Vacation Surprise

As we walked down the hall, Toni asked me, "How much did you really lose?"

"Actually, I was up about $50 when you arrived."

"Then how did the other guys know to go along with you?"

"Well, we were discussing whether any of us had ever discussed sexual fantasies with our partners and I told them about our discussion -- while having sex about a year ago -- when you said you had thought about having sex with other men while I watched", I explained. "Then about a week before our vacation started, you said we ought to do something this year to make our vacation more exciting than past years. As they told me about their group, we then began to plan how to get you to agree."

She immediately asked, "But what would you have done if I refused? I wasn't sure I would have agreed until we already started -- I was mad at you thinking you had lost a lot of money and as I figured out it was a set-up, I was already committed to it."

"If you had balked, we have claimed it was all a joke and I was sure you would get over it in a day or so."

"Well, I have to say I didn't come to this room expecting to get fucked by three strangers while my husband cheered me on -- but it has long been a fantasy of mine and now that it is done, I'm glad I did."

She turned to me and finished, "Don't forget, you have told me your fantasies also -- and some of them are going to happen on this vacation! For now, I need to shower and douche."

I sat in the room while she was in the bathroom and began to think about what to say when we met again. We expected to see them at the pool the next day when Mike's and Tony's wives would be present. I was getting excited thinking about both what had just happened and the things that might be happening over the next few days.

When she finished and I was in the shower I began to stroke myself and my penis was raging hard when she entered the bathroom. She laughed and said, "I see you are thinking about our next meeting with them and looking forward to meeting the wives! I'm not ready to agree to a long term arrangement but let's play with them awhile and see if we are interested in it. Now stop playing with yourself and save that for when you come to bed."

In bed, I snuggled up behind her and pressed myself against her buttocks. She rolled onto her back and I moved into the missionary position and entered her. She reached behind me and spread my buttocks so she could push a finger into my anus. I loved this but her arms were not long enough to allow very deep penetration but it was still pleasurable for me. She spoke softly into my ear, "You have always loved this but I know you want deeper penetration. Some time ago, I asked if you would like to have a man penetrate you there while you were fucking me and you said yes. I have often wondered how I could arrange that for you and now I think I can. I'm going to do my best to have another man fuck your ass while you fuck my pussy -- this week!"

With that, I poured my load into her and moaned from excitement. As I rolled off her and she lay against me with her head on my shoulder she said, "You like that, don't you?"

"Yes", I agreed.

She rolled me onto my stomach and she knelt over me. She pushed one and then two fingers into me, probing until I moaned again. Then she rubbed fingers from both hands in her vagina, coating them with a combination of our juices. She inserted fingers into my anus and when she had a finger from each hand inside me, she suddenly stretched me wide causing me to cry out in pain. She said, "You once told me you would like to feel a little pain there. Do you still feel that way? Because if I can find a man with a really big dick, it might hurt! I remember my first time and I want you to remember your first. So I want you to agree now to allow me to arrange it and do it my way?"

By now I would have agreed to almost anything she suggested. "OK", I murmured.

When she returned from the bathroom this time we snuggled and soon were both asleep.

The next morning, we were at breakfast when we saw the bus return from the observatory trip and we couldn't help but speculate which of the women were Kim and Linda as several couples and a group of six women entered the dining room. When Tony and Mike arrived, we learned which their wives were. The four of them came over and proper introductions were made. I decided that sex with these two women was likely to be wonderful. Of course, at this point neither woman knew what had transpired the evening before.

The other wives went to their rooms to nap as they had been up most of the night. Toni and I were scheduled for a tour of a nearby historic area and we left on the bus. During the tour, we made little conversation about our new friends, except to agree that if this vacation was to be the time we explored new ideas for our relationship we would need to participate in new activities with new people.

After our return to the hotel we dressed for dinner and when we entered the dining room our friends were at a large table and motioned us over. We enjoyed a good meal together with a few double entendres referring to the night before -- and possible future events -- which made it apparent the wives had been filled in on the details.

As we enjoyed coffee afterwards, Toni and the other wives all left for the ladies' room. Doug asked if we had discussed joining their group and I admitted we had agreed to do so for the remainder of this vacation and decide later whether to continue in the future. They were planning a visit to a local nightclub the next night and invited us to join them. Mike explained that the nightclub was a BDSM place and that he and Linda were going to participate while the others watched. They had experimented with such play closer to home but wanted to be able to engage in more intense activity where they were even less likely to see people they knew. I agreed to discuss with Toni whether we wanted to go along and watch.

The girls returned from the power room and Toni winked at me and said in a low voice, "Would you believe Tony is bi-sexual and Kim assures me they will help us fulfill your fantasy?"

Kim was whispering to Tony and he was smiling. Kim turned back to the group and said, "Ric has a fantasy Toni wants to fulfill for him. We also discussed some more things but we will discuss them later. Ric and Toni need a little privacy to discuss whether to do this in their own room in relative privacy or to do it in Doug's suite in front of all of us. So they are going to go for a walk while the rest of us have an after dinner drink." With that, she winked at me.

Toni and I excused ourselves and strolled out on the patio. From there we strolled along a garden path as we quietly discussed the evolving situation. She told me the girls had discussed Tony's bisexual nature. Kim liked sex with both genders as well. Toni told me she really wanted to carry out my fantasy tonight as well as another of hers she had never told me about, that of her being doubly penetrated vaginally and anally. She said the other women wanted to watch it all and she was willing. She asked me to spend the remainder of our vacation exploring new ideas and sex acts with our new friends and just to go along with what happened. I agreed to do it her way and we could decide after we returned home whether we would continue or just call it a vacation adventure.

We returned to the dining room and we all agreed to meet at Doug's suite in one hour. Toni and I went to our own room and, once there, discussed what we thought was about to happen. She wanted to power her body and apply perfume to her armpits and pubic regions (even though she had showered and applied her normal stuff just an hour and one-half before). Before she re-dressed, she stood before me and turned slowly around, asking, "Do I look like a slut about to be fucked by four men? Or, like a hussy ready to have her husband fucked in the ass?"

"Both, I guess.", I said as I fingered her vagina.

Within minutes we were walking down the hall and saw Mike and Linda at Doug's door. We joined them just in time to enter when Doug opened the door and said, "Good, we're all here." I could see Tony and Kim on the couch.

We all sat in the living room a few minutes before Doug said, "The best way to do these things is to just start. Toni, go into the bedroom and get undressed. Get on the edge of the bed and, Ric, you follow and get undressed and enter her. You should both be on the edge of the bed so Tony can stand next to it -- we have done similar things before."

I followed Toni into the bedroom and we positioned ourselves as Doug had instructed. I entered Toni and moved to and fro a few times but stopped as the others entered the room.

I was inside Toni, not moving in fear I would climax before the others were ready. I sensed, rather than saw, that Tony was undressing as the others watched. I was tempted to twist around to see if his member was as large as I remembered but suppressed that desire.

I felt hands spreading my buttocks as Tony positioned himself. Fingers spread lubricant into my anus. "Tight." said Kim.

There was a brief spasm of pain as he pushed through the ring of muscle and I gasped. He paused to give me time to relax before withdrawing and plunging back into me. I began moving inside Toni but a rhythm was hard to establish. I pushed all the way into her and held it there as Tony began moving inside me until he climaxed. He withdrew and I began to move inside Toni until, first she, and then I climaxed.

As the three of us made trips to and from the bathroom, Kim (now undressed) lay on the bed and Doug and Mike began to caress her body as Kim started to do a striptease as if she was hearing music the rest of us could not hear. Someone said it was time to fulfill Toni's desire and asked who she wanted to do her. Soon Mike was on his back on the edge of the bed with Toni riding him. Tony positioned himself behind her and the rest of us took up positions where we could watch as she moved up and down on Mike's member as Tony pushed into her behind. I marveled at how easily Tony's large penis could penetrate her there. Kim was spreading Toni's buttocks so that we could all see it enter.

"Oh, fuck me hard!" Toni cried out as both men pushed into and out of her passages. It was so intense and over so fast that we all just sat down wherever we could.

Linda suggested that we all move to the living room where there were more places to sit while she and Kim made drinks for us all. We all remained nude as we did so.