A sissy-boy is born
"Some say boy-cunt is next best to plain ole cunt. Others say it's better. I'm one of those others. It's a verifiable fact that boy-cunt runs hotter. It just does. And tighter."
"Jess, I think you gave him too much."
"Nonsense." Jess said. "He's starting to come 'round already. That shit don't last long."
"But if he wakes up and starts to fight us off, then calls the sheriff?"
"Won't happen, Bo. This boy was makin' eyes at me at Darryl's long before I slipped him the ruffie. C'mon, let's get his pants off."
The voices belonged to two figures directly above me. I was lying down. My head was spinning, my vision blurry. Last thing I remembered was sitting at the bar of a truck stop last night. Or was it still tonight? I had come in off the highway, looking for a motel. Judging by the room and the bed I was now on, it looks like I found it.
A pair of hands began to fumble at my waist, unbuckled my belt and unzipped my fly. Another pair grabbed the bottom legs of my trousers and yanked them off.
"Damn, would you look at that! This boy has no hair on his legs. Just like a girl. You sure know how to pick 'em, Jess."
"Yessir," Jess whooped. "We gonna have us a time now!" Jess gripped my left shin and slowing ran his rough hand up to the smooth soft skin of my inner thigh.
Jess was right. I was making eyes at him. I had spotted him soon after walking into Darryl's Roadside. Dressed in a red-black flannel shirt and faded blue jeans, he looked about 55 or so. He was scruffy. His white-grey stubble covered a well-worn face that looked to have had too much fun in the sun over the years. I figured him for a trucker, and one who was secure enough in his masculinity to accept a blowjob from a guy out in the parking lot.
But who exactly were they calling boy? It couldn't be me. I was a grown man, in my mid-30s, with a wife and a kid, and my own business to boot which was now just entering a period of growth. That's why I was on the road these days. Traveling also provided the perfect cover to explore a side of my sexuality that I had fantasized about ever since I was a teenager. To date I had jerked off and/or blown about two dozen men, mostly truckers. You'd be surprised how open truckers are to a warm mouth going down on them in the cabs of their semis.
It was true about my hairless legs. Earlier this week I had I stopped in a drugstore and purchased a waxing kit on a whim. It was advertised on the box as a complete hair removal system. I did this because I noticed that the men I would blow often groped me down the back of my pants. They'd squeeze my buttocks, but they'd stop short of penetrating me with their fingers - something I very much wanted to explore. Much more than having my cock and balls fondled. You see, I was learning that I was a complete 'fem' in the hands of these men. I wouldn't even get hard while I sucked them. A burning desire was there, sure. But it ran much deeper than what hung outside my body, like an itch I couldn't reach on my own. So to encourage that exploration, I waxed off the hair back there to make it as smooth as a woman's backside. You know, to make it more like what they were used to with their women back home. While I was at it, I waxed my legs, chest and stomach too. My groin area I didn't wax, but I did trim the hairs down into a neat finish.
I swear I felt so feminine after that! For days I fantasized about being taken by one of these truckers, just like a woman. But that was just it. It was a fantasy at this point, while the situation I found myself in just now felt a little too real. It was spiraling out of control fast. I became uneasy.
Bo circled around to the side of the bed and pulled my shirt over my head and arms, holding them by the wrists above my head by one hand. The other hand he ran across a hairless armpit, causing me to twist away from the tickle. "And no hair up here too," he says.
"Grab hold of him good. Let's roll him over and get his underwears off," says Jess. The second my 'underwears' hits the floor he scrambles onto the bed and straddle my legs. His hand gives me a sharp smack on my ass, then another, and another. He rubs it tenderly.
"You like that, boy? Huh? Yes you do, I know you do. You got some flesh back here. Now let's see what kind of secrets you got inside." I feel his hands begin to part the cleft of my buttocks. I start to move away in protest. I even clench my buttocks together real hard. But I quickly realized I wasn't going anywhere. With Jess' full weight on my legs and Bo's tight grip on my wrists, I was helpless. And scared. But it was an exhilarating feeling nonetheless, being manhandled by these two strong men.
"This is boy-cunt at its finest, Bo," Jess mumbles, as he leans in. I first feel his rough stubble, then his hot breath, then his tongue exploring the tight ring of my anus. As he licked and penetrated me with his wet tongue some of the tension that had built up in me since I first came to in this room began to dissipate. I was coming around fast. My head was almost completely clear, clear enough to understand that I was no victim here. I wanted this as much as they did.
Jess shakes his entire face in my ass, jiggling my fleshy cheeks against those of his face. He stands up and rolls me over. Bo releases my wrists and I feel them staring down at my groin. I look down. I'm mortified! A feeling of extreme shame courses through my body and I quickly cover myself with my hands. Neither of them says one word. I know I don't get hard with guys, but this was ridiculous. With my balls tight around the base of my cock, I was barely a nub. Almost the entire length of my cock had retreated back into my body, effectively making my cock only as long as my cock head. Gently removing my hands, Jess takes a hold of my tiny penis between his index finger and thumb. His looks at it curiously for a few moments, then runs his eyes repeatedly over the entire length of my body. As he does, he pinches the little baby mushroom he has between his fingers. But instead of my cock responding, I feel this powerful desire well-up inside me. It was as if whatever urges I used to have as a man down there had transitioned elsewhere, to a place that, ironically, only another man could access. Jess looks over to Bo and says in a very serious tone,
"Bo, what we have tonight is something special. Very special. This here is the kind of boy you meet only once in a very blue moon. A boy whose body transforms itself the best it can into a girl whenever it is in the presence of a real man."
"Whaddya mean?" Bo asks.
"He's a sissy-boy. A genuine, 100% sissy-boy." Jess gazed down at me. "Isn't that right, you're a sissy- boy?"
"No-ooo," I say, my voice cracking slightly. It sounded more high-pitched than usual. "I've sucked some guys off before. But no more than that." Bo must have been undressing behind me all this time, for the next thing I knew his fully erect cock was poking me against my face. I felt the pre-cum against my cheek and turned, instinctively opening my mouth to take him in. I raised my hand to cup his balls and tried to sit up to get a better look at him. He was younger than Jess, but not by much. Between the two, he was the more handsome. But Jess had that rugged, grizzled look that some women swoon over. He was now busy undressing at the foot of the bed and slowly caressed my lower legs while doing so.
"Natural-born cocksucker. Dammnn!" Bo sing-songs, placing his hands behind my head so as to guide it.
I threw myself into my assigned task. Sucking cock was so much better on a bed than trying to crane your neck under a steering wheel! You can have your man straddle your chest and really get access to him. Especially underneath him. To have him rest his cock on your face while you licked the underside of his balls was pure heaven. I think what thrilled me the most was that it was all so much more submissive than sucking from above. I imagined that the only thing better would be to kneel in front of a man, like some ancient virgin worshipping the pagan cock-gods.
As Bo face-fucked me, Jess took one of my hands away from where they were kneading Bo's muscular ass and guided it towards him. I couldn't see Jess, but understood that he was standing next to the bed. My hand came into contact with what I initially thought was the forearm of his other arm. Only it couldn't have been, it was softer. It even slightly squished when I gripped it. Impossible, I thought. It's much too big to be... I strained around Bo to have a look.
In my hands was Jess' cock! By far the biggest I had ever seen in person. Easily 8 inches in length. And the girth? My fingers could just barely encircle it. And it was only 85% or so hard! When I release it, it swung heavily down from his body to hang between his legs. The weight of it alone was impressive. It was so engorged with blood I couldn't take my eyes off of it. Bo, seeing how his friend's cock affected me, cried out,
"Gawd damn it Jess! You promised I'd have first dibs before you pulled that thing out."
"Fine, fine," Jess says as he pulls away from my hand and retreats out of my line of sight behind Bo, still sitting on my chest. Bo tried desperately to get my undivided attention back on his own cock. "I'll come back in exactly 20 minutes. Remember, just her mouth. Nothing more."
"Yes, sir, just her mouth," Bo says in a tone of frustration. By the time Jess dresses and leaves the room, Bo is at half-staff. I give it my best to keep him hard. He's angry. I didn't fully understand the dynamics of their relationship, but Bo obviously didn't like being ordered around by another man. Unlike me, as I was discovering.
"You like that big dick of his, huh? I hope you ready for that. 'Cuz after I'm through with you, he's gonna come back and fuck your little sissy-ass hard with it. Toss you around like a little ragdoll. And you better not cry, 'cuz that'll just get him madder." Bo started to get hard again. He obviously liked the rough stuff and got off trying to scare me. He started slapping my face with his cock, calling me all sorts of degrading names. But instead of scaring me, it just got me hotter and I urged him on. Because I knew that as soon as I got Bo off, Jess would come back to me. Bo may have been younger and more handsome, but throw in Jess' magnificent cock into the equation, and... well, it was no contest who I wanted more in my bed.
Bo got off of me and stood next to the bed, grabbing a fist full of my hair and dragging me off as he did. I was suddenly kneeing before him. My eyes were tearing from the hair pulling.
"Don't cry, bitch. Open your mouth and look up at me while you suck. And look like you mean it!" He began to mercilessly fuck my mouth and I sucked as hard as I could, making this slurping sound each time he slipped out. After a few minutes he realized he could only get his cock so far into my mouth. He grabbed me by the hair again, clearly frustrated. Jess had given him a 20 minute window to cum and it was closing in fast. He positioned me on my back, with my head hanging off the bed. He was now upside down when I looked up at him.
"Tell me you want your throat fucked hard. C'mon! Tell me you're a useless little bitch and then open your sissy-mouth wide so I can ram it in." I told him just that, and he did as he threatened. Positioned as I was now, he had clear access down the entire length of my throat. As he rammed his cock all the way down, his balls slapped against my nose and partially covered my eyes. He stayed that way for a few seconds and I started to panic, because I couldn't breathe. I slapped at his thighs with my hands as a signal.
"Can't breathe, can you?" He thankfully withdrew. But before I could answer and before I could catch my breath properly, he rammed it back down. Only this time with more force. And he held himself down my throat just a while longer, taking his pleasure. As he swiveled his hips, his balls squished over my nose and eyes. But no sooner did he withdraw again that he was ramming himself back down. Ram, withdraw, repeat, each time rougher and longer. I didn't know which was worse, the suffocation or the pain of the ramming which I knew was taking its toll on the delicate lining of my throat. Tears were streaming out my eyes and down my forehead. After a few minutes of this brutal face fuck, I was full blown crying and trying to get him to stop. But it was then, and only then, after he had fully broken me, that he announced that he was about to cum. I expected him to deposit his seed in my belly, but he withdrew instead, grabbed me by the hair and shot his load all over my face. Once he wiped the last of his cum on my face from his cock, he gave me a final look of pure disgust, put on his clothes and left without saying a word.
I was alone. I went into the bathroom and turned on the light and looked at myself in the mirror. I was the picture of a total whore slut. My face, wet with tears and semen, had great globs of white cum hanging from my cheek bones and chin. Scooping some up with my fingers, I greedily sucked it into my mouth. I had to admit that that brutal scene turned me on immensely. My self-satisfaction was immediately ruined, however, when I suddenly realized that Jess would be back any minute. I had to make myself pretty for him. Exiting the shower minutes later, I heard him calling out to me. My man was here! I was joyous. I may have been the happiest little girl in the whole wide world just then.
"I'll be right there," I sang out in a high pitched tone that I hoped didn't sound too ridiculous. After drying off, I stepped into the room naked and there was Jess, working open the buttons of his flannel shirt. He greeted me with a warm smile that made me virtually skip over to him. Placing my hands around his neck, I nuzzled my face against his deep hairy chest and purred. He was about 6 inches taller than me. A perfect height.
"Bo didn't hurt you, did he sweet thing?" he asked.
I looked up at him and batted my lashes. "Not too bad. But it was worth it because now I have you."
"You are a special thing, aren't you? Go over and sit on the edge of the bed while I finish undressing."
I did as I was told, eager to please my man. Sitting with my knees together so that my balls bunched up, I proudly displayed my little penis.
"Darling," Jess says to me as he hikes his underwear down, releasing his massive cock, "you are something to be savored over many nights. Unfortunately we only have this one." He stepped forward with a manly self-assuredness that made me ache. Gently pushing me back, he placed my feet flat on the edge of the bed. He lifted his cock and let it drop down so that it fell between my thighs and alongside my own tiny cock. The size differential was astounding. It surely couldn't be the same human organ.
"Tell me," Jess asked, as he pinched my baby penis again between his fingers, "You were never really able to satisfy a woman with this, were you?"
"No," I said sheepishly. I was in complete awe of this man and wanted nothing more than to submit to his raw masculinity.
"You know why? It's because you were put on this earth to service other men. Like me. You see... sometimes Mother Nature messes things up. She messed up with you. Well, tonight we set things right once and for all." Jess picked up a brown paper bag off the floor and pulled out a tube of KY and a box of extra-large condoms. He must have bought these while I was alone with Bo.
"I'm scared you won't fit in me," I said. "You're very big."
"Nonsense. I've taken smaller boys than you. Let me tell you a secret." He picked up his cock and placed it in my hands ,and proceeded to tell me how he never got harder than what I could now feel. I looked down. His cock was the same massive size as before, about 85% hard. He continued, telling me that while this was just hard enough to penetrate me, it was still soft and pliable enough to navigate the curves of my boy-cunt. All this talk was making me quiver. And it all made perfect sense.
"That way all of you will get to be inside me," I said. Jess nodded, smiling. He took a large glob of KY, and applied it to my virgin hole, using a single finger. I opened up so quickly that he quickly added another finger inside me. Working in the third finger took longer, but he lovingly took his time, wanting me to be as loose as possible before he attempted to penetrate me with his cock. After awhile his thumb was pressed just under my balls, with his index, middle and ring fingers completely buried inside me. He could now pinch my prostate gland between his thumb and fingers and massage it at will. I was losing my mind and gripped his wrist firmly with both hands.
"Sir, I can't stand it. Please take me," I begged, reaching up to caress his broad shoulders and arching my back. "Make me your sissy-boy." He leaned down, still with his hand in my ass, and placed his mouth around one of my nipples and pulled hard. This act suddenly made me realize I had tits. I told him I wished they were bigger, like a girl's, for him.
He shook his head, "No, sissy-titties are always sweeter that plain ole titties." I squealed with delight! He rose up and reached for the condoms and put one on. He gripped the top part of his cock and proceeded to rub his cockhead all over my sloppy, KY-slick anus. I stiffened a little, knowing that this was the moment.
"Try to relax. I want you to take a deep breath and push down while I push in, OK? Can you do that for me, sweetie?" I nodded and felt him push. I breathed in as he said and pushed down with all my might and felt his cockhead pop past both my external and internal sphincters. It was painful and I'm glad he pushed no further. I felt so vulnerable in that moment. Had this been Bo I'm sure he would have proceeded to tear me open. But Jess would take his time and patiently work his massive member back and forth into me, making each thrust go just that little bit deeper and every once in awhile pausing so that I could catch my breath.
Pain slowly turned into pleasure as my sphincter muscles relaxed to accommodate him. Each movement he made, whether withdrawing or thrusting, would cause his cock to rub against my prostate. He was so large that there was simply no way to avoid it. I focused on this sensation and then noticed Jess looking intently down at me. I looked down as well and witnessed a thin stream of clear liquid slowly oozing out of my little penis and down the side of my stomach.
"I'm coming!" I exclaim.
"No, you're not. Do you feel any orgasm? No, you don't. That there is what I call sissy-juice. Basically, you're body is transitioning from man to woman. Don't you see? We need to help that along. What I'm gonna do is fuck whatever remains of a man out of you."
Encouraged by this result, Jess began to work his cock into me with renewed vigor. I saw that he was now more than halfway buried in my boy-cunt. I did what I could to give him more access, like lifting my legs. But my attention was mainly drawn to that flow of pre-cum sissy-juice. It mesmerized me. Each thrust of Jess's cock release a little more. I watched it for many minutes and then laid back to savor the fullness of Jess inside me. Was this the way women felt when slowly fucked? I clenched my pectoral muscles with both hands and squeezed them together, imagining they were full female breasts that I could offer to Jess. I reached down to my hips and grabbed what little fat I had there, imagining I had an hour-glass figure. I pouted my lips, I bit my lower lip coyly, I purred and made high- pitched short squeaks each time Jess thrust into me. The more I mimicked the way women are and act, the more excited both Jess and I got.
I then felt a strange sensation deep inside me. At first it was barely discernible. But it grew in intensity, along with a burning that was as terrifying as it was pleasurable. I raised my head and saw that Jess' body was very close to mine. This meant that he was almost completely inside me. But there was something else too. He seemed to have grown harder. I reached down and grasped the little bit of cock that was still outside of me. And sure enough it was as hard as a rock.
"I lied to you before when I told you I never get completely hard. I actually do, but only when I'm deep inside a genuine sissy-boy like yourself." With that he withdrew his cock so rapidly that it snapped up like a steel spring against his belly. I was hypnotized by its size, easily 9 plus inches now. I couldn't resist reaching for it. Its base was so thick that I could no longer wrap my hand around it entirely. This cock had its own pulse too, and I could feel Jess' heart racing through it, just as mine was now. I tore my hand away and fell back, lifting my legs.
"Oh gawd, fuck me, make me your sissy-boy," I cried in a daze. Jess put more lube on and plunged without ceremony into me. This time my boy-cunt enveloped him with ease. Further and further down he went until I felt him slow down to a complete stop. I understood that we were at the wide base of his cock which had not yet been inside me. I took a deep breath and pushed down while Jess pushed in and just like that he was balls-deep. I closed my eyes and placed my hands flat on my stomach and imagined Jess' cock must be somewhere just above my belly button, maybe an inch or two down below the surface. His manhood had rearranged my insides by its shear length, width and strength. My sissy-body had thoroughly accommodated him.
Assured that I had now fully opened myself to him, Jess widened his stance at the edge of the bed, grabbed my hips and began thrusting into me with great force. His body would connect with mine with a loud smack, his balls lightly bouncing off my tailbone. What was previously a painful friction was now a pleasurable burning that quickly localized in my lower belly. It began to grow hotter with each deep thrust. I imagined this was where my lust was now to be found. No longer in my penis, but here, deep inside. Something which could only be sparked and flamed by the presence of a real man's cock. This burning sensation then spread like wildfire and I opened my eyes and saw Jess' forehead beading with sweat, his entire body damp from exertion. He was singly focused on something down below. I followed his gaze and saw what must have been the 2nd or 3rd spurt of cum erupting up and out of my little penis. A great pearly glob of it already formed on my belly.
"Now I'm coming!" I exclaim again.
"No, you're.... just... ejaculating," Jess' huffs between thrusts. "That's the last... of your manhood... being... fucked out of you." He increased his thrusts. He was pounding me so aggressively and violently that the entire bed shook, frame and all.
"Wh..." I began to ask, but my body answered my own question. For suddenly out of nowhere an orgasm like no other gripped my entire being. It was as if a great hand inside me clenched down around Jess' cock and stroked it. I knew he felt it too because he stopped thrusting. There was simply no reason for him to move as the insides of my body did all the work, convulsing around his cock, massaging it, urging him to deposit his man-seed deep inside my sissy-womb. Jess' leaned down to my contorted face and tried to kiss me, but his own face became contorted by his own orgasm which left him so weak he collapsed with his full weight on top of me.
I learned in this moment that a sissy-boy's orgasm is unlike a straight man's orgasm which has plenty of warning when it arrives. As a straight man you can very easily announce to your partner 'I'm coming' and still have 4 or 5 good thrusts before it hits. But when the sissy-boy comes, truly comes, it is sudden and without warning, always taking the sissy-boy completely by surprise. Sure, there may sissy-juice or full blown ejaculation sans feeling before that, as it was during my first time with Jess. These events may even be accompanied by the more common and highly pleasurable prostate-orgasm. But none of this prepares the sissy-boy for the full onslaught of that orgasm which belongs to him and him alone, that orgasm which fully possesses both his mind and body and transforms him into a little girl at the very depths of his soul.
Jess and I were spent, but my insides were not. They continued to convulse around his cock.
"Do you feel that?" I ask. Jess raises himself by his arms and gives me the passionate kiss he meant to moments ago. I embrace him and start to cry, this entire experience simply too much for me. He looks tenderly into my eyes and gives me one last kiss. He then rises, withdraws his cock from me and then lies back down next to me. I scurry down and remove the condom. He's still half-hard and I suck him clean, then lap up my own cum that stuck on his belly when he fell on me. Placing my head on his broad chest and playing with the black and grey hairs that grow there, I begin to speak nonsense. Pure sissy-speak. He shushes me quiet. He's right. There are no words. We sleep.
I awake the next morning, alone. There is no trace of Jess. I wrap myself in a sheet and step onto the motel balcony and look around. His semi is gone. I lean forward on the cold railing and think about what other men the future might bring to me.
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