From Man to Milkmaid

From Man to Milkmaid

Blog Entry - 5/15

Not much new, as usual. Working from home in the Post-Covid World has its benefits, but one of the drawbacks is you're stuck home alone in your apartment all day. Well, if you are single and unable to meet anyone like yours truly. I did hear through the laundry room grapevine that they finally rented the place across the hall, so at least I'll have the excitement of watching them move in through the peephole.

Blog Entry - 5/17

Well, I met my new neighbor and what a nice surprise. She is gorgeous! She looks to be maybe 10 years older than me, in her mid-thirties. Her name is Bella and she has that Classic Mediterranean look going on. Long black hair and one of those hourglass figures that makes it hard not to stare (I managed to resist, don't want to be giving off creepy neighbor vibes lol). Looks like she has a sweet TV and sound system. She mentioned she's a self-professed luddite and would have to find someone to set it up, along with Her PC and a few other techy items. Her face lit up when I told her I work in IT and I'd be glad to do it (and practice my non-creepy checking her out).

Blog Entry - 5/19

I can think of worse ways to spend a Saturday then helping the hot new neighbor with stuff. I wound up spending more time at Bella's than planned, as there was a mix-up with getting her Internet and Cable turned on so I spent way too much time on the phone helping her sort it out. The fringe benefit of being there awhile is at one point she asked if I'd mind if she grabbed a shower while I was setting up her sound system. She popped out in a short robe 15 minutes later and I think I need more practice discreetly ogling her. She told me she works as a Financial Analyst, and it must pay well judging by her furniture and electronics. She offered to pay me but I refused, like a good neighbor. I need to go back for a few hours tomorrow and she said she'd find some way to make it up to me. I know Those Letters to Penthouse were purely fiction, but that image of her in that robe is stuck in my head lol

Blog entry - 5/20

OK, I take back the thing I said about Penthouse Letters. But let me back up a bit. I went back to Bella's and got her PC up and online. She works from home like me, so she was very happy. She also confided she occasionally sees clients in her apartment which is against the lease, but I swore her secret was safe with me. We chatted on her sofa after I was done, and she made me a cup of the best tea I've ever tasted. I asked her the brand but she said it was an old family secret, with a conspiratory wink. After my second cup I told her I should be going, but she put her hand on my knee and told me to hold on a minute.

"I need to thank you for all the help, Sweetie. You didn't want any money but I think I have a better idea. I think you deserve a nice milking." She said softly, her hand moving slowly up my leg.

"A what? Bella, you don't need...' I stammered as her hand made its way to my rapidly hardening cock. I wasn't sure if I was imaging this or not, as the tea had made me a little light headed. I almost felt like I was moving in slow motion and before I knew it, she had my pants undone and her soft hand wrapped around me.

"Sssh Sweetie it's OK" she whispered in my ear. "A good helpful boy like you deserves a nice milking, don't you? You said you don't have a girlfriend so you need a nice milking to get all that stuff out of you, don't you?"

At this point she was pumping my cock at a nice steady pace. She reached over to grab some lotion off the end-table and quickly applied it while she continued her whispering

"That's it Sweetie, just relax and let Bella milk you. Oh, you like that, don't you? I can feel your stiff little peepee throbbing in my hand."

I had never considered my 4" small, but was in no condition to argue with the sexy woman stroking, I mean milking, me.

"You're going to squirt for me, aren't you Sweetie? A nice fast milking, such a good boy. Now go ahead and squirt and we'll get all your milk out. That's it... mmmmm"

I swear her sexy whispers alone were probably enough to make any man cum, I mean squirt, but combined with her touch I came as hard as I could remember under her ministrations.

"There we go." She said, "All milked so your balls are all drained and you peepee is nice and limp like it belongs." She added, handing me a tissue to clean up with and planting a small kiss on my forehead.

"Oh, my look at the time. Catch your breath and then head home Sweetie, I have a date in a few hours and need to get ready."

Before I realized it I was back in my own apartment, wondering if I'd imagined the whole thing. The stains on my pants proved otherwise.

Blog entry - 5/22

It was hard for me to get Bella out of my thought for the last few days. Her soft touch and the things she whispered kept replaying in my head, it was so erotic. I must admit I jerked off thinking about her milking me the day after. Naturally, I was thrilled when she knocked on my door today and asked if I could come over and help her tomorrow. She bought several smart home devices and needed help setting them up. I couldn't help but wonder if she'd milk me again.

Blog entry - 5/23

It only took about an hour to get her smart devices set up, after which she made me a cup of that delicious tea and joined me on the sofa. I think she saw me glance at the lotion and tissues on the side table and smiled.

"Thanks again for your help Sweetie. I'm a wizard with numbers, but just don't have the touch for all these electronic gadgets."

"I'm glad to help Bella, that's what neighbors are for."

"That's so sweet. Well, I think you deserve a reward for being such a helpful boy. You enjoyed your milking the other night, didn't you?"

"Well yes, it was so hot." I said, blushing.

"I think helpful boys deserve a reward, don't you? I think you need to be milked again, don't you?" She said softly, moving her hand to my leg. "Would you like that? I can see your peepee is all hard through your pants. Do you need me to drain all the milk out of you and make it nice and limp again? Just ask me to milk you Sweetie and I'll make you spurt it all out." She whispered, rubbing me through my pants.

"Please milk me..." I moaned as she started undoing my pants.

"Such a nice polite boy." She said softly, pulling out my stiff member and teasing it with one finger softly. "Ask Bella to milk your little peepee like a good boy." She whispered in my ear, pouring some lotion onto her hand.

"Please milk me Bella, please..."

"Ask like I told you Sweetie." She said, lightly stroking me.

"Please milk my little peepee Bella." I groaned, already starting to dribble pre-cum.

"Good boy, now let's get you milked. Let Bella drain all the creamy milk out of those tight little balls so your peepee is nice and limp. That's it, I can tell you're close. Boys like you need to be milked regularly, to keep them limp and small and well-behaved, don't they?"

"Yessss... "I moaned, putty in her skilled hands.

"Good boys spurt their milk nice and fast, don't they? I can tell your close, don't fight it Sweetie, just let it out... almost there, nice and fast... open your eyes Sweetie, look down at your peepee... You need to watch the sweet milk come spurting out.... There you go... good boy... see it spurting out.... Give it all to me... every drop.... Such a good boy for me...."

I almost passed out as she finished, coaxing every drop from me.

"So much milk, and now you're nice and limp like a good boy." She purred in my ear, "Nice creamy milk..." she continued, scooping a gob of my cum, my milk onto her finger and bringing it to my lips. "Go on, taste the delicious milk for me."

I felt so light-headed I couldn't resist as she slipped her finger into my mouth and I tasted my own cum, my milk for the first time.

'Such a good boy. I love the way your peepee looks now, soft and tiny after it's milking, just how it belongs. Why don't you clean up and head home, you look ready to pass out and it's getting late. After you thank me for your milking of course."

"Thank you for milking me, Bella, I better go, I can barely keep my eyes open. Is there something I can do to make you feel good too?"

"Not tonight, Sweetie. There's nothing like a good milking to tire a boy out, is there Sweetie? Why don't you come over tomorrow evening and we can chat some more."

I was so drained I barely got changed and into bed before I fell asleep. I swear I dreamed about her.

Blog entry - 5/24

What a night! I don't know where to start... Bella texted me around 7 PM to come over here place to talk, but with a winking face. I had been thinking about what was going to happen all day, thinking about being milked again. It had been almost a year since I had gotten laid, so her the thought of her soft touch and sultry voice whispering in my ear had kept me in an erotic fog all day. My cock had been hard almost non-stop. I thought about jerking off during the day but I knew how happy she'd be if I spurted out a nice big warm load of milk for her.

I knocked on her door and she ushered me in to her living room, a cup of her special tea already waiting for me on the table. She apologized and said she had to make a quick work-related phone call, and that I should just relax on the sofa for a few minutes and enjoy my tea. I had just finished it when she returned, pored me another cup and joined me on the sofa.

"Thanks for being such a good boy and being patient Sweetie. I wanted to talk to you about something." She said softly, putting her hand on my knee. She smiled as I instinctively spread my legs a little.

"Oh my." She chuckled. "It looks like someone is eager for his milking. Is that a stiff little peepee I see in those pants? We'll see about that after out little chat and you drink your tea, Sweetie."

"That sounds wonderful Bella." I replied, trying to hide the disappointment in my voice that I wouldn't be milked right away.

"You asked me last night if you could make me feel good, remember Sweetie?" She asked sweetly, moving her hand a little higher. "I have a little confession to make... I have kind of a little fetish. A milking fetish. Finding sweet good boys and helping them stay well -behaved with constant milkings is what makes me feel good. Helping boys like you behave by keeping them drained, keeping their cute little peepees soft and limp is what gets me off. Boys like you Sweetie." She purred, rubbing me through my pants softly with one finger. "I think you need to be milked constantly sweetie, to help you behave. Would you like that? Regular milkings by Bella to keep you sweet and soft and small? You can tell me Sweetie." She said, now lightly rubbing me and driving me out of my mind.

"Yesss Bella, I need milking, please milk me to help me be a good boy." I moaned.

"Regular milkings Sweetie, on a schedule set by me that'd you have to adhere to. To keep you milked and limp and soft... do you need that? You can tell me..." She intoned huskily, slowly unzipping my pants.

By now I knew what she wanted to hear. "Please Bella, I need regular milkings. I need you to help me be a good boy and keep me drained and my peepee limp and soft."

"I was hoping you'd say that sweetie." She said, her face lighting up. "Now there will be rules to follow from here on in, but I know keeping you a good boy will help you follow them. You want to follow Bella's rules, don't you? Good boys follow my rules and get lots and lots of milkings."

"I want to follow your rules, Bella." I groaned, my cock throbbing and dripping pre-cum.

"I know you do Sweetie, I know it's not easy to be good with your peepee getting hard all the time but we're going to take care of that. Now the first rule is unless I say otherwise, is you're to be naked for you milkings unless I tell you to wear something. So, stand up and strip for me."

Despite being milked by her several times I still felt nervous undressing in front of Bella, but quickly complied and stood before naked and erect.

"Doesn't that feel better Sweetie?" She purred, tracing the length of my quivering cock with her finger before reaching up and fluffing my pubic hair. "Rule # 2 Sweetie - this hair must go. I told you about my fetish, I like to see a small peepee like yours all smooth and bald, no more hair. It makes you look so small and adorable, like a little boy. I'll give you some cream to take home to put on before you shower that will take care of all that hair, and just use it regularly. You'll stay smooth and bald, won't you/" She asked sweetly, lightly stroking me.

"Yes, Bella, I'll keep myself smooth for you." I said, my knees buckling a little as she sped up her stroking a little.

"You'll keep your peepee smooth Dear. That's rule # 3, from now on you never refer to it as anything but a peepee. It's too small to be a cock, it's just a tiny peepee from now on. Now tell me again..."

"I'll keep my peepee smooth Bella, I'll keep my tiny peepee hairless for you... Ooooh..."

"Good boy. Now I think that's enough rules for tonight, except maybe one more. But I think you deserve a milking now, don't you?

"Please milk me Bella.... "

"You mean milk your tiny peepee Sweetie..."

"Please milk my tiny peepee Bella..."

"Good boy! Remember to ask that way from now on." She said increasing her pumping. "You've been so good, I know your little peepee squirts so fast when it's being milked.... Go ahead, go ahead and spurt out your milk for me. Remember, you always have to watch it spurting, watching the milk being drained from you.... you enjoy watching the milk spurt out..."

That was all I needed to hear as I surrendered to her ministrations, groaned, and began to spurt out my milk under her direction. I hardly noticed as she grabbed my almost empty teacup and with her other hand and used to catch my squirts in.

She helped me sit down as I was feeling light-headed and drained. "Last rule for tonight Sweetie... good boys always drink their own milk." She said smiling, raising the cup to my lips. In my euphoric post-orgasmic daze, I was happy to drink down the mixture of tea and my milk.

"Oh Sweetie, this is how I like to see you, this is how you belong, it's how I'm going to keep you..." She whispered in my ear as she reached down and fondled my now limp peepee. "I can't wait until you come back tomorrow for your milkings, all hairless and cute, you'll look even smaller, like a good little boy. Now catch your breath and get dressed while I go get that hair removal cream for you. Remember to use it. I want you back here tomorrow morning at 8 AM and we can discuss your new milking schedule."

Even limp I felt my peepee quiver at her words. I couldn't wait until tomorrow.

Blog entry - 5/27

It's been a few days since my last entry, quite a bit has happened.

I used the cream Bella gave me and sure enough, my peepee is now completely hairless like a little boy. She texted me to come over at 8AM that morning so she could milk me and discuss my new routine. We had a cup of tea and she told me that I would need 3 milkings a day to start, to keep me drained and well-behaved.

Her eyes lit up and she got a huge grin after I finished my tea, stood up and stripped and she saw my smooth little peepee for the first time. She told me how adorable and tiny I looked, now that I was all smooth and how she normally would prefer me limp but this time she couldn't resist teasing me with one finger for almost 15 minutes so she could watch my bald little guy twitch and throb.

She made me promise to use the hair removal cream twice a week to stay hairless for her, and how could I resist? After I asked her properly to milk my tiny peepee again she began stroking me, whispering in my ear what a good boy I was, how this is what good boys with small baby peepees need. I must admit I never thought of myself as small down there, but looking down at myself all shaven I realized she was right, as always.

She whispered that I shouldn't worry, that even though I was too tiny to ever satisfy a woman with it, that she'd keep me happy and milked. That was all it took to make my spurt into my teacup, which she asked me to hold from now on so she could concentrate on the milking.

I then sat down and drank it all up, like a good boy. I realized I had previously finished the tea and was just drinking my own milk, but had gotten used to the taste by now and even looked forward to watching it spurt out of me.

Then Bella indulged her fascination with my tiny limp peepee, gently fondling it for 15 minutes or so whispering soft affirmations in my ear of what a good boy I was for her. She told me this would be our weekday schedule, milkings at 8 AM, 5 PM and 10 PM as our schedules allowed. She whispered I'd probably be milked more on the weekends.

By now I was craving her touch, and could refuse her nothing. I couldn't wait for Saturday.

Blog entry - 5/27

What a day today was. I'm going to love the weekends even more from now on!

When I got to Miss Bella's for my morning milking, she poured me some tea and explained she had a few new rules that good boys need to follow.

The first of those was that I should call her Miss Bella from now on, as a sign of gratitude for her keeping me empty, soft, and well behaved. After all she's been doing for me, how could I refuse?

She told me the next new rule as I was undressing. She said she can hardly wait to see my hairless little peepee when I come over, so from now on I should just come over naked so she doesn't have to wait. She could tell by my face I had misgivings about that, but quickly pointed out that I lived right across the hall and she'd keep her door ajar for me. She always makes perfect sense.

She guided me to the sofa, using my peepee as a leash and had me sit beside her. She lightly teased the tip of my tiny member and told me on weekends I would be milked a minimum of 5 times, our schedules permitting of course. I gasped in pleasure at the thought as she began stroking me.

She whispered to me that a quick miking is a good milking, and good boys spurt nice and fast. She told me she was going to count the strokes it took for me to spurt, and she knew it would be less than 20. I closed my eyes in ecstasy as she softly began counting down, but she reminded me that well behaved boys always watch their small peepees squirt, so I immediately opened them and watched her milk me.

Sure enough after 16 strokes I groaned as I felt my peepee throb and begin to spurt out my milk. I reached for my teacup but realized I'd left it in the kitchen. Seeing the look on my face Miss Bella softly told me not to worry, just concentrate on getting all my milk out for her. She wanted me drained and limp like a proper boy.

I sat there in my well drained have and saw that my milk was all over Miss Bella's hand. It seemed in slow motion to me as she brought it up to my face and slid one of her milk coated fingers between my lips and into my mouth.

"That's is Sweetie, relax and let Miss Bella feed you're your warm fresh milky treat. Good Boy, lick and suck it all off and then you can do the other fingers... Just like that, doesn't it taste so much better this way?"

As usual, she was right.

Blog entry - 5/30

Miss Bella has changed my life for the better. Being regularly milked has helped me keep focused and well-mannered. I'm crushing it at work and have started working out again, and just seem to have more energy and be in a better mood overall.

She did have upsetting news this morning though. After my morning milking as she was fondling my limp peepee she told me she had to go away on business for 2 or 3 days so I'd have to go without being drained during that time. She reminded me that I'd promised only she could milk me, so milking myself was out of the question. She said she knew I was a good boy but felt that she needed some extra insurance that I wouldn't give in to temptation, and took a small metal chastity cage out of a drawer and showed it to me.

She could see I was nervous but assured me it was just for when she was away, that she loved seeing my bald little peepee too much to hide it away in a cage. She said she'd milk me the morning she was leaving and then help me put it on. It always makes me calm and relaxed while she rubs my soft tiny peepee, so I felt better about it.

Blog entry - 6/1

Miss Bella's only been gone a day but my need to be milked is so strong. It's a good thing she caged me. I wasn't as bad as I thought, she milked me the morning she left and then put my soft little peepee into the tiny metal cage, I think she said it's a "nub" model. Hopefully she'll be back tomorrow night with the key.

She said she's going to miss my sweet little member. She even took a picture of it on her phone to look at while she's gone.

She did call today to tell me she knows how difficult it must be, but she knows I can keep on being a nice good boy for her. She even had a surprise for me. She sent me a link to a video she posted on a porn site just for me. She said it would help me keep my composure.

I already watched it twice today. I don't know where she found so many clips of tiny peepees, some even smaller than mine. She said I must miss seeing my own hairless one, so I could watch these. Some of them were even dribbling out milk, which I must admit had me licking my lips. She also added an audio track of her whispering some of the phrases she softly says to me during my milkings.

"You're my good little boy who just spurts it all out for me so he stays well-behaved..."

"You're so cute how you just sit there while I milk you. I'm so happy you realize now this is the best way to keep you well-behaved for me. You never need to touch it ever again, do you Sweetie? Now come on, do another big spurt for me..."

"I'm so glad you understand Sweetie. I know all your little guy friends have girls who suck their cocks and do dirty things for them, but I don't want you to be like those boys anyway. It's much better just to drain it all out of you every day, don't you think? You'll see baby..."

" That's it Sweetie, just let it all flow out. You know this isn't to make you feel good, don't you, it's just to help you stay well-behaved for me. You do understand, don't you baby? That's a good boy..."             

"There you go. Pump it all out. You're much better once your balls are empty, aren't you? You love this, you need it. And you squirt so fast now, just 7 strokes..."

"Look how hard you are Sweetie. This is what you really need, isn't it. I know it's hard to admit at first, but you just want Miss Bella to control it and get all the stuff out for you don't you. That way you'll stay a very good boy won't you, and you won't think about pussies or start playing with yourself like a naughty boy. Do you want me to do this for you every day, Sweetie? Tell me."

She told me I should watch it every time I would normally have a milking scheduled and it would help relax me. I think it's doing the opposite though. My peepee is throbbing in its nub cage, and dripping non-stop. It's not dripping milk, just the clear dew drops that it makes before the milk. I can't resist scooping those up and sucking them off my finger, though they don't taste as good.

I miss seeing my own peepee squirt so much, I can't wait for her to come home and empty me.

Blog entry - 6/3

I was never as happy to see anyone as I was Miss Bella this morning. I waited up last night but she must have gotten in very late. I had trouble getting to sleep, anticipating her return and just lay in bed for a while thinking about peepees squirting and dribbling.

She finally texted me around 9 AM and I practically ran across the hallway, naked and caged. She must have been tired and forgotten to leave her door ajar, so I had a tense minute standing there softly knocking before she let me in and apologized.

She had a cup of her relaxing tea all ready for me, and I could feel my stress slipping away just from being in her presence and sipping it.

"I hope it wasn't too difficult while I was gone Sweetie. I did miss you and your soft little peepee. Oh my, it isn't so soft now, is it? Why it looks like it's trying to break right out of that tiny cage. Hold on dear, let me get the key. I hope I can remember where I put it... "She said with a mischievous smile, before going into the other room.

I must admit I did have a few moments of panic before she returned, flourishing the key

"Here we go, let's get your little cage right off. Oh, someone's glad to see me, standing right up." She chuckled. "I hope it wasn't too much of an ordeal Dear, being all locked up. But tell me the truth now, would you have bene able to stay a good boy while I was gone if you weren't?"

"No Miss Bella. "I admitted as she lightly cupped my balls in her hand. "I wouldn't have been able to resist playing with my peepee while you were gone."

"Such a good hones answer. "She purred, lightly fondling them. "You feel so full Sweetie, why I swear I can feel all that pent-up warm milk churning away in there. Did you finish your tea? I think we may need the cup today, There's so much milk..." She whispered in my ear, moving the cup into position. "Is there something you need to ask me Sweetie?"

"Please milk my tiny peepee Miss Bella, I've missed your control so much, please help me be a good boy..." I moaned almost frantically.

"I know you need this, Sweetie." She said, taking her hand off me and watching my throb and pulse. "Let your smooth tiny peepee enjoy its freedom for another minute. We both know it won't take many strokes today, will it? I know it didn't like being all caged up, even though that helped it stay soft and tiny, its natural state. Don't worry Dear, you'll only be caged when I must go away. Though I should warn you, I may be going to Europe for a few weeks on vacation in a few months. So of course I'd have to lock you up then."

Hearing that was enough to make me groan and start thrusting my hips, desperate for any kind of contact.

"You already admitted you need to be locked up when I'm gone, didn't you? And you do want to stay me well-behaved boy, don't you? You're so close to making milk, aren't you? Now be a good boy and ask to be caged when I go away..."

At this point I would have said anything, almost out of my mind with denial.

"Oh Please! Please Miss Bella! Lock my peepee in a tiny cage when you go away, please."

"Such a good boy. So close now too. "She purred, leaning closer to whisper in my ear. "You need that extra control when I'm not here, I know. Don't fret baby, I'll send you more videos of peepees squirting. And maybe some real cocks too, they squirt so much more milk. And you slid right into that small cage so easily, I think next time I go away I'll find a smaller one. One of those flat ones should do. And who knows, if we keep you in it for a few weeks it may even shrink your peepee a bit. Wouldn't that be just perfect Sweetie, your limp little peepee getting smaller and tinier?"

Hearing that was all it took to send me over the edge. I let out an animalistic groan as my peepee, even with no one touching it, pulsed and begin to squirt out thick milky streams.

"Oh Sweetie!" Miss Bella gasped, her eye lighting up as she caught my spurts in the teacup. "That's my good boy, so sensitive he squirts untouched now! Oh, look at it Sweetie, watch it pump out all that built up milk." She cooed, dipping a finger into the rapidly growing puddle and sliding it into my waiting mouth so I could finally taste my milk. 'Poor little peepee, so much to pump out. It wants all the milk drained, so it can be small and soft again, just like it belongs."

I must have kept squirting and then dribbling for at least a minute or two. It was hard to keep track to time, I was in a dreamlike state, almost floating, watching myself dribble and deflate, sucking the gobs of milk off Miss Bella's fingers before she brought the cup up to my lips for me to drain.

Blog entry - 6/7

It's nice to be settled back into my regular routine with Miss Bella. She was right (as always) about how sensitive I've become and how I squirt so fast now. My morning milking usually ends with me spurting out my milk without even being touched while she whispers in my ear. This drains me but leaves me craving my next milking more.

She keeps sending me links to videos to watch too, which of course I do. She says it's the only porn I need now. Between my small peepee and how fast I squirt I'm past the point where I could ever satisfy a woman, so there's no sense looking at naked females anymore. I don't even want to; I just want to hear her voice and look at tiny peepees squirting. She even filmed mine a few times and added them in, which always makes me tingle to see.

She's added quite a few shots of big cocks too, just to remind me of how small I am. I must admit being jealous of how much thick white milk they pump out compared to my squirts. Now and then a clip of a peepee in a flat cage is in there too, one was even dribbling out milk while caged! She hasn't mentioned taking any more trips of locking me up again, but those scenes do keep me thing about it.

Blog entry - 6/12

There's going to be another disruption of my schedule this week. Miss Bella is having her kitchen remodeled, so there's be a contractor there during the day. He'll be arriving early and working all day, so I may be cut back to one evening milking. I hope it's not for long, but she thinks it could be 4 days or more as it involves plumbing and electrical work.

I hope it doesn't take too long!

Blog entry - 6/14

I'm not even sure where to begin, it was so unreal.

Last night Miss Bella managed to milk me around 8PM. She told me Dave (The Contractor, I'd seen him in the hallway) was working long days to try and get the remodel done in one week. It only took 5 strokes before I started spurting milk though, and I felt so good when she told me how proud she was of me as I nursed on her milky fingers.

But tonight, everything changed.

She texted me to come over for milking around 7 PM, and I eagerly raced across the hallway and into her place. I certainly didn't expect to see the sight that greeted me. Miss Bella was sitting on the sofa smiling at me, while milking Dave! He was sitting next to her on the sofa with his pants down around his ankles and his eyes closed while she was slowly pumping his cock. I was unsure what to do, but she smiled and beckoned me over.

"There's my best boy, coming over for his milking. Oh, don't worry, Sweetie, I told Dave all about you. I thought he deserved a milking for the good work he's been doing, but explained to him how important it is to keep you well-behaved and soft and he doesn't mind. Come have a seat next to me and I can milk you with my other hand, we know it won't take very long."

I sheepishly sat on her other side on the sofa. I was so mortified to be naked in front of another man, but I also desperately need to be milked due to the reduced schedule. Dave glanced my way, smiled, and nodded at me, then closed his eyes and resumed enjoying Miss Bella's expert touch.

"Oh my Sweetie." She said chuckling, "It looks like your tiny peepee is shy all of a sudden. I swear it was stiff when you came in but now it's all soft and tiny, like it's trying to hide. Why don't you go ahead and ask nicely and I will fix that."

"P-please Miss Bella, will you milk my tiny peepee?" I could feel my whole-body blushing as I whispered.

"A little louder please Sweetie, I don't think Dave could quite hear you." She said, lightly rubbing my balls with her pinky finger while continuing to stroke Dave with her other hand.

"Please Miss Bella, milk my tiny smooth peepee." I said louder, and noticed Dave smirk a little.

"That's better dear." She cooed, rubbing the tip gently, coaxing it to life. "Oh look, now it's waking up! I think it must have been intimidated by Dave's big cock, don't you Sweetie? Look at it, why it must be twice the size of yours and much thicker. He's starting to drip now Sweetie, go ahead and look and tell him about your little endowment"

Dave's cock was almost 8" and thick, Miss Bellas was right as always.

"I have a smooth tiny peepee that needs constant milkings to keep it soft and small, to help me be a good boy." I groaned as she began milking me in earnest.

"Good boy. And look how stiff you are now. I think looking at Dave's big cock made your peepee nice and hard. Now let's see if you can squirt for us in under 5 strokes today. Look at Dave's cock while I stroke and count Dear 1.... 2... 3... "

That was all it took to send me over the edge, as it had been almost 24 hours since my last milking but I was accustomed to at least 3 a day. I groaned as I spurted out into Miss Bella's hand. To her credit she caught all my milk while continuing to stroke Dave, faster and faster, until he groaned "I'm close Bella..."

"Just a minute Dear." She said to him, "I need to feed Sweetie his milk, he craves it you know." She said sweetly sliding her fingers into my mouth to suck clean. "There we go, all done. Now Dear, sit there and rub your soft little peepee while I finish Dave. Let's watch and see how much that big cock of his spurts out."

I complied, and sat there rubbing myself in my post-milking haze. It wasn't more than a minute later when Dave groaned loudly and began pumping out thick white streams, his volume putting mine to shame.

"Enjoy your reward for your work today, Dave, I hope you perform as well tomorrow." Miss Bella said, having managed to catch all his milky discharge in a tissue. I was disheartened to hear he'd be back tomorrow, meaning I was still on a schedule of just one milking a day.

Dave began pulling up his pants, but what Miss Bella did next was completely unexpected. She scooped up a big white glob from the tissue with her finger and pressed it to my lips.

"Here Sweetie. His milk is still nice and warm and fresh, why don't you try it?" She asked sweetly, as I reflexively opened my mouth and let her finger slide inside with a thick coating of another man's milk on it. I found myself licking and sucking just from habit.

"That's it, that's a good boy. Doesn't his milk taste good, different from yours?" She asked sweetly, feeding me another drop. "it's alright to wonder what another man's milk tastes like, it's nothing to be embarrassed about, it's only natural." She added, continuing to feed me with one hand while fondling my soft peepee with her other.

I didn't even notice when Dave left.

Miss Bella had me stay at her place for a while longer. Over a cup of tea, she continued to reassure me that there's nothing wrong with sampling milk from other sources, so I did go home with my mind more at ease.

Burt also wondering what was going to happen tomorrow.

Blog entry - 6/15

Today was a repeat of yesterday, but with one big difference at the end.

Miss Bella texted me to come over around 7:30 for a milking, but gave me advance notice that she'd be milking Dave also.

I walked into to the same scene as yesterday, Miss Bella sitting in the middle of the couch stroking Dave, sitting on her right. She gestured for me to sit on the other side of her.

"There's my good boy, so eager to be milked like Dave here. And look, your peepee isn't shy anymore, it's nice and stiff. Of course it looks extra small today, all bare and smooth, in comparison to Dave's big cock. Come sit down Dear, and I'll give you your 3 strokes 1... Make sure to watch yourself spurt., I know you enjoy that. 2... Why you even enjoyed watching Dave spurt yesterday, didn't you... and 3! Good boy, that's it, pump it all out for me. So nice and fast now. You're coming along nicely Sweetie. Once you're back to your proper soft state I bet you'd like to see Dave spurt again, wouldn't you? Don't be shy." She said huskily, as I cleaned the last of my milk off her fingers with my eager mouth. "A polite boy would ask him though, and you are my soft polite boy, aren't you? Go ahead and ask him."

I felt like I was turning beet read as I obeyed and stammered out "Dave, may I please watch you spurt?" as Miss Bella beamed at me with pride.

He just grunted "Uh-huh" and nodded his head as Miss Bella sped up her stroking. Then Miss Bella's phone sitting on the table rang.

"Oh Dear," she said. "I was expecting an important work call, I'm afraid I'll have to take this." Unhanding Dave's stiff cock and picking up her phone. "Just a minute please." She said to the caller, and then pressed the mute button, turning her gaze upon me.

"Sweetie, this will take a while and Dave must go soon so I need you to be a very good boy and help me. Dave has to go in a few minutes but we can't leave him in this state. Just wrap your hand around his big cock and finish his milking, would you? You've seen me milk you enough times, I'm sure you know what to do."

"Miss Bella I... I.." I stammered, surprised by her request.

"I don't have time to argue, I have to get on this call." She said with a flash of annoyance. "Dave, slide over next to him. After all the milkings I've given you Dear, I hope you can do this little thing for me." She said, grabbing my arm by the wrist and guiding my hand into Dave's lap. Almost of its own volition it wrapped itself around his stiff, already lubed cock and began stroking, just as I'd seen Miss Bella stroke me so many times.

"That's a good boy. My little helper, my little milkmaid." Miss Bella said with a smile, before stepping into the other room to resume her call. Far enough away that we could hardly hear her, but still in a position where she could watch us.

If felt so strange to be stroking another man's cock, I couldn't help but stare at it. I must have been doing a good job because I noticed he was beginning to leak clear dew drops. I almost felt like I was watching one of the cocks in the videos Miss Bella had me view. Even though I'd just been milked myself I felt all warm and tingly in my soft little peepee.

I was so focused on the sensations I hadn't noticed Miss Bella return; her call must have finished faster than she'd anticipated. Instead of resuming her spot on the sofa though, she walked behind it so she could lean forward and whisper into my ear.

"That's it... nice steady strokes... you're doing so well Sweetie, such a good little milkmaid helping me like this... now cup his balls with your other hand... that's where all the warm milk is..." I wasn't watching it but I swear the head of my peepee pulsed hearing that and managed to dribble out a drop of milk.

"He's getting close... see his hips moving now, feel him throbbing... go ahead, make him spurt like a good milkmaid... drain him..."

With that Dave moaned loudly and began pumping out his thick milk all over my hand as Miss Bella continued whispering to me.

"That's it, milk him dry Dear. Make sure you empty him all out like a proper milkmaid, like Miss Bella does to you. Catch it all in your hand just like I do, that's my milkmaid... good... good... feel how thick and warm it is?"

My whole body was throbbing as the last drop dripped out of him. I felt it hard to even think as Miss Bella reached down and guided my hand, coated with his milk, up to my mouth. "Now here's your reward for being a good milkmaid, nice warm fresh milk." She purred, guiding my unresisting fingers into my mouth to lick and suck clean. I closed my eyes savoring the taste and basking in Miss Bella's praise.

"You did such a good job Sweetie; I think you were born to be my milkmaid." She said chuckling as she fingered my limp, tingling peepee. "I think you enjoyed his milk, didn't you? Too bad tomorrow is his last day. Maybe we can get you one more taste before he leaves, you'd like that, wouldn't you?"

I felt like I was floating and all I could do was mutter "uh-huh" and nod my head. She is always right after all.

Blog entry - 6/16

I was on pins and needles all day today. Would Dave be at Miss Bellas when she summoned me? Would there be a repeat of yesterday? Did I want a repeat of yesterday? My head was spinning. I'm not gay, or even bi, yet yesterday I had stroked another man's big cock until he spurted, then tasted his milk! Part of me was mortified, but another part had... enjoyed it? My peepee kept plumping up every time I thought about it.

Luckily Miss Bella was thinking of my well-being, as always. She texted me that she knew I probably had mixed feelings about yesterday. She said there was nothing to be ashamed of. That Dave had told her that morning that he couldn't remember the last time he squirted as hard as when I milked him. She said that made her proud of me, that I was such a good little milkmaid for her. Reading that did put my mind at ease.

Miss Bella suggested a long hot shower would help me unwind. She reminded me to use the hair removal cream, but suggested that I use it all over my body from now on. Milkmaids are always smooth and hairless from the neck down. It felt odd afterwards, seeing myself hairless in the mirror, I think it made my peepee seem even tinier. My peepee must have liked it, as it plumped up at the sight of my new look.

She had given me a container of her special tea and suggested I have a cup or two while working, that it would help me relax. She also suggested after the tea I watch some of the videos she had sent me. She said that watching peepees and big cocks spurting always helps a milkmaid relax. As always, her advice was sound and after some tea I felt much better, watching her latest video. This one seemed to have more big cocks than small peepees in it, but they were all gushing out thick delicious milk. I found myself recalling how Daves had tasted, and wondering what some of the milk in the video would taste like.

I managed to focus on work for the rest of the day, until around 3 PM when Miss Bella texted me that Dave was finished and would be leaving in about 10 minutes, but he had asked if her milkmaid could come over and say goodbye. I felt a quick flash of panic, but realized my peepee was rock hard and even had a dew drop on the tip at the thought. I quickly stripped like a good boy and headed across the hall.

I entered her apartment to find her and Dave on the sofa again, but this time at opposite ends with a space in the middle. I was also surprised (and a little disappointed) to see Dave didn't have his cock out.

"There's our little milkmaid, come in and sit down Sweetie. Oh and look at him, all smooth and hairless!" Miss Bella said, patting the spot between them. Look how excited you are, why that tiny thing looks ready to squirt right now!" She chuckled. "Don't fret Dear, we'll get you all drained and small again soon enough."

"Hi milkmaid." Said Dave, grinning, "I'm glad you came to say goodbye, you did such a good job on me yesterday. You have a real knack for making cocks squirt, did you know that?"

"Umm No, I didn't know that. Um, thanks," I stammered, blushing.

"I have exciting news." Said Miss Bella sweetly. "Since it's his last day, and he did such an outstanding job, I promised Dave a special goodbye milking. I even gave him a choice as to who would milk him, me, or you... and guess who he picked? You Sweetie!"

I was floored, and just sat there with my mouth open.

"I know you enjoyed playing with his big man-cock yesterday, Sweetie, and I thought I heard you make a yummy sound when I fed you his milk. I know you want to be a good boy, a good milkmaid for me, don't you?"

"Y-yes Miss Bella, I want to be your good boy."

"I know you do Sweetie. And you want to be a good milkmaid for Miss Bella, don't you? And milk a big hard cock?" She said softly, as Dave stood up and started taking off his pants. "Go ahead, I know you want to say it."

"I want to be a good milkmaid and milk a big hard cock, Miss Bella."

"Good boy, so well behaved now. And look Dear, right next to you, it's a big hard cock just waiting for a smooth sweet little milkmaid. You can't take your eyes off it, can't you? Your own tiny peepee is stiff and quivering at the thought." She leaned in and softly whispered. "Go ahead and ask me Dear, good milkmaids always ask permission...'

She was right, I couldn't tear my eyes away from Dave's cock. Even only half erect it was bigger than mine.

"Please Miss Bella, may I milk the big cock for you?"

"Of course, dear, it's what you were made for. But this time let's do it like a proper milkmaid." She said, taking me by the hand and leading me over in front of him. "Look at it Sweetie, get nice and close." She whispered, gently pushing down on my knees. "Can you smell it? Can you see it's getting harder just from having you near it?" She asked, my face just inches away now.

"It's time you became a milkmaid for real Sweetie. We all know you want this, to drink the milk right from the source. To suck it out right from the big hard spigot in front of you." She said, gently pushing my head forward until my lips grazed the tip of the cock before me, and then it slid into my warm welcoming mouth.

I'm not even sure how long it took, I was in a daze between the cock in my mouth and Miss Bella whispering praise and instructions in my ear and toying with my limp peepee with one finger.

"Good boy, just like that. Mind your teeth now, that's right..."

"Lick and suck, that's how milkmaids do it Sweetie, use that clever tongue of yours on him..."

"Back and forth dear, move your head back and forth while you lick and suck..."

"Hear him moan? Feel his head swell? He's getting there... remember, men don't squirt as fast as you do so be patient..."

"Now use your hand to stroke while you lick his balls... that's good. Remember, that's where his milk is. Can you feel it churning around? Good boy, now suck on them.... Warm that milk up..."

"Good job, now quickly put his cock back in your mouth... he's close, I can tell. I have to warn you Sweetie, once he spurts, once you drink the milk right from the source you'll be addicted. There'll be no going back, you'll be a milkmaid from now on. You'll see how much better the milk tastes this way. You'll crave the sensation; your mouth will become a milk hole for cocks..."

By now I was out of my mind with the need for his milk. I sucked and licked as hard as I could, and was rewarded with him crying out as I felt the first jet of warm milk shoot out into me. I gave a cry of pleasure myself, as best I could with my mouth full. Miss Bella, ever helpful, held my head firmly on him from behind to make sure no milk leaked out.

I was back in that dream-like euphoric state from the taste and sensation. I'm not sure how much time went by before Miss Bella gently tapped me on the head and said "Sweetie, time to stop sucking now and let go of him. I think you drained him quite dry a few minutes ago and by now he's nice and clean."

Dreamily I let his now deflated cock slip from my mouth. He looked down at me smiling contentedly and said "Good job milkmaid, I feel completely drained."

"And look Sweetie" added Miss Bella, pointing down between my legs. I saw my peepee, all smooth and soft, and a teacup below it containing my little spurt of milk. "You were so happy and excited to become a real milkmaid, your peepee squirted all on its own while you were busy milking Dave." She added, bringing the cup up my lips.

As I drank down my own milk, I realized she was right as always. My own milk tasted good, but it didn't compare to getting if fresh from a long thick fleshy spigot in my mouth, my milk hole.

Dave said his goodbyes shortly after while I stayed and had some tea with Miss Bella while she fondled my soft peepee and ran her hands over mu now smooth body. Miss Bella explained that she knew that I was now a milkmaid, and would crave sucking it fresh from the source. She said she had a sense of responsibility towards me and would do her best to make sure I had a constant supply. She had a lot of male clients that stopped by on occasion, and she was sure most of them would be glad to help feed her hungry little milkmaid.

She was right again.

Blog entry - 7/1

It's been a while since my last update but it's been so busy between work and my milkings... and my duties as Miss Bellas Milkmaid.

It was just a few days after that fateful encounter with Dave that I began to feel the urge for fresh milk again. I think Miss Bella realized it and told me she had a male client coming over that afternoon, who probably wouldn't object to meeting a hungry little milkmaid.

She had me come over to her place a few minutes before he arrived, and milked me. It just took 2 strokes this time. She had me squirt into a cup of tea and drink it all down to help me relax. The milky tea certainly did that. This would become part of my pre-milkmaid ritual.

When there was a knock on the door, she told me to get down on my knees in front of the sofa, and to make sure my legs were spread so her guest could see how smooth, soft and small my peepee was. That way he'd know I was a hungry little milkmaid who wanted nothing better but to empty his balls. She also told me not to speak unless spoken to, as some men would prefer it that way.

I could hear them whispering before she led him into the living room. I felt more relaxed when I saw him smile when he saw me. He sat down in front of me, undid his pants and took out his cock, long and already hard.

"Get to work milkmaid." He said, with an amused look on his face.

I didn't need any more coaxing to lean in and start licking and sucking on his full balls, to warm up the milk inside. As before, Miss Bella positioned herself behind me to whisper praise and helpful directions in my ear.

"That's a good milkmaid, first the balls, then nurse on the tip."

"Don't forget to use your tongue and mind your teeth, Sweetie."

"You're doing so good. Remember, real men don't spurt in 2 strokes like you, you need to work on that cock for at least ten minutes."

"Oh Dear, did you just make a 'Mmmm' sound. Oh, you are a natural little milkmaid."

"That's it, suck and lick. And move your hips a little, I want to see that soft little peepee dangling and swinging."

"He told me he hasn't spurted in 2 weeks; just think of all the milk you'll be swallowing soon. Oh, that made your peepee try and plump up, didn't it?"

"My Little Milkmaid needs this all the time, don't you? Oh, I heard you go 'uh-huh', keep it up Dear, he's getting closer. Can you feel him throbbing, can you taste his little dew drops? Don't' worry, keep being a good milkmaid for me and Miss Bella will make sure you get a steady supply of fresh milk all the time."'

"That's it... that's it... here he goes... here comes your reward... get ready to drink it all down. Yes. Yes. Good Milkmaid. Swallow. Every drop."

It was just like the last time, the sensation of him shooting streams of milk into me overwhelmed me and put me into a blissful, almost trace like state. Miss Bella had to remind me again to stop nursing on him.

True to her work, in the days that followed Miss Bella made sure I had a steady supply of fresh milk from her male clients. Sometimes even 2 or 3 a day!

She's still helping me be a good boy, and a good milkmaid. She had a few suggestions that she said would make the men I milk more relaxed, which would make then squirt more milk into my milk-hole, which is what she calls my hungry little mouth now.

She had me start wearing a little bit of lipstick, she explained men like seeing bright red lips wrapped around their cocks, which makes perfect sense. She added just a touch of eye makeup too, so when I look up at them, I look sexier. She had another great idea, and ordered a blonde wig with pigtails so I'd look like the maid on those German Beer Labels. She said that would make the men squirt extra hard, and I know better than to doubt her.

She's going on vacation soon and I'll be caged again, this time in the flat cage so I won't look like I even have a peepee. She's so considerate though, she's going to arrange lots of milk dates with her clients while she's gone to keep my craving sated. She may be gone 2 or 3 weeks and is hoping all that time in the flat cage might make my cute peepee even smaller.

She still milks me regularly too, to keep me soft and tiny. I'm so sensitive now I rarely last more than2 strokes, and most of the time I start dribbling milk before my peepee even gets completely hard. That's Ok though, as Miss Bella explained, I really don't need erections anymore.

I'm her good well-behaved soft boy now, and all good boys need is their milk.

Milkmaids too.

(Authors Note: I hope you enjoyed this story. I always wanted to write a first-person journal type story. I was inspired by 2 of my favorite tales here, My Wife the Wet Nurse by ppeaks42 and Bedtwetter by Satanicsissybitch. Miss Bella is named after a character in a story by The Incomparable Camenica Diaz, if you've never read her stuff, it's great. And a final shout out to Princessa NS, who helped me experience so many new wonderful things).