Someday Is Now

[15 years ago]

Just a couple of seniors in high school talking. That's how the idea got planted in my head.

"Hey, Tim. What porn star would you bang if you had a chance?"

I paused to consider the question.

"Lisa Mynx."

"You know she's already 30 years old, right?"

"So what? She's still hot as hell. Who would you bang?"

"That teen sensation, Jamie Spark."

"Ah, teens don't know how to screw. Lisa knows a lot of tricks that would make it very pleasurable."

"Her bio says she's married."

"Since she's doing porn, obviously her husband don't care if she bangs other guys. And you did ask who I wanted to bang, not who I wanted to have a long-term relationship with."

"You are technically correct - the best kind of correct. Well, I gotta breeze. Catch you tomorrow."

[Present day]

I wouldn't say I spent every moment daydreaming about meeting (and banging) Lisa Mynx from that point on. But the thought did surface frequently in my head.

Time dragged on. I finished high school, finished college, got a job, had the occasional girlfriend. Now I myself was in my 30's. And my job was requiring me to move to a small town that was an exurb of an exurb of a big West Coast city. Well, nothing for it: I was between girlfriends, so there was nothing tying me to my current location.

I packed up and hired movers, and a week later, I was installed in my new lodgings. The apartment wasn't large, but it suited my needs.

I decided that on the first weekend I had, I would explore the town a bit. I ended up going for a walk in the city park and sitting on a bench. There wasn't a whole lot happening: the town was the definition of "quiet."

A woman who looked to be in her late 40's walked over to me and sat on the bench. "Howdy, new kid."

I stuck out my hand. "Tim Rogers."

She shook it. "Lainie Martin. What brings you to our little neck of the woods?"

"Work. I got transferred over this way."

"I'm retired. I made a good living and had the better lawyer when my ex-husband hit his mid-life crisis and decided he wanted a divorce. He was porking his half-his-age secretary and decided to set up house with the little tart. I don't hold a grudge - I got even right away when the judge made him hand over a large slug of money from his savings. He ran a highly successful business, presumably he still does. We don't talk - no reason to, no kids together or anything."

Lainie seemed nice. I decided I wanted to get to know her better. And not because she was wealthy: I made a very comfortable living myself, so I didn't need to find a sugar mama to support me.

"I've never been married. I've had the occasional girlfriend, but nothing ever seemed to work long-term. Guess I just never found the right one."

"Young women can be hard to deal with. It's easier to deal with older women: they don't play games."

Did that mean there was a spark of interest from Lainie, as well?

"Are you implying that you'd like me to ask you out on a date?"

"Not at all. I'm explicitly asking you out on one. Would you like to meet me at Jake's Cafe at 1 p.m. tomorrow for lunch?"

"Lainie, I'd love to."

I made sure I was freshly showered and wearing clean, casual clothes the next day, easily found Jake's Cafe, and was there 5 minutes early.

Lainie showed up 3 minutes later. "Hi, Tim. Glad you could make it."

"I'd like to spend time with you. Of course I was going to make it."

"You're young enough that what you really mean is that you want to spend time IN me. I'll let you do so eventually if you show yourself to be a good person."

I blushed. Lainie was quite attractive. Not "attractive for her age", attractive. Period. Trim, toned, decent chest, pretty face, salt-and-pepper hair (emphasis on the pepper), and a 500-watt smile.

"No, I definitely meant with you."

She teasingly punched me in the arm. "Your lying skills need a lot of work, Tim. I caught you eying me in the park yesterday while we were talking. But it's all right. I know I'm still very sexy, even if my ex was won over by the blonde bimbo doubling as his secretary."

She said it without a trace of venom. I was surprised how little she cared. I guessed that getting all that money from him in divorce court made the sting a lot less.

"What do you want to order?" I pulled out my wallet as I tried to divert the conversation.

She lightly slapped my hand downwards. "Put that thing away. I'll pay for my own lunch."

We purchased our sandwiches and drinks, and after we sat down and spent a couple of minutes filling our stomachs, I asked Lainie about her previous work experience.

"I was a programmer and systems designer for 10 years before the divorce. It only happened last year, you know. In fact, three days ago was the first anniversary of my freedom."

"I am duly in awe, Lainie."

"Don't be. Men do that job all the time, and it doesn't require physical strength that only males possess, so women can do it too."

"I'm a mid-level manager. That translates to disciplining employees who screw up and pushing paper, but it pays a lot. Probably because I have to negotiate office politics."

"Not bad, Tim," Lainie grinned.

I made a quick calculation. "What was your job before you hit your mid-30's?"

She blushed. "I don't talk about that part of my life. But it paid well and let me study programming and system design."

I decided it was better not to push.

"Where did you meet your ex-husband?"

"We were high school sweethearts. Got married right out of high school, he got a bank loan to start his company a year later and talked a venture capitalist into investing, and things just kinda took off from there. We were married for almost 30 years."

"Sorry he... split from you."

"Don't be. I'm doing quite fine on my own."

"I interned at the company I work for while I was in college, and they hired me right away and I've moved steadily up the ladder."

"You seem very sensible. I like people who are stable. No mid-life crisis for me, I didn't hire any 18 year old pool boys to seduce."

I laughed. "I try."

A week later, we met again, this time for dinner at a local restaurant. Lainie ordered a steak and I had a hamburger. The conversation was genial and general.

"What do you want to do next, Lainie?"

"Have you ever attended a play?"

"No, but I'm sure I'll have fun attending one with you."

So we did. And the weekend after that, we went to a free concert in the park where a local band was performing.

"Do you like picnics, Lainie?"

"I sure do, Tim."

So after consulting with Lainie about the food, I packed a picnic basket the next Saturday and met her back in the park. She brought the blanket to lie on. The food was tasty, and afterwards she cuddled up against me and we dozed in the sun with her head on my chest.

When we lazily opened our eyes, Lainie gave me a smile. "Would you like my lips to interface with yours?"

"Yes, please."

Lainie slid her body up a few inches and very gently touched her lips to mine. The kiss wasn't long or deep, but it felt wonderful.

"Lainie, that was amazing."

"I think you like me, Tim... a lot."

She said she liked directness, so...

"And how do you feel about me, Lainie?"

"You're starting to win me over. I appreciate the fact you're letting me set the pace and not trying to rush things."

We re-packed the basket and headed back out of the park. The next weekend we saw an afternoon movie. When I walked Lainie back to her front door, she consented to give me another kiss. This one lasted a bit longer, though it was still closed-mouth.

"It may be taking you a while to develop feelings for me, but I've sure as heck developed them for you," I told her.

"I know, Tim. Don't worry, I'm not going to pull some juvenile BS move and threaten to break up with you."

Four weekends later, she finally allowed me to come inside her house. I was supposed to be showing off my cooking skills. An Iron Chef I was not, but I did manage to draw praise for my cheeseburger/side salad combination. "Simple but tasty," Lainie informed me.

She led me to the living room afterwards and bade me settle on the couch. She settled next to me.

"Thank you for being so patient with me, Tim, and letting me have time to sort through my feelings. Coming off a divorce, I wasn't initially sure if I was ready to start a serious relationship yet. You've convinced me that I am, and I'd like to go just a little further sexually than kissing."

"How much further?"

"I'm willing to expose my chest and let you kiss my breasts and suckle my nipples. If you would like to."

"Lainie, you're a stunningly attractive woman. I would love to."

We shared a gentle, open-mouthed kiss, our tongues touching but not trying to jam them down each other's throats. Then Lainie broke the kiss and stood up. She removed her T-shirt and unhooked her bra before slipping it off.

"Very lovely." I estimated her breasts as perhaps C-cups. There was a little bit of sag, but not much. They were still pretty firm.

"Thank you, Tim." Lainie settled back on the couch. I kissed her neck, softly, and she shivered slightly. I then proceeded down to the top of her chest, taking my time. I unhurriedly laid a trail of kisses through Lainie's cleavage, and she smiled.

I then cupped her orbs gently in my hands and brushed my lips against one of her nipples. Her smile intensified. I slipped my tongue out and circled the nipple. Then I took it into my mouth and gently suckled, drawing an almost indiscernible sigh from Lainie. I switched back and forth between her nipples about once per minute, keeping my suckling very gentle. Her body relaxed and she lightly wrapped her arms around my head.

"Mmmmmm. Tim, that feels wonderful."

She let me suckle for a bit longer before disengaging my face from her chest.

"Take off your shirt and let me return the favor."

I peeled off my T-shirt. Lainie's tongue traced an intricate design on my neck, and I whimpered quietly.

"Wow, Lainie."

"Then you'll love this."

She slowly kissed her way down to my chest, while her fingertips played a concerto of sensations on my bare skin as she caressed my arms and my flanks. Ltille sparks of pleasure were shooting all throughout my body. I moaned and shivered.

When her tongue played across my nipples, I thought I would black out. I had never realized quite how sensitive my nipples were. Lainie was clearly an expert at what she was doing. I closed my eyes and let the sensations flow through me.

After a bit, she stopped, and I came out of my pleasure haze.

"Lainie, how on earth...?"

"Finish your question, Tim. I like directness, remember."

"How did you become so good at giving pleasure? I've had blowjobs and intercourse that didn't feel that good, and all you did was touch my upper body."

Lainie smiled. "I'm considerably older than you, so I've had a ton of practice. And you know what they say about practice making perfect."

That made sense.

"May I practice pleasuring your chest again next weekend?"

"You most certainly may, Tim. You're pretty darn good at it yourself."

The next three weekends were a repeat of this one, sexually speaking. Except that I was definitely getting better at pleasing Lainie. She thanked me for being willing to learn, and for taking her needs into account.

"I know you've been eagerly awaiting making love to me, Tim. And I appreciate your patience. Next weekend it will be rewarded. I'm ready."

"I guess good things really do come to those who wait."

For the first time, Lainie came over to my place. That in itself was a signal that she had full trust in me. Bearding the lion in his den, so to speak.

"The formalities must be observed," Lainie grinned, bringing in a small bag of groceries. Her cooking skills were considerably better than mine, and of course the meal was delicious. Veal piccata, mashed potatoes, a superb salad with pine nuts and arugula in addition to the usual vegetables.

"And now," she grinned, "please escort me to your bed."

"Yes, dear."

We both stripped completely. That was when I noticed the small tattoo on her rump. It was a rose. I had seen it before, somewhere...

"I got it when I was 19." She had noticed where I was looking.

"It looks wonderful, as does the rest of you."

"Flatterer."

"It's not flattery if it's the truth."

We climbed on top of the bed and kissed. It was a slow, tender kiss. One of Lainie's traits was that when engaged in sexual activities, she didn't like things to be aggressive. Gentle and soft was the watchword.

In tune with that, my exploratory caresses of her legs as we lip-locked were very careful. We had all night, so what was the rush?

Her hands were softly running over my flesh also, and sending tingles of plesure rocketing through my skin. I kissed her neck, then she kissed mine. Her tongue was doing magnificent things.

I slid my body downwards a bit so I could kiss and suckle her breasts. She gave the usual moans of approval.

"Tim, have you ever eaten pussy?"

"A few times."

"Then you'll have to let me guide you."

I kissed down her belly to her mound. She spread her legs and I saw a glimmering of moisture on her slit.

"Lick around the edges. Be gentle. You may also caress my legs if you like."

I caressed her legs, slowly, while I traced my tongue along the outside of her lower lips. She tasted wonderful. Why would I have expected anything else?

"Now, along them."

My tongue slid back and forth along her slit. More honey began oozing out. I greedily slurped it up.

"You may slip inside."

I obediently slid my tongue between her folds. Her taste and smell were heavenly. I instinctively moved my tongue in circles, trying to collect every drop of her nectar.

Lainie's moans increased in intensity. I continued to move my tongue within her. One of her hands found mine, and she moved my fingertip to a small nub. I very softly brushed it. Her body shivered with pleasure.

I continued brushing against the nub. Lainie's fluids were being produced more rapidly, and her body was quivering. I moved my tongue more quickly to collect them.

Her legs locked around my head and she blasted my trapped face with a geyser of fluid. I gulped down as much as I could. When her body stopped shuddering, she released the grip her legs had around my skull and lifted me away. I ended up lying next to her.

"Excellent job, Tim."

Lainie wrapped a hand around my pole, and I moaned.

"Oooh, nice and hard."

She slid her hand slowly up and down. My rod twitched at her touch. She knew exactly how to stimulate me without getting me too close to the edge.

"You're wonderful, Lainie."

She grinned and kept stroking me. After a bit, she removed her hand.

"I'm ready for lovemaking now, Tim. Would you object to doing me doggystyle?"

"I would not object."

Lainie adjusted her position so that she was on her hands and knees. The tattoo on her butt was quite visible.

It suddenly occured to me where I'd seen it before.

I rubbed my cock against her slit, lubing myself up with her juices, then eased my way in. "You used to be Lisa Mynx."

"How did you...?"

Lainie was unable to finish her question. I hastened to put her at ease.

"The tattoo, dear. And I've always thought you were gorgeous."

"Always?"

"Since I first saw Lisa Mynx, I always wanted to make love to her. Now I get something better. Making love to you."

I moved my hips slowly, and Lainie matched my pace.

"That's the part I didn't want you to know about."

I leaned my torso forward and reached out a hand to caress her face.

"There's no shame. Lisa Mynx wasn't real. But she helped put Lainie in a good place."

"Thank you for being so... understanding."

I cupped Lainie's breasts as i continued my steady pumping. She gasped slightly as I brushed my fingertips against her nipples.

I sped my rhythm up just slightly. Lainie's body shivered. I held her gently but securely as I pumped away. She tensed up momentarily, then shuddered through a climax.

I continued to slide in and out in an unhurried fashion. Lainie's moans were quite encouraging. I worked her gradually to a second orgasm, then a third. By now my balls were quite full.

"Pull out and cum on my ass, please, Tim."

"Gladly."

I slid my hips backwards, slipping my rod out of Lainie's box, then wrapped my hand around my shaft and jerked it. Within seconds, I was shooting streams of cum onto Lainie's sexy rear.

We lay on the bed next to each other, slowly recovering. Lainie nestled herself close and rested her head on my chest.

"Mmmmm. Thank you, Tim... for everything."

"You're quite welcome. Would you like to spend the night right here?"

"Yes, please."

I gave her a smile and kissed the top of her head. "I'm very lucky to be with you."

I turned off the light. Lainie and I closed our eyes...