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Title: Baby Doll Nighties
I'm from the 50's generation. Thats when I started to mess around with nighties that were see-thru with ruffled lace trim and nylons, garterbelts and sheer panties and bras. Having four older sisters and me the only boy and the youngest was like being in sexual heaven. At the age of 10 and just starting to masturbate, I would watch and spy on my sisters as they paraded about the house wearing their dainty lingerie. By age 12 my two oldest sisters had moved out and got married. That left me able to focus on the last two who would be around for several more years. The third oldest sister, Barbara became the one who really turned me on and got me into full-time crossdresser that has lasted all my life. All of us had our own bedrooms but Barbara and I had rooms with a common wall between us. In that wall was a heater vent at the very top that was centered in the middle of that wall.
Having a set of bunkbeds in my room allowed me to sit on the top one and look through this vent without being seen or heard. This became the "eye on the world" for me. I would sit there in the dark pretending to be asleep and watch her dress and undress morning and at night. Spying on her at night was best. Barbara would go into her room and casually start to strip naked and put on one of many babydoll nighties and matching panties. Like all the other girls in her age group, 14 and up, she'd stand infront of her dresser with the big oval mirror on it and slowly remove the skirt and blouse she'd chose to wear that day. As the skirt fell to her feet she'd step out of it and unbutton the pure white blouse and toss it on her bed. As Barbara stood dressed in only her 32b white bra and panty set along with a lacey white garterbelt attached to silky tan nylon stockings, she'd begin to twist and turn admiring herself in the mirror.
Let me explain what Barbara looked like. She stood about 4'8", weighed 95lbs. Her reddish-brown hair fell down to the middle of her shoulderblades. She has green eyes and is quite petite and in shape. That ass of hers is pert and rounded like most cheerleaders. Her nipples stuck out like sharp erasers with an upward tilt. Barbara is still my biggest dreamgirl. I was watching this and rubbing my little cock for all it was worth. As Barbara removed her panties, bra and garterbelt with stockings still attached she gently started to rub her pussy every now and then. Once she was naked she opened the second drawer of her dresser and pulled out a baby-blue colored babydoll nighty and ruffled bikini panties that matched. She closed the drawer and turned around to face our common wall which allowed me to see her reddish-brown full bush. Back then girls didn't shave their pussies. Of course Barbara's pussyhair was soft and downy looking. I could makeout the lips of her vagina pretty easy. I had to stop jerking my penis in fear of dropping my load too quickly. Barb bent over at the kness and stepped into the see-thru panties one leg at a time. In one slow movement her hands slid them up her legs and around her waist. As she stood straight I spotted her right hand slip into the lacey waisband and massage her pussy for a few moments. My mind was reeling with carnal lust. I knew exactly what she was doing from overhearing the sex talk my mother had given my sisters the year before when they were turning into young ladies.
As she removed her hand from inside the blue panties I could see that it was shiney and wet looking, but what surprised and delighted me most was that she raised that hand to her mouth and proceeded to lick the clear juice from each finger. My poor stiff pecker was on fire to say the least but I forced myself not to touch it until later. Well, as I watched intently Barbara grabbed the babydoll nighty and stepped into it through the neck opening. She slid it up her legs and over her titties then put her slender arms through the frilly shoulder straps. She adjusted the top part in place so her tits fit into the triangle shaped cups of the nighty. Her pert nipples poked thru each one and I could see them clearly enough as if she was naked. Pulling her bed covers back she climbed onto the bed and propped up her pillows and leaned back on them. She layed there just as calm as can be and put her righthand back down into her panties and slowly at first rubbed her bush. Her lefthand moved up to her breast and began pinching and tweaking the taut nipples. I could barely make out the sounds coming from her mouth but it surely sounded like low toned moans and such. In this family we were taught to respect eachother's privacy and never just walk in to one anothers room at night especially. With that said, we didn't have to worry about being caught playing with ourselves. That comes from our parents needing their own private time together. Basically, if the door to our room was shut, don't come knocking!
Well, as Barbara was laying there rubbing herself to an orgasm I started to once again stroke my burning cock up and down, matching her strokes in tempo. After what seemed like forever Barb reached over to her night stand and retrieved from its drawer a long looking pink thing. It had a helmet shaped end and smooth shaft about 8" long. Taking this object to her mouth she started to lick it all over. I later found out that this is whats called a dildo. Her righthand was still inside her panties but not much longer. Holding the helmet end in her mouth she took both hands and slipped the ruffled panties down over her thighs and stopped them just above her knees. I know my mouth dropped to my chest as Barbara pulled the dildo from her mouth and gently inserted its end into her pussy inch by inch until she could barely grasp it. Well I guess that proved that Barb was no longer a virgin of sorts. Watching her pump her fake penis in and out was amazing enough. I sometimes jack-off now to this vision to this day, 40 plus years later, especially when I'm wearing the same kind of babydoll nighty as she was. However I've added a pair of pantyhose minus the crotch panel and a matching garterbelt with tan nylons attached to it.
When Barbara had done this for awhile she shoved it all the way in herself and slowly pulled the panties back over her hips and got up in a kneeling position. Once comfortable she began pumping her cheerleader ass up and down. As she began to bounce her butt she leaned forward with her hands placed on the bed infront of her and picked up speed with the dildo being held in by those lovely blue ruffled panties. By this time with all the stroking I was doing I couldn't hold back my climax anymore. I shot several spurts of cum all over myself. I had fallen back as I came and covered my stomach and chest with my jism. When I had finished I noticed I was sticky from my cock to my upper chest. Before I cleaned up I sat back up to see Barbara coming to her own orgasm. When she came it caused her to fall over on her right side and afforded me to see between those wet thighs she has. The crotch panel was soaking and the end of her dildo could be seen poking through. Barbara's breathing started to slow some and she pulled her panties down again but this time she grabbed her toy dick and pulled it from her stretched out pussylips. Bringing it to her mouth she sucked it totally clean and layed it next to her body on the bed. The bed where she was kneeling had a big wet spot. As she removed her panties the rest of the way off she got up and grabbed a towel from the floor and wiped between her legs then went to the wet spot and wiped over it several times to dry it as best as she could. Barbara's face told the whole story, she had been fucked good by her own hands.
Still spying on her I watched her pick-up the pink cock and replace it in her nightstand, then she just layed on her bed with no panties, pull the covers over herself, flipped the light off and go to sleep. As I started to clean up my own mess I realized what my next move was going to be. I enjoyed the sex show she didn't know she was giving me but I became totally engrossed into the lingerie she wore. I needed to try them on. From the panties, bra, garterbelt, nylon stockings and babydoll nighties and anything else she had, I knew right then and there that I was going to put them on any chance I got. For the next several days all I could think about was Barbara's lacey and sheer see-thru lingerie. My perfect chance came when I got grounded for not doing my chores. I acted really upset but inside I was jumping for joy. Mom and Dad both worked on Saturdays and my sisters were going to the beach all day as well, so there I was with nothing to do but wait until the house was empty. I just stayed in my room until my folks and sisters were gone. By ten a.m. I had the whole house and garage to myself. The garage becomes my privated dressing room later on. My twelve year old mind and body was on overload at that point as I walked into Barbara's bedroom. I didn't even bother to close the door once I was in there. I wanted to be able to hear if someone came home. Just in case. As I looked around I noticed that Barbara was very messy. Clothes and stuff all over the floor and her dresser drawers were hanging part way open with things sticking over the tops of them. I wanted to make sure I put the items I was going to try on back the same way I found them but that became a no brainer seeing how she kept her room. The bed had the top sheet and blankets pulled down to the foot of the bed and other than that it was clear of everything else except the two pillows. I began to strip myself of all my boy clothes as I stepped in front of her dresser. Not wanting to lose them in her pile of clothes on the floor I layed them at the foot of the bed. Turning to the dresser I started to shiver and shake a little. My hands reach out to the second drawer and pulled it fully open. I knew that this was my new treasure chest from watching her. It was jammed full of frilly types of lingerie. All the different colors was awesome to my young eyes. My hairless young body, especially my cock was going bananas.
I first selected a red bra that was so sheer. Following that color scheme I next grabbed a red garterbelt that was at least 6 inches wide. It came with four garterstraps that were adjustable. This was followed by a pair of red satin full brief panties. I took those and rubbed my already erect dick with them for a moment or two. The last item I spotted was a red see-thru babydoll nighty and ruffled matching panties. With all the other garments in hand I grabbed those and placed everything on the bed. I realized that there were no nylons in that location but figured out that they were there somewhere. So I opened the very first drawer and eurika I had hit the motherload of nylon stockings. This was years before pantyhose. I started using those in the early seventies along with nylon stockings. I found a pair of light tan ones that peaked my interests so out they came. With everything layed out on the bed I began my very first crossdressing session. The first of thousands upon thousands of such joyful sessions. Following exactly the same steps as Barbara had performed putting on her lingerie I started with the red lacey garterbelt. I clipped the backhooks together first then bending over at the waist I stepped into the waistband opening and slipped them up until it was around my upper hips with the hooks at the rear. Continuing with this I carefully gathered each nylon up into a roll and pointed my toes as they slipped up along my legs. The feeling was and still is incredable, especially now with my shaved legs. I shave myself totally bare from my neck down. With soft blond hair its pretty easy especially my cock and ball sack.
As the nylon tops reached the garterstraps I attached each clip and adjusted them to my height. Barbara was only an inch or so shorter then I at the time. I sat on the bed and rubbed both legs together enjoying the silky sensation it created. I still do this almost everyday. Picking up the red satin briefs I stepped through the lace trimmed legholes and pulled them along my nyloned legs and to my now raging hardon. I stretched them out and over my cock and balls then let the waistband snap in place. I couldn't stop myself from running my nervous hands over the bulging front. Not wanting to stop I forced myself to try on the sheer red bra. I put it around my waist with the two rows of hooks in the front at my stomach. Hooking these in place I rotated the bra until the sheer cups were now infront. I stretched the bra straps one at a time over each shoulder until each cup covered my very erect nipples. As I looked down I could see that each nipple made the material poke out about a half an inch. I couldn't help but tweak them as I'd seen Barbara do. Since her sixteen year old titties weren't that big the bra of hers fit me perfectly.
At this point I walked to the hallway bathroom to get a better look at my lingeried body. The mirror in there was as long as the bathroom is. Standing there I modeled back and forth as I seen Barbara do. With every twist and turn I felt this silky material cause quite a sensation to my body. Even my cock poking the front of the panties out delighted me and made me wonder if anyother boys did this. That thought would prove to become another source of sexual pleasure I experienced later on. I slowly walked back to Barbara's room enjoying how my legs felt with each step and them rubbing my cock as well. Stepping up to the edge of her bed I decided to try on the red babydoll nighty with its rumba panties. Taking my thumbs of both hands I stuck them into the waistband and shimmied them all the way down to my nylon encased feet. I was dizzy with delight as I put the other panties on. The front panel showed every detail of my crotch while the ruffled back panel encased my tiny hard ass. Once again I massaged my entire groin area and around to my ass. I couldn't believe how much I was feeling. I'm already hooked on wearing women's undergarments and I haven't even begun to explore this type of sexual pleasure yet. I reached over for the final garment, the see-thru sheer red babydoll nighty with the ruffled trim at the top and bottom hems. Holding it in both hands I spread open the top elastic and stepped each foot through it. As I pulled this lovely piece of sexy material up my body I could feel my cock begin to pulse and twitch. Feeling panic I pulled the nighty into position over my bra covered tits and put each elastic strap over my shoulders. I barely had time to look down at myself when I felt the urge to cum. Quickly I popped my pecker out and shot my first of many loads all over the floor. I grabbed my shaft and stroked furiously while directing each spurt away from anyother garments laying about. Luckily I only sprayed the floor. I really could not believe what I had done and how good I felt at that very moment. When it was over I layed back on Barbara's bed exhausted. This happened before noontime and I knew I had lots more time to do it many times again that day, which I did. I will always remember that day and I am truly going to continue this lifestyle until I'm dead. In fact, I am going to be wearing lingerie to my grave.
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