First Time Out In Woman 'S Wear


Anal, Gay, Transvestite
I have always been fascinated by the cool soft feeling of women's dress against my peel. Betty was away on a business trip for 7 Day and my weekend had started a pair of hours ago and it was now 4:30 in the afternoon.

I had always had an effeminate look to me, at 6'0"and as thin as a rail even at 26. I was a scrawny shag and Betty kept saying how fragile I looked. I had bought a red wig to go with the kit I had picked out for myself when Betty had told me about her trip 2 months age. I had opprobrious 6"heeled boot, melanise stocking, a blackened garter belt and red panties and red halter bra laid out on our bed. side by side to them were a short bootleg skirt and a little black tube top. Man I was standing tall just thinking how I would seem like and find.

I took a exhibitor and used some hair removing emollient on my finish dead body except for my foreland. My leg and arms were silky smooth along with my ass. In Betty's and my elbow room I put on the pantie and bra first slipping some silicone breasts into the bra that I had picked up, so now I was a C cup. I then slipped on the garter bang and then the stockings. Ohhh I just love the way they felt against my smooth hide. I tucked my cock away and slid on my skirt then put on my thermionic tube top and pulled on and zipped up my knee high boots. I applied some mascara, some red lipstick and with the some final tinge, I put on my wig. Damn, I was hot and looked like a $ 1000 dollar hooker. I was so hot it was heavy to keep my manus off myself.

I was just lying around the mansion all dressed up when suddenly I a truck pulling into the labor way. I started to panic and rushed for the door peeking out of our peek hole. It was only the ring armour man with a prominent box. I opened the door slowly and said howdy in a delicate vox and the mail service man smiled,"Going out tonight !"he said with a blanket smile as he looked me over. I smiled back and tool the box and he left. Man I was shaking with care and excitement ; no one had ever seen my dressed like a cleaning lady, not even Betty.

When I calmed down I decided to go out for a crapulence, but I knew that I had to go to the early side of town so none of my neighbors would find out or see my. I was going to see if I was hot enough to get the bozo all hot and steamy as they bought me drinks.

At the bar I stopped at several guys there turned and watched me walk up to the bar. The bar ship's boat's name was chuck and looked very intimidating, at 6"4"with a muscular, toned organic structure, looking like was thirty-something to forty, and about 220 lbs. He had dark embrown peel, short-change smuggled whisker and a deep voice. Some of the guys asked me to dance and bought me drinks, but chow seemed to be keeping an eye on me.

I don't know where the time went, but soon I found myself sitting at the bar with eats smiling at me."Everyone's gone home and it only you and I, baby."He said coming from behind the bar. I turned on the bar crapper and Chuck reached to beguile me as I got up and wobbled a little. One of his handwriting found my genital organ and he jumped back and looked back at me. He just shook his chief and walked over to the threshold and locked it.

'' Damn you're hot for a fag ! ”. Chuck said walking back over to me. He took my hand, smiled wide and gave me a yank to fall out him as he headed for one of the slope room access."I live above the bar and I want you to see my situation !"Chuck said pushing my through the doorway and up the stone's throw. I didn't know what to do being caught like this ; I felt sort of ashamed and excited being caught in this predicament. The apartment was humble more like a two-dimensional with the bed off to one side and a tabular array with 2 chairs and a belittled kitchen, the bath room was the exclusively room that really was break from the others.

chow grabbed me by the waste matter and pulled me close. He whispered in my ear that at firstly he was shocked, but after thinking about it, he was really turned on by the way I looked. I looked down at his cock and could recount by the bulge in his drawers."Don't try to run !"grub said in a firm ton then opened and dropped his pants."darn"His cock was a colossus and had grown to about 11.5 column inch of rock-and-roll hard dark pith with thick veins. I gasped a nervous swig and he pushed me to my knees.

Before another news was said, I was sucking on his huge prick. I had never thought about being with another man, but I felt my cock getting aroused. I could only go down about halfway on his enormous pole before I gagged. Chuck placed his bridge player on the backrest of my straits and started pumping his cock in and out of my sass. Each sentence I went down as far as I could, he would push me a little further. I was able to swallow about 8 column inch of his fat cock as Chuck fucked my mouth. I could feel his pressure sensation building and without word of advice, he shot his juicy load straight down the back of my pharynx. I was a little surprise at the vividness in which he came and tried to swallow every shoemaker's last drop. I was hot and wanted more than ; feelings inside me that I had never felt were exploding throughout my body and mind.

Chuck pulled me up and said that he hadn't had a blowjob like that since he was in high-pitched schooltime. I thanked him and told him to wait as I peeled off my halter and skirt. grub kissed me and I could feel his deal thrust aside the scanty as I played with his freak pecker. I felt his finger's breadth slide in up my ass then he lifted me up with his other arm and placed me on my breadbasket on his bed, so that my virgin ass was in the air waiting for him. I could finger him shift his postponement on the bed, then I felt the sarcoid tip of his cock goad at my tight hole and my psyche went racing. Even though he had just loosened my ass with his finger, I felt a burning star as he entered me for the start clock time and screamed in annoyance and joy. He slowly worked his way in and then started pounding all 11.5 inches ball deep in me. I swear I could savor his cockhead in the back of my throat as I cried out at first then moaned and groaned. I felt full, I felt whole and somehow it seemed natural.

My face was buried in the bed, and my hands were outstretched and gripping at the blankets. Chuck was pounding me with foresightful deliberate strokes, almost pulling himself out completely, then ramming it back in. IT felt so good to have a cock in my ass and I could find the force per unit area building deep inside myself and in him as his putz seemed to expand more. He started to shoot his hot sticky lode oceanic abyss into my ass and I started to spirt out a hot gluey load right into my panty. Chuck rolled off me and smiled at me, then made a motility down to his pecker, and I knew what he wanted me to do. So I took his cock into my mouth once again and cleaned him off from top to bottom of his shaft that was still erect. I cleaned both of his nut with my slutty lip ; he tasted so good, the dessert salty seminal fluid.

I looked into his eyes, and he looked into mine and. I sighed with relief and curled up next to him, with my mind on his lap. Smiling I began to roleplay with his dick, waving it around, sucking on the head word and slapping my own typeface with its fat long shaft and head word."SO you are a slut after all !"chow said as he slapped me on the ass. I decided to return him some more head and focused on his fat head of, sucking it like a tootsie pop. eats moaned in rapture.

He was still on his spinal column when I swung my girlish hips over his waist and placed his cock between my ass buttock. I looked at him seductively and raised my ass so that the tip of his shadow monster was right at the entering to my ass. I asked him what he wanted from his strumpet. Chucks answer was that he shoved his whole cock deep into my ass. I was in a state of shock ; all I could do was slip down it and rested with his cock in my ass and my balls on his pelvic area. He raised his knee so that I had something to lean back on as he grabbed cargo hold of both my boots and spread my branch apart."Now you're gon na drive me like a cowboy rides a bull !"He said then gave me a cowboy hat off his bedpost. I put it on and started riding that BIG strapper of his. I was bucking my hips and waving the hat in the air keeping one helping hand on his chest for support. I was moving up and down and Chuck pumped like a hazardous bull. This continued on for about 10 minutes, me waving the hat around holding onto his chest while I had his 11.5 column inch putz up my ass.

I could feel him start to thrust as if they were his lastly few and knew I was in for a big surprise, and boy was it a big surprise. Chuck fired off another hot unit of ammunition of cum up my ass and I was moaning at the top of my lungs. I collapsed onto chuck and he held me there feeling the cryptic warmness of his body.
The succeeding morning I awoke around 11am with the taste of cum in my sassing and my ass a sore as hell from the hardcore fucking that happened the Night before. I looked around and did not see Chuck, but I could hear him. So I got up and looked around finding him on his balcony on the speech sound. Chuck grabbed my script and pulled me out onto the balcony with him, I was still dress only in my red panty and bra, nigrify stockings and supporter belt

"Alright, 5 o'clock sounds great, see you then."He said, and then attend up the phone.

"Who was that ?"I asked smiling.

"Just a Friend, He will swing out by later tonight."He replied.

I shrugged my shoulder and thought naught of it. grub had on his boxers and I still had makeup on my fount from the night before. He dropped his boxers right there on the balcony and his pecker was semi-hard. I needed no prompting for what he wanted me to do. I don't know why, but I fell to my knees and engulfed his member in my wet warm mouth. It was like it all can natural to me, I started slowly working my lingua over his dark turncock and took as much of it into my mouth and throat, probably about 8 inches.
Without warning, eats grabbed the vertebral column of my head and thrusted forward shoving the rest of his hardening dick down my pharynx. I could feel my pharynx stretching as his long blockheaded shaft violated my pharynx. He proceeded to fuck my throat slowly ; I gagged a duad of times then was able to command my gagging. I could feel his pubic hairs against my nose and his balls slapping against my Chin. Man it felt unbelievable and I'm sure it felt better for him since he was moaning.

"Ohhhh ! return all of it you fucking slattern"“ Take my big shaft down your slutty pharynx. Oh you like that don't you ?"Chuck grunted out as I took him.

"mmmmmm"was all I could negociate to say with my backtalk and throat stuffed.

He pulled his hammer out of my athirst mouth. Then told me to lie down on the lawn chair with my leg over its top so that my head was hanging over the bottom character. I was upside down with my mouth at cock stratum. Chuck stuffed his cock back into my back talk and rammed it down my throat.
"MMMMMMMMMM"escaped my throat as he did.

"Oh bitch, you're a natural pecker sucking bawd !"he said to me.

Chuck was fucking my pharynx and his big globe were slapping against my forehead. I loved the way he used me and made me feel like the slut I now knew that I was destined to be. He grabbed my legs and pulled them to him so that I was almost folded in half. Then he licked two of his fingers and shoved them into my ass and I let out a muffle moan as he penetrated my man twat with his loggerheaded fingers. I was beginning to gag on his dick with his libertine thrusts, which he must have enjoyed since it made my throat contract. eats pulled his prick out of my lip and told me to stand up and I did like the respectable fornicatress that I had become. He sat down and told me to call for a butt ; I knew where he wanted me so I straddled him and placed my hungry ass pussy directly over his throbbing cock.

I slowly lowered myself onto his big gumshoe and it was still a stringent fit for him to get his cock into my thirsty ass. Even though he had ravaged my ass last night. As his cock's brain went in retiring my sphincter muscle, I let out a petty squeak of pleasure. He placed his hands on my shoulders and pushed me down onto his cock, it felt incredible to be filled by such a monster. I was able to sit all the way down on his cock and I could find it hitting my tail off-white.

I slowly began to stand up up on his shaft, letting it come almost all the way out before I lowered myself back down. As my ass got more used to his girth, my pace picked up and I was soon bouncing up and down on grub's rock hard cock. He was just sitting there with his hands on my hips, and each time I went down he pushed me down as far as he could. Then he helped raise me up and our motions became fluid. This continued for about ten minutes and I could palpate an orgasm building in me, as well as chow as he started to groan loudly.

"Oh damn bitch, I'm gon na fill you up, I'm gon na cum"Chuck moaned.

"Don't spot, don't stop ! Harder, HARDER !"I cried out not caring who might hear.

He began fucking me furiously and I felt his cum outset shooting deep inside my ass, which sent me over the bound and I began to shoot stream after stream of cum onto his stomach and mine. It was the most intense orgasm I had ever had, and I didn't even have to touch my cock. We slowed down, and I slumped onto him and rested my pass on his shoulder. grub whispered into my ear,

"I bet you like your married woman could fuck you like this !"

"I wish she could, but she doesn't even know that I like to ware women's clothing"“ but then if she did, I wouldn't get to do this with you from now on."I found myself saying.

chow looked into my eyes and just smiled. I slowly climbed off of his lap, and I felt his still knockout turncock pop out of my ass. My son of a bitch was gaping wide as his cum began to dribble out and down my leg. I looked at him and smiled then dropped to my genu and started cleaning his big dark cock. After cleaning all his cum from his tool and lump I said that I should probably go shower. He winked and said that he would be right behind me.

We went and showered together. While in there, I washed his hefty physical structure giving his pecker a lot of attention and he played with mine. We made out for a bit, and then got out. By now, it was 3 in the afternoon. We dried off and he went and got dressed. Chuck put on some black silk shorts and a tankful top then told me that I should get ready.

"Ready for what ?"I asked.

"Just get ready for a fun night."He said.

Over the next two hours, I prepared myself for chow and his Night. I went to the bathroom and shaved, put on some mascara, eyeliner, rouge, and red lipstick. I sprayed some perfume onto my satiny smooth skin so that I would smack as upright as I looked.

I got dressed in the bath way and when I stepped back into the primary room it was almost 5:30pm and I stopped in my raceway. There sitting with chuck were three other men. They were talking as I walked in, but immediately stopped when they saw me enrol the room. grub looked at me and then to the guy and said.

"fountainhead, here she is, as promised. Doesn't she look like such a dirty whore ?"

The foremost man, who I later found out was haystack, gave out a wolf whistle and said"the pits if she doesn't, she is just begging to be fucked."

The former two smiled and stood up. All three of them were in good shape. rick had curtly black pilus and a byssus and was probably around 6 groundwork tall and was almost as sinister as eats. The other two, Chris and Tom were roughly the same height and weight. Chris had brown hair and a odorous smile, and Tom had blonde fuzz, a brawny build and was definitely the cutest of the three.
chow came up next to me and whispered in my ear"I thought you would like to party tonight. These are my finale friends and they want a go at you."He looked me in the eyes and winked. I got a big smiling on my expression, like a kid in a candy depot.

Chris, crick, Tom and eats all dropped their pants and I was in Heaven. Standing before me were 4 in effect looking previous men. grub definitely had the biggest cock. kink's was probably the second heavy at about 9 column inch and very slurred. Tom's was probably about 7 inches with one Hell of a big read/write head on it, and Chris's was about 6 inches, but the juicy one of them all. My heart was pounding in my chest and my drumhead was spinning.

I sank to my knees and gobbled up Tom's cock. I engulfed it and used my tongue to swirl around his headspring and lick the underside of his cock. I worked my way down to his clod and sucked on both of them at the same time. By this meter all the men were standing around me with their rooster in their hands getting harder by the second. I was still sucking on Tom's cock as I grabbed haystack's and Chris's cocks and began to hitch them off. I began to deep throat Tom as he grabbed the side of my pass and began to fuck my mouth like a wash buck at the lead. He did this for about a minute until Chuck told him"Don't waste all your DOE on his pretty oral fissure, his ass is very fuddled and just begging to be fucked."

I looked up at Tom and he smiled as he saw my jolly eyes looking up obediently like the slut I was. I removed my mouth from his dick and began to form on Chris's fat pecker. It was so fat that I could barely get my sassing around it. I thought that sucking a sal soda can down my throat would be light. I was really enjoying the flavour of being used and being treated like a slovenly woman and thought what Betty would say if she could see me live.
By this fourth dimension, Tom had moved behind me, pulled my pelvic arch up so that I was bent grass over and had lifted my skirt. He pulled my panties to the slope and began to lick at my ass. It felt so incredible to induce my ass rimmed while I had a fat cock stuffed in my mouth and two men standing on either side of me with their turncock in my hands.

"flavour how much the slut loves this."Chris said."You have a capital jade here."Rick complimented Chuck.

Tom had stopped licking at my son of a bitch and asked whether or not he needed to use protection. Chuck looked at me, then back to Tom and said"Nah, lets fill this picayune slut up with as very much cum as possible. I want her to be sore for a week."Tom grinned and placed his 9 inch cock at the incoming to my ass. It was still a bit wet from me sucking him, and my SOB was just begging to be fucked. He began to push his cock into my ass and when his chief popped in he thrusted all the way in.
"MMMMMMMMMMMMM"I moaned loudly.

I must feature been a sight to see, here I was dressed as a slut. I had a fat stopcock in my lip, and one now completely buried in my ass, while simultaneously jerking off two men. I felt unscathed, I felt complete. This felt …right at home, like this was what I was meant to be.

Tom began to slowly fuck my ass, all the while saying"Oh shit is this slut tight. She is so lucky to be being shared by Chuck, you love this don't you bitch ?"I mumbled"mmmmmmm"with Chris's putz still in my mouth. Chris Pulled his rooster out and slapped it on my cheek, making a"thwack"sound every meter. He moved aside so that Rick and my eats could use my sassing. My optic popped wide when instead of them taking routine, they got side of meat by position and pushed both their cocks into my mouth at the same sentence. Man it was incredible, I slurped and sucked happily on the two big rooster ravaging my mouth.

They then started fucking my mouth, as one would pull out, the other would push in. It was an amazing feeling. All the while, Tom was behind me fucking my ass, his pace increased as he watched chow and hayrick fuck my mouth. Chris was standing on the side of me jerking his cock. I took my rightfield hand and pushed his aside and began to jerk him. I couldn't even get my hand around his fat shaft. I could feel Tom thrusting harder and deeper, then all of a sudden I felt him explode oceanic abyss in my ass as he let out a trashy moan. He slowed down then pulled his cock out of my ass. He shot so much that I could feel his cum dribbling down my leg.

As he moved, Chris took his piazza. He sat down on the bed and gently pulled me on top of him. I was now hovering above Chris's pole while grub and hayrick face fucked me. Chris guided my ass down onto his fat cock and I had to focus on my external respiration since his cock was so big it felt like he was splitting me with a bat. rick pulled his peter out and I focused down on chuck, but only for a moment because it was replaced by tom turkey. I tasted his come and my ass and gladly cleaned him up. I was so turned on ; they could deliver done whatever they wanted to me.

Chris had stuffed all of his fat cock down to its al-Qa'ida in my ass and was pulling me up so that I was riding his putz and sucking two others at the same meter. Chris did not cobbler's last as long as Tom had, probably because he had fucked my rima oris the longest. I could feel his prick grow bigger and extend inside me, then it burst filling me with his seed. He was not very long, but fucking tinker's dam he shot off a lot of cum. There must own been about 9 or 10 spurts of hot, viscous, stocky cum pumped into my ass.

His cock began to get mild and I stood up and he popped out of my yaw arse, now his cum literally flowed out of my gaping man twat. Chuck quickly replaced him, which was who I was looking forward to having fucked me the most. Chuck slipped underneath my crouching ass and stuffed my gaping hole. He pulled me down without warning and impaled me on his massive 11.5 inch monster. I let out a loud"yip"as he hit my seat off-white with his gigantic cock. He laid back then pulled me back so my back was on his stomach. He bent his legs lifting my legs into the air and draped over his knees. Rick stood there looking between our legs and lifted my legs completely into the air and unfold them broad. I looked Rick in the centre and gave him a nod with a grinning on my font.

grub's putz already filled with my ass, but Rick now slid his good sized prick into my sore ass. He positioned his cock pass right above Chuck's cock and slowly began to push. At beginning it was not easy, but he began to fight harder. I braced myself and tried to push my anatomical sphincter out to earmark him comfortable access. This did help a little, and he was able to labor his cock brain in my ass. Once he got the oral sex in kink pushed harder and he was able to push the sleep of his dick into me.

I was so fucking horny ! I now had two big turncock deep into my ass, while there were two other men jerking their prick at the quite a little of me being split in two by these two men."tinker's damn if Betty could see me"I thought as I moaned. Once he was completely inside me, he and chuck began a sawing round and worked my bastard so well that I never wanted it to end. grub began to osculate and bit me on my shoulder which drove me waste. I started to sway my ass back and forth to fuck their tool. Chris came over snap up my head yanked back and shoved his now thick dick back into my mouth so that his clod were on my forehead. Tom wasn't one to be left out and came over and placed his cock in my sassing as well. I was now being human face fucked by two well-endowed men, while my arse was being violated by two big men.

They continued pounding at my asshole ; and must make been hitting my prostate gland because I erupted with such an intense orgasm I thought I would pass out. I felt grub and rick pick up their pace and force slamming harder and harder into my ass. chuck began to spasm as his monster jerked inside me, he dig his fingerbreadth into my waist and burn my shoulder joint. He shuddered and moaned as he filled up my ass with more cum than he had the Nox before. wrick fucked my ass furiously and he too came filling me with thick hot cum.

Because kink was fucking my ass so furiously, he was making my hale body go up and down. This forced me to throat fucking Chris and Tom. I thought they both would cum in my throat, but Chris pulled out and Tom grabbed the side of my head and shoved his rooster down my throat. I couldn't help but gag, and this sent him over the edge. He shot his secondment payload straight down my pharynx and into my stomach. I milked his cock with my throat muscularity until he pulled out and Chris replaced his cock. He too pushed his prick down my throat and came with such effect that I gagged and almost passed out.

chuck and Rick pulled out of my ass and I was so bed weak from the intense fucking they had given me that I couldn't even move. I just laid there as the men got dressed and asked when they could do it again. Chuck looked at me, then said.

"How about next weekend, and see if you can get anyone else to total with you."

The men all agreed and soon they were gone. As I lay there in a sex and cum induced shock, I saw Chuck pass over to his T.V. and I freaked at what he lifted from beside it. grub had recorded the altogether affair ! It turned me on knowing that now I was really a fornicatress and it was all on tape.
eats smile down at me wickedly and I knew then that he had the final say in what happened to me. He was now my"pa ”, my"Pimp ”, and my"Lover !"He lay down beside me covered me up and hold in me tight smiling…..
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