Walking Home from Work

This is my first attempt at writing about my experiences and fantasies dealing with cross-dressing, so my apologies if it seems not that well written.

I have been a closet dresser for most of my life; starting from the first time my older sisters dressed me as a girl for Halloween when I was 10 - but that's a whole different story of its own.

The experience I have chosen to write about occurred when I was about 22. At the time I was living in a small town in southwestern Pennsylvania working as a maintenance contractor for a local office building that needed some interior structural repairs. I was able to do the smaller repairs during the day while the offices were open, but preferred to do the larger projects in the evenings and sometimes on weekends. I had worn women's clothing under my work clothes several times while working late at night and discarded my work clothes once I made sure nobody else was working late. At 5'10" and 125 lbs with shoulder length hair, my body was passable although my face was not.

On this particular night I put on black fishnet thigh highs held up by a black lace garter, a pink satin thong with ruffled white lace trim and a white bow in front, along with a matching pink bra with the bow on the middle of the cups. Of course I filled the cups out with my 'enhance me' silicone pads which gave me a cute little 'A' cup. Over this, I wore a white peasant midriff blouse with a wide ruffled collar and short sleeves that laced up the front so it could be as open as you chose. With it I wore a blue and white plaid schoolgirl skirt and black strapped sandals that strapped above my ankle.

I put the sandals in my backpack and put my work clothes on and walked to work(I only lived 4 blocks away). I made my rounds when I arrived to make sure the building was empty and got to work. They were turning an unused area of the building into an employee lounge/ dining area and tonight I was finishing one of the counters that would hold one of three microwave ovens. Things went smoothly and I finished a bit earlier than I expected. It was about 2 am and I was cleaning up getting ready to walk home when I had the brave idea to put my work clothes in my backpack and walk home dressed as I was. I had never ventured out in public dressed before and my mind was racing back and forth worrying and imagining all kinds of things that could go wrong, but in a matter of minutes I found myself outside locking the building behind me.

OK, I was really going to do this; walk home dressed as a girl. I figured as long as nobody got too close I would be fine, but as a precaution I decided to walk the alley instead of the street. As I crossed the street into the next alley I caught sight of a few guys walking down the cross street coming my way. I quickly stepped into the alley and kept walking at a faster pace, I make it half way to the next block when I hear them turn into the alley behind me. "Oh shit" I thought to myself "I just had to try this, didn't I" I quickened my pace and just as I get to the end of the block, two men step into the alley in front of me. I tucked my head down to obscure my face and went to pass by them only to be grabbed by my arms and guided back into the alley.

My mind is going crazy, I don't want to yell out for help and wind up being outed but I don't want to wind up beat up or dead either. The two men pin me up against a wall and as I feel their hands roaming all over my body, I hear one of them say to me "Don't worry, nobody wants to hurt you. We just thought you'd like a little fun." Then he leans in and whispers in my ear "You do want to have some fun, don't you little boi?"

There it was, I was busted and now their three friends that had followed me into the alley had caught up and I was surrounded by all five. The one that had whispered to me took my left hand and guided it to his crotch and I instinctively started running it up and down the length of his cock through his jeans. His partner followed suit and as I was stroking them both through their jeans, one of the three others stepped between them and put his hands on my shoulders and told me to get on my knees. I took my backpack off and placed it in front of me and knelt down with my knees on top of it. I was now face to face with three male crotches, each with a hard-on growing under the fabric.

I resume stroking the first two while the one in the middle steps forward and places the waistline of his jeans an inch from my mouth. He unbuckles his belt and jeans, then tells me to pull his zipper down with my mouth. I reach out and get the zipper between my teeth and slowly start to pull it down as I undo the belts and zippers of the other two with my hands. I may be terrified, but they've also got me super horny and I figured I might as well get some enjoyment from it too.

As I get the zipper in my mouth worked all the way down, his cock springs out and hits me right between the eyes and what a beautiful cock it is. not too thick, about 1 1/2" diameter, but a good 8" to 9" in length. I start to lick the underside of the shaft and it bounces up and comes back down to smack me in the face again; god I wanted that cock down my throat. I stretch my head up and take just the head into my mouth and twirl my tongue around the edges of it and along the opening at the tip. I could taste the sweet, salty pre-cum oozing from him; mmmmmm so tasty. The cocks in my hands are now free from their confinement; the one in my left hand a bit thicker than the one in my mouth and just as long. The one in my right hand was the thickest, I could barely get my hand around it. It was a little shorter than the others, I'd say about 7" but it would be the hardest one of the three to try to fit in my mouth.

By this time the other two had closed in I was feeling more hands all over my body, fondling my nipples and massaging my ass and inner thighs. I had forgotten my fears and was enjoying the feeling of a cock sliding in and out of my mouth and pumping two more with my hands while hands glided over my body. One of those hands found it's way to my thong covered rosebud and started gently rubbing up and down along it between my cheeks. every time he brushed over my rosebud, my back arched driving my head further down the cock in my mouth until my nose hit the trimmed hair at it's base.

The two I was stroking stepped closer till both their cocks were in my face, so I started sucking each of them alternating between the three. I managed to get a little more than the head of the thicker 7" one in my mouth when I felt the cool finger start rubbing circles around my now puckering hole. I let out a little gasp when it slid inside and as I did, Mr. 7" grabbed my head and pushed another 2" of his fat cock into my mouth. He started face fucking me slowly as I was being finger fucked. Each time that finger plunged into me, his cock stretched my mouth further until I was taking his whole member without choking. After a few minutes of me deepthroating him, he pulled back and shot a thick, hot load of cum into my mouth and across my cheeks. I swallowed what I had in my mouth and licked the cum from around my lips just in time to have my mouth filled with cock again.

This time it was the man who had done the whispering, he had a nice 8 1/2" cock about 2" thick that slid all the way down my throat with the first plunge of his hips. As I sucked on this juicy dick, I was raised up off my knees so that I saw bent over at the waist still sucking and jerking two others at the same time. Hands started rubbing my ass again and I felt the finger return to my well lubed hole. It was soon joined by a second and then a third. When the fourth finger slid in, I drove my head down on all 8 1/2" of the one in my mouth and was rewarded with my second load going straight down my throat. He stepped away and was replaced by the one I had started sucking first.

As I was enjoying him thrusting his cock in and out of my mouth I felt the fingers withdraw from my now gaping hole and let out a whimper. Then I felt the warmth of flesh sliding up and down between my ass cheeks followed by a gentle rubbing and prodding at my hole. Whoever was behind me was taking their time and making me ache for them to plunge that dick into my empty ass. My head was being held in place while I was being face fucked and I couldn't turn and see who it was, but I wanted them in my ass NOW! I felt the tip press against me and I pushed my hips back causing the head to enter and wiggled my ass to urge him to give me more of it.

I didn't have to wait long, he held me by my hips and started to slowly feed his dick into my tight little ass. It seemed like forever before he finally had my ass against his groin, his cock had to be at least 10" long but it was slim enough not to tear me apart. When he had his cock buried completely in my ass he started gyrating his hips, sending ripples of lust through my body and sending the guy in front of me over the edge. His cock throbbed and swelled and he pulled from my throat, leaving the head resting on my lips as he shot a huge load into my mouth and on my face.

I guess it was the 5th man that got in front of me now and started lightly slapping my cheeks with a glistening dark 10" cock. The huge cock in my ass was picking up it's pace and as my ass was bouncing off his groin I felt someone spray a load of cum across my ass. I grab the cock in front of me and lick the pre-cum from the tip, as well as all the cum along the sides from it slapping my cum covered face. I start feeding his pole down my throat as the guy behind me is thrusting his cock as far into my ass as he can and it hits me, the most intense orgasm I had ever had. My body starts shaking and bucking, driving them both deeper into my ass and mouth which sends even more waves of pleasure through my body.

These two 10" cocks have me lost in lust as they plunge into me at both ends. I open my eyes to see the other three standing close and stroking their cocks near my face while watching their friend's huge cock disappearing down my throat. Even though I had a mind blowing internal orgasm, I had not ejaculated and needed to badly so I reached down and started playing with my own slim 7", lightly rubbing along the underside and over my tightening balls. I start stroking it in pace with the two cock filling me only to have my hand pushed away by someone. I hear the two men fucking me start to groan and feel their cocks start throbbing harder and I know they are both ready to cum. Just as they both start to fill me with their loads, the three shoot their loads over my face and the cock in my mouth, just then I feel a mouth close around my cock and I start shooting the largest load I'd ever produced into that warm mouth.

They collected themselves and left me in a quivering slump and as I scooped what cum I could into my hungry mouth I got hard again. I shook my head to clear the 'cum webs' in my brain and changed into my work clothes before gingerly walking the last block home.