Chapter 31: Jessie Redux

Leah Tarred & L. O. Sailor

The following day, after school and some getting in shape kind of running, I was luxuriating in the hot-tub with Mrs. Whitestone.

"But I was giving her some good advice about the excess make-up, why did she get so pissed that she had to run off like that?"

Gerry didn't answer me at first, preferring to send her right foot between my legs, ultimately lifting my dick up to the surface where she could see it.

"Aubrey, my dear, apparently there is a lot you don't know about women. Please don't take offense, for someone your age, you know a remarkable amount about what women want, need, and like. What I'm getting at is most women are cursed with insecurities because of ... well, the media and what they say a woman should be. We're bombarded with crap. You see it in the newspapers, on TV, and those God-awful magazines like Cosmo, just to name one. Women always have to compare themselves with visions of perfection, and as a consequence, always come up short. And why wouldn't they?

"So when little miss ... what's-her-name, heard you say she wore too much make-up ... well, she kind of blew a fuse. You had just made love to her. Undoubtedly made her feel better, and more womanly then she'd ever felt before. That is, if you gave a half decent performance. And I expect you did. Experience tells me there's nothing like a fresh pussy to inspire a man.

"Give her a day or two to think things over. Women analyze every word spoken, every facial expression, every possibility of their time with a man, and so given sufficient time to think, she'll come around to your reason for saying what you did, and she should, if she has an ounce of brains in her young head, conclude that you meant well by her when you told her about the excessive make-up."

"You think?" I said, as a feeling of relief swept over me.

"Aubrey, I absolutely guarantee it, now put that rising pole of yours into my pussy. It's starving for the kind of affection only you can give it."

Gerry slid down in the tub and locked her legs around my waist as I sank into her cunt. We both sighed with that satisfaction, me on feeling her tightness closing down on my cock; she on feeling my shaft parting her vaginal walls. It's almost beyond description, the loveliest of feelings surpassed only by the moment of climax ... and nothing beats that feeling.

We settled into a leisurely fuck and I used that to ask Gerry another question I considered important.

"So, do I wait for her to come to me?"

"No, you go to her, apologize. She'll accept it and you'll be back in her good graces. Might even blow you right then and there," she said laughing.

"While we're on the subject, how is it that Hank doesn't mind us getting together like this?'

"Because men are naturally predators when it comes to women and sex, I encourage him to get laid wherever he can with only one proviso."

"What's that?"

"That he stays free of STD's"

"I thought women preferred men ... their men to remain monogamous."

"Most women do. But again, that's because of their basic insecurities. Women who have worked in strip clubs, or prostitutes have much better insights into how a man thinks, and what a man wants in a woman."

"What's that?"

"They'd like to come home to a different woman every night, or at least some nights.

"Some women change their mannerisms, such as the way they dress, hair styles, even wear wigs. Hank and I used to agree to meet in a lounge. We'd arrive separately, and he would pick me up. I would try to look different each time. And for a long time that sufficed."

"So, what happened?"

"One night, another guy moved in on me before Hank arrived. I was enjoying the attention, and let the guy sweet talk me, even after I saw Hank come in. To my surprise, Hank signaled me to keep going, and at a given point, when Johnny, that was his name, had to take a ... I mean go to the bathroom, Hank pretended to move in on me. It was what he said in Johnny's absence that got me about as horny as I'd ever been to that time."

"What the hell did he say?" I asked and accidentally slipped out of her pussy. I made a quick refit and we continued to move so slowly back and forth that if it weren't for the jets in the tub, I doubt we'd have made a ripple in the water.

"He was about as nervous as I'd ever seen him, but he asked me if I wanted to fuck the guy."

"And?"

"I said yes, but only if he was there with us."

"You didn't!"

"I did, and he agreed. We went home with Johnny and they took turns fucking me silly. It was so good that we agreed to meet again the next Friday night, and do so for about two months."

"What happened?'

"Johnny was in an accident. He was in the hospital for several months. By then Hank and I had turned to swinging. Do you know what that is?"

"Um, making it with a group ... something like that?"

"Yeah, something like that. Now let's get serious here, I need a good cum, baby."

I leaned closer and kissed her as my hands slipped underneath her to grab two handfuls of her asscheeks. After the kiss, Gerry laughed and propped her legs up as high as she could on my body to give me what depth she could while keeping her head above the surface of the water.

I pumped in and out of her in short, fast strokes. They were not as pleasurable as running myself in and out of her for what my length allowed, but it was all I had the mental energy for. I moved from her lips and put my face in the hollow of her neck. She whispered to me; I do not remember what she said, but it was a comfort as my orgasm built. She began to squeeze me with her pussy, which only quickened the approach of my release. I sucked where her neck joined her shoulder knowing it would leave a mark but wanting to mark her even if only temporarily. I knew Hank wouldn't mind.

It was all over too quick for me. I pulled out as far as I could and thrust into her one last time. Gerry knew what it meant; and at the bottom of the stroke as I hesitated, she gave me the last bit of stimulation by squeezing and releasing me. I felt it just inside my ass; the ting of pressure being released. I felt my balls relax as my load flowed up my dick, and as I came, she marked me by sucking in the same place I had her.

Gerry kept squeezing and releasing me, milking me until I collapsed on top of her. She whispered to me as she stroked her hands up and down my back. I still could not separate what she was saying into distinct words. They brought me back down to reality slowly though. I tried to move to her side, but she gripped my body with her legs and arms to keep me in place.

"Stay here, like this," she said. "Just stay a little longer."

I wanted to please her, so I did just that. She rewarded me by telling me what women saw in me.

My guess is that she was reiterating what she saw in me. But her phrasing was what women in general, saw. And I was fascinated.

"They see your mouth," she said. "It calls out to them. They want to feel your lips on theirs. Next they notice your ass. Yes, your tight little butt. Women like a man with a firm ass. They seem to think it makes for a good lover. I think they really mean a good ass means they guy's a potential pile driver when it comes to fucking. Women love that. Almost all of us fantasize being screwed in an alley someplace, our dress up around the hips, with our back rubbing against a filthy wall, being jack-hammered to orgasm after orgasm, by a brute of a man with a big cock."

"Really?"

"Really. You also have marvelous eyes, Aubrey; they are marvelous, absolutely marvelous."

"You're beginning to sound like Billy Crystal on Saturday Night Live," I told her, and we both laughed.

"I'm so very wet, Aubrey," she said. We were standing on the edge of the hot-tub. Gerry sat down on one of the lounges and spread her pussy with her thumbs. "Look here, Aubrey. Come closer, take a good look. Tell me what you see."

I see ... pink ... and the lips appear swollen, but I guess that's..."

No! Not that. Look closer."

I did, but couldn't offer any new insight that might satisfy her.

"Do you see your reflection?"

"Huh?" I realized how stupid that sounded and apologized. "I'm sorry, but I..."

"That's okay. Only one guy ever saw his reflection in my wetness."

"Who was it?"

"Never mind. He ... he's gone.'

"Dead?"

"Yeah ... he's dead. A long time now," and she began to cry. I pulled her into my arms and tried to sooth her, to end her crying, but couldn't.

We walked inside, side by side and I put her to bed, and after twenty minutes saw that she was sleeping, and I left before Hank came home.

The following day I made it my business to use the track at the football stadium, where the cheerleaders practiced. I saw a couple of them watch me as I ran past them, including none other than Jessie Von Broklin.

I ran and kept running until the girls were finishing up with their practice. Only when I saw their coach leaving did I trot towards the cheerleaders. Jessie stepped away from them to meet me.

I didn't get any hugs or kisses, nor did I expect any. But I did get a big smile and an apology.

"I'm sorry about running off on you," Jessie said.

"I'm glad you are. That was a terrible thing to do. I mean I could have been eaten by a grizzly bear, or something."

She appreciated my attempt at humor and laughed louder than she should have. I was back on firm ground with her.

"Walk with me?" she said imploringly.

"Sure," and I fell in alongside her.

"I still tingle, from ... you know."

"It's known to have long term effects sometimes." I said for laughs, but she thought I was serious, and agreed.

"It does, doesn't it? I'm amazed, really I am."

"Want a repeat performance?"

"Oh, yes!"

"When?"

"Um ... I'd like it now, but Larry's supposed to pick me up ... so..."

"I'll take a rain-check, then. You still have my number?"

She bit her lip. I knew she'd tossed it, and asked her to get a pen and paper. Jessie scampered over to the other girls and asked for pen and paper, which one of the girls provided.

I scribbled my number down and pressed it into her hand. We were close enough so that at least some of the other girls could hear us, and I deliberately said, "Don't lose it, or there won't be a next time."

Glancing around to see if Larry was on the scene, I saw that the coast was still clear, and I pulled her close and asked her if she wanted me to kiss her.

"I..."

"Yes or no, it's a simple question."

"Yes!"

I kissed her, replicating the famous kiss bestowed by the sailor in Times Square on V J Day. You must have seen the picture, it's a classic. Then I walked slowly away, leaving Jessie standing on wobbly knees, with all the other girls as witnesses.

My phone was ringing as I walked into the house. My mother was at work, she usually worked until six or six-thirty. It was four-fifteen. I picked up on the next ring and said "Hello."

"Aubrey?"

"Yes."

"Jessie. Can I see you?"

"Sure, nobody's here but me, want to c'mon over?"

"I'll be there in ten minutes, okay?"

"I'll be waiting."

Twenty minutes later we ended a torrid kiss, and Jessie wriggled away from me, got up and slowly, provocatively, stripped her clothing off.

"Very nice," I said, and watched as she lay down on my bed and spread her legs, then, using her thumbs, spread her pussy open, showing me the pink.