First In: Femdom Stories of First-time Strap-on Sex

by Olsen, Brett

  Soon, Jenny's pounding her cock into my asshole harder than I've ever fucked her -- harder than even Mike has fucked her, I bet. It's all I can do to hold on for dear life, digging my fingers into the pillows.

  As she slams me forward with each thrust, my dick smacks against the sheets. Jenny reaches around me and caresses my cock. She doesn't jerk it -- not at all. Rather, she just teases.

  "You want that handjob I promised you, baby? You want it while my dick's inside you?"

  I nod furiously, begging her. "Please, Mistress, please, Mistress--"

  Jenny viciously digs her fingernails in to the flesh of my cock. I moan. She doesn't jerk me off. She just holds my cock still and pulls back again.

  "Come on, baby. Fuck your asshole onto my dick."

  I obey her, with great difficulty. I'm stuffed full, and my cock and balls hurt like hell. Nonetheless, I fuck myself onto her cock. I can feel the cockhead hitting what must be my prostate; little flashes of extreme pleasure blast through me as her cock hits its deepest point inside me.

  Jenny reads my thoughts. "Feel that? Feel how good that feels? I'm hitting your G-spot, baby. My dickhead is hitting your G-spot. Show me what a horny bitch you are. Show me what a slut my little sissy cunt fucktoy is. Show me what a little panty-wearing cockwhore you want me to make you. Show me how much you love dick, Kendra. Show me how much you love to fuck."

  I ride her cock desperately. I pump myself onto her until, suddenly, white hot pain and pleasure mingle in my tortured dick.

  Hot streams of built-up cum explode from the head of my cock as Jenny dis her fingernails deeper into my flesh. The pressure causes pain at the jizz blasts out -- but she won't let me stop. She hisses, "Keep going, baby. Keep fucking yourself."

  I wail in pain and pleasure, feeling the spasms of my painful orgasm as my asshole contracts around my wife's cock.

  Half of my jizz seems to have gone into Jenny's cupped palm. While I keep fucking myself onto her cock, Jenny shoves her cummy hand into my face. She pushes her cum-slick fingers into in my mouth.

  She doesn't have to tell me what to do. I suck them clean.

  When I'm utterly spent, I can barely even move.

  It's Jenny's turn again to take the active role - no longer making me fuck myself onto her. Now she just wants me to be a limp little bitch. She pulls her cock out of me and pushes my legs up high, bending them over her shoulders.

  My soft little cock sits there underneath her gorgeous body, tucked against my belly and drizzling cum.

  Jenny looks deep into my eyes and starts to fuck me.

  Panting, she asks me, "How do you like missionary position, Kendra? We're almost like husband and wife, huh?"

  I hear the buzzing of a vibrator; at some point Jenny has reached down and turned it on. The egg-shaped device sits on her clitoris -- and as she fucks her cock into me, each thrusts causes pressure against her.

  Jenny looks into my eyes as she starts pounding me viciously...fucking me harder than any guy would need to fuck a woman to cum.

  But Jenny needs to do me hard and deep to get herself off.

  It takes a long time for her to fuck me till she cums. She's been teasing herself as well as pleasing me -- she needs to cum bad. When she finally gets off, Jenny cries out in pleasure, moaning as orgasm floods through her.

  Jenny finally pulls her huge cock out of my ass. Obediently, I help her get the harness off. She caresses my face and smiles.

  "You know what's next," she tells me.

  I nod, shamefully.

  I get out of bed and go to the dresser.

  I bring her my chastity tube

  Now that my dick has been utterly spent, I'm soft enough to put it on.

  But Jenny wants to do the honors.

  She makes me get on the bed and spread out in front of her. She fits the plastic device around my cock. The spikes don't prick me, since I’m entirely soft. But before she closes the hasp, she makes me put my finger in the device, so I can feel how sharp they are.

  "That'll be your incentive to think like a girl," says Jenny.

  She fits the tube around my cock and closes the padlock with a click.

  #

  Once my cock is locked away, Jenny breathes a sigh of relief.

  I'm exhausted, but Jenny doesn't care. She rolls onto her back and spreads her legs.

  "Put on your harness, Kendra. I seriously need to get fucked." She grins. "And I'm not like you, baby. I want the big cock." She caresses her pussy. "Mike's really opened me to new experiences, baby." She laughs at her pun.

  Jenny caresses my chastity-locked penis.

  "Do you think your clit could do that?"

  Eyes down, I say, "No, Mistress."

  #

  I feel strangely peaceful strapping the harness to my body and fitting the biggest of the dildos into it. I almost feel like a girl.

  Dripping sweat and exhausted, I mount my spread wife. With the huge strap-on dildo, I penetrate her for the first time in months. I feel that exultation of first penetration as Jenny gasps, struggling to take it. Then I feel suddenly humiliated... it's not my dick that's inside her.

  Or is it?

  I feel the base of the dildo rubbing against my pubic bone as I fuck her. It's not an unpleasant sensation. I feel Jenny riding my cock underneath, fucking herself up onto me as she talks dirty, telling me all about how good this feels -- how my cock is bigger than Mike's, all I needed to be a real man was for her to make me a girl. I feel the escalating pleasure of dominance as I fuck Jenny harder and harder, even though I'm seriously winded and pouring sweat.

  Jenny's dirty talk really gets me going. She coaxes me into fucking her harder.

  It turns me on more and more. As I pound her, I feel a strange, growing pain.

  My cock is swelling.

  I try to stop; I try to pull out. Jenny wraps her legs around me and pulls me hard onto her. She pins me from underneath, holding me down on top of me and working her legs so I don't have a choice. She fucks herself up against me.

  She whispers filthy words into my ear, telling me all about how she loves getting fucked, what a man I am, how I'm bigger than any of her boyfriends.

  It turns me on more. My cock gets half-hard. It continues to swell.

  The spikes dig in.

  "Please, baby," I whimper desperately. "Please, ow, it hurts--"

  Jenny laughs at me, wrapping her legs around my ass and pulling me onto her. When I panic and try to get free, my wife flips me hard and comes down on top of me. My cock has slipped out of her -- my strap-on cock, that is. My boner continues to swell, and the spikes of the chastity tube cause a screaming pain as Jenny spreads the lips of her slit and fits them over the thick head of my strap-on cock again.

  My wife moans as she fucks herself onto me.

  Arching my back, I claw the sheets in pain.

  Jenny's hot breath flows against my neck. She growls in my ear as she rides me.

  "Do you love me, baby? Do you like this? Is this everything you've ever wanted? Did you always want this?

  She pounds her body against mine, laughing as I squeal in pain.

  There are tears in my eyes as I moan, "Yes, Mistress!"

  My wife rides me harder with every thrust.

  Daddy's Boy by Elizabeth Colvin

  "Come on, boy. Come over here and tell Daddy how much you appreciate his hospitality."

  I take the cigar out of my mouth and smile at him.

  Lounging in the armchair, I reach down and unzip my leather pants. I pull out my cock and start stroking it. My boy looks at the big, thick shaft of my cock and licks his lips.

  Then he goes down on his knees and plants his mouth on the head of my cock. He takes my shaft into his mouth until the head nudges the top of his throat. Then, without hesitating, he swallows, forcing the shaft down his throat without even a hint of a gag reflex. That sends a shudder through my body; I can feel my pussy aching. He starts working on my cock, sucking it like an expert.

  I d
on't look much like any daddy I've ever known. The tight leather pants, big black boots and Harley Davidson T-shirt could belong to a daddy, sure. But there's no disguising my broad hips or the way the pants hang so low on them, revealing my flowery tattoos and my navel ring. And I haven't strapped down my tits, which are big enough to stretch the T-shirt and, even with a sports bra underneath, show my nipples as they get hard in response to the sight and feel of my boy's mouth on my cock.

  But it doesn't matter, because I'm a daddy; I've got the big, thick cock to prove it. Silicone, yes; maybe not as sensitive as a real daddy's cock. With this daddy's cock, it's not just a matter of licking and sucking around the head or teasing the underside of the shaft. Sucking this cock is a lot more work. My boy has to push and work his head around and suck my cock harder, pushing the base of the dildo against my clit to make my pussy throb in response. But I don't care and my boy doesn't care, either, because my boy knows I'm his Daddy. I've got the cock to prove it -- and the armchair.

  And a boy is exactly what he is, tonight. Torn jeans, so faded they're almost white, hug his lithe body, showing off the big bulge in his pants, swept to the right and getting bigger as he sucks me. His tight white T-shirt, so tight it's almost see-through, shows off his perfect chest. He looks like some boy hustler I picked up on the street, offered a place to stay in return for a blowjob. The big white athletic shoes are a decidedly adolescent touch.

  The whole package makes my pussy so wet I can hardly stand it.

  And when he looks up at me with his mouth around my cock, there's no question that this is my boy, servicing me.

  "Come on, boy, suck it better than that. Earn your keep."

  He launches more eagerly into it, his mouth pumping down on my cock and forcing it deeper into his throat. He's obviously a skilled cocksucker; he doesn't even hesitate when the head of my cock presses against his throat. He just swallows, knowing that's what I want. I want to feel him take it all the way, feeling it in his belly, just like he will when I put it up his ass.

  His eyes turn back up to me and I grin down at him, flicking ash off the end of the cigar. "I think it's time you sucked a little ass, boy."

  I pull him off of my cock and turn around on the armchair, pulling my leather pants down over my hips. When I've got them down around my knees, I bend over, pushing my ass out for him. He leans in and obediently presses his face between my cheeks, his tongue sliding into my ass. I have to stifle a gasp that I know will sound way too feminine, and I barely manage to replace it with a manly grunt as I reach back behind me to grab his hair and push his face more firmly into my ass. His tongue works its way deeper into my asshole. He alternates between teasing the entrance with big long swirls of his tongue and pushing hard into it like he's fucking me with that limber little organ. I want to reach down and rub my clit; I want to come so bad it's driving me crazy. But instead of rubbing my clit I reach down and begin to jerk off, stroking my cock, pumping it hard up and down, and that only makes me want to come even more. When I push the dildo down I can feel the base against my clit, almost direct enough to make me come, but not quite. God, I want to fuck him so bad.

  I'm so turned on I can hardly speak. But I manage it, barely, working hard to maintain a gruff rumble in my voice instead of a girly squeak. I turn my head and look down at him over my shoulder. He's beautiful, his mouth planted between my cheeks, licking me. His eyes are turned up toward me, and I look into them as I growl at him.

  "You take it up the ass, boy?"

  His mouth comes away from my ass and he says, "If I have to, Daddy."

  "You have to, boy," I tell him.

  He moves back and I get off the armchair, still stroking my cock. I watch as he shucks his white T-shirt, showing off his beautiful chest. I run my hand down it, working my cock faster. He unzips his jeans and peels them off, kicking his way out of his white athletic shoes. He's not wearing socks. I look at his gorgeous cock, standing there hard, the tip glistening.

  "You can suck it if you want," he says weakly, not meeting my eyes.

  I grab his hair and pull his face close to mine.

  "No kissing," he says, sounding petulant and whiny. "I don't do that. I'm not a faggot."

  The sound of that helpless plea sends a new surge of arousal through my pussy and into my cock. I've got him right where I want him.

  Ignoring him, I press my lips to his and thrust my tongue into his mouth. He lets me for a moment, then begins to respond with his own tongue against mine. I kiss him deeper, then spin him around and shove him against the armchair. He climbs onto it, knees pressed to the thick, padded arms, legs spread, ass in the air. He reaches back and parts his cheeks as I grab the bottle of lube on the end table.

  I pour lube between his cheeks and work two fingers into his cock -- not even bothering to start with one. He gasps as I penetrate him, and I reach between his legs to feel his cock pulsing with excitement.

  "You like that, boy? You like taking it up the ass?"

  "If I have to, Daddy," he says nervously.

  "You have to, boy," I tell him. "You have to like it. And I know you're going to."

  I add some lube to the head of my cock and push his back down till he's crouched down low and his ass is in the right position. I nuzzle the head of my cock against his tight entrance. His ass opens right up as I thrust into it; he lets out a shuddering gasp as I drive it in to the hilt.

  I start to fuck him; for some reason, this position pushes the base of the dildo against my clit at just the right angle. Or maybe fucking my boy in the ass just turns me on more than anything. I reach up and grab his hair, listening to him moan as I shove my cock roughly into his ass, each thrust harder, building up speed.

  His hand is underneath him, pumping his cock. His hips start to work, pushing him onto my cock. Like he's trying to get it over with at first -- then, as his hand quickens on his cock, like he wants it. He shoves hard onto me, his ass opening wider as it engulfs my cock. I pull his hair, making him squeal. At one point I reach down and spank his ass, which makes him fuck back onto me with even more urgency.

  I don't even feel it coming, really. I've been working the dildo into him, pressing the base against my clit for so long that when I finally reach the breaking point I barely know it. It happens when he lets out a little whimper and I feel his body shaking -- he's coming, shooting his load all over Daddy's armchair. I start to fuck him harder, faster, as his lips go slack and he leans hard against the back of the chair. I pound into him and that drives me over the top, my own orgasm sending my pussy and clit into tight spasms, my ass tightening as I feel the cooling moisture of my boy's spittle from where he tongued me. I collapse onto the chair on top of him and it groans under our combined weight as my body surges with pleasure, my high-pitched moans as feminine as it gets -- but my boy doesn't seem to care.

  He reaches back and strokes my hand where it still grips his hair. "Did my tight ass get you off real good, Daddy?"

  "You have no idea," I said, still panting hard.

  "Oh, I think I have some idea," he smiles, and squirms around under me to hold me in his arms. He begins to stroke my long hair gently and whispers, "Thank you, Daddy. Thanks for fucking me so good."

  I curl up in my boy's embrace, sighing contentedly.

  Copyright Information

  "Tonight's the Night" first appeared as "Tonight" in Sweet Life 2: Erotic Fantasies for Couples, edited by Violet Blue. Cleis Press, 2003. Copyright © 2003 by the author. Used by permission of the author. All rights reserved.

  "Starting Small" is previously unpublished. Copyright © 2013 by the author. Used by permission of the author. All rights reserved.

  "A Little Push" first appeared in Sweet Love: Erotic Fantasies for Couples, edited by Violet Blue. Cleis Press, 2010. Copyright © 2010 by the author. Used by permission of the author. All rights reserved.

  "The First Stroke" first appeared in Lips Like Sugar: Women's Erotic Fantasies, edited by Violet Blue. Cleis Press, 2012. Copyright © 2
012 by the author. Used by permission of the author. All rights reserved.

  "Strap-on Morning" first appeared as a stand-alone e-book. Deception Press, 2013. Copyright © 2013 by the author. Used by permission of the author. All rights reserved.

  "Sissy Lockdown" first appeared in Chastity in Lace: Forced Femme Stories of Chastity and Tease & Denial. Deception Press, 2012. Copyright © 2012 by the author. Used by permission of the author. All rights reserved.

  "Daddy's Boy" appeared in Sweet Danger: Erotic Stories of Forbidden Desire for Couples, edited by Violet Blue. Cleis Press, 2010. Copyright © 2010 by the author. Used by permission of the author. All rights reserved.