Dressing Up For Him

latinluva

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When I was 18 years old, I started a new job at this Mexican restaurant. I was hired on as a bus boy, cleaning tables and serving chips and salsa. I am fairly cute, 5'3" 125 lbs., sexy lips, eyes are soft and inviting, and my body is firm, curvy with an ass that would make any man leak in in his pants. my downside is, I'm shy, nervous around other men and my penis is tiny....like 4 inches erect tiny. I am very fashionable and love dressing sexy, as sexy as a guy can dress without being overly gay. I mean, I'm not new to the sex scene. I've jerked off with other guys my age, tried some light anal penetration with my fingers and small toys. But nothing prepared me for my experience with Jason, Jason was my manager at the restaurant. He was about 6'4" 225lbs and slightly rugged. He was white and had great arms with hair and a slight muscular build. Jason was about 45 and loved hot young chicks. He was always bragging about fucking some of the girls he'd hired. Once in a while he'd mention how short we were on new hires, especially females. "Fuck, I need to hire some hot chick as bus girls".
He looked at me and said, "Why couldn't you be a chick?" Then laughed, I looked at him and thought, "Fuck, I'd your cock so good if I was...".

A couple of weeks later, Jason told me that he'd hired a new girl, about 20 years old, super sexy and horny as fuck I guess. Cause just before closing, he came out from his office bragging about how he'd just fucked her. I said, "Shut up , no way!". He said, "Here smell this!" As he proceeded to put his fingers to my nose. Wow! That pussy smelled so good, I was like, "Fuck, I wish I could fuck her!". A few days went by, and I saw her going into his office, it was a lil slow in the restaurant, so I took off to the bathroom where I started masturbating, someone called me up front for a while. When I returned to the bathroom, I started masturbating again. I was so into thinking about Jason fucking that new girl, that I didn't even notice him enter the bathroom. He opened the unlocked door and caught me wanking. "WTF are you doing?". I said, "Oh shit, I'm sorry!". "I couldn't help myself, the ideal of you fucking that new girl, I mean I saw her go into your office!". There was a long pause of silence..............then he said, "You wanna suck on it, I still have her pussy juice all over my cock?". He unzipped his pants, pulled out his large uncut cock and forced me to my knees by pushing on the top of my head. The taste was amazing, her juice were still wet from his cock being so deep. It didn't take long before he shot his load all over my face.

Jason eventually had to fire that girl, she was always late and never worked, but fucked Jason a lot. After Jason and I had our lil episode, things got weird over the next month, then one day he came to me and said, "You know, if you were a chick, I'd fuck you so good. You could be my lil bus girl!". I was super confused by that statement, I mean what was he trying to tell me? A few days later, he walks up to me and asked,"You wanna come over for a beer after work?". I told him, "Sure!". Not really knowing what the purpose of it was, but I was gonna find out.

We entered his place and had a few beers, "So, have you thought about what I said, you know about being a chick and letting me fuck you?". I nearly choked on my beer, and replied, "Oh you meant that?". He said, "Uh yeah, look...you are cute, but I'm not into guys. So I figured if you dressed up like a girl, that would really help me get off!". "Look, if you don't want to, that's fine....but I know you loved sucking my dick!". I thought, "Fuck! He's such a manipulator, how does he know I want his cock?". So I asked hesitantly, "What do you have in mind?". He said, "Look, I have a friend, and she's really good with make up....so I'm gonna have her help you on your day off". He gave me a list of things to buy and some extra cash, and told me to be here Friday night at 7 pm and dressed up. I had to buy a wig, heels, fish net stockings with garter belts and lace thongs along with a top and ruffled short dress that mimicked a server at a restaurant, my nails were done, oh and hoop earrings. I was all lotioned up with the sweetest perfume. I have to admit, I looked very sexy and felt amazing. It was as if I got all dressed up for cock.

I pulled up to his place and knocked on the door, he opened and said, "Well look at you you sweetie, don't you look hot.". I was like, "Fuck I feel sexy and ready for anything.", "So this is what it feels like to be a woman!". I loved it, it was making my cock soil and leak. The best part is, I knew what I was coming here to get, there was no guessing what was underneath those clothes. We took off to his room, he groped me all the way there, and as we stood at the foot of the bed, he ran his hands all over my petite sexy body. Slightly tugging on my thong just under my skirt. He shoved his tongue down my throat and I could feel more precum surface to the tip of my cock. I swear I thought i was going to cum. My asshole was already relaxing, as if it knew what was coming or cumming. He had the room all set up a good time, lube on the night stand and porn on the TV. The lights were slightly dimmed. I undressed him and fell to my knees where I took his cock in my mouth, sucking on it like I had been sucking cock for hundreds of years. He told me, "Fuck you know how to suck cock, you look so hot!". I devoured his balls and worked his cock, all while stroking my tiny dick! I could feel my juices in my hand and taste his in my mouth. As he pulled my up from my knees like a gentlemen, he said, "Lets get you up here on my bed sweetheart, I wanna eat that ass and suck on you big clit". I was like, "What? Did he just say big clit?". Who cares, I was so horny that it didn't matter what Jasons said....I was his lil bitch tonight. He ate my ass and I almost shot my load, flipped me over and took my lil dick...I mean big clit in his mouth. "Oh Gawd....please eat that pussy for me....feels so good baby!". He had my legs up and my thong pulled to the side...and I was biting the pillow and grasping for sheets as he had my body in over drive. He lifted my hips and pulled my panties down, leaving me exposed and vulnerable. He flipped me on my stomach raised my hips as I heard the bottle of lube get pumped for preparation. He moisturized his cock and rubbed some over my asshole, continuing to finger my asshole in hopes of relaxing me even more so. But I was ready, I needed this, I wanted this and I was gonna fuck him like no other woman has ever fucked him. He begin to slap his cock all over my ass, sliding it between my cheeks. It was getting harder every time he slapped against my ass. He asked me ,"Before we get going, can I aske you for one more favor?". I said, "yeah, sure...what is it?". He asked, "Could you put this on?". "What is it?". He said, "It's a chasity, it will make things better for me. I promise you won't regret it.". I obliged and we continued.
It did feel sexy, as if he was telling me, no cock, no dick...I love pussy! i laid on the bed again, as he climbed on top of me, full body to body contact. He asks, "Okay, are you ready baby girl?". Oh my Gawd, that drove me crazy, I could feel him lift his hips up, just enough to pull his cock forward and slowly enter my asshole. I was like, "Whoa, bay go slow, it hurts!". He was so good at listening to me, it took a while but he managed to get most of it in. I have never felt anything like this, he was definitely working with a magic stick. it took a few minutes, but eventually my lil pussy open up like a full bloom flower, taking every inch balls deep. I was saying things I thought would never come out of my mouth, "I fuck yeah baby, gimme the dick, gimme the dick Daddy!" and "I can take it all now, I can it all now....fuck you're so deep!", "Oh fuck yeah Daddy, I wanna have your baby, gimme all that nut inside of me....make me a mother!". We fucked for a good hour and all that dirty talk drove us crazy, he yelled, "I can feel your guts, that's how deep I am bitch!" and "I'm gonna make you my Queen of spades". I was like huh? Anyways, it wasn't long before he was pounding my ass harder, shoving deeper, slapping his balls against my chasity and grunting about how he was gonna dump his white seed in my man pussy. The bed was squeaking, I'm sure the neighbors could hear us, then he let out a big moan and grunt, as he released millions of sperm inside my hole. Though his strokes got weaker, his cock stay hard, I'm sure there was more cum leaking out with every stroke. We stayed like that for another five minutes or so, before he flopped all his body weight on top of me, cock still throbbing inside of me. after he pulled out, he begged me for that cum, "C'mon baby, push that cum out of your pussy!". "That a girl, let Daddy see that big load of cum.". I wasn't sure what he was asking for but I assumed he wanted me to push that cum out of my ass, so that's what I did, and it came oozing out of my ass as he gathered it all up and re-inserted back into my ass with his cock. Fuck that felt good.

We saw each other like that every Friday at 7pm, I really fell in love with Jason and our situation, you know, dressing up like a slut for him. But things got weird after 4 moths or so, when he invited a friend over and asked me to let him fuck me like I let him fuck me. Now I know why he called me his l Queen of spades. Jasons friend was a handsome black man, with a cock that would split open anything it tried to enter. Well, that's a whole different story. From that point on, Jason was setting up fuck sessions with men, and I realized that he wasn't in love with me, at least not like I was in love with him. I would do anything for him.....but it just got weird. He must have set up ten or so fuck sessions with acquaintances. I was tired of being used like that. Anyways, it's been many years since Jason and I fucked. But one thing I have learned to enjoy, is dressing up like a lil bitch and making a satisfying a man that know s how to treat a lady.