The Dare

The letter came in the mail, a small, neatly hand addressed envelope, almost hidden amongst the junk mail and bills that makes up 95% of what I get. There was no return address but the post mark was local. I get so few real letters now, what with Facebook and emails, that it was the first piece I opened. How many people can identify the instant their life turned in a new direction? I can. It was the moment I opened that letter.

“Dear Claudia.

While we’ve met, you don’t know me. But I know you. I think you are smart and beautiful; the most beautiful woman I’ve ever encountered. When I hear your sweet laugh, I want to caress your smiling face. And make love to you. Not just to taste your beautiful body, but to meld my physical being with yours. I know you are happily married and the chances of your being swept away, like in a fairy tale, are slim. But I’m hoping that your sense of adventure will be intrigued by what I’m about to suggest.

I’m going to dare you to do five new things. If you do them, faithfully and fully, it will be the most erotic experience of your life. Perhaps at the end, we’ll make love. That will be entirely your choice. But you’ll always know the excitement of this adventure. And it will change you. I hope you will take a chance. On yourself. If you wish to begin, dress in all white on Monday.”

The letter was unsigned. Was this a joke? I’m not a risk taker and I lead a conventional life. In truth, while I am happily married, the sizzle had gone out of my sex life with Sebastian. Our love making was the same predictable process. Some foreplay, he grabs my backside, enters me, and within 30 or 40 seconds, he ejaculates. He mumbles some words of satisfaction and rolls over. Not storybook material. In my husband’s defense, he could make complaints about me. I don’t participate much in our love making, don’t make suggestions, and am not assertive. There was a time when he tried to get me more engaged sexually, but I was raised that that’s not how women should behave. I know that’s old-fashioned thought, and I should do better. I guess we’re both stuck.

Does that justify playing erotic games with a stranger? No way; I’d have to be mad. But is this person a stranger? Clearly, we’ve met. At my work? Maybe he’s someone from the gym I belong to. Or that creepy cashier at the supermarket who always seems to look at my breasts. If it were him, that would gross me out. But maybe it’s the cute guy at the gym who rides the exercise bicycle the same time I do and is always smiling at me. He’d be acceptable.

Wait, what am I saying? Cheat on Sebastian? Never. But the letter didn’t propose cheating — or at least it was just an option. A few erotic games isn’t being unfaithful. Is it? I was in a quandary. Tempted but afraid. I’d need to sleep on this.

And then the second letter arrived the next day.

“Dear Claudia:

I’m sure my letter yesterday was a shock. It was meant to be. I want you wondering who I am, what you would do, where this would lead. All great adventures begin with the first step. Don’t disappoint me. Most of all, don’t disappoint yourself. A world of pleasure awaits you. Be brave. Dress in white on Monday.”

The weekend dragged on forever. Then it was Monday. I stood in the walk-in closet for a long time. Then I dressed and went to work. Happily, it was a bright Summer’s day, so my white slacks and white blouse fit in perfectly.

I was like an Indian scout all day, eyes alert and scrutinizing every person I came into contact with for the slightest sign of something out of place. I did all my normal activities. To the gym after work; buying a few groceries at the store. No one looked twice at me. Maybe this was a prank. I began to feel foolish.

Until the next letter arrived.

“Dear Claudia,

Thank you. Seeing you in those lovely white slacks caused my heart to skip a beat. You’ve earned the first adventure. There will be five in all. You are to go without underwear tomorrow. No bra, no panties. The entire day. Note who notices, who does not. And how differently you feel. I’ll be watching.”

Now, I never go without underwear. And I need a bra. I’m well proportioned, but big enough that I need the support. My breasts bounce around inside a shirt without one. Would I have the nerve to do what this stranger tells me to do?

I did it. Sort of. I skipped the underwear, but wore an outfit with a skirt, a blouse and a jacket. The jacket mostly concealed my top. But as the day wore on, I felt guilty. I wondered what my secret admirer would think when he saw me, as I knew he would. Would he say that I cheated? That’s how I felt. I took off the jacket. The blouse beneath stretched snugly over my breasts. The nipples were prominent and obvious. No one could see that I lacked panties (unless I did a “Basic Instinct” move), but knowing that I was naked beneath the skirt electrified me. A few people at work clearly noticed my breasts, although no one said a word. I was so nervous, so excited by my overt sexuality, that I could hardly focus. After work, when I went to the gym, I couldn’t avoid a sports bra (I’d be naked otherwise) but there were no panties beneath those form fitting stretch pants. My vagina strained against the fabric. The dreaded camel toe look was there for all to see. What would people think? I worked out in a sweat, and not from the heat.

When I got home, Sebastian noticed that I didn’t have a bra.

“That’s a new look for you,” he said. “I don’t think I’ve ever seen you go to work without a bra.”

“Well,” I improvised, “I got an insect bite on my left breast, and the bra irritated it, so I went without.”

“I like the look,” he said with a smile.

I did too, but I didn’t say it. Then Sebastian came over and kissed me, and caressed my breasts through the blouse. He hadn’t done that outside of bed for years. It was nice.

Another letter arrived a few days later.

“Dear Claudia:

Congratulations on completing your first dare. I got a glimpse of you and you looked spectacular. I hope you felt the same. Your second challenge will be easy; you just have to enjoy it. I’ve arranged for you to get a full body massage at the Pampered Woman studio in town. It’s prepaid; call and ask for Marcel. I won’t be able to observe you this time, so I’ll need you to tell me how it went. I include an email address at the end; it’s a proxy which will forward your message to my actual email address. I’m not ready to reveal my true identify yet.”

Marcel is a French name. Of a man. I’ve had a massage before, when Sebastian and I went on a cruise, but the masseuse was a woman. I could see where this was headed, and I was not comfortable with it. I’ve never been naked with a man not my lover, especially one who is going to run his hands all over me. Would he touch my breasts, my groin?

I was frozen. Maybe this had gone too far. Why am I doing what a stranger tells me to do? Enough. I did not call.

The next letter arrived at the end of week.

“Dear Claudia:

I am disappointed that you have not booked your appointment with Marcel. I suspect you are worried that I’m going to entrap you in some orgy. Let me assure you that Marcel is a professional. He will not violate your privacy. It is a full body massage, but you’ll be in control. If you ever want out, Marcel will terminate the massage immediately. Don’t disappoint me. Make the appointment.”

Damn this guy. He won’t take no for an answer. I booked the appointment.

I snuck out from work early to get the massage. The studio was clean and modern and very professional looking. That eased my nerves somewhat. The receptionist directed me to one of the rooms and instructed “Hang your clothes on the hooks provided in the dressing area. Put on one of the robes. Marcel will come in shortly.”

I went into the dressing section and began to hang up my clothes. I removed the bra. I thought about leaving the panties on, but that would look silly. And I’m sure this masseur has seen hundreds of bodies before, better looking than mine. But I was nervous as a cat. I wrapped the thin robe around me like a coat of armor. A nice thought. Which would not last long.

Marcel came in, introduced himself and asked a few basic questions about my history of getting massages (once), if I had any specific ailments (none); any special areas of the body he should work on (no, although I thought of saying, “don’t touch me.”) Then he asked me to remove the robe and lie face down on the table.

A brief moment of panic. How had I so easily been talked into stripping naked before a stranger? What was I doing? I stripped off the robe and crawled naked onto the table.

He poured some warm rubbing oil onto his hands and began to massage my back. He immediately noticed how tense I was, the shoulder and back muscles rigid.

“You need to relax. I’ll put some music on.”

He went to a machine and soft music began to play. I willed myself to relax, and his hands swirled over my back, down to the base of the spine, over the buttocks, down the outer side of the legs, to my feet. It was very pleasant, soothing. Then he moved my legs slightly apart so he had access to the inner leg and thighs. I knew he could see my sex. I began to tremble slightly. He did not touch the vagina, but he rubbed near it. I trembled some more.

“Are you nervous?”, he asked me.

“No,” I lied. “My skin is sensitive.”

“You’ll get used to it,” he said.

I lay there and absorbed the soothing feel of his firm hands, the warm oil, the soft music playing. I stopped trembling. I was getting used to this, as he said. It was admittedly a little erotic and very pleasant.

Then he asked me to turn over, onto my back.

On one level I certainly knew this was coming. But on another level, I was shocked. The soft eroticism of a back rub was about to be ended. Rolling over onto my back would be surrendering myself to this man. I didn’t move. It probably wasn’t long — 10 seconds? 15 seconds? But every second that I did not move was like an hour. I had to decide. Now.

I rolled over. I looked into his face. He was placid, undisturbed. I tried to hide what I was sure was a terrified look on my face, closing my eyes to make this all go away.

He covered my groin with a small towel. What a lovely gesture of modesty. That wouldn’t fool anybody. Then he began to rub the warm oil onto my shoulders and neck. And then circled the breasts.

“So how did you decide to get a massage today, when you’ve only had one in your life?” he asked.

Was he going to make conversation while I lay naked before him, him groping my breasts?

“A friend arranged this for me, as a gift,” I answered.

“That’s very thoughtful. It must be a good friend,” he said.

I didn’t answer. I couldn’t say, “No, it’s a stranger,” that would have been weird.

“Your body is muscular. You must work out,” he continued.

His hands were running down my sides, heading toward my middle.

“I do work out regularly. And I’m a runner,” I said, justifying my toned body.

“Yes,” his head nodded, “I feel the firmness in the thighs.”

His hands were on my thighs, rubbing the front, then kneading the muscles on the inside of the thigh. I couldn’t see, lying on my back, but I knew that tiny towel over my groin had moved. He had to be staring at my vagina. His hands moved closer to that sensitive spot. I gasped.

“Are you okay?”, he asked. “Am I hurting you?”

What was the answer to that question? I was trembling inside, my sex was throbbing. I wanted his hands to stroke me, to bring me to the orgasm that was waiting to be released.

“No, you’re doing fine,” was all I could say.

The massage continued. It was very pleasant. He never “violated” me, never was inappropriate. But his firm fingers had brought me to a fevered pitch. I was spent when he finally finished.

I thanked him, dressed, and gave him a tip.

Now I had to compose an email to my secret admirer.

“Thank you for that wonderful treat. It made me tremble with more excitement than I’ve felt in a long time. You are releasing feelings in me that have lain dormant. Who are you, what’s your name? Why are you doing this? Claudia.”

Now that we had email contact, the next reply came quickly via email.

“My name? You can call me Ishmael. [My friend had a sense of humor. I got the joke; named after a large dick.] I am taking you on an erotic adventure which neither of us knows where it will lead. I hope it ends with you in my arms. But your journey isn’t over yet. You have the third dare ahead of you. You are to sunbathe topless in your backyard. On your back. Tell me when you’ve completed it.”

This was a new level. The first two dares had essentially been limited. Now I was going public. My backyard has a small pool, and I’ve sunbathed there before. But the area can be seen by houses to the side and in back. I’ve always worn a bathing suit. It hadn’t occurred to me, but might my admirer be one of my neighbors? Would he be watching? I didn’t know if I could do this. There would be no going back after public nakedness.

I did nothing for a few days. It was cloudy, anyway. But on Sunday, the sun shone warmly and brightly. I cursed the sun. Sebastian was running errands, which I was glad of. I should have an hour to get this done before he returned.

I was nervous as a cat. I surveyed our surroundings carefully. I couldn’t see any neighbors out on their decks or at their windows, although obviously that could change in an instant. I lay down on the chaise lounge and nervously unhooked my bathing suit top. I lay down on my back, closed my eyes, let the sun warm me while I tried to still the silent terror running inside me. My breathing was heavy, the anticipation of discovery ever present. But with time, I relaxed. It felt good for the breasts to be free, to feel the breeze, to feel the sun.

I was startled into reality when I heard the wolf whistle, clearly directed a me, a predator signaling his sexual approval. I sprang upright on the chaise, searching for which of my neighbors had discovered me. But it was Sebastian, with an approving but questioning look on his face.

“What’s gotten into you Claudia? I’ve never seen you sunbathe topless,” he asked.

“You startled me,” I covered my breasts with my arms. “I wanted to get an even tan. I’m sorry, I know I shouldn’t be doing this.”

“I not criticizing you,” he said kindly. “You know I love to look at your body. I’m just not used to everyone else being able to, too.”

“Yes,” I stammered, as I fled inside to cover myself. That God damn Ishmael. I wished the whale had swallowed him.

But after collecting myself, I calmed. It had been an enjoyable and arousing experience. If Sebastian had not come home, I could have stayed out there longer. I was turning into an exhibitionist.

“Dear Ishmael,” I typed. “So I did it. Half frightened me to death, but in the end, it was okay. How am I doing?”

Ishmael didn’t reply until later that night.

“I am very proud of you. You are doing great. I wish I could have been there with you. Maybe someday soon? In any event, it’s time for your fourth challenge. I want you to describe a sexual fantasy that you would love to experience. Be explicit about what erotic desires, yet unfulfilled, lie within you. No one but you and I will ever see what you write.”

Oh my God. What am I getting into? And do I even have a sexual fantasy? I’ve never done anything scandalous, just normal sex with my few boyfriends and then Sebastian. What do I want? I know there has to be more than the missionary position, our default. But what?

I pondered this question for hours. I remember seeing a movie once, in which a pirate has captured a lady. He ties her to a pole on the ship, and with his knife, carefully cuts away her clothes. She is stripped slowly, her blouse shredded, then her camisole cut as the breasts spill out, then her skirt falls away. She is nude except for her panties. The pirate massages her groin, as she groans with terror mixed with pleasure. Finally the panties are cut and she is naked. He removes his clothes and moves toward her. The movie didn’t show actual intercourse, but suggested enough. I remember how excited it made me. I have no desire to be raped, but a handsome stranger firmly taking me, that would be exciting.

So I wrote. “Dear Ishmael. I would love to role play that I am a lady, captured by a handsome and muscular pirate. With me helpless, he will forcibly remove my clothes. He’ll run his hands all over my body, inflaming the clitoris, probing into the vagina, finding the G spot, igniting passion within me. I’ll respond to this unexpected pleasure, and insist on kissing his body, cupping his testicles and penis. Using my tongue, I’ll excite him to full length. Then he’ll make me knell on all fours, while he enters me from behind, fondling my breasts. He’ll collapse on me, and we’ll embrace and make love the night long, with me on top, with him aside me, with different positions until we’re exhausted. I will wear him out with my passion.

So there you have it Ishmael. The hidden me, lustful, adventurous, taken by a handsome stranger. A fantasy fit for a romance novel, but alas, not for real life. Pirates are few and far between nowadays.”

It took a day for the reply.

“Dear Claudia. That was a wonderful fantasy. You have done great with my four challenges. Now it’s time for the fifth and final one. You are to realize that fantasy within the next 7 days. It’s up to you to find the person to do it with. It can be with someone you know, with a stranger, or even your devoted admirer, me. That decision is yours. But you must act out that fantasy. Let me know who the lucky man is and what happens.”

This was the most dangerous challenge. Not only must I find someone to be physically naked with, but I’d be emotionally naked too, exposing my inner lustful self. Of course, Ishmael was the obvious candidate. He knew me — but I didn’t know him. What if he were physically unattractive? Should I ask first him for a photo? And what if it were that creep at the grocery store? And what about Sebastian, whom I love? If he ever found find out, would he leave me? Would I trade a night of passion for my marriage?

Ishmael had left me with a dilemma — but I was determined to go forward. His series of adventures had awakened my passionate side. I would not settle for Sebastian’s missionary-position, monotonous sex, anymore. I couldn’t very well advertise for someone on Craig’s List, so it had to be Ishmael.

But first I had to set some ground rules. Sebastian must never find out. And I had to find out more about Ishmael. I’m not a reckless person.

“Dear Ishmael. I owe you a debt for awakening my sexual side, and showing me what I want. I am tempted by your offer to fulfill my fantasy but who and what you are is a mystery to me. IF we were to do this, it would be a one-time affair. My husband must never know. I love Sebastian completely. I will never leave him. And I will never cheat on him by offering my love to another — even if I offer my body to you. We do this once and then go our separate ways. Can you agree to this? If yes, then it’s time for the blindfold to be removed. Who are you? Can we meet for coffee at a public café? Claudia.”

I sent the email. And waited. And waited. There was no reply. Three days went by and only silence. Had I offended him? Was he so infatuated with me that my offer of a one-time affair was unacceptable?

On my end, I had accepted the idea that I’d fulfill my fantasy within the 7 days Ishmael had decreed. I wanted it. I was angry with Ishmael that he was so rude as to apparently reject my offer.

“Ishmael. What is wrong? Is it not enough that I’ve offered by body to you? Are you not going to reply to me? If you are not going to be my “pirate”, I will find someone else.”

Still no response. Screw him. I would find someone else. But my only option really was Sebastian. I’d have to recruit him into my fantasy. On the 6^th day, after dinner, I went to sit by Sebastian on the couch. He was watching TV.