Jenn's Master

Story Info
Date becomes much more.
11.2k words
4.64
56.8k
5
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
slvjenn
slvjenn
27 Followers

//:: Story written by slvjenn@hotmail.com

//:: Copyright maintained by the author

//:: If you like the story please send encouragement to the above email address. It's

//:: always nice to know people are actually reading your work.

++++++++++++++++++++++++++++++

Background

I've wanted to write a story for a long time. I've actually started on a few, but never gotten around to finishing them. Lets hope I do better with this one.

To follow along, this story is mostly true with a few things changed to just help readability. It starts in the past and will end in the present. I guess that will allow for future chapters as they take place J.

++++++++++++++++++++++++++++++

Chapter One The Meeting

Master and I met at a bar, but he didn't exactly "pick me up" as we were both with mutual friends. It was all so natural. We just started talking. There was no pressure, and it never seemed like he was hitting on me at all. Though in retrospect I suppose he was.

The night was over all to fast and he was leaving with his friends and I was leaving with mine. Of course the second we got in the car, I got the usual grilling. "So, what did you think?" "You were aweful chatty tonight." "Did you get his number?" I laughed and blushed.

I didn't get his number though, and I did like him. I avoided the questions pretty well and after getting home I laid awake thinking about him. I guess being that this is the type of story that it is, I'll include the fact that my fingers found their way under the waistline of my panties. I came with images of him in my head.

The next day at work my mind wandered and it seemed like a very long day. Finally around four a friend (Kim) called inviting me back out that night. Of course, I never would usually go out on a Tuesday, but I couldn't say no today and miss a chance to spend another night getting to know the person who had been occupying my head all that day.

Now, the last 45 minutes of work would be REALLY long. What would I wear? What would I wear UNDER it? Would I let him see what I wore under it if he tried to find out? Would he even be there? If he was what would we talk about? If he wasn't, then what would I do?

It was finally 5 O'clock I practically raced out of my building. I don't recall the hour drive home. I was in the shower, and thoughts of masturbating entered my head. I resisted though, convincing myself that some pent up sexual energy would be good tonight. In my towel I flicked through the clothes in my closet. "No, no, no…no…maybe." One outfit half thrown on the bed, then another, and another. In all I think there were 5 I was considering.

I tried each on, glancing at the clock the cable company conveniently placed in their box after each one. He was only wearing jeans and a t-shirt last night. I didn't want to over do it. It wasn't summer yet but I thought I could get away with a white spaghetti string pullover that showed my belly. Now I needed a strapless bra though or it would look kinda tacky. I decided against a skirt and for a pair of jeans that had a nice low cut waistline and was form fitting down to the knees where it flared out into sort of a bell-bottom.

Underwear could now be decided on. I found a white strapless bra that looked good enough for a guy to see should it come to that. Panties were a little more difficult. These jeans would show lines if I didn't wear thongs, but I hate thongs so I tried to avoid them. After trying on 3 pairs of bikini briefs and examining my ass in the mirror I resigned the fact that I had no choice. Thongs had to be worn. I decided that white was the way to go with the white bra, and also I suppose to seem more innocent. (should things go that far)

Comcast's gift said it was past seven; Kim was picking me up at 7:30. No time to eat, and I didn't want to chance getting anything on my shirt anyway. I was nervous; I reapplied some deodorant, and put on my favorite perfume. I checked my teeth just to be sure, and used some Scope. I checked Comcast again.

Now I was waiting, the worst part of any date. But this wasn't really a date was it? No, I was just going out with some friends. I didn't even know if they guy would be there. I looked in the mirror again. I check my ass, no underwear lines. I smiled at that. I looked out the window down to the street. I opened the refrigerator. I looked inside. I closed it. I opened the cabinet. I closed it. Finally I heard a horn.

I ran into the bathroom and checked my face and teeth again. I put some powder on my face even though I loathe makeup. I bit my lower then upper lit to get a little extra blood flowing into them. He might be in the car after all.

The car's horn sounded again as I walked downstairs. My platform style shoes wouldn't allow me to even attempt to run. I took a deep breath as I opened the front door of my building. The car was there and only Kim inside of it. I walked out to the car and she greeted me.

"Well?" I asked looking over at her as she pressed on the gas pedal. "Well what?" she asked back with a huge grin on her face.

I faked a giggle as I blushed and asked my question again, "Is he going to be there?"

Kim was laughing now, "Would I have even invited you on a Tuesday night if he wasn't going to be?"

"I guess not" I let out through my smile.

"Am I dressed ok?" I asked.

"Sure, he'll be talking to your chest all night."

"Well if he does you don't have to invite me next time." I told her.

"And if he doesn't?" she asked half joking.

"If he doesn't, then we'll just hope that he's the one doing the inviting."

We were in the parking lot, and I suddenly felt over dressed for a Tuesday night. We slowly walked toward the bar together, crossing the street then toward the door. My heart began to thump in my chest. The first 2 minutes would be the most awkward.

We walked in, the guys were already there and Kim and Shawn met half way between the bar and the door, first hugging then a quick peck on each other's lips. The man I was there to meet looked me up and down. I didn't mind, I wanted him to look, as long as it didn't turn into an uncomfortable stare. I smiled at him and he smiled back. He ordered hard lemonade for me without asking what I wanted. I suppose that would have put off some women, but I wasn't.

I walked up to the bar grasping the drink. I thanked him while smiling. He smiled back and nodded. There was nothing to really watch on the TV tonight, and Shawn and Kim were obviously not going to help us get into any conversation.

He grabbed a few dollar bills off the bar and asked if I wanted to help him pick some songs on the jukebox. I smiled as I nodded and started following him to the rear of the bar. The bills were fed into the machine and we picked 9 songs. All were rock, and we agreed easily on each one.

Once back at the bar conversation was a little easier. We talked about music for a while, then sports. I love baseball and can talk about the Yankees all day long. From baseball we moved to work, from work to schools. We started with high school then to college, from there we talked about friends, and ex boy and girlfriends. That led the conversation to sex.

It was my fault really. I knew it as soon as I had said it. No matter how I phrase it, if I'm honest I just can't avoid people wanting to know more. One of my ex-boyfriends and I broke up on fairly bad terms all revolving around sex.

He wanted to know if the guy just sucked in bed, or what the story was. He seemed concerned. I was on my third hard lemonade and excused myself to the bathroom. I grabbed Kim and we walked to the rear of the bar. I wanted to look back and see if he was watching me walk away, but resisted the temptation until I made the turn into the door. He was looking, that was a good sign.

Kim was asking a million questions. I barely heard her. My mind was on what I'd tell him about my sexual habits. I usually don't broach the subject until much later. Maybe I should just tell him that I'm not comfortable talking about it right now. That's what I'd do, but I just hope it doesn't make him uncomfortable.

After a short chat with Kim we headed back to the bar. I sat next to the new interest in my life and took a deep breath as quietly as possible. I looked at him, and he looked back as if waiting for me to say something. I smiled uncomfortably and took a sip of my drink.

"Look, if you don't want to talk about it, that's fine. It's no big deal." He said finally.

Now I felt even more obligated to tell him the truth, but I really didn't want to yet. "Lets just say that he didn't meet my sexual needs, and he took it very personally." I ended up telling him.

He quickly changed the subject to lighter things. The uncomfortable 5 minutes were forgotten and we laughed at each other's stories for another hour. Kim was nudging me, saying that we had to go after this drink. I relayed the information down the bar.

This was the moment of truth, would he make arrangements to see me again or not? He surprised me by excusing himself, and heading out the door. I was confused. Kim shrugged.

He was back within a minute though. He was carrying a cell phone. I was really confused, but tried to just look casual.

"OK, here is the plan." He said.

"We'll go out to dinner or something tomorrow night, I'll call you on here to confirm." He handed me the cellphone.

He broke out a more detailed explanation. "If everything goes to our liking at dinner, and we want to see each other again, I'll call you again. If we don't get along, I take the cellphone back and you never hear from me again. When you're comfortable enough to tell me about the ex, we shouldn't need the cell anymore. That sound good?"

I was somewhat taken by all this. He didn't ask me out. He said we were going out. Was he being arrogant? Was he just confident? Could he read me that well? The cell gave a good comfort level. I wouldn't have to change my number if he turned into a wacko after dinner tomorrow night. I liked it. New, interesting, yeah, I defiantly liked the idea and told him so.

The drive back to my apartment was filled with questions from Kim. I filled her in the best I could during the 15 minute drive. She seemed satisfied with the details I gave and she seemed happy that I'd hit it off with one of her boyfriend's friends.

As I walked up the stairs my new cellphone rang. It startled me at first, but I answered it quickly.

"Hello?"

"Oh good, just wanted to make sure it worked" I heard from the other end.

"I'll talk to you tomorrow." He said before I could respond.

I heard a click and I opened my door. After I got inside I was undressed and in bed within minutes. It was late and I was tired. My dreams were filled with images of him, always standing over me.

++++++++++++++++++++++++++++++

Chapter 2 The Date

Work was hell. The day dragged as I looked forward to the dinner that was planned. I thought about where we'd go, what I should order, if I should offer to split the check, who would drive, and if I wanted him to see my bedroom.

The day was finally over and I was half way home when the cellphone rang. I answered while fumbling it.

"Where are you?" he asked.

"On my way home from work." I told him.

"Yeah, but where?" he retorted.

"Umm, just coming up to 14a on the Turnpike." I said as I watched a plane landing.

"You get off at 15W right?" he asked.

"Yup" I said, trying to sound playful.

"Cool, park in the Kmart parking lot then, I'm picking up a PS2 game, I'll meet you out front." He said, with little worry that I'd not be willing.

"Umm, Kmart?" I said unsure.

"Yeah, I didn't take your phone number, what would make you think I'd want to know where you live? When you feel comfortable you'll show me."

"OK" I smiled, "makes sense."

We hung up and in 20 minutes I was waiting for him outside of Kmart. I felt pretty strange standing out there. I was dressed for work. Wearing a plain gray business jacket with a matching skirt, and a white blouse.

He came out of the store holding a small bag. Major League 2001 he told me. He must have been coming home from work too, he was wearing a polo shirt with khaki pants and Kenneth Cole shoes. My personal favorite. I'm sure he saw me looking him up and down, but I didn't mind.

"My car is over here" he guided me in the right direction.

He opened the door for me, then closed it once I was seated. We drove into the next town, taking the main street, which took longer than taking the back highway. He turned down a small street I had never been down before. We went about 2 blocks and pulled into a parking lot. I had never seen this place before, but lived only about 3 minutes away. It was an Italian place, with an empty bar, and mostly empty seats.

It's Wednesday, you can't even get a reservation on the weekends I was told. I smiled and nodded as I was led to my seat. I looked over the menu already knowing I wasn't ready to eat.

A bottle of wine was being ordered. A blush. I like wine but don't know much about it and am always afraid to ask.

"Know what you want yet?" I was being asked. Something about the night seemed surreal for some reason.

"No" I answered. "To be honest I'm not even really that hungry yet."

"Oh, you don't eat dinner this early I guess. I like my dinner right after work, that way the rest of the night is mine." He told me.

We sat in an oddly comfortable silence for a few minutes. It was only our first "real" date, but somehow I felt so at ease with this guy. He seemed to just reek of trustworthiness. I decided to take a leap of faith.

"I want to tell you what happened between me and my ex, before this goes any further." I said, then quickly sipped my wine.

"OK" was all he said.

I fished in my purse for my cigarettes. I never considered myself a smoker, but recently it seems I've had more and more excuses to light up. Tonight it was extreme nervousness, bordering on fear.

I leaned closer to him, then looked around. No one seemed to be in earshot.

"This is going to be very difficult to tell you, I've only recently admitted it to myself, and the first man I told hated me for it."

"Well I don't know you well enough to hate you for anything, so don't worry about that." He told me in a reassuring voice.

"Well, I get bored in bed very easily." I sipped "I mean I need" I felt myself blushing "more than just normal sex."

He smiled, "Well what exactly does more mean?"

I sipped again, took a drag of the cigarette. "Well, for example blindfolds are nice. It's fun to not quite be sure of what is gonna happen next."

He smiled the biggest smile I've seen on him up till now. "That isn't so bad, anything else?"

He wanted more, I was hot, almost sweating. "Well, my arms tied to the bedposts while I'm blindfolded is good too."

"That sounds like it would take a lot of trust in your partner, wouldn't it?" he asked.

"Well yeah, I guess that is part of the excitement."

We talked back and forth for a while about this, he had a lot of questions, but he made sure not to make any of them vulgar. A lot revolved around trust, and how I decided if I could trust a guy enough to let him tie me up. The waiter was back, and then sent away, still without our orders. He asked some more questions, changed the subject a few times, but seemingly only to let things sink in, then coming back to the topic at hand.

He had taken this much better than my ex. I guess that it's better to find out what your potential girlfriend likes before the fact than it is to find out that she doesn't like anything you've done since you started sleeping with her.

Then it was there. The question I was fearing. "What else?"

"What else?" I asked back.

"Yeah, What else? I don't think he'd have freaked out just cause you like a little pepper on your food."

An interesting way to put it I thought. "Well how much do you know about the entire subject?" I asked.

"I know enough I guess." He told me.

"Well, I'd rather not go into details here, and now, but yes, pepper is good, so is oregano, and crushed red pepper. But I guess if you scale it like that, I'd probably be happier with ground red pepper, lots of Tabasco chili peppers, and anything else that might burn your tongue."

"I see." Was all he said.

The waiter was back again, and this time we were ready. He ordered the backed manicotti and said that he recommends it highly as their best dish. I decided to take his advice and go against my always on a diet status.

By the time we ordered it was after 7, by the time our dinners arrived it was 8. Before 9 I was carrying my doggy bag out to his car.

Conversation had been light throughout dinner. I wasn't sure if he was mad, just thinking, or what. When we got in the car he asked me to come back to his apartment. I was assured it was to just talk, and maybe play a game of baseball. He pointed to the disk successfully trying to be cute.

I agreed, but as soon as I did he told me that he wanted to know more about my sexual habits.

"It'll be easier to talk about in a place where no one can overhear us." He assured me.

He lived in the next town over, one more town further away from my apartment and my car. We took the back highway and were there in less than 10 minutes. He showed me in and asked if a coke was ok. It was an soon I had a glass of it in front of me. The ice mellowed the sweetness and I took a sip. He excused himself to his bedroom and came out with a pair of sweatpants and a gray t-shirt in his hands.

Pointing at a door he said, "If you wanna change, the bathroom is right there. I need to get outta my work clothes. I'll be right back." He handed me the clothes.

This is the oddest first date I've ever had. I wasn't sure what to do. I was uncomfortable in my work clothes, but I wasn't sure I'd feel any better in HIS clothes. I had just met him after all. I decided that what he gave me wasn't threatening, and felt fairly sure it was done out of thoughtfulness not had no malicious intent. I went into the bathroom and changed. It felt good to get my stockings off.

When I came out his bedroom door was open and I could see him sitting at a desk. He motioned for me to come in. Still carrying my work clothes I stood next to him. He was getting on the web.

He looked at me, "Oh, want a hanger for those?"

"Umm, no it's ok."

"Well here." He said with his arms reaching for the clothes.

He got up and put them on a chair. He told me to sit in front of the PC and show him some websites that have the kind of things I like. He said it so casually, but it embarrassed me anyway. He told me that he wanted to learn about what I was talking about. He said that it sounded very interesting. I knew then that this really could go someplace.

After a few minutes on Altavista and Google, I found a site that I had bookmarked at home. I pointed, then got up, he started reading.

I looked around his bedroom. His apartment was much bigger than mine, and it was more than obvious only a man lived here. It was neat, but just overbearingly masculine. He was reading, I wandered around and found my coke, I took a sip of it. He must have realized I was getting bored and asked if I wanted to try out the baseball game. "get some practice in before I play him" as he put it.

I opened the game and loaded it up. I sat on his bed and started a game. I of course was the Yankees. It was the third inning, the bases were loaded on Roger Clemins when he turned around to ask if I was submissive, or just liked bedroom games. I paused the game.

I stuttered back that I was submissive. He only nodded then went back to reading. In the bottom of the fourth inning he asked if I was a masochist. I replied that I was not, that I haven't found any pain to be pleasurable. Again he nodded and went back to reading. In the top of the sixth, he asked if we could try a few things.

slvjenn
slvjenn
27 Followers