The story so far:
Nick expected Holly to beg for forgiveness after discovering her affair. Instead, she coerced him into admitting he was a crossdresser. She dabbed the sherry sauce from their meal onto her pussy, forced him to lick up the creamy white liquid, then sent a video of him doing it to her boyfriend.
Chapter 2/27: A Disney Fairy Tale
I woke the next morning to the soft touch of Holly's finger on my hard cock. She kissed my lips, straddled me, and said, "I thought you'd never wake up."
I adjusted the pillow beneath my head and said, "Sometimes it's fun to play possum."
She laughed as she aligned her cunt with my cock, then slid down. As usual, her pussy was so wet that my cock slid in without a hint of resistance.
I said, "I love it when you're on top."
She rose up, then slid down. Once her weight was resting on my groin, she leaned over to feed me her tit, which I playfully kissed and sucked while we talked. She said, "We have a lot to do this morning before we pick up the girls."
"I didn't think we had any plans."
"We didn't, but we do now. We have to get some frilly clothes for our new little princess."
"Are you serious?"
She pulled up until my cock was about to vacate her pussy, then drove her hips back down. "Of course, dressing you up will be the most exciting thing that's happened between us for ages. Now that I know the truth about you, we are going to live it to the fullest."
"I'm still the same person."
"Yes, but now I know that person is a crossdresser."
I shook my head in silent despair.
"I think you should dress as a woman all the time."
"No. Please. I don't want the girls to know."
"So what if they find out? They'll learn that the great guy who's their father is also human. Is that so bad?"
"Well, yeah. Of course, it is. It would be nice if someone in this family had a little respect for me."
"I respect you."
"Are you sure about that?"
"I'm willing to accept you for the sissy that you are. You're the one who's having trouble with it." She impaled herself again, then said, "Now shut up and fuck me."
I pushed up with my hips to drive my stiff rod into the depths of her wet cunt, slid most of the way out, and then thrust up into her again. With each descent, she bore the whole of her weight down upon me. Then, without hesitation, she quickly pulled away, egging my hips upward and waiting for my cock to pierce her again.
I did the best I could to make it last, but Holly kept me perpetually off-balance. Her expression of affection always left room for doubt. She might praise me for how generous I had been, when I wanted to hear how sexy I was, or she might say that a night out had been sweet when I thought it had been exciting. At first, I thought it was due to some failing of mine, but I soon realized that it was more complicated than that.
Holly was a stunning woman who enjoyed a good fuck and knew how to do it. She'd had sex with ten times as many partners as I'd had, and she never hesitated to tell me about the length of the longest cock or the girth of the widest. She'd talk about how full they made her feel and how much she enjoyed that feeling. Afterward, she'd stroke my shoulder and say my cock was the prettiest, or the most agile, or some other half-compliment that made me feel like she was stretching to find something nice to say. It was like everything she said was all part of a grand scheme to keep me second-guessing myself. On some level, I knew I was a desirable mate. I might have even thought that she loved me, but I was continually trying to prove myself to her. That morning, with her on top of me, I desperately wanted to show her that I was a better lover than Dan. I tried to bore my steel-hard cock in and out of her for hours, but it wasn't five minutes before I'd shot my wad into her unsatisfied pussy.
She brushed the hair out of her face and lowered her tit into my mouth, encouraging me to suck and nip at the brown flesh of her breast while my cock softened. "Did you like that?" she asked.
I brushed off my disappointment in my own stamina and said, "Yes. I haven't woken up like that in a long time."
"I thought you'd like it. Sissies like to be on the bottom."
There was no arguing with her.
She said, "I have a present for you." as she walked up my body on her knees until her pussy was over my face. "Here you go, princess. Your first real cream pie." The lips of her pussy were stretched and moist. At her slit glistened a white glob of my cum. "Go ahead, sissy, it's all yours."
Even though I'd known it was going to happen, I was surprised by how effortlessly she'd worked me into the position I was now in. I couldn't move without her planting my cum on my mouth. There was no point in pretending I was above it, so I stretched my neck to lick the first glob of cum before it dripped.
"How does your seed taste when it's fresh from my cunt?"
"It's almost as good as your cream sauce." I licked her oozing cunt a second time.
She said, "I thought you'd like it. Sissies always like eating their cum." She let me lick her moist slit one more time, then said, "Okay, Baby. Now it's time for you to get it all." She lowered her hips down upon my face, briefly squeezed my head between her legs, and then began to twist back and forth while she rocked forward and back, driving her pussy hard into my mouth. As she did, I sucked and licked cum from her wet hole.
She sat with her pussy pressed firmly to my face as her hips slowly rocked to and fro. "This is where you like to be, isn't it, Baby? You love sucking my pussy. It's what you were born to do."
Once I'd taken the last drop of my cum, I rolled her over so that I could bring her pussy to a boil. She leaned back and spread her legs, giving me the freedom to touch her where and how I needed. Instead of telling me how good I made her feel or complimenting how well I knew her body, she said, "I'm so proud of you. You're such a good cum-eater." I responded by nipping at the tender flesh next to her clit. She reacted by pressing her fingertips into my scalp and thrusting her hips forward to hold my head in a tight bind. I slipped my finger into her cunt and flicked as I sucked at her clit. Her hips froze as her hands drew tight and her world stopped spinning for just an instant. She moaned softly, and then her body sank back into the mattress.
I cooled her pussy down with long slow licks and soft luxurious kisses. After a moment, she adjusted the pillow and then said, "Dan is going to be so happy to know that you will be eating his cum."
For some reason, the thought of Dan knowing that I would be licking up the residue of his sex from my wife's cunt got me excited. My cock swelled as I thought of his cock inside the pussy I was eating.
"Think about it, sweetie, you'll be dressed up like a little girl licking my lover's cum from my pussy. The pussy that his cock had pumped full with your willing consent."
Why did her degrading dirty talk get me so revved up?
Holly must have read my reaction through my mouth's contact with her pussy, because she kept going. "Whenever Dan comes inside me, he'll know that soon you'll be down there where his cock has just spewed its jizz to lick up every last drop. You'll see it in his eyes when the three of us are in the conference room. You'll think about it when you're out on the floor, making the money that he spends on dinner, jewelry, and hotel rooms where he fucks me. You'll know that you are the one making it all possible."
I was humiliated that the woman I loved would talk to me this way. I was embarrassed that I enjoyed hearing her do it, and I was petrified that she would be sharing it with my boss. But more than any of that, I was thoroughly aroused.
Holly's foot rubbed against my rigid cock. "Are you hard again?"
I paused for an instant and then tried to change the subject by nipping at her clitoral bud.
She was undaunted. "Your recharge has never been that quick before."
I tried to ignore her, but she lifted my head by the chin. "Baby, does the idea of licking Dan's cum make you hard?"
"I think it's that that you are going to tell him about it."
"Oh, I'm going to do more than tell him. We'll make a video of me coming home with soggy panties and you waiting on your knees wearing nothing more than a cock cage."
"You want to cage me?"
"Of course, I don't want you beating off while I'm with Dan."
I shook my head. "This just gets worse and worse."
She wrapped her hand around my rigid cock and said, "The little man doesn't think so. He likes what's happening." She stroked my cock and said, "Come on little hobbit. Let's give the princess a second breakfast." She rolled on top of me, adjusted her hips, and guided my cock back into her waiting vagina. She slid up and down my pole a few times and then continued telling her story. "You'll be so horny that you'll do anything for relief. You'll wait on your knees while I take a seat. I'll hold out a foot and demand that you suck my toes while I recount what I did with Dan. I'll tell you about the fancy restaurant where we ate, how much money he spent, and what gifts he gave me. I'll show you his bracelet on my wrist and his ring on my finger. I'll tell you how big his cock is and how full he makes me feel when it's inside of me, and all the while, your cock will be straining at the cage, and your tongue will be licking the soles of my feet."
She slid her drenched pussy up and down my rigid pole as she spoke. "I'll tell you that Dan is spectacular in bed. That he's got so much endurance that sometimes I wonder if he's ever going to come. He's not like you, who have to eat me to get me to come first so that we can sync up later. No. He just fucks me, on and on, for what seems like forever. It's fantastic."
I loathed hearing her speak of Dan's sexual prowess, and I desperately wanted to prove my worth to my wife. I pressed my cock up into her, making the most of what I had. Unfortunately, my pleading eyes and heavy breathing encouraged her to share more about her lover. "His apartment is amazing. It's the penthouse with everything. His hot tub has a built-in wet bar and a panoramic view of the city. It's his favorite place to take me."
She slid up and down my rigid erection a couple of times, then asked, "What do you think about that, cuckold? Do you wish you could be the man Dan is?"
I said, "I should have never told you..." but she cut me off.
"He might let you watch us someday. You'll sit on a bar stool wearing your lacy panties and feminine bra. He'll lean me over the edge of the tub and mount me from behind. Your feminine penis will throb as you watch my dangling tits sway against the city lights as he has his way with me."
I pulled my still-rigid cock from her excited pussy and said, "I can't handle this. It's too much."
"What's the matter, Baby?"
"Maybe you're right. I'll never be able to compete with Dan, so if you want to be with him, just go."
Holly must have realized that she'd pushed it too far. Her expression turned from tease to concern. "Hey, I never said that."
I exhaled. "Well, maybe not in so many words, but that's the point of your story. He's got the money, the cock, the stamina. He's got everything, and I'm inadequate in every way. Why in the fuck are you still here with me?"
She gently fondled my humiliation-stiffened penis while she cooed into my ear, "Dan is a stud, but you are everything he isn't. You're supportive and kind. You are the one I come home to. You are the one who mends my wounds and minds my daughters. Dan could never be any of that. He is brash, impulsive, and proud. He's a fun night out and a great fuck, but you're the one I married."
"Maybe you made a mistake when you married me. You don't need a husband. You need a dog, a good loyal dog."
Holly laughed, "Why would I get a dog when I've got you?"
"That's fucking pathetic. I don't want to be your dog. I'm like you. I want more. I want someone who loves me for who I am, and I want to love her for who she is. I want my life to be the way it's supposed to be, where she is everything for me, and I am everything for her."
Holly calmly smiled as she shook her head. "Someone sold you a Disney fairytale when you were young. The truth is that fairy godmothers don't exist. Handsome princes don't rescue maidens from boring, sad lives, and no one can ever be everything to anyone. You have a choice. You can either cling to the fairytale and choose a small world where you settle for a stifling marriage to a woman who is every bit as unhappy as you are. Or you let go of the fantasy and open yourself up to a bigger world where you accept yourself for who you really are and accept your wife for who she is."
She grabbed my chin in her hand and forced me to look her in the eyes. "I'm offering you the second option, where you accept the fact that you are a crossdresser who likes to watch his wife get fucked by his boss. Where you can live as a crossdresser, who knows his wife needs him just as much as he needs her even though she gets something on the side."
"That just sounds like a different kind of fairytale. How am I supposed to know that you're not falling in love with Dan?"
"I do love Dan."
The blood drained from my face as the bottom fell out of my already frail emotions. Last night being Holly's cuckold had almost seemed exciting, but if she loved Dan, my hold on her was slippery at the very best.
Holly tried to recover. "But I don't want to marry him. I want to be married to you."
"What does being married to me mean when you love Dan, and you're living that bigger life with him, his hot tub, and his million-dollar view?"
"I don't know yet. You just have to have faith."
"Faith? A relationship based on faith?"
"No marriage can survive without faith."
"You're just selling me a different fairytale."
"Maybe, but in this fairytale, you don't have to pretend you're someone you're not. You can crossdress and know that I'll still be there for you. Just like I'll know that you'll be there for me."
I shook my head. I was no longer sure that either of us would be where we were needed.
She took my head in her hands, and earnestly looked me in the eyes. "Look. I've been married four times, and I've had more boyfriends than I can count, so it's not like I know what I'm doing, but I do know a lot of what doesn't work. Please try this with me. If it doesn't work, you can divorce me a few months later than you might have."
Well, at least she was being honest.
"Please, just give my way a try. Just for a little while. What do you have to lose?"
"I guess you're right. I mean, how much worse can it get?"
Holly laughed. "That sounds like the basis for a good relationship."
I took a deep breath.
She asked, "So, are you in?"
"That depends. What exactly do you want?"
"When we return to that conference room on Monday morning, I want you to tell Dan that you'll continue working for him."
I nodded. "I suppose I could do that for a month or two."
"And when I come home late, you'll share the excitement of the affair with me rather than being bound up with resentment."
"Shit. This is going to be hard. What do I get out of it?"
Holly smiled at me and said, "Let's go find out." She looked at the clock and said, "We've got to hurry, though. We have to pick up the girls at noon."