The Teenage Dream

The night my lover, Jake, told me about his first sexual experience still resonates in my mind when I’m feeling sensual. It’s been the background for many adventures over the years, and no man has ever complained.

As I settled in next to him on the bed, Jake started talking about his first real relationship. Stroking my arm softly he began, “I never tell this to anyone. It’s embarrassing. But shit. When I was about fifteen, I mowed lawns in the summertime for spending money. My dad was old school about money. You wanted something you had to work for it. An allowance? Pfft. What was that?” He laughed.

“So, you mowed lawns- and?”

“My ma was friends with a lady in town who asked her if I could do her lawn for her. Her husband was out of town a lot and she didn’t think she could handle it.”

“What did this lady look like?” I teased.

“I was fifteen and horny.” He joked, “It didn’t matter- No. But, seriously, she was hot- well, hot for an old lady.”

“How old was old?”

“I think she was late thirties or something. But man. She’d come out to bring me iced tea in these tight shorts whenever I was there mowing.”

I interrupted him. “You drank iced tea out of her shorts? That is pretty hot.”

“You’re a smart-ass, you know that?” Anyway, he continued. “I hated iced tea, but I always drank the whole thing down so I had an excuse to check her out while she waited to take my glass inside.”

“Very clever.” I mimed applause.

“One day her car wasn’t there when I started mowing. By the time I got to the backyard, she’d gotten home and asked me to help her bring in some stuff from the car.”

“Of course, you said, ‘No, ma’am. I don’t want to go inside because you might seduce me.’ Right?” I joked.

“Not likely. By that time, I’d done it with her in my head about a thousand times. If there was a chance, I was going for it.” Rolling lazily to his side, he leaned on his elbow and continued his tale. “I’m hauling bags of shit into the kitchen for her, and she starts making a big deal out of a run in her stocking. Next thing I know I’m getting a free show of her thighs as she hikes her skirt up high enough for me to see the tops of her stockings. She says to me, ‘Come over here and look at this run in my stocking.’ So, being a helpful guy, I did. Then,” he continued, “she pulls her skirt up a little higher and she wasn’t wearing underpants. I mean. I was there staring at everything and not knowing where to look.”

“ I’ll bet you didn’t know where to look.”

“Man. There she was in her stockings and heels, her dress hiked up, and she whispered to me, ‘Do me on the kitchen table.’ Holy shit- a teenager’s dream come true.”

“Did you have to fight her off? Did you finish mowing the lawn?”

“Hell, no. I hopped on that before she could change her mind, and anything I imagined before was nothing like the real thing. She took me to the bedroom and destroyed me. Literally destroyed me.” He reminisced while stroking my thighs and turning me into a hot mess. “I crept back home about ten o’clock that night and Ma was up waiting for me, mad as a wet hen.”

“So, that was it? Did you go over there again?”

“Shit, I practically spent the summer at her house. It was like she never got tired. When school started again in the fall, I’d skip classes to see her.” He said, “Then, one day I skipped Chem class to see her and there was a strange car in the driveway. Every time I tried to see her again that same car was there and that was it. It was over.” He reflected, “I guess she wanted someone with a driver’s license!”

“She was crazy to let you go. Wanna pretend I’m a horny housewife and you’re fifteen again?” It was a good night. A good night, indeed. Just call me Mrs. Robinson- and yes, I did put my silk stockings on for him and let him destroy me.