Dear Mrs Ringer

When a young boy, my across the street neighbor was Billy, he introduced me to oral pleasures between boys at age 12. Just as we were becoming able to squirt. He also had a gorgeous mom, and 2 older sisters, whose bras, girdles and stockings I frequently saw hanging around drying. His moms lingerie was even hotter to a young boy, heavily paneled high waisted long leg girdles with 10 denier stockings, and gorgeous under wired longline bras. I frequently used to suck on Billy while wishing I was dressed in some of his sisters or better yet his moms lingerie, though his moms would definitely not have fit. One Fri night while bored I told my folks I was going across the street to spend the night with Billy, they had no idea what we did when together. After ringing his doorbell, his jaw dropping mom answered the door wearing a lack lace bodysuit, barely covering her breasts. When I asked if I could spend the night with Billy she replied his dad had taken him and both sisters to visit his mom in Texas for the weekend, she said sorry. Then I screwed my guts up and asked her if I could come in and talk to her privately, she said she supposed so. I followed her to the icing room where I knelt beside her recliner while she finished her tv show.
After her show was over, I took her hand and while almost crying told her how beautiful I thought she was, how I wished I could experience what it felt like to dress as beautifully as her and her daughters. I begged her not to let my folks know, to which she agreed. But she replied she wasn't sure she should do it, I swore an oath than nobody would ever find out. So she finally relented and told me to follow her upstairs to her eldest daughters room. When we got there she told my to disrobe and sit on the foot of her daughters bed, while she dug through her daughters drawers. She pulled out one of the most beautiful girdles, hot pink with a split crotch, and a matching underwire bra. She proceeded to put both on me, then rolled a sheer stocking on each leg. Then had me stand up while she rummaged in a closet a brought out a beautiful taffeta home coming dress her daughter had, and proceeded to put it on me, then zip it up. I was in sheer Heaven by this time, which she could tell by my the time she could see my bulge, which was 9 1/2 inches by that age. I told her thank you, and asked if I could spend the night dressed like this, she replied sure if I really wanted to. She also told me to go to the bathroom if I needed to relieve some pressure. I politely said no thank you ma'am, and went back downstairs with her to watch another tv show.
After it was over, she said I could spend the night in Billy's bed if I wanted. I said since she and her husband had a king size bed, could I sleep where she did, so I could smell her perfume. She said sure, and also put some of her perfume on me. While laying there in bed beside her, I asked if I could hug her, she reached out and hugged me to her side, burying my head in her cleavage, while I wrapped my arms around her. After a few minutes I rolled my head and kissed the side of her breast, she let out a long breath and said she was waiting for me to do that, and I didn't need to stop. At which time I started making small sucking on the flesh of her boob, when she reached out and lowered the zipper on her body suit, exposing her nipple. Which I quickly took in my mouth, and hungrily sucked on it, while letting my hands roam her gorgeous body. After about 5 minutes of my nipple sucking, she reached over and felt me up through the dress I was wearing. She said she was wondering if I was still hard, of course I was. She then reached her front zipper and unzipped it all the way down around her crotch. Then she lifted my dress and pulled my cock out of the split crotch in the girdle I was wearing.
She then directed me to rollover in between her knees, lifted my dress, reached down and took hold of my cock, and told me to bring my hips forward, while she guided my erection into her moist, eager pussy ! Jackpot ! I had dreamed of her being my first experience, but my luck doubled, because I got to experience my first woman while fully crossdressed. I didn't last long, but she said that was ok, she understood, and I would be able to last much longer later that night. Wow was she right.
Several years passed, while we got together whenever the family was out of town. Nobody ever got the wiser about what was going on.. By the time I was in high school, her husband would take the k**s to Texas for a whole month every summer. And I got to stay with her for a month at a time. Those were glorious times, she would keep me completely dressed every day, and take me to her office to work for her, in heels with a wig and full makeup. The other women in the office thought it was kind of sexy. One of the other women in the office asked her if she could borrow me sometime and take me home with her. Which she proceeded to do the next day, what an experience ! When we got back to the office the next day I was wearing a new dress Mrs Ringer didn't recognize, but she winked at me and asked if I had a nice time. I said sure, but admitted I had missed her. That stopped when I hit 19, and the Ringers all moved to Texas permanently. But she was my first and greatest, I will forever thank her for introducing me to bras, girdles and sheer stockings !