Never in a Thousand Guesses

My phone lit up while I struggled to stay alert during a compliance meeting. Patience testing endeavors made necessary in a world run rampant with oppressive government oversight, digital fraud, and the potential of litigation due to just about anything.

The call was from Dylan Langford, general counsel of a long-time client of mine, and someone I could excuse myself from this meeting to speak with, if only for a few minutes.

"Hi Dylan, listen, I left a compliance meeting to take this call, so I can only talk for a about ninety minutes."

"You know Greg, I run meetings like that. I really do appreciate if my audience pays attention."

"If you were running this meeting, I'm sure I would be riveted to your every word, but alas, you're not. How are you, what's going on?"

"I'm fine," she said. "Sort of."

"Hmmm, ominous. Anything I can do to help you?"

"That is the question. And yes, yet not that easy to ask," Dylan said

Odd response to a generically rhetorical question. Can't be anything wrong. We just went through a thorough review with her company. They couldn't be reconsidering our contract, could they?

"Anything Dylan, well, anything within reason I suppose," I said. "I probably won't kill anyone for you. Probably."

"It's not that drastic. I've spent a lot time pondering this Greg," she said somewhat hesitantly. "Well, here goes. I need your penis."

She had always been direct and to the point, however, this was off kilter. I was more than slightly flummoxed.

"Ah, pardon me?"

"You heard me," Dylan said.

"Are you..."

"No, I'm not kidding," she said.

"Ah, sure, is everything alright?"

"It will be. Text me your address, I'll be there at seven o'clock." She hung up.

I doubt if she was drunk or high, it was two in the afternoon, unless there was a problem I wasn't aware of. There was also the outside chance that someone else had grabbed her phone and, doing a great Dylan impersonation, called to prank me. While not totally out of the realm, somewhat more difficult given the password protection of the latest iPhones.

I called her back.

"Yes," Dylan answered curtly.

"Did you just call me?"

"Yes."

"Are you sure you're okay?"

"Yes."

"Did you really say..."

"Yes, I said what you heard me say. It took all I could muster to do so. Listen Greg, if I've miss played this, let me know now and you can forget I ever said it."

"Yeah, I don't think I can un-hear that."

"Then we're good then, for tonight?"

"Sure, but.."

"Greg, the less you think about it the better. See you at seven."

The less I think about it. It's all I could think about. Don't let anyone kid you, when a woman, especially a woman as accomplished and attractive as Dylan, states emphatically that she needs your penis, well, there isn't much else to think about other than why.

What, exactly, did she need my penis for? I know that she had been married for a short time when she was in her thirties and never had children. But she's my age, mid-fifties. My guess is she's not looking to get pregnant.

Maybe she needs me to get someone else pregnant. Maybe a lesbian friend; a younger lesbian friend. Maybe Dylan's a lesbian, and the two of them are going to come over for a threesome and I'm supposed to get her young lesbian lover pregnant. Okay, now I was going off the rails. If she wanted me to donate sperm, she would have asked me straight away. In the same manner she just stated she needed my penis.

I was more than a little dumbstruck. I had known Dylan for more than a decade, and I could describe my relationship with her as with all my female collogues: professional, respectful, and platonic.

This wasn't a #MeToo occurrence. Not that I didn't find some of the women I worked with attractive; there were times a coworker or colleague got caught up in my masturbatory fantasies, but never someone I had direct contact with, and never Dylan. It would be too difficult to sit across from someone in serious conversation knowing that earlier that morning I spanked off to the thought of them blowing me while I sat on the edge of my pool.

And it's not like Dylan wasn't spank worthy. She was tall, probably 5' 9", though there were times when in heels she could almost look me in the eye. She had long black hair, deep brown eyes, and a darker, a Mediterranean-like complexion.

She had a largish mouth and perfect teeth that glimmered when she smiled. And, depending on her undergarment choice of the day, either a decent bust line or a set of boobs that could smother you. After all these years I still wasn't sure about that one.

She was also extremely fit. Years ago she had played division two basketball. She had carried her athletic instinct with her to this day. Last week she competed in her tenth mini triathlon. Plus, if all that wasn't enough, she was smart. Really smart. Much more so than me.

My mind began to churn from adolescent-like anticipation to deep concern. On one hand, and now that I had a moment to process this, Dylan had a playful side. She was very self-aware and confident, and from time to time I thought she was flirting with me. Had I met her in a different setting I would definitely be interested in something more carnal than casual. But this call, this call was weird.

At exactly seven o'clock the doorbell rang. There was a polite greeting, a hint of smile from Dylan as she came through the door, and a boat load of awkwardness.

"Nice house," she said, quickly scanning what could be seen from the foyer. "What are these, nine-foot ceilings?"

"Thank you, and yes, nine feet," I answered.

"Nice. Mine are eight," she said. "Though I might move."

"Eight's standard, I think," I said. "Where might you move? Just for higher ceilings?"

"Don't know. Maybe I won't. Window treatments cost more. Your drapes are nice."

"Thanks. They came with the house."

"Oh, that's nice. Floor to ceiling treatments are expensive."

"Yes, so I'm told."

The inane conversation on décor came to an end. Then, eerie silence.

As she looked around, I looked at her. Professional, yet different than normal. The suit, dark blue skirt ending just below her knees with matching jacket, I'd seen before. But her cream-colored blouse was a tad too sheer for the office. Her patent leather black pumps featured an inch or two more heel than standard fare. The glitter from her bangle necklace seemed more appropriate for after dark. Matching earrings dangled in her hair look like it's just been blown out.

There was also the fact that one more button was undone than usual on her blouse, a guy notices these things, and her choice of bra was more cleavage defining than what she would wear in the office. And the red lipstick, that delivered an entire message on its own.

I was in jeans and a golf shirt with deck shoes. One of us was either over dressed or underdressed. I broke the ice. "Can I get you something to drink?

"No, maybe later."

"Did you have trouble finding the place?"

"GPS Greg, so no."

This was as icy an interaction as I've ever had with her. I couldn't quite tell which of us was more nervous. Why I don't know, but there was palpable tension.

"You didn't wear that outfit to work today, did you?" I tried again.

"I wore most of it."

"It's nice. Very, what's the word, oh yes, uplifting."

"Yes, I suppose it is," Dylan said.

"Would you like to take a look around the house?" I was grasping here, no idea what say.

"No, not really."

"Dylan, I'm not sure what to do. This is your meeting, so to speak."

"Yes, I know."

Dylan wet her lips with her tongue and brushed her hair of the side of her face with the flick of her left hand. I've never known her to be at a loss of words. She was either rethinking the entire endeavor or trying to figure out how to take the next step. Time to expunge the elephant in the room.

"You said something about needing my penis."

"Yes, yes I did."

"Is that still the case?"

She hesitated, gazed at me from head to toe and back, and said, "Yes, still the case."

"Can you be more specific? Do you need me to stand naked so you can draw it for an art class? Do you need me to donate sperm for a particular friend or cause of yours?" I said, purposely dancing around the edges.

It's not like I didn't want to say, 'do you want to jump on it and ride into the sunset,' but Dylan was more sophisticated than that, and if it was the case, saying something like that may lessen the chances of it happening. And, despite our purely professional relationship, looking at her here, in my house, after her tossing the first salvo, that's about all I could presently think about. The professional relationship stuff, that left the building when she entered my house sporting maraschino cherry-red lipstick and a push-up bra.

"No, no, I'm sorry," she said, breaking her stoic cadence and returning to the Dylan I knew. "This is a big ask, and I feel, well, a bit uncomfortable, and to some extent, embarrassed. But you know me well enough to understand that if I need something, I'm going to do everything I can to get it."

"Absolutely."

"And I believe I know you well enough, that, despite the unconventional nature of my request, I can count on your complete discretion."

"Am I the right person for this, whatever this may be?" I asked, hoping to hell I was as my imagination continued to run in all sorts of erotic directions. I know she didn't wear that blouse with that bra to the office, so I can only surmise that it's a component of some sort of seduction.

"Greg, trust me, I've run over this 'till I'm exhausted. Despite what outwardly appears as hesitation or second thoughts, not only are you the right person, you're the only person."

"Only person for what, exactly?"

I've never seen Dylan look more vulnerable. She broke eye contact, glanced around the room, took a deep breath, and said, "I need it, your penis, your cock if you will, in my mouth."

There's no protocol for a genial response to this statement, so I played it with as much humility as I could forge.

"You're kidding," I said.

"Do these lips and breasts look like I'm kidding? Come on Greg, let's leave naïve role playing for another day."

"Not in a thousand guesses would I have gone there," I lied.

"Seriously, a thousand guesses. So around guess 475 you wouldn't think, 'hey, maybe Dylan wants to suck my dick.' You need to begin thinking more highly of yourself. You're a very good-looking gentleman. Besides, I know deep down, despite your professional façade, you've always had a bit of a thing for me. I've caught you staring at my boobs a million times."

"Maybe a bit more than a million."

"Probably."

Silence once again filled the room. Now I know what she wanted, though still a bit suspect, but what next. Whip it out, say 'here you go, have at it.' Not the elegant choice.

"Okay, I'm all in, discretion and all. Thank you, I guess."

"Wait until it's over before thanking me," Dylan said. "I'm assuming you have a serviceable penis, right. No diseases."

"Maybe you should have asked that first," I said, pausing for minor effect. "No worries, I'm clean as a whistle."

"Wonderful. Where do you propose this takes place?"

"The bedroom is back this way."

"No, that won't do. This isn't a bedroom blow job, Greg. I assume you have a home office."

"I do," wondering what the differences were between a bedroom blow job and non-bedroom blow job.

"Perfect. Let's go there."

As we stepped into my office, I sensed there was a shift. As if I had fumbled the football deep in my own end of the field and Dylan recovered. She tapped me on the shoulder and indicated I should turn around. Her radiant smile had turned into a quasi-evil smirk. She ran the middle finger of her right hand from my chin, down my neck, chest and stomach, and came to rest on my crotch.

I had been semi-erect the moment Dylan walked into my house, and now I was feeling quite full. She gently cupped my cock through my pants, gave it a little squeeze, unzipped my fly. I guess we were really going to do this.

I moved to unbutton her blouse and liberate her swelling breasts. I had indeed spent an inappropriate amount of time sneaking peeks at those, though apparently not as covert as I thought. My fingers were met with a swift swat from Dylan.

"No touching. This isn't about you, Greg," she said. "I guess I should go over the rules. Keep your hands to yourself. If you put your hands on my head, I'll bite your dick off. No talking, though you can offer praise from time to time on how good it feels, and I guarantee it'll feel very good, at least most of the time. Other than a pleasurable moan here and there, don't say anything. Except when you're about to cum. I can't stress this enough, please tell me when you're about to cum. I don't want this to end poorly."

Her mini lecture softened me a bit, an occurrence that didn't escape Dylan as she began to lower my pants to the ground.

"It is going to get bigger, right?"

"I guess that depends on you."

"Fair enough. Have a seat and let's see how big this guy can get when he's excited."

Dylan began by rubbing my balls and running her hand up and down my shaft. After a moment or two she let go. She kicked her heels off and turned away to grab a cushion from the chair in the corner. She placed it in front of her and descended to her knees, and slowly circled the tip of her tongue around the head of my penis. Time and time again, around and around. Finally, she kissed it ever so gently before bringing it into her mouth. She cradled it there, running her tongue underneath while slowly sucking on the head.

She pulled away, licked my cock from stem to stern, repeating the process to ensure not a fraction of skin went unbathed. Dylan then shifted her attention to my testicles, bringing one then another into her mouth, swirling them around, and letting them escape with a subtle "pop" before she once again lathered my dick with her tongue.

She methodically stroked me with one hand and completely removed my pants from around my feet with the other. Dylan then spread my legs wider so she could have better access to, well, everything. She firmly sucked my right nut into her mouth and pulled away from me while stroking my cock in the opposite direction. This is where I let out my first audible sigh.

Dylan let my testicle fall out of her mouth. She said, "You like that, do you? I was wondering if I was having any affect."

"No, you're having the desired effect."

Dylan looked up at me and said, "Interesting you say that, given you don't really know what effect I desire."

She rose up tall on her knees and removed her jacket—tossed it aside. Positioned above my cock, she firmly grasped the base and went down on me, easily taking half my cock into her warm, salivating mouth. Dylan bobbed up and down, now with some pace, while twisting her head right and left, generating the always welcome sound of cock slurping.

"Oh god Dylan, that feels good. Really good."

She responded with a sort of hum, "hmm, hmm," while maintaining the rhythm she'd developed. This motion was her focus for a few minutes, continuing up and down, left and right with her mouth, never losing contact. She then palmed my balls, massaged them as she rolled each between her forefinger and thumb.

Dylan slowly let my cock slide out of her mouth. She looked up at me with a shit eating grin and ran her lips over the tip, then down one side and up the other. With her thumb and forefinger of her left hand firmly wrapped around the base of my cock, Dylan began to slowly stroke me with her right hand, her mouth now literally sucking on the head as if she was attempting to draw out my cum.

"Oh god, mmm, that feels so good, oohhh," I said, and checked 'needing your penis' to learn how to give a blow job off the list. This felt amazing, and the percolation of pending orgasm suddenly appeared. "Oh shit, Dylan, I'm about to cum."

Without hesitation she let my cock drop out of her mouth but tightened her grip on its base.

"Seriously? What's it been, ten minutes?" she said somewhat mockingly. "What are you, 16 years old. Come on, get some staying power."

For my part, remembering the virtual no talking rule, all I could do was pant and let out a sigh. After she suppressed my ejaculation, Dylan stood, flung her hair around with the whip of her neck, and left the room.

"Don't go anywhere," she said, "and definitely don't whack off."

After what seemed like an hour, but was probably only a few minutes, Dylan walked back into my office. She had found something to tie her hair back, and there was one less button fastened on her blouse. She also had a glass of wine.

"This is pretty good stuff," she said, and took an elongated sip before placing the glass on my desk. "Okay, now where were we. Oh yes, you were about to prematurely ejaculate. Not a good idea."

Dylan knelt before me, a somewhat subservient gesture on her part given how this has progressed and resumed sucking my balls. She brought one into her mouth, played with it with her tongue, exchanged it for the other. Then something happened that no one had ever done to me before—she opened wide and managed to get both of my testicles into her mouth at the same time. The sensation of the warm, moist confine cradling my balls was titillating.

"Aahhh, oh my god, ohhh, aahhhh."

My erection retuned and bounced off Dylan's cheek. She softly grabbed it with her fingers, caressed both sides of her face with it before she lifted it to her mouth. She rubbed her lips with the tip, flicked the frenulum, and gave it a big kiss before slowly sliding it back into her mouth.

Dylan gently scraped the head of my cock with her teeth. When she got to the rim of the head, she softly bit down while securely wrapping her lips around it as well. She tightened her fingers around the base of my dick and pulled my cock away from me with her mouth, essentially putting me in oral traction. She sucked hard on my head before again traversing down my shaft.

"Oh shit," I blurted out as a surge ran through my loins. "Oh man, does that feel good."

Dylan murmured her acknowledgement of my compliment. She methodically worked her mouth up and down my shaft, stopped each time about halfway; each time she stopped I was hoping she'd take it all. This went on for a while, with intermittent twirls of her tongue around the head. Despite being in the middle of what was easily the best blow job I'd ever had, I couldn't quite shake the idea that it would be even better if I could at least see Dylan's tits, if not play with them.

She paused to lap-up some pre-cum and looked up into my eyes with a wicked smile. She just stared for a few seconds, and then began to run her fingernails up the underside of my cock. The further her fingers went the bigger her smile.

"Oh my, oohhh that feels wonderful. Oh, Dylan, I'm, I think I'm ready to cum again. I know you don't want me to, but shit, yeah, I think I'm going to cum."

Dylan's smile turned to a frown. She put the head of my cock into her mouth and bit down on my head, not too hard, but enough to send a message.

"Ouch, what the hell Dylan."

"What do you mean, what the hell, Dylan? What the hell Greg," she said before she firmly gripped my dick and closed around it like a vise. "Hey, I know I'm good at this. Actually, I'm great at this, but please, try to hold out. I think it's fairly evident, I'm not done yet."

I've had my fair share of blow jobs, though at this moment I don't even know what that means, many good, some not so much, a few excellent. I found it odd when some of the women who were good, who knew what they were doing, either were embarrassed by it, or flat out in denial. Not Dylan, she owned it.