A bet lost and won
The whole week had been hot. Actually, the whole damn beginning of the summer had been hot. And now, a small vacation. 24 free hours. 24 free hours were going to be spent in a nice, clean, quiet, motel room. But, that was yet to come…
Kathy bound out the door toward the car. Naturally, being the gentleman I am, I opened her car door for her and took her bags. I carefully placed her luggage in the trunk and quickly got back into the driver’s seat. Although we both knew what lay ahead this weekend (sex), of course, casual small talk took over. We had known each other for about a year at this time. Sex became something to look forward to for both of us. But, we wanted to put a deliberate twist into our sex to liven things up. Quite a few subjects were tossed in the air and commented on as we drove to the motel. But, not much substance to the conversation could be recorded. Ultimately, like all conversations where some anxiety or anticipation is present, the topic we returned to often was the weather. And, ironically, it was an appropriate subject. It was hot. And, it wasn’t going to get any cooler.
Through the whole summer, we had exchanged letters. We often met on weekends and had frequent retreats to motels. Sometimes motels could wait, sometimes hotel rooms were paid for in haste with no real sleeping involved, and sometimes we bummed around Indianapolis first to highten the anticipation for what was to come. After each liason, our letters would often jump into the subject of sex–literally. One subject never connected to another. These discussions would often lead to fantasies that we would both someday like to bring to reality. Unknown to myself, one of those fantasies we discussed would soon be reality.
I was soon surprised. Our favorite cuisine for that summer was Korean and Chinese food. As we were sitting in a Chinese restaurant, Kathy casually dropped her plans right in my lap.
“So, Allan, are you up for tonight?”
“Well,” I responded, “that all depends on what is going to happen tonight.”
Kathy smiled mischievously, “Well, I have a lot planned for tonght. Are you up for a bet?”
Quite surprised at Kathy’s new lack of shyness I asked, “Uh, what kind of a bet do you have in mind?”
“Mmm. I have a very challanging bet for you. I bet you I will give you the wildest time of your life tonight. However, there is a switch. If you let me be in complete control of everything from the time we leave this restaurant, I will give you the best and most interesting sex in your life…up until now. But, that is not the bet. I bet you that I can give you the best sex you have had up to this point. If I win, I get as much oral sex as I want for a whole weekend.”
“And, if you lose…if you don’t give me the best sex I’ve ever had?”
“I haven’t considered losing.”
“Oh, so you are so sure you can do this?”
“Yes. But, to be fair, I’ll give you this–if I lose, I’ll consent to having sex in public with you.”
“Even if it is the Mall? In Fredericks?”
“Right. I wouldn’t bet this if I wasn’t so sure.”
“Well, don’t be so sure.”
“You wait Allan…You wait and see. You’ll soon be using that tongue of yours.”
“You’re on. I’ll take that bet.”
We finished eating, snickering the whole time, not believing either one of us could win that bet. Admittingly, it seemed pretty bizarre. Not totally out of line, but a little bizarre. I knew Kathy. I wasn’t too sure she could do it. Writing about fantasies and what one wants sexually is one thing, but actually doing it is another. As soon as we were finished eating, we took a half hour walk to help digest our food, then drove to the hotel.
Leaving out all the usual exciting pleasantries of getting the room key….
According to the bet, Kathy was in control as soon as we got back in the car from the restaurant. But, I never knew it. I didn’t see any evidence of it until we entered the room.
Being the common man I am, I immediately had the boob tube turned on. Within a few seconds, *click* off went the TV.
“Allan, there won’t be ANY television tonight. None at all. Now, you accepted this bet, and I am in complete control. Get out of your clothes, put them in the extra trash bag over there and tie it up. Then, go take a shower. Every inch of your body better be SQUEAKY clean. And don’t take more than half an hour. I’ll read while you are showering.”
Now I knew she was serious. She ignored me as I disrobed. I was a little slow to see what she would do, “Hurry up! What do you think this is anyway. Get those rags off and in that bag!” Now I really knew who was in charge.
I quickly shed the rest of my clothes, placed them in the extra garbage bag that was inside the plastic pail, tied up the sides in a granny knot, and raced into the bathroom. I turned on the shower to a nice warm, strong stream, and began washing my hair. Soon, I had washed my hair three times, cleaned the rest of my body twice, and shaved.
I vigorously dried myself, combed and dried my hair, and brushed my teeth…twice. As soon as I opened the door, I was grabbed and faced toward the motel room door. “You barely made it Allan. Don’t turn your head. Keep your nose to the door. You are my piece of meat for the rest of the night.”
I listened for Kathy as she walked away from me. She went into the bathroom and took a shower herself. I knew better than move. I was never sure when she might be looking. Even though the water was on, I couldn’t be sure she wasn’t in the shower. It seemed like a long time. I could see out the peep-hole and felt very exposed as I watched people pass by and enter and exit their rooms. What did seem like a long time was not probably. About 30 minutes later, I heared Kathy’s voice behind me, “Don’t move. I’m putting a blindfold on you.”
This was no ordinary blindfold. First, Kathy put a sleeping blindfold over my head. These blindfolds are usually used to sleep in. And, they are quite effective at keeping the light out. But, next, Kathy put a bandana around the blinfold and tied it snuggly on my head. “There, that should keep you deprived of your sight.”
“Now, put your hands behind your back.” Soon, I heard the tell-tale click of handcuffs and felt the cold metal against my skin. “That should keep your hands from getting into trouble. And these should keep your from running away.” The next feeling I had was what felt like handcuffs on my ankles. This confused me. I knew none of the handcuffs I had would even fit!
“These are leg-cuffs. I bought them from a police supply house in St. Louis. When you walk, take small steps. There is only about two feet of chain between them. I don’t want you falling. I can’t damage my merchandise.”
Kathy was playing this role to the hilt!
“Now, turn around big boy. Slowly. I’ll guide you.”
Kathy was treating me, truly, like meat. As soon as I was turned sufficiently, Kathy stopped me. Then, I felt something rough around my neck. It was a collar. It felt skinny, but big enough to be a dog’s collar. Soon, a leash clicked into place around the front of my neck.
“I will lead you now. Follow the pull of the leash, doggie, and you will be quite safe.”
Following the leash, I had no idea where I was going. Soon, to my surprising embarassment, my cock began to enlarge and grow to a full erection.
“Now, sit back. There is a chair behind you. When you sit, make sure your knees are parted.”
I moved back, hesitantly, until the front of the chair bumped the backs of my legs. Now I knew where I was going. The feeling was reassuring. I sat down and spread my legs as asked. My handcuffed wrists stuck out behind the back of the chair.
“Now,” Kathy announced, “about the bathroom. I don’t know how many times I ask when we are together, but you left a mess. You’ll have to pay. And, you will probably regret the mess you made as I have never spanked a man before, but you don’t know how many times I wanted to. So, I have been reserving my feelings for some time. You won’t be disappointed. 20 strokes ought to be enough, but, to make sure, I think I will write down some numbers on pieces of paper and let you pick the additional strokes that should make you remember your paddling.”
Now I knew she was REALLY serious. But, my cock responded by getting as hard as I think it has been in quite a while. But, how was I going to pick those pieces of paper?
Soon, I found out. Pressed into my face was a hat. I couldn’t figure out what kind of hat it was since I hadn’t worn any. But, that’s what it was. “Open your mouth and grab a piece of paper. There are five in there.” Kathy shook the hat a little and replaced it over by face. I opened my mouth and found nothing. So, I stuck out my tongue and touched a piece of paper, brought it to my lips and held on. I Mmhmmed as a signal that I had one.
“Ok, let’s see what we have here.” Kathy took the paper from my mouth and giggled. “Boy, you are going to get it. This is pretty good. This piece of paper has the number 20 on it! You will be getting 40 on the ass. I will make it red too. Maybe you won’t soon forget to be civil and keep after your messes!”
Kathy began tugging on my leash. I got the signal and stood. “What’s next Kathy?”
“Did I give you permission to talk, boy? I don’t think I did. How would you like to pick another number out of the hat?” I shook my head. “I didn’t think so. Consider that a warning.”
Kathy then pushed me from behind so that my calves met the bed. I wasn’t sure what side. She helped me up to my knees on the bed. “Now, I have planned this for quite some time, as if you didn’t notice. In front of you are three instruments. One will be my hand. The other will be your very own belt. And the third will be one of those paddles from a ball and paddle game from WalMart. They don’t lay in order in front of you. You will pick a number from 1 to 3. I will then pick that instrument from right to left using the number you give me. I will then use that instrument to give you your well-earned spanking. Now pick.”
This was very interesting and exciting. Now only was I being deprived of most of my senses, I was having to pick my own outcome in this punishment! I was in control of my destiny (so-to-speak) yet, Kathy was in total control. It was driving me wild. So far, I felt like she was well on her way to winning this bet! I had never experienced anything like this. It was erotic/semi-humiliation/and exciting.
I was apprehensive. I could pick any number, and it could be anything but Kathy’s hand. I decided not to waste any time and anger her. So, I picked number two.
“Ah, you got lucky. It is only the paddle.” Only the paddle!?! Oh my.
Kathy stood me up and began to tease me. She knew how much I like my penis stimulated in any way. She gently caressed my balls and traced her soft fingers around the head of my cock. Pre-cum had already oozed out the tip, but she spread it around to make room for more to come.
Surprising me, Kathy sternly turned me around and unfastened the handcuffs. But, before I could do anything, she left my right wrist secured, brought my wrists in front of me, and relocked the handcuffs. Then, I was bent over Kathy’s knees. I was beginning to get apprehensive.
Kathy carefully made sure my cock was between her knees. I could tell she was naked, and enjoying herself. Even though I couldn’t see, I knew she was smiling. And, she was enjoying this. So was I.
The first blow fell with a resounding SMACK. It didn’t hurt too much. But, no sooner than I began to think about how intense it was, another fell *SMACK*. Gradually, Kathy paddled my ass, slowly increasing the intensity. All through the spanking, Kathty made sure to move her thighs about, mostly up and down. This was sheer torture for my cock which was buried between her milky thighs. Several times I came close to ejaculation…she knew it. And, she laughed each time. By 30, I was praying she would stop early. But, she didn’t. She prolonged my anxiety. At 30, she slowed the pace of her ‘blows’ waiting for a random amount of time between each one. She also made each stroke much harder. At 38, she warned, “Now, these last two are going to be quite hard. Don’t move…or I shall have more fun with you later on.” As promised, the last two were quite hard. However, they probably felt worse than they actually were after all the others I received.
She let me recover a few minutes and caressed my red ass, rubbing in what I thought was baby oil. My ass was hot, but it was going to be soft too.
Kathy again guided me to my feet. This time, I was lead to a bed (I wasn’t sure which one at this point). Carefully, Kathy helped me lie face up on the bed. I heard Kathy enter the bathroom. The wait was terrible. But soon, Kathy was back.
I felt the bed give as Kathy got up on the bed. I was limp once again, but there was quite a bit of pre-cum on the head of my cock. I jumped slightly as Kathy bent down and swallowed my limp cock whole. Kathy was good at oral sex and she was quite proud of her skill. She slowly brought my limp cock back to life using her warm, wet mouth. It felt like my cock was in slightly unsolidified jello. Warm and silky.
Soon, with all the heavenly attention, my cock came back to life. It was rock solid in less than a minute. Kathy keep slurping loud enough so I could hear, something she normally does not do. Her tongue was torture on the head of my cock. It traced firm circles from the base of the head, slowly like a corkscrew to the tip, taking time to lick all the pre-cum, and then back down to the starting point. She continued this treatment until I was moments from orgasm. Then, suddenly, she stopped. The frustration got the better of me and I moaned and sighed.
Kathy raised an eyebrow to that, “So, do you disagree with the way I am treating my slave?” She giggled.
I chose to play safe and not let any sounds escape my mouth. I lay on the bed for quite some time, and once again became soft. “I want my slave to last when I fuck him. So, we will make him cum. We just can’t have him cumming before I do.” Again, she giggled.
This time, she didn’t use oral sex to tease me. She got down to business and used her wonderful hands. One of her hands grabbed my balls, and she gently began to caress them. With her other hand, she used a few fingers to dance around the skin of my cock until slowly it began to grow to its full length. As she continued to caress my balls with her hand, she began to stroke my cock. She started low on the base of my cock and worked her hand up to the head, then back down. She knew my pace and rhythm. Slowly, she picked up the pace, pumping her small, soft hand up and down my shaft. Soon, I found myself arching my back. Kathy picked up her pace and pumped faster and faster. She fondled my balls more vigorously, sometimes squeezing gently, and pulling firmly toward the mattress. Within a few seconds, my cum was shooting up and all over her hand.
Kathy cleaned up my cum, and let me rest….
—
After about 20 minutes, I felt the bed again give way. I was surprised that I didn’t fall asleep with the blindfold still on. Kathy took off the handcuffs and transferred my wrists to some sort of ties on each side of the mattress. They felt like neckties or some sort of very soft rope. One thing was for sure…I couldn’t move my hands very far. Before I had time to think about it, I felt Kathy crawl toward my head and her sexy thighs stradle my head.
“Ok slave Allan, now its my turn. Unlike males, females need a jumpstart. I need to get my motor purring so I can help out your ego by cumming when you do. Start licking sweety.”
With that, I felt Kathy move up over my head and hook her calves under my arms. She squeezed, now cutting off another sense…my hearing. She lowered her pussy to my face, bumping it first along my nose, making sure I would get a snootful and helping me to orient myself. Since I couldn’t move my head too well, I was restricted to how and where I could lick. Then, I figured out that that was the way she wanted it. She didn’t want to be teased. She wanted to get down to business. I opened my mouth so my lips could meet her pussy lips. As my lips met her sex, I was again surprised. She was clean shaven! Never had Kathy consented to shaving her pubic hair with the exception of her usual bikini area hair.
I began to lick the outsides of her lips. As soon as my tongue touched her lips, I knew this whole evening was turning her on as well. She was wet. I never knew her to be as wet as this. I was in heaven. I began recklessly lapping like a dog drinking beer. I wanted more. Soon, though, I felt her thighs begin to squeeze. I immediately saw that a signal to improve my oral sex technique. I slowed my pace and moved to her inner lips. I snaked my tongue up to her clitoris, then back down, around. I again attacked her clitoris. She began to sway her hips, moving them in small circles. I inserted my tongue into her vagina trying to fuck it. She pressed her pussy back against my face as I tried to stick my tongue in as far as I could. I pulled my tongue out and slid it back to her clitoris. I made small, but firm circles around the hood, then licked it directly. Kathy jumped a bit. I then sucked her clitoris between my lips and tugged the best I could and released it. Kathy began to moan. I sped up my tongue and drove it back into her vagina. I then moved it back to her inner folds and licked faster. I moved to her clit again, and sucked it between my lips still stimulating it with my tongue. I felt Kathy shudder, her legs quivered, and finally, her low, throatly moan and then she shook a bit.
She didn’t move for a while, but released my head. Soon, she moved off from over my head and moved to the side of the bed. She took my cock in her mouth and began to suck my cock back to life again. Kathy was soon on top, slowly guiding my resurrected cock into her slick tunnel. Very slowly she lowered herself fully onto my shaft. Then, she sat for a few minutes. Slowly, she raised herself up to the tip of my cock, and slowly lowered herself back down. Kathy continued this slow fuck pumping up and down ever so slowly. Again, Kathy slowed to a stop. This time, however, she leaned forward and unfastened my wrists. Then, she reached back and took off the leg cuffs. She wanted my movement.
Kathy started once again. She warned me that she was to be in control and I was to cue off her movements. Up and down she slowly fucked herself, and me. It was mind boggling. She increased the tempo slowly to a comfortable pace, but again stopped, and sat only moving her hips gently in a circle. Over and over again, she would fuck me slowly, then stop. Each time, she increased the tempo, and would stop. After doing this six times, I thought I would go mad. Kathy removed my blindfold. I squinted at my new surroundings after being deprived of light for what seemed like days.
I caressed Kathy’s breasts and massaged her thick nipples. She began to rock her hips backwards and forwards pressing her pubic bone into my hips, trying to get clitoral stimulation any way she could. She began to pump up and down my cock at an increasing pace, this time not holding back. She began to moan and gurgle as she always does when she nears orgasm. I met her downward thrusts with upward thrusts of my own. Soon, the bed began to bang against the wall in that tell-tale way associated with many motels. Kathy began to sigh and squeal. I began to moan myself. I felt an orgasm coming, but it wasn’t near yet. Kathy began to thrust harder. She reached back behind her and under her ass and began to caress my balls. She knew how to pull my strings and enhance my stimulation. Soon, I was nearing ejaculation and she was near an orgasm. As I tried to keep massaging her breasts and nipples, she began to shudder. I thrust harder upwards to keep up the pace as she began to lose control. Within seconds we were both in a frenzy of erotic babblings. Kathy squealed quite loudly and I let out a long, and unusually loud moan as we came together.
As we layed there under the covers, cuddling, and fondling, we rested from our recent ectasy. Kathy coyly smiled and asked, “So, who wins the bet?”
No question at all in my mind. “You do.”
Kathy smiled. “Good. I knew I would. Next weekend when we meet, you’ll need to pay up.” She giggled, then winked.
–the end–
by Ted Wagner