“A perfect fit,” I gushed. I felt myself turn bright red.
My stiff penis and tight balls were cradled at the left side of my crotch, the leggings highlighting their bulk. What a perfect thing for girls, I thought, leggings. We boys have nothing like that, that’s for sure. Daddy walked over and put his hand on my penis, feeling the way it stood out in the pink fabric. His touch was exquisitely satisfying, as if were made for each other.
“Tonya, see?” Big Daddy said, gently squeezing my prick. “This is the ideal cock, firm and ready. You see how it stands out, the muscles rigid? Absolutely beautiful, very touchable. Tonya,” he turned to look at her and Sissy, “touch it, feel it, love it!”
Tonya and Sissy let go of each other’s dicks, pushed themselves up from the bed and walked toward me. My penis pulsed, ready for their soft touch. I felt Tonya’s curious probing fingers.
“Mm. Very, very nice. Stiff like you are, Daddy. Go ahead and touch it, Sissy.”
Sissy leered at me and touched my swaddled cock, stroking and massaging the hungry muscle.
“Not bad,” she grinned, “Not bad at all.”
I stood frozen, feeling the gurgle surge through my belly as she lightly stroked my penis, when the explosion gripped me, throwing me into a haze of confusion. The scum shot out of my prick into the pink leggings. I almost lost my balance, the semen saturating the material at my belly, but I didn’t care. The moisture looked very natural and proper. Sissy admiringly fondled my penis as Tonya pressed herself against Daddy’s side, her arm around his shoulders. My forehead was wet with sweat. I put my arm around Sissy.
“I gotta sit down,” I gasped, breathless, collapsing onto the couch.
Sissy fell down beside me, cuddling next to me.
“Take it easy, take it easy, baby,” she said. “Everything will be wonderful. I just know it will.”
I sighed out the satisfaction I was feeling. “I think so, too. Everything is going to be wonderful, like you said.” I kissed her and felt her tongue slip into my mouth.
It was almost 11:00 P.M. by the time me and Sissy started walking back to the Lower East Side. Big Daddy wanted us to take a cab. “I’ll pay,” he’d offered, but I refused. Tonya nodded, saying a walk would do me better than just sitting in a cramped, bouncing cab.
“I should know,” she said, patting her nice, big ass. “This girl has spread her cheeks many a time, and each time is so much better.” She smiled at us as we turned and I slowly limped along the street, Sissy holding my arm and helping me home.
After walking a block, I didn’t feel bad at all. I’d been nervous and tense when we started out, but my tension had shifted into a natural movement, a bounce, really. I began to feel totally soft and different. Sissy kept looking behind me, then suddenly sulked, “You know, you really do have a cute little butt. Round and bouncy, just like a teenage girl. All those beatnik perverts in our neighborhood are gonna be after you, that’s for sure. I’m jealous.”
“What do you mean, ‘teenage girl.’ Don’t be ridiculous.” We’d reached St. Marks Place with its bookstores, record shops, and bars and cafes where the locals hung out. “‘Teenage girl,’” I huffed again. “That’s crazy.” But then I saw a man staring right at me, a tall man wearing a rumpled suit and tie under his wrinkled raincoat, dragging deep on his cigarette and staring hungrily at me. I felt myself blush and pulled her across the street.
She turned back to look at the man and leered at me. “Bet you he’s a queer in a business suit, look at that wrinkled suit. If he is a ‘businessman.’ Probably just your run-of-the-mill writer, trying to look like an intellectual. The whole Lower East Side is filled with them, all writing novels to their lady loves,” she smirked up at me. “Or should I say man love?”
I gritted my teeth. “Oh, shut the fuck up, will you?” But she just smirked and kept looking at my backside.
“I must say, you really do have a cute butt.”
I was totally pissed and I felt my face burn red. We were on the corner of St. Marks Place and 1st Avenue near a pizza shop. There were people hanging around and they must have overheard her, because they gave her and me a curious eye. I didn’t know if it was her seductive look that disgusted me but I shook her off and starting walking fast down 1st Avenue.
“Hey, wait a minute,” she ran after me. “I didn’t mean anything.” But when we got to 7th Street she looked a little nervous. We were right across from the diner where her mother worked. This late at night it was closed. She took my arm again. “You’re very cute,” she said, leaning up to peck my cheek.
We crossed the street, holding hands again as we got to my apartment building.
“I’ll meet you tomorrow,” I said.
She nodded. “In the park near Avenue B, that’s my favorite spot to sit and watch people.” She winked at me, pecked my cheek again, then walked away. I watched her to the corner, then she disappeared down 4th Street. I knew what kind of pickup place the park could be. I shook my head and went into my building.
Going up the stairs in the dark made me nervous tonight. The building seemed even darker than usual, and I imagined a rapist or molester at each step. Some beatniks, or maybe hippies, lived on the second floor, but other than a loud conversation and the smell of marijuana, the stairs were quiet.
I reached my floor. For many months I’d jerked off on the landing as I gazed at Pips’ door, but now I didn’t want to do that. There were new rooms behind Pips’ new door. Probably a beatnik would rent it. I frowned and opened my apartment door.
The apartment was almost as dark as the landing; Mom had already gone to bed. I made my way to my room, bumping into a kitchen chair. Mom called, “that you, Vinnie?”
“Yes, Mom,” I said. “Go to sleep.”
She said something but I didn’t quite hear what it was. I was about to shut my bedroom door when she said something again.
What the hell?
I went to her room, knocked and opened her door. Her light was on and she lay in bed smiling at me.
“I’ve been thinking very hard, and you know I love you, don’t you, Vinnie?” she gushed, turning red. “No matter what you are, queer, straight, gay, or obnoxious, even, I just don’t care. You will always be my one and only son, and even if you were a sissy, it’s none of my business. I’d still love you very much, Vinnie.” She smiled up at me. “You love girls, you love boys, same difference to me, it’s what you want to do. Whoever, whatever, you love whoever you want because I love you, too.”
My eyes instantly got wet and I ran to the bed and fell onto her, weeping but very happy, too. God, did I love Mom!
She hugged me and we both wept happily, sniffling, talking about our past, our dreams and hopes for the future, until I wiped my joyous tears and finally left her room and went into mine. I was ecstatically happy!
I always kept the curtains drawn but Mom had opened them earlier in the day to let in the sunlight. I drew them closed and turned on the light. Mom had always tried to cheer up the room by opening the window or sometimes bringing in some flowers, though I always took them back out again. “It’s my allergies, Mom,” I’d protest, pretending to sniffle. “What allergies?” she’d pout, but she never bothered to put them back. I’d sure act differently from now on! I shook my head. I’d been such an asshole about things!
I took my shoes and shirt off and started pulling off my jeans. Holy shit, I forgot I had the pink leggings on! I stood in front of my big mirror and leered at myself, impressed with the way my huge hard-on looked in them. Had I gotten hard from seeing the leggings, or had I been hard the whole time I’d walked home in them? Damn. I grabbed my stiff dick and fell into my chair.
Ow! Holy shit, what the fuck was that?
A pain shot through me, like a big dick tearing into me. I grimaced. Daddy’s big dick, I knew, his memory was in me for all time. We never forget the first one, do we, especially if it was as big as Daddy’s! The first ones will fuck us forever, at least in our memories.
; I straightened myself and inched over to the bed.
Man, fucked in the ass by Big Daddy! I felt myself redden. And I liked it, too! Oh, don’t be ridiculous, I told myself. But I have to admit it wasn’t really that painful. Unbearable pressure, but then the bursting through to a new and beautiful manhood. What could be better than that?
I stroked the outline of my cock in the leggings. Tonya was sweet, I knew, giving me her leggings. I wished I could fuck her in the ass as well, besides doing it to Big Daddy—all fuckers or fuckee wannabes. I smirked and squeezed my cock and almost instantly shot out. Where? Into my leggings! The splotch of scum bubbled in the pink crotch. I didn’t care. I rubbed my fingers in it, spreading the sticky moisture. A nice scent rose to my nostrils, mingled perfume, sweat, and scum. I licked my fingers. One lick and another, and then I was reaching for more scum so I could lick that, too. It was delicious!
I finally slept.
“Vinnie!” Mom was shouting so I could hear, but I couldn’t figure out what she was saying. “Vinnie, pink? You wear pink now?”
My eyes opened wide. I was lying in bed and Mom was standing at the foot, but she had her hands up to her face. I realized I was still in my pink leggings. I felt myself turn red.
“Oh, Vinnie,” she said, sounding defeated. “Pink.”
I sat up, realizing that I was hard.
I tried to cover myself. “Mr. Polsky suggested I wear them.” I was lying. Polsky was the sports coach back in high school, a big brute of a man I sometimes saw on the street. But all the students knew he was a pussy fag once he got you in his clutches. “You know how big I am, Mom,” I lowered my eyes. “It’s embarrassing sometimes.” I wasn’t any bigger than other boys my age.
“Yes, but pink? Didn’t he have any other color?”
“No, Mom,” I shook my head. “The big boys in the football squad took those. All he had left was this fruity color.”
Mom looked at me and shook her head.
“I don’t know about Polsky, he is one strange man.” She looked at my erection, turning red. “Well, as long as you wear your jeans over them, I suppose they’ll do.”
I nodded and said, “Why were you in my room, anyway? Looking for something?”
“No. I heard you talking in your sleep, sounded very bothered. Thought I’d see what was wrong.”
“I was?”
She nodded.
“Uh-huh. Well.” She got even redder. I wondered what I’d been saying. Something perversely sexual? “Good, that’s over with,” she said. “But sleep is sleep; I can’t remember much when I get up.” She checked her watch. “Oh, my, look at time. Have to get ready for work.”
She left my room, shutting the door behind her. I started to lie back down, then winced, a pain drilling deep in my ass. I lay back down, but I didn’t think I’d be able to stay in bed much longer. I heard Mom run the shower and turned over. I yawned and when I opened my eyes again it was an hour later. I’d slept again and felt pretty good.
Shit, but why had I mentioned Mr. Polsky to Mom? He was a closet fag that most of the students kept away from unless they were “on his team”—football players, my ass! Many of them did wear leggings for their brawny physiques, but they’d wear black or brown or even white, certainly not faggoty pink. A guy wearing pink meant one thing, that he was a fag, a sissy boy who took it up the ass and liked it, too. Liked it? No, I loved it!
I came again without even touching myself, the semen wetting the left side my leggings. A beautiful mood swept over me, making me feel relaxed. I hadn’t touched myself, hadn’t done anything but think of big Mr. Polsky. But why was I thinking about Kid Paulie, too? They looked alike, didn’t they? Paulie and Polsky. Oh, fuck those assholes!
I sighed, caught up in my beautiful feelings and looking at the lovely splotch on the pink leggings. I frowned; I couldn’t go out with them looking like this. Sure, I’d be wearing jeans, but still.
I sat up and pulled the leggings off. They were Spandex and wouldn’t take long to dry, I thought. I felt happy and went into the kitchen, taking the box of Tide detergent from under the sink. I took a whiff of the leggings. Did a barely discernible fragrance still emanate from them, or was that my own lustful imagination? I filled the wash basin with water, sprinkled some Tide in and put the leggings in. The moisture saturating the material made me think of someone cuming in them and lying on his stomach to spread the moisture. Where did these sexual feelings come from? I was holding a garment meant for a woman, but the “woman” who was supposed to be wearing them had turned out to be a male. Was I a woman? Was I a man?
I picked up the leggings, ran the soiled water out of the basin and refilled it with fresh water. What would Mom think if she saw me washing these leggings? I never picked up after myself and here I was, Little Miss Homemaker, washing clothes. I felt myself blush. I really was a sissy, wasn’t I? I rinsed the leggings and squeezed them dry, then took them into my room. I set them to dry on the open window in the sunlight. I felt good. That was one good deed I did today. I dropped onto the bed looking at the leggings, then slowly squeezed my hard dick. Jerking off while looking at my leggings, who’d think you’d get aroused at that? But I certainly was aroused—I was stiff as hell!
I shook my head to break the spell and got up from the bed, walked around a bit. My ass wasn’t too bad. Just a memory of something huge drilling into me, an almost comfortable feeling. I went back to the window and, holy shit, the leggings had almost dried!
I smiled. Sissy Godiva, I’m a-cuming!
Chapter 36 Another sunny day, but not as humid as the last few days; comfortably warm instead of unbearably oppressive. Hot summers in New York are like that, full of surprises, which I like, anyway.
I went to Tompkins Square Park, slowly making my way toward Avenue B, where Sissy said she’d be. She was late, as usual. A few people sat around reading newspapers or just staring into space. I was planning to sit on the bench where I’d met her, but a tall old man sat there, holding his cane and looking at the people. Except for the cane, he reminded me of Pips. Wonder what he looks like naked? I felt myself blush as I approached. I nodded “good morning” and sat on the bench with him. He nodded back at me.
“Nice day,” he said. I smiled. “A perfect day couldn’t be any better.” I was talkative this morning! I didn’t usually say anything to someone just yapping at me. I wasn’t only a sissy, I was a chattering one, too! “I sure am enjoying the lovely weather. You?” I winked at him and he winked back.
“Yes,” he agreed. “Extremely nice day, and about time, too. It was too hot for days on end. Much better now.”
Ah-ha, so he was very talkative, too!
“Have to meet my, um, girlfriend.” I felt myself blush as I looked around, “I guess she’ll be here soon.” I winked again. “You know how girls are, always late.” I smiled at him, and he smiled back.
“Girls, boys,” he sighed. “I’m too old for all that. All I can do is look and dream,” he said.
I nodded at him when I saw Sissy Godiva coming from Avenue B, Kid Paulie walking beside her. And not just not walking together, holding hands! God, what the fuck was that all about? They came toward me, Sissy blushing and Paulie looking right at me. I noticed the tall man sitting next to me was blushing, too.
“Tsk, tsk, picking up young boys, Sidney?” Sissy said. She’d turned red and was shaking her head. “I thought you didn’t do that anymore? Sidney, Sidney, what can we do with you?”
I narrowed my eyes at her. It was obvious that she knew the man I was sitting next to, but what the hell was Paulie doing strutting beside her and holding hands with her like they were lovers? What the fuck was that about?
“Paulie had an awakening,” she said, turning to me, “after his dad tried to beat him and his mother up. Isn’t that right, Paulie?” She tugged Paulie’s arm up and down. Paulie shrugged.
“Hey, I’m sorry, I was such a shmuck,” Paulie said to me, though he sounded boastful. “Life on the Lower East Side, you kn
ow how it is. It isn’t always pretty, coaches and weird people. But you know that.” Damn, horny Mr. Polsky; Paulie must have been one of his boys.
I nodded, shrugging at him.
“His dad’s in jail for beating up some cops,” Sissy explained. “His mom’s at the hospital from the beating he gave her. When I got home last night, Paulie was sitting on the stairs, crying. My heart went out to him.” She looked up at him. I could see the fascination in her eyes. Kid Paulie just smiled and nodded, as if he was a shy little boy. What rot!
“She took me to her apartment,” Paulie confessed, “where we made love.” He said this like he was boasting, then stooped down and kissed her. Was that his first time, I wondered. I knew it wasn’t hers, that’s for sure. She kissed him back and giggled. He was feeling her up, his hands all over her body.
“Paulie,” she shrieked, “I told you I don’t make out in front of people.” I knew that was a lie! But Paulie wouldn’t let go of her and drew her to him.
I watched them and felt beaten. My yearning for Sissy was defeated, laid to waste. Whatever I had wanted was meaningless now. The girl of my dreams—or boy, I should say— was taken by my worst enemy, Kid Paulie. He’d come right out of the closet and just taken what he wanted, as always, simply because it was there for the taking. He was Sissy’s boyfriend now, and I wasn’t. What could I do about it? A big, fat nothing!
I winced. Paulie and Sissy held each other tight, giggling and kissing. I thought there would be a terrible scene if she ever got bored and tried to let him go. Or maybe there wouldn’t. Perhaps Paulie was a real wimp, a real sissy who’d been faking his toughness all along. I watched them as Sissy started to resist Paulie’s advances.
“What have I gotten into?” she giggled, but I saw the lust in her eyes. Paulie grabbed for her again and she shrieked, “Paulie, stop it! Be a good boy or I won’t take you anywhere.” She looked bashfully at me, but I saw that she liked it, drawing attention to herself. I suppose they were made for each other. But who knew?
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