Seduced into Boi-Hood Pt. 03

Story Info
Gerri continues Unsuspecting Steven's conditioning.
4k words
4.78
15k
21

Part 3 of the 6 part series

Updated 01/28/2024
Created 10/22/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"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.

Steven seemed quiet, almost sulking as they sat at a table in the bar section a few hours later for an after-work drink. Gerri had deliberately steered them to a secluded table in the corner for privacy.

"Gerri, I'm still kind of sticky down there. I wish you hadn't done that ..."

"Baby you know I have trouble resisting your adorable little peepee. It's so cute and sexy, I'd been thinking about it all day. How much I love taking care of it. And you know it's not all my fault, is it? Your little squirter doesn't need much we both know that."

"It never used to be that sensitive, I don't understand."

"Don't worry Baby, I think it's hot that you find me so sexy that you can't control yourself. Plus, I remember reading somewhere that a lot of men around your age with small baby penises turn into premature ejaculators." She lied.

"It's who you are Baby, you should never feel bad about it." She continued softly. She could see that talking about this in a public place, even speaking in hushed tones, was embarrassing him, just a she had planned. "Never apologize for who you are Baby Boy. Other women might find a tiny peepee that squirts so fast a turn off, but I love it." She had slipped one of her shoes off, and discreetly extended her pantyhose-clad foot up under the table to give his crotch a quick rub with it, winking at him. "Plus, you're getting so good with that mouth of yours, I get a feeling tonight might be the big night for me once we get back to my place."

"That would be great. I feel guilty you make me squirt all the time but I still can't return the favor."

Gerri smiled, it still made her happy that thanks to her that he now used the terms "peepee" and "squirting" referring to himself. Another layer of his manhood stripped away.

"Just let me finish my drink and we can get going Baby." She added, before lowering her voice and leaning forward. It had been several hours since she made him cream his pants, so she knew he would be ready to go again. "I love it when you're naked for me, so I can look at your cute smooth little peepee. That's why I get so turned on when I sit on your face for your licking lessons. I can look down and watch your peepee drip and twitch while I teach you how to finally, please a woman." She said, licking her lips and resuming caressing the front of his pants under the table with her foot.

"Oh don't ...." He moaned, to no avail as she rubbed harder.

"You love it too, don't you? You love looking up at my wetness as I lower myself onto your face, I can tell. I see you drip and hear you moan as I tell you just where to lick and suck, when to slow down and when to speed up ...." She could tell he was trying to control himself, so she pressed harder with her foot. She could feel how excited he was even through his pants. "I know you think my ass is sexy, you're always telling me that. You must love having your face buried in it while you're doing your lickies. I bet you've even been peeking at my tight little bumhole like a naughty boy, haven't you?"

"Omg yessss" he whispered, eyes half closed and mouth slightly opened as her foot rubbed back and forth, any signs of protest gone at this point. She had him right where she wanted him and she knew it.

"As a future Nurse, I keep myself nice and clean down there, don't I Baby?" As she lowered his voice even more. "You like looking at my pink little asshole, I know you do. Go on, admit it, tell me what a naughty little boy you are ..."

"Ooo yess, I like looking at your pink little asshole ..." He softly moaned, almost trance-like.

"Good Boy." She replied, pushing him right to the edge with her foot. "Because you admitted it, I have a special reward for you. The first time, after your lickies make me cum, I'm going to slide forward and you can give my pretty asshole a nice little kiss Hello. Would you like that?"

That was all it took to push him over the edge. He groaned a little louder than he intended, and gripped the sides of the table as she firmly pressed her pantyhose clad foot into his crotch. She saw his now familiar squirting expression on his face, and swore she could fell him spurting out into his boxers. She felt him rubbing against her foot as he drained himself, and held it steady for him to hump until he slumped back in his chair.

"You poor messy boy, let's get you back to my place and get you cleaned up. Don't go into the bathroom here and try, I want to do it"

Gerri asked for head start and arrived back at her place a good 10 minutes before Steven. That gave her time to roll a joint, change into sweats and get ready for him. She saw him pulling up in his car and was waiting for him at the door when he walked in.

"There's my messy boy! Quick, let's get those messy sticky pants off. All your clothes too Baby, you know we keep you naked for wipies and shaving." She felt herself start to cream as Steven's hairless limp penis came into view, covered in white crusty goo. "Oh, such a sticky mess, that looks so hot and sexy! Come over here now that you're undressed and let's get high before I wipe you, it might take a while, so much goo in your pants! Oh, you know what, I'll sit here at the kitchen table while we smoke, but you better keep standing up, you're covered in dry cummies and I don't want to get them on my chairs." This was a new part of his conditioning. She wanted him to get used to being naked around her while she remained clothed, and making him stand while she sat would help reinforce her dominance.

"I have good news too Stevie" she said as they finished smoking. She led him into her bedroom where she usually tended to his peepee. 'Remember how I was always having to wash my towels because I'd have you lay on them for your milkings and cleanings? Well, I picked up some of these" She said, holding up a crinkly folded plastic sheet. 'They're disposable changing pads, just perfect for you. Here we go, all unfolded on the bed, now up you go and lie down. Doesn't that feel nice and soft and crinkly, better than a towel even."

"I guess so, yes" Steven replied dreamily, the buzz from the pot starting to kick in.

"Ok you lay right there. You squirted so much all over yourself I think a nice warm facecloth would better than Baby Wipes, for tonight at least." She headed off to the bathroom to get the cloth. She wanted to give the weed time to kick in, as she found it made him more compliant and open to suggestion. She deliberately took her time soaking a light blue washcloth with warm water before returning.

"There we go, now you just float and let me take care of you. I see some stubble down there so I'm going to give you a nice touch up shave too. You know why I'm going to do that?" She had started asking this every time she shaved him, and he knew what she expected to hear.

"Because I have a baby peepee and baby peepees should be smooth and bald and powdered." He replied docilly as she gently wiped his crotch area,

"That's right Baby. Because it makes me all hot and excited to keep you that way. Sometimes all the shaving can be a chore though, and hard on your smooth soft skin. We have some new cream at The Hospital that prevents hair growth for a while, I was thinking we could try that. We'd only have to rub it on you once week or so, don't you think that might be worth trying? To make it easier for me?"

"Ok, if it makes it better for you, sure." He half mumbled as she continued to softly caress him with the warm cloth.

"Good Boy. Ok baby, lift your legs up now. You dribbled so many cummies that some leaked back by your bum-bum so that needs a little wipe too. Such a messy boy. There we go. Oh my, I never noticed how hairy you were back here too, I think I'll use the cream back here too, to get rid of all that yucky hair so cummies won't get stuck in it. Ok, put your legs down, I'm going to do some more peepee wipies and then make you smooth. Are you feeling good Baby? All that squirting tired you out?"

"I'm OK Gerri, just super relaxed."

"Ok that's how I like you. Shaving you will take a few minutes; you know I like to go nice and slow so we don't get any cuts. I don't want you getting too bored so I get you a little treat." She said, holding up a Tootsie Pop. "It's your favorite, Root Beer." She said, unwrapping it and popping it into his mouth before he could say a word. "There we go, now you just lay there all chill and suck while I take care of you." He actually didn't need shaving, but Gerri liked to use these rituals as a way of reinforcing her dominance. She looked down at him laying on a changing pad, eyes closed sucking on his lollipop and decided his peepee was ready for her again. Plus, the sight of him like that had her practically dripping.

"There, all smooth now. I'll be right back with your Baby Powder; you lay there and drift."

"Here we go." She said retuning, applying a light coating of powder to his limp peepee.

"Gerri, will you please sit on my face so I can try and make you happy?" He asked, eyes half-closed.

"That's the perfect way to ask Stevie, and so sweet of you. But ..." She said, pouting a little, "When I went to bathroom before I think my time of the month is almost here, so let's wait until next weekend. But I think it's so cute and sexy that you can't wait to lick me until I cum and then kiss my bum-bum. Don't worry Baby, we'll get there." She lied. She wanted him to spend all week thinking about orally satisfying her. By the time she was done with him, he would crave it.

"But I do want to get off, I got so hot cleaning off your peepee so I'm going to use this." Gerri said, holding up a small 9" vibrating wand. "Would you like to watch me Baby? You get me so aroused it won't take me long." She said truthfully.

"OMG Yes!" Steven said, suddenly fully alert, his eyes wide open.

"Mmmm just watch Baby Boy." She purred, kneeling as she switched on the wand and moved it between her legs. 'Oh that feels so good Stevie, I'm going to imagine it's your mouth down there ....aaaaaaaaaah .... Yes that's it..." She glanced over and saw his peepee hard as a rock a she watched her. She had been turned on all evening, and that sight was all it took to push her over the edge.

She pressed the tip of the wand against her needy clit and came hard, moaning and grinding. It took her a minute just to catch her breath, and when she glanced over, she saw Steven's peepee had started to drip from the sight. Just as she had planned.

"That was so good. Oh, it looks like you enjoyed the show too." She moved over to him, taking the leaky tip between her finger and thumb. She lightly stroked and was rewarded with a big drop of pre-cum.

"Gerri that was so hot ..."

"Mmmm you make me hot baby Boy. Lie back on your changing pad, I want to try something."

Before he could protest, she lightly pushed him down, turned the vibe back on and held the tip of it against his penis.

"Omg Gerri, what ... that feels ... Omg."

"Feels good doesn't it, Baby? Your tiny peepee likes being rubbed like this ....up and down and all around with the buzzy wand."

Steven had never felt anything like this before, and his mouth opened to speak but only an almost animalistic groan came forth.

Gerri had planned this all long, which was why she had milked him twice already. She didn't want him squirting too soon as she got him used to the sensation of the wand on him. She continued to edge him with it for another 5 minutes fascinated that he could still produce as much pre-cum after his prior squirts. She brought him right to the brink over and over, and knew he had reached the point she wanted when he let out a loud whimper.

"Tell me what you need baby Boy." Gerri asked, watching Steven's peepee drip and throb.

"Please, my tiny peepee needs to squirt again! Please!"

"You peepee seems to love Mr Buzzie, doesn't it? It feels so nice. I think rubbing like this is perfect for you, you're so tiny. I think you've always been too small to stroke and pump, and we should rub like this for now on for your milkings. What do you think?" She asked, continuing to vibe and then remove.

"Yes! Yes! Anything! Oh God! Please!"

"Ok then Baby Boy, just say it for me so, I'm sure. Say - My peepee's too tiny to stroke, just rubbing from now on."

"My p-peepee's too small to stroke, just rubbing ...nnngh." Hearing those magic words was all the incentive Gerri needed to press the wand firmly down on Steven. She was rewarded seconds later as he let forth an almost animalistic yell as a small river of semen came trickling out of him. The sight of his weak ejaculation was too much for her, and she quickly shoved the wand back between her legs and had a huge orgasm herself seconds later.

Sated, they both lay side by side catching their breath for several minutes before she got up to begin his wiping and powdering ritual.

"There we go baby, all limp, clean and powdered again just like you belong."

12