I Didn't Mind Losing This Bet

I jumped the short distance off the boat into waist deep water and waded to the shore. That's when I had a sudden thought and yelled back to Master.

"What if somebody comes out here in their boat from the opposite side of the island and you don't see them coming?"

"Then you had better keep an eye out for that and be prepared to swim back to the boat. But you can't do that until they have actually set foot on the island."

"You are a cruel Master."

"I know it."

Master went a whole lot further than a couple of hundred yards from the shore to fish. He went out at least a quarter mile to get away from the main channel where the fish would be. I walked around the entire island and saw him way out there when I returned to my starting point. I eventually found the Maple and picked a leaf. No one else came to the island. Master came back to pick me up when he saw me and my tits bouncing up and down on the beach with one hand holding the Maple leaf high up in the air and waving it like I had just found a million dollar lottery ticket. I really enjoyed the time I spent alone and naked on that island. I loved it with just me and nature and nobody else. Master picked me up and we cruised to the far end of the lake and then back to the cabin. I sat in the lounge chair naked for the entire trip. Never did have much use for that bikini.

Tracy showed up the second night. Master and Tracy sat on the sofa in the living room and chatted up a storm for an hour. I stood in silence, still naked and in the slave position with hands behind my head and feet spread wide apart, facing them in the middle of the living room the entire time. They also took a moment here and there to humiliate me. They both kept issuing orders to me during that entire hour. There was a constant flow of orders to play with my tits, pull out my nipples, finger my clit, spread my pussy lips open, finger my cunt, show them my asshole, put a finger in my asshole, finger fuck my asshole, and the list went on and on. Tracy went out to her car at one point and returned with a butt plug and a vibrator. Now the orders were to put the plug in my asshole, vibrate my clit, fuck my cunt with the vibrator, turn it on low, turn it on high, don't you dare cum or I will use a riding crop on your pussy, ass, and tits for an hour.

Then they were both telling me to kneel on the coffee table with my tits touching the surface and my ass aimed toward them was just about the most humiliating command I was given. I still had the butt plug in my ass. Tracy pulled the butt plug out with a little struggle and then handed me the vibrator with orders to fuck my ass with it until I was ready to demonstrate an anal orgasm. Then Tracy pulled a small video cam out of her purse and told me she was going to videotape my entire asshole orgasm to show all of her girlfriends that it can be done. I finally reached the point of an orgasm, received permission to cum, and demonstrated a really nice anal orgasm for the both of them and for Tracy's friends.

Tracy asked me if I had ever thought about touching, and being touched, by another girl. I told her the idea had crossed my mind a few times over the years but the thought of getting it on with a girl had never really turned me on. I told her I had engaged in a very long French kiss with another girl, at a party on a dare, while everyone at the party cheered us on and tried to get us to play with each other's tits. We didn't go any farther than the kiss.

"I won't tell you to do anything that is against your moral values JoAnne, but do you think you might want to try us touching each other tonight? Master would enjoy watching that I'm sure."

"Do you want me to do that Master? Do you want to watch Tracy and I getting each other off for you?"

"This is completely your decision my little newbie slave. Everything we have done this past day has been mostly casual and introductory. I would never ask or command a slave to do something totally against her belief system. This is entirely up to you my pet."

I thought about this for several minutes. This actually scared me. I was afraid I would like it or even like it too much. I'm not a lesbian in any way or form and I didn't want to become one, as if playing with another girl one time was going to turn my entire sexual desire in reverse. Master and Tracy kept totally silent and both were staring at me while I was making my decision.

"I will try it once Tracy, but I want to be able to stop at any time I feel too uncomfortable in going any further."

"That would be just fine with me JoAnne. If you choose to stop at any time, I will just continue on getting myself off while you and Master watch me. Since you have never done this before, may I direct you on what to do?"

"That's fine with me."

"All you need to do is what you would do if I were a man. The only difference is that my body parts are a different shape. You know what feels exciting when it is done to you. I feel the same excitement when it is done to me. We can do to each other what we want a man to do to us but we can do it much better because we are both girls and we already know what girls like."'

Master, feeling left out of the conversation, reminded us that he knew exactly what girls liked. Tracy countered with the rebuttal that men weren't as soft and gentle as girls were.

"Are you trying to tell me that the next time I fuck you that you want me to do it gently?"

We all laughed at that and the tension was broken.

Tracy got up off the sofa and walked over to stand directly in front of me. She is a very pretty girl and has a body to die for. I think she is much sexier looking that I am. Without touching me, she leaned forward until our lips were touching. Our mouths opened slowly and our tongues began to come together. They touched and explored and we pushed our mouths together in a much harder passion.

"Do you want to take my top off and play with my tits?"

I didn't answer that question. I just began unbuttoning her shirt until it was just hanging loose. Tracy wasn't wearing a bra. I put my hands on her upper chest and slowly dragged them down until they were covering her beautiful breasts. Her nipples weren't half as long as mine but they were wider and stood up with pride. I put a hand under each mound and lifted them up with a thumb on each nipple. I rolled and pushed on her buds and they got even harder. Tracy was breathing a little faster now.

"May I suck those super long nipples of your JoAnne?"

"I would like that."

Tracy's mouth sucked in my left nipple and immediately began to softly bite on it and pull on it with her teeth. She would get a light bite and pull out until the nipple finally pulled out of her mouth. She was squeezing and pulling on my other nipple with her other hand at the same time. I began pulling and squeezing hers also.

"Would you like me to play with your clit JoAnne?"

"I would love for you to play with my clit."

At this point, it would be safe to say that I was no longer feeling any fear or anxiety about touching and playing with Tracy's body. My hand went down to her pussy and I worked a finger into her wet slit and slowly ran the tip from top to bottom with a little jab into her vagina. I brought my finger up to my mouth and licked it clean with Tracy watching me closely. She smelled and tasted much different than I did. That was when I first noticed that Master was using Tracy's video cam to tape this entire encounter.

We spent the next half hour exploring each other's bodies and the passion grew at a steady rate. Tracy led me over to one of the living room chairs and had me put my ass against the back of it. She then slowly pushed the upper part of my body until I understood what she was trying to do. I leaned back over the chair until my head rested on the seat. This put my pussy and asshole aiming straight toward the ceiling. I brought my legs back to my chest and then spread them wide apart. This left my vital areas completely open to whatever Tracy wanted to do with them. Master was getting close-ups of everything, starting with Tracy's tongue action. She started at my anus, gave it a little push just inside the hole, and then very slowly licked up all the way past my now very hard and erect clit.

We kept at it for another half hour. Master videotaped everything. His dick was trying to make a new hole in his pants the entire time. We did everything from fingering vaginas and assholes to licking and sucking on each other's pussies. We sucked clits at the same time while lying on the thickly carpeted floor. We did everything we could think of and it seemed to become a contest of who could get the other off first. Tracy won that one but I got her off with my mouth sucking her clit and a finger in each of her holes at the same time. Once we had really started getting into this girl/girl action, I just totally forgot about all of my fears and reservations. Being 'bi' was OK once in awhile was my final thought before burying my face in her sloppy wet cunt with my tongue jammed up into her vagina and sucking up her juices.

When we were orgasmed out and sitting facing each other and lightly kissing one another, Master put is face right up next to ours and said: "Both of you girls smell like wet pussy."

We both joined together to attack Master's rock hard cock. We sucked his balls, put our fingers all the way into his asshole, each of our fingers at the same time at one point, and sucked the cum out of him like it was going to be our last opportunity to taste his cream. We took turns sucking his cockhead into our mouths in a back and forth manner. When Master was obviously going to blow his load, Tracy grabbed his cock and began jerking him off like a pro. We put both of our faces together and she jerked him off until his hot goo sprayed all over both of our faces and hair. All three of us were happy campers. We all got up to take a shower together in the huge glass stall in the big bedroom. We washed each other completely, inside and out. The bed was a king in that room so all three of us slept together in the one bed with Master in the middle fingering both of our cunts as we drifted off to sleep.

One of the things we did the next day, at Tracy's suggestion, was to start my training in converting pain to sexual stimulation and arousal. I love being spanked so having my ass as a target of a paddle, a crop, or a soft leather 'cat' wasn't hard to accept. Having this done to my tits with my super sensitive nipples was much more difficult to handle but they were both very careful when they did this. One would be playing with my clit or fingering my vagina while the other was applying the strokes. I was actually able to cum more often that way but the orgasms weren't nearly as powerful.

"Don't worry about how intense these kinds of orgasms are at first," was Tracy's advice. "With practice, you will learn to cum just from a crop impacting on your pussy and clit. Master even taught me how to cum without even being touched by anything at all. It's totally different but you will be amazed at how nice and relaxing an orgasm like that can be.

Master told me that there is a big difference between punishment and using pain to enhance an orgasm. You will learn pain/arousal and then beg for even more pain to add to your getting off. We will find your limit on the amount of pain you can accept and still be able to combine it with your increasing sexual arousal. With punishment, it is an entirely different set of circumstances. Punishment is used to keep you on the right path. If you wander off the path during your training, you will be punished. If you do something wrong, you will be punished. If you don't do what you are supposed to do or have been ordered to do, you will be punished. If you deliberately disobey me for any reason, you will be punished severely. If you ever cum without permission or become rebellious in your attitude, you will be severely punished for a length period of time. There are no safe words during a punishment.

Master also told me that I can say 'yellow' at any point that I need to temporarily back off a training session. He said I can use 'red' to stop a session that is just totally overwhelming me completely. He said that I can do this at any time without punishment but that I must be very careful if I should ever need to use either of those safe words.

"They are never to be used to stop a training scenario that you just don't happen to like or don't feel like dealing with at that moment. They are only to be used in a case where your senses are being overwhelmed or you no longer understand the purpose of the training. Believe me, I can tell the difference my little cum slut. You know all too well just how deeply I can see the truth inside of you. Using either safe word without justifiable cause can easily cost you your status as my submissive slave. I will kick you out in a heartbeat if you ever deliberately misuse our mutual trust in each other. Am I quite clear in that my pet?"

"You are quite clear on that Master."

Tracy and I went out in the canoe together one time. We were both naked of course. We didn't go very far. We just had a lot of fun being naked in a canoe on a large lake.

Just before Tracy had to leave us and return to her daily routine, Master ordered me to sit in one of the living room cushioned chairs that faced the sofa, put my legs over the arms of the chair and move my ass until it was just over the front edge, and masturbate. That position opened up both my pussy and my asshole for easy access and viewing. I was told that my parting gift to Tracy was fingering my clit to a climax, finger fucking my pussy and my wrinkled brown eye to an orgasm, to cum again using a vibrator in both of my holes, and to create a big orgasm with the vibrator on my clit. They both watched me intently through each erotic explosion. The entire scene was videotaped. When I had cum with the big one, which was last, Tracy came over to me, knelt down, and tongue kissed my asshole, my vagina, my clit, both nipples, and then a long one on my mouth. She thanked me and said that I was a very special submissive and that I would have no trouble in eventually being collard by my Master. She made me promise to invite her to that ceremony, no matter where it was given. I kissed her again and promised her I would. I didn't see her again during the entire month that Master Bill and I spent together.

It was a never ending spree of learning, playing, training, and experiencing for the remainder of that month. Master bought a remote vibrator egg set at an adult store in a nearby town on one occasion. He inserted one egg in my pussy and one up my ass. Each had a small wire that hung down outside of my two holes. I then had to wear a mid-thigh skirt that barely covered the wires and he took me to a famous college campus that is one of the oldest in the entire country. We spent half a day sightseeing and walking through the little town center made up of dozens of tiny stores. He literally kept my body in a state of total arousal during that adventure. No panties either. I never get to wear panties or bra anymore. The entire time we walked around that campus, Master would randomly fire up the eggs. Sometimes at low speed and leave them running for awhile and a couple of times at high speed until I had had a walking orgasm. Some of you reading this story probably know exactly how difficult it is to maintain any dignity while having a walking orgasm. He gave me another climax in a restaurant while we were eating lunch. When we returned to the cabin, I came so hard, so many times, that I lost count halfway through.

I fell totally in love with my Master before the first week had ended. Master fell in love with me just as he said he probably would. I moved back to California with him. I earned my collar in just over a year. Tracy did come to the ceremony. We both completed college with degrees. We have a nice home and we have two children. We also have two grandchildren. And I have been Master Bill's totally committed submissive slave for the last 40 years. We are both 60 now and we are both lucky enough to have stayed extremely active sexually in every way. We can do the exact same scenes that we did when we were kids. It just takes a little longer to complete them.

My love to all of you reading this very true story and I pray that all of you find the happiness Master Bill and I have found together.

Love...JoAnne