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

by Olsen, Brett

  It was quite a bit of effort getting it in at first. For the first few times, I had to go real slow and let her breathe through it as she struggled to accept me inside her. She took it like a champ, though...and loved it. I've always liked a challenge, she said. Once she'd gotten used to it, she loved every minute of every fuck. And we fucked with great frequency, no doubt about it. By any standard, Amy was horny. Her cunt took a long time to get used to the size of my cock -- but her brain was all but obsessed with it.

  Even so, it surprised me when Amy said she wanted to try anal. She'd never been done that way before.

  At first, I thought she was joking. Then I thought she was crazy. But she wasn't crazy...she was horny and kinky. Maybe Amy was a little bit too horny and too kinky for her own good. Don't get me wrong...I like ass as much as the next man. But Amy and I had a hell of a sex life. I had no interest in doing something that might hurt her. I didn't want her to feel like she needed to do that to keep me interested.

  To be frank, Amy was a little insulted. She told me, I'm not the least bit worried about keeping you interested. But if you feel like my ass is too precious for your big, dangerous cock, maybe you want to give me something of equal value?

  At first, I didn't get what she meant. Then I didn't believe she really meant it. I thought she was teasing. But Amy never teases...or, rather, when she teases, she always makes good. I'll admit, I was a little afraid of the idea, but when Amy gets started talking dirty, she's very persuasive.

  Next thing I knew, she had me face down on the bed, with my butt in the air and her face planted between my cheeks.

  It wasn't just that I'd never been rimmed before. I'd never even had my butt touched, really, before. Not in that way. It was a wake-up call. How the hell had I been ignoring this part of my body for my whole life?

  Amy's eager tongue woke me up. It was warm and wet. It wriggled its way up my asshole, gently teasing me open as her hand caressed my cock and my balls. She drooled and spat so she could use it as lube. It wasn't long before I was about to cum. Just before I did, I felt Amy's left hand working up between my cheeks. It took over where her tongue had left off...and it went a lot further. I felt two of her fingers working into me just moments before I came. It was surprising and shocking, maybe even scary.

  But oh, holy fuck -- when I shot my load, it was like an explosion blew through my body. I think I saw stars. I almost passed out.

  After that, I was hooked on the idea...as was Amy. I said that she knew her ass better than I did, so if she thought she could handle me...we could try anal if she really wanted.

  Amy laughed at me. She knew how much I wanted it now. She'd woken a sleeping giant...but I had, too.

  "Oh," she told me. "That offer's off the table. Your cock's a hell of a lot bigger than my finger," she teased me. "If you want my ass, you're going to have to give me yours."

  My own cock started to get hard. I could tell from the mischievous sparkle in her eye that she'd decided to play a little game with me. Apparently she'd been annoyed by my reluctance to give her what she wanted. When Amy gets annoyed, she thinks up devious ways to get back at me. The good news is, they're usually hot. They almost always involve sex. The bad news is, she's really good at taking control...and she not only knows how to fuck me like an expert. She knows how to mindfuck me.

  By liking it so much when she put her tongue up there, I'd practically begged my wife to fuck me in the ass. She felt it was her duty to give me what I needed. And Amy was more than happy to answer the call of duty.

  I said, okay, if I had to, I would bend over. She'd been the one who wanted to do anal...but I was the one left begging for her ass, and offering mine in return.

  She insisted on a deal. It was her ass for mine...but she got to do me first.

  She wiggled her ass in my face and slapped it. She parted her cheeks and showed me her pink hole.

  "If you want this," she told me in a nasty voice, "you'll have to earn it."

  That made my dick seriously hard. It felt like it had been hard ever since.

  In had definitely been hard, intermittently, all through this afternoon. We went shopping in the city, hitting several boutiques and buying some new boots for Amy. The main event of our trip was our final stop: a sex shop known as Toyland, known for its wide selection of harnesses, as well as its helpful staff.

  It was a lesbian-oriented shop, all right, but the hot butch dykes at Toyland seemed to like the idea of straight wives and girlfriends giving it to men up the ass. They seemed to take pleasure in my blushing discomfort as they showed us the ins and outs of different harnesses -- always talking to Amy, but making sure I was listening.

  Amy liked to make sure I was listening, too.

  "I want something really heavy-duty," she told the clerks as she patted my ass. "My boyfriend likes it rough." When she saw me blushing, she added, "It's his first time, but he's kind of a pig. I don't plan on going easy on him. His sweet little cherry's been asking for it."

  I don't know if the dykes thought Amy meant I was a "pig" as in a "sexist pig," or a "pig" as in the kind of bottom who craves a really big cock and plenty of it. If it was the latter, it takes one to know one. I think I'm an awful lot more of the latter than the former, so I was going with that one.

  They helped her select a model of harness that would support the kind of plowing she wanted to give me. They helped her select a cock that was just about as big as the harness could stand. I could only hope that it wouldn’t be bigger than I could stand.

  The harness she picked was a model called The Deep Impact. It was made for hard fucking. It was a sturdy piece of leather that strapped tight around her waist and her thighs. It buckled securely and had three different rings to hold cocks of different girths. As the staff at Toyland put it, "This one will allow vigorous thrusting. Very vigorous thrusting, with a very large cock, if you choose."

  From the wicked look on my girlfriend's pretty face as they told her that, it was obvious to me she planned on testing that claim, even before she smiled and said, "Oh, I choose, all right. How big a cock do you think he can take?"

  I reddened under the laughing scrutiny of the four or five women who worked at Toyland. It was a slow day, and they'd all come over to "help." It was obvious they'd picked up on the vibe between Amy and me, and not only approved but found it intriguing. Besides, Amy is hot. They clearly liked her. She'd never been with a woman before, but from the way she was flirting with the clerks at Toyland, I was far from convinced she wouldn't be with one pretty soon. Any one of these hot girls would be more than welcome to do my girlfriend...as long as I get to watch.

  But that isn't what we were at Toyland for earlier today. We were there to buy my girlfriend a cock...and the staff was very helpful in helping her purchase the biggest, hardest cock they imagined my tight virgin ass might be able to take.

  One of them, a handsome young punk dyke whose name badge said "Corey," cautioned Amy. "You might not want to jump right to using the biggest cock possible," she said, looking me up and down. I could tell she had to give Amy the warning, to conform to standards of professional ethics. But I also could tell she liked the way I squirmed.

  "You could start smaller," Corey said with a cocky look at me. "And work up to the size he wants."

  The size "he" wants? It was Amy who was so fucking hot to make me take a big one. But then, I was the one whose dick pulsed every time Amy teased me about how deep and rough and hard she was going to shove her dick into me.

  "Start smaller? Whatever for?" laughed Amy. She told them in a naughty whisper: "He's really hung. He didn't let me start small. I didn't get to work up to his size." Her eyes flickered over me. "Believe me, if we weren't in public, I'd make him unzip. I'd make him show you...then you'd understand. We've been going out for almost a year. I've been taking it regular. Look at that! It's getting harder! See that? Do you even believe he's been putting that in me? I wouldn't feel right if I didn't reciprocate."

  My dick was getti
ng harder, and I wasn't doing much to try to hide it. There wasn't much I could do, with five employees watching me. They seemed to like the way my face turned red when Amy tormented me, but they also seemed scandalized. I couldn't tell if they thought it was cool or disgusting to have her discuss my big cock in front of them.

  But I'll say this much: When your girlfriend brags about how big your cock is, it's a remarkably humiliating experience -- especially if she's talking to women who don't seem to much like the flesh-and-blood kind of cock.

  And if you're a perv like me, it can be hotter than hot to have your girlfriend embarrass you in public. I thought she was crossing the line with the clerks, but it quickly became evident that they were eating it up.

  By the time we left, my cock was throbbing. Amy made me drive. It wasn't easy paying attention to the road with Amy taking her cock out and feeling it up as I drove. She stroked the shaft and caressed the head, down low where no one could see it. Then, as we drove on the freeway, she lifted the cock to her mouth and started to suck it.

  "You're going to get us arrested!" I said.

  Amy's mouth came off her new cock. She slurped and swallowed.

  "Well," she teased me, "If I do, then at least I'm already outfitted for my stint in women's prison." She pouted. "Too bad your cell mate will get your cherry instead of me."

  "Knock it off," I said, but I couldn’t help but laugh. I blushed deep. "I've got to pay attention to the road."

  "Good idea," she said, lowering her new cock and spreading her legs. She guided the head of her dick up under her skirt. She rubbed it up her slit and let out a gasp.

  "My," she said. "That is big. No way am I ever fucking that!"

  She saw my wide eyes and laughed.

  "You're a much bigger person," she said. "You've got more room in there, baby. It'll be fine." She winked. She blew me a kiss.

  "Don't worry," she told me. "I'll make it fit."

  #

  Amy didn't feel like she was asking that much of me. After all, I was just taking cock in the second of my two available holes, just like Amy did on a regular basis. One of her holes was just a little differently placed. At least, that's the way she saw it.

  But it isn't like Amy was a virgin when we got together. She'd already fucked a lot. Her pussy may have been pretty tight for a cock the size of mine, but at least it was well-accustomed to fucking.

  But my ass wasn't accustomed to anything except the "usual." I was a virgin back there...hell, more than a virgin. I didn't even know I wanted it until Amy's tongue slipped in there. I was a back-door virgin...but not for much longer.

  #

  Stretched out on our bed, I was just a few hours out of the dildo store, and it was time for me to take it like a man.

  As soon as we got home, Amy had made me go into the bathroom and do the three enemas we bought at the drug store on the same block as Toyland. I felt tight and open and empty and clean. I felt ready for anything...almost. I was about to find out if I was ready for that monster between my girlfriend's legs. The thing looked bigger and bigger, the closer it gets...but my cock swelled with excitement as I saw it. I wanted to do this.

  #

  Amy came to the bed and stood alongside me, reaching down to run her hand up my leg and grasp my swelling cock.

  "You want this, boy? You wanna suck cock?" She was trying for a gruff, "Daddy" kind of voice, which she's always thought was hot coming from me. I think it's cheesy, so I only give it to her on special occasions. She saw from the frown on my face that the voice didn't work. I didn't wanna get fucked by "Daddy." I wanted to get fucked by my gorgeous wife, wearing a giant cock.

  Amy got the picture. She let her girly, breathy, sex-kitten voice return and said, "Come on, baby. Suck my cock." She groped my cock with one hand -- and with the other, she pulled down her briefs.

  Her huge cock popped out of the jockey shorts. Anatomically contoured, it was exactly the color of Amy's deep-tan flesh. Other than its size, it looked highly realistic. Her cock was reasonably narrow, and not all that much bigger around at the head than my own cock. But it was in the length that made it look so huge. It was twelve inches measured from the base to the tip, according to the clerks at Toyland. This cock had an exceptional stiffness to it -- "30% stiffer than our other models!" The additional length would give Amy more room to work with. "And if you're only going to be using it with a male partner," said the clerk, "the depth shouldn't be too much of an issue. Just be careful." They'd basically said that I could take twelve inches if she gave it to me nice and slow.

  I wasn't so sure about that. There was an awful lot of cock. But their point was that I didn't have to take it all. There was no reason, they meant, for Amy to fuck me to the hilt. These women didn't know my wife.

  And she wasn't only going to be using it anally. Amy had teased me earlier: "If you wanna take cock, you've also gotta suck it."

  And now was the time. It was time to suck my wife's cock. She put one slender, smooth knee up on the bed...and then she shoved her cock in my face.

  I propped myself up just enough to reach the head. I took hold of the shaft with my hand. I guided it into my mouth and felt the pressure of Amy's slender fingers on the back of my head. She held my cock with her other hand, jacking me slowly through my briefs. I was fully hard as I guided the head of her cock into my mouth.

  The taste of the silicone was artificial and a little intoxicating. It felt strange to have a cock-shaped appendage in my mouth, but when I looked shyly up at Amy and saw her gorgeous body above me, I wanted more. I opened wide and took it as far as I could in my mouth. There wasn't much left of my mouth, and plenty left of the cock.

  Amy purred, "Yeah, you like that, don't you? You like sucking my cock?"

  I didn't have to answer. She could feel my response in the way my own cock throbbed hard in her grasp. Amy let me bob up and down on her strap-on dick. I drooled all over it. My spittle collected around the shaft and dribbled over my fingers. I stroked my wife's cock up and down, using my own spit as lube.

  "Yeah," Amy purred, careful to use her most feminine voice, because she knew that was what worked on me. "Get it good and wet. You know where it's going. Your mouth feels good on my dick, but it's going someplace real hot and tight next."

  Leaning over a little as I sucked her, Amy pulled down the front of my briefs and took out my cock. I could feel her tits on the top of my head. She caressed my dick lightly as I sucked her. Well aware of how aroused I was, she only touched my cock gently, so she wouldn't bring me too far, too fast. The last thing either of us wanted was for me to blow my load before she even got her dick in me. That would be a particularly humiliating kind of premature ejaculation.

  "Take off your top," my wife ordered.

  I did, lifting my white cotton tank top over my head. To my surprised, she seized it from my hand and stuffed it in my open mouth. Then she leaned over me, reached down my back and slapped me on the side of the ass.

  "Roll over," she told me.

  "Yes, Ma'am," I said, my words barely distinguishable through a mouthful of sweaty white cotton. But Amy knew what I'd said. It comes from years of hearing me talk with my mouth full.

  "That's Mademoiselle," she teased me, using her sexiest girl voice. Although Amy and I are married, she says she'll never think of herself as a wife. She's never liked being called Ma'am, and I should have known that. But Amy didn't hold grudges.

  As I rolled over, Amy pulled my briefs down my thighs to my knees, then over them and off. I felt acutely naked. Amy planted her knees on the insides of my thighs and forced my legs open. She grabbed my hips and pulled my ass up against her. I could feel her cock rubbing my crack. As I lay there, face-down, ass-up, Amy reached up and made sure the top was well situated in my mouth.

  "I can't have you waking the neighbors when I stick you, baby," she explained. "That’s why I wanted you gagged."

  Then she licked her way down my back.

  Amy took her time, planting her mouth i
n my crack as she parted my cheeks with her slender fingers. I moaned as her wet, supple tongue made its way up into me, swirling around my clean asshole. I felt sensitive still from the water I'd pumped in and out of it less the than an hour ago.

  Amy's tongue wriggled deeper into me. My cock gave a jump. She licked harder, and I moaned into the tank top.

  When came up for air from her rim job, reaching up to pull my tank top out of my mouth -- and then replaced it with my briefs.

  She laughed, "Here, this'll work better." The briefs were as clean as Amy's, since we'd both dressed up for the occasion...but it still felt deliciously humiliating to have my girlfriend shove my underwear in my mouth.

  Amy's body mounted me. She still wore her jockey shorts and had them tugged down over the sculpted balls of her cock.