Diary, Part 7, Michael

It was Michael’s second session with Brandi.  I was watching through the hidden cameras.  Michael came in and you could see he already had a hard on.

“Hello, Michael, how are you today?  I can see you’ve been thinking about our session today.”  Brandi deliberately looked at his pants and gave him a smile.  She came closer and gave him a hug.  Michael did not return the hug but stood shyly while her arms surrounded the young lad.

“Did you consider masturbating before our session today, Michael?”


“Did you masturbate?”  He shook his head.  “It would have been okay if you did.  Sometimes boys will masturbate before they go out as a way to get that first one out of the way since the second one always lasts longer.  Also, Michael, remember our rules.  Speak to me in complete sentences.  I want you to be more verbal and when I ask you a question try to answer it with more than a simple “yes” or “no.”  She lifted his chin and looked him in the eye.   “Okay?”

“Y-y-yes, Brandi, I will do my b-b-best.”

“Very good.”  She kissed him on the cheek as a quick reward.  “Today we are going to demonstrate the pleasures of denial.   I need you to get undressed and lie on the bed on your back.”  After an awkward moment of silence, Michael began to undress while Brandi watched him.  He had virtually no hair on his chest but his lower arms showed some light fuzz as did his lower legs.  Brandi shook her head at his tightie-whities.

“One day, we’ll have to take you shopping for some sexier underwear.”  Michael got up on the bed and laid down, his long thin pole sticking up in the air.  Brandie stood next to the bed and put one hand on his chest.

“Alright I am going to touch you and I want you to enjoy my touching but I don’t want you to come if you can help it.  You must not under any circumstances touch your dick.  Tell me if you feel an orgasm coming on.  Okay?  Let’s start with a kiss.”  She leaned forward and kissed him softly on the lips.  His remained closed.  She pulled back.

“Have you ever made out with a girl?”

“N-n-not exactly.  I’ve k-k-kissed some b-b-but never made out.”  Brandi smiled, amazed at how inexperienced he was.  By his age, Brandi had a full range of sexual experiences.

“When our sessions are over, you will be an expert lover.  I will teach you how to please a woman in many ways.  And you will learn to control and own your own sexuality.  You will be confident and be able to get just about any woman you want.”  His body jumped a little as her hand inadvertently moved across his chest.

“There are two aspects to excitement.  One is physical and the other is mental.  Working on both will make you a great lover.  So you notice how talking about sex excites you?  Same with women.

“So, let’s start with kissing.  When you kiss, open your mouth a little and relax your lips but move them.  Imagine an ice cream cone and you are biting it with your lips.  You don’t want to use your teeth but you want to pull the ice cream into your mouth.  Pay attention to how I do it.”  They started to kiss.  At first Michael was passive but opened his lips a little.  As Brandi kissed his lips sweetly, he joined in and did very well.  After a few minutes, Michael put his arms around Brandi.  She encouraged him with a moan.  She began to use her tongue, licking his lips, and he did the same.  Then he over did it strictly licking her lips and moving faster.

“Relax, Michael, use your tongue sparingly.  Let’s try opening our mouths a little more and letting our tongues touch.“  Michael was panting a bit not used to kissing and breathing at the same time.  He took instruction well, however, and soon his kisses were having an effect on Brandi.

“Wow, you really learn fast.  That’s great.  You’re a natural kisser.  Of course, kisses can work on other places as well.”  She leaned forward again and placed a kiss on the side of his face, then next to his ear, then placed on directly in his ear.  “How’s that feel?”

“N-n-nice.”  She held his face in her hands and kissed him around in a circle from cheek to forehead to cheek, ending on his lips.  His arms went around her again until she leaned back.

“There is more you can do with your arms too.  When you hold someone, don’t be afraid to move or slid your arms to new places.  Or sometimes just a little finger movement.”  She trailed her fingers through the bottom of his hairline at his neck and down the slope of his shoulders.  “And you can tease someone’s mind without saying a word.”  Her hand trailed across his chest down to her stomach and rested there for a minute before sliding over to his hip.

“I know you were wondering if I was going to keep going and touch your dick, weren’t you.  Well, girls think like that too and it can be exciting to think that he’s going to touch my breast or put his hand down my pants.”  With that she moved her hand down his far leg, her wrist touched his cock and slid down it.  Michael moaned.  “This is what I can the inadvertent touch.  It doesn’t appear as though I am trying to touch your dick but, of course, I do.  It can often be used to touch a girl’s breast.  And moaning is very exciting to listen to and if you listen carefully to her you can tell what excites her.”

Brandi’s hand moved up from his thigh and cupped his tight balls.  She moved slowly up and gripped his cock.  Looking into his eyes she started to rub up and down the shaft.  Michael’s whole body began to fill with tension.

“Tell me if you think you are going to cum.”  She pulled up and down a few times and then stopped.  She placed a gentle hand on his stomach.  Michael twisted his body his erect cock reaching for something other than air.  She rubbed his chest.  “Just relax.”

Brandi continued to play with Michael like this for what seemed like hours to Michael.  For about 20 minutes, she would touch his cock – sometimes avoiding the most sensitive underskin – for a few strokes, then move away.  It was torture for Michael but she knew it was for his own good.  All of this time she remained fully clothed.  She placed three fingers on his sensitive underskin; against the Corinthian ripples of his circumcision.  She just laid her fingers against him and pressed.  Michael began to move his hips trying to rub himself against her but she moved with his movements, minimizing the friction.

“I think I’m going to cum,” Michael stated without a stutter.  Brandi squeezed his cock hard enough to hurt and pulled down trying to block off his ejaculation.  There was a small oozing of cum out the top but it seemed as though she was able to prevent his ejaculation.  She got on the bed, straddling him on all fours but not touching him.

“Kiss me.”  Their lips touched and Brandi was almost as excited as Michael.  It was one of the real pleasures she got out of this job.  She was in control and had this boy at the very edge.  She fed off of the electricity and tension running through his body.  The kissing was hungry and hot.  Both of them totally engaged.  Enough, she thought.

“Michael, may I put my face between your legs?”


“Just okay.  Is that all I get?”  She began moving down his torso with a few small kisses here and there.

“Please, Brandi, p-p-please put your face on my thing.  Please let me cum.  Please, please, pretty please.”  She had his cock in her sights and positioned her head below it.  Licking it from the bottom up, her eyes watching his expression.  His face contorted eyes closed.

“Look at me!”  He lifted his head slightly and watched as her lips surrounded the tip of his pole and went down on it.  Her eyes never left his but he couldn’t stand it.  Closing his eyes he thrust into her mouth deep catching her by surprise and causing her to choke on his long pole.  She grabbed the base of the pole measuring the remainder so his thrusts no longer were too deep.  Twice, three times, and on the fourth she felt the warm sweet essence of the man he would become – that she would make him into.

She wanted to cuddle with him afterward.  This was generally not recommended but she felt genuine warmth for this boy who was becoming a man, so she did for a minute while he caught his breath.

“Like that?”


“Sometimes it’s fun to make it last.  You did wonderfully.”

About rushmorejudd

Independent author of erotic stories. https://rushmorejudd.wordpress.com/ https://www.smashwords.com/profile/view/Rushmore
This entry was posted in Diary, Erotica, Fantasy and tagged , , . Bookmark the permalink.

5 Responses to Diary, Part 7, Michael

  1. marica0701 says:

    It’s been fun to read these “diaries”.

    Enjoy your vacation! 🙂

  2. I have really been enjoying your series! You’re doing an excellent job of writing!
    Have fun on your trip!
    HUGS!!! 🙂

  3. Pingback: Index, Diary of a Sex Therapist | rushmorejudd

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