Educating Cassidy

Gwen approached me after the class I had been leading. I wasn't sure of the events, but we had met on other social occasions, so when she arrived at my evening writing class I knew who she was. I suspect we had been to a number of the same parties and knew she was a bit younger than I was by a few years. I thought she was pretty good looking, blonde hair that was a bit curly and just hit her shoulders. Nice solid figure with a great ass that I had admired on more than one occasion. She had decent breasts and was not the skinny model type. If she wasn't married, Gwen was definitely the type I would have tried to ask out and I was always happy to talk with her. She had waited until all of the other students had filtered away before coming up.

Gwen had a daughter that had just graduated from high school and was going to the state university in the fall, so Gwen fully met the requirements to be classified as a MILF. And that was what she wanted to talk to me about. Her daughter was going off to college with a rather limited experience with people of the opposite sex. And she wanted to introduce her daughter to sex in a safe way. For some reason she had decided that I was a good candidate to be the one to help. It came as a bit of a surprise, but she figured that I would be a safe choice, not too young and overly rambunctious and that I would be able to control my emotions as well as my lust.

So she explained that this was going to take place over four or five weeks. The first week it was going to be an audition, a sort of try out with just the two of us. That would allow her to decide whether I had the temperament and talent to meet her needs and therefore would be a good experience for Cassidy to learn from. Part of the requirement was that I would have to ejaculate at least twice during that session, once from a hand job and once from a blow job and still be able to have enough of an erection to give it to her after that. She didn't care if I was able to cum again a third time, just that I could stroke it to her. Condoms would be used for intercourse, but not for the blow job, she hated the taste of latex.

I was confident in my l longevity, but not so sure about being able to climax multiple times, I wasn't as young as I used to be! But I figured even if I failed the audition, I was still going to get sex with a great looking MILF out of the attempt. Who in their right mind would walk away from an opportunity like this? And if I did pass the audition, there were other delights to experience.

My bigger concern was about her husband. Gwen explained that he travelled for work at least one week a month, and that when he was in town he had a couple of weekly events, but regardless, what she also wanted was to come to my place. That way there was no way he could walk in on anything going on, even if he should come home early. The two of them could always go "out shopping," even if he was in town.

If I passed the audition, her daughter would come over the next time to observe the two of us. The basic scenario was expected to be pretty much the same routine as the first round. This would introduce her to the basics of foreplay and what she should expect.

The third round was the one that really had me revved up just thinking about it. Both of them in the bed with me! This was to be a real hands on experience for her, giving Cassidy the chance to touch and feel me and experiment with both oral and hand jobs. It would allow her a close up view and experience the ejaculation she caused personally.

The fourth round was going to be Gwen completely hands off as she coached Cassidy as she worked through the entire pre-coitus route, all the way up to the actual losing intercourse.

If there was a fifth night, it was going to be entirely up to Cassidy. It could be a straightforward repeat of the prior session. It could also result in me taking her virginity, Gwen was pretty sure she was still a virgin, but only if that was what Cassidy wanted. And Gwen was not going to be in the room, though she was planning on being in the house as a safety valve.

The Audition

To say that I was a bit nervous would be an understatement. I was about to have sexual relations with a married woman, the first time I had done that, at least the first time that I knew about. There had been some earlier encounters in my life that could have been questionable, but I was young and didn't care. And perhaps with her daughter, if I could pass muster with mom.

My teaching schedule was a few evenings a week, with a few weekend seminars or workshops. Being a writer and a part time professor certainly provided for a flexible schedule. I had developed enough of a standard presentation that I could fill any requested presentation from 30 minutes to eight hours. And I didn't come cheap for a full day workshop.

I'd shaved carefully and trimmed up my beard, gone and worked out earlier in the day. I made sure I had on a good pair of underwear, though hopefully it wouldn't be on for long. A pair of jeans and a polo shirt. I went with one of my tighter ones. I wasn't what I would call a jock, but I wasn't a total bookworm either. I worked out on a regular basis and took advantage of some of the classes at the gym. My stamina was pretty good and I could do a 5k in about 23 minutes, not bad for a guy getting close to 50. I stood just shy of six feet.

I heard the garage door opening. I'd given Gwen a remote for the 2 car garage, she could pull in and close the door prior to getting out of the car and no one would see her and no one could spot her car if they drove past looking for her. After hearing the door start to close I opened the door and welcomed her. I had a bottle of wine and some glasses on the kitchen counter just inside the door, but didn't know if that fit the agenda, better prepared than not.

She came in and dropped her purse and a bag by the door as I shut it behind her. I picked them up and set them on the counter in the entryway.

"Would you like a glass of wine?"

"Yes I would, a white, Riesling or Chardonnay. If you don't have one, provide me what my choices are." Fortunately, I had a couple of bottles of Chardonnay to choose from and presented them to her. She chose one quickly, "Pour me a glass of that one and strip." No doubt that Gwen was taking control.

"Strip?"

"I didn't stutter, Al, strip, I want to see what I'm considering."

I popped the cork and poured the glass and handed it to her. She took a sip and wrinkled her nose, "Next time make sure it's chilled."

"I will!"

I moved over to the carpeted area near the couch and stripped my shirt up over my head. Like I said, not a bodybuilder, but my belly was pretty flat and my shoulders and arms were well toned. Gwen looked good, she was wearing a tight pair of leggings, gray with some patterns and cutouts and a colorful blouse that came about halfway to her knees. She was wearing a pair of chunky heels in black. They made her stand about four inches shorter than I was in my bare feet and they made her ass look great!.

She walked over and ran her hands over my chest. "Flex, like a bodybuilder."

I took a couple of poses I'd seen some of the heavies at the gym using, trying to highlight some of my muscles. She ran her fingers over my arms and shoulders and sighed, "Well, you are certainly in better shape than my husband. Lose the pants."

I felt like a piece of meat, but I figured the reward was going to make it all worthwhile. Her fingers had sent some little shock waves through my system. I tried to avoid looking clumsy while sliding my pants down, but it isn't something I had given much thought to in the past, so it was more challenging than I would have expected. I tossed them next to my shirt on the couch and looked at her.

"Keep going." She licked her lips, which were colored a dark red that matched her fingernails. I was certainly aroused and it was a bit awkward sliding down the white briefs. Her fingers slid down the side of my torso and traced the faint appendectomy scar before sliding over to my penis. Even though I was expecting it, I jumped when she made contact. She was surprisingly gentle as she probed around my cock and balls, even curling some of the pubic hair with her finger. My cock was fully erect and at its maximum eight inches. It bobbed slightly as she bounced it in her hands a couple of times. She let her fingers trail around my waist as she moved around my body, pushing a bit at my ass, which didn't give at all to her pushes.

Returning to the front, she squatted down. My penis was throbbing and a bit of pre-cum glistened at the tip. Gwen touched the tip with her finger and put it in her mouth. "Nice! We are going to have to do something about that forest, though. Show me around."

She grabbed her bag and I gave her the quick tour. With my books trickling in royalties on a regular basis, the teaching and numerous articles, I was fairly well off. Certainly not rich, but more than comfortable. The house was a three bedroom ranch, with a walkout to the patio and lake in the lower level. The first bedroom was set up as my office, the view looked out over a lake, then the master bedroom on the back side of the house. The front side had a bathroom and the other bedroom facing the road. She walked into the master and on into the master bath. It was pretty large, one of the big luxuries I had gone with. It had a large walk in shower with multiple shower heads and a big bath with massage jets. Even the toilet was deluxe with the latest in wash systems, built in bidet and a heated seat. Even the floor was heated in here.

"Very nice. Who decorated?"

"Mostly me, but there was some input from a couple of girlfriends."

"Any current girlfriends?"

"No, not right now."

""Good, we won't have to compete for your time and attention. When was the last time you were with someone?"

"About two months ago, but what does that have to do with... "

She cut me off, "I'm evaluating the risk of any STDs, I'm not going to be responsible for any transmission to me or my daughter."

"Got it! Two months and I've seen the doctor since then. Given I have been somewhat active, I made sure he tested for anything, just to make sure. I almost always use a condom, but wanted to make sure I was okay."

"That is good on several levels, so, sit!"

She pushed me to the toilet. I sat down and she made me get up and open the lid first. Reaching into her bag she brought out a small razor device and proceeded to denude my penis and balls, shortening up the rest of my pubic hair. "Use some hair conditioner when you get in the shower, it will help with the itching."

My first thought was, yeah, right, like I have hair conditioner. But there was probably some from a prior girlfriend around, maybe I had some from some hotel stays when I went to conferences. I'd have to dig around.

"Okay, so far, so good! Get me another glass of wine." She was direct with what she wanted which was refreshing, at least I didn't have to guess what was going on.

It felt a bit strange walking through the house naked as I usually put on some shorts at least. I poured the wine and returned after taking a hit from the bottle myself. Gwen had pulled back the comforter and top layers to leave the bed with the bottom sheet and pillows. And had removed most of her clothes in the process, I walked into a full moon, with the curve of a black thong across her hips. I think my mouth fell open as she turned to face me.

"Like what you see?" I could see she was teasing me rather than being upset.

I stammered and managed to shake my head up and down as I handed her the glass. A lacy black bra barely held her breasts up and certainly did nothing to hide the dark red nipples. The dark red matched her lipstick and fingernails closely enough to make me wonder if she had colored them. The swell of her hips and the slight grin on her face was really completing the appealing look she had.

"Good! Now lay down!" I quickly went and laid down on the bed and then she really took charge. Before I realized what was happening, she had handcuffed my one arm to the bedpost.

"Hey, what's this?"

"Well, you don't think I'm going to leave anything to chance do you? This makes sure that we follow the script all the way through. So far, you've been doing very well. You have been polite, courteous and well behaved. Physically you are everything I was expecting, actually a bit better than I expected, so that's a good thing. But I do know what happens when a man gets excited. So put your other hand over there and let me fasten it to the other post. Or are we done here?"

I can't say that I was upset by the situation. She had taken charge from the start and it was kind of exciting. So it only took a moment of thought before I stretched my arm out to the post on the other side. Gwen clicked the cuff into place and then proceeded to use a band and rope to securely fasten each of my legs to the bottom legs of the bed. The sound of the velcro ripping apart as she did it actually excited me even more. She smiled and took a sip of wine as I watched. After turning off the majority of the lights, she pulled open the doorwall drapes and sat down on the bed. She started playing with my cock with one hand while she continued to sip the wine with the other, a smile dancing across her face once in a while.. Once she finished her wine, she set down the glass and then put her full attention on the cock in front of her. She knelt down and got her face within inches of the tip.

"Now don't cum too soon! I'm looking for some indication of control here!"

Her nails were slowly teasing my balls and the shaft as she occasionally glanced at my face as I struggled to keep my cock under control and not spew into her face. Gwen would rub her fingertips and nails until my balls started to crinkle up and then back off for a minute. After a good fifteen minutes of teasing, she decided to have pity on me. She pulled off her bra and grabbed a bottle of lube from her bag. A few globs on my penis and she put another in the valley between her tits. She crawled up from the bottom of the bed and slid my dick in between those heavenly breasts and slowly started rocking back and forth. Even in the semi-darkness, illuminated just by the light from outside and the glow of the bedside lamp, the view of my dick head popping up between those mounds just inches from her face was all it took. I shot a large load that arched up into the air and splattered down on my own face.

She laughed, "Normally, I would have made you wait longer for that first orgasm. But I do want to see what your recovery time is like. You had quite a load there! How long has it been since you orgasmed?"

"Day before yesterday, I did want to pass the audition! Umm, not that I've been really trying to measure, but would it be safe to say that Cassidy is not as well endowed as you are? Not sure she can do what you just did."

"True, I'll adjust a bit when she's here." Her smile made me feel good. She crawled further up the bed and laid on top of me, looking into my eyes. Her's were brown and seemed to dance in the dim light. With her fingers she began channeling the cum on my face toward my mouth. While half of it was pushed through my lips, she would occasionally lick her fingers or even my face. It was amazingly sexy and I found my dick starting to rise to the occasion once again. She moved up a bit further up and let me suck on her tits, cleaning them up from the results of my ejaculation. It became clear that the dark red color of her nipples was totally natural.

"I like what I'm feeling down there! But you've gotten to cum, now it's my turn!" She flipped around and then sat on my face. My nose was buried between her ass cheeks and her slit was pressed into my face. I wasn't sure when she had removed her thong, but the mound was smooth and obviously shaved. It didn't take a genius to figure out what she wanted. I felt a bit handicapped by not being able to use my hands, but went to work. She smelled and tasted faintly of cinnamon with a nice mix of sweetness and bitterness. I liked not having the pubic hair to worry about, and could understand why she would want to trim mine.

Working my tongue into the folds I couldn't see anything other than the curve of her ass as she moved. I have no idea how long it took but my tongue was getting tired. Eventually I felt her thighs starting to tense up. The soft moans, muffled by her legs over my ears, became louder and her breathing was more ragged before everything locked up and she shuddered. A flood of juices covered my face and I almost blacked out trying to breathe. Gwen fell off to the side and I was able to take a real breath, gasping for air as she slowly came down from her climax. I was light headed, and felt all sticky from her juices cooling on my face.

"Wow, Al, that was intense. Easily one of the best organsm I've had in years. My husband is more than adequate, he's actually pretty good, but routine has set in and this break is going to help in a lot of ways! I suspect that he is going to benefit greatly from your attention to me. Halfway there! Now, let's give you a nice blow job. I've had some pretty close up views of your tool and I'm looking forward to burying it in a couple of places, but let's start with my throat!"

She went to the bathroom and returned with a warm washcloth. After clean-up up my face and neck, she applied it to my groin. To my satisfaction, my cock was already getting hard, the face riding had gotten me going again and given me some time to recover. I also appreciated the fact that while Gwen was clearly in control, she wasn't taking any delight or interest in actually hurting me or being mean.

Gwen once again knelt between my legs, still stretched wide apart. She began running her nails up and down my inner thighs and eventually getting to the shaft. Finally she grabbed it firmly and slowly started sliding it into her mouth. About two thirds of it had disappeared between her lips when her head started coming up again. Over the next couple of minutes she would slowly lower her head and then rise back up, going a little bit further each time, until I could feel her nose touching my pubic hair. The sensation was amazing. I actually realized that it was probably a good thing that I was tightly fastened to the bed. I could flex my hips a bit, but only a few inches. If my hands had been free, I likely would have gone wild and grabbed her head while pumping my dick down her throat with a lot of force. This way the blow job lasted a lot longer, to the point I was groaning and begging her to make me cum. She just looked up through her lashes and wisps of her hair and even in the darkness her eyes shone. With a shout I finally let go. My second ejaculation in an hour, but I have no idea what the quantity was, Gwen just looked up at me as I felt her tongue and throat throbbing around my cock as she swallowed. The sensitivity was making my entire body shudder as she continued to stimulate me.

It seemed like forever, but after a minute she came up and smiled at me. She reached over to her bag on the nightstand and then rolled something onto my dick.

"There, that will help keep you hard!"

I couldn't really see from my vantage point, but I suspected she had rolled a cock ring over my shaft, snugging it up against my balls. I could feel it there, but it didn't hurt. I figured that if it helped me pass the audition, it was a good thing. She checked my toes and fingers, commenting that she didn't want them to be too tight and then freed one of my hands. A quick trip to the bathroom and she handed me a glass of water to drink.

"Can't have you getting dehydrated! This isn't meant to be a torture session, but I am going to be in control!" We talked for a few minutes, it seemed rather bizarre, me stretched out with three of my four limbs securely fastened. We chatted about normal things, like exercise routines, my house and the lake it was on and her family. I hadn't realized it, but Gwen had an older son, who before he left for college a year ago, had been pretty protective of his little sister. He had pretty much scared off anyone that took an interest in her. Gwen took the glass and then refastened my arm. Another reach into her bag and she brought out a condom, rolling off the cock ring, which was doing its job, and immediately replacing it with the latex sleeve.