Prepping for Date Night

Kyle is a really nice kid who's been dating our daughter Heather for most of their time together in high school. He's a good looking guy with shaggy blonde hair who looks like a surfer. He and Heather go out pretty much every Friday night and we've come to think of him as a member of the family. Both kids will be headed off to different colleges at the end of the summer so their future together is uncertain. And I'm probably just as sad about it as Heather, considering the "interesting" relationship we've found ourselves in.

It all started about a month ago. Heather had been late in getting home from work and was scrambling to get ready for their Friday night date. She yelled down the stairs for me to call and let him know she'd be a little late.

"Hi Sue, Heather asked me tell Kyle she's not going to be ready for about another half hour, can you please let him know?"

"Actually, that's just as well Joan. I don't think he's done masturbating yet, so I'll give him the message."

Did she really just say what I thought?

"Excuse me?"

"Oh my god, I can't believe I let that slip out. Please, please, please don't tell Kyle I told you that! He'd kill me!"

"Well, there's certainly nothing wrong with that. I'm just surprised he's so open about it."

"Oh he isn't usually, but in this case he's doing it because I asked him to."

"You asked him to? What in the world for?"

"Joan, you'll probably think this is crazy, but after Kyle and Heather started seeing so much of each other, Jim told me a part of him felt sorry for Kyle because of all the sexual energy he would need to deal with. He said lots of times when he was at the heavy petting stage he'd get so worked up on a date that all he could think about was getting home so he could relieve himself."

I got to thinking about it and asked him if it would have made things easier if he'd done the 'reliving' part first. He said he wasn't sure, but that at the very least it would have made him better company because he'd be more likely to engage in conversation than obsess about the physical stuff."

"Are you sure you won't tell any of this to Kyle, Joan?"

"Go on."

"So I said to Jim, what do you think about trying it with Kyle? He obviously masturbates. What red blooded eighteen year old boy doesn't? Jim said it was OK with him, but that he sure as hell wasn't going to be the one to lay down the law with Kyle."

"So you're really not making this up?"

"No. I figured I'm the mom and moms always have to do the hard stuff. So one day after school, I went to his room and told him the plan. He turned beet red and tried to deny that he 'did that'. I told him that was hard for me to believe, but that it didn't really matter because he was going to have to start if he expected to have any kind of social life. It seemed like a big deal at the time, but now it's become so automatic that I don't even think about it. I guess that's why it slipped out just now. We call it 'prepping for date night'."

"That's the most bizarre thing I've ever heard. But how do you know he actually does it?"

"That's simple. He saves the evidence on some tissues and I make him show it to me before he leaves the house."

"You're kidding!"

"Nope. Simple, but effective."

"Does it help him?"

"I don't know for sure, but he seems happy enough. And if we're right, he's more of a gentleman with Heather. Something you might be able to appreciate."

"I'll have to think about that one, but it does make me wonder what Heather's doing when she gets home."

I was a little embarrassed with myself because I realized the conversation had turned me on. The feeling didn't get any better when Kyle showed up a little while later.

I put on my best poker face, but the fact that I knew this sexy young boy had masturbated less than 30 minutes ago, and that he had no clue that I knew about it was hugely arousing. The knowledge was so intense I wondered if he could read my mind; but of course that was impossible.

After he and Heather left, I couldn't think of anything else. My husband Bob was on a business trip and not due back until later that evening. Even though I knew we'd fool around when he got home, I was desperate for some immediate relief.

I poured a glass of wine, drew a hot bath, and settled in for a nice relaxing session of self-love. My soapy hands moved over my small breasts as I imagined Kyle watching me and getting turned on. I pretended it was his hands caressing my nipples and making them hard. I took my time – relishing in the sexual tension building in my body. I poured another glass of wine and shifted the object of my attention. I thought about Kyle getting excited as he watched me explore my inner folds. I separated by lips and pretended to show him my clit. I thought about watching him while he masturbated such a short time ago. I thought about him getting naked, playing with himself and ejaculating into a handful of tissues before showing them to his mother. I replayed this scene over and over as my orgasm approached. I was oblivious to the world, completely lost in my forbidden thoughts when I realized with a start that I could actually make this happen! I had the leverage to make Kyle do almost anything. The thought of actually watching him do it sent me into a thunderous climax. As soon as a measure of my composure returned, I began working out the details of my plan.

Bob and I had amazing sex that night. He had no idea what had turned me into such an animal, but he certainly wasn't complaining.

My lucky break came the very next date night. I knew Sue and her husband were going to be out of town for the weekend. It took a bit of deception, but it wasn't hard for me to maneuver Kyle into arriving an hour before Heather would be home. I'd been thinking about this caper all week, and I was as nervous as a school girl when he arrived; right on schedule.

I explained that Heather wouldn't be home for a while and offered him a Coke. We chit-chatted for a few minutes before I dropped the bombshell.

"So Kyle, since you're not being supervised this weekend, I wondered if you still prepped for your date."

He turned beet red.

"I don't know what you're talking about," he stammered.

"Oh, I think you do Kyle. Your mom let me in on the secret. She didn't mean to, but apparently it's become such a regular part of your routine that it just slipped out when I called last week. She asked me not to tell you, but obviously I've decided not to honor that request. So I repeat my question, did you prep?"

"I really don't think that's any of your business, mam."

"I'm sorry Kyle, but I disagree. I'm Heather's mom, and I have a right to protect her. Besides, can you believe how much damage would be done to your mom's reputation if your little deal just happened to appear on someone's Facebook page? I'll bet it would make your life a little more interesting too."

"You wouldn't dare!"

"Are you really willing to take that chance? Now why don't you answer my question?"

"OK, you win. Yes, I did. Now are you satisfied?"

"Actually, I don't think I am Kyle. How do I know you're telling the truth?"

"Why would I possibly lie about something like that?"

"Could it be that you see it as a new opportunity with Heather?"

"That's simply not true! You have no right to think that!"

"Perhaps; but there's an easy way to remedy the situation."

"I don't know what you're talking about."

"Isn't it obvious? All you need to do is prep right now."

"Oh no mam, I just couldn't! I'd be too embarrassed. Besides, I don't know if I could do it again so soon."

"Kyle, don't you think it would be more embarrassing if the whole world knew what's been going on?"

He shot me a look of resignation.

"OK, you win. I'll just go to the bathroom see if I can."

"I'm afraid that doesn't work for me Kyle. How do I know you'll really try? You're a clever boy. All you'd have to do is wait awhile, come back and say you couldn't produce. I'd like to trust you Kyle, but there's a limit to how far I can go. I'm afraid the only way for me to be sure is to watch you do it."

I smiled at him sweetly. He knew he was toast, and so did I.

"We better get started, Kyle. Heather will be home before too long. I think her bedroom would be an appropriate place, don't you?"

When we got there, I pulled back her covers, plumped up the pillows and said, "Now why don't you just slip out of those clothes and try to relax. You can start with your shoes."

He gave me a look that said he could not believe what was happening and reluctantly took off his shoes.

"You can keep your socks on if you want – just in case Heather comes home early."

I knew that was not a possibility, but couldn't resist the chance to insert a little urgency into the situation.

Next his tee-shirt and shorts came off, but he balked when it came to the finale. Apparently he needed a little more encouragement.

"Oh come on Kyle, don't be such a baby. Are you really that afraid to show me your penis? Or maybe you're ashamed to show it to me."

My affront to his courage and manly ego did the trick. He inched down his underpants and stood before me awaiting further instructions. He was perfect! Not too small and not too big. He was circumcised and his scrotum hung down loosely with one testicle a little lower than the other. He was not at all intimidating, and had the perfect equipment for an eighteen year old girl's introduction to the male anatomy. I worked hard not to show my arousal, but I could feel myself getting wet.

"That's good, Kyle. Now let's start with a few questions. I'm curious. Does your mom's strategy work for you? I've asked Heather if there's any reason why she should be on the pill, and she says 'no' so I know you're not having outright sex. But you wouldn't be normal teenagers if you weren't fooling around? Am I right?"

"I suppose so mam."

"Why don't you tell me what she lets you do? Surely she lets you touch her breasts."

He nodded.

"Does she let you take off her bra?"

"Uh huh."

"How about her vagina? Does she let you touch her there too?"

"I guess so."

"Outside of her panties or inside?"

"At first just outside; but now she lets me do both."

"I see. Does she let you put your fingers inside?"

"Yes, mam."

"And do you rub her clitoris?"

"I do when she wants me to."

"Does she like it when you do that?"

"She didn't at first because I didn't know how to do it right; but then she showed me how, and now she likes it a lot."

"That's interesting. Tell me more."

"At first, I thought you had to rub right on it, really fast. But she said it was way too sensitive for that, and that it would feel much better if I squeezed it gently from both sides while moving my fingers up and down. It was hard to do at first, but now I know exactly what pleases her the most. Sometimes she asks me to put the fingers from my other hand inside and move them in and out while I do it."

"And does that give her an orgasm?"

"Yes mam, she says it makes her feel excited and basic, like a woman."

"From the looks of your penis, I'd say it makes you feel that way too."

He was so absorbed in telling me his story that he forgot about his nakedness, and didn't realize that he had become hard.

"It's OK, Kyle. It's normal for boys your age to get an erection just by thinking about girls. I'm glad you're excited. We wouldn't get very far if you weren't, would we? I have one more question before. Does Heather return the favor after you give her an orgasm?"

"No mam, not yet."

"Do you want her to?"

"More than anything mam."

"That must be very frustrating for you. Do you think the fact that you've prepped for your date helps you to cope?"

"I guess so, but I still usually have to do it again when I get home."

He was really opening up to me.

"After so much excitement, I can see how you'd need to do that. I'm afraid we're running out of time Kyle. Now I want you to lean back and get started. Here are some tissues for you to squirt into, just like you do at home. Does it turn you on to be in Heather's bed? Can you smell her perfume? I'll bet she's masturbated right where you are hundreds of times – maybe even this morning before she went to work. Does that thought excite you? I'll bet her wetness has soaked into those very sheets. When you think about Heather do you think about the smell of her vagina? Do you use that smell on your fingers to help you play with yourself after a date? Would you like me to find some of Heather's soiled panties in her hamper to help you remember that smell?"

"No mam, that's OK."

As I suspected, this little speech was all the incentive he needed. He couldn't wait to get started.

"OK Kyle. Now just forget I'm watching and do what you normally do when you're alone."

I was impressed by his approach. Rather than going directly for pay dirt, he started by gently caressing his face, chest and nipples with his fingertips. Next, he spent some time on his inner thighs – savoring the anticipation. Apparently he had forgotten all about the sense of urgency I had tried to create.

"That's very good, Kyle. Just relax and take your time."

Gradually, his fingers worked their way to his scrotum and he began to caress it very gently. I doubt if his penis had ever been harder.

"That looks like it really feels nice. You're being a very good boy."

Finally, he could no longer resist direct stimulation. His technique was one I had not seen before. He encircled his erection with the fingers of one hand and slid them down his length. The other hand followed just as the first completed its journey. I could tell he was using all of his fingers to stimulate the underside of his glans as they slid by. That's Bob's most sensitive place too.

"That's a very unusual technique, Kyle. Have you always masturbated that way?"

He managed to tell me he did it that way the first time and he still likes it the best, but he has a one-handed method that he uses sometimes too.

"Tell me what you're thinking about Kyle."

"I'm thinking about Heather and how exciting it is to put my fingers inside her pussy; and the way it squeezes around them when she cums. I'm pretending she's doing what I'm doing to myself right now; and about how proud I would be to shoot for her over and over again so she would know how much I love her and that I'm a real man."

"You're doing a very good job of expressing your feelings Kyle. Why don't you pretend I'm Heather? She wants you masturbate for her. She loves that you're not ashamed to do it while she watches. She wants to see you cum for her. Show her what a man you are! Do it now!"

I knew he was getting close because a big drop of precum had emerged from his opening and his breathing was getting more and more rapid. He abandoned his two-handed method and began frantically rubbing his most sensitive place with his right hand. His testicles retracted and he was moments away. A few seconds later, I could see him pass the point of no return. He leapt up, grabbed the tissues and began to ejaculate into them. I lost count after five or six spurts. I was mesmerized. Finally, the eruptions subsided, and he used his hand to milk out the last few drops. He was bathed in sweat. And so was I. The tissues were soaked; and he obviously didn't know what to do with them.

"That was very impressive Kyle. Here, give me your mess and I'll flush it down the toilet so no one will find it."

He sheepishly handed me the semen-soaked tissues. It was clear that this was no repeat performance.

"So Kyle, are you sticking with your story about having prepped for your date tonight?"

"I guess not."

"I thought not. Don't you ever lie to me again. I'll forgive you this one time, but in the future you need to do exactly what I say. If you do, we'll get along fine, and you won't have to worry about people finding out about the deal with you mom. And of course, you'll never have to worry about my telling Heather. Now you better get dressed. She'll be home soon. Aren't you glad you we had this little session? I don't see how you could have gotten through the night otherwise."

After he had gone, I examined the semen-soaked tissues. He had produced so much that it had not all soaked in, and there was enough for me to savor the feel of the slippery goo between my fingers. The smell was a profoundly compelling; probably not unlike what Kyle feels when he savors Heather's essence on his fingers. It was time for anther bathtub session before Bob got home. I desperately needed the release – and to figure out what I would make Kyle do the next time.