Man, I really DO feel like a woman

As a young boy, i had always been intrigued by women's clothing. More so, the colorful panties that all these girls wear. But what really got my attention more than anything else was the ever so sexy and sultry thong underwear. It amazed me to see how the thong can just go up a girl's ass and make it look sexy. And of course I wanted to know what it was about the thong that girls liked wearing them, other than the current excuse of so that the panty line doesn't show through their pants. I am sure it is because they love to feel something stringy and thick ride up their ass crack, which is the main reason why i began wearing them after i bought a pair of them at a department store nearby my home. 

as i turned 18, i began feeling more and more the urge on how it feels to dress like a girl, seeing them in tiny skirts during the summer that is so short, you can see just a bit of their ass cheeks pop out from under their skirt, and also to my surprise, most girls i see in tiny tiny skirts wore thongs, and that's when the cross dressing fetish really began right after high school. As I started going to college, I moved out of my parent's home, and settled in a studio apartment close to the school. It's pretty small, but at least i could finally have privacy to do whatever I wanted to do.

Then the thought hit me so quick. why not buy some girls clothing and see if it makes me feel sexy. After all, i really wanted to feel what that song that shania twain sang that time, you know the one saying "Man, I feel like a woman". So why not give it a shot?

So I went to a department store a few blocks away from my apartment complex. As I went in, the first thing I did was dart to the juniors section and began buying all these sexy clothing that young girls wore. First let me begin by describing myself...i am a 5'5 latino boy, a bit voluptuous (or thick in body mass), but i got a plumpy ass so round...well, i will get to that shortly...but anyway...

First, I bought a few of the tight butt hugging bell-bottom jeans...4 actually. all at a size 10 short, so that the leg fabric won't drag on the streets. Then I bought some t shirts that had to look like anyone can wear it since I didn't want to completely "open" myself up yet. And besides, I wasn't thinking about if i was actually gay...instead I saw myself more of a cross dressing straight person, and in truth i was hoping to find a girlfriend who would accept me for what i wear as well as for how much she loves me in general...

well, after the outerwear, i darted to the skirts and bought a short pleated towel-like fabric black beach skirt that was really short that even when i bent down one or two inches, my ass cheeks would show. Also I bought a white pair of the same material. As soon as that was done, i zipped to the panties section, and that's where i did the most of the shopping. I bought about 50 thongs, all on clearance, since I didn't want to spend 20 bucks on only 3 pairs, even if it was a good deal, still it was a bit expensive. and besides, it wasn't like i was going to attract any guy yet...or so i thought...because as I was loading up my cart with my 50 thongs, all at 1 or 2 bucks a piece, as well as a few tanga or samba brazillian bikinis that ride up my ass as well, i was getting checked out by an older man who was with his wife in the panties aisle.

This man looked about in his mid 40's, or maybe in his early 50's, and was a black guy. Pretty tall too, about 6 foot 1 or something, and he was pretty built too. As he kept looking at me, i was getting really nervous to the point where i began sweating profusely because....I didn't know what to do at the time. I wanted him to notice me (or any guy for that matter) and i wanted him to lust me too, but also i began to fear about he might just be plaing with my head and see if i would react sexually to his sexy smiling dirty brown eyes, which i wanted to so badly. Then he came up to me and looked to see if his wife disappeared into the petites section so that he could "chat" with me for a bit. 

"Buying those for yourself?" he asked.

"uhh...well...not really. it's kinda for my girlfr--"

then he abruptly whispered to me "you don't have to lie, baby. i know they're for yourself, and believe me, for a little boy like yourself, i'm sure you got a sexy booty that's so round like a girl's ass would be. I can't stop checking your hot ass, baby"

That really got me shaking to the point where I wanted to faint, but he told me to relax, as he rubbed my back with his hand, sliding it down to my ass and then slipping his thick big hand into my flare legged jeans, but these were a bit loose so that i wouldn't give my parents any wrong idea about be liking to dress up like a little girl. Then he began squeezing my left ass cheek, and began feeling the fabric of my panties. I actually had a bikini on, but this bikini was like those that rode up my ass, so he pulled the fabric up in my ass, which, embarrassingly, caused me to moan slightly. While stroking my ass cheek, making sure it was safe again and that there were no cameras in the area, he pulled me into the fitting room right in front of where i was buying my panties. we quickly went into a room and locked it and then pulled his pants down to show me his thick black cock. I've seen cocks before but being plowed into a girl's snatch, but never have i seen a cock in the flesh. This made me want to explore another thing, the thing that would determine the outcome of me...to feel what a girl feels when she gets fucked deep inside her, even if it's in my ass. 

His dick was thick...and cut. about 9 inches and about as thick as a trial size axe deodorant spray in circumference. He asked me to play with it. So I did. I began massaging his tool to the point where it grew thicker and thicker and began leaking out pre cum out and letting it drip onto the floor. I wanted to suck it so without waiting, i slowly let my tongue approach his cock and began licking his head and tasting his pre cum. 

"ooohh baby, you're making me wanna fuck you now. you mind if a 55 year old man fucks a little boy like you?"

I said I just turned 18 last week to him. But I didn't want to tell him that I was a bit nervous into just telling him to fuck me, although my insides were desperately wanting his cock drilling in my ass.

So then he stopped me and told me to wait for him in the counter because he was going to tell his wife that he forgot his cash at home and that he was going to go back for it so that he could use it to pay for their dinner tonight. although the real truth was he was gonna make me feel like a woman in bed. 

So as I was about to pay for my clothes, he stopped me and said "i'll pay for it. I'll do it because i just gotta see you wear those for me" he whispered.

I was about to pay 300+ dollars on all my clothes and i felt really bad i made him pay for all of it. but he insisted so i didn't know what else to say to him other than thank you.

So he drove me to my little apartment and asked me to do a little runway modelling to him in my new clothes.

So first I put on my bell bottom jeans that were really bell bottomed, unlike those flare jeans that aren't so bell bottomed, and this one was nicely tight on my ass that the thong i was sporting on as well, the lines were showing through the jeans. I thought jeans wouldn't show much of the lining...but oh well.

So I walked to him, turned in a circle so that he could see all of it and asked him how it looked. He just slapped my ass, making me let out an 'ooooooooo' and told me to put on the white skirt and then he will tell me what he thinks.

I knew where he was going with that. 

So i left my black and white striped thong panty on and slipped on my white skirt and walked to him again asking him how it looked. But before I could turn completely, he stopped me with my back showing to him. He lifted my skirt, began softly carressing my thonged up ass cheeks, while he "french kisses" my ass cheeks and began saying:

"baby, this is what i meant by you looking hot. you are so damn sexy for a little boy. you should have been born a girl. just looking at your ass makes me wanna fuck you and show you what girls are made for"

That really made me wet, more so by feeling his hands gently rubbing on my ass and making my nerves jolt with each kiss he gives my ass.

Then he pulls out his cock and told me to continue where i left off. So I began slowly going down on him, licking the head and completely covering the head full of his precum...then shortly i began to slowly engulfing his cock in my mouth, slowly bobbing my head up and down on his thickness, and enjoying the feeling of his thick hands on my ass cheeks while i suck him a bit steadily. 

"ooohh...you suck so good baby. a lot better than my wife does. oh daaaaaaayyyuummm, you were meant to be a girl. mmmmmmmmm come on suck my dick a little more. go deeper on my cock baby girl".

And with that, i slowly began to deep throat him, as much as i could, trying not to gag but everytime i did that, i would gag. So I had to stop deep throating him. Then he told me to get on my knees on the mattress i am sleeping in. He went to my bathroom and took out my vaseline, and told me "you know what, you really have been ready for this huh? you know that the vaseline would let my dick slip right inside you without so much pain?"

I had no idea, really. But regardless of it, i was on my knees, my ass up in the air with my thong on, and then, he got a pair of scissors and cut a hole on my thong that would let his dick slip right through it. Slabbed some vaseline on his thick as fuck cock and then slipped some inside my ass and moved his finger in circles to get me lubed. I began bucking to the feeling of his finger lubing me up in circles. 

Then i felt his finger slide out, and then he said "this might hurt, but i guarantee you will never want me to stop after a while."

He grabbed my hip with one hand, and positioned his cock with another, and then began sliding his cock inside my asshole slowly. feeling his dick slide inside me made me clinch my teeth in pain, and i really wanted to tell him to pull out. But he knew i would feel the pain which is why he told me to relax. it's like when a girl gets her cherry popped for the first time, it's always an excruciating type of pain. No kidding. I wanted to cry. 

So as soon as he was able to slide about six inches inside me, he began to relax on top of me so that I could take a few minutes to adjust myself. after about 5 minutes, he began rocking my ass. I was still hurting a bit.

"oooowwww...mmmmmmmmmm...wow that hurts but it feels so gooooooooood" i moaned.

"see? i told you it would feel good. you'll get used to it in a few more minutes, by then your oowws will turn to oooooohhh, ok?

ok i said.

He started out slowly on me, pumping my ass on his cock, still feeling a bit of pain...but after 10 minutes, i let out my first "oooooooooohhhh" to him.

"mmmmmmmmmmm...yeaaaahhhh...yyeeaaahhhh....so this is what a girl feels when she's getting her brains fucked out"

"oh yeah baby this is what a girl feels. my wife always loves that feeling" he said as he kept on with the rhythm.

"mmmmmmmmmmm....baby...you got a hot ass...you were really meant to be a girl...dammmnn...your so fucking gorgeous...i wanna make you feel like a woman" he serenated to me.

"mmmmmmmmm yeaaaaaaaaaahhh...fuck meeeee...fuuuuckk meeee...make me feel like a woman....make me feel what she feels gettin fucked so hard"

"oooooooooohhh...i love your hot ass' he said also.

His fucking went on for about 20 minutes, but never inbetween were we bored or quiet. I kept moaning out for him to fuck me.

Then he began going a little faster and made my moans get a bit louder "oooooooooooooohhh..........YYeeeaaaAHHHH....MMMMMMMMMMMMMM....OOOHHH FUCK ME JUST LIKE that...that's right...fuck your baby girl just like that....fuck me like you fuck your wife. fuck me like you fuck your wife...mmmmmmmmmmmmmmmmmmmmMMMMMMMMMMM....yyyyyyyyyyeeaaaaaaahhh!!

Then he stopped, and i began moving my ass to his cock pumping his tool deep into me like a crazy whore.

Then he told me "damn baby you look so fucking hot while fuking you in your thong. you gotta wear a thong everytime you get fucked. guys love seeing a girl in thongs while they get hot, but don't ever take yours off while you get your ass fucked hard....oooooooooooooooo daaammmnnn.....AAAAAAGGHHHHH" as soon as he yelled that, he began fucking me harder 

"YYEEEEAAHHH.....YEEEEEAAAAAAHHHH, FUUUUCKK MEEE FAAAASTEEERR...FUCK ME HAAAAAAARRDDEEERRR....HARDER, HARDER, FASTER, FASTER...MAKE ME A WOMAN AND CUM INSIDE MEEEEEE....CCCUUUUUUMM DEEEEPPP INSIDE MEEEE!!

Then I heard him say Oh yeah bitch, im cumming, oooooooohh...OH OH OH>...Im CUMMING....AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA!!
AAAAAAAAAAAAAAAAAAAAHHHHHHHHHHHHHHHHHHHHHHHHHHHH!! OOOOOOOOOOOOOHHHHH! OOOOOOOOOOOOOOOOOOOOOHHHH!!! MMMMMMMMMMMMMMMMMMMMMMMMMMm!!!!

With that, he came hot and hard and full of it. As I felt his cum, I also climaxed, creaming up my thong panties so damn much, they got so damp. I felt his cum comming in jet loads, and it felt like thick squirts, one after another....my desire was fulfilled. my fetishness really paid off and with such good reason. Shania twain was not kidding! Man, i really DO feel like a woman after this heavenly lusty fuck in my ass in cloud 9. MMMMMMMMMMMMMMMMMMMMMmm i needed it again.

He laid on top of me for about 15 minutes, still rock hard, believe it or not after he had come so massively deep inside me, pumping my ass slowly to make me feel wanting more of him, but then he pulled out, letting all the come slip out of my ass. 

"How do you feel now sexy?"

"I...i feel like a woman now. all thanks to you and your cock."

"Baby, i loved fucking you today, and i really wanna fuck you every chance we get. this won't be the last time you'll feel my cock dumping out my lust inside you, so please make yourself available every night after i head home from work so that i can fuck your hot little baby girl ass!"

"I will, only for you."

So that said, it's been one year since he met and fucked me at the same time. Since then, he would always come to my apartment at about 11 at night from his job and always relieve his tension by letting out his come deep inside me while i wear my thongs for him. Still to this day, not his wife nor my parents nor ANYONE who we know, know about our little fuck buddy relationship. And although i do have about 6 sex partners, all in their late 30s to late 50's, always leaving their come inside me (i never fuck by the way...as the girly type that i am, i suck and get fucked like girls do), no one can compare to my first fuck partner. And I am glad he still fucks me to this day and never have we gotten sick of each other. 

I am glad i know how a girl feels when they get their brains plowed by a thick cock. now...if you'll excuse me, he's actually knocking my door...and it is him. ready to fuck me again...and AGAIN.

I wonder since i like sex this much, i wonder if i should just get a sex change...eehh...maybe soon but...right now i am comfortable to be what i am right now as long as i always get some. bye now.