Civil Penalty Pt. 07

When he warned me he was about to cum, I squeezed the base of his cock hard until he indicated it was safe to continue. Considering his nerves, I wanted him to last at least two minutes the first time. I smiled up at him encouragingly while I did so. It was delightfully easier than the acting I had been doing for my previous callous clients. I genuinely wanted this gentle boy to enjoy his experience.

By squeezing his cock and pausing while sucking the head of his cock, he made it to three minutes before erupting without warning into my mouth. I hadn't deep-throated him because it seemed unlikely that Emily would be willing to do that initially. I also didn't show him his cum on my tongue as a good slave should because Emily wouldn't do that either.

I cuddled him and reassured him he'd done well - it was clear that the entire evening was about building his confidence rather than his skills. "OK, Zack, next we will work on you fingering me and then going down on me. If you want Emily to look forward to sex, you must learn how to please her with your tongue. You should try to give her an orgasm first before making love to her each time. It will mean the world to her that you put her pleasure first instead of being focused on your own."

"Sit at the head of the bed with your knees apart." I leaned back between his legs, resting against his body. "Zack, play with my boobs again." He reached around and cupped them both, feeling their weight. Three weeks of Horny Juice, and they were already a little larger. I guessed I was between a B and a C cup and would need a new set of bras in the next week or so.

"Zack, while you do that, use your thumbs to play gently with my nipples." "Hmm, yes, just like that." He remembered what I'd said earlier and rolled both nipples gently between his fingers. "A little harder, Zack." He tried again, and the sensation was exquisite. "You can gently tweak them, pull them out a little and gently squeeze at the same time. .... That feels good, Zack, do it again."

"Now reach down with one hand, and explore my womanhood. Run your fingertip up and down to gather some juices to lubricate your finger."

"Can you feel a little button at the top of my vulva? That's my clit, don't touch the tip of it until I'm close to cumming, form a 'V' with your fingers and rub each side of it or circle it with your fingertip." I laid back to enjoy having my clit diddled. This was like having my own personal slave. It was just the tonic my soul needed.

I was getting close to orgasm, but this wouldn't bring me off. "Zack, now we will practice cunnilingus. Let's swap places. I'll lie back, and you lie between my legs. Now, explore my vulva; you can touch me anywhere; run your fingers along my labia. Feel the bottom of my slit, and slip two fingers inside the opening."

"Can you feel how wet I am? You need to get Emily that wet from kissing, playing with her nipples, and giving her oral sex before you try to insert your fingers or your cock. Remember in Game of Thrones, where that wild man from the North told Jon Snow to get Ygritte as slick as a baby seal? That's what you need to do."

"Now reach all the way in and explore my insides. Run your fingertip along the top of my vagina. Can you feel that spot, yes, right there, where it feels a little different? That's my G-spot and rubbing that will bring me to orgasm. Curl your fingers up so you scrape over that spot each time you withdraw your hand."

Again, I laid back and enjoyed having my G-spot rubbed. "Zack, now speed up and press on that spot harder as you do. Mmmm, Oh Zack, that feels so good. Keep on doing that; Emily will love it."

I let my orgasm build. I wanted to build Zach's confidence, and nothing would do that better than him giving me an orgasm.

"That's it, Zack; I'm cumming; feel my pussy clench." The spasms started, and I moaned for his benefit. It wasn't an earth-shattering orgasm, but he looked pleased as punch that he'd been responsible for it.

"Now, Zack, you can give me another orgasm with your tongue. Lift my thighs onto your shoulder, which will tilt my hips up and give you a better angle. Look at my pussy closely. See the inner and outer lips. You start by kissing all around the outside of the outer lips and then kiss and suck the outer lips. After that, you can kiss and suck the inner lips; only after that can you lick up the centre in nice long, steady strokes. I do best with a consistent rhythm, but other women prefer other things. You need to learn what makes Emily feel good."

I laid back like a pillow Princess and simply enjoyed having my vulva pampered, even if it wasn't with consummate skill.

I let him do that for 5 minutes. "Zack, do you remember the button at the top of my gash? Lick all around, kiss, and then lick it before sucking it into your mouth and pulsing your lips on it while sucking.

I laid back again, he needed a little further clarification, but he got me there, and I had an even better orgasm the second time. I sighed and wished I had more sessions like this.

"Zach, you've brought me off with your fingers and tongue. Will Emily be OK with you losing your virginity to me so you know what to do when you make love to her?"

"Yes, Emily and I promised we'd never keep secrets, so I got her permission to see you tonight and permission to do everything needed to be prepared."

"Good. You are going to bring me off on that lovely cock of yours. It's a bit bigger than I'm used to, but it will be fine." I said reassuringly; after all, every man wants to hear he's better endowed than his peers. His uncircumcised cock was a very average 5" but thick enough that I'd feel him OK.

"Emily will be very tight the first time, and it will be easier for her if she is on top and can control the speed of penetration. If her hymen is intact, that's a little crescent of skin that covers the bottom of the vagina opening; you can break it with your thumb first or let it break as she sinks on your cock; remember, that is her choice, not yours. Lie on your back, and I will slowly lower myself on your cock like Emily will."

I sank down on his cock and moaned to encourage him, "Oh, Zack, your cock feels so good inside me. I'm sure Emily will be delighted." I rode him for a while and then told him, "We will try several different positions now. First, we will do it doggy style with me on all fours, then with me on my back and my legs wrapped around your waist, and lastly, with me on my back and my ankles on your shoulders so you get a deeper penetration to bring me off. Zack, you must control your orgasm by stopping or slowing down whenever necessary. Your goal is to last longer than Emily does, and as soon as she cums, you can stop fighting it and cum too.

The boy did it; I enjoyed my third orgasm while he had a look of quiet desperation from staving off his own relief. "Cum for me. Cum, now, Zack." And he did, yelling Emily's name with his release. As I stroked his back, I felt his babymakers squirting deep in my love canal. I was sure by now we'd covered the basics, and he would have a lot more confidence to handle their first night together.

His final lesson was that most women want to be cuddled after sex and that he wasn't to rush off thinking it was over. He held me while I got him to tell me more stories about Emily and how he'd fallen in love, and how he'd proposed.

Three days later:

Zack knocked on my door and stammered, "Doctor Cartwright, please may I talk to you about what happened?" I smiled and beckoned him. He shut the door and stood, pensively wringing his hands, unsure where to begin. I broke the ice.

"Are you still glad you saw me?"

"Oh, yes, it was wonderful. I'm so looking forward to my first night with Emily. I'm feeling a lot more confident."

"How much did you tell Emily?"

"I told her everything we did in detail at least three times as she wanted to learn all she could, which is why I'm here now. Doctor Cartwright, I know this is possibly inappropriate, but Emily asked if she could see you before the wedding instead of me seeing you twice. I tried to sign up again, but your sessions are fully booked. Is there anything you can do for her?"

I giggled; this was priceless, another session where I would be explicitly asked to top from the bottom, and I could make sure my own needs were met too.

"Zack, my Sundays are free. You'll have to sign her into the building and then wait in the penthouse sitting room. But, yes, I'd love to spend an hour with Emily."

******

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