First Time Out In Woman 'S Wear


Anal, Gay, Transvestite
I have always been fascinated by the nerveless voiced look of women's clothes against my skin. Betty was away on a business trip for 7 twenty-four hour period and my weekend had started a couple of hours ago and it was now 4:30 in the afternoon.

I had always had an emasculate look to me, at 6'0"and as thin as a rails even at 26. I was a scrawny fuck and Betty kept saying how fragile 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-up 2 months age. I had dim 6"heeled charge, black stocking, a black garter belted ammunition and red panties and red halter bra laid out on our bed. Next to them were a short blackness skirt and a little Shirley Temple metro top. Man I was standing marvellous just thinking how I would look like and feel.

I took a rain shower and used some hair removing pick on my all over torso except for my mind. My leg and arms were silklike 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 love the way they felt against my suave tegument. I tucked my turncock away and skid on my skirt then put on my tube top and pulled on and zipped up my knee gamy thrill. I applied some mascara, some red lipstick and with the some final speck, I put on my wig. Damn, I was hot and looked like a $ 1000 buck floozie. I was so hot it was strong to go on my workforce off myself.

I was just lying around the house all dressed up when suddenly I a truck pulling into the ride way. I started to panic and rushed for the room access peeking out of our glance hole. It was only the mail man with a orotund box. I opened the door slowly and said hi in a soft voice and the mail service man smiled,"Going out tonight !"he said with a wide smile as he looked me over. I smiled back and tool the box and he left. Man I was shaking with fearfulness 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 deglutition, but I knew that I had to go to the early side of town so none of my neighbors would line up out or see my. I was going to see if I was hot enough to get the hombre 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 gens was Chuck and looked very intimidating, at 6"4"with a muscular, toned body, looking like was thirty-something to forty, and about 220 lbs. He had dour brown skin, myopic black hair and a deep phonation. Some of the guy wire asked me to dance and bought me drinks, but eats 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 chow smiling at me."Everyone's gone home base and it only you and I, baby."He said coming from behind the bar. I turned on the bar BM and chuck reached to catch me as I got up and wobbled a minuscule. One of his hands found my fork and he jumped back and looked back at me. He just shook his promontory and walked over to the doorway and locked it.

'' tinker's damn you're hot for a fag ! ”. Chuck said walking back over to me. He took my helping hand, smiled wide and gave me a Yankee to follow him as he headed for one of the side door."I live above the bar and I want you to see my seat !"Chuck said pushing my through the room access and up the steps. I didn't know what to do being caught like this ; I felt kind of ashamed and excited being caught in this predicament. The apartment was pocket-size more like a flat with the bed off to one English and a table with 2 chairs and a humble kitchen, the tub room was the only room that really was break from the others.

chuck grabbed me by the waste 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 cock and could narrate by the bulge in his pants."Don't try to run !"chuck said in a firm ton then opened and dropped his pants."Damn"His pecker was a monster and had grown to about 11.5 inches of rock tough dark kernel with thick veins. I gasped a anxious draft and he pushed me to my knees.

Before another discussion was said, I was sucking on his huge cock. I had never thought about being with another man, but I felt my rooster getting shake up. I could only go down about halfway on his enormous pole before I gagged. eats placed his hand on the rachis of my head and started pumping his cock in and out of my mouth. Each fourth dimension I went down as far as I could, he would push me a little foster. I was able to swallow about 8 column inch of his fat cock as Chuck fucked my mouth. I could feel his insistency building and without warning, he shot his juicy shipment straight down the binding of my pharynx. I was a little storm at the intensity in which he came and tried to eat up every last driblet. I was hot and wanted to a greater extent ; tactile sensation 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 schooling. I thanked him and told him to look as I peeled off my halter and skirt. Chuck kissed me and I could feel his paw push aside the panty as I played with his monster pecker. I felt his finger 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 Virgo the Virgin ass was in the air waiting for him. I could sense him switch his delay on the bed, then I felt the fleshy tip of his shaft prod at my tight hole and my mind went racing. Even though he had just loosened my ass with his finger, I felt a burning whiz as he entered me for the first time and screamed in infliction and joy. He slowly worked his way in and then started pounding all 11.5 inches ball 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 full-of-the-moon, I felt unit and somehow it seemed natural.

My face was buried in the bed, and my bridge player were outstretched and gripping at the mantle. Chuck was pounding me with long deliberate CVA, almost pulling himself out completely, then ramming it back in. IT felt so near to have a cock in my ass and I could finger the insistency building deep inside myself and in him as his stopcock seemed to expand more. He started to fool away his hot sticky payload trench into my ass and I started to spurt out a hot sticky load right into my panties. eats rolled off me and smiled at me, then made a motion down to his pecker, and I knew what he wanted me to do. So I took his prick into my mouth once again and cleaned him off from top to bottom of his putz that was still erect. I cleaned both of his balls with my slutty mouth ; he tasted so good, the sweetened salty cum.

I looked into his eyes, and he looked into mine and. I sighed with reliever and curled up succeeding to him, with my head on his lap. Smiling I began to play with his dick, waving it around, sucking on the head and slapping my own face with its fat long shaft and forefront."SO you are a loose woman after all !"Chuck said as he slapped me on the ass. I decided to apply him some more head and focused on his fat top dog of, sucking it like a tootsie pop. Chuck moaned in ecstasy.

He was still on his spinal column when I swung my schoolgirlish hips over his waistline and placed his tool 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 entry to my ass. I asked him what he wanted from his slut. grub answer was that he shoved his completely rooster deep into my ass. I was in a state of matter of shock ; all I could do was skid down it and rested with his cock in my ass and my balls on his pelvic field. He raised his knee so that I had something to tend back on as he grabbed hold of both my bang and spread my legs apart."Now you're gon na hinge on 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 hips and waving the hat in the air keeping one paw on his bureau for support. I was moving up and down and grub pumped like a wild bull's eye. This continued on for about 10 min, me waving the hat around holding onto his dresser while I had his 11.5 inch peter up my ass.

I could feel him start to thrust as if they were his live 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 oceanic abyss warmth of his body.
The next dayspring I awoke around 11am with the taste of cum in my back talk and my ass a sore as hell from the hardcore fucking that happened the Night before. I looked around and did not see grub, but I could see him. So I got up and looked around finding him on his balcony on the earpiece. chow grabbed my deal and pulled me out onto the balcony with him, I was still coiffe only in my red step-in and bra, black stockings and garter belt

"Alright, 5 o'clock sounds bully, 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 naught of it. chow had on his pugilist 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 prompting for what he wanted me to do. I don't know why, but I fell to my human knee and absorb his member in my wet warm mouth. It was like it all can natural to me, I started slowly working my tongue over his dark cock and took as much of it into my mouth and throat, probably about 8 column inch.
Without warning, chuck grabbed the back of my head and shove forward shoving the sleep of his hardening cock down my throat. I could palpate my pharynx stretching as his tenacious thick dick violated my throat. He proceeded to roll in the hay my throat slowly ; I gagged a couple of metre then was able-bodied to control my gagging. I could feel his pubic hair against my horn in and his glob slapping against my chin. Man it felt incredible and I'm sure it felt better for him since he was moaning.

"Ohhhh ! takings all of it you fucking slut"“ Take my big shaft 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 cock out of my hungry mouth. Then told me to lie down on the lawn chairman with my leg over its top so that my head was hanging over the freighter component part. I was upside down with my mouth at tool level. Chuck stuffed his cock back into my mouth and rammed it down my throat.
"MMMMMMMMMM"escaped my throat as he did.

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

grub was fucking my throat and his big orb 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 peg 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 bitch with his thick fingers. I was beginning to gag on his rooster with his fast thrusts, which he must give birth enjoyed since it made my throat contract bridge. Chuck pulled his cock out of my mouth and told me to stand up up and I did like the skilful hussy that I had become. He sat down and told me to submit a seat ; 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 prick and it was still a tight fit for him to get his pecker into my hungry ass. Even though he had ravaged my ass survive night. As his pecker's head went in preceding my sphincter, I let out a little narrow escape of pleasure. He placed his hands on my shoulders and pushed me down onto his peter, it felt incredible to be filled by such a monster. I was able to sit all the way down on his rooster and I could sense it hitting my tail ivory.

I slowly began to rise 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 Chuck's rock and roll arduous hammer. He was just sitting there with his hands on my hips, and each prison term 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 moment and I could find an climax edifice in me, as well as grub 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 spot, 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 cryptic inside my ass, which sent me over the edge and I began to shoot stream after stream of cum onto his tummy and mine. It was the most intense 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 head on his shoulder. grub whispered into my ear,

"I bet you wish 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 oculus 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 knee and started cleaning his big dark cock. After cleaning all his cum from his hammer 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 hefty organic structure giving his prick a lot of care 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. grub put on some calamitous silk underdrawers and a tank 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 dark. I went to the bathroom and shaved, put on some mascara, eyeliner, rouge, and red lipstick. I sprayed some perfume onto my silky politic skin so that I would smack as honest as I looked.

I got dressed in the bath 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 other 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 cat and said.

"well, here she is, as promised. Doesn't she look like such a dirty woman of the street ?"

The number 1 man, who I later found out was Rick, gave out a wildcat whistle and said"Hades if she doesn't, she is just begging to be fucked."

The other two smiled and stood up. All three of them were in just frame. hayrick had short black haircloth and a face fungus and was probably around 6 animal foot magniloquent and was almost as dark as chuck. The other two, Chris and Tom were roughly the same height and weight. Chris had brown tomentum and a sweet grinning, and Tom had blonde hair, a muscular chassis and was definitely the cutest of the three.
Chuck came up future to me and whispered in my ear"I thought you would wish to party tonight. These are my closes friends and they want a go at you."He looked me in the eyes and winked. I got a big grinning on my fount, like a kid in a candy stock.

Chris, Rick, Tom and chuck all dropped their pant and I was in promised land. Standing before me were 4 secure looking previous men. Chuck definitely had the biggest stopcock. hayrick's was probably the indorsement biggest at about 9 inches and very thick. Tom's was probably about 7 inches with one underworld of a big head on it, and Chris's was about 6 column inch, but the juicy one of them all. My philia was pounding in my pectus and my drumhead was spinning.

I sank to my knees and gobbled up Tom's turncock. I engulfed it and used my tongue to whirl around his head and lick the undersurface of his cock. I worked my way down to his globe and sucked on both of them at the same sentence. By this fourth dimension 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 rick's and Chris's cocks and began to jerk them off. I began to deep pharynx Tom as he grabbed the side of my promontory and began to eff my mouth like a race horse at the track. He did this for about a moment until Chuck told him"Don't waste all your energy on his pretty mouth, his ass is very tight and just begging to be fucked."

I looked up at Tom and he smiled as he saw my fairly heart looking up obediently like the strumpet I was. I removed my mouth from his cock and began to turn on Chris's fat cock. It was so fat that I could barely get my mouth around it. I thought that sucking a soda can push down my throat would be easier. I was really enjoying the look of being used and being treated like a jade and thought what Betty would say if she could see me know.
By this time, Tom had moved behind me, pulled my pelvic arch up so that I was bent over and had lifted my dame. He pulled my panties to the side and began to lick at my ass. It felt so incredible to have my ass rimmed while I had a fat turncock stuffed in my mouth and two men standing on either side of me with their prick in my hands.

"face how much the hussy loves this."Chris said."You have a great slut here."Rick complimented Chuck.

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

I must have got been a sight to see, here I was dressed as a slut. I had a fat hammer 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 get it on 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 gripe ?"I mumbled"mmmmmmm"with Chris's rooster still in my mouth. Chris Pulled his prick out and slapped it on my face, making a"thwack"sound every time. He moved aside so that wrick and my Chuck could use my mouthpiece. My eyes popped astray when instead of them taking bout, they got incline by incline and pushed both their cocks into my mouth 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 other would promote in. It was an vex belief. All the while, Tom was behind me fucking my ass, his stride increased as he watched Chuck and wrick fuck my mouth. Chris was standing on the side of me jerking his pecker. I took my right hand and pushed his digression and began to yank him. I couldn't even get my bridge player around his fat turncock. I could experience Tom thrusting harder and deeper, then all of a sudden I felt him blow up deep in my ass as he let out a gimcrack moan. He slowed down then pulled his cock out of my ass. He shot so practically that I could experience his cum dribbling down my leg.

As he moved, Chris took his position. He sat down on the bed and gently pulled me on top of him. I was now hovering above Chris's rod while chow and Rick face fucked me. Chris guided my ass down onto his fat putz and I had to focus on my respiration since his cock was so big it felt like he was splitting me with a bat. crick pulled his cock out and I focused down on Chucks, but only for a moment because it was replaced by Toms. I tasted his come and my ass and gladly cleaned him up. I was so steamy ; they could have 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 cock and sucking two others at the same fourth dimension. Chris did not last as long as Tom had, probably because he had fucked my oral cavity the longest. I could feel his cock grow great and expand inside me, then it burst filling me with his germ. He was not very long, but fucking red cent he shot off a lot of cum. There must experience been about 9 or 10 jet of hot, sticky, duncical cum pumped into my ass.

His cock began to get soft and I stood up and he popped out of my gaping 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. Chuck slipped underneath my crouching ass and binge my gaping pickle. He pulled me down without warning and impaled me on his massive 11.5 inch lusus naturae. I let out a forte"Yelp"as he hit my tail bone 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 wooden leg and lifted my legs completely into the air and spread them broad. I looked Rick in the eyes and gave him a nod with a smile on my facial expression.

grub's stopcock already filled with my ass, but kink now slid his good sized dick into my sore ass. He positioned his cock pass right above Chuck's cock and slowly began to labor. At first it was not easy, but he began to push harder. I braced myself and tried to crowd my sphincter out to allow him easier access. This did facilitate a little, and he was able to advertize his cock read/write head in my ass. Once he got the head in Rick pushed harder and he was able to labour the balance of his cock into me.

I was so fucking horny ! I now had two big cocks deep into my ass, while there were two former men jerking their cocks at the spate 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 Chuck began a sawing rhythm and worked my asshole so well that I never wanted it to end. chuck began to kiss and bit me on my shoulder which drove me wild. I started to rock my ass back and Forth to have sex their rooster. Chris came over seize my nous yanked back and shoved his now thick cock back into my mouth so that his balls 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 sonsie men, while my prick was being violated by two big men.

They continued pounding at my asshole ; and must give birth been hitting my prostate because I erupted with such an vivid orgasm I thought I would pass out. I felt chuck and Rick pick up their tempo and military unit slamming harder and harder into my ass. Chuck began to spasm as his monster jerked inside me, he dig his fingers 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. kink fucked my ass furiously and he too came filling me with thick hot cum.

Because Rick was fucking my ass so furiously, he was making my solid 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 sides of my mind and shoved his cock down my throat. I couldn't service but gag, and this sent him over the edge. He shot his second lode straight down my pharynx and into my stomach. I milked his peter with my throat muscleman until he pulled out and Chris replaced his dick. He too pushed his prick down my throat and came with such force that I gagged and almost passed out.

grub and rick pulled out of my ass and I was so have a go at it feeble from the intense screw 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 come with you."

The men all agreed and soon they were gone. As I lay there in a sex and cum induced daze, I saw chuck walk over to his T.V. and I freaked at what he lifted from beside it. eats had recorded the whole thing ! It turned me on knowing that now I was really a slut and it was all on tape.
grub 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"buff !"He lay down beside me covered me up and held me crocked smiling…..
Sign-in {% trans 'to add this to Watch Later list' %}
{% trans 'Sign-in' %} to perform this action