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.