Bold, Once

I had to be courageous once. Just once in my life I had to step out on the ledge and take the risk of stepping slightly too far, and allowing myself to take a risk. It wasn't an overwhelming risk, but it was way out of character for me. Someone told me a long time ago that the reason so many opportunities had passed me by was that I could see a dozen bad results for every potential good one in anything that came my way. And that was certainly true when it came to sex.

Dating, dining, dancing, socializing, and all of that happy part of sharing with a woman were things I'd done, and in retrospect there were probably a dozen or more times when if I had simply asked, or shown some initiative, the result would have been sex beyond my imagination, with many the subject of rather x-rated fantasies. There were a couple of shocks along the way, to be sure. Barbara, who invited me over for dinner, shooed her daughter off to bed, and then more or less ripped my clothes off while we sat in the living room. I learned much later, and thankfully not the hard way, that she was searching for another husband, and refused to have "protected" sex in the hopes of landing one the shotgun way. Perhaps because I was so timid with all those others, I was spared this fate. Louise, who oddly enough had been in the same quest, had the most unresponsive nipples I'd ever been close to, and had learned that the best way to give oral sex to a man was to simulate him having his cock pushed through a cheese grater. Tina, a wildly charged dynamo, who had a clit the size of a peanut M&M, and gave me oral sex in my car. Sandra, who seemed an interesting sort, came to my home, listened to some music, and bluntly asked if I wanted to fuck. Yes, there had been some encounters. All of them in their own way good, but none of them involved me being assertive, seeking and getting.

A classic example, and the subject of this story, was Rit. One of those bright, entertaining, intelligent women who just naturally became my friend, rather than something more. Although Rit was both beautiful, and un-ashamedly blunt about her sexuality, it seemed she had a quite narrow monogamous perspective. She didn't experiment with other partners much, and while she did have a very serious relationship which cost me a lot of sleep, when the guy turned out to be less than loyal, and I talked with her until she fell asleep or he came home, she had placed me - or so it seemed - in that category of "Friends" but nothing more. And I had to respect that. At one point in our lives she was very upset by the comments she began receiving from various men in the social circle we were in, some of them as vulgar as it gets, I had assured her that of all the men in that crowd, I was the one whom she could count on to never have to tell "No" more than once.

So, the world turns, and turns, and I found myself taking her out one night, when she was between relationships. We had a wonderful dinner, and went out dancing. An excellent evening, and when we got to her house, she didn't hesitate to invite me inside. I sat on the couch, while she excused herself to go "freshen up." Wow, I thought, maybe this is the one opportunity to share some wonderful sensuality with this incredible woman. So, I listened to some music for a few minutes, and had a glass of water, when it seemed she'd been gone a long while. Thinking it was her waiting for me to seek her out, I cautiously went looking, and upon stepping into her bedroom, saw her passed out on the bed. I don't mean sleeping lightly, I mean passed out. Most men would have been upset, or enraged, or perhaps worse, I just smiled, tucked her under the covers, and left, locking the door when I did. She called the next morning in abject apologetic mode, and said she just couldn't believe she had done that to me. It was a source of laughter, and a wistful memory for me, for a very long time.

Rit and I remained friends, and several years down the road found ourselves on the phone discussing sex, and the conversation turned downright steamy. She described the things she liked, and didn't, and talked of the good and bad partners, and I did likewise. I noticed a bit of a catch in her voice when I told her something I had always found highly erotic was watching a woman masturbate. And on this day, hearing that sound in her voice, and knowing that it was a HUGE risk to our friendship, I took a step I had never taken with anyone. I asked her directly for what I wanted.

"Rit," I started, "I want to ask you something, and if you say no, I'll never talk about it again. I'd like to ask if you'd watch me masturbate, and allow me to watch you do the same." It was out there now, and in that old phrase you can't unring a bell. I'd just taken a step that could have thrown ten years of friendship right in the trash. She didn't say anything for a long while, but she hadn't hung up the phone either.

After a bit, I had to ask "Was that too far?", and hoping it wasn't. She cleared her throat, and said, in a rather soft voice, "Bring whatever you need with you, and come over here at 3:00 pm today.", and hung up. I was astounded, and energized, and scared, and delighted, and a thousand other emotions. So, I set about getting what I needed.

What I needed wasn't much. A small tube of hand cream, and a soft cloth, and that was that. I once again learned the agony of slowly creeping time as I checked my watch every five minutes, or so it seemed, until 2:30 when it was time to leave my place and drive to hers. I put the cream and cloth in a small box, and drove to her home. Parked in the driveway, sat for a second or two to calm my nerves, picked up the box, and exited the car, and walked to her front door, and rang the bell.

Just as I was about to ring it again, she opened it, sort of hiding behind the door, and told me to come inside. I did, turning to close the screen, and then shut the door and locked it behind me. I'd been to her place a number of times before, and the comfort of the familiar surroundings was a soothing feature of how nervous I felt.

She was dressed in a long dark nightgown, and was wearing three-inch heels. The nightgown wasn't transparent, but it didn't conceal much either. My first real chance to look at her body, and it was a joy. Her breasts weren't large, and had the effects of gravity that time and three kids will exact, but they were lovely, and drew my eyes. Looking lower I noticed she was natural, unshaven, and a bit thick. Although I'm fond of shaved women, it was so small a matter as to be irrelevant. Taking me by the hand she led me to her bedroom, and once there gave me a hug, and I could tell she was a bit nervous too. "How would you like to do this?", she asked.

It was a question I'd thought of the answer to for years. "I'd like you to sit right beside the bed in this straight back chair, and watch me. I'd be happy if you felt free to comment, or encourage, but I don't expect you to do anything other than watch. If you're even remotely uncomfortable, I want you to tell me, and we'll stop." She smiled, nodded, and pulled up a chair. "Why don't you get out of those clothes and lay down?", was all she said.

Now, a little bit of shyness, but I was so dialed into what was happening that it was not possible for it to get in the way. I removed my shoes, shirt, and socks, then undid my belt, and stepped out of my trousers. I took my briefs down, and stepped out of them, and turned to face her. "Go ahead and look, Rit, it's alright." She did, and the softest smile I've ever seen was on her face when she saw how erect I was. "Is that because of me?", she asked. I could only nod, and then I laid down on the bed. I opened the box, and took the soft cloth, actually a square I'd cut from an old t-shirt that functioned well as a dust rag, and laid it on my lower abdomen, to function as a cover for what was going to happen. Cautiously, I opened the skin cream, inhaled it's familiar scent, and expelled some on my hand. I glanced at Rit, and noticed was intently staring at my cock. It twitched in excitement, and I put my hands down to it, and started to massage the cream into it, in gentle strokes, up and down, and some swirls, teasing the head, stretching the skin tight, then loosening. Taking more cream I began to put more effort into the touch, and heard her whispers, "beautiful", and "it's so hard...", and "mmmmm...". Soft, non-judgmental, and encouraging, everything I hoped for.

I had reached down to tease my balls, and give them a caress, while never letting go of my cock. I just glanced at Rit, and noticed she was fidgety in her chair. Perhaps this was getting to her as it was for me. Inspired by her intent look, I began to seek that release in earnest. Rit's comments became more vocal, and more motivating. "That's right, David, stroke it hard. Show me how that cock works.", and the like. I must have telegraphed it with my breathing, as she looked up at my eyes, and began to exhort me, "Come for me, David, come hard. Show me the cream, come for me! Make that hard cock explode!" My had moved as fast as it could, which was normal for that point in masturbation, and I blurted out "Hold my balls Rit!", without missing a stroke. Like lightning her left had reached out, and I felt that gentle touch, and her bright red nails hold on to my balls. "Do I squeeze?", she asked, seeking to do what ever it would take for me to climax. I couldn't speak, I just shook my head and in an instant my body convulsed, and I shot an immense amount of cream over my chest, onto the cloth, and as the intensity of the orgasm was so strong, on up past it onto my skin. I sat there shaking in the afterglow, while she just stared in fascination at my climax. Starting to regain control of my breathing I looked over at her, and she met my eyes, and just said "Incredible!" As I recovered, she did some housekeeping, using the cloth to clean me off, and spent a few moments cleaning my cock, which had of course deflated. She never lost the smile on her face. Amazing.

I realized that I hadn't noticed she had something cold for me to drink right beside the bed. I took some sips, looked up, and took a deep relaxing breath. I looked at Rit, and saw that genuine smile, and returned it with one of my own. I couldn't help asking, "Was it ok?" Her smile said yes, and she kind of had that special look on her face when she said, "OK? It was beautiful! You were so consumed with those feelings, and your body was so tense it was amazing. And you came so hard, and so long!" Well. That put everything to that point in the light I had hoped for, no had dreamed of.

When I recovered completely I sat up, and she said, "Now it's my turn, I guess."

Moving slowly, I took the robe she offered me, and sat down on the chair. She was a little nervous, or so it seemed, and I wanted to make her feel at ease, so I said, "Rit, if you're not comfortable with this, we don't have to continue." For a moment I saw doubt in her eyes, and she blurted, "Don't you want to?" As confidently as I could I assured her that I very much wanted to, in fact I'd been dreaming of this for a very long time. Again, that smile. "So, sit still, and I'll show you how it is - for me." I wasn't going anywhere, short of a nuke strike.

Rit went the bathroom, for a moment, and when she came back, she had a couple of towels, a small basin of water, a razor, and some shaving soap. When I looked up, she just grinned, and said, "I want you to see everything." Oh my, I thought. She laid the towels on the bed, and soaped up her hands, and then applied that soapy substance to her pussy. For a moment I thought she'd forget to shave and just continue her caresses, but she had it under control. She reached for the razor, and with even, gentle strokes, she steadily changed from a natural pelt to a slick bare pussy. It couldn't have taken her more than five minutes, but I could have watched for hours. Cleaning off the razor, she then used the towels to remove the soap, and then set them aside. She reached to the bedstand and pumped some skin cream on her hand, and gently massaged it into her freshly shaven mound. When I caught her eye, she said, "Keeps the skin soft after the shock of the razor." I was too astounded at the display to speak, so I just nodded and continued to stare.

Having finished her ablutions, Rit, undid her nightgown completely and set it at the end of the bed. Curiously, she didn't take off her shoes, choosing for what ever reasons to keep them on. No matter, they looked incredibly sexy to me. She propped up a couple of thick pillows, reached in a drawer and removed a vibrator the size of a tiny flashlight, and opened her legs. Running her hands around her mound, and slowly touching the skin there, she began caressing her body, including the gentle tugging of her nipples. They hardened immediately, and were I her lover rather than an audience, I would have inhaled them on the spot. Her hands slowly began to draw smaller circles around her pussy, and eventually she reached the outer lips, and began to push them up, and down, alternating from the left to the right. The movement of her hips suggested an arousal, made obvioius when her caresses parted the lips and I could see the glistening nectar within. Her lips were delightfully puffy, and she began to tug and pull them opening her canyon, and closing, as her fingers teased over the hood of her clit. I was fairly sure she was aroused, but I was completely certain that I was.

After a few moments of this she began to run her fingers over her clit, along the sides, sliding it left and right, almost duplicating the motion earlier against her lips. In a moment, she used the fingers of her left hand and slid the hood back, and began to tease the top of her clit with one of the long red nails on her right hand. I notice her hips moving as she did, and her chest began to move faster with her breathing. Her thumbs began to alternate across the hood, and her hips were moving in earnest...and in a flash she reached for the little vibrator, turned it on and teased it against the opening to her pussy. She showed me the vibrator, holding it up to my eyes. It was glistening with that nectar. And with one gentle but firm movement she inserted the humming device into her ass and tucked it home.

Her body began to shake, and her hands were now a blur against her breasts, and her pussy. Gasping for air, she moaned, "Talk to me David, help me there."

I began to speak encouragement to her. "Show me how you come, Rit. Show me how your pussy comes. Give it to me, I want to see it. I want you to come for me. Come hard, Come now, Rit." And more of the same.

Without much warning her body convulsed violently, her knees came together and up to her chest, and she rolled to the side, as one of her hands gripped the bed with a force that any vise in the world would be jealous of. A long, erotically charged moan escaped from her lips, and the shudders continued to rack her body for almost a minute. When I started to pay attention to what I was seeing again, I noticed she was sobbing. Not hysterical, just sniffles, and sobs. Fearing the worst, for that is my nature, I asked, "Rit, are you alright?" It took her a moment, but she eventually said, "Yes, it's just that when I come that hard, I lose all control and sometimes I start sobbing from the feelings, they're so powerful."

Wow. Wow and a half. I just sat there stunned, and almost afraid of saying anything, fearing it would spoil the mood that was so special. Finally, I had to tell her, and I just said, "That was exquisite, Rit. I've never seen anything so beautiful in all my life." She rolled to look at me, and dragged me to sit beside her on the bed, and crawled into my arms, and just said, "Hold me, please." And, to my delight, she stayed there for more than an hour. It was one of the most incredible hours of my life.