The Last Time We Met

Author's Note: This is my first entry in the Valentine's Day Story Contest 2023, and my first foray into romance. Those who have read my other works won't be surprised at some of the twists. For those who are reading me for the first time, I encourage you to read all the way through. I trust the ending will be satisfying and, perhaps, thought-provoking.

"Do you remember the first time we met?" he asked.

"Of course," I replied, "It was right here, two years ago. You were waiting for me here. You bought me a cup of mint tea. It was raining and I was so nervous about meeting you, but you set my mind at ease. You were quite the gentleman."

"And you were quite the lady."

"Until I wasn't."

----------

February: First Meeting

I was in the desperation round of trying to create the perfect personal that would attract the man I was seeking. With the demise of Craigslist, I was left to the not-so-tender mercies of Doublelist to find him, a fool's errand at best. I had finally crafted what I thought to be the ad that would hook him, if he was available to be hooked.

Who will unleash my inner maiden?

Who will bring out my inner submissive woman? While, as a 60+ year old MWM, I'll never be mistaken for a starlet, I am still fully capable of passion. As a submissive with a strong oral fixation, I want you to show me how to bring you pleasure as often as you desire, in the manners you desire. I want you to seduce me and make me yours, eager to worship your body, from head to toe, and to offer you my body, to dress as you desire and to use as you wish.

More than that, I want you to shape me into the submissive maiden that you and I desire. As a person of mature years, I'm not interested in becoming a sissy bimbo (leave that to the youngsters). Rather, I want to be your woman, not necessarily in outer appearance, but in the demure manner in which I approach you, being the lady to your gentleman, being able to carry on an intelligent conversation and being the perfect mature lady in public while being your passionate lover in private.

If you're looking for a quickie, this is not the ad for you. I would like to find a man who will mold and guide my feminine side into your special lady (a passionate slut at times, and more than willing to be shared by you).

I'm looking for someone special, someone who is literate and sensual, who needs my passion as much as I need his taking possession of me and molding me into his perfect giver of pleasure. Is that, perhaps, you?

The first few replies were predictable. The number one reply, not surprisingly, was "can u host?" I wept for a generation that was too lazy to spell the second person pronoun correctly. Most of the others were some variation of "On your knees, bitch!" For an area that prided itself on the number of high tech and higher education facilities, the online literacy was downright depressing.

Donald's reply stood out: it was literate and to the point. He was a middle aged divorced professional who enjoyed having his cock sucked by men who wore stockings and panties. He was clear that he was no Adonis and that his cock was average at best. Not exactly Dom of my dreams material, but he could write in complete sentences and sounded sane...and I really liked wearing stockings and panties.

I appreciated his honesty and let him know that I, too, was ordinary at best and that as long as his cock could feed me cum, it was the right size for me. And let's face it: at my age, the most I could hope for was a decent guy who wouldn't mind feeding me his cock every now and then.

In the next email, I learned he shared my love of bad movies and good music, as well as kinky sex. He was sharing a house with another man who wasn't wild about him bringing men home, but he told me that, if we hit it off, he would be glad to get a room. I offered to split the cost, but he declined. "A gentlemen always pays." He immediately moved to the top of the list.

In the third email, he suggested meeting at a nearby Starbucks for a cup of coffee. I hated Starbucks, but I wanted to be the proper submissive, so I agreed.

We met on a dreary, rainy February day. I had emailed him a description of what I would be wearing, including the panties and stockings that would be under my pants. What I didn't mention was the dark red bralette I had added. That would be a surprise for him if things progressed to that point. If they did, it would also highlight my chest hair and reinforce that I was a man dressing up in girly stuff. Of course, that didn't matter: guys wanted their cock in my mouth, not a fashion show.

I arrived a little late and, as usual, hadn't brought an umbrella. Of course, the only parking spot I could find was a good distance from the entrance. I walked quickly into the coffee shop and was only a little wet from the drizzle. I looked around and saw a man watching the entrance. He saw me and waved. I took a deep breath to give my inner maiden a moment to prepare herself to meet him.

He stood up when I got to his table, extended his hand and shook mine. It was a firm handshake, but not a macho death grip. He held it a second longer than was usual.

"Hi, I'm Donald. Please sit down."

"Thank you. I'm Roger. Pleased to meet you."

I sat and made sure my knees were touching. My knees were at one end of the chair and my feet on the other, as a lady should sit.

"What can I get you, Roger?"

"A cup of hot mint tea would be nice."

"Coming right up." He went to the counter. My chair faced the counter, so I could watch him as he moved. He was dressed in the business casual that was the norm for the area, but carried himself like someone more accustomed to power suits. He was stocky, but not chunky, and his ass filled out his pants well. So far, so good.

He smiled as he walked back with my tea. It was a pleasant, reassuring smile, and I relaxed. His face was smoother than his age suggested; there were a few wrinkles, but they were distinguished rather than baggy. His eyes were a clear blue, which complemented his dirty blond receding hair. Overall, an ordinary but not unattractive face.

I took the tea from him and blew on it to cool it down. He watched as I took a sip. I lowered my eyes.

"So, how's your tea?"

"It's good, Donald. Thanks for getting it."

"My pleasure, Roger. So, how long have you been doing this?" He was direct,.

"Exploring this side of myself? Off and on for several years, mostly off."

"Why mostly off?"

"I've never really had a lot of friends, and those I do are friends of the family. They're all very conservative and religious, and I don't confide in them....actually, I don't really confide in anyone. And I don't really do much with my coworkers. I don't drink and I don't like partying, so I don't do the bar scene. I've never really socialized."

"You're doing a pretty good job right now, Roger. And I know this area isn't exactly tolerant of, shall we say, the more interesting practices? I know parts of it are gay friendly, but it's not particularly open to kinksters."

"It's not just that. I guess I've been submissive from an early age, but didn't know what to call it. When we played war games, I'd want to be the soldier who was captured and tied up. And I got along better with girls my age than with boys. I'd look at the Sears catalog and lust over the lingerie section. I wanted to wear the nightgowns and the bras, but I knew that was perverted and bad."

"You were taught that?"

"Yes. I had a strict religious upbringing and knew only sex with my wife would be proper. Even today, I have bouts of guilt over what I do...I'm sorry, Sir. That's way too much information, I know."

"Not at all, Roger. I'm glad you feel comfortable enough with me to open up like that."

"I'm not sure why I am, Sir. Normally, I'm the one strangers confide in. But, if I may," ready to deflect this conversation away from showing him what a loser I was, "what was it about my post that attracted you?"

"You mean besides pushing all my buttons? It looked like it was written by someone who's well educated, literate and wants more than something in his mouth. Frankly, you sound like someone who could be a lot of fun."

I appreciated his lowered volume and careful choice of words, as Starbucks isn't exactly known for its privacy.

"And now that you've seen me?"

Far too many times in the past, this was the moment where the man shook his head and said sorry, you're not my type. I took another sip of my tea and looked at the table, waiting for the inevitable rejection.

"Now that I've seen you, Roger, I think you look awful cute sitting there. You know how to talk, you have all your teeth and hair, and I hope your mouth is just as good for other things. Besides, I can't wait to see how you look in your bra."

I looked up in surprise and embarrassment. How did he know I was wearing a bralette?

"Next time it's raining, Roger, you may want to wear a jacket if you don't want your bra straps showing. Don't worry: no one will notice unless they're looking...and I was looking. Now, the big question: shall I get a room?"

"I would like that very much, Sir."

"I'm glad. There's a hotel nearby where I have a lot of points. I'll text and reserve a room when I get in the car. Why don't you ride with me? Your car will be safe here and we can talk on the way."

"Thank you, Sir. I'd like that."

"By the way, my name is Donald. But I'm curious: why are you calling me 'Sir'?"

"I'm sorry, Sir...er, Donald. I don't know why I did that. Force of habit, I suppose."

He smiled. "It's a very nice habit, but let's wait until I earn it, okay?"

"Yes...Donald." My heart skipped a beat. Earned the title Sir? He didn't look like a Dom, but still...he clearly had some knowledge, and understood the concept of earning respect. I realized I was starting to respond to him and regretted wearing light khakis. I hoped the panties would stop any leakage.

He held the door open for me and we stepped out into a downpour. He pulled out his umbrella, opened it and held it over us while he led the way to his car, a sports model that belied his somewhat nerdy look. Again, he held the door open for me and I sat down before pulling my legs in together. He got in and started the engine.

While he booked a room on his phone, I looked for his telltale bulge. I found one, not huge, but enough to let me know he was definitely enjoying this. He caught me staring and rubbed my hand over it for a moment. I squeezed it briefly, but he moved my hand back to my thigh, taking the opportunity to give my crotch a friendly grope.

"I'm glad you like it, but no distracted driving, please."

The hotel was about fifteen minutes away. When we arrived, he opened my door and held up his umbrella while I brought both feet to the ground and stepped out of the car, adjusting myself as stealthily as possible. Donald deliberately looked away to give me privacy. He was always the considerate one. We walked to the covered entry.

Just before we reached the electric eye controlling the door, he said, "Why don't you go in and sit in the waiting area while I check in? I'll text you my room number."

"Good idea, S...Donald."

I walked in and took a seat in the lobby area. A minute later, Donald walked in and went to the main desk. I made a show of checking my phone while he picked up the key and walked to the elevator. After about ten minutes, just when I wondered what was keeping him, I received a text message: 314. I got up and took the elevator to his room. In the elevator, I adjusted my cock and licked the drops of precum that had accumulated on the head. My heart was pounding with the anticipation of a long needed feeding.

I knocked on the door and it swung open. I walked in and closed it. Lying on the bed, under the covers, was Donald. I saw his clothes on the desk. His briefs were on top.

"I hope you don't mind, but I wanted to be ready when you got here. You can get ready in the bathroom."

This was looking more like my typical encounter: meet a visitor in a hotel room, put on my stuff in the bathroom and come out and give him what he wants: usually a quick blow job. I had performed my share of lullaby head. Plus ca change, as the French say... I answered in my most sultry voice.

"I'll be right back, Roger...don't you go anywhere."

I turned the corner to the bathroom. Since his line of sight was blocked, I didn't bother closing the door. I stripped off my clothes and took a look in the mirror. Staring back was a dumpy looking man on the far end of middle age, wearing black thigh high stockings, a pair of black bikini panties with a shrinking bulge and a wet spot, and a red bralette surrounded by a sparse but noticeable growth of chest hair. I wasn't a gorilla, but I wasn't going to pass any time soon.

The middle age spread completed the picture. It wasn't a full on beer gut, but sucking it in barely pulled it lower than my bralette. I should have known better than to look in the mirror: it destroyed the illusion I had built up in my mind. I had one chance: Donald wore glasses and he had removed them to get in bed. With any luck, he wouldn't notice what a mess I was until I had his cock in my mouth. When I started making love to his cock, he wouldn't care what I looked like...until he came.

I took off my glasses, which rendered the world a blur, and got into my best slutty cocksucker mindset, walked out into his presence and struck my vamp pose.

"My God," he exclaimed, "You look amazing! Come here, Regina, and say hello to my little friend.

Regina...I liked that. I strutted toward him, one foot in front of the other to get the hips swaying, while he threw the covers off. I knelt at the end of the bed between his legs and started the slow crawl up.

I kissed the soles of his feet and gave them a lick. They were hard but not callused, manly feet. Hearing him moan in approval, I took each toe in my mouth and sucked it, giving him a sample of my mouth and tongue. The toenails were clean and trimmed: he was a man who took pride in his appearance. From the sounds he was making, he was also a man who enjoyed having his feet worshipped. My cock was rising to the occasion. I wanted to linger for a while, but his cock summoned me.

I kissed my way up his legs, admiring the sparse, dark hairs. I stopped at his knees and turned onto my back. I took one leg and gently kissed and licked the back of his knee. He gasped in pleasure.

"Where did you learn that trick?"

"I like to explore a man's body and discover all his erogenous zones, especially the ones that aren't so obvious."

"Well, you found one of mine."

"You ain't seen nothing yet," I replied, turning back over and continuing my lingual exploration of his legs. I was mostly licking him now, loving his taste on my tongue. I rubbed my stocking clad legs against his and felt them pushing back. I could smell the musk in his crotch; it was having the desired effect. I had planned to continue my exploration to the top of his body and back, but I knew I wasn't going to be able to resist his cock.

Sure enough, it was fully erect, about the same length as mine, but thicker. It was oozing precum and I had to get a taste. I ran my tongue up his shaft, intoxicated by the salty sweet flavor, and licked the nectar off his cock head. I held it and gazed in adoration. It was a magnificent specimen: smooth except for the main vein going up the shaft. I kissed my way up that perfect shaft and circled the head with kisses, concluded with a kiss on the slit.

I licked the precum off my lips and slid it into my mouth. I held it tight and let it rest against my tongue, once again letting a man's cock own me and make me his woman. I ran one hand along his thigh and gently massaged his balls with the other. I lay my head on his stomach and closed my eyes, nursing on his precum and humming contentedly. I was where I belonged.

And then I heard him cry out and felt the pulsing that told me I was about to receive my reward. I raised my head and starting sucking in earnest. One, two, three...hard pulses that filled my mouth with his wonderful cream. I swallowed it as quickly as he filled my mouth with his pleasure. His legs were shaking and his hands went to my head to pull it away, but I was not to be denied. I went to my knees with his cock still in my mouth and went after every drop he had. I coaxed his balls and, wrapping my lips over my teeth, squeezed the base of his cock and slid my lips up until only his head remained in my mouth. I was determined to drain every last drop he had. His hands slapped the bed and he bucked.

"Stop! Stop! I can't take any more," he cried, and I smiled.

I had taken him to that special place of pleasure/pain that signified a job well done. I took one last slurp and slowly released his cock. I lay my head back on his stomach, kissed his shrinking cock, looked up at him and smiled.

"I hope I pleased you, Sir."

"I haven't had that good a blow job in...ever. Get up here, Regina."

I slid myself up his body and rolled into his outstretched arm. He wrapped it around my shoulder and pulled me into him. He was on his back and I was on my side, nestled into him. I placed my head on his shoulder and ran my fingers through his chest hairs and down his stomach. He had a bit of a paunch, not quite as much as I did, and an outie. He looked good and smelled good; I felt warm cuddling with him.

I moaned with satisfaction as he rubbed his hand along my arm, then felt his way around my bralette and down to my stomach. All the while, his legs were rubbing against mine, and we were playing footsie. My own cock was straining against my panties and I could feel the wetness of my own excitement.

"You feel so good, Regina," he said, staring at the ceiling.

"I"m sorry about the body hair," I said, softly.

"Don't be," he said, stroking the hair on my stomach, "It feels nice and soft. I love it. And your clitty is so wet."

He fed me my precum on his fingers. I sucked them greedily, then looked up at him. Normally, when a man is finished, I see in his eyes he's already moved on and is thinking about getting dressed and getting home. Donald was staring at me, with a warmth in his eyes I hadn't seen before in a man.

"Please, hold me, Sir," I whispered urgently. In that moment, I was, indeed, Regina.

He rolled against me and hugged me tightly to his body. His arms felt good around me. I buried my head in his shoulder and kissed it over and over, not wanting to leave his embrace. Our legs intertwined, striving to be one. I could feel my cock squeezed between us. His hands ran over my back and slid under my bra. One hand made its way down my back into my panties. He slid a finger into my ass crack and pulled me against his crotch while trying to insert the tip of his middle finger inside me.

I could take no more. I moaned into his neck as I lost all control — my warm cum spreading over our torsos, somehow finding a way though our embrace and cementing us together as one with its warm stickiness. He squeezed me even tighter and started kissing my neck. I froze, knowing if I dared move my head from its present hiding place, I wouldn't be able to avoid his lips on mine and I had to avoid that at all costs.

We remained locked in that position while my breathing returned to normal. I wondered if he could feel the pounding of my heart. All too soon, the post-orgasmic glow faded and I was aware of my situation: rapidly cooling sperm on my body threatening to make a mess of the bedsheets. I turned over on my back and stared at the ceiling, sighing.

Donald went to the bathroom. I closed my eyes in exhaustion, physical and mental, listening to the sounds of the room: the air conditioner, urine hitting the toilet, a flush, water in the sink, bare feet on carpet. Then, the warmth of a damp washcloth cleaning my torso and shrunken cock. I opened my eyes and saw him smiling down on me.