Pilot in Command Ch. 01

PILOT IN COMMAND — Chapter One

Author’s note: This is a tale about a 22 year old woman’s journey of sexual discovery with an experienced, older lover – and others. When her journey begins she is not a virgin, but she is inexperienced.

The first chapter is how the journey began.

Special Gratitude to ChancesAre for skilled editorial help that taught me to recognize problems in my work.

As always, your feedback and ratings are valued. I appreciate hearing how my stories are received.

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ONE — AHKI and TESSA

Ahki began her journey of sexual discovery after a late night revelation by her best friend Tessa.

Tess lived in Chicago, three hours from Ki’s apartment in Madison, but often drove up to spend long weekends with her. It was late one night on such a visit when Tess confessed she was in an ‘arrangement’ with a Chicago lawyer in his fifties. She admitted that it was his wealth that provided the considerable start-up money for her fashion photography business. Ki didn’t voice her revulsion, but it was clear enough from her expression.

Tess rushed to explain. “It’s not like that” she said. “I picked him. I posted on a website and got a ton of responses and he’s the one I picked out. I…chose…him…Ki.”

“Show me the website” Ki said. They looked at it together. Sitting on the couch with glasses of wine and their legs tucked beneath them, they looked with the iPad between them. Ki tried to keep an open mind as Tess described how it all worked but eventually had to react. “This is young women offering to have sex hook-ups with older men for money!” She stated reproachfully.

“Sure” Tess countered, “But it doesn’t have to be. I used it to find what I wanted.”

“What did you want Tess?”

“Well…I guess I didn’t even know until he found me.” She looked at Ki. “We talk sometimes — his name is James — about how remarkable it is that we found each other on this site, or found each other anywhere.” Tess looked wistful as she continued “He courted me. He knew what to say. He played me like an instrument and I knew he was doing it and it still felt wonderful.” She paused thoughtfully and continued “It was like living in the past when men wooed women romantically.”

“What do you do together?” Ki asked.

“We’re lovers” Tess said matter-of-factly, relieved that her secret was finally in the open between them. She needed Ki’s approval, but knew it might be a long time in coming. “He’s a wonderful lover. He knows how to touch me and tease me and talk to me and hold me. He knows how to take me as his and how to let me go.” She studied Ki’s muted reaction and continued “He pleases me over and over and over, and loves it. When his tongue is sliding into my pussy, probing and licking and tasting me, I know I’m adored. When he licks my breasts and sucks my nipples into his mouth it feels like he’s suckling my soul.”

Ki’s stern expression softened, a bit, so Tess pressed on. “When we make love it is other-worldly. Little things are magnified. He owns me with his lips on my neck or his nipping teeth. What scares me Ki, is what I will do if I lose him. How did we find each other? Together we are perfect lovers but is it only serendipity that we found each other at all? Can love be so capricious?”

“You love him? ” Ki asked with concern. Then quickly added “Why would you lose him?”

“I do.” Tess admitted. “I’ve never told him I love him. He’d never ask me and I’d never ask him.” She sighed, “It’s an arrangement. When the scents and sounds and heat of our lovemaking fade — it’s an arrangement.”

Tess continued “Sometimes I think that, for sex, ‘love in the moment’ is as good as it gets? When James makes me cum it feels exquisite, but I know it excites him more than it does me. I can feel it. I can feel his pleasure in my satisfaction. And it’s the same when he cums for me. When I take him into my mouth and I’m licking and sucking and I feel his cock swell and I know he’s about to cum – I’ve actually whimpered for it. When the first jets gush into my mouth I love it so much I wonder if it’s really me having the orgasm, and maybe it is as he cums for me and I suck and gulp and swallow every precious drop.”

Ki was wide-eyed. Blinking. Awed by her friend’s radiance and her graphic words. She ached inside but sat in exaggerated stiffness.

“I feel beautiful in that moment. I feel sexy and powerful and when I make him orgasm it’s proof of my beauty. My mouth is full of proof. It is real and warm and I taste it.”

Ki blushed so deeply it burned her cheeks.

Tess began again. “That isn’t even the best. The best is when we cum together. Google it! It’s supposed to be so rare for lovers to climax simultaneously. We do all the time, more often than not, and it’s usually my second or third one.” She was beaming at Ki, “sometimes the fourth and once the fifth!

“Do you know what that’s like?” Tess asked. “Can you imagine?”

“No.” Ki replied uncomfortably. She closed the iPad, asking “But an older man, how sivas escort old?”

“59” Tess replied. “Do you really think it could be like that with a man our age? Do you think it could be like that with Jim Jensen?” He was a classmate of Ki’s that she’d dated for 5 months.

“Not even when he’s 88!” came the quick reply. They laughed then, comfortably – gratefully – with less tension. Then Ki asked a flurry of questions, wanting to understand why Tess’s lover was so special. How could Tess feel that way with a man who was almost 40 years older?

“I’ve thought about it,” came the reply. “I think it’s because he’s older – not despite being older.” She faced Ki on the couch and took her hands. “He’s not trying to get off as much as he wants to feel and kiss and taste and be inside me. I feel special because it’s me he’s sliding his experienced cock into.”

Despite Tess’s intense sincerity, Ki almost laughed aloud, saying “Experienced cock?”

“Yes!” Tess proclaimed, undeterred. “Think about when you had sex with Jim. Think about what it felt like when HE was inside you.”

Ki did think about it. She remembered it felt like he was “doing something” inside her. She remembered her surprise and disappointment when he came. She remembered wondering what all the fuss was about. Mostly, she remembered her detachment. “He used my body to jack himself off” She said with disgust.

“When James slides himself into me it’s to be inside me. He loves to watch my face as he’s pushing his cock into me. He told me he wishes I could see how beautiful I look in that moment. A man penetrating my sex, stretching and filling me and knowing exactly how it makes me feel. And God Ki, it’s when I’m stuffed full of that cock of his that he begins to fuck me. I feel the head as he pulls almost all the way out and then pushes inside me again. Every inch. And out again, and in. Slowly. And again – until I’m clawing at his back and wrapping my legs around him and begging him to fuck me. When he finally loses control and starts driving into me with his powerful thighs and I’m gasping and I know there’s no stopping him until he’s filled me with his thick load and I’m screaming for it and craving his cunt-searing cum deep inside me – it’s pretty damn clear to me I’m being fucked by a man. And yes, by a man with an experienced cock.

“Jesus Tess,” Ki said hoarsely. “T M I.”

Tess replied defiantly “You called it sex hook-ups for money, and I’m sure that’s most of what comes from that website. But I want you to understand that’s not what I’m doing with James.”

“OK Tess. I do.” They hugged, and held each other. “I do,” she said again.

Later, Tess fell asleep quickly as they snuggled in bed. Ki lay awake for a long time, listening to her friend’s relaxed breathing, feeling left behind.

TWO – AHKI

The images of that late night conversation glowed inside Ki for the next week. She wandered the internet searching topics like “sugar babies discuss their sugar daddies” and “why young women prefer older men in bed”. She even read some May / December erotica on Literotica.com.

In a chat room a young woman explained why the sex in her arrangement was the best she’d had. “That’s all it’s about” she wrote. “Pleasing each other physically is our whole thing when we’re together. Not talking about bills or life plans or obligations or who should take the damn garbage out? We meet solely to please each other sexually.” When questioned by another participant, the writer agreed it wasn’t like that for everyone. Her friend’s arrangement was with a sugar daddy who only wanted to be ‘serviced.’

When Ki logged onto the arrangements website again, she told herself it was ‘for the money’.

Creating her Bio looked easy enough, mostly filling in boxes. Why not?

EARTH GIRL (She picked that title for her Bio because her full name – Ahkiiwan -meant “of the earth” in Ojibway)

23 / slim / Native American / 5’2″

In the “about me” section she wrote: “I’m a college student working towards a Masters in Behavioral Neuroscience and Psychology. I love to laugh and go on adventures. I consider myself to be fun, kind, intelligent.”

In the “seeking” section she checked the boxes for: “men / attentive / discretion / flexible schedule / luxury lifestyle / no strings attached / vacations.”

In the place where she was supposed to describe what she was seeking she wrote “I am looking for something casual and with someone who is able to have a flexible schedule. I am looking for help with bills and some extra money. Vacations are nice too, but not required.” Finally she added “I’m looking for real.”

And what about her pictures? She debated which pictures to use until she gave up and went to sleep without posting her Bio. In the morning, in the day light, it ALL seemed like a bad idea.

On the phone that night she read the Bio to Tess, who had one suggestion. “You should add that you prefer older gentlemen. Most of the younger guys who responded sivas escort bayan to my posting were assholes and jerks, number one. And frankly Ki, they didn’t have the money.”

Ki’s response was immediate. “I thought it wasn’t about the money?” she demanded.

“It’s not,” Tess replied evenly “but it sure is nice. Besides, older men are upfront about the money and it’s a good way to gauge how serious they are?”

The next twenty minutes were spent deciding which photos Ki should add to her posting. They picked two that featured her smile. For a ‘private’ pic they chose one where she was standing on a beach in her skimpiest swimsuit, facing away with her head turned back towards the photographer (Tess). Her hand was at her chin coquettishly. The most prominent feature throughout the photos was her luxuriously long black hair.

After the call, Ki added “I prefer older gentlemen” to her Bio. She reread the entire Bio twice. Finally, just before falling asleep, she clicked ‘submit.’

When her eyes popped open in the morning she filled with dread. OH NO! She rolled to her side, grabbed the iPad and turned it on. It opened still on the website and she saw she’d gotten eight responses. Two were “Hey” messages and four were variations on “How are you?” Ki had no stomach for ANY “I’m fine, how about you?” message strings, much less six of them! Click. Delete. Six times.

The seventh message was longer but demonstrated a shocking inability to communicate in coherent sentences. Click. Delete.

The eighth message was from “Pilot in Command”. Really, she thought derisively, pilot in command? Just a bit full of ourselves, aren’t we? To top it off, he didn’t include a picture in his Bio. She read his longish message anyway:

“Hi, I appreciate your ‘to the point’ bio. You are gorgeous.

“I’ll also get right to the point. I have been in two arrangements. The first lasted over ten years and the most recent lasted 3 years before it ended. They both worked because the chemistry between us was quite real though our meetings were always private and usually in hotel rooms. Over time it was like we carved a separate reality that was apart from the rest of the world, apart from the rest of our lives – a place we escaped to together.

“I’m looking for that same sort of relationship again. Obviously with our age differences it wouldn’t be like seeing a boyfriend but I expect you would enjoy the genuine warmth of my caresses and my adoration of your physical beauty.

“Brief erotic escapes together. A genuine connection, with sexual adventure and passion and affection and mutual satisfaction and benefits. A smile and a soft shared laugh and until next time.

“So, the practical aspects. I understand the need for a clear understanding of the base of our arrangement. I run several companies and time is one of the things I have the least of. I would want to meet privately, usually in the Madison area, on weekdays during the day, a couple times a month. I am not available any other times. I would very discretely and quietly give you a gift of $1,000 at the outset of each meeting. If our arrangement becomes long term I’m sure there will be other financial needs I cover for you.

“While I’m not willing to post pictures on this site I will share a picture if we have a promising email conversation. I am generally considered to be a handsome and fit older gentleman.

“An ‘arrangement’, yes, but more so I’m seeking an affectionate relationship where we both genuinely look forward to the next time we are together. I want us to miss each other when we’re apart.

“What are you looking for?

“If you want to discuss this further my preference is email.

“Thanks!

Gus”

[email protected]

After reading the message, Ki looked at his Bio.

“PILOT IN COMMAND

“60 / slim / white / 6’2″/ married

In the “net worth” and “income” sections there was no amount shown. He simply filled both in with “High”.

In the “about me” section he wrote “I adore a natural beautiful woman. I am fit and work out regularly. I am gentle and kind.”

In the “seeking” section he clicked four of the boxes: Discretion / Friends with benefits / Long-term / and No strings attached.

In the text portion of the “seeking” section he wrote: “I am looking for a woman to have intimate, private encounters with on a regular and long term basis. I’ve been in two long term arrangements. They worked because the chemistry was right and because we took the time to learn each other’s likes and triggers so our encounters were fun and fulfilling for both. Absolute discretion is essential. I am generous.”

Ahki reread his message. She knitted her brows. She wondered if he was for real, or what part of him was for real. She wondered if she was for real when she posted her bio. She was frozen with indecision even as she was overwhelmed by the need to decide.

She agonized for ten minutes before deciding. She deleted her Bio. She escort sivas didn’t temporarily suspend it — she deleted it. Done.

It was 8:10AM when she hit ‘delete’. Just ten hours after first posting it. Just seconds after copying Pilot in Command’s message and pasting it into her iPad.

THREE — GUS

Like always, Gus got up before dawn. He checked private email on his phone while the coffee was brewing. There was nothing from ‘Earth Girl’.

She intrigued him. His message to her was straight up. He was in two arrangements. They were as he described. His life was good without them but they added a sparkle he missed. The responses he got from the website were discouraging. He was ready to give up. When his wife entered menopause 13 years earlier, she lost all interest in sex. Maybe it was time for him to accept that his sex life was over too?

At the office a few hours later he rechecked his private email. Still nothing. It was 9AM before he logged into the website to see if she’d even read his message. Where he expected to see her Bio, there was a circle with a diagonal line through it and a message that read PROFILE BLOCKED. It said “This member’s profile can no longer be found because they deactivated it or blocked you.”

“Well OK” Gus thought “I guess that’s not happening.” He reread the message he’d sent Earth Girl and was struck by how transactional it was. He wondered whether it offended her, or grossed her out, or whether she closed her whole account, but quickly decided it didn’t matter. He wasn’t going to meet her. It wasn’t going to happen between them. Dispirited, he logged off. There was something about her smile he thought with genuine regret.

Over the next couple of weeks, Gus got several notices from the website saying that he’d received a message. None of them were from Earth Girl so he didn’t log in. He thought about his last lover. Kait contacted him on the website, less than a week later they met in person and 90 minutes after that they were naked together. Whirlwind. And the whirlwind had carried him into the most intensely passionate physical intimacy of his life. It only grew more intense over three years as lovers. He hadn’t known it could be like that. He was stunned. He was on the website because he desperately wanted to experience a physical connection like that again.

It wasn’t just sex he was missing. He was wealthy and handsome enough and accomplished and powerful and travelled frequently – he knew sex was readily available if he wanted. Women of all ages would let him know they were ‘available’ through a ‘look’ or their posture or a lingering glance back as they walked away. They let him know through a word slipped in that was accompanied by a smile.

And it wasn’t love that he was missing – not really. He deeply loved his wife. She was the “love of his life”. They fulfilled each other, completed each other, for over 30 years. They were comfortably married and he would never let anything change that. Physical passion was in the past, but he cherished her. He would take care of her and love her forever. She knew that in her marrow.

Yet what he and Kait had was real. A physical joining so complete that it defined passion. Not ‘sex’ even as it was the most intense sex of his life. Not ‘love’ even as it was as pure a love as he ever experienced. Two people, naked and joined sexually with nothing held back. Giving themselves to each other without expectation or obligation or commitment. His cock inside her and their tongues swirling were only paths to a combination so absolute that skin no longer separated flesh and their hearts beat as one and they came as one. After, in bliss, holding each other, they gradually – reluctantly – became two again. Two lovers holding each other as they became aware it was time to return to their lives…

He needed what he’d found with Kait — then lost.

He shook his head as if to clear it. He was meeting his sales manager at the airport and flying them both down to Oklahoma City. They were pitching the airport manager at Wiley Post Airfield and he needed his head clear for the flights down and back and for the pitch. Hell, forget the flights and deals, he needed his head clear for his life.

He deleted his Bio.

FOUR – AHKI and GUS

Gus idly checked his private email a few days later and saw he had a message from ‘abearheart’ with “What you described” as the subject. He opened it in ‘safe mode’:

“Hello Gus,

It’s Earth Girl from the arrangements website. I’m also looking for something very discreet. I’m looking for the same thing you are. You described what I want better than I could have 🙂

Please email back if you are still interested? My name is Ahkiiwan, but my friends call me Ahki or just Ki.

Thanks, Ki.”

Two pictures were attached to the email. The first was a smiling close-up. The same beautiful young woman from the posting. The same eyes and long black hair and enchanting smile. The second was taken on a beach. She was wearing a skimpy bikini, half turned away and looking back at the photographer over her shoulder. Her smile back to the camera pierced Gus. It was as if she was looking back to no one but him. It was her dark eyes. Her figure was perfect – slim and willowy, with well-defined bone structure, smallish breasted.