Need to take a fakeboys virginity, telling him that we’ll go slow, that I know it’s his first time and it can be scary but that I promise I’ll be gentle, I’ll take it at his pace, making sure to establish a safe word and come up with a non verbal tap out system,
Getting him nice and comfortable, stripping in front of him and letting him examine my body, letting him approach me at his own pace, his hands shakily exploring my soft skin, constantly checking;
“I-is this ok? I-I’m not hurting you am I?”
Assuring him that I’m fine, that he’s free to explore, that I’ll let him know if he does anything I don’t like or that doesn’t feel good and that he should do the same for me,
Let him get nice and comfortable, running his hands along my torso, brushing past my breasts a time or two before taking one in his hand, letting out a soft moan and giving him a little smile,
Letting him play with my cock, bashfully admitting that it’s the first time he’s seen one in person, taking his hand in mind and wrapping his fingers around myself, letting him feel me get hard in his hand,
His breathing and heart rate quicken and intensify as I slowly begin to stroke myself using his hand, explaining the importance of rhythm and pressure, letting him feel my heartbeat though my cock for a moment before asking if he’d like for me to touch him too,
Watching as he goes red and starts to retreat back into himself, reminding him that it’s ok to say no, and if there are parts of him he does want me to touch and parts he doesn’t want me to touch that’s more than ok,
Watching him shift for a moment, eyes unable to meet mine, before sheepishly and quietly sliding out of his hoodie and sweat pants to reveal an over sized pair of boxers and slightly stained wife beater,
Noticing that he’s not wearing a binder, trying not to stare too long at his little A cups, knowing there’ll be plenty of time later, whether she likes it or not,
Putting my hand on his exposed thigh and feeling him shiver, running my soft fingers across his legs, just starting to get hairy from the T he’s started a few months back, its effects only beginning to peak their way through,
Running my hands up his legs and past his boxers to his tummy, pausing before sliding myself under his shirt to make sure it’s ok, asking if he’d like me to touch his chest, he sits there for a moment, hesitant, before giving a quick little nod,
Checking once again, making sure he has the time to think, explain that it’s ok if he doesn’t want me to, that I won’t, letting him think for a minute, before he covers his face and lets out a quiet,
Darting under the fabric, slithering my hands up his torso to his sensitive little breasts, a look of shock followed by an overwhelming ecstasy rushes across his face as I cup them gently in my hands,
Massaging them softly as I ask him if this is ok, his slack jawed look and glazed over eyes being all the conformation I need, still making sure he admits that, yes, hes loving it,
Letting him sink into himself for a moment, get lost in the feeling washing over him, before pulling my hands away, and once again making my way back down to his boxers,
Sliding the tips of my fingers under the waist band this time, lightly scratching at the burgeoning meadows of hair that are beginning to work their way up his tummy,
Listening to his breathe hitch as the rising and falling of his chest quickens, slowing my pace as my hand lowers further and further until, suddenly he’s grabbing at my hands, pulling me out of his boxers, sliding himself up and away,
Face red and eyes darting, clearly embarrassed and scared, quickly removing my hand and checking in with him, after a few minutes of coaxing, reassurance and plenty of head petting, I finally getting it out of him, he doesn’t like when “it’s” touched, that nothings ever been in there before and that he just wants me to fuck him,
Smiling and telling him that I understand, that yes i can do that, but that it may be a lot all at once, that it’ll probably hurt a bit, making sure that he understands that I’ll pull out immediately if he needs me to,
Laying him back and sliding his boxers off him, he goes to cover his face as it continues to fall a deeper shade of red, gently and playfully pinning the hand he tries to cover himself with,
“Let’s see that pretty face of yours”
The red spreads faster now, smiling down at him and lining up with his hole,
“Just look up at me sweetheart, don’t worry about anything else just focus on my face ok?”
A little nod followed by a gasp as I place the head of my cock against his entrance,
“Deep breathes ok? Just remember to breathe”
As I part his lips and begin to slide in, he’s tight, and as I warned him, it hurts, lacing his pinned hand into my fingers and letting him squeeze hard,
“It’s ok handsome, it’s ok, I’ve got you, just breathe and relax, I’m gonna start moving here in a minute, tell me if it’s too much ok?”
He nods at me frantically, his nails digging deep into the skin of my hand as I shift to slide out, then back into him, reminding him that this can end anytime he wants, that neither of us have to cum, that once he’s had enough or it gets to be too much to tap out,
Making sure he nods along in agreement before sliding back into him, slightly deeper than before this time, his face and insides contorting as I begin to fill him more and more,
Reminding him to breathe as I lower my body on top of his, our breasts resting against one another as I work myself in deeper,
His free arm wraps around my back as he tries to look for something, anything to ground himself, the searing pain emanating from between his legs, slowly letting way to a trickle of pleasure with each thrust, It still being too much for him, even with all of my assurance and work,
After a moment he lifts his hand above my back and lightly taps me twice, the agreed signal to stop, and though he thinks he feels me pause for a moment, he just as quickly feels me slide back into him,
A little confused and slightly worried he assumes I didn’t notice, he taps again, harder this time, but yet again nothing changes, if anything my grip on his hand is tighter, my hips rutting deeper into his with each thrust,
“H-hey I, I asked you t-to stop”
His eyes dart to meet mine, the fear in his face evident as he looks up at my expressionless gaze down at him,
“I know princess, but I’m not done yet” as I hilt the rest of my shaft into her pussy, the pain is overwhelming as I press myself against her cervix, feeling her contract as her atrophied hole stretches to fit my length and girth,
A sharp and sudden scream emanates from her mouth before I’m able to clamp my free hand down over it, letting out a long and low
“Fuuuuuccccck” as I finally seat myself inside of her, her bodies frantic fighting doing nothing more than draw me in further,
Her arm which was wrapped around me starting to punch and slam at my back, quickly raising myself up, removing my hand from her mouth and hitting her hard in the gut, hard enough for the scream to stop and her breath to be knocked out of her,
Repositioning her arms above her head as she flops and gasps for air beneath me, pinning them above her head before starting up again, faster now, she may not want it, but her body can take it,
“Yo-you-you pr-promi-I-sed you-ud STOP!!” She hiccups through broken sobs upon catching her breath,
“I know what I said princess, but fuck you’re just so tight and soft, and it’s been so long since I’ve fucked a virgin hole, and you’re already starting to take my shape”
Using my free hand to grab at her tits, sinking my nails into her skin and watching her face contort,
“You’re gonna have to start getting used to this, you’re gonna be a mom here soon enough” taking her nipple in my mouth and sucking hard,
Feeling her wince at the word mom, sinking my teeth into her nipple as the forced moans turn to broken screams, her voice, which just started to drop, cracking beautifully,
Continuing my assault upon her body for what to her must feel like hours, my hands exploring every soft crevasse, cupping all her curves and leaving marks everywhere, nails and teeth to remember me by, not that she’ll ever be able to forget,
Finally feeling myself getting close, finding a good rhythm, lowering my body down onto her to crush her completely with my weight before whispering
“I’m so close princess, just stay nice and still, I’m gonna cum inside ok?”
“PLEASE DONT CUM INSIDE PLEASE DONT CUM INSIDE ME PLEAS-“ wrapping my fingers around her neck and squeezing hard, watching her face turn red and eyes bulge before her head falls limply to the pillow below,
Her cunt squeezing so tight I have to steady myself to not get pushed out, pulling myself into her by her neck til I’m once again situated against her cervix, then, finally unloading the contents of my balls in her deepest part,
Releasing my hand and watching her slowly fade back into consciousness, blinking hard as her eyes readjust, feeling her loosen for a moment before tightening up once she remembers where she is and what’s happening,
The fight back in her as she pushes hard against my hand on her wrists, holding her in place with my weight until my cock goes soft inside her, making sure every last drop of my cum ends up in her cunt,
Finally as I’m sure they’re empty lifting myself off of her, hooking my free arm under her body and lifting her up towards myself, cradling her in my arms, pulling her into my chest and holding her wrists steady, other hand still wrapped round her back and cradling her head,
“Shhhh sh sh, there there princess I’ve got, you’re ok, you’re gonna be ok, just let it all out” waiting patiently with her in my arms until all the screaming and the carrying on has worked its way through her system, her arms finally going limp against my torso, her chest still heaving against mine, sobbing into my shoulder, screaming in a more feminine pitch than I know she’d like to be able to emit, caressing her back as she tries to shy away from me, my hands, so comforting mere minutes ago, now like scalding irons against her flesh, watching as a red and white trickle begins to leak its way out of her,
Pulling her in as close as possible and in a whisper asking “did you enjoy your first time?”
(Got carried away thinking about vaginismus and the few times I’ve been able to crack a really tight cunt open for no reason in particular……)
