Training A Sissy Cuckold (fiction)

I am an attractive single woman who enjoys cuckolding and humiliating submissive guys and training them for domestic and sexual servitude. Having a subservient beta male who worships the ground you walk on and who is completely supportive of your relationships with other men , while at the same time remaining chaste at all times himself , is an extremely satisfying lifestyle which most women , once experiencing it , will want to adopt permanantly. I advertise in the adult personals for exactly what I'm looking for and usually get more responses than I can answer. Although most of the time I will advertise for sissies , I also occasionally look for dominant men to punish and degrade whichever current sissy I'm using at the time. When I accept a sissy for training , I want complete obedience. He is given a list of all possible tasks he may be ordered to perform before we start dating , and must agree to do all of them prior to meeting me in person. These tasks include , but are not limited to: doing all my housework and laundry , as well as housework for anyone else I assign , whether they are friends or romantic interests. He must agree to be displayed in feminine attire , panties , lipstick , make up , a wig , etc. in front of anyone I choose to show him off to at any time , as well as in public if I desire. He must agree to serve me orally and serve anyone else I demand him to , and this means total body worship. I let him know that he will be required to perform my two favorite most degrading tasks: foot and anal worship - both for me and for my boyfriends. He may also be urinated on as well. He also has to be willing to take frequent beatings , which can often be expected to be severe . At least , I try to make sure they're severe ! When I advertise for a dominant guy , I specifically request a tall , strong well muscled stud - not just for me but because a well built guy is more likely to be able to administer a really good flogging to my sissy's backside. I look for guys who have a mean streak in them ; a cruel man with a strong arm is well worth the effort it takes to find . After just a couple of meetings between the two men and myself , my sissy cuckold slave will actually fear my stud boyfriend ! Believe me when I tell you , when you're dating two guys at the same time , you want one of them to be completely cowed by the other ; it's an unbelievable turn on.
Last Friday , I introduced my latest stud , Michael , to "Joanne" , my current sissy cuckold.  Joanne got there first , to clean up and get everything ready. I arrived a short while later , and  ordered Joanne , who was in her maid's apron , panties , wig and make up , to curtsey to each of us and then kneel and kiss our shoes. Joanne then served us drinks. After about half an hour , I announced that it was time for Joanne to receive his maintenance beating. I told Michael he needed to give it to him good because it had been quite some time since anyone had really tanned his hide , and that none of the guys I'd dated recently had flogged him as well as I would have preferred (I always tell my new boyfriends this - no matter how hard my sissy has been beaten previously). I ordered Joanne to go to the bedroom and fetch the large rattan cane. This is the heaviest one we have , and he looked rather frightened as he went down the hall. I always prefer my slaves to remain unrestrained while being beaten ; this makes it more entertaining. Invariably , he will try to move his bottom out of reach of the cane and make it more challenging for my boyfriend to wear out his backside. I ordered sissy to pull his panties down and get down on all fours. Then . as Michael got into position , sissy raised his butt as high as he could get it to give Michael a nice target. Michael took off his jacket , rolled up his shirt sleeves and began the wonderful process of thrashing my sissy slave's backside. He got into an easy , relaxed rhythm , raising the cane high in the air and then bringing it down good and hard across Joanne's waiting buttocks. It really was delightful for me ; watching this strong , capable man impose his will on my slave's bare bottom. After the first few strokes , Michael began hitting sissy even harder , grunting from the exertion as he swung the cane home. The loud cracking sound made by a bamboo cane in the hands of a skillful master when it makes contact with an exposed bottom is absolutely thrilling for me. Sissy started breaking down , crawling slowly away , not wanting to incur my anger but needing to lessen the impact of the blows. I got my small 30 inch leather horsewhip off the mantel and got in front of Joanne to cut off his escape. Each time he shifted his bottom away from Michael , I moved in behind him to continue his punishment. When Joanne reached the wall , I used several well placed slashing cuts of my whip to herd him toward the corner , where Michael and I proceeded to just beat him silly. It ended up being one of the hardest floggings he's ever gotten - and believe me , he has gotten a lot of them. When he was crying and sobbing profusely , I had Michael stop for a moment so I could examine his bottom. It had been a good butt whipping session , but I still told Michael to give him six more of his best and hardest swings ; I generally like the skin on his bottom to be broken in at least two or three places - this helps ensure he'll remember the beating for awhile.
Having finally gotten his bottom to the ideal red , welted and slightly bleeding state I like to have it , I sat down on the couch with Michael and ordered Joanne to service our feet. He starts by removing our shoes , then massages our feet with lotion , then I have him lie on his back so my boyfriend and I can place our feet on his face. I love to cuddle and make out with my boyfriend while my sissy is beneath us licking and kissing the soles of our feet. If you've never tried this , I highly recommend it , it's absolutely exhilarating , and great for relieving tension and stress after a long day. I always have him worship my and my boyfriend's feet for at least 45 minutes to an hour.  I'll tell him provide personal attention "One through Twenty" ; this means he is to service each toe individually , gently sucking on them one at a time , kissing up and down the length of the toe and washing between our toes with his tongue.  I kissed Michael passionately and rubbed his **** as sissy continued to cover our feet with wet , slobbering kisses. God it was fantastic ! My stud boyfriend and I luxuriated in sissy making love to our feet for over an hour while I played with his big ****.  I was getting really horny and I wanted Michael to **** me. We went to the bedroom and I lay on my back for him to penetrate me. Once he was completely inside me , I ordered Joanne to get between my boyfriend's butt cheeks and lick his ******* while we ******. Any sissy of mine learns early on that one of his primary responsibilities is regularly service and pamper my boyfriend's feet and *******. This is a tremendously pleasurable position for lovemaking - being sumptuously screwed by a well hung stud with my sissy ******'s face between his butt cheeks , making passionate love to my boyfriend's butthole !  I'm very demanding in how I want sissy to french kiss my man's butt - I want him to use his lips to form a seal around the anus , sliding his tongue as far up the guy's ******* as possible when he's pulling out , then flatten his tongue out and create maximum friction against the walls of his rectum each time he plunges back in , massaging my stud's inner passageway with his taste buds to stimulate the sensitive nerve endings of his rectal lining. When this technique is applied properly , it drives my boyfriends crazy with pleasure and I can feel every pulsation of the guy's throbbing penis when he's coming inside me , his sphincter spasming and contracting on sissy's tongue as stream after glorious stream of his ***** spurts from his twitching , erupting prickhead against  the tender back wall of my bucking *****. I then cuddle with my boyfriend while sissy licks us both clean and then spends the next hour or so making love to both our feet , kissing and licking the soles and gently sucking our toes until we drift peacefully off to sleep. In the morning , sissy serves us breakfast in bed , once again using his lips and tongue to lavish his adoration on our feet while we enjoy our meal. Having an obedient sissy to present to my boyfriend is a powerful turn on for me ; it's also an ego boost for him knowing that his feet and ******* are the center of sissy's universe. Restricting sissy's sexual activity and only allowing him to serve my boyfriends keeps him focused on my lover's feet and *******. I take great pride in keeping sissy's mouth on my boyfriend's feet and his face up his butt as much as possible so he can have an intimate relationship with the love of his life - my boyfriend's butt !
billlewis billlewis
41-45, M
5 Responses Feb 23, 2012


He still did not answer the question?

U say your a female but your name billlewis shows a man, so what are u?

Anyone is meant to be more than you would allow. I feel sorry for you; lacking compassion.

who are you to judge?

Hello, I'm Jenny and my sissy is Bobby and he dresses 24/7. I caught him one day wearing my square dance petticoat and dress and now I make him wear the petticoat and a dress everyday at home, then make him wear capri's and girls tops when I take him shopping to humiliate him more.<br />
Just wondered what all you do to make fun of your new sissy?