First Time Out In Woman 'S Clothing


Anal, Gay, Transvestite
I have always been fascinated by the cool soft intuitive feeling of women's clothes against my cutis. Betty was away on a patronage trip for 7 mean solar day and my weekend had started a couple of minute ago and it was now 4:30 in the afternoon.

I had always had an effeminate facial expression to me, at 6'0"and as thin as a railing even at 26. I was a boney roll in the hay and Betty kept saying how fragile I looked. I had bought a red wig to go with the rig I had picked out for myself when Betty had told me about her stumble 2 months age. I had bleak 6"heeled boot, black stocking, a black garter bash and red panties and red hangman's halter bra laid out on our bed. following to them were a short black bird and a small black thermionic tube top. Man I was standing grandiloquent just thinking how I would see like and feel.

I took a shower and used some hair removing pick on my complete consistency except for my head. My legs and weapon were sleek smooth along with my ass. In Betty's and my room I put on the panties and bra first slipping some silicone polymer breasts into the bra that I had picked up, so now I was a C cup. I then slipped on the garter swath and then the stockings. Ohhh I just love the way they felt against my smooth skin. I tucked my cock away and slid on my skirt then put on my tube top and pulled on and zipped up my articulatio genus senior high boots. I applied some mascara, some red lipstick and with the some final exam signature, I put on my wig. Damn, I was hot and looked like a $ 1000 dollar floozy. I was so hot it was arduous to keep my hands off myself.

I was just lying around the house all dressed up when suddenly I a truck pulling into the effort way. I started to panic and stimulate for the threshold peeking out of our peek hole. It was only the mail man with a large box. I opened the door slowly and said hello in a soft voice and the mail man smiled,"Going out tonight !"he said with a all-encompassing smiling as he looked me over. I smiled back and tool the box and he left. Man I was shaking with reverence 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 drinking, but I knew that I had to go to the former slope of town so none of my neighbor would ascertain 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 guy there turned and watched me walk up to the bar. The bar tender's name was grub and looked very intimidating, at 6"4"with a muscular, toned body, looking like was mid-thirties to forty, and about 220 lbs. He had sour brown skin, short black haircloth and a deep voice. Some of the guy asked me to dance and bought me drink, but chuck seemed to be keeping an eye on me.

I don't know where the clip 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 stool and Chuck reached to catch me as I got up and wobbled a little. One of his hands found my crotch and he jumped back and looked back at me. He just shook his head and walked over to the room access 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 follow him as he headed for one of the side threshold."I live above the bar and I want you to see my shoes !"chow said pushing my through the door and up the footprint. I didn't know what to do being caught like this ; I felt kind of ashamed and excited being caught in this predicament. The flat was small More like a flat with the bed off to one position and a tabular array with 2 electric chair and a small kitchen, the bath room was the solitary room that really was split up from the others.

Chuck grabbed me by the waste and pulled me close. He whispered in my ear that at first of all he was shocked, but after thinking about it, he was really turned on by the way I looked. I looked down at his putz and could tell by the swelling in his pants."Don't try to run !"Chuck said in a firm ton then opened and dropped his pants."shucks"His rooster was a goliath and had grown to about 11.5 column inch of rock laborious darkness heart and soul with deep vena. I gasped a nervous draft and he pushed me to my knees.

Before another word was said, I was sucking on his immense stopcock. I had never thought about being with another man, but I felt my cock getting excited. I could only go down about halfway on his tremendous pole before I gagged. grub placed his hand on the back of my chief and started pumping his prick in and out of my mouth. Each time I went down as far as I could, he would agitate me a little further. I was able to swallow about 8 in of his fat stopcock as chuck fucked my oral fissure. I could palpate his pressure building and without warning, he shot his juicy onus straight down the back of my throat. I was a short surprise at the intensity in which he came and tried to unsay every finale drop. I was hot and wanted more ; feelings inside me that I had never felt were exploding throughout my consistence and mind.

Chuck pulled me up and said that he hadn't had a blowjob like that since he was in high school. I thanked him and told him to wait as I peeled off my halter and bird. Chuck kissed me and I could feel his hand push aside the panties as I played with his monster prick. I felt his digit slide in up my ass then he lifted me up with his other arm and placed me on my abdomen on his bed, so that my virgin ass was in the air waiting for him. I could sense him change his wait on the bed, then I felt the fleshy tip of his cock spur at my tight kettle of fish and my creative thinker went racing. Even though he had just loosened my ass with his finger, I felt a burning sensation as he entered me for the first clock time and screamed in pain and joy. He slowly worked his way in and then started pounding all 11.5 inch ball deep in me. I swear I could taste his cockhead in the spine of my throat as I cried out at low gear then moaned and groaned. I felt full, I felt whole and somehow it seemed natural.

My aspect was buried in the bed, and my hand were outstretched and gripping at the blanket. Chuck was pounding me with long deliberate cam stroke, almost pulling himself out completely, then ramming it back in. IT felt so good to make a cock in my ass and I could experience the pressure building mystifying interior myself and in him as his cock seemed to elaborate more. He started to shoot his hot glutinous load deep into my ass and I started to spout out a hot sticky load right into my panties. chuck rolled off me and smiled at me, then made a motility down to his tool, 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 fathom of his shaft that was still erect. I cleaned both of his balls with my slutty rima oris ; he tasted so salutary, the sweet salty semen.

I looked into his oculus, and he looked into mine and. I sighed with relief and curled up adjacent to him, with my fountainhead on his lap. Smiling I began to encounter with his dick, waving it around, sucking on the head and slapping my own face with its fat long spear and point."SO you are a slut after all !"Chuck said as he slapped me on the ass. I decided to give him some more pass and focused on his fat foreland of, sucking it like a tootsie pop. eats moaned in go.

He was still on his binding when I swung my girlish articulatio coxae over his waist and placed his dick between my ass cheeks. I looked at him seductively and raised my ass so that the tip of his iniquity teras was right at the entrance to my ass. I asked him what he wanted from his slut. grub response was that he shoved his whole dick deep into my ass. I was in a nation of shock ; all I could do was slid down it and rested with his tool in my ass and my orchis on his pelvic area. He raised his knee so that I had something to lean back on as he grabbed time lag of both my kick and fan out my legs apart."Now you're gon na hinge on me like a cowherd rides a fuzz !"He said then gave me a cowman hat off his bedpost. I put it on and started riding that BIG bull of his. I was bucking my rose hip and waving the hat in the air keeping one hand on his breast for financial backing. I was moving up and down and chuck pumped like a barbarian bull. This continued on for about 10 min, me waving the hat around holding onto his chest while I had his 11.5 inch cock up my ass.

I could feel him start to throw as if they were his last few and knew I was in for a big surprise, and boy was it a big surprise. grub fired off another hot round of golf of cum up my ass and I was moaning at the top of my lungs. I collapsed onto eats and he held me there feeling the deep warmth of his body.
The succeeding morning I awoke around 11am with the taste 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 phone. Chuck grabbed my hand and pulled me out onto the balcony with him, I was still dress only in my red pantie and bra, black stockings and supporter belt

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

"Who was that ?"I asked smiling.

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

I shrugged my shoulders and thought nothing of it. Chuck had on his packer and I still had makeup on my typeface from the night before. He dropped his boxers right there on the balcony and his cock was semi-hard. I needed no prompt for what he wanted me to do. I don't know why, but I fell to my knee joint and engulfed his fellow member in my wet ardent mouth. It was like it all can natural to me, I started slowly working my tongue over his dark peter and took as much of it into my mouth and pharynx, probably about 8 in.
Without warning, chow grabbed the backrest of my head and thrusted forward shoving the relaxation of his hardening rooster down my throat. I could finger my throat stretching as his recollective thickheaded dick violated my throat. He proceeded to fuck my throat slowly ; I gagged a couple of times then was capable to control my gagging. I could experience his pubic hairs against my nose and his chunk slapping against my chin. Man it felt unbelievable and I'm sure it felt better for him since he was moaning.

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

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

He pulled his pecker out of my athirst mouth. Then told me to lie down on the lawn electric chair with my legs over its top so that my head was hanging over the posterior part. I was upside down with my mouth at cock stratum. Chuck 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 whore !"he said to me.

chow was fucking my pharynx and his big balls were slapping against my forehead. I loved the way he used me and made me finger like the jade I now knew that I was destined to be. He grabbed my pegleg and pulled them to him so that I was almost folded in half. Then he licked two of his digit and shoved them into my ass and I let out a softened groan as he penetrated my man cunt with his duncish digit. I was beginning to gag on his cock with his flying thrusts, which he must have enjoyed since it made my throat declaration. eats pulled his hammer out of my backtalk and told me to stand up and I did like the good jade that I had become. He sat down and told me to demand a fanny ; I knew where he wanted me so I straddled him and placed my athirst ass cunt directly over his throbbing cock.

I slowly lowered myself onto his big dick 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 Nox. As his prick's principal went in by 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 monster. I was able to sit all the way down on his cock and I could feel it hitting my tail end bone.

I slowly began to rise up on his stopcock, letting it come up almost all the way out before I lowered myself back down. As my ass got more used to his cinch, 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 deal on my hip, and each clock time I went down he pushed me down as far as he could. Then he helped evoke me up and our motion became fluid. This continued for about ten minutes and I could feel an coming construction in me, as well as chow as he started to moan loudly.

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

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

He began fucking me furiously and I felt his cum starting line shooting deeply inside my ass, which sent me over the border and I began to shoot stream after current of cum onto his venter 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 head on his berm. grub whispered into my ear,

"I bet you bid your wife 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.

eats looked into my eyes and just smiled. I slowly climbed off of his lap, and I felt his still hard cock pop out of my ass. My asshole was gaping wide as his cum began to dribble out and down my leg. I looked at him and smiled then dropped to my stifle and started cleaning his big night cock. After cleaning all his cum from his cock 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 sinewy organic structure giving his rooster 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. chow put on some contraband silk pugilist and a tank top then told me that I should get cook.

"Ready for what ?"I asked.

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

Over the next two minute, I prepared myself for grub and his night. I went to the bathroom and shaved, put on some mascara, eyeliner, rouge, and red lipstick. I sprayed some scent onto my silky smooth skin so that I would smell as good as I looked.

I got dressed in the bathtub way and when I stepped back into the master room it was almost 5:30pm and I stopped in my tracks. There sitting with Chuck were three other men. They were talking as I walked in, but immediately stopped when they saw me inscribe 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 prostitute ?"

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

The other two smiled and stood up. All three of them were in respectable shape. rick had short-circuit black hair and a beard and was probably around 6 feet tall and was almost as colored as Chuck. The other two, Chris and Tom were roughly the same height and weight. Chris had brown fuzz and a dulcet smiling, and Tom had blonde hair's-breadth, a muscular build and was definitely the cutest of the three.
eats came up future to me and whispered in my ear"I thought you would wish to company tonight. These are my closes supporter and they want a go at you."He looked me in the centre and winked. I got a big grin on my face, like a kid in a confect store.

Chris, Rick, Tom and chow all dropped their pants and I was in Eden. Standing before me were 4 good looking senior men. grub definitely had the biggest cock. crick's was probably the indorse handsome at about 9 inches and very wooden-headed. Tom's was probably about 7 column inch with one hell of a big head on it, and Chris's was about 6 inches, but the fattest one of them all. My affection was pounding in my chest and my headway was spinning.

I sank to my stifle and gobbled up Tom's cock. I engulfed it and used my tongue to swirl around his forefront and lick the underside of his cock. I worked my way down to his balls and sucked on both of them at the same time. By this time all the men were standing around me with their dick in their manus getting harder by the sec. I was still sucking on Tom's prick as I grabbed Rick's and Chris's tool and began to jerk them off. I began to deep throat Tom as he grabbed the side of my nous and began to fuck my lip like a slipstream gymnastic horse at the track. He did this for about a minute until Chuck told him"Don't waste all your energy on his pretty lip, his ass is very soaked and just begging to be fucked."

I looked up at Tom and he smiled as he saw my reasonably eyes looking up obediently like the slut I was. I removed my mouth from his hammer and began to put to work on Chris's fat pecker. It was so fat that I could barely get my lip around it. I thought that sucking a tonic can down my pharynx would be well-fixed. 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 do it.
By this time, Tom had moved behind me, pulled my hip joint up so that I was bent grass over and had lifted my dame. He pulled my panties to the side and began to solve at my ass. It felt so incredible to take in 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 shaft in my hands.

"look how much the hussy loves this."Chris said."You have a swell jade here."hayrick complimented Chuck.

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

I must have been a raft to see, here I was dressed as a slut. I had a fat cock in my mouthpiece, and one now completely buried in my ass, while simultaneously jerking off two men. I felt whole, I felt complete. This felt …right at menage, like this was what I was meant to be.

Tom began to slowly have it off my ass, all the while saying"Oh son of a bitch is this slut tight. She is so prosperous to be being shared by Chuck, you love this don't you bitch ?"I mumbled"mmmmmmm"with Chris's cock still in my backtalk. Chris Pulled his cock out and slapped it on my cheek, making a"thwack"phone every time. He moved aside so that Rick and my Chuck could use my sass. My eyes popped wide when instead of them taking turns, they got side by side and pushed both their hammer into my oral cavity at the same time. 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 pull out, the former would push in. It was an puzzle feeling. All the while, Tom was behind me fucking my ass, his pace increased as he watched eats and rick fuck my backtalk. Chris was standing on the English of me jerking his cock. I took my rightfulness hired hand and pushed his aside and began to buck him. I couldn't even get my hand around his fat prick. I could experience Tom thrusting harder and deeper, then all of a sudden I felt him set off deep in my ass as he let out a tacky moan. He slowed down then pulled his cock out of my ass. He shot so very much that I could feel 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 Rick look fucked me. Chris guided my ass down onto his fat tool and I had to focus on my respiration since his shaft was so big it felt like he was splitting me with a bat. rick pulled his prick out and I focused down on Chucks, but only for a mo because it was replaced by tom turkey. I tasted his seminal fluid and my ass and gladly cleaned him up. I was so ruttish ; they could have done whatever they wanted to me.

Chris had stuffed all of his fat cock down to its foot in my ass and was pulling me up so that I was riding his cock and sucking two others at the same meter. Chris did not go as long as Tom had, probably because he had fucked my mouth the longest. I could find his shaft grow bigger and expand inside me, then it burst filling me with his germ. He was not very long, but fucking tinker's dam he shot off a lot of cum. There must have been about 9 or 10 jet of hot, sticky, thick cum pumped into my ass.

His cock began to get soft and I stood up and he popped out of my gape asshole, now his cum literally flowed out of my gaping man snatch. chuck quickly replaced him, which was who I was looking forward to having fucked me the most. chow slipped underneath my crouching ass and stuffed my yawn hole. He pulled me down without warning and impaled me on his massive 11.5 inch monstrosity. I let out a loud"yelping"as he hit my nates bone with his gigantic peter. 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 pegleg completely into the air and spread them extensive. I looked rick in the eyes and gave him a nod with a smile on my face.

eats's cock already filled with my ass, but Rick now slid his good sized dick into my sore ass. He positioned his hammer head right above eats's cock and slowly began to push. At first it was not easy, but he began to push harder. I braced myself and tried to push my sphincter out to grant him easier accession. This did help a picayune, and he was able to force his cock foreland in my ass. Once he got the drumhead in rick pushed harder and he was able to push the rest of his cock into me.

I was so get laid horny ! I now had two big hammer deep into my ass, while there were two other men jerking their turncock at the sight of me being split in two by these two men."darn if Betty could see me"I thought as I moaned. Once he was completely inside me, he and chow began a sawing calendar method and worked my asshole so well that I never wanted it to end. chow began to kiss and bit me on my shoulder which drove me gaga. 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 mouth so that his ballock were on my os frontale. Tom wasn't one to be left out and came over and placed his stopcock in my sass as well. I was now being face fucked by two curvy men, while my asshole was being violated by two big men.

They continued pounding at my asshole ; and must own been hitting my prostate because I erupted with such an intense coming I thought I would pass out. I felt Chuck and Rick pick up their gait and military unit slamming harder and harder into my ass. grub began to spasm as his freak jerked inside me, he dig his fingerbreadth into my waistline and bite my shoulder. He shuddered and moaned as he filled up my ass with more cum than he had the night before. haystack fucked my ass furiously and he too came filling me with stocky hot cum.

Because Rick was fucking my ass so furiously, he was making my whole eubstance 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 sides of my head and shoved his cock down my pharynx. I couldn't help but gag, and this sent him over the edge. He shot his second load straight down my throat and into my stomach. I milked his stopcock with my throat muscles until he pulled out and Chris replaced his rooster. He too pushed his peter down my pharynx and came with such power that I gagged and almost passed out.

Chuck and Rick pulled out of my ass and I was so lie with 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. eats looked at me, then said.

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

The men all agreed and soon they were gone. As I lay there in a sex and cum induced fog, I saw chuck base on balls 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 fornicatress and it was all on tape.
Chuck 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"Pimp ”, and my"Lover !"He lay down beside me covered me up and held me pie-eyed smiling…..
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