On The Road Again Ch 01

My name is Gwen. I'm 26 years old, a paralegal and I live in St. Louis, MO. In college, I dreamed of being a lawyer, but alas, my LSAT scores were not good enough to get into a top flight law school. I just don't test well and if I am honest with myself, I don't handle stress well enough to be a lawyer. Still I am good at research, writing and administration so I found my niche where I could work in the law, even if it wasn't as glamorous as getting top billing. I worked under several lawyers who understood the contributions I made to the firm. Plus the hours were closer to normal compared to the insane amount a first year associate has to work.

Even though closer to normal meant not working 60-70 hours a week, 50 hours meant a work/life balance was difficult. I am young, attractive and smart, but I always found it difficult to keep a steady boyfriend. Plus I had always had a thing for "bad boys" so if I wanted someone more compatible with me in bed, that pretty much meant long term relationship prospects took a back seat. But that was OK for now. I figured after I established a career I could settle down.

My firm had offices in New York City, Chicago, St. Louis, Kansas City and Phoenix. Occasionally I had to travel for a week or two in order to help out on a big case. I guess my reputation was strong because these trips became more frequent as my skills became known in the firm. Unfortunately they also were definitely work trips with long hours so I couldn't really enjoy the cities. The one thing I did arrange was to always fly home the day after whatever casework was resolved. That meant I could go out the night before and indulge my need for a bad boy in a way I could never do at home. I don't consider myself a slut, but a one-night stand in a town where I'm not known became the norm for my need to release my work stress. But even this, over time, lost its appeal as I felt a need to connect on a deeper level with someone. Then came a company meeting in Chicago.

Being less than six hours to Chicago by car meant I had been there many times and always enjoyed myself. But since I was going to be in our office most of the time and it was near Union Station, I decided to take the train. The time was about the same, but it was much cheaper than gas and I wouldn't have to worry about driving or carpooling. In my suitcase I packed two business appropriate suits as well as a short skirt, silk blouse and my four-inch spiked heels. I called those my hunting clothes. I was undecided whether I would go out and let myself get picked up for a night of meaningless sex, but I figured I should be prepared.

Since this trip was for meetings, on nights one and two we went out as a group for dinner and drinks. When I get a couple glasses of wine in me, I get flirtatious. I had to be careful around my co-workers as it was definitely inappropriate to fish off the company pier, especially for just a couple hour fling.

The meetings went well and were scheduled to wrap up on Wednesday and everybody seemed to be heading to the airport soon after. I had kind of given up on going out hunting on Wednesday night, but I kept my hotel until Friday so I could go explore the city on Thursday. That seemed like a good plan and the company was fine springing for a couple extra nights since they were so pleased with my work. My boss said it was an "unannouced" bonus, meaning don't tell anybody, but I had earned it. It was a perfect plan except for my dream Tuesday night.

I had a bit too much to drink at dinner on Tuesday. That is what I blamed for my dream. It wasn't unusual for me to dream about a hunky stranger taking me back to my hotel from a bar. But this time it wasn't a man. It was a woman. She wasn't hunky, but she was confident, beautiful and knew she wanted to be with me. Before you wonder where these thoughts came from, back in college I did make out with a couple of different girls at parties. Alcohol was always involved and usually a dare from other people at the party spurred the action. I never admitted it, but I always got turned on by kissing another girl and when I would get home after the party I always masturbated to the experience. I never went further than that, but after I woke with a wet pussy from the dream, I thought to myself, why not have a one-night stand with a woman and find out what I had been missing. I didn't think I was changing sides, or even that I might be bisexual. It was just that my travel adventures had grown stale and maybe this would be an adventure. Besides, if I got a bad vibe at the bar, I could always just go back to the hotel. A quick Google search located a lesbian bar on the near West side not too far from my hotel.

It was just after six, far too early to go out, but not too early to masturbate thinking about getting picked up by a woman. It was even better than my dream and I came quicker than I usually do. That sealed my fate as I knew this was what I wanted to do. A quick shower and some time doing my makeup and I was ready. A short Uber ride, with a driver who seemed disappointed that I was gay (Based on my destination and I didn't tell him I was just pretending as he wasn't my type) and I was sitting at the bar drinking a red wine by 8pm.

I didn't know if the protocol of trying to get picked up for a hookup was different between women compared to with a guy. I was accustomed to having my pick of guys trying to get my attention, usually within a few minutes of my arrival. But this was different. As I sat at the bar and looked around for a woman to catch my eye, I didn't have many women approach me. A couple did, but they seemed to sense my inexperience and that seemed to turn them off. This surprised me. I didn't tell them I was a lesbian virgin, but I guessed I was putting out that vibe. I figured turning a straight girl would be a notch in their bedpost they wanted, but maybe I was wrong.

30 minutes later I was almost done with my second glass of wine and ready to head back to my hotel. I guessed it wasn't meant to be that I would find somebody to take with me. Then she walked in. She was a redhead. I didn't realize I thought that was hot until that moment. Actually, I had not really thought about what I was looking for, but this woman was definitely it. She was taller than me, probably 5' 10". Even in my heels I was 5' 7" at best. She had on a smartly tailored business suit as if she had just come from an office. She looked like so many of the female lawyers I worked with and even though I had seen her less than five seconds I sensed an aura of confidence in how she carried herself. I liked that too. She was kind of a bad boy in spiked heels.

As she walked in, she looked at me. There were a couple other women at the bar, but I got a sense she was sizing me up instead of looking for a place to sit. Unfortunately her gaze shifted quickly to a couple of women sitting at a table. Apparently they were friends as she walked over to them and engaged them in conversation. My hopes dashed, I decided to finish my drink and head out. It wasn't too late to go find a regular bar I figured, or maybe even the hotel bar so if I didn't find anybody I could drink safely. Dejected, I focused on my glass. I didn't slam the second half of my drink. I sipped it slowly, enjoying it, but I felt stupid for coming here. Just as I was finishing, I felt a tap on my left shoulder.

I turned and saw the most beautiful piercing green eyes looking down on me. I opened my mouth to say hello, but no words came out.

"You look lost," the red headed woman said. "Join me at my table and let's talk."

She held up her hand and I passively put mine in hers.

"How many of those wines have you had?" she asked. Finally finding my voice I said, "Two."

"How long have you been here?" she continued. "About half an hour," was my reply.

She looked me up and down as if to gauge my weight. "You should only have one more," she said loud enough for the bartender to hear her. I had not noticed, but the bartender had already begun refilling my glass. My new friend guided me off the stool and then took my glass and led me toward the back of the bar and an empty circular booth. Using my hand to direct me, she had me slide into the booth. She then placed my wine in front of me and sat down herself.

"I am Victoria," she announced. "And you are?"

"Gwen," I replied.

"I have never seen you here before," she said, stating the obvious.

"No, I am from St. Louis," I replied.

"Ah, so are you looking for a hook-up?" Victoria asked.

Until she walked in that was exactly what I was looking for, but there was something about her that made me question that. "I'm not sure," I said. I know I didn't sound confident. There was something about her that made me nervous. I wasn't scared, but suddenly things went from slow to fast and I wasn't in control of the situation. Then again, I wasn't sure I wanted to be in control.

"I see," she said and then added, "I myself don't do the hook up scene. I'm not against quickly taking someone new to my bedroom, but I have to be sure we want the same thing."

I felt a bit lost because I didn't necessarily know what I wanted and I was sure I didn't know what she wanted. Fortunately she was comfortable driving the conversation and I found myself opening up to her questions. Soon we were discussing my life, my lovers, my job, my family and how I saw my future. At some point she softly began running her manicured fingernails up and down my arm. I felt a thrill go through my body. In response to a couple of my answers, she looked around as if to check to see if anybody else could hear her and then leaned close to me to whisper in my ear. Her hot breath on my skin was far more important than what she said. The thrill of her touch became shivers of excitement.

I am 100% sure she understood the effect she was having on me. She didn't need to ask me. My body language was obvious. She turned to face me. While she continued to stroke my arm with her right hand, she deftly guided her left hand to the hem of my skirt. Without saying a word she was asking my permission to stroke my thigh. Without a word, I gave it with my eyes and a small smile. She continued our discussion about me while she slowly and softly touched my left thigh. Each time she slid her fingers up and down my leg she went a little higher. Her right hand now touched my neck. Neither of her hands applied much pressure, but her simple touches made me quiver. By the time my third glass of wine was empty, her left hand was almost up to my panties and her right hand was possessively holding the back of my neck. The question of whether I had ever been with a woman was about to be asked. She had danced around the subject as we discussed my lovers. I was worried since she wasn't into hook-ups that turning me on was some kind of game she played for the amusement of her friends.

I couldn't see the other side of the bar to know if anybody was watching us. I knew she was about to find my panties were soaked. I closed my eyes and sighed. I know she said something, but I didn't comprehend what she asked. It was then she applied pressure to my neck.

"I asked you a question, Gwen," she said, this time with a touch of forcefulness that had been missing until this point. "I expect an answer."

"I'm sorry," I babbled. "Your hand is distracting."

As if to make sure I was distracted, she rubbed the front of my panties.

"I asked if you had ever been with a woman before," she repeated. I moaned. Victoria had a sultry voice and every word she spoke seemed to go right to my soul.

"If I say no will you stop touching me?" I finally managed to respond.

"You don't need to ask questions," she replied. "I already know the answer. I already know all about you and what you need. But I want to hear you say it."

My body was squirming trying to get her fingertips to touch my panties. I had never felt like this with any of my hook-ups. My ability to form a rational thought was impaired, but finally I got myself together enough to admit that I'd never been with a woman before. It was then she finally rubbed the front of my panties with more force. Although the thin material kept her from making direct contact with my labia or clit, I felt my pussy gush in anticipation. Victoria smiled a devious smile. Then she pulled both her hands back away from me. I probably looked like a sad puppy when she stopped touching me.

"If you want me to touch your pussy, go into the bathroom and remove your bra and panties," she told me. Almost as an afterthought she added, "And leave your phone here unlocked for me."

I am embarrassed to admit it took me less than a second to decide to do what she asked. I slid out of the other side of the booth and then looked around for a sign indicating where to find the bathroom. I had to walk past the table of women Victoria had spoken to when she first arrived. I kept my head down to avoid making eye contact with them. I bet they knew I wasn't going to the bathroom to pee. Well, not just to pee. Having finished three glasses of wine, I did need to go.

I sat on the toilet having peeled my soaked panties down. I desperately wanted to touch my clit. I knew I could get off very quickly. But I heard the door open and somebody else entered the bathroom. I had a vision of it being Victoria, following me and ready to molest me. But the person didn't knock on my stall door and instead took up residence in the stall next to me. I didn't think I could silently rub one out so I put the idea of getting off out of my mind (temporarily) and unbuttoned my blouse so I could remove my bra. My nipples were standing at attention. My boobs are not huge, but my nipples are pretty big and they definitely are very sensitive. Because of the other occupant of the bathroom, I avoided rubbing my pointy nubs. Much like rubbing my clit, I didn't think I could be quiet rubbing my nipples. I was also worried about the sounds I was making taking off my bra and putting my blouse back on. I had to stifle a moan when the cool silk of my shirt grazed over my hard nipples.

This night was not turning out as I had imagined it would, but I couldn't deny I was aroused much more than I anticipated. I put my bra and panties into my purse and tried to make myself presentable before I left the stall. I hurried back to Victoria's booth. I half expected to find her friends had joined us, but instead I found Victoria had slid over to where I had been sitting and another glass of wine was on the table where she had been. I started to slide into the booth when she told me to lift the back of my skirt so my ass would be on the vinyl seat. I looked around to see if anybody was watching and then did as she told me. I sat next to her waiting for her next move. She reached over and rubbed my left nipple. My intake of breath was very noticeable.

Victoria then took her right hand and slid it under my skirt. I don't think I exhaled waiting for her to touch my pussy. She just smiled and rubbed my slit up and down. Then she slid her middle finger (I think) into my pussy while her thumb found my clit. I moaned for the second time.

Victoria keep asking me questions about myself much as she had done before, only this time she was finger fucking me. More accurately, she was tapping on my g-spot (I'd never tried to stimulate it, but I understood where it was) while rubbing my clit. My mind was a blur and I am sure my responses to her queries were gibberish. I didn't dare look around. I was sure her friends were watching her and I was sure she was determined to make me have a sloppy orgasm for their amusement. I grabbed the glass of wine and took a big sip.

When I did that, she slowed down her finger movements. She kept her finger inside of me, but she stopped tapping my g-spot and her thumb slowed down its manipulation of my clit.

"Just relax and enjoy your wine," she told me.

I smiled weakly and tried to remain calm, but staring into her eyes while she slowly teased me had me gushing on her finger.

"As I told you, I don't do hook-ups. I also only take lovers who can follow directions. So far you have passed that test," she told me. It felt good to have her happy that I took off my bra and panties. She took that opportunity to start rubbing me with more force.

"If you're willing to delay going home for a day, I will open your eyes to the world you have been imagining. But you have to play by my rules," she said.

Once again my mind was spinning with arousal and I wasn't fully comprehending what she was saying. I was more focused on the orgasm building deep in my soul and was worried at how loud I was going to be as she brought me off. She obviously sensed I was getting close because maybe 30 seconds later she stopped frigging me and withdrew her hand. She then licked her finger and smiled at me.

"No orgasm until I give you permission," she told me. "That is rule number one."

I can't say I really understood, but I nodded.

"Lift your left leg up onto the booth and lift your right leg over mine," she commanded. I obeyed. I'd have done anything to get her fingers back on my pussy right then. Or my fingers for that matter. This position left me spread wide, although thankfully hidden by the table.

"Finish drinking your wine," Victoria said. We talked as if we were old friends as I slowly finished my drink. Except for having my legs spread and my lack of underwear, I could have been out with a colleague. My rock hard nipples gave away my excitement to anybody who walked by, but I wasn't embarrassed. I needed to cum and I needed Victoria to provide my release. I felt confident she was going to finger me to orgasm or at least take me home to pleasure her and earn my release, but she had other plans.

"I need to talk to my friends for a bit," she informed me. "Give me your purse."

I quickly handed it over assuming she wanted to see my panties. Instead she put a small box into my purse from a bag she had. She didn't explain what it was.

"I want you to go back to your hotel. Don't open the box. When you get back to your room, I want you to shower and get cleaned up. You can dry off, but don't put on any clothes. Leave the lights on and the blinds open. I texted myself from your phone so you have my number. Text me when you are done with your shower and I will send you instructions. Do you understand?"

"Yes, Victoria," I said without thinking about the consequences of what I was saying.

"I know you're desperate to cum," she added. "But you have to earn that. Do you understand?"

I didn't really understand, but I answered in the affirmative.

She pulled a $20 bill out of her bag. "This is for a cab. Sit in the back with your legs spread like they are now. Touch your nipples during the ride to your hotel, but don't touch your pussy. I know if you did you won't be able to stop until you cum. That is reserved for later. Now go."

And just like that I was dismissed. She didn't say another word. I looked at her briefly, but her eyes said not to question her or her instructions. I closed my legs and slid out of the booth. Nobody seemed to have noticed the game we played, although I did see Victoria sitting down with her friends as I walked out of the door. I assumed she would relate the story of what I had done. But it didn't matter. I had instructions I needed to complete and I could feel my wetness running down my inner thighs.

I felt like a total slut as I stood on the corner trying to hail a cab. I could feel the cool night air blowing up my skirt chilling my wet slit, although that did nothing to cool my arousal. Fortunately it didn't take long for a cab to pull up. I told the driver which hotel I was staying at and sat in the middle of the back seat spreading my legs as Victoria had instructed me. Although she had not told me to lift my skirt like I had done in the booth I did it anyway. Something about sitting bare-assed on what I was sure was a dirty back seat of the cab was exciting. I definitely wanted to rub my clit and get myself off instead of just teasing my nipples, but the driver looked a bit sketchy so I refrained. Also, I wasn't sure how Victoria would know I came without her permission, but somehow I figured she would. So in between the driver's glances in the mirror to look at me, I discreetly touched my nipples. I didn't have to rub them to get the effect Victoria wanted.