My "Uncle" Caught Me in Pantyhose! Pt. 06

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Part 6 of the story of a young crossdresser.
3.5k words
4.54
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Part 6 of the 6 part series

Updated 06/07/2023
Created 11/07/2015
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JHouston
JHouston
455 Followers

"You will make a hot little sissy in those heels and dress." said a man's deep voice behind me.

I was startled. I was shopping alone in a boutique and adult novelty store near my new rented apartment. I had just moved in two weeks ago to be closer to my new college, and, I was picking out a few sexy outfits for crossdressing fun.

I turned around to see a tall dark black man towering over me. He must have been at least 6'4', mid-thirties, attractive and very well toned.

I blushed. "Yeah, funny! These are for my girlfriend."

"Why are you going to lie to me like that, man?" he said in mock resentment.

"I know you are buying them for yourself. Don't you know it is disrespectful to lie to someone?" He said.

"I am not lying. I'm telling you the truth! Why would I lie?" I protested, tying to sound convincing.

"You can't lie to me, man, I spent two years in jail. I know a sissy when I see one. You are going to go home, put on some make up, and these girly clothes, and probably sit on a big fat dildo... I recommend a black one." He said with a wink, then, he walked away.

I was extremely embarrassed by this encounter. I thought I could purchase these items with the cover that they were for my girlfriend. But, I hadn't fooled that black man. He saw right through me. I suddenly felt very apprehensive.

I became anxious to leave the store. But, the black man was right, I did need a dildo. For weeks I had been aching so bad for cock... Roberto's cock... But, I would not see Roberto for at least a month, so, I had to find something that could scratch my itch until then.

I missed Roberto very much. He is my dad's best friend whom I called my "uncle" growing up. In Part I, I explained how he caught me cross dressing in pantyhose one day that he was staying over at my house because of a fight with his wife. My parents were both at work and I thought I was all alone in the house. I put on the sheen pantyhose I had stolen from my mom and walked around the house in nothing, but, that shiny pantyhose.

I wanted to die when Roberto caught me like that! I ran to my room and cried like a little girl. But, Roberto turned out to be very supportive. He did not tell anyone about my secret. He bought me sexy girl clothes and encouraged me dress up in them. Then, when my dad had to cancel a camping trip with me, my 'uncle' stepped in.

Instead of going camping, however, we went to Dallas. First, he took me to a mega boutique and adult novelty store where a make-up lady did my make-up and helped me pick out fake hair and fake tits. She did her magic and I was transformed into a hot young babe, Raquel. Roberto took me dancing and I turned heads everywhere.

We danced, we kissed, we fooled around, and on the second night,... Roberto fucked me... hard. I was a virgin, but, he did not go gentle on me. It hurt really bad. Roberto is very well endowed, and, to make matters worse, he is very dominant and aggressive... He has BDSM tendencies in the bedroom.

He is a nice guy; a very sweet and tender kisser that made me feel like a girl in love. But, he is different fucking. He becomes something mean and scary. His wife was not into that BDSM stuff, so, he used me as an outlet for his demons. I took a lot of abuse from him. At first, it hurt and I felt used and violated,... but soon,... I started liking it... I mean, really liking it... He tied me up, pushed me around, threw me in bed, spanked me, pulled my hair, pinned my head on the bed while he ravaged me doggie-style or pulled my legs up to my ears and pounded me mercilessly with his big and mean cock... and I loved every second of it! We were made for each other.

While I was in community college Roberto and I saw each other about three time a week. But, since I moved from the community college to a four-year university in Forth Worth, we only get to see each other about once each month.

So, here I was in the store buying a few things to wear for him and things for solo play. I had a picked a maid costume, student costume, faux leather corset, g-strings, bras, vinyl garter belt, fishnet stockings, shiny red tights, silver metallic pantyhose and red stripper platform heels. Last thing I needed was the dildo. But, I was very nervous about picking up and buying a big dildo.

I had never bought a dildo before. I looked around to make sure the black man was gone. I did not want him coming back to tease me, again. I made my way to the dildo area and was overwhelmed with how many there were to choose from. I quickly picked one that was about Roberto's size, it said 8 inches, and it was white. It looked realistic with big thick veins and it had a suction base to keep it in place. I grabbed it and darted to the cashier.

The cashier was a white lady in the 50s. She did not ask questions or look at me with disgust. To her, it was like ringing up groceries.

"These are for my girlfriend." I blurted out. I don't know why, but, I felt compelled to say this. She glanced at me for a second, but, I couldn't tell what she was thinking. Did she believe me or was she giving me the you're-not-fooling-anyone stare? She finally said, "Well, she will feel very sexy in these heels and outfits."

I exited the store, and took a deep breath, thinking the worst was over.

"Hey doll." I heard someone say.

I turned around to find the black guy I had seen in the store and he was with two more black guys. One of them was similar in size to him, and the other just a tiny bit taller.

"I'm not a doll", I said.

"How about you dress up for us in your new sexy girly clothes?"

It was dark out. This was beginning to seem creepy. "I have to get home." I said and walked to my car.

I heard footsteps and turned around. They walked over to me, catching up to me before I could get in my car.

"No need to run away scared, doll!" The black man said. "What is your name?"

My heart was pounding. What was going on, here? I have nothing against black people, but, my experience with black people is limited to just a handful of blacks in the town I grew up in. Were these guys thugs? Did they want money? Did they want to rape me?

"I am Rick." I said, trying not to sound frightened, but, my voice was trembling.

"My name is Mike." said the guy that had been in the store. "And, this is Henry and Tony." He said, pointing at the other black as tall as him and the slightly taller one. They were dressed in nice clothes, and did not look like thugs, but, I had no way of knowing right then if they posed a threat. What do they want? - I wondered.

"Hi guys." I said, trying to smile and appear friendly.

They towered over me. I looked up at them, but feeling a little intimidated, I looked down at the ground. I felt so tiny around them. Henry said, "Yeah, he's a sissy alright."

Looking was standing in front of me about three feet away. He said, "When I was in prison, I had a little bitch like you." To emphasize his point, he bent his knees and started acting like he was fucking someone doggie-style, and he used his right hand to imitate an ass slapping.

Taking his cue, Tony positioned himself were the prison bitch's mouth would be, and pretended to grab the prison bitch's head to force his cock in the prison bitch's mouth.

This display was crude and shocking! I felt really uncomfortable and threatened. "I have to go." I said and started walking away, but, Henry said, "Wait, wait, watch this." He pulled his zipper down and he pulled out of his pants his huge cock. It was shockingly big and thick!

I thought Roberto's cock was huge, but, Henry's flaccid cock was as long as Roberto's cock when hard. I guess I stared at Henry's cock a little too long, and, they all burst out laughing.

"See how he stares at it? He is salivating, man!... Licking his lips!" teased Henry.

I was really scared at this point, but, I was also getting angry, and I said, "Fuck you!" which was a big mistake.

The joviality stopped instantly and Henry looked at me menacingly, "What did you say?"

"Sorry, man, I didn't mean it, I just don't like to be made fun of." I said very sheepishly and apologetically.

"Yeah, you better be sorry! You better get on your knees and suck this cock to show me how sorry you are, bitch!" He said.

My heart was pounding with terror and I was beginning to feel sick. I glanced around to see if I could make a run for it or call someone for help. But, it was late and no one was around.

Then, they all burst out laughing again. It was all just a big joke. I pretended to laugh, too."

"We're just playing with you, man, lighten up." said Tony.

"I'm not playing, I really want him on his knees sucking my cock!" said Henry with a serious expression, but, I knew he was joking this time.

His big black meat was still hanging out of his pants and I wanted to look at it, but, I did everything I could to resist the urge.

"Alright, guys, nice to meet you all, but, I really must get going." I said, trying to put on my friendliest and cool voice.

"It's not going to suck itself." said Henry, looking me in the eye and pointing at his cock. I pretended to laugh, trying to ingratiate myself with him.

"Not today, maybe, next time." I said.

He winked at me, and, with some effort, stuffed his monster cock back in his pants.

Then, Tony took a few steps closer to me and said, "Look man, we ain't going to hurt you, just wondering something, though... Mike here said you were buying some girly outfits, so we think maybe you a queer dude, a crossdresser, a tranny."

I was about to protest, but, Tony stretched his hand out to stop me from interrupting.

He said, "Look, it is alright with us... We're not haters, we're money-makers." The three of them giggled.

Henry spoke next, "What my associate is trying to explain is that, we run an upscale private club in town and also an escort service. We've got lovely ladies and good clientele... professionals, like lawyers and doctors and business executives. Lately, we've had special requests from our VIP customers. Some want young boys that dress like girls, you know, trannies and sissies. We've never had that before,... but, different strokes for different folks, right? So, we be looking around to see if we can find a boy that can fill this void,... but, not having any luck... Then,... Mike spots you in the store buying girly outfits."

I was about to protest again, but, Mike came forward and put his arm on my shoulder. Looking me up and down he said, "You've got a petite, skinny and scrawny little body,... you're young,... and you got a pretty girly face. I bet you'll look pretty damn hot with that maid outfit you picked out. Yeah, I saw that... Look, you don't need to start escorting right away,... just, start out as a crossdress waitress in our club, flirt with some of our special customer, then,... when you ready,... you get a promotion to cocksucker." This made them all laugh.

Henry made the final pitch, "You gonna make a lot of money if you join our crew!"

They finally paused to give me a chance to respond. I was blushing and nervous and shocked. I couldn't believe this was happening! In my most masculine voice, I said, "No guys,... seriously,... I'm not what you think. I've got a girlfriend and I bought these outfits for her. I'm a straight dude." I prayed that they would believe me.

I felt a chill down my spine at the realization that these guys were pimps. They did not have to ask nicely for my cooperation. They could beat the shit out of me and force me into prostitution.

The three of them glanced at me for a second, then, glanced at each other. My heart was beating so fast that I felt like I was about to have a heart attack.

"Okay, then." Said Mike.

Henry handed me a business card. It was a slick and classy card, black in the back and color in the front with the name of the club, "7 Deadly Sins" and his name, title of President, and his telephone number. I did not want to be rude, so, I took the card and placed it in my pocket.

Each of them said, "later" to me as they turned and walked away. "See you guys later." I replied.

My hands were trembling and I had trouble putting the keys in the ignition.

I felt my body still trembling when I got home. I sat down on my couch and tried to relax. Then, I felt the bulge in my pants. What?

I was mystified to discover that, not only was I hard, but, there was a big wet spot on the crotch of my pants. I didn't know how long that had been there.

Had it been there when I was talking to the black guys? Did I have a hard-on when I was with them? I was so confused.

A few more minutes passed, and, my mind was going to a very strange dark place. I thought about what it would have been like to get raped by those guys.

I was terrified of this when I was with them in the parking lot... Why was I was eroticising it now.

In short time, my level of arousal was ridiculous. I was so damn horny! I was suddenly overwhelmed with lust for my would-be assailants!

I tore my clothes off and put on one of my new girly outfits - a slutty plaid schoolgirl outfit, white g-string, black fishnet stockings and red stripper platform heels.

I put on a little bit of make-up, but, could not think straight to do more than just basic stuff I could do in five minutes.

I ran to the closet to find my wig and put it on.

I imagined Mike, Henry and Tony seeing me like this and teasing me about what a sissy I was.

I grabbed my new 8-inch dildo and tore it from its package. It seems as big as Henry's cock had been flaccid. It must be a few inches bigger when he gets hard! I thought.

Using the suction cup on the dildo, I got it to stick on the fridge in my kitchen.

I dropped on my knees and closed my eyes. I imagined being pushed down on the ground by them, forced on my knees to suck their huge black cocks!

Their cocks are so big and juicy, I can hardly open my mouth big enough for Henry's, but, he yanks my hair, and this makes me open my mouth wide for him.

I take the big dildo in my mouth and let the dildo fuck my face.

I fantasize taking Henry's big black meat in my mouth, and down my throat. Then, Mike takes his turn. Then, it's Tony's turn.

I gag on the dildo a few times, but, this does not stop the abuse. I try to deep throat.

My fantasy continues - they take their clothes off to reveal tall, strong, beautiful, black, muscular bodies.

I imagine the taste of black cocks and their pre-cum... delicious!

Oh, my God! I am so wet, I am dripping pre-cum on my kitchen floor! I don't remember ever being this horny in my life!

I open the fridge, and scooped up some butter to use as lubrication on my asshole.

I adjust the dildo for my rear. Time for Henry to fuck his little bitch, I thought.

"No, please, Henry! Don't fuck me in the ass! I'll suck your cock all night, but, don't fuck me in the ass!" I beg him.

"It won't fit inside me! You'll tear my asshole!" I cried.

But, the Henry of my fantasies was a strong, determined and brutal black hunk.

I positioned my asshole on the head of the dildo, then, violently impaled myself on it. It was so thick and long! It went all the way inside me, hitting something deep inside me - was that a bone?

Oh God, the dildo hits my bone violently several times and this produces both a sharp and intense pain and an incredible pleasure.

I felt the gigantic dildo stretching my asshole to the limit.

"Oh, Henry!" I cried. "Not so rough!... Please!... That hurts so bad!"

But, the Henry of my fantasies was ruthless! His big black hands grabbed me and pulled me hard towards him as he violently thrust inside me.

Our bodies smashed hard together and my insides burned with the nasty pounding I was getting.

Mike was right, I should have gotten the black dildo. I also wished I had bought two more dildos for a proper spit roast.

I imagine looking behind me to see Henry's big and strong sexy body, his black muscles glistening with sweat. I imagine him looking mean and tough... like a thug in those hip hop music videos.

I fuck the dildo harder and faster... harder... faster.

"Oh, God!". I cry out.

"Oh!... Oh!... Oh!..." I moan like a crazy and possessed bitch! My neighbors might hear my yells of ecstasy, but, fuck it!

Henry brutally pounds my little hole until I am extremely sore inside. Then, Mike and Tony also take their turns ravaging me.

I did not touch my little 'clit' during this fantasy, because, I was so horny that a touch of my clit would set me off.

But, I felt the orgasm growing inside me. Its going to be a whopper of an orgasm!

I impaled myself on the dildo like I was possessed by a demon bitch in fiery heat! It was worse than any pounding I had received from Roberto!

"Oh!... Oh!... Oh!... Ahhhh!... Ahhh!... Oooooooh!" I moan like a crazy and possessed bitch!

I yell out each of their names when the orgasms finally hits me. It is a tidal wave. My body convulses and spasms violently.

I cum on the inside!... I lose control... Is it one long orgasm or 20 orgasms? I feel like I pass in-and-out of consciousness, my brain is overwhelmed with orgasms too strong to process.

I collapse on the floor, light-headed, trying to catch up on my breath. I even feel some tears flowing down my face.

Shit! This dark fantasy has given me the strongest orgasm of my life!

When my brain regains oxygen, it occurs to me that I could easily fulfill this fantasy. If they saw me dolled up as Raquel, they would want to take me, before turning me over to their VIP customers. This thought both terrifies me and excites me.

God, no!... I cannot!... Please brain, do not tempt me... It was one thing to be Roberto's little sex bitch. He pounded me and abused me, but, we had a long history together, he was like an uncle to me. He encouraged me to explore my sexuality. What we had was special.

If I get fucked by these three guys, what does that make me? And, I don't want to be a hooker, no matter how much money I can make.

No, I cannot become that... But, there is no harm in fantasies, right? This new fantasy is the crack cocaine of fantasies... One hit and I am addicted to it!... But, it must remain just a fantasy.

I need two more dildos to make this fantasy more real. While one dildo is fucking my ass, I need two dildos to take in my hand take turns sucking on them. That will make the fantasy of a foursome feel a lot more real.

I realize that I need to go back to the same sex shop tomorrow... But, what if I run into those guys, again?... I have to avoid them.

I decide that I must go back to the sex shop as Raquel, whom they will not recognize. Yeah, that should work.

JHouston
JHouston
455 Followers
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6 Comments
Tom599Tom5994 months ago

Good up till the end then a let down

Where did the uncle go

Bottfeed2Bottfeed2over 5 years ago
Don't stop - please

Don't end. More please. Keep Raquel going. This is a really really hot series.

AnonymousAnonymousover 6 years ago
Amazing

This is a great set of stories. I wanna read how Raquel whores herself for Henry, keep up the writing.

AnonymousAnonymousover 7 years ago
great

I love this submission as all the rest of your subs but you have to stop doing this to me,starting a theme and not carrying on,please please please bring them up to date and stop teasing

Sissy6869Sissy6869over 7 years ago
Great story

Absolutely a wonderful story. I would love to have someone do this to me. Thank You so much for sharing. I can't wait for chapter 7. Especially since I live between Dallas and Ft. Worth so I've know some of the places you write about.

AnonymousAnonymousover 7 years ago
I fucking loved it!

So fucking hot! Please write more!

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