A Boy's First Time Wearing His Sister's Panties, Sheer, Stockings And Suspenders

My practical experience of trying on and enjoying lingerie, began at 13. I told you in my previous post about my panty envy and slipping into my sister's tennis frillies. They were heaven to wear. Every movement sent tingles all over my slim body.

As you might have read, I later inherited my sister's bedroom when she left home to go to university. The intention was to move her stuff into another bedroom, but I ended up with cupboards and drawers full of nightwear and underwear. I'm so lucky that she loved frilly, silky, sensual stuff. I'm sure my hobby would not have bloomed at all, if she had been a "cotton" girl.

Instead, I was temped by the most feminine, girly, frothy, sissy undies. Of course at that time, I didn't know that there were any other teenage boys who also looked longingly at lingerie. I bore a terrible secret. It was a mixture of sheer enjoyment, and deep fear that I would be discovered.

Back in the 1960s, it was not unusual for women and girls to wear suspenders and stockings. Yes, tights were around, but maybe it was just more economic to discard a laddered stocking!

My stockings debut came a few days after moving into her old room. She kept suspender belts, socks and stockings in the drawer below her delicious panties. I discovered two of these mysterious items tucked behind the long socks. One set black and one white. I remember the fascination as I handled them, and the tabs dangled down.

The house was empty, and would be for a few hours, so I had plenty of time to experiment. I was standing naked, and blushing with excitement as I slid the suspender belt around my waist. I fiddled with the clips, by turning it back to front and then linked up the hook and u bit that formed the joint. I slowly rotated the belt around so that all four parts dangled in just the right places. In moments I was pulsing with shame.

I found two matching silky black stockings in the drawer, and took one off them. I sat down on the edge of the bed. I knew I had to gather the stocking up in my hand, by making that familiar to and fro movement I had seen my Mum and sister do to compress the stocking. Then I slipped my toes into the waiting opening. I can't believe how naughty and sensuous it felt as I unrolled the sheer nylon up my boyish legs. Finally, I fumbled and clipped the stocking to the tag. Then I did the same thing with its twin. With both front suspenders securely fastened, I stood up and clipped the two back tags as well.

The stocking tops were stretched tight, and now pulled as I moved. It is not a feeling that us guys should experience, but oh did it feel so sexy. I caught sight of myself in the mirror behind me. My blood pressure and arousal surged. The result was very evident.

I caressed my legs and touched that bare bit of leg at the top. Something had happened to me nerve endings. Wow! Electricity was flowing in my most sensitive places.

The feelings of pleasure overcame me. I felt great, and my long slender legs looked so delicious encased in those sheer black stockings.

My transformation wasn't yet complete. I still had to complete my sexy outfit with some panties, or knickers as we called them in the UK.

I slowly opened the treasure drawer. My fingertips explored the dozens of nylon pairs jumbled inside. The silkiest were black, with frilly leg openings and rows of lace along the back. The crotch was double nylon, rather than cotton lined. Perfect! I might even try on a few pairs? Perhaps also the lovely pink pair too.

Once again I sat on the edge of the bed. I pushed my stockinged foot through the leg opening, and let the elastic grip my calf. Then I slipped in the other foot in to the other leg hole. I was really tasting the forbidden fruit now. My excitement rose in proportion to pulling on my new discoveries.

I didn't want to pull the panties up and into place too quickly. Instead, I gradually drew them up. All of this reflected for my view in the wardroab mirrors.

The black panties glid up my legs, then came to the tops of my stockings and then past the tabs and around my slim, but now girlish waist. I smoothed them into place, and admired my round panty covered behind. I loved the look of the suspender tabs emerging from my pretty panties, and then connecting to the hose. I didn't matter from which angle I saw myself, I loved the effect. The lacy edges of the knickers gripped my slim legs.

My guilty dreams had come now true, after seeing and actually envying my Mum and sister and many fashion catalogue photos of this same combination, I was finally actually wearing panties, stockings and suspenders. I couldn't believe how good it felt.

It was just like a seductive drug. My panties tenting, almost until they split. I turned around and saw my reflection from all angles.

It was a strange combination of my male testosterone surging, and the image a a very sexy, sissy teenage boy. What appeared to be opposites, were in perfect harmony. I knew this was the ultimate turn on.

I now know that many males feel exactly the same way. Back then, I really thought I was the only one. I wanted to be like this the whole time. I didn't want to be a girl, or have a sex change. I just wanted to wear lingerie, for my male side to enjoy.

My legs in stockings, my **** in panties. It was so enjoyable. Why was it out of bounds for boys?

Just walking around wearing the outfit, made my heard beat like a drum.   

My uforia was broken by a sudden sound. The doorbell rang three times. Oh God!  It was the arrival code used by my best mate, and in my dreamy state I had lost all track of time. We had arranged to knock about together today.

My  room was just above the front door, so I knew that I could open the window and call out without my pantied lower half being seen. That is exactly what I did, making the excuse that I'd overslept.

I hurriedly pulled on my sweat pants and a tee shirt. And then put on some socks to cover my stockinged feed and toes. My erection subsided and I hoped my flushed face returned to its normal pale colour, as I dashed downstairs to open the door.

My mate Gerry had know idea that I was wearing stockings, suspenders and frilly nylon panties as I offered him a cup of tea. But I could feel everything under my trousers pulling and sliding as I walked. The sensation was delicious. I'm sure my heart was pounding. Now and again I could clearly see my suspender bumps under my jogging bottoms. Two little bumps on either side.

I could feel the panties slipping and sliding around too. It's a wonderful sensation of being panty aware. My male underwear never did this. I was aware of every movement.

My imagination was running wild, that he would suddenly discover my secret. Half a dozen times I hoisted up my trouser tops, so that the suspender belt or pretty panties would not show above the male waistline.

I began to think about the excuses I would make, and the humiliation I would feel, if my best friend knew I was really a panty boy. What would he say if he knew I loved wearing frilly, sheer, nylon panties? What would he think if he knew I had been wearing a pink frothy feminine baby doll nighty and bloomers in bed that very morning? How would he react to knowing I was addicted to my sisters dainty things?

Somehow, being under cover in lingerie was very thrilling.

But, it was a secret that must never be revealed by me or anyone.

My nervous state had made me a little careless, and in an instant the cup of hot tea fell out of my hand and onto my leg. The scalding liquid drenched my thigh. Gerry was up in a flash and grabbed a tea cloth. He was trying to mop the hot liquid off the tops of my legs, when his fingers hit an unexpected obstacle. By then my guard was completely down. He dropped the cloth and gripped the suspender tab between his fingers. Then his other hand probed the other side. I was caught.

He looked up and straight into my eyes. His lips smiled, and he broke the silence that felt like 100 years, with words that burned into my ears.

"I know what you are wearing!" ......

"Suspenders and stockings."

"And frilly, silky, girls panties too, I bet?"

At that point, I was about to pass out. my face burned, and denial was useless. I was trying to concoct an excuse, such as "I lost a bet.." or " She made me do it!

But it was too late, the world as I knew it had ended..and I would be an outcast and labeled a sissy boy.

Gerry broke the painful silence..

"Let me see?" " I want to see your knickers.." he continued.

He had me, and I couldn't deny it or run away. This was my best mate, and very soon to be my ex-best mate.

I'm sure my eyes welled up with tears. Partly overwhelmed with fear, and partly at the thought of news spreading about my kinky state of dress.

"Please don't tell anyone, Gerry.." I blurted out. "Please, I've only done it once. Today is my first time."

"Let me see your pretty pink knickers" He insisted..."Go on, drop em!"

"I will if you PROMISE not to tell.." I begged.

"OK, I won't tell anyone"...he promised, whispering. "On my life..!"

I slowly lowered my outer sweat pants waistband, and showed the top of my panties. Then pulling them lower and lower to my suspenders and stocking tops. His smile grew broader, as he saw my outfit.

"You look as if you are really enjoying wearing that stuff, Mikee?" ..."I thought pink would be your colour?"

I just hung my head in shame. "Please don't tell, I pleaded."

"I'm your best mate, why should I? Don't you trust me?"

"I'm sorry" I said, by now suicidal thoughts were entering my head... " If you do, I'll kill myself"

He just stood in front of me smiling, with both hands resting on his own jogging bottom waist. As he smiled, he tucked his fingers into his trousers and slowly moved them downwards. Just three inches was enough to let me see something that shocked me.

I could see the pink and lace covered waistband of shiny nylon panties, and he was wearing them. My best mate was also in girl's panties!

"I won't tell on you, if you won't tell on me!" He said.

"How long have you been wearing your sisters stuff? " He asked.

"A few months, before she went away to college.." I replied. 

"Wow, I tried on my sisters knickers on about 6 months ago, I was really horny one day and they were in a big pile of clean laundry near the dryer."

By now the intense burning embarrassment in my face had been transformed into amazement. Now, I knew I wasn't the only boy in the world with an unexplained and highly secret taste for wearing frilly panties and other girly underwear items. It was a thrilling revelation.

Gerry told me that he too had been fascinated by his old sisters undies. We laughed out loud as we confessed each detail. He like me, had been unaware that anyone else had the same taste. It was incredible that my best friend and I shared this special secret hobby. 

I said,  "Come with me...." And we both bounded upstairs to my bedroom, the one that was formerly occupied by my sister.

I went straight to the chest of drawers in the corner, and pulled open the top drawer. Gerry peered into the layers of pastel, nylon silky panties.

"Wow..." he said. "You lucky bastard..." His fingers dipped into the mounds of beautiful knickers. 

"They are SO sexy..." He said.

"They are all mine.." I laughed. "Lucky bugger" He quickly answered, laughing out loud.

"Would you like a sample, she'll never know"

Gerry picked up a pink pair with little ruffles across the back side.

He held them in front of himself. I could see that his track suit bottoms were tenting slightly.

"I think they'll fit like a glove..." I said.

"Why don't you slip them on, use the bathroom.."

Gerry was gone in a second. A few minutes later, he emerged with the panties clearly visible and showing above his waistband.

I asked them how they felt?  "Delicious" he said with a misty look in his eyes. By this time, I was holding up a blue, frothy nylon babydoll set. It consisted of double layered full transparent panties, and a layered top. The arm holes were finished just like the panties, with frilly lace around them.

It was one of three similar sets, I think my aunt had bought them for my sister a few years back.

I held it up to Gerry. "Your size exactly.." He almost swooned with delight.

I lifted the pillow and showed him the yellow one I had worn last night.

"How about a pyjama party right now, I asked?"

In a flash he take the set and rushed back to the bathroom.

I quickly ******** off and pulled on the babydoll panties, then the top. My heart was pounding again as I did it. In the mirror, I could see my boyish frame covered in the most feminine, frilly, sheer babydoll nighty.

Withing seconds Gerry came out of the bathroom. His looked even better.

mercedes260e mercedes260e
31-35, M
2 Responses Jan 1, 2012

Nice. And same.

Great story, are you still in touch with Gerry? and do you both still dress up?