Cuckolds in High Heels

Your wife had invited her closest female friend over—she had told you to dress especially feminine for the occasion. You had noticed that their strap-on dildos were on the nightstands, and you had to entertain them both. It was the first time you had to be on all fours taking two dildos at the same time—few experiences can be more feminizing, but they both praised you a lot for being a good sissy.

Being caught out by your mother-in-law had consequences. Under the threat of telling your wife everything, she gradually feminized you more and more, started using her strap-on dildo on you, and turned you into an expert at licking pussy. Once you had become a perfect sissy, she introduced you to your wife dressed in a maid’s uniform and said, “I think you’re going to have to find a real man, if you don’t already have one—you can also use your sissy husband for your pleasure, but not in the ways we like best when we’re with a truly virile man.”

Your wife had told you that she was going to invite her lover over. The day he was going to come over for dinner, you were terribly anxious. In the early afternoon, she led you to your master bedroom and showed you what she wanted you to wear. After she had finished your total transformation, she said, “Sweetie, whenever my lover is over, you’ll be my friend Anne.” You wondered for how long she had known about your most secret longings—perhaps for very long.

MOTHER'S MAID

MOTHER'S MAID

Their wives are close friends; the two have worked hand in hand to mold them into extremely effeminate husbands—whom anyone would mistake for two beautiful, sexy, and ultra-feminine girls. They have learned to serve their wives as sissy-maids, to be attentive servants to their wives' lovers, and to be extremely skilled at cunnilingus—even at performing it simultaneously on either of their wives. They have also become very close; their wives have allowed them to have some sissy-to-sissy sex, but they almost always wear chastity belts—so that they lust after each other all the time without being able to relieve themselves. Being so frustrated, they are even more eager to sexually satisfy their wives in the ways effeminate husbands do. Who wouldn't want to come being kissed and licked by those lips and tongues?

You heard your mother-in-law whisper behind you, “It’s a very sissy lingerie set, isn’t it? My daughter would love to see you on it. Let me buy it for you.” You blushed deeply, not only because of what your mother-in-law had said, but mainly because you wanted to have and wear it.

MOTHER'S MAID

MOTHER'S MAID

Once their unmanly husbands have reached a high degree of feminization, it is quite common for wives to encourage them to begin having intimate contacts with other sissies under their strict supervision—few things can reinforce their effeminization as much as sissy-to-sissy sex. Once the sissies begin to seek it without being encouraged by their wives, imposing strict control on them becomes imperative. These two sissies have been talking about their wives and their wives’ virile lovers, and it led them to a state of almost uncontrollable sexual arousal. Their wives have been very far-sighted—their chastity cages will prevent them from even mutual masturbation and will remind them that it is their wives who are in charge, as it should always be.

You look utterly feminine and beautiful, sweetie! You look absolutely perfect for your first sissy-husband-swapping party. I can see how proud you are of it. You know I’m very close to Helen; when she told me that she would love to peg you, I knew that you had to look the best for her. She’ll be kind to you; reward her by being the most submissive sissy—the most eager to please all her sexual demands. Think of yourself as the most personal present of mine for Helen, and don’t embarrass me—be the most effeminate and classy sissy for her.

His wife is hosting a private sissy-husband swapping party—his wife has told him how to dress for the occasion. Jane, a close friend of his wife, has told him, “Sweetie, let us go upstairs to see your room.” He has noticed that she is holding a strap-on harness and dildo in her hand. It’s going to be his first time being pegged by a woman apart from his wife, but he likes Jane—she is beautiful and loving, though assertive—and he knows he is going to love fulfilling any of her sexual demands.

Truth be told, you no longer miss your sex life as a man. You realized long ago that nothing compares to those moments when you sit back in the armchair and watch your wife come as a well-endowed man’s cock fills her pussy, or those other times when your calves rest on her shoulders as she slowly and lovingly penetrates you with her strap-on, and also the occasions when you’re your wife’s lipstick lesbian, when you can cover her with kisses from her forehead to her toes, lingering as long as necessary on her breasts, her vulva, and her clitoris. Who cares if someone might say you’re effeminate and a cuckold—or that you’re your wife’s sissy maid.

Your fiancée was clear-cut: “Sweetie, whether you sleep with me as a sissy or in another bed because I’m having sex with another man, these are the clothes you’ll have to wear on our wedding night—Mom chose them for you.”

Sweetie, I'm planning a romantic 4-night escape with Mark—book an ocean-front suite at Maui and plane tickets for him and me. Now that you are my sissy cuckold assistant, it's part of your job.