Hopeless, Romantic

3 min read

I walked into the office and said to my PA, “Ms. Gale, please block out the week of September fourth through September tenth. I’m going on vacation.”

She looked up from her desk, her blue eyes shining with curiosity through her wide-rimmed glasses, and asked, “Vacation? Where?”

“That’s right, vacation. I’ve gotta get outta here. I booked a resort hotel for Lo and me on a beach in Maui.”

“Ooooo, really?” she squealed with excitement. “Are you going to propose to her there?”

The question took me by surprise. “Propose? Why would I do a darn-fool thing like that?”

“Because, Mr. H., that’s what people do at those romantic resorts on the beach.”

“People,” I said with scorn. “I am not people.”

“You’re in love with her, aren’t you? Why are you just stringing her along?”

“Ms. Gale, you are correct, I am madly in love with Lola.”

“So why don’t you get married to her?”

“Because I am madly in love with Lola. I am not madly in love with marriage. Marriage is a comfort that, once achieved, leads to the erosion of love.”

“Oh, Mr. H., you’re such a stick-in-the-mud.”

“And you, Ms. Gale, are a busybody twenty-something who has never been married, divorced, or lived fifty some-odd years to learn from experience.”

“Well, that’s no reason to not get married.”

“If you’re so crazy about marriage, why don’t you marry Lola?” I asked as I walked out of the reception area where Ms. Gale had her desk, slamming the door to my private office.

That was how my day started. It only got worse from there. Needless to say, by the end of the work day, which was nine at night for me, I was in no mood for Lo’s tomfoolery.

I walked into the bedroom, found Lola naked under the sheets, doing what Lola is always doing when she’s naked under the sheets with easy access to her phone, and I began to undo my tie and remove my button-down shirt.

“Oh yeah,” Lo moaned.

“Is that meant towards me, or your porn video?” I asked as I removed my pants.

Without taking her eyes off the video or her hand from between her legs, she replied, “Yes.”

I washed up in the bathroom and returned, taking off my pants and getting under the sheets next to Lo. “Well, Daddio, am I going to get any tonight?” she asked as she was rubbing her pussy lips under the covers with one hand and holding my flaccid cock with the other hand, the phone with the video still playing next to her, flat on the bed. I could hear the couple in the video moaning and groaning.

“You have to get me hard first,” I said.

“That seems to be an insurmountable obstacle,” she replied, lifting and dropping my soft dick.

“Really? I never thought I’d hear you say that.”

“I never have had that problem… with other men.”

Within moments I was asleep, or so Lo told me the next morning. She had to get her rocks off without me… again.

When I woke in the morning, I found her curled up next to me, her eyes already open. “You can fuck me if you want to,” were her first words to me.

Luckily, having expelled all my bad feelings of the previous day through my sleep, I was very “up” that morning.

“Roll over on your back and spread your legs,” I said. My first words to her.

“Oh, Daddy! You’re so romantic!” I honestly couldn’t tell if she was being sincere or sarcastic.

I positioned myself over her naked body and took a good look at her. “You look good,” I said.

“Prove it!”

“The proof is in the puddin’, and I’m puddin’ it in you.” I slid in. She was dripping wet. “Lo,” I said once I was deep inside her.

“Yes, Daddy?”

“How long have you been up?”

“I don’t know. Why?”

“Did you jill it?”


“This morning.”


“How many times?”

“Daddy, I’ve been jillin’ it since last night. I have no idea how many times. I’m sore and soaked and I want you.”

“What have you been jillin’ it to?”

“Daddy, I can’t remember it all. Just shut up and fuck me. Please.”

I shut up and gave her what she asked for. But she asked, “Can I turn over, Daddy, please?”

I let her turn onto her tum and she put her ass up in the air to be had from behind. But then I saw her grabbing her phone and looking at it. One hand held it up for her to see and the other was manipulating her clit. I tried to see what she was looking at, but couldn’t quite make it out.

“Lo, what is that?” I asked as I leaned forward and put my hands on her shoulders to see better.

“Never you mind. Just get back there and do your job. I want to feel you, hard and deep and hard.”

I complied with her demands. She came. At the moment when I felt her pussy clench on my cock, I came too, deep inside her. She collapsed into the pillows, dropping her phone. I fell on top of her. Eventually, I slowly pulled out. Looking down at her, I quoted one of her favorite films, “Little full, lotta sap.”

She laughed and then said, “Clean me up.”

I took care of her and then suddenly she was up and out of bed.

“I have to go now,” she said.

“But you only just came!”

“Work, Daddio. I have a job, remember?”

She went into the bathroom to get ready. I picked up her phone and went through her browsing history. I was shocked by what I saw, but I figured I’d ask her about it that evening, when we could explore her fantasies together. I put down her phone as if I wasn’t looking at it just as she opened the door to the bathroom. She was putting on her makeup. “Honest answer,” she called to me, “do I look like a trollop to you?”

“Honestly? — Not enough of a trollop.”

“Perfect. That’s just what I’m going for.”

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