I have been wearing my mom's, older sister and younger sisters bra's and panties since i was 6 or 7. over the years i have become limited to what i could wear. Especially since my little sister is half my size. However my older sisters bra's and her and my mom moms panties still fit. Only a hand full of my mom bras fit. But a real limiting factor is that my sister has gone away to college leaving only a few article of clothing at home, so when she comes back after term, i take the liberty and poach some of her bras and panties. and now have a few sets to relish in.
Any who; this specific experience started this past summer with me and my friends.
So after building up the courage over the years, the summer was drawing to a close before i was to go off to college i had a dream about me and my female best friends. the dream was one of those where if i acted on it then i new it would work out. So after hanging out with all my friends i made sure i dropped her off last. as i was driving i kept sighing and stuff, and she picked up on it. she asked me what was wrong. i told her about that i had a dream that she was wearing a white bra and thong, white micro fishnet thigh high stockings and white stiletto ****-me-pumps, and that i was wearing the exact same thing in black. also that in the dream that she was proud of me for doing that and that we walk around in only the lingerie. then dream ended, and when i finished relaying that to her, she laughed, and asked what did i want to do about it? me in sheer bewilderment asked if she wanted to act out the dream and she whole heartedly agreed. she even offered to let me wear one of her bra's and panties. i said no since i had my own (i didn't tell her that they were my older sisters, i made up some story about they were from a costume and that i never wore them because the costume fell through). so we drove somewhere secluded and i put on a black thong and bra and she got undressed and we walked around outside in just our bras and thongs, and then left.
Now about 2 weeks later and after the whole first best friend lingerie experience, i decided to see if i could possibly do something similar with my two best male friends. Well me being a big guy trough out high school has led two of my best friends jokingly to grad, poke, pinch or fondle my man-boobs. I had asked them to stop periodically but it never really did. One of my frineds one time said that if i wore one of my older sisters bra's for a day they would stop. but i never took them up on it until now . So in the closing week of summer, i was house sitting for a family friend who happened to have a hot tub. i invited my two best friends over to have a beer or two and hangout in the hot tub. upon arriving one of my friends pinched my man-boob. I again asked them what would make them stop grabbing my man-boobs? One of them replied that if i wore one of my older sisters bikini's into the hot tub and for the rest of the night, they would stop. to there amazement i said ok, and that i was tired of them grabbing my man-boobs. so i ran home as they got the hot tub ready to get my favorite skimpy bikini that i knew my sister had left. to my dismay, my sister was in her room, so i thought for a second and i decided to grab one of the bra's and panties that i had poached. so i grabbed them and headed back over to the house i was watching. when i arrived they asked what i got and i told them that i couldn't get a bikini, but i got something else. they said that they would have to approve of it, and as long as it wasn't one of my moms bra's. i slipped into the bathroom where i undressed and put on my older sisters pink ******** bra with purple lace trim on the top of the cup and a matching very-cheeky style pink ******** pair of panties with purple lace trim around the leg openings and the top waistband. i stepped out of the bathroom and struck a pose. they laughed and asked where i got the bra and panties from. i told them that i stole them from my older sister. they laughed again, and said they approved. then we headed out to the hot tub and preceded to hang out, them in there swim trunks and me in my lingerie.
In the closing day of summer, one of my friends from the hot tub was house sitting for a mutual family friend. and they had daughter a year younger then us in school. so on our last night before i left for college, i suggested a panty raid through the daughters room as well as the mothers room being as she is milf. the friend said only if i put on something. so we first went through the mothers room and couldn't find her panty drawer to our dismay. in the daughters room we found her panty drawer and went through it. he said ok were done, and i said no were not. he says o yeah the deal, and he gets up and leaves me to the drawer. i pick out a v-string thong and a simple bra. i put them on and walked down the stairs to hang out with my friend. Upon seeing me in the girls panties and bra, he chuckled and asked if i wanted to do one more drive around town, and i said yes. i got my clothing on with the bra and thong still on, and we drove around town. felling bold, i actually striped down in the car to just the bra and thong for part of our excursion. I even got out of the car, in only the lingerie to run a lap around my high schools track for old time sake. once i was back in the car, i put on my clothing, and headed back to the house he was watching. the next day i left for college.