by Jamie Knight
Hayley flinched away from me. She looked up at my face for a second then dropped her eyes to the floor like an ashamed puppy.
I clamped my mouth around my next outburst and tried to cool my temper. Picking up the dropped cup, I salvaged what I could of her drink, apologized to the barista, and taking Hayley gently by her shanking hand; I handed her the cup.
She looked down at it like I had handed her a snake.
“Shall I get you a fresh cup, miss?” the waiter asked as he finished cleaning up the spill.
Hayley looked at him. “Yes…I mean, no. I’ll have hot chocolate. I hate coffee, it’s disgusting.”
Why didn’t she say anything earlier?!
Staring at her and the distant look she had on her face, I felt embarrassed. My feelings were only made worse when the barista looked over at me and raised his eyebrows, seeming to indicate that I was rude to not get my date what she wanted. But she had never said anything.
I sat down, trying to get my mind off of my annoyance, but it was hard with wet pants and everyone still staring.
This was probably a bad idea. I wasn’t good with women. I should have ignored what Ann and Vicky said. Hayley would never make a good fake fiancée for Carl’s wedding. The girl obviously could not stay calm, and there was no way we could get along.
It was the hot chocolate that was the final proof. Not the fact that she preferred that to coffee, which could admittedly be pretty disgusting, but that she didn’t even bother to tell me. How could I deal with a woman who wouldn’t even talk?
To be fair, she also hadn’t said a word since we had left Ann’s office. It was a form of selective mutism I had seen before, generally brought on by trauma, or at least intense fear. I didn’t know what she had heard about me, but it was a safe bet that it wasn’t good. It was a mistake to ask her out, cute as she was.
“I won’t bite,” I said after a few moments of silence.
“I-I know,” she said, still not looking me in the eye.
“What’s wrong, then? Your shaking like a Chihuahua in a thunderstorm.”
That actually got a giggle out of her, which was a nice surprise. I really hoped I wasn’t as scary as I seemed.
She glanced at me out of the corner of her eye, then immediately looked back down at the table again. “I-I’ve just never been on a date with a rich man before. Y-your also really s-sexy, it’s, you know, intimidating,” she managed.
Her words hit me hard. On the one hand, I was happy that she thought I was sexy. On the other, did she only think I was sexy because of my money? I wasn’t really interested in a gold digger, even if it was just supposed to be for one night. Women like that were hard to get rid of.
“Well, thanks for the compliment, but you don’t have to be scared,” I told her calmly. “I have money, yes, but it hasn’t really changed me that much.”
We paused as the waiter brought over her hot chocolate and set it on the table before giving me another judgmental look. I tried to ignore him.
“I’ve heard of that, I think,” Hayley said when the man had gone.
“Self-made men?” I asked.
“Yeah,” she said, looking down at her new cup.
As I waited quietly, she blew on the cup a little to cool the liquid, then took a hesitant sip. It must have been fine because she settled in her seat a little. However, she still wouldn’t look at me.
It didn’t appear that she was going to say anything more. Conversation with this woman was almost impossible.
“Did you hear something about what I did in the war?” I asked.
“No, not really, just that you were there and then parlayed your military training and a keen mind for tactics into one of the most successful security companies in the nation.”
Wow. A full sentence.
Too bad it wasn’t an original thought that was hers.
“You read my write up in Forbes.” She had quoted it almost word for word.
“Yeah,” she said blushing.
“You memorized it?”
“No, I just remember things. I don’t know why.”
Okay.
“Must be useful in your line of work,” I said, trying to keep the conversation going, not that it had ever really started.
“Yeah,” she said.
And that was it.
I could tell she was winding down, closing off again. I couldn’t read minds, not really, but I could read people, and more to the point, their feelings. It was a skill I’d always had that had only gotten stronger during my service.
It was clear the whole fake fiancée thing hadn’t been a good idea. At least to try and do it with Hayley. The last thing I wanted to do was hurt or scare her. The evidence told me I was doing at least one, if not both of these things.
I knew I had to find a way to let her down easy. It would be better in the long run. I cleared my throat, something that actually got her to turn toward me.
“Well, I should get going,” I told her, standing up.
Hayley looked up at me, her eyes wide. It was like she was wondering if she had failed a test. “Already?” she asked, slightly breathless again. “Your coffee isn’t even done.”
I couldn’t help it. All my frustrations from that morning started to overflow. How could she possibly expect me to stay when she hadn’t shown the least bit of interest in me?
“You’ve barely said one word to me this whole time,” I snapped a little too loudly. “It is obvious, by your silence, what you think of me, and I won’t bother you any longer. I’m going to head up to Ann’s office now. By the time you finish your hot chocolate, I will be gone, and you won’t have to ever see me again.”
I picked up my cane and left without looking at her.
Chapter Four
Hayley
The disaster of a date was mercifully short, and my lunch break at the time was thirty minutes, so I had to get back to work after my hot chocolate was done. I had thought that Liam asked me out as a joke, but when he snapped at me, I wasn’t quite sure what was going on. Was he really interested? Did he indicate that he was? Maybe he had, and I hadn’t noticed, being too busy hiding in my shell. He did seem to think that my inability to talk was rude.
I guess I could kinda see that. I certainly hadn’t meant it that way.
In any case, things hadn’t gone well, and I got back to the office feeling deflated and a little annoyed with myself for being so honest about how I had never been on a date with a billionaire before. I had even been stupid enough to say ‘rich guy’ rather than his actual title of CEO.
The God’s honest truth was that I had never been on a date at all. Men never noticed me, ever. I was really quiet and tended to stay in my shell. My body wasn’t too bad, but I never really tried to show it.
My job at Howell and Howell was the first time I had worn a skirt for any extended period of time. I actually wore tights under it just in case. I was nothing if not modest.
I didn’t have the nerve to go chasing after cock, no matter how much I might have wanted to. Meeting Mr. Adams hadn’t helped. Just knowing that there were such men in the world stoked my fires even higher. It wasn’t even his money that attracted me to him but how he had gotten it. He was obviously quite clever with an amazing amount of business acumen to go from a wounded veteran to a self-made billionaire. That, combined with his good looks and super-fit body, made me want to let him take my virginity, even if I did have to be on top.
As I sat at my desk thinking about Liam, the tightness in my pussy got to be too much. I was literally squirming in my seat, my legs tightly crossed as I imagined him naked before me. Looking around to make sure no one was looking, I snuck away from my workstation, hoping that Ms. Howell wouldn’t need anything before I did what I needed to do.
One of the advantages of my job was that I had the key to the supply closet. I hadn’t been working for Ms. Howell for long, but the supply closet had already become a much-valued escape, particularly when I was feeling overwhelmed, which was quite a bit in the v
ery early days — the city itself taking its toll on my nerves.
Getting into the closet and closing and locking the door behind me, I looked for a good place. Finding a relatively comfortable patch of carpet near a corner, I sat down, my back against the wall and spread my legs. The relief was nearly immediate. I debated with myself as to whether I should actually take my tights off or leave them on. I decided to leave them on, in case I needed to get ready quickly.
I hiked my skirt up around my waist and slipped my hand into the front of my tights. The urge was to plunge my finger in my pussy and start pounding away, but I held myself back, knowing that my pussy was too tight and sensitive for that. It was not the sort of mistake that one tended to make twice.
Gently cupping my aching little pussy, I imagined Liam in front of me.
I was in a bed, completely naked and he had just come in wearing only a tank top and a pair of jeans. He took them off as I watched, first peeling off the tank top revealing his powerful chest and rippling abs. Then, he slowly unbuckled his belt, gradually pulling it out loop by loop. The belt dropped away, and I imagined him coming towards me, unbuttoning and then unzipping his jeans as he approached. He was in front of me before his jeans came down, revealing his cock, already well on its way to full hardness.
I gasped both in my head and in real life at the sight of it.
Liam gently stroked my cheek and then cupped his hand under my chin, tilting my head back, making me look at him. I did, my breath catching again both in my head and in real life. He really was perfect.
He lowered his head, kissed me tenderly on the lips, then gradually opened his mouth with me following suit, and slipped his warm tongue between my lips. As we moved closer together, his hand slowly migrated down to my boob, softly caressing my skin as it went. It was soon joined by its comrade, each of them taking them up one of my breasts, kneading them lovingly, and paying particular attention to my pert, hard nipples.
He kissed his way down my neck and over my chest. Introducing his mouth into the equation, he gently sucked my nipples and kissing the soft, tender flesh around them, making my pussy dripping wet.
As though reading my mind, Liam repurposed one of his hands. Gently cupping my aching pussy and lightly stroking my tender, pink lower lips, he made me moan softly as he used his other hand and mouth to keep working my breasts.
After a while, when I was good and warmed up, he slipped two fingers inside my pussy. I did the same in real life, trying to match the sensation as far as I could, even realizing that his fingers are a good deal bigger than mine.
Working me to the edge of an orgasm, the Liam in my head dropped to his knees between my thighs, running his tongue up the length of my pussy lips — giving my clit gentle little flicks with the tip of his tongue with each pass almost making me scream in pleasure. Doing this a few more times, he put his fingers back inside me and worked my g-spot masterfully as he licked my clit in a hard-circular motion.
Suddenly, right before I came, I imagined Liam getting back onto his feet in front of me and putting his hand on the back of my head, guiding my mouth down to his cock. After a moment’s hesitation, I dropped my entire mouth on his long, thick cock, taking in as much as I could, sucking like my life depended on it.
I could feel him tense and could tell he was getting ready to unload. I was eager to get my first mouthful of cum, so I kept going, sucking him off with every fiber of my being eagerly awaiting his torrent to fill my mouth. It came soon enough, and I instinctively swallowed, taking in every last drop of his sweet cum.
When I had recovered, Liam took me softly by my shoulders and guided me onto my back. I knew what was coming next and spread my legs wide, offering my young virgin pussy to him to do with as he wished.
Putting my legs up, so my knees were hooked over his elbows, holding me firmly in position, Liam once again stroked my pussy, again making me cum super hard. He knew exactly how to touch me.
When I was ready, he eased the warm head of his gorgeous cock against my tender little pussy.
“You’re the only woman for me,” I heard him say in my head, slipping his cock into me as he did. “I wanted you from the first moment I saw you. You’re perfect.”
He didn’t go in too far at first, just pushing in a little past the head and then paused, letting me get used to it before continuing. A few seconds later, he slipped about three-quarters of his huge, throbbing cock into my tight little pussy. It stretched me open and made me feel wonderful.
“Now you’re truly a woman,” he told me when he was inside, starting to slowly thrust in and out of my core.
“Yes,” I said, nodding quickly. “Take me. Make me yours.”
Liam started to pump his huge cock in and out of my virgin pussy, rapidly releasing me from my innocence. The pain, more a pinch really, quickly gave way to an all-consuming pleasure rippling through me in hard, crashing waves.
I held on tightly to his arms, bracing as he fucked me and brought me to hitherto unknown realms of pleasure. I realized soon enough that it was my first orgasm as a woman. If I thought the orgasms with his fingers and tongue were intense, this was even stronger. Probably because he was hitting my clit and my G-spot at the same time with his rapid movements.
I came in real life, nearly banging my head against the wall behind me, actually knocking a pack of printer paper off of one of the shelves. Quickly cleaning up, I replaced my clothes to their proper position. I returned the pack to what I figured was its place and slipped out of the supply closet, looking around the immediate area to see if someone might have heard. The coast was clear, and I hurried back to my desk as stealthily as I could, with my mind still focused on my daydream.
It was too bad that the fantasy would never be real.
Chapter Five
Liam
Most people thought that driving a Hummer was a bit much. Particularly considering I loved in the city. Bakersville was one thing, but L.A. was supposed to be civilized and advanced. Usually said by people who had never been to Echo Park where I had grown up, back before the infamous gang injunction.
People often wondered how I could be so calm around gunfire while in action. The truth was I had been hearing it since I was born.
The Hummer was also the closest to the military vehicles I had been driving almost exclusively for two decades since enlisting at eighteen. I had tried to drive other vehicles but could never really get used to them. A habitual response that did not, however, extend to guns.
I could still field strip three different kinds of firearms while blindfolded but had no desire to. I hadn’t actually touched a firearm since handing in my service weapon after being honorably discharged due to injury, following an unfortunate meeting with a roadside IED. I pulled up into the driveway of my mansion, retrieving my cane from the passenger seat as I opened to the door. The house was one of those almost laughably tacky modern constructions built exclusively for the neuvou riche. There were even stone loins set up to guard the electric gate. I mostly bought it because it was what I thought a millionaire was supposed to do. I quickly bought a second house, a much more modest beachfront bungalow in Big Sur, where I spent as much time as I could when I wasn’t working.
Because of the mansion’s new building status, it was easy to get the permissions needed to put in an elevator. The door of which was on the main floor as close to the front door as possible without compromising the structure. Pushing the button with the end of the cane, well before I got there, the elevator doors were open by the time I needed to step in. I hit the button for the third floor and waited patiently as the box cranked its way through the guts of the behemoth structure.
The bedroom was fucking huge. The floor space coming out to at least twice of most of the apartments I’d had before starting my company and making my fortune. It was still mostly open space; my furniture needs still being fairly sparse. There was a king-sized bed in one corner, made with hospital corners, and an uber-efficient modern style desk across from
it. I had heard most of the kids had switched over to their phones as their main devices. I’d grown up with desktops, however, and was still mostly used to mouse and keyboard. Desktops no longer widely available, I compromised with attaching an external keyboard to an older model desktop. Not because they were cheap but because they were easier to use, and I wasn’t afraid of breaking it in half by typing too hard, which was often the case with some of the newer slim models. I had attached a holder to the edge of the computer desk to hold my cane. Hooking the handle into it, I sat down in the retro chair made of metal and upholstery as opposed to plastic and vinyl and sighed.
Things hadn’t gone well with Hayley. It was really no one’s fault. I was who I was, and she happened to find that intimidating. I couldn’t really blame her for that. Everyone had their own perspective, and I could understand her perspective, able to put myself in her place were our positions reversed. I felt a bit bad for putting her through all that in the first place.
I wasn’t really ready to give up on going to the wedding, and I still didn’t want to show up alone. My ego just couldn’t take it. I decided that if I was going to go along with the fake fiancée idea, I might as well try and find someone who I knew would be open to it. I would have preferred a female friend, but I hadn’t really had any of those since high school. There were a few women I knew in the military, but I tended to be focused on the job at hand and was one of the few to actually take the anti-fraternization regulations seriously.
This really only left the idea of an escort. There was part of me that recoiled at the idea. People could do what they wanted with themselves, but I didn’t feel quite right about exploiting this fact. The only real conciliation was I wasn’t planning on fucking her, making the whole thing basically an acting gig. Which I was okay paying for.
Being both an obsessive and something in desperate need of efficiency, I actually looked up a list of the best escort sites before embarking on my search. I didn’t want to waste my time with dead ends and human traffickers. I still had my standards.