Second Time Fun

I met Stuart on the Internet. I had posted on several sites, and my posts ran something like this: "Athletic, extremely exhibitionist bottom likes to please and be watched. Seeking fit man, fifties or early 60s, bearish. Must be discreet. Would like to enjoy mutual masturbation. If we click, anything is possible."

I was looking for an older man, and because I'm just this side of forty I specified that the age of my potential lover should be in his fifties or early sixties. I included a picture of myself from the neck down, naked and showing an erection. I'm in shape, and I'm well endowed. Including a picture, I thought, would bring responses.

This was the first time I had posted. I'm married, and at that time I had only had sex with a man once, five years prior. It had been an enjoyable experience and had served as fodder for many solitary fantasies. It was time to relive the experience.

When the replies started to come, I almost called off the adventure. They were hard and abbreviated messages, with an air of impatience. I was not looking for a relationship, but neither was I looking for an encounter entirely devoid of personality and connection. Finally, one message stood out. It was more than a paragraph long, and the writer seemed educated and kind. He wrote of his interests, and he stressed that he was fine with meeting just for watching and masturbating. He invited me to write back.

We exchanged emails and determined that we might be suitable for each other. We each had some interesting sexual proclivities. He enjoyed water sports ( for which I could not agree to share his passion). And I had long fantasized about showing my stuff in front of a man wearing only high-heeled women's shoes. To my surprise, he responded favorably to my fantasy, even agreeing to supply the shoes. He wrote me his phone number, and we agreed to try and get together.

I called him the next day from a public phone. I was doing everything to ensure my anonymity, as I needed this experience to be parenthetical to my life. His voice reassured me. He told me he was on his cell phone, driving home after shopping for groceries. We had a short introductory conversation, after which he gave me his address and directions.

A half hour later I parked in front of a large condo complex in Studio City. When I rang the doorbell, a man in his mid-fifties opened the door. He was wearing shorts, a button-up shirt with the tails tucked out, and a baseball cap. He sported a closely trimmed beard and mustache. He was shorter than I but far stockier. He looked like a regular guy.

"Come on in," he smiled. "I'm Stuart." I stepped into his living room, feeling as if I had arrived for an interview. He waved me toward his couch, then faced me in what looked to be his favorite chair. "You're very handsome," he said. He seemed pleased. "Would you like something to drink?" I really didn't. We spoke a little about his marriage, his divorce. He acknowledged having regular sexual relations with about three or four men. We also spoke of safe sex, the use of condoms. When we came to a pause in the conversation he rose and began drawing the blinds. The light dimmed. It gave me a thrill. Sitting back down, he said, "I would really like to see what you look like."

"I would like to show you." My voice sounded small and and a little shaky.

"If you like," he said. "You can take off your clothes in the bathroom."

"That would be fine," I said.

"I've left shoes in there for you," he said. "It would really turn me on if you wore them."

I thought that was nice of him, to encourage me in that way. I rose, thanking him. The bathroom was just around the corner. It was a small first-floor bathroom with a toilet, a washbasin, and a small cabinet. The shoes were in front of the cabinet. I felt myself blushing. They were red with two-inch heels. I took off my clothes and put them on the cabinet. I sat naked on the toilet seat. Trembling, I reached down and strapped on the shoes. Standing up, I felt precarious, delicately balanced, deliciously naked. I could feel every inch of my skin. A mounting excitement took hold of me. As if hypnotized, I opened the door and walked into the living room.

Walking in heels gives a curious effect to one's walk. I was trying hard not to strut or mince. Still, being on raised heels is like walking on tiptoes. The weight comes down delicately and moves up through the hip bones, accentuating and slowing down one's stride. I stopped in front of his chair.

He stared at me intently. "You're hot," he whispered.

I took a deep breath. "What would you like me to do?"

He sat back and started rubbing his crotch through his pants. "Run your hands up and down your sides. Feel your tits."

Although I have good pecs, I've never thought of them as tits. I placed my hands on my hips and ran them up my waist. I began to sway my hips. I pushed my pelvis forward.

"Oh, yeah," he sighed.

My cock was heavy when I came in. Now it was getting hard. I slid my hands down my stomach and cupped my balls. My cock grew harder, and I pressed it against my belly with the palm of one hand while continuing to caress myself with the other.

With one motion, Stuart brought his shirt over his head. He was barrel chested, hairy, and broad shouldered with a small but taut pot belly. He stood up and brought his pants down. His cock was hard, and he remained standing while starting to masturbate. "Show me what you've got," he breathed.

I rotated my pelvis while fondling my cock. Stuart kept masturbating. I liked what I saw. The man with whom I had previously had sex had shared a body type similar to Stuart's, but his dick had been tiny. Stuart's cock, on the other hand, was a size plus, not just long but thick, an ample slab of muscle. I couldn't take my eyes off it.

We were in sync. It's hard to imagine in advance how something like this will take off, but just as happened previously, it was effortless. We were completely turned on by each other. I found myself sitting on the edge of the couch. Stuart stood over me, rubbing the head of his cock over my nipple. I looked up at him; I didn't have to say anything. He knew right away and bent down to French kiss me. I took his cock in my hand and stroked it.

"I want to see your ass," he said.

"I want to show you." We spoke in short, stacatto sentences, voices low and breathy from excitement. I moved away and bent over, spreading my cheeks.

"Nice and tight," he said. I turned to face him again. We stood, jerking off, eyeing each other hungrily.

"Do you want to fuck me?" I asked.

He nodded. "Upstairs, on my bed."

We drew together. He put his hands on my waist, and I threw my arms around his shoulders. We kissed deeply. We ground against each other.

"Go first," he breathed. "I want to see you walk, I want to see your ass."

It took us a while to make it up the stairs. He was all over me, his hands everywhere on my body. His mouth devoured me. I had to urge him to be careful not to leave marks. As I climbed the stairs he moved his hand between my legs. I stopped and offered him my ass. I'd always wanted a man to feel me like this. That it was happening seemed remarkable.

When we entered the bedroom I fell onto the bed, flat on my back. He disappeared into the bathroom and came out with lubricant and condoms. He stroked my cock with one hand while inserting a lubed finger into me with the other, then two. He was slowly stretching me. It felt delicious. I pushed him back and sat up. "Give me one of those." I put the rolled condom onto the tip of his cock and used my mouth to roll it down. He sighed deeply. I licked his balls. Standing up, I pushed him down onto the bed and squatted over him, legs spread wide, weight on my shoulders. I lowered myself onto his thick cock.

He held me by the hips, drawing me down. His fingers dug into the flesh of my buttocks. He raised his pelvis to meet me. I lowered myself slowly, being careful because I was being stretched and also to sustain the pleasure. When he was in me fully, I slowly guided him out, then balanced briefly on the head of his cock before letting myself slide down the shaft again.

Only then did I lean forward to take his tongue in my mouth. The heavy French kissing prompted him. He began to fuck me hard. My ass heaved in the air with his thrusts. I sucked his tongue.

When he flipped me over, we moved as one. He dragged me to the edge of the bed so that he could put his feet on the floor. Without altering the rhythm of his thrusts, he raised himself up onto his hands. He looked down on me.

"I love this view," he said. My cock was bouncing hard against my belly. He took it in one hand and began to stroke me in time with his fucking. I raised my arms above my head, clutching a pillow. I closed my eyes. I listened to the sound of flesh slapping against flesh, letting myself be pounded.

I usually feel myself coming, but this time there was hardly any warning. I felt a weakness in my knees and a numbing of the crotch. I spurted a copious amount of thin white liquid, after which great gobs of cum drooled from the head of my penis. Stuart spread it on my stomach. A few thrusts later he pulled out and discarded the rubber sheath. Eyes bulging, he started stroking his cock. "Cum on me," I whispered. He stroked frantically, then bent, groaning. He ejaculated with force. I was surprised at the volume of his cum and at how it felt hot on my skin.

He remained bent over, leaning on his straightened arms. I raised my head . My stomach and part of my chest were soaked. Wads of his cum clung to my skin. Finally, he moved away and stood up. "Let me get you a towel," he said. "Don't get up. You're really covered."

When he came back I carefully wiped myself. I sat up and removed the shoes. "That was fun," I managed to say. We walked down the stairs. I asked him about a picture that was hanging on the wall. Now that the "interview" was over, it was as if he were walking me toward the elevator. We each dressed, not saying much, and just before I left, he told me that I could feel safe to explore there anytime. I thanked him.

Driving home and for the next day I felt an utter lack of interest in anything sexual. The world was emptied of eroticism, and at the time I wondered about it. Had I made a mistake?

It didn't take me long to realize that it was the result of my having thoroughly emptied myself, a result I cannot achieve with women.

That night, I received an email from Stuart. He had found it a pleasant surprise, he wrote, and would love to meet again. We tried, but at some point I backed out. Time passed. I lost his email address. And we didn't see each other again.

Become a Patreon to support Taletopia!

written by renmarlin