Dressing up with my sister and her friends
When I was a kid, my adopted sister (does that make her my stepsister? We had different parents so I guess we weren’t true siblings…) who was three years older had always liked dressing me up in her clothes, putting lipstick and even makeup on me and pretending I was her little sister. We had done this for years - our adopted mom thought it was so cute!
When I was half of twenty and she half of 26, she asked me if I wanted to play dress up again. I said, “Sure - if I can dress you up in my clothes too!” and so we went up to her room. She made me strip down to my skivvies, then handed me a pair of her nylon panties and said, “You have to put these on!” I started to put them on over my tidy whities but she said, “No, you have to take those off first” so I turned my back to her, dropped my drawers and slid her nylon panties up. I turned around and she was smiling at the bulge I made in her knickers. “Now my bra,” she insisted, so I put my arms through the straps but she told me to turn around so she could fasten it. It was really tight on my little chest, but with some adjustments she made it fit over my nipples. She even pinched my nipples through my/her brassiere!
Then it was time for a blouse and skirt - it felt weird having my thighs rubbing together without pants against them! Then she sat me down at her dresser and put makeup on my cheeks and carefully applied some lipstick. When she was done, she took me to her mirror and let me look at the two of us side by side. “If we only had a wig…” she sighed.
“Your turn,” I demanded. So I picked up the tee shirt, skivvies and cutoff jeans I had worn into her room. She crossed her arms, tugged up her blouse and pulled it over her head, and stood there in her bra. “I had to take my underwear off,” I pointed out, so she began to reach around her back. “No, let me,” I suggested, so she turned around and let me unfasten her bra. I tossed it onto her bed, and she turned back around showing me her little 32A tits (I knew what size they were from reading the tag in the laundry). She pulled my tee shirt over her head and smoothed it down over her little chest, her nipples making tiny points through the thin fabric.
“Now the rest,” I told her. She unzipped her skirt and stepped out of it, showing just her white panties and reached for my skivvies. “Nope, I had to take mine off first,” I reminded her, holding them just out of her reach. She made a face at me, then shrugged and hooked her thumbs through the waistband and drew them down and stepped out of them, revealing her curly pubic hairs to my eager sight. Then she put her legs through my underwear and drew them up, snugging her pubic mound into my nut pocket. I couldn’t help sticking my finger inside the pee flap of my skivvies, just to feel her curly pubes! I handed her my cutoffs and she zipped them up, though they were a little loose. She pulled her hair back into a ponytail and we went back to her mirror, looking at my “little brother” and her “little sister”.
”I’ve got to call Francine and Nancy to come over and see us!” she exclaimed. They only lived a block or two away, so she called them and they were there within minutes. Nancy had a younger sister my age, and Francie was an only *****, so neither had a brother to play with. They had often played with me as kids, but were now beginning puberty as my sister was. They oohed and aahed over my sister’s handiwork, and came over and Francine even wanted to feel my bra. “Here, let’s give your brother some boobs!” she declared, and began stuffing tissues into my bra until it no longer looked like a deflated balloon. She patted my butt in the wool skirt, and said I had a nice ass.
With the attention of the three girls, I was getting very hard! Nancy said, “What’s wrong with his skirt?” pointing to how it was bulging out in front. “I don’t know?” my sister said, “Let’s see!” She lifted up my skirt and my little prick was straight out, stretching her panties out. “What’s THAT?” Francie gasped, looking right at my stiff penis. She had never even babysat, and with no brothers, it was the first male organ she had ever seen. “I think it’s his willie,” Nancy explained, as she had done some babysitting and changed boys’ diapers. “But ew, it’s so big!”
The two girls came closer to inspect what was tenting my sister’s knickers. “It’s his dick,” my sister explained. “All boys have one.” “Really? Are they always like that?” Francine marvelled. “Can I touch it?” looking at my sister.
”OK with me,” I said, thrusting it out a bit. “Go ahead.”
She tentatively touched one finger to the tip, then traced it back to my groin.”It’s really hard!” she exclaimed, “and warm.”
”Go ahead and feel me all you want,” I suggested, and she wrapped her fingers around my erection. Her hand felt so soft and smooth, unlike my own hand when I would jack off every night (and often times my morning wood, too..). As her grip tightened, I began thrusting my cock in and out of her fist. “Ooh, it’s getting bigger!” Francie cooed as my dick swelled in her hand. “Nancy, come feel this!”
Nancy was a bit reluctant, but with the two other girls urging her and daring her, she finally ran her fingers over my now painfully hard organ. “Wow - it’s so much bigger than babies have!” she observed, her only other basis for comparison.
“Would you like to see it?” my sister suggested. “YES!” both girls agreed. My sis tugged her panties down to my ankles and my dick jutted out, proud to be seen in its entirety. They eagerly eyed it, my tip now glistening with precum. Francine, ever the bolder adventuress, reached for it again and felt its silky surface. “It’s so smooth but hard underneath,” she said as her soft hand rubbed slowly up and down its length. “But what’s that underneath?”
”Those are his balls,” my sister explained, taking them into her own hand. “That’s where the stuff to make babies comes from! Here, you can touch them too but don’t squeeze because it hurts them.”
Francie let go of my dick and shyly fondled my nuts. “Easy!” I warned as she got a little carried away. “Be gentle!”
“It’s like they have little almonds inside!” she murmured. “Here, Nancy, you’ve gotta feel these!”
Nancy, the shy one, finally agreed to touch them, but really only tickled them a little. I was so fucking hard right then I begged Francie,”Please grab my dick again!” She smiled up at me and took me into her hand again like a velvet glove. “Now stroke it like you were doing!” I pleaded with her as my cock became slippery with my precum. “”Harder - grab me harder!” My sister was watching, right next to me, so I grabbed her tit through my t shirt she was wearing and squeezed her little nipple hard. “That’s right. - FASTER!” I moaned, as my whole body began to tingle and shake, my balls wanting relief as I began humping Francine’s hand. With a shudder I ejaculated suddenly, my cum spurting all over Francine’s hand and hit her right in her blouse. “Gahhh!” I groaned as my penis throbbed in her hand, spewing my seed all over her.
”What was THAT?” she exclaimed, looking down at the mess all over her hand and blouse. “Did you just pee on me?”
”No, that was cum,” my sister reassured her. “It’s the stuff boys squirt to make babies.”
Francie got a shocked look on her face.”Is that going to make me pregnant?” she wondered.
” Only if he puts it inside your vagina,” my sister explained. “ It won’t do it if it’s on your hands - or in your mouth…”
”How do you know?” the girls asked my sister, who just smiled a wicked smile…
When I was half of twenty and she half of 26, she asked me if I wanted to play dress up again. I said, “Sure - if I can dress you up in my clothes too!” and so we went up to her room. She made me strip down to my skivvies, then handed me a pair of her nylon panties and said, “You have to put these on!” I started to put them on over my tidy whities but she said, “No, you have to take those off first” so I turned my back to her, dropped my drawers and slid her nylon panties up. I turned around and she was smiling at the bulge I made in her knickers. “Now my bra,” she insisted, so I put my arms through the straps but she told me to turn around so she could fasten it. It was really tight on my little chest, but with some adjustments she made it fit over my nipples. She even pinched my nipples through my/her brassiere!
Then it was time for a blouse and skirt - it felt weird having my thighs rubbing together without pants against them! Then she sat me down at her dresser and put makeup on my cheeks and carefully applied some lipstick. When she was done, she took me to her mirror and let me look at the two of us side by side. “If we only had a wig…” she sighed.
“Your turn,” I demanded. So I picked up the tee shirt, skivvies and cutoff jeans I had worn into her room. She crossed her arms, tugged up her blouse and pulled it over her head, and stood there in her bra. “I had to take my underwear off,” I pointed out, so she began to reach around her back. “No, let me,” I suggested, so she turned around and let me unfasten her bra. I tossed it onto her bed, and she turned back around showing me her little 32A tits (I knew what size they were from reading the tag in the laundry). She pulled my tee shirt over her head and smoothed it down over her little chest, her nipples making tiny points through the thin fabric.
“Now the rest,” I told her. She unzipped her skirt and stepped out of it, showing just her white panties and reached for my skivvies. “Nope, I had to take mine off first,” I reminded her, holding them just out of her reach. She made a face at me, then shrugged and hooked her thumbs through the waistband and drew them down and stepped out of them, revealing her curly pubic hairs to my eager sight. Then she put her legs through my underwear and drew them up, snugging her pubic mound into my nut pocket. I couldn’t help sticking my finger inside the pee flap of my skivvies, just to feel her curly pubes! I handed her my cutoffs and she zipped them up, though they were a little loose. She pulled her hair back into a ponytail and we went back to her mirror, looking at my “little brother” and her “little sister”.
”I’ve got to call Francine and Nancy to come over and see us!” she exclaimed. They only lived a block or two away, so she called them and they were there within minutes. Nancy had a younger sister my age, and Francie was an only *****, so neither had a brother to play with. They had often played with me as kids, but were now beginning puberty as my sister was. They oohed and aahed over my sister’s handiwork, and came over and Francine even wanted to feel my bra. “Here, let’s give your brother some boobs!” she declared, and began stuffing tissues into my bra until it no longer looked like a deflated balloon. She patted my butt in the wool skirt, and said I had a nice ass.
With the attention of the three girls, I was getting very hard! Nancy said, “What’s wrong with his skirt?” pointing to how it was bulging out in front. “I don’t know?” my sister said, “Let’s see!” She lifted up my skirt and my little prick was straight out, stretching her panties out. “What’s THAT?” Francie gasped, looking right at my stiff penis. She had never even babysat, and with no brothers, it was the first male organ she had ever seen. “I think it’s his willie,” Nancy explained, as she had done some babysitting and changed boys’ diapers. “But ew, it’s so big!”
The two girls came closer to inspect what was tenting my sister’s knickers. “It’s his dick,” my sister explained. “All boys have one.” “Really? Are they always like that?” Francine marvelled. “Can I touch it?” looking at my sister.
”OK with me,” I said, thrusting it out a bit. “Go ahead.”
She tentatively touched one finger to the tip, then traced it back to my groin.”It’s really hard!” she exclaimed, “and warm.”
”Go ahead and feel me all you want,” I suggested, and she wrapped her fingers around my erection. Her hand felt so soft and smooth, unlike my own hand when I would jack off every night (and often times my morning wood, too..). As her grip tightened, I began thrusting my cock in and out of her fist. “Ooh, it’s getting bigger!” Francie cooed as my dick swelled in her hand. “Nancy, come feel this!”
Nancy was a bit reluctant, but with the two other girls urging her and daring her, she finally ran her fingers over my now painfully hard organ. “Wow - it’s so much bigger than babies have!” she observed, her only other basis for comparison.
“Would you like to see it?” my sister suggested. “YES!” both girls agreed. My sis tugged her panties down to my ankles and my dick jutted out, proud to be seen in its entirety. They eagerly eyed it, my tip now glistening with precum. Francine, ever the bolder adventuress, reached for it again and felt its silky surface. “It’s so smooth but hard underneath,” she said as her soft hand rubbed slowly up and down its length. “But what’s that underneath?”
”Those are his balls,” my sister explained, taking them into her own hand. “That’s where the stuff to make babies comes from! Here, you can touch them too but don’t squeeze because it hurts them.”
Francie let go of my dick and shyly fondled my nuts. “Easy!” I warned as she got a little carried away. “Be gentle!”
“It’s like they have little almonds inside!” she murmured. “Here, Nancy, you’ve gotta feel these!”
Nancy, the shy one, finally agreed to touch them, but really only tickled them a little. I was so fucking hard right then I begged Francie,”Please grab my dick again!” She smiled up at me and took me into her hand again like a velvet glove. “Now stroke it like you were doing!” I pleaded with her as my cock became slippery with my precum. “”Harder - grab me harder!” My sister was watching, right next to me, so I grabbed her tit through my t shirt she was wearing and squeezed her little nipple hard. “That’s right. - FASTER!” I moaned, as my whole body began to tingle and shake, my balls wanting relief as I began humping Francine’s hand. With a shudder I ejaculated suddenly, my cum spurting all over Francine’s hand and hit her right in her blouse. “Gahhh!” I groaned as my penis throbbed in her hand, spewing my seed all over her.
”What was THAT?” she exclaimed, looking down at the mess all over her hand and blouse. “Did you just pee on me?”
”No, that was cum,” my sister reassured her. “It’s the stuff boys squirt to make babies.”
Francie got a shocked look on her face.”Is that going to make me pregnant?” she wondered.
” Only if he puts it inside your vagina,” my sister explained. “ It won’t do it if it’s on your hands - or in your mouth…”
”How do you know?” the girls asked my sister, who just smiled a wicked smile…
4 months ago
