Getting Nailed

"Sarah please let me cum?!"

"All in good time Jack, all in good time."

I made my eyes focus on my nails and I couldn't believe what I was seeing. My fingers moved and if I just looked at the hands below the scarves tying me to the chair, you could believe that the hands belonged to a woman. My hands are very small in comparison to my body and the effect was unbelievable. I was mesmerized as I drummed the nails on the arm of the chair.

"Well what do you think Jack?"

"They are beautiful!"

"I know, even though I don't have time to keep my nails done up this way, I still am a bit of an artist." "Don't you agree?"

I had to admit that Sarah was unbelievably good at doing nails if she could make my hands look like this.

"Great, now can you let me out of this chair, please?!"

"Just a minute Jack, let's go over our bet first." "Remember, you have to prove that you can cope with the nails to win the bet!"

"Yeah yeah yeah, please untie me!" "My legs are falling asleep and my dick needs relief!"

"Well Jack, I think you need to get used to your new nails doing some routine tasks before jumping into heavy sex." "If you break your nails in a moment of passion, you would lose the bet, so I think it would be wise to get used to them for a while first."

"What do you mean, I lose the bet if I break a nail?"

"Of course Jack, if I am at work and break a nail just before the big client presentation I am screwed." "Can you imagine the horror a woman feels pointing to visual aids with a broken nail?" "You think it is easy or at least no big deal to have nails, so you have to prove you can do typical things without breaking your nails or anything else!"

I had to admit Sarah had a point, but I didn't think I could stand to not cum.

"OK Sarah, you win, but can't you give me some relief sexually without me risking my nails?" "Maybe a blowjob or something?"

"Would you like to get that dick into my pussy?"

"Yes, please I can't go on without some relief."

"OK Jack, but to protect your new nails, I am going to have to keep you tied up."

"OK Sarah, please I am desperate for relief!"

Sarah went into the closet and got out our box of sex toys. I hadn't seen the box in over a year but knew what she was after. Sarah pulled out the sex cuffs that were padded and could be worn for hours without any risk to your arms or legs. Sarah released me from the chair and pulled my by my cock over to bed. She pulled back the covers and had me lay down in the middle of the bed. Taking a cuff, she attached each of my arms and then legs to the corners of the bed. I am now tied spread-eagle and even more helpless to resist any new torture Sarah can come up with.

Sarah gets between my legs and starts to nibble on my cock. I never get quite enough stimulation from having my cock sucked on, but little love bites can drive me completely crazy. Sarah gets me near explosion again and then takes my cock into her mouth and slowly sucks and bobs on my cock. I can't cum, but the wet oral stimulation keeps my right on the edge. Again I beg for relief.

"Please Sarah, I am desperate for relief"

"That is your problem Jack, I have already had a couple of good orgasms tonight and frankly I am getting tired. I think we should finish tomorrow morning. After all, you have over 23 hours to go on our bet!"

"Sarah, you said I could get my dick into your pussy if I let you tie me up on the bed!"

"Well, I guess a promise is a promise, so I will have to let you in my pussy if you still want to."

"Thank you, thank you!"

Sarah jumped off the bed and ran into the bathroom. She came back with several condoms and started putting one on my dick.

"Hey, we don't use condoms anymore, what is that for?"

"You are just too hot and I am tired." "If we are going to have sex, I don't want you to cum before I get relief and this will slow you down."

Sarah proceeded to roll two more condoms on my cock. She rolled each condom past the ring on the prior condom and they were having the effect of a cock ring. I was now 3 layers away from the velvet sensation of Sarah's pussy. She slid up my chest and sat her pussy on my face. I was so horny that I just went crazy licking her pussy and when her juice was flowing fully, she moved down and impaled herself on my dick. The warmth was immediate, but I could not quite feel her movement. It was just a whisper in the night. I knew it was happening, but could not realize the full effect. As Sarah rode up and down faster and faster she began to talk.

"Your nails really turn me on, you know?" "I have always has a little bit of a lesbian fantasy but no interest in actually having sex with a woman." "I think to prove that you can handle the long nails, you need to do everything a woman would have to do!" "Don't you agree?"

I didn't care anymore, I would agree to anything to get relief. If she asked me to commit murder at that moment, I am sure I would agree!

"Yes, yes, yes!" "Anything you say, just let me cum!"

Sarah exploded in her third big orgasm of the night and collapsed on my chest. I was twitching inside her cunt but still no climax. Sarah rolled off and started kissing and stroking my face. I was out of body just watching the scene. The cock was the center of my universe and the rest of the room was just spinning slowly around the cock. I say the cock, because it was in charge and I was just a slave to it.

"To prove you can make love as a woman, I am going to let you masturbate a real cock!" "How does that sound?"

"What do you mean, a real cock?"

"I am going to release your hand and you are going to masturbate your cock with your new nails, just like a woman would have to if she was in a car on a date!" "What do you say?"

I quickly agreed. Anything to get relief. Sarah released my left hand from the cuff and it flew to my cock. I was right handed, and with the long nails, it was very clumsy, but I was desperate to cum. Grabbing my cock, I started to pump it up and down, only to find the three condoms in the way.

"Please Sarah, take off the condoms?!"

"If I take them off, you lose the bet"

This was impossible, I didn't think I could get the three tight condoms off and giving up on the bet was not an option. My long denied orgasm was driving me crazy and I had to stop reacting to my cock and concentrate. Slowly I explored getting the outer condom started up. My new nails kept me from grabbing it and rolling it back off over the bands of the other condoms was not going well. Sarah climbed up on the bed and adjusted a pillow so that she was sitting at the foot of the bed facing me. She started masturbating in my plain view as I struggled with the condoms. I felt like I was spending as much energy working on that condom as I would in a basketball game. Suddenly I got the outer condom to roll over the band of the other two using my fingertips and keeping the nails out of the way. The next condom was much easier and I was finally able to remove the condoms.

Sarah told me to just use the edge of the nails on my cock head to get it sensitive. I did as instructed, after all she wasn't asking me to kill anybody yet and I knew even that was possible right now.

Sarah tells me to start pumping my cock, but to keep all 5 nails in contact with my cock flesh as my hand flies up and down. Sarah stuffs more pillows under my head to insure that I am looking at my cock. I am racing toward orgasm and close my eyes.

"Open your eyes Jack!"

I open my eyes and see a beautifully manicured hand flying up and down a rockhard shaft. My out of body experience ends and I collapse back into my body. I can't help myself and just explode. I am thrashing about on the bed and spewing sperm high in the air. Sarah has been rubbing her breasts with one hand while fingering her clit with the other and explodes in orgasm herself.

This is the closest I have ever come to having the unbelievable over-the- top orgasm like Sarah has. I am drained and my body tingles all over. Then I hear Sarah's voice.

"What a mess you made, I didn't think you could possibly have that much sperm in you!" "You better clean up your mess Jack!"

"I can't, I am all tied up except for my left hand and I can't reach the other cuffs."

"You have to do it like a woman would, and clean it up with your hands and tongue!"

"Come on Sarah, that is not part of our bet!"

"Are you admitting that you lose the bet Jack?" "Then get to work, if I was making love to you and you exploded, I would clean you up with my hands and mouth, so get to work!"

I looked down at my hand with the beautiful nails soaked with my sperm. Slowly I brought my hand to my mouth and as the sperm dripped off the tip of a nail into my mouth, I had a second orgasm. Not a large orgasm with sperm flying, but my whole body was climaxing over and over again. I could not believe it, I was slurping my sperm off my own fingers, and shaking in multiple orgasm after orgasm. My hand was flying back down to my dick, scraping up any sperm I could find and back to my mouth. Over and over again until I could not find any sperm on my dick, stomach or chest.

I was coming down finally when I saw a bright flash. Sarah had gotten off the bed and was taking pictures with our Polaroid. The look of horror on my face stopped Sarah from taking pictures and then she started laughing at my predicament. I looked around the bed and saw what must have been a dozen pictures taken of me from every possible angle. Fingers dripping with sperm jammed in my mouth, clearly my own hand with painted nails covered with sperm being sucked clean and nothing but lust on my face.

I was speechless and then Sarah collected the pictures and left the room. When she came back I asked what she did with the pictures.

"I hid them for those nights when you are on a business trip and I need to masturbate to get to sleep." "I am going to take them out of their hiding place and remember this night again and again!" "This is probably the most exciting sex I have ever had and Jack, I plan to relive it whenever I get the chance!"

I was in shock, on one hand I knew she was right, this was the only time in my life that I had been able to keep climaxing like a woman's multiple orgasm. On the other hand, if anybody else saw those pictures, I was ruined in my mind.

"We need to get some sleep now, because you are going to have a long day tomorrow"

Sarah started untie me while explaining that I was to clean up, go to the bathroom and comeback and lie down again. She was going to put me back in the cuffs to protect my nails during the night. Sarah explained that I wasn't used to the nails and if I tossed and turned during the night they might get caught in the covers, come off and I would lose the bet.

I was so exhausted, I didn't even argue. I simply got up, went to the bathroom, cleaned up a few stray drops of sperm, emptied my bladder and came back to bed. Sarah put me back into the bondage and pulled the covers up for sleep. Sarah kissed me gently and played with my cock until she drifted off to sleep.

I went over my situation in my mind as I was nodding off myself. I had on super glue nails that were obscenely long, my dick was hard again in my sleeping wife's hand and I had a full day ahead to win or lose the bet. I was afraid and excited at the same time, what a night.

As I dropped off to sleep, I could hardly wait for morning and the start of day ........

Chapter 2, The Start of a Long Day

I couldn't believe what Sarah did to me to wake me up on Saturday. She released my right hand from the cuff and tickled my nose with a feather. When I went to reach my nose to scratch the tickle some beast with deadly talons and a terrible cackling screech attacked me. As I came rushing to full consciousness, I realized that the terrible beast scratching my face was my right hand and the cackling screech was just Sarah laughing hysterically.

It was a good thing that Sarah still had me tied down on three corners, or I would have killed her.

"Good morning sleepy head."

"You are such a bitch when you want to be Sarah!"

"Now, Now Jack, don't get pissed off so soon, you are going to have enough frustration today getting things done with your new nails." "Don't waste your energy on this little event."

"What do you think happens to me when I scratch my face during the night and I have long nails on?" "Are you ready to give up already?"

I wasn't and besides, I needed to get out of bed and take a piss.

"OK, just let me up so I can go to the bathroom."

"I am going to go to the store and pick up a few things and you can get cleaned up for the day." "Take a shower, shave and anything else you need and I will be back in a few minutes."

As Sarah was took the cuff off my other hand and as she headed for the door she reminded me that I better be ready when she got back.

Getting my other hand free enabled me to sit up and if I leaned way over, I could just reach the cuff on one of my legs at a time. I had to work at it long enough that I thought I would have to wet the bed if I didn't get it off soon. I felt a great sense of accomplishment just getting it unbuckled. The second leg cuff was a piece of cake and I ran for the bathroom as my bladder was starting to relax.

The shower was next and I could hardly hold the bar of soap. It kept slipping out of my hand and then I had a devil of time picking it up off the floor. Giving up, I got out a washcloth and took my shower that way. I had not used a washcloth since I was a little boy and found it very odd to see my body being washed by a beautifully manicured feminine hand holding a washcloth while I was alone in the shower. Next was the shampoo and after struggling with the lid, I got it done without any severe damage to my scalp. The nails kept getting caught in my longish hair (for a man) and it took twice as long to complete this simple task.

After the shower, it was shaving and brushing my teeth. I was starting to get the feel for the nails by now and could do simple tasks by extending my fingers out straight and working the fingertips. This angle kept the nails from digging in.

I was blowing my hair dry when I heard Sarah in the bedroom.

"Come on Jack, I have been gone an hour and you are still getting cleaned up!"

This was shocking, I had spent three times as long getting cleaned up as normal, but at least I still had on all 10 nails.

"Hey, I am beginning to get the hang of these nails, they aren't so bad once you get a little practice!"

"Glad to hear it Jack, because now is you time for the next challenge."

I stopped breathing and fear rushed over me. I could not believe how terrified and excited her words made me as Sarah handed me a package of pantyhose.

"Put them on Jack."

"You have got to be kidding!?"

"No Jack, I have to do this every day and it is not that easy." "If you are going to prove your point and win the bet, you are going to have to show me!"

I was stuck and Sarah knew it. Sitting down on the bed, I started opening the package. Using my teeth, the bag was not much of a challenge, but the next step was very unfamiliar. I had watched Sarah do this many times and had a clue but not much else. Working my feet into the hose, I started smoothing them up my leg. The nails kept getting caught and the hair on my legs was being bent backwards, but with patience I got them up over my knees.

"Hurry up boy, I would be late to work everyday if I took this long to put on my pantyhose!"

Standing up, I started pulling and tugging the hose up over my thighs. It wasn't working anymore. The new hose were just not long enough, but I kept working the material higher and higher. Just about had the hose up to my crotch when it happened.

The hose ripped, one of my nails went sailing across the bedroom and a run shot down my leg.

"You lose, you lose, you lose!"

Sarah was gloating and I was so embarrassed that I turned red.

"That's not fair Sarah!" "You run nylons all the time and you don't have long nails anymore and you lost a nail before and and ....!"

"Jack, you lose!" "You said it was easy and this proves I won the bet!"

I was frantic, I didn't want to lose the bet (male ego I guess) and had to get a second chance. I proposed to Sarah that one single incident wasn't enough and that we needed a point system to determine who won the bet. It took a while but Sarah finally agreed, provided I did something else in return.

"Jack, I want you to shave your legs and under arms."

By now, I was willing to go along with Sarah on just about any condition. While Sarah glued my lost nail back on and touched up the polish, I kept trying to talk Sarah out of the shave, but she insisted. I went back into the shower and started shaving my legs and under arms. After 20 minutes and 3 razors, I was about done when Sarah came in to take a peek. Sarah reached into the shower and started rubbing cream on me and said it would soothe the razor burn. She was taking great care to rub my dick and chest and even worked it into my ass cheeks. I was starting to build for orgasm as she worked a finger up and down my crack and found my asshole. Then Sarah stopped and said I had enough "help" and I needed to rinse off.

After I got out of the shower, Sarah was helping me dry off when she told me to look in the mirror. I could not believe the picture looking back at me. She had used a hair remover and I was completely bald from my neck down to my toes. I was not very hairy to begin with, but this was shocking. My hardon looked even bigger without any hair on my pubic area. I wanted to protest, but Sarah was rubbing my dick and telling me how much fun this bet was working out to be.

Handing me a new package of pantyhose, Sarah told me to put them on and come down to the kitchen. With the new smoothness of my shaved legs and experience from my first attempt, I was successful this time getting the pantyhose all the way on. The sensation of hose on my legs was great. I always liked Sarah to rub her nylon-covered legs against mine when we made love and this was almost as good. The only draw back was all this sensation was giving me a hardon. The result of my erection was kind of comical when I looked at my profile in the mirror. I was interrupted from my state by Sarah's voice.

"Jack, are you done yet?"

Going down to the kitchen, I was strutting like a proud peacock. I was thrusting my hips a little forward to make sure Sarah couldn't miss my erection when I made my "grand" entrance. Sarah wrapped me in her arms and kissed me deeply. Rubbing my erection through my pantyhose she whispered in my ear.

"I see you like dressing up in women's underwear as much as you like wearing long fingernails."

I pulled away and again turned red with embarrassment and humiliation. Sarah calmly pulled me back to her and told me how much this was turning her on as well. I relaxed again as she continued to rub me through the pantyhose, bringing me close to orgasm again. Then she stopped her stimulation and returned to a very business like manor.

"Jack, I have revised our agreement and you need to review it and sign the new bet"

Revised Nail Bet Between Jack and Sarah

1) Sarah will put long nails and polish on Jack. 2) Jack will wear the nails until he gives up or any of the following conditions are met. 2a) 24 hours pass with Jack successfully wearing the nails. - 2 points for each nail damage event. - 1 point for each failed activity (including damage to any article). 2b) Jack fails if he earns 10 or more points. 2c) Some emergency occurs, in which case the bet will be suspended to a future time. 2d) Sarah agrees that Jack has proven that wearing long nails is "no big deal". 3) The loserr of the bet will be the sex slave to the winner for 2 weekends.

I was down 3 points already, but if I didn't agree to this change to the bet I would already lose. With not much of an option, I signed.