Getting Nailed

When the hour was up my jaw ached. Sarah inspected the dildo carefully and proclaimed that I was indeed learning to be a good dick-licker.

"I have one more surprise for Sissy Jacquelyn to help her become the biggest sissy slut of all time. It is a device that will help you learn control of your big sissy clit. I am going to have you wear a device called a Kali's Teeth Bracelet or KTB for short."

The device was going to help me keep my erection from ruining the look of my silk dress when I was dressed up. Sarah described it as a positive feedback device. When she showed it to me, I was shocked by the cruel simplicity of the device. It was a steel ring that locked onto a flaccid dick and was lined with hundreds of very sharp points. Once I was locked into the KTB device any attempt to gain an erection would cause extreme discomfort.

Sarah went to the kitchen and returned with an ice pack to apply to my groin. Very quickly, my dick was flaccid and Sarah quickly locked my dick up for training. It is a very well designed device and once locked on properly, there was no to remove it without Sarah's help.

"The goal is for you to concentrate on my pleasure and not on your own little dick. This will help you pay attention to me and not to your own desire."

Sarah released me from the chastity trainer and lay on the bed and told me to give her a rub down to relax her and when she was ready for it, I was to lick her ass as long as it took to please her. I worked her muscles from her neck down to her toes and back several times. When Sarah was ready for ass worship, she slid a pillow under her pussy and told me to begin. As she lay there relaxed I started kissing her ass cheeks and eventually was licking her cleft and getting closer to her rosebud. Sarah was making little moaning sound and I began to tongue fuck her asshole. She was soon squirming on the bed and grinding her pussy into the pillow. I was getting very excited, but each time my dick tried to harden, the sharp teeth of the Kali's bracelet dug in and caused me to shrink again. When Sarah was satisfied, she rolled over and told me to give her a front side massage and when she was ready I could lick her pussy till she was satisfied.

It took over and hour before Sarah decided that she had enough. I lost track of how many orgasms she received from my hands and mouth. It was so sexy to watch my beautiful nails tracing Sarah's nipples and it was having a torturous effect on my dick. The whole time my dick wanted to harden, but could not because of the KTB device.

Sarah had me do my lipstick and made me up, dressed me in fresh silk panties and sexy hose attached to the garters of the corset and gave me a list of chores to perform. I worked off my list all day and whenever Sarah got to feeling horny again, I was commanded to lick her pussy or ass again while she talked about Frank's ability to satisfy her pussy. I was getting a supper workout sexually, but was unable to achieve an erection. Sarah was very satisfied and I was completely frustrated.

Late Sunday afternoon, Lori called and said she was ready for us to come over. I got dressed in my sweets and we went through the gate. Frank had just left to go to the gym and play basketball. The second we got to the bedroom, I knew Frank had just fucked Lori. After removing my sweets, Lori wanted a detailed inspection of the KTB device and a demonstration of it working. I made love to Lori and licked Frank's sperm from her pussy for an hour and not once did I even want to get hard due to the pain it caused my poor little dick.

"That little dick of yours is worthless now Sissy Jacquelyn! You can't even fuck Sarah if she gave you permission. If you were a real man, you would get hard from eating all this gorgeous pussy today and you have not had a single erection!"

We left before Frank got back and went back to our bedroom where I licked Sarah's ass and pussy to several orgasms. I was sent to make dinner and when I was done cleaning up after dinner, Sarah put me in the chastity trainer and removed the KTB.

"I can't leave it on at night, because you might get a sleep erection and hurt you little dickey. The purpose is to help you learn complete mental control of erections, not cause you damage."

I was put to bed for the night after licking Sarah to one more orgasm to see if I had learned control. I failed and gained an erection without permission. Sarah told me not to worry; it was my first day using the KTB. She said that I would soon be completely impotent without her permission to have an erection and that the only pleasure I was going to receive was from having my ass/cunt fucked. I thanked Mistress Sarah for the KTB gift and for all the training I had received this weekend!

Monday morning Sarah removed my corset and spent over 30 minutes removing my nails. When we finished Sarah took me to the bathroom to apply a special solvent and removed the breast forms from my chest. It felt weird to lose the weight from my chest after 2 days. I was getting quite used to having them on and their absence was a bit unsettling to my balance.

After getting showered under Sarah's supervision, I dressed in the silk panties selected for the day and put on a new pair of hose that Sarah gave me that had a lace top that was elastic and would hold themselves up. On the outside my business suit maintained my appearance. I was to wear panties and hose under my suit from now on and I had to have the Kali's Teeth Bracelet locked on my dick every day to keep me from getting an erection and masturbating at work. Sarah let me take out my earrings at work, but at night, I always put on earrings to keep my piercing open.

My weekly routine had me living two completely different existences. At work I was viewed as a professional man and at home I was a sissy slut. I was not sure anymore which was my natural state and which was role- playing.

This weekend was Frank and Lori's Halloween party, and all week Sarah talked about the surprise costume I would be wearing. I was afraid to guess what Sarah and Lori was cooking up. Sarah took every opportunity to tease me sexually and not only denied me release, she had denied me erections. My dick not only was inadequate compared to Frank's but it was now useless to me or Sarah locked in the KTB device. Each time my dick tried to harden, the KTB caused me so much pain that I quickly lost the erection.

Friday night came and Sarah told me how pleased she was about my training and she was going to put me in the chastity-training belt and release my dick from the KTB to see if I was ready to take control of my clit. To monitor my dick, Sarah took out a strip of 1-cent postage stamps and glued the stamps around my dick in a tight circle. If I became erect the stamp ring would tear and give proof positive that I had failed to control my dick. Sarah promised me an orgasm if I could remain in control of my little dick. I licked Sarah's rosebud and worshiped her ass for several small orgasms and one big climax.

When she checked my dick the stamps were not broken and so far I had kept from becoming erect. Next Sarah sat on the edge of the bed and had me kneel between her legs and start to worship her pussy. I licked her to several strong orgasms and I knew I was doing OK on controlling my little dick. Then Sarah started talking about fucking Frank and how good it felt to be filled up with a real dick. She talked about how tight her pussy was when he stuck it in her and how I could never satisfy her pussy with my little dick again. She said the best thing was when Frank had finished splitting her pussy wide open, I had licked his sperm right up like it was honey. I must be a real sissy slut to eat sperm so willingly!

When Sarah grabbed my hair and pulled my face into her pussy and locked her legs around my head and shuddered to a major climax I felt the delicate stamps tear. I was going to be frustrated sexually again tonight. Sarah encouraged me by saying that it had only been 1 week of training in the KTB and that I had made good progress. She concluded that I would need a lot more practice in the future to finally solve my dick control problem.

When Saturday morning arrived, Sarah had me remove all my body hair again, locked my dick in the KTB and let me know we were going to visit Lori to pick up my costume for the Halloween party tonight. We also had an appointment to have my hair, nails and makeup done at the beauty shop.

Lori put on my breast forms with the glue and laced me tightly in the corset. I went over to Lori's alone and she was waiting in bed with her legs up keeping her pussy filled with Frank's sperm. She gave me a gift- wrapped box for tonight and told me not to open until Sarah gave me permission.

I knelt between Lori's legs and cleaned Frank's sperm from her abused pussy. Her pussy was stretched more than ever and Lori told me that Frank had fucked her twice this morning. Frank got very excited by Lori recounting how I had tongue fucked her asshole last weekend and after he came the first time, he just kept fucking her as she talked about my oral service. The load was huge and it took me quite a well to lick it all up. When Lori was satisfied, I cleaned up my face and put on my lipstick before returning to Sarah.

This time my appointment was during regular hours and the shop was very busy with girls getting fixed up for parties tonight. Sarah had dressed me in a simple silk blouse that showed my nipples very well and a very short and tight skirt. I had to be careful not to let the skirt rise and show my stocking tops and garter. As I walked on my heels into the salon, all the women gave me dirty looks. Was I a she-male friend of the shop owner or was I just a slut.

With all the people getting worked on it took till 1:00 for me to get my hair, nails and makeup finished. The women working on me put me in a chair in the front window and positioned me so that people looking in the shop from the street could see my panties, garters and hose. I kept trying to pull the tiny skirt down, but with my nails being worked on, it was impossible to avoid the humiliation of strangers staring up my skirt. When I was done, Sarah took me home and had me relax until it was time to get ready for Frank and Lori's party. About an hour before the party, Sarah gave me permission to open my costume package.

Inside was a black silk French Maid outfit including several stiff taffeta petticoats. Saran applied some makeup to the area where my breast forms were glued to my chest so I would have better appearance with the low neckline and started helping me get into costume.

First, she slid on crotch-less panties that were a black silk with stiff red lace sewn on them. Next I put on black hose and attached them to the garters on my corset. Then the very stiff taffeta petticoats and finally the very short maid dress. It was so tight that it took Sarah about 5 minutes to get it zipped up. With all the stiff petticoats, the very short skirt didn't even cover my whole ass. If I bent over, my asshole, dick and balls would be visible through the slit of the crotch-less panties. For the final effect, Sarah gave me permission to get hard and she licked my dick a few times. I was so horny that I got a full erection almost instantly. Sarah took out a satin hair ribbon and tied a snug bow around my dick and balls.

Sarah had me lift my skirt up and turn around in front of the mirror. My erect dick and balls stuck lewdly out from my body and the stiff taffeta petticoat was the only thing keeping my erection from view. The ribbon was going to keep the blood trapped in my cock and I was very horny from the sexual denial this week.

Sarah put me in black high-heels and had me walk around to practice before we left for Frank and Lori's. The costume had a nasty surprise for me. As I walked, my dick swung back and forth rubbing the head in the folds of the stiff taffeta petticoats. I was getting my dick rubbed for the first time in almost 2 weeks and it would keep me hard all night. Sarah smiled as I recognized that this was part of her and Lori's plan.

"One last touch for your costume Sissy Jacquelyn!"

Sarah rolled a bright red condom on my dick and told me that it was to keep me from dripping pre-cum all over Lori's house as I walked around. If I sat down or bent over during the evening, the whole party would notice my red erection bobbing around.

Sarah went to change into the long silk Geisha Girl dress and when she was ready, we went over to join the party.

There was no pretext of hiding my identity tonight. Lori and Sarah drug me around to everyone to meet and they even told people to call me Jacquelyn tonight. The men made jokes about what a wimp I was to let the girls play "Barbie" with me. The women told me how much fun it must be for me to get to wear such a sexy costume. As people got a little drunk, I was also getting groped my men and women. Lori asked me to help her serve drinks and handed me a big tray with wineglasses on it. I had to go around the room and serve the wine in my French Maid outfit to people sitting in the low furniture. If I bent down, my ass would hang out completely, so I just kept my back straight and lowered myself by bending at my knees.

The word got out among the women that I was somewhat naked in my petticoats and they started brushing up to my erection at every opportunity. One good friend of Lori's who had just gotten divorced reached under my skirt and stroked my dick as I held the tray of wineglasses for her. Nobody but me knew that she was stroking my dick under my skirt. The whole time that she was playing with my dick, she was looking me in the eye and telling me how much I must like being a French Maid, because it was obviously very sexy for me. She said that she was just going to ask Sarah to loan me to her the next time she needed to "entertain". After that, many of the women found a way to give my cock a squeeze and make some humiliating remark. I was terribly horny and all the stimulation of my dick was driving me crazy with lust.

At last the party was over and I had won the best costume prize, a "Victoria's Secrets" gift certificate. Frank said that since I was a French Maid, I could clean up the party mess while he and the girls relaxed. When I finished picking up, I came back to Sarah's side.

"Jacquelyn we have been telling Frank a little about your costume and how much sexual teasing you have gotten lately. I also told Frank that you obviously know he fucked my pussy last weekend since we outed you as Jacquelyn tonight and that Lori and I felt that you should get to fuck his wife in fairness. Frank refused, because he said Lori's pussy is for him only. Besides after fucking Frank so many times, your much smaller dick would not give Lori much pleasure if any. Anyway, Lori suggested that since she has never had anal sex and never could with Frank, that perhaps she could let you fuck her in the ass.

I stood there open mouthed as they chatted on about all the options they had considered that would be fair and acceptable to all. Frank had a couple of additional requests. First, he wanted to see me make lesbian love to Lori like last weekend and second, If I got to take Lori's anal virginity and if I was going to enjoy something that he never would, he wanted an equivalent gift from me. He wanted to take me in the ass, since with his big dick he had not had anal sex with anyone since he left the juvenile reform prison. Lori then said that she wasn't going to be left out of our orgy and that if Frank got hard again watching me make love to Lori, she wanted me to ask him use his big cock on her pussy again.

It was up to me they said. But with one catch. Sarah said that if I wanted to cum tonight, it was going to be in Lori's ass, take it or leave it. I was so horny that I had no choice. I accepted the terms and we got started.

"Get your sissy ass over here and make my dick hard again with your lips and those sexy nails." Frank commanded.

I did as ordered and removed Franks pants and knelt down to start playing with his cock and balls. He was very excited by the scene and I had him erect in a matter of seconds.

"You better get my dick very wet or I might rip your ass bad when I fuck you Jacquelyn!"

I was sure that Sarah would let me use lubricant, but the threat insured that I used my mouth well to lick Frank's huge shaft and prepare him for fucking my ass. Sarah had opened my up a lot with the dildo training, but Frank's cock was going to hurt a lot if I didn't have plenty of lube!

Frank said he was ready to take me in the ass and Sarah helped me remove my maid dress and petticoats. I was still in my corset; hose and crotch-less panties as Sarah helped me get ready for my first real dick. Lori and Sarah had already gotten out of their dresses and were stroking their pussies through their panties as they prepared to watch the show. After lubing my asshole and Frank's dick I got on my knees for Frank.

"He will probably make a lot of noise, so we need to find a way to keep him quit!"

It was decided that I would kneel between Sarah's legs and eat her pussy while Frank took my anal cherry. That way if I made any sound it would get MUFFLED. (They all laughed at Sarah's pun.)

I got into position and as I licked Sarah's pussy, Frank pressed the head of his dick against my asshole. I could not believe how hard he was pushing and the head of his dick was not going in. Lori sat on my back and pulled my ass cheeks apart and Frank started pushing again. This time the head popped in and I screamed into Sarah's pussy. When I screamed, Sarah shook with a small orgasm. Lori slapped her hand down hard on my ass and told me to be quite. Frank started rocking back and forth to open me up and soon I was sure that I would die from his monster cock. Each time I made a loud sound, Lori spanked my ass and Sarah pulled my face tighter into her pussy. Frank started rocking back and forward a little faster and each time he pushed his dick into me, my mouth pushed into Sarah's pussy. In about 5 minutes, Frank had me opened up enough to get 1/2 of his cock in me. I was in major pain and almost sobbing as he had his way with my ass.

"Spank his ass Lori if he doesn't shut up his blubbering!" Frank commanded.

We settled into a rhythm, Frank slowly stroking in me deeper each time, shoving my mouth into Sarah's pussy and Lori spanking my ass in time to Frank's withdrawal. I was completely humiliated and turned on at the same time. I was licking Sarah's pretty pussy and getting fucked like a queer at the same time. When I felt Frank bury himself to the hilt for the first time, I moaned loudly and Sarah's body was shaking with orgasm after orgasm. Then the fucking started in earnest. Frank was pounding away faster and faster, Lori was spanking my ass as hard as she could and Sarah was coming so much that I could not lick up all her pussy juice. Very quickly Frank moaned and started bucking his hips and coming up my ass.

"Oh God, your ass is so tight, Oh God, it feels so good on my dick, Oh..."

Frank shoved in as hard as he could and held his dick in as he came down from his orgasm. We were locked up like a pair of dogs. My ass was clamping tight on his dick after the abuse and as soon as he quit working his dick in and out, we locked up. It took several minutes for some of the blood to leave his dick and as he shrunk slightly he pulled out of my. I was so open, that my asshole would not close completely when he withdrew. I was very turned on. My dick was throbbing, but the pain had been too much for me to cum.

"That was fantastic Jacquelyn! What a tight fuck you are!"

I was sent to the bathroom to clean up my ass and to bring back a damp cloth to clean up Frank's dick. I sat on the toilet and let Frank's cum run out of my ass. My asshole was still wide open and it took several minutes of clinching my ass muscles to get it to close again. At least Frank had not broken my ass permanently with his big cock.