“Just… relax, babe,” Jessie whispered in my ear.
I tried to. Focusing on her soothing voice, I spread my legs a little further apart and exhaled slowly.
When my roommate offered to give me a massage, I would have never expected things to turn out the way they did. I’d known Jessie for years – we went to college together, and then moved into midtown Manhattan when we both secured places in the law firm of our dreams. We’ve spent late nights sitting by a laptop binging our favorite shows, laughing and crying with a tub of strawberry ice cream between us. We’ve spent early mornings trying to beat pounding hangovers and making sure we got one another onto the ‘1’ train in time for work. We’ve cried over men, laughed over bosses and gossiped about the lawyers we’ve seen in bars with strange characters that definitely weren’t their spouses. We’ve shared our deepest secrets, our hopes, dreams and fears. We were like open books to one another.
Looking back, I realized there was no one in the world I was closer to than Jessie. Neither my parents nor the one man with which I shared an uncharacteristically long relationship with came close to having the bond that I did with Jessie.
Looking back, I should have seen this moment coming.
Jessie skipped into the apartment with an oddly vivacious spring in her step.
“Bonus?” I asked, lifting an eyebrow.
“Nope, just the day off tomorrow!” she cooed, setting her bag down on the table, “I’ve needed it, really. Been feeling a little burnt out since we took on the Matther’s case.”
“Mmmhmmm,” I nodded, sharing the sentiment. “Wanna’ do a rewatch of Gilmore Girls tonight babe?” I asked.
“Actually… I was going to ask if you were up for a massage,” Jessie said with a mischievous grin.
“At the parlor you mean? Tonight?”
“No… I mean with me! Remember how I’ve been taking those classes at lunchtime? I think I’ve done enough to give a decent massage…” she smiled, wiggling her fingers in my direction.
“Uh… you think?” I asked, unsure.
“C’mon babe I promise it’ll be fun!”
Our massage began normally, but I felt things shift as Jessie finished kneading into my lower back. Jessie casually pushed aside the small towel that covered my butt, before playfully toying with my cheeks. I giggled, thinking of it as nothing more than girlish cheekiness at first, but then, I felt her soft fingers trembling.
Quietly, she pulled my cotton panties to the side, and plied my bare ass with her hands. Ever so carefully, she inched towards my sex, teasing, but never actually touching it. I heard her breathe heavily. My heart thumped in my ears as I quietly succumbed to her lustful, intricate touches. Then, I felt the first, subtle tingle of excitement between my legs.
I blushed, too afraid to turn around. I didn’t want her to stop, but I was too shy to tell her to continue. My sex began to burn with excitement, begging her to touch it. I knew it was becoming wet, and I knew that she would soon see the small, soaked spot on the crotch of my panties.
I felt her fingers dance tentatively over my sex, and then pull away. I heard her nervous breathing behind me.
Please don’t stop.
Then, I felt her hair brush the side of my face as she leaned into me from behind, and placed her lips next to my ear.
“Turn over,” she said.
I turned over. As I did, the towel that was wrapped loosely around my waist fell open, and slipped off the bed. I blushed, knowing Jessie would see my glistening pussy, and see how aroused her deep, sensual touch had made me.
Gently, she pulled my knees apart and pressed her soft, slender fingers onto my pussy. I gasped. Her touch was so tender, yet so incredibly gratifying. Gently, she toyed with my lips, running her fingers between them.
“So… I got this, uh. This thing,” she suddenly stammered.
“Hmmm?” I asked, my eyes still closed as I relished her delicate touches on my sex.
“It felt… amazing. I thought you might wanna’ try it. It’s a part of your happy ending,” she giggled.
“Ooooh, a toy? I’ve never used one before, if you’ll believe me,” I said, opening my eyes as she rummaged by her bedside drawer with her free hand.
She pulled out a long, pink device from her drawer.
“Woah… nifty,” I mumbled, admiring its smooth, matte exterior.
“Very,” Jessie smiled. “This thing has given me countless memorable nights, babe. Who needs a dick when you have one of these babies,” she giggled, comically yet seductively running her fingers along the tip of the device.
“What does that, uh… that pointy thing off the top do?” I quizzed, noticing the toy had an extra, rabbit-eared appendage on it.
“You’ll see,” she said, smiling.
Slowly, she pressed the tip of the toy against my lips, and firmly rubbed it against my pussy. I tensed involuntarily when I felt the cool silicone surface brush against my heated sex, my legs stiffening from the crisp, cold probing of the toy.
“Just… relax, babe,” Jessie whispered in my ear.
Steadily, Jessie began pushing the toy past my lips and into my pussy. I whimpered quietly as I felt it filled me up, its bulbous tip stretching me out as it probed into me.
“It’s going to find that special, little spot of yours,” Jessie whispered reassuringly, as she pushed the toy further into me, an inch at a time, till I felt its rabbit ears rub up against my clit.
“Mmmh, oh, so t-that’s what it does,” I smiled, my cheeks reddening.
As Jessie eased the final few millimeters of the toy into me, she rhythmically gyrated it in my pussy, easing my small, tight sex into the new sensations I was feeling. As she did, I began to feel the toy’s swollen head begin to dig into my g-spot, just like Jessie had promised.
“Oh, mmh, babe thi-mmmmh¬… this feels fucking amazing,” I whimpered, my fingers digging into the sheets beneath me as she pushed the toy deep into me while it tickled my clit from the outside.
“There’s more,” Jessie said, before pressing on a button on the bottom of the device.
“O-oh, oh, oh my god,” I stammered, as the toy came to life inside me, buzzing firmly.
“Mhmm, that’s what I’m talking about babe. That,” Jessie smiled, thrusting the toy into me as she watched me squirm under her.
“Ugh, babe, this is mmmmh, this is fucking amazing,” I moaned, beginning to thrust my hips against the toy as Jessie held it securely in place against the bed.
“You look so… beautiful,” she sighed, her eyes travelling across my naked body.
I blushed, panting quietly as I continued to rock my hips against the purring toy. My eyes locked with hers, and we shared a moment of endearing intimacy. Her gentle hazel brown eyes twinkled blissfully as we smiled at one another, and I slowly lost myself in her gaze.
Pressing the toy into me firmly, she pulled her shirt off and climbed over me. Pressing her lips against mine, she kissed me fully. Smoothly, her tongue slipped past my lips and locked with mine. She swam inside my mouth, deftly teasing me with the dexterity of an experienced lover. As she pulled away, we opened our eyes together and looked into each other again.
“Kiss me again, please,” I begged, the toy lodged deep inside me, buzzing firmly against my g-spot and nudging my clit.
My juices poured, soaking the sheets underneath me as Jessie kissed me over, and over again. Slowly, she moved down to my neck, licking and sucking tightly on my skin.
“Mmmh, babe, you’re gonna’ give me a hicky,” I whined, “You know I have that big meeting on Tuesday.”
Jessie looked up, flashed me a cutesy smile, and continued kissing down my neck. Slowly, she wrapped her lips around my left tit, and began flitting at it with her tongue. While her right hand reached for my other tit, pinching and massaging it between her fingers, her left hand quietly snaked down between my legs, and began fiddling with the toy that was pressed deep into me.
I felt her fingers search around the base of the toy, and then I heard the click of a button.
“Oh… my go-mmmmh, fuck, fuck, fuck,” I moaned, as the intensity of the toy’s vibration shot up a notch. “There was a second level?” I gasped, unprepared.
“Mhmm. I told you this thing was the shit,” she winked.
As her tongue continued to run circles around my erect nipples, her hand thrust the toy aggressively into my wet, swollen pussy lips. I arched my back, my hips shuddering as I found it difficult to contain myself. Jessie’s motions with the toy were clearly borne from experience, and I could feel her hitting all the right spots with her rhythmic, circular motions. Panting, I began thrusting my hips against her plunges, aching for the feeling of the toy’s vibrating, swollen head against my g-spot.
“Harder, please, harder,” I begged, my eyes glazed over with unabashed, wanton desire.
“Beg for it baby,” she said, biting down hard on one of my nipples.
“Mmmh, please, please Jessie, fuck me harder,” I squealed as her teeth tightened around my tit.
I felt the speed of her thrusts increasing as she began to pummel me between my legs mercilessly. Locking her wrist, she ploughed into me with ferocious speed as the toy buzzed firmly between my lips. I felt like I was being torn apart, and I was enjoying it thoroughly.
“Oh my god, babe!” Jessie suddenly exclaimed.
I looked down, and watched as my pussy squirted against the toy and all Jessie’s arm and bed.
“Oh… my god. That’s never happened before,” I said panting, my pussy still aching for more of Jessie’s delightfully forceful pounding.
Smiling, Jessie brought her wrist to her lips and licked the shiny juices I’d showered her in.
“Tasty. A little teaser of the future?” she asked teasingly, grinning.
My face flushed instantly.
As she climbed back over me and continued her onslaught on my pussy with the vibrating toy, I closed my eyes and fantasized about just that. I imagined Jessie dip down between my legs, pull my thighs open, and press her lips against my pussy. I imagined feeling her warm, wet tongue pull along the lips of my soaking, dripping pussy for the first time. I imagined grabbing her by her long, brown hair and pressing her lips against my cunt, and rubbing the length of my pussy across her small, petite face. I imagined squirting all over her, covering her lips in my juices. I imagined her slowly crawl up to me and press her wet lips, covered in the taste of my sex, onto mine.
“I’m cumming Jessie, I’m fucking cumming,” I whimpered, my hips riding her thrusts as I felt my pussy clench around the probing wand.
Jessie shoved the toy as deep as she could into me, and held it in place. Then, she watched as I spun my hips desperately, nudging the vibrating toy’s head against my g-spot in a frantic delirium. I squealed as the toy buzzed firmly against it, throwing my body into an involuntary convulsion. My back arched, and I writhed in a frenzy with the toy lodged deep inside me, and its buzzing rabbit ears assailing my swollen clit fervently.
“Oh my god, mmmmmh. Oh my fucking shit!” I panted, sweat pouring from my forehead as Jessie smiled gently.
I looked down, and watched as she eased the toy out of me while my shuddering orgasm ebbed. She delicately teased by lips with the tip of the toy, toying with my wet, puffy lips before she kissed it, and then placed it on her bed.
“Fun?” she asked.
“I think… we can do without boys for a bit,” I giggled, biting my bottom lip.
Jessie winked, and lay her head in my bosom. Exhausted, our eyes closed, and we fell asleep in one another’s’ warm embrace.
Heterosexual sex that involves my female wife using a handheld dildo to anally penetrate me, her mal...
Today was really a crazy day for me, first my secretary took ill and didn’t come to work. Secondly, ...
I sighed as I stared at the empty placemat in front of me. Here lately, it seemed to be empty more o...