Intro to Jolene

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I had the pleasure to meet Jolene during a business class I was taking at the community college, many years ago. On the first night of class, she came in late, due to a fender bender, and there happened to be an open spot next to me. She sat next to me, and I had to struggle to pay attention to the professor, and not to her.

Jolene is a bombshell of a woman. She always has been. 5’7″, flowing auburn locks that fall just below her shoulders, 32b bosom that is just full enough to be fun, and an hourglass figure that is just a touch bottom heavy. Being just shy of 150 lbs, though she will rarely admit it. She is a head-turner.

As many classes do, we were paired in teams, so I scrambled to make sure I was paired with her. We went over our case studies, and when the class was done, I asked if she needed a ride due to her accident. She thought I was cute, and suggested we go for coffee instead.

Coffee. Right. I was almost certain I had struck out. I had no idea…


She needed to take care of some things, so we agreed to meet the next day. I was sure the only reason she wanted to get together was to go over any notes she may have missed. I walked into the cafe the next morning, and I had to bite my lip so that my jaw would not drop. Across the cafe sat Jolene, with her hair pulled back into a ponytail, designer frames casing her amazing ice-blue eyes. A silk white blouse beneath a heather grey blazer, and matching pencil skirt. The accessories were sparse, black heels, and a simple diamond pendant.

“My god,” I thought, “who is this woman?”

I felt like I was going to meet my lawyer, unprepared.

“Hi Brian,” said Jolene as she stood, “I’m glad you could join me. Can I get you anything?”

I told her that was not necessary, and excused myself long enough to grab a latte.

“So, you seemed to have a rough night last night. Is today going better for you?” I posed. Jolene took a sip of her black coffee and smiled.

“Yes, last evening was crazier than I would prefer. I am glad it didn’t go any worse. Thanks for your concern.” She took another sip, savoring the bold flavor of her dark roast. “That was why I wanted to see if you would meet me for coffee.”

She wanted to meet for coffee because I showed concern? Now I am getting a bit confused.

“Brian, I am going to be blunt. I am a busy woman, and I don’t have time for any extra drama.” She took another sip of her coffee, just to draw things out, “Are you seeing anyone?”

Whoa. Straight shooter this one. And I thought I didn’t stand a chance.

“Well Jolene, that is blunt indeed.” I took a sip of my latte, providing equal suspense to what she afforded me. “You would be in luck. I am not presently seeing anyone. What did you have in mind?”

“Had in mind. Perfect choice of words. I had in mind, a bit of a negotiation,” she smirked, “if you’re up to it, that is.”

“I’m listening. Go on…” What is happening here, I thought. I can’t pinch myself, she’ll see. We’ll just have to wait and see how this plays out.

“Well Brian. I gathered from your behavior last night that you were ‘into me’, as it were. Found me attractive, if you will. I was hoping to capitalize on that…” She sat back and took another lingering sip of her coffee, watching me. In return, I was watching every move she made, not knowing what to expect next.

“Alright, I can admit, I do find you attractive. What do you mean by ‘capitalize on that’?” I inquired. I feel like a guilty child, all of a sudden. The pretty girl knows I like her, and now I can’t run away. Oh boy, here goes nothing.

Jolene leaned in a bit closer, and adjusted her glasses frames. I could smell a hint of vanilla emanate from her. Damn was this distracting. “Brian, I have a dilemma. I have a crazy schedule, and sometimes I need to travel for work. That can make things difficult for me. What I am looking for is something specific. So I must ask you a few questions first.”

She leaned in a bit closer still, and looked me in the eye. If I didn’t know any better, I would say I was in an interrogation.

“You are unattached. You find me attractive. Would you be interested in having sex with me, Brian?”

My jaw almost hit the floor. Still in shock of what I heard, I responded, “Yes, please.”

“Mmm, please? I like that. But we’ll get to that later.” She grinned. “You don’t seem to be having a problem with a dominant woman. You don’t mind a woman in charge, do you, Brian?”

Oh, man. I think we took a left turn at the rabbit hole, and I have no idea where we’re going. Nevertheless, my heart is racing and my jeans are beginning to tighten. I think I may just have to stay the course, and see where this ship takes me.

“No, no problem. I find a strong woman to be intoxicating,” I replied. Here goes nothing.

“Good, then I am sure we will have plenty of fun!” She smiled deviously, before she went back to her coffee.

We spent the next hour discussing everything from literature to current events. Not tandoğan escort that it really mattered much, because the entire time my mind was racing around the fact that she came out and asked me if I would have sex with her. You don’t encounter that very often.

Before we went our separate ways, Jolene and I exchanged phone numbers, emails and addresses, the typical information. She told me that she had a meeting to run to, but she would be in touch. She stepped in and gave me a kiss on the cheek, before whispering in my ear, “I look forward to playing with you later. I will be in touch.” She turned and left, making sure I had the opportunity to watch her in that skirt.

“Wow,” I thought to myself. “How did I slip into this opportunity? Don’t mess this up, this could be truly amazing.”

I went home, and went on about my day. Working around the yard, running errands. I kept thinking ‘this can’t be happening.’ I kept looking at my phone, thinking she would reach out to me. She had not.


Three days, and no word from Jolene. What was she doing to me? Had I misunderstood something? I had begun thinking that this was a great tease, and nothing would actually come of it.

That afternoon she called. “Hi Brian, its Jolene. Remember me? Do you remember what we spoke about at the coffee shop on Tuesday?”

My heart raced, I was nervous all of a sudden. “Hiya, Jolene. I remember. How could I forget? How are you?” I chirped, realizing I was speaking much faster than normal.

“I am doing well, thank you for asking. I am thinking we need to get together soon, and make good on our conversation. How does tonight work for you? You don’t have any plans, do you? If you do, you may want to reschedule them.” She lingered.

“N-no plans tonight, no. What time would you like to get together? Your place or mine?” I was able to get my speech pattern back to normal. I can’t believe myself. Why is this so difficult?

“I’ll tell you what. Why don’t you show up at my place tonight? Seven-thirty, sharp. Bring a bottle of wine with you. You pick it out.”

“Wow, ok. Anything else I should know, or should bring?” I asked, not sure yet what she had in mind.

“No, that’s it. You and a bottle of wine…” she trailed off. “We’ll find out what you’re made of.”

“Ok, I’ll see you tonight then.”

“Seven-thirty, sharp. Right?” she inquired.

“Right. Seven-thirty sharp.” I responded, noting how important the time seemed to be to her.


I pulled into her driveway at 7:25, knowing I was just a touch early. This way I had time to check myself in the mirror before grabbing the wine and walking up to the door. I rang the doorbell at 7:30 on the dot. In a matter of seconds, the door creaked open. There was the angel I met earlier this week. Her hair was up in a bun, she wore a pink cardigan over a black cami, with a black skirt similar to what she wore on Tuesday.

“Hi Brian, you’re right on time. I like that. Ooh, red wine, I like that. No need to chill it. Come on in.”

Jolene closed the door behind me. She touched me on the shoulder briefly as she took the bottle of wine and walked to the kitchen. I followed.

She poured us both half a glass of wine, before leading me to a couch in the living room. Handing me my glass of wine, she started up the conversation again.

“So Brian, I haven’t spoken to you in a few days. How have you been?” I noticed a slight smirk, as she took a sip of her wine. Then there was a look in her eye.

“It’s been a strange week, to be sure. The highlight has been my coffee date with you, though.”

“So far, you mean. After all, tonight is only beginning. So, then what has been going through your head since that coffee date? Nothing too crazy, I hope.”

I chuckled, “to be honest, I haven’t really known what to think. My mind has been all over the place, trying to figure out, just what you had in store.”

Jolene reached up, and undid her bun, letting her hair fall. She shook her head making sure her locks were free. I caught the scent of vanilla emanating from her again.

“Oh Brian, there are plenty of things we could do. But first, why don’t we enjoy some more of your fine wine?”

She unbuttoned her cardigan, revealing more of her cami. I had not seen her this casual yet. It was unusual, and arousing, at once.

We sat and chitchatted for a little while, nothing too meaningful. She had slipped off her heels, and finished her glass of wine.

“So Brian, the real question is, are you ready, or do you need another glass of wine first?” she asked, as she sat up toward the edge of the couch.

“Ready? I don’t understand. Ready for what?” I posed, thoroughly perplexed by what she was up to.

“I’m not going to tell you. Yet,” she giggled as she played with her hair. Standing, she continued, “You just have to decide if you are ready, or if you need more wine.”

“Err, ok. I believe I am ready.” I finished the last of what was in my glass, so I could set türbanlı escort it aside. As I did, Jolene took off her cardigan, and threw it on the couch, next to me. I glanced to where it had landed, when I heard her voice.

“Good, because I need your help.” She was standing directly in front of me now. “First thing first, I am going to put you to work. You need to unzip the back of my skirt for me.”

She spun around, and playfully wiggled her derriere at me, being certain I knew where to focus. “I can’t get to the zipper easily, so I want you to do it.”

I obliged. I reached up, grabbed the waistband of the skirt and the zipper. I slid the zipper down its quarter length, before leaning back some. “There you go.”

I was surprised that she would have me unzip her skirt, though after Tuesday’s coffee, I got the impression that anything was possible with Jolene. And she didn’t disappoint.

“Thanks hun.” She maneuvered in such a way, so that the skirt fell to the ground, and she stepped forward out of it. This was my first glance as her teal green bikini cut panties. “So Brian, do you like the view?”

I almost bit my lip before I could respond, “Why, yes I do. That shade of green looks quite good on you.”

“You think so?” Looking over her shoulder at me. Reaching down, she grabbed the bottom of her cami, and pulled it over her head, revealing a matching teal green bra.

“This color looks good on me?” she teased.

“Very good indeed. In fact, you should turn around, so that I can see how the rest of it looks on you.” I teased back. I might as well have fun with it, right? She is.

I heard Jolene let out a slight giggle before she continued.

“Do you like my ass, Brian?”

“I do. That is a great ass. You know it’s a great ass. That’s why you’ve made sure I had plenty of chances to check out said ass.”

“What would you do with my ass, Brian?” asking as she wiggled again in front of me.

“I’d love to squeeze that ass, Jolene. To smack it.” I told her, proudly.

“Oh ya? How about this, would you kiss it? Would you kiss my ass, Brian?” she bated.

“Kiss it? Sure, why not. I’d kiss an ass like that.”

Jolene gasped. “Why not? I’m insulted. Either you like my ass enough that you would want to kiss it, or you don’t. I’m not some middle-ground property.”

After a moment went by, she spoke up again.

“Now, let’s try that again. Would you kiss my ass, Brian?” This time I did not want to upset her. She’s already stripped down this much. I want to keep this going.

“Jolene, I would be happy to kiss an ass like that.” I responded.

“Well, don’t just sit there.”

Oh, I thought we were just talking, I didn’t realize she actually wanted me to kiss her ass. This is going to be a first.

Standing up to walk to her, Jolene spoke up. “On your knees. You’ll be the perfect height then.”

I readjusted, dropping to my knees, before making my way to her. This is unreal. Only a few days prior, and we were complete strangers. We’ve met once for coffee, and now I am on my knees behind her.

“Ok, so how would you like me to kiss your ass?”

“Well, take a look at where you are. On your knees for me. You don’t think a quick peck will suffice, do you? You have to make it count.”

Taking her cue, I placed my hands on her hips, and firmly, affectionately placed a kiss on either side of her perfect spheres.

“Now was that so difficult? Now that you have properly worshipped my ass, I think it’s time to watch you undress.” She turned around to watch me, though now I did not have a chance to really focus on how she looked in her bra and panties. “Go on now, down to your shorts. Time’s a wasting’.”


So here we were, Jolene in her matching bra and panties, and now I had to strip to my boxer briefs. She had told me she was a dominant woman, but I didn’t expect things to move this quickly.

“I…, ok.” I was unable to think of anything else to say. I pulled my shirt over my head and slipped off my sneakers.

“So quick you move. Slow down. Enjoy the tease,” she suggested.

Following her suggestion, I slipped off my socks and reached for my belt.

Unbuckled, I tried to draw things out. I slipped the belt out from around me, brought it up and around my neck before dropping it to the ground.

She grinned, “Now you’re getting the right idea. Go on.”

I looked down briefly while I unbuttoned my jeans, before looking back up at her and pausing momentarily.

I had her attention, and continued to keep my focus on her while I slid the zipper as far as it would go. I had watched enough exotic dancers to have an idea of how to move. So, slowly I turned to face away from her, while moving the waistband of my jeans back and forth.

“I will tease her as much as I am able,” I thought to myself.

To draw out the anticipation, I turned so Jolene was now behind me. Doing my best stripper impression, I bent at the waist while sliding the jeans over my rump. Keeping hold of them as they went, so that I could control their descent, before stepping from them. Once I was free of them, I dropped them next to my belt and other items.

I turned back to meet Jolene, “Well Jolene, you have me just how you wanted me. So, what is next?”

“How I wanted you, you say?” She checked me out from head to toe. She had watched me undress this far.

“Not quite. You are still wearing too much. Your undershorts, off. Now.” She directed.

As I grabbed for my waistband, to comply, she had more to add. “I don’t want you to throw them aside like you have everything else. I want you to remove your undershorts in front of me, fold them neatly, and present them to me. Do you understand me, Brian?”

Taken aback briefly, I nodded in acceptance.

“That is not good enough, Brian. I want to hear your obedience.” She dropped her smile. “Now, I ask again, do you understand me, Brian?”

I swallowed as my heart skipped a beat. “Yes Jolene, I understand. I am to present my undershorts to you.”

“Good,” she let out a giggle as she adjusted. “So what are you waiting for?”

Wow, I have a stunning woman sitting on the bed in her bra and panties, and she is demanding my boxer briefs. Who would have thought.

I grabbed the waistband of my shorts, and slid them to the ground. As directed, I bent and picked them up off the floor, and folded them in four, like I would when I did laundry. Now presentable, I proceeded to place my shorts in Jolene’s hands.

She smacked my thigh, while applauding me for doing as I was told.

“Now you apparently have me as you want me. What would you have me do next?”

“Mmm, that’s better. Now I suppose I should match you. However, I don’t feel like doing the work. So, that’s where you come in. I want you to take off my bra, and hang it over the chair over there. I need to keep my things nice and tidy, you know.”

She really was enjoying this, and I couldn’t blame her.

Doing as I was told, I stood, and reached around to unhook her bra, when she corrected me.

“Not that way. I will turn around and you can work from there.”

She spun, with a little bounce for exaggeration. While unhooking the bra from behind was easier, it was not as exciting of a view, and that was what she was going for. I slid the straps down her arms, and let the bra fall away. I kept one end in my hand, so it would not fall to the floor. I don’t want to be penalized for such a drop, if I don’t have to be.

I walked the bra over to the chair in the corner of the room. Hanging it over the back, like the delicate item it was, I spun to return to Jolene. She had sat on the corner of the bed, in only her panties. Teal, bikini cut. Legs spread.

“On your knees. I like the feel of you crawling to me.” I dropped to all fours, focusing on nothing but the fit of that teal garment in front of me. I crawled to her, pausing when told, drawing out the anticipation.

Jolene was content to torture me with every breath, if she could. Once I reached my mark, she told me to stop moving.

“I can’t help but notice how intently you are focusing on the pretty material in front of you. You love seeing me like that, don’t you?”

“Yes mistress, you look amazing.” I whimper only due to my crawling position is my excitement concealed.

She giggled to herself. “Before I allow you to go any further, you need to greet your mistress properly. I want you to kiss the fabric in front of you. If you can follow directions, we won’t have a problem.”

I couldn’t believe what I was hearing. Jolene wants me to kiss on and around her sweet lips through her teal panties. This is like oral sex light. In what universe would I say no to this?

“May I begin for you, mistress?” I offered.

“Hmm,” she paused, torturing me. “When ever you’re ready, hun.”

I moved in close, letting her feel my warm breath through her panties. Feel the pressure of my lips, exploring her sensitivities. She moaned and giggled as I did what she wanted. I was so tempted to do more for her, but in the back of my mind, I knew that was a bad idea.

Once she felt she had been greeted sufficiently, Jolene stood in front of me, again spinning so that I worked from behind. “You kissed my ass so wonderfully, I thought you should have another look before we continue. I want you to slip my panties off, and hang them alongside my bra for me. If your good, I may even have you help me put them all back on.”

Boy, she really likes to tease.

“Actually Brian,” she interjected, “following your little worship session, I want to feel you caress my bottom before you take those off. Now go on, have a quick feel!”

If I wasn’t excited before, I was now. Running my hands over her firm, tight bottom in those gorgeous teal panties. I ran my hands across her bottom, gently squeezing, doing exactly as she requested.

“That’s better. Now, go on. Let’s continue…” I paused. I slid my fingers into the waistband of her panties, and began to shimmy them off of her. Slipping beyond her hips, the material fell slack as her full form was revealed. Once out of them, Jolene stepped forward, allowing me to watch her up close. I picked up her teal panties.

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