5 on 1 Ch. 01: Dora

Author's Forward:

This is a story about five young ladies in their 20's "seducing" a former instructor of their's that is in his late 40's. It is going to start slowly, in this chapter at any rate. The others may pick up faster, and be shorter because of it. I am not sure. There will be more than 5 chapters, since other shenanigans will commence, once all the players are introduced. Any resemblance to real people is either a mistake or an intentional copy. In the case of the copy, names and details are changed to protect the guilty. I enjoy constructive criticism, so if you see somewhere I can improve, let me know. Same if I made any errors that I did not catch when I was proofing and tightening up the story. All Characters engaged in sexual activities are over 18. Enjoy!

5 on 1 Dora

She looked so adorable, sitting there, her face turning red from embarrassment I smiled gently at her. "Come on Dora, I know you want to say or ask something, you know you want to say or ask something, so just let it out. I am not going to laugh or get mad or offended." I said softly, encouragingly.

"I..was it...can y...damn it!" She stammered, looking even more frustrated than before.

I took pity on her. "Look at me." She did, and I smiled gently. "I don't know what has you so tongue tied, but let me ask you this. If it was over text would that be easier? Rather than trying to say what has you all knotted up?"

Dora's eyes opened wide in surprise "Y..y...yeah, that would be easier." She stuttered a bit, but began to look hopeful.

"OK then, I am going to go for a walk in the parking lot. Type out what you want to say, and we can text back and forth for a few minutes. Sound like a plan?" I said while looking into her lovely brown eyes. She nodded her head, and I stood up and walked towards the door to the restaurant, tapping the pocket of my slacks to verify my phone was where it was supposed to be. I looked over my shoulder once and saw Dora busily typing away on her phone. I walked out the front door into the amazing sunset of Las Vegas, took a cigarette from my pack and lit it. While putting my lighter away I felt my phone vibrate. I pulled it out and read and replied to the message while I walked across the parking lot.

Dora:

Thank you so much for thinking of doing this! I just could not put the words together. This is kind of embarrassing What I wanted to know is this. Was what you said to TJ true, or were you just bringing him down a peg or 2?

Greg:

Ummm, which thing I said to TJ? Just like all of the students, I said many things to him. I don't know which of them would have you so tongue tied. And you know I had to take him down a few pegs more than once! lol

Dora:

About...oh god, this is still embarrassing!

Greg:

Come on hon, you can do this. Just let fly and get it over with. I lay odds you are making this much more difficult than it really needs to be.

Dora:

OK You told him that you made all your girlfriends orgasm so hard they passed out. True or BS?

I was blown away. I could not see how any guy, even TJ (who was way to cocky and tended to run his mouth), would tell a woman that! I figured it needed correction, at least in detail.

Greg:

That is not exactly what I said. What I said was that it had happened with several gf's over the years, that it freaked me out the 1st time, and that to make it happen you had to pay attention. So, yes and no.

Dora:

So yes you have, but not all of them?

Greg:

Correct. I am shocked that he told you this.

Dora:

Ummm, he didn't exactly.

I was nearly done with my smoke by this point. I was also wondering WTF? I turned and headed towards the door to the steakhouse.

Greg:

Are we passed the difficult part now? Can I come back in and talk to you?

Dora:

NO!

I was typing my reply to that when her next message arrive.

Dora:

I have 1 more thing to ask, and I want to explain a few more details.

I turned towards my truck, this sounded like it might take a while. I deleted my incomplete reply, and typed a new one.

Greg:

Sure, go ahead.

I dropped the tailgate and hopped up to sit on the bed of my truck while I waited for her message.

While I am waiting, maybe I should give you all a few details. First, my name is Greg. I am an instructor at an adult education program here in Las Vegas. I am divorced, 45, stand 6'3" tall, with wide shoulders, a deep chest, a full head of brown hair, and blue eyes. I weigh in at a solid 250 pounds, a lot of which is in my shoulders, arms, and legs. While I don't have 6 pack abs, I am not packing a beer gut or a muffin top. All in all, I am in pretty good shape. Ours is a 6 week program designed for working adults to come and learn a new set of skills to change careers, or maybe enhance what they know to improve their career. (We get a few of the second type now and then.) The school runs 7 days a week, and I am the straw boss on the weekends when the program head is off. Both the program head and I have our phone numbers posted in the classroom, and we instruct all the students to put both of our numbers in their phones, so they can send a text or call if they are going to be late, or not coming in.

Dora is a former student. She finished up a few weeks ago, and we wished her good luck in her new career. She is 23, a Latina (I think, I never asked) with a fairly light complexion, about 5'5", brown hair, brown eyes, a cute face, and a very nice ass. She is solidly built, not skinny, not stocky, not fat...just a nicely solid form. She looks every bit a woman even in work clothes, but she is no willowy thin thing. Before she walked in this evening, I could not even have guessed at her bust size, since she always wore either baggy t-shirts, or bulky hoodies to class. But when she walked in this evening wearing a little black dress, it was evident she is proportionally built with probably, a nice set of C's.

Anyway, she texted me a few days ago, and asked if I would like to go to dinner with her Wednesday night. I was surprised to hear from her, because, let's face it, I am nearly double her age...and more than old enough to be her dad. I considered turning her down for a few seconds. It was not a job concern, the school has a policy that discourages fraternization with the students when they are attending class, but realizes that people are people, and trying to forbid a relationship with a former student was stupid. They recommended against it, but it was not breaking any rule or policy. No, my temptation to reject her came solely from a recognition of the age gap. But, I am a naturally curious person who loves a puzzle, so I said yes, and asked her if she had a place in mind. She named the restaurant, and asked to meet at 4pm. Cool.

This evening, she walked into the restaurant in her little black dress, and I was not the only guy checking her out. She was wearing black hosiery of some kind; a modestly cut little black dress that clung to her curves, especially her ass; black heels that were probably three or four inches high; a black lace choker around her throat, full makeup, and had her hair up in some complicated style that set everything else off. She smiled when she saw me, I stood up and smiled as I bowed elegantly wile waving to the booth seat as I did so. She laughed and slid in. I told her that I assumed she wanted to talk about something specific, but let's leave that for after we eat. She agreed, and we had a wonderful meal with good conversation...right up until I asked her what she wanted to talk about...which is where we started this tale. Ope, looks like she has finished typing.

Dora:

OK What happened was this. TJ was talking to a few of the other guys and Aria overheard them. She is curious, but you know how shy she is. We got talking last week and she told me about it and that she was too shy to ask you about it. She got me interested also, so I said I would ask. So I messaged you, and here we are. The other thing I wanted to ask you is this. Will you do that to me?

Whoa. This whole conversation was not going the way I had half expected it to. When she showed up in a dress and heels, I thought she was going to flirt and that maybe, she wanted to go to bed. But this...

Greg:

Ohhh kay, this is going to take some explanation. I am coming back in now.

I slid off the tailgate of my truck, closed it, slid my phone into my pocket, popped a mint in my mouth, and walked back into the restaurant. I smiled at the hostess, and wended my way back to our table. I smiled at Dora as I sat back down in the booth next to her. She wouldn't meet my eyes, looking down at the table. Quietly and gently, but in a deep register, I said "Dora, look at me." She twitched, but didn't look up. "Please?" She looked up at that and saw the small smile on my face. "Better!" I said, my smile growing a bit larger. She smiled back nervously.

"OK, listen. Remember I told you that I told TJ that it was important to pay attention?" She nodded, so I went on in an low voice. "OK, do you have any idea what I meant by that?" She shook her head. "What I meant by that was this. The guy has to pay attention to every little thing about the woman he is with. What turns her on, what she likes, what she doesn't, and when she is about to cum." She shuddered a bit at that last. I filed that away. "There are two reasons I have found that most likely cause it to happen. The first is hyperventilation. You know how fast you breath during sex, most women stop breathing at the peak of their orgasm. Usually this is only for a second or so, but, if it goes a few extra seconds, it could cause a blackout. The other cause has some large medical name, but it basically causes your blood pressure to drop rapidly, and you faint." Her eyes widened.

"Oh." Her eyes were still wide, but she was obviously listening.

"Yeah. So, here is the thing. I can TRY to do this for you, but I can't guarantee success." I said as levelly as I could. Her breathing deepened a bit. Hell, I would try my damnedest. Seriously, how often does a 45 year old get to go out with a good looking 23 year old woman who tells him she wants to have sex with him, and why? Not very damn often in this country anyway! I had a thought. I turned it around, and looked at it from every angle I could think of, and it looked like a solid idea.

I said, "I just had an idea. I know a few things that are necessary for this to work. I am not going to ask you to tell me the answers, because you may or may not know them. I want to try a series of test on you. Your reactions will give me the answers to the questions. You don't have to do it, but it should help answer the question of if it will work." I looked at her with an eyebrow crooked/

Her eyes had widened a bit at the mention of tests. "What kind of tests? Where at? When?" Her breathing had sped up a bit. Hmm, this just might work.

"Nothing hard, I promise." I looked deep into her eyes. "Do you trust me?" I asked quietly.

She stared back for a few seconds, considering. Then she nodded and said, "Yes...yes I trust you." with a firm little nod of her head.

"OK then, take you hands and place them on the table with your fingers clasped together." She did so. I covered them with my left hand. "Right, now close your eyes. I want you to imagine that your hands are tied to the table." Her eyes flew open and she stared at me. "Close your eyes, this is part of the test." She looked at me for a long, thoughtful moment, then closed her eyes. "Can you see your hands tied to the table in your imagination?" She said she could. "OK, now, you can open your eyes, or keep them closed, whichever you prefer." She kept them closed, which I found interesting.

We were sitting in a booth on the same side, with her on my right side. I started to run my fingertips lightly over her hair and she gasped a bit, but kept her eyes closed. Her breath stuttered a bit when I started, but smoothed back out. I worked my hand down her head, to her ear, which I traced lightly around the edge of, making her breath shudder a bit more. Down her neck, up to her chin, along her jaw until I got to the area below her ear. I lightly scratched her here on my way down, and rubbed it a bit more firmly on the way back up. She trembled and sighed. Excellent. I ran my fingers around her neck and up into her hair at the base of her skull, tight against her scalp. I massaged her here for a bit before I tightened my fingers together, trapping some of her hair between my fingers. I slowly made a fist and tugged her hair gently. Her back arched, her breath hitched for a second, and she moaned quietly when her breath came out. I whispered in her ear, "That's a good girl, we are about done." I saw her lips curve up when I said this. I reached over with my left hand and put it lightly on her side, then ran it lightly across her breast, discovering that her nipples were hard...which was the point. She gasped a bit at that, but no more. Again I whispered, "Are your eyes still closed?" Her head nods. I placed my left hand on top of both of hers. I want you to imagine me untying your hands from the table now. Are your hands free?" She said yes very quietly. "Now, the last part of your test.. I want you to lift your butt up a little bit, pull your skirt up above your hips, and sit back down." She turned to me, her eyes wide.

"What? Here?" She managed to keep her voice down, but she was obviously getting worked up over this.

I looked into her eyes again. "Quietly." I said with a note of command in my voice. "Think about this for a second before you say anything else. We are in the corner of a dimly lit dining room. The table cloth goes all the way to the floor. I am between you and the edge of the seat. If you do what I ask, no one will know a thing, not even if the waiter walks up. There is nothing for them to see." I saw in her eyes that she calmed a bit. I just looked at her calmly. She finally huffed out a bit of air and did as I asked. After she sat back down, I whispered in her ear, "Good girl. Now, I want you to put your hands back on the table where they were." She did. "Close your eyes. Good." I put my hand back over hers. "Now, imagine me tying your hands back down. Can you see that they are tied?" She whispered yes.

"Right. Now, the last thing I want you to do is to spread your legs. She opened her left eye and looked at me. I just stared back calmly, like it was a forgone conclusion that she was going to do what I said. She closed her eye again, and her legs parted. "Wider." She complied.

I started to lightly run my fingertips up and down her outer thighs, 1st one, then the other. Crossing at her knees, and across the small area above her mound that I could reach due to the way her dress was bunched. I worked my way across the top of her thighs and slowly onto her inner thighs, but I very carefully avoided her pussy. Her breathing was deep and getting ragged by this point. My left hand caressed her breast again, this time just rubbing her nipple to verify it was hard. Yup. I leaned into her again, my right fingertips still lightly tracing mindless patterns on her thighs. "You're a good girl. You are enjoying this aren't you?" She started to shake her head, but she stopped as just then, I pulled my fingertips firmly over her panties, my middle finger following the crease of her pussy, and my ring and index fingers tracing up her swollen labia. Her panties were drenched. She wasn't about to drip through them at the moment, but if I kept this up for a few more minutes, she would be in danger of it. I pulled my hand from under the table. "You can never deny being turned on when someone can feel your panties. I know this turned you on. That is great, by the way." She turned her head towards me, her eyes opening. I smiled. "It means I can probably get you to pass out...which is a hell of a weird thing to tell someone, by the way!" I said with a small chuckle. She laughed at that, a surprised little laugh.

"Well, yeah, since you already know the answer, yes. It turned me on." She said softly, her cheeks turning pink. I reached out, took her left hand, and ran it down the bulge in my slacks. Her eyes widened in surprise I moved my hand, and she traced then lightly squeezed my cock. "Wow." she breathed as she took her hand away.

"Close your eyes for a moment." She did, but looked confused. I put my hand on hers. "I just untied your hands. Go ahead and fix your dress." I said as I took my hands off of hers.

While she is fixing her dress, let me explain my thoughts here. I am a dominant, and have dated submissive women by and large. I was testing Dora to see if she is submissive. I can't ask her that, because social media has made that a curse word among most western women. I was also testing for a few tell tales, how certain things affected her. She also likes light bondage, and she has a really good imagination. I figured if she was one of the vanishingly rare, poor women who are, or think they are, dominant...this was unlikely to work. She would either never have complied with the bondage visualization, or would have moved her hands at some point. She didn't...not even when I slid my fingers the length of her pussy. Only someone who will submit to a dominant would have pulled up their dress and spread their legs in a public place when told to. Everything I said was true, there was no risk, but the fear of it, would keep most people back from it. I still don't know if I can give her what she wants, but I am convinced there is a better than even chance.

"How could you know if you can do it, from just that?" Dora asked after she sat back down after fixing her dress.

I just grinned at her. "I don't think you have any idea how much information I just gathered in that few minutes." Hmm, time to throw out a sheet anchor. "OK, look at me." She did. "There are a couple things. First, yes, I think I can get you to cum hard enough you pass out." She beamed a smile at me. "Before you celebrate, I gotta warn you. Most women that this happened with, it did not happen the 1st time we fucked. The first couple times it was random. I was trying for it the third time it happened, because I was curious if I could control the effect, or if it would remain random. That 3rd time took about 10 days to pin down something that worked." I looked at her seriously. "Are you sure you are ok with sleeping with a guy that's old enough to be your dad once, let alone multiple times?"

She looked down, blushed deeply again, squirmed a bit on the seat. "Yes." She said very quietly, still not looking at me.

"Oh? And how can you be so sure?"

Still blushing and squirming, she nonetheless looked me in the eye and said, "I am sure. Maybe I will explain it later." She said steadily and quietly. Well, ok then. I thought things through for a few moments, trying to figure the logistics of the situation.

"OK If you are sure." She nodded her head. "I have a couple questions then. First question is, when did you want give this a whirl? Tonight?" Another nod. "OK, and second is this: How far do you want me to push your boundaries?" Aah, that got her attention.

"Ummm, push my boundaries?" She asked, one eyebrow lifting slightly.

I chuckled quietly. " Yes, push your boundaries Look, do you think something like that happens when you are in your comfort zone, and everything is going along smoothly?" I shook my head slowly. Her expression changed to thoughtful. "If this is something you really want, I am going to push you out of your comfort zone by pushing you to the edge of what you find acceptable. If I push you to do something you will not do, all you have to do is say STOP. I will stop, and we are done for this evening. I don't know if I can push you that far the first time we meet...I will try my damnedest, so it won't be for lack of trying, I promise you that."