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My First Boyfriend 2
“Holy Fucking Shit!” Sam pronounced each syllable clearly, his dark eyes stared down at mine. I was cradled in his arms, his strong arms, and then he gently lowered me the rest of the way down to the floor. He still sort of cradled me in his arms, and I couldn’t read the flurry of emotions flashing across his eyes.
I was terrified. Surely I had to say something to him, explain to him why I was dressed as I was. Tell him that it wasn’t what he was thinking. Make up some excuse... But what the hell could I say. I’d been caught red-handed (or, I suppose more literally, red-panty-ed) dressed like a girl.
“Holy fucking shit,” Sam said again, only this time I saw a grin form on his face. Then he stood. I could see him looking up and down my body and his expression became more menacing. “I can’t fucking believe it. Tommy, a fucking little faggot-girl?”
I wanted to die. Right then and there, I tried to focus on my heart and make it stop beating. Why the hell had I been so stupid? It didn’t even register that he called me Tommy, which I always responded to with a sharp, “My name is Tom, thank you!” I was waiting for him to start calling me names, to start punching me. I knew he’d tell my mom. Then everyone would know what a little freak I was. I could even imagine my new step-father, Sam’s dad, throwing me from the house and locking the door behind me. Though, all the older boy did was look at me, a mischievous-looking grin coming over his face.
“No fucking way,” Sam’s eyes got big for a moment as he stared at my belly, “You got cum dripping all over yourself.”
I finally found the strength to move and curled into a ball, so that I was facing away from my step-brother.
“And you even got a pretty little ass, don’t ya,” he said as he checked-out the side of my body I’d just turned toward him.
Chaos filled my mind and emotions. I didn’t know what to do. There wasn’t anything to do. I’d been caught. Sam had seen everything and once he told his father and my mother, well, they’d probably send me to one of those military schools to straighten me out. Or worse, they’d simply throw me out the front door yelling at me to never come back.
“Stand-up,” he said softly. I couldn’t move. I couldn’t do anything, not even cry. Then he spoke again, only this time his voice was much louder and more commanding, “I told you to stand-up, you fucking little girl! Stand-up and face me.” I jumped and did exactly as he said.
With the incredibly impish grin on his face he looked me over. I wobbled a bit, trying to keep my balance in the high-heels, as my step-brother walked around me. I could almost feel his eyes on me and, much to my horror, I realized that this whole time, my dick never went soft. I was more excited than I could ever remember being. Terrified, but so aroused I could feel my dick trembling.
As Sam looked me over, he kept mumbling things like, “I can’t fucking believe it,” or, “This is just perfect.” When he was behind me, I heard him doing something, then felt him putting the long, blond wig back on my head.
I stood there with my eyes cast down to the floor, trying to keep myself from falling again. After Sam had moved all the way around me, I could see the lower part of his body stopping right in front of me, my eyes downcast as they were. He was much closer to me than I’d have liked.
“Look at me,” he said, using the more commanding tone of voice.
As I raised my head to look into his face, I finally felt a tear fall from my eye and drip down my cheek. And as I looked up his body, I noticed that there was a pretty big lump in the front of his jeans. But when I got to Sam’s eyes, all thoughts of what he had between his legs were gone. More tears poured down my face and I wanted to sob, but I couldn’t.
“Fucking little girl,” he said, his voice sounding almost hateful. “I can’t believe it. Playing dress-up with Mommy’s clothes.” His expression was hard and I almost expected to feel his fist punching my jaw. And I did feel something on my face, but it wasn’t Sam’s fist. It was his fingertip. The touch was soft, so unlike the harsh look on his face. I focused on his nose, not able to look him directly in the eyes. Then he said, “Well, I suppose you are sort of cute,” and he moved the tips of his two fingers from my cheek to my lips and rubbed across them.
I felt more tears running down my cheek and after a moment, the tall, dark-haired older boy moved his fingers from my lips back to my cheek and I could feel the wetness of my tears being spread over my skin. I felt Sam’s other hand on my arm, moving up to my shoulder and over, grabbing hold of the straps of the slip and bra I wore. The older boy pulled me closer to him, so close that I could no longer focus on his nose and I was forced to look him right in the eyes. Though I was barely breathing, I could smell him. He smelled good, a bit sweaty maybe, though very masculine. Our faces only inches apart, with one hand rubbing my tears into my own cheek, Sam moved his other hand down my chest until it was at the silk-stuffed cup of the bra I wore.
“Nice little titties,” Sam hissed, looking me right in the eye, though his fingers were all over my chest and the bra. I felt another surge of tears flowing from me. All of the sudden Sam’s face closed the few inches between us and at first I thought he was going to kiss me. That in itself was enough to send another wave of chaos through me. But what he did shocked me even more. His tongue extended and he licked my tears from my face. At the same time, he reached his hand down the slip and into the bra, finding one of my little nipples and giving it a pinch.
I was about to cry out, not so much from the pain of the pinch (which I did feel quite sharply), but from the way it sent a jolt right to my balls, and I knew I was starting to drip pre-cum again. The cry, however, never escaped. Before it got out, Sam’s mouth was covering mine and he was trying to shove his tongue down my throat. I did make a sound, but it ended-up being more of a groan than a cry. Within a few seconds both of Sam’s arms went around behind me and he started pulling me tight against his body, as he kissed me more and more fervently. Before I knew it, my arms were around him, and I was holding him just as tightly as he held me.
I couldn’t have helped it if I’d wanted to. Other than a few pecks in my childhood, I’d never actually been kissed. Not like Sam was kissing me, anyway. And I’d rubbed my body against other boys and girls, but not wearing a slip, bra, panties and nylons, along with the wig, the gloves and the high-heeled shoes. Not to mention that none of the little boys or girls I’d played with ever smelled as potent and virile as Sam did at that moment. Huffing and puffing as he kissed me deep and rough.
I let out another sound, an attempt at a warning. I felt one of Sam’s hands tighten around my back, his other hand sliding down to my butt and started pulling that part of my body against his. And, well, it was a good thing that Sam was basically supporting my weight, otherwise I would have surely fallen when I started to come. It took Sam a moment to figure-out what was happening, and when he did, he pushed me away from him and looked down between our bodies.
I’d already spurted a couple wads, which had soaked right through the slip and left a big wet-spot on Sam’s jeans. He was still supporting me mostly, and we both watched the next few shots fired, oozing down the slip and even to the bright red panties underneath.
“Holy shit!” Sam said with a constricted voice, “You just shot all over me.” I stood there, frozen in fear. At least I wasn’t moving as long as you didn’t count my wobbly legs and the heaving of my lungs as I tried to get a breath. If Sam hadn’t had his hands firmly gripping each of my arms, I’d have surely fallen over. “I turn you on so much, you fucking little pussy-girl, you shot your snot all over my jeans.” My head sank and indeed, I did see a big gooey mess on his pants. “Get your pansy-ass down there and fucking lick it up! I can’t have a big ol’ cum-stain on my jeans.”
It was not a request. And considering Sam was still holding me by the shoulders, as he pressed me down, I got to my knees. I felt the blond wig fall from my head, then I felt my face being forced against the crotch of Sam’s jeans. “Get that fucking tongue out and start licking, you fucking little slut.” I did as commanded. I’d tasted my cum before and had never really liked the taste. It was a bit different, lapping my semen from the worn denim, but I could still taste the bitterness. I could feel heat from Sam’s body, and after a moment, I realized exactly where I was and what was on the other side of the thin layer of cotton.
Sam’s smell was much more potent between his legs than it had been while we were embracing. I could even feel the tingle in my gut a bit, as the last dribbles of the load I’d just shot dripped between my body and the sheer fabric of the slip and panties. I had my mouth against the big lump of cock and balls in my gorgeous, older step-brother’s jeans. I could feel it throbbing against my face and Sam’s hands on the back of my head, keeping me firmly in place.
“You want my cock,” I heard him say softly, “don’t you?”
My head tilted a bit, my lips on either side of the cotton-covered shaft of his cock. I did want it. I wanted it more than I’d ever wanted anything. But I couldn’t say it.
Sam’s hands tightened their grip on the back of my head and I felt my hair being pulled. “I asked if you wanted my cock, you fucking little faggot,” and he pulled my hair a bit more. “Tell me you want it!”
I felt my head nodding a bit, though I didn’t release the lump between my lips, and somehow I managed to utter, “Yeah, I want it.”
“Yeah?” Sam said, his voice soft again. “Say it then. Say, ‘I want your cock Sam,’ I wanna hear it.”
Still without moving my lips too much off the bulge in his pants, I said, “I want it Sam. I want your cock.” And I figured it wouldn’t hurt to add something like, “Please, I want it so bad.” And here’s the thing, I was telling the complete and honest truth. I did want his cock. I’d wanted it for almost a year.
Like I said, I had a big crush on Sam. And when I could, I watched him. I just happened to have to go into the bathroom, right after he took a shower. He looked great wearing only a towel, and I remembered seeing that big lump in his towels, the same big lump that was now pressing against my face. I’d wondered what this would be like. Other than being dressed in women’s clothing, I’d imagined this scenario between my step-brother and I, almost exactly.
Before I knew it the pressure at the back of my head was gone and right before my eyes my step-brother was unfastening his jeans. “Fuck yeah,” Sam crooned as he went at his pants, “You really do want my cock.” I didn’t speak, but I nodded, keeping my eyes focused on where his hands were doing quick work of his jeans. With one quick shove, the tall, muscular older boy’s pants fell down his thick thighs, stopping at his knees. I got my first close-up look at a ‘real-man’s’ cock.
It was long, quite a bit longer than mine, and it was also quite a bit thicker than mine. It was standing-up proud, hard as a rock, I could see a patch dark pubic-hair spreading out from the base of the shaft. And I noticed that his huge balls (they were easily the size of a normal-sized hen-egg) were also covered with a bit of dark fur. I only had a bit of peach-fuzz at the base of my dick and my balls were as hairless as most the rest of my body. I did know, from the few occasions I’d seen Sam without a shirt, that he did have just a little bit of hair growing on his chest. A tiny patch right in the middle and a few dark hairs circling each of his big, dark nipples. But the thing that amazed me most about Sam’s body was that his cock was un-circumcised. I could see right where the thick bulb of his knob was, but it was covered by smooth skin and tipped-off by a wrinkly nub.
It didn’t take long for his hands to get to the back of my head again, only this time he was guiding me to his hard cock. I closed my eyes just before I felt the hot shaft brush against my nose. Then it pressed tight against my face. I could feel the more-fleshy skin of his scrotum pressing against my chin, changing to the more rigid, though somewhat soft skin of his cock-shaft. He dragged it across my face until I felt the wrinkly skin at the tip pushing against my lips.
“Open-up and suck it,” he said as his hands pulled my hair to emphasize his point.
I opened my mouth.
Now before I go on, you have to remember that I’d imagined myself sucking a dick almost every night for at least a year. But I never would have ever actually imagined that it would be Sam’s dick that I sucked (well, sure I’d fantasized about it, but fantasy and reality are completely different), nor would I have ever imagined that I’d be doing it dressed like a girl. But I had imagined that I’d have my first taste of dick forced on me. Some of the big, strong, straight guys I fantasized about would never ask me to do it, they’d just make me. Though, Sam had always seemed a bit withdrawn and shy, and I never would have thought he had it in him.
So I opened my mouth and from that moment on, I could never honestly deny being a cocksucker. I remember thinking about how full my mouth felt with Sam trying to shove his cock deeper and deeper. I remember feeling a different texture of skin, as he pulled his foreskin back, uncovering his cockhead, which was firmly lodged in my mouth. Then, I remember the taste. I’ve since figured-out that it was cock-cheese, but at that moment, I had no idea what the disgusting taste filling my mouth was. It was salty and sour and bitter and tasted rotten. I remember trying to pull my mouth away, but Sam wouldn’t let me.
It didn’t take him long. Less than a minute after he’d yanked-back his foreskin and started stroking himself a bit, moving the uncovered head of his cock around in my mouth, he started to pant and I could feel his cock puffing-up even more in my mouth.
“Oh fuck!” he said once. “Oh Fuck!” he said again. Then, with one more “OH FUCK!” he moved his hand away and sank his cock as deep down my gullet as he could get it. I could feel him tensing and a second later, my mouth was being filled with liquid heat. My only choices were to start swallowing or drown. I chose to swallow.
“Oh fuck yeah,” I could hear through Sam’s panting breath. “Eat my scum, you fucking little faggot-girl.” He tried pressing his cock deeper and made me gag. For a moment, my step-brother just kept trying to shove himself into my throat. Well I was gagging and coughing, and when my muscles opened to expel that which I was choking on, Sam took the opportunity to sink his cock right down my throat. I thought I was about to die, though, if it came to that, well, it’d have been one hell of a way to go. But Sam pulled back, shooting a couple more wads into my mouth, before he finally pulled it all the way out. I coughed and sputtered, trying to catch my breath. I could even feel remnants of my step-brother’s load in my sinus-cavity, some streaming out my nose.
“That was fucking incredible,” Sam said, trying just as much as I was to catch his breath. His fingers went to my face and this time, I felt him spreading his cum on the skin of my cheeks, where he’d rubbed my tears only a few minutes before. Then he shoved one of his cum-coated fingers into my mouth and told me to suck them clean. A moment later, his cock, which was still dripping with the remnants of his ejaculation, was in front of my face and I was being ordered to clean it with my tongue. So I did as I was told.
“I sure am glad I had my mom drop me off a day early,” Sam said as I licked his cum from his still-bone-hard cock. “My guess my dad forgot to tell you I was coming here a day early?”
Sam made me stop licking his dick when it was starting to feel too sensitive and he couldn’t take it any more. Then he made me take off his shoes, so I could get his pants off, and then I had to put them in the washer to get all the cum (both mine and his, some of which had escaped my mouth and dripped down as he shot) cleaned. We still had well-over two hours before our parents would get home from work, and up until about four-thirty, Sam refused to let me change out of the girl’s clothes I had on.
“I think I’m gonna let you be my girlfriend,” Sam told me, as he had me take his shirt and socks off him, which left him totally naked. He made me fix him something to eat, get him drinks. I was still wearing the bra, panties and thigh-high nylons, all covered by the silky, ivory slip. He wouldn’t even let me take off the white gloves and he made me put the wig back on as I waited on him. A little after four o’clock, my big and manly, and naked, step-brother sat on the edge of the couch with his legs spread wide.
“Come here and let me give you a big kiss,” he said. I went and stood in front of him. He grabbed me and pulled me down, onto his body and he kissed me. Then he pushed me down, so that I was on my knees starting at his big, hard cock. “You’re my girlfriend, right?”
“Say it,” he hissed, his voice sent a chill down my spine. “When I ask you something, I wanna hear you answer.”
“I’m sorry, Sam” I said, feeling as though I should look up to his eyes, though I was scared to see his expression, and I couldn’t tear my eyes off his huge cock. Then, remembering the question he’d asked, I did manage to look up and softly said to him, “I am your girlfriend.”
“Good,” he said, and he didn’t look mean, as his voice had suggested, his expression was more, well, devilish. “Now do what a good girlfriend is supposed to do and suck my cock.”
I did what I was told, and while it took longer this time, it was only a few minutes before my boyfriend was squirting another load of cum into my mouth. Knowing what to expect, I did a better job of swallowing as much as I could, though there was so much that some managed to leak from between my lips. After he wiped all his cum from my face, making sure I sucked each and every drop from his fingers, he made me lick his now deflating dick clean, then he made me get his pants from the dryer and dress him, shirt and socks and all, before I went upstairs to change.
“And don’t you dare get yourself off again,” he said as I wobbled on the high-heels over the carpet to the hallway, “My dad’s gonna take your mom out for dinner and a show tonight, so we’re gonna have a few hours alone and I want you at your best.” I’d actually been thinking about jerking a quick load out, when I finally got to my room to change. I wondered if he somehow could read my mind.
I hid my mom’s old lingerie in the bottom of my closet and got into the shower. My dick was stiff as a board the whole time, but remembering Sam’s command, I didn’t touch it (other than with a bit of soap to clean the dried and crusted cum away). My mom got home just as I was drying-off, and I assured her that I was feeling better, though I wanted to take a nap. So I stayed upstairs in my bed, thinking about everything that had just happened and wondering about what the rest of the evening would bring. I heard my step-father come home, he talked to my mother for a bit, then I heard he and Sam talking. I’d just about drifted-off to sleep when my mother came up and told me she’d made dinner for me and Sam. And I noticed she was wearing the skirt I’d had on earlier, which didn’t help at all with the knots in my stomach.
Sam and I ate as our parents prepared for their evening out. I was putting our dirty dishes in the dishwasher when his father told us, “The show doesn’t start until eight-thirty and won’t get over ‘till at least eleven. And we’ll probably go out for a drink afterward, so don’t expect us home anytime before midnight.” Then Mom asked, “So what are you boys doing tonight?”
“With Halloween coming up,” Sam said, “there’s a classic-horror movie-marathon on tonight. Tommy’s gonna pop up a big batch of popcorn and we’re gonna sit in front of the tube all night and get the begeesus scared out of us.”
My mother gave me a look, surely expecting my, “My name is Tom, thank you!” but for the second time that day, I let it pass. She gave me a look. I tried to ignore her, hoping she wouldn’t realize I noticed her.
“We better not come home to find every light in the house turned on,” my step-father said on his way out, “just because you boys are scared of the dark.”
Then they were gone and the atmosphere changed instantly. Once we heard the car pull out and the automatic garage-door-opener closing the big door, Sam looked at me with that mischievous grin on his face and he said, “Let’s go upstairs and find something sexy for you to change into.” The knot in my stomach tightened.
First we went into my room and Sam told me to strip. I felt a bit strange standing there naked, while my step-brother stood there looking at me, him fully-clothed. I got into the bottom of my closet and pulled out the slip and other under-garments I’d been wearing earlier.
“You ain’t putting on that dirty shit,” he said pointing at the lingerie I was holding. “You got cum all over that.” then, he started out of my room, calling behind him, “Let’s check-out what your mom’s got in her room. I’ll pick something out for you.”
But before we got there, I told Sam about the boxes I’d found in the basement. “The clothes down there fit me better, and Mom won’t notice we’ve been digging through her drawers.” I was still naked and Sam made me walk in front of him as we went down the two flights of stairs. “I wanna get a nice look at that girly, little ass of yours,” he said, pushing me in front of him.
I stood there naked and barefoot in the chilly basement shivering (though I think my shivering was due more to my nerves), while Sam dug through the boxes of my mother’s old clothes and chose what he wanted me to wear. “Damn, your mom sure did have some slutty clothes.” He pulled out a pair of fish-net stockings that had strange little buttons on the top of them, then he threw something else to me and told me to put it on. I didn’t even know what it was. “It’s a garter-belt,” Sam informed me, though I still didn’t know what to do with it.
But with a bit of coaching, I soon was wearing the belt, which had straps hanging from it. Sam explained that the straps connected to the weird buttons on the tops of the stockings and within a minute or so, I was standing there wearing only fish-nets and a garter-belt, which made me feel even more naked than I’d felt before I’d put them on. And much to my horror, I felt my dick starting to get a little stiff.
“Holy shit,” Sam said, pulling an odd looking pair of panties from the box and throwing them to me. “Put these on.” I’d heard about crotch-less panties before, but I’d never seen a pair before that moment. Sam told me to put my dick through the hole. Even with one more item of clothing on my body, I still felt extremely naked. And my dick had gotten a bit stiffer as I fumbled to get the panties on, with my dick hanging out of the hole in them.
A few minutes later, I was standing there with my outfit complete. Along with the fish-net stockings, the garter belt holding them up and the crotch-less panties, Sam had picked out a bra (which he stuffed had me stuff with a pair of old socks), a short mini-skirt and a tube-top. He also found an even higher pair of heels than I’d worn earlier, then topped it all off with a long brunette wig. The shoes weren’t easy to walk in at all, and Sam laughed at me as I tried.
“God-damn, you’re pretty,” he said once I had everything on and straightened as best as I could. “Now let’s go back upstairs so we can put the finishing touches on you.” I wasn’t sure what he meant until we were in the upstairs bathroom and he started digging through my mother’s make-up drawers. He threw me a tube of lipstick, some mascara, and a hard-powder compact. “Get yourself all dolled-up, then we’ll go have some fun.”
Having never put make-up on, I didn’t do a very good job of it. Looking at myself in the mirror when I was done, I saw what looked like a young girl with long, thick dark hair, who seemed to have dressed-up in the sluttiest possible outfit, wearing too much make-up. It was only my little bump of an Adam’s-apple and the bulge in the mini-skirt that made me actually realize that it was a boy looking back from the mirror. The only part of my outfit that bothered me (other than the basic fact that I was dressed like a girl) were the straps of the bra over my shoulders, which were bared by the tube-top barely covering my chest.
“Oh yeah,” I heard Sam crooning from behind me, staring at the same image in the mirror I saw, “that’s much better.” I felt his hand on my bare arm, moving slowly from my elbow to my shoulder then back again. His caress was soft and I felt my already-stiff dick get even stiffer. He moved a bit closer to my backside and I could feel the heat of his body. His face nuzzled next to mine, pushing the long hair away from my face and neck. I felt his breaths against my ear, then his soft lips moving against my skin as he said, “I’m so fucking lucky to have a pretty girlfriend, like you.” His hand continued rubbing over my arm and I felt the front of his body make contact with my back. Then he started kissing my face and neck and cooing things like, “You’re such a hot, little slut,” or, “I can’t wait to feel my cock spreading those pretty, painted lips of yours.”
My dick was hard as a bone and I could feel the top of the hole in the crotch-less panties digging into my skin, right at the base of my dick, where my little puff of pubic-fuzz had sprouted.
Then after a moment, I felt one of his hands moving around to my front, over my hip and around to where my bulge was tenting the mini-skirt. “You’re fucking hard as a bone. You like this shit, don’t you?” I felt him push his hips forward and could feel the bulge in his jeans pushing against my butt, which thanks to the several inches of height I’d gained by the high-heels I wore, were almost about the same height. “Fuck yeah,” he crooned in my ear between his kisses and nibbles, “you’re gonna take good care of your boyfriend tonight, aren’t you?”
Well, I’d just been standing there, trying not to think too much about what was happening, and trying to keep myself from shooting as I felt my good-looking step-brother’s body against my back side and his hand still rubbing the big lump in the front of the skirt I wore.
“I asked you a question, slut!” he hissed in my ear and I felt his hand, which had been rubbing up and down my arm move around a bit and slap my butt. “You’re going to take good care of me tonight, aren’t you?”
“Yes,” I said quick but softly, “sorry, Sam.” I nodded slightly and felt his hand cup one of my buttcheeks through the skirt.
“Fucking right you are,” he said and pressed himself even tighter against me, I could still feel the breaths of each word he spoke right against my ear. “You’re gonna do whatever I tell you, and if you do everything right, I might just let you shoot a load too.” He gave my hard cock a tight squeeze through my skirt, then all of the sudden I felt coolness against my backside and when I looked, Sam was walking out of the bathroom. “Come on slut,” he called out behind him, “we only got a couple hours before they get home.” It was barely seven-thirty and at the earliest, our parents would be home in four and a half hours...