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Intro:

My name is Rob, but my sissy name is Hillary Rose, a combination of the first name being a beautiful girl I went to elementary school with and the last, a sexy last name of a distant relative. I’ve been a sissy as far back as I can remember, maybe about the age of 11. I used to think to myself how sexy my sisters looked in their catholic schoolgirl uniforms, and I would often put them on, stockings, panties, bra, skirt, heels and all when they would leave them on the bathroom floor. Which eventually led me to “borrow” (without the person knowing) girls clothes from whomever and wherever I could. As I grew older, I amassed my own wardrobe, complete with wigs, breast forms, makeup, and all the lingerie, clothes, heels and toys a sissy could need. It was all behind closed doors, and thanks to the wonder of the internet I progressed from dressing whenever I could, to taking orders from men over webcam and eventually constantly looking forward to my next opportunity to please a man in person. Although I am sexually attracted to both, I could never bring myself to date men, only women. This led to hiding clothes from girls I lived with, and infidelity, whenever an online exchange with a man drove me to want to please him sexually. The story that follows is both a mix of factual events in my life and some fantasy. I may eventually post entirely factual stories of my sexual adventures, depending on how well this takes off. SO PLEASE COMMENT IF YOU LIKE OR EVEN IF YOU DON’T, IT WOULD ENCOURAGE ME TO DO MORE…. OR TO STOP…

Well, as I said, I’ve lived with a couple of girlfriends over the years, and had my hidden stash of clothes, toys etc…. One day my girlfriend, Kelly, a short 21 year old brunette, with a tight body, 34C cups, nice abs, and an ass that would make a gay man turn his head, was slated to work late, and head to her evening class at the local college right after, not due home till about 8pm. We had known each other about six years and had been dating about four, the sex life was almost non existent now, and we were really caught in a rut, both so caught up in life, me with work and trying to get onto the Fire Department, her with work and going to college. The monotony was almost painful; at this point we were essentially just roommates who fucked every couple of months.

Arriving home about 3pm from work that day, I figured I would have plenty of time to dress as Hillary and be a sissy cam whore for men on yahoo. I rushed into my apartment, a small 1 bedroom located immediately thru the main apt building door as you walked in from the parking lot, it was a dingy run down 3 story apartment building. Locking the door and securing the chain, as insurance, I turned on the computer (they were slow to power up back then) which was situated in the small kitchen/dining room you walked into when entering the apartment. I started stripping as I headed to the bedroom, so as to maximize my time as Hillary. Totally naked now, my body shaved all over (which I had achieved by telling Kelly that body hair disgusted me, she agreed) except for a little patch of hair I left just above my sissy clit, so that when tucked it had just the right amount of hair to add to the illusion, that I might actually have a pussy between my legs. I opened our shared closet, and pulled out a black sparkly, short dress that Kelly had, but had never worn in the four years we had been together. I undid the padlock on the footlocker that contained all of Hillary’s things, which Kelly believed contained valuable baseball cards, as fast as I could. Pulling out my black padded bra, black garter belt, black lace thigh high stockings, black lace thong, and my 7″ vibrating suction cup dildo. To finish off the outfit I grabbed a pair of Kelly’s black high heels from the closet floor. Dressing as fast as I could, I headed back into the dining room and placed the dildo on the table next to the computer, having only to attach my garters, and put on my heels.

I sat down and opened up my favorite messenger program. While waiting for it to open and sign on I completed my transformation in what I thought was one of my sexiest outfits yet. I entered a chat room, turned on my webcam and waited for the horny men to message and direct me.

In no time flat, I was both riding my dildo, and jerking my pathetic little 5″ slender sissy clit, giving the perfect camera angle for the maximum amount of 25 horny men the program would allow. Taking orders, doing everything from demonstrating my blowjob skills on my dildo to pissing in a cup, and everything in between, virtually anything that 25 horny men could possibly dream up for a sissy whore who was desperate to please, with the exception of blood and scat, even sissies have limits…

Having watched more than a few of my viewers shoot impressive loads, from their hard, mouth watering cocks, dreaming of their thick, delicious, smooth loads, sliding down my throat, I had my heels up on the edge of the table, the camera pointing mersin escort down giving the viewers a shot of my black lace garters, my thong pulled to the side and me stroking my little prick while I’m burying all 7″ of my lovely fake cock, taking it up to the balls, bounce after bounce the cock slides deep in my sissy pussy, pounding my prostate. The top of my little excuse for a penis was now moist with precum, glistening in the light from above. Most of my remaining viewers were requesting I shoot my sissy juice.

I grabbed the shot glass I always use when masturbating…easy clean up… convenience should I become thirsty. I begin to feverishly stroke my tiny clit using two fingers, as I balance myself on the arm of the chair, giving me leverage to continue the glorious pounding my ass is receiving. I’m so close now, my balls tightening, so caught up in the moment, when I hear keys slide into the door….

“SHIT!” I think to myself, I jump up, hit the power button on the computer, as the door opens an inch its suddenly stopped in its track by the chain, my heart pounding out of my chest a mile a minute, as I run around the corner into the bathroom, trying not to let Kelly’s black heels click on the tile floor as I run, I drop the dildo in the chaos, quickly scoop it up and close the bathroom door.

I hear Kelly yell “ROB! ROB! WHAT’S GOING ON? WHY IS THE CHAIN ON?” Moving at lightning speed now, I take off the dress, then the bra, the garter, panties, stockings and heels all in one quick swoop…

“Where to hide it, where to hide it”… my mind racing, I open the cover of the trash can and jam it all in, throw on a pair of boxers left on the floor and run to undo the chain, hoping it was all quick enough to not arouse suspicion. “Hey babe, why are you home?” Trying to cover the fact that I’m out of breathe and my heart is racing…

“Class was cancelled, why the hell was the chain on the door.”

Thinking quickly… “I was taking a nap, wanted the extra security” looking her in the eyes, trying to see if she’s buying it, trying to read from her actions, see if she caught a glimpse of her sissy boyfriend running in a panic…

“Okay….” she said, skeptically. I think I’m in the clear… I sit down on the couch and turn on the TV, my heart rate slowing, regaining my breath. Kelly heads into the bedroom to change out of her work clothes.

Thinking to myself, “Did I lock the foot locker? I did… ok, I think I’m still good.” Kelly came out, wearing her typical yoga pants, and tank top that both hug her tight body and show off her tits and ass so well, she heads into the bathroom… not unusual, sometimes she did that after work…”I’m still good, why would she look in the trash” I thought to myself. The toilet flushes, the bathrooms quiet for what seems like an eternity, but in reality probably just a minute or two. The door opens, Kelly walks out, what’s that in her hand…Shit it’s her dress…

“What, the FUCK, is THIS?” holding up the dress, “and THIS!? ” Holding up the dildo she was holding behind her back…

Fuck, I’m busted…”I… I just do it to get off… it’s nothing…I’m sorry…”

“UNBELIEVABLE” she said, just one word, that’s all, and she headed for the bedroom, throwing the dress and dildo onto the floor of the bathroom on her way by before slamming the door.

Kelly was a hardcore Christian, brought up by god loving parents, who prayed before dinner every night, and went to church every Sunday. It was a miracle that I even got her to let me finger her tight moist pussy, after dating for only a year. It took a full two years of dating, me finger fucking her, and her jerking my little dick, before I was finally able to convince her to let me take her virginity. After the next two years of fucking, and eating her pussy, she never did anything else, no blowjobs, no lingerie, no kinky movies, she was straight vanilla.

I sat in the living room, a scared, broken, pathetic excuse for a man as I wondered what would happen next but I knew….I knew the dildo alone would be enough to make her end it. She thinks of a man with a dildo and her Christian upbringing, and straight edge parents have all but trained her to think faggot, never mind the girl’s clothes, no need to even consider that aspect, what added insult to injury was that it was her little black sparkly dress to begin with.

I walked into the bedroom, Kelly was lying on the bed on her back, staring at the ceiling with the most blank look on her face I had ever seen…”I’m sorry Kelly.” I said as I hung my head low.

“What are you gay? I can’t believe I’ve wasted all this time with you.”

I replied. “I’m not gay Kelly, I love you, and I just do this because it feels good.”

She laid there in thought for a second…”No, no your gay, no straight man would do this, we’re done, this was falling apart anyway, I want you out” She said.

“But babe…”

“No, kocaeli escort we’re done ROB; I can’t believe I wasted my time with you.” She said.

She’s hurt, I thought, maybe it will pass, I packed up some things and headed to my parents a few towns over…I knew that was it, she arranged for me to get my things thru email when she wasn’t home, and I never saw her again. I pleaded thru email, but never received a reply.

When I got on the Fire Department just a few months later, I even thanked Kelly extensively, thru voicemails and emails for pushing me to achieve my dream of becoming a firefighter. Still no reply… life went on.

Living with my parents, really hurt my time as Hillary, so I progressed to finding men on the internet, for sex in person, and that meant I could be Hillary, I could be the perfect sissy I wanted to be, either at their place, a hotel, or outside, and I loved it.

My first time riding a dick I shot the biggest load ever, without even touching my little prick, and it was soft when it happened. Being like that, on all fours, getting fucked from behind, dressed like a slut, cumming as a hard cock is thrusting in and out of my ass. I felt like I was born to be a sissy, and to my surprise I was good at it.

I was better at having sex and pleasing men than I ever was with women. It just seemed to come naturally, all the married men would tell me I was better than their wives at sucking their dick, all the gay men would say I was better than their boyfriends.

The schedule I had at the Fire Department, gave me a few full days off a week, more than enough time to meet men, some regulars, some random strangers, and show them how good a whore Hillary is. But the new job wasn’t all it was cracked up to be, I mean I loved the job, and the time it allowed me as Hillary, but the people on my group were bad. It was more than hazing a new firefighter, it was hatred.

One firefighter in particular, Cheri, a cute, petite, brunette, great all around body, great shape like Kelly and sexy as hell. She had a little bit smaller tits than Kelly but otherwise, different face, same body, the exact opposite of what you would think a female firefighter would look like, very feminine. Being in a fire department that was 99% men, you know Cheri gets hit on regularly, and its so blunt sometimes it borders on sexual harrasment, but she doesn’t mind, she enjoys the attention. She knows she’s good looking and she’s a bitch because of it. All the other guys drooled over her, I didn’t like her attitude, so I refused to pine over her, besides I had all but stopped getting a hard on for women anyway, I was so caught up in being Hillary, perfecting my sexual skills and pleasing men I didn’t give her the time of day. Perhaps because of that, she seemed to have it out for me, more than the others. She would order me around, insult me, ignore me, make me look stupid, do anything she could to belittle me, as a result, I hated coming to work, I hated my dream job, I just looked forward to the next day off, to becoming Hillary and serving and pleasing men.

I had vacation time, being a new firefighter, turned out by the time I had earned it I needed to use it as soon as possible or I would lose it. So I took a week (two 24hr shifts) off, the 2nd day off I needed to head in to drop off some paperwork in the Chiefs mailbox. The station was empty, they were on a fire call, and I put the paperwork in the Chiefs mailbox and ran up to the bunk room to put some spare uniforms in my locker. The bunk room had one bed when you walked in, a wall of lockers and on the other side, 2 beds, 1 on each side of a desk. The one to the right of the desk was Cheri’s; she often put her backpack on the desk, and at the end of every 24hr tour she would change out of her uniform into civilian clothes before heading off to wherever she went. I couldn’t resist, I knew everyone was out of the station and would be for a while, besides I would be able to hear over the loudspeakers if they were returning.

I reached over, opened the zipper just a bit to peak, my adrenaline pumping now, my heart racing. Peeking in, I saw a pink satin bra, with black lace trim and a black bow in the middle, I turned away, questioning myself, was this right, should I be doing this… the urge was too strong, I opened the zipper fully, took out the bra, underneath was an equally sexy pink satin thong, with black lace trim and a black bow just over the crotch.

I sat down on Cheri’s bed, made up with her light purple sheets, the panties and bra next to me, again I thought to myself, “Do I want to do this.” I did, I couldn’t resist, I closed the door to the bunk room, it didn’t lock but I was good. I had the radio over the speakers as warning enough.

I stripped off my clothes, naked; I sat down on Cheri’s bed. I slid her thong on, over my smooth, freshly shaved legs; I stood up, so that the thong would fit snuggly into my behind. samsun escort I sat back down, wrapped the bra around my waist backwards, and clasped the double clasp, putting the bra on just like women do, turning it around, and sliding it up to my chest.

“If I’m going to do this, I need to cum quick” I thought to myself, with the radio chatter I had heard the fire was out I had maybe 20 minutes tops before the guys checked for extension of fire, wrapped up the hose, and headed back.

So I thought if I needed to cum quick, I need something up my ass, I had learned from the past few months without Kelly, with men, that something in my ass when jerking my 5″ excuse for a dick would make me cum in no time. Thinking quickly I looked in the bag, Cheri had a hair brush, the handle, hard plastic and bumpy, looked like it would feel great in my ass, I sat back on her pillow as I did I got a whiff of her shampoo off coming off the pillow, it was intoxicating, I had smelled it before as she walked by, the smell of that, and look of my pretty pink bra, and my little dick under her panties made me hard almost instantly. I spread my legs on the bed, sucked on the end of the hair brush a bit and slid it into my fuck hole.

Sitting on Cheri’s bed, in her bra and panties, dildoing myself drove me insane, I imagined her, how she dominates me, how she belittles me, I imagined how I would fuck her pussy hard, so hard releasing my anger, shoving my little dick in her as hard as I could, how I would slap her as I fucked her for being such a bitch, I was shoving the entire brush in and out of my sissy pussy now, up to the bristles with each thrust, jerking my little dick with my thumb and 2 fingers furiously now, getting so close, my balls tightened, I panicked, I couldn’t cum on her bed, I looked around feverishly, luckily someone had left and empty cup nearby, I grabbed it, plowed my sissy hole a few more times and stroked my cock a few more, aiming my clit hole at the cup ready to shoot.

The door flew open “What the FUCK!” It was Cheri, little did I know she was never on that fire call, she had come in late that morning and missed the rigs heading out, she was milling about the station the whole time awaiting their return.

Busted, there I was again, flashing back to just where I was with Kelly almost a year ago. Frozen like a deer in headlights, there I was on Cheri’s bed, in her bra and panties, her hair brush handle fully in my fuck hole, my hand aiming my dick at a cup ready to shoot.

“Don’t let me stop you, you fucking faggot, might as well finish”

Of course as she was saying that she was pulling out her camera phone from her uniform shirt pocket, I was so close to cumming I went to remove the brush handle from my ass and the feeling of it sliding out made my cock start spurting stream after stream of cum into the cup as Cheri snapped away. I didn’t want to get it on her sheets, I was helpless until my cock stopped cumming. Finally after a few seconds it stopped, I quickly put the cup on the desk, stripped the bra and panties off and put my clothes on faster than I probably ever had in my entire life.

Cheri was blocking my exit between the lockers and the wall so I sat back down on the bed opposite hers, my head hung low “I’m sorry Cheri, please don’t tell anyone”

“Oh, I don’t know about that, this is too good, hahaha” she said with that bitchy laugh I had heard all too much in the previous months.

“Please Cheri”…

“You know what Rob?”

“What?” I said, my head hung low, staring at the ground in disgust of myself, pondering my future.

“Guess who I take night classes with, yeah that’s right, Kelly, she found out I was a firefighter and told me before you even got on what a faggot you were and that you were trying to get on here, I heard all about your computer, sissy faggot, jerk off session”.

Stunned, I had nothing to say, I just sat there, the same sick feeling in my stomach I had with Kelly, I thought I was going to puke…she must have noticed.

“You ok, need something to drink?”

She slid the cup of my cum across the desk… I just looked at her, and put my head back down….

“No, you’re going to drink it if you don’t want people to know Bitch”

So I picked up the cup, put it to my lips, looking at her again with a question in my eyes…”DO IT” she reasserted… down it went, that delicious, salty, creamy cum, sliding down my throat, the feeling and taste I had grown to love so much since Kelly, flash… Cheri had taken another picture…

“Get the fuck out of here homo, take my panties and bra too, and take my brush, I don’t want that shit now”

Shoving it in my pocket in case I bumped into anyone else on the way out I headed out of the station to my car and threw up from nerves. I had to wait a whole 5 days before coming back to work, Cheri could tell the world by then, she could spread those pictures around the department in no time.

The next week, I walked into the station, nervous as all hell, trying to act normal, as if nothing the week before had happened, I walked into the day room, where the Captain had the meetings every morning, everyone looked at me, and turned back to their conversations, of course the only seat in the room was next to Cheri.

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