My name is Derick and girlfriend's name is Nancy we are in out late forties and have been a couple for about 5 years. We both came out of bad marriages that came about from youth and hormones and what we both thought was love at the time. Neither of us had any children and that time has seemed to pass us by. We are both very happy and have thriving careers. We are not rich but make enough money to enjoy some of the finer things in life. We both like to travel and since we live in the northeast of the United States, we tend to go to tropical climates for a couple of vacations a year. That is fine with me since I love looking at Nancy in a bikini and truth be told she loves me and others looking at her as well.
Nancy is about 5' 10" tall with medium length red hair. She fills out her bathing suit very well with her 36DD breasts which are matched in beauty only by her long legs. I guess she would be considered a full figured today in this age of toothpick models. I just love that her curves are in all the right places. I have greying hair, just over 6' and weigh about 230 pounds. I have a few more pounds than I should but Nancy says she wouldn't have me any other way. We have an active and imaginative sex life and make love 2-3 times a week and have what I would say would be raw sex on at least one of those nights.
On our vacations, it is common for us to frequent a topless or nude beach. She knows I enjoy showing her off and once relaxed, typically after an umbrella drink or two she enjoys the looks she gets. Her only rule is that if I want her to sun bath totally nude that I must join her. It is her little way of having me put up or shut up but I think she gets a kick out of watching me try and keep my erection down as I look at the other women on the beach. The excursions to these beaches regularly lead to hot sexual encounters where we fantasize about the day's events which often involve her telling me about some guy who caught her eye or perhaps she caught someone looking at her. She'll tease me about what might happen with these guys if I wasn't around. One common theme would be that we were at the resort, but it was a working vacation for me. It would be some sort of conference and as a result I could not be with her all day. This left her alone on the beach by herself. Typically, a guy would see her sun bathing topless and stop by to offer to buy her a drink and strike up a conversation. She would change up the age and even ethnicity of the guys which kept it fresh and exciting especially when a black man was part of her story. In the end, they would inevitably end up back in our hotel room or his in a passionate round of sex. Her level of detail in her descriptions of these encounters would very much depend on how I was responding and her mood at the time. When she saw that I was very aroused and asking a lot of questions she would feed off that and play into my eagerness to know more.
We had often shared our fantasies with each other. We spoke about them most during one of our "sex" sessions where we tended to be more kinky than other times. She knew of my most common fantasy situation was to watch her with another man. She has heard several different versions of this fantasy from me. They ranged from simply giving her a "Hall Pass" where she meets a guy she likes, and it turns into a sexual encounter to situations where we would go out as a couple to a bar where I would watch her get picked up. In this fantasy, we would arrive together but go into the bar separately. I would go to one end of the bar and she the other and we would see who would try and pick her up. This fantasy had many different outcomes but all seemed to turn us both on and enhance our sex together.
We actually acted on this last fantasy once. My birthday was coming up and we had a trip to Vegas planned. A week or so before we left she asked if I wanted anything special for my birthday. Just by asking she knew she was setting herself up. I said that I would like to experience one of our fantasies specifically the one where we went to a bar to see if she could get picked up.
She looked at me with a knowing look but smiled and said, "If that's what you want, we can give that a try. It will give me a chance to wear one of my dresses that you never see me in."
The day came and I could sense a little bit of excitement in her as it came time to get ready for the evening. She played into my fantasy without any encouragement from me and got dressed up in a very sexy little black dress and heals. It was one of those dresses that was short enough to cause issues trying to sit up on a bar stool. The dress rode up her legs almost to the cheeks of her ass. She rejected my request to leave her panties behind in the room but did agree to wear just a thong and not to wear a bra, she looked gorgeous!
We stayed at the bar we picked out for a little over two hours. During that time 4 guys made an attempt to pick her up. Two bought her drinks and one got couple of dances out of her. I really thought this guy might have an influence on her since she seemed to enjoy her time. She even stopped looking my way while she was dancing which included one slow dance where he placed his hand on her ass and even seemed to reach up under her dress at one point. However, when the dance was over, he had to go to the men's room and Nancy came rushing over and grabbed my hand and said we had to go.
As we left the bar, she said she was very horny and had to have me. We quickly got a cab back to the hotel. During the cab ride, we made out almost nonstop. Her hand made its way to my crotch and she moaned slightly when she realized I was rock hard. She stroked my cock as we kissed and I reached under her dress and managed push the small patch of fabric in the front of her panties a side that was covering her, easily slipping a finger into her very surprisingly wet pussy. She moaned even louder when I penetrated her which caught the attention of the cab driver who I saw out of the corner of my eye. He smiled acknowledging what was going on and I continued my exploration lifting her dress up even further to a point where I was sure he had a reasonable view of her exposed pussy. Nancy at this point was either just not aware or just didn't care as she started to hump my hand wanting more.
Just as she was quickening her pace to an orgasm the cab pulled up to our hotel. The cab stopped and was now lit up by the lights of the entrance way of the hotel which provided a much clearer view of my hand and fingers inside her for the cab driver to see. Rather than quickly pulling my hand out and straightening her dress up she reached down and slowly withdrew my fingers from within her leaving herself fully exposed to the cabbie. She then pulled my fingers into her mouth and licked them clean while looking directly into the cab drives eye as he watched through the rearview mirror. I guess she did know he was looking.
We paid the driver and quickly ran to the elevator wanting to get to our room as soon as possible. Nancy exited the elevator first and walked about 4 steps in front of me. When she got about half way down the hall she started to kick off her clothes. She started first with her heals and then her thong and lastly, she slipped her dress down over her body stopping briefly to kick it aside. I followed from behind picking up the pieces of her wardrobe as I went. We got to within the last few feet of the door to our hotel room with no one in sight. Just as we approached the door a couple came out of their room about 10 feet away and started to walk towards us. Nancy panicked as I "fumbled" with the key, taking a couple of swipes to open the door and giving the couple enough time to get a good view of Nancy. They smiled as they passed behind us and continued walking as if what they saw was perfectly normal.
Nancy bolted into the room shocked at first but once the door was shut, she laughed and said that was "exhilarating" while pulling me to the bed ripping my clothes off as we went. Needless to say, that night ended up with a wild session in bed which lasted well into the early hours of the morning. Nancy admitted that she got very turned on with the last guy that she was with and even more so when they were dancing. I was thrusting deep inside her while she was on her hands and knees she kept talking about the guy. She confirmed during their last dance he reached his hand up under her dress and fondled her bare ass cheek. It was at that point she said that if she had stayed any longer that I might have gotten my fantasy fulfilled since she didn't know how much more she could have resisted his advances.
As I always did in these situations and encouraged her that she should feel free to follow through with her impulses. I said we loved each other and that I was secure enough in her love that if she had a sexual attraction to someone, man or woman I would say, that she was free to have an adventure. My only rule was that I got to watch, or she told me every detail and if possible, send me pictures. Sometimes she would just call me a pig when I spoke of this fantasy but most times her responses were more along the lines that she could never do that as she loved me or that she could never see herself doing that. Sometimes she would tease me and say that there was a time and a place for everything which was enough to keep my hopes alive.
She also worried that I wanted her to be with another guy because I wanted to be with another woman. Although I had fantasies of a threesome like most guys that was not my motivation. I loved the idea of seeing her being pleasured by another man who was preferably larger than me and in return her getting lost in the lust of a more endowed man that could fill her up, I wanted her satisfied completely. I have an average size dick. Nancy keeps saying it is nice and thick but we have talked about our sexual pasts and I know she has experience men larger than me and being thick is nice but being able to fill her up deep inside is not an experience she has had with me.
With all that background, fast forward to last week. Nancy's company had just finalized a big contract that they had been working on for over a year. Some of her coworkers were going out to celebrate. This included Joy who was a close friend of Nancy's that she worked with and Jack who was one of her other coworkers. Jack had been a frequent topic of our fantasy games. It all started when Nancy started mentioning him from time to time in random conversations. He apparently had made the rounds with several of the women in the office which made him the subject of conversation with the ladies in the office and as a result we started to talk about him. I had met him a couple of times and Nancy always said how nice he was to her at work. I started to tease her at some point that maybe she was a little attracted to him.
He was a good-looking guy a lot younger than we were, only in his mid-thirties. He was in good shape, tall and muscular but not body building muscular just fit. He was also single which only added to my level of teasing, because he was available. From time to time Nancy would blush and agree with me that he was nice looking and even "hot" as she said on one occasion after a couple of drinks. Over time this lead to me adding him into my sharing fantasies while we were in bed together. A few times I even got Nancy to call out his name as we were in the throes of our love making session.
