by Olsen, Brett
FIRST IN
Femdom Stories of First-time Strap-on Sex
EDITED BY KYLIE COOPER & N.T. MORLEY
Published by Deception Press
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This anthology is intended for an adult readership and may concern explicitly sexual themes including bondage, BDSM, Domination, submission, threesomes, voyeurism, exhibitionism, public sex and other forms of sexual variation. Do not read it if you find such themes offensive.
First In © 2013 by Kylie Cooper & N.T. Morley. All Rights Reserved.
Cover and interior layout by Aisha Trance. Photo: Fotolia.
Table of Contents
Tonight's the Night by Elizabeth Colvin
Starting Small by Brett Olsen
The First Stroke by Erica Dumas
A Little Push by Felix D'Angelo
The First Stroke by Erica Dumas
Strap-on Morning by Dexter Cunningham
Sissy Lockdown by Kendra Jarry
Daddy's Boy by Elizabeth Colvin
Copyright Information
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Tonight's the Night by Elizabeth Colvin
I've been saving it for you. I know it's a big fantasy of yours; you confessed as much after our long first night of making love, when we both lay tangled in the sheets together. I've even showed you my cock, watching as you squirmed a little, contemplating what it would feel like to take it inside you. You seemed so titillated that I've done this before, that I seemed too casual about it. Maybe you thought I'd want to do it right away, and in one sense I really, really did. But I've saved it, waiting for the perfect moment to surprise you with it.
I know tonight's the night. It's a Friday night; both of us had long days at work. While you're downstairs making dinner, I take a long hot shower, feeling my muscles relax and my pulse quicken as I think about what I'm going to do to you tonight. I step out of the shower, towel dry and take out the strap-on harness. As I fit the dildo into place and step into the harness, I picture you splayed before me, taking my cock into your ass. I can feel the pulse of my pussy as I buckle up the straps of the harness.
I put on a t-shirt without a bra and a faded pair of jeans just tight enough to display the long, hard bulge plainly in front. I go downstairs to the kitchen, where you're chopping vegetables. Your butt looks so good in those boxer shorts you're wearing; I get more excited as I come up behind you, put my arms around you, and grind my crotch against your ass.
You tense against me, then relax. I put my lips very close to your ear and breathe warmly. "I've got a very special surprise for you tonight," I tell you, just as you realize what the bulge against your ass means.
You catch your breath, squirm against me. I reach down under the counter and feel your cock swelling in your boxers. I smile and kiss your neck, satisfied that I've had the desired effect. I back off and go into the dining room to set the table.
All through the delicious dinner, I can see the anticipation and nervousness on your face. I can see you shifting uncomfortably on your seat.
When we've both finished, I smile and ask if you'd like to watch some TV. You catch my drift right away; we go into the living room and recline on the couch. You relax into the soft cushions and I lay alongside you, careful to place myself in the superior position, atop you, leaning hard, letting you know that you can't get away. I know you want this; I know you want it even more than I do. But even if you changed your mind, there's a part of me that wouldn't care. There's a part of me that would wrestle you down, drag your ass up high in the air, and give it to you without lube, listening to you scream as I take your ass with all the force of a heartless, uncaring bastard, the bastard you so sweetly need me to become. I know there's always a chance of you backing out, chickening out on me. And there's a part of me that wants you to, so I can date rape you. You think you can flash that adorable ass at me in those tight boxer shorts and then not give it up, you tease? Not a chance. You're going to put out whether you want to or not -- you know it and I know it, and that's why I'm so fucking wet.
You seem to be paying extra attention not to touch my crotch -- maybe a little frightened of it? But I can see that your cock is half-hard under your boxers.
You pick up the remote and ask what I'd like to watch. "Start the DVD player," I tell you, and you do. The wide-screen TV is filled with an image of a gorgeous guy down on his knees, using his mouth on a woman's strap-on. He's young, younger than you, and she's a standard-issue porn bimbo. But her strap-on is huge, and he's sucking her cock like it's the sweetest thing in the world. He's sucking her cock like he's desperate for it. Her cock is peach colored, just like mine, matching her light skin tone so it almost looks like she's a hermaphrodite wearing a leather cock ring. Almost like it's a real cock. Almost like she's going to shoot her cum all over his face, down his throat. Or is it that she's going to roll him over and shove her cock up his ass, filling him up with her magical sperm? My pussy is tense, so tense, swollen with anticipation and hunger, alive with all the possibilities of having a cock.
I feel you squirming. I put my arms around you and kiss your neck.
I'm a little afraid I've gone too far too fast; after all, I've done this before many times, and you haven't. "Shhhh," I tell you soothingly. "Don't worry, I'll go slow. You'll open right up for me. That ass of yours is beautiful. I'll slick you up right before I ram my cock in you." You tense at my aggressive words -- but then you seem to relax, knowing I'll take care of you. I always have, and I always will.
We sink into the couch and begin kissing, my nipples hardening under the t-shirt as you run your hands over them. I stroke you through your shorts, feeling how hard you've gotten -- hard, insistent as you grind your hips against my hand. You want me to jerk you off? You want me to suck your dick? On any other night, that's exactly what I'd do -- I'm as hungry, as savage, as much of a little piggy as you are. I want to suck you as bad as you want to suck me -- but you need it more. So tonight I'm the one who's going to get sucked. You're the little cockwhore, down on your knees servicing me. You're going to swallow me, deep throat me, and then you're going to roll over and put your ass in the air.
Your hands feel good on my breasts, but I want you to feel the tool that's going to violate you, make you mine. I take one of your wrists and push your hand down into my crotch. Your fingers curve around my bulge, stroking it as if it were a real cock, your body tensing as if every stroke of your hand reminds you how it's going to feel sliding down your virgin throat, being pushed up into your virgin ass. I moan softly as if it was really my cock; the feel of pressure on the base of the dildo is rubbing my clit and I almost think I could cum. I almost think you could jerk me off. And the best thing about my cock is that when I shoot my load it doesn't go soft. It just gets harder, and I get hornier than ever. I stroke your cock as you stroke mine -- and then, to my surprise, you bend down and unzip my pants.
You look up at me, a little scared, a lot hungry. God, you look like a fourteen-year-old girl about to suck her lover's cock for the first time -- just like I was, ten years ago, when I did it the first time. It's the sexiest thing I've ever seen -- your gorgeous face, about to be penetrated by my hard cock. Your gorgeous face, not knowing if it belongs to a fag or a whore or a little virgin girl -- just knowing, beyond the shadow of a doubt,
that it belongs to a cocksucker.
"You give head, baby? You suck cock? Yeah, I've been wanting you to suck my cock since I first laid eyes on you. Suck it. Come on, don't be shy. I won't tell anyone. Just suck it. I know you want to."
And you do, looking up at me a little scared at first, but then giving in as a rush of sudden hunger takes you over. You take my cock in your mouth and swallow it.
It's been a long time since I had a lover who was willing to play this way with me; I feel my pulse pounding as I watch you savoring my cock, sucking it. I coax you on with dirty words: "Oh, yeah, you look so good sucking that... you're so pretty with your mouth around my cock." The dirty talk seems to heighten your interest, and you slip your hand down between the straps of the harness to work two fingers inside me, pressing up against my G-string. I run my fingers through your hair as you bring me closer to orgasm, getting still closer when your thumb works its way under the base of the dildo and presses my clit. I could almost believe my cock is real, that you're sucking me off and I'm about to come in your mouth. The thought sends an explosion of hunger through me and I come, unexpectedly, all of a sudden, in an intense rush of sensation. "Oh yeah," I tell you. "I'm coming in your mouth. Swallow it..."
But I'm far from satisfied; my cock doesn't get soft when you suck it off. Rather, my appetite for more of you has been heightened, and I guide you onto your back so I can lift your legs up over my shoulders and raise your ass off the couch. I put my mouth on your balls, totally ignoring your cock though my mouth is watering for it. But tonight I want to pleasure you another way.
I lick lower and part your cheeks gently, reaching down to take the dental dam from where I've placed it under the couch, getting it out of the plastic bag, stretching it between your cheeks. My tongue finds your musky, puckered hole, wriggling inside as I feel it loosening up. You moan as I lick my way up and down your crack. I can tell you're ready for me, and I smoothly reach under the couch to where I've stashed the towel and the lube. I spread the towel on the couch, then lean back and look at you.
"You want this?" I ask, glancing down at my cock. "You want me to fuck you in the ass?"
You nod, hungrily.
"If you want to get fucked, get up on your hands and knees. Put that pretty ass of yours in the air."
You do it, positioning yourself over the towel the same way I've done more times than I could count. You gasp as you feel the cold dribble of lube between your cheeks; I rub more of it on my hand, warming it before sliding one finger into your asshole. You're really very tight; it excites me that you've never done this before. I put more lube on the head of my cock and rub it all over, then gently nuzzle my cockhead into the cleft between your buttocks.
I use one hand to guide the dildo and one to reach under you, stroking your cock as I press into you. "Breathe out," I tell you, and push the head in; you take a sharp breath as you feel it popping into you. I've selected a particularly small dildo, but it's still a big step for someone who's never been fucked like this. I feel your muscles tense underneath me; then slowly you relax and I sink into you, stroking your cock as mine enters you all the way.
Hearing you moan like this makes me turned on all over again. I could easily make myself come, but now I'm more interested in feeling your cock surge and spurt in my hand. I lift myself up with one foot on the couch so I can have more control as I slowly give you my cock, stroke after stroke. I hear nothing but pleased noises from you, but I'm very careful to go slow -- however much I want to fuck you harder and harder until you scream.
The whole time I'm fondling your cock, feeling it hard in my grasp, feeling dribbles of pre-come running down from the head. It would be easier if I made you stroke yourself, but I want to feel it as you come with my cock inside you. I hear your breath quickening. I pump your cock harder, sensing your anus loosening as you relax into the sensations, then tightening as you get closer to orgasm. Then, all at once, I realize you're at the point of no return. Your body shudders, your cock throbs and spurts in my hand. I keep stroking, in and out of your ass, back and forth on your cock, until I hear a gasp from you and know you need me to pull out. I gently ease back, waiting for your tightened anus to release me of its own accord. My cock slips out and you let out a relieved sigh. I lay down on top of you, feeling you slump onto the couch. I rest my cock in the curve of your ass as I nuzzle your neck and whisper, "Now you're mine. All mine."
Starting Small by Brett Olsen
Amy entered the bedroom with her jockey shorts bulging. She looked gorgeous packed into tight white men's underwear and a snug little sports bra. The bra flattened her tits and gave her upper body just the hint of a masculine contour. But it was really that bulge that makes her look different than usual. It didn't make her look like a guy; her body is too feminine for that. But with her jockey shorts bulging, my girlfriend could have passed for something pretty close to a guy in the dark.
And I knew she was going to fuck me like a guy fucks a guy -- hard and rough and deep and dirty.
My wife was going to fuck me with her huge, new cock. It scared me a little, but it also turned me on.
Her new cock was much bigger than mine. In fact, it was fucking enormous. Amy's eyes always were bigger than her pussy. How did she ever get me to agree to take a cock that big in my butt? I didn't have to think too hard about that one; Amy is hot. She looked so fucking hot with the strap-on bulging her shorts, in fact, that I knew I was going to let her fuck me just the way she wanted to -- however she wanted to. My wife was in charge.
But it made my butt ache just to look at that giant bulge. It jutted out hard and firm. With the shaft forced into an upward curve by the tightness of its white cotton prison, the tip almost stuck out over the waistband.
Amy looked mischievously down at her cock and then at me. She ran her slender fingers through her short blonde hair. The new haircut was partially inspired by her decision to buy herself a cock. She'd been talking about cutting her hair short for summer, anyway, but getting to fuck me in the ass provided the perfect excuse for her to go ahead and chop it.
The short hair accentuated her tomboy smile. Like I said, she doesn't quite look like a guy, but she could probably pass. If she did, though, she'd look underage.
Amy isn't a big girl; she's five feet in socks and a hundred pounds wet. I thought that maybe that means the size of the cock is surely at least partly an illusion. After all, an average-sized cock would look huge on a five-foot guy, right? How would it look on a five-foot tomboy? Maybe her slender, boyish hips and narrow frame are making the cock seem bigger than it is. That seemed likely, right? Right?
I wasn't sure I cared. My own jockeys bulged as I looked at her cock. Like I said, Amy's eyes have always been bigger than her holes. Maybe mine are, too.
She rubbed her cock through her jockey shorts. When she did that, she looked more like a horny teenage boy than ever. She looked like she was ready to fuck for the first time.
I guess in that sense, she was a virgin. But I was the one who was going to bend over for my wife's new monster. And as turned on as I was, I was apprehensive.
But I knew Amy would do me right.
#
When Amy first talked about fucking me in the ass, she teased me about it. She always loves to tease me about it...and about everything. She's a very playful wife.
And this round of teasing was about how big her cock should be. Amy said, "If we're gonna do this, we're gonna do it right. None of this 'starting small' nonsense. I wanna be hung."
I gulped. "That sounds risky," I said.
"I mean, I've never done this before. Maybe we should start small."
Amy smiled and said wickedly, "Did you let me start small, baby?"
"No," I admit, proudly glancing at my crotch. "But that's hardly my fault."
"This isn't about placing blame," Amy teased me with a smirk. "It's about giving me a cock at least as big as yours. Come on! Don’t blame me if I have penis envy! You're the one who gave it to me, John Hol
mes." She cradled my junk as she said it, and I started to stiffen.
I was right, but so was she. I sure as hell didn't have a choice about whether to let Amy "start small." She was adamant in her demand that she get a cock at least as big as mine...tit for tat. And I've gotta admit, that aroused the hell out of me. The fact that Amy wanted to do me right was almost more of a turn-on than the fact that she wanted to fuck me at all.
So it wasn't a choice, except I could have made the choice not to get what she'd promised me...her sweet ass. And that was a prize I was more than happy to work for. If that work involved bending over for my hot, sexy wife? Well, then. I'd take it like a man.
When I say I'm pretty hung, I don't mean to brag. I'm just stating a simple fact, and any of my prior girlfriends can verify it. It's been a pleasure and a danger throughout my sexual life, but when I started dating Amy, her petite frame made it something of a dangerous pleasure.
Despite her size, Amy loves big cock -- because she loves all cock, and the more of it the better. But she'd never been with a guy as big as me. At least, that's what she said. She might have been trying to flatter me -- or giving me added encouragement to go slow and be gentle. I didn't need either flattery or caution...I was used to doing it nice and easy, at least the first few times.