Sometimes men don’t understand how a woman could lack…confidence.
They don’t know what it’s like to be pretty. And popular. And to have had so, so many boyfriends yet, at the same time, to not understand their own desires. That being pretty was keeping up appearances; popularity was being constantly compared to others. That, sometimes, lots of boyfriends means lots of bad boyfriends.
I had a lot of bad boyfriends. They made me anxious and insecure. They took sex from me and I spent my early twenties believing I was submissive when in truth I was scared and confused. That wasn’t the case anymore, though, because now I had my lovable dork.
A year and a half. That’s how long I’ve been taken care of. I’ve been encouraged. I learned what it felt like to be told I was beautiful instead of hot. I’m cherished and protected, not controlled. And, well, after a year and a half, I learned that I wasn’t submissive because submissive women don’t make him happy.
“I make you happy, don’t I?”
I look down to see the bulging of his Adam’s apple as he swallows and smile with my lips slightly parted. “Yes,” he admits.
I’d be lying if I said the little tremble in his voice didn’t make me squirm with delight. A pleasure for him as I was sat squarely on his midriff with the seat of my ass just barely putting weight on his crotch.
“I’m not too heavy, am I?”
“No,” he murmurs. My breath barely has time to catch in my throat before he corrects himself. “No, mistress.”
“Good boy!” I squirm again, swaying my hips from side to side as my tight backside slides across the prominent hipbones. “I bet you wish these boxers were off…”
I reach past my thigh and hook my thumb into the elastic waistband of his boxer-briefs to give them a tug. With a snap, they lash against his skin and I giggle to myself. He’s a big boy. I bet it didn’t hurt in the slightest. In truth, he could easily throw my tiny ass off him if he wanted to. I’m just a petite, delicate little thing that stands a whole foot shorter than my lover. In public – even just outside of the bedroom – I’m nothing but a little mouse compared to my lion but behind these doors…
“I wore this for you,” I say, “because you’ve been so good recently.”
I gesture to my little outfit: a white blouse that’s only buttoned across my belly and the tiniest checkered mini-skirt I could find. It’s complete with a pair of frilly ankle socks and black short-heeled shoes. Maybe I’d have been able to delude myself into thinking I was an innocent schoolgirl if my black lace bra and matching full-back panties weren’t on full display.
My hands trace across his bare chest. Embroidered gloves made of lace, he likes those. He especially likes when they’re soaked in lube and I squeeze his cock. Right now, though, that cock is kept safe underneath a pair of jet black Calvins so I was free to bounce on his crotch to my heart’s delight.
“In fact,” I continue, “you’ve been so good that I was thinking that I’d get your favorite toy out tonight.”
I smile as his eyes light up. “Oh. You’d like that, wouldn’t you? Naughty boy…”
My thumbs gently stroke his nipples. They’re stiff. He’s shy about it but they’re probably more sensitive than my own. “I know you’ve been begging,” I gasp lightly for a bit of dramatic flair as I ease lower onto the stiffening bulge below my backside, “for a little strap-on action recently.”
His cheeks flush and those cute little ears instantly turn scarlet. “I wasn’t begging…”
“Oh you were…begging like you always do, looking at me with those puppy eyes and treating me so sweetly. Do you think I can’t tell when you’re trying to butter me up?”
“I’m sorry.”
“Don’t apologize. I think it’s cute.”
He swallows again.
“I think it’s cute,” I say, “how such a big strong man wants to put his legs in the air and have his girlfriend fuck his ass for him. Is that what you want?”
“Yes, mistress.”
I moan softly. This time it may have been involuntary. “You make the cutest sounds,” I whisper, “when I shove my big, thick cock up your ass and you’re oozing lube all over the sheets.” I reach behind me, finding his cock and balls with my hand so that I could give them the lightest squeeze into a gentle massage. “And this thing here just drips with yummy precum, dribbling all over my cock.”
I can feel his eyes on me, focused on how my nipples grew stiff as I talk about fucking him in the ass. His eager cock swells to match and the dampness in my crotch betrays how turned on I am by the way his body reacts to my touch. “You want me to fuck you tonight, baby?”
“Yes, please…”
“Yeah?”
“Yes, mistress.”
“Good boy!” I giggle as I lift one leg over his torso. My movements are slow and erotic. I know he likes looking at my ass and I give him a good eyeful as I turn to crawl away off the edge of the bed. The fact that he wants to touch, but doesn’t have permission to makes me feel even more impish than usual. I find the time to stick my tongue out over my shoulder before standing up. Once I do, I thrust my hips backwards to lift my skirt and give him a final peek at my panties.
I cross to the other side of our bedroom and bend at the waist as I retrieve the harness and step into it one leg at a time. With a shimmy and a jump it slides over my rump and a few tugs lock it into place.
“I hope you’re ready,” I tease, turning with hands clasped behind my back to reveal my tool: seven-and-a-half inches of smooth, black rubber. My little frame makes it look even more menacing as the tip hangs halfway between my thighs. Them being toned and slender makes the phallus look even more girthy by comparison and I see that reflected in his eyes.
“Don’t be afraid,” I say as I cross the room with a seductive gait, “you picked this out.”
“Will you be gentle?”
I make a disappointed tutting sound as I sit near his shoulders. “Of course! I would never hurt my sweetie, would I?”
“Thank you,” he whispered.
“It’s okay,” I respond, leaning over to give him a sweet kiss on the brow. “You’re a big boy. I know you can handle it.”
That swallow again. It makes me shiver.
I take the bottle of lube from the bedside table and move to his waist. “Get these boxers off,” I say with an authoritative tone as I position myself. The sight of a man lifting his legs in the air as he strips in preparation of being penetrated gets me riled up every time. Just something about his thick, hairy thighs raised in surrender. He knows to hold his legs up as I dump a liberal amount of lubricant onto my palm and work it into my fingers.
There it was, him groaning in pleasure as my gloved hand found his crevice. He’s hairless between the cheeks. Even his cock and balls are completely free of anything unsightly. It helps establish contact as I lean forward, on my knees with one hand planted into the sheets, and I grope his manhood.
My slippery fingers move to the crack of his ass where my fingertips teased the rim of his asshole and upwards again until I grapsed his swollen gonads in the palm of my hand. From there, I wrapped my fingers around his shaft and moved them along the length until I could press my thumb firmly into the underside of his cockhead. “Whose is this?” I ask with a deceptively cheery tone of voice.
“It’s yours, mistress,” he gasps.
My thumb applies more pressure, rubbing firmly against his frenulum until his legs tremble. “Is it going to cum?”
“No, mistress!”
“No?”
“Not until you give it permission, mistress!”
“Good boy!” I say as I transition to several slow strokes along his shaft. I move my hand to wrap my fingers around his cockhead and fill my grip with lubricant as I give my boytoy a little reward for being so eager. Slowly, the room becomes full of the sound of my wet hand gripping tight over his cockhead and massaging the sensitive tip. Over and over, I gently squeeze and release his crown while my fist rolls in a slow, circular motion. The lace of my gloves enhances the sensations, making my lover whine like a bitch in heat as he struggles to keep his legs up and parted.
“Remember,” I tease, “no cumming. Not until I say so!”
He can only groan in response but I allow it. From the beads of sweat populating his brow, I know it’s difficult for him to hold on. After all, it’s been almost three weeks since I’ve allowed him to bust a nut.
“Do you think tonight’s the night?” I ask. “Or should I just torment you until you’re a whiny, oozing mess again?”
“P-please…”
“Hmm?” I pretend to think about it as I watch the lube drip down his manhood and sink into the plump crevice where his pussy laid waiting for me to plunder. “Maybe I won’t let you cum. That’s right. Maybe,” I shift to my knees, fingers still wrapped around his cock, “I should just take this beast here and…fuck you!”
I thrust my hips forward and allow the dildo to glide beside his cock, up into the space betwen his thigh and his junk. He moans, quivering as I drive my hips against his ass and the tip of the weapon reaches just below his navel.
I moan. “That’s right,” I say with a wicked grin. “I’m just going to fuck you,” I thrust again, “fuck you, and fuck you some more and I’m not ever going to let you cum!”
“Please, mistress, no…”
I laugh. “Are you begging?” I keep massaging his cockhead with renewed vigor, even as the muscles in my forearms burn. “Let me hear you beg for it.”
“Please,” he gasps. “Please, please, please…oh fuck…”
“No!” I bark, squeezing tight and driving my thumb into the underside of his penis. “No!”
He whines again, practically howling as his legs give and his body grows weak.
“That’s a good boy. Stay just like that,” I whisper. My fingers start manipulating his cock again, even as spasms start overriding his instructions to remain still.
The dildo remains between his legs and I incorporate it into the stroke session by laying it over his prick as though comparing sizes. Then, I stroke both shafts together by working my fingers along their lengths until the rubber glistens with a mixture of lubricant and precum.
“I think,” I say softly, “it’s time for me to have some fun.”
I finally let go of his cock, smirking as I see a string of dick-drool flow onto his stomach when the stiff rod falls backwards. My hands move to the back of his knees so I can lift his legs and mount his rump while my strap-on remains wedged against his cock.
It takes some angling but, finally, I get the base of the dildo against my clitoris and I begin humping in earnest. He whines, but he always whines when he realizes he isn’t getting his dick milked as he wants it. He knows the frustration only makes the final release sweeter, though, and behind every pained and disappointed whimper is the joy of a man who knows his place.
“Good boy,” I gasp as I drive my hips forward with clumsy thrusts. He’s big, and thrusting isn’t really something I’m cut out for. What I do know, however, is that the metal ring and firm rubber pressed against my clit through my lace panties feels really good and grinding againt his junk is going to make me cum soon.
My body leans over his in an almost-comical fashion. I know what it’s like to be him now, feeling small and afraid while someone uses your body to get off. My rubber cock glides across his manhood several times, each overstimulating the already sensitive organ as I listen to our combined gasps and moans of pleasure. Finally, I climax and he, in obedience, does not.
I collapse onto his chest, breathing heavily and hips still thrusting with my shallow, awkward motions. He doesn’t move, partially to avoid stimulating my sensitive clit further and also because it’s the first time I’ve allowed him a reprieve from the relentless stimulation against his cock.
“Was your orgasm good, mistress?”
“Mm-hmm,” I moan, already a little winded. I plant little kisses across his chest, growing up his neck and along his jawline. “You were a very obedient boy,” I whisper into his ear once my lips get to his earlobe, “but I’m still going to fuck you.”
Source: reddit.com/r/Erotica/comments/rwjd1l/frotting_with_my_strapon_mfgentle