung too. The more I was fucked, the more my ass stuck up in the air and my lower back would bend downwards. Jerry just laughed, as he knew; what was going on and occasionally slap my raw ass. I felt moist inside my shorts and from within my ass crack and thighs, what a sight I must have been in the dimmed pub lighting. My ass was slapped so many times, I had gotten used to it. I felt embarrassed but very happy at the same time. By the end of my shift, I was sticky, sore; but very pleased.
When my shift ended I changed in the storeroom, and when I removed my shorts; they dropped to the ground with a heavy sloppy thud. I must have cum several times by the look of all the cum in the front half of my leather shorts. Luckily I only work Saturdays and I had three sets of shorts, a red, pink and purple ones. I changed and went home, and to a warm bath.