DISCLAIMER: This is a fantasy depicting homosexual acts involving adults and teens.
The story is intended for adult readers and not minors.
IF YOU ARE NOT OF LEGAL AGE TO BE READING THIS STORY OR IF YOU FIND SUCH MATERIAL OFFENSIVE, PLEASE LEAVE. All characters are fictional and in no way related to any person or persons living or deceased.
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You know how my panty boy history started. Like so many of us it was sisters or moms panties in the laundry pile that led to that first "try them on" experience. Pure magic the first time you are all enclosed in nylon, satin or lace. It only grows from there.
So earlier my sister, Lisa, had caught me playing with myself wearing a pair of her sheer nylon panties. She encouraged a playdate to continue and at the end offer to let me have her cast-offs. True to her promise to her now panty boy brother, later that evening she brought a small pink little girl backpack to my room. The parents must have been busy downstairs as we did not get disturbed.
Lisa tossed me the pack and told me to check it out. I unzipped it and discovered a treasure chest of not only panties but a few bras and one pair of white thigh high lace top stockings.
"You like? I bet you do."
"Yes. Thank you."
She told me these were ones she had grown out of that would probably fit me. "There are a few of my early bras to little brother. Some were training bras as they are called. Normal construction but very flat cups. That was ok with my as I had not boobs to fill them out anyway. As she talked I glanced at the pile on my bed. Everything looked sexy.
"There are 2 bralettes in there also. From last year or so but because you just pull them over your head and the lace cups will just stretch to whatever they might excite you too. I expect a modeling show next weekend when the parents are at aunties house."
"OK, I answered with a bit of quizzical tone in my voice. I was going to put this stuff on for my sister to check out? Well she had seen me naked and in panties already so what the heck.
That night, after school the next day, and the rest of the week were consumed with trying on every panty, bra and nightie in the pack. A few were way to tight so I tossed then deep in a trash bag covered with all the wastebasket collection on my weekly chore list. The bras were amazing. I had to ask Lisa about how to get the hooks done so I got a lesson on that one. She helped me into a normal one and a bralette style one too.
"I can't wait for your fashion show baby bro." the commented after the dressing instructional session.
I was surprised my dick made it to the weekend in one piece. I think I jerked off in every item.
I will keep saturday's session story quick but it sure was amazing.
After the parents left, Lisa pranced into my room in an insanely hot lace underwire bra and panties to match. Tanga shorts she called them. They had a full front but little in the back revealing her marvelous mounds of fine ass. I has already donned a pair of yellow satin panties with lace leg trim and a white training bra in nylon with a few pink bows. She told me how cute I looked and I told her that too. She had me try on most everything and assisted me with the bras mostly. I had to get the hang of the hooks.
I guessed that we were both horny as hell based on both of us displaying very hard nipples in our bras. Lisa gave me a few hugs as we went on. I think she was trying to keep my dick hard all day. Then a new subject came up.
"Brian, my little sweet panty boy brother, you should learn how to take a girls bra off as well as putting them on yourself. It is a handy skill when you start dating. You like girls right."
"Yes, girls are hot!" Later that attraction might shift.
"Stand in front of me". She directed. "Put your arms around me."
In that position she took me step by step thru the skills of unhooking the back fasteners without scratching her or stretching pricey lingerie out of shape. Each time I unhooked her the bra never came off completely and she merely had me retook it again. Damn I loved seeing my sexy full boobed sister in a bra. I was young but I was oozing for sure.
Lisa turned away from me and asked that I unhook her current underwire bra. Without turning around she tossed it to the bed and gathered another one from her stack. It was all lace and looked a bit strange as she started getting into it. She explained as she went that it was a front hook design so it went on like a shirt with one clasp in the front. Once she had slithered and adjusted somewhat she turned to me, pointed to the single clasp and said "See? You give this one flick and it is off!"
Sis brought my hands to the fastener and explained how it worked. Pull the side slightly together and slide it apart. Wow that was quick. My eyes lit up. My gaze bore into her chest.
So hot as she grasped the two sides and opened then up like curtains at the theater. Holy Shit! Her tits were amazing. So big, round full, creamy pink with darker rings and stiff nipples burning into my vision. Both her hands went to the sides of my head and drew it to her right boob. "Suck my tits panty boy! Show your loving sister how well a boy in girly underwear can suck a woman tits! Use your tongue. Keep going! Lick around the sides, up under the bottom and bury your wet face between them. OOOOh that is soooo good. You could be a great lesbian. Someday I'll have to train you to eat pussy. None of my boyfriends or girlfriends ever worked my boobs like this. You are hired for life.!"
Suffice it to say the rest of the day was purely wonderful. After our fashion show we napped. Lisa had me wear a satin teddy it was called. Short nightgown. She wore one too and before we broke it all up I learned how to finger a girl to multiple orgasms. I leaked so much I thought I had actually come. No, but it was exciting anyway.
After that day Lisa decided that I should always wear panties under my normal clothes. I did not disagree. They felt so good against my skin. Any flopage in the front felt great only exceeded by my tight firm ass globes swaying around in the back. Satin panties were my favorites. We played around on and off thru my junior high years and she constantly would supply me with new "outfits". A few she bought just for me. Others were donated by her friends although I don't know if they knew they were for her panty boy brother to wear.
I did learn to eat pussy before I was 14 and Lisa even secretly raved to her really close girlfriends what a tongue master I was to her tits and her cunt. She said they were jealous.
More on that another time.
It was time to step up to the High School housing grades 10 thru12. As I said way earlier I was excited. All the girls now had nice boobs to gaze at and daydream about what kinds of bras they had on. I wore panties under my jeans every day except for gym. I was hooked and thinking of my panty-of-the-day made classes fly along.
My algebra teacher was Miss Friar. Pretty, maybe 30, with oh-so-long legs and a great chest. I called her "underwire friar" as it was obvious thru her semi sheer blouses that she preferred underwire style bras, many of which were lacy and that balconette style with like half a cup. Her mounded breast were pretty obvious to those like me who studied those things. Kind of wondered if the panties matched.
My other teacher of note was Mr. Paul for english. He was not real old, early thirties too i guessed, but very handsome. I was never really attracted to guys but some gayish fantasies had surfaced over the last few years when masturbating in my bras and panties. If i was not dressed they were not there. Anyway he seemed nice.
Towards the end of week one we had to write an essay on our summer experiences and then present them orally to the class. If only I could have written about my sister and I but I would have been expelled reading that or arrested. Anyway out came a boring, but nicely verbally embellished tale of my job planting bushes and things around the town all summer.
Mr Paul told me it was good but as I returned to my desk I dropped my notebook and my essay papers. Unthinking I bent over to scoop them all up then scurried to sit back down. Resting back in the chair i realized that in bending over my shirt had pulled out of the waist and I was pretty sure that I had accidentally exposed my teacher to a full view of the wide lace waistband of the pale blue satin panties I had worn that day. Maybe he wasn't looking at the moment. I twisted and turned about to get my shirt retucked into my pants and stopped worrying about being exposed.
We all turned in our papers and left.
The+ next assignment was writing and speaking about what we hoped to do in our life. Mr Paul told us to keep it brief, under 5 minutes of speaking time. When my turn came later that week to speak I thought about what had happened the last time and vowed to hold my papers more securely this time. As I gave my talk I swear my teachers eyes were locked on my ass instead of my face. Did he know? Was he wondering what I had on today like I wondered about Miss Friar? Talked and returned to my seat without an incident.
English was second period that day so it was still early went the bell to change classes rang. On the way out of the classroom Mr. Paul stopped me briefly and ask me to come by after classes as he wanted to talk to me about my paper.
"See you at 3:15. Right Brian?"
"Yes sir."
What was that about? Stay tuned to find out.
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