On the Road Again Ch. 02

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Gwen's second day under Victoria's guidance.
9.3k words
4.85
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Part 2 of the 2 part series

Updated 11/23/2023
Created 11/23/2023
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If you have not read chapter one, I highly suggest you do or you will be very lost...

Heather's boutique was obviously a high end shop. The front showroom was a combination of lingerie and dresses, skirts and blouses. I let my hands roam over the silky material of a camisole but I didn't look at the price. I think I was scared to look. Heather kept walking toward the back of the store and turned back to look at me.

"I keep the kind of stuff Victoria likes back here," she said. "Come with me."

I scurried to catch up to her. "I appreciate you opening early for me," I told her.

"Victoria is a very good client and apparently has high hopes for you," she told me. I wondered how much information Victoria had shared about me with this alluring woman. I also wondered if Heather shared Victoria's interests.

She brought me into a room in the back of her shop that had floor to ceiling mirrors on two sides and several racks of clothes, mostly leather and a few other materials I didn't recognize. They were all black.

"Take off your clothes, Gwen, so I can measure you. You can put them on that chair," Heather told me pointing to a chair in the corner. It didn't sound like a command like Victoria would have used. She sounded like she really just wanted to take my measurements. Well, in for a penny, in for a pound. I quickly disrobed. I was sure she meant I should take off my underwear as well even though she was not specific.

Heather was methodical in taking my measurements. She did complain that her assistant wasn't there to write down the numbers, but she didn't come in until 10. I wasn't embarrassed standing naked in front of Heather, but I wonder if being in front of two unknown women would have been different. No matter. Heather was efficient and asked me for my shoe size instead of measuring my feet. She said her shoe selection was a bit limited right then but she would try to find me something. "Give me a few minutes and I'll be right back," she said before leaving the room. Now I felt a bit self conscious. Standing naked in front of the mirrors reminded me of how unplanned this trip was ending. Fortunately Heather did not take too long. I suppose Victoria had already specified what I was to wear and Heather just needed to get the right sizes.

"Do you need to go to the bathroom?" she asked. "You might want to before you get dressed."

Weird. But sure. That sort of made sense. Heather escorted me out of the room and to a small, but thankfully clean, bathroom. I just peed. She was waiting for me back in the dressing room.

"OK. Let's get started with your lingerie," she told me.

Normally it takes me trying on many bras until I find one that fits correctly. Even if the size is supposedly right, I struggle to find the right one. Heather walked up with a leather bra (I'd never worn one before) and had me slide my arms through the straps. She then cupped my breasts as she made sure the bra sat correctly. My nipples immediately reacted to her touch. And speaking of my nipples, it was a good thing they got hard, because the bra had reinforced circular cutouts allowing my nipples to poke through. At first I didn't understand. But as she hooked the straps pulling the bra tightly around my form, I got it. First off, the bra seemed a little undersized. At least undersized from what I would choose. However that fact lifted my breasts and formed a deeper cleavage than I am accustomed to having. Oh, and the cutouts force my nipples and a bit of areola to pop through the front. No matter what kind of top I wore, my girls would be on display.

Next up was a leather thong. This was not difficult to step into, but I quickly realized it was different from any panty I had ever bought. First off, because it was leather it was firm. That wasn't particularly problematic, although I was concerned it would not absorb any juices if Victoria decided to tease me. I'd never particularly worried about that until yesterday. Second, the thong strap disengaged from the waistband. I didn't understand why until Heather snaked it between my legs and split my crack with it. It was like a g-string only much stronger. As she clipped to the waistband, I heard a click. She then tugged the side straps and they didn't move a millimeter. It was only then I noticed a hard protrusion in the front of the panty nestled firmly against my clit. I took a deep breath as I realized what that meant. I reached around and felt where the strap clipped to the waistband.

"Don't worry Gwen," Heather said. "Victoria has the key."

I suppose that is why she wanted me to go to the bathroom first. This thong wasn't coming off until Victoria took it off, at least two and a half hours from now. As I took a step, part of a twirl I made to look at the bra and thong from different angles in the mirror, I realized the purpose of the protrusion nestled on my clit. You might think I should have realized its purpose immediately. Subconsciously I probably did. But when I moved and my clit rubbed against it, my conscious mind realized walking was going to be pure torture. Correction. Not being allowed to cum was going to be torture.

Heather briefly left again and returned with a pair of thigh high stockings she tossed to me and told me to put on. She left again, this time returning with a white cotton dress and a pair of white pumps.

"I'm sorry these are only three inches high. They are the only one's I have in white and your size."

I had noticed most of the shop had black clothes so I wondered why Victoria wanted me in white. It couldn't be because she thought I was virginal. It didn't matter. The dress was perfect for my curves without being obscenely tight. My nipples pressing against it were a bit obscene, especially since I was concerned the weave wasn't tight enough to keep them from poking through. The length was to my mid thigh and covered the tops of my stockings. It rode up when I sat down, the stocking tops would be uncovered, but at least if I was standing, I would be properly covered. The shoes fit fine and I was happy there was only a three inch heel as I didn't usually wear anything higher.

We finished up just as Heather's assistant was arriving and the shop was opening. I had expected the entire experience to be more sexual than it was, but finishing this task got me closer to seeing Victoria again, so I had that going for me. I sent her a text that we were done and Heather suggested I send her a picture. I gave Heather my phone and she snapped a couple of shots from different angles. I felt like a model. Victoria responded affirmatively and gave me an address and office suite number while reminding me to arrive exactly at noon. I thanked Heather and paid for my new outfit. It was more expensive than I would have bought normally for myself, but I didn't mind as it was going to get me into Victoria's office. While paying I was temporarily distracted by the thong doing what it was designed to do. That distractio continued as I walked about 40 feet from the counter to the curb. I didn't see any cabs so I ordered an Uber back to the hotel. I had a little time to kill.

Normally I would have taken a walk to kill time, but the thong made that risky. I was worried that if I walked around I would force myself to cum. But you know what? Sitting around my hotel room didn't make those feelings go away. I ended up pacing back and forth and even rubbed my nipples through my dress. The only saving grace was when I had to stop and catch my breath, I didn't look out of place since I was alone. I looked up the address of Victoria's office and saw that it wasn't far from my firm's office. That was a problem. A, it was too close to take a cab. I'd have to walk. Slowly. B, I ran the risk of seeing somebody I knew. I think that worried me more than cumming while I walked down the street.

Victoria didn't send any more messages. I watched the clock and tried not to rip off the dress and somehow get the thong off. I figured it was a 5 minute walk to her office. I left at 11:30 to give myself extra time to stop if I needed to quell my arousal. But as I walked out of the hotel lobby, feeling like everybody could tell what was happening under my dress, a wonderful thing happened. Much like last night when my desire to please Victoria suddenly gave me the emotional strength not to climax, it happened again. Not all at once mind you. I was taking tiny steps to minimize the friction on my clit. I was sure I was going to lose the battle and cum in front of the other people walking between buildings. But just as I was reaching my peak, my mind found a peacefulness like it had last night and told me I was going to make it. I could feel my juices squishing against the firm thong and I could smell my arousal. But I didn't think I wouldn't be able to control myself. It was a wonderful feeling.

I was able to cover the short distance quicker than I anticipated. In my mind, I even looked normal, although my nipples gave me away. I hurried past our building while praying nobody I knew would see me. I made it safely. I ended up in front of Victoria's building 15 minutes early. I didn't know the layout of the inside, so I stood out front trying to calm my beating heart and cool the fire in my pussy. Yeah, that didn't work so well. It was an older building and thankfully there was no guard I had to talk to before I reached the elevators. Up I went. I wasn't sure if Victoria worked at a big company where I would have to talk to a receptionist. As I entered the elevator lobby, I saw there were two hallways leading in opposite directions and the office suites looked fairly small like they might be just for small companies. I found her suite. There were two doors close to each other, but on one door was the lettering Victoria Andersson, Psychologist. She had not told me what she did for a living, but it made sense that she was a psychologist given how she had basically interviewed me in the bar and then told me all my inner secrets when we had phone sex. When I had phone sex, I mused. I didn't know if she got off during our conversation.

I was a bit distracted when I suddenly remembered I wasn't supposed to go in until her assistant left for lunch. I hurried down the hall away from the elevators and hid around the corner to the stairs. I'm not sure what I was feeling as I peeked around the corner looking for someone to leave the office. A few minutes later the door with the lettering opened and a professionally dressed older woman (early 40s?) came out and headed toward the elevator. As soon as she turned into the elevator bank I hurried back to Victoria's office and went inside. There was a desk, a couch and another door, which was open. I moved to that door. Victoria was sitting at a desk and there was a chaise lounger, another couch and another closed door. She put her fingers to her lips and then waved me in.

She had a monitor on her desk that showed a camera in her reception room and another view of what must have been a second office accessed via the other door. As I approached the desk she softly said the other office was a place for her patients to collect themselves if necessary before leaving. I looked at the monitor and there was a woman sitting on the couch in that office.

Victoria whispered again, "I like that dress on you. Were you a good girl this morning?"

I obviously had followed her instructions to buy the clothes so I assumed she meant did I cum without permission. Taking a cue from her low volume I whispered back, "Yes, Mistress, but it was very difficult."

Fortunately the woman in the other room stood up and walked out of the door into the hallway.

"Good, she's gone." Victoria said in her normal husky voice. "So, you didn't cum. That's good. How much effort would it take me to make you climax? You smell like you need it."

"Honestly, Mistress," I replied. "Much like last night I'm pretty desperate to cum. I didn't think I'd make it walking over here, but then I had a clarity in my brain that let me hold off climaxing in order to please you. But it wouldn't take much if you told me to cum right now. I could probably just rock back and forth in this dastardly thong and orgasm. Who designed this thing?" I wasn't expecting an answer, but it wouldn't have surprised me either if she knew.

"You're learning faster than most women," she told me. I took that as a complement. "I did promise you would get your pussy licked as a reward for being good last night. But I get mine first."

I remember her telling me I would have my pussy licked as a reward, but I didn't remember her saying I could climax. Still, as amped up as I was, I think it was preordained that I would have another thrashing orgasm if she ate my pussy. I watched lustfully as Victoria unzipped her skirt and let it fall to the floor. She wasn't wearing panties and her pussy looked wet already. I wondered if that was in anticipation of my arrival or a byproduct of the woman who left. It didn't really matter. She told me to turn around and put my hands behind my back. I then remembered last night her telling me she intended to bind me. The cool metal click of a set of handcuffs immobilized my arms and sent a new gush of juice against the thong. She then spun me around and pinched my nipples before she spun me around again and lifted my dress up over my butt. I bent forward, thrusting my ass against her.

"Not yet, my pet," she said teasingly. "I get mine first." She then backed away and I turned as she hopped up on her desk and spread her legs. "On your knees, slut, and service me," she ordered. It was an order I was happy to obey.

Victoria knew I'd never licked a pussy before, but I gave it my best effort. It was much tastier than I anticipated. I also loved that she held my head in place. It was a very possessive act and it filled my soul with warmth. Alas she seemed to be in a hurry because before she climaxed, she lifted my head up and told me I needed practice. I'd failed, but she told me not to worry about it. We were on the clock before her next client would arrive. She also told me she would give me more practice later. That made me feel better. She had me stand so she could remove the handcuffs. Then she told me to strip.

"Normally I would have you do it slowly and more erotically," she told me. "But unfortunately, time is not our friend right now. Just put your dress on the couch and take off the bra. I'll get your panty's key."

I definitely didn't feel sexy stripping off my clothes in such a perfunctory manner, but I was happy I didn't have to wait until tonight to see Victoria again. Heck, after our phone sex session last night I wasn't sure I'd see her again at all. I presented myself to her wearing just the locked thong, stockings and heels. She told me to hold my hands behind my head while she knelt down and unlocked the thong. I knew my arousal scent was strong. When I get excited, you'll know. But I had not thought about how Victoria would react to having her nose so close to my pussy. I was a bit embarrassed when she said, "Oh my. My slut is excited." Of course I was. That was the purpose of this thong. And although I was uncomfortable with being called a slut, I couldn't really argue as I was standing naked in the office of a woman I'd only met once and then for about two hours.

Victoria didn't touch my pussy and thankfully didn't rub my clit. While I'd put my need to climax behind me walking to her office, if she touched me, I think I would have failed to wait for permission to cum. She told me to lay down on the chaise lounge. I knew that is where her patients sat. I wondered how many women had been in this position. I also thought about how I squirted last night. If I did that again, the chaise would be soaked before her next client arrived. Weird things were running through my mind, especially when she started to wrap leather cuffs around my wrists.

She pulled my arms above the top of the chaise and affixed them to what I assume was a chain on the back. This was the first time I was restrained where I couldn't move. It kind of felt like laying on my bed last night, although now it was real. I pulled my wrists testing the bonds. I had some movement, but not much. She then cuffed my ankles. She then told me to spread my legs and put my feet on the floor. This time a chain went under the chaise forcing me to keep my legs spread open. I was now at her mercy and prayed she wasn't kidding when she told me my reward was getting my pussy licked.

Her final preparation for me was a blindfold. Now with the room dark, it felt much more like my hotel room last night. It was just as quiet. All I could hear was my heartbeat pounding. Then I felt her hot breath on my ear like she had done at the bar. "I have to get something from the other office. Give me a moment." As if I had a choice but to wait for her.

I heard the door open. Soon after I felt her weight on the end of the chaise. Had she retrieved a dildo or vibrator to fuck me? I hoped so. Then I felt her warm breath blowing along my slick folds. "Oh yes, Mistress," I groaned. Before I felt her tongue, I felt her finger softly run along my slit, but not inside. It felt different than last night, but then again, I was a different person now. After a few teasing circuits along my pussy, I finally felt her tongue lick the length of my slit from bottom to top and then across my engorged clit. I thrust my hips upward as much as the chains would allow. It wasn't much, but I assumed Victoria would appreciate me trying to force my pussy against her mouth. Then the most shocking thing occurred. I felt hot breath on my ear again while the tongue was still just grazing my slit. "You're not the only one being rewarded here, pet," the lust filled voice spoke into my ear. Instantly I struggled against my bonds as I realized Victoria wasn't the person eating me. Or should I say teasing me since she really had not started pleasuring me with as much gusto as I had tried to give my Mistress.

"The woman between your legs is my friend, Mary," Victoria explained. "She's not submissive like you, but she does do some favors for me in exchange for me fucking her on occasion. Her husband isn't very good in bed so when her needs reach a certain point, I help her out. I was going to take care of you myself, but she needs a good screwing, so I told her I would help her if she ate your pussy."

"Um," I stammered. "I don't know what to say." My arousal buzz dropped precipitously by the revelation that Victoria wasn't the woman between my legs.

"Don't worry, Mary," Victoria said. "She'll warm back up quickly." How did she know how I felt? I didn't say anything. "She'll flood your mouth quickly," Victoria said with confidence. "But remember, you don't cum before she does." I smiled knowing that I wasn't the only one with restrictions on our climaxes. "Oh, and don't think you just get to cum when you want Gwen. You still need permission."

Mary moaned into my pussy and I felt her press forward against me. I couldn't see it, but I could picture Victoria wielding a strap-on and mounting her from behind. I was now in the unique position of trying to hold back my orgasm in a competition with Mary holding back hers. Victoria was right that soon my arousal would reappear with a vengeance. Mary was much more skilled than I was at eating pussy. I suppose she had lots of practice with Victoria. Soon I was squirming against my bonds as I heard Victoria fucking Mary with great passion. Every thrust drove Mary against me and every thrust squished her juices on Mistress' cock. I was moaning, Mary was moaning, although muffled by my pussy, and Mistress was alternating between cheering us on with a series of derogatory phrases and names and reminding us not to orgasm.

I was the first to beg for permission to cum. Mary didn't, although her oral ministrations had mostly stopped and my stimulation was pretty much just riding her face as Mistress pounded her from behind. I had a vision in my mind about what they looked like as the sounds of fucking echoed off the wall.