Chapter 1

A Night with a Lover and a Friend

It was payday Friday and as was the norm, my best friend, Debbie, and I were on our way to happy hour at our favorite bar. Debbie and I had been working in the same office for the past three years and had become the closest of friends. We told each other everything that was going on in our lives, our family dramas, our problems at work and even the intimate details of our love lives. Every Friday after we got paid, we would go out for our little girls’ night out, have a few drinks and chat about our lives.

I was currently dating a guy that lived in a town about an hour away. We normally saw each other on the weekends, as we took turns driving to

each other’s town to visit every Friday night. On the Fridays that I went out with Debbie, Gary would drive down and let himself into my condo and watch TV or whatever until I got home. On this particular Friday, Gary had left his job early to meet me at my condo and go to the bar with Debbie and me. Debbie had agreed to Gary coming with us since they got along fine and always enjoyed kidding around with each other or ganging up on me.

Debbie followed me from work to my condo, where I was going to drop off my car so we could all ride together. When we arrived, Gary was already there, sitting in his

car waiting for us. I parked nearby, got out and tapped on his window to let him know I was there. He looked up, smiled, and got out of his car. He gave me a hug and a kiss, then walked me over to Debbie’s car for the drive to the bar. When we got to her car, Gary said he would sit in the backseat so the two of us could talk.

Gary and Debbie greeted each other warmly as we got in the car and Debbie asked whether Gary had enjoyed a good week. Gary responded that he had, but that he was looking forward to just relaxing here in town over the weekend. About twenty minutes later, we arrived at the bar and walked inside. We went to the same bar all the time and many of the people that worked there, now knew us and recognized Debbie and me when we walked in.

Susan, one of the waitresses, walked over to greet us and I introduced her to Gary, and she showed us to our usual table. We liked sitting off to the side, back in a corner where we would not be bothered and could talk in some semblance of privacy. Susan took our order for our first round and left us. Gary got up to put money in the jukebox and asked if we had any requests. Debbie said no as she trusted his taste in music and Gary went off to program music.

As we waited for our drinks to arrive, Debbie commented that she was more tired this Friday than she could

remember in a while. I agreed that it had been a long week and that I had been looking forward to spending the evening chatting with her over a few drinks. Debbie commented that they would have to refrain from talking about sex since Gary was with us, but I told her that Gary would not mind and would probably offer his two cents when he felt like he had something worthwhile to say. Our drinks arrived, along with a bowl of popcorn, just as Gary got back to the table. Music began to play, and I immediately recognized it as Gary’s favorite band, Chicago.

We sat sipping our drinks, glad the work week was over and chatted about a variety of subjects. Gary was quiet, content to just listen to the two of us ramble on about different things. Truth be known, I could tell that he was enjoying just sitting in the booth with the two of us. Debbie is quite attractive, and I know that Gary has always enjoyed looking at her and flirting with her. She has a body

very similar to mine, short, athletic, very small breasts, and a killer smile.

When we finished our first round of drinks, Gary offered to go get us our second round and we sent him off to the bar. While he was gone, I commented to Debbie that I thought Gary was enjoying looking at her. She asked me if I wanted to have a bit of fun with him and I

nodded and asked what she had in mind. Reaching under her top, she unhooked her bra, slipping the straps off her arms. She then pulled the bra out from under her top and put it in her purse. She winked at me and told me to take off my bra as well, to see who he looks at more.

I took my bra off and put it in my purse as

well but told her that he would be looking at her, as Gary sees my breasts all the time and hers would be more of a novelty. It was then that I noticed that her top was a bit sheer and her nipples were barely visible through the material of her blouse. I told her what I could see and that if she got the slightest bit cold it would be obvious to Gary that she was braless. She told me she just wanted to warm him up for what he would be enjoying with me later in the evening. I asked her why she had not started dating again and she related that no one that she considered interesting had asked her out. I told her that I would have to be on the lookout for someone for her, or that maybe Gary had a friend that he could introduce her to.

Gary came back with our drinks and his gaze immediately went to Debbie. It was obvious that he could tell that she was braless. He did not just outright stare at her but would pretend to move his gaze around, always coming back to her. Debbie announced that she needed to use the ladies’ room and would be right back. When she left, Gary looked at me and asked me whether Debbie had taken her bra off while he was getting drinks. I told him that we

both had, as it was just our way of saying thanks for being a gentleman tonight and letting us have the evening together.

Gary said he always knew that Debbie was small, but he did not realize how big her nipples were. I reached across and playfully punched him in the arm and asked if they were nicer than mine. He said that mine were the prettiest he had ever seen, but it was fun having a look at Debbie’s, especially since she was intent on showing him.

Debbie came back to the table and she and I continued to chat, while Gary had fun listening and watching us. At one point, I looked over at Debbie and either she was cold or was enjoying having Gary look at her, as her nipples had become quite prominent and were very visible through her top. I giggled a little and Debbie asked me what was so funny. I told her that she must be either very cold or very turned on as her indicators were certainly in full reveal mode. She looked down and saw that she was in fact, showing. With a smile, she looked at Gary and told me that she

was not cold.

After chatting for a few more minutes, we had all finished our second drink and decided one more would probably need to be our last. Debbie would need to still be able to drive us back to my condo and then on to her house. We sent Gary up to the bar to get us one more round, and I

excused myself to go to the ladies’ room. When I came back, Gary had already arrived with our drinks and was talking to Debbie.

As I neared the table, I overheard him tell Debbie that he thought her breasts were quite attractive and that her nipples were very sexy in that top. I cleared my throat, and Gary suddenly sat back in the booth as if nothing had been going on. I leaned over and gave him a kiss, allowing my top to fall open a bit so that he could see my breasts. As I started to pull away, Gary reached up and put his hand on one of my breasts and cupped it. I moaned and slid my tongue into his mouth for just a moment while he caressed me.

When we finally separated and I went to sit down, Debbie commented that she still

was not cold, but that her indicators seemed to be even more prominent than before. I just smiled and told her that I was glad she had enjoyed the show but that she needed to find herself a guy so she could enjoy some of the same thing from time to time. She sighed and said if she could find someone as nice as Gary, she probably would be dating already, but that I had already snagged a great one and there were not that many great guys out there.

Gary excused himself and got up to go to the men’s room. While he was gone, I turned to Debbie and asked her if

she would like to borrow Gary for a weekend some time. Debbie said that while it might be tempting, she could never go to bed with someone else’s boyfriend and that for now she was just enjoying the atmosphere here at the table with us. We continued to chat until Gary came back, and this time, he leaned over and kissed me, again putting his hand on one of my breasts, gently massaging it. I could feel my nipples hardening, and they were now poking into the material of my blouse.

Gary separated from my lips but continued to lean over, sliding his hand inside of my top and rubbing my nipples under my blouse. I started moaning and told him

he had better stop before someone caught us. Gary moved away and went to sit back down on his side of the booth again. I looked over at Debbie and she was just smiling, but I also noticed that her right hand was in her lap and she was clearly rubbing herself.

The three of us continued to chat until we had finished our drinks and I suggested that we probably should head home. It was almost ten o’clock and we had been sitting there for about four hours. Gary said that this had been such a fun evening with the two of us that he wanted to get us all a glass of champagne to toast the evening. I asked Debbie how she was feeling, and she said she thought she could handle a glass of champagne. I told Gary to go ahead and get us all a glass and we would have

a ‘nightcap’ toast. I was anxious to get home and get Gary in bed as he had me horny at that point after playing with my breasts a couple of times. I quite often went braless as I was small enough for it to not matter, but tonight, my nipples had gotten extra sensitive for some reason and I was ready to fuck.

Gary came back with three glasses of champagne, all filled close to the top. He said the bartender had asked if he could just finish off the bottle for us and Gary had agreed, so we probably had more in our glasses than normal. Gary sat down and proposed a toast to a wonderful evening with two great friends for letting him tag along for the night. We clinked our glasses together and each of us took a drink. Then Debbie said she wanted to make a toast and lifted her glass to her best friend and her boyfriend, for motivating her to find a boyfriend for herself, quickly. Another clink of the glasses and we all took another sip.

I piped up and declared that if they were both going to toast, I would as well. I raised my glass and toasted Gary as the guy I loved to

fuck and to Debbie, the woman that I would fuck if I had any bisexual tendencies at all. Debbie and Gary both looked at me for a moment, but then we all clinked glasses and finished the last of the champagne. Gary remarked that those were three interesting toasts and that he was extra glad that he had suggested the champagne. Debbie’s nipples looked like they were about to tear right through the fabric of her top and she had a very strange look on her face.