Advanced Cuckolding

[ This is an original fantasy story, a continuation of the Cuckold Initiation story. Please attribute properly. ]

It’s been about 6 months now since my wife and her boyfriend Richard initiated me as her cuckolded husband. I have written previously about that experience.

Two months ago Richard moved in with us. He has taken over many of the things which used to be “mine”, the most significant of course being my wife. He’s moved into the master bedroom with her. They now share the closet we used to share for our clothes, and he now uses the dressers and nightstand that I used to use. And of course he sleeps each night with my wife in the bed she and I used to share.

But that’s only the beginning of the changes that have happened since I became her cuckold.

Richard makes more money that I did, so they had me quit my job. I now dress as a woman 24×7, and stay home to take care of the house, cook, clean, do their laundry and errands, and more. I even go shopping as a woman now. Fortunately I am very passable, and it’s never been a problem.

They’ve decided that I should have real breasts as well. One of them watches every morning to ensure that I ingest the hormone cocktail they found on-line, which is pretty rapidly reforming my body. My breasts have grown to nearly C-cups, my nipples hre substantially larger and more sensitive, and my body fat is redistributing.

I think my testicles are shrinking too, and I’m certain my cock doesn’t get hard as it used to. I used to really strain against my chastity device, and the spikes inside the cage used to really bit into my glans. But lately it just feels snug when I get aroused, and the spikes don’t seem to dig as deep. I suspect that the hormones will eventually make me impotent. My wife still talks about castrating me, and at this rate there won’t be any reason not to do so.

Richard sometimes likes rough sex, which my wife is not into at all. So they decided he could use me as his slut whore when he is feeling like he wants to get aggressive sexually. If work was particularly stressful, he will use me when he comes home, often forcefully face and/or throat fucking me until he cums. I’m learning to accept it.

At bedtime there are other little rituals they enjoy. If my wife doesn’t want to suck Richard hard, they make me do it. Other times they have me lay on my back and Richard sits on my chest and dangles his balls in my mouth. He likes it when I run my tongue around his scrotum while I suck gently on his hairy balls. It’s humiliating to watch my wife’s lips slide up and down his fine cock as I stimulate his manly balls to produce more cum.

Here is another rough ritual they both enjoy often. They tie my ankles to the foot of the bed corners, bend me forward, and truss my wrists to the corners at the top of the bed. If Richard does ties me up, he likes to make the bondage very tight. They put two thick foam pads under my waist to get my ass to just the right height for Richard’s cock. My genitals point down, so that as Richard fucks me I can feel his large manly balls slapping against my small, shrinking nuts.

My wife then lays on the bed with her legs spread and her pussy about a foot from my face. She plays with herself and masturbates while watching my face as Richard has his way with me. She like to smear her pussy juices under my nose, since her smell forces me to try to get hard. I’ve realized this conditions me to eroticize what happens afterwards. Richard steps behind me and spreads my ass cheeks far apart with his strong hands. In that moment I feel (and am) utterly helpless yet very turned on.

One of Richard’s favorite techniques is to put the tip of his cock right at my anus and move it in little circles. By his moans I suspect this really turns him on. During this time he expects me to hold my anus tightly closed. Then, without warning, he will plow his cock all the way into me. This usually makes me scream and start to cry.

My wife loves that part. Often she will encourage him to do it again. And again. He pulls completely out, and when he’s ready, slams balls-deep into me again. My wife usually brings herself to orgasm during this part while I’m screaming and crying. Sometimes Richard will make be beg for more, which is humiliating and degrading. I always comply, and feel like an utterly debased sex object, which is appropriate, since I am.

The intensity of the invasion that his thick, hard cock causes as he rams it past my tightened little asshole is impossible to describe. Once he’s done piledriving, then Richard will usually take his time fucking me, sometimes 20 minutes or more. He seems to enjoy calling me all sorts of names like his bitch, slut, whore, a wimp, pussy, and faggot. I end up craving his orgasm, since feeling his cum finally spraying inside me ends the anal onslaught. I always have to thank him afterwards.

Since Richard prefers that my anus remain tight to maximize his pleasure, they avoid using butt plugs or dildoes on me. My ass would probably hurt less afterwards, but I realize that Richard’s pleasure is more important. The one exception is our heavy metal plug, which Richard has me use for anal training. Every morning I do my “exercises” which involves tightening my sphincter to hold it inside as long as possible. I have to chart my reps and durations so they can monitor my progress.

Richard also doesn’t like to use much lube. In fact, just a little of his spit, whatever is left after it runs down my ass crack, is usually all he uses. He doesn’t like it too slippery, the friction arouses him more. The result, however, is that my anus ends up pretty raw and sore. That’s another reason why I cry while he rapes me, but his pleasure comes before mine.

Sometimes they have me sleep in what they call the Slave’s Room, which is my bedroom. Sometimes they tie me up for the night just for fun, sometimes not. For punishment they will make me drink lots of water (or their pee) before bed, or even make me administer one (or more) enema solutions to myself. I have to put on a diaper and plastic pants — my bed already has a waterproof mattress cover. After a night of bondage in my own waste, I usually have learned a valuable lesson.

Most nights I am fortunate enough to join them in the master bedroom. There is a mat on the floor at the foot of their bed. A padlock is used to lock my chastity device to a short chain at the foot of the bed. So literally, my cock is chained to the foot of the bed that my wife shares with her lover. Richard had me install buttons for the two of them which release a retracting key for the padlock. In that way they let me unlock myself to do things for them after they’ve gone to bed.

One of these night-time chores is being their urinal. They don’t have to get out of bed, walk through the cold house all the way down the hall, just to use the toilet. I save them the trip and pee on their behalf later. I’ve found that I prefer to drink their night piss, since morning urine has a much stronger and less desirable taste and smell.

When Richard wants to pee, he will sit up on the end of the bed and I put slippers on his feet. Then I get between his legs and he puts his limp cock in my mouth. He’s trained me to guzzle properly. I swallow 10 times, then he stops his stream so I can take a breath. This repeats until his bladder is empty. I then relock myself at the foot of the bed. I’m not allowed to wake them to use the bathroom myself nor wear diapers in the master bedroom. So some nights I don’t get much sleep because my bladder is so very full. They insist this is good training, and that my bladder will enlarge so it can hold and more more over time.

Of course they make love while I’m chained to the bed. At least twice a week I get to hear them enjoying each others bodies while they completely ignore me. I’m so happy that Richard is able to provide so much pleasure to my wife. It is music to my ears to hear her enjoy his attentions, and to orgasm thanks to his cock, hands, tongue, or whatever. It’s so important to me that she be sexually satisfied.

During the days, Richard sometimes has me do favors for him with some of his work clients. Typically this involves me delivering some paperwork to a client at their hotel, as they are usually from out of town. Richard sets it up so that about half the time they are expecting me to give them a blow job as well. I don’t know when Richard has or hasn’t told the client, but my orders are to ensure they are fully satisfied.

During the days, Richard sometimes has me do favors for him with some of his work clients. Typically this involves me delivering some paperwork to a client at their hotel, as they are usually from out of town. Richard sets it up so that about
half the time they are expecting me to give them a blow job as well. I don’t know when Richard has or hasn’t told the client, but my orders are to ensure they are fully satisfied.

It’s an interesting predicament. I can’t risk them not using me for their pleasure, since they might expect it. I’ll be punished if they didn’t “get some”. But they tend to be cautious so it’s impossible for me to tell who knows and who doesn’t. I end up awkwardly letting them know that I “want them to be fully satisfied with my services”. They usually take the hint, and before long their cum is trickling down my throat. A few have gone further and forcably raped my ass, but I don’t dare say anything. I bring a sanitary pad just in case so that, as I’m driving home, their cum running out my behind doesn’t mess up my clothes or the car.

Richard and my wife entertain in our house too. Sometimes I am just a vanilla maid; no one seems to really notice. For their sex parties they outfit me in various embarrassing ways in order to ridicule me as the sissy, chaste, cuckold husband of the hostess. One time I had to serve the guests all night dressed as a baby, wearing ten diapers at once, a bonnet, and pacifier. I was required to suck on a baby bottle that they kept refilling with their piss. All their guests are free to use me as they wish during their sex parties.

The good news is that my wife has wonderful sex with Richard. They make love several times a week, as far as I know, perhaps much more than that. They don’t hide it, in fact they prefer that I am aware. My wife makes use of me as her “cum dump”, letting Richard’s big loads run out of her pussy into my mouth. She much prefers this to “wasting it down the toilet” and having to walk to the bathroom herself. I always have to thank Richard for the privilege of swallowing his cum.

One Saturday they gave me a long list of household chores to complete. They were going out for a full day of shopping, eating out, driving around, and having fun. I had to wear my locking 4-inch heels with a short chain between my ankles, which was just long enough to permit me to use the stairs. My elbows were tied 18 inches apart behind my back. My wrists were locked to an 18-inch spreader bar in front of me, and that bar was chained to my locking collar. They took all the keys with them, so there was no chance for me to get unlocked.

Most chores were much, much more difficult in this bondage. I could sit to pee, of course, but could not reach to clean my ass (which explained the series of large enemas early in the morning). About noon Richard called to tell me a client was stopping by to drop off some papers for him. I was nervous as I opened the door for him, being tied up as I was. It wasn’t long before he had made me suck him hard and then brutally raped me. He seemed to really enjoy himself.

After he left I tried to catch up on my chores. I did not complete them all. Understandably, I was punished severely. Perhaps another time I will share the details of that extensive “corrective experience”.

My life has certainly been transformed. Looking back at my cuckold initiation, I was just a sissy, pantied, chaste, cuckold husband. Now I am also a maid, slave, whore, toilet, servant, cum-dump, sex toy, and she-male. I don’t dare predict
what they plan for me in the future, although things like eunich or transexual seem like possibilities.

A sissy can always dream.

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