The Last Time We Met

"Passion is good. I expect that. Sluttishness is not."

"I understand, Donald. And, thank you for giving me another chance."

"Make no mistake, Roger. This is not about second chances for you. If I just wanted a cocksucker, I could get one. But Regina showed flashes of something special. I want to see what makes her tick."

This was going to be the mother of all role-play games. Did he know how much I enjoyed that? Was that why he was pushing these buttons? If I managed to keep my sanity, this was going to be the ultimate sensual experience for me.

"You and I will meet like this when either of us thinks it's necessary to make sure things aren't going overboard. I want you to feel comfortable about this, Roger, and I want to be sure you know me well enough to trust Regina to me. I hope we can be friends."

"I'd like that very much, Donald. It's going to be a challenge, but I'm excited about it. I'm REALLY excited: don't ask me to stand up right now."

"That goes for both of us," he laughed. I had come here expecting a brush off, but found...what? I wasn't sure, but I knew I was going to feel his body against mine...I mean, his body against Regina's...and I was eager to taste his cum again.

"And, Roger," he added in a completely serious tone, "don't screw this up for us."

"No, Donald," I answered nervously, "I won't...I want this to work. I need it to work. Please, don't let me screw it up."

"We'll meet at the same hotel Thursday. Be there at 4:30. I'll text you the room number. The door will be unlocked. Go in and put on what you find there. When Regina is ready, text me. I'll knock. Check your inbox when you get home. As for clothing sizes, I'll send you an email this evening with the information I need. Be sure to send me all the sizes I ask for in the email. And, Roger..."

"Yes, Donald?"

"I expect Regina to wear what I give her and do everything I tell her, no matter how she feels about it. Am I clear?"

"Yes, Donald."

"Oh, and one more thing. No orgasms for you, only Regina."

"Sir?"

"You may not be my lover, Roger, but you most assuredly are my sub. I'm not going to let you mess this up."

I hadn't considered the possibility, but I twitched in my pants when he said that. I had to take square roots in my head to avoid ruining them.

"Thank you, Sir. That means a lot to me."

"We shall see. Do you have any questions? Concerns?"

"Not at the moment. If I do, may I email you?"

"Sure you can, Roger. By the way, 'Return to the Chateau' sucked."

"Thanks for the heads up. Actually, I was going to read 'Solaris' next. They're showing it in a couple of weeks and I want to be ready for it."

"The Tarkovsky version, I hope."

"Yes, it is. Are you a science fiction fan, Donald?"

"I'm a bit of an eclectic; more of a film fan. Let me know when it's playing. I'll go with you."

"That would be great. I don't normally go with anyone. I think I'd enjoy your company."

"It's a....movie night, then. I have some errands to run. I'm looking forward to seeing Regina Thursday."

He left and I sat there processing what had just happened. I couldn't be that lucky, could I? Sure, it sounded extremely strange, if not bizarre, but I was used to that. It appeared Donald was, in some way, as much of a freak as I was. I wasn't going to complain, as long as we both focused on the ground rules. I would finally get to do what I had always wanted: role play a woman and get a mouthful of cum every week.

But what about how I had felt at the hotel? If anything was bubbling under the surface, it was about Regina, not Roger. I was very good at siloing my private play from my real life. Let Regina be the helpless maiden who becomes Donald's kept woman. Roger would remain Roger. And, who knows? Donald appeared to have excellent taste in movies: this might be the start of a wonderful friendship...any friendship would have been wonderful.

I was a bundle of nerves by the time Thursday rolled around. It was hard to focus on work, though I was wearing nothing distracting. Regina wore the panties in the family and Donald was providing those. He was in charge and I was happy to follow his lead. He seemed to know what he wanted and how to get it. I wondered briefly where this was going, but I knew: to the hotel and a wonderfully kinky time in some slinky lingerie sucking Donald's cock.

The sun was out, but starting to dip toward the horizon. It was breezy and cool: a far cry from our last meeting. I worked on my breathing and continued reading 'Solaris.' I had almost finished the chapter when my phone dinged and I saw his text: 417.

I entered the hotel and took the elevator to the fourth floor. As he told me, the door was off the lock. I pushed it open and went in. On the bed were a red polka dot swing dress, red bikini panties, a red bralette and black fishnet thigh highs. Sitting at the end of the bed was a pair of low heel black pumps. On the desk was a wig stand with a medium length brown wig. It had streaks of grey in it and was parted to one side.

It was surprising how ordinary the outfit was: something that would be worn by a housewife out for an afternoon at the mall, though the fishnets might suggest she was on her way to an assignation. It was not the look I had expected, but Donald was a man of surprises. Was this how he envisioned Regina? It was not my idea of who she was, but, after all, he was the sugar daddy and Regina was his kept woman.

I took off my clothes and put them on hangers in the closet. Once naked and the closet door shut, Roger was gone and Regina was about to emerge.

The panties were a cotton modal blend that felt very smooth. They were large enough not to expose any of my boy bits but tight enough to keep me tucked. I pushed my balls into their pre-puberty hiding places, pulled my cock behind me before it could become too excited and pulled the panties up to keep everything in place. I inspected the front and noted with approval that it was smooth.

The bralette was a slightly different style than the one I had worn. It was tight around the outside of the cups and I was able to push enough of my man boobs into them to create what would pass for an A or B cup. This time, I didn't look in the mirror: I wanted to wait as long as possible before destroying the illusion.

Next, I pulled on the fishnets, luxuriating in how they felt. This was my first time wearing fishnets and I fell in love with them, though they made me painfully aware of my leg hair. Oh well...Regina was obviously a liberated woman who didn't need to bow to the patriarchy by shaving her legs.

Finally, the dress: the first dress I had worn in all my years of exploring. Teddies, yes; nighties, yes; baby dolls, yes; but never an actual dress. I picked it up and felt it against my cheek. Why had I taken so long to have something like this in my hands?

The dress fit almost perfectly, a little tight in the waist, but otherwise perfect. The sleeves extended halfway to my elbow and the collar was cut low enough to expose my throat but not my chest. I smoothed it out and now dared to look in the mirror. I was amazed at what I saw. I've always said I wasn't passable and didn't want to be seen in a dress, but I looked in the mirror and saw a woman looking back, a woman who wanted nothing more than to please her man. My transformation was almost complete.

I sat on the bed and slipped on the pumps. They were plain black leather with what appeared to be two inch heels. I had worn stilettos that were much taller, but these were designed for comfort, not porn. I took a walk around the room, becoming accustomed to them and working on my heel to toe, one foot in front of the other, gait. The dress swirled as I walked, and the feeling of cloth against skin started a wet spot in my panties. I was thankful they were tight enough to hold the tuck.

Finally, I turned to the wig and, with a bit of trial and error, figured out how to size the cap and place the wig on my head so it wouldn't shift. I fluffed it and returned to the mirror. I recognized the woman who stared back at me.

"Hello, Regina," I greeted her in a sultry alto. I patted the hair, which fell to just above my shoulders with a part on the right. Regina wasn't a sissy and she wasn't a slut. She was a woman, no, a lady, of a certain age and refinement who was still lusty enough to show her man how much pleasure she could give him.

I texted Donald. "I'm ready for you. Regina"

I sat on the sofa with my knees touching and ankles crossed. It was a pose that took some thought to maintain. I made a note to practice it until it was second nature. My heart was beating wildly and I was holding my knee tightly with both hands to keep from shaking. My breathing exercises were going to get a workout during this relationship. I hoped my mouth would, as well.

A light knock on the door focused me. I stood up as gracefully as I could, walked to the door and opened it. Donald was standing there in a polo shirt, cargo shorts and deck shoes with no socks. I hadn't noticed before how good his legs looked.

"Are you going to invite me in?"

"I'm sorry, Sir. Please, come in." I stepped aside as he entered and closed the door behind him. He held me at arms length and looked me over.

"Damn, Regina, you are one gorgeous lady. Where have you been all my life?"

"Waiting for you to arrive, Sir," I said in my best coquettish voice. Looking at his pants, I added, "And I see someone's happy to be here."

"You're right about that, sexy lady. My pants are getting a bit uncomfortable."

"Let me do something about that, Sir."

I lowered myself gingerly in front of him (at my age, one doesn't drop to one's knees unless one wants a trip to the orthopedic surgeon) and unsnapped his cargo pants and let them drop to the floor. His briefs were tenting and a wet spot was starting to grow. I couldn't have him ruin his underwear, so I pulled them down to his knees and greeted his cock with a kiss and a lick.

The sight of his magnificent cock and balls so close to my lips was more than I could endure. I cupped his balls in my hands and kissed each one, savoring the musky scent trapped in his pubic hair. I took them in my mouth and slathered them with my tongue, grinning with satisfaction as I heard him mutter, "Oh...my...God..."

I looked up at him and smiled. "I'm glad you provided easy access, Sir. I'm awfully hungry."

His reply was interrupted by a gasp when I licked up his shaft and took him into my eager mouth. His thighs were trembling and I realized he was already primed and ready. I grabbed his tush with both hands and pulled him into my mouth, until my nose was mashed against his crotch. I squeezed his buns tight, rubbing them while I tightened my suction grip on his cock and targeted it with my tongue.

He grabbed my hair (good thing I had figured out the wig cap) and held me in place as he pulsed into my waiting throat. I swallowed in self defense and dug my fingers into his buttocks. As he emptied himself in my mouth, his grip on my hair loosened and I was able to pull my head back so his cock could deposit the residual nectar on my tongue.

I pulled my head off his cock and looked up at him adoringly. I stuck out my tongue, proudly displaying his seed, then swallowed it and cleaned up his cock. His thighs trembled and twitched as I licked his shaft clean and gave his head a last suck. The sight thrilled me.

I made sure his cock was no longer sticky, then pulled his briefs back up, followed by his cargo pants. I zipped them carefully and rearranged him. I sat back on my heels, straightened my dress and addressed him.

"I'm glad you're here, Sir. I hope I gave you an appropriate welcome."

Donald looked down at me and smiled. "I'll have to wear cargo shorts more often."

I rubbed his legs adoringly: so manly, with just the right amount of hair. "I must say, Sir, your legs are very sexy."

He laughed. "That's the first time I've heard them called 'sexy.' I like that, Regina. You know how to make a man feel wanted."

I bowed my head. "And you, Sir, know how to make a woman feel wanted. You've been so good to me; I want to give you the pleasure you deserve."

"And so you shall, Regina...so you shall. Now, let me take a look at you."

He lifted me to my feet and stepped back. I attempted a pirouette, but lost my balance and nearly fell over before he reached out and steadied me.

"You have to learn to walk before you can strut, sexy lady. We'll work on that."

My heart fluttered a little at his words: I was his sexy lady. He walked around me and hummed appreciatively.

"You're beautiful, Regina, and you're going to be even more beautiful. I have such plans for you..."

"Plans? What sort of plans, Sir?"

"I want you to be the very best lady you can be, Regina, but you need some refinement. I'm going to teach you how to walk, how to deport yourself, how to be treated as a lady. You will learn what pleases me and it will become what pleases you. You are going to be my perfect courtesan.

"Each time you come here, you'll find your attire for the day. I want you to learn how to wear a variety of clothing, each one making you more a woman. Each time I arrive, you'll greet me as you did today. After that, we shall work on your femininity. And if you please me with your effort, I shall reward you with another serving of my nectar. How does that sound?"

"Like sissy boot camp, Sir."

"You're hardly a sissy, Regina. Consider it more a finishing school."

"As you wish, Sir." This role play was beginning to sound like work. And Donald was starting to sound even weirder than me. Still, I couldn't deny how sexy he made me feel. If he wanted me to be his personal Barbie doll, who was I to complain?

"I'm glad you agree, Regina. You have no idea how much that pleases me."

Why did my clit start to get wet when he said that? I was glad my panties were still pulled tight.

He took my hands in his and kissed each palm. He moved gently up my arms and feathered his way back down with his fingertips, bringing a gasp to accompany the goose bumps.

"You have soft skin, Regina, but there are a couple of dry patches. You should use moisturizer on your hands and elbows every day. The same goes for your feet. Sandal season will soon be here."

"I'll do that, Sir, but I don't wear sandals."

"Roger may not wear sandals, but Regina most assuredly will. And, while you're at it, you need to start getting a mani/pedi at least once a month. I want your hands and feet looking their best for me. No need for polish just yet."

I was sure he added "just yet" to see my reaction. My reaction was no reaction.

"I want to look my best for you, Sir. Do you have a recommendation for a place to go?"

"I'll email you the name and number of the woman who does my pedicures. She has a private practice and is very good at what she does."

"Thank you, Sir. But I didn't know you had pedicures."

"Don't be so surprised, Regina. Many men enjoy a good pedicure. It's very relaxing and stimulating at the same time. Besides, I have to look my best for my sexy lady, don't I? And speaking of relaxing and stimulating, I'm going to relax on this sofa while you stimulate me by showing me how well you walk."

He sat back and kicked off his shoes while I walked around the room, making sure to put one foot in front of the other and stepping heel to toe. After some initial clumsiness, I started to fall into a rhythm and stopped thinking about my movement. The fabric of the dress massaged my legs as I walked.

"Keep your head up, Regina. A lady doesn't look at her feet when she walks. She has confidence in herself. Don't take long strides: you're not in a hurry. Keep your body straight. Men slouch when they walk. Ladies stand tall and proud of who they are.

"You are the possessor of a lovely body and lovely clothes. Lift your head back up, Regina. Come over here."

I stood in front of Donald, flushed from the unexpected exercise and from his words. He looked me firmly in the eye. I looked down.

"Look at me, Regina. Look at my eyes and stop turning away. Do you think I'm playing a game with you?"

"What kind of a game, Sir?"

"Don't insult my intelligence. When I ask you a question, I want a direct and honest answer. As long as it's truthful, it won't hurt me. Do you understand?"

He was dead serious, with no trace of a smile. I licked my lips and wondered what I had done wrong. Was I about to mess this up again?

"I'm sorry, Sir. I'm trying to understand the question."

"The question, my dear Regina, is very simple: do you think this is all just a bit of kinky dress up fun so I can get a man to blow me? If that was what I wanted, don't you think I could go online and find a cute young sissy to give me a blow job a whole lot cheaper than getting a room here and buying you these clothes?"

"Sir," I replied, my voice quivering as his words struck me, "I don't know what I've done to upset you, but I'm sorry for whatever it is. I know you can do a lot better than me. I'm trying my best to please you, but I don't know what I'm doing wrong! Please, tell me what I need to do so I don't ruin this."

I was almost in tears and Donald stood up and hugged me tight to him. I stood stiffly, not sure what to do.

"Regina, I'm sorry I snapped. I didn't mean to hurt you. I would never want to hurt you. But, even more, I don't want you to keep hurting yourself."

Great: another person trying to tell me what I already knew. I pushed him away and looked at him angrily.

"What do you mean, Donald? Do you think I sabotage my relationships? Do you think I deliberately set myself up for failure? Do you really think I'm that much of a loser? Or do you think I'm so stupid I can't see what I really am when I look in the mirror?

"You could definitely do better online. You could do better anywhere. I don't even know what I'm saying right now. See? I'm doing it again. Why are you even bothering with me? You're a wonderful man! You could have anyone you want. Why are you doing this to me?"

"Sit down, Regina, and I'll tell you exactly why I'm doing this to you. I said, sit down!" There was fire in his eyes and I sat quickly, planning my path to a quick exit, just in case.

Donald took a step back and stood a couple of paces away from the sofa. He closed his eyes and slowed his breathing. After taking a deep breath and blowing it out, he opened his eyes.

"This isn't easy for me, Regina, and I don't want you interrupting me until I'm finished with what I have to say.

"Do you want to know what set me off? I'll tell you: every time I tell you how beautiful you are, you look down or turn away. And I'm getting tired of you calling me a liar.

"Don't even think about interrupting me, Regina. Yes, you are calling me a liar. You turn away because you think I'm playing a game. I'm not: I don't play games with people's feelings and emotions. Do you really think I'm that sort of heartless bastard?

"No, stop trying to interrupt me. I'm going to tell you the cold, hard truth about yourself. These are facts, not fantasies, not role play...and don't question my integrity by thinking otherwise. Here's the truth about Regina:

"The first time I saw you here, I knew you were someone very, very special. I already knew you had a sharp mind, which is 90% of what attracts me to someone. But when you presented yourself to me, I saw so much more.

"It wasn't just what you were wearing. It's that you wore it so comfortably, in spite of your concerns about your appearance. You were born to wear lingerie, Regina: simple truth.

"But when I saw your eyes, I was enraptured. I don't know what you see in the mirror and I don't care. Here's what I see: you are beautiful from the inside out. Your eyes are so warm, they send a glow throughout your body and make it the one thing I desire most.