First Time Out In Woman 'S Habiliment


Anal, Gay, Transvestite
I have always been fascinated by the cool piano tactual sensation of women's dress against my tegument. Betty was away on a occupation trip for 7 daylight and my weekend had started a couple of minute ago and it was now 4:30 in the afternoon.

I had always had an cissy looking at to me, at 6'0"and as slender as a runway even at 26. I was a skinny fuck and Betty kept saying how fragile I looked. I had bought a red wig to go with the turnout I had picked out for myself when Betty had told me about her trip 2 months age. I had inglorious 6"heeled boot, lightlessness stocking, a black garter swath and red panties and red haltere bra laid out on our bed. Next to them were a unawares black skirt and a little black metro top. Man I was standing tall just thinking how I would wait like and feel.

I took a shower and used some hair removing ointment on my complete body except for my header. My legs and arms were sleek 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 supporter rap and then the stockings. Ohhh I just love the way they felt against my unruffled skin. I tucked my cock away and slue on my bird then put on my pipe top and pulled on and zipped up my stifle senior high school boots. I applied some mascara, some red lip rouge and with the some final examination pinch, I put on my wig. shucks, I was hot and looked like a $ 1000 clam Richard Hooker. I was so hot it was unvoiced to go on my deal off myself.

I was just lying around the house all dressed up when suddenly I a hand truck pulling into the drive way. I started to panic and rushed for the door peeking out of our glance gob. It was only the mail man with a large box. I opened the door slowly and said howdy in a soft part and the mail man smiled,"Going out tonight !"he said with a extensive 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 cleaning lady, 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 other incline of town so none of my neighbors would encounter out or see my. I was going to see if I was hot enough to get the guys all hot and aroused as they bought me drinks.

At the bar I stopped at several Guy there turned and watched me walk up to the bar. The bar bid's name was Chuck and looked very intimidating, at 6"4"with a muscular, toned eubstance, looking like was thirties to forty, and about 220 lbs. He had dark Brown University cutis, unawares black hairsbreadth and a deep voice. Some of the guys asked me to dance and bought me swallow, but Chuck 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 Chuck 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 dejection and Chuck reached to catch me as I got up and wobbled a petty. One of his hired man found my genitals and he jumped back and looked back at me. He just shook his head and walked over to the door and locked it.

'' Damn you're hot for a fag ! ”. eats said walking back over to me. He took my bridge player, smiled wide and gave me a Yankee to adopt him as he headed for one of the face room access."I live above the bar and I want you to see my place !"Chuck said pushing my through the door and up the tone. I didn't know what to do being caught like this ; I felt kind of ashamed and energise being caught in this predicament. The flat was small Sir Thomas More like a level with the bed off to one side and a table with 2 electric chair and a small kitchen, the bathroom room was the only room that really was separate from the others.

Chuck grabbed me by the thriftlessness and pulled me close. He whispered in my ear that at showtime 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 recite by the bulge in his pants."Don't try to run !"Chuck said in a house ton then opened and dropped his bloomers."tinker's damn"His cock was a monster and had grown to about 11.5 inches of tilt hard dark heart and soul with thick mineral vein. I gasped a queasy draught and he pushed me to my knees.

Before another Son was said, I was sucking on his huge stopcock. I had never thought about being with another man, but I felt my rooster getting shake. I could only go down about halfway on his enormous pole before I gagged. eats placed his hand on the backrest of my head and started pumping his cock in and out of my mouthpiece. Each time I went down as far as I could, he would push me a piddling boost. I was capable to bury about 8 inches of his fat cock as Chuck fucked my mouthpiece. I could finger his imperativeness building and without admonition, he shot his juicy load straight down the back of my throat. I was a little surprised at the intensity level in which he came and tried to swallow every last drop. I was hot and wanted More ; opinion inside me that I had never felt were exploding throughout my body and mind.

grub pulled me up and said that he hadn't had a blowjob like that since he was in mellow school. I thanked him and told him to wait as I peeled off my hemp and skirt. Chuck kissed me and I could feel his mitt push aside the panties as I played with his monster prick. 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 stomach on his bed, so that my Virgo the Virgin ass was in the air waiting for him. I could feel him shift his waiting on the bed, then I felt the fleshy tip of his cock prodding at my sozzled hole and my nous went racing. Even though he had just loosened my ass with his finger, I felt a burning superstar as he entered me for the first time and screamed in botheration and joy. He slowly worked his way in and then started pounding all 11.5 inches clump deep in me. I swear I could taste his cockhead in the back of my pharynx as I cried out at first then moaned and groaned. I felt wide-cut, I felt totally and somehow it seemed natural.

My face was buried in the bed, and my mitt were outstretched and gripping at the cover. grub was pounding me with long deliberate strokes, almost pulling himself out completely, then ramming it back in. IT felt so dependable to deliver a cock in my ass and I could find the pressure building deep inside myself and in him as his shaft seemed to expound more. He started to scoot his hot steamy load oceanic abyss into my ass and I started to gush out a hot sticky load right into my panties. Chuck 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 shaft into my oral fissure once again and cleaned him off from top to bottom of his shaft that was still erect. I cleaned both of his balls with my slutty mouth ; he tasted so adept, the seraphic salty semen.

I looked into his eyes, and he looked into mine and. I sighed with ease and curled up side by side to him, with my head on his lap. Smiling I began to play with his peter, waving it around, sucking on the head and slapping my own face with its fat long diaphysis and head."SO you are a slut after all !"Chuck said as he slapped me on the ass. I decided to consecrate him some more head and focused on his fat head of, sucking it like a tootsie pop. grub moaned in rapture.

He was still on his back when I swung my schoolgirlish hips over his waistline and placed his stopcock between my ass cheeks. I looked at him seductively and raised my ass so that the tip of his dark monster was right at the entrance to my ass. I asked him what he wanted from his slovenly woman. Chucks response was that he shoved his totally turncock oceanic abyss into my ass. I was in a state of shock ; all I could do was slid down it and rested with his tool in my ass and my balls on his pelvic surface area. He raised his knees so that I had something to lean back on as he grabbed clench of both my iron boot and broadcast my leg apart."Now you're gon na tease 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 bull of his. I was bucking my pelvic arch and waving the hat in the air keeping one mitt on his chest of drawers for support. I was moving up and down and chow pumped like a wild bull's eye. This continued on for about 10 minute of arc, me waving the hat around holding onto his chest while I had his 11.5 inch putz up my ass.

I could finger him start to thrust as if they were his hold up few and knew I was in for a big surprise, 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 chuck and he held me there feeling the deep warmth of his body.
The next morning I awoke around 11am with the taste of cum in my lip and my ass a sore as perdition from the hardcore fucking that happened the Nox before. I looked around and did not see chow, but I could hear him. So I got up and looked around finding him on his balcony on the phone. Chuck grabbed my mitt and pulled me out onto the balcony with him, I was still curry only in my red panty and bra, black stockings and supporter belt

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

"Who was that ?"I asked smiling.

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

I shrugged my shoulders and thought cipher of it. chuck had on his shorts and I still had makeup on my face from the dark before. He dropped his boxers right there on the balcony and his cock was semi-hard. I needed no prompting for what he wanted me to do. I don't know why, but I fell to my knee joint and engulfed his member in my wet warm mouth. It was like it all can natural to me, I started slowly working my natural language over his benighted cock and took as much of it into my mouthpiece and pharynx, probably about 8 in.
Without warning, chow grabbed the back of my head and thrusted forward shoving the rest of his hardening cock down my throat. I could feel my throat stretching as his long boneheaded dick violated my throat. He proceeded to fuck my pharynx slowly ; I gagged a couple of times then was capable to ensure my gagging. I could finger his pubic hairs against my nose and his balls slapping against my chin. Man it felt incredible and I'm trusted it felt better for him since he was moaning.

"Ohhhh ! Take all of it you fucking slut"“ Take my big cock down your slutty throat. Oh you like that don't you ?"grub 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 hungry oral fissure. Then told me to lie down on the lawn chair with my wooden leg over its top so that my oral sex was hanging over the fundament function. I was upside down with my mouth at dick level. eats stuffed his rooster back into my mouth and rammed it down my throat.
"MMMMMMMMMM"escaped my throat as he did.

"Oh bitch, you're a natural turncock sucking working girl !"he said to me.

Chuck was fucking my throat and his big balls were slapping against my forehead. I loved the way he used me and made me find like the slovenly woman I now knew that I was destined to be. He grabbed my leg and pulled them to him so that I was almost folded in one-half. Then he licked two of his digit and shoved them into my ass and I let out a repress moan as he penetrated my man cunt with his deep fingers. I was beginning to gag on his pecker with his fast thrusts, which he must have enjoyed since it made my throat contract. Chuck pulled his cock out of my sass and told me to bear up and I did like the sound trollop that I had become. He sat down and told me to take a buns ; I knew where he wanted me so I straddled him and placed my hungry ass cunt directly over his throbbing cock.

I slowly lowered myself onto his big putz and it was still a tight fit for him to get his prick into my athirst ass. Even though he had ravaged my ass last night. As his putz's oral sex went in past my sphincter muscle, I let out a little 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 demon. I was able to sit all the way down on his cock and I could feel it hitting my behind bone.

I slowly began to rise up on his cock, letting it make out 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 concentrated cock. He was just sitting there with his hands on my pelvic girdle, and each time I went down he pushed me down as far as he could. Then he helped raise me up and our motion became fluid. This continued for about ten hour and I could find an orgasm building in me, as well as chow as he started to groan loudly.

"Oh damn gripe, I'm gon na fill you up, I'm gon na cum"grub moaned.

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

He began fucking me furiously and I felt his cum start shooting deep inside my ass, which sent me over the edge and I began to sprout flow after stream of cum onto his stomach and mine. It was the most acute coming I had ever had, and I didn't even have to have-to doe with my pecker. We slowed down, and I slumped onto him and rested my head teacher on his shoulder joint. eats whispered into my ear,

"I bet you wish your wife could make love 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.

Chuck looked into my eyes and just smiled. I slowly climbed off of his lap, and I felt his still difficult prick pop out of my ass. My mother fucker was gaping wide as his cum began to dribble out and down my leg. I looked at him and smiled then dropped to my knees and started cleaning his big dark cock. After cleaning all his cum from his pecker and balls 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 muscular physical structure giving his cock a lot of attending 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. eats put on some black silk boxers and a armored combat vehicle 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 60 minutes, I prepared myself for Chuck and his night. I went to the can and shaved, put on some mascara, eyeliner, rouge, and red lipstick. I sprayed some fragrance onto my silky politic hide so that I would reek as good as I looked.

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

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

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

The early two smiled and stood up. All three of them were in honest contour. Rick had short pitch blackness hair and a beard and was probably around 6 feet tall and was almost as morose as chow. The other two, Chris and Tom were roughly the same height and weight. Chris had brown hair and a scented grin, and Tom had blonde hair, a powerful bod and was definitely the cutest of the three.
Chuck came up next to me and whispered in my ear"I thought you would like to party tonight. These are my closes friends and they want a go at you."He looked me in the centre and winked. I got a big grin on my typeface, like a kid in a candy shop.

Chris, haystack, Tom and grub all dropped their knickers and I was in Shangri-la. Standing before me were 4 expert looking older men. grub definitely had the expectant cock. rick's was probably the second freehanded at about 9 inches and very thick-skulled. Tom's was probably about 7 in with one hell of a big head on it, and Chris's was about 6 inches, but the juicy one of them all. My heart was pounding in my thorax and my headspring was spinning.

I sank to my knees and gobbled up Tom's cock. I engulfed it and used my glossa to swirl around his head and lick the underside of his cock. I worked my way down to his lump and sucked on both of them at the same metre. By this time all the men were standing around me with their hammer in their hands getting harder by the second. I was still sucking on Tom's cock as I grabbed kink's and Chris's shaft and began to jerk them off. I began to deep pharynx Tom as he grabbed the slope of my pass and began to be intimate my mouth like a race horse at the track. He did this for about a mo until grub told him"Don't dissipation all your energy on his pretty sass, his ass is very tight and just begging to be fucked."

I looked up at Tom and he smiled as he saw my somewhat eye looking up obediently like the slut I was. I removed my mouth from his cock and began to function on Chris's fat hammer. It was so fat that I could barely get my sass around it. I thought that sucking a soda ash can knock down my throat would be easier. I was really enjoying the feeling of being used and being treated like a slut and thought what Betty would say if she could see me sleep together.
By this time, Tom had moved behind me, pulled my rosehip up so that I was knack over and had lifted my chick. He pulled my step-in to the side and began to lick at my ass. It felt so incredible to cause my ass rimmed while I had a fat cock stuffed in my rima oris and two men standing on either side of me with their cocks in my hands.

"flavor how much the strumpet loves this."Chris said."You have a great strumpet here."crick complimented Chuck.

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

I must experience been a slew to see, here I was dressed as a slut. I had a fat pecker in my mouth, and one now completely buried in my ass, while simultaneously jerking off two men. I felt whole, 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 patch saying"Oh dogshit is this slut tight. She is so lucky to be being shared by grub, you love this don't you bitch ?"I mumbled"mmmmmmm"with Chris's putz still in my mouth. Chris Pulled his cock out and slapped it on my buttock, making a"thwack"speech sound every metre. He moved aside so that Rick and my Chuck could use my mouth. My eye popped wide of the mark when instead of them taking turns, they got face by incline and pushed both their shaft into my mouth at the same prison term. Man it was incredible, I slurped and sucked happily on the two big cocks ravaging my mouth.

They then started fucking my mouth, as one would rip out, the other would force in. It was an amazing feel. All the piece, Tom was behind me fucking my ass, his stride increased as he watched Chuck and haystack fuck my mouth. Chris was standing on the side of me jerking his prick. I took my right hand and pushed his divagation and began to flick him. I couldn't even get my hand around his fat rooster. I could feel Tom thrusting harder and deeper, then all of a sudden I felt him explode deep in my ass as he let out a loud moan. He slowed down then pulled his stopcock out of my ass. He shot so very much that I could experience his cum dribbling down my leg.

As he moved, Chris took his place. He sat down on the bed and gently pulled me on top of him. I was now hovering above Chris's pole while Chuck and kink facial expression fucked me. Chris guided my ass down onto his fat cock and I had to concentrate on my ventilation since his cock was so big it felt like he was splitting me with a bat. Rick pulled his cock out and I focused down on Chucks, but only for a here and now because it was replaced by gobbler. I tasted his come and my ass and gladly cleaned him up. I was so ruttish ; they could get done whatever they wanted to me.

Chris had stuffed all of his fat cock down to its base in my ass and was pulling me up so that I was riding his putz and sucking two others at the Same time. Chris did not last as long as Tom had, probably because he had fucked my mouth the foresighted. I could experience his cock grow bigger and elaborate inside me, then it burst filling me with his seed. He was not very long, but fucking red cent he shot off a lot of cum. There must have been about 9 or 10 spurts of hot, viscous, thick cum pumped into my ass.

His tool began to get diffused and I stood up and he popped out of my gaping dickhead, now his cum literally flowed out of my gaping man cunt. grub 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 goggle hole. He pulled me down without warning and impaled me on his massive 11.5 inch monster. I let out a flash"yip"as he hit my after part bone with his gigantic cock. He laid back then pulled me back so my rachis was on his abdomen. He bent his legs lifting my ramification into the air and draped over his knees. Rick stood there looking between our wooden leg and lifted my ramification completely into the air and spread them wide. I looked haystack in the centre and gave him a nod with a grin on my face.

chow's cock already filled with my ass, but Rick now slid his good sized peter into my sore ass. He positioned his dick head right above Chuck's cock and slowly began to promote. At first it was not easy, but he began to campaign harder. I braced myself and tried to labor my sphincter out to allow him easy access. This did help a little, and he was able to push his cock head in my ass. Once he got the head in wrick pushed harder and he was able to push the residue of his cock into me.

I was so bloody horny ! I now had two big cocks deep into my ass, while there were two early men jerking their tool at the lot 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 prick so well that I never wanted it to end. chow began to kiss and bit me on my shoulder which drove me untamed. I started to rock my ass back and forth to fuck their cocks. Chris came over take hold of my head yanked back and shoved his now thick cock back into my lip so that his clump were on my forehead. 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 voluptuous men, while my asshole was being violated by two big men.

They continued pounding at my asshole ; and must have been hitting my prostate because I erupted with such an intense orgasm I thought I would pass out. I felt Chuck and Rick pick up their pace and strength slamming harder and harder into my ass. grub began to spasm as his monster jerked inside me, he dig his finger into my waist and bite my shoulder. He shuddered and moaned as he filled up my ass with more cum than he had the night before. Rick fucked my ass furiously and he too came filling me with wooden-headed hot cum.

Because Rick was fucking my ass so furiously, he was making my unanimous body go up and down. This forced me to throat fucking Chris and Tom. I thought they both would cum in my pharynx, but Chris pulled out and Tom grabbed the incline of my head and shoved his cock down my throat. I couldn't help but gag, and this sent him over the boundary. He shot his endorsement lode straight down my throat and into my stomach. I milked his dick with my pharynx muscleman until he pulled out and Chris replaced his prick. He too pushed his putz 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 nooky weak from the acute 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. grub looked at me, then said.

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

The men all agreed and soon they were gone. As I lay there in a sex and cum induced shock, I saw grub walk over to his T.V. and I freaked at what he lifted from beside it. chuck had recorded the whole matter ! It turned me on knowing that now I was really a slut and it was all on tape.
eats smile down at me wickedly and I knew then that he had the last say in what happened to me. He was now my"Daddy ”, my"pimp ”, and my"Lover !"He lay down beside me covered me up and carry me crocked smiling…..
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