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“Just once.”
Those two words ran through my mind again and again since they were whispered by Delany a few months ago. It was the last short sentence of a much longer, maddingly flirty, conversation we shared at a local brewery after work one day.
Delaney and I have similar jobs in a big organization. Our offices are adjoining and we share projects, staff, goals and are a strong two person leadership team. Over the course of several assignments and a few years, we rarely went a day without spending at least an hour or more in each other’s office resolving problems or designing a new strategy in support of the company’s
She is incredibly smart and moved up quickly in our field. At five foot ten, fit and feminine, Delaney is a beautiful blonde who inspires admiring glances because of her perfect bottom, long legs, proud chest and piercing blue eyes. She dresses in snug tops with skirts and slacks that accentuate her y figure. But to me, her iness is sharpened by her humor and brilliant mind. She is one of the smartest people I know. It is such a turn on.
It doesn’t help that she is also a flirt. If she walks behind me, she’ll routinely run a finger along my shoulders and announce, “passing,” as if I didn’t know she was there. Or if walking toward each other down the hall, she will reach out and tap my upper arm, commenting, “oooh, someone’s been working out,” then wink and pass without stopping.
I do my best to roll my eyes or let these little gestures pass without responding, but her teasing touch and comments leave me horny and fantasizing the rest of the day. She had to know the impact she inspires.
In spite of that playfulness, the boundaries have until recently remained intact. She shares stories about her husband and kids and I speak openly about my wife and son. We offer each other counsel when life is stressful at home or work, and can tease without offending. She calls me her best friend and I feel the same towards her.
Occasionally we leave the office early and meet at a local tavern with our laptops in tow to get a little work in without the interruption of coworkers, subordinates, or family. Our favorite spots are the high top chairs along the bar because they provide access to outlets for computers and phones. Seeing her skirt ride up her toned thighs when she crosses her legs to get comfy on a barstool is a delightful bonus.
Inevitably our conversations turn from work to fun or other personal topics. During one gettogether, starting her third drink, Delaney closed her laptop and said, as if she were asking about how to get a stain off a carpet, “How many women have you slept with?” I was a bit taken aback. That was blunt, even for her.
I thought for a moment, doubled the number just for the hell of it and said, “12.” I exaggerated to see if I could get a disgusted response from her. Then I’d confess to the lower number. Instead, even before I could admit to my veracity issue, she raised her eyebrows then began a rapid fire interrogation. Who was best? How many were onenight stands? Had I been in a threesome?
During the course of the ual Q&A, Delaney swiveled her chair to face me. She put her feet on the rail that wrapped my stool and spread her toned legs. A short red dress that normally covered her knees ever so slowly, and tantalizing, rode up her thighs. Between her questions, and the exhibitionism, my cock was stirring under my pants.
When she took a moment to sip her drink, I turned the question back on her and asked her about the number of lovers she had prior to her husband. “Only two,” was her quiet, almost apologetic, answer. She described a classmate in college to whom she lost her virginity and became her boyfriend till graduation. Then someone she met in her first professional job he was ually voracious and so was she. So they were a great physical match. “How did it end,” I asked? I was curious but also needed to tone down the topic. My hardon was now visible through my khaki slacks and I was afraid I would soon be oozing a precum stain if I didn’t relax.
That was all it took to move the topics to more inane subjects, allowing me to calm myself and head to the restroom. When I returned I suggested it was time to wrap and Delaney gave an exaggerated frown but agreed. We split the book, gathered our belongings and headed out.
Our cars were both parked near each other and as we walked, Delaney asked how I was getting home. “What do you mean? Driving.” I wondered if I seemed drunk after two beers.
“Don’t you need your keys?”
“Oh shit,” I had tossed them on the bartop and forgot to snag them when we finished. “Well, here’s your car,” I said. “I’ll head back to get them and see you tomorrow.”
“You won’t find them in there, I grabbed them when you went to the restroom.”
I held out my hand. “Thanks!”
“Nope,” she smirked. “You have to find them.” I looked at her for several seconds trying to decide if she was starting a game. She gave a quick smile, bit her bottom lip, and said, “I haven’t played hide and seek in years.” My stomach flipped for a second and my cock stirred again.
We had flirted but this was a new step. Tentatively, I reached for her purse. “Cold!”
She held her arms out, inviting a pat search. The move raised her shoulders and lifted her dress up her legs. The impact was instant. The feeling in my stomach and crotch was making me more anxious.
Delany encouraged me by taking one hand and placing it on her hip. I pulled away slightly but left just a fingertip on her side. “You can do better than that,” she admonished.
She moved closer and took me by the wrists. Placing my open palms on both sides of her waist. she simply raised her eyebrows and encouraged me more. “Still not warm enough.”
She was now close enough that I could smell the wine on her breath and the light scent of her perfume. The moment was surreal and my hands began, almost involuntarily, to slide up and down from her hips to her arms. Feeling her bra strap under her outfit, my horniness was rapidly turning to lust.
Thoughts of my wife, Delany’s husband, and our working relationship snapped sense into me and softened my desires. I realized it was safest simply to release my hold and demand she just hand over my keys.
She shook her head. “I noticed how much you enjoyed discussing our ‘ histories’ back in the bar.” Delaney looked down at her perfect breasts, pulled the top of her blouse open to reveal a black bra and said, “Maybe I put them here for safekeeping.” Her blue eyes teased in the light of the evening sun and her freckles were ier than ever.
I looked around and saw the neighborhood was teeming with people. I work out, stay in shape, but am 55. She is 45. Groping a beautiful blonde on a downtown street was not good form. My cock strained against my pants. Delaney looked down and noticed my dilemma, raised her eyebrows again and gave a naughty smile.
Though the thought of lingering under her bra and stroking her luscious breasts was driving me insane, I insisted I was not going to reach in her top, especially in public even as the daylight faded.
As quickly as the game began, it ended. Feigning disappointment, she retrieved the keys, dangled them in front of me, grinned and said as if implying much more, “Just once?” She laughed, opened the doors and slipped into the driver’s seat. “See you tomorrow!”
I stumbled to my car holding my laptop in front of me to hide my cock and the wet spot on my pants. Slipping behind the steering wheel, I sat for a full five minutes before starting the engine and heading home. Adrenaline and testosterone were fogging my brain. “Oh my,” I wondered, “Is something more underway?”
The next day, I was both relieved when Delaney dropped by my office and while leaning against the door frame, tilted her head and said, “I had a blast last night but sorry it almost got out of control.”
“Almost,” was my immediate response? “Don’t worry, it was fine and I’ll behave better in the future too.”
She said, “I don’t know if I’ll behave better, but as long as one of us does!” She smiled, spun on her heels, and padded down the hall to her office.
We didn’t discuss it again.
A few weeks later I left the office a little early and stopped at a nearby tavern for a light dinner and a beer. My wife is a spin instructor and would be teaching late. She wouldn’t even notice if I didn’t go home after work. So it was a good chance to relax and get some work done.
Scrolling through a document while seated at the bar I heard a cheerful, “I knew I’d find you here,” and Delaney scooted onto a barstool next to me. So much for getting work done, I thought. But I welcomed her company since we always enjoyed these meetups. Tight blue slacks and a low cut blouse made the visit even more welcome.
Delaney ordered a glass of white wine and we worked for about an hour. Eventually the conversation moved to office politics and then to life at home. She spoke more than usual about her husband and her sadness with their relationship.He played video games constantly, slept on a couch in the basement, and wasn’t looking for work after getting laid off from a contract position. She admitted to being at her wits end. He was clearly depressed and she seemed very vulnerable.
She asked me how things were going with my wife, Ginni. Since Delaney and I shared so much she had heard quite a bit, and provided several hours of amateur therapy over the last years. So she was aware of my vulnerabilities. After 20 years, Ginni and I had drifted to separate paths under the same house.
We rarely had . Following each of our last few sessions, she would sigh and lament that she just doesn’t enjoy it anymore. In fact, she said penetration actually hurt.
Our interests were not aligned, but neither of us had the energy or interest to really make a break.
After sharing my latest frustrations and to be fair, those of Ginni Delany announced, “Well, that’s depressing, let’s have some fun.” She was on her third glass of wine when she grinned and said, “Truth or dare.” Ok, I thought, time for some silliness.
I started us off. “Truth.”
She took a large gulp of her wine and asked, “What’s your favorite position?” She slammed her empty wine glass on the bartop like a shot of whiskey and motioned to the bartender for a refill.
“Well, you’re in a mood,” I laughed. My response? “Doggie when drunk and aggressive and cowgirl when in the mood for slow and sensual.”
Her eyes went wide and she licked her lips. “Mmm. Me likey. Now, it’s my turn and you don’t get to choose. I’m gonna have you give me a truth.”
“Uhhh, isn’t that cheating?”
“It’s my game we get to play it the way I want to.”
She giggled and took another long drink of wine. Then she poked me in the chest and said, “My truth is also going to be what my favorite position is.”
“OK. Not sure I want to hear that!”
“Well, it’s somewhat of a coincidence that my favorite is cowboy also. I consider it my specialty. I love to grind while I’m on top of my partner and feel his dick in all my favorite spots. Up and down, backandforth, side to side. Leaning on his chest for support. Reaching behind me and tickling his balls. It’s my easiest way to orgasm.”
A little verklempt, I replied, “Oh my, that was a little more descriptive than my answer. “
She took another sip of wine and said, “I’m probably gonna win this game because I’m clearly better at it than you are!”
I rolled my eyes. “Whatever.” She squirmed a bit on her stool and my cock was responding to the details of her truthshare.
We went back and forth with some y and innocuous reveals. Who would you do from work? What celebrity would you do? Where could you live if you could?
Finally, I broke the ice and said, “Dare.” Her tipsy grin widened into a smile. She raised her eyebrows, looked down and teased, “I dare you to run your hand along that hardon of yours!” I couldn’t believe where this had moved. And not sure where it was headed.
Delaney looked at my lap and realizing the effect the little game was having whispered, “I so want to throw my leg over your lap and feel that against my crotch.”
My cock now twitched and strained against my pants. We were both loving the impact of her teasing. “Wow,” was all I could mumble.
The thought of her long, fit legs draped around mine and her body grinding on my lap was nearly overwhelming.
Not even bothering to be discreet, she lightly bit her lower lap and kept peering at the outline of my hard cock. “But I am better at this than you as I already told you. So I think that I should do your dare for you.”
Turning toward me on the stool and spreading her legs, Delaney scooted closer and leaned in to look at the screen of my open laptop. She clicked a key and it lit up. Pretending she was studying something, she dropped her hand onto my lap and ran her fingers over the bulge showing through my pants. “Yum,” she said, not taking her eyes off the screen.
No one at the bar saw her massaging me or how I shivered in response. After about a minute of her agonizing play, Delaney leaned back in her chair and removed her hand. I was so hard it hurt.
“Oh my god,” she said quietly and slowly. “I am so horny. I think I soaked through my panties.”
Getting braver, or more reckless, in the moment I pushed for more. “I don’t believe you, your dare is to prove it.” Her mischievous and y smile came back. “Hmm, I need to think about it. But first I have to use the restroom.” Her beautiful ass swayed ily as she slipped off her stool and walked away from the bar.
My head was spinning when she returned and scooted back onto the bar stool. After she was settled, I felt something land softly on my lap. I peered down into the shadow from the bar to see she had dropped her panties on my crotch.
Her teasing smile came back and she said, “See for yourself.” I raised them a bit, still below the bartop but could feel how damp they were. I moved the crotch of the panties between my thumb and fingers and massaged them to get the full effect. Slick grool coated the tips of my fingers. Dropping the panties back onto my lap, I raised my hand and took a slow, deep breath and mouthed, “Oh. My. Gawd.”
“See what you do to me,” she whispered?
I imagined smelling her pussy and running my tongue along her slit. Though the sticky residue I sensed was obviously her slick juice, I told her I didn’t believe her and that she could have wet them from a faucet.
Delaney looked around, then widened her legs. The dark and nearly empty bar provided sufficient privacy. She slid her hand inside the waistband of her slacks. Her knuckles pressed out against the stretchy blue fabric of her slacks. Softly biting her lip, she moved her arm lower, stopping when she reached her crotch.
Her hand pulsed in and out against the front of her slacks. I looked up to see her eyes were closed and she was biting her lip. After about 60 seconds, she pulled her hand out and displayed shiny, glistening fingers. Pretending to point at my screen again, she wiped her juices on the back of my hand.
Abruptly Delaney announced, “Well,I guess we should go.”
“Wait, what? What is going on?”
“I am having so much fun, but I told my family I’d be home by 7.”
“Holy shit. You tease!”
,
Delaney laughed and said, “Whatever!” Then continued. “I had to park in a spot where I could use a ride.” We paid our bill and walked out. My hard on was hidden by my laptop as we walked to my car.
As we reached it to my car, she slipped her hand into her blouse and the car beeped as doors unlocked remotely. She had hidden my keys in her bra again. Dangling them in front of me, I reached out, but she pulled back and stuffed them again into her bra. “You’re going to need to work harder for them this time.” I could barely walk and now she was flirting even harder.
I moved in behind the steering wheel and she moved into the passenger seat. “Where are you parked,” I asked?
She didn’t answer and instead closed her door and reclined the seat. She pulled her blouse open from the top and said, “Don’t you need your keys first?” Erect nipples poked against the lace of a green bra as her other hand started massaging her pussy on the outside her slacks.
With my will power weakening by the second, I brushed my hand over the material on her left breast, slowly searching for my keys. Softly, I caressed her. “You’ve hidden them well,” I complimented her. And slipped the strap down her arm. “Guess I’ll have to look more closely.”
The cool air made her nipple even harder and she moved her hand from outside her slacks to deep under her waistband. She slowly started working her pussy while I massaged her soft, warm, gorgeous boob. It wasn’t enough to just rub her nipples between my fingers, so I shifted to taste her and lowered my mouth to lick and kiss her sweet tips.
She moaned as I swirled my tongue around her areola. Slight salty with the soft scent of her perfume now swirling around my head, she was intoxicating. Here we were, two middleaged plus adults, licking and tasting and groaning like teenagers. And we both knew what we were doing was wrong.
Just as that thought was starting to consume me. The keys fell out of the other side of her bra and dropped to her lap. I instinctively pulled back and we both laughed. The delirium of passion that was building was interrupted just in time for us to both realize our situation.
“I think that’s someone’s way of reminding us we have families at home,” I whispered.
“I agree. The Fates are telling us to chill.” Delaney pulled her hand from her pants and showed me her wet fingers. “But look what you do to me.”
She said that since I was responsible, I had to clean her fingers before she went home. Just as I was calming down, my gut, and groin, surged with lust again. Lightly touching her first and middle fingers to my mouth, the scent from her soaked pussy filled my nostrils. It was heavenly.
I parted my lips and she slid her fingers between them. Slipping in and out, her juices were replaced with my saliva. Then, holding her hand in front of my eyes, she turned it back and forth and purred, “Nice work.” She dried them by running up my pants from my knee to my bulging cock.
“You taste delicious and are an amazing temptress. But you know we need to stop now before we do something we’ll regret even more than this.”
With an exaggerated pout, she sighed, “Of course you’re right. And you need to stop too, you crazy flirt.” She straightened her clothing and I drove her a few blocks to where she had parked. The sun was fading as we hugged goodnight. She slipped into her car and headed home.
The game had gotten more serious but ended before it really started.
Just before I arrived home, my phone buzzed with consecutive texts. I picked it up and saw a series of messages from Delaney.
“I had fun tonight. Thanks for cheering me up.”
“And sorry for the boundary issue.”
“We probably need to stop. For our spouses and our friendship.”
“I wish though…”
“Just once.”
That night as I laid in bed, my imagination raced with the thought of making passionate love to Delaney. Sleep, then more . Then sleep, then even more . I was hooked but it had to stop. I stroked myself till I came. Then I immediately fell asleep.
We would occasionally mention what we dubbed our “boundary issue” and how we need to ensure we don’t cross too far. To this point, we both agreed.
Yet we continued to push our flirting to the limit. She would text me when she was horny just to tease. At an after work happy hour, I would dare her to touch herself, an ask she would discreetly fulfill.
It was fun, frustrating, and not healthy. We agreed that since we would never cross to a real affair, the flirting needed to stop. Then we would play again.
ero
