Comfort Zone

I'd had no idea that night was going to turn out so well. It started off being incredibly awkward. I was so far outside my comfort zone that I didn't know what to do with myself. But perhaps that's why it turned out the way it did . . .

Let me start from the beginning. Back then I was newly separated. My wife of six years had cheated on me, and I'd moved her out. That was the first big change. I was normally meek. When I was younger, I had been in a similar situation, and had stayed with my unfaithful girlfriend for a much longer period than was reasonable. I promised I would never let myself get into that kind of situation again. To my and my wife's surprise, I managed to keep that promise. So, for the first time since I was eighteen, I found myself outside a relationship. We had not gone through divorce proceedings yet, but were officially separated with no hope of reconciliation.

I had resolved myself to loneliness. Don't get me wrong—I'm not a bad-looking guy, and thirty is not so terribly old (even though sometimes it sure felt like it), but I had no hope of finding anyone new. Between my acknowledged meekness and my unfamiliarity with the dating scene, it felt impossible. My love life seemed to forever be limited to porn, fantasy and masturbation.

This got old fast, however. I never thought I'd say this, being an avid fan of self-pleasure, but there came a point where I chose not to bother anymore. It was less frustrating to just go to sleep rather than try to fulfill my own needs.

It's a sad truth that those things we cannot have are those things we obsess most over. So it became that rather than enjoy my hard-earned bachelorhood, I spent most of my time depressed and brooding over the fact that I had no one—no prospects, no hopes . . . not even a friend with benefits. No one to touch and to touch me back. Girlfriends, wives . . . they just weren't worth it. I tried to convince myself of this. My track record wasn't great. Better to find distraction and stop being moody about it.

Still, no matter how hard I tried, I couldn't stop wanting those things I couldn't have. I would drink too much and stay up late daydreaming, lusting. At a couple of points, I even broke out the carefully-stashed sex tapes my wife and I had made. It disgusted me that I could still be aroused by her, even after all she had put me through, but I couldn't deny that she was the best I'd ever had.

One such night was when I resolved to change this. Emboldened by alcohol and spurred on by my own self-loathing, I sat myself in front of my computer and started joining dating sites. This was another thing I never thought I'd do. I even posted a photo of myself along with my hastily-typed profiles. I had no hope these profile would lead to anything, but I had to try something—anything.

Before giving up and turning in for the night, I commented on a few profiles, choosing women who lived close by and seemed interesting. Over the next week I checked the sites off and on, not expecting anything. I had a couple of brief conversations that went nowhere, but nothing else. I was about to delete my profiles and sink deeper into depression when I finally got an interesting response.

It was from a young woman named Janice. Too young, I thought at first. She was barely nineteen. But she had found me, she it wasn't as if I'd been creeping on the profiles of young women like an old pervert. Her messages showed intelligence and humor. The two of us quickly became friends, moving from the site's messages to actual e-mails, and then instant messaging. Soon after that she was calling me. Our conversations, which had become frequent, were light and not too filled with substance. It seemed as though we were forging an easy friendship rather than wooing each other. This was fine by me. I had found the distraction I'd been looking for.

However, distraction wasn't enough for her. Soon after we'd moved exclusively to phone conversations, she'd begun asking when we could meet in person. I was a bit nervous about this, partially because there were no photos on her profile, and every time I asked her for one, she changed the subject. Plus, I was not used to playing host. I always had trouble with new people and situations. As I mentioned earlier, I'd been in relationships for all of my adult life. As it seemed important to her, I reluctantly agreed. (Also I'd run out of excuses.) Seemingly feeling safe enough to be alone with me, she got my address and the next night I found myself answering the door to an enchanting sight.

Janice was short and curvy. Not slim, but not fat. Her curves were in all the right places. She was pale with creamy, smooth skin and a smattering of light freckles. Her hair was long and as black as her wispy skirt and low-cut button-down blouse. Her makeup was well-done and understated, accentuating her big brown eyes and full lips.

As I looked her over, I realized she was doing the same with me. After taking in the sight of her, the awkwardness that would be present for the start of the evening set in. We were too close for a handshake, and not close enough for a hug, so I stammered a greeting and gestured for her to come in. She slipped off her sneakers and followed me into the living room, where I spent most of my waking time. (I had taken to sleeping on the couch after moving my wife out. I didn't want to sleep in the bed she had misused.) She was clearly as nervous as I was—after our initial up and down looks, we had trouble looking at each other for a time.

We exchanged pleasantries. I hadn't thought to get a selection of alcohol, which would have done wonders to loosen us up, but she accepted a beer. I figured it was just for something to occupy her hands, as she'd mentioned in an earlier conversation that she didn't like beer. She sipped at it, as I did with my own bottle. We chatted, went through two bottles each, testing the waters. I sat on my big worn couch, and she sat cross-legged on the floor across from me.

After a terribly long time of stammered and faltering conversation, I found myself chuckling at how silly we were being.

"What's so funny?" she asked, arching an eyebrow.

"We are," I said, lightly, taking a swig of my beer. "We talk over the phone and on-line as though we've been friends for years, but once we get in the same room as each other, we're jittery teenagers."

When I put it that way, she had to laugh too. She finally managed to meet my eye. A darling mischievous look took over her face as she said, "I technically AM still a teenager, you know . . . "

"Don't remind me," I said, groaning. I downed the rest of my drink and smirked at her.

"What's wrong?" she asked, a mocking edge to her voice as she got up and sat next to me on the couch. "Feeling like a creepy old man when I'm around?" She elbowed me in the ribs.

"Kinda, yeah, " I admitted, setting my bottle on the floor and half turning to her.

"Well, maybe I like creepy old men," she suggested. "You think of that? Maybe that's why I'm here?"

There it was—the topic had been broached, albeit in a joking way. But since it was out there, it spurred me on. "Is it? Why, I mean. Look at you—you could be with anyone right now, but you're wasting your evening with me." I didn't say it with pity intended, regardless of how it sounded. I was still smirking.

"Don't be silly," she said, blushing a little. "I like you. I've been looking forward to meeting you for weeks now."

"Same here," I admitted. "But I do have a question. Why didn't you let me see a photo of you?"

She looked down at her hands, flushing. Just when I thought she wasn't going to answer, she said, "Eh, I'm nothing special."

I was quick to contradict her. I let her know how attractive I found her, that I never expected to find someone so beautiful on a dating site. This led into a talk about our histories. It turned out she had created her dating profile after breaking up with her boyfriend. The relationship had left her with some self-image issues. He'd been the one to take her virginity, about three months prior, and not long after she'd dropped him. The sex was spectacularly awful, and after she'd finally relented to his advances, that was all he wanted. They had only done it a couple times and there had been no variety to it, no foreplay, nothing. Nothing he'd done had excited her, which made her wonder about herself. But, after ridding herself of him, she'd started wondering if the problem was him. Maybe what she needed was an older, more experienced man.

She was really red by this point, and hastily added that she didn't really have ulterior motives, and had actually connected with me. Once she realized she was babbling, she trailed off. My heart pounding in my chest, I looked at her as she stared down at the floor, blushing furiously, and knew I had to go for it. There wouldn't be another chance like this. With my finger crooked under her chin, I tipped her face up until she was looking at me. Her eyes were quivering, as though itching to look away, but I held her in my gaze. Not knowing what I was saying, I told her, "It's okay. You don't have to make excuses. We both want . . . need experiences, so I think we should just take them. Do you agree?"

She didn't respond, just kept looking, her eyes quivering, lips shaking.

Surprised by how firm my voice sounded and how quickly I'd pushed away my nerves, I insisted, "You have to say yes or no, Janice."

So softly that it was almost a breath, she said, "Yes."

That was all the encouragement I needed. I drew her to me and our lips met in a kiss. Her lips were hot, but soft, her mouth dry. She started shaking, so I held her upper arms in my hands, steadying her, letting the kiss become more insistent, frantic. She started kissing me back, hesitantly at first, but with rising eagerness.

As for me, I was lost in the moment. Not realizing it, my left hand had gotten tangled in her hair, my right was somehow clutching her breast through her blouse. Small, but round and firm, it felt amazing . . . but I needed more. Her hands were in her lap, and her eyes were squeezed shut. Her breathing was coming fast and shallow. My fingers moved deftly from button to button until her blouse was open. Without pausing, my hands travelled around her back and released the clasps on her bra. Now that there was some slack, I was able to snake my hands under her bra to touch her breasts skin on skin. Just as I'd expected—this was much better. The sudden feel of my hands cupping her drew a gasp from her, finally breaking the kiss. Her eyelids fluttered and she looked at me from half-lidded eyes, as though just coming out of a trance. (Which, I suppose she was.)

I removed her blouse and bra, meeting some half-hearted resistance. (I later learned that she had never been comfortable being fully naked.) Once the way was clear for me, I lay light kisses down her neck, pausing halfway down to nip her lightly. I nipped again when I got to the crook of her shoulder, and kept my way steadily down until I reached her right breast. While kneading the other, I attacked this one with my mouth and tongue, reveling in the gasps and soft moans I was drawing from her. I moved to the left breast, not wanting to leave it out. She arched her back, giving me easier access.

While doing this, my free hand roamed over her leg, pushing her skirt up. I relished the feel of her smooth, soft thighs. My hand continued on its path until it gripped a naked buttock. Surprised, I felt around with my fingers, locating the thin band of a thong. My wife had not been into sexy underwear . . . or skirts or makeup for that matter. To my regret, I had married a tomboy.

There were so many differences about this experience, and I had only ever been with two women before this, so of course I was incredibly aroused. Knowing her inexperience helped me hold myself back. I didn't want to rush due to that, and also because I wanted to make this last as long as possible. I was a little surprised that she hadn't touched me yet, so I lifted my mouth to her ear, noting her shudder as my slight breath touched her sensitive skin. "Touch me . . . " I said, simply. It was somewhere closer to a demand than a plea, and she responded instantly.

Her hands started exploring my body, even as mine continued over hers. She ran her fingers down the side of my face to my neck and down to my biceps. She felt my arms and moved on to my chest, but feeling my shirt blocking the way, she desperately tried to tug it off me. Smiling, I helped her along. Once my shirt was gone, she felt along my bare chest, running her fingers through the tangled, soft hair. She ran her hands down my back, lightly dragging her nails across my skin. I may not be hugely muscled like some guys, but I take care of myself—I was lean and firm. Her hands showed her appreciation.

One hand went down to my flat belly, fingers stroking lightly over the front of my jeans. She started to pull her hand back, an uncertain look on her face, but I wrapped my own hand around hers and led her back to my crotch gently. With my hand holding hers, she seemed to find more courage, and her small hand clamped down, tracing the rigid outline of my erection through the denim.

Now, I hadn't been idle this whole time. My free hand had returned to her thigh, kneading, drifting . . . once she clutched onto me, my hand took that moment to dive between her legs, firmly clutching onto her lace-enclosed mound. She gasped loudly. To this day I'm not sure if her gasp was from what I was doing or what she was, or a combination of both.

"Mmm," she murmured, her widened eyes drifting back to closed. My hand released hers and moved to unbuttoning and unzipping my jeans, as I continued to press and work my fingers under the hem of her panties. Once the path to my cock was free, I again guided her hand, this time through the opening in the front of my shorts. The feeling of her warm, soft fingers curling around my shaft was amazing, and I let out a little moan, which seemed to encourage her. She began moving her hand along my length, softly, but steadily.

Slowly I ran my finger along the slit of her pussy, reveling in the warmth and wetness. With excruciating slowness, I worked my finger inside. It was amazingly tight . . . I couldn't get much inside at first. Still, she moaned softly at the feel of it. My finger drifted in and out a couple of times and then curled up, easily finding her small, hard clit. My finger danced over it, touching lightly, testing, then with increasing pressure. It had the expected effect—her breathing became a pant, her fingers tightened on my erection, and her moans became steady, rhythmic.

I let my fingers move back to her opening, pleasantly surprised to find the entry was easier due to the increased lubrication, my index finger snaked further in and rotated as my thumb met her clitoris and began massaging it. "Nnngh," she moaned, her free hand clutching my arm, her eyes rolling back before again being hidden by her lids. I quickly found a rhythm and went with it, feeling her body tighten against me. Her moans and breathing became wilder, and yet she still clung to me with both hands, one above and one below, as though riding me towards her fast approaching climax. Suddenly she bucked against me and cried out, her guttural sounds becoming almost a howl of pleasure as her orgasm raged through her. Her cunt pulsated and throbbed against my hand, drenching it in her fluids. My hand stopped moving, but I left it where it was as her shudders stopped and her moans trailed off. She was breathing fast, sighing as she came down from her peak.

I pulled my hand away and her eyelids fluttered open. She gazed at me dreamily for a moment before her lips curled into a smile, a hungry look coming over her face. She scooted back on the couch, pulling down my jeans and shorts with my help, and practically pounced on my cock, which was as hard as it's ever been. She started with sweet licks from the bottom of my shaft up to the head and with no warning, my cock vanished into her warm, sweet mouth. Inside the confines of her mouth, her tongue cradled me, slipping up and down. She sucked, then released, looking up at me, as though seeking direction. I let my eyes close and moaned lightly as encouragement. I could tell she hadn't much experience in this, but the sensations were divine, and ones I'd never thought I'd have the pleasure of experiencing again.

She sped up her movements and gagged a bit, not able to take all of me in. I leaned forward and took her hand, leading it to the base of my cock. This seemed to help her, and she was able to bob her head with more of a steady rhythm. It wasn't too long before I felt my orgasm building up. Before I got to the point of no return, I pressed back on her shoulders, which caused her to lose grip on me. I came out of her mouth with an audible popping sound.

She looked up at me with a mix of disappointment and confusion. "No good?" she asked, sounding shaky.

"No," I disagreed, my voice thick with desire. "That was amazing. I'm just not ready to come yet."

She smiled, letting out a relieved breath. "Good. I was hoping I was doing that right."

"Oh, you were," I assured her. I stood and helped her up, turning her away from me. I ran my fingers down her back and to the top of her skirt, unbuttoning it. I let it fall and she tried to grab at it, but wasn't fast enough. While she was distracted, I pulled her silky thong down in a smooth sweeping motion, letting it also fall to her ankles. She slowly stepped out of it and I turned her back to me, letting my eyes drink her in, now that she was completely nude. She was blushing again, looking away and biting her lip. One hand was draped over her breasts, the other cupping her crotch. I move her hands away to get a better view, and she let them fall to her sides. She was shaking and murmured, "Can we . . . turn off the lights?" Smiling, I nodded and crossed to the light switch on the wall, stepping out of my jeans and shorts as I went. I flicked the light off, but left the lamp on the other side of the room glowing, so I could still see her. In the relative darkness, she seemed to relax a bit.

I crossed back to her and took her in my arms, loving the feel of skin on skin with nothing getting in the way. Because of the height difference, my cock was pinned between us, pressing against her belly, still throbbing and aching for release.

We kissed again, vigorous and insistent, and I lay her back on the couch, her head lying on the overstuffed arm rest. My lips moved back down her neck, shoulder and back to her breasts, kissing the fleshy undersides, my tongue travelling over the goose pimples on her puffy areola. Her nipples were still rigid, and I took one into my mouth, biting down on it lightly, which made her gasp. Her moans were increasing and I wondered idly if I could bring her to orgasm just by playing with her tits. I was too impatient to try at the moment. I continued my explorations downward, laying kisses on her soft belly, onto her rounded hip, and down to one thigh. Then I moved inward, pressing my lips against her mound, breathing in her musk.

I pulled her legs apart, meeting more resistance. She grabbed my face and drew me up and away, her lips meeting mine in a kiss. I wouldn't be distracted so easily, however, so I soon broke the kiss and made my way back down to where I had been. She tried to pull me away again and my tongue shot out, licking directly on her clit. Her hands fluttered uselessly against my face and she moaned, surprised by the sudden sensation. I looked up at her and made as though I was about to move away, when to my delights, her hands moved to the top of my head, and, looking away, she pressed my face back down.

Permission thus given, I dove back into her folds, excavating with my tongue, tasting her sweet juices. My tongue dipped inside her and she gave a humming moan, fingers tangling in my hair, thighs pressed against my cheeks. She was as tight a fit for my tongue as she had been for my finger, and I made a mental note to go slow once I finally got inside her. Slowly and indulgently, I got to know her with my mouth and tongue, licking up and down, in and out, rolling her clit around and sucking it into my mouth, pressing and releasing. With seemingly no build up, she exploded against my face, her moans becoming gasping cries of delight, her belly rising and falling, the walls of her cunt contracting against my tongue, which I'd again plunged inside her. Her legs clamped against my face like a vice and her fingers pulled at my hair in a lovely, painful way. After what seemed like several minutes she came back to herself and released me, still gasping.