Penelope

He loomed above her and slowly lowered himself until the tip of his cock was touching he vulva.

"Stick it in me," she said. "Make my Oscar our cuckold." She guided him into her very wet slit and gasped as he stretched her open opening more than it had ever been stretched.

"He will begin wearing his collar tomorrow,'" she said. He began slowly sawing in and out of her. She yelped a time or two when he forgot his promise to go slow. But, for the most part, she simply submitted to his male power.

******

I stood a few feet from my marital bed. Maria stared at me and smiled. "What?" I said.

"You okay?" said Maria.

"Yes, I think so. It's just it's been so long. But, this time; well, it feels right, well, okay anyway. I guess because I trust you and your husband. And, you, well, I know you," I said.

"I appreciate that," she said.

"So what now? What are we going to do until they call us?" I said. I was getting a bit nervous. She hadn't said anything, and I hadn't been given any kind of a heads up by Penelope either. She took a deep breath.

"We're going to get you ready for your part in tonight's activities.

"Oscar, Juan has made the request to; well, anyway. As you know, I told him no way if you were totally opposed to it. But, actually, he wants for us to go a bit farther than we had originally planned."

I took a deep breath, "Okay, what is it we are going to be doing." I said.

She went to the bed where a small box I'd not noticed till that moment was sitting.

"These are for you tonight. Juan wants you to be in drag when he takes you."

My eyes got big, "In drag!" I said. "Maria, I don't..."

"Oh, don't be silly, it'll add to the moment, the excitement. You'll get off on it if I'm any judge," she said, giggling. I sighed. I shuddered, but resigned myself to my fate.

"Okay, I guess," I said.

She took the box back to the bed and shook the contents out onto the covers.

Panties, bra, hair ribbon, breast forms (falsies), and another small box with no descriptive pictures or wording on it: he may have wanted me in drag, but not exactly dressed to the nines. My heart sank.

"It's going to be fine, Oscar. You'll see. But, we have to clean you up first and we don't have forever, so let's get moving okay?" she said.

"Okay, I guess," I said. It was humiliating and exciting at the same time. How Penelope would react when she saw me was the one variable that I wish I could control, but it was the one I had the least control over.

Maria had me strip naked and pulled me into the bathroom. Clean me up, she'd said. Well, I guess the bathroom was the place to do it.

Naked, she looked at my cock and giggled. You are tiny aren't you. But, for tonight's activities that'll be a plus," she said.

"Oscar, I'm going to shave you," she said as she was stripping herself. Let's get in the shower; it'll be easier in there.

She wet me down and then sprayed shaving cream all over my back. Taking one of the razors she'd brought into the shower with her, she proceeded to take care of my back.

The rest of my body got the same treatment. Twenty-minutes later there was nary a hair below my eyebrows. She dried me off and we went back into the bedroom where she took a seat on the edge of the bed and beckoned me to come to her by crooking her finger.

She picked up the small, nondescript box and held it in front of me. She smiled. It's your cock cage, Oscar. Only Penelope will have the key to the little lock that's going to imprison your privates from now on," she said. I swallowed hard and I knew my face showed fear, but as I stood there, I allowed her to slip the tube over my penis and attach the rings that encircled my scrotum.

"Ready, my friend?" she said. She was holding the small padlock up so I could see it."

"Ye—ye—yes," I said. She fitted it through the eyelet and snapped it shut.

"There," she said. "That ought to keep you horny enough for the next while." I had to allow that she was most likely correct.

She sensed that I was very nearly on the verge of a nervous breakdown. She decided to give me some good news to help me calm down.

"Oscar, Penelope and I talked long and hard about this, about denying you. She's of the opinion, and I concur, that you can't last six months without some relief. You need to be able to fuck her on occasion no matter what. But, that said, one of the big things underpinning a man being his wife's cuckold is her denying him intercourse. So, we came up with a solution," she said.

I was suddenly very interested in what she was saying. "Solution?"

"Yes. You can have Penelope any time you want. But, whenever you avail yourself of that freedom there will be a consequence. The following day you must willingly submit to serious punishment for availing yourself of her pussy."

"Huh?" I said.

"Yes, a major spanking: fifty spanks with a switch. A switch of a particularly cruel design." She walked to the closet and returned with a thin piece of wood, maybe three feet long and very nasty looking.

"Jesus!" I said. "She'll kill me with that thing," I said.

"No, as a matter of fact, it will not kill you. It's made of rattan. No, it's not lethal, but I can guarantee you that you will not be sitting down for a day or two after having gotten your just due from it," she said. "But, it is a way for you to have some control over your needs; I mean if you agree to accept the idea as a way for you to pay for them." I think I mouthed a very quiet okay; I'm not sure.

I thought that she was done with me and that she was going to take me downstairs to face my fate. I was wrong. There was a little more to do.

"Almost done now, Oscar. I need to do your face," she said.

"My face? My face?" I repeated.

"Yes, if you are going to allow him to fuck you, you need to feel as girlish as possible. Come here," she said seating herself at my wife's vanity. This final operation took a little time: eyes, lips, cheeks, and finally the perfume—my wife's favorite perfume, mine too if it came to that. Well, it was my favorite when it was on her.

"You know, I think you do need to wear a little something else besides your bra and panties," she said. She went into the walk-in closet and hunted. She emerged with a summer dress that Penelope loved and so did I. She slipped it over my shoulders and stepped back to appraise her work.

"Not too bad," she said. "If and when we do this again, we will take more time to plan and get it really right," she said, laughing.

"Anything else,' I said, showing a heightened level of exasperation. She took my hand and looked me in the eyes.

"No. Now we go down," she said. "Oscar, this is supposed to be sexy and fun. I know that you will never have a chance quite like this to make it work for you and Penelope. Two women that care for you. A bull, who will cuckold you make no mistake, but, who will take care to make sure that you keep a bit of dignity in the doing of you. Okay."

"Okay," I said.

*****

She led me down the stairs. We paused at the door to the guest room. It was quiet in there, I noticed. I think they heard us coming and were anticipating my, our, entry.

Maria led the way. They were lying on the bed nude and obviously already well fucked. At my entrance several thing happened simultaneously or so it seemed to me.

One, I looked over at Maria and noticed a slight, but very clear, look of—what—dismay. She looked at me, and I thought that I saw a woman who needed an anchor at that moment. I mean there was her husband doing, actually having already done, the one thing that she had at all costs wanted to not do, albeit with her permission. She was at the very least disconcerted.

Two, the two on the bed reacted predictably toward me. Penelope covered her mouth to suppress her laughter at my appearance. I had to look ridiculous to her; hell, I'd seen myself in the mirror and I looked ridiculous to me!

Third, There was Juan. He was smiling, but not in an amused sort of way. No, he was clearly pleased. And then there was me.

I felt absolutely humiliated. I wasn't at all sure that I was going to be able to make it through the evening. I was determined to try, but sure of it, not even.

"Who is she?" said Juan, speaking to Maria. Maria looked at him and finally smiled herself.

"Why, this is Olivia," said Maria. "Treat her with respect, and be gentle with her. I was more or less ready for something like this, having been dressed as I was and made up to be as female as the limited amount of time had allowed.

"Bring her here," he said. "Introduce us properly."

Maria marched me to the bed. "Penelope Whitman, Juan, this is Olivia. She'll be joining us for tonight's fun."

"Nice to meet you, Olivia," said Penelope, still trying more or less successfully to stifle her laughter. She took hold of her partner's cock and aimed it at me. "We girls get to play with this tonight. Won't that be fun, Olivia?"

I swallowed hard. "Yes, miss," I said.

"Would you like to touch it?" said Penelope. Not waiting for an answer, she reached out and took hold of my hand and pulled me to him. "Here, hold it, stroke it," she said. I did as she said.

The huge tool was not only long it was thick, very thick. For the first time I was actually afraid of what I knew he wanted to do to me. I think it showed. He tried to calm my fears.

"Don't worry, Olivia," he said. "I know how to treat a woman. I make it my business to make sure my partners always enjoy themselves. You don't have anything to worry about. Trust me." And, for some reason, I did trust him.

Maria came to me. I released my hold on his cock. She pulled me down on my knees along side of her. Kneeling just a few feet from the bed, we both stared at the man's sex engine. Juan had slung his legs over the side and spread himself wide in anticipation of what he hoped was about to occur.

"See Olivia, Penelope's juices and smell are all over him. You're her cuckold and his too now, little man. Time to do your duty. Go on lick it. Suck it," said Maria. I looked at her, leaned in, and licked his cock. Taking hold of it I did as I was told.

Penelope had moved close in to watch as I licked and sucked him. For the moment I was the star. That figured to change though as Penelope, and I assumed Maria, would be sharing the limelight with me.

"That's it honey, suck him nice. Make him ready for us," said my wife. He suddenly jerked his cock from my mouth. I was surprised, but he just smiled.

"Don't want to cum in your mouth, Olivia," he said. "I want to cum in your butt. Get up her on the bed and lay down on your back." I think I showed a little concern. I mean I knew it was going to happen, but I wasn't sure that I was quite ready for the reality. Nevertheless, I did what he said.

He slipped my panties down exposing my caged penis. I know my face had to be as red as a fire truck. "Nice," he said. "I guess you're not only a cuckold now, but a damn horny one for sure. God it must be awful to be caged like that, but it's what your wife wants, so you have to obey her. Them's the rules." I swallowed and glanced over at Penelope. She was clearly fascinated. Her lips were slightly parted and she was absently licking them.

"Come her, girl, and push some of this stuff up his—uh her—butt. She's going to be needing it really bad." He handed Penelope the tube of KY. She took it and came closer to me. He held one of my legs up high in the air, and Maria held the other, as Penelope, scooted down and got between them. I saw her load a glob of the stuff onto her fingers and felt her begin swabbing and finger fucking my ass to get me lubed up good.

"God, honey, it is going to be so hot watching him screw you. Try and relax; he's awfully big. You have to think like a woman for the next little while. Because for the next little while you are going to be treated like a woman," she said.

"Okay," I said.

"I love you," she said.

"Put some of that on me, girl," he said to Maria. She did as he asked.

******

At that moment I hated the sun. But, I did have to get up. I looked down at my sleeping wife. Would I be able to stand being denied? I honestly didn't know. But, I was going to try. What was certain, was that I was condemned to just exactly that for the next six months; well, sort of. I watched her stir.

"Morning, hon," she said, as she rubbed her eyes. She stopped her rubbing and looked at me with a very serious expression. "You okay, my little cucky?" There it was: my status as her cuckold. With his Juan's cum still up my ass, there was no doubt what I was and what my life would be like, at least for the next six months. The cock cage imprisoning my penis was the guarantor of that. Oh, I could have my wife, as we agreed, and such at Maria's suggestion. All I had to do was to submit to punishment the next day for each time I got any. The punishment? Fifty across my naked buttocks and thighs with the switch: a thin, whippy, nasty little thing that would make every minute of pleasure with my wife a very expensive proposition.

"Yes, ma'am, I'm fine. But, don't bother putting the switch away. I'm of the opinion that by nightfall, I will be beggin for you to take me to task with it tomorrow," I said. Her smile was a mile wide.

"Looks like we've found the right formula," she said.

"Looks like," I said.

*****