I earn a trip to Hawaii along with several other salesmen in my region.
I was the top salesman in my territory last year and that earned me a two-week vacation in Hawaii. There were nine other territories in our region so ten of us were headed there. It was just for the salesmen however and not our wives. We were told that there were going to be a few sales training seminars. Besides I really couldn’t afford to pay for my wife to go to Hawaii with me. Besides who would we get to stay with the kids? It was best that I go alone.
I checked in at the Buffalo airport. My flight would get me into Chicago and then I would have to transfer to a San Diego flight. From there I would transfer to another flight that would take me to Hawaii. As a salesman myself it was cute when the girl behind the counter pointed out that the San Diego to Hawaii flight was non-stop.
The flight to Chicago was non-eventful. I had an hour layover so I walked around a little bit. Then they called for us to board our San Diego flight. Since the company had made the reservations for all of us it was a big surprise that four of us were from the same company and sitting together. The two guys sitting in front of me and the lady that was sitting next to me near the window were some of the other top salesmen. It hadn’t dawned on me that a top salesman could be a woman. Samantha was a very attractive blonde. Samantha was wearing a tight black mini skirt with a white silk blouse. Her black bra was visible through the white material. The more Samantha twisted in her seat the higher her skirt rose. She caught me looking at her lovely legs more than once and we hadn’t even taken off yet. Samantha didn’t seem to mind me looking.
Soon Samantha started to question me about where I was from, about my wife and children, and about my sales territory. She also offered the same information about herself. Samantha had been married for five years and had a three-year-old daughter. Samantha surprised me when she asked if I was a member of the “Mile High Club.” I told her that I wasn’t. I just about died when Samantha asked me if I wanted to join it with her. Yes! Hell yes! I certainly would! So believe it or not she actually asked the stewardess to cover for us and she said that she would. The stewardess said that the bathrooms were way to small to fit in comfortably but she said the galley was perfect if the woman bent forward and the man slipped it into her from behind. She said that she would come back and get us after they finished serving a snack.
Sure enough the stewardess did give Samantha and I a signal and we both headed to the back of the plane. The stewardess pulled the curtain closed and stood guard like she said she would. I watched as Samantha lifted her black mini skirt above her waist and removed her white cotton panties. They were not sexy or even thong panties. Samantha put them on the counter and grabbed onto it to steady herself. I dropped my pants and underwear to my knees and stroked my cock a few times before aiming it at her pussy lips. Samantha reached down and helped me guide it into her wet pussy. I was already pretty excited and Samantha was very sexy so I came fairly quickly, to quickly in fact. I apologized but she just smiled and said that it was okay. Just like a wife to accept a piss poor job of sex and act like it was okay, it wasn’t okay. Samantha then shoved her panties into her pussy to soak up the wetness and pulled her skirt back down into place. I pulled my underwear up and tucked my cock back in and then pulled my pants back up. We both thanked the stewardess for her help and took our seats. I reached between Samantha’s legs and tickled her clit for her every now and then to make up for my bad performance. She sure liked that. Just before we landed the pilot came back to us and gave Samantha and I a pair of pink wings with MHC engraved in them. We were officially members of the Mile High Club. Samantha pinned her wings to her black bra strap but they were still visible through her white silk blouse. I decided to pin my wings to my shirt pocket so that everyone could see them. Hell I was proud of them. I just wasn’t proud of my performance that’s all.
As we exited the plane we seemed to get special treatment. In San Diego Samantha and I were upgraded to first class for the long flight to Hawaii. We were sure that it was because of our pink wings. When we boarded Samantha sat down and let her skirt raise up considerably. She said to me that she had decided to let loose. She was never going to see any of these people again so what did she care if they saw her panties or not. I had forgotten about her white cotton panties being in her pussy but she had used the ladies room in San Diego, washed them out, and had put her wet panties back on. Soon her skirt was high enough where even I could see the white crotch. That pleased her. At Samantha’s request we joined the “Mile High Club” two more times during that flight. Each time the sex got better. We decided to do it in the restroom on that flight but Samantha still asked the Stewardess to keep an eye out for us. Samantha liked the cramped quarters and the fact that everyone in first class had seen us walk in there together. They knew exactly what we were doing. Samantha even hammed it up a little by not pulling her skirt back down in place until she had stepped out into the corridor. The second time we were greeted with applause when we exited. As a way of saying thank you Samantha lifted her skirt back up to her waist, did a little spin, and walked to her seat. Before landing in Hawaii the stewardess handed me four more pink wings. I gave two of them to Samantha.
When we checked into our hotel in Hawaii Samantha made sure that she and I had rooms with connecting doors. They graciously accommodated her request. That first day the ten of us top salesmen were taken on a bus tour of the island and treated to a wonderful seafood dinner. There were two women in our group. Later that evening Samantha and I made use of the hotel pool. She sure looked good in the new bikini that she bought. Apparently her normal one covers her up too well. She was a liberated woman, at least for the next two weeks. That first night Samantha and I slept in my bed together after our first really comfortable love making on a real bed. It was very exciting. Neither one of us had thought about cheating on our spouses before but we just clicked. In the morning we showered together and met the rest of our group for breakfast. That day we were taken to the beach and Samantha decided to go topless. Debra the other woman in our group was much more conservative and wouldn’t go topless. Samantha seemed to enjoy the fact that I was taking a lot of digital pictures of her topless on the beach. I took a lot of other pictures too. Later I would download them to my lap top computer. The other guys said that I was very lucky to have joined up with Samantha. I felt the same way too. She was one very special lady and not just because I was fucking her either.
After a full day of ‘fun in the sun’ we went back to our hotel and made love before going to dinner. Later that evening Samantha and I took a walk on the beach and admired the beautiful sunset. Samantha wanted to pose for me in her top and out of it too. She loved being my nude model and I loved taking pictures of her. That second night we fell asleep making love again.
The next day Samantha talked Debra into going topless on the beach with her. I could tell that Debra wasn’t comfortable doing it. After all it was a very big step to show her breast to eight men that she technically worked with. From what I knew of Debra already she hadn’t shown them to anyone but her husband and her doctor since marriage. The other guys and I sure enjoyed seeing them though. Samantha and Debra were two of the finest looking women on the beach that day. Many other men noticed them too.
Samantha mentioned that her nickname was Sam and that SAM were also her initials. Her full married name was Samantha Ann Morgan. Debra laughed and said that her nickname was Deb and that DEB were also her initials, which stood for Debra Elizabeth Brown. What a coincident.
That evening after dinner Samantha talked Debra into coming to her room. Of course with our connecting doors open and the fact that Samantha was sleeping with me Debra wound up in my room too. Samantha opened a bottle of wine and they shared it. Samantha coaxed a very tipsy Debra into trying on a beautiful red silk nightgown. I took some very sexy pictures of Debra in it. Since I had taken a lot of topless pictures of her earlier that day on the beach she was not as concerned as she might otherwise have been. Samantha undressed to show off her sexy blue bra with matching panties. This time they were thongs. I took lots pictures of her too. Halfway through the second bottle of wine Samantha managed to talk Debra into trying on her white transparent negligée. I got some great pictures as Samantha grabbed the bottom of the red silk nightgown she was wearing and lifted it up over Debra’s head to remove it. Debra cooperated fully! Samantha then tucked her thumbs into Debra’s panties and lowered them to the floor and had Debra lift her feet to remove them. Samantha flung them at the camera and I actually caught them in flight with Debra nude in the background. Samantha fumbled with the white transparent negligée on purpose so that I could take more pictures of Debra completely nude. She slowly helped her on with it but made sure not to cover her breasts until the very end. Then of course once Debra had it on it sure didn’t cover much. Samantha removed her blue bra and blue panties and this time flung her panties at the camera. I tossed both pair of their panties into my suitcase. After the girls finished off that second bottle of wine Samantha removed Debra’s white negligée and kissed her very passionately. They looked unbelievably beautiful breast to breast, pussy to pussy, and mouth to mouth. They must have kissed for a good ten minutes before starting a very sensational sixty-nine. I took hundreds of pictures of these two women as they tried to devour one another. After they passed out completely exhausted I fucked Debra. Right in the middle of my making love to her Debra opened her eyes and just smiled at me. I gave her another orgasm as she fell asleep again.
In the morning Samantha was sucking my cum out of Debra’s well used pussy when I woke up. Debra was lovingly stroking Samantha’s hair at the time. I got up and took some more digital pictures the two women. This time Debra was fully sober and smiling like she was really enjoying herself when I took the pictures. We showered together and then dressed for lunch. We had missed breakfast completely. After lunch Debra moved her suitcase into Samantha’s room. That way the other guys would not know that we were going to have a threesome every night from now on.
However the other guys started making comments about Debra and Samantha. They suspected that the two girls were lesbian and actually started leaving them alone. The girls started having a contest to see which one of them could wear the least, be more revealing, or get topless first. The other guys sure took notice of them after that. The girls loved all of the attention that they were getting but had made up their minds that they didn’t want to sleep with any of them. The girls actually liked each other but would let me fuck them whenever I wanted to. I enjoyed seeing them make love for hours.
The girls started getting very nice topless tans. It was a lot easier to see when they removed their bottoms for me. They had cute white marks where their pubic hair used to be. Being topless and wearing thong bikini bottoms didn’t really leave a lot of unexposed skin.
The girls took a couple of lessons and learned to do the Hula. All ten of us went snorkeling and the tropical fish were just gorgeous. We all attempted to learn to surf too. A couple of us did manage to stay up for a short period of time. Every night the two girls would entertain me by making love to each other until I couldn’t stand it any more. Then I got my choice of one or both of them. I usually took turns.
Samantha and Debra fell in love and I loved them both. The two weeks flew by all too quickly. None of us wanted to leave Hawaii. Samantha, Debra, and I pledged to stay in touch and even try to get together from time to time.
On our flight home from Hawaii Debra asked me to induct her into the “Mile High Club.” Samantha had put her up to it. This time it was Samantha that covered for us. Debra and I had sex in the tiny bathroom twice while Samantha and I had sex in there only once. However, Samantha had gotten very bold and offered her body to the seven other salesmen if they wanted to join the Mile High Club. Samantha spent almost the entire flight in that cramped toilet getting fucked. Several other passengers fucked her to join the Mile High Club too. The copilot handed out the pink wings to everyone before we landed in San Diego. He handed out about twenty of those pink wings and gave Samantha a gold pair that represented service above and beyond the call of duty. Samantha displayed that pin very proudly.
Boy was my wife ever glad to see me when I got home. She fucked my brains out for the next three days. When she found the two pair of panties in my suitcase I told her that I had met a pair of very nice girls. My wife surprised me by putting them up to her nose and then saying that she would love to make love to the owners of those panties. Then she showed me the four pink wings that she had found too and asked me what the MHC stood for. I explained to her about the Mile High Club and she didn’t get upset at all. Then I showed her some of the topless beach pictures that I took of Samantha and Debra. She definitely wanted to make love to them after that. This was a new side of my wife and one that I had not seen before.
Over the next week I mentioned more and more of what actually had happened in Hawaii. My wife got more and more sexual the more I told her and she got more aggressive in bed too. It was interesting to see her so physical when we made love instead of just lying there like she usually does. My wife started wearing more sexy nighties in the evening too. She purchased sexier clothes and started wearing them out in public when she was with me. Eventually I showed her every single picture that I had taken of Samantha and Debra in Hawaii.
My wife called them both at work and personally thanked them for taking such good sexual care of me while I was in Hawaii. After that she started emailing them and keeping in touch.
Eventually my wife found out that both Samantha and Debra were going to be in Philadelphia on business for three days and suggested that we meet them there. The girls agreed and we booked a suite for us with two bedrooms. My wife was so pleased to finally meet Samantha and Debra. I was very glad to see them again myself. That first night in Philadelphia my wife made love to both women for over an hour. She loved her very first experience and was no longer a lesbian virgin. I took several pictures as usual. After that I made love to Samantha then to Debra before going to sleep. In the morning I made love to Samantha again before they had to start their day. My wife and I talked about what a great time she had with both women then we took in some of the sights.
After work Samantha and Debra rushed right back to us. My wife and the two girls dressed very sexy to go to dinner with me. It felt great when every eye in the place turned our way when I walked in with three extremely sexy women. Like in Hawaii the three women didn’t think that they would ever see any of those people again. Therefore they could do things that they would never have dreamed of doing before. During dinner my wife crawled under the table and gave me a blowjob. Wow! After that it seemed to be a game to see who could out do whom. I loved it.
My wife went wild and the other two let her go. My wife kissed each girl passionately right out in public. In the hotel elevator my wife knelt and ate Samantha’s pussy with two married couples in there with us watching her do it. My wife offered to do the other two ladies too but they politely declined. She gave them our room number anyway. Sure enough an hour later one of the women from the elevator knocked on our door. She decided to accept my wife’s kind offer to lick her pussy. All three of my women took care of her. I even got to fuck the lady’s pussy just before Debra ate her out a second or third time. I took plenty of pictures of course.
All in all my wife fell in love with Samantha and Debra too. We have been very close friends ever since.