One the Road Again - Chapter One By subKaren92
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.
Although the drive to the hotel was short, it definitely felt long, mainly because I wanted to get into my room and strip my clothes off. I texted Victoria before I took my shower to let her know I'd made it safely to the hotel. She didn't respond so I took my shower and by the time I was done, I didn't feel like a dirty slut any more. As I sent Victoria a second text, I felt like a clean slut. This time she responded telling me she would be available soon, whatever that meant. She reminded me not to get dressed, to leave the blinds open, the lights on and then added I was to sit in a chair facing the window and tease myself. I had mixed emotions about that. I wasn't worried about someone seeing me. There was an office building opposite of my hotel and it was late enough I figured nobody would be working. My main issue was masturbating without cumming. I didn't know if I could do that.
As I positioned the chair in front of the window I noticed the room light combined with the darkness of night made the window almost a mirror. I'd never looked at myself when I masturbated or when I had sex. It was an interesting experience and it made me feel like somebody in the building across the street was watching. I had a friend who told me she liked watching in a mirror when her husband did her doggie style. At the time I didn't give it much thought, but now I could see why she found it exciting. It would be like starring in your own adult movie without the embarrassment of other people finding out.
But back to the matter at hand, it didn't take long for me to feel the first pangs of an orgasm building. The fact that Victoria could have made me cum at the bar but chose not to meant my body quickly responded as I teased my nipples and rubbed my clit. My breathing was ragged. I had to slow down a couple of times to keep from orgasming. I didn't understand why following Victoria's instruction not to cum until she allowed it meant so much to me. But it did. Tonight was already better than any of the hook-ups I'd had before. I don't know how long I waited before I heard my phone chirp with another text. It could have been five minutes or 30, but however long it was, I was glad she messaged me again. At least I hoped it was her and not somebody from work.
The message was simple. "Retrieve the box I got you. Get your headset or earbuds for your phone. Call me when you're done."
I had not considered that I was going to talk to her again. I know that sounds weird, but because she had texted me before, I kind of thought we might just sext. Besides never looking at myself while masturbating, I'd never had phone sex either. I didn't know if that was what Victoria had in mind, but I was excited to find out. I got the box and opened it. It was a short curved vibrator. Fine, but I'd hardly need that to get off. My fingers would work for that task. I then got my earbuds and connected them to the Bluetooth on my phone. Finally I took a deep breath and dialed the new number in my phone from the text messages.
"Hello, Gwen," Victoria answered, sounding even more sultry if that was possible. "Have you been a good girl and followed my instructions?"
"Hello, Victoria," I replied, trying to sound confident. "Yes I did."
"Good," was her response. "You should be even more desperate to cum than you were at the bar."
"That I am," I said. "I could hardly touch myself facing the window. I was worried I would orgasm."
"I am proud of you for slowing down. What we did at the bar and what you did in your room is called edging. Has a lover ever done that to you before?"
"No," I confessed. "Guys just want to hurry up and fuck. I usually have to finish by myself after they are done."
"You won't have that problem tonight," she told me. That sounded promising. But then she added, "But you still have to play the game and follow my rules." I didn't understand that, but that was fine.
"I need to cum," I told her.
"I know you do. I know more about what you need than you can imagine. Did you open the box?"
"No I didn't," I lied. "You told me not to."
"Were you curious about the contents?" she asked.
"Very," I said.
"OK. Open the box," she instructed.
I felt like a kid at Christmas. Inside the box was obviously a sex toy. I knew it was a vibrator although I had not seen one like it before. It had one wide side and a narrow, flexible arm connected to a small side. I kind of thought I was stupid for not knowing what it was. Victoria remained silent for a few moments while I looked at it.
"It's a Lush," she finally told me. That really didn't help me.
"Um... OK," I finally replied.
"It's a remote control vibrator, silly," she added. I remained quiet. I didn't know things like this existed or how they worked. Was she standing outside my hotel room somehow? I didn't remember telling her where I was staying.
"I put an app on your phone while you were taking off your panties and bra at the bar. After you turn it on and connect it, you'll send me a link and I will control its speed."
I still didn't get it, but I assumed she knew what she was talking about so I said, "Sure."
"Don't worry," she said. "You're gonna love it. I already know you like having your g-spot stimulated. This will do that better than my finger did. From what you told me about masturbating in front of the window, I'm sure you're wet enough to insert the Lush, right?" she asked.
"Safe to say," I replied. Secretly I was worried that I would cum just from being penetrated.
"Open up the Lovense app on your phone and then turn on the vibe. They should pair," she instructed me. I did as she asked and the process was surprisingly seamless. She then told me how to create the long distance control link and I quickly texted it to her. The toy came to life briefly in my hand.
"I want you to shut the curtains, turn off the lights, pull off the blanket and lay on your sheet," Victoria continued. I was glad she let me close the curtains. With the lights off, the room was very dark. Just a bit of light came in under the door and a soft red glow came off the smoke detector. I hopped onto the bed with my phone in one hand and the vibrator in the other. Victoria told me to center myself with my head on the pillow.
"I want you to slide in the Lush in that beautiful wet pussy," she commanded. Her voice took on a harder edge that I liked. Even without it being on, a moan escaped my lips as I felt it fill me. As she predicted, it nestled quite nicely against my g-spot. I wouldn't say that scared me, but as wild as Victoria drove me with just her finger, I was a bit nervous about her controlling a vibe there. She gave me 15 seconds or so before giving me another instruction. I was guessing it would be to play with my nipples some more or even to rub my clit. But instead she told me to place my phone on the bed and spread my arms and legs to the corners.
"The next time I see you, I am going to tie you down," she told me in a matter of fact tone as if that was perfectly natural. "This will let you decide if you want that to happen." Before I could formulate a response, the vibe sprung to life, albeit at a very slow pace. Still my hips jumped at the sensation.
"OK Gwen," Victoria cooed in my ear. The earbuds made her sultry voice very intimate, similar to when she put her mouth next to my ear at the bar, but even more immediate. "I'm going to tell you what I know about you while I control your Lush. If you cum without permission, if we ever meet again I will punish you." The Lush sped up and I moaned instead of responding. I got the sense responding wasn't that necessary as our conversation seemed more like a monologue.
"Actually, there is a good chance being punished is why you will want to see me again," she continued. I definitely didn't understand that, but she sounded confident. The Lush slowed back down leaving me instantly wanting. I knew I could make myself cum almost instantly by rubbing my clit and likely by pinching my nipples.
I don't know exactly how long Victoria teased me with the vibe and perfectly described my life and how I felt about relationships, my sex life (why it was unsatisfying) and my deepest desires for what I really craved. She controlled the vibe with expert precision bringing me to the brink of what I sensed would be the biggest orgasm I ever experienced only to bring me back down. She also had the uncanny ability to remind me to keep my arms and legs spread and not to touch myself. I don't know how she knew so much about me. I know we talked very intimately at the bar, especially after I had removed my panties. But she knew my deepest feelings in a way we had not talked about. To say she was in my head was an understatement. To say I was determined not to cum until she gave me permission was an understatement as well. I wanted to please her in a way I'd never felt about someone else. She talked, I quivered and moaned. Occasionally she would have to repeat herself when she asked me a question because I was so focused on trying not to orgasm, that I didn't really hear her.
Victoria told me the reason I was so excited by hook-ups was that I was looking for a dominant partner, even if I didn't realize that. I remember discussing at the bar that my parents were very strict. I thought my wild side was the result of my rebelling against them. Victoria told me in no uncertain terms that actually I wanted someone to give me rules and structure. I kind of argued, not forcefully as she had turned up the vibe as she told me that and I was really focused on that, but as she turned it down, she reminded me that I was following the instructions of a stranger and had already begged several times for permission to cum. She then turned the vibe up full speed for the first time. Unfortunately it was for less than five seconds, but that was enough to convince me that she was right.
"Am I correct that you need rules and structure?" she asked me.
I breathlessly answered, "Yes," although I wasn't sure exactly what that meant or if I really believed it. I enjoyed the rules and structure of her game and I needed to cum so I played along.
"What about discipline?" she asked. That was a bit further outside my comfort zone, but my pussy spasmed and clamped down on the Lush when she said it. My body was telling me that was true. "Yes," I replied mixed into a couple of moans.
"I will let you cum soon," Victoria told me. "But I want to see you tomorrow. Can you delay going home an extra day?"
If it meant I got to orgasm, I'd agree to stay a week.
"Yes," I answered. She didn't need to know I already planned on staying until Friday. The vibe sped up, although not nearly all the way. Just enough to know that she liked my answer.
"Once I let you cum," she cooed, "I expect you to follow my instructions for the morning and then meet me at my office at lunchtime."
"Of course," I replied, my voice dripping with lust. She could have told me to walk naked into the hallway and I would have done it right then to earn my orgasm.
"Good girl," she said. That warmed my heart for some reason.
Finally she gave me permission to cum, although there were a couple of qualifications I never would have thought of on my own.
"I am going to turn up the vibrator to full speed. You need to pinch both your nipples forcefully. I am going to count down slowly from 20. You may orgasm when I reach zero. When I reach ten, you will rub your clit hard with one hand while still pinching one nipple. If you cum before zero, when I see you tomorrow I will spank you. If you make it all the way, you will be rewarded by having your pussy eaten in my office."
"Oh my God," I said without grasping everything I was agreeing to. She called me a good girl again and then said "20."
The Lush sprung to full power and I grabbed both my nipples. How I didn't orgasm instantly I don't know. Victoria counted very slowly. It was quite maddening but with each new number her telling me that I needed rules and discipline rang in my head and my desire to please her somehow kept me from orgasming. I was hanging by a thread. I'd never actively tried not to cum, especially while touching myself. By the time she reached ten and I moved my right hand down to my clit, I was crying and shaking in need. But I didn't want to disappoint her. I wasn't even worried about her promise to spank me. If she wanted to do that, I was happy to let her. And even though I wanted to experience a woman eating my pussy, I would gladly skip it if that meant she was pleased with me.
By the time she reached five, I was screaming for permission to cum. I hoped the rooms next to me were vacant. The room above and below me too. My pussy was pulsating and I felt like I was going to piss myself. After saying four, Victoria spoke again. "You're doing well pet. Just a bit longer. Then you can cum for me."
I'm not sure if it was her calling me pet or telling me I was going to cum for her, but I think I fell in love with her at that moment. I could feel my juices leaking out of my pussy. I'd never had that happen except during my best masturbation sessions with a Hitachi wand and then only during my orgasm. I had not cum yet and somehow I felt at peace and that I was going to make it to zero. I did have a screaming moan at three and my hips rocked back and forth.
Victoria didn't seem to be in a rush for the last couple of numbers. She couldn't see me so she couldn't enjoy the show I was putting on. But maybe it was just my subservience to her commands that excited her. Maybe she was masturbating silently and wanted to cum at the same time I did. I don't know why the last few seconds seemed to last longer than the ten before them, but my mind was content that I wouldn't cum until she said yes. She could go another twenty seconds and I think I could make it. Or she could just say "Cum now," and I would explode.
Being in a dark room with my legs spread wide open didn't hurt my arousal. Victoria had told me to imagine being tied that way and the thought was exciting. I'd never been tied up. Nobody had ever asked if I needed discipline either. I pictured myself bound and at Victoria's mercy. I kind of remember hearing her say, "Two." My body had started convulsing. Much like how my pussy leaking fluid had only happened during a massive orgasm before, the same could be said about convulsing. But I hadn't peaked yet. If I had been capable of rational thought at that moment, I might have been worried. But rational thought left the building a while ago. "One," she said. I felt energy radiating out from my clit and nipples merge and shoot up toward my brain. There was a brief pause as I was consumed. Then I blurted out, not as a conscious decision but more as an erotic reflex, "Please Mistress. My your slut cum?"
The pause continued for what seemed like an hour but was likely not more than a second or two... "Cum for me Slut Gwen. Cum for your Mistress."
Words can not describe the release I had. You probably already guessed that I squirted for the first time, although I didn't realize it at the time. I clamped my legs together and rolled from side to side as my body spasmed. I didn't even really know how long my orgasm lasted as I think I might have passed out from the pleasure. When I finally came down from my high, I realized the bed was soaked. Apparently I was a sprinkler as I rocked from side to side. The Lush had turned off, probably after I had stopped screaming in pleasure and the call had disconnected. My heart was pounding for at least five minutes and I just lay in the wet bed for at least 15 minutes calming down.
As I started to recover, I tried to remember what I had said to Victoria and what I had promised. Seeing her tomorrow was a memory, but I couldn't remember any details. I pulled the vibe out of my well used pussy and licked it clean. I'd done that before with my cock shaped vibe, but since this one was oblong, it somehow felt dirtier to clean my cum off of it. But I was far past worrying about that. I got out of bed long enough to put my phone on the charger. I also cleaned the vibe with soap and water and found its charging cable in the box. I knew I could use it again with me in control, but that seemed wrong. I also knew my body wasn't ready for round two. I needed sleep.
The sheet felt cold since it was wet with my squirt. It was kind of disgusting actually. But as I pulled it over my overheated body and then the blanket on top of it, it felt right. I created the mess with the biggest orgasm of my life and sleeping in it was my way to keep the feeling going. I'm sure I dreamed of Victoria that night since I woke up with my fingers on my (still?) wet pussy. Looking at the clock I saw that it was 7:30am. I never sleep that late. I was ready for round two and I wondered how long I could tease myself with the Lush before giving in to my desire to orgasm. I picked up my phone to launch the app and saw a text that had come in during the night. It put an end to my plan. There was a simple message. Well, simple in that it was instructions for me to follow.
"Remember slut that your pussy belongs to me. No touching it without permission. Shower and clean yourself up. When you are dressed, send me a text. I will send you an address to a boutique a friend owns. I have instructed her what to fit you in. You will purchase the items. Her shop opens at 10am, but you will be there by 9. After your fitting, send me a picture. If it pleases me, I will send you the address of my office. You will arrive at exactly noon. Wait in the hall until you see my assistant leave for lunch. If you decide against continuing, that is fine. Enjoy the memory of last night and the Lush is yours to keep."
I read the message several times and my pussy got wetter each time. Then I remembered Victoria promised to eat my pussy if I didn't cum without permission. That helped me decide to continue her game. I didn't know what kind of boutique her friend ran (my lustful mind instantly thought sex toy store or bondage emporium since Victoria promised to tie me up) but I figured I would find out soon enough. I placed an order for room service breakfast and dashed to the shower to wash away my night's events. I was clean and in a robe when the waiter arrived with my breakfast, although the bed was still a fright and the Lush was still charging on the dresser. He didn't mention it. I'm sure he's seen worse. I wasn't even embarrassed.
I sent a quick message to Victoria, along with a selfie of me with the robe hanging open. She didn't ask for it, but since she said she owned my pussy, I figured she might want to see it. While I was eating my phone buzzed. The message was an address and her friend's name Heather. That was all. No comment about my picture and no instructions how I was to act at the store. I guess she figured I already knew what she expected. I suppose I did. Heather was opening the store early for me because of her friendship with Victoria. I would be nice, do as she said, buy what she was selling and not do anything to make Victoria look bad. I looked up the address and it was on the near West side about a mile and a half from the hotel. An Uber got me there 15 minutes early. I waited outside until a beautiful older woman (early 40's I estimated) opened the door. She correctly guessed I was Gwen and ushered me inside, locking the door behind me.
Was it wrong that my pussy was getting wet and I was hoping she would tell me to pleasure her?