Cheryl was friends with Jack’s wife, but she was single. She needed manly advice from time to time. So she caught her son, Alan, jacking off and asked me to talk to him about it. He was 15 and always horny. Of course, she had no idea I was bisexual. I took her up on the idea to talk to him. What started as me innocently talking to her teen son about masturbation descended into a twisted tale.
I went to Alan's house after work one day to talk to him. His mom was single and she need a male figure to discuss masturbation since she had caught him doing it. I rang the bell. I heard footsteps on the stairs and then the door opened.
"Oh, hi Mr. Jones."
“Can i come in?”
“Sure,” he said holding the door open.
“Alan I have to be home soon, so let me just say this quickly: I know your mom caught you jack--err--masturbating to some porn on the computer."
"Yes," he blushed. “I need images, my mind can't just think of girls, I am visual.”
“I understand but the computer is in her room. Lets go have a look.”
We walked upstairs and into her room. Sure enough, her desktop pc was on her desk.
I was intrigued. “So, what kinda stuff do u watch? Let me see and tell you if it's appropriate.
He blushed. “I prolly sholdn't.”
“Look I told your mom I would talk to you. So show me”, I said sternly.
He went to page called Milf lesbians.
“OK look you should probably just watch straight porn ok? I mean you have a younger sister who doesn't need to be seeing lesbians”
“She won't see I always look the door,” he retorted.
“Is this what you were watching when your mom caught you?”
“Yes, she has a key to the room of course.”
“Well, this won't do at all. I don’t want her catching you again. Here I brought you this.”
I handed him a magazine of mostly nude girls, but also with a couples section that showed girls sucking large cocks. I wanted him to get used to seeing more cocks. No more of this lesbian shit!
“Now you use this and stay out of mom's room, she needs the computer for her own business. Ok?”
He looked at the magazine and said ok.
Now I placed a hand on his shoulder. “Look Alan, you're a teen boy. This is natural.”
He surprised me by asking, “Did you jack, err, maturbate at my age?”
“Yes of course I mastur, err, jacked off a lot.” I winked at him and he seemed to relax some.
I went home to dinner with the family.
The next week I dropped by Alan’s house, hoping to catch him jacking off.
I rang the bell. I heard a window open upstairs.
"Who is it, " I heard Alan say
“OH come in the door is unlocked.”
I went upstairs where he was shirtless and still showed signs of a waning boner inhis shorts.
“Alan” I asked, “were you jacking off?”
“Well, I just...”
“Nevermind, it’s ok “ I laughed. Did you like the magazine?
“Oh ya! Thanks.
Well here are two more.
He didn't really look thru them . One was couples only. The other had solo girls but one tranny section. I wanted to get his reaction.
I opened it to the Tranny section.
“I didn’t know this was in here when I bought it,” I said holding up a page with a beautiful Latin tranny with panties on. Her dick was hidden.
“What’s wrong with her?” he gazed, she is fine!
I turned the page and revealed her huge cock sticking out from under her skirt.
"What the Fuck!?" he exclaimed. “What is that?”
“They are called shemales, or transexuals Alan.”
Y”es I heard but I never SAW one.”
“Well , like Isaid Im sorry I didnt know it was in there. Here I can take it back.”
But he drew his hand away, keeping the magazine.
“No its cool” he said, “I can just skip her.” he laughed.
And I said.”Do try and be discreet.” I pointed to this thick cock. he blushed.
Again I put my hand on his shoulder. it ok its natural. some men even like transsexuals they get so horny!
“To each his own,” h e laughed.
That weekend I had a nasty plan developing.
It was Friday night and as usual, Alan';s mom was out partying. So much the better. Alan was shocked at the lovely lady I had brought to his house.
"Hi,” she said to him, cupping his chin in her feminine hands. "I hear you have a need for a girl."
“Y-y-yes,” he stammered as he looked at her giant tits just inches from his face.
"Yes, and I am all woman," she retorted.
He looked confused as she sat by him.
“How about a backrub you sexy man?” she said.
“I will return.” I said as I left to get a beer.
"MY name is Andrea” she said to him
“I am Alan" he said. "You sure are pretty."
"Thanks she said "and you are handsome."
She turned and kissed him gently. Her tongue found his mouth and played gently as he moaned.
She rubbed his cock thru his jeans as he moaned. He grabbed roughly for her tits, an obvious beginner.
“Hold it baby, ”she said.
She pulled down her top and told him. "Suck these titties"
Alan greedily sucked at each nipple in turn as she rubbed his cock lightly.
“Yes,” she coaxed him, that's it.
I returned with a beer. Alan looked upset
“Can't you leave us alone for a minute?” he asked me.
“Take a break and have a beer,” I said.
They talked and seduced Alan as he downed 3 beers, easily giving him a buzz.
Andrea continued rubbing his cock thru jeans as he sipped his beer. My intention was to get him a little drunk so he didn't freak out when he realized what was happening.
I moved over and pulled out my cock . Andrea started sucking and Alan now knew it was safe. He started jacking off, but she stopped him. "I want all your sweet cum baby," she said.
Andrea straddled his lap with her perfumed tits right in Alan's face. True to teenage form, he dove in mouth first and sucked and licked her beautiful tits. He started groping his ass as she grinded her privates on his lap and stroked his hair.
Alan was by now ready to pop. Andrea got on her knees in front of him and kissed his rock hard cockhead. she gave it a lick and then took his length into her pretty mouth.
Just a few strokes and he started moaning saying "Oh, I'm gonna cum baby!"
She removed her lips and jacked him off with her pretty painted nails as he the milky cream shot out of his cock over and over. I now knew he would do anything for Andrea, she was a goddess, even if...