Dreaming of Jolene By Steve Slavin

Let me tell you just one thing about me: I have always been – and always will be – a strictly heterosexual male. End of story!

You’re probably wondering why I find it necessary to make this statement. Well, back in the eighties and nineties, no one needed to say that. You were a guy, you were a girl, or maybe you were bi. That was it! You had three choices – not a whole fuckin’ menu!

But today? Shit! I mean the definitions and sexual identities keep changing every couple of months. Which, I happen to think, is complete bullshit. I’ve always looked at it this way: You’re either straight or you’re not. End of argument. Finito!

Yeah, yeah, yeah – I know what you’re thinking. Who is this ignorant, completely out of touch schmuck?  Am I right? And you probably think I’m some old dude who can’t stop blabbing about the good old days.

Whatever. I always thought fifty was old – so I’ve still got a couple of years to go.

Look, I’m sorry I got into all that shit, but if you’re going to understand what happened to me, then you need to know exactly who I am – and what turns me on. OK?

What I’m going to tell you all happened exactly ten years ago, almost to the day. It began on a Thursday night. I was living on the Upper Westside, and early one evening I saw this hot-looking chick in the supermarket. I could see that she was interested when we smiled at each other.

She was about as tall as I am, which is unusual for a girl. That’s because I’m a shade over six feet.

I used to have a friend who wrote a book to help singles meet in the city. Her theory was that if a person was attracted to you, you could say anything, and they would respond.

“Come here often?”

She laughed. “Is that the best you can do?”

“Look, I have this friend who wrote a book about meeting people.”

“And did your friend suggest that line?”

“Well, you’re talking to me, aren’t you?”

We both laughed. Then I said, “I am so attracted to you!”

“Really?” she said.

“Well, yeah. Or else, why would I make such a complete fool out of myself?”

“You tell me!

“So, can I have your phone number?”

“You know what?” she said. “Maybe it’s better that we just have our fantasies.”

You are my fantasy!”

Exactly! And I could never live up to that.”

“Maybe our reality could be even better than our fantasy.”


“Look, I’ll bet you’re as attracted to me as I am to you.”

“What makes you think so?”

“Because you’re still talking to me.”

“Point taken.”

“I’ll tell you what. I live just a few blocks from here. Come back to my place and I’ll fix you dinner.”

“Very smooth.” We both laughed.

“Look,” she said.  “I’ll tell you what: Here’s my card. I’ve got some stuff to do now. Why don’t you come over in a couple of hours?”


 “OK, but remember what I said. Fantasy is better than reality.”

“I’m going to prove you wrong.”

# # #

I glanced at her card on my way home. Her name was Jolene – and she was an art therapist — whatever the hell that meant.

The only time I ever heard of that name was in a movie I had seen years ago. The actress who played Jolene was maybe semi-attractive and pretty flat-chested.

But I loved the name. And my Jolene was the opposite of flat-chested. And she had very long, light brown hair. I supposed that in the sixties she would have been called a “hippie chick.”

She had high cheekbones, big brown eyes, and a great smile. When she smiled, you smiled.

Jolene had long legs that looked like they never quit. You want a fantasy, Jolene? I’ll tell you mine. I wanted those long legs wrapped around my head. But I’ll bet she already knew that. And I’ll bet she also knew a lot of other things.

# # #

Two hours later, I rang her downstairs bell, and she buzzed me into the building. When she invited me in, she gave me a light kiss on the lips. I was smart enough not to push it.

We sat at her kitchen table drinking tea. We talked and talked and talked. And finally, we started to make out.

Slow and easy, I thought to myself. We had all the time in the world. But I had this huge erection and I knew that she could feel it. We must have been kissing for at least half an hour. Then she said, “Look, John, why don’t we continue this tomorrow night?”

I just looked at her. I couldn’t believe that she was going to send me home with the worst case of blue balls. Very, very reluctantly, I began to disengage.

She took my face in her hands. “We both have to go to work in the morning, and it’s already past midnight. But tomorrow’s another night.”

Maybe she was right. And besides, horny as I was, I was in this for the long haul. Didn’t mama say there’d be nights like this?

So I limped the eight blocks back to my apartment and within a few minutes I was dreaming about Jolene. This time we went a lot further.

On my way to work, I laughed thinking about what Jolene had said about fantasy and reality. I could hardly wait to see whether or not she was right.

We had a date for eight p.m. I brought her flowers. She put them in a vase. Five minutes later we were rolling all over the floor making out.

Soon I was humping her with my thigh. She arched her back and I could feel her shuddering. This was going to be easier than I thought. If I could do this to her with my leg, then just imagine how hard I would make her cum once I was inside her.

Our tongues were practically entwined. I thought she was actually going to deep throat me. I don’t know where she learned to kiss like this, but she knew a hell of a lot more than I did! Teach me, Jolene, teach me!

I had never been so aroused in my life. Now we were lying side by side. She was stroking my cock through my pants and I was fondling her breasts through her bra. As much as I wanted to take things to the next level, I think I could have just kept doing what we were doing forever. This was, by far, the best sex of my life, and I was barely at second base.

I was smart enough to know that she needed to be in control, so I let her move things along at her own pace. Soon she unzipped my fly and reached in.

Now she had complete control. She had her tongue in my ear and my cock in her hand. She wasn’t giving me any choices. In less than a minute she made me cum.

After we caught our breath, she kissed me and said, “There’s something I need to tell you.”

I just stared at her.

“I can’t sleep with you right now.”

I just starred. I didn’t know if I was mad or sad – or maybe both.

“It’s a physical thing. I’m not physically capable of having sex right now.”

“Are you ill?”

“No, not exactly.”

“Do you want to talk about it?”

“Maybe another time. Maybe if we get to know each other a little better.”

“OK. Look Jolene, I want you to know something. You are the most exciting woman I have ever been with. I don’t know what’s wrong with you, but I really, really like you.”

“I know that, John. I know that.”

“Can I stay over? We can just hold each other. I’d really like to do that.”

She kissed me. “Maybe soon, John. But not tonight.”

I helped her up, and we kissed good night. By the time I got down to the street, I was thoroughly confused. What was wrong with her? Was she dying? Did she have a social disease?

As I walked, I considered a few more possibilities. And then I began to wonder what was happening to me. Look, I was thirty-eight years old, and maybe for the first time in my life I was actually falling for somebody.

Well, I could have done a lot worse for myself. And even if we found that we didn’t have all that much in common, to paraphrase that old Captain and Tennille song, “Sex will keep us together”.

I’m not a very patient guy, but I was willing to wait till Jolene was ready. I knew I could trust her. No matter what – I’d do whatever she wants. Isn’t that what love really is?

I wanted to tell her that even though we barely knew each other, I would be there to help her with whatever she was going through. I mean, isn’t that how you know who your friends are?

Even though we had only just met– and we had not yet been intimate – I felt I already knew her body better than any other guy she had ever been with. And even though we hadn’t actually “done it”; it still was, by far, the most exciting sex I had ever had.

I could stop looking. No other woman could come close. Ladies and gentlemen — I have an important announcement. My search is over: We have a winner!

When I got home there was one message on my phone. I was hoping that it was from Jolene, but it was from my friend, Larry.

He and I were basically party friends – not real friends. We partied together, occasionally talked on the phone, but never just got together.

It was too late to call him back, so I went straight to bed. Needless to say, I dreamed of Jolene.

When I woke up I decided to call Larry, and then Jolene. Maybe she would agree to see me tonight. We had not yet gone out on a real date. The only problem was what happened later. Maybe I could just walk her to her door and say good night. Fat chance!

So I reached tor the phone and called Larry. He probably wanted to tell me about some party. Well Larry, I hate to tell you, but my partying days are over.

When Larry picked up he got right to the point. “John, I heard you’ve been seeing someone.”

Wow! News travels fast! How did you even hear about us?”

“You know the old grapevine.”

“So you know her?”

“No John, not directly. But I know a couple of guys who do know her.”

“Are we talking about the same girl? Her name’s Jolene.”

“Same girl.” There was something in his voice I didn’t like. He seemed to have taken on the tone of a funeral director. I was beginning to get the impression that just maybe it was my funeral.

“So Larry, what’s the story?”

“In a word?”


“John, you better sit down.”


“Jolene’s a guy!”

I didn’t say anything. I couldn’t say anything. My stomach was going through violent contractions. I was having a very bad case of the dry heaves.

Larry must have been able to hear me. He kept asking if I was OK.

It took me about half a minute until I could gasp, “No, not really!”

He then patiently explained everything. It turned out that Jolene was a pre-op guy waiting to have a sex change operation.

“You mean they haven’t cut it all off yet?”

“You got it!”

“Holy fuckin’ shit!”

“Yuh can say that again! So John, let me ask you a question.”

“The answer is ‘No!’”

“No, you didn’t fuck her?

“Larry: stop and think! If I had fucked her, you don’t think I would have noticed something?”

“Yeah, that’s true. So John, why are you so upset?”

“You want to know why I’m upset? I’ll tell you why I’m upset! I’m upset because never in my entire life did I ever meet someone so beautiful, so sexy, so sensual, such an unbelievable turn-on.”

“Yeah, so what’s the problem?”

“You wanna know the problem, Larry? I’m the problem! I just can’t do it!”


No! I’m a guy! And Jolene – well she’s a guy!”

“John, you just said you practically love her. And after she has the operation, she will be a woman. If you’re so fuckin’ attracted to her now, then just think how attracted you’ll be once she’s all healed.”

“Larry, listen to my words: I’m a guy. And operation or no operation she’s a guy! End of story!”




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