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The art of the handjob

imJen said:
Step mom / son imagery like this is always a hot thought.
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Reminds me specifically of an older woman who used to hit on me in my tennis playing days. Super sexy woman whose kids were getting lessons at the courts. I wanted her but so way too afraid to do anything other than cum thinking of her. The more she complimented my body, my tennis playing, my everything, the more i would need to jerk off.
 
WendyTrilby said:
In college, I learned the true art of the hand job. I was a teaching assistant for an extremely popular professor about 20 years older than me. He was married, and while I had a crush on him, I knew his wife (another professor) and respected that boundary. But, God, did I want him inside me.

One night at the campus pub, she (Mrs. Professor) granted me permission to give her husband hand jobs. This conversation came with him sitting right next to her.

She knew his female students were fixated on him, and some wanted to seduce him. To prevent him from straying, she allowed him to get hand jobs. She was very cold and clinical and reminded me of Lilith (Frasier’s wife from Cheers). She never used the word “hand job”, instead referring to it as masturbating her husband. She explained that she did not feel a woman masturbating her husband was sexual, but rather just helpful massage and release, allowing him to concentrate on his creative work. And it was all our job to help him be as creative as possible.

Without asking if I was interested, she listed the rules, and there were many:
  • No intercourse
  • No oral (either way)
  • No kissing
  • His hands could not touch me
  • He would ejaculate into a towel that he would bring home for her inspection.
  • He was not allowed to pleasure me in any way
  • One hand only
  • It had to be my right hand (I am a lefty)
  • His eyes would remain closed during the massage
Strict rules, but still relatively progressive on her part.

There wasn’t much in this for me. I suppose it would lead to an excellent recommendation on his part at the end of the semester, but that wasn’t discussed.

But I wanted to do this. Why? Because I was (still am) competitive as hell. If other female students had jerked Mr. Professor off, I wanted to do it better. I wanted it to be the best hand job ever.

Two nights later, after correcting a mountain of term papers, I delivered them to his office and asked him how he was doing. He was uptight and suffering from writer’s block. This was the cue.

He sat on the couch, unzipped his pants, and pulled them to his knees. His cock was a nice size. Not huge, but a little more than average, and I could see where it could deliver a lot of pleasure. But it was off-limits to everything but my right hand. It was semi-hard and unable to stand erect at this moment. He was waiting for me to do my job.

Realizing most girls just reached over and jerked him off, I tried to think outside the box. I stood on the couch so he could look up my skirt. He was a little shocked as this was already out of his norm, but it did not break the rules. He looked up and could see my panties under my mini skirt where my pubes were poking out (I was in a hipster no-shave mode that year).

I stepped over and slid my body in behind him. This was also new to him and still within regulation. He was forced to lay back against me. I reached into my bag and pulled out my hand lotion, and slathered it on his cock from behind. No rules against using a lubricant. I used my right hand to give him a slow massage, gently spiraling my grip up and down. I would then suck my finger and trace it from his balls upward along the spongy tube that runs along the bottom of a penis. I swirled my finger around the tip of that tight band of sensitive skin below his glans and above his foreskin. Then back to a full grip, going slow, then fast, then painfully slow. I tightened my grip, constricting blood flow, attempting to bring a little discomfort. I could tell he liked it.

I was tempted to put my finger in his ass and milk his prostate, a favorite of my middle-aged lovers, but that would have violated Mrs. Professor’s rules.

Still masturbating him from behind, his head turned to the left, eyes still closed per the rules. I wondered what he was doing. I saw his nostrils flare and realized he was inhaling the scent from my armpits. As I said, this was my no-shave era; the room was hot, and I was probably more spicy than usual.

I’m a good poker player and was able to see this tell. I raised my arm to allow his face to get under my arm. His cock responded in kind.

But my best move was yet to come.

He was (still is) a well-known author. I had read him and studied him before meeting him. Looking back, the armpit thing was in some of his works, but his real go-to description was sexual asphyxiation. It appeared in at least three of his novels. One is a random, twice could be a coincidence, three times – that’s a thing.

I put my left hand around his throat and gave it a gentle squeeze. Not enough to constrict his breathing, but sufficient to send the message – I know what you want, I thought.

His cock answered that question by stiffening, and I could see he was ready to cum. He leaned into my hand, trying to make me grasp him harder, so I did.

I had found something special that did not violate the rules. The secret ingredient even Mrs. Professor did not know. I now felt in control and told him to cum in the next 30 seconds, or I would stop, and he would have to finish himself off.

My hands were busy with his cock and neck, so I was unable to use the towel to catch his ejaculation. He fired off ropes of cum that splashed against his Brooks Brother’s shirt, ruining it. Mrs. Professor was not going to be happy.Hand job over, I released him. We said nothing, he cleaned up, and I left with a victorious smile. No way he had ever cum that hard in the past. I win.

That night, Mrs. Professor called me. We met at the pub. I was afraid she was pissed, and I was going to be fired as his TA. She made me describe the entire hand job from start to end in detail. She wasn’t sure if the armpits and choking part were acceptable within her rules. I offered to give her the same treatment so she could make a first-hand determination. Her office was just a short walk from where we sat.
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