My first and last date with a girl

Everyone in this story is 18+.

Thanks to my new arrangement with Frank, I had a lot more free time these days. I didn’t have to worry about rent, I didn’t have to work… all I had to do was swing by every Friday and do what he asked. All in all, things were pretty great!

Between weekly visits, I decided to start looking for a girlfriend. Or at the very least, someone to hook up with. I spent a few days scrolling and swiping before I finally found the right one.

Marissa.

She was absolutely gorgeous, and funny too. We hit it off right away, and we already had a date planned for Thursday. A fancy dinner, and to quote her, “dessert if you’re lucky.” I could only hope.

Thursday finally arrived, and dinner was wonderful. After I paid the bill - thanks to Frank, of course - I proposed heading back to my place. To my surprise, she agreed. Back at my place, I opened the door to my apartment and showed Marissa inside.

“Such a gentleman,” she teased.

“But of course,” I replied. “May I take your coat, madam?”

“Andrew! Already trying to take my clothes off?” The two of us shared a laugh. “I’d say buy me a drink first, but you already did that…” She winked at me, then removed her coat and tossed it over.

I caught it, goofy smile and all, then turned to hang it up.

“I love your place,” Marissa commented, entirely too kindly. She lingered nearby, taking in the grand view of a tiny one bedroom apartment. “What is it you do again?”

My heart fluttered for a moment. “I’m, uhh… sort of a… personal assistant, you could say.” Recent evenings with Frank flashed through my mind. I pushed the thoughts aside; it would be best to change the topic. “Do you want a tour of the place?”

“How about you just show me the bedroom instead?” she asked.

A minute later, we were rolling over each other in my bed. We were passionately making out, hands traveling as we explored each other. I touched her breasts. Then her ass. She had one hand running through my hair, the other on my bare chest. It was thrilling and scary and exciting all at once.

Her second hand began to slide downward, and I felt my heart racing. Slowly down, brushing past my stomach. She kissed me harder. Her hand slipped under my waistband. I inhaled sharply as her fingers slid down, reached for my dick, and…

Marissa broke our kiss. “What’s the matter?” she asked. “Too much to drink?”

“Nothing!” I said quickly. “I think I’m just nervous.” Yeah, nervous. That was it. I just needed to ease into it.

She let go of my soft dick and sat up. “Maybe you need to get out of these pants first,” she suggested. Marissa proceeded to help me take my pants off, then my underwear, revealing a limp and not-at-all excited penis. A frown appeared on her face, but she quickly hid it.

“Sorry,” I said, laughing nervously. “I promise it gets bigger.” I sat up, propping myself up with arms extended behind me. Naked and feeling incredibly shy, exposed, hoping I hadn’t blown it.

“No worries,” she said with a disarming smile. I felt some of the pressure fade away. Then she leaned in and kissed me again.

Her hand went for my dick, taking hold of it and gently tugging on it. We made out, our tongues colliding and entangling, my hands exploring her body, hers still touching my dick. I was so desperate to make this work… desperate to please her… desperate to prove to myself that I was straight.

But nothing happened.

Minutes later, my dick was still soft.

“Maybe I should go,” Marissa said.

“Wait! Just a bit more! I promise I’ll get hard.” It was so embarrassing to say it out loud. I was completely naked, she was fully clothed, and I was begging her to stay. But no matter what we did, I couldn’t get hard.

“I’m sorry, Andrew.” Marissa kissed me one last time, then collected her things. I said nothing as she left.

I remained on my bed and stared at my pathetic, limp cock. What was wrong with me? When I was with Frank, I couldn’t stop myself from getting a boner. Just being within a hundred feet of the guy’s house got me hard! It didn’t make any sense…

Last time I was with him, my dick was hard as a rock. I rubbed his feet while he jacked off, staring up at him from my little spot on the floor, right in front of his couch. I remembered his heavy balls bouncing with every stroke, swinging up and down. His hand wrapped around his fat cock, pumping it. I remember being unable to look away.

I glanced down and saw that I was starting to chub up.

That was a crazy night. And at the end of it, Frank shot his load straight into my underwear. He covered my dick with his cum. The whole walk home I had to keep it tucked into my waistband because it just wouldn’t go down.

Aaand, now I was rock-hard.

I hopped off my bed and started digging through my laundry basket. A minute later, I found what I was looking for: a crusty pair of underwear, covered with Frank’s cum.