Early in March, before we were all sheltering in place and working from home, I ran into my friend Ed. I wasn’t planning on being out long, so I had just done some minimal makeup, put my hair into a ponytail, and put on some jeans, and a white tee shirt. Christie had texted earlier and said to “wear white,” meaning we would both be wearing matching white bras and panties. The white bra was clearly visible through the shirt, and it was drizzling, so I added a thin white sweatshirt top. My nails were a subtle pink shade.
Ed and I have known each other since school, but hadn’t really kept in touch. A few years ago, I was cocktailing for Christie at a charity event and he recognized me. We’d gone out once after that. He was a nice guy. I’m not sure how I would describe our relationship. He knew about my becoming Christie’s “girlfriend,” and seemed supportive. We were friends. He definitely wasn’t gay, but we’d had sex twice, once after the charity event, and once after we’d been out for drinks.
Ed asked me what I’d been up to, and if I’d gone out or done anything fun lately. I replied that it had been pretty much just work, but I did tell him about New Year’s Eve.
“That sounds like a fun time,” he said. He was disappointed that I didn’t have pictures. I’m terrible about pictures.
He went on to tell me about a group he’s been playing poker with. It was a monthly game, rotating between the players’ homes. One guy hosts, and another supplies food and drinks, he explained. The next month, the food and drink player hosts, and another player brings refreshments, and the rotation goes on. He asked me if Christie and Lexi would like to supply the food and drink. “You could be the waitress,” he added.
I started out with an “I don’t know, Ed,” but he persisted. It was his turn to supply food and drink, and he was tied of the same old chips and salsa. I agreed to ask Christie, although I knew what she would say. “But me waitressing…how would you explain it? In a big group, like those big events, it’s easy not to get noticed. Most people are too into their own fun. This seems pretty obvious.”
“I’ll just say I won a bet with you, or something. Please? Ask Christy, ok?” he begged.
Christie, of course, was enthusiastic. She checked with Lexi, who really did most of the organizing work, and over the next week, Lexi and Ed worked out the details. It wasn’t a large group, just the seven players and maybe one or two stand-by players. Lexi, Christie and I would set up the food and bar, but then they would leave. I was to do the serving.
On the day of the game, Christie came over to my place to help me get ready. I had showered, shaved my body, and washed my hair. Christie helped me do my hair in loose beachy waves. She also shaved my back and shoulders, just to be sure they were smooth. Then she did my makeup and nails. I do my own makeup most of the time, and it was quite a treat to have Christie do it. She laid out the clothes I would wear – a short black skirt, a black halter-style tuxedo top with a bow tie, black pantyhose and a pair of low, black heels. She loaned me one of her bras – a black halter-style lace one – so the straps wouldn’t show under my top. I chose a black lace thong that almost matched the bra.
She drove me over to the host’s house. The host, Hal, met us at the door. He stared at Christie and me for a minute, and then greeted us. “You must be Christie,” he said, reaching out to shake Christie’s hand. “And you must be Gee. Damn. Must have been a hell of a bet! Come on in.”
We came in and found Lexi in the kitchen, setting up the food. There were a few steam trays of hot food that I would have to pass around, some other things set up buffet-style, and a bar area. The house had a very nice wet bar. Ed had let Lexi know what drinks the players liked, so she had arranged all of the fixings for me. Earlier in the week, Christie had made sure I knew how to make the drinks and practiced each one.
Ed was the next to show up. After we all greeted each other, Hal congratulated Ed, speaking to all of us. “I don’t know how you set this up, but this is amazing. The food and drink looks great – way better than the usual snacks. The bar set-up is fantastic. And, I don’t know how to say this, but your waitress looks fine! I don’t even want to know what the bet was!”
Everyone laughed, at that, and Hal went to greet the players as they arrived. Lexi and Christie hugged me, asked if I had any questions, and got ready to leave.
Christie pulled Ed aside. “Take good care of her, ok?” she asked, looking at me.
“Of course,” replied Ed. Lexi and Christie left.
Ed looked around the room. We were alone. “You do look great,” he said, holding my hands. “Just relax. These are alright guys. Hal told everyone it was just a bet between us, like I told him. You’ll do fine.”
The players were starting to show up, so I grabbed a tray of various snacks and went out to the front room. Most of the remarks were directed toward Ed, about how he really outdid everybody else as far as food and drink. Ed shrugged it off, saying “I know some people.”
I eventually got everyone situated with food and drink. The host moved everyone to the table, and things got a little easier. The players concentrated on the game – they were very serious – and the two stand-by players just watched. I refilled drinks, occasionally bringing more snacks, too.
I hung back by the stand-by players, waiting for someone to need a refill. One of them, Tony, leaned over to me. After making it obvious he was looking me over, he asked me “so, Hal says you’re a dude.” The other stand-by player snickered and shook his head.
As quietly as I could, I replied “Yes, I’m…a dude. But tonight, I’m serving drinks.” I walked back to the bar. Some of the players’ drinks were running low.
Eventually, one of the players cashed out, and Tony took his place at the table. As I was making a round of the table, I felt a hand up my skirt. Tony had slid his hand well up my leg and onto my butt. “Excuse me,” I said, stepping back. The other players looked at Tony.
“What are you doing, man?” asked one of the players. Tony quickly produced a few dollars and said he was trying to put a tip into my stockings.
I set Tony’s drink down. Hal looked at him for a long few seconds, and said “let her alone.” The players all stared at Tony, and he eventually put the few dollars onto my tray. I thanked him.
I finished my round of the table, and went back to where the other stand-by stood, then back to the bar. The other stand-by followed me. He introduced himself as Barry.
“Don’t be mad at Tony. He’s not a bad poker player, but he’s kind of a jerk. You do look really, um, amazing.”
“Thank you,” I replied. “I wasn’t sure about doing this, but Ed and I made a bet, and I thought ‘If I’m going to do this, I have to do it right. So I got my friend Christy to help me.”
“Yeah, I’m not really sure how to say it. I mean, I know you’re a guy, Ed’s friend. But you do look…hot. If I didn’t know, I wouldn’t have guessed, I guess.” He was nervous.
“Thank you, Barry.” I said. “I appreciate the compliment. We spent a lot of time on all this, and I’m glad it seems worth it.”
“And it was just a bet?” he asked.
“This part of it was a bet,” I replied. “I should get back to work.” I made my way back to the table.
The game broke up after a few more hours. It was well after midnight. A few of the players left me a tip as they left.
I was in the kitchen, finishing the dishes, when Hal and Ed came in. Hal was pleased.
“That was absolutely the best. You were great, by the way,” he told me. “You really know how to do this. We were a little worried it would be too much of a distraction, you being our waitress, but you were perfect.”
I thanked him. Ed looked at me. “Ready?” he asked.
“I’m ready. Thank you, Hal. I’ll pass your compliment along to Lexi and Christie. We really appreciate the opportunity.”
We headed toward the front door. Ed reached it first, and opened the door for me. I smiled and thanked him. As we walked to Ed’s car, he offered me his arm, which I kind of instinctively took. We reached his car; he opened the passenger door for me, and helped me in. I noticed Hal was watching from the porch.
We made small talk on the way home. Ed complimented how I looked and how I managed the food and drink. He handed me an envelope. “It’s from the guys.” He explained that everyone decided to put in a percentage of their winnings, if they had any. There was a lot more there than I expected.
We arrived at my place, and Ed jumped out of the car to open my door. He walked me to my door, where I invited him in for coffee.
We sat on the couch for a few minutes and talked.
Ed leaned over and kissed me, stroking my thigh with his hand. I didn’t quite know what to do with my hands, so I just put them in my lap. To my surprise, he reached under my skirt and began to rub me.
A few minutes later, he stood up and led me to my bedroom. I sat on the edge of my bed, undid his belt and fly, and reached into his pants, pulling out an enormous cock. I leaned down and put it in my mouth.
“God, that feels amazing. How did get so good at this?” he said. I told him how Christy had taught me. Ed stood me up and undressed me slowly. The he gently slid me back on the bed, pushing my legs apart. I felt self-conscious, but managed to reach to my nightstand and get a condom and lube.
He positioned himself between my legs. I was worried about how big he was, and hoped he would go slowly. He held my ass and hips and worked his way into me. It was intense. I thought of how my first time with Christie felt weird and a little frightening. It’s something feel it through my entire body. I describe it a tight sensation in my throat, like what you feel after a bad scare. But it’s an exciting feeling, not scary at all. It kind of spreads out all the way to my fingertips and toes.
I felt Ed’s body tense just before he came. When he withdrew, he took off the condom.
“What should I do with this?” he asked, grinning. Remembering what Christie likes me to do, I opened my mouth. That surprised him, but he emptied the contents onto my tongue.
We lay down on the bed and cuddled, and I fell sound asleep.
I had no idea how late it was when we fell asleep, but it was nearly 9 am when I awoke. Ed was gone, and my phone was alerting me to a message. It was Christie.
“Let’s wear blue today,” she texted.