Dinner with Joey and Phoebe

We pick a night that works for both of us. We get babysitters to watch our kids for the night. We book two rooms at the same hotel.

Monica and I check into the hotel, then get ready in our room. It takes much longer for her to get ready. She shaves her legs smooth, she doesn’t take off her pubic hair but she cleans it up. She does her hair and makes sure it has long curls and waves. She does her makeup. She pulls out a brand new matching set of bra and underwear. She puts it on. She puts on heels then struts around the room teasing me.

She asks, “How do I look? Would you fuck me? I’d fuck me.”

Before I get up to grab her, she runs back to the bathroom to put on her dress. Her dress reveals her nice pale cleavage. She pushes her boobs together and says, “Damn this bra makes my boobs look good.”

I stand up and pull down my pants. I ask, “Does this underwear make my bulge look good?”

Monica smiles and says, “You should ditch the underwear tonight. Just let your dick feel the fabric of your dress pants.”

So I go commando to dinner, my dick and balls swinging loose inside my pants. It gives me a boost of confidence I’m not expecting. Maybe people will see the outline of my cock head on the inseam of my pants.

We chose a restaurant that was within walking distance of the hotel. Joey and Phoebe are already seated when we get there. They sit facing each other an empty chair next to them. Monica sits next to Joey and I sit next to Phoebe.

As soon as I sit down Phoebe puts her palm down on the top of my thigh. My dick moves. Twitch. They greet us and we make small talk. We have a few drinks before ordering dinner.

I have loosened up and say, “You’re in for a treat tonight Joey. Monica has gone all out. She’s lucky I didn’t take her before we left the hotel room.”

Joey looks at Monica and says, “Aw you didn’t need to do anything special. I think you’re attractive anytime I’ve ever seen you.”

Monica laughs, “You’re too sweet and that’s a lie. You haven’t seen my fat rolls yet. It’s not attractive.”

“Don’t be so down on yourself,” says Phoebe. “Joey is into you. Just be cool with it. We all have flaws. For instance, I honestly forgot to shave and I have a big black bush between my legs.” Twitch.

Monica laughs, “Lucky for you, I know from experience that doesn’t stop Chandler. He’s been Indiana Jones cutting his way through the jungle to get to my vagina.” Then she looks at Joey a little embarrassed. “But not tonight. You’ll have a clear path.”

Phoebe squeezes my thigh. Twitch. I take a sip of my drink. I look over at her. She winks at me. I ask, “So how many times have you done this before?”

“With couples?” Phoebe responds. “Two. But one was a lesbian couple. Joey was so disappointed. They weren’t interested in him at all! It was basically a lesbian threesome with Joey occasionally putting his dick in me.”

“Most awkward hour of my life,” Joey says. “I didn’t know what the fuck to do. I should’ve just left and played Xbox.”

Phoebe continues, “It was great for me. And was like watching a slow porn he couldn’t fast forward for Joey. But the other couple was straight. We ‘met’ them online. They made sexual videos and posted them to websites. I reached out and asked if we could join them for a video. So if you search really hard, you can find Joey and I having sex with strangers online.”

Monica says, “Oh my god.” I knew Phoebe and Joey did some wild things, but I never imagined that they’ve publicly post their escapades.

“It’s not as hot as it sounds,” Joey says. “Someone had to hold the camera the whole time. We had to discuss what positions we were doing and what would look best on camera. It was like 10 minutes of sex with 2 hours of debating how to fuck. Like the chick looked hot in her videos, but then we we got there, whoa buddy. They do a lot of editing and camera work not to get her bad side. And before you ask Chandler, I’m not telling you how to find the video. I’ll admit the video looks good, but the memory ruins it for me.” He finishes his drink. “So honestly our swaps with couples have been pretty bad so far. But I have high hopes for this one.”

Monica laughs and finishes her drink. With her glass to her lips, her eyes make contact with mine and she raises her eyebrows. She might be regretting this already.

Phoebe says, “Don’t let that discourage you. This is a much different situation. We all know each other, and are all here to have fun.” She squeezes my thigh. Twitch. “I know Chandler has been wanting to do this for a while.” She looks in my eyes.

I say, “Hold up. Why do you think that?”

She rubs my thigh. Twitch. “I saw how you stared at my ass when we all went on that hike when we met. I was wearing some tight leggings and my ass looked great so I can’t blame him, but he was checking me out the whole time.”

I respond, “You mean the hike where you told Joey and I to pose for a picture on a boulder, and then said ‘Get your dicks out. Let’s see whose is bigger.’ That hike?”

“What?” Phoebe says. “I’ve always wanted to be a judge in a dick measuring contest. That was not me hitting on you. In fact, I’ll probably compare you two tonight.” Her hand moves from my thigh onto my dick and rests there. Twitch.

I stare into her eyes preparing my comeback. She knows how to work me up. The food gets delivered at that moment. The tension is broken. Phoebe moved her hand away from my lap.

As we eat we discuss that boundaries for the night.

1. Condoms must be worn

2. Nothing too rough or degrading

3. No anal sex

4. All the sex takes place together in the same room

With the rules established, we finish dinner and head back to the hotel.