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.