A First Timer’s Tale

Whatever reservations I had melted. Along with everything else, I’d had hammered into my thick skull that I was given what I had been so I could help people when they needed it. Wendy’s plea for help was exactly the right tactic to flank my rapidly crumbling walls.

I didn’t say it was okay. I didn’t tell her to go ahead. I just withdrew my hand from between us and stopped trying to stop her. She decided to take that for assent.

Wendy’s nether lips were so swollen and I was so hard, neither of us had to guide. I felt something slick and hot press against my tip and then part to engulf me. A tight sleeve slipped over my shaft and down, down, down.

“Ah.” Wendy sighed when I was almost fully ensconced. “That helps. It’s helping. A little. It’s not quite so bad, now.”

The warm moist sleeve sheathing my shaft felt incredible. The pinch of my underwear and jeans on my scrotum just behind my balls, not so much. My eyes were opened to just how tempting actual sex could be, but I wished like hell if we were going to do this I could get my pants lower.

Then, Wendy began to move.

If she’d bounced up and down, sliding that slippery molten heat along my length, I wouldn’t have lasted more than maybe two or three trips. But, she didn’t. Instead, her hips worked back and forth pulling my cock away from my belly and causing me more discomfort on top of the pinch behind my balls.

But, the little shifts her motion allowed, letting me slide just a tiny amount inside her was enough I would have let her break my dick right off.

On one last hard thrust of her hips I thought she had. Pain shot through me, overwhelming my enjoyment, and I felt wetness coating me down where I couldn’t see.

“Aaargh!” Wendy groaned to the car roof. “Yes. Oh, that’s better. So much better. Thank you, Kevin. You have no idea how much I needed that.”

Wendy slipped off me, back into the driver’s seat. She pulled her pants back up her left leg while I was still checking to make sure the wetness I felt coating my still erect cock wasn’t blood.

“Could I have my clothes, please?” Wendy asked, her cheek pressed against the steering wheel as she laced her boot back up.

“Uh, yeah.” I tucked myself back in, still hard, and leaned forward to retrieve her bra and sweater from between my feet. “Here.”

“Thanks.” Wendy said and set about slipping her bra back on and pulling her sweater over her head while I wrestled my shirt back over my shoulders and buttoned back up.

“Seriously, Kevin.” Wendy leaned across and turned me to face her. “Thank you. I can’t tell you how much you helped me. How much better I feel.”

Then she gave me a gentle kiss.

“I’m glad I could help.” I said. “So, uh, what else did you want to do? Dancing, I guess? I think that’s about all that’s still open.”

“Actually, I have an early class.” Wendy said, cranking the ignition. “I should probably take you back to your car and think about getting some sleep.”

“Oh.” I said. “Why didn’t you tell me?”

“Because I wanted to see you, silly.” Wendy laughed, swinging out onto the street. “I wanted to spend some time with my boyfriend. Didn’t you like what we did, too?”

Please wait…

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