Chapter 18: A Guy’s Dream Weekend: Saturday Night

I awoke, a little over an hour later, to find both girls still sleeping. Cheryl had her head on my chest. Megan had rolled away, but her butt was pressed up against my leg. I tried to be still, so they could sleep a bit longer. But Cheryl noticed the difference in my breathing, or something, and opened her eyes and stretched, and that movement in the bed awakened Megan, who rolled back over to face us. Two wonderful women, pressing their naked bodies against mine. I could stay like this forever. But I had plans.

“Girls,” I explained, “I told you I had made some arrangements for us for tonight. What you need to know right now is this. In a few minutes, I want us to get up. You have to pull on some clothes, and then head over to your apartment. Take anything from here with you that you need for tonight.

“When you get to your place, I want you to get cleaned up, and dress up for me. Tonight, we’re going out. And it will be fancy, so make it good. Pack an overnight bag, with everything you need for the night and some clothes to pull on in the morning. I think you mentioned you had some sexy sleepwear picked out for me, so maybe you could bring that along. Questions?”

Cheryl and Megan looked at each other, then back at me.

“No, Sir. Seems clear. Should we walk or take the car?”

“Why don’t you take the car. With the workout your cunts and assholes have had today, you likely couldn’t walk that far anyway! I’ll walk to your place later, and then we’ll take the car when we go out. I’ll pick you up at about 5:30. That will give you a couple of hours or so after you get to your place.”

Megan got up first, and pulled on some pants and a bra and a shirt. Cheryl snuggled for a minute longer, then followed suit. They grabbed a few items of clothing and some toiletries, kissed me goodbye, and headed out the door. I tidied the apartment for a bit - did the lunch dishes and picked up the bedroom - then shaved and had a shower. I threw some clothes into a bag along with my bathroom stuff, dressed in good pants, a tie, and a casual jacket, and then headed out the door about 15 minutes before I was due to meet the girls.

It was a lovely late autumn afternoon. I hadn’t been outside at all since we’d gotten home from the Thistle last night, and it felt good to use some muscles that I hadn’t been using. The sun was shining, the air was crisp but not cold, and everything smelled like fall. I saw a couple of people I knew, who had either stayed in town for reading week or had already arrived back. I enjoyed the walk, and by the time I got to Cheryl and Megan’s apartment building, I was feeling refreshed and invigorated.

I buzzed up and Megan let me in, but it was Cheryl who opened the apartment door for me. They had clearly not wasted the time I’d given them. Both of them had spent time getting their hair and makeup just right, and the dresses they had chosen were perfect. Cheryl was in a short, emerald green cocktail dress. It was sleeveless, and the hem was about halfway between her knees and her butt. It was the perfect colour to go with her red hair. She had a black shawl wrapped around her shoulders. Megan was in black. Her dress was longer than Cheryl’s, but slit way up her right thigh. It also had a plunging neckline that revealed her ample cleavage. Both girls came and gave me a hug and a kiss.

“I hope that you are pleased with our choice of clothing, Sir,” Cheryl said.

“I am very pleased, Cheryl. You know, you could climb out of bed in the morning, pull on an old t-shirt and a pair of my sweatpants, and look beautiful. But tonight, in that dress, you are breathtaking. Really. And you, Megan. You always look good too. But you are absolutely gorgeous tonight. I will be the envy of everyone who sees us.”

Cheryl moved in for another kiss.

“Oh, by the way, Sir, in case you wanted to know. You can see everything that I am wearing. I thought you might like me not wearing a bra or panties tonight.”

Before I could respond, Megan came up for a second kiss as well.

“Sir, I have to wear a bra. Boobs like mine don’t do well without one. But I followed Cheryl’s suggestion, and I’m not wearing panties either. Would you like to see?”

With that she started to raise the hem of her skirt to show me. I shook my head.

“No, Megan, I don’t want to see. At least not right now. I’d like to let those images live in my imagination for a little while longer.”

The girls pulled jackets on. I hated to see them cover up those lovely dresses and the even lovelier bodies underneath them, but it was cool outside. They each grabbed a small bag, and together we headed down to Cheryl’s car. I drove. Cheryl climbed in beside me, and Megan got in the back. It was hard to keep my eyes on the road, especially since the shape of the front seat and the carefree way that Cheryl had climbed into the car meant that her thighs were very exposed. I could see the tops of the stockings she had on. Obviously they weren’t pantyhose.

I drove us to the outskirts of town, near where a large multi-national company has its offices. There was a new hotel there, that catered mostly to business types. It had a well-reviewed restaurant on the main floor, with a bar attached. I parked, and asked the girls to leave everything in the car and come with me. I led them into the bar, took their coats, and asked them to sit down and order a drink and wait for me, and that I would be back to take them in for dinner in just a few minutes.

Then I dashed back to the car, got the luggage, and went to the front desk and checked in. Last night, when I came up with this plan, I had reserved a room for us: king size bed, huge jacuzzi, walk-in shower, sitting area ... the works. It was an executive suite, but because executives don’t stay in hotels on weekends, it was fairly cheap to book it. And I was sure that the fun we could have with the amenities would be worth the expense. I deposited our luggage in the room, phoned down to the front desk to arrange for a bottle of champagne to be waiting on ice for us when we came up, and then headed back down to the bar to meet my ladies and take them in for dinner.

I froze as I entered the bar. There were my women, dressed so beautifully, sitting on barstools, cocktails in front of them. And standing behind them, chatting them up, were two older guys. They had to be in their early thirties, and it was obvious what they wanted. This was why I’d never had a girlfriend. I was always afraid that any girl I dated would ultimately reject me for someone else. And of course, with a girl as gorgeous as Cheryl, it was bound to happen. Especially when I had asked her to dress up like this and come out here with me. Having Megan along was just an extra draw to the guys who would try to win Cheryl away from me.

As I was hesitating near the door, wondering what to do, Cheryl looked up and saw me. Her face brightened immediately. I realized I’d been holding my breath, and I exhaled, and started towards her.

“Here’s our date. John, I was beginning to think you’d gotten waylaid by someone! We’ve been chatting with Paul and Devon, here, but I think it’s time for dinner, don’t you?”

With that she climbed off her stool and came over to kiss me. Megan followed suit, and brought Cheryl’s glass as well as her own. As we headed towards the hostess’ booth, I heard one of the guys commenting to his buddy.

“Damn, man! How does a guy like that score not just one but both of those hotties?”

I tried not to react, but I know that both girls heard it, and both of them knew that I had heard it too.

The hostess led us to our table. I pulled the girls’ chairs out, and sat between them. We were tucked into a quiet corner. Our waitress introduced herself, and we all ordered drinks - another round of cocktails for the girls, and a beer for me. Then she left us with the menus. When she came back with our drinks, Cheryl told her we needed a few minutes before we would be ready to order, and she disappeared again, telling us to take all the time we wanted.

As soon as she was gone, Cheryl leaned in close.

“John, I want to pause the game for a moment. Can I do that?” I nodded, and she continued. “John, I saw the look on your face when you came back to the bar.”

Megan, who hadn’t noticed me when I came in, immediately looked worried. “Oh, gosh John, it’s my fault, not Cheryl’s. Don’t be mad at her, please. I was the one who started talking to those two guys when they came up to us. Please don’t be angry with her.”

“Megan, he wasn’t angry. He was worried. John, listen to me. No, Megan, sit, please. You’re my best friend. And there is no need for you to leave. You can hear what I have to say.

“John, I know you’re insecure. And I realize we haven’t been dating very long. But I’ve dated enough other guys to know that you’re the one I want to be with. Sometime, if you want, I can tell you about each one of my other boyfriends, and what they were like, and why they were ok for a while. But none of them were right. You are. I know that. And I will talk to other guys. If we’re out like we were last night and there’s a guy I trust and that I think you trust, I’ll even dance with him. If it’s a guy like Ian, maybe I’ll even flirt with him a bit. But you are the only guy I will ever go home with. You are the only guy I will ever sleep with. You are the only guy I will ever whisper ‘I love you’ to.

“I realize this might sound a bit odd, after I’ve spent the weekend encouraging you to have sex with my best friend. But I will never want to have sex with another man. I’m certain of that. I’ve been with enough guys to know that no matter what any of them have to offer, none of them will be able to give me what you give me. I lost you once, and I am not going to be that stupid again.

“I know you think I’m out of your league. And we even roleplayed that a bit this morning. But you need to know that I am not out of your league. I am in your league. I am your league. In fact, I’m even more than your league. I’m your team. So when you see me talking to another guy, don’t worry. Don’t think, ‘I knew this was too good to be true, and now she’s going to leave me for him.’ Instead, think, ‘Look at that poor loser trying to chat up my girlfriend. She is so out of his league. Because she’s in mine.’”