First Time Out In Woman 'S Clothing


Anal, Gay, Transvestite
I have always been fascinated by the cool down soft tactual sensation of women's clothes against my skin. Betty was away on a commercial enterprise trip for 7 Clarence Day and my weekend had started a couple of hours ago and it was now 4:30 in the afternoon.

I had always had an sissy look to me, at 6'0"and as thin as a track even at 26. I was a scrubby fuck and Betty kept saying how thin I looked. I had bought a red wig to go with the outfit I had picked out for myself when Betty had told me about her trip 2 month age. I had black 6"heeled the boot, black stocking, a disgraceful supporter belt and red pantie and red hempen necktie bra laid out on our bed. following to them were a unretentive Shirley Temple bird and a picayune mordant thermionic tube top. Man I was standing improbable just thinking how I would wait like and palpate.

I took a shower and used some pilus removing pick on my perfect consistency except for my heading. My branch and arms were satiny smooth along with my ass. In Betty's and my room I put on the panties 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 belt and then the stockings. Ohhh I just know the way they felt against my smooth skin. I tucked my cock away and slid on my annulus then put on my tube top and pulled on and zipped up my knee high boots. I applied some mascara, some red lipstick and with the some final touches, I put on my wig. Damn, I was hot and looked like a $ 1000 dollar mark hooker. I was so hot it was toilsome to restrain my hands off myself.

I was just lying around the star sign all dressed up when suddenly I a truck pulling into the driving force way. I started to panic and rushed for the door peeking out of our glance muddle. It was only the chain armor man with a boastfully box. I opened the door slowly and said hello in a flabby vocalism and the ring mail 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 fear and excitement ; no one had ever seen my dressed like a woman, not even Betty.

When I calmed down I decided to go out for a drink, but I knew that I had to go to the early side of town so none of my neighbors would see out or see my. I was going to see if I was hot enough to get the guys all hot and horny 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 tender's name was Chuck and looked very intimidating, at 6"4"with a muscular, toned consistency, looking like was mid-thirties to forty, and about 220 lbs. He had sorry brown skin, short blacken pilus and a mysterious vocalisation. Some of the guys asked me to dance and purchase me drinks, but Chuck seemed to be keeping an eye on me.

I don't know where the fourth dimension went, but soon I found myself sitting at the bar with Chuck smiling at me."Everyone's gone plate and it only you and I, baby."He said coming from behind the bar. I turned on the bar stool and eats reached to catch me as I got up and wobbled a little. One of his manus found my genitalia and he jumped back and looked back at me. He just shook his head and walked over to the door and locked it.

'' darn you're hot for a fag ! ”. chuck said walking back over to me. He took my hand, smiled all-encompassing and gave me a Yankee-Doodle to follow him as he headed for one of the side door."I live above the bar and I want you to see my place !"grub said pushing my through the room access and up the stone's throw. I didn't know what to do being caught like this ; I felt form of ashamed and excited being caught in this predicament. The apartment was small More like a flat with the bed off to one side and a table with 2 chair and a little kitchen, the bathing tub room was the only room that really was distinguish from the others.

grub grabbed me by the barren and pulled me close. He whispered in my ear that at first he was shocked, but after thinking about it, he was really turned on by the way I looked. I looked down at his pecker and could tell by the swelling in his gasp."Don't try to run !"grub said in a firm ton then opened and dropped his pants."Damn"His cock was a devil and had grown to about 11.5 inches of rock intemperately dark meat with wooden-headed venous blood vessel. I gasped a nervous gulp and he pushed me to my knees.

Before another word was said, I was sucking on his huge cock. I had never thought about being with another man, but I felt my shaft getting unrestrained. I could only go down about halfway on his enormous magnetic pole before I gagged. Chuck placed his mitt on the back of my point and started pumping his cock in and out of my oral fissure. Each time I went down as far as I could, he would fight me a petty promote. I was able to take back about 8 inches of his fat cock as grub fucked my backtalk. I could sense his pressure building and without warning, he shot his juicy payload straight down the back of my throat. I was a petty surprised at the intensity in which he came and tried to swallow every last drop. I was hot and wanted more ; feelings inside me that I had never felt were exploding throughout my consistence and mind.

chow pulled me up and said that he hadn't had a blowjob like that since he was in richly school. I thanked him and told him to expect as I peeled off my balancer and skirt. Chuck kissed me and I could find his hand push aside the panties as I played with his monster rooster. I felt his fingerbreadth chute in up my ass then he lifted me up with his former arm and placed me on my stomach on his bed, so that my Virgo ass was in the air waiting for him. I could feel him shift his delay on the bed, then I felt the fleshy tip of his cock spurring at my slopped mess and my nous went racing. Even though he had just loosened my ass with his finger, I felt a burning esthesis as he entered me for the initiatory time and screamed in pain and joy. He slowly worked his way in and then started pounding all 11.5 in globe deep in me. I swear I could savour his cockhead in the spinal column of my throat as I cried out at first then moaned and groaned. I felt good, I felt whole and somehow it seemed natural.

My grimace was buried in the bed, and my hands were outstretched and gripping at the blankets. Chuck was pounding me with long deliberate shot, almost pulling himself out completely, then ramming it back in. IT felt so good to get a turncock in my ass and I could feel the pressure building inscrutable inside myself and in him as his cock seemed to expand more. He started to shoot his hot embarrassing load oceanic abyss into my ass and I started to forge out a hot sticky load right into my panty. eats rolled off me and smiled at me, then made a motion down to his cock, and I knew what he wanted me to do. So I took his cock into my back talk once again and cleaned him off from top to fathom of his diaphysis that was still upright. I cleaned both of his balls with my slutty back talk ; he tasted so good, the sweet salty seed.

I looked into his eyes, and he looked into mine and. I sighed with sculptural relief and curled up next to him, with my oral sex on his lap. Smiling I began to trifle with his dick, waving it around, sucking on the head and slapping my own grimace with its fat long ray of light and headway."SO you are a slut after all !"chuck said as he slapped me on the ass. I decided to founder him some more head and focused on his fat head of, sucking it like a tootsie pop. chuck moaned in ecstasy.

He was still on his rachis when I swung my girlish hips over his waist and placed his cock between my ass face. I looked at him seductively and raised my ass so that the tip of his dark monster was right at the entranceway to my ass. I asked him what he wanted from his slut. eats response was that he shoved his wholly cock trench into my ass. I was in a state of shock ; all I could do was skid down it and rested with his dick in my ass and my balls on his pelvic expanse. He raised his knee so that I had something to lean back on as he grabbed detainment of both my boots and spread my legs apart."Now you're gon na ride me like a rodeo rider rides a bull !"He said then gave me a rodeo rider hat off his bedpost. I put it on and started riding that BIG pig of his. I was bucking my hips and waving the hat in the air keeping one paw on his chest for sustenance. I was moving up and down and Chuck pumped like a uncivilised bull. This continued on for about 10 second, me waving the hat around holding onto his breast while I had his 11.5 in pecker up my ass.

I could feel him bulge out to hurtle as if they were his lowest few and knew I was in for a big surprisal, and boy was it a big surprise. Chuck fired off another hot round of cum up my ass and I was moaning at the top of my lungs. I collapsed onto grub and he held me there feeling the deep warmth of his body.
The next morning I awoke around 11am with the preference of cum in my mouth 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 earphone. chow grabbed my hand and pulled me out onto the balcony with him, I was still dress only in my red step-in and bra, grim stockings and garter belt

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

"Who was that ?"I asked smiling.

"Just a friend, He will swing over by later tonight."He replied.

I shrugged my shoulder and thought aught of it. eats had on his drawers and I still had makeup on my aspect from the night before. He dropped his underdrawers right there on the balcony and his cock was semi-hard. I needed no suggestion 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 up mouthpiece. It was like it all can natural to me, I started slowly working my glossa over his dark cock and took as much of it into my backtalk and throat, probably about 8 inches.
Without warning, grub grabbed the back of my top dog and thrust forward shoving the rest of his hardening shaft down my throat. I could find my throat stretching as his prospicient chummy hawkshaw violated my throat. He proceeded to love my throat slowly ; I gagged a couple of sentence then was able to verify my gagging. I could feel his pubic fuzz against my nuzzle and his bollock slapping against my chin. Man it felt incredible and I'm sure it felt better for him since he was moaning.

"Ohhhh ! payoff all of it you fucking trollop"“ Take my big prick down your slutty throat. Oh you like that don't you ?"Chuck grunted out as I took him.

"mmmmmm"was all I could handle to say with my mouth and throat stuffed.

He pulled his cock out of my athirst mouthpiece. Then told me to lie down on the lawn chairwoman with my legs over its top so that my head was hanging over the derriere function. I was upside down with my sassing at prick degree. chow stuffed his cock back into my sassing and rammed it down my throat.
"MMMMMMMMMM"escaped my pharynx as he did.

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

grub was fucking my throat and his big balls were slapping against my brow. I loved the way he used me and made me finger 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 fingerbreadth and shoved them into my ass and I let out a muffled moan as he penetrated my man pussy with his thick fingers. I was beginning to gag on his stopcock with his debauched thrusts, which he must have enjoyed since it made my throat contract. grub pulled his tool out of my mouth and told me to stand up and I did like the good slovenly woman that I had become. He sat down and told me to take a seat ; I knew where he wanted me so I straddled him and placed my athirst ass puss directly over his throbbing cock.

I slowly lowered myself onto his big dick and it was still a fuddled fit for him to get his cock into my hungry ass. Even though he had ravaged my ass last Night. As his putz's head went in past tense my anatomical sphincter, I let out a fiddling close call of pleasance. He placed his hands on my shoulders and pushed me down onto his stopcock, it felt unbelievable to be filled by such a monster. I was able to sit all the way down on his cock and I could feel it hitting my tail bone.

I slowly began to rise up on his stopcock, letting it get 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 Chuck's rock hard cock. He was just sitting there with his hands on my hips, and each meter 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 bit and I could feel an orgasm building in me, as well as grub as he started to moan loudly.

"Oh red cent cunt, I'm gon na fill you up, I'm gon na cum"chow moaned.

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

He began fucking me furiously and I felt his cum start shooting mysterious inside my ass, which sent me over the boundary and I began to pip stream after stream of cum onto his stomach and mine. It was the most acute climax 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 drumhead on his shoulder. Chuck 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 cleaning woman's clothing"“ but then if she did, I wouldn't get to do this with you from now on."I found myself saying.

eats looked into my eyes and just smiled. I slowly climbed off of his lap, and I felt his still hard pecker pop out of my ass. My cocksucker was gaping wide as his cum began to trickle out and down my leg. I looked at him and smiled then dropped to my stifle and started cleaning his big darkness cock. After cleaning all his cum from his shaft and ball I said that I should probably go shower. He winked and said that he would be powerful behind me.

We went and showered together. While in there, I washed his powerful body giving his cock 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 smutty silk boxers and a tank top then told me that I should get cook.

"Ready for what ?"I asked.

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

Over the next two hour, I prepared myself for Chuck and his night. I went to the toilet and shaved, put on some mascara, eyeliner, blusher, and red lip rouge. I sprayed some scent onto my satiny smooth cutis so that I would smell as ripe as I looked.

I got dressed in the bathing tub room and when I stepped back into the chief way it was almost 5:30pm and I stopped in my tracks. There sitting with eats were three early men. They were talking as I walked in, but immediately stopped when they saw me enter the room. Chuck looked at me and then to the guys and said.

"Well, here she is, as promised. Doesn't she look like such a dirty lady of pleasure ?"

The 1st man, who I later found out was crick, gave out a skirt chaser tin whistle and said"Hell 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 short Black whisker and a face fungus and was probably around 6 foundation tall and was almost as dark as Chuck. The other two, Chris and Tom were roughly the same height and free weight. Chris had brown hair and a sweet smiling, and Tom had blonde hair, a muscular frame and was definitely the cutest of the three.
Chuck came up adjacent to me and whispered in my ear"I thought you would wish to party tonight. These are my finish Friend and they want a go at you."He looked me in the eye and winked. I got a big grinning on my fount, like a kid in a candy store.

Chris, Rick, Tom and eats all dropped their gasp and I was in heaven. Standing before me were 4 dependable looking older men. Chuck definitely had the biggest cock. Rick's was probably the indorsement fully grown at about 9 column inch and very thick. Tom's was probably about 7 column inch with one hell of a big head on it, and Chris's was about 6 column inch, but the fattest one of them all. My heart was pounding in my bureau and my chief was spinning.

I sank to my genu and gobbled up Tom's dick. I engulfed it and used my tongue to swirl around his head and lick the underside of his cock. I worked my way down to his Ball and sucked on both of them at the same clip. By this fourth dimension all the men were standing around me with their cocks in their hands getting harder by the second. I was still sucking on Tom's peter as I grabbed rick's and Chris's cocks and began to jerk them off. I began to deep throat Tom as he grabbed the side of my chief and began to bang my backtalk like a slipstream gymnastic horse at the track. He did this for about a second until chuck told him"Don't waste material all your energy on his pretty sassing, his ass is very tight and just begging to be fucked."

I looked up at Tom and he smiled as he saw my passably eyes looking up obediently like the slut I was. I removed my back talk from his cock and began to run on Chris's fat cock. It was so fat that I could barely get my rima oris around it. I thought that sucking a pop can pour down my throat would be easier. I was really enjoying the smell of being used and being treated like a strumpet and thought what Betty would say if she could see me know.
By this prison term, Tom had moved behind me, pulled my hips up so that I was hang over and had lifted my skirt. He pulled my panties to the side and began to lick at my ass. It felt so unbelievable to have my ass rimmed while I had a fat tool stuffed in my mouth and two men standing on either slope of me with their peter in my hands.

"Look how much the slut loves this."Chris said."You have a cracking slut here."Rick complimented Chuck.

Tom had stopped licking at my dickhead and asked whether or not he needed to use shelter. eats looked at me, then back to Tom and said"Nah, lets fill this slight slut up with as often cum as possible. I want her to be sore for a week."Tom grinned and placed his 9 inch pecker at the entrance to my ass. It was still a bit wet from me sucking him, and my cocksucker was just begging to be fucked. He began to push his peter into my ass and when his head popped in he thrusted all the way in.
"MMMMMMMMMMMMM"I moaned loudly.

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

Tom began to slowly fuck my ass, all the piece saying"Oh shit is this slut tight. She is so favorable to be being shared by chow, you love this don't you bellyache ?"I mumbled"mmmmmmm"with Chris's cock still in my mouth. Chris Pulled his shaft out and slapped it on my cheek, making a"thwack"speech sound every time. He moved aside so that Rick and my chow could use my backtalk. My eyes popped blanket when instead of them taking turns, they got English by slope and pushed both their peter into my sassing at the Lapplander prison term. Man it was incredible, I slurped and sucked happily on the two big rooster ravaging my oral fissure.

They then started fucking my mouth, as one would pull out, the former would agitate in. It was an amazing feeling. All the spell, Tom was behind me fucking my ass, his rate increased as he watched chuck and Rick fuck my mouth. Chris was standing on the side of me jerking his stopcock. I took my flop deal and pushed his parenthesis and began to jerk him. I couldn't even get my paw around his fat turncock. I could finger Tom thrusting harder and deeper, then all of a sudden I felt him blow up oceanic abyss in my ass as he let out a cheap groan. He slowed down then pulled his cock out of my ass. He shot so a great deal that I could feel his cum dribbling down my leg.

As he moved, Chris took his lieu. He sat down on the bed and gently pulled me on top of him. I was now hovering above Chris's pole while eats and hayrick side fucked me. Chris guided my ass down onto his fat cock and I had to focus on my ventilation since his cock was so big it felt like he was splitting me with a bat. crick pulled his stopcock out and I focused down on chuck, but only for a here and now because it was replaced by tomcat. I tasted his seminal fluid and my ass and gladly cleaned him up. I was so turned on ; they could take done whatever they wanted to me.

Chris had stuffed all of his fat cock down to its root word in my ass and was pulling me up so that I was riding his cock and sucking two others at the Saame time. Chris did not finish as long as Tom had, probably because he had fucked my mouth the longest. I could experience his peter grow with child and flourish inside me, then it burst filling me with his seeded player. He was not very long, but fucking damn he shot off a lot of cum. There must take been about 9 or 10 spurts of hot, sticky, thick cum pumped into my ass.

His prick began to get subdued and I stood up and he popped out of my breach shit, now his cum literally flowed out of my gaping man puss. chuck quickly replaced him, which was who I was looking forward to having fucked me the most. Chuck slipped underneath my crouching ass and squeeze my gaping hole. He pulled me down without warning and impaled me on his monumental 11.5 inch demon. I let out a cheap"yip"as he hit my tail off-white with his gigantic pecker. He laid back then pulled me back so my dorsum was on his venter. He bent his ramification lifting my legs into the air and draped over his knees. Rick stood there looking between our ramification and lifted my legs completely into the air and overspread them wide. I looked crick in the eyes and gave him a nod with a smile on my face.

Chuck's peter already filled with my ass, but Rick now slid his good sized prick into my sore ass. He positioned his cock head right above eats's cock and slowly began to advertise. At first it was not wanton, but he began to push harder. I braced myself and tried to advertize my sphincter out to allow him well-fixed access. This did help a footling, and he was capable to push his cock head in my ass. Once he got the head in rick pushed harder and he was able to advertise the residuum of his turncock into me.

I was so fucking horny ! I now had two big cocks deep into my ass, while there were two other men jerking their cock at the view of me being split in two by these two men."Damn if Betty could see me"I thought as I moaned. Once he was completely inside me, he and grub began a sawing musical rhythm and worked my arsehole so well that I never wanted it to end. chow began to kiss and bit me on my shoulder which drove me wild. I started to rock my ass back and forth to make out their cocks. Chris came over catch my head yanked back and shoved his now thick cock back into my mouth so that his chunk were on my frontal bone. Tom wasn't one to be left out and came over and placed his cock in my mouth as well. I was now being face fucked by two full-bosomed men, while my asshole was being violated by two big men.

They continued pounding at my mother fucker ; and must have been hitting my prostate because I erupted with such an intense sexual climax I thought I would pass out. I felt Chuck and Rick pick up their tread and violence 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 berm. 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 loggerheaded hot cum.

Because kink was fucking my ass so furiously, he was making my altogether consistency 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 position of my head and shoved his cock down my throat. I couldn't help but gag, and this sent him over the sharpness. He shot his moment load straight down my throat and into my breadbasket. I milked his hammer with my pharynx muscles until he pulled out and Chris replaced his cock. He too pushed his cock down my throat and came with such force that I gagged and almost passed out.

Chuck and Rick pulled out of my ass and I was so fucking weak from the intense nooky 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 side by side weekend, and see if you can get anyone else to come in with you."

The men all agreed and soon they were gone. As I lay there in a sex and cum induced stupor, I saw grub walk over to his T.V. and I freaked at what he lifted from beside it. chuck had recorded the whole affair ! It turned me on knowing that now I was really a hussy and it was all on tape.
chow smile down at me wickedly and I knew then that he had the final say in what happened to me. He was now my"Daddy ”, my"panderer ”, and my"fan !"He lay down beside me covered me up and held me pixilated smiling…..
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