Getting Nailed

5) My only option for fucking was to be penetration of Sarah or Lori in the ass. Frank could not have anal sex with the girls because of his big dick and in return for ruining Sarah's pussy for my small dick, I could fuck Lori in the ass with Frank's permission. It was fair they said, because Frank got both pussies and I got both assholes. Each of got what we could use best with our individual cocks.

5a) Frank would receive several blowjobs from me each month with Sarah's permission and in return, I would be allowed to cum in Sarah's ass an equal number of times. I would not get to climax more times than Sarah felt appropriate to maintain my motivation to serve as their sexual slave.

5b) Frank would have anal intercourse with me about once a month. That would give my ass time to recover and thus, maintain the tightness of my asshole for his pleasure. I would be encouraged to learn to cum from having my ass fucked by Frank as a second form of sexual release. In return for taking Frank's dick in my ass, I would get to fuck Lori in her ass an equal number of times. However, if I came from Frank fucking me in the ass, I would forfeit my penetration of Lori's ass (Frank's idea).

6) Frank was not homosexual and he would not touch me sexually in anyway, but if I liked being a sissy slut, he would go along with my humiliation.

7) To keep me motivated as a sex slave, I would continue my chastity training under Sarah's control. I would be kept sexually stimulated every day and denied sexual relief without permission. I would be given some sexual relief, but not enough to blunt my desire to serve as Sarah's sissy slave. My dick would be kept in the KTB device when I was out of Sarah's direct control and in the chastity trainer at night.

The discussion had my mind spinning as Lori kept teasing my little dick in my petticoats. I would have balls to maintain my sex drive and be denied my cock to obtain release. If the sultans had removed dicks instead of balls, their harem eunuchs would have gone mad, female pussy everywhere with an intact desire for sex and no chance for release without a cock. That was what they were purposing for me. I would become a dickless eunuch for Frank's pussy harem and my balls would keep me in a constant state of sexual frustration. Sarah would drive me mad with desire, use me as her pussy slave, cuckold me with Frank's big cock, end forever my fucking of a woman's pussy and give me a life of sexual humiliation with Frank and Lori's help.

Sarah again explained that if I said no, then none of us would ever speak about the agreement again.

"I think that the three of you get more out of this than I do!" I pointed out.

"You may be right, but I think we each get our needs met by this agreement. Lori gets oral sex and a gentle lover on top of Frank's big dick that she loves but wears her out. I get to fuck the big cock I always wanted and still get to have you perform oral sex on my pussy and asshole as much as I like. I like having you as my sissy sex slave. Frank gets enough pussy to satisfy his sexual overdrive and an occasional blowjob or anal sex from a sissy slut just like when he was in juvenile prison. Sissy Jacquelyn gets what she wants deep down.

I have watched you the last 16 days since our bet and you are perfect for this life. You get off on being forced to wear sissy clothes and you are completely turned on by the humiliation. You can almost cum from licking my pussy after Frank fucks my pussy and his cum slides past your lips. When I make you eat your own sperm after you cum, your cock stays hard and the look of lust on your face when I made you lick your own sperm off Frank's cock was priceless. You are into being Sissy Jacquelyn more that I thought possible, I believe it is your sexual destiny."

"If you end this tonight Jack, you will always know in your heart that you made a mistake. My pussy will recover a lot in a few weeks and I will be able to feel your little dick again, but you will have denied me the pleasure I need sexually. I was never completely satisfied with your little cock before and now I could never be satisfied with you after having a real man's cock like Frank's in my pussy. Your little dick is just that, little. It may be average compared to other men, but to me it is just inadequate and Frank has made it impossible for me to enjoy fucking you. Lori and Frank will go on having sex problems to the point that it could easily ruin their marriage and you can help save their marriage. You will have an itch that you can't reach if you kill Sissy Jacquelyn tonight and deny yourself a life as my sissy slut. Take it or leave it, but tonight you have to make your choice, Jack or Sissy Jacquelyn!"

After a few seconds I gave my answer...

Epilogue

I made my decision that night to live as Sissy Jacquelyn. It was a very hard decision for me to give up my wife's pussy to Frank's cock. I would never have normal sex with a woman again if we stayed with this relationship. My little dick was never going to be wrapped in warm, wet pussy again. I can almost cry if I think about it, so I don't unless Sarah makes me remember as part of keeping me sexually tense.

"Does Sissy Jacquelyn want to stick her little dick in my pussy? I bet you wish my pussy wasn't so stretched out and that you were still man enough to fuck your own wife! My pussy gets more dick than it needs from Frank's monster and I don't miss your little dick at all. I do miss the look of ecstasy you used to get when you slid your little cock into my hot pussy. Maybe I will let you have sex again someday, but I don't think it will be with me. I could bring home one of the divorced girls from work who won't know cock size any better than a teenager and let them have fun with your little dick. They would be happy for the attention and you would get to put your dick in a warm pussy again. No, that would never workout, you might decide to try going back to living as a man and I would not get to fuck Frank's dick anymore. I guess your little dick will just be a big clit on a sissy slut."

Sarah drives me crazy with lust when she talks about getting my dick into a warm wet pussy. I miss that feeling terribly and think about pussy constantly. I long for the feeling of my dick sliding in and out of Sarah's pussy, but don't want to give up serving as Sarah's sex slave just to get pussy. I have more sex than ever and I am kept constantly horny and respond to Sarah's sexual needs instantly. I lick her pussy as much as Sarah wants and that serves to make me desire her all the more. The sexual frustration builds for days and then I have the best orgasms of my life when I finally get to cum.

I can not cheat on Sarah even if I wanted too, she keeps my cock locked up all the time. The chastity trainer at night and the Kali's Teeth Bracelet (KTB) at work. If I start to get horny, the KTB devise painfully grips my cock and prevents me from obtaining an erection. I have a permanent case of "blue-balls" and I live to give sexual pleasure in the hope of obtaining my own climax. You can not imagine how crazy with lust you can get until your mistress takes away your cock. Sarah controls my erections and uses her sexual power to keep me focused on her pleasure. The silk cloths and forced feminization treatment by Sarah and Lori coupled with spending so much time licking pussy makes my sexual fulfillment the driving force in my life. Sarah makes sure that I always want more and that I remain motivated to serve.

Lori has made me several lacing corsets now and Sarah has decided to add diet and targeted exercises to my life. With Lori's tighter corsets and Sarah's diet and exercise plan, my body is taking on a more female shape. The have kept me in the corset so much that my stomach muscles are starting to lose strength and I feel a strain when I am out of the tight corset. They have my waist down nearly 4 inches now and Sarah thinks I will get down 1 or 2 more inches. I will soon have to start wearing a corset without breast cups under my business suit and male clothes for support.

Sarah had me purchase two small plungers for sinks (plumber's helpers) and remove the handles. She will make wear the suction cups on my tits for over an hour to stretch them out. Just before I remove the plungers, Sarah wraps twine tightly around the base of each pulled out tit so that they will protrude for several hours. When she has me take off the plungers, I have nice "A" cup breasts. The plungers leave a red ring around my little tits that won't fade for a day or more. The treatment makes my little nipples very hard and tender. The twine helps keeps my "tits" swelled out, but is not tight enough to cause damage. When Sarah finishes giving my tits a workout and removes the twine, my body will shake from the stimulation of the renewed blood flow.

A few weeks ago Sarah added suction tubes from an old snake bite kit. The small tubes have an opening about the size of a fingertip. I have spent hours with the devices attached to my nipples so they will stretch out for Sarah's amusement. Now my breasts and nipples are quite sensitive and I can hardly stand having to wear a starched dress shirt even with a silk undershirt.

Sarah wants me to be embarrassed to go without a shirt because of my developing tits and nipples, but does not want me to have hormone treatment. She wants my hormones to be 100% male so that my sexual frustration will be max. I have both nipples pierced and Sarah likes to play with the rings in my nipples to torture them along with the suction cup treatment. My nipples have grown enough that the nipple rings have been replaced 2 times.

Lori will lock my hands behind my back with the cuffs and remove the KTB from my dick so that it can get hard. Lori then licks and sucks my nipples until they are starting to get very sensitive. While she sucks on one nipple, she gently rolls and pulls the other nipple with her fingers. I get so turned on that I try to hump my dick against the air to find some direct stimulation and obtain some relief. Lori says that it is her goal to make me cum by just sucking my nipples. I think that she will soon reach her goal. When Lori is done sucking my nipples, she likes to hang a small bell from each nipple ring so that she can keep track of me when I am at her house.

Sarah is planning to have my dick tattooed with the words "Sarah's Slave" and "Sissy Jacquelyn" along the sides of my erect cock. She will take me to the tattoo parlor, put me in a cock ring so I can't get limp again and get me hard. She will have the words added to my dick so that I will always know my place as Sarah's sissy slave. It will show very nicely when I am erect, but will be unreadable when my little dick is flaccid. With the KTB device installed, nobody will read my tattoo without Sarah's permission, but anytime I am able to get an erection, everyone will know who owns me. Sarah is also thinking about having my dick pierced horizontally through the head. She will have a D-ring installed so she can attach a leash to the head of my dick. She thinks it would be great fun to cuff my hands behind my back and leash me to the foot of the bed while she fucks Frank. She can also pull my dick back between my legs and tie it to my corset when she want's a smooth line in my panties. It should be much faster than using the tape to hide my little dick. She thinks that such a piercing will take months to develop enough that she can use it with a leash.

The girls like to play "Barbie" with me and dress me up in all kinds of clothes. I have been made into everything from a pre-teen girl in short skirt and knee socks to a slut streetwalker who has on whorish makeup. I now do my own nails and makeup except for special occasions when Sarah takes me to Pauline's. Sarah likes to make me beg to lick her pussy after Frank fucks her and Lori likes me to lick her pussy before Frank fucks her and tongue fuck her ass after he has cum in her pussy and I have cleaned up that mess. I lick up every load of sperm Frank gives up when he fucks Sarah and about half of his loads deposited in Lori and I always eat every drop of sperm that I produce. Most of the time I am so horny that eating the sperm is just part of the experience. But, when I have just climaxed, having to eat Frank's sperm still makes me queasy. I have given up all my hobbies and spend all my non-work time being a sissy slut sex slave for Sarah, Frank and Lori.

Frank has gotten into humiliating me more than the girls do. It is now over five months since I became Sissy Jacquelyn permanently and I have not put my little dick into Lori's ass once in that time. Since I only get to fuck Lori when Frank fucks my ass and without me having a climax from his fucking, he has been able toy with me sexually. Frank's big dick has made me cum each time before he climaxes and I must wait the next 3 or 4 weeks before I get my next chance at Lori's ass. His big cock fills my ass completely and my prostate is stimulated to a point that I can't hold back my orgasm. He gets very excited making me beg to give him a blowjob so that I can earn a climax in Sarah's asshole. It is always humiliating, but I am kept in such a state of excitement that I beg for the humiliation with little prompting.

Frank tortures me for a week in advance of my ass reaming by not letting me give him a blowjob no matter how much I beg. He comes over to our house and fucks Sarah in my bed. I have to get Sarah ready for his big cock by licking her to several orgasms and then Frank has me suck his dick to prepare him for fucking Sarah. I beg Frank for a taste of his cock and I promise to make his dick feel good with my lips and long nails. I am very horny and I know if I can make Frank cum in my mouth, I get to fuck Sarah in the ass. Frank lets me bring him close and then he pulls out of my mouth.

"I can't believe how bad you are at sucking cock! If you were any good at giving blowjobs, you would make me cum in your mouth. Everybody knows that real men like blowjobs as much or better than pussy and you can't even make me cum in your mouth. I guess you just don't want to cum bad enough. Perhaps if you learned to give better blowjobs you would get to cum more often. I just can't pass up Sarah's sweet pussy for your poor effort at sucking my cock!"

My whole body was sexually charged and I get no release again that night. Frank then takes Sarah with his huge cock and has her describe for me how good it feels to have a real cock in her pussy. He cuckolds me in my own bed with me watching on my knees, hands cuffed behind my back and wishing I could suck cock better. When Frank finishes he gives one more chance to make him cum with my lips as I clean his sperm and Lori's pussy juice from his shaft. Frank pulls out of my mouth before he can get fully hard and tells me to do better in the future if I ever want to put my little dick in Sarah's bottom again. Frank goes home to fuck Lori and I spend the next hour or so licking Sarah's pussy and asshole. Sarah never lets me quit until there is no trace of Frank's sperm in her pussy. The whole time my dick remains flaccid in the KTB device.

Sarah's says that her pussy is ruined for small cocks like mine and her pussy is so stretched out that she has quit using tampons during her period. A few weeks ago, Sarah had me suck Frank to get him hard and then she had me make a mold of his big cock with this fast setting compound. Then she sent the mold off to a small plastic shop that makes sex toys as one of their product lines. Sarah has received back an assortment of dildos, which are perfect replicas of Frank's cock. The various versions of Frank's dick are a constant reminder to me of how much difference there is between our cocks. Sarah loves to hold the dildo up next to my dick when I am hard and ask me if I can deny her the pleasure of a real cock.

The one I hate the most is part of a mouth gag. One end is the head of Frank's cock and slips into my mouth. The part in my mouth is about 1/2 as long as Frank's real dick, but just as big around. The short end is held in my mouth and fastened like a ball-gag with a leather strap. The other end juts out from my lips with a complete replica of Frank's hard dick, all 10 or so inches. Sarah will make me fuck her pussy with this gag in my mouth. I give her pleasure as she talks about how small my own dick is and that it just won't fill her pussy up enough to give her pleasure. Now with my mouth dick I get to fuck her all night and practice licking Frank's dick at the same time to please Sarah.

I feel this terrible humiliation without end and my sexual needs builds a frenzied desire to give Sarah satisfaction. The smell of her pussy is all over my face as her juice flows out. She loves to have me lie down and she slides her pussy up and down until her pussy can't take anymore stimulation. When she is finished her pussy juice has run down the shaft of the fake dick and into my mouth and nose. I am overwhelmed with her pussy and I have not even been able to directly touch it. When she is satisfied, Sarah has me clean the dick gag with my mouth and put it away for my next humiliation.

The night of my ass reaming by Frank arrives after he has denied me sexual release for over a week. I report to Frank after giving myself enemas until my ass is perfectly clean. Only then can I go over to Frank and Lori's bedroom and serve as their sex slave. Frank has me use my mouth to get Lori ready and his dick hard. He then fucks Lori to a big climax with me watching while I kneel at the foot of the bed. When he pulls out, I must beg to clean his dick and get it hard for my ass fucking.

"Please Master Frank, let Sissy Jacquelyn lick your dick and make it hard so you can fuck my sissy cunt! Sissy Jacquelyn needs your cock in her ass badly because she is so horny! Please let me make your big dick hard again!"

After Frank thinks I have humiliated myself enough to earn his dick, he lets me use my mouth to clean his sperm off his cock.

When Frank is ready to go again, he gives me Sarah's key and lets me removes my KTB device. I get an erection immediately and put a condom on my small, hard dick to catch my sperm. I kneel between Lori's legs so I can lick her pussy while Frank fills my asshole with his cock. Frank's cum is running out of Lori's wide-open pussy and Frank is working my ass for all he is worth. After several days of having no release, I eat Lori's pussy like a madman. Frank's cum is draining out of her pussy very fast, but I drink it down like nectar.

I am now stretched to the point that Frank has only minor trouble getting his dick into my sissy asshole. Frank has denied me climax for over a week while he and the girls have sexually tormented me. Frank has just cum in Lori's pussy and he has a very unfair advantage in our perverted race to see who will cum first. While Frank pumps his big dick into my ass, I rhythmically squeeze my asshole to give his dick the best ride I can. I am desperate to fuck Lori, but Frank seems determined to deny my access to Lori's asshole.

It is not much of a contest and Frank makes me cum very quickly with his big cock. During my ass fucking, Frank taunts me about being such a big sissy slut. When I start to cum, my asshole spasms wildly on Frank's cock and he picks up his pace to fuck my faster, which makes my dick spurt more sperm into the condom. Frank isn't done and he continues to fuck me for several minutes until he has his second climax. I continue to lick Lori's pussy as she pulls my mouth tightly to her pussy. By the time Frank is done, my asshole is ruined for several days and I won't be able to sit down comfortably for a week. Frank points out that I prefer to have my ass reamed over getting to fuck the lovely Lori.

"I can't believe you like to have your ass fucked so much that you can't wait long enough for your orgasm to earn a chance to put your little dick in Lori's beautiful ass. Lori was looking forward to having you fuck her, but you are undisciplined!"