Chandler’s big black boss

We learned some things on that cabin getaway.

1. I can do ridiculous things when I’m drunk, horny and angry
2. Chandler liked hearing about my sexual history
3. Chandler liked to watch
4. Chandler learned that I like big penises

About that last one: it’s still about how you use it, of course, but I just enjoy the feeling of one filling me up and stretching me out. Chandler’s is great. But. That night reminded me what a really big dick felt like.

So I told Chandler I was open to doing something like that again if he was up for it.

He didn’t ask, but we would still talk about it. I would tell him stories as I jerked him off. He loved hearing about my exes. I could get him to finish so quickly if I brought it up during sex. One time I asked if he wanted me to fuck one of his friends. He came so hard. Then cuddled against me thinking about it. He said, “No. Not my friends. That could bring up a lot of complications.”

We didn't actively pursue it. It just became another fantasy we talked about. And it was best not to sleep with other people right before I moved across the country to go to grad school. Long distance would be hard enough.

So I went to grad school for a year on an accelerated program. We saw each other maybe six times. It was hard and I missed him so much, but we made it through. Once I graduated, he moved back to the Midwest and we moved in together.

He proposed. I said yes.

We were getting married! I was so excited. I decided to bring up our fantasy again.

One night on the couch, my head on his shoulder, my hand in his lap, I said, “We should do something crazy to celebrate our engagement.”

“Yeah?” Chandler looked at me. “What do you want to do?”

“I’ve been thinking about that night at the cabin. You thought it was hot seeing me with other men. I know you want to see that again. I’m curious to see how you look pleasuring another woman. Sooo I’m thinking we should find another couple, then we can swap and watch each other.”

“You wanna see me with another woman? You won’t get jealous?” He looked surprised.

I held up my ring finger, “You’re mine, and I’m yours. Besides I’m going to ride you so hard afterwards, you’ll forget that you just had sex with another woman.”

He smirked thinking about it, “Hmm now we have to find another couple. And we have to make sure the guy has a big dick for you.”

Of course. I didn’t say it, but of course I wanted a guy with a big dick. Like I said, Chandler’s was nice but I was itching for a new experience.

“Let’s think about how we can find another couple,” I said, rubbing the hard wood in his pants. “I want to make this happen before our wedding.”

We checked websites, but those made me nervous. I didn’t want to get murdered. I would prefer people we had some knowledge about.

Then one evening Chandler came home from work and told me that his boss and the lady from HR wanted to take us out to celebrate our engagement.

A man and a woman. That was a couple.

I asked innocently enough, “What does your boss look like?”

He saw the look on my face. “Oh No! Did you not just hear me? My boss and HR! That would be a complete disaster!”

“Or they could really enjoy their time with us, and maybe you’d get a promotion,” I joked.

He rolled his eyes, “They’re not even a couple. Like maybe we could get one to join, but not both.”

I could tell: the more he thought about it, the more he wanted it. I didn’t know a thing about his boss or this woman from HR, but if he was actually considering it, then I knew it would be a hot pairing for both of us.

“We’ll just get them drunk, and I’ll turn on the charm,” I said grinning at him. The bulge in his pants was noticeable.

He said, “I’ll think about it. I might have to get a new job whether we succeed or fail.”

“Perfect,” I said. “You hate that job anyway.”

He eventually agreed to it. He didn’t tell me anything about them even though I kept asking. I enjoyed being kept in the dark though.

We picked a nice restaurant we could walk to from our apartment. I wore an outfit that wasn’t too provocative, but still showed off my curves. Chandler couldn’t stop checking out my boobs. I had to swat him away.

His boss and H.R. Business Partner were already sharing a drink at a tall table in the bar. His boss stood up and introduced himself as Eric. He towered over me. Chandler’s boss was a very large black man. His head was shaved so smooth it shined. He had a neatly trimmed beard. His hand engulfed mine in the handshake. His smile melted me, and heart tried to beat out of my chest. I had never been with a black man before, and I had never been with a man this large. His upper arms stretched the fabric of his red polo. If his dick didn’t match his body, I was going to be shocked, especially since I could see a decent bulge in his khaki pants. Chandler knew what he was doing when he said yes to this swap.

I introduced myself, and Eric said, “It seems like Chandler and I have the same taste in women. You’re gorgeous.”

“Thank you,” I said blushing.

“Stereotypical black man fawning over a thick white girl,” a woman’s voice said. She got up from the table and shook my hand, “Hi! I’m Karen! Congratulations! You’re getting such a great guy in Chandler.”

She reached and patted Chandler on the shoulder. Karen was a middle aged black lady. She was shorter than me. She had beautiful smooth caramel skin. A pinch of grey seasoned her short locks that dangled on her head. Her shirt opened to reveal cleavage with a faded tattoo above one boob. (That gave me a hint that this night might work out. This HR lady definitely had a wild side to her). She wore a black skirt that hugged her substantial backside. Yup I could see why Chandler would be cool with this swap.

We were led to our table and seated. Eric ordered another Long Island. Karen asked me if I wanted to share a bottle of wine. “Something sweet, please.” Chandler ordered a Manhattan.

The conversation was friendly. I told them how Chandler and I met. They enjoyed the story, especially when I told embarrassing parts about Chandler. I carried most of the conversation with Chandler staying quiet as usual.

Eric and Karen seemed so comfortable around each other. After a glass of wine, I had to ask, “Have you two dated before?”

Eric bellowed laughter, “She wishes! She’s too old for me.”

Karen swatted at him, “I’m not that much older than you.”

“13 years is a lot,” Eric said.

“Do you mind me asking how old you are?” I asked timidly.

“59,” Karen answered.

I screamed, then covered my mouth, “Oh my god! You look fantastic! I would’ve said 40.”

“Black don’t crack,” Eric said. I did the math in my head: he was 18 years older than me. By far he would be the oldest man I had ever been with. And Karen would for sure be Chandler’s oldest. She was almost twice his age! A very experienced swap.

The dinner was fun and filled with laughter and occasional flirting. They praised Chandler. They made me proud that he was my fiancé. Everyone seemed so comfortable around each other. Maybe that was a consequence of the ****. Eric had four long islands. Chandler had three Manhattans. Karen and I shared two bottles of wine. The boss paid with his company card.

I said, “This has been so much fun. I don’t want this night to end. You should walk back to our place. We can have some coffee before you go home.”

Karen said, “That might be a good idea. I don’t feel comfortable driving at this moment.”

“Yeah,” Eric agreed. “Let’s keep the party going. You lead the way.”

“You just wanna check out my ass,” I said.

He winked, “Maybe.”

This was going to work.