Getting Nailed

"Please fuck Sissy Jacquelyn with your big cock! I need to be fucked, fuck me like the sissy slut I am!"

As I begged, Sarah moved around behind me and gave the butt plug a pull. The pain of removal was short and I was left with the feeling of an empty hole.

"Please fill up my ass, I need your cock in me. Make me cum with your big dick. Sissy Jacquelyn needs to be fucked like the slut she is!"

Sarah pushed the dildo in with one quick thrust. I was held tight by the ropes and when her loins pressed against my raw ass I thought I was going to die. Sarah had her way with me, as she was quite horny herself by now. She was rocking back and forth against a much-reduced resistance because of the stretching from the plug.

"Keep begging for a fucking and moan like the sluts on the tape!"

I began to beg again. "Please fuck me with your big dick, I need to be fucked! Slam that monster in me and make me scream"

I was begging and moaning for all I was worth when I started shaking again. I don't know how loud I was, but I was begging and moaning for all I was worth.

"Yes, yes, yes, fuck me with your big dick!"

Then Sarah reached her orgasm and started shaking. She rammed her cock into me as hard as she could 3 times and then twisted her arms and legs around mine so both of us were supported on my abused legs. Sarah hung on my back with the dildo as deep as she can push it as her body continues to shudder and twitch. Every twitch makes the dildo twitch and it rubs me deep inside and I convulsed in my body. I think Sarah kept jamming her fake cock into my ass for at least 5 minutes as she kept both our bodies racking with sexual release.

"That was a fantastic fuck you slut Jacquelyn! I don't think I have ever had a better piece of ass in all my life!"

I didn't know how many times Sarah had put on a dildo harness and ridden someone to satisfaction, but I knew I had never been fucked like that!

"I think you deserve a reward for being such a good fuck Jacquelyn. I am going to release your clit and give you one more fucking before I stop and take off your nails! Won't that be fun?"

"Please fuck me again with your big dick Mistress Sarah!"

Sarah released my hands and I all most fell over, but she steadied me before I fell. Next she moved my hands behind my back and hooked the cuff together. She removed the cuffs from my legs and pulled my panties all the way off and hooked the garters back. Sarah had me spread my legs and she gave the tape a hard tug to free my trapped dick and balls. My abused dick quickly gained an erection.

"Sissy Jacquelyn has leaked pussy juice, what a slut to leak pussy juice all over your clit!"

Sarah rubbed the pre-cum off my dick and had me suck her fingers clean.

"You are going to look so pretty with those red lips wrapped around a real cock. I wish Frank was here right now, but I guess we will have to improvise."

Sarah led me over to the ottoman and had me lay on my stomach with my head down by the floor. She put a pillow on the floor and had me slide forward a little more. I have always been flexible, but I was surprised how much I was able to keep curling up as Sarah pushed my head and shoulders toward my ass and kept pulling my ass to my head. Then Sarah got behind me and pushed my legs as far apart as she could. When Sarah pulled the ottoman out, I was suspended by my feet spread very wide and by my neck and shoulders on the pillow. The most amazing thing was that I was looking right at my hard dick just inches from my face.

"I am going to fuck your cunt until you cum Sissy Jacquelyn! You can just come from the fucking or you can help yourself along by using your mouth! Which ever way you cum, I am not going to stop before you cum and you will lick up every drop!"

Sarah started working her cock in to my ass again. This time, her pushing on my ass caused me to curl a little more and then my dick was bouncing against my nose and lips. I could not help myself and when my body curled a little more, I opened my mouth and sucked the head of my dick in.

"You look perfect with your red lips wrapped around a real cock Jacquelyn!" I bet you can't wait for Frank to let you taste his big dick!"

I could wait forever to suck a dick; I was not a cocksucker I thought as my own dick was in my mouth. As Sarah worked her dick into my ass, my dick would push in a little further and when she pulled back, I could keep it in my mouth by sucking hard. We built a steady rhythm and pretty soon I was building to my orgasm. Faster and harder Sarah thrust her dick into my ass and the harder and longer I sucked on my own dick.

I shuddered to my biggest orgasm of the day from the double sensation of my ass fucking and the self provided blowjob. My cock started spurting and my ass was having spasms every time my dick spurt into my mouth. Sarah felt the spasm and started pushing her dick in sync with my spurts. I think Sarah was able to pump at least a dozen or spurts out of my dick directly into my mouth. I sucked each spurt down and swallowed every drop.

Sarah pulled out and helped me onto my side to take the pressure off my neck and shoulders.

"You looked fantastic with your lips wrapped around a dick! Beg me to get you a real dick to suck, so you can give a real blowjob to a big dick, not your own little dick!"

I knew my dick was not little, but to have Sarah taunt me like that was humiliating and exciting at the same time.

"Please bring Sissy Jacquelyn a real dick to suck on! I need to suck on a real cock, not some overgrown sissy clit like mine!"

I was over the edge again and I was slipping further into the mental state of a sissy slut! I could not believe how far I had come in just 2 1/2 days. Here I was begging Sarah to bring me a real cock to suck and I had never had any interest in sex with a man!

"Soon enough I will let you suck a real cock, don't worry your little head! I know you will like sucking Frank's cock and it will help Lori out since she can't take the big thing in her mouth!"

After I rested a few minutes, Sarah helped me up and helped me back to the bedroom. She sat me down at her dressing table and I jumped back up!

"Owe, my ass is way to sore to sit on it!"

"Ok, Sissy Jacquelyn, you can kneel down and let me work on taking your nails off."

It took Sarah over an hour to get the nails off. First she removed all the polish and them she started working super glue remover under the edges of the fake nails. After she was done, she used a polishing compound on a battery powered little tool and buffed up the nail surface to finish the cleanup.

"The natural shine will last a few days and people will almost think you have clear nail polish on!"

I didn't care, I was just glad to have my normal looking hands back even if nothing else was normal anymore.

"We can't play anymore today, tomorrow is a big day and you need to relax and get ready for your presentation to the Client."

I agreed and I started to get out of the silk things. As we put out toys away and washed up the lingerie, Sarah and I both grinned as we handled each item. It had been an amazing weekend with the best sex we had ever had.

I looked at my ass in the mirror and it was going to be sore for several days. Sarah had done a number on it with the switch and it was red as the lipstick Sarah had used on my lips!

We had a light dinner and went to bed early (I slept on my stomach).

I could hardly wait for next weekend to get here and as I drifted off to sleep, I kept seeing the image of a big dick between my lips!

Chapter 5, First Week of Service

Monday morning came too soon. I was excited about the big Client presentation and could not sleep the night before. It didn't help that every time I started to drift off to sleep, the kinky sex weekend started playing like a movie in my head and I would panic when I got to the point that someone out there knew about Sissy Jacquelyn.

I was happy to hear the Monday morning alarm and I could get started on what would be the biggest event ever for our project team at work. I was humming to myself in the shower when I turned and the hot water hit my raw ass. I made so much noise that Sarah thought I had fallen and broken my neck!

"Are you alright Jack?"

"Yes, but you did a real number on my ass yesterday, the hot water made me think my ass was on fire!"

I could not believe that Sarah thought it was funny. I finished my shower and took a good look at my ass in the mirror. It was still quite red and had deep red streaks where each blow of the switch had landed. I was going to have a terrible time sitting today.

When I finished shaving and came out to get dressed, Sarah was waiting to give me her helpful hints.

"Jack, by the looks of your ass, you are not going to be able to wear your regular underwear. I think you are going to have to wear the lightest and softest underwear possible or your not going to get through your presentation!"

Sarah was holding up the pink silk tap panties that we had carefully hand washed yesterday.

It didn't take me long to realize that the silk was going to be a lot more comfortable than my regular "guy" briefs. Sarah knelt down and sucked my dick in her mouth as she had me lift each leg and step into the silk panties. As my dick stiffened, she let it slide out of her mouth and she slid the panties up my hairless legs. By the time she had them pulled up to my waist, my dick was fully erect and she kept rubbing it through the silk panties.

"Jack, you are not going to be able to finish getting dressed if your clit keeps sticking out so lewdly! Do I have to get out my tape and make you flat again?"

"Sarah, quite playing with my dick and let me get dressed! You're going to make me late!"

Sarah released ma and I put on my undershirt and dress shirt while I let my dick go down. By the time I had on my socks, shirt and tie on, I was down to normal and could put on my pants. I headed to the kitchen for breakfast while Sarah finished getting dressed.

We headed in to the office, but I had to have Sarah drive so I could sit on my hip instead of on my butt cheeks. The Client presentation went very well, and I just stood up to address the Client team as we went through our materials. They were impressed with the work our team produced and we won the project.

The senior managers planned to take the team out for a quick celebration after work, so I could not cut out early. All day I could not sit still because my ass was so raw. When people asked me why I was stirring around like a cat on a hot tin roof, I just said that I was excited by the big win on our Client proposal.

When we got to the bar for post work celebration, I just kept on my feet and made my rounds to all the team members, congratulating each one. As the project team started home, I looked around for Sarah, but she was no where to be found.

"Oh Jack, Sarah went ahead. Her friend Lori came and picked her up 30 minutes ago and she asked me to tell you to just come home when thing wound down here." our friend Pat told me.

A few minutes later I was on the road home and it was the most uncomfortable drive of my life. If a cop had seen me twitching around in the car seat I am sure I would have been stopped. Luckily I made it home without incidence.

"Sarah I'm home, where are you?"

"I'm back in the bedroom Jack, come on back I have a surprise for you."

I went back to the bedroom and on the bed was over a dozen silk panties and just as many silk tank tops.

"I got rid of all your ugly old rough underwear and got you new things! Aren't your excited!"

I was excited all right, but I was also terrified at the same time.

"I can't go around in that stuff all the time Sarah! It is OK when we are home, but I can't change in a locker room or go to the doctor in that stuff!"

"Not to worry Jack, I got you a few pair of men's silk boxers and you can wear them when you have to do some manly ting!"

Sarah had covered all the bases in her mind. I was not sure whether I was more excited or scared by the new cloths.

"Come on Jack, get out of your suit and into your robe so we can eat dinner and relax."

I got out of my suit but left the panties on. When I went for my terry robe it was gone and a new silk robe was in its place.

"Sarah, where is my robe?"

"I got you a new one Jack, besides the old one was worn out."

I slipped on the robe and went out to eat. Sarah had candles light and a nice light dinner all set on the table. As she handed me a glass of wine she made a toast.

"Welcome to the world, Sissy Jacquelyn!"

We toasted and sat down to eat. Or at least Sarah sat, I kept shifting around to try and find a spot that didn't hurt on my bottom. After we finished eating and cleaning up, we went back to the bedroom to relax and watch a little TV and share the rest of the wine. We enjoyed an old movie together and when it was over it was time for sleep.

"Jack, I want you to save all your sperm for this weekend, so I need to keep you from playing with yourself before Friday. I am going to put you in the cuffs each night this week to make sure that by the weekend you have a full load for me and I purchased a new chastity trainer for you."

Sarah had me stand and she took out a strange looking leather belt. She had me take off my panties and step through the leg straps. As she pulled it up I could see how it worked. It was like a jock strap, that had a flat leather front with a hole and a steel ring where my dick was located. She pulled it up and pulled my flaccid dick and balls through the ring, and then she pulled the center strap back between my legs. After buckling the wide belt tightly around my waist, she was ready to hook the divider strap in the back.

"I almost forgot the best part Jack, bend over and grab your ankles!"

Sarah worked some lube into my ass and started pushing a plug in. It slipped in much easier after the workout yesterday and she pulled the divider strap tight to hold it in place. When I stood again, Sarah hooked each wrist cuff to a D ring on the side of the belt.

"Now you can't play with yourself, and I can stretch your cunt all night! I have a whole set of plugs to work you up to Frank's dick size. Very soon, you will be able to take a good ass fucking like a true sissy slut!"

Sarah had me lie down with her and she kissed me, played with my nipples and rubbed my cock until it was hard. The steel ring was sized so that my dick could harden, but the blood was now partly trapped in my erection by the steel ring. I was at Sarah's mercy. Plug up my bottom, dick trapped in a steel cock ring and Sarah making me horny.

"You are so hot Jacquelyn, I have to fuck you!"

Sarah put me on my back and sat on my face. I was desperate for relief, and I ate her cunt like a madman. Sarah rode my face to 3 orgasms and then collapsed on my chest. After she got her breath back, she got out 3 condoms and rolled them on my hard dick. She had picked the size of the steel ring perfectly. It helped trap blood in my dick to keep my erection very full, but it was not so small that my dick was turning purple. I could wear the belt for hours without damage to my cock!

"I need to get my cunt filled up Sissy Jacquelyn, but your don't have a real cock to do the job, so I am going to have to use your fake cock for my pleasure! I don't like the feel of plastic or latex in my cunt as much as real cock flesh, but this is the best we can do for now!"

Sarah slid her wet cunt on my pole, but with all the condoms on I could not get enough stimulation for any pleasure of my own. Sarah rode me till she had a huge explosion after many small orgasms. As she fucked herself crazy on my "numb" cock, she was forcing my raw ass down on the bed and each time she pushed it down, I tried to push my ass off the bed just as hard, the result was the hardest fucking Sarah had ever received. I had no idea how many times she climaxed, but I could feel her cunt juice running out of her and all over by legs. I sure hoped the leather chastity trainer was of very good quality if it was going to handle all this wetness.

When Sarah was done, she took off the condoms and inspected them for cum.

"Good, you did not lose a load! You are going to be good and horny by the weekend!"

As Sarah curled up and lay her head on my shoulder, I drifted off to sleep with no hope of getting at my dick to masturbate.

The rest of the week went much the same, I dressed in my new silk things each day and slept in my chastity trainer at night. Sarah had me eat her cunt to several orgasms each night and if her cunt was not sore, rode my latex covered dick to her biggest orgasms. She was completely satisfied each night and I was hopelessly horny! Each night she put in a bigger plug in my new cunt and said I was getting close to being a real fuck slut. It no longer pained me to receive the plug and it even felt strange to not be filled up during the day at work.

Thursday night Sarah had me do the hair removal cream again so I would be very smooth for the weekend. Friday morning I was getting dressed when Sarah held up a pair of fine silk hose.

"You need to start wearing hose under you slacks for work Jacquelyn." Sarah informed me.

"How am I going to hold them up all day Sarah?"

It didn't even occur to me that I should refuse, I was molding more each day into Sarah's sex slave and it was only a question of how to comply, not if I would comply!

"Well Jacquelyn, I thought about having you wear a garter belt under you suit, but the straps might show. I don't thing you are ready for that much exposure in real life, so I came up with plan B. I have some special double sided adhesive tape that we are going to stick on your thighs at just the write height and when you pull up your stockings, they will hold tight."

With Sarah's help, we found the right location for the tape and put 4 2 in. by 3-in. pieces of the double sided tape on each leg. The stocking tops were rolled over the tape and pressed firmly in place. I was holding very tight and was still going to be invisible under my suit.

"If you get cold feet and try to take off the hose Jacquelyn, the tape will not re-stick and I will know! You better come home with the hose stuck tight tonight!"

Off to work we went on Friday with me in silk and hose under my suit. All day when I moved, I thought about sex and wanted to masturbate. There was no escaping from my chastity at work and I was getting desperate for release! At least my ass was no longer sore and I could sit comfortably during the day.

Friday night Sarah put me in the chastity trainer again and used the largest plug to fill up my cunt for the night.

"Well Sissy Jacquelyn that is my biggest training plug. The wide part is supposed to be as wide as Frank's dick, but the training width is a little less once it slides in all the way."

The widest part had been hard to slide in, but it didn't make me feel like the thing was going to rip me apart. If Frank's dick was that big, I think I could make it through the ass fucking. What was I thinking, I was not a "queer" and yet I was resolved to taking Frank's dick up my ass when Sarah wanted to make it happen. Sarah had me eat her to orgasm several times, but she didn't ride my latex covered dick so she would not get sore before the weekend.

I woke up Saturday morning more horny I have ever been before. Sarah had used me and teased me unmercifully all week and given me no release.

"Well Sissy Jacquelyn, now you are mine for the next two days to do what I will. You are to do everything I ask per the terms of our bet or you will get switched again. You will get switched as many times as necessary to keep you in line and following instructions without question! Is that perfectly clear Jacquelyn?"

"Yes Mistress Sarah, Sissy Jacquelyn understands."