A Rough Conference Hook-Up

I used to be in a good place. I was thirty years old. I started a new job, which was a big step up in my career. To make it even better, I had a beautiful girlfriend, Abigail, who loved me. At least I thought she did.

Then it turned to dust.

We had plans to move in together. I honestly thought she was the one. We were dating for over a year until she broke up with me.

“It’s me, not you,” she told me with the stereotypical breakup speech. “I love you, but I’m not in love with you. I need to find myself.”

I found out, through a mutual friend, that going to find herself meant finding herself in my best friend Brad’s bed.

“Sorry, man!” my ex-best friend apologised. “We never meant this to happen.”

Yeah, bullshit.

Just when I thought I had it all, I was short a girlfriend and a best friend. I was short of several friends because what Abigail and Brad’s affair did was fracture our friend group. I cut off anyone who stayed friends with Abigail and Brad. Those who cut them off to stay friends with me were extremely supportive and were furious with Abigail and Brad for what they did.

“Harry, Harry,” a voice called out, breaking my melancholy. “Are you okay?”

I looked up and saw my boss, Meredith, watching me with concern.

“I’m fine,” I smiled weakly back.

She looked at me carefully before telling me firmly, “Come to my office!”

Meredith sat at her desk, her chin resting on her clasped hands, making her lean far enough forward that I could see just a little down her blouse. Her eyes were studying me. The office door was closed behind me.

Meredith was a strong woman who took no prisoners. I had only been in the company a short while, but long enough to hear the not-very-nice names she was called behind her back. Old battle axe, ball-buster, to name two. If she were a man, I’m sure she would have been respected.

However, despite the names she was called, those who worked for her wouldn’t hear a bad word about her and even defended her. She had a matriarchal concern for anyone who worked under her. Once you joined her team, you developed a deep loyalty to her because you knew whatever happened, she had your back.

Meredith was around fifty years old, attractive for her age, and her figure was envied and admired in equal measure. I knew she had children, and from what I heard, they were at university.

“Now we are alone, will you tell me what’s wrong? I don’t like seeing any of my team down in the dumps like you are. I have been delighted with your performance. So much so that I have been considering ending your probation period early. However, last week and this week, you’ve barely done any work. All you have done is stare into space. I want to know what has caused such a change.”

She smiled at me. It was such a warm and disarming smile that “Honestly, I am fine” wouldn’t cut it.

I closed my eyes and sighed, “My girlfriend broke up with me. I then found out she left me for my best friend.”

A small tear ran down my cheek, and Meredith reached across her desk and took my hand to comfort me.

“I’m so sorry,” she said, her expression laced heavily with sympathy.

“I thought she was the one I was going to marry.”

“And you would have made a wonderful husband. It’s her loss, I’m sure,” Meredith said with such certainty that I had to believe her. “You’re a good-looking and kind man, Harry. You have turned heads, so I know there are women here who will be very interested to know you are single again.”

Meredith has a way of saying things with such confidence that it makes it hard not to believe her because her words make you feel so good.

“I suppose you’re right,” I replied, smiling for the first time since Abigail broke up with me.

“That’s the spirit!” Meredith exclaimed with a smile. “We have a conference coming up in six weeks, which will last a week. It will mean staying in a hotel. I think it will be good for your career, and it will be good for you to get away and forget about your ex-girlfriend for a little while. What do you think?”

“Sounds great!”

“Good!” Meredith squeezed my hands encouragingly before letting go.

I don’t know if my imagination was running away with me after Meredith’s words, but the women in the office appeared to give me more attention. They became more tactile and made time to talk to me. Although I wasn’t ready for a relationship, the attention boosted my self-esteem.

Strangely, whatever affected the women affected Meredith, too.

It turned out that this conference was a big deal. My company would have a large presence, and Meredith would be making an important keynote speech.

Meredith put me on point for the grunt work for the conference preparation, and it would be my focus until we left for the conference. This meant regular one-to-one meetings with Meredith.

On the days we met, Meredith always wore short skirts with high heels. She always had an extra button undone on her blouse, revealing more of her cleavage. She often complimented me on my work. She also began to compliment me on my clothes and my haircut.

I wasn’t sure what to think.

Yes, I did. I’m not naïve.

We always sat close at the small table in her office, Meredith, with her legs crossed over her thigh. I often felt the soft warmth of her leg on mine, unsure if the contact was accidental. She would lean into me as we read a document or email together. A “friendly” hand would be placed on my thigh under the table.

“Have you been working out?” she asked me as she stroked my thigh.

“Yeah,” I nervously confessed. “It helps me get over my girlfriend.”

That answer didn’t impress her.

“Well, you need to get over her sharpish. I want no sour faces at the conference, only smiles.”

Our team wasn’t the best performing for no reason. Meredith had high standards.

I know what you’re thinking. A cut-and-dried case for sexual harassment. She was grooming me. Yeah, you’re right, but she selected her prey well, for I was enjoying the attention too much to complain.

The conference arrived, and six of us, including Meredith, travelled and stayed in the same 5-star hotel where the conference was held.

We spent most of the conference apart, either listening to speeches, schmoozing potential new clients, or being schmoozed by potential new vendors. Meredith was in her element. I knew she was good at her job and highly paid, but she was a magnet for everyone in the industry.

In the evenings, we all ate dinner together. Somehow, I always sat opposite Meredith, and I often felt her foot rub up my leg. Amazingly, she could do it while talking with someone else without giving a hint of what she was doing under the table.

Although we were away from home, we didn’t stay up drinking until late. The other four had families and wanted to call home to talk to their children and spouses.

Meredith and I often had a last drink and talk before going to bed. We were there to work after all.

On the second-to-last day, Meredith walked confidently on stage to give her speech. The auditorium was packed, with several people standing at the back who arrived too late to get a seat.

I was nervous as hell. Most of her speech contained the work that I did in the build-up to the conference.

I needn’t have worried. Her speech was a success. Amongst the applause, she looked in our direction with a smile and a nod, acknowledging our hard work. That smile and nod meant so much to us. That small gesture was incredibly motivating.

Meredith, to show her gratitude, insisted that we all go out for dinner and drinks with her. She was footing the bill. She wanted all phone calls to families made before we went out.

We all changed out of our work clothes into clothes appropriate for dinner and a night out. Meredith dressed herself in an eye-catching short red dress.

As the only single guy there, I couldn’t stop staring at her now and again. Whenever she caught me, she would smile.

Family people, being what they are, don’t like staying out late, and we were back at the hotel by 10 pm.

“Not so fast, Harry,” Meredith said firmly as I headed to the lifts. “If it’s too early for Cinderella, it’s too early for me. I didn’t get dressed like this to go to bed now. You’re joining me for a drink!”

She directed me to a secluded booth at the back of the bar and joined me with two gin and tonics.

“Time for a real drink,” she smiled. “Cheers!”

We clinked glasses.

“Your speech went down well…“

Before I could finish my sentence, she pressed her lips to mine and forced her tongue into my mouth.

When we parted, I was in shock. She had an unimpressed expression.

“Harry, I’m very disappointed in you.”

“I’m sorry,” I replied. “Was there something wrong with the work I did for your speech?”

Meredith waved her hand in the air dismissively. “The speech was a success. I knew it would be. No, I’m disappointed in you because I’ve been throwing myself at you for weeks, and you have made a move.”

“What?”

“I want to fuck you, Harry,” she told me plainly. “I didn’t think I could have been more obvious.”

“But you’re married!” I objected, shocked at what she wanted and her language.

Meredith sighed even more in disappointment, “Does it look like I’m bothered by that? Yes, I’m married, and I love my husband very much. Here is the deal: we have an open marriage on my side only. My husband has a medical condition that means he can’t get an erection. At the same time, I started to go through my menopause. Normally, that wouldn’t be a problem. Unfortunately, I’m one of those women whose libido goes through the roof.”

Her hand made its way up the inside of my thigh to my groin, and my cock instantly began to harden. Meredith smirked at my reaction.

“I thought I could get by with oral sex, but I need to be fucked. My loving husband allows me to have sex with other men occasionally, and you are the lucky guy who gets to fuck me tonight.”

She took my hand and slid it up her dress, past the tops of her black stockings and onto her damp panties.

“Do you feel how turned on I am right now? I’ve been like that for weeks. I expect you to do something about it because you are responsible.”

She put her spare room key card on the table and downed her gin and tonic in one.

“Finish your drink and get your dick under control. My room is 506; I expected you there in ten minutes!”

I breathed out after she left and closed my eyes, willing my dick down. My dick had already made my decision for me. I couldn’t help but smell the fingers that touched her damp panties. Her smell was intoxicating.

I quickly finished my drink and headed to her hotel room.

“You’re late,” she told me, unimpressed, lying sexily on the bed in only her lingerie and stockings. “Harry, I have a very stressful job with a lot of responsibility. I expect you to dominate me and treat me roughly. Sex is how I relieve my stress. The safe word is Marmaduke. If I say it, you stop. Do you understand?”

“Marmaduke?”

“He was my dog when I was a girl.”

It’s not every day your older female boss demands rough sex from you, and it didn’t feel like I should turn her down, and my cock was telling me that no wasn’t an option.

“Come here and on your knees!” I demanded.

“I’m sorry?”

“Come here and on your knees!” I demanded again but more firmly, pointing to the spot in front of me.

Meredith took a moment to realise what was happening before she obeyed and knelt before me, her face in front of the bulge in my trousers.

“Do you want it?” I asked her.

“Yes,” she whispered in a demure voice that I never knew she had.

“I don’t believe you.”

“YES!” she cried louder.

“Then take it out.”

Her hand appreciatively stroked the bulge before she undid my trousers while I took off my shirt.

With my fully erect and hard cock in front of her, I told her, “What are you waiting for?”

She didn’t need to be asked twice. Her mouth opened, and she began to make love to my cock.

“Holy fuck!” I moaned. She was better than good. She knew exactly what she was doing. How far to edge me before stopping?

But she wanted it rough. I grabbed her hair and face fucked her. With each thrust, I could hear her gag as my dick hit the back of her throat. She kept her arms limp at her side to show she was okay with it despite her eyes watering.

Not wanting to cum so soon, I told her,

“Get naked and lie on the bed!” Then, “Keep your stockings on!”

She did as I ordered. I knelt on the floor and started to lick her sopping pussy.

“Harry, Baby!” she moaned loudly before she orgasmed with two of my fingers inside her while I sucked on her clit. I never expected to hear her call me baby.

I kissed up her body to her spectacular breasts. Every flick of my tongue on her nipples elicited a moan. I reached her lips, and we kissed, my tongue deep in her mouth.

“Fuck me!” she breathed when parted.

“Beg!”

“Please! Harry, Baby. Fuck me. I’m begging you!”

I couldn’t believe she begged.

I stood up and roughly pulled her to me before I entered her. I wasn’t gentle. I didn’t slowly ease into her. I was balls deep in one hard thrust.

I pounded her soaking pussy, my balls making a loud slapping sound with each hard thrust.

Meredith lay on her back moaning in ecstasy, begging me to go harder, only going quiet to orgasm.

I then withdrew and flipped her onto her front to enter her from behind, gripping her hips tightly and her plump ass with the occasional spank, which made her whimper.

Watching her ass quiver with each thrust was too much, and I came with a loud growl.

Neither of us moved. We stayed still with me inside her, breathing hard.

“Marmaduke,” she whispered.

I withdrew, she turned around, and we kissed.

“Thank you,” she gasped with a flushed smile from her post-orgasmic bliss.

“I wasn’t too hard?”

“No, it was just right. Let’s shower, then you can hold me for a while.”

We took turns washing each other before returning to bed.

Meredith’s expression looked softer. She looked relieved and less stressed.

I needed that as I held her, kissing each other softly, in contrast to the rough sex we had.

“Look, Harry, you can stay the night,” she told me with a serious tone. “If you agree to make this a regular thing. You were good, Harry, better than I could have hoped. I haven’t felt this relaxed for a long time.”

“How would it work? How would we act in the office?”

“I’m still your superior. Nothing will be different there. No one will know what we are doing. When I want sex, I will call you. We’ll go to a hotel for the afternoon. I love my husband deeply, Harry. He is my priority. Other than sex, we will have no relationship other than you being my subordinate. Every time I have sex with another man, I consider it a gift from my husband, not from the other man. If you disrespect my husband in any way, we will stop, and it will harm your career. Do you understand?”

“Yes,” I replied meekly, intimidated by her threat.

“I know that it sounds like I am using you, and I am, but I am offering you regular, carefree sex with me. I expect discretion. No one must know about us and what we do. I can’t have my husband humiliated. I love him too much.”

“I understand. What if I start dating again?”

Meredith’s tone softened at my question, and she kissed me gently. “I hope you do. What your girlfriend and best friend did to you was cruel. I hope sex with me will help you heal. You’re good, you know. If she says otherwise, she is lying. If you find a girlfriend, we will stop with my gratitude and no issues with your career. All I’m concerned with is having sex and protecting my husband.”

“No, I get it. You’re a lucky woman to find someone so understanding.”

“You have no idea. He is more than a man to me. I know it hurts him that he can’t be the one to have sex with me, but I love him more than ever.” Meredith yawned. “I need to sleep. Set an alarm for 6 am, I don’t want anyone seeing you leave.”