ready or not

I was sixteen when I lost my virginity to a man. I had only been with one female, and I had given my boyfriend, Omar, many blowjobs. Still, I had yet to let any guy take me all the way. Omar told me that he was okay with the slow pace of our relationship, but there was always something about the look that he got whenever he said that to me that made me question whether or not he would wait around much longer for me to be ready. I decided that my cherry should be his twenty-seventh birthday gift, since I didn’t have any money to get him a real gift. I also knew that his turning twenty-seven only three days after I had turned sixteen was an omen that he was the one. By that time, I already knew that he cared enough about me to deserve the privilege.
The idea of his huge nine and a half inches prying its way into my tiny opening frightened me, to the point of anxiety. If I could survive the entrance of the enormous head, I could get through it, or so I tried to reason with myself. I tried to control my convulsions as he laid me on his bed and began to kiss down my shoulders and back. He and his wife’s previous fuck had left the unmistakable stench of his ball’s sweat on the sheets, and I became instantly aroused. My heartbeat thundered against the mattress, drowning out his moans and the slurps of his tongue. He commenced licking the top of my cheeks as he ripped my pants all the way down, and then began to slide his tongue up and down the length of my crack.
“Relax!” he demanded, as the shock of him inserting a dry finger caused me to jerk in pain. He forced my chest flat against the mattress again. “Take it, baby! You know I wouldn’t do nothing to hurt you.” His words were muffled by his task of nibbling my cheeks.
“You are hurting me,” I pointed out as he pushed two big fingers inside me, knuckle-deep. I fought back a scream as he removed them.
“You told me you were ready for all this.” He sat on the edge of the bed, taking in deep breaths to control his temper, “If you going to act like a bitch over two little fingers, what you going to do when you get all this dick?”
Something told me that Omar was not going to make good on his promises to take it easy on me. Still, when I looked at the picture of his wife and children on the nightstand, I felt smaller than he could have intended to make me feel with his harsh words, but it wasn’t due to what he said. It was because of how immature I was acting. Here I was with a man who had risked losing everything, for the past eight months, just to be with me: his wife and kids, his job as a youth minister, and his position as assistant principal at the local middle school, not to forget his freedom. Enduring a little pain was the least I could do for someone who was willing to jeopardize four years of marriage and risk a jail term just for me.
“I didn’t say stop,” I attempted to appease him as I rubbed his back. Unfortunately, my hands were too clumsy and shaky to be seductive, “I’m ready for you to fuck me; really, I am, but—
“There can’t be any buts, Jerrin! Fuck it! Just get dressed; I’ll just drive you home and go pick up somebody whose sure about if they love me or not! I think you got doubts.”
He was even more handsome when he was angry. I definitely had no doubts about wanting to feel those coal-black muscles quiver all over my skinny, yellow torso. I even anticipated the pain of the six- inch circumference of his tip, smashing its way into my ass. At that point, I would have let him have me any way he wanted. I just wanted to know one thing before that happened, just so I would know whether or not to fall completely for him.
“Omar, the other day you said that if the world would accept you and me as a couple, you’d leave your wife and raise your kids with me?”
He nodded, and sexily arched a thick eyebrow in anticipation of where the conversation was heading.
“Did you mean it?” I finished, and cast my eyes to the ground, as I often did whenever I felt that I had stepped over my boundaries in the relationship. I knew that I always sounded stupid to a guy as experienced as Omar.
“I can’t believe you’re asking me this shit. Not on today of all days, Jerrin! This is my birthday, baby! My wife and the boys are all the way at her mama’s house in Florida. You are all I have; please, just let me have you.”
“I just want you to tell me the truth!” I shuttered, fighting back nervous tears, “I’m going to let you fuck me either way, but you have to tell me what it means to you; you owe me that.”
“What kind of bullshit is that?” he sort of laughed. I was crushed by the fact that my sincere concerns humored the man that was about to deflower me, but I was aroused by the baritone of his voice and the strength of his strong hands as he grabbed my chin to force me into eye contact with him, “So, you don’t believe I love your stupid ass?”
“That’s not what I’m saying! Look, this isn’t like sucking your dick, Omar! It’s going to hurt like hell, and it’s going to change me forever. Before I do this, I got to know if you really care about me, or if I’m just the faggot boy down the street, who you let suck your dick. I already told you that I’d still let you fuck me either way, so be honest.”
He sat silent for a while, and I felt like a complete ass for spoiling the perfect mood. At that moment I completely understood why he never invited me to hang out with his friends whenever he had boys’ night. Everything I said made me sound like the stupid kid that I tried to make him forget that he ever saw me as.
“I know I’m being stupid,” I finally spoke, “I’m scared though, baby.”
“I think you’re sexy when you’re stupid,” he teased, sucking the back of my neck. Once again, I was pushed flat on the bed, and he mounted me, grinding his scorching erection against my cheeks. He continued to leave love bites all over my pale torso. I would have to worry about explaining them to my dad later; right now, it felt too good just being underneath the weight of his body.
He positioned my body, rough and demanding, jerking my limbs uncomfortably, until he had me on my knees. My butt was raised enough for him to bury his face between my furry cheeks again. This time he reached under me and began to jerk my dick for me. I twisted my own nipples in response to the pleasure. Once again, his magical tongue was replaced with a finger. This time I bit the sheet to hold in my protest.
“That’s right,” he coaxed, “Yeah, you ready for this dick now, aint you?”
“Yes!” I retorted, willing to withstand anything but the jagged fingernails again.
He flipped me onto my side and hoisted one leg over my shoulder. Spitting on the tip of his penis, he positioned himself for entry: the antagonizing head pressed against my pucker, pulsing and waiting for its chance to rip me open. Pre-ejaculates and saliva allowed just the tiniest portion to slide in, causing me more of a tingle than pain. He held my hands and we counted together, between kisses, as he prepared to enter on the count of three:
“One… two—
“OOW, shit!” I wailed out, because he was too impatient to let me get to three. I started to cry before I could fully process the pain of his jab, and he withdrew, leaning all of his weight against me as he reached for a jar of his wife’s hair grease. It was thick, and one shade darker black than Omar’s beautiful skin. As he rubbed it on my rim the room became saturated with the smell of pine tar. I wondered if the chemicals in it would burn me, but I would chance it before allowing Omar to enter me again, only using spit.
As I watched him massage some grease on his throbbing, crooked dick, I began to revamp the horror stories I had heard at school: guys getting stuck together and having to be carried out in that condition via ambulance, guys getting torn and having to be stitched up, thereby being called out to the entire world before their proper time. I suddenly wasn’t sure I could actually go through with the ordeal. What if Omar got stuck inside me? What if he got stuck inside me, and then the doctors ripped me trying to get us apart? Then I’d be the faggot who got stuck and needed stitches, two walking queer clichés in one.
“Oh, no!” I yelped, feeling him thrust every inch of himself inside of me. All my what-ifs subsided; I was forced to deal with the current pain.
“Don’t cry!” he whispered, sticking the two fingers he’d just retrieved from my ass into my mouth to silence my whimpers. The sight and sensation of me sucking his fingers began to turn him on more, and he let me know by going faster, rocking me with each deep thrust, and whispering in my ear that he loved me. Even love couldn’t help me endure the pain.
“Stop! Omar, if you love me, stop!” I begged, and as soon as he did, I scrambled from beneath him.
He looked at me with belittling eyes, wiping my blood from his penis, which jerked up and down with excitement, “What now, Jerrin?”
“I think we should be using a rubber.” This time I didn’t look away. Being the older one, Omar should have been the one suggesting protection. If he thought otherwise, he should have felt as small as he always made me feel when I questioned him. Of course, Omar didn’t agree. He looked at me with so much disgust that I wished that I could become a turtle and retract into my shell until his stare ended.
“You think I got something?” he asked, grabbing me so hard that my biceps began to spasm from poor blood circulation, “Look me in my fucking face and tell me that you truly think that I have a disease! How long haven’t you been sucking my dick?”
“If you cum in my mouth I can spit it out, but if you cum in my ass it’s already in my bloodstream; I read that in health. So, do you have a rubber or not?”
He sat, huffing and cursing, for a few seconds; he then went to his bottom drawer and removed a Trojan condom. “Jerrin, my wife counts these! You’re starting to make me fuck up!”
“Go to the gas station’s vending machine and buy one back when we’re done,” I suggested. I certainly was worth eight quarters.
“Are you really going to be that silly?” he pouted, “You’re the faggot; if anybody should be questioning who might have something it should be me, asking you whose dick you be sucking when you aint here! I know I don’t fuck nobody but my wife!”
“How do I know that? How do you know who she be fucking? And if you let a faggot suck your dick, what does that make you?”
“I’m sorry I said that to you,” he whispered tenderly, and pulled me towards him. He began to grind against me slowly, making his dick graze mine as we swayed and he whispered in my ear, between nibbles, that I was his thug-baby. The condom became obsolete at that time. I could have noticed puss boils all over his body, and I still would have licked him from head to toe, and then let him have his way with me. The combination of his deep voice and his strong hands on my ass was always too much to resist.
“You have to trust me,” he instructed, placing me on my back this time. My legs were forced over my head, in an uncomfortable position, and my feet were placed against his chest. He twisted my arms above my head and thrust inside me. The pain was intolerable, and he was still only halfway inside of me.
I stopped biting my tongue long enough to beg for a second to adjust, but he was already too far into the ordeal to listen. He began to kiss me, attempting to muffle my screams as he humped in and out of me. Between the weight of his body against mine, and the vicious kisses, almost engulfing my entire mouth, like a cat stealing a baby’s breath, I felt like I was dying.
“Yes sir!” he huffed, letting go of my hands, “This pussy sure was worth waiting for! I’d wait another eight months just so it’ll feel this good.”
I wished I could say the same thing. The only sensation I was feeling was the sting of the pine tar grease, and the force of him slamming in and out of me recklessly. I reached between my thighs, hoping that playing with my dick would take some of the pain away from my ass, but he grabbed my hands again, and they were forced over my head.
“I’m going to make you cum,” he promised, “I’m going to fuck you so long and deep that you shoot that cum everywhere, without having to touch your own dick.”
I had heard of that happening, but I doubted that he could achieve the feat that night. I wasn’t enjoying the sensation of him stretching me at all. I sat up and began to suck on his nipples, not knowing what else to do with myself.
“Whoa, easy baby! Don’t do that,” he pleaded, “That’s going to make me cum too quick. I’ve been dreaming about this for a long time. Let’s just be here together for a while before its over, you feel me?”
He withdrew from me, and I thanked god aloud. He then inserted his dick into my mouth and straddled me. For the first time, he took my semi-erect penis into his mouth and began to pleasure me back. I was in heaven, until those damn fingers found my hole again. This time the feeling was more erotic than painful, and I began to work my hips in slow circles, feeling his fingers dig deeper and deeper into me as we made love to each other’s mouths. Omar sucked my dick like a seasoned pro, taking more of mine in his mouth than I could ever fit of his, but then again, he had me beat by two and half inches.
“I’m ‘bout to cum!” I tried to warn, but he didn’t even try to pull away; he went farther down on my dick as my liquids spewed out into his hot mouth. I flapped round on the bed like a fish out of water, and he stood over me, his eyes smiling at me as he rolled me unto my stomach. Once again, his fingers stretched my cheeks so far apart that I feared my hole would rip. He then spat my load into my hole, and began to spread the mixture of melted sperm and hot saliva with his fingers.
“Damn, baby!” I breathed as he slid his spit-covered tip across my hole, causing me to buck in pain. He tried to push all of it in too soon. I took a deep breath and bit down on the blanket. It took him longer than the last time to get in, but once he was inside the pain wasn’t nearly as severe. I began to enjoy the fullness, the slippery sensation of my sperm and his spit mixing with the grease as he plowed me, but the most gratifying was the smell of his sweat dripping unto my body.
“You want me to hurry up and cum?” he teased fucking me harder and faster, “Talk dirty to me and make me cum, then I can take all this dick out of your little pussy!”
“I don’t know what to say!” I trembled, turning even redder with embarrassment than the pain had caused me to become.
“You know what I want to hear; tell me this is all my pussy!” he demanded, smacking my skinny cheeks so hard that I released tears on the impact, “Tell me I’m the only man you’ll ever let get this little redbone pussy!”
“You know that, Omar!” I begged as he fucked me even harder, “Oh, god baby, this ass is always going to be yours only; you know that shit!”
“You goddamn right I know that shit’ ‘cause when I get done with this ass, no other dick is going to be able to touch all your walls at once again! I’m going to stretch this little pussy so that my dick is the only dick that you can ever feel again!”
By then, he was fucking me so viciously that the impact of his nuts and thighs, smacking against my ass with each thrust, echoed through the room, assisting Omar, who had pushed my face in the mattress, in drowning out my screams. His own moans and curses roamed free above my head, and sometimes directly in my ear, whenever he leaned over to dig deeper into me.
“This shit hurts!” I pleaded as he bounced in and out, so hard that the lumpy mattress danced halfway off the bed. Even when I had to balance myself on my fingertips to keep from hitting my face on the marble floor, he continued to fuck me with malice, as if he hadn’t just looked in my eyes and told me how much he loved me five minutes earlier. It was as if he was angry with me that he was enjoying himself as much as he was.
“Stop crawling bitch!” he thundered, smacking my ass so hard that I did actually attempt to jump away from the pain at that moment. I hadn’t been crawling at first; he was pounding away at me so roughly that I was sliding off the slippery, satin sheets.
His arms looped under my armpits, and jerk my arms up, and into an inescapable full nelson. Holding me so tight that I couldn’t breathe, he stood, and I was forced to stand too, with his dick still deep inside me. Nothing of me touched the floor but the very tip of my big toes, as I was five-seven and Omar was six-two. All I could do was try to work my ass in circles and make him cum so that he could stop slamming in and out of me with all his might. On my tiptoes it was a difficult task.
“Stop trying to fuck my dick and let me fuck that ass!” he demanded, squeezing me harder still. He walked us over to the large mirror and I could see the pain on my face, and the ecstasy on his as he fucked me so violently that my legs, and my lifeless arms, swayed to and fro, making me appear to be an oversized Raggedy Andy with my curly, reddish-brown afro and flushed cheeks.
The pine-tar grease, which he had spooned into my ass earlier, began to melt and trickle down my ass and onto his curved dick and his balls. It looked extremely disgusting, but it appeared to turn him on, because he became even more sadistic. Dropping his hold on my arms, he spread my already stretched hole even wider so that he could watch it leak around his dick as he fucked me and grunted, “Yeah! Hell yeah, boy; take this anaconda!” over and over again.
By this point, my hands had fastened around the towel rack, just above the mirror. My feet rested, daintily, against the glass just enough to keep me from falling as he bucked in and out of me, only holding on to my ass.
“I’m gonna cum!” he announced, fucking me faster yet.
One deep, unexpected thrust caused me to kick out in pain, shattering the beautiful glass in six pieces. He cursed, and pulled me away before the falling fragments could do any more harm to us than had been caused to my left foot, which was squirting longer and longer jets of blood with each bounce I took against his dick.
I felt him cum deep inside me, and I watched in what was left of the mirror, as the product of his labor leaked out and was pushed back in by his crooked monster over and over, until he couldn’t stand the sensation any longer and snatched free from my walls, opening the floodgate for the trapped mixture of red and white juice that bubbled out, mixing with the pool of pine-tar.
“Goddamn it! Baby, you came in me!” I observed, in terror.
He smiled in response. Leaving a trail of bloody semen and tar behind, he toted me to the shower, and held the injured leg up for me, backing me against the wall and pushing his dick inside me again, he began to urinate in me, and try to convince me that it would kill any infection. Of course, I wasn’t buying it, but the sensation of the hot liquids against my throbbing walls was so phenomenal that I went along with it.
“Don’t take it out!” I begged as he sucked my neck and twisted my nipples, all the while his hot piss sloshed around inside my cavity, only leaking out in tiny droplet at a time. I grew so hot that I felt faint, and thanked god that he was holding my thigh, and that I was supporting myself against the shower walls on my fingertips, or I would have smashed my face when the spring of cum burst forward, painting his rippled abs. He hadn’t lied after all; he did make me cum without having to touch my dick. Regretfully, that was the first and last time that anyone would accomplish that feat.
“Here I go again!” he screamed, removing his cock, “I’m gonna nut again!”
My ass made a sound like a plunged drain, and his piss shot out. He tried to stop the flood with his dick, which was erupting with its own hot larva. Finally he gave up and fell against me, forcing my back so hard against the shower that I lost my breath.
“I really do love you,” he whimpered, when we were both able to speak again, “so don’t ever doubt that shit again, especially not to my face!”
“I love you too!”
I shuttered at the feel of the shower stream, and melted at the feel of his sweet lips against mine, and his hands soaping my body up ever so gently. I wished at that moment that I was older, and then my parents’ curfew couldn’t make our night come to an end in less than twenty minutes.