Are You Willing?

For years my wife and I had a great sex life, but it grew more exciting after our 10th anniversary. That's when Cyndi and I started playing "Are You Willing?" At first we used the game to just ask questions: Are you willing to tell me how you lost your virginity? Are you willing to share your masturbation fantasies? Are you willing to admit the kinkiest thing you'd like try in bed?

And then we started asking: "Are you willing to do everything I say?" If the other agreed, the initiator would then propose various sexual dares and later provide a sexual reward. (My wife's usual prize was having her ass licked, something I never really enjoy doing). I was willing to be spanked hard with a ruler, wear a butt plug out to a local pub, and have Cyndi watch me masturbate on cam to a stranger. She was willing to have her exhibitionism explored: I had her flash her tits to highway truckers, model naked in the woods, and wear short skirts to show off her panties in bars.

This past spring we booked a June trip to the Dominican Republic. Our "Are You Willing" game was the highlight of "How I Spent My Summer Vacation".

* * * * * * * * * *

We flew out of New York early Saturday morning. By 4PM we were on the beach, drinking rum and 'Presidente' beers. We traded the crowded city for ocean breezes, tropical sunshine, and sand between our toes. Vacations loosened us both up, and Cyndi brought a string bikini that was more revealing than what she normally wore. She's 5'6, a natural blond and even by June had a nice tan. She had always been thin, skinny even, but after switching to a sedentary 9 to 5 job her body filled out. Her butt and belly thickened, she looked sexier than ever.

We spent our first afternoon on the beach. Reggae music drifted from the resort. We floated in the waves and dozed in the sunshine. We checked out both men and women in skimpy swimwear. I buried her feet in the sand. After dinner, we attended a Motown show on the outdoor stage, then made wild and wonderful love to the sound of the surf outside our room window.

Sunday and Monday were equally carefree. Tuesday morning we had breakfast in the open air plaza, followed by snorkeling at a nearby reef. Back at the resort, as we ate lunch she initiated the game. "Are you willing to do everything I say today?" I smiled, my cock already tingling in anticipation. Her first request: "Are you willing to buy me one of those ... thong bathing suits?" We had seen a selection of extremely revealing swimwear in the resort shops. At the time she had wondered how women could wear those. Somehow her tune had changed. "Something slutty so all the men will stare at me on the beach..."

As if her string bikini wasn't slutty enough! But I agreed, and she returned to the room while I went shopping. The store's selection included one-pieces, skirts, full bottom bikinis and skimpy thongs. My cock perked up as I examined the latter, and eventually I picked out a white thong bottom with a pink bra top. When I let myself into our room Cyndi was reading on the bed in a tee shirt, panties and socks. She stood and kissed me, examined my purchase, then had me get her ready for the afternoon.

After I peeled off her clothes, I wrapped the top around her breasts and slid the thong up her legs. God, she looked sexy. Her breasts were nearly popping out of the bra; had I gotten a size too small? The thong left most of her ass exposed, all but a small white triangle in the back. She pushed the thong's front to the side, revealing her neatly trimmed pubic hair. "I wonder if some lucky guy will get his cock in here...." I couldn't wait until the game was over because I knew I'd be that lucky guy!

She wore a white mesh cover-up that didn't cover up much. On the beach we found empty chaise loungers, then soaked up the sun. Summer here was more relaxing, more carefree than the summer we left back in New York. I drifted into a nap. When I opened my eyes Cyndi was face down on her lounger. Sunlight glistened in the lotion that glazed her body. Her thong exposed the tan lines from the bottom she usually wore. I admired how her body had gotten fleshier these past years. I drifted into another rum-induced nap, complete with a sex dream.

When I awoke Cyndi was sitting up, watching two women in their twenties topless at the water's edge. Seeing me awake she asked: "Are you willing to have me go topless?" I was mildly shocked, as she had never been willing to do this in the past. But everything was different down here, and when I readily agreed, she leaned forward and had me unclasp her top. There she sat, exposing her tits, white circles of untanned skin, with nipples fully erect. She lotioned up the virgin skin. "I could get used to this," she laughed. "And you don't mind all the men seeing my breasts?"

"Nope." To be honest, it turned me on.

We were on the private 'adult' section of the beach. There were three cabanas to our right: two unoccupied, but one with a good-looking guy in his twenties. All afternoon he had been watching us. Watching Cyndi, I should say. We jokingly nicknamed him 'Cabana Boy,' and later, as we returned to our chairs after a dip in the ocean, she asked: "Are you..." She stopped and thought carefully before continuing. "Are you willing to ask Cabana Boy to put lotion on me? All over my body?"

That threw me for a loop. While she had occasionally agreed to flashing strangers, and while we had incorporated other men in our fantasy talk, we had never incorporated physical contact with another person into our sex play. I was unsure if I was ready to watch this, and equally unsure if I could actually ask him to lotion up my wife. How would I even bring up the topic?

Cyndi rolled onto her stomach. She clenched her ass cheeks. "You don't want me to burn do you?"

No, of course not. Looking over I noticed that Cabana Boy was watching us. I knew that Cyndi would never cheat on me so I doubted that this dare would go beyond touching. And would this be any different than her getting a massage? (Of course it would be different, but this was my rationalization.) Woozy from the hot sun and cold drinks, but refusing to end the game, I stood up. As I walked across the hot sand I mentally rehearsed different conversation starters.

At the cabana I introduced myself. He told me his name was Mark. I got tongue-tied. "My wife and I- Cyndi there... We were wondering if you'd, uh... she'd enjoy it if you'd... help to.. lotion her back. She'd like that. " Then, in hurried voice: "I mean, if you'd rather not, well, you could-"

He held up his hand to stop my blabbering, eyed me carefully, then looked over to Cyndi. She had her head turned to us. She picked up the lotion and waved it. Naturally he was surprised at the request. "You don't mind having anoth-?"

"No". I shrugged. "She'll enjoy it."

He took a sip of his beer, and gave me a look like he was trying to figure me out. (What kind of husband would do this?) But then he set the bottle down, and without speaking stood up. I followed him across the sand and when we reached Cyndi, we both looked at her lying there: her blond hair tied in the back, her bronzed body, the tan line where her bra strap used to be, her full ass in a white thong - a tiny white patch, her cheeks browning in the sun. "So, you'd like some assistance, Miss..."

"Cyndi." I told him.

She held up the lotion to him. "Please." She sounded nonchalant but I knew she was trembling inside.

"It will be my pleasure." He crouched down, shook the can, then sprayed her back liberally. I watched his hands rub circles over her skin, at first lightly, then deeper. He kneaded his shoulders, then moved down to her lower back. "You have great skin. And a great body..." When his hands moved too close to her sides she giggled at being tickled. "And your bathing suit..."

"My husband bought it for me. I guess he doesn't mind showing me off."

"Or having me do this." As he said this his left hand ran over butt. When he looked up at me, I couldn't decode his thoughts or his impression of me. I felt somewhat jealous, even a bit emasculated, but I was also aroused. After spraying her right leg he wrapped his hands around her ankles then moved up her calf, around her knee, and up her thigh. Then he moved to her other leg, spraying lotion and massaging skin. When his hands rubbed the top of her thigh, his palm dipped between her legs, his pinky brushing her ass cheek.

Cyndi spread her legs slightly. If she was offering him the option to touch her there he didn't take the hint. Instead he sprayed lotion on both cheeks, then used his hands to rub it in. He took his time, his fingers covering every inch of her ass. It was a turn-on to see her being touched by another man for the first time. He even pushed the thong away from her crack and sprayed the lotion. He quickly ran a finger down the crack and before she could object he replaced the thong.

He was kneeling in the sand but he straightened up. "Why don't you turn over," he said in a soft, calm voice.

I was in the sand on her other side. I watched as she slowly rolled over, instinctively keeping her breasts covered with one arm. I looked at the front of the white thong -- was that a wet spot? As Cabana Boy shook the lotion can he eyed my wife greedily. Before anyone could speak, he quickly sprayed the top of both legs, then set the can on the lounge. He placed his hands on each of her ankles, then moved them slowly up her legs. When he reached the top of her thighs his thumbs brushed against the thong. Once again he moved his hand quickly before she could protest. He certainly knew what he was doing.

When he picked up the can, preparing to lotion her chest and stomach, Cyndi shook her head. "No, no, I think I'm good yup here." She was ending this challenge. "But thank you."

He nodded politely. "Of course. No worries." I was thankful that he didn't push the issue. Sensing we were done with him, he stood up. His trunks bunched up around an obvious erection. (I had one, too.) "The name's Mark," he told use before walking away, "if you need further assistance..."

After he was gone Cyndi gave me a nervous stare, unsure if I was upset. To reassure her I kissed her lightly on the lips and whispered that I loved her. "Good," she said, followed by, "If you really love me you'll fuck me right now."

"Here?"

"No, in our room. But now!"

Not bothering to put on her bra, she threw on the cover-up, her nipples poking through the mesh. We left our towels and bags on the loungers and headed off the beach. Waiting by the elevator she gave me a deep soul kiss. Once inside the elevator she rubbed my erection through my trunks. "You gave Cabana Boy a hard-on, too," I told her. Back in our room I closed the door and she knelt on the floor and stripped off my trunks. I held her damp hair in my hands as she sucked my cock. She slurped loudly, and stared up at me with slutty eyes. But this was just quick foreplay. She stood up and grabbed my cock to pull me to the bed. We shared another a long kiss as she pushed the front of the thong to the side, offering me her wet pussy. I slid inside her and felt her vaginal muscles tighten around my cock. I thought she might begin talking dirty about Cabana Boy, but the only thing she said was, "I have a special reward for you." When her body started to quiver she grabbed hold of me tighter, one hand on my back, the other on my ass.

We were in an unusual (and not totally safe) contraceptive phase, me using condoms or pulling out, so when I felt my orgasm near I started to pull out. "I'm going to cum," I told her. But with her arms around me she pulled me tighter. "No, don't, not today.... I want you to cum with me... Cum in me..." She bit my lip as her first orgasmic wave overtook her. "I want you to fill me up..." I thrust in and out of her, faster now, and felt her legs grip me tighter and her fingernails scratch into my back, and I placed my mouth on hers, my tongue inside her, our spit mixing, and a swelling in my cock, and then a burst of hotness rush through my head, and I felt my cock pulsing and pulsing, my cum erupting and filling her, Cyndi, my hot sexy wife, my lover.

* * * * * * * * * *

After allowing me to cum inside her Cyndi ran to the bathroom hoping to pee out my semen. When she returned we fell into a long, deep nap, and awoke later in the afterglow of great sex. After dinner and dancing we strolled the beach, hand in hand, under the light of a full moon. The following day was an 'adventure excursion' that tired us both out. It wasn't until Wednesday evening, as we dressed for dinner, that I asked, "Are you willing to do everything I say?"

She smiled. "Of course!" She was already dressed to go out, but I asked her to go braless. "In this?" Her sundress was sheer; in a certain light it would clearly reveal her breasts. But I nodded and she turned around for me to unzip the back. "I'm glad you don't mind other men seeing my tits." After removing her bra and zipping up, she asked, "Does this meet your approval?" I rubbed her breasts and watched her nipples harden, forming 'pokies' that lasted throughout our walk to the restaurant.

I picked a table next to a foursome of older men. I had her chair face them, and asked her to undo another button of her blouse. Their glances kept her - and me - aroused. After dinner and dessert I asked, "Now, are you willing to remove your panties?" She was. She checked to see who was watching, then somehow slipped out of her thong right there at the table! She gloated as she set the black silk panty before us. When the waiter stopped by to say good night we both waited for the other to hide it from his view. Neither of us did. The waiter spied the sexy undergarment and snickered.

On our way to the open air plaza two men strolled behind us, keeping our pace. My suspicion that they were checking out Cyndi's butt was confirmed when they followed us into a gift shop. "Are you willing," I whispered, "to give those guys a peek at your ass?" She turned to see them, then smiled. The shop was empty, just the four us and a bored cashier. Cyndi went to a rack in the corner while I moved to the exit. The men stayed in the middle, pretending to browse a rack of polo shirts but keeping Cyndi clearly in their view. My wife picked up some trinkets, then crouched down to supposedly examine something on a bottom shelf. As she did, she leaned forward. Her dress rode up and revealed the bottom of her panty-less ass. After giving a show, she stood up, turned around, and brushed past the pleased men.

We danced salsa in the plaza, then headed to the disco. We sat at the bar, Cyndi still without panties. A few seats from us sat Cabana Boy with two friends. He held up his glass to acknowledge us. We ordered drinks - Cyndi was tipsy already - and as we sat I kept my hand on her upper thigh. "I bet Cabana Boy would love to fuck you," I told her, and moved my hand to brush her pussy. Was she already damp?

Shortly thereafter, Cabana's friends left and when the couple next to Cyndi departed, Cabana Boy slid down two seats. "It's Mark," he told us. "Can I buy you guys a drink?" We agreed and made small talk about the resort and the week's perfect weather. There was no mention of the beach massage he had provided. When he visited the men's room, I asked Cyndi if she was willing to dance with him. "You'll have to wait and find out," she answered with a grin. After he returned and a new song came on, she announced, "I love this song. And I want to dance!" She looked at me. I feigned unwillingness. She then looked at Cabana Boy - Mark - and he gladly offered. She winked at me as he led her onto the dance floor.

It was exciting to watch her move in that revealing dress. When the spotlights hit just right I could make out her breasts. And once, when she spun around, her dress lifted to reveal her naked ass to anyone paying attention. As they returned to the bar, Mark had his hand on the small of her back. Cyndi looked breathless and flush. "Your wife's a great dancer," he told me before turning to get the bartender's attention.

Cyndi kissed my cheek, looking like the cat who swallowed the canary. "I felt him get hard while we were dancing. But he was a gentleman." She raised her eyebrows. "Mostly."

I surreptitiously touched Cyndi between her legs. "Did he feel how wet you were?"

"Not yet," she laughed.

I thought about how she had him rub lotion into her back, legs, and even her ass. I'll blame it on the alcohol but I decided to up the ante. "I bet he would love to feel your wetness." How much further could I could push her? And how much further did I want her to go? But then these words came out, surprising even me: "Are you willing to let him feel how wet you are."

She looked at me in surprise. "You're not serious-?" She squeezed her legs around my hand, trapping my wrist, then releasing it. "Are you?"

"You might enjoy it. And it would just be a touch. Nothing more."

"Just a touch, huh?"

"Just a touch. Like on the beach..." (Although, no, this wouldn't be just like that...)

Before we could say more Mark finished with the bartender and returned his attention to us. I nudged Cyndi's to have her swivel on her stool towards him. They struggled to converse over the loud music. It was fun to watch him maintain eye contact with her and yet also steal occasional glances at her breasts and legs. She turned her head, looking back at the dance floor. I knew she was mulling this over, and I still doubted that she would proceed.

But then she swiveled the stool further, moving one leg but not the other. To the unsuspecting it looked innocent, but she had actually spread her legs and positioned them to give Mark a peek at her pussy. He glanced down, but when he caught me watching him, he looked away -- out at the dance floor, too.

Cyndi leaned in and whispered something to him. "It's OK to look," I found out later. He didn't waste time. He sat back in his chair, grinned at me, then glanced down. Again, the unsuspecting wouldn't know what was happening. But I knew -- another man was eyeing my wife's pussy!

She was still eyeing the dance floor behind her. There was a fierceness in her look; she was steeling herself, I thought. What she did next was this: She turned in her seat until she faced the bar, still with her legs spread. Then she leaned close to Mark. She widened her legs further until her leg was pressed against his.

He had his right hand on the bar, tapping his fingers on a napkin. Cyndi reached up and grasped his wrist, then slowly, tentatively, she lowered it below the bar and onto her thigh, near the knee. Again he eyed me for a reaction. I just nodded. 'It's your lucky night,' I wanted to tell him.

Cyndi took the initiative to guide his hand to the middle of her thigh, and then down lower. He must have squeezed her leg because she bit her lip. Lowering my gaze I saw her hand caressing the back of his, then she slid it up her thigh, over her smooth skin, until his hand slipped under her dress and dipped lower. I think all three of us were holding our breath.

Here's what she told me later: At first his fingers rested on the inside of her thigh, his pinkie resting where her leg met her groin. Then he gently flipped his hand over so that the back of his fingers rested against her mound. He waited before turning his hand over. That's when his fingertips felt her moist lips. And then a finger lined itself against her slit. Soon a fingertip ran up and down, opening her lips. Would he stop? No, he pushed his finger inside her, then deeper. Finally, emboldened, he slid a second finger in her pussy.

Suddenly she flinched. She jerked her body and pushed his hand away. She was shaking her head, visibly upset.

What happened after that is a blur, but somehow we managed to extricate ourselves from Mark's company. We hurried back to our room in silence, Cyndi clinging to me. I thought she was angry at being pushed too far, but when we got the room she closed the door, leaned backed against it and pulled the hem of her dress up, revealing her pussy to me. She had that fierce look again. She looked sultry, sexy, wanton.