On the Road Again

On the Road Again - Chapter Three

By SubKaren92

I was too far gone in my post orgasmic haze to comprehend what Victoria said. I watched her head toward the kitchen, but I couldn't move for several minutes. When I finally joined her, I saw two plates set on a small dinette table along with several cartons of Chinese food. There were two chairs pulled out one of which had a thin dildo attached to the chair with a suction cup. I assumed that was my chair. I started walking toward it when Victoria stopped me and told me to face her. I immediately did and she grabbed my left breast. She didn't squeeze it or play with my nipple unfortunately. Instead she took a marker I had not noticed in her right hand and drew a long straight line about three inches long down the top of my breast.

"Just so we don't lose track," she said. I didn't grasp at first she meant my orgasm count, but that had to be the purpose of the mark. I smiled. "Do you want me to sit down, Mistress?" I asked, trying to sound alluring.

"Yes, pet," she responded. I straddled the chair with the dildo. It wasn't wide enough to fill me, but it felt good nonetheless and the kink factor of sitting on it at dinner was off the chart. Victoria sat down on the other chair facing me. She served me a combination of food and before I could dig in she told me to spread my legs. As I did she lifted her right leg and put the tip of her boot against my pussy. She then started rocking it from side to side against my clit. I looked at her in deep appreciation for giving me this unique experience.

"You said you struggle to reach orgasm number two during your encounters," Mistress began our dinner conversation. While that is true, I never had a gorgeous woman teasing my clit with the tip of her boots right after she gave me a massive orgasm either. My arousal had dipped a bit after my climax, but it quickly started building again. I was eating dinner, but I was also bouncing slowly up and down on the dildo. I needed to lean forward to do that which had the wonderful side effect of pushing downward on her boot. By the end of dinner I was begging for permission to cum again.

"So I guess you lied when you said a second orgasm was difficult for you?" Victoria asked in a condescending tone.

Breathlessly I replayed, "No, Mistress.

I mean it always has been, but with you it is different."

"Tonight I will be generous with your climaxes because I want you to learn about yourself, learn about me and reinforce that I can give you pleasure you have never experienced."

"Thank you Mistress," I replied. "Can I cum now?"

"You may, my beautiful slut," she said with pride.

There was that word again. It triggered me just like the last time she used it with me. Instantly I started cumming. No it wasn't as massive an orgasm like the last one, but what could be? Still it was a good one. If I am honest, it was probably as good as the kind I usually gave myself after one of my male partners had given up. It was just, by comparison to the two previous ones Victoria had been a part of, it was disappointing. I think she sensed what I was feeling because she commented that, "They can't all be screaming, squirting messes." I just chuckled, amazed and grateful that I'd had another orgasm in a matter of 20 minutes or so.

When I calmed down, Victoria once again grabbed my left breast and made a second line parallel to the first. "Clean up the dishes," she told me. "Then you can join me in the living room where you will learn how to pleasure me." That opportunity excited me so I hurriedly rinsed the dishes and put them in the dishwasher. I was probably only alone in the kitchen for about two minutes, but I already missed being with my Mistress. I hurried out to the living room to begin my tutoring.

Victoria had put down a yoga mat near the window. She was also holding another suction cup dildo, although this one looked much wider than the one in the kitchen. I watched as she deftly slid it into her pussy. She gave herself a couple long, slow strokes with it. My pussy felt jealous, although I soon found out it didn't need to worry about missing out. Victoria pointed at me and curled a finger indicating I should join her. I walked over and she pulled the dildo out of her pussy and held it up facing my mouth. I didn't need to be told what she wanted me to do.

I kissed the tip of the dildo, savoring her flavor, and then went down on it sucking off her juices. The taste was wonderful as she had obviously been aroused by giving me a boot job at the kitchen table. She didn't have me suck the dildo for long. Perhaps ten seconds. She then walked to the window and licked the suction cup enough to affix it to the glass. I recognized that the height was appropriate for a girl backing up to it while on her hands and knees. Victoria then laid down on the yoga mat and spread her legs facing the dildo. She pointed to the floor between her legs and I quickly got in position on my hands and knees where I could lick her pussy.

"I am going to teach you the proper way to eat me. You are to just keep the tip of that dildo inside of you. Do not rock back on its length until you make me cum. That will be your reward for doing a good job. Do you understand?"

"Yes, Mistress," I replied. I wiggled my butt trying to find the dildo. This window was facing North so I didn't know if anybody in the building next to us could see us. I had to reach back to hold the dildo firmly enough to insert the tip into my pussy. This one was much fatter than the one I rode in the kitchen and I prayed I would please Victoria and she would let me rock back and fuck it. But I knew I had to earn that pleasure. I then leaned down and took a tentative lick of her slit. It took all my willpower not to rock back and impale myself on the dildo. True to her promise, she began instructing me.

Victoria first told me about a series of foreplay techniques, although they would be wasted on her as she was already aroused and ready for me to get to the main course. She specified that I needed to learn and practice them for future encounters, but for now, we could skip them. She then told me about the pancake technique.

"Keep your tongue flat and pointed down toward your chin," she began. Flat and wide and don't move your tongue. Move your entire head making contact from the bottom of the vagina upward until you reach the top of the clit. Then break contact and repeat. I did my best to get it right and I could tell Victoria was enjoying it. She added that I should go slowly and use the minimum amount of pressure necessary to make my partner cum. In my mind, I questioned how I would know how much pressure that would be, although in the moment, I didn't question her teaching.

"When you are more experienced, you will learn when to be fast, when to be normal, when to go slow and when to go agonizingly slow to tease her," Victoria added. "Although if you tease me, you will not like my response."

I wasn't trying to tease her. I was trying to find the right pace to make her cum. That was my only goal. Well, that and getting to slide down the full dildo as a reward. Victoria's pussy juice was flowing on my tongue. I took that as a good sign that I was getting better. At some point, she grabbed my head, holding it still so I couldn't move my tongue.

"That was close," she said. "You almost sent me over the edge. But I want to teach you about the vortex."

I was pleased to hear she had almost cum. Yes I enjoyed the pleasure she gave me, but in my soul I needed to be able to please her as well. Actually that was more important to me. She taught me that the vortex was a series of techniques designed around sucking a woman's clitoris. Basically you wet your lips and make an O sized appropriately for the size of your partner's clit. I had not noticed before, but Victoria's clit was significantly larger and more pronounced than mine. I didn't know if that made her more sensitive, but I did my best to capture her clit on the first attempt. I think I did good because she told me about four variations.

"The constant vortex," she began, "is the easiest so start there. Apply a constant level of suction until you need to breathe. Then break contact, take a breath and do it again. You can make many women cum this way, especially if you performed your foreplay and the pancake properly."

I started out this way. She continued to give me instructions, but there were mews and moans in between her comments. I took that as a good sign.

"The rhythmic vortex works great if you have music on in the background. You suck her and release the pressure rhythmically. You can set the tempo, slow, fast or to the beat of a song, but listen to what her body tells you and gauge what she prefers. The main take away from all these techniques is to match what she needs at any particular time. Her preferred method will change based on what she's feeling, so you need to be proficient in all of them."

The rhythmic vortex made sense. I had a boyfriend do that once. It was one of the few times I came with a man. Victoria also told me about the hard vortex, basically sucking in quickly with a strong pressure and slowly releasing it and the licking vortex, which I quickly determined was her favorite. Under her instruction, I sucked in her clit firmly and held it there, similar to the constant vortex, but while latched on, I used my tongue to flick her clit. I determined this was her favorite because probably 15 seconds after I started it, she started to orgasm. I felt very proud of myself and made a mental note to memorize these techniques. With guys it is easy. Suck and lick their cock until either they squirt or they fuck you. Women are far more complex.

Victoria was bucking against my face as she rode her climax pony. That forced me a bit further down on the dildo. I liked that, although I did worry she might get mad. Then I realized she wouldn't be noticing anything I did at that moment. I held my position kneeling before her pussy until she calmed down. She then ruffled my hair and said thank you.

"That was pussy eating 101," she told me. "Your reward is to fuck yourself while you begin pussy eating 202." I didn't have to be told twice. I rocked back impaling myself on the phallus. I then rocked forward, enjoying the feeling of the dildo sliding out of me, putting my tongue back in the pancake and loving the taste of her post-orgasmic pussy. She warned me to give her clit some time to recover before diving back in and to just lap at her folds. I understood that from my own experiences. Victoria added several new techniques. I wondered if there would be a test. This time since I was fucking myself, I wasn't as sure I'd be able to memorize them. Would it be weird to ask later for her to repeat her lesson so I could take notes?

She taught me about the under pressure, a variation of the pancake I could do while she was still recovering and how to edge her, by doing something else pleasurable like kissing her inner thighs when I sensed she was close to climaxing to let her cool down a bit before resuming. I certainly understood that one based on the last day's experiences, but again she warned me not to do that to her. I wondered why she was teaching me this unless she planned on me doing it to other women. I put that thought out of my mind as I was concentrating more on the feeling of the dildo I was enjoying. In fact, I was quickly reaching orgasm number three. I did my best to get Victoria off again before I came. I used the under pressure and the licking vortex. I could tell she quickly was reaching another plateau, but so was I and I had to break contact with her pussy to beg for my own release. Surprisingly she gave me permission and immediately my pussy clamped down on the dildo and my endorphins began to flow. Again, it wasn't the massive release as I had when I had been teased all afternoon, but it was stronger than my kitchen cum.

Victoria rolled off the mat without her own second climax as I lay spent on the floor. She returned with a glass of water for me. I sat back up and took the glass thanking her for the kind gesture and apologizing for not being skilled enough to make her cum again. She was kind about it and told me not to worry. "I have many more techniques to teach you. You will get another chance to please me soon." I smiled at that and wasn't surprised when she grabbed my breast again and made a third line. She then went into her bedroom, at least I assumed as much, and returned with a video camera and a mirror.

"Sit up on the couch," she told me. "Have you ever looked at your sex while masturbating or having intercourse?" she asked. I had to reply no.

"Your ass looked amazing reflected in the window as you fucked yourself," she told me. I'd forgotten I was putting on a show.

"I want you to play with your pussy and tease your nipples," she told me. "I'll hold the mirror so you can watch yourself."

Victoria held the mirror so I could see my pussy. It was already showing signs of abuse from my first three orgasms, but I wasn't about to stop now. I started rubbing my clit with vigor and pinched my left nipple. Victoria had opened my eyes to the pleasure of a bit of pain and even though I had just cum, my clit welcomed the attention of my finger. Here I was shocked that I'd had three orgasms, working on my fourth and applying very firm pressure with my fingers to achieve that result. I was watching myself in the mirror. That was a new turn on. I hardly noticed that Victoria was holding the video camera in her other hand. Within minutes the video recorded me asking for permission to cum. It wasn't begging, at least not like before. I felt like I could cum, but I wasn't desperate to cum yet. I would have been fine if she said no. But again, she surprised me and gave me permission when I first asked. Victoria said she was proud of my first porno and that her friends would love it. I didn't really hear her as I was busy cumming. She did immediately marked my breast with a fourth line and said "She meant it." I didn't understand what she was referring to, but I didn't want to admit that so I stayed quiet.

We both took a break after that until she told me it was time for the pussy eating 303 class. I didn't get the reward of fucking a dildo for fingering myself as she taught me the proper way to finger her while licking her clit and how to find her g-spot. My reward was a faceful of cum as she squirted on me. I also got to rub myself to orgasm number five. This time I had to do it standing, facing the window and leaning forward with my legs spread. Victoria told me I had to be ready to display myself and put on a show when ordered. I couldn't see her but I'm pretty sure she was recording me again.

This orgasm took the longest. In fact I only came because I was fantasizing about Victoria touching herself while looking at me. I admit I considered faking this orgasm because it was taking so long, but I knew Victoria would know I did that. I didn't want to risk any punishment so I kept rubbing my clit until a small, but real, orgasm flowed through me. Victoria was ready with the marker to draw a diagonal line through the four vertical marks on my left breast.

"You're halfway there," she said proudly. "If the coin had been heads we would have been done."

I smiled weakly. The last two orgasms really were not that great. How was I going to cum five more times? I didn't have long to ponder the great mystery of my night. It was time for my pussy eating 404 lesson, stimulating the g-spot externally by applying pressure to her mons pubis instead of with a finger inside her pussy and using both hands to stimulate her g-spot (both methods) and asshole at the same time.

I proudly wore a second shower of squirt as Victoria obviously enjoyed my new skills. I felt like a drowned rat as my hair was getting matted down from her juices. After that orgasm I was rewarded with her finally fucking me with her strap-on. We started with me riding her cowgirl while she sat on the couch. I love being on top and I quickly was aroused to the point of nearing orgasm. I asked nicely, but this time I didn't get permission right away. That was fine. I was riding an arousal high again and I knew my eventual orgasm would be much better than the last two if I waited. I asked again about a minute later, this time with more urgency, and again the answer was no. Another minute and more urgency. I got the impression Victoria was setting me up to fail so she had an excuse to punish me. Soon I was begging again continually. I knew she liked that.

I thought she would finally let me cum, but instead she told me to dismount. I was afraid she decided to edge me. Instead she told me to get on my knees on the couch and bend forward. When she pressed the fake cock into me from behind, it felt bigger. I howled from the pleasure. She started fucking me and spanking me at the same time. "Please Mistress can I cum!" I shouted. I was going to cum. The only question was if I would have permission. She responded by fucking me harder. It was primal and it was savage. Her spanks were also harder. These were not the love spanks she gave me early.

"Cum my slave," she hissed. I was expecting her to say slut as a term of endearment, but slave worked too as it triggered my release and a loud sloppy orgasm. No squirt, but a lot of juice nonetheless and multiple screams of passion. Still Victoria kept fucking me. She pounded me straight through my orgasm. Each slap of her hand on my ass sent a lightning bolt of pleasure straight to my clit. I had barely left the peak of orgasm number six when she buried the dildo deep inside of me, grabbed my hips and pulled me to the floor. As I slumped down, the dildo pulled out of my pussy and I rolled over on my back as my body continued quivering.

"Keep those legs spread whore," Victoria hissed. Another demeaning term, another wave of pleasure coursing through my body. I spread my legs like I'd done for so many strangers on my trips, only this time I expected to really enjoy myself. No, that's not quite right. I always expected to enjoy myself and usually did. But this time I expected Victoria to be the best fuck I'd ever had. She mounted me like the confident lover she was, burying the strap-on deep in my pussy.

So here is my review of getting fucked by a strap-on, especially by someone who knows how to use it. It's amazing. First off, she doesn't cum too soon before I can climax. I suppose if she wanted to tease me she could have stopped, but at least tonight, that wasn't her plan and I was grateful. But more importantly, when she did me in the missionary position, it was way better than having a guy do it. Guys may not understand that their cock, by itself, while pleasurable, probably isn't going to make a woman climax. It's his hips rocking our pelvic bone which stimulates our clits that does the trick. Unfortunately, most guys don't get the motion right. I'm not blaming them. They do what feels good to them. It's just why I invariably have to finish myself. But with Victoria it was different. Not only did she understand how she needed to impact me more than penetrate me to bring me pleasure, the front of her harness seemed to increase the clitoral friction as she slammed into me over and over again. I'm sure she understood exactly what she was doing as she towered over me in complete control.

I didn't even have to ask permission to cum again. She hissed at me to cum after maybe her seventh stroke since mounting me and I responded on stroke nine. But still she kept fucking me. I lost track of how many strokes she pounded into me as I rode through my orgasm. My clit was hypersensitive, as yours would be after seven orgasms, but still Victoria kept fucking me. I finally calmed slightly from my climax, but Victoria was relenting promising to fuck number eight out of me before she stopped. I am ashamed to say it didn't take that long and I didn't make her work for it. My entire body was constricting and quivering, but still she kept pounding me until I finally had to scream, "No more!"