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

by Olsen, Brett

  The bottle is cold. It sweats.

  Her face serious and seductive, Jenny looks in my eyes.

  She says, "Please, Kendra?"

  I know what she's doing. Sissies don't drink beer. When we drink, guys get us drunk on wine coolers and take advantage of us. Just like Jenny's going to take advantage of me...with the huge strap-on cock I've just laid out for her.

  My own pathetic cock gives a surge, bulging through my pants. Jenny smiles at me flirtatiously and strokes my bulge.

  Reluctantly, I drink the wine cooler.

  Jenny hands me the rest of the four-pack. She picks up a bottle of vodka from the freezer and drinks a couple of slugs of it from the bottle as she pushes me into the bedroom. She throws me on the bed and makes me do the same with the vodka, chasing it with the wine cooler. I try to argue -- I don't like to drink, and certainly not vodka. But Jenny won't take no for an answer, and I'm on the second wine cooler before she's finally satisfied. My stomach revolts. We haven't eaten dinner. Well, I guess I ate dinner...I've gobbled enough of Mike's cum to keep me nourished for days. It sits in my stomach mingling with the vodka and wine cooler.

  But my stomach quiets as Jenny starts to take off her clothes. It doesn't take long; there's not much to remove. I watch her as she slowly lifts her yellow slip dress over her head. She's naked underneath, her glorious body revealed in the moonlight from our big open windows. The curtains are open, but I know that Jenny hates to close them. This time, I don't even ask.

  Jenny spreads her legs and fingers her cummy pussy as I watch. My dick throbs. Thirsty, I drink the wine cooler automatically. The more I drink, the more I realize it's not that bad.

  Jenny lets me look at her body more than she has in months. She does a little dance for me, crawling over me on the bed like a lap dancer. The touch of her naked body makes my skin feel electric even through my clothes. She rubs her hair against my body and dangles her tits in my face. When I try to kiss them, to suck the hard nipples, she grabs my hair and pushes my head down and then grinds her wet pussy on my cock through my jeans.

  She really works up a sweat. She's panting and dripping by the time she finally slides onto the bed next to me. She's probably been dancing for me for half an hour, and I swear -- it's like I was in heaven. My second wine cooler is gone, and I’m feeling very, very drunk.

  "Your turn, she tells me."

  I go to embrace her. She slaps my hands away. "What, baby?"

  "Your turn!" she says harshly. "Take your clothes off. Dance for me." Winded and thirsty from her dance, she polishes off her beer. "Kendra, baby," she begs. "Would you go get me another one?"

  I'm delirious with desire for her after having seen her dance -- Jenny is a hell of a dancer. I go get her a beer, and one for myself. I realize as I walk into the kitchen that I’m getting very drunk.

  When I come back with the two beers, Jenny snatches them both from my hands.

  She smiles and says, "Thank you, Kendra. You brought me two!" The stern look she gives me as she puts my third wine cooler back in my hand makes it obvious she doesn't want to hear any arguments.

  I don't drink beer now...that seems to be the message.

  Still high from the dance my wife gave me, I'm feeling too submissive and obedient to argue with her. I just bring my third wine cooler to my lips and drink from it. And when she hands me the vodka bottle? I drink from it obediently...three times in rapid succession until she's satisfied.

  I realize I'm very drunk. My wife's brutality suddenly seems less important. I have always wanted this...sort of. I even told her about it...whispered her fantasies. They weren't as rough as this, but...Jenny knows what's best for me. She always has. Feeling drunk and increasingly uninhibited, I realize that I'm going to let this play out. I'm going to give myself to my wife tonight...however she wants me.

  Jenny purrs, "Strip for me, Kendra. And don't rush through it, minuteman. I want to see you take your time for once." She laughs.

  She mouths the words to her favorite filthy song as she stretches out on the bed, touching herself shamelessly. We've made it through most of the CD, on the tenth or twelfth remix version. They're increasingly obscene. Jenny's lips form the words as I watch her, blushing, humiliated. I just can't do it.

  She slides up to the edge of bed, stretches her foot out and nudges me in my blue balls with the toe of her high-heeled shoe.

  "Dance, Kendra," she laughs lightly. "Come on, what are you waiting for?"

  Humiliated, I strip for her.

  I try to rush through it at first, feeling awkward, my hands feeling huge, my body feeling very, very masculine. It's degrading to have to dance like a woman, even though, in my drunken state, I can't help but be a little turned on by it.

  My clip-on hoop earrings dangle against my neck. I had almost forgotten I was wearing them. Did Jenny mean what she said? That she was going to get my ears pierced soon?

  My heart races as I think of myself wearing earrings. It would be so humiliating if she made me wear them out in public...maybe even to work...

  That thought only makes me dance sexier, working my hips and grinding with the music, feeling the obscene lyrics penetrate my drunken brain and make me even hornier. They're influencing me. I'm your slave/I'm your cunt/I'm your whore/Use me/Take me/Fuck me/Spank me/Hurt me/Give me your cock...

  My arousal mounts as I shimmy and grind with the music. Drunk and increasingly loose, I'm having a good time. But Jenny is not satisfied. After a few minutes of watching me dance, Jenny chides me for not following the rhythm, for not doing it slow and sexy. She makes me slow down until I'm grinding with the music. She makes me take my time. She makes me pull my jeans down to the top of my boots and bend over and work my ass back and forth in time to the music.

  She makes me pull the panties down and turn away and bend over and show her my asshole, never stopping the slow, increasingly sensuous moves of my dance.

  It takes me a long time to get the hang of it, but with Jenny's guidance, I start to loosen up.

  She gives me pointers. "Work that ass back and forth like a girl, baby. Think of how you like to see it when you're at a strip club."

  When she's not giving me instructions, Jenny mouths the words to the obscene song. "I'm your slave/I’m your whore/I'm your cunt/I'm your bitch/Take me/Use me/Fuck me/Hurt me..."

  Seeing my beautiful wife mouth those suggestive lyrics with her perfect red lips, I find myself inspired. My inhibitions melt away. Before long, I'm dancing like a girl; I've wriggled my way out of the jeans and boots, and I'm dancing for her, almost like a stripper. Almost like a girl.

  Jenny purrs at me happily, claps and giggles and even cheers me between lip-syncing lines about taking it in the ass. I'm naked except for my panties and dancing with increasing ease, my movements getting fluid as I undulate back and forth, getting more turned on as I see the yummy reactions my wife gives me. She rubs herself as she watches me. It's so gratifying to know I’m actually turning my wife on that I dance more energetically, building up a sweat.

  "You're doing so good, Kendra," "See if those white stripper pumps of mine will fit you, baby."

  "Huh?" I ask her. "Darling, they won't...your feet are size fives."

  "Just go ahead and see," Jenny tells me. "They're on the top shelf in the closet."

  I go there. I take the shoes down. I realize that even though I've always thought these shoes are incredibly sexy, I've never seen Jenny wear them. I've even jacked off fantasizing about her wearing them...but I've never seen her wear them.

  When I hold them in my hands, I realize why. They're not Jenny's size. They're mine.

  Blushing, covered in sweat, exhausted, I step into the white pumps and secure the buckle.

  They fit like a charm.

  The heels are much higher than the ones on the red boots she made me wear earlier. My cock has never stopped throbbing and my erection has never dwindled. But I swear, having my ass forced into that unnatural stripper posture from six-inch heels and a thong
that rubs my butthole actually makes my cock actually feel like it grows.

  Covered in sweat, dripping from the exertion of dancing, I finish the third wine cooler. Jenny takes the fourth one from the cardboard four-pack on the nightstand. She waves it at me. I go to the bed and get it from her. She pulls me halfway onto the bed and kisses me -- stopping me with her own high-heeled shoe in my balls when I try to climb on the bed all the way.

  Her kisses taste like beer, vodka, and Mike's cum. My own mouth tastes like wine cooler and pussy. I feel incredibly drunk.

  "Make it slutty this time. Why don't you play with some toys?"

  I take a deep drink of the wine cooler and stumble drunkenly on the heels as I go to what used to be my underwear drawer. I take out a heavy flogger -- one of the two that I told Jenny I found sexy. The smell of the leather intoxicates me. I makes me feel drunker than I already am.

  Wearing just my panties and the high heels, holding the whip, I start to dance for my wife.

  This time, I play with the whip as I drop to the floor and grind around like a stripper. I know I could rub my dick on the hardwood floor....maybe even rub myself to orgasm. But I won't, because that would displease Jenny.

  I hump the air, hump the whip. I even whip myself, slashing the fronds across my back and wincing from the pain. I get more and more turned on. I'm less inhibited by the minute.

  When I'm finally exhausted so I almost can't go one, Jenny smiles.

  She tells me, "Good girl, Kendra. Now bring me my cock so I can fuck you in the ass." She laughs. "I think we'll break you in with the small one."

  The small one? That's a laugh. Even the "small one" is the size of Mike's dick -- and I've already seen that fuck Jenny once today. It's fucking huge. It may be the smallest of the three cocks my wife has purchased, not counting the internal plug that fits in her strap-on harness so she can cum while fucking me. The cock she's going to "break me in with" may be smaller than her other options...but it's still going to rip me in two, and she knows it.

  Nonetheless, I don't even think about disobeying her.

  I don't want to.

  #

  My wife stretches me out on the bed and sits on my face. She makes me eat her as she wriggles into her harness. The harness has an open keyhole arrangement so her pussy stays accessible. The clerks said that a metal ring can be attached so she can put a dildo inside her if she wants -- or she can leave it open so she can have her slave suck her cock and finger her cunt at the same time.

  Instead, Jenny just makes me lick her pussy. "I want Mike's dick to be the first one you suck," she purrs as she smothers me.

  Jenny buckles the harness, riding my face harder and faster as she secures it. Even after all these hours, the taste of Mike's seed inside her is still strong. I obediently lick her pussy and clit, almost suffocating when she gets excited enough to ride me hard, face-fucking me viciously. She sucks and fucks my face so hard that the bed creaks.

  She guides my hand up to her strap-on, and makes me jack it off.

  As she rides me and I jack her off, she sighs: "Get used to this, baby. You'll be giving my boyfriends a lot of HJs from now on."

  Soon, Jenny is breathless from the pleasure of riding my face. She won't let me get her off; she keeps stopping me when she gets close. Her cock bounces against my smooth, waxed chest. Her sweat runs down onto my body.

  Jenny laughs, her crotch rocking and her hips pumping as she forcibly rides my face.

  "Ready to get fucked, Kendra?"

  She lifts her pussy off my face just far enough that I can whimper out a softly obedient "Yes, Ma'am."

  #

  Jenny lifts herself off of me and stands by the bed, her huge cock jutting from her crotch at a very fuckable angle.

  She says to me, "Kendra, bring me the cock and vibrator attachment for my harness, so I can cum as I fuck you."

  Jenny is already standing by the bed -- and our bedroom is not large. The dresser is maybe four feet behind her. But she still makes me get up and hobble over to get it, stumbling on my high-heeled shoes from the ache in my balls.

  I bring her the attachments. She sits on the edge of the bed, makes me kneel and help her get them on.

  The second dildo is very short and extremely wide, with a curved head that's designed to stroke her G-spot as she thrusts into me, according to Dusk. Despite its enormous girth, the dildo fits easily into her cunt.

  Jenny laughs. "I guess Mike's cock really stretched me, huh, baby? You think your clit could do that?"

  I answer automatically. "No, Mistress."

  Jenny gets up onto her knees.

  "Get me the lube," she says.

  I stand. I go to my underwear drawer and get the tube of thick lube the clerks recommended. Jenny motions me onto the bed.

  Suddenly frightened, I stall. "Should--um, should I take my panties off...Mistress?" The word comes so easily to my lips that I don't know why I haven't called her that all along...since before the wedding. Since our first date.

  Jenny shakes her head.

  "Those skimpy things? No, Kendra, I'll just pull them out of the way. Now bring me the lube and get your ass up here. Time to lose your virginity, baby."

  I obey my wife, getting on all fours in front of her. Jenny squirts lube onto her fingers. She wastes no time, but forces one finger easily into my asshole. I squeal.

  "Quit squealing like a pig, Kendra. Unless you want to be one."

  She's done this to me before -- one time, early in our relationship, she surprised me during a blowjob by sticking her finger up my ass an instant before I came. It made me feel angry and humiliated at the time -- but that didn't stop me from cumming in Jenny's mouth harder than I've ever cum in my life.

  Until now. I know when -- if -- my wife finally lets me shoot, it'll be incredible.

  I want to cum so bad I can taste it. I almost feel like my swollen balls have backed up into the back of my throat. But I know that's just the lingering flavor of my wife's boyfriend's cum...which she made me lick out of her.

  After he fucked my wife's brains out.

  Just like she's about to fuck me.

  Jenny fingers my ass until it's slippery with lube, giving me two fingers... then three. Even three fingers is much, much smaller than the huge cock that's jutting out behind me. But I know that Jenny won't take no for an answer...and I don't even want her to, anymore.

  "She says, come on, Kendra. Show me what a whore you are. You get to fuck yourself onto my cock to get yourself ready for my boyfriend. Show me how much you want to be my bitch."

  To my shame, I do want to be her bitch. So much that when I nuzzle my ass backwards and rub my slick hole up and down on the shaft of her cock, the way she rubbed her puss on my cock, I want her inside me. More than I've ever wanted anything. I feel suddenly, deeply eager to take my wife's cock in my asshole....to give herself to me utterly.

  She's lubed the cock up as well as my asshole, and my cock throbs, stiff with need, as I push my asshole against the thick head of my wife's dick.

  I push myself onto it. The pain is excruciating at first. Jenny makes me slow down and tease her cock, laughing.

  "Don't rush it, baby. Really enjoy it. Let yourself feel what I've been feeling from Mike all these months."

  Her mention of Mike doesn't even faze me. It just makes me hornier.

  I go slowly. I want her, but I force myself to wait, teasing her.

  It isn't long before Jenny gets impatient. "That's good, Kendra," she says. "You're ready, now. Put it in. Put my cock inside you."

  It seems too big; there's no way I can take it. But I know that I have to.

  I whimper as I push myself onto her cockhead. The fullness of her big black cockhead is almost more than my asshole can bear. I feel my hole stretching. I feel her cock opening me up, punishing me as I force my way onto it.

  I push myself onto her cock, gasping in pain as my asshole is violated.

  I moan wildly a moan as I finally force myself past the cockhe
ad. Now the huge cock is embedded in my body, and Jenny whispers, "Shhhh," into my ear. "Stop whining and let yourself feel the pleasure. Come on, baby. Show me how you like it."

  I push myself further onto Jenny's dick -- forcing her cock up into me until it the wider base stretches my hole even more than the mammoth cockhead did.

  I'm breathing hard, in big, gasping shudders, whimpering, moaning.

  I fuck myself onto her, picking up speed as the agony dissipates. Jenny starts fucking me. Harder. Still harder. My hoop earrings brush against my shoulders as I rock my head back and forth in response to waves of pain and pleasure.

  I howl as she fucks me.