Jenn's Journey

"Tonight?" I said, exacerbated. "Why in the world would you spring this on me tonight?"

"I'm not springing anything on you young lady," Mom replied sternly. "It's a special night for me too and I want to bring someone."

I gave her a hard stare but it didn't work.

"He won't hamper your good time. Just be polite and introduce yourself. After that you can go out with your little friends like you had planned."

Her words had finality. There was no point in arguing. But I was still mad about it.

"I knew you've been up to something," I said, then I stormed off to the shower to get ready for the night ahead.

Ahead of me was a night that was sure to change everything: My high school graduation. I'm a realist so I didn't see it as some kind of major accomplishment. However, I couldn't help but feel like mother was trying to steal my thunder by bringing her new boyfriend to the ceremony.

Actually, "new boyfriend" is probably a misleading term. I've been suspicious for almost a year that she was dating someone and thought it might be getting serious. My family had speculated and whispered about it but she was always evasive when asked directly.

"He's just an old friend," she'd say. "I'm not sure you'd call him a boyfriend."

It wasn't until a few months ago that she actually acknowledged there was a man. When I asked when I would meet him, she would never say for sure.

"In due time," she would always reply. Tonight, that due time had lapsed.

The moment I met him stands out as a clear, pleasant memory. Though I had no idea that moment would take me to where I now sit.

* * * *

"Congratulations," he said, standing behind mother after the ceremony. He extended a handshake. I just stood there, struck by how handsome he was.

"I'm Francis, by the way" he said.

My mouth was agape at the sight of him. It was not that I lose it over guys but he was different. Fit, handsome, well-dressed and well-spoken. He was around 40, just a bit younger than mother. He had a tan complexion, with dark hair and eyes to match.

"Jenn," I said back, suddenly embarrassed. I've never loved the way I looked but I remember feeling particularly self-conscience at the moment. I've always been overweight, but at the time I was 284 pounds. I'd ordered the biggest graduation gown in the catalog but it still managed to hang on me like a frumpy dress rather than an oversize robe like it was supposed to. I had just turned 18 a week before but he met my gaze an offered a smile that made me feel suddenly like a child. I pulled the stupid mortar board cap off my head and started fixing my short, brown hair.

After our introduction, I went on about my business the rest of the night -- going out with my little friends, as mother had put it. Though there was much more to think about that evening, the thought of him continually came back to mind. I was shocked, for lack of a better term. Don't get me wrong, my mother was very beautiful, especially for being 42 years old. She was fit, never smoking or over eating and always taking great care of herself by jogging every day. However, she always seemed to date losers and poindexters one after another and -- thankfully -- never for very long. I'd only known him for a second, but Francis seemed like he was actually worthy of her. Maybe that's why she took so long to introduce us.

* * * *

As weeks went by that summer I began to see more and more of him. Though he lived in downtown Phoenix, only about 30 minutes away from our suburban home, he would often stay over on Saturday or Sunday nights. He made mother very happy, which made me feel even more guilty about the thoughts I had about him. As he visited more often, our routines started to change. He brought a touch of luxury to our small, two-bedroom house.

In some ways, that was annoying. For instance, mother began insisting that I keep the house spotlessly clean.

However, it wasn't all bad. I remember one evening where the three of us were sitting down to a dinner, enjoying some Italian dish he'd prepared that we'd never had before. I came to the table surprised that he had poured me a glass of Italian wine.

"What's this," I said.

"Sassicaia," he replied. " It's a red wine from outside of Tuscany. It complements the dish. Tell me what you think."

I looked at mother for approval. She didn't object so I assumed I had it. The taste was deep, stronger than I had ever had before but I wasn't much on wine at the time.

"Well?" Francis asked.

"It's strong. I like it though." Mom never interjected, commenting only that she liked it as well. We all three drank up that night, Francis never bothering to stop pouring. Still sitting at the dinner table, the buzz I got off of that wine helped me realize something I had until this point been afraid to admit to myself: I wanted to have sex with my mother's boyfriend. A few weeks later I acted on that urge, but it didn't work out as I had planned.

* * * *

After high school ended I had no idea what I was to do with my life. I applied at a couple of colleges around the region but the cost of higher education made it seem unobtainable. So for the moment, I was a 3rd shift fast food worker. Each shift seemed like an endless living hell, so I looked for anyway to make it better -- sometimes to my own detriment.

One such indulgence was that I would always steal food as I cooked it. One Saturday night that July, my boss caught me hanging over the griddle with a mouthful of hamburger. He screamed at me about stealing company property, warned me that I was on thin ice and sent me home hours before my shift ended. It had been a rough day, but I remember seeing Francis' car as I came up the driveway. That made things a bit brighter.

Though I was home early, it was still the middle of the night. I crept in quietly, figuring everyone was asleep.

"Jenn?" I heard him whisper as I slowly shut the front door behind me. I turned and saw him leaning in from the back deck.

"Francis. Is that you?"

"It's me. C'mon out." He was sitting alone on the deck alone, a bottle of Sassicaia beside him. It was a curious scene but I didn't hesitate of course.

"Where's mom?" I asked him as I walked out and situated myself across from him on our high-top deck table.

"Asleep a bit too early for me," he said. "Figured I'd wait up a bit and have a drink."

I was more interested in him than the drink, but I told him go ahead and pour me a glass. I wasn't sure exactly how to handle the situation. I loved my mother and had no intention of trying to steal someone she cared about. At the same time, however, it wasn't up to me. He was strong, engaging and, more than anything, in control.

Though I stank like fast food, I felt that I looked pretty that night. My face has always been my strong point. Men always complemented me on my big brown eyes, pearl skin and full lips, which I had painted pink with lipstick that night. Francis didn't talked much as he poured me glass after glass and let me vent about everything -- from the rough night I'd just had to my frustrations about not being able to go to college.

We sat in the moonlight and talked for an hour or so. I loved every second of it, of course, but the bottle -- and in essence, our time that night -- ended more quickly than I would have liked. Finally, he said what I had been dreading since I sat down.

"You need to go get in bed. I'm already in enough trouble for getting you drunk."

"I'm not drunk," I said back. "You don't have any more?"

"To bed," he said firmly. He had never talked to me like that before -- so stern, like a parent. Part of me loved it and part of me resented it. However, I didn't feel that arguing was in my best interest. He helped me out my chair, grabbing the glasses that we'd used and opening the door for me. I stepped into the darkness of the house. Neither of us turned the lights on as we moved forward.

I was seething. I couldn't stand the thought of our time coming to an end. Maybe it was the wine, but I decided to make my move, pulling the door shut then rubbing his crotch with my fingers as I drew my hand back.

He slapped them down. "Bed," he repeated.

I was crushed. I felt my heart flutter a bit, hoping he wouldn't tell mother that I had touched him. I turned and began walking across the living room in the dark toward my bedroom. He walked past me not saying a word and entered my mother's room.

I closed my bedroom door and switched on the light. Once in, I pulled off my clothes and headed for the shower in my attached bathroom. It felt good to wash the fast food stench off but it also gave me a second to think about what just happened out there.

"If it comes up, I'll deny it," I thought to myself. Satisfied with that, I turned off the water, wrapped a towel around myself and headed back into the bedroom.

Then, something on the nightstand caught my eye.

It was a whole bottle of the Sassicaia and the glass I had been using. A note lay beside it.

"Thought you could use a night cap -- F."

A peace offering, no doubt, but it was one that started my motor running again. I let the towel drop on the floor and poured myself a glass of the wine. The bottle was nearly full. I sat there in the still of the night, naked on my bed enjoying a sip and a thought about him, touching me, commanding me in his stern way. I dimmed the lights as I finished the first glass. I poured another, sat up on the bed with my legs open and began rubbing my clit.

For several minutes I sat there, groping my own tits and rubbing my pussy. I imagined it was him going inside me. The night was still and silent. Then, out of no where, I began to hear the most faint moan. I leaned against the headboard, still fondling myself. It was coming from mother's room, a moan of pleasure. I sat there a while and listen it seemed to grow louder.

I poured another glass, finishing the bottle. I flipped off the light and listened as my mother got what I had been desiring all night. My head was against the wall as I listened and continued to rub myself. I've heard her have sex before but this was the first time I ever remember enjoying the sound. I closed my eyes, thinking of him, finished my wine and continued to rub myself as I heard her moans get louder. Finally, my hips clinched and my body tightened as I reached a climax. He'd just made us both cum at the same time.

The next morning things were different between Francis and I. I didn't get a moment alone to thank him for the wine but he knew I was grateful. We shared a few smiles at the breakfast table and he was off, back to his side of town. For me, it was back to the grind as well, with nothing to look forward to until his return the next weekend.

Or so I thought, anyway.

* * * *

I walked into my room about three nights later. It was 5 a.m., and I had just finished another long shift over a greasy fast food griddle. My only wish was to shower and go to bed.

I reached into the shower and twisted the facet handle then turned toward the closet and reached for a towel. Then, just as a few nights before, something out of place caught my eye.

A small, plain envelope sat on the towel shelf in my bathroom. It was unsealed, "Jenn" written on the front. Quickly I opened it up wondering where the hell it came from.

"You and I should talk away from your home. Come to my office downtown at 2 p.m. tomorrow -- F."

At the end of the note there was an address. My mind fluttered and my heart raced. I was as good as there.

* * * *

The next day I told mother I was going shopping with friends, then made my way downtown. On my way there I thought about everything that had happened and what would come next.

It was the middle of summer, so I had an excuse not to wear much. I had on a short purple dress that showed off my tits, my prettiest black bra and lacy black panties underneath. I woke up early, after barely sleeping anyway, and meticulously fixed my hair and did my makeup. And I stole a pair of purple heals from my mom to complete the outfit.

Sitting at a red light, I stared at them, thinking of what else I was trying to of steal from her. It wasn't that I wanted to take him away. It was that he treated me in a way no other man ever had. Not to mention he had some sort of unexplainable control over me. There had never been a man I wanted to please so much, sexually or otherwise.

* * * *

After parking my car, I made my way to his suite.

"Jenn?" A receptionist called out as I walked off the elevator and into Francis office.

"Yes," I replied.

"Right this way," she said, leading me to a seating area behind her station. "I'm sure he'll be right with you."

The receptionist was kind and gorgeous and I was instantly jealous of her. She had a tiny figure, probably no more than 100 pounds, but her tits were bigger than mine. She wore a tight, form-fitting skirt that showed every inch of her off.

"I'm Mel," she said, "Can I get you something to drink?"

"No," I replied, trying not to sound resentful toward her. I hated that she seemed sweet.

Mel walked back to her station and called Francis.

"Sir, Jenn is out here." A few seconds passed. "Yes Sir." She hung up the phone. "He'll be right with you."

I sat there for several minutes, looked around a bit at my surroundings. The office was elegant, a large window overlooking downtown behind me. My chair was facing inward, toward Mel. She stood there working with her back to me. I remember looking at her shoes -- tall, 6-inch heels. I found it peculiar that she didn't have a chair.

Did she stand all day in heels like that, I thought to myself. No wonder her calves were so tone. I wanted to ask but thought better of it. Finally the phone buzzed and she answered.

"Right away Sir," she said into the phone. With that she signaled me to follow her.

* * * *

Francis sat behind a large, beautiful desk in front of a huge window in his office.

"Jenn," he said, "I'm so glad you accepted my invitation. Sit."

I had never seen a chair like the one he had waiting for me. It was bright red with two indention in the seat that formed a V-shape coming from the back. I sat down and immediately notice how difficult it was to cross my legs with them in the indentions. The back was circular, pushing my chest out.

"Mel bring us some water please," he said.

"Yes Sir," she said.

"Jenn I don't want to waste your time. And I assume that because you came up here you are interested in me, correct?"

My face went red. He was always very blunt but I didn't expect he would be so forward. I was a deer in the headlights at the moment.

"It's OK. Nothing you say here will leave this room."

I shook my head. And he asked again.

"Are you interested in me?"

"Yes, I am," I said finally.

"Good," he replied. Mel entered the room again with two glasses and a pitcher of water. She began pouring as we spoke.

"Now, how familiar are you with the world of BDSM. Has your mother told you anything," he asked.

"No," I said. "I've heard about it of course."

I gave him a puzzled look. "I didn't realize that was the nature of your relationship."

"It's OK," he said. "I didn't think she would have said anything. Tell me, have you ever been curious about BDSM?"

It was true that I had always been curious about kinkier forms of sex but I had never engaged in anything serious, save for a spanking or two. His line of questioning aroused me greatly, it turned out. I sat there with my legs forced open by the chair, now realizing why he owned such a device, and felt my pussy begin to get wet.

Mel finished pouring the water and stood behind me -- not speaking, just waiting for instructions.

"Yes, I have been curious," I said finally.

"Excellent," he said. He began to explain the lifestyle to me in simple terms. There are Dominants and submissive, and in some cases Masters and slaves.

"I'm a Master," he said. "I train submissive women to be slaves, sometimes for myself and sometimes for others," he said. "I only work with those who are completely willing. And I only work with women who are willing to prove to me that they are worthy of being my slave."

I sat there shocked by his ideas. It ran contrary to everything a girl is told growing up.

"It's a long process," he said. "Mel here has been under my wing for more than 4 years and she is one of my finest. It can be a transforming experience for the right woman."

I didn't know what to say. I knew there was something coming but I couldn't have begun to guess what it was. I had nothing but questions in my mind. Finally, I started to blurt a few of the stupider ones out.

"What would I do? Would I work here?"

He smiled. "You could live your life. You could continue living at home and work here if you like. Or I could get you your own place. Or I could get you a better job than the one you have. I could even pay for your college if you like. I can pull many strings if you're willing to accept the role."

"What all would I have to do," I asked.

"You would have to trust," he said. "There will be many requirements, trials. Everything will be controlled -- your meals, your dress. You'll be whored out, humiliated both mentally and physically for the sexual gratification of others. And that's just the beginning. If some pervert can imagine it -- there's a good chance you'll be asked to do it. "

"Why would I agree to that," I said.

"That's a fair question," he said. "You have to ask yourself if this life is for you.

He paused for a moment, then continued, "Are you aroused right now? Could there be something to that?"

I stared blankly.

"I know your type, Jenn. I'm rarely wrong," he said.

"Do you see all women as your underlings," I asked.

"Absolutely not," he said. "Some women are dominants. I know women who are far crueler than I, some sickeningly so. And I'll warn you, if you accept the role as my slave you absolutely will have to serve some of them as well. Many times I seek their advice when training a new submissive."

I had never been with a woman but always had been curious about bisexuality. I felt like I was in completely over my head and I think Francis recognized it.

"Look," he said. " You don't have to decide today. In fact, if you don't want to, we never have to discuss this again." At that moment he reached into a drawer on his desk and pulled out a nicely wrapped gift.

"I will be back at your house in 10 days, at my usual time. If you are interested in pursuing this lifestyle, answer the door in the outfit I've enclosed. If you're not interested, then simply don't. And I will never ever ask you about it and pretend this conversation never took place."

"That's it," I asked. "What if I decide to put it on, is there any going back?"

He smiled at me, I think because he knew I wanted to submit.

"You'll be given plenty of chances to back out early on," he said. "If you decide to put the outfit on, you'll be acknowledging that you're a sub and you'll be treated as one. However, you'll be asked to perform three tasks as sort of an initiation. You'll be free to give up at any time during those task. Once you've finished those, you'll be branded with a tattoo-- something you'll have to ask for, mind you. Before you receive the tattoo you're still free to leave the lifestyle. But once you've completed the tattoo branding ritual, you're acknowledging that you're a permanent slave."

I swallowed hard at the prospect. "What do you mean," I asked.

He looked at Mel. "Show her."

Mel didn't hesitate at all. I could tell she'd been given the order before. She stepped in front of my chair, pulled up her tight skirt and bent over the desk. She wasn't wearing panties. There, tattooed onto her right ass cheek was a symbol.

I starred at it for a long moment as she bent over in front of me. There was something beautiful about it, about giving everything up and accepting the role of a slave as she had.