My “Uncle” Caught Me in Pantyhose! Pt. 01

My “Uncle” Caught Me in Pantyhose! Pt. 01


tumblr_nnoyxgdltU1taas3no1_500“Rick, why are you wearing your mother’s pantyhose?” Uncle Roberto asked me with a shocked expression on his face. I did not know he was in the house, I thought I was alone!

It was morning on the second week of my summer vacation after graduating high school. My parents were both at work. My dad was a salesperson and traveled a lot. My mother was a school teacher. My little sister was away at camp for the summer. No one was supposed to be at home.

What the hell was Uncle Roberto doing in our house? I wondered. I remember my parents talking about Uncle Roberto and Aunt Rosa, how they were fighting a lot and might be getting a divorce. Roberto is my dad’s best friend since childhood and I call him my “uncle”. He is a handsome tall olive-complexion latino in his late 40s. He has always been a charmer with the ladies and keeps himself in great shape.

Uncle Roberto must have gotten into a big fight with his wife, again, and she probably kicked him out. He works the graveyard shift at a 24-hour diner, so that explains why he is at our house this morning. He must have crashed late last night while I was asleep.

I have heard my parents talking about how he cheats on his wife. My dad defends him, arguing to my mother that uncle Roberto cheats because aunt Rosa is a frigid woman that doesn’t take care of his sexual needs. But, my mother argues back that aunt Rosa cannot have sex with uncle Roberto as often as he wants it, because uncle Roberto has a monster-sized dick, and to make matters worst, he is very rough in bed. I heard my mother say that aunt Rosa is sore and bruised for days after sex with uncle Roberto and needs time to heal.

“Rick? Are you a closet queer?” Uncle Roberto asked me. I am frozen. I was naked except for my mother’s dark lurex shimery pantyhose, and I had been walking around the living room like that, not knowing he was lying down on the couch watching me.

Oh, shit! Shit! Shit! Shit!

I could not answer him. I finally just ran to my room closed my door, and locked it. I collapsed on the bed and sobbed.

My dirty secret was discovered! He would tell my parents, I was sure of it! My life is over at 18!

This dark secret of mine started a few years ago. Pantyhose have always had a strange effect on me. I love to see women in pantyhose, it is the sexiest thing in the world that a woman can wear.

One day, my mother left her pantyhose in the bathroom floor. I picked it up, looked at it, touched it, and felt the nylon on my skin. I got so horny that I took my clothes off and masturbated while I touched my body all over with the nylon.

25703261240_31f4d77b09_bThen, I felt an intense desire to try the pantyhose on. It was the logical next step. A part of me said, “No! Pantyhose are for women, you freak!” But, another voice inside me said, “Put them on, right now! Just do it! This is so exciting!”

The second voice beat out the first, and I put them on. This awakened in me something new. It was like discovering masturbation all over again.

Wearing pantyhose felt amazing, and if I looked in the mirror from my waist down, and hid my penis between my legs, my reflection in the mirror was like looking at a woman.

I was quite flattered by how sexy my legs looked. It was like being both a boy and girl at the same time, and the boy part of me could masturbate checking out the part of me with the sexy girly legs. It was weird, I know, but, I could not help myself. In my head, I knew this was very wrong and that it would be a very bad shock and disappointment to my parents if they ever found out.

But, the urge was overwhelming. I became hooked on wearing pantyhose ever since the first time I tried them on. I stole a few pantyhoses and tights from my mother and my sister and put them on whenever I had the opportunity to be alone.

But, I was not alone today!

“Rick, it’s okay! Hey, get dressed and come out so we can chat. Don’t worry, I’m not going to tell anyone. Just relax, okay, buddy. Everything is cool!” Uncle Roberto said right outside my door. I was sobbing uncontrollably and he must have heard me sobbing.

Could I really trust him not to tell my parents?

I wiped my tears and got dressed in jeans and a t-shirt. I hesitated for about 10 minutes, but, I finally came out of my room with my head down.

He towered over me. He was at least a eight inches taller than me. “You have nothing to be ashamed of, buddy. Trust me okay. I was 18 once, too. Your hormones are raging, and, with still being a virgin with no girlfriend to put your dick into, it’s natural to do crazy experiments.” He said. I guess it was obvious to everybody that I was still a virgin.

I looked up at him, “Really, I’m not a sick freak? Did you wear pantyhose to get off when you were my age?” I asked him.

“No, nothing queer like that, but, I did other things. We all have particular tastes and fetishes.” He said.

“You think I am a queer?” I asked.

“No, no, that’s not what I meant. Look, you can experiment with queer things, like dressing in ladies’ clothes, and it does not mean you are a queer. Doing queer things to get your kicks is not the same as actually being a queer. But hey, even if you are a complete queer, that is cool, too. Don’t worry about it.” He said.

Then, he added, “You know, you can be yourself around me. Don’t let me interfere with your fun. I’m going to spend the next week or two here. Don’t mind me at all. Heck, I can even help you out.”

“Help me out, uncle? How?” I asked.

“Well, if you are going to experiment cross dressing, go all the way with it! Don’t stop at just pantyhose! Experiment with different girly clothes! And, don’t be ashamed of anything, you have every right to explore your own sexuality. Don’t ever let anyone judge you on that.”

What uncle Roberto said made me feel better. I do not think any other adult would have been so encouraging.

“But, I am afraid that I’ll get caught if I borrow more clothes from my mom and sister.” I explained.

“Yeah, it would be risky to borrow their clothes. You could leave a stain on something or forget to put it back where it was, the same way it was.” He agreed.

Soon, the conversation shifted to another things like school and work and I told him about a girl I was beginning to date, Karen, but, had not gotten to first base with yet.

The next morning, uncle Roberto woke me up and said he had a surprise for me. He had a few boxes that he said were for me. 36910947-150x1502015836904

651495494-150x150One box had a few mini skirts and tank tops. Another box had panties, bra and lingerie. A third box had white platform high heels and a black thigh high boot. The last box had a long blond wig and a short black wig. I blushed red, but, I really wanted to try these things on.

“Just consider this my early Christmas present.” He said. “I can keep this safe in my room while I stay here, but, you will need to find a safe place to keep this stuff when I am gone. And, if you ever get caught with this, you must absolutely swear never to tell anyone I bought this for you, you swear?”

“I swear it uncle.” I said.

I had never planned to cross dress beyond wearing pantyhose. But, presented with this gift of sexy girly clothes, I felt a strong urge to try them on. I felt my dick twitch just from thinking about wearing them.

Uncle Roberto was right. What harm could come from just experimenting with girly clothes. I am not queer. I like girls. I have been hanging out with this girl, Betty, and I am very attracted to her. I get nervous around her and I get a boner just thinking about her. So, I am definitely straight, right? – I convinced myself.

Maybe I just wanted to see a hot chick in the mirror, so that I could imagine banging her. Yes, that was it! I was just creating a reflection that I could use for masturbation; a picture of a girl in the mirror that I could masturbate to. I could make this girl bend over, spread her legs, anything, because I controlled her!

Uncle Roberto said, “Go on try something on, let’s see how you look.” This statement from uncle Roberto caught me by surprise. Why did he want to see me dressed like a girl? Was he just being supportive?

In the bathroom, I picked a red bra and panty set. I stuffed the bra with tissue paper. Next, I put on a black fishnet pantyhose. Next, I put on a vinyl black mini skirt and a black low-cut tank top. I tried on the black thigh high boots. Finally, I put on the short black wig. I could not believe the mirror! There was the reflection of a really hot chick that I wanted to bang!

I pulled out my dick and started to masturbate imagining myself fucking the chick in the mirror.

But, then, I nearly slipped and killed myself, because, I did not know how to walk or even stand in high heels.

Uncle Roberto heard the noise and came running to the bathroom, “Is everything all right?” He asked outside the bathroom.

“Yes, uncle, I almost slipped wearing these thigh high boots you got me.” I said on the other side of the bathroom door.

He chuckled, “Let me see!”

“No!” I said. “I am embarrassed!”

“Let me see!” He insisted.

“No, I look completely like a girl!” I said.

“Damn it, Rick! Open the fucking door, now!” He said, and his voice was cross and demanding.

I unlocked the door and he opened it.

I was afraid of him because of his harsh tone. But, his frown turned into a warm smile quickly.

10329916_731856663531599_278770584061681582_o“Woo, baby! You look hot!” He said smiling.

I blushed.

He walked over to me, and for a minute, I thought he was coming over to kiss me. But, instead, he patted me on the shoulder.

“It feels great doesn’t it? Eliminate the shame and self-loathing and just do whatever turns you on.” He said.

His hand rested on my shoulder and then moved up to the back of my neck. He rubbed the back of my neck and my eyes closed on their own.

Something was happening to my body. Dressing sexy like this, being this excited, and being touched on the back of my neck was a powerful combination, and I was feeling light-headed.

Uncle Roberto rubbed the back of my neck for a couple of minutes, then suddenly, he stopped. I looked up into his eyes and he gazed back at me. I felt a sudden charge of electricity.

“I’ll give you some privacy now.” he said and walked away. Now he decides to leave and give me my privacy? – I complained to myself. For some reason, I wanted him to stay and tell me more about how hot I looked. But, why did I want this? I wasn’t sure.

Had I actually wanted him to kiss me? Oh my God, what the hell was happening to me? Was I attracted to him? No doubt that he is a very handsome older man, but, most of all, I like how kind, supportive and nonjudgmental he is with me.

I started masturbating by thinking about banging the hot chick in the mirror. But, this fantasy started to fade as another fantasy was forming in my head. I fantasized Roberto kissing me and caressing my legs, my sides and my chest.

I am not gay! I told myself, trying to shake free from this stupid queer fantasy.

But, this fantasy took a hold of me. It kept coming back despite my best efforts. Finally, I relented, telling myself – It is just a fantasy in my head. No one knows what I am thinking, and besides, it would never happen in real life. There is no harm just jerking off to this weird queer fantasy.

For the next week he was there, uncle Roberto gave me space to dress up and walk around the house in my new girly clothes. I learned how to walk in platform high heels and thigh-high boots.

He stayed mostly in his room to give me privacy. But, When he came out of his room to see me sitting on the couch watching TV in my girly clothes, he would flatter me with cat calls.

One time he told me I looked like a hot girl that he could bang for hours, and he said that he would pop my cherry when I became legal. I took all this in jest. He can say crazy shit just to be funny!

Except for patting me on the shoulder and rubbing the back of my neck in the bathroom, Roberto did not touch me while he was at my house.

He returned home to his wife after a week, and, part of me felt jealous that he was back with her.

Roberto had been very supportive and kind to me, and I wished he had spent more time with me.

When I dressed up in the clothes he bought me, I always ended up masturbating to the fantasy of Roberto kissing me and caressing my body with his big strong hands. There was no sex in these fantasies, just a lot of kissing and sensual touching. My orgasms from these fantasies left me breathless, dizzy and light-headed. I had to lie down in bed for a while after cumming. Why were these fantasies so intense?

I still continued to have normal fantasies about banging girls in my class, but, these orgasms were not as powerful as the orgasms I had when I was wearing girly clothes and fantasizing about kissing Roberto.

In the middle of the summer, Roberto said he had a special surprise for me. My dad was supposed to take me camping, fishing, kayaking and white water rafting near Big Bend, but, he had been really busy with work. Roberto asked my parents if he could take me, instead.

Both of my parents were delighted. They thanked him very much for being so thoughtful. I prepared all my camping equipment and I was very excited to go camping and fishing with Roberto.

When Roberto came over to pick me up, he whispered in my ear that he had something else planned besides the camping and fishing activities, and he told me that he had bought me four new boxes of clothes and that we were bringing along on the trip.

I did not know exactly what he had in mind, but, I was excited to open the boxes and find out what sexy girly clothes he had bought me.

About that weekend: So many things happened! I really need to write another part to this story that describes all the events that changed my life completely. There were times that I was terrified!

I discovered that Roberto had a very rough and dark side to him. He likes to dominate, humiliate and inflict some pain. But, he is not a bad person. This is just his game, his thing, like I have my thing. He let me be me, so, I let him be him. We discovered that we played well together, we complemented each other.

Once I was able to adapt to the pain of his roughness, I learned to enjoy Roberto’s games. I let him do to me what he needed to do. In one weekend, I went from being a clueless virgin to being tested and pushed to my extreme limits in a way that few people ever get to experience. Though there was a lot of pain and fear involved, there were also many rewards. I had to admit things about myself that I was reluctant to admit, but, this opened up a new world for me. Roberto helped me discover levels of pleasure that were beyond anything I could have ever imagined.

I will write part 2 to describe all these things that happened over that weekend.

Also, it did not end with the weekend. I saved Roberto’s marriage by being there for him whenever he needed an outlet for his dark rough side. And, I needed to be with him as badly as he needed to be with me. We were very smart and discreet and no one ever suspected a thing. I finally starting having sex with Karen, and it was great, but, it could never be as thrilling or intense as when I become “Raquel” and spend time with my Roberto. We are perfect when we are together.

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