Sex Toy Tales: Tales

“Whatever you do, don't forget the dildo,” she warned, her voice low so that the taxi driver wouldn't hear. Annie and I were on our way home from a Brenda K. Starr concert at the Copacabana, still humming the tune to that signature song “I had a dream that some day you and me…”

“How could I?” I asked incredulously, fingering her dark spiral curls. I loved playing with her hair. My girlfriend had purchased the pretty, translucent purple toy at a local Manhattan sex shop days earlier on her quest to bring something fun and new on our upcoming vacation to Jamaica. Not that we'd need it; we usually managed to have sex anytime, anywhere, anyway, and I was certain that a tropical locale would only raise our libidos. Mine had dropped a little recently, along with the air temperature: the nights had been subzero for over a week now. It would be our first vacation together, a mid-February jaunt that harkened back to the days of carefree Spring Breaks. I couldn't have been more excited.

“You can stop here,” Annie told the driver as we pulled up to my Chelsea apartment building. “Are you packed yet?” she asked as we entered the small second-floor two-bedroom. The evidence of my attempts at locating what summer clothing would hug but not squeeze my winter weight-enhanced body was strewn around my room. “Guess not. Well, make sure to do it by tomorrow night, because the flight is early on Sunday, and I don't want to wind up running like maniacs through the airport.” Annie could be a little bossy sometimes. But I liked it, and we both knew it. We crawled under my down comforter and slept close for warmth. I fell asleep thinking, Only two more days!

At least that had been the plan. I awoke to my cell phone shrilling Canon in D at 7:30AM. Who would be calling so early? Dad. “Kiki, honey, have you looked outside?“

Fumbling to pull aside the window curtain that grazed my bed, I answered groggily, “No, why?” Oh, that's why. The ledge of the window opposite mine, my sole view of the outside world, was coated in snow, and the marshmallow-sized flakes (and I don't mean the mini variety) were falling at a rapid pace.

Answering before I could ask, he continued. “It's a region-wide blizzard; we're supposed to have twenty-four inches by tomorrow morning. Beginning tonight, airports will be closing.” Fuck. A departure glitch. There was no way I was allowing snow to interfere with the warming sunburn that would fade into a deep golden tan over the week… “You might want to try and leave early, Kiki.” He'd said enough. I thanked him and hung up, quickly beginning frantic mental preparation. Annie stirred next to me.

“What's going on?”

“We're leaving for the airport. Now,” I answered, already grabbing from the shelf her L'Oreal Springing Curls and my Sun-In Blonde Highlighter and dropping them into a cosmetics bag.

Annie joined me in high gear. Her energy level, sexual and otherwise, had never failed to match mine. “I'll go to my place, pack, and make sure American can get us on the soonest flight out. I'm an Advantage customer, so it shouldn't be a problem. You call your dad back and ask him to take us to La Guardia. We can meet him outside here in half an hour.” Bossy again, but I was glad to be given motivational direction.

So motivated was I that I managed to remember my plan to bring my overstuffed laundry bag with me in order to pass it along to Mom and Dad on our way. I was just far enough out of college—five years—that their confidence in my self-sufficiency made them comfortable serving as my cost-free laundromat.

The purple dildo was propped up on my black wooden desk, just as it had been displayed so beautifully in the store. The light from the snow made it almost glow, and I felt a rush of excitement surge through me as I placed it on my bed, next to my new black and silver bikini. I was certain it would be a sex-charged vacation, and here lay the new player in our games.

“Kiki, you're up already?” My roommate, the cute, Martha Stewart-esque Lily, stumbled sleepy-eyed out of her bedroom, clad in a powder-blue bathrobe. I informed her of my expedited departure. “Good luck! Oh, favor to ask you,” she said through a yawn, “Tim will be in the city for the early part of the week. Any chance he can stay in your room?”

“Of course, no problem.” I liked her older brother a lot. “Tell him I'm sorry I didn't have time to make the bed.”

Twenty-five minutes later, Annie and I were gleefully interlocking gloved fingers in my parents' BMW, which had thankfully sped from Scarsdale to Manhattan in record time. We were booked on the next AA flight, direct to Montego Bay. Score.

Passing through airline security, we exchanged nervous glances. Would the dildo show up on the security monitor? I couldn't think of any weapons that a dildo directly resembled, but nowadays, with tweezers constituting the next holdup danger, you never knew. Annie had once been humiliated, she'd told me, by being asked to remove‹and turn on‹a vibrator that was in her bag. Luckily, we were not questioned about the item, and we sailed to our gate. The short plane flight gave me every bit of confidence that I'd be oversexed‹and happily so‹by the end of the vacation. The same stroke of luck that had gotten us onto the earlier flight had also landed us next to an empty seat. Annie lay across the seats, her head in my lap, and I read aloud to her, albeit quietly, from erotica books she'd crammed into her Jansport. We entered Mile High Club status as she drew the navy blue airplane blanket over her lap and whispered up to me, "Touch me." Shockwaves of attraction ran through my body as I reached my hand down under the elastic of her pants and into her panties. Finding her wet, as she usually was, I massaged her clit with my fingers until she was moaning into my gray hooded sweater. I reached further to gently put two fingers inside her, and she came, hard but silently, the tremors in her body betraying the strength of the sensation inside her. Fortunately, the elderly couple sitting across the aisle from us were headphoned and ostensibly rivited by the feature film The Object of My Affection.

“You're the object of my affection,” I said giddily to Annie, love making me feel sappy and warm. She touched my long golden locks.

“Ditto,” she whispered, kissing me. “And speaking of objects, I have some plans for breaking in our hotel room…”

Okay, so it wasn't actually a hotel, more a downtrodden bungalow, but the hand-carved bed looked like it could fit us both, and hot water did emerge from the showerhead, at least for the first five minutes of use. And we were in Jamaica! Soaping myself under the shower water, I felt some sympathy for the freezing New Yorkers, but not enough to trade places with them. The outside temperature was close to 90. I exited the stone-floored bathroom, my long, drenched hair sticking to my back and soaking the top of the white terrycloth towel I had wrapped around my small frame. Annie was seated on the bed wearing a white tank top and shorts. I could see her nipples through the tank top. The tropics commanded bralessness. Better that way. I stood in front of the canopied bed and she looked up. She placed the island guidebook next to her. “Take off that towel.” That's it, Annie, tell me what to do, we both like it that way. I dropped the towel to the floor, and she pulled aside the draping folds of the white gauzy mosquito net to allow me to move into the enclosed area. She ran her hand down my body, from my pale neck down past my now-erect pink nipples, to my bare pussy, which she had shaved in preparation for the trip. “East access that way,” she always said, grinning.

Her hand dropped to my thigh, but I took it in my own and moved it back to my pussy, where I wanted it to remain. “Oh, baby,” she said, discovering that I was already wet with anticipation. “Come here.” She pulled me on top of her and we fell back on the Hawaiian-print sheets together, the shoddy bed creaking with our combined weight. Her brown ringlets fanned out around her face, coating the pillow, and my straight blonde locks penetrated the curls as I tumbled onto her. She lifted me up and took one of my breasts into her mouth. I slipped one of my legs between both of hers, pushing them apart, pressing my knee up into her cunt. She moaned and sucked harder on my breast.

“I want you,” I breathed into her ear. Annie knew not to spend too much time on my breasts. I was more responsive to the other stuff and could usually come only from penetration. “Oooh baby, yeah,” I said into her ear in a sing-songy voice. I was quoting Brenda K. Starr again. She reached her hand between my legs, running it up my thigh and then pushing her palm into my pussy. I sat into her hand, feeling a chill rush through my now overheated body, and she pressed into me harder. I was getting wetter by the moment, dripping onto her palm, my juices trickling through her fingers and starting to soak her tan shorts. I dug my knee further in between her legs, knowing that she could do anything to me with expert execution and still match my wetness. Sometime she even came along with me, still clothed. She slipped one finger into me, and I tensed up.

“Relax, baby.” I obeyed. That's nice, tell me what you want from me, Annie. She obeyed. “Now sit on my fingers, and let me feel you move on top of me.” I felt her insert another finger, and I moved down further, until my weight was resting on her abdomen. I was moving on top of her, letting her fingers massage my g-spot, when she ordered, “Now stop.” I was still. “I want to fuck you with that new dildo, Kiki. Go get it for me.” Yes, Annie, whatever you say. My hair and pussy both dripping, I shifted off of her and out through the mosquito net. To save time, I dumped the contents of my backpack onto the floor and began pawing through them for the object of our mutual desire. Approximately two minutes later, Annie sat up. “Kiki, are you coming,” she paused for a beat, “back?” She laughed.

“Fuck!” I shouted.

“What?”

“It's not here. The dildo. It's not with my stuff. I know I packed it—I mean, it was right there with my new bathing—" And then it hit me. The bikini, too, was missing. When Lily had called me out of my room to ask about my early wake-up, I had abandoned those items on my bed. I could swear I could recall dropping the dildo into the bag, but apparently I had not. And when my dad called to say he was waiting in the car outside, I had simply tossed some remaining garments into my laundry bag, grabbed that and my backpack, and dashed out the door. Which meant that the dildo was— “Fuck!” I exclaimed again. I was on a roll. “I left the dildo on my bed. And Tim is going to find it!”

“Tim?”

“Lily's brother. He's sleeping in my room this week. Holy shit, I am going to die of humiliation. Maybe he'll think it's‹does it even resemble anything else?”

Annie's face betrayed a combination of shock, disappointment, and, to my chagrin, amusement. “Whoa! Uh, no, it really just looks like a big purple dick.”

A big purple dick. Lovely. “Fuck!” I really needed a new line. I felt woozy as I tried frantically to recall the events of those final harried moments in my room.

“It's okay, Kiki, at least you didn't put it in with your laundry. Can you imagine the look on your mom's face if she found it?” Annie dissolved into giggles, but I froze.

“Oh my god! No! Annie, I could totally have accidentally dropped it into the laundry bag. It's all a blur.” I vaguely recalled sliding some clothing items off the edge of my bed and into my backpack. Had the dildo fallen in, too? It was all too much to think about. I sat on the floor in disbelief.

Annie came over to me. “It's okay, Kiki, we can wait until next weekend to use it. There are other—” Stunned, I cut her off.

“This isn't about getting off, Annie!” I yelled, tears starting to form in my eyes. Usually I loved the fact that her mind was so one-tracked, but now I was just irritated. “In one week, I will be either mocked by Lily's entire family or disowned by my own.” The image of my innocent mother holding up the purple toy with an expression of—disapproval? awe? confusion?—hit me like a punch. My life was ruined. My racing mind fast-forwarded to me finding myself a nice shanty in Montego Bay. I could learn hair-braiding; it wasn't that challenging. New York would be too frigid a place to return to, that was certain.

“Sorry,” she said, “I just don't want you to be upset for a week when there's nothing you can do about it from here.” She was right.

“You're right. I'm overreacting. I'm just going to relax.”

“You do that.” She stroked my arm. “Hey, I have an idea.” Annie always had ideas.

“Get dressed.” I was able, in the wake of the missing dildo dilemma, to derive some small happiness from being able finally to don a sundress and sandals. I applied Coppertone 45, grabbed my new DKNY sunglasses, and was ready for…

“The vegetable market!” I didn't believe her. “Kiki, I'm telling you, I used to do this with my ex-girlfriend all the time. She loved it. Nothing fucks quite like a good cucumber.” I didn't like hearing about what her ex loved, but I was highly intrigued by the adventure on which we were about to embark.

After walking along the dirt path that led out of the cluster of villas that we were calling home, the blazing sun all but melting us, we crossed a short bridge and entered the outdoor marketplace. Covered stands displayed fresh, multichromatic fruits of familiar and unfamiliar types, resembling to me those pretty plastic colored balls in pools at theme park Kiddie Lands. Annie wasted no time admiring the fruit. “We need…zucchini!” she announced, spotting a bin of green vegetables and taking me by the hand. I had only a moment to wonder whether my girlfriend was certifiably insane before we were standing before a large bin of zucchinis. “You want one that's hard, right?” she asked, an air of efficiency in her voice.

“Shhh!” I said. I noticed that the Jamaican vendor was eyeing us closely. “Spring break, girls?” he asked.

Annie looked at him with cooler-than-thou exasperation. “Please. I'm thirty years old,” she said. That shut him up. She turned back to me. “He doesn't care why we're here. We're giving him business.” I, too, shut up and followed her lead in feeling various zucchinis for their firmness. “Found one!” she announced, holding up the vegetable like a torch. “It's long enough for you, too. I know you take it deep.”

I kept my mouth shut, but my cheeks were flaming as I whispered, “Um, yeah.” I noticed that the vegetable was long and straight, like a cucumber, until the very tip, where it got smaller and curved upward a little. Annie led me confidently out of the marketplace, proud, I knew, of her find. I shook my head and smiled bemusedly. Who knew a produce market would become our Jamaican sex top shop? As we approached the bridge, I heard the vendor call out to us.

“You ladies come back soon. I find you Jamaican husbands next time.”

Annie leaned over to me and whispered, “I think we've got enough dick right here, thank you very much!”

“You're fun,” I said, looking at her admiringly.

“I know,” she answered. “Now, when we get back, I want you to take off your clothes, get on the bed, and…” Awed by her boldness and creativity, I zoned out her words but could feel myself getting wetter with every step along that dirt road.

“Good girl,” she said as I removed my clothing again and reclined on the bed.

“I like when you call—,” I began, but her mouth muffled mine as her tongue circled my own, stroked the depths of my mouth, dashed over my teeth. I reached up and ran my fingers up into her hair at the nape of her neck, pulling softly on it. “Now you can finish what you started, Annie.”

She reached down to find me wet again. “Good girl. That's what I want.” I writhed in anticipation of her plunging her fingers into me. But she wasted no time with fingers this time around. “Stay still.” My eyes were closed, but I could hear her unwrapping a condom and rolling it over our recent purchase. “Tell me how you want it, okay?”

“Yes,” I breathed. I could feel the cold tip of the vegetable make contact with the lips of my pussy. I shuddered.

“Stop?” she asked.

“No!” I said forcefully. “I mean, no I want it. I want…you.” My blue eyes locked into her brown ones as she slowly inserted the firm zucchini into me. It was about eight inches in depth. “Wow.”

“I knew I'd find a way to fuck you, Kiki, because I love fucking you deep and hard. And I know you like to take it from me.”

Understatement. “Yes, Annie, I love the way you fuck me.” My breath caught in my throat as she plunged the makeshift dildo even deeper into me. She moved it in and out of me, in rhythmic pattern, fucking me with concentration, skill, and passion. My body felt simultaneously numb and overstimulated. I was tingling and shaking, my blood pumping fast through my veins as I succumbed to the incredible sensation passing over and through me. “Harder,” I whispered. I could feel the nobby tip of the vegetable running over and over my g-spot in a way that no ordinary dildo could.

“I can feel your heart beating,” Annie said from her place on top of me, her mouth near my ear, her hand still pumping.

“Don't stop.” As I said, it, I came, a rush of heated sensation rocketing through my body as I spasmed and squirted my juices out and onto her white tank top so that it clung to her stomach. There were no words. I'd never come like that in my entire life, the new dildo having created a simultaneous stimulation of all of my sensitive inner parts that jarred my mind and body.

“I know,” she said, and she did. I knew she could feel with her own body the height of my reaction.

When I recovered my breath, I smiled up at her lovingly. “You know, it was almost worth it to have forgotten that toy,” I mused, laughing, “just to discover this new one. Who knew?”

Annie grinned. “So you don't mind that your mom—“

I put my finger to her lips. “Don't mention my mom now,” I said sternly. “Bad timing. Quiet.” We both giggled.

“Well, in that case, can I show you something?” Annie got up from the bed and crossed the room. She reached into her Jansport and pulled out…

“The dildo!“ I exclaimed in shock, as she held up the translucent purple toy. “What the—?”

Annie burst out laughing. “Gotcha!” She sat on the floor, stroking it. “I thought I'd have a little fun with you. At the airport, I switched it from your bag to mine and decided to introduce you to something a little different before you get too addicted to this thing.” I wasn't sure whether to be furious with her, amused at the turn of events, or just relieved that the dildo was not being scrutinized at this very minute by either Tim or my mom. I decided upon the latter two. We were, after all, on vacation.

“You bitch,” I teased, laughing. “This is so typical of you.”

“Always mixing it up,” she responded.

“And as your punishment,” I continued, tossing the zucchini into the wooden garbage pail that lay next to the bed, “I may just have to initiate you with that now rather passe dildo. Poor Annie.” I mock-pouted. After getting me off like that, I didn't think she'd mind relinquishing control for a brief while. “And if you're good, and only if you're good, we can return to that vegetable stand tomorrow…”

“Yeah,” she smirked, "because I think I know a hot Jamaican man who could really use a wife…”