Chapter 13

Tenelle told us to call her if we decided on New Mexico for our trip then left.

Rain was contacting female escorts that she knew that could accommodate her clients based on what they requested and what the escorts were willing to provide. She was basically confirming that the escort did in fact offer the requested service and tried to keep the cost and time the same.

Almost all of the escorts she called were more than happy to pick up a regular client and agreed to accept the current price and time that had been agreed upon. There were only two that she was having trouble with. The first was the client that liked to whip, flog, or beat the escort. He would only be accepted by one escort who did offer this service, however, she wanted $150 more than what Rain charged.

I finally said that I would pay the difference from what Rain was charging if she accepted the client and the client was satisfied with her service. Rain objected but after a very stern look from me and the fact that I picked up a cane, stopped her objections. The escort and Rain finally settled on an agreement they both felt benefited them. I would pay her the difference once a month based on if there were two or three meetings and provided, she only charged what Rain had originally set and the client provided a stellar report on her performance.

The second was a client that liked to mix things up and never really had a constant menu he would follow. There was just too much unknown even with Rain listing everything he had done in their meetings. It truly was an anything goes type of contract Rain had agreed to.

I suggested that she call the client and let him know that she was no longer available for him and that she was trying to find a replacement and need him to give her a list or menu that he would follow and would have to negotiate with the new escort anything different from this list or menu. The client thanked Rain and said that he had just accepted a new submissive/slave and was going to let her know that he would no longer be requesting her services. So that worked out.

With all the clients and new escorts introduced and in contact with each other. Rain was now free from any obligation except to me.

To celebrate I told River to put Rain in her locking restraints and for Rain to put her in her restraints then both to wait for me in the playroom.

I locked the front door and began to undress, folding and placing my clothes on the back of the couch. Totally naked I entered the playroom and found both girls in their restraints including a ring-gag for River and tube-gag on Rain since those were the closest match to what their restraint colors were.

Since both of their mouths were still accessible, I had nothing to complain about except the fact that I had not given instructions to put gags on, but then again, I had not given instructions not to put gags on, and their mouth was still accessible even more so if you were to argue the point.

I took each of them, Rain first then River on the spanking bench, orally and then vaginally finally finishing anally. Then we moved to the bed and I had River restrained first this time legs up over head spread with arms over her thighs and down to the foot of the bed in a frog-like position. The order of penetration was the same, oral, vaginal, and finally anal. Then Rain and River traded places and I did Rain a second time.

After the bed fucking was done, we showered with just a little fondling which was quite a strain on all of us. Then we moved to the regular bedroom and slept together with the restraints still on each girl. I slept great and the girls claimed to have slept great as well.

I woke the next morning with the girls arguing over who was going to suck me off first. I began to laugh and said that since neither of them woke me with a mouth around my cock they both would now be punished. I told them to crawl behind me to the playroom. I remember seeing a 14” dildo that was I think about 2.5” in diameter. Entering the playroom, I went to the junk drawer that had all the miscellaneous items such as dildos, vibrators, nipple clamps, gags, condoms, lubes, and such.

I found the dildo and was shocked to see it was 16” long but only 2” in diameter. As a threat or more like a joke I had drilled through the midline of the dildo leaving 8” on either side of the 550 cord I pushed through the hole. The original idea at the time was to make Rain take one end as a gag and tie it in place with the 550 cord and have her fuck another female with the other 8”.

But I now had the idea of tying a loop on each side of the dildo and use those to tie the dildo as a double gag between the two each choking on their own 8” and mouths touching like a kiss. Using a large strap through each of the 550 loops and going around their heads after they deepthroat their 8” and buckle the strap tight. With each tilting their head opposite the other in a kissing position and 8” of dildo down their throat.

I allowed Rain to work with River to get her to the point of swallowing or deepthroating 8” and surprising both Rain and me she was able from the start. Telling us she has always had NO gag reflex and it was listed as an emergency medical issue like allergies. Since her lack of a gag reflex increased her chances of choking.

Rain just cussed saying she has trouble with deepthroating and asked to be allowed to warm up herself before I buckled them together.

It was crazy and cool at the same time once we began and I had them face each other and lick the dildo before slowly swallowing their end until they had deepthroated their 8” and were kissing. Then I slid the strap into place and buckled it tight. After that, I flipped a coin. Heads = Rain tails = River as to which I would fuck first while the other supported them by kneeling for them to lean on.

Tails was what it landed so River got fucked first leaning on Rain and I enjoyed the sounds of both choking and gagging as I fucked River. I stopped before I orgasmed and had them switch places and fucked Rain while she leaned on River. It was even more exciting as Rain gagged as each thrust forced the dildo just a slight bit deeper every thrust.

Again, I stopped before I had an orgasm and removed the strap and let them pull the dildo out of their throats. Then I had them kneel side by side while I jerked off and cam all over both of their faces.

We had another shower and then sat and talked about where we should go for a vacation. River would have to go home to get her passport and a few other items for a trip so I sent her on her way with instructions to return in less than an hour or else.

Rain knew of a private island in the Caribbean that was kind of a nudist like resort and checked for cost and availability. I checked on flights available and costs. It happened to be the off season and prices were 25% – 35% less and I had her make reservations for three.

I found that it would only be $300 more to hire a private flight than to take first class commercial flights so I made arrangements with a company called CS&S.

The flight was enjoyable, the crew consisted of two pilots and a hostess/Flight Attendant, she made a point of suggesting that if we wanted privacy, she could ride up front with the pilots. We could just use the call button if we needed her. Both girls wanted to make the mile high club. I was happy to help them and they insisted on doing oral, anal, and vaginal.

We did all six before calling for the hostess to provide food and fluid to replace lost fluid and refuel our bodies. I caught the hostess giving both girls a thumbs up.

We were met by a shuttle bus from the resort, it normally picked up multiple people from the airport, the driver a female [Ki] as her name tag read, commented on that fact. Ki was fast moving our luggage to the back space on the shuttle and asked us to sit near her so she could talk with us. She had a lightweight linen jacket that only had two buttons and she hadn’t even buttoned either of them, allowing us to see she was wearing a string bikini underneath and deck shoes.

The drive was surprisingly long as we had to drive to the other side of the island. Since the island is mostly a mountain we were forced to follow the coastline on our drive to the resort. The scenery was beautiful and Ki explained that the other resorts were on the same side as the airport, the larger of the two was a very short drive from the airport going the other way. The smaller, more private resort kind of like the one we were going to was about a mile past the large resort.

The resort we were going to was actually in a lagoon that was protected by a large coral reef.

The resort remined me of the TV show Fantasy Island, there was a dock out onto the lagoon, several golf carts with the multiple seats, small cabanas, and a large southern style mansion.