I had gotten ready for an evening with Diane. We had talked that morning before work about our plans for the evening. She had asked me what I would like to do this evening and I told her that I was not going to make the plans tonight that I was leaving that entirely up to her. The only thing I was going to say was I wanted to have fun tonight and that she was to handle all the rest of the details and to let me know sometime today what I needed to wear. Later that day I got a text message on my phone telling me to wear shorts and a shirt and to be prepared to have fun.
I made the drive down to her house which is about an hour away. As I walked in Diane was already dressed in a mid thigh halter dress that was cut low to show off her 34C tanned tits. As she embraced me I reached around to her perfect round ass to realize she didn't have any panties on which usually meant she was very frisky herself and up for a lot of fun. I asked her what she had planned for us this evening and she looked and me a grinned and said:
"Jack it is time to go and you need to feed me well because I'm hungry and I think I will need a lot of energy tonight."
We pulled out of her drive way and made the 30 minute drive to downtown to eat at a very nice restaurant. The whole entire drive Diane was very frisky as she flopped around in her seat, grabbing my cock, kissing me and just very giddy. I asked what she was up to and she said nothing that she was just glad for the evening and was in a very good mood. We sat and laughed and talked and of course I kept asking what she had in mind for the evening or what she was up to and all I kept getting was nothing just to enjoy the evening. We finished our meal and as the valet pulled the car around I asked what she would like to do now. She looked at her cell phone and said why don't we find a bar and have a drink and kill a little time. Now I know that I'm not the sharpest tool in the shed but when a woman has to look at her cell phone to figure out what we're going to do I know she is up to something. Once again I ask and once again I get the same devilish grin and the same answer "nothing".
This part of the evening is pretty funny to the both of us even to this day. You see Diane is a head turner, I'm just your average Joe nothing special but Diane with her petite frame standing at 5"2" and weighing in at maybe 110lbs with a sexy round ass and those 34C tits which she loves to show off and a set of fine shapely legs. Once we were in a restaurant and I got up to go to the restroom and when I came back 2 men had come up and ask her to leave with them in that short period of time. So back to the story we drive maybe 2 miles and see a sports bar. Good place to get a drink I'm thinking, so we pull in and go to the door and there is a cover charge. I don't think anything about it because it's Friday night so might be a band playing or something. I pay the guy as I notice he's eyeing me but my mind is on what Diane is up to and she has already went on in so I follow like a dog in heat with my nose to the ground. She takes a place at the bar and I grab the seat next to her and we order a drink. I look up and scoop out the crowded bar and it doesn't take long for me to notice that Diane is the only woman in here. I lean over and tell her that tonight she is not going to be the center of attention that I will be. We both get a good laugh that we have wound up in a gay bar.
Diane looks at her phone again and gets up to go to the ladies room. When she returns she says that we need to leave. I ask her what's up and all she will tell me is that the evening is about to become a lot more fun and that she will fill me in while we are in the car.
"Jack you know that we share a lot of fantasies together right?"
"Yes we do"
"There is one that you have shared with me several times and I want you to know that tonight you are going to be able to have that become a reality and it won't be a fantasy anymore. That's all you need to know at this time and I will explain the rest to you in due time."
After about 20 minutes she tells me to pull in to this bar and we go in and take a place at the bar and order drinks. I'm a people watcher so I'm just looking around at all the people in the bar and in my mind I am trying to figure out what is in store for me the rest of the evening because my interest level is just about off the chart. After about 10 minutes I look back over at Diane and she is locked in a very passionate kiss with a very large black guy. When they break their kiss I recognize him to be a guy we had met a couple of times but it had been over a year since we had seen him. Now Robert is a personal trainer who stands 6'4" weighs around 230 with a Van Diesel type body and a cock that matches his body size. It's around 11" long and around 5" thick (that is no exaggeration). That's how we had met him off an adult site when we were looking for a very well hung black guy to fulfill a fantasy we both had at the time of me watching her fuck a big back guy.
So after their long embrace while I just sat there and watched they sat back down at the bar and ordered Robert a beer. I asked Diane what was up and she turned her bar stool around to me kissed me very passionately.
"Didn't you say today that you didn't care what we did tonight as long as it was fun and different?"
"Yes I did".
"And don't you have some fantasies that you want to have fulfilled?"
"Yes I do"
"I'm going to ask you another question and I want you give me your honest because your answer will determine the rest of tonight and what happens. Do you want to leave right now or do you trust me enough to give you what you have wanted in a fantasy tonight without knowing what it is?"
"I don't want to leave but I would like to know what I'm agreeing to"
"Yes or no do you want to leave now?" She snapped back
"I want to have one of my fantasies fulfilled tonight."
"Good just remember you asked for this one"
Well she wasn't playing fair because the whole time she was asking these questions she was rubbing my cock and I was rock hard. We share our fantasies with each other and there are several that we had talked about but we had not acted on yet so I had no clue which one she was referring to but I was so hard that it really didn't matter at that moment. I looked her in the eyes and they were filled with passion and it really didn't matter I thought because I was game for whatever she had planned. In my mind I was thinking Griff had brought several of his buddies or another woman but I was soon to find out what was in store for me that night.
She swung her chair back around to face the bartender who was back in front of us to ask us if we wanted another round. Diane held up a finger as to say wait a minute and turned to Robert and asked a question that took me totally off guard.
She said "Robert do you think we could make Jack our bitch for the night and show him how we like to fuck?" The bartender liked to have swallowed his tongue and I liked to have swallowed my glass. Griff turned and looked me up and down and said "I'll think he'll do for one night anyway." Diane looked at me and said "now you will do as you're told when you're told and how you're told for the rest of the night since you decided not to leave."
She then turned to the bartender and said "we will have one more round." All the blood in my body I think went to my face I could feel my face turning beet red and I was in total shock. All the fantasies we had ever shared the one with me being a cuckold was way down on Diane's list of ones to fulfill. She had even told me that one would probably never get fulfilled because she only liked strong men. Boy was I blown away and embarrassed all at the same time. The only problem was I still had this raging hard on as I was trying to get my thoughts back together. Diane looked at me and said:
"I contacted Robert today and he agreed to meet me tonight which is why we are here. All day since we talked this morning the only thing I have been able to think about was having his massive cock and all that you need to do was be a good bitch and do as you are told and not to say anything unless you were spoken to."
I looked down and noticed he was rubbing the inside of her thigh with his big black hand and that he had her dress pushed up and that her hand was rubbing his leg while she was telling me my instructions. When the bartender returned with our drinks Diane leaned over and gave Robert a kiss as the bartender just looked at me and had this shit eating grin on his face. Diane told me that they would finish their drinks and when they got up to leave I was to get up and walk behind them and just wait to be told what to do. I noticed the bartender went over to I take it that they were regulars in the bar and all four of them was looking at us and laughing. I finished my drink pretty quick and was about to order another when Diane broke off her conversation with Robert.
"I'm ready to be fucked good is my little bitch up for this"
I just nodded my head and stood up and walked behind them as they were arm in arm toward the door. As we got to the door she told me to get the door as they stopped and embraced each other in a deep kiss. I held the door opened and waited on them to finish as everyone in the place was staring at us. Once we were in the parking lot she told me that she was going to ride with Robert and for me to follow behind and not to get lost if I wanted to participate in the rest of the nights festivities. It was clear who was in charge of this evening and it was turning out not to be the evening I had thought it was going to be when I had picked Diane up. I thought it was going to be a night of dinner and maybe some dancing and then wild love making. I got into my car and followed his truck out of the parking lot with him driving and her nearly in his lap with one arm around his neck and I could only imagine what the other hand was doing. We pulled onto the interstate headed north and we didn't get to the end of the entrance ramp before Diane disappeared. I was only guessing he was getting one of Diane's out of this world head jobs. We only went up one exit and got off and pulled into a hotel. They walked to the room with me walking behind them as people once again stared at us.
When we got inside the room Robert turned and grabbed Diane and pick her up off the floor and said he was going to jump into the shower and get clean and fresh for her and her bitch. She said that was fine that she needed to speak to me anyway. He went into the bathroom and I heard the shower turn on as Diane turned and said:
"I need you to get the room ready for us and fix us a drink and get naked and sit in the chair by the bed. I'm going to go and help Robert with his shower."
With that she disappeared into the bathroom. I quickly became busy with my "chores" turning the bed down, making them drinks and there was a candle on the nightstand that I lit and adjusted the lighting. I remove all my clothes and sat in the chair. I waited and waited for them to return as my stomach was churning and my dick had gone limp and after about 20 minutes I got up and went to the bathroom door and turned the handle to see if everything was alright but it was locked. On the way back to my chair I opened one of the bottles of liquor and had myself a few large swigs to help calm me down.
After another 10 minutes or so I finally heard the shower cut off and Diane came out first with just a towel wrapped around her with Griff right behind her and he was totally naked and I noticed his cock wasn't hard just hanging down in all of its massive glory. They both got their drinks and made small talk like they were in the room alone. Diane finished her drink and reached for his cock and said:
"Oh my we have a problem here you shot all your cum in me and now your love tool needs to be brought back to life."
