"MMM that's it Baby Boy, you must have really needed to be milked tonight, you squirted so fast. Why it only took what? 10 little strokes before your tiny peepee couldn't hold it and squirted out all your cummies for me" Gerri whispered into Steven's ear as he lay on her bed, drained and sated from his milking.
'It feels so good when you milk me Gerri, but I wish we could fuck sometimes like other couples" Steven said softly.
"Oh Baby, you know what happened the last few times. Your peepee just gets excited too fast and you make your little mess before you can get inside me. Then we have to get The Baby Wipes and clean it all up. Remember we agreed that your little baby peepee just is not cut out for pussy. And you enjoy your milkings, don't you Baby?" She asked, pouting.
"Oh no, I really love them Gerri, you make me feel so good."
"That makes me so happy baby Boy, and you know how much I love your little squirter." She punctuated her comment by leaning forward and planting a little kiss on the tip of his flaccid little member. "Now let me clean you up your The Baby Wipes, make sure you're shaved nice and smooth, get you all powdered up and I can give you some more lessons in how to make me happy using your clever little mouth, if you have the energy."
"I'd love that Gerri, I want to learn to make you feel as good as you make me."
It wasn't long before Steven lay naked on Gerri's bed, his peepee freshly shaved and powdered as she knelt over his smiling face. For his first few attempts at orally pleasing her they tried him kneeling before her and licking, but she explained that by lowering herself onto his face she had more control over where his tongue was focusing, making it more pleasurable for her. It was actually to reinforce his submission to her, and it also allowed her to look down at his smooth soft peepee as she taught him how to bring her to orgasm orally.
"That's it Baby, Oh you get better and better every time you do this. Soon you'll be the best little pussy licker ever. Mmm I think nature made you a natural born lick-boy to compensate giving you a baby penis, don't you? Oh don't try to answer, just keep licking, a little faster now, just like I taught you .... Just ... like that ..."
Gerri had a small satisfying orgasm as she ground her buttery pussy onto Steven's mouth. She wasn't quite ready to admit he was able to make her cum that way yet, as she wanted to his face between her legs for awhile longer. It was somewhere he'd be spending longer and longer periods of time in the future.
"That was good Baby, I almost came. It won't be long now before you can make me cum over and over, just like I do you."
"I want that Gerri, I really really do."
'I know you do Baby, and don't fret, you will. Oh and look, your little peepee likes it when you lick me, look it's trying to get stiff again. It's so sexy and hot when it's like that, trying to get hard when it's not ready yet, when it plumps up just a little, trying to get hard like a real cock, but it's not a real cock, is it? We both know that, don't we Sweetie?" She asked sweetly, leaning forward and gently stroking the tip of his semi-hard little member with her thumb and finger.
"Nngh no, I don't have a cock, I have a little peepee..." He moaned, as she coaxed a few little drops of precum from him.
"Good Boy, now let's have some licking lessons for a little while more and then I'll give you another nice milking. I know that little peepee needs to constantly make it's little squirts, you just can't control it, can you?'
That Friday night they both were working waiting tables. Gerri' saw Steven at one of the service stations, folding linen napkins. Since his back was to everyone as he worked, she decided to have a little fun with him.
"Hi Baby, it's been busy all night, eh? This is the first lull we've had." She said, moving next to him as he worked.
"Yeah, it's been crazy, but at least we're making good money."
"Feels like a long day though." She added, before leaning in and whispering in his ear. "And I can't wait to get you back to my place. So, we can get you nice and shaved and powdered up for you milkings. I'm really looking forward to watching your tiny peepee dribble for me."
"Mmm that sounds nice." Steven replied, then gasped lightly as Gerri discreetly reached over and rubbed the front of his pants. She was gratified to feel him instantly become hard.
"Gerri, please stop that." He whispered urgently. "We could get in trouble."
"Relax Baby, no one can see us from this angle." She purred, rubbing faster now as she continued to whisper in his ear. It was time to reinforce some of his conditioning. He hadn't been a premature ejaculator when they started out, but thanks to her he was squirting faster and faster now, requiring less stimulation. She needed to remind him that in addition to being too small, his baby penis squirted much to fast to ever be able to satisfy a woman again. "It's Ok Baby, I know what you need. It's your little peepee, isn't it? It needs to squirt all the time, doesn't it? It feels so good to just let it all out whenever you feel that urge. It's OK, I read in some books at Nursing School that it's very common for men with tiny little peepees to squirt uncontrollably. I don't want you all frustrated, go on Baby, let it out, squirt for me, I know you have no control."
She was rewarded by seeing that familiar look on his face, as he let loose a whispered moan and pumped out a load of warm jism into his pants.
"Gerri I .... I need to use the restroom." He said, his face almost bright red from embarrassment as he quickly walked off.
Gerri smiled; she hadn't been sure if he was sensitive enough yet to make him squirt in public. She had been using his frequent milking sessions to help reduce his stamina as part of her plan. Now it only took around 10 strokes to get him to squirt, and if things continued as planned, she'd soon have that number down to 5 or less. She would use that as reinforcement that his peepee wasn't meant for pussy ever again, and looked forward to hearing him admit it out loud. She had started subtly having him repeat phases during his milkings, almost as mantras. Reminders about his small size and uncontrollable squirts. Reconditioning him to associate a degree of humiliation with sexual excitement. She wondered if she could get him to the point where he would squirt in his pants hands free, just from her whispering in his ear.
She had also been mulling when the perfect time would be to invite him to move in with her. Currently he shared an apartment with 2 roommates and wound up spending the night at her place 3 or 4 times a week. Once she had him under her roof, she could get him more fully under her spell and step up his training.
Gerri realized she had to get back to work or she'd need to go clean up in the bathroom too, as thinking about her plans was making her quite wet herself.