First time out in Woman’s clothing
Introduction:
I love the feeling of woman’s clothing next to my skin
I had always had an effeminate look to me, at 6’0” and as thin as a rail even at 26. I was a scrawny 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 2 months age. I had black 6” heeled boot, black stocking, a black garter belt and red panties and red halter bra laid out on our bed. Next to them were a short black skirt and a little black tube top. Man I was standing tall just thinking how I would look like and feel.
I took a shower and used some hair removing cream on my complete body except for my head. My legs and arms were silky 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 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 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 hooker. I was so hot it was hard to keep my hands off myself.
I was just lying around the house all dressed up when suddenly I a truck pulling into the drive way. I started to panic and rushed for the door 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 wide 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 other side of town so none of my neighbors would find out or see my. I was going to see if I was hot enough to get the 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 body, looking like was mid-thirties to forty, and about 220 lbs. He had dark brown skin, short black hair and a deep voice. Some of the guys asked me to dance and bought me drinks, 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 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 door 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 door. “I live above the bar and I want you to see my place!” Chuck said pushing my through the doorway 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 small more like a flat with the bed off to one side and a table with 2 chairs and a small kitchen, the bath room was the only room that really was separate 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 tell 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 cock was a monster and had grown to about 11.5 inches of rock hard dark meat with thick veins. 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 cock getting excited. I could only go down about halfway on his enormous pole before I gagged. Chuck placed his hand on the back of my head and started pumping his cock in and out of my mouth. Each time I went down as far as I could, he would push me a little further. I was able to swallow about 8 inches of his fat cock as Chuck fucked my mouth. I could feel his pressure building and without warning, he shot his juicy load straight down the back of my throat. I was a little 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 body 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 skirt. Chuck kissed me and I could feel his hand push aside the panties as I played with his monster cock. I felt his finger 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 virgin ass was in the air waiting for him. I could feel him shift his wait on the bed, then I felt the fleshy tip of his cock 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 sensation as he entered me for the first time and screamed in pain 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 throat as I cried out at first then moaned and groaned. I felt full, I felt whole and somehow it seemed natural.
My face was buried in the bed, and my hands were outstretched and gripping at the blankets. Chuck was pounding me with long deliberate strokes, almost pulling himself out completely, then ramming it back in. IT felt so good to have a cock in my ass and I could feel the pressure building deep inside myself and in him as his cock seemed to expand more. He started to shoot his hot sticky load deep into my ass and I started to spurt 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 cock into my mouth once again and cleaned him off from top to bottom of his shaft that was still erect. I cleaned both of his balls with my slutty mouth; he tasted so good, the sweet salty semen.
I looked into his eyes, and he looked into mine and. I sighed with relief and curled up next 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 head. “SO you are a slut after all!” Chuck said as he slapped me on the ass. I decided to give 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 back when I swung my girlish hips over his waist and placed his cock 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 slut. Chucks response was that he shoved his whole cock deep into my ass. I was in a state of shock; all I could do was slid down it and rested with his cock in my ass and my balls on his pelvic area. He raised his knees so that I had something to lean back on as he grabbed hold of both my boots and spread my legs apart. “Now you’re gonna ride 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 hand on his chest for support. I was moving up and down and Chuck pumped like a wild bull. This continued on for about 10 minutes, 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 thrust as if they were his last 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 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 panties and bra, black stockings and garter belt
“Alright, 5 o’clock sounds great, see you then.” He said, and then hung 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 boxers and I still had makeup on my face 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 knees and engulfed 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 inches.
Without warning, Chuck 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 thick dick violated my throat. He proceeded to fuck my throat slowly; I gagged a couple of times then was able to control my gagging. I could feel his pubic hairs against my nose and his balls slapping against my chin. Man it felt incredible and I’m sure 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?” 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 chair with my legs over its top so that my head was hanging over the bottom part. I was upside down with my mouth at cock 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 whore!” 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 feel like the slut I now knew that I was destined to be. He grabbed my legs and pulled them to him so that I was almost folded in half. Then he licked two of his fingers and shoved them into my ass and I let out a muffled moan as he penetrated my man cunt with his thick fingers. I was beginning to gag on his cock with his fast thrusts, which he must have enjoyed since it made my throat contract. Chuck pulled his cock out of my mouth and told me to stand up and I did like the good slut 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 hungry 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 cock into my hungry ass. Even though he had ravaged my ass last night. As his cock’s head went in past my sphincter, 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 bone.
I slowly began to rise up on his cock, 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 hard cock. He was just sitting there with his hands on my hips, and each time I went down he pushed me down as far as he could. Then he helped raise me up and our motions became fluid. This continued for about ten minutes and I could feel an orgasm building in me, as well as Chuck as he started to moan loudly.
“Oh damn bitch, I’m gonna fill you up, I’m gonna 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 deep inside my ass, which sent me over the edge and I began to shoot stream after stream of cum onto his stomach and mine. It was the most intense orgasm I had ever had, and I didn’t even have to touch my cock. We slowed down, and I slumped onto him and rested my head on his shoulder. Chuck 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.
Chuck 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 knees and started cleaning his big dark 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 muscular 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 black silk boxers 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 Chuck and his night. I went to the bathroom and shaved, put on some mascara, eyeliner, rouge, and red lipstick. I sprayed some perfume onto my silky smooth skin so that I would smell as good 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 guys and said.
“Well, here she is, as promised. Doesn’t she look like such a dirty whore?”
The first 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 other two smiled and stood up. All three of them were in good shape. Rick had short black hair and a beard and was probably around 6 feet tall and was almost as dark as Chuck. The other two, Chris and Tom were roughly the same height and weight. Chris had brown hair and a sweet smile, and Tom had blonde hair, a muscular build 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 eyes and winked. I got a big grin on my face, like a kid in a candy store.
Chris, Rick, Tom and Chuck all dropped their pants and I was in heaven. Standing before me were 4 good looking older men. Chuck definitely had the biggest cock. Rick’s was probably the second biggest at about 9 inches and very thick. Tom’s was probably about 7 inches with one hell of a big head on it, and Chris’s was about 6 inches, but the fattest one of them all. My heart was pounding in my chest and my head was spinning.
I sank to my knees and gobbled up Tom’s cock. 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 balls and sucked on both of them at the same time. By this time 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 cock 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 head and began to fuck my mouth like a race horse at the track. He did this for about a minute 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 pretty eyes looking up obediently like the slut I was. I removed my mouth from his cock and began to work 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 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 know.
By this time, Tom had moved behind me, pulled my hips up so that I was bent over and had lifted my skirt. 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 cock stuffed in my mouth and two men standing on either side of me with their cocks in my hands.
“Look how much the slut 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 protection. Chuck looked at me, then back to Tom and said “Nah, lets fill this little slut up with as much 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 asshole was just begging to be fucked. He began to push his cock 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 cock 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 while saying “Oh shit is this slut tight. She is so lucky to be being shared by Chuck, you love this don’t you bitch?” I mumbled “mmmmmmm” with Chris’s cock still in my mouth. Chris Pulled his cock out and slapped it on my cheek, making a “thwack” sound every time. He moved aside so that Rick and my Chuck could use my mouth. My eyes popped wide when instead of them taking turns, they got side by side 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 push in. It was an amazing feeling. All the while, Tom was behind me fucking my ass, his pace increased as he watched Chuck and Rick fuck my mouth. Chris was standing on the side of me jerking his cock. I took my right hand and pushed his aside and began to jerk him. I couldn’t even get my hand around his fat cock. 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 cock out of my ass. He shot so much that I could feel his cum dribbling down my leg.
As he moved, Chris took his 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 face fucked me. Chris guided my ass down onto his fat cock and I had to focus on my breathing 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 moment because it was replaced by Toms. I tasted his come and my ass and gladly cleaned him up. I was so horny; 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 time. Chris did not last as long as Tom had, probably because he had fucked my mouth the longest. I could feel his cock grow bigger and expand inside me, then it burst filling me with his seed. He was not very long, but fucking damn he shot off a lot of cum. There must have been about 9 or 10 spurts 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 gaping asshole, now his cum literally flowed out of my gaping man cunt. Chuck quickly replaced him, which was who I was looking forward to having fucked me the most. Chuck slipped underneath my crouching ass and stuffed my gaping hole. He pulled me down without warning and impaled me on his massive 11.5 inch monster. I let out a loud “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 legs and lifted my legs completely into the air and spread them wide. I looked Rick in the eyes and gave him a nod with a smile on my face.
Chuck’s cock already filled with my ass, but Rick now slid his good sized dick into my sore ass. He positioned his cock head right above Chuck’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 allow him easier access. This did help a little, and he was able to push his cock head in my ass. Once he got the head in Rick pushed harder and he was able to push the rest of his cock 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 cocks at the sight 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 fuck their cocks. Chris came over grabbed my head 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 well-endowed 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 force slamming harder and harder into my ass. Chuck began to spasm as his monster jerked inside me, he dig his fingers 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 thick hot cum.
Because Rick was fucking my ass so furiously, he was making my whole body go up and down. This forced me to throat fucking Chris and Tom. I thought they both would cum in my throat, but Chris pulled out and Tom grabbed the sides of my head and shoved his cock down my throat. 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 cock with my throat 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 fucking they had given me that I couldn’t even move. I just laid there as the men got dressed and asked when they could do it again. Chuck looked at me, then said.
“How about next weekend, and see if you can get anyone else to 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. Chuck had recorded the whole thing! It turned me on knowing that now I was really a slut 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 tight smiling…..
