Where it happened: her bedroom
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My playful, teasing stepsister started my life-long appreciation of older women. She didn’t intend to do it, I don’t think. It just happened. One morning when I was15 and Sonny was 18 we were alone in the house, and she was trying on the dress that she planned to wear to the prom the following night.
We had lived together for four years, since my dad had married Sonny’s mom. During that time, there had been many occasions in which I had caught glimpses of Sonny in various sages of undress. Once I peeked into her bedroom and saw her half turned in my direction, buttoning her blouse. Once I saw her stepping out of the shower with a bath towel draped carelessly (and ineffectively) over her shoulder. Once I saw her pulling her pantyhose on under her skirt, during which I caught a glimpse of her panties while her skirt was hiked up to her waist. And once I peered quietly from the top of the stairs while Sonny and her boyfriend were making out in the den. He had pushed her dress up quite a ways on her thighs and was busy at her breasts, which he had managed to release from her dress top and bra. (I turned away shortly after that because I wasn’t sure I wanted to see any more.)
Also, when I did laundry on Saturdays, I would often discover Sonny’s bras and panties … and would enjoy the feel (and scent) of them for longer than I should have. Her size was 34C, which I thought — and still think — is perfect.
On this particular Saturday morning, I had just finished the laundry and was heading back to my room when Sonny called to me from her room, up the hall from mine.
When I peered into her room, she was standing there in her prom dress, a satiny light blue strapless, knee-length gown. It was “full,” requiring petticoats underneath, but she hadn’t put the petticoats on for this “trial run.” She looked great in it.
My widened eyes told her the story. “You like?” she said, and did a playful little turn.
“It’s great,” I said. “Really great.” I also noticed that the zipper that ran down the gown’s back, to Sonny’s waist, was not fully zipped.
“Give me a hand?” she said, presenting the zipper to me. “It’s stuck.”
Standing behind my stepsister and reaching for the zipper’s tab, I didn’t know if she meant for me to pull it up or down. I tried to tug it up. No luck. I tried down; no luck.
“See? It’s stuck,” she chuckled. She said the dress was a little tight, and that might be the reason the zipper wouldn’t work.
I tugged up again. Nope. I tugged down again. And the zipper started to move. Sonny stood still. She smiled back over her shoulder. “Keep going.” So I did. I unzipped her gown all the way to her waist.
The band of her beige strapless bra was showing.
“Please?” she said coyly.
I hesitated.
“I’m gonna take it” — the bra — “off and see if it” — the dress — “zips without it,” she explained. “Could you undo me?”
Oh. Shit.
With nervous fingers, I fumbled with the clasp of her bra until it came undone.
“I sorta hate to take this [the bra] off; it a feels so, I don’t know, dreamy on me,” she said, out of the blue. “Here, feel.” She located my hands behind her and drew them around her body, placing them against the silken fabric of her bra cups, made delightfully firm by the curve of her breasts.
I exhaled loudly.
Sensing that I was about to pull away, Sonny held my hands in place.
“Feel good?” Her voice was a little hoarse.
“Yeah,” I croaked.
We stood there for the longest time — maybe 45 seconds — with her hands holding mine against her bra-covered breasts. The bra’s fabric was slick and wonderful. Her breathing and mine started getting ragged and loud. Presently, I felt her nipples getting hard beneath my palms.
I don’t remember where our parents were during this event, but they must have been not too far away because I remember Sonny saying to me, “Shhhhh.”
At some point Sonny sort of sagged backwards against me. Her skilled touch showed my fingers how to work her nipples, an act which caused her to squirm and wriggle her butt against the front of me. “Oh, man,” she whispered hoarsely. “More of that,” she pleaded softly, and then, “This is crazy.”
But not crazy enough for us to stop. No, sir.
For moment upon moment, we stood there listening to each other breath, truly enjoying the experience. Her nipples clearly were “hot” spots for her.
Her voice was raspy, barely in control, when she said, “”Johnny … “
Time stopped. “Go ahead. … Go underneath it.” Her hands showed me that she wanted my hands on her bare breasts, under her bra. I happily did as she showed me, although I had no idea where, exactly, this was going. I was having a lot of fun, though.
Her skin was soft, smooth, her breasts alive against my fingers.
Sonny turned her head and glanced toward her bedroom door, which was open. We were standing close though to it that she said, “Close it.” I reached back and swung the door mostly closed, without slamming it.
Events of the last few minutes had gotten my penis pretty hard. Especially with her pressing her butt against it, grinding a little. Things started happening fast. Sonny took her hands from mine and stripped her bra off, tossing it onto her nearby bed. Then she busied her hands at the skirt of her gown and next thing I knew the gown was hiked to her waist. She changed her stance a bit to allow her to part her legs; she leaned forwad a little, increasing the pressure of her butt on my hardening penis.
Then she reached back and undid my jeans, pushed them down a ittle, and fished my hardon out from my briefs. “Stay still,” she whispered.
My chest was still pressed against her back. She placed my penis between her legs, at the top of her thighs. My penis slid against the drenched crotch of her panties. She held me tight agsinst her panty crotch while she rocked back and forfth. She was going “Uhhh, uhhh, uhhh” with each of her thrusts.
My fingers continued to work at her breasts and nipples.
Down below, we were moving together, back and forth, back and forth, back and forth.
“Uhhh. Uhhh. Uhhhhhhhhh!” The tempo was picking up.
The way she was holding my penis against her panty crotch, and with her panties as wet as they were, I could feel the hotness and wetness of her vaginal slit through the fabric. And I could tell that when the rim of the head of my penis passed over a certain part of her down there, it caused a huge spike in her pleasure.
“Don’t go in, okay?” She panted. I didn’t understand right away. But then she quickly pushed her panties down a ways and quickly put my penis back in contact with her slit. It was heavenly. So soft and open and wet and slick. “Don’t go inside, okay?” she repeated, breathlessly.
I nodded.
With each thrust, I was close to reaching climax. And she was, too. As desperate as we were and as slippery as she was and as hard as I was, it’s amazing that I didn’t poke into her vagina.
Then — all of a sudden — I came. Hard. I could feel my semem, warm and silky, gushing against and over and between her fingers. And then Sonny came. In her thrashing against me during her orgasm, she presed my penis in just the right way … and I slipped inside her.
“Ohyes. Ohyes. Ohyes. Yesyesyes,” she cooed, and held me inside her while she came. We finished our orgasms with my penis inside her. It was great.
After that, we stood there for several moments, savoring it. Then we sagged onto her bed and just snuggled for a while, getting the prom dress wrinkled as hell.
That was 45 years ago. I still experience a niggle of excitement whenever I hear the word “prom.”
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