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Getting Nailed

By: SouthernScribbler



I can’t think of too many other things that make a woman look more feminine than long, well manicured fingernails. Even hair, or lack of, doesn’t hold that stark reminder of feminine sexiness like fingernails do. I’ll never forget one encounter where my lover had her nails, all hers I might add, at a length of about an inch and a half in length. They were tapered down to a nice round pointed tip. She knows that I love the dark red colors, and this night she had painted them a dark red, almost burgundy color. She was very picky about her nail polish and always bought the expensive kind. I guess its like a auto body person picking out a color to paint a car. You want the finish to be perfect. In any case, the color she had picked was not only the perfect shade, but the polish had a depth to it once it was on the nail. Deep and rich with a perfect tone and sheen.

We had spent the hottest part of the day at poolside, which most times meant that poolside was accompanied by several mixed drinks. Hers were tropical, pina colada, and daiquiris’ while mine were basically spiced rum and coke. By the time we had decided to come in from the heat, we had already removed all of the clothing that we had on when we were at poolside, albeit skimpy enough to really not notice being now, nude.

The first ritual after sunning was to jump into a nice hot shower to rinse away the lotions and the chlorine from the sparkling pool water. Showering together was always fun. Getting to watch the other as they got all sudsy and glide the thick bubbles all around into all the nooks and crannies was always a turn on, visually. On a more practical side, the other could help when it came to washing the others back too, which always feels so damned good. I stood in the back and let her soap up first, not only to show a courtesy but to enjoy the view as well. There is something very sensual about seeing a naked woman all wet and lathered with bubbles. I have yet to refrain from helping to spread the lather around when we shower. 

My arousal was quite obvious to her as I watched her glide and roam her hands over her entire body, watching as her fingers and nails would disappear from my sight under the thick lather or into the soft folds of her crotch and the crevasse of her tanned butt cheeks. She began to rinse and passed the bar of soap to me, as a runner would pass the baton in a relay race. I began to spread the soap all over my front, before dropping the soap to the floor of the shower. 

As I began to slide the bubbles all around me, spreading the thick foam on my naked wet flesh, she knelt down to retrieve the skittering bar of soap. She looked up from her kneeling position, her face a mere two inches from my out stretched cock, and smiled as she said “ Heat get to ya?”. I smiled back and replied that the heat from the show of her washing got to me. 

I stepped into the stream of the shower head and rinsed the front, watching the thick lather dissipate into the rushing water on the shower floor and disappear down the drain. When I turned to rinse my back side, she told me to keep my back to her. She gathered the thick lather from my shoulders and spread them over my back. As she massaged the bubbles into the flesh of my mid section, I felt a very relaxing feeling from her massage. Then with her nails, oh those long beautiful nails, I felt her begin to lightly scratch every inch of my back. It’s no wonder that a cat will arch it’s back when someone beings to scratch it. Which is exactly what I did, too. Oh my God! It felt delicious. She really surprised and aroused me though, when she moved one hand to my ass and began clawing at the thick meat of my right cheek. My cock sprang back to its rigidity when she did this. The massage and back scratching had relaxed me into a nice lull, causing me to lose some tinsel strength of my previous excitement. 

I turned around, now facing her wet naked, nicely scented body. Her breasts glistened as the water beaded and ran down her chest and tummy, collecting into a nice funnel at the pelt of the Y shape of her crotch, and then down her legs to the floor. She taunted me by raking her crimson nails over her breasts, firm enough to leave little white streaks from the pressure and only to disappear as quickly as they had shown up. She slowly and firmly dragged her nails over each erect nipple, causing the pliable nubs to bend from the pressure, only to rebound with a more erect posture. 

With her back to the wall, she leaned back and took her nails of each hand and placed them on each of her full pussy lips. She spread the lips apart and asked that I move so she could make sure that all of the soap was rinsed away. I did as she asked, but couldn’t resist a closer look and knelt down in front of her as she was still spread apart as she was when she rinsed. I could feel the thumping of water from the shower head as it rained on the back of my head as I looked at her long nails as they kept her pliant flesh spread apart. The thumping of the water matched the thumping of the blood, as it raced through my cocks pulse as I gazed. The look in her eyes was lustful as she peered down at me as I looked. I stuck my tongue out and leaned in the two inches to feel the soft velvety texture of her softest spot against my dripping tongue. I wagged my tongue across the slightly raised cover of her swelling clit. I felt my tongue as it met the talons that held her flesh apart so I may have a taste. I glided my hungry tongue over each of the claws, feeling the shiny smooth surface as I did. She released her lips and grabbed a thick handful of my hair with one hand and lifted slightly, guiding me back to an upright position.

Off to the bedroom we headed. Once there, she stopped and turned and knelt down in front of me. She then placed each of her hands onto my chest and stomach. With her face level with my protruding cock, she opened her mouth and slowly slid my length into her hot mouth. Her tongue grazed and bathed my sensitive underside until the tip of my cock rested at the back of her throat. I felt that my balls were nestled tightly against the base of my cock base from excitement. Once she had me in her mouth as far as it would go, she then clamped her lips around the shaft tightly and began to lightly suck. At the same time, she dragged her nails down from my chest and over my stomach very slowly and deliberately. It felt like every nerve ending in my body was directly under the flesh that she was clawing. Her hands didn’t stop until I felt the nails lightly clawing around the base of my cock and finally scratching at my scrotum. She began bobbing her head back and forth on my engorged cock. With the suction that was created with her clamping her lips firmly around the base, each time she pulled her head toward the tip, it made the suction that much greater. All the while, her nails were raking my heavy balls until they hung back down into the sac. Knowing that I couldn’t take much more of this play, I stepped back from her. 

I helped her to stand, and walked her to the wide bed. I crawled onto the bed next to her and slid my body onto her reclined position. I asked if she would spread herself for me as she had done in the shower. She smiled, before asking me if I had liked that, already knowing my reply. I slid off of her and repositioned my self so I could watch her play her tingling flesh with her crimson talons. At first she used the palm of one hand to rub her pubic mound while the other grasped at one breast. I was startled when she smacked her pussy with the fingers of her exploring hand. My surprise was her delight, and she smacked it again for good measure. Then she slid the other hand down to spread her soft folds apart. She only used two fingers, aligning the meaty folds between her first and second finger then spread them apart. My cock was burning with desire as I watched her two slender fingers, crowned with long burgundy claws, spread the puffy lips apart, exposing her flesh covered trigger. It was more than I could resist.

I lowered my head and began to taste her. Her fingers never faltered as she kept her lips apart for me. I licked hard over her now fully erect clit. It reminded me of a flesh speed bump. I put my lips on either side of her swollen bud and tried my best to create a suction, and then tug, hearing a small pop as it popped from my lips, only to dive back in again to repeat the same technique. Her moans were growing in intensity as I continued to lap and lick at her. I asked her if she was ready for some good loving. She looked at me through glazed eyes and inserted two of her fingers deep into her soft pussy. She drew her fingers out. They glistened with her wetness. I grabbed her hand and pulled it to my lips. I slowly licked each finger, watching her watching me as I did. I slid my tongue under the long talons and tweaked the sweet nectar that had collected there as well. 

I climbed atop her reclined and leg spread position. My aching cock slid easily into her folds. I felt her heat as my cock etched slowly into her hot tunnel, until my cum laden balls rested against the cheeks of her ass. I began to saw in and out of her, filling her with each stroke. My pace quickened after several minutes. I would fill her, then pull out an inch or so only to delve in again. I kept my short hard chopping strokes for a few minutes and replace those with long full thrusts, alternating from time to time. When I gave short hard strokes, I could feel my ball sac as it would cling to the sticky cheeks of her ass when I’d withdraw. 

She told me that she wanted to change positions. I climbed off and she scampered onto the bed on all fours. She told me that she loved it this way. I replied that it wouldn’t be me to deny her what she longed for. Again, I easily slid my full length into her and began sawing in and out of her at a fervent pace. Her chest was resting against the pillows and she had one hand tucked under her, wildly massaging her clit. I could feel the tip of her clawed fingertip every few strokes as it would touch my cock as it pistoned in and out of her. Her moans were now turning into cries of passion. My balls ached with anticipation and I knew that I would “take her there” before I released my pent up lust. It was as if she heard my very thoughts. She took her one free hand and reached way down in between her thighs and began clawing at my churning balls while I thrust into her with long , hard , deep strokes. The enticing clawing sent my cum, bubbling from my depths and racing up from the base of my cock, as I cried out that I was going to “spurt hot cum” deep inside of her . Much to my relief and delight, she came exactly at the same time as the first jet of cum spewed from the tip of my convulsing cock. I felt the walls of her pussy rapidly grasping my cock as her climax began and then started to ebb as her waves of desire flowed from her.

Completely spent, I withdrew from her and as she rolled and lay down I lay down next to her. After we regained a more regular breathing pattern, I told her that it felt as if I had cum a lot. She slid two fingers deep into her dripping punani and pulled them out. Her fingers were smeared completely from her knuckles to the tips of her long nails with our emulsification of juices. Her crimson nails were clouded by the thick creamy color. As I had done before, and much to her surprise, I grabbed her hand and licked our fluids from one of her fingers and nail. She smiled, and repeated the same thing that I had just done. We then kissed each other deeply, tasting our efforts before she snuggled to me as I cradled her into my arms for a nice rest. 

Getting Nailed



This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something else. The author retains all rights to this story. You may re- post the story unchanged, provided there is no intent to profit from this story (it is not nice to make money from someone else's work). 

The author enjoys reader comments on his web published erotic fiction, so if you wish to reach him, e-mail him through the link below.


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Chapter 1, The Bet

Sarah and Jack

We have been married for several years and we both were experiencing very active professional lives. Our jobs are quite demanding, requiring us to work long hours and consuming most of our creative energy. This daily grind had the same effect on us as most other couples in the 90s. Our love life was shrinking down to one or two times on weekends without a great deal of inspiration. We both longed for our early days of our relationship when sex was very regular and was our first choice in recreation activity. 

One thing I missed a lot was Sarah's long fingernails. Sarah is a great looking woman, a complete package of brains and beauty. She is almost 6 feet tall, has light red hair and green eyes. I have always thought she has the perfect figure with great breasts and a butt to match. 

Sarah used to keep her nails long and manicured. Her work requires her to use a computer most of the day and she found the long nails to be problem. Little by little her nails got shorter, until today they are just about the same length as mine. 

I still get a little rush when I think back to those long nails and how she would use them to tease me sexually. Taking the edge of her shaped nail and running it along the veins in my cock and around the head. I think she could keep me on the edge of orgasm for days if she wanted to with her fingernail tricks. Then she would take my dick into that perfect pussy and while she rode me she would lightly rake my chest with her nails. Not quite breaking the skin, just enough pressure to drive me crazy with lust. Sarah could take the edge of those nails around my nipples bringing the little nubs to rock hard points and then when she reached orgasm she would pinch my little nubs as we pounded our bodies together and I was cumming like a mad man.

Always the next day the warm shower would bring little red lines on my chest to a visible state and when I was shaving seeing the marks in the mirror made me stiff again. 

Friday Night: The Actual Bet

"Your late Jack and now I don't want to go out for dinner this late. Here we go again, a Friday night finally gets here and we are stuck with nowhere to go and nothing to do."

"I'm sorry Sarah, but I had to get my budget input completed for the consulting proposal we worked on all week. If I didn't stay until it was done, I would have to go in tomorrow. If I went in to the office, I would have been sucked-in to help finish other parts of the proposal for Monday and I didn't feel like blowing my weekend because others didn't get done today."

"Your trying to make me feel better by telling me it could have been worse?"

"No, I'm only trying to explain why I ended up working late. How does a movie sound? You said you wanted to go to see some chick-flick that's out now"

"What a great way to ask me out for a date, asking me if I want to see some chick-flick you can't even remember the title of, Jack. Why bother, just forget about it. You can run over to the video store and check out a rental movie and I will make us a chef salad."

"Are you sure? I asked lamely"

"Yes Jack, and knock off the puppy dog look. Open that bottle of wine in the refrigerator and pour me a glass. By the time you get back, I will be chilled out."

"Sarah, this is starting to sound like a good plan."

I ran over to the video store and picked up a couple of movies that might be interesting. I was hoping that one of them might be sexy enough to give us a libido boost, as we were way overdue for some good sex (any sex even bad sex). I also picked up some dark chocolate and some fresh strawberries. If the movie failed to get a spark started with Sarah, the chocolate and strawberries were pretty surefire.

When I got back, Sarah had finished the salad and had set up a "picnic" on the den floor. She had some nice candles burning and pillows available for getting comfortable. This was much better than going to see that "chick-flick".

I threw in one of the movies and we started to enjoy the good food and wine. The movie was not that good, but as we were more involved in our various appetites, so it didn't seem to matter. By the time we finished the salad and were snacking on the strawberries and chocolate the videotape had been stopped. 

Sex was on our mind and we had all evening to share our lust for each other. We had not had sex for days and I wanted to take some time. Abstinence has different effects on Sarah and me. Sarah takes much longer to orgasm and I take much less time. As we indulged in foreplay, I kept reminding myself to slowdown and put the energy into making Sarah as hot as I could. 

I was so horny that my dick hurt in my pants. I needed more room and getting Sarah and me out of our cloths became my focus. As I undressed Sarah, I kissed every inch of skin I could find. Sarah's neck is glorious and is a highly erotic zone for her. She can almost orgasm from my kissing and stroking of her neck. I began working my way down from her neck, slowly unbuttoning her blouse, and kissing her warm flesh as inch new area is exposed. By the time I am down to her bellybutton, she is pulling my shirt off with no regard to my personal safety. I have to stop what I am doing and give better access or I might get strangled in the process. We are back to kissing and I am working on getting her lace bra off. I could unhook it and get it off in a few seconds if I wanted it that way, but I wanted to make this as sensual as possible. After what seemed to be forever but had to be a minute or two, I had Sarah's bra off and her beautiful breasts were now the center of my universe. After kissing all of the soft skin of her breasts, I took one then the other nipple into my mouth. Running my tongue around and over her nipples brought them to a very hard state. Sarah is starting to move into that special zone where her whole body becomes sexually charged. Her body starts to tremble and her eyes are a pool of lust. 

Being so close to orgasm without quite getting over the top was frustrating Sarah. She grabs at my belt and urgently drags my pants down over my briefs and hard cock. I know that as hot as we both are, I would explode very quickly if I entered her wonderful pussy. I quickly shuck Sarah's shorts and lace panty. Kissing my way down her belly, I start teasing her pussy. Sarah has the best tasting pussy in the world and giving her head is a great joy for me. I lightly stroke her outer lips as she spreads her legs. Sarah is very close to going over the edge, but I want to drag her orgasm out as long as possible. I slide down further to give Sarah's pussy the tongue-lashing I so enjoy providing. Sarah wants me to shift around to a 69 position so she can return the oral stimulation, but I refuse. I don't want to change positions and lose my concentration. 

When Sarah gets into this zone, she is having small orgasm after small orgasm and keeps building to a large crashing climax. My world is Sarah's pussy by this point. I keep working Sarah closer and closer to the edge by licking and sucking her clit then going back to licking her pussy lips. The only part of my body Sarah can reach is my head and she has her fingers twisted into my hair and she is pulling my mouth into the pussy. Her body starts to quiver and suddenly she goes stiff for a moment and then begins to shudder. 

I move my hand from Sarah's butt and insert a finger into her pussy. Taking the wet finger around to her asshole, I start finger fucking her rear entrance. That finishes her and takes her over the edge. A major orgasm starts and goes on for several minutes, drenching my face with her lovely nectar. Sarah has these major over the top orgasms most of the time when we make love, but when we have gone without sex for a while, the result is unbelievable. Her pussy juice is flowing so hard that I can't even lap it all up, her body rocks and convulses so hard that she gets cramps in her legs and toes and Sarah moans for so long that she completely runs out of breath.

It is over, and Sarah has collapsed into a limp pile. Sarah's clit is ultra- sensitive now and she can't stand to have any more additional stimulation. I slide up next to her and hug her as she comes down from the climax. She starts licking her juice off my face and crushes me against her breasts. Sarah says that she goes completely out-of-body when she has these powerful climaxes and I am both amazed and jealous of her orgasm. My dick is still throbbing in my briefs and I almost came myself without being touched. I slide my briefs off and put my erection between Sarah's legs, but not in her pussy. As Sarah clamps her legs together my dick is trapped against her clit and her pussy juice is flowing over my cock. She rocks her hips slowly to rub her clit against the top of my dick as she comes down some more.

After several minutes Sarah can talk again and begins to relax her legs and arms so I can move again. Now it is my turn, but Sarah is a little pissed that I teased her so long before taking her over the edge. Figuring that what is good for the goose is good for the gander; she starts to tease me. I tell Sarah that I am already hot as can be and just want to fuck. No way is Sarah going to let me off that easy and she starts tweaking my nipples and asking me questions.

"Jack, why are you so cruel to me when I am ready to climax and want your hard dick in me"?

I explain that it is so rewarding to me when I take her over the edge like that and if we are fucking my orgasm might occur too quickly for her major orgasm. This is especially true when we have not had sex for a while.

"Besides Sarah, you are not so innocent of sexually teasing. Remember how you used to tie me up and tease me with your fingernails for hours? You would make me beg to come and make me eat you to orgasm after orgasm. Then you would leave the bedroom for a while, come back when my erection was starting to droop and start all over again."

Sarah got this evil look on her face and started to tease me about my fascination with her long nails.

"Well Jack, I think you have a little bit of a fetish when it comes to long fingernails."

"If I do, it is because you taught me to respond to your nails with your sexual teasing."

"I think you have a little too much interest in my having long fingernails."

I was starting to feel defensive and tried to push back on Sarah.

"I really can't remember your long nails that well, since you have kept them chopped off for so long." "I mostly remember the great sex we had back then and how often you put some real energy into pleasing me."

I had hit a little below the belt with that remark and Sarah looked hurt.

"Are you trying to say I don't put energy into sex anymore, huh Jack"?

"Not exactly, but you used to keep your nails long for me and now you don't" "This is one example of how we let our work lives interfere with our sex lives."

I thought by using the "our" sex lives line, that Sarah would get back to our love making and forget about this budding argument. I wasn't quite that lucky.

"Jack, you are so full of shit." "Do you have any idea how hard it is to keep long nails?"

"I watched you take care of them, and I don't think it was that big a deal Sarah."

"It isn't the time it takes to do your nails, it is the extra time routine activities take when you have the long nails."

I should have just agreed, but I had to have the last word.

"I think you are exaggerating how hard it is to have long nails."

"You want to bet, buddy?"

Now I was really stupid.

"You got a bet Sarah!"

I had no idea what I had just got myself into, but my male ego just walked me into a bold statement with implications that I had not considered.

"OK Jack, you are going to have to prove to me that it is no big deal to have long nails."

"You're on!"

Sarah went on to set the terms of our bet, then we put it in writing and both signed it.

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. 2b) Some emergency occurs; in which case the bet will be suspended to a future time. 2c) 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.

There, it was done. It was time to put up or shut up. After all the times I had wined to Sarah about not having long nails, I was about to find out what the wearing of long nails was like.

I had lost my erection by now, but I was horny as could be. Sarah had a major orgasm, but I was still without for over a week. The earlier activities had given me a case of "blue-balls" and all I really wanted to do was get my dick into Sarah's hot pussy. Sarah had other plans. She took me into the bedroom and sat my naked butt at the dressing table. She had an antique armchair at her dressing table with a padded seat and back but ornate carved arms. She sat me down in the chair and took several silk scarves out of the dresser. Sarah started tying each of my arms to the chair.

"Hey, what is that for?" I asked.

"I don't want you to try and back out after I get started."

Sarah sat in my lap and started kissing me. Running her hands over my face and down my chest, she kept it up until I regained my erection. Grabbing my dick, Sarah starts masturbating me, kissing me and rubbing her breasts against me. Her tempo starts building and she is getting me closer to orgasm, then simply stops.

"Hey, don't leave me like this!"

Sarah just laughs as she dances into her walk-in closet. I can see in the mirror that she is looking for something and then changes. When she walks out of the closet, she is wearing the short silk robe and matching panties that I bought her for Valentine's day. She looks unbelievable with her figure accented by the drape of silk. Sarah goes about collecting various items she is planning to use. She keeps moving from side to side as she gathers and discards items. I know she is doing this to set a physiological edge to our bet. Somehow, the whole show Sarah is putting on keeps me fully erect without any direct stimulation.

"I see that you find getting your nails done exciting?!"

"That is not fare Sarah, you know how good that silk makes you look, and besides I am the one with blue balls."

Sarah just smiles and plops down in my lap. She sets her tools down on the table and starts dressing my nails. She shapes my cuticles, trims and files each nail just the way she likes it. All this time, she keeps rubbing her beautiful ass against my erection. As she works, I try to look over her shoulder, but she keeps shifting around to block my view and rub my cock. This was making me even more excited and that didn't seem possible.

"Now to put on your nails!"

Sarah looks in her fingernail kit and finds her glue is dry.

"I guess you are going to have to wait here while I go get some more glue."

"Sarah, please don't leave me like this." "Can't we finish having sex and then go get some glue?"

"Poor baby, are you getting that desperate?" "Maybe I can find some more glue around the house and won't have to go out."

Sarah turned around in the chair and started kissing me again. She slid off her panties and is sliding her cunt up and down the bottom of my cock. Sarah grinds her hips against my cock, trying to crush my cock with her clit. I am at the edge of ejaculation when Sarah jumps off my lap, gives my hair a quick toss and jumps out of the room to look for glue. I can't believe it, my dick looks purple. It is twitching and throbbing but she stopped just short of my orgasm. If she keeps this up, I will be a complete drooling idiot. An erection with a body existing to provide nourishment, all other life events forgotten as the controlling erection seeks orgasm.

"Looks like I don't have to go out after all!"

"Hold on there a minute, that's super glue" "You can't take that stuff off, can you?"

"I'm not sure Jack, I never put nails on with super glue and I think they make some kind of remover, but I guess we will just have to find out."

"No way Sarah, please don't use that glue?"

"Beg me!"

"What."

"You heard me Jack, beg me or else, I am going to use super glue for your new nails!"

I started begging Sarah like crazy. She sat on my lap facing me again and started rubbing her tits on my face and pressing my dick against my stomach with her sopping wet cunt. I could not concentrate and before long I was begging her to let me cum and I forget all about the super glue. 

"Please let me cum Sarah!?" I begged.

"You can't cum until we finish your nails Jack."

"Please hurry up then, your driving me crazy!"

"I have to go to the store and get some more glue and that could take an hour with traffic and all."

"OK, OK use the supper glue!" "Please, just hurry"

Sarah just stopped and laughed at my predicament. She was getting turned on to the whole scene and was so excited herself that her nipples were hard as rocks and her cunt lips were glistening in the soft bedroom lights.

Turning around, Sarah bends my cock down and sits in my lap. She squirms around until my cock is nestled in the folds of her cunt lips and she can rub her hard clit along the top of my shaft. She rocks back and forth giving herself direct stimulation and driving me to greater and greater lust. Suddenly Sarah stops rocking and a small shudder shakes her body and she lets all the air out of her lungs as she climaxes.

"What about me?" I begged.

"I told you Jack, that you can't cum until we finish your nails!" "Besides, that was only a little orgasm for me." 

As Sarah goes to work on my nails she keeps rocking her hips randomly so that my erection keeps pressing up into her clit. Her nectar is flowing down over my cock and I can feel the wetness leaking over my balls. I am sure some of the wetness is pre-cum from my dick, but I can't see my erection.

I can't stand the frustration and simply close my eyes and concentrate on breathing. I think I was just about to pass out and it took all of my concentration just to force air into my lungs. I started thinking, and realized that I had been on the verge of my orgasm for about 2 hours now. I don't think I can survive much longer in this state of arousal.

"There, all done!"

I looked down as Sarah got off my lap. I didn't look at my nails yet, because I had to look at my cock. It was twitching and throbbing, was red in spots and had a purple cast to its coloration. It was covered with pre-cum and pussy juice and it seemed to belong to itself. Sort of a symbiotic relationship. The cock existed for one purpose, orgasm. The body existed to provide nourishment to the cock and in return got to experience the orgasm with the cock. I never understood why men gave nicknames to their cocks until now. It was a life-force of it's own.

"Well Jack, what do you think?"

I saw my nails for the first time and almost fainted. Sarah had put on the longest nails in her kit. The longest nails must have been 1.5" to 1.75" and even the nails on my little fingers are 1" long. Sarah has painted them a color I would call candy-apple-red if it were on a car. I can't believe what I am seeing and my cock starts to jerk up and down. Sarah realizes my cock is about to erupt and grabs my balls. Squeezing them to the point of pain, Sarah breaks the stimulation path and halts my orgasm. Reaching over the wine bucket, she grabs a handful of ice, starts rubbing my cock and balls. I think death must be near and then a split second later I come down to earth. My cock is still purple and fully erect, but my balls have shriveled up into my abdomen.




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.




Getting Nailed



"OK Jack, you get to make me brunch now."

"I didn't lose this bet yet, how come you are already treating me like a slave?"

"Silly boy, this is just the next test." "You need to prove that you can cook with long nails, or else you are saying that the nails do interfere with real life."

I had to work very hard on this bet and Sarah was getting treated like a queen. Somehow, she was winning even if she lost the bet. Sarah always was a clever woman.

Sarah wanted me to make omelets for brunch and I didn't like this idea. I would have to chop a lot of items to make omelets and it was a lot of work without the long nails. She had chosen wisely. I started to go back to the bedroom and get dressed, but Sarah had other ideas.

"Jack, I like the way you look, just put on an apron."

Sarah got out her most frilly apron. It was handmade by her aunt, pink and white checks with stiff lace sewn onto the apron for feminine decoration. The sleeves were ruffled and it was the least masculine apron in the house. I blushed again as Sarah tied it tightly around me.

Getting to work, I chopped the meat and vegetables for the omelet and it only took a little longer than normal. After making the coffee and juice, the griddle work started. It was a real trip working the spatula, but I managed. Sarah made me do the whole drill, set the table and serve her. I make omelets one at a time, so I went back to work on mine after serving Sarah.

When I sat down, Sarah was already done and as I ate she started teasing me about how sexy I was in the pantyhose and apron. She described how much it turned her on to watch me working in the kitchen with my legs and butt highlighted by the hose. To her, my apron was "adorable" and made her think about her lesbian fantasy. I wasn't sure where she was going with this conversation, but as she talked my erection returned and was making my apron peak up. The tightness of the hose was causing some discomfort but, the nylon was also rubbing my dick to a point of extreme sensitivity. As I was finishing brunch, Sarah came around the table and started rubbing my chest under the apron and working her hands down to my dick.

"You really like being dressed up like a little horny housewife, don't you Jack?"

"That's not exactly right Sarah, you keep making everything we do sexual and that is what turns me on." "It's you, not the apron and hose!"

It was a lie, this whole scene was making me hot, not just the feminine clothes and not just Sarah. She knew this and worked her point a little more.

"Then how come you had a hardon when you came out of the bedroom in your pantyhose?"

"I guess you are right, being made to wear forbidden cloths is a bit of a rush"

Sarah slid down in my lap and started kissing me and feeling me up everywhere her hands could reach.

"Jack, make love to me like a woman!" "Just use your hands and mouth, OK?" "Your hands are very sexy with the long nails!"

I started kissing Sarah back and getting turned on big time. This was not a great position for making love, so I started to stand and pick up Sarah.

"No Jack, a woman would not carry me to bed!" "Take my hand and gently take me to bed or the couch on the sun porch."

I tried it Sarah's way and led her to the sun porch. This was one of Sarah's favorite rooms to make love in, but I didn't like the furniture for good old fashioned fucking. This wicker stuff was good sitting but not for a good pounding of my dick into Sarah's wet pussy. Sitting down on the love seat, we kissed and stroked each other's face. I gently unbuttoned Sarah blouse and tried to act like the extra time the nails made me take was part of a slow seduction. Finally I got the blouse unbuttoned and began to caress her breasts through her bra. As her nipples stiffened, she took a deep breath. 

"Take my bra off Jack!"

Her words made a chill run up my spine. I had enough trouble getting her bra off without nails, and I realized that this bra was Sarah's tightest. I started working on the clasp, but I could not get enough slack in the material to open the little catches. Sarah was rubbing my dick through the hose and would slide the hose up and down my erection. The material has a grain to it and it began to rub my dick a little raw. 

"Come on Jack, I am so horny, get my bra off!"

I couldn't do it, her bra was so tight I could not get my fingers to pull up on the fabric to get some slack.

"If you can't do it Jack, give up the bet and I will do it."

That did it, I redoubled my effort and dug the bra away from her back with the nails. I got the 3 little catches to release and the bra came free. Pulling her blouse free of her shorts, I soon had her topless.

"Jack, use you nails on my breasts!"

I went to work on her breasts using the nails. It was so sexy gently raking the nails along the sides of her breasts and tweaking her nipples. I remembered how Sarah had done this to me when she had her long nails and I tried to repeat her motions. She was breathing heavy and her eyes were glazed over as she kissed me again and again. Her rubbing of my dick was erratic and the unpredictability kept me completely off stride in my response. The stimulation was causing me to leak pre-cum on the panty hose but was not going to give me any relief. 

"Finish undressing me Jack!"

The shorts were a little tight, but I was able to work the zipper pretty quickly. Pulling her shorts off with her panties I was shocked by the wetness leaking out of her pussy. I was drawn to her pussy by the nectar and knelt down to taste her pussy. Licking at her cunt lips I can feel her building to a climax. I part her lips with my fingers and accidentally scraped Sarah with the edge of my long nail. She shuddered and grabbed my hair, pulling me up to the seat again.

"Use you nails on my cunt!"

I start rubbing the tips of my fingernails along the edge of her pussy. I remember how Sarah used to drive me crazy by scrapping her nails along my dick and tried to copy her technique. With my other hand I pulled Sarah around so that her back is against my chest. Now I could reach her breasts with one hand while using the other on her wet pussy. Sarah was trembling all over and her breathing is short and fast. Looking down, I can see my wife's beautiful body being made love to by two hands that should be on another woman. It is like watching a porn movie where two women are performing mutual masturbation. Sarah's is smashing my dick against my body and I can feel it throbbing in my pantyhose.

"Open your eyes Sarah and look at my hands on your body!"

Sarah looks down and can see what I have been watching. Two hands with long red nails massaging her breast and cunt. Faster and faster I finger her cunt as she races to orgasm. Watching the whole scene is overwhelming to me, so Sarah must be close to one of her out-of-body orgasms. I take first one finger and slide it into her cunt. I start finger fucking her and take a nipple in the tips of my nails like a pair of needle- nose pliers. Now I have 2 fingers in her cunt and am working them in and out as fast as I can in this position. Pumping and pumping my hand Sarah is having multiple small orgasms, but is not quite over the top. I pull my hand out to the tip and run the edge of my nail around her rock hard clit and quickly jam 3 fingers in her cunt. She is starting to stiffen her whole body when I do it again, twice more quickly. She reaches her peak and has the big orgasm. I keep rubbing my nails along her breast and outer cunt lips as she orgasms for what seemed like several minutes until she completely collapsed.

I hold her and rock her for several minutes as she comes down.

"Now you can make me come like I am your lesbian lover Sarah."

Sarah spun around and asked me if that was what I wanted. I said it sure was.

"OK Jack, but first you need an enema"

"What?"

"I am going to fuck you with our vibrator and you need to be clean before I use it on you!"

Our vibrator was bigger than my dick and was one of the models shaped like a real cock with a harder plastic vibrator in the center. Sarah says it feels very real when I use it on her (and when she uses it herself because I am out of town). 

"I don't think that is such a good idea, I can't take that up my butt!"

"Yes you can, you just don't know it yet." "I will work you up to it and you can stop me anytime you want Jack." "I won't force this one as a condition of the bet, just trust me."

I had never been so sexually charged in my life and I really did trust Sarah with my life, so what was my asshole compared to that?

"Ok, you can do it."

Sarah led me to the bedroom stroking my pre-cum soaked dick trough my pantyhose all the way. 

"Before we start, lets review the score Jack." "You chipped your polish on one nail on the left hand and one nail is almost completely off on your right."

I looked down and she was right. In the middle of our lovemaking, I had done some serious damage to my new nails.

"You also scratched my back taking my bra off, so you scored a total of 5 points plus your prior 3 to bring your score to 8!"

I was shocked to see my points pilling up so fast and it wasn't even noon yet.

"That's not right Sarah, I damaged my nails doing one task, the fact that I damaged 2 nails counts the same as 1 nail or 10 nails as long as it happens during the same activity."

"Well Jack, since we didn't clearly state the rules regarding this per event vs. per nail rule, I am going to let you have it your way." "Let's see, that makes your score 6." "Your not going to make it Jack, want to give up now?"

"No, I am only a little over halfway there on score and about the same amount of time has gone by." "I think I still have a great chance to win the bet!"

Sarah just smiled and sat me down to fix my nails again. She replaced the severely damaged nail using a lot of super glue, removed all my polish and redid my 10 nails. They looked wonderful again. I could see what time and effort Sarah had put into her nails based on the last 13 or so hours to agree that it was not easy, but I didn't want to lose the bet so I kept my mouth shut.

Sarah told me to sit still and let my nails dry before we moved on. She slid around behind me and again started rubbing my cock through the pantyhose. You can't imagine how good something can feel and still hurt until someone masturbates you with pre-cum soaked nylons. I think it is like a little "Scotch" pad rubbing away layers of skin cells, stimulating you while hurting enough to hold you short of orgasm.

"Don't go away, I have to go potty." "And whatever you do, don't touch anything with your wet nails, it will smear the polish and I will be pissed if you make me redo them!"

She did it again, bringing me to the edge of orgasm and then stopped in the nick of time so that I am getting a second case of "blue-balls" in as many days. I close my eyes and relax in Sarah's armchair at her dressing table. I don't know how long I waited, but when I opened my eyes again, Sarah was taking Polaroid pictures again. She was dropping them on the floor and had taken good six or seven pictures of me sitting at her dressing table wearing a very frilly apron and pantyhose. These pictures were more humiliating (if that was possible) than the first. Before, I was clearly tied up and could at least argue that I was under the control of someone else. This time I was sitting there untied in an apron wearing pantyhose and I had a huge bulge in my apron where my dick was sticking out.

"Hey, no pictures!" "You can't keep those, give them to me!"

"Jack, I am not going to share these with anybody!" "I just want to be able to take them out when we are old and have kids around keeping us from playing sex games like this on a Saturday." "Nobody will ever see these pictures but us, I promise!"

"We will talk about it later, but for now I guess you can keep them."

"Good, now sit still and I will show them to you!"

Sarah flew into my lap and sat down on my dick. After I yelped in pain, she pulled up my apron and sat down so that her cunt was on top of my dick and we were front to back. Sarah kept wiggling her but as she showed me the pictures, she was going to make sure that I didn't lose my erection as she showed me the pictures.

"See how sexy you look in your apron and hose Jack?" 

"If you say so Sarah."

"Oh I do and besides, if you grow your hair out a little longer, you can let me give you a hair-do to go with your nails" "Wouldn't that be sexy?"

"I don't know anymore Sarah, this is already way beyond what I thought my limits were in sexual matters!"

"You look great in pink Jack and I think I am going to have to dress you up more often!" "It is sort of like playing Barbie with a life size doll, doing makeup with a girlfriend and having great sex with your husband all in one." 

I didn't know about the first two, but I knew that this was the best sex we have had in a long time.

"I guess so, but playing like this will take a little getting used to."

After a few more minutes, Sarah said my nails were dry and we needed to move on to our "girl-on-girl" sex. Taking me into the bathroom, she got out the enema bag. I have a very sensitive asshole, and the idea of getting an enema was not high on my list of activities. Sarah went about getting things ready and filled the bag up with a lot of warm soapy water.

"That looks like a lot of water Sarah!"

"Don't worry Jack, you can take it." "Yea, take it like a man!"

I didn't like her little joke, but my hardon and blue-balls kept me cooperative. Sarah bent me over just so on my knees, pulled down my pantyhose and started working some KY jelly into my ass. Soon she was finger fucking me and I was moaning in pleasure. Now she was fucking me with longer strokes and I was really starting to like this feeling. Sarah, stopped moving in and out of my ass and I felt the pressure. She had been fucking my ass with the enema nozzle.

The warm water was rushing in very fast, and I let out a "Sarah!" to let her know I didn't like this. She slowed down the water and let me get used to the pressure. Before I got completely use to the pressure, she was done. Sarah quickly popped the nozzle out of my ass and pulled up my pantyhose. Standing upright again, I looked down at the bulge in my front, it could not have been any bigger. My guts were full beyond belief and Sarah was rubbing her tits against my back and rubbing her hands on my stomach.

"Do you think being pregnant will feel like being full like this Jack?"

"How would I know, I have never been pregnant and never will be."

"I know Jack, but close you eyes and imagine being pregnant." "When I was in highschool, one of the girls got pregnant, and a couple of us gave each other enema's and tried to imagine what it felt like to be pregnant."

This was the first time Sarah had ever mentioned doing anything like this with other girls and I wondered if this was the basis of her lesbian fantasy. 

"Jack, telephone!"

I had not heard the phone ring as I stood there thinking about Sarah's words, but I went into the bedroom to see what was going on.

"It's your Mother and she wants to say hi!"

I pick up the phone and said hi to my Mom.

"I didn't hear the phone ring Mom, but thanks for calling."

"Sarah called and said we hadn't talked in a while so she was going to make sure her husband kept in contact with his mother." "Wasn't that nice of her!"

The cramps in my gut hit about the time my mom got to the part about how nice Sarah was.

"Yes Mom, Sarah is special that way"

I very quickly reached the point of agony and had to get off the phone. Sarah was sitting across the room grinning ear to ear over my predicament.

"Can I call you back tomorrow Mom, I was just going out the door to help a buddy with his car and I want to get going so I can get done and back home to Sarah." "Sarah is being a little trouble maker, calling you as I was going out the door."

My Mom thought that this was extremely funny and she would be happy to get my call tomorrow. I hung up the phone and ran to the bathroom. Getting the panty hose down was a lot easier than putting them on, but it was still difficult when you are about to blow. Somehow I made it and sat down on the toilet.

"Sarah you can be such a bitch at times!"

She had put the toilet seat up and I had sat down in the cold water. I don't know how, but I managed to pick up my butt, put the seat down and sit back down before the worst could happen.

It was a major league sensation as the water rushed out of me. I had never had an enema even as a child and this was overwhelming. As I was coming to my senses again, I saw the flash of the camera again. I was numb, and only looked at Sarah as she recorded my current humiliating position. She stopped and showed me the pictures. There I was with pantyhose pulled down, in a pink and white apron, and my manicured hands resting on my nylon covered thighs. The hose were black and the red polish was clearly visible. My face had a strangely satisfied look and you could easily believe I was very happy to be sitting on the toilet like a woman in nails, hose and apron.

Sarah darted off to put away her new treasure. When she returned, she told me to take my time and when I was ready, take off the apron and hose and shower up again. She wanted me clean inside and out.

It took a few more minutes before I was ready, and I reached for the toilet paper and froze. I could not image how to wipe my butt with these nails. Sarah had been hiding just around the corner and she poked her head in when I froze.

"If I have to wipe your butt, you lose Jack!"

I made up my mind to not lose after all I had been through. Working carefully, I managed to complete my paper work (pun intended). Getting into the shower was a perfect idea and I slipped into the warm water. After a few minutes, I looked around for some soap and the only thing in the shower was one of those nylon net body washers and liquid soap.

"Sarah, bring me some soap, please."

"Just use the liquid soap, we are out of your bar soap."

I soaped up the body washer and washed up. The texture of the net against my hairless skin was very erotic. I was getting quite aroused again when it hit me how much this soap smelled. Sarah had put her strongest perfume soap in the shower. I was going to smell like no man I had ever been around after this.

When I got out of the shower, Sarah was again ready to dry my off. She worked the towel against my skin until my skin was pink all over. Sarah grabbed me by my hard dick and led me into the bedroom. Turning me around she put her naked body against me and started kissing me. I tried to kiss back, but she stopped me.

"Not that way Jack, remember you are going to let me make love to you like a woman."

I relaxed and let Sarah take the lead. She kissed me and caressed my very smooth and soft skin (at least for me). Every time I tried to move Sarah along, she told me to relax and let the sensations come to me. I was hard as a rock and reaching the point that I didn't care what Sarah did next, I just wanted to feel everything she could make me feel. Then she stopped.

"Time to get dressed Jack."

Sarah drew my attention to the bed and I saw what she was pointing to. On the bed was a pair of very shear stocking, a garter belt, pink silk panties and a matching pink silk camisole. I was hesitating and then Sarah simply said "Please, for Me." and I was putty in her hands.

Sarah helped me this time with each article of clothes as she got me dressed just so. When she was done she showed me my reflection in the mirror. I almost exploded in my panties, but she pinched my nipples very hard through the camisole to bring me back to earth.

"Get on your knees, on the bed and put your hands at the corners."




Getting Nailed



Sarah put my hands in the cuffs again and started kissing me all over my face and neck. She slid up and down my body, got on the bed under me and was truly making every inch of my sensitive skin tingle. The feel of the silk sliding over my hairless body was a new and wonderful sensation. Sarah worked around behind me and started sliding my panties down in the back. The front couldn't clear my dick, so they would only come down enough for Sarah to reach my asshole but not my balls. She had hidden some lubricant and started working it into my hole.

"I am going to treat you ass as if it was your cunt." "I will take my time opening you up like the virgin you are, so tell me if I am going faster than you like."

"Why did you have to tie my hands for this?"

"You get to control how fast and what limits you have, but I get to decide what happens!" "Don't you think that is fair?"

I didn't, but at this point her finger was starting to feel quite good in my ass, I mean cunt. As Sarah worked my new cunt, she told me that many women can't orgasm with just stimulation of the vagina, and needed to have their clit stimulated also. She kept asking me if my clit needed stimulation to reach orgasm or could I experience a "vaginal" orgasm like her. I had no idea, but I was willing to keep going. Sarah pushed in some more lubricant and started working two fingers in and out of my "cunt".

I was moaning now and knew that trusting Sarah was going to get me well satisfied. I was feeling a little fuller now as Sarah worked three fingers into my "cunt". I adjusted quickly now and started rocking back against her hand. Sarah had converted me, I knew that having my ass fucked, finger fucked, vibrator fucked was now well within my limits. 

I looked back over my shoulder as Sarah let out a little moan. She had the dildo/vibrator in her own pussy and was working it in and out slowly.

"I am warming it up for you, I don't want you to lose your virginity to a cold phallus."

How kind of Sarah, worrying about my "de-flowering" and wanting it to feel as good as possible, even if she had to get some pleasure in the process. Sarah worked some more lubricant into my "cunt" and put the tip of the dildo against my anus. With the stretching she had done, it went in right away. She started working the dildo in and out and each time the thrust went a little deeper. I was being fucked and liking it. As she worked the dildo I rocked my hips back to meet each thrust. Then Sarah stopped fucking me, turned on the vibrator and started kissing me on my ears and neck.

"Don't stop!"

"Beg me Jack!"

"What!"

"You heard me Jack, beg me." "Beg me to fuck you until you cum!"

I begged, oh how I begged!

"Please fuck me Sarah, please!" "I'm so horny and need you to keep fucking my ass!" "Make me cum with your fucking!"

Sarah kept me begging for several minutes while she teased me and then she suddenly got off the bed. When she returned, she had put on a strap- on harness. I had forgotten we even had the darn thing. Someone had given it to Sarah as a gag at her bachelorette party and it had gotten tossed in the closet and forgotten. The dick was even bigger than the vibrator up my ass and looked very real.

"That is bigger than I can take, don't, please don't!"

"You get to control how fast we go Jack, not what we do, remember!" "If it starts hurting, I will wait until you are ready for more."

Sarah got up on the bed behind me and started working the head of the dildo into my "cunt". As she pressed forward, I felt the head slide in. I let my breath out and Sarah waited for a minute. As I adjusted, she started working it in and out slowly. Very quickly it was going in halfway and I was moaning again in pleasure. As I started rocking to meet her thrusts, she pushed further in each time until I felt her pubic hairs against my ass. I was hooked. She was picking up the pace and I was rocking back in complete synchronization. She had taken me past a new limit and I didn't even care. With each thrust she reached the hilt and I let out a moan when she buried the dildo in me. The dildo harness setup had a clit stimulator built into it and Sarah was getting worked up herself. I don't know how long she kept rocking into my ass and running her hands over my silk covered body, it could have been all day as far as I was concerned. I was almost out of body with sensation and I was for certain out of my mind with lust.

Sarah started to climax, her body shaking strongly as she reached orgasm again. I was still rocking, but she wanted to hold still for a moment. When she relaxed again, she reached up and unbuckled my hand.

"You must need to have your clit stimulated to reach orgasm."

My hand flew to my dick and I drug my pre-cum soaked panties over the head of my dick and started stroking.

"Slow down, and set a rhythm on your clit to keep pace with my fucking of your cunt!"

Sarah started rocking into me again and I matched her thrusts with my manicured hand on my own dick.

"Just use the tips of the nails and get your dick ultra-sensitive."

Sarah had me in a place I had never been and I liked it a lot. As she pumped my ass with that big dildo, I used my nails to rake up and down my own cock. I closed my eyes and imagined what Sarah must feel like to get fucked and it was wonderful. Faster and faster she worked the dildo in and out of my ass until she let out her breath and started to orgasm again.

I went over the top, and started spewing all over my hand as she was slamming into my "cunt" and climaxing herself. I think I had the longest orgasm of my life as she reamed me good.

"Time to clean up your mess Jack."

I knew what she wanted and started licking my hand clean and Sarah kept reaming my ass as I licked up my own sperm. I felt total humiliation over being a cum- eater cross-dresser and total exhilaration with all my new sexual sensations. My hand would go down to my dick and grab all the sperm I could find and flash back to my mouth to be licked clean again. The sperm dripping off the long nails was so erotic and totally humiliating. Like the night before, I kept having small orgasms, one after the other for a good five minutes (as time goes during orgasm). Finally I just collapsed on the bed and Sarah fell forward driving her dick into my ass. She just lay on my back whispering into my ears about how good it was for her and how much I must have enjoyed my first fucking. I could not believe how many new sexual experiences we had enjoyed since last night and did not want it to end.

After a little more rest, Sarah got up and pulled the dildo out of my ass and I hated the empty feeling.

"I will never be the same after that."

"I know just how you feel, loosing your virginity is almost always a life- changing event Jack." "You truly will never be the same."

"This is the second time I lost my virginity and it is more memorable than the first!" "I didn't know what I was doing then and I was so excited that is was over almost before it started." "This was one of the best orgasms I have ever had and that isn't true about my first straight sex experience."

Sarah undid the other cuff and we cuddled up and took a nap. 



Chapter 3, End of a Long Day

I heard Sarah's voice calling me back to real time and slowly woke up.

"Jack, wake up." "I am not going to let you win the bet by doing nothing this afternoon!"

The sun was down a bit and we must have slept for 2 hours. Sarah was draining me with all this stimulation. It was exquisite to feel like this. I looked at my body as Sarah was rubbing my silk covered chest.

"Where did you get this silk stuff Sarah?"

"When I went out this morning, I ran over to Sally's Boutique and picked it up." "She always has some really nice items like this in the store."

"This isn't your size, so who did she thing they were for?!"

"Don't worry Jack, I told her that I had to rush to a bridal shower for a girl at work and hadn't been able to get off from work in time to shop."

I was relieved and amazed at how fast Sarah had put all these sex scenes together in such a short time.

"Sarah, if I didn't know better, I would say you had been planning this for weeks."

"Jack, I was so excited last night I woke up after a couple hours of sleep and just had sex thoughts running through my mind." "I tried to masturbate myself back to sleep and planned this out as I fantasized about you."

This was high stakes sex and Sarah just kept taking me a little further past my limits. Once I had a new barrier in my head, Sarah shattered it.

"Time for nail inspection!"

Checking my nails out, Sarah found one of them chipped badly. I must have done it when I pulled my panties down to get at my hardon. I had almost ripped the panties tugging on them and I hadn't even tried to avoid putting pressure on the nails.

"That is two more points Jack, you are up to 8!" "Are you ready to give up?" 

"Not a chance Sarah, you have to earn the last 2 points before I will admit you win."

"OK, have it your way." "Get up and let me fix you up again."

Sarah took one look at my cum and lubricant stained panties, then chastised me on my poor hygiene and upkeep. She took the lead and pulled off the soiled panties and surprised me with a second pair of matching pink silk panties.

"I girl has to plan for accidents Jack or maybe I should start calling you Jacquelyn." "You can put on your new panties after we clean you up!" "You will also have to hand wash these items to keep them nice."

I shot her a dirty look as Sarah sat me back down in the armchair and repaired my nails again.

"Jacquelyn, since you seem to be leaking so much, I think you need to put in your tampon!"

"What are you talking about Sarah?"

"Well Jack, you cunt is full of pussy juice after fucking and you don't want it to run out and ruin you new panties do you?" "Besides, this will be your next test." "One thing I never liked was putting in a tampon when I had long nails." "If you want to win the bet, prove you can do this task I have to do each month."

My repaired nails were dry, so I followed Sarah back into our bathroom. She got out a couple of tampons and showed me how the applicator system worked with one and handed me the second.

"Sit down on the toilet and put it in your "cunt" to absorb the discharge Jack, then wipe your bottom and you'll be all done"

Listening to Sarah talk like that was spinning my head again. I think she has been thinking about this stuff a lot longer than last night while I slept. Putting the applicator against my "cunt", I pressed it in. The thing slipped right in with the lubrication and stretching I already had. Step 2 was to press the applicator and I was stuck. How do you hold the damn thing with the nails getting in the way and still make it work? The more I worked at it, the more the lubricant made it hard to hold. Sarah flashed a picture just as I got it to slide home and a smile broke out on my face. I had to laugh a little bit as Sarah was so excited to snap the picture at just the right time. When she showed me the picture, you could see me sitting on the toilet, dressed in silk and hose, playing with my own ass and smiling like an idiot. If anybody ever saw these pictures I was dead.

"Now don't forget to wipe Jacquelyn"

I did as told and got up, put on the new pair of panties and let Sarah lead me by my hand to our bed.

"Jacquelyn, now it is your turn to fuck me like a lesbian!"

"How am I going to do that Sarah, I have a real dick and not a dildo in a harness?"

"Well, I have an idea or two." "Just start making love to me like we have been practicing and I will show what I have in mind."

I was sitting on the edge of the bed with my naked wife, dressed in silk boudoir wear and had a tampon up my new "cunt". If all the kinky sex we had ever done was an 8 on a scale of 10, we were now over 20 on the 10-point scale.

My horniness was no longer at a peak with all the sex we had since starting this bet, so it was pretty easy to keep myself from racing toward fucking. Kissing Sarah could be an event not just foreplay. We kissed each other a very long time and slowly my dick/clit began to stiffen. Sarah was gently stroking my face and letting me hold her as we frenched each other. A passion was building, but not with my usual urgency. Sarah moved my hands to her breasts and whispered in my ear that she was ready for me to use my nails on her. I thought that having long manicured nails scraped against your flesh was my fantasy, but Sarah was turned on by the sensations as much as me. My nail fetish was her nail fetish.

As I traced my nails along her breast I was mesmerized by the look of the nails against her skin. Candy apple red and long, highlighted by the milky white flesh of her breasts. I was fully erect now. My second pair of silk panties was a "tap pants" style and had a lot more room for a hardon, so I was not terribly uncomfortable. Sarah would lightly brush my dick through the silk to add to my sensation. Sarah leaned back on the bed and pulled me down with her. Her breathing was getting deeper and her eyes had that lust in them again as we continued our kissing and breast play.

"Use your nails on my pussy Jacquelyn!"

I kind of had the idea now what I could do to play with Sarah's pussy using my nails. Lightly scraping her pussy lips as we kissed was getting her very excited. I took just one nail and ran the edge along her moistness and gently scraped her clit with it. Insert one or two fingers in her pussy, then keep working the sharp edge of my nails on her sensitive spots. My erection was stretching out my panties but Sarah had drained me so much that I couldn't see any pre-cum stains on the pink silk. We went on like this for a long time and Sarah had several small orgasms. Kissing stroking and pinching her nipples while using my nails on her pussy was a lot of stimulation, but not enough to take Sarah over the top and a major orgasm.

"Time for my dildo fucking Jacquelyn!"

"You want me to fuck you with the dildo now?"

"Not exactly, we have done that lots of times, what I want is for you to simulate what I did to you with the big dildo and harness!" "Let me show you what I mean!"

Sarah pushed me flat on the bed, pulled my silk panties down and took my dick in her mouth. She was bobbing her head up and down aggressively and this always takes me very close without letting me cum. When she had me as hard as she liked, she reached over to the nightstand and got a little bag of stuff. I watched as Sarah took out a roll of gauze. I was amazed as she started wrapping the gauze tightly around my dick. She started at the base and worked up to the tip. Back down again, around behind my balls in a tight band, a third smooth layer wrapped on my dick. Sarah repeated this process until the whole roll of gauze was wrapped tightly around my dick. The effect was amazing. The gauze was holding my erection like a cock-ring and would insure my erection was not going to go down anytime soon, while the layers of gauze made my dick much thicker. Next Sarah took out a condom and rolled it down my shaft. It was very tight, but she managed to get it on over the layers of gauze.

"One size fits all you know!"

With a smile and her sexiest look, Sarah started masturbating my dick. Nothing, I could not feel a thing, except the pulling and pushing of my dick as she went up and down. She had turned my own dick into a dildo.

"Fuck me Jacquelyn, start from the rear"

Sarah got up on the bed on her hands and knees and I stood in the floor behind her as I pushed my dildo/dick into her pussy. Her pussy was very wet and I had no trouble sliding in.

"Ah, that feels so good Jacquelyn!" "It is so much thicker than my husband's dick, fuck me!" "I need a thick dick up my pussy to get this horny!" "You're fucking my brains out Jacquelyn, fuck me deeper!"

I knew Sarah was saying these things to humiliate me and excite me, and I was responding. I was a little pissed off and was really trying to pound into Sarah's pussy. I was pounding away for all I was worth and all I could feel was a 2 direction tugging of my dick. I wondered if that was what Sarah felt when she fucked me in the ass today... I decided not, she at least had the clit stimulator on her dildo harness and I wasn't getting the tip of my dick rubbed by anything. She was the winner of this comparison as well. Sarah was climaxing again and again as I held her hips and pounded her pussy. 

After a while I was a little board with the lack of stimulation for my body and started watching the action in the mirror to get some visual stimulation. I was shocked my what I saw! If I ignored my face and lack of tits, my wife was getting the dildo reaming of her life on our bed by a "woman" in beautiful silk bedroom wear tightly gripping her hips with hands tipped in the longest nails I had ever seen.

"Don't stop Jacquelyn, my husband never fucks me long enough!" "You make me cum again and again!"

It was true, I never could last this long when we fucked. Sarah could orgasm for days if I could keep up with her. Even on my best days she always wanted more than I could give. She said no man could fuck her as long as she liked. I wondered if she had been dildo fucked by a woman before? Maybe when she did the enema play in highschool?

Sarah had a big orgasm and clamped her cunt down on my dick. I could feel the vice like pressure and stopped fucking her as she collapsed on the bed. I kept my dick buried in her pussy, fell forward with her and gently stroked her neck and face as she came down. After she relaxed slightly, she asked me to lie down on the bed. I lay on my back and she straddled my dick. Sliding down she wiggled until I was completely buried in her pussy. Rocking back and forth, she started talking.

"Jacquelyn, you are a fantastic lesbian lover!" "My husband is a wonderful lover, but he can't make me cum like this!" "As much as I like it when he cums in my pussy, it is never enough!" "He rushes as his climax approaches and I love it but it ends way to soon!" "He has a nice dick, but your dick is much thicker and it gets me so horny!"

As she talked she started working her pussy up my pole and down to the hilt. I told her to open her eyes and look in the mirror. Sarah broke out in a great smile as she watched herself ridding up and down on my dick/dildo.

"Put your hands on my tits and use your nails Jacquelyn!"

I didn't like her calling me Jacquelyn, but this was her trip and I was not going to argue as she fucked herself to death on my dick/dildo. Up and down she went as I worked my hands along her breasts and pinched he nipples lightly with the tips of my nails. She was flowing so heavily, that it was dripping down my balls and soaking the sheets. When she finally climaxed this time, she fell forward against my chest and was kind of flopping like a fish as her whole body was racked with her climax. I held her tight so she would not rip my dick off my body with her convulsions.

Sarah was sobbing lightly as I held her. She had never had a climax like that before and I was again jealous of her.

"Why are you crying?"

"I can't explain, it was just more than I could take."

I held her for a good 15 minutes as she came back to normal. Slowly she got enough strength to pull herself off my dick/dildo.

"Jacquelyn, that was unbelievable!" "I have always wanted to make love like this, but didn't know how to do it and not hurt Jack." "Now I know what it feels like to be fucked with a big fat cock and I was faithful to my husband at the same time!"

We lay in each other's arms (me in the wet spot) for several minutes when Sarah sat up and looked at my dick.

"Poor baby, we better get you some air!"

Sarah pulled the rubber off and started unwinding my dick. As the gauze came off, I could see how purple my dick was. If she had left this on much longer, I sure it would not have been safe. As she pulled more and more gauze off, my dick spun around like a little crank and fresh blood came rushing in as she went. I groaned in mild pain coupled with the sexual stimulation.




Getting Nailed



"Did it hurt?"

I told Sarah that it did not until she pulled off the gauze, but now it was returning to normal. She held me for a few minutes more and then got up and pulled me up off the bed. She spun me around and checked to see if my tampon was still in place and after tugging on the string, she seemed satisfied.

"Pull you panties up, go make us a little snack and I am going to put on some cloths"

"That was amazing Sarah, I kind of wish you had some pictures of making love like this." "I am sure you would think that they were better than all the pictures you have taken so far!"

Sarah just smiled and pointed to the closet. She had left the closet door open slightly and on the tripod was our video camera.

"I got the whole thing on tape!" 

I couldn't even breathe when Sarah told me she had made the video! I pulled up my panties and headed for the kitchen.

Fifteen minutes later Sarah joined me in the Kitchen. She was dressed in tight black jeans, simple white T-shirt and her black boots with heels that make her taller than me. She didn't have a bra on and her breasts were beautiful in the tight white shirt. We sat down to the little snack of soup and fruit, while sipping a glass of wine in blissful silence. 

"Time for nail inspection!"

Sarah inspected my nails for a long time, but could find no new damage.

"You are still at 8 points Jack, maybe you have got a chance after all."

I was starting to get a cocky little smile on my face when she scared me to death!

"One last test, time to go out of the house!"

I was not going to agree to this, now way, no how!

"Forget it Sarah, I am not going out of this house with these nails and that's final!"

"Come on Jack, I think you have enjoyed this bet as much as I have and you know I won't do anything to hurt you or publicly embarrass you!"

Her words were calming me down, but I still thought the risk was more than I wanted to take.

"Sarah, I have not been sexually stimulated and satisfied like this since we were first in love or maybe ever, but I just don't think I can do this."

"OK Jack, let me fix you up the way I want and you can look at yourself in the mirror and tell me if anybody will know you are wearing nails." "If you can tell, I won't make you do it." "If you can't tell in the mirror from any angle, then we go." 

I agreed, because there was no way Sarah was going to cover this up and take me out in public. She then went about collecting some items and before I knew it she was back with her treasures. I did not see anyway that the items she had with her would do the trick, so I told he as much. Sarah just laughed and said that time would tell.

Last summer I had taken an old pair of jeans and made some cut-offs. Sarah had gotten the bottom of the legs from these old jeans out of the ragbag, one of my belts and some twine from the garage. She started poking a series of holes in the jeans legs, then Sarah slid each jeans leg up one of my legs. She then put the belt around my waist and threaded the twine through the holes she punched. By fiddling with the twine, Sarah could adjust the old pants legs so they reached the tops of my feet as well as a tailor.

Sarah had me stand up and she checked that the jeans legs came to the tops of my feet. She spent a great deal of time checking her adjustments until completely satisfied. Next Sarah picked up a top outfit she got from her closet. It was one of those "layered" knit things with the different colors. The outer layer was a black sweater thing, and the inner layer was a white knit turtleneck. Sarah separated the two parts and she had a turtle knit thing that would come down to the tops of her breasts and had no sleeves. They used to sell something like this in men's stores and we called it a "dickey". She pulled the "dickey" over my head and adjusted it just the way she liked it. Next she had me put on my running shoes and stand back up. I took a look in the hall mirror and was not going anywhere like this. I saw the silk camisole with matching panties, stockings and garter, and these incomplete articles of clothing. It was worse than being naked. Now Sarah picked up my "London Fog" trench coat that I wore over my dress cloths and zipped out the liner. She helped me on with the coat, buttoned it up, tied the coat belt and told me to put my hands in the pockets. Sarah pushed me down the hall to get a good look in the mirror. 

"I think we are going out Jack!"

I was shocked, there was not any way you could tell that I was in silk and wearing nails. Sarah had covered my so that anybody who saw me would think I was dressed for a cool fall evening, nothing more. I turned every way I could and there was nothing that gave away my humiliating state of dress. I would be in public and in mental bondage if we went out that door and no one would know but Sarah and me.

"I don't know about this Sarah, I looks OK, but in the bright outdoors, who knows."

"That works out fine Jack, I want to go to the movies and that is very dark!" "Remember that chick flick I wanted to see, well we are going to see it together."

My head was spinning, I didn't have any reason not to do what Sarah wanted, except my fear. 

"Remember what we agreed, If you could not tell, we would go!"

I was trapped and Sarah knew it.

"Don't go away, I will be right back."

Sarah was back in a flash. She had put on my old leather motorcycle style jacket and she looked great. It was a bit of a gender reversal, her in tight jeans, T-shirt, leather and a little taller than me, while I was in silk, hose, garter belt, and wearing my long manicured nails.

Sarah put her arm in mine and led me to the garage. She opened the passenger door for me and got in to drive. My heart was pounding all the way to the theater. I might as well been handcuffed, the mental bondage kept my hands buried deep in my pockets. I was alternating from blushing to chills as we drove past our familiar landmarks. I was so relieved when we got to the theater without having a wreck, that I took my first deep breath since she started the car. Sarah put her arm in mine and we walked up to the ticket window.

"Let me get it Jack, I have more cash than I like to carry on me."

Sarah turned just a little, so I could see her T-shirt wrapped breasts jiggle in the open jacket as she wiggled her hands into the tight jeans and got her money. Paying for our tickets, we headed into the theater. The ticket taker was very disinterested and I could have been naked without him noticing a thing. Sarah grabbed my arm and drug me to the concession counter as she got a big drink and some popcorn. This was the early show and the movie had been out for a few weeks, so we had no trouble finding some secluded seats.

"I told you no would know how you are dressed Jack."

I didn't care, I was so nervous that I can't remember anything about the movie, except that it started and ended. Sarah kept me in a constant state of arousal throughout the show. She would slide her hand in my coat and rub my dick through my silk panties until I was about to cum and then take a sip of cola and eat some popcorn. She would stick the straw in my mouth and hold the coke in place until I took a drink. She stuck the straw in my mouth so much that I must have drank well over half of the coke. 

Finally, the credits started to roll.

"Lets go home and fuck some more." I whispered in Sarah's ear.

Sarah took my arm and we headed out the exit to our car. 

"Jack, my eyes are hurting and I need for you to drive home."

Sarah was quick when she wanted to be and she just darted ahead and jumped in the passenger seat and locked the doors again.

"Sarah, let me in the car!"

"You know the code Jack, let yourself in!"

We had a touch pad on the driver's door of the car and if you pushed in the right code, it unlocked the door.

"I can't Sarah, people will see my nails!"

"If you don't get in here, people will think you are trying to attack me in the parking lot and then you will really have a problem!"

I don't think anybody was paying any attention, but Sarah had created the image in my head and I was convinced everyone was looking at me.

"Sarah, open up now!"

Sarah just smiled at me and shook her head. I was getting frantic, all the coke Sarah made me drink was making me have to pee! I was shuddering and holding back my flow for all I was worth and Sarah was getting the biggest kick out of my predicament.

"Please Sarah, open the door!"

"Not a chance Jack, if you want to go home, get in yourself." "If you don't get in soon, I am going to leave you here!"

I was frantic, the cool air was blowing up my coat and my full bladder was protesting. I was not going to take these hands out of my pocket for any earthly reason. The longer I stood there the more desperate I got. Taking my hand out of my pocket, I started poking in the digital code that would give me safety. I was so nervous that I hit the wrong keys several times and still could not gain access.

"Remember Jack, If you enter the code wrong 4 times, you have to wait 5 minutes before it will work again!"

I was shaking so bad that I didn't think I could do it correctly. I had entered it wrong at least 3 times and if it didn't open this time I would have to wait the 5 minutes. With all my concentration, I entered the code and my whole world changed when the door lock popped up.

"You are such a bitch at times Sarah!"

Sarah just smiled as she handed me the keys.

"I can't drive, I don't have my license and I can't let anybody see my nails!"

"Well, I am not going to drive tonight and as far as I am concerned we can sit here all night."

My bladder was about to bust, so I slowly reached for the keys and started the car. I drove with my hands at the bottom of the wheel and made sure that I obeyed all traffic rules as we headed for the house. Sarah had her hands back under my coat stroking my silk covered cock all the way. My head was spinning, my heart was pounding and my dick was throbbing. 

At last, the house was just ahead and I was beginning to feel safe, when Sarah reached over and honked the horn and waved at our neighbors Lori and Frank out taking a walk. My heart stopped for several beats as they stopped at our driveway for a friendly chat. Sarah jumped out of the car and headed down the drive. It took a few seconds longer for me to get out of the car with my hardon sticking out in front. The humiliation of the situation was helping my erection shrink, but I still needed time to compose myself. 

"Come on Jack, come say Hi!"

I gave a big wave while I was still standing in the shadow of the garage, stuffed my hands back in my pockets and walked down the drive. I could feel my face blushing and my heart was pounding.

"Jack, are you feeling OK?" Lori asked.

"I think I may be coming down with something, I feel very flushed."

"You better get to bed and try to get rested before Monday, or you could be sick for the big presentation!"

Sarah and Lori talked a lot, and she knew our proposal was going forward Monday and I was expected to make the customer presentation.

"I think your right Lori, I am going to take Jack straight to bed."

We said our good-byes and headed into the house.

"Sarah, you can be such a bitch when you want to be!"

I grabbed Sarah, sat down in a chair and pulled her across my knee. I just started spanking her ass as hard as I could with my bare hand. It was hurting my hand after about 20 swats, so I stopped and got her pants pulled down to her knees. I really laid into her panty-covered ass now. I could see her skin turning red through her shear panties. Sarah was wiggling around, and I realized she was grinding her cunt against my leg. I didn't know Sarah liked getting spanked, but after all the other things we tried in the last 24 hours, I wasn't surprised. Her pussy juice was leaking through her panties onto my nylon-covered leg. The faster and harder I went, the more she would grind her cunt into my leg. I spanked each ass cheek over every inch of skin and when she spread her legs, I spanked her between her asshole and her pussy. I finally gave up, my arm was worn out and she wasn't phased in the least by my spanking. I pulled Sarah off my lap and stood up. No one said a word, but we both headed for the bedroom.

As we went down the hall, Sarah was dragging my cloths off, getting the twine lose and pulling my 1/2 pants off. She seamed desperate to have me back down to just silk and hose. I got her naked just as fast as I could, pulling cloths off as we stumbled into the bedroom. I literally threw Sarah on the bed, pulled my panties down and drove my cock into her wet pussy. I have never been able to enter Sarah without foreplay, but the spanking had her nectar flowing freely. With both of us so sexually charged, we didn't last long. After only a few thrusts, Sarah started climaxing and her body was soon shaking. Then I exploded into her pussy, trying to punch through to the other side. Then I was spent and so much energy went out of me I think I blacked out for a moment.

When I recovered, Sarah was lightly stroking my face and telling me how much she loved me.

"I know Sarah, and I have never felt closer to you than right now!"

"Jack, we have done so many things, acted out all these different fantasies, I was afraid it was more than our relationship could take!" "I can't believe the sex and passion we have shared."

"Just rest Sarah, we can talk about it later." "Right now I just want to hold you and melt into the feelings."

We lay together for several minutes until my bladder started protesting again.

"Sarah, I have to get up and take a piss, be right back."

When I went into the bathroom, I was reminded how I was dressed by the image in the mirror. I was a mess, but I still had on the silk camisole, hose and garter belt. I took a good look at myself as I emptied my bladder. It was weird, I had never thought about silk and hose for me, but I had so much fun in my outfit, I knew we would play this way again. I was done and flushed the toilet.

"Jack, time for nail inspection!"

I had forgotten about our bet. But Sarah was going to make sure we both knew who won and lost the bet. I was kind of afraid to look so I just went in to let Sarah do her inspection. Before she even looked at my nails, she inspected my pink camisole, adjusted the garter belt, looked for runs in the hose and finally checked to see if my tampon was in place.

"Well Jack, you have not been very careful with your delicate silk items, but I think they will be OK after being hand washed." "Let me see your nails."

I presented my hands, nails up for inspection. It didn't take long for Sarah to find 3 damaged nails.

"I have good news and bad news Jack!" "The good news is we are going to have a lot more fun next weekend, the bad news is you have ruined 3 of your nails and you lose the bet with 14 points!" "I also don't know if I can get the super glued nails off without filing them off!" 

I looked at the nails for the first time in hours, and they were pretty beat up. I don't know if I did it trying to punch in the code on the car, when I was spanking Sarah or when I was pulling off her cloths. It didn't matter, I lost fair and square.

"I don't care if I lost or won Sarah." "I lost the bet and will be you sex slave for 2 weekends, but I would volunteer right now to do it without a bet!" "I didn't think I could do half the things we did in the last 24 hours, but I have become addicted to this wild side sex!"

We held each other and kissed warmly for several minutes while we chatted about some of our sexier moments. I had never been happier in our relationship and told Sarah so.

"Do you mean that Jack?"

"Yes, not a doubt in my mind!"

"Jack, I have always wanted to do these things with someone, but I needed to trust them completely to have enough confidence to actually do them." 

"I am hooked Sarah, we can play anytime you want."

She knew I meant it and she was grinning ear to ear.

"Do you want to play now Jack?"

Laying in bed with my beautiful naked wife, dressed in my pink silk camisole, wearing stockings held up by my garter belt and with a tampon up my ass/cunt, I could only give one answer as my dick started to harden......... Yes!

"Then clean my pussy, after all you made the mess and I didn't say you could cum and from now on you are going to recycle all the sperm you shoot and I hear it makes you cum eating sissy men horny to eat your sperm and you are going to pay for spanking me, I liked it and you can spank me anytime you want, but you are still going to pay because I am going to use a switch on your ass tomorrow and you will not be able to sit down Monday at work and maybe I will have you wear your silk panties under your suit and when I have the girls over next month I may have you serve us in your pink apron and panty hose and that way they can see your nails and you need to beg me to let you suck your sperm out of my pussy, say 'Please let Sissy Jacquelyn lick her sperm from Sarah's sweet pussy, Sissy Jacquelyn has to eat sperm because it makes her horny.' and I don't want to ever see any body hair on you again and I think you will look good with lipstick that matches you nail polish and you need to learn how to cum when I fuck you in your ass/cunt because it may be the only way I will let you cum for a while and I think we will need a bigger dildo for fucking your ass/cunt and I want you to grow your hair longer so I can style it and Lori says she hates to give Frank head because he is so big and since you like sperm so much I may loan you to Lori when Frank wants a blowjob or Lori can come over after Frank fucks her and you can beg her to let Sissy Jacquelyn suck Frank's sperm from her pussy and if we get your nipples pierced, we can use weights on them to make them bigger and ........!"



Chapter 4, Sunday Brunch

I hate waking up to bright sunlight and the sudden glare in my face from opening drapes was agony. I tried to cover my face, but Sarah had bound me to the bed in my sleep. With my eyes tightly closed against the unwelcome light, I couldn't see Sarah running to jump on my stomach. If I was prepared, it would be no big deal, but I thought I was going to die from a burst bladder as she landed in my midsection.

"Good morning Jacquelyn, are you ready to get up?"

"Yes, and get off me! I am going to wet the bed if you keep bouncing up and down on my gut!"

"Not so fast Jacquelyn, do you remember our discussion last night?"

It all came back in a rush of excitement. How could I forget eating my sperm from Sarah's well-fucked pussy as she promised to make me into her cum eating sissy slave? I knew that eating Frank's sperm was not going to happen, but the rest of her plan was making my dick harder.

"You said you want to play sissy Jacquelyn whenever I want and you lost the bet, so you are my slave for 2 weeks!"

"Sarah, the bet payoff does not start until next weekend."

"I know Jacquelyn, but you have a problem. You see you have on long nails they won't come off without some help from me! You are going to have to do everything I say, or I will not take them off for you!"

I could see by the smile on Sarah's face that she was planning to drag out my situation as long as she could today. 

"If you don't want my help, you can drive yourself down to the hardware store and get some super glue remover and take the nails off yourself!"

I was stuck; I needed these nails off before tomorrow, when my presentation was going to be given to the Client. If Sarah didn't take them off for me, I was going to have to go out in public and buy something in a store. There was no way I was going to do that and show my nails in public.

"OK Sarah, I am your slave for the rest of the weekend, just take these nails off and let me up to take a piss!"