Chapter 5: Getting Randall Laid

I got a call from Rhonda after the bar bash, thanking me for the help I'd given in putting it together.

"Nah ... really it was mostly Elaine who did it."

"Well, I heard that it went pretty well."

"So ... how did your brother, Randall make out?"

Rhonda giggled.

"He didn't."

There was a pause.

"Oh ... forget I said that. It was cruel, kinda." She added.

"It didn't turn out very well?"

"Nope ... he's still far too shy."

"Rhonda ... tell me the truth. I know I asked you before, but is there any chance your brother is gay?"

There was a long silence.

"No, I really think not. Like I said, I once caught him whacking off to regular porn ... video of some guy with tats and a teenie chick."

"Okay ... so what do you want from me?"

"Ummm ... maybe you could talk to him..."

"I will but what do you see coming out of this?"

"I just want him to be better adjusted. To stop thinking of women as china dolls, fragile and sensitive. Women are people, just like guys."

"By that ... I guess you mean 'horny'?"

Giggles.

"Well, as I recall you don't really act like you are fragile and sensitive. And you are his sister, so why doesn't he take his cue from you?"

"I really don't know. Maybe our Mom ... she is really a 'proper lady' in public and very guarded around Randall, for some reason."

"Sorry for your dad, then."

Rhonda laughed.

"Oh, don't worry about that, she really is the proverbial 'whore in the bedroom'. I found that out by accident ... fortunately in my early teens."

"Okay ... I will talk to him. Now ... one more time, why me?"

"Ermm ... well, I talked to Elaine..."

"So?"

"She says you have exactly the right attitude toward women. You love and appreciate them but have no bigotries where sexuality is concerned. She said you didn't blink an eye when she told you she had a lesbian relationship."

"Well ... I got to admit I blinked a 'mental eye'. But when I thought about it, I realized it didn't matter, in the larger scheme of things. But it is just her opinion about what is the right attitude."

"It's mine as well. I've tried to talk to Randall but he gets really uncomfortable ... and he said he hates how most guys talk about women and sex."

"So ... what you're saying is he never was 'socialized' to his peer groups."

More chuckles. "Hell ... exactly what is a nerd peer group?"

"Good point. Okay, I will think of a way and then talk to him. Here's a question ... what about if I do more than that? I have an idea to bring him outside the bubble. And somewhere else, so he isn't concerned about whether he runs into the girls again?"

"That's a great idea"

Actually I had someone in mind for him to meet. Jenny lived near Miami's South Beach and the chances of them meeting here in Toledo were next to none. She did love sex, and once the ice was broken made no bones about it. And she loved men.

She would probably be considered a 'slut' in some circles but I knew she was simply a 'breeder'. Meaning she was a prospective wife and mommy who simply hadn't met 'Mr Right'. And she was cute but not what most would consider a 'beauty'. She wasn't a real smart girl but by no means 'dumb' or stupid.

Once she had realized I would treat her like any other woman I met and that I wasn't judgemental, she confided that she loved showing off for the camera. And she felt comfortable in that I was way out of her age range, thus the sex ... Friends/benefits style ... would be no problem.

I had, over a few months, convinced her to stop the dangerous practice of picking up men in bars, instead cultivating a few close relationships with guys she could trust. For her, that ended up being a mix of educated and/or intelligent successful guys she met at work, school or church. Mostly, because they were the least likely to want to take things past the casual stage, these guys were married. I suspect she also liked the game of arranging their clandestine meet-ups.

I emailed Jenny letting her know I was traveling down to Miami for a week or so and was bringing along a shy young friend who I'd like her to meet.

I left it at that.

What experienced young woman wouldn't like breaking in a virgin? Especially if he was fairly attractive.

The worst thing that could happen is that Randall would be intimidated by her open sexuality. And later when she went for multiple positions and orgasms. Ie; she fucked like the proverbail bunny. That didnt bother me; she came a lot while I fucked her, but who knew how he would look at it.

Meanwhile I had to convince Randall to come along with me. Fortunately it was near Spring break at our local college, and better, that break came a few weeks prior to most northern schools.

Rhonda actually did the most to arrange that, I was invited to meet them at the student cafe, we'd decided to bring up the subject of my trip, then. Rhonda had already been nagging him to get away during the break, he never had done that, before.

His argument was that he had no desire to be a 'party animal' on a beach, in beach bars, or anywhere else. He believed it was childish and immature.

So when I invited him to tag along with me on a business trip that just happened to be at break week, he thought about it a little and agreed. I told him that he would only have to pay airfare, and for a few meals, I'd spring for everything else and put it on my personal business expenses.

While we were on the plane I gently brought up the subject of his female relationships. After beating around the subject for a while he admitted his main problem was that he felt he wouldn't be able to satisfy a woman because he was so quick on the trigger. I prodded a little and he finally said that, even if he masturbated just prior to a date, he'd shoot off in his pants shortly after starting to make out with whoever he was dating.

I just looked at him and replied;

"So... ?"

"Well ... that's embarrassing!"

"Hmm ... do you lose your erection when that happens?"

"Umm no. But it's a sticky mess. Who wants to let a nice girl see that!"

"Well did you ever talk to the girl about that?"

He looked at me with shock on his face.

"No ... of course not!"

"Not even Rhonda? How about your dad, or your mom? A buddy?"

More shock.

"Of course not. Who wants to admit they have a problem with premature ejaculation!"

I just laughed and, to leaven it a little, winked and smiled at him.

"Son, take it from me ... if your pecker stays hard, it's not premature. What it is, is sort of like the first course."

He stared back with doubt on his face.

"Seriously ... if it happens and the girl you are with knows anything about sex and sees that hardness still there, she will probably take that as a compliment."

Still, doubt remained.

"Let me ask you this ... did a girl you were making out with ever have an orgasm while you were just kissing and feeling her up?"

He thought a few moments.

"Yeah ... come to think of it, I guess so."

"What did you think about that?"

He colored a little. "Well, I wondered if she wasn't maybe a little easy. Or maybe I was taking advantage of her."

"And you never asked Rhonda about that?"

"Heck, no ... she's my sister!"

"Randall, trust me ... you have a lot to learn about women. They aren't that much different from us. They just have to be lots more careful."

"I dunno..."

"Believe me or not, you could have talked about it with Rhonda. And you will be able to do that pretty soon."

The pilot called the descent and, as soon as we got into the terminal, I texted Jenny to meet us at Cafe Robles in an hour.

We caught a cab to my condo which is two blocks in from the beach, dropped the bags, and walked to the cafe.

She was waiting for us when we walked into the foyer. Wearing a simple sundress, and probably nothing underneath it, I was struck at how cute she was. A moderate tan despite the hours per week she spent sunning on the beach, no facial wrinkles as yet. She'd told me the key was in high end makeup and moisturizing emollients.

Whatever, she never failed to increase my pulse, just on speculation.

She gave me a beaming smile a big full body hug and a peck on the lips.

"Randall, this is my friend, Jenny ... Jenny, Randall. I'm an advisor for his engineering fraternity and he came down to sort of keep me company and check out what my business is about."