Note from Sylvia: After publishing three of my girdle memoirs, a number of girdle lovers wrote me and told me of their earliest girdle thrill, often describing an unexpected and life-changing erotic experience with their first girdle- induced orgasm during early puberty. Many of these memoirs began with trying on a mother's or sister's girdle, sometimes resulting in their very first ejaculation into the garment. This story is derived from my own experience and those of a number of others. Thanks to all who wrote me at dfmorgan32@gmail.com.
Malcolm, my newest and most exciting girdle sweetheart, had purchased for me a new condo apartment in a luxurious fifteen story building, a place where he could dress and keep his rapidly expanding wardrobe of girdles, lingerie and other feminine attire, and where I could live in unaccustomed ease and comfort. Although only one bedroom, it had a large living room for entertaining my many T- girl friends and their lovers and admirers. Almost every weekend, Malcolm and I would host a gathering where the finest in both modern shape wear and vintage corsets and girdles were on display and where their erotic stimulation could be fully satisfied. I'll talk about one of those parties in a future story.
Meanwhile I want to tell you about Billy, a darling young boy of twelve who lives in the building with his parents. Almost from the day I first moved in, I noticed this boy watching me admiringly whenever we would meet - in the elevator or lobby, or at the Starbucks on the corner where I often stopped. He was about five feet, four or five inches tall, slender, with a sweet face and longish blond hair.
One day in the elevator, I introduced myself as a new resident and he told me his name. "Glad to know you, Billy, I hope we'll be friends," I said and he nodded shyly and smiled. I was wearing a form-fitting skirt and rather tight sweater and I could see his eyes going over my feminine form with the eagerness of a young fox. I felt a very naughty surge in my Rago 6210 at the thought of introducing a virginal boy clit to my kind of pleasure.
A few days later, I was at the coffee shop in the late afternoon when Billy came in, obviously on his way home from school. I invited him to sit with me and treated him to a frozen latte. We got to chatting about one thing and another and he finally said, "I really like the way you dress, Sylvia."
"Why, thanks, Billy, what a sweet thing to say! I try to look nice. What do you like especially?"
"Oh, I don't know. You're always look sort of, you know, dressed up, neat looking. I mean, you mostly wear skirts instead of slacks or jeans. And I like stockings, I guess." With that he glanced down at my crossed legs, thrust out from the side of our small table. I reached down and pulled the skirt up a bit and smiled at him.
"You like looking at my legs in stockings?
He blushed and stammered, "I guess." His eyes didn't leave my nylon-clad legs and I moved slightly so that the skirt rose high enough for the top of my hose and a garter to appear. His eyes glowed and his mouth opened slightly. I saw his hand go instinctively under the table and his lips whispered, "God!" I reached out and touched his arm, the hand of which I was sure was grasping his boyish erection.
"Are you okay, Billy?"
"Oh, yes, it's just that I never saw."
"Saw what?"
"Stockings with a top and that black thing attached," he stammered.
I laughed, "I get it. You've only seen panty hose. Is that what your mother wears?" He nodded and I went on, "I only wear regular stockings and that black thing is a garter. There are six of them that come down from my black girdle to hold up the hose."
"You wear a girdle?"
"Always," I smiled.
"I found some old fashion magazines in the attic of my grandma's house that had lots of pictures of women in girdles, you know, ads."
"Did you like looking at them?"
"Yeah, it was neat to imagine seeing a woman dressed that way. You know, a girdle, bra and stuff."
"Maybe someday you will," I said. I rose, gave him a quick kiss on his cheek and said, "I've got to run, Billy, but I hope to see you again soon."
" `Bye, Sylvia, thanks for the latte."
Our next meeting was a week later. I should explain that our condo building has a fully-equipped exercise room with a Jacuzzi in the basement and that area is next to the laundry room that has both machines and a sink for hand washing. It also has dryers and a small drying room for delicate things. Naturally, I always wash my precious girdles, bras and pretty lingerie by hand and hang them to dry.
On that day, as I was coming to unload the dryers with my sheets and towels and take from the line the under things I had washed earlier, I noticed Billy pedaling fast on an exercise bike. I waved to him and said, "Hi, there," and he waved back. A few minutes later, I had filled one basket with the machine-washed stuff and I was folding my girdles, stockings, slips, bras, panties and nightgowns and putting them in a smaller one. Billy came in beside me, watching carefully what I was doing.
"Doing your laundry, huh, Sylvia?"
"Yes, I have a lot today." Just then I was folding a high- rise, long-leg panty girdle and I could see Billy studying it avidly.
"Do you like wearing a girdle, Sylvia?"
"Yes, I love the way they make me look and the way they feel. Why do you ask?"
"Oh, I don't know. I heard my mother say that girdles are torture and that she'd never wear one."
I laughed, "Each girl to her own taste. I love that tight feeling. For me, it's like a loving caress."
"Really? How do you mean?"
"Here, feel this," I said and handed him the panty girdle. It was pale peach color with satin panels, a side zipper and six garters. "As you can tell, it's elastic and those firm shiny pieces keep my tummy and butt in shape."
He took the girdle in his hands as if it were rare treasure and fondled it eagerly. His eyes were glowing. Suddenly I realized that this might be the time for girdle seduction. What a naughty thought! Then I looked down at the shorts he was wearing for exercise and saw an unmistakable bulge and knew what I had to do.
"Billy, would you mind helping me carry my laundry back to my apartment? I'll carry these sheets and stuff if you'll bring the basket with my lingerie." He eagerly agreed and we went to the elevator, then up to my place and inside. "Just take that basket into the bedroom and I'll put this stuff in the pantry. You can take my things out of the basket and lay them on the bed." When I rejoined him in the bedroom, he had again picked up a girdle and was fondling it.
"Sylvia, what does it feel like? When you wear it, I mean."
" If you really want to know, why don't you try one of mine on?"
"Are you kidding? I couldn't do that."
"Why not? Lots of guys like to wear women's lingerie."
"Really?"
"Sure, Billy, it doesn't mean you're gay or a sissy or anything."
I could see he was tempted but scared at the idea. "Here," I said and handed him a cute pink four-garter, boy leg panty girdle. "Just go in the bathroom and put it on. Then call me when your covered and I'll come in and make sure it's in place."
"You won't tell anyone? Promise?"
"Of course not, dear. Our secret. Go on."
He went into the bathroom and after a few minutes, he called out, "Okay."
When I opened the door I saw that he had stripped off all his clothes and the girdle was around his boyish form. As I hoped, he had pulled it up so that his cock was upraised and already swelling against the elastic fabric. He was looking at himself in the full-length mirror and I could tell he was excited at what he saw.
"How does it feel, Billy?"
"I don't know. It really feels good."
"I can see that it excites you."
He glanced down at the mound in the front panel of the girdle, seemed to realize for the first time that he had a hard-on and put his hands down to cover it. He said, "Oh, my God, Sylvia, I'm.."
I went next to him and took his hands in mine. "Don't worry about that, Billy, I'm glad that it makes you feel sort of sexy. Let's look at you." I made him turn around and I ran my fingers over the fabric as if I were checking the fit, lightly grazing his upraised cock. "That's nice. Now for some stockings."
I had brought a pair of light beige seamed hose in with me. "Just sit on that bath stool and let me help you with these." I slowly rolled the stockings up each of his fuzz covered legs, smoothed them into place, then made him stand as I gave them a final tightening and attached the four garters. By this time, he was breathing hard.
"There, Billy, now look at yourself in the mirror." He looked and I could tell he loved what he saw, then a look of panic came over his sweet face. "What's wrong, honey?"
"It feels real full down there. Like I've got to pee. Right away."
I laughed lightly, "I don't think that's the problem, Billy."
"No, really, Sylvia, it feels like something is about to come out."
"Let me ask you a question, love: Have you ever had an ejaculation?"
"What's that?"
"Well, if you don't know, maybe you haven't. It's when some thick white stuff shoots out of your penis."
"Oh, yeah, my Dad was trying to explain it to me. No, I never have. The kids at school are always talking about jacking off. One of them tried to show me how but nothing happened."
"Well, maybe that's what my girdle is doing to you. Bringing you off. It's perfectly natural for a boy your age."
"It really feels full, Sylvia, I'm trying to hold it back." Just then his hips shot forward as if to thrust his young cock deeper into the girdle. "Oh, Jesus, what's happening?" He clasped both hands over his straining cock and I knew his spasms were starting. "Oh, oh, oh."
He staggered slightly and I went to him and put my arms around him and held him close as he pressed his girdled cock hard against me and whispered, "Oh, Sylvia, I love you." Finally, his virgin orgasm quieted, he stepped away from me and looked down at the spreading stain in the girdle.
"I'm sorry, Sylvia, I've made a mess."
"That's alright, dear, we'll just take off that pretty girdle and wash it right away."
I knelt before him, detached the garters, rolled down the hose and helped him pull off the girdle. There was a little thread of cream still hanging from the end of his softening cock and I reached for it with one finger. "That's too good to resist," I said and licked the cum from my finger.
"Do you like the taste of that?"
"I adore it. Try it yourself, if you want." He reached down, took a tiny pearl on his finger from the glistening head of his now dangling cock and studied it. "What does it taste like?"
"Sort of like creamy sea water, but not quite as salty. Go ahead and try it, it won't make you sick, although some people don't care for it." He licked it tentatively. "Well?"
"It's nice. Kind of smooth tasting." My heart leaped a little. Could it be that Billy had a natural taste for it? Calm down, I thought.
"Well, Billy, I'll just put the girdle in to soak, but first let me clean you up a bit." I dipped a washcloth into warm water, wrung it out and, before he knew what was happening, knelt down to clean his tummy and cock. He flinched slightly at my touch.
He whispered, "What are you doing that for?"
"We can't have you going home with your cock all sticky and smelling like sex, can we?" Of course, his cock began to stiffen again at my touch and I laughed and said, "We can't have any more of that today." I wanted so badly to bend my head toward him just a few more inches and take that sweet little boy stick into my mouth but I had sense enough to slow down.for the moment at least.
When Billy was dressed, he came out of the bathroom and met me in the living room.
"Thanks, Sylvia."
"You're more than welcome. Want to come back another day and maybe try on some more of my things?"
"Oh, yes, may I? But remember your promise not to tell anyone, especially my Dad."
"As I said, our secret." I gave him my cell number and, sure enough, two days later he called during his lunch recess.
"Sylvia, can I come to your place after school? My parents are both out until dinner time."
"Do you want to play dress up again?"
"Yeah!"
"Good, I'll have some lovely things ready and maybe we can dress together."
"What do you mean?"
"We can try on some of my things together."
"You mean I can watch you dress in a girdle and stuff?"
"If you'd like that."
I could almost hear him gulp into the cell phone. "I'll be there at 3:45, right after school."
When he came to the door, I was dressed in one of my prettiest flowing dressing gowns and had taken special pains with my make-up and scent. I had laid out on my bed a nice selection of girdles; both panty and open bottom and a couple of pretty garter belts. That morning I had bought a bra that I thought might fit him and, of course, there was a pile of panties, slips and other feminine things. I led Billy into the room and said, "We ought to be able to have a good time with all of these, don't you think? What would you like to put on first?"
He went to the bed and ran his hands through the piles of filmy and firm garments and finally picked up my favorite firm-control long leg panty girdle, the Rago 6210. "Can I try this on?" I nodded, "Sure just slip off your clothes and we'll get started."
I could see he was hesitant to disrobe and I said, "Come on, Billy, we're secret friends, remember?" With that I slipped off my robe and stood before him in my open-bottom 18" Crownette and long-line bra, well filled with my nippled forms. He gazed at my girdled form adoringly and immediately stripped off his clothes. His boyish cock was filling but still not yet hard. He picked up the panty girdle and pulled into place and I knelt beside him to attach the side hooks and zip up the closure. By the time the firm garment was in place, I could see his cock was fully erect.
"Can I ask you a question, Sylvia?"
"Of course, Billy, anything at all."
"When you were a kid, like me, did you ever try on a girdle and do what I did the other day? You, know, cum in it?" Then he stopped as if he was thinking. "Oh, but you wouldn't have because you're a girl."
"I'm a special kind of girl, sweetheart, and to answer your question, yes, that happened to me, too. I tried on my sister's girdle and, bingo, I came off."
"But, I thought that girls.." I interrupted him, "No more talk, Billy, let me help you with some stockings and I bought a cute bra for you to wear!" Within minutes the wonderful spell of girdles and lingerie wove their magic over young Billy and he stood before a full-length mirror in a long-leg panty girdle, a-cup bra with a soft nylon panty rolled in each cup, and stockings.
"God, it feels so wonderful! Can I just stay like this for awhile?"
"As long as you want. Are you getting that full feeling yet?"
"When I first put on the girdle, I thought maybe it was going to start. But now it just feels good."
"But you do want to cum again while you're dressed?"
"Oh, yes."
"Well, now is the time for your special treat. Remember I told you how much I love the taste of your love cream when you came in my girdle the other day?" He nodded. "Well, this time I want to taste it as it spurts out." With that I knelt in front of him, reached into the split crotch of his panty girdle and guided his stiff boy boner so that it thrust out of the opening. I held it lightly and took it between my lips, licking and kissing it with all the loving gentle skill I could.
I knew he wouldn't last long but I leaned back once to ask, "Does that feel good, Billy?"
"Oh, yes, but I've got that feeling again. I'm going to shoot in your mouth."
With that, I put my hands on his girdled bottom and lightly rubbed as I took his sweet cock into my mouth again. Sure enough, his spasms started immediately, he cried out and I felt the cream shooting, gob after gob. Oh, how I adored the sensation of that young boy-sized cock between my lips, squirting in response to its first suck.
Of course, I was totally aroused but I was wearing a gaff under my obg so that my cock was still tucked back. I wondered, was now the time to reveal my true sexuality to my girdle student? I'll reveal all in the next episode.