Second Time Around
Something about her was familiar. I could swear I'd seen her face before, but she said, "I'm sure you're mistaken." And she didn't say anything more.
So we continued with the software training class at my company, a big enough roll-out that we had the software company's President overseeing the tech support, training, and customer relations on site. I'd seen the President's name on the contracts, but she had not been directly involved in the sales process. That was what the rest of the team was for. Was I mistaking her for someone else, as she said? I might be 50, but that's a long way from losing my memory, and supposedly a side effect of my exercise routine was improved memory. So where the hell do I know her from?
She was sexy, one of those women who inspires lust in men from high school to assisted living places. But who was she? It—and she—were driving me crazy. This blonde was dressed very professionally, in a tailored, stylish, fashionable way, but clearly was a MILF. The blue eyes were familiar. Not all blue eyes are the same, and hers were distinctive. I closed my own eyes, sitting along the back wall of the conference room in an extra chair we'd dragged in when the room became filled. I couldn't place her, but knew I wasn't mistaken. When I opened my eyes, I looked in the direction of the speaker, who was using the laser pointer on the screen and explaining the document cross-reference interface. The instructor's boss, my mystery sexy blonde, stepped alongside the speaker, directly in front of me, and leaned over the table to check out the printed talking points. She had a fine ass in that stylish, tight, slit skirt, with those legs, those runner's legs ... wait a minute ... BINGO!
I must have gasped, because she turned to look at me. A smile came to her slowly. She saw me make eye contact and stepped closer, leaning toward me. Yes, that was further proof, now with a full view of her bent-over cleavage and that smile, how could I not have immediately recognized her?
I said, "How are you, Dolly?" and she said, "How are you, Stu?
Through the too many miles and the too little smiles, I still remember you."
We stepped out of the conference room. "I hadn't recognized your married name—or your full legal first name on the contracts. No, her driver's license didn't say, "Dolly.”
"Stu, I didn't know how you'd react, so when I saw your company, your name, I just let my team do their jobs. But it’s so good to see you. You look great. I wish we could catch up."
"That's the beauty of us being the bosses—we can," I said to Dolly. "It’s almost lunch time, and I don't mind missing the turkey sandwiches the deli is bringing in. Do you still like sushi?"
"That depends. Do you still eat it with your fingers, because chop sticks baffle you?" Wow, she remembered THAT?
It seemed like a fairy tale—years ago, helping my buddy and her friend move their stuff together—her stuff into his place—when they had gotten engaged. All that trudging up and down stairs, from one third-floor walk-up to another, in hot weather no less. How sexy she looked in a tank top, toned but sexy arms, her tanned skin glistening with sweat! Her legs, God, what legs—fit, muscular, but not large, just like the fitness instructor type who does fitness pageants on the side. As we made small talk carrying boxes, I found out that was exactly what she did on the side when she wasn't writing code for a major defense contractor. She was sexy and fit, with brains, a body, and the smile of a toothpaste commercial model. At the end of the day, leaving our friends in their new love nest, I drove the U-Haul back to the rental location, across the street from the strip mall where we'd left our cars. It was dinner time and dark by the time we got to the cars. I asked if she'd like to get some dinner. She pointed to the sushi restaurant and said, by luck, it was her favorite sushi place. So we walked in, hot, sweaty, and thirsty. A couple of beers and some nigiri and sashimi later, I was in full lust mode and loved how she could dish it out like one of the guys, busting my chops for eating sushi with my fingers.
"I'm not good with chopsticks."
"So that's your pick up line? Get a woman drunk, then tell her you're no good with your hands? How's that working for you?" Dolly took a big swig from the long neck beer. The beer was cold, the room was not well air conditioned, and the condensation ran down the side of the bottle like the sweat that had been running down our bodies. She winked at me as she took her swallow. Then she played with her tongue around the edge of the bottle. "Well?" she asked.
Did this smoking hottie with the killer body just offer to suck my cock?
"There's more cold beer for this hot night at my place. And you're too drunk to drive anywhere, Dolly."
"Looks like I'm going with you then." She just looked at me, the beer bottle still in her hand, one swallow left.
I asked for the check, left a couple of twenties for a $26 dollar tab, took the bottle from her hand, and drank down her last sip without asking. "Hey," she started to mock-protest, clearly not upset, but rather smirking at me having stepped up my game in response to her challenge about being good with my hands. "Don't worry, that beer was getting warm, anyway," I told her as we stepped back outside into the humidity. "I'm sure we can find something good for you to swallow at my place." At that point, I didn't know if I'd overplayed my hand, but I was feeling the beers too. When Dolly slipped her fingers between mine as we now held hands and she squeezed, I knew I was going to have a great evening ….
Back in the present, Dolly and I took the elevator down, bounced dates back and forth, as we tried to figure out how many years ago it had been, and we nailed it because I remembered that I was already out of business school and where I was living—a place I lived for only one year, a couple of jobs after business school. And Dolly worked her first job for the big company for only two years, she told me, before deciding she needed to be her own boss and sold everything she had to put the money into her company. It was a gamble that had turned out well, I told her, and she agreed. So that placed her in her late 30s and the passage of time at about 16 years.
When we got to my car in the parking garage, I started to walk Dolly to the passenger's side, but she said, "Uh-uh" and shook her head, steering herself, and now dragging me by the hand to the drivers' side. She pressed me back against the door. "My turn this time," she said, as she placed her hands on my chest, leaned in, and kissed me in a take-charge aggressive way that seemed to be, well, more, much more, than anything I remembered. One thing I didn't remember at that time was the wedding ring on my hand. Had Dolly seen it, I wondered as I relaxed my tongue and kissed her back, forsaking whatever commitment I had to that ring for at least the moment. My hands moved to her hips and then, in response to Dolly pressing her body against me, from her hips to her ass. I thought, Oh, God, yes! Now I remember how this ass felt. I felt myself sliding back across the years ….
So back when we were too beer-buzzed 20-somethings, I walked her to the passenger door of my car, pressed her up against the door, and kissed her. For a verrrry long time. She initially simply received the kiss, not kissing back. After a moment, though, I guessed I must have done something right, perhaps when I sucked her bottom lip, inhaled her body's frankly less-than-fresh aroma, and decided I wanted to bathe in this girl's sexy essence. She didn't stink of sweat; she instead tasted vaguely of the salt of her sweat, the sushi, and the beer. And she smelled ... kinda like sexual excitement. Dolly kissed me back, matching my tongue swish for swish and flick for flick. Only when we heard, "Get a room!" did we break that young kiss, laugh, and get in the car so I could drive the short distance to my apartment with a raging hard-on and a hot 'n’ bothered sexy babe stroking my leg with her hand, saying, "Oops" each time she "accidentally" stroked my cock. The third time that she swore it was just an "accident,” I told her that I was very glad she was so accident prone and hoped she would continue her clumsiness all night. "Oh, I'm likely to have lots of accidents tonight. I hope you have insurance. You know, health insurance? Because when I'm done with you, you're going to need it."
The more mature versions of ourselves finished a spicy tuna roll and a California roll. Even though it was lunchtime, and even though I was married, I asked this sexy woman, who I noted was NOT wearing a wedding ring, to have a beer with me for old time's sake. When we finished that beer, she asked if, for old time's sake, I had more beer back at my place. I looked down at my hand, in plain view on the table, wedding ring and all, and said "We don't keep beer in the house; it’s too much temptation for my high schooler." I emphasized "we.” Dolly reached over and took my hand, "Well I do keep drinks in MY house. My very private house. Or is that too much temptation for a high schooler's dad?" Then Dolly asked for the check, left about $20 too much on the table, and took my hand as she led the way out. "Don't worry, I've got a client I can charge this lunch to. I'll throw in some extra benefits for him." She had me hard again.
Dolly gave me driving directions. It turned out she lived only 15 minutes from my office. I pondered the odds. I thought of how, in 16 years, I'd gotten married after a whirlwind romance and then we'd gotten pregnant on our honeymoon, which seemed okay since I was already in my 30s. But I did think about how I was no longer living the life of a 30-something that I'd lived just a year before that honeymoon, when I had met my fantasy fitness babe doing what proved to be the last volunteer help a friend move afternoon of my life. It was clearly the best day of carrying boxes I'd ever had, and now I was having a completely unforeseen reunion. Only now, Dolly didn't pretend it was an accident that she was stroking my cock as I drove, and she'd deftly opened my fly and taken my cock out. My married cock. Her tanned hand with sexy red manicured nails was pumping up and down, getting smeared with my pre-cum.
"I remember how thick you are. This is going to feel so good inside me again," Dolly purred, and then she leaned over and licked a dab of pre-cum from the purple head of my cock—a cock that was just aching to go exactly where she wanted it to go. When she directed me to park, she leaned over for one more lick, this one slow, up the length of my shaft, which elicited a major twitch as she cradled my cock and then smiled at me with glee. "Put that thing away long enough to follow me.” I did as I was told again. Watching her ass and legs walk in those fuck-me pumps from behind was not relieving the swelling in my shorts. The only relief I wanted was from her, and that would have to wait at least a little longer until we got into her high-rise penthouse. Hot digs for a hot lady!
Our first, youthful fuck had been in my bachelor apartment, back when a framed movie poster passed for artwork on the wall. That time, we got inside after struggling to keep our hands off each other while I drove, or at least limiting our foreplay in the car to things we could do while buzzed without getting into a wreck. But once inside Chateu Stu, we started stripping the sweaty moving clothes off each other—OMG—I'd never seen a nude body like that in person, not even in strip clubs. Those girls were never in the shape that Dolly was. She had been a high school and college athlete and competitive runner, I learned. We stripped right inside the door as soon as it was closed, hungrily kissing each other whenever both our mouths were available. Once the clothes were in a sweaty pile, we closed in, and my cock felt her hot, wet folds embrace the base of my shaft as our bodies lined up to embrace and grope. Okay, I wanted my mouth all over her and, young as we were, I knew there was a better way. "Shower with me?" I said when I broke a kiss for air. Dolly didn't answer; she just looked around and then raised her eyebrows, an internationally understood version of "Which way to the shower for sex?” Or at least, that was my interpretation.
That was the bar soap era, before today's liquid body wash. Both being single, neither of us cared about the scent coming off my bar of Irish Spring. Hey, I was young and single, still using the deodorant soap I'd used since high school sports. Unlike Dolly’s, my jock career didn't extend to college and beyond. We soaped up, groped, stroked, lathered each other's hair with my non-designer shampoo, then plunged back into deep French kissing and very explicit manual foreplay. I flicked my fingers a few different ways until I got the correct direction, speed, and pressure against her slick, cream-coated clit and heard, "Right there! Yeah, more!" before she sucked my tongue back into her mouth, harder, more passionately. Feeling her mouth begin to tremor as her first orgasm reached her face from the rest of her quivering body was a rush. I had two fingers inside her and one from the other hand doing the outer twiddling, while Dolly had a freshly washed leg wrapped around me, one hand on my cock that stopped its stroking when her body stiffened, and the other hand around the back of my neck. It slid down to my shoulder and her nails dug into my flesh, as she cried out, "Oh, God! Yes, I'm cumming, oooooh yesssss, ahhhhh, fuck yessss!"
This time, however, modern married Stu followed successful independent business owner babe Dolly into a professionally decorated penthouse to which the private elevator opened directly. Nice! It makes my cock hard just watching her walk, seeing her body move, so fluid, confident, strong. When Dolly dropped the jacket of her designer suit on the chair just inside her family room, I noticed for the first time that her blouse was sleeveless. Seeing those arms made me recall the sexual strength I felt back in the day when we were in mid-fuck-embrace. Damn, she's opening a bottle of Merlot and pouring a couple glasses, looking like the fitness instructor of every man’s dreams, all dressed up and ready to get undressed. She peeked over at me and smiled, "Not that I need to ply you with alcohol …" to which I replied, "You had me when you said you wished we could catch up." Another smile. Damn, she gets me harder with every sexy part of her. And to think my cock will be entering that sexy, beautiful mouth. Oh, who am I kidding? It’s not as if I'm going to be doing something TO her. Dolly is the one who is going to be in charge—screwing my brains out—so I should say that her beautiful mouth is going to take my cock, take it deeply, bring me to the edge, coat me with saliva, lick and drive me crazy, and swallow as much as I can deliver before kissing me to let me taste myself on her lips. She loves it, loves the power she has over men. God, how I wish I could have been with her during these years ….
She pretty much had attacked me after the younger versions of ourselves toweled each other off. She knelt down, naked and glisteningly clean, and deep-throated me, teasing my balls with her fingernails on the hand that wasn't steadying the base of my cock. I ran my fingers through her still-moist golden blonde hair. I was turned on from the lean shoulder muscles of her young athletic body when she was facing downward and also twitching with desire when her deep blue eyes locked on mine, on fire with lust. I didn't want to finish in her mouth in my bathroom, but that's just the way it happened. Dolly sensed it, heard me gasp "Oh, God, Dolly, if you don't stop, I'm going to cum in your hot mouth," and that just seemed to motive her to turn her suck-meter up to 11 after she was already at 10. I shook my pelvis into her mouth, grunted, and then finished with "Arghhh, oh, oh, God damn, Dolly, oh my God ...." The sheer victory in her eyes when she finished slowly licking my overly sensitive, freshly spent dick and then stood and embraced me strongly and kissed me, full cum residue and all. That was a novelty to me in those days, tasting a bit of my own, and it just felt so ... so intimate. After what her mouth had just done to me, I'd have done anything for her. "Take me to your bed and taste how wet and sweet you've made me," was what she commanded young Stu, as I think of myself back then. "You got it."
When I saw thoroughly modern Dolly unbutton a couple more buttons on her blouse after she'd set the wine down in her bedroom (nice water view from the walk-out terrace!), I took the hint and stripped, glad that I work out, though nothing compared to what Dolly does. She stepped forward again, helped me off with my trousers, and once more stroked my cock, commenting on the pre-cum stain seeping through my boxers. "Did I do that to you? Seems fair, considering how wet and sweet you make me. So you do remember what I like you to do about that, right?" Another cock twitch in her hand, and she half grinned in victory, half squinted with desire. "You were good at that. I bet you're even better now." Her blouse and then her skirt joined my clothes on the chaise lounge in the sitting area of her room. This time when we embraced, it was less violent, more patient, knowing that we were going to be pleased with our results. Instead of youth and sweat and salt, her body tasted of arousal and just the right, subtle wisp of an elegant perfume that drew me in. I needed to be her lover again. Her legs I now saw were in thigh highs, when she asked me, "Want these to stay on?" Hmmm, a fitness model's tanned toned body, D-cup breasts with just a hint of being perhaps a millimeter lower than when she was in college, a flat, toned tummy, legs of an Olympic track and field champion, an ass that could crack walnuts between her cheeks, no tan lines, fully shaved nowadays where a landing strip had once existed, the fashion of the day when she'd first taken me to heaven in bed. "Yes, Dolly, keep your thigh-highs and your heels on." She took me by the hand, backed up without looking, felt the back of her thighs hit the bed, and moved back onto that bed. She beckoned me to follow, slipping one hand down between her legs, rubbing herself, dipping a finger in her own sweet sauce, brushing that finger on my lips. "Kiss these lips as well as you do my mouth. Do it for me again, Stu."
I guess I'd emerged from college with decent pussy-eating skills, because, as a younger man, I got a lot of compliments on the work I did between a woman's thighs. I hadn't set out to be such a cunnilinguist, I just had a few girls that would do everything but go “all the way,” as we used to say, when I was an undergraduate. Dolly had been so slender hipped, not an ounce of fat, jiggle, or cellulite, so perfect, like a statue the Greeks would have carved if there'd been a women's bikini or fitness competition more than two millennia ago. I explored all around, licking up and down her slit, really drinking it in, softly kissing her big fleshy labia, dipping my tongue into her sex, feeling her body's heat, gently sucking her clit, then less gently, then rubbing my lips across her clit and through the sea of sweetness. I thought that I counted two orgasms, though her thighs squeezed my head more than that, which I just thought was more of her sexual desire for control. She later told me there had been three, the third very close after the second, and that's when I learned about after-shocks. She lapped up her own aroused pussy's flavor from my chin, the tip of my nose, and my lips when she commanded me to get my "sweet pussy-loving mouth up to her man-pleasing lips” so she could taste the treat she was giving me. I was more than happy when she got so turned on by her own flavor and rolled me onto my back so she could lick me back to full mast, which wasn't a far trip considering the turn-on factor of going down on her, plus my youth, as I look back now. Nowadays, a young person moves apartment to apartment and calls two men and a truck to do the heavy lifting. Those two men probably aren't doing what my fellow mover and I were engaged in back then.
Dolly hadn't had any toys with her when we'd become young lovers. But now that I was back in big girl Dolly's penthouse, the drawer was opened and what to my wondering eyes did appear but a modified sonic electric toothbrush--brush removed, smooth rubber nub substituted. "My dentist says it vibrates ten thousand times a second. Can't beat that," and suddenly my mouth was sucking and licking a completely saturated sex palace that was humming with a hypersonic pulse. My fingers moved from her ass. Clearly, Dolly had been doing lunges and running for years. My God, she'd been only young and firm-assed back then; now she had a championship gymnast's type ass. It didn't take her long to progress through a series of three thigh-clenching, "Oh shit, yes, ooooohh yessss, keep licking, oh that's it, suck me, such me there ..." orgasms. Dolly gave me a kiss that was mostly licks. "Sixty-nine me?" Dolly asked. What, as if there was more than one way to answer that? She had to ask? Really, I was on my back and she was in control during the entire sixty-nine. Oh, to be in the clutch of her hands and legs during sex. I did my part, obeyed her commands to insert fingers, plural, and where to tickle her inside while sucking on her sex nub outside, while the electronic sex brush, er, toothbrush, did the rest. She hit two more high notes while she gave a one-handed (hey, the other one was holding the vibrating wonder stick) stroke and suck session, this time with more spitting than I'd recalled, more porn style, as if she'd lost that last half of one percent young girl she'd maintained up through the time I got her back at my apartment. I spread my legs, trying to find something to brace myself against as the pleasure took hold. I couldn't fight the urge to pump my hips and face-fuck Dolly. She took all I could try to give and loved it all. I knew I was welcome to cum down her throat. She dropped her vibrating toothbrush toy when I started to spurt, strongly embraced me from the sixty-nine position, and again took all of me down her throat. She'd spiked me only twice with her heels. So sexy, I never got wild porn style sex with the heels still on at home. Or anything else remotely Dolly-like.
My mind was scrambled, the thrill of sixty-nine to completion with Dolly, along with just the fact of the reunion with Dolly. I was catching my breath and recalling when I'd gotten her out of the shower and into my bed the first time around. I was younger, thinner, more flexible. It was as if she'd been in suspended animation--athletically, physically, she really seemed as great or better. She hadn't lost any flexibility. Back then, I toweled her off and led her by the hand to my bed. She said, "I hope you like doggie," as she got on the bed on all fours, facing away from me. Starting off sex in anything other than missionary position was new to me, and it felt so dirty--in the best possible pornographic sense of the word “dirty.” I took a condom out. put it on myself, and then rubbed the latex coated head up and down her wet sex. Dolly, young, hot and bothered, and impatient, half turned around, reached back, held me still, and began to rear herself back onto me. Oh my God, the feeling of heat, the scent of her arousal. To show off, she was flexing and unflexing her pussy around my cock as I went deeper into her. "You do feel good, mmmmmm," was all she said. Then Dolly started rocking back and front, finding a good working speed, as I grabbed her sexy slender hips and tried to keep up. She was still reaching back, twiddling herself. Again, it was so hot and dirty to see that. I got into the porn act, too. For the first time in my life, I spit on a girl as I let some drool drop onto Dolly tight young ass in front of me and smeared it over her inviting bung hole. I'd never ass-fucked, and I didn't that day, but I did work a finger in her up to the first knuckle. When I did, Dolly's head dropped to the mattress and she groaned in pleasure. In my youth and excitement, it was an amazing doggie style fuck with this fitness goddess and all of her sexual mannerisms, the finger in her ass followed by her whispers, "Do you want to fuck my ass? That's it, finger fuck my sexy ass, and keep doing my pussy with that nice thick cock, stretching me out." I wondered if she watched porn. My knees started shaking as I felt it build in the base of my cock and balls, and then I shuddered and emptied into my cocker, moaning in guttural satisfaction. She hadn't quite gotten there yet, so I tried to keep pushing as my cock softened. She grabbed my hand, told me to use two fingers, directed where she wanted them inside her, and twiddled herself on the outside, smearing her own generous amounts of body-produced lube until she came, silently this time, but with internal muscle contractions that pushed my wilted cock out of her. What a damn sensation! She rolled onto her back and told me to get over there. I canoodled with her as we made out like teenagers. She wasn't all that many years past being one, looking back.
And now here I am, looking back on the amazing time-travel aspect of fucking a woman twice, a decade and a half or so between encounters, and the similarities and differences. I'm on my back, and, as Dolly rides me, having sucked me back to life, she is slower, more sensual. The feeling is more stimulating, whereas the first time felt more like excitement than stimulation. There’s more eye contact now, my hands allowed to roam where I want them too. She specifically asked me to feel her up and to be rougher than I had been the first time she rode me back in the bachelor pad. Teasing me both times with her hands, she clearly has the libido of a succubus and has always been directed to please herself while pleasing her lover. We had moved through more positions more quickly during our first time together. In contrast, my sense of our love-making now was that she was playing to my speed. Did I call it love-making? I knew it wasn't. Never considered it the first time, but that was perhaps just me. For all I know, she's been this sensual her entire sexual adult life, and she was merely adjusting to whom she was with. These days, you look up middle-aged and you see my picture. I had finished a second time inside Dolly, covered of course, standing missionary up against the wall when I was younger. It had always been a fantasy of mine to do that, and here she was, so slender and sexy, and I was still young enough. Now, after an increasingly intense riding session, Dolly leaned forward and kissed me as she let me feel her climax on me. Because I hadn't popped, she bit my ear lobe and whispered, "Want to switch, you be on top?" Has anyone ever refused this woman? She slowed to a halt, but with me inside, grasped me with four toned, sexy limbs, and initiated a still-linked roll. Presto, missionary. The heels dug into my ass a couple times, then one leg went over my shoulder so I could get more swaying and pumping room. This was how I finished, spurred on by the feel of her thigh highs rubbing against me and her fingers tweaking my nipples as she and I deeply kissed, passionately, for what seemed like much longer than it could possibly have been.
The first time, I had cuddled and made pillow talk, though when Dolly tried to get me hard again, I was more than happy to shut up. Alas, it was the end of the day and I was tired, having shot my last load. Dolly said she had to get up the next day due to a family obligation, and, as much as she'd like to stay, could I please get her back to her car? I asked her all of the "When can I see you again, you're great, are you dating anyone," questions I could. She never returned my calls. Through our mutual friend, when I asked, I learned that Dolly was travelling a lot. She had sensed I wanted more of a girlfriend than she could be and didn't want to lead me on. I obviously was at the stage of life where I was looking for a wife--I met my wife just weeks after my exhausting box-carrying (and then box-licking and box-filling with Dolly) day.
Fast forward to Dolly on her tummy, me on my back, smiling like old friends who'd been so comfortable with each other, chatting it up with her asking questions about me. "Dolly, I ..." but she put a finger to my lips, crawled forward, and kissed me softly. Such soft lips! "I'm not looking for a husband any more than I was the first time, but I sense you might just be in the mood for a less committed, more private relationship. I'd like to keep earning your company's business the legitimate way, so let’s consider this separate, okay? No, I don't do this with all my clients."
I couldn't stay. She sat in a short terry cloth robe while I showered, looking extremely cute, her legs always looking great no matter with heels or not, and she'd stripped off the shoes and thigh-highs moments after we finished and intertwined her legs with mine. The softness of her skin contrasted with the firm, toned muscles beneath.
So as she walked me to the door, I said, "So it won't need to be another 16 years?"
She flashed the Dolly smile. "It might not be 16 days either—this was fun. It won't be too much longer than that, but you can't call and ask. I've got a complicated life and schedule, so let me do the inviting, okay?" Again, does anyone ever refuse an offer like this? As I walked away in silence, it’s strange how you never know. But we'd both gotten what we'd asked for such a long, long time ago.
Purely fictional fantasy for your reading pleasure.