Getting Nailed

Sarah had no plans to let me up just yet. She reached back and started stroking my cock.

"I don't think a sissy like you should have such a big clit. It will get in the way of all the pretty silk clothes Sissy Jacquelyn will get to wear. You are going to have to learn to control this thing or I will have to control it for you"

I didn't like the sound of that, but I needed to get to the bathroom.

"If you quit playing with my dick Sarah and let me take a piss, it will not be so big."

"Ok Jacquelyn, I will let you up if you promise to quit calling your clit a dick and do exactly what I say."

I agreed immediately and Sarah then laid out my first activities of the day: 1) I was to go to the bathroom and relieve my self by sitting like a sissy girl on the toilet and removing my tampon from by bottom. 2) I was to shave my face twice to get off my entire beard. 3) I was required to cover my entire body below my neck with hair removal cream for 20 minutes and let it remove any trace of my body hair. 4) I would then take a scented bath to soften my skin and after soaking for 15 minutes I had to rub my whole body down with her scented lotion. 5) After all that, I was to get dressed in whatever she lay out on the bed and then fix brunch for Mistress Sarah.

I quickly agreed and Sarah let up to get started. A little over an hour later, I returned to the bedroom and saw Sarah sitting naked on the bed stroking her pussy slowly.

"Get dressed Jacquelyn."

I was not sure I wanted to wear what Sarah had set out for me. There was a butt plug on the bed that I had never seen. It was way too big to go up my ass and it was going to hurt like hell to get it in.

"Sarah I can't put that thing up my ass!"

"Does Sissy Jacquelyn want me to help her prepare for her new friend?"

"No, please don't make me take that thing up my ass!"

"Well Jacquelyn, beg me to stretch you out so you can take you new friend in your sissy cunt. Besides, that plug is not as big as Frank's dick, so you better get used to it before Frank has his way with your sissy ass!"

I was stuck; begging Sarah for anal stretching would cost me now but save me pain later. It would also move me further toward the humiliation of having Frank stick his dick into some part of my body if Sarah was serious.

"Please Sarah, help Sissy Jacquelyn get her bottom stretched out for Frank's big dick."

Sarah made me beg for several minutes before she finally agreed to "help" me. She had me get up on the side of the bed and reach back and grab my ankles. Sarah then put the cuffs on my wrists and ankles so she could hook them together. The next thing I felt was Sarah working her fingers into my ass and loading lubricant into my sissy cunt. I was grateful for the lube, but could not take my mind off the plug she was planning to plant in my ass.

"Beg me to fuck your cunt Jacquelyn"

I begged like there was no tomorrow.

"Please fuck my cunt Sarah, Sissy Jacquelyn needs to have you stretch out her cunt for Frank's big dick"

Sarah soon obliged me and put on the strap-on harness with the dildo and started working it in and out of my ass. Sarah was already horny from playing with herself and it didn't take her long to work up to fucking my ass long and hard. I could hear her breathing hard and nearing an orgasm as my ass/cunt began to loosen up. As she worked her pelvis back in forth, the backside of the dildo was putting pressure on her clit and my bottom was starting to like the feeling of fullness. Back and forth she went slamming into my ass. My dick was getting hard as a steel rod and Sarah would reach around and stroke it once in a while.

"I want Sissy Jacquelyn to come for me when I fuck her bottom! If you don't come this way, I am not going to let you come at all!"

Sarah's words were driving me crazy. I had come so many times the last 2 days, there was not much chance of my getting off this way, but the more she worked that dildo in and out of my ass, the more I began to think I could come from ass fucking. Then I herd Sarah's orgasm and she collapsed on me driving in the dildo in deeper than I thought it would ever go and driving my hard dick into the bed. After a Sarah recovered from her thrashing of my bottom, she pulled out of me.

"Now Sissy Jacquelyn that is the biggest dildo we have now, so you are going to have to relax if I am going to get this plug into your cunt."

I tried to prepare my self for the plug, but I began to complain as she started working it into my ass.

"Now you better shut up Sissy Jacquelyn, or I am going to call Frank up right now and have him come over and open you up himself!"

I bit my lip, and pushed my face into the bed as my ass was stretched beyond anything I thought possible and them suddenly the plug slipped in.

"See, I knew that your sissy cunt would take the plug"

The shot of pain had taken my erection away and my balls just shriveled up inside me! Then I felt something very cool as Sarah rubbed alcohol on my dick, balls and the rest of my crotch.

"I told you I didn't want your clit sticking out so unladylike. You obviously can't control that thing, so I am going to help you learn control."

Sarah took a 3 inch roll of flesh colored surgical tape and cut off a six inch piece. My dick and balls had shriveled up from the pain and cold and Sarah quite easily pulled everything back and up into me with one hand and pressed the tape in place with the other. After a few minutes of effort my dick and balls were pushed up in my belly, Sarah had the effect she wanted and released the cuffs.

I looked down, and my sex was gone! Sarah had pressed the flesh colored tape in place so that my groin was smooth and flat. I didn't look like a man and I didn't look like a woman. I was more or less sexless!

"I like the new look! You need to quit relating to your clit as your sexual identity and learn to think of your cunt as your sexual organ! Then and only then will you get any sexual relief"

I didn't know what to say, but the only accessible area that could receive sexual stimulation was my asshole.

"Now you need to finish getting dressed Sissy Jacquelyn"

I looked at the rest of what Sarah had out for me to put on. It wasn't much, but it was all black, silky and sexy. I put on the hose quickly, pulled up the silk thong panties and added the garter belt. These were Sarah's best fancy hose with lace tops and seams up the back. I always got a hard-on watching Sarah put them on and the thought of Sarah's sexy legs in these very hose make my dick try and stiffen. There was no room for it to get hard and it just caused me pain. I took my mind off the silk and hose and my dick settled down a little. Next Sarah handed me a matching black silk camisole and held out her hand with a tube of lipstick.

"Sissy Jacquelyn needs to learn to put on her lipstick now." Sarah informed me.

I was starting to get into character by now and I just followed her over to the dressing table as she taught me how to put on the lipstick to make my lips look their sexiest. It took me about 10 tries to get it on to her satisfaction, but I finally got it.

"Ok Sissy Jacquelyn, quit primping and get to the kitchen to make brunch. Oh, don't forget to put on your shoes to keep from ruining your hose."

Sarah was holding a pair of black high-heeled bedroom slippers with a big poofy ball of lace on the arch strap. Sarah had picked them up at a garage sale a few weeks ago and I had told her at the time that they went out of style in the 50s and were not going to fit her feet. Now I remembered the smile on her face as she told me not to worry, that they would not got to waste.

I took the two slippers from her like they were dog turds.

"Hurry up Sissy Jacquelyn, I am very hungry and you need to get going on brunch."

I put on the slippers and tried walking to the kitchen. It took me several minutes to get the feel of walking in the high-heeled slippers and by then my arches and calf muscles started hurting. It took me a good 40 minutes to get our brunch fixed with me walking around on the heels and with the intruder up my bottom. The whole time Sarah sat reading the paper and sipping the coffee with that impish grin on her face. I started to set the table when Sarah made her dining preference known.

"Take it out to the sun porch Jacquelyn"

I was horrified, the sun porch was floor to ceiling windows and any neighbor who tried very hard could look in on us on the sun porch and if they had binoculars they would get quite a show.

"Please don't make me serve brunch on the sun porch!"

"Now stop complaining Sissy Jacquelyn, nobody is going to pay any attention to you so just get going"

Brunch was moved out to the sun porch and served. I was in a constant state of panic as we ate and only caught about half of Sarah's conversation. She was getting angry with this and told me to pay attention to her or I was going to regret it later.

She took the longest time eating and chatting about all the sales in the Sunday paper. Every sale she brought up was for lingerie. An hour of talking about sexy silk clothes was more than I could take, but Sarah did not let me see the sports page and always changed the conversation back to lingerie.

Finally we finished and she set me to cleaning up the food and dishes while she read the paper some more. I was told to report back to her when I was done in the kitchen.

"I am done in the kitchen Mistress Sarah." I said when I reported back.

"Good, now I want you to take down those two large hanging planters Jacquelyn."

I didn't know what she had in mind, but I was guessing that she planned to hang something else from the planter hooks. When I had them down and set where she wanted them, she sent me back to the bedroom to get the padded cuffs. When I returned Sarah pulled my hands up high with the cuffs and then pulled my legs well apart by tying them to the two heavy planters. I was tied spread-eagle with very little slack. My legs and feet were already sore from making brunch in the heels and they started hurting a lot more as I could only shift my weight a little bit.

"Sarah, please let me out of these heels!"

"No Sissy Jacquelyn, you need to learn to spend the entire day in heels. Those heels are not that high and when women go to work, they have to stay in their heels all day. How are you going to learn to be a good sissy without practice?"

I tried to quit complaining, but as I stood there watching her read the paper and sip her coffee, I started up again.

"My legs are killing me, please Mistress Sarah can you take off my heels?"

Sarah didn't say a word, just got up and left the sun porch. When she returned she had some things that were not going to make me any more comfortable.

"Open wide Sissy Jacquelyn. You might as well practice sucking on a cock while you practice standing on your heels."

When I hesitated, Sarah pinched my nose until I opened up to accept the dildo from her harness. It was bigger around than my cock and it made me open my mouth so far that it stretched my lips. Then Sarah took a long ribbon and wrapped it tightly around the base of the artificial cock several times, took the ends around my neck, crossed them behind me and then tied the ends off in front of my neck like a choker. I was now unable to complain about my position. Next Sarah took out her silk boudoir eye cover and tied it over my eyes to blind me.

"Now Sissy Jacquelyn can concentrate on learning to be on her feet all day in heels and practice her cock sucking at the same time!"

The next thing I felt was Sarah putting headphones on my head. She then started playing a tape recorded from a porno movie where a female voice begged to have her cunt filled with a big cock and then when I could hear the sounds of heavy fucking the woman started begging for a big cock for her mouth. After a while all I heard on the tape was the sounds of fucking, sucking and orgasm after orgasm.

In this state of deprived sensory input, I lost track of time. The tape went on and on with begging for big cocks and the sounds of fucking leading to screaming orgasm after orgasm. Then it would start over again. Suddenly I was startled to feel someone touch my skin. I was so sensitive to touch with all my hair removed and having been deprived of sight, the touch made me shudder all over. It was almost like an orgasm, but no one could even touch my imprisoned cock.

When I quite shaking, the hands started touching my body all over. Light touches and the feel of a ribbon being pulled around different parts of my body. It took a while for me to realize that the hands were taking my measurements. That was when someone started kissing my face and neck and rubbing my tits through the silk camisole.

There were two sets of hands on my body and I tried to scream, but the cock in my mouth kept me quite. I only got out muffled sounds and then I could hear giggling in the distance over the fucking sounds in the earphones.

The hands started rubbing me all over, stroking and rubbing. The measurements were all taken, but the hands kept me on edge while the tape played on. Then suddenly they left me and shut off the tape. I could hear their feet walking around me and to the front door. The door opened and shut and then footsteps back to the sun porch.

Sarah removed the earphones and blindfold and after a few seconds I quite blinking, I could see Sarah's beautiful face in the bright light on the porch.

"I let you figure out that someone else knows about Sissy Jacquelyn so later when I have you serve as my maid around visitors you will not resist. You have already been 'outed' and it is only a question of who I trust to share Sissy Jacquelyn with."

I must have looked like I had been shot.

"Do you understand Sissy Jacquelyn?"

I nodded my head yes.

"Now one more thing before I let you down and take off you nails. Last night when you spanked me, I had such a powerful climax that I want to return the favor to Sissy Jacquelyn. I am not as strong as you are, so I am going to use a switch on you instead of my hand. It is only fair that you receive the same level of spanking that I did."

I looked with shock as Sarah took a long switch she had cut from our willow tree. It was about 4 feet long and was as big as my finger at the base, tapering to fine tip at the end. I tried to say something in protest, but with the cock in my mouth I only got out grunts.

Sarah walked around my body flicking my legs, back and crotch with her switch. After about 3 trips around me she stopped and released my garters to pull down my panties. Then she refastened the garters.

"The garters form a perfect frame for your spanking. The top of the picture frame is the garter belt, the bottom is the top of your hose and the pulled down panties and the garter straps make up the sides of the frame. I am going to color in the white space inside the frame like a coloring book! Won't that be fun and artistic at the same time?!"

Sarah started on by hairless ass with the switch. I tried to scream out when the first blow landed, but the cock in my mouth kept me from making much of a noise. I think she gave that first swing her all. I could hear the switch whistling through the air as Sarah swung it against my bare ass. It was like an electric shock ran through my body. Then just about the time I could take a breath, the next blow came down. This time I think she backed off a little or else my skin was already in overload and the second blow did not have the same effect.

Then the switch began to strike every inch of my bare ass. First Sarah went from side to side as each arm tired and laid parallel lines across my ass. After a while, she switched to a bit of an angle to cover in the little white spaces between the red marks. I had long forgot about the pain in my legs and feet from the heels. Now my whole world was focused on my flaming hot ass.

"I do think your ass is a thing of beauty. I have colored in the whole area now and it is a wonderful shade of red. In fact, it is very close to the color of your lipstick! The only problem is the vertical white stripe in the middle."

Sarah then took the switch and struck me between my ass cheeks over and over until she was satisfied with the color of the flesh in my crack. The cock in my mouth kept me from scaring the neighbors. I have never felt a hot pain like that. The flesh in my ass crack was very thin and her blows with the switch were unbearable.

"Now your cunt lips are as red and pink as a real slut, don't you think Jacquelyn!"

I had no idea what my ass looked like but I knew how it felt! It was on fire! My face was streaked with tears from my switching. Sarah came around in front and started kissing my tears away as she rubbed her body against mine. She let her silk robe fall open and pressed her breasts against my chest, kissing me and rubbing me seductively. As she kissed me all over she started rubbing my tits and pinching my nipples. The camisole had ties for shoulder straps and she untied them and let the silk slide down to my waste. Now she started sucking and lightly biting my nipples. I don't know how long she worked on my nipples, but they were getting quite sensitive to her touch. Then she stopped and went behind me again. I now realized that my dick was throbbing under the tape. It could not get hard and was the tape made it painful, but I hadn't notice before because my ass was hurt so bad.

Sarah's hands reached around me and as she pushed her naked chest against my back, she pinched my right nipple to make it very hard. Then she placed a clothespin right on the tip of my nipple. The pain ran through me like a jolt and I started shaking again. My body was convulsing and twitching and I could feel my prostrate spasm. Then Sarah started pinching my left nipple and as she put a cloths pin on it she bit my neck and sucked hard to make a hickey. I had not had a hickey since I was a teenager, but I was getting the biggest hickey ever. Sarah was sucking on my neck like a vampire. Again my body was racked with spasms and my whole groin was twitching with sexual energy. My dick was trying to get hard, but the tape held tight and everything was kept pulled up into my abdomen. I was sexually charged and denied at the same time.

Sarah moved around in front and started removing the ribbon from my neck.

"I want to kiss you and feel your lipstick coated lips against mine!"

Sarah removed the cock from my mouth and after a few seconds I could close my mouth again.

"Pucker up Sissy Jacquelyn"

I had no resistance left and put my lips together for her to apply a fresh coat of lipstick. When she was satisfied, she stepped back and plucked the cloths pins off my nipples. A pain shot through my chest as the blood and feeling returned and as I opened my mouth to groan Sarah slammed her mouth against mine. She kissed me as though she was raping my mouth. I lost track of time as she kissed me and rubbed her tits against mine. I closed my eyes and floated into a trance.

"Owe!" I groaned into her mouth when she grabbed my red ass. As Sarah kissed me deeply, she began to rub her hands over my abused flesh. Over and over she stroked me until my hips started bucking and my body twitched all over. I nearly passed out from sensory overload and then Sarah stopped.

"I think you are close to learning how to climax without anybody touching your clit!"

Sarah was right, my dick was still trapped up inside of me and I had not even been able to get an erection. Yet, I had had several body convulsions that were stronger than the orgasms I enjoyed when Sarah and I fucked. I felt like my whole body was one sexual organ.

"Beg me to fuck you ass Sissy Jacquelyn!"

I was over the top and I started to beg to be fucked like the porno tape Sarah made me listen to.