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

by Olsen, Brett

  I withdrew my finger.

  "I can't," I said.

  "Is it the music?" she asked. "I've got David Bowie--"

  "No, I just can't," I said.

  "Can't?" pouted Carrie. "But my ass, Jack... my virgin tight ass..." she wriggled her perfect apple cheeks back and forth, clenching, releasing, slipping one middle finger down to caress her crack; then she whimpered as she began fingerfucking her own ass, and --

  "Fuck it," I said, and lurched forward.

  "My sentiments exactly," said Carrie, letting me nudge her finger out of the way to replace it with my own, rubber-clad, slick with lube, gently working her open to be quickly replaced by a second, which made her gasp and hiss and whimper, rocking her hips as she pushed herself onto me.

  "Cock, baby," she moaned softly. "I want your cock."

  "We're supposed to go slow."

  "Then I want your cock slowly."

  "You're getting it." It wasn't so much that I worried about hurting my girlfriend -- I did, but then Carrie was very much capable of letting me know if something didn't feel right. Quite the contrary; I worried -- no, best not to think about that now.

  I worked in a third finger, and Carrie pressed back onto my hand, sliding rhythmically back and forth like she was giving a lap dance. Her muscles clenched tight and I let her relax as I worked all three fingers in deeply, till they formed a little heart-shape, holding her asshole open stretched and eager.

  "I think I'm ready," she said. "I want your cock."

  "Do you want a condom?"

  She made a disdainful noise and a sour face. "Fuck no. We're tested, remember?"

  "Wouldn't it be smoother?"

  "Than your cock? I don't think so," she said. Then, deep, hot in a low, sensuous purr: "I want your cock naked inside me, Jack... put it in already, will you?"

  I leaned firmly forward. My cock, still wet from her spit, slid easily into my grasp and as my fingers went softly slurping out, I felt the snugness of her asshole up against my naked cockhead.

  "Breath in deep, and then--FUCK!"

  She gave a little push back onto me, whimpering. My cockhead popped in, and she made a bestial sound as she pushed her snug ass slowly down my shaft, looking over her shoulder to make sure I saw the rapturous expression on her face as she took me into her virgin hole. "You were saying?" she asked me.

  My eyes rolled back into my head. I fumbled the wet rubber glove off of my hand and threw it on the floor. I let her snuggle down onto me, and gradually acclimate herself to the bulk in her hole. She started clenching-releasing, clenching-releasing, each time relaxing more. I felt a quick rubbing and realized she was stroking her clit fervently, periodically dipping two fingers into her cunt. When she did that I could feel her ass tighten, even feel the pressure, a little, of her fingertips against my cock.

  "Bolero" rose in mounting rhythmic fuck-sounds; things were getting serious.

  "All right," she said softly. "Now fuck me."

  I started slowly, gradually, working in and out inch by inch, shocked at how different ass felt than a cunt. As I came partway out, she smeared lube on me with the hand that wasn't on her pussy. Then, "Harder," she begged, and I gave it my best, thrusting deeper until her asshole was around the very base of my cockshaft, then drawing back until I almost slipped out. I leaned forward, pinning her down so I could get more leverage with my hips. I started thrusting, slowly then quicker, quicker, quicker, as Carrie squirmed under me, the thrusts getting easier with each stroke. I was close -- fucking close, fast as hell since her ass was so tight and the turn-on was tangible.

  "Um -- I'm ready -- you want it --"

  "Yeah, yeah, up my ass," she said irritably, breathlessly. "Come in my ass. Wait -- not -- not yet --"

  She rubbed harder, almost violently; I struggled to hold still while she went at it. Then she let out a low keening wail and her ass tightened rhythmically; she gave a yelp of surprise as my cock popped smoothly out.

  "Back in," she pleaded, and I worked it back in. Her ass was still spasming as I drove deep inside her and started thrusting. In another moment I started to come, giving a girly little whimper as I gripped her hair and pounded her ass. Borne into the bed by my weight, Carrie lifted her ass to meet my thrusts. Her ass went slick with my semen. "Bolero" screamed its final whining cacophony, yowling to its violent end.

  I grunted. I finished. Her cunt and ass were still twitching, little "Oooh" sounds escaping her lips as she felt the afterglow of her orgasm. After a time I rolled off of her, lay on my back panting. Affectionately, she snuggled on top of me.

  The CD started again: Bum, da da da, ba da da da da da bum da da da... Christ, was Carrie really going to tell people for the rest of her life that she lost her anal virginity to the strains of motherfucking "Bolero"? Adding insult to perversion, though I admitted the rhythm was mildly soothing, however much my ass-cheeks were clenching.

  She must have read worry on my face; she gave a broad grin, giggling evilly.

  "Oh, don't be nervous, baby... it was my first time, and tomorrow it'll be your first time." She laughed.

  "Tomorrow? I thought we said 'some time.'"

  Carrie gave me her best innocent face. "Come on, baby, you're not going to make me wait, are you? I didn't make you wait... well, not very long, at least. Please?"

  "All right," I said. "I guess so. If you're sure it won't--"

  "No, it doesn't hurt, baby. And you know you want it. Or at least you know you're curious about it."

  I shrugged, trying to play cool.

  "Don't give me that," said Carrie, and kissed my chest wetly, with lots of tongue. "Of course," she breathed, "I would never want to do anything to you that you weren't totally into. You can always puss out... and go back on your word... and get your girlfriend to give up her ass, but be chicken to --"

  "Forget it," I said. "I'll make good on our bargain."

  Carrie gave her most mischievous grin, her whole body seeming to hum with excitement from the prospect -- or maybe it was that she just got fucked in the ass.

  "Would you... show me?" I asked.

  Carrie looked surprised.

  "I mean, you already bought it, right?"

  "Yeah, but I thought... I figured we'd wait until..."

  "Please? I'm just curious."

  "Sure," she said. "That's hot. You don't want..."

  "Tonight? No. I just... I'd just like to see it."

  "Maybe suck it a little?"

  "Suck it? That's weird." I grinned.

  "Men," she said, smiling. "All right. Fashion show. You wait right here, baby." She got out of bed.

  Carrie's campus apartment has shared baths between each pair of bedrooms. She seized a black plastic bag with a dog-collar logo from the decrepit particleboard laminate wardrobe, and paused at the door.

  "Don't go anywhere," she said, and shut the door behind her.

  I rolled over onto my belly, felt immediately self-conscious -- since that put my ass in a direct line-of-sight from the bathroom door. I rolled onto my side. My cock ached from the fuck; Carrie's asshole was tight, and the heat of my first anal fuck was as hot as the excitement of taking Carrie's anal virginity.

  But with Carrie, nothing is ever simple; what's more, she's fantastically persuasive. When I'd made my thoughts clear -- that anal sex was fucking hot, and I couldn't wait to do it -- she conceived of a bargain. She'd never done it before, but she would. I could be the man to initiate her into the pleasures of back door love. If I'd offer her the same consideration.

  Oh, don't get me wrong. I played hard to get. I blushed, hemmed and hawed, wasn't sure I could do that -- still wasn't. But the night she suggested it, fuck! how my cock swelled and throbbed.

  Ever since then -- three weeks, now, long enough for her to buy a strap-on and me to read three neurotic books on safety, tips, guidelines and precautious -- I'd been half-obsessed, careening wildly between imagining Carrie's tight ass snugged around my slick cock, and her cock, buried deep -- motherfucker, I cou
ldn't even think about it without popping a hard-on, which I did, and before I knew it I was stroking -- my cock wet with lube and Carrie's ass, my ass feeling suddenly hungry. My cock was sore, the tip stung slightly, and still I fucking stroked it, reaching back to touch my own firm cheeks -- good God, was I a pervert?

  "Baby?"

  "Patience!" she cried back. "This thing's not sweats and a god damn T-shirt, Jackie Boy, and it's not attached to me!"

  "Sorry," I said meekly.

  I went back to stroking gently, almost hyperventilating. I'd decided: Why put off until tomorrow... my cheeks clenched. I squirted lube and reached back there.

  I was tight -- tighter than Carrie. Two fingers took some work to get in. Three was almost impossible at first. Four -- well, once I'd done three, four seemed like an awesome idea, and then I was fucking, wetly, eyes rolling back into my head. I was clean, I'd seen to that, knowing this was a possibility -- since my vivid fantasies had me doing just this, fucking Carrie's ass and then... oh fuck. I thrust fingers deeper, pumped my cock, felt my asshole relaxing...

  "Bolero" was pulsing louder.

  "Baby?"

  "God damn buckles! Just a minute."

  I watched, panting and stroking, as I waited for the door to open. The CD had started over before it did; she sashayed out adorned and gussied; I stared gape-mouthed as her eyes flickered over my lube-slick cock. I'd slid my fingers out of my ass, and was caressing my prick with both hands.

  "You like, I guess," she said.

  "Those boots!"

  "They match the harness," said Carrie.

  "Expensive?"

  "I hope my Dad doesn't check his credit card statement this month. I'm just saying."

  Her hand went gliding slowly down her body, fingers nuzzling her tits, her belly, then circling the big flesh-colored cock jutting out of her harness.

  "It looks so real," I said, sitting up on the edge of the bed.

  She stroked her cock as she made her way across the bedroom, spike-heeled patent-leather knee-high monstrosities spearing lube packets and discarded comic books. "I thought... you know, smooth, purple or something, that'll be less, er, real. But then... you know, there's something hot about how it looks like a real cock. Isn't that kind of hot, Jackie? Jackie? Oh, my..."

  My mouth engulfed the head of her cock and I felt a powerful charge of excitement go through me. Oh, fuck, I was actually going to do this.

  I took her cock down easily to the back of my throat, my head bobbing up and down as she ground her hips forward. It wasn't just the anal sex books I'd learned from; never having seen her strap-on before, I had already gauged the angle of the base. Line drawings can be so helpful. I calculated its proximity to Carrie's clit, which, let's be frank, I knew the location of pretty god damn well. I started sucking, hand around the lower portion of the shaft, got the base of the dildo tight against Carrie's clit, and -- drunken sailors never moaned so loud when street whores' throats went tight around their cockshafts.

  I felt wires, but didn't think twice about them; I was too fixated on sucking Carrie's strap-on. I started working fervently, my hand around Carrie's firm body, gripping that perfect ass I'd just fucked and pulling it hard against me cock down my throat. She held me, her crotch against my face, her hands gripping my hair as I struggled to keep her down as deep inside me as I could.

  "I've been practicing," I rasped when I came up for air, which was not for a good long time.

  "You little whore," she said. "You've been playing hard to get."

  Don't make me beg, I thought. I'll puss out.

  But she didn't she just let me suck and suck, my own cock throbbing, until I looked up at her with big wide eyes and she gave me a little push onto the bed.

  "On your knees, lover,"

  "But you said tomorrow," I whined with a vague smile, even as I obeyed her push and got on my hands and knees.

  She got behind me.

  "But your ass says now, now, now." She didn't bother with a glove; she'd trimmed her nails short. I'd left the lube half-opened, leaking goo onto her pillow; I groped after it, handed it over my shoulder, and felt a cool slick stream joining the thick coat that still greased my asshole.

  I made girly sounds as her fingers worked into me. Carrie's fingers were considerably narrower than mine; she got two, three, four in there, easy as pie, and then before I even knew it a shockingly realistic dildo was up against my asshole and my eyes went wide with momentary fright.

  Then with a little push, my girlfriend entered me. The cock was not enormous, but she had not gone mini, either; it was healthy in its thickness and my asshole opened slowly. But she got it in, a little push, another, another, another, sliding easily back and forth until Carrie's thighs settled tight against mine and I could feel her cock all the way in my ass.

  Between pulses of "Bolero," I heard a click, then a buzz, felt a throbbing. Carrie moaned.

  Holy fuck. She was going to fuck me till she came. Just like a real assfucker -- just like me, in her ass, that gorgeous ass flexing and releasing with every thrust of her cock into me, an ass filled with my cum --

  I started stroking.

  Carrie moaned louder, one hand steading herself on the small of my back, the other working the wired vibrator, varying its pulses as she teased herself to climax as the music built louder and louder to cacophony.

  Then she came, her thick cock pounding deep inside of me, her thrusts matched to the spasmodic jerks of her orgasm, shuddering pleasure raging through her cock and into my ass. The assfuck gave every possible hint of realism except her cum pumping -- and I provided that part, hot streams shooting over my hand and arm, soaking the bed as I cried out. Whether she came first or I did, I really don't know, because she was making noises for a good long time as she drove me down into the bed and bit deep into the flesh of my shoulder and neck, leaving hickeys, I was sure of it. When she was good and done and sated, she switched the vibrator off and I felt the buzz dissipate.

  We lay like that through another half-playing of the CD, as Carrie's hot breath ruffled my hair and her fingers caressed my arms.

  "Are we even, Jackie baby?"

  "I don't know," I said. "You've got a pretty awesome asshole, baby. Maybe a few more times should do it..."

  With a little push, I eased her out of me.

  Strap-on Morning by Dexter Cunningham

  It was early on the morning of our wedding anniversary when Katie woke me up for a surprise strap-on fuck.

  She did it the way she usually wakes me up...with her perfect body rubbing up against mine and her beautiful lips uttering a feral growl.

  It's a sound that always tells me that Katie wants sex. And Katie wants sex all the time...especially in the morning. Especially very early in the morning.

  This time, I don't just mean it was early in the morning. I mean it was motherfucking early in the fucking morning, and Katie was ready to fuck. Katie's a morning person, you see. She wakes up early and often, and she always wants to cuddle when she does. And when I say "cuddle," I mean "fuck."

  That's where the problem begins. Katie rarely gets what she wants because I'm her husband, and I’m not a morning person. In fact, the very idea of sex in the morning bewilders me...most of the time.

  Don't get me wrong; I get morning wood just like any other healthy red-blooded man. In fact, most mornings I wake with a boner, which Katie often takes as an invitation to start stroking, sucking, or even fishing around for a condom.

  And most mornings, as long as Katie's willing to do all the work, as far as I'm concerned she can go to town.

  "Just don't wake me up," I often joke. But it's really not a joke.

  On the morning of our anniversary, though, my wife wouldn't take no for an answer. She had her hands all over me, her tongue against my naked chest, her lips locking tight around first one nipple, then the other, as her tongue worked fervently over them. That that good for a while through the sleepy haze of barely being awake. But when she started to bite lik
e the feral beast that she is in the mornings, it was too fucking much for my sleepy brain.

  "Hey!" I said irritably. "What the fuck time is it?"

  Katie said guiltily, "About five-forty."

  "Five-fucking-forty?" I groaned. "It isn't even light out!" I tried to push Katie away, but she was like a cat insistent on morning pets. I told her, "I promise I'll fuck your brains out. Soon."

  "When?" she asked, her perfect lips against my neck, her breath warm and hungry.

  I rubbed sleep out of my eyes.

  "Let's say eleven-thirty?"