Milk Maid: The Beginning

"I don't understand. You told me the surgeon got all of the cancer and that I was basically cured." I said staring at the disgusting diaper the nurse was holding. No way in hell I was wearing that.

"Calm down. I know this is gonna be hard for you to hear but you need to listen to me. One, the surgeon did in fact get all of the cancer and you are cured... as far as the cancer goes. However as we discussed with you many times both before and since the operation, there was always the possibility of lingering damage and I'm afraid that's what we have here." The nurse tried to explain but I was overly distracted by the thought of wearing that disgustingly huge diaper and her awesome titties.

"So what are you saying, I'm gonna be a bedwetter from now on? And what about the pain in my chest?" I asked still transfixed on the huge diaper the nurse wanted to put on me.

"There was some damage to both the hypothalamus and pituitary glands and while it's entirely possible that your bedwetting problem is temporary, you will have to wear an absorbent brief. At least for a while. Now, as for the pain in your chest, that is a bit more complicated. You see the damage to your pituitary is causing an elevation of the hormones prolactin and oxytocin. These are usually present in nursing women. The pain will begin to subside a little as soon as the breasts have had enough time to expand to accommodate the excess milk production. Your probably a full A cup or bigger now but your gonna get bigger." She explained.

"Milk production... milk production? I'm a guy not a woman. I'm not producing any goddamn milk." I Stated knowing full well that what I stated meant nothing.

Fuck. What the hell?

"Look, I already lost damn near a whole year to this cancer thing and I'm planning to attend college in four months. I can't wear a diaper or produce milk. I just can't." I said and was overwhelmed, I actually tried to hold back tears but to no avail. I hadn't cried real tears since I broke my leg eight years ago when I was eleven.

Men do not cry.

"Now don't worry. That's just another sign of the hormones. You may be a bit moody or emotional until your body begins to adjust. There are medications we can prescribe but not till after we get your blood work back to let us know where to begin. For now you need to be wearing this to prevent further embarrassments. After I've gotten you diapered, I can get you an orthopedic device to help with the pain in your chest. Now up on the table." She said patting the exam table like I was a kid or something.

This can't be happening, I'm nineteen years old, I dont need a diaper. I'm a man and men don't produce milk. MEN DO NOT CRY... EVER.

As I got up onto the table to let a hot nurse put me in a diaper, I kept thinking about how I was going to explain this to my mom seated just out in the waiting room. I was humiliated beyond belief but weather I was mortified by the fact that I was being diapered or by the fact that the hot nurse was staring right at my dick which was undersized due to the cancer, I wasn't sure. Probably both.

I sobbed a little and was humiliated even further by my tears making everything worse.

The diaper was absolutely horrid. It was thick beyond belief and made a disgusting crinkling sound anytime I moved even slightly.

I pulled on my pants and was further humiliated when I realized that not only did the diaper extend up my waist far enough to be clearly visible above my pants by a couple inches, but also the bulk was plainly clear to see for anyone who looked.

"Now wait here and I'll be back with something for the chest pain." The nurse said. while I waited, I put on my shirt and realized it was too short to tuck in or hide my diaper in anyway. I realized I was gonna have to suffer with it till I got home and found better clothes to wear.

"All right, here we go now. This is for younger girls but it should provide some support as your breast grow in response to the elevated hormones in your bloodstream." She said holding up a bra... A real goddamn bra.

"I can't wear that. It's a... I mean it's a girl's bra for christ sake." I stammered.

"You are in the middle of growing breasts due to gynecomastia and if you do not have support, they will begin to hurt more and more. Especially as they begin to produce milk. This is really for your own good." She explained holding up the ridiculous thing.

By this time I was ready to give up completely and so I allowed her to take off my shirt and put the bra on me. I don't think I actually heard one word of her explanation about how to put it on and take it off.

She then left me alone to sob a little as I put my shirt back on. The nurses station had a huge bag of diapers waiting for me and four extra bras as well.

"These will do for the immediate future but you will need to buy more as soon as possible. As for the bra, you will need to buy another bra with a larger cup size as your breasts develop. We should have your test results back in a couple weeks so I scheduled another appointment for two weeks from today." The nurse said and handed me the usual stack of paperwork and I headed back into the waiting room where my mom waited for me.

The drive home was humiliating even though mom didn't say anything. She read through the paperwork and cast a quick glance first at my diaper bulge and after some more reading, at my chest area.

Fuck me, what was I gonna do now? Beating the cancer was the best day of my life, this was the second worse just behind the day I found out I had cancer.

I had no idea what to do when I got home so I tossed my bag of diapers in the corner of my room. It's not like I had any friends to come over and see them anyway. I then dumped the four extra bras in my sock drawer.

I then went into the bathroom to see if the doctor had been right and my breast had developed a little. Being a skinny kid I never really looked at myself in the mirror much, not to mention I had a fairly poor self image. Much to my surprise, I had real lady breasts. They were small maybe an "A" cup and I would probably never have noticed them if I hadn't gone to see the doctor but they were there. And sensitive to the touch. I gingerly squeezed one nipple and sure enough some liquid came out.

It's bad enough the cancer gave me a small dick but titties too. And diapers to add to the mess.

I went through my clothes trying to select the best clothes to hide both a thick diaper and a bra. I was a real skinny dude and most of my clothes consisted of blue jeans and T shirts however I did find a couple pair of pants baggy enough to hide my diaper and a few flannel shirts that should conceal any telltale signs of a bra. I had to admit that wearing it made my nipples chafe a lot less.

Baggy pants and flannel shirts... in southern California. Fuck it's gonna get hot.

I was about to get online and lookup some info on my condition when mom yelled upstairs, "Riley, your phone is ringing."

Fuck, I forgot to bring it up with me. Not really surprising since I did most of my online stuff on my desktop in my room and I had no real social life to keep my phone busy anyway.

I ran downstairs cursing the thick diaper that was hugging my ass as I did and grabbed my phone. It had stopped ringing by the time I got to it but soon rang again. It was the doctor's office.

"Hello." I answered.

"Is this Riley Kinkaid?" The voice asked.

After answering and providing the last four of my social security number to confirm my identity she said, "I'm sorry, we were supposed to provide you with some nursing pads for you to wear in your bra to help with unwanted discharge. You can pick them up anytime."

Great, more bad news.

As I started to go back up to my room mom stopped me and said, "Riley, you don't have to hide from me you know. I'm your mother. This is nothing to be embarrassed about." And she pulled gently on my flannel shirt and added, "It's gonna get pretty uncomfortable if you wear this all summer."

"Yeah, I know. I was just looking for less revealing clothes, you know, for when I go out. I don't want people to see is all." I answered. I knew mom was genuinely worried. She had sat with me in the hospital and I never doubted her but still, I had no desire to be seen diapered and in a bra by her.

I got back to my room and because mom was right, the flannel shirt was oppressively hot and uncomfortable for SoCal, I decided to take it off. I then sat at my computer and began searching for medical info related to my condition.

Everytime I thought I had a line on some info that might help I ended up getting linked over to a porn site. It was an eye opener. I had watched a lot of porn growing up, hell, other than school work it was the number one reason I had a computer in my room the first place.

I always watched the pretty girls but when I typed in my condition I got linked to some really weird shit. Dudes in diapers playing with themselves, guys proud of their so called micro penisis, crossdressers and most intriguingly, dudes with tits playing nursemaid to both other guys and women. I swear there were videos of men with huge titties letting other men and women suck the milk right out of them.

It was some pretty weird shit and it made my dicky hard as a rock.

I don't know why I did it but I reached down inside my jeans and started to rub my diaper just like the queers in the videos and way sooner than I had expected, I shot a small load of cum into my diaper.

I kept looking at the porn going from one site to the next but one caught my eye. It said there were men willing to pay top dollar to suck the milk out of titties.

I thought about it and figured that if I were rich, maybe sucking on some milk rich tits might not be entirely out of the question. The site where that info was posted had a chat room and so I logged it to see what was going on.

There were men making offers to women for a little nursing fun and the money they discussed was in the hundreds and one was offering a full thousand. It seemed that anything kinky was on the menu on this site.

Not actually planning to do anything, I posted my actual situation just to see if anyone really wanted to nurse on a boys titties.

I had no idea what I was doing.

I got more than a few private messages. Some wanted to fuck me and some called me jailbait and others expressed their disgust while others just wanted to talk dirty online.

But one seemed nice... ish. He claimed to be a man who was interested in a boy with feminine features, particularly breasts. He also seemed to have quite an interest in my diapers. I don't know why I kept chatting with him but something about chatting anonymously appealed to me so I continued.

After about an hour he asked if I would show him my tits and perhaps my diaper on cam. I had long since learned how to do cam privately for online porn, mostly with girls so I agreed. I turned on my webcam and he appeared on my screen. He was about thirty or so and seemed well built and could probably get a date with any girl.

I slowly took off my flannel shirt exposing my bra clad breasts and he noted that there was a wet spot on both cups.

"Take off your pants and show me your diaper girl." He asked calling me a girl.

I took off my shoes and socks then pulled my pants down and stepped out of them leaving me in nothing but a bra and a diaper for his amusement.

"Damn, the cancer did a number on you kid, you look like a real girl. Hips too. Everything. Ever fantasize about being with a man?" He asked.

The doctors had said that my body had been producing an excess of female hormones for quite a while but up until the man on my computer made that comment, I didn't realize just how feminine my body was and when I looked in the mirror, I was shocked at what a new perspective revealed.

We chatted for a good hour with me in just a bra and diaper before he offered me five hundred dollars to let him nurse on my titties. He said if we did anything else he would pay more but I told him I was only interested in titty play.

I wasn't really interested in titty play when the conversation had begun but somehow I had been talked into it. And it was five hundred dollars if it wasn't all just some bullshit.

He asked me if I wanted to meet tonight. I thought for a minute. It's not like I had a curfew or anything but I had no car and told him so. He offered to pick me up so I offered a location not too close to my house and agreed. He said he would take me to his house and bring me home afterwards. He also asked me not to wear the flannel shirt but something where the bra was visible.

I won't try to explain how I felt because I have absolutely no idea. I was curious and five hundred bucks was a lot of money to me.

I quickly donned my baggy jeans and grabbed my second choice for a shirt. A button down blue shirt I had worn a couple years ago to have my highschool yearbook photo taken in for graduation. The bra was visible but only if you cared to look. I also grabbed my old school backpack to carry some extra diapers.

I yelled back to my mom as I headed out that I would be back later and walked to the meeting place which was a strip mall about ten blocks from my house where I used to hang out when I was still in school and I waited. Soon his Bentley showed up.

I was suspicious when he said he drove a Bentley but here it was.

"I wasn't sure you'd come. Most don't actually show up. Can I get you something before we go, A soda maybe?'' He asked.

"Um, no, I'm good." I said way to nervously and he held open his car door for me and closed it when I had gotten in. He got in the other side and we drove off.

"How did it feel to have a man hold the door open for you?" He asked out of the blue.

"I didn't really think about it." I lied. It had felt weird.

"A man always holds the door for a lady. You don't mind me calling you a lady do you?" He asked further.

"It's kinda weird and all. No offense." I said knowing how naive I must have seemed to him.

We made small talk till we arrived at his house in Malibu. An oceanfront home. I guess he was really rich.

He escorted me from the car and into the house again treating me like a lady by holding the door open for me. He wasted no time in taking me up to his bedroom. A room by the way that faced the ocean.

"Go ahead now, show me." He said and since it was what we were here for, I kicked off my shoes and socks, pulled down my pants and then unbuttoned my shirt and removed it leaving my clothes in a pile on the floor next to my backpack as I stood before him clad in just a diaper and a bra neither of which I had ever worn before this very day.

"So, five hundred then to nurse on you? Unless you're interested in making more?" He said suggestively.

"I dunno, what would I have to do?" I asked hesitantly.

"If you wear a dress for me I will throw in an extra five hundred plus if we have sex, I would give you a grand for oral and another grand for anal." He offered.

"I aint never done that before." I said truthfully but not saying no and I cursed myself inwardly for such a noncommittal answer.

"I'll tell you what, I'll go find a dress and then we'll just see how it goes. That okay with you. I promise no one will see you." He said trying to reassure me.

"I guess." I said. I wasn't really into wearing a dress but for another five hundred, why not? He returned shortly with a yellow dress with a floral pattern. It wasn't sexy or anything, just a normal ladies sundress.

I allowed him to take off my bra and then help me pull the dress over my head making me officially a crossdresser. My dick got hard as a rock in my diaper. For once I was actually glad I had a tiny dick so he couldn't tell I was hard.

The dress had flaps on each side to allow a woman to breastfeed her babies.

The man sat me on the edge of his bed and opened the nursing flap on my left breast. He got on his knees and put his face at my breast, took my nipple in his mouth and began to gently suck.

Oh fuck that felt good. I was hard and getting harder as if a small dick like mine could get any harder. I accidently let out a moan of pleasure as he nursed on me and he responded by reaching up my dress to fondle my diaper.

I hadn't realized it but my diaper was slightly wet and when he squeezed it I got such a thrill. He knew I was hard and continued to rub me through my wet diaper as he nursed.

Then he used his other hand to pull out his cock and start stroking himself right there as he sucked on my left tit. When my tit was spent, he switched to my right one all the while playing with himself.

For the second time in one day I shot a load of cum into my diaper just as he finished milking my right breast dry. He then stood up and pointed his cock straight at my face. I almost felt obligated at this point but I was also curious so I gently kissed it and began to lick the head of his cock like I had seen countless women do in pornos.

He took my head in his hands and inserted his cock into my mouth and began to literally face fuck me. God I liked it. It was about seven inches and not too fat and felt comfortable in my mouth.

I only sucked for a couple minutes when he said, "I wanna fuck you girl." I responded by leaning back slightly on the bed and opening my legs inviting him to ravish me.

He pushed me up further onto the bed and placed some pillows under my diapered ass. In his strong arms my legs were lifted onto his shoulders. Then came the humiliating crinkling sound of my wet diaper being untaped. His finger was at my virgin ass and quickly inside of me.

One, then two and after some whimpering on my part, a third finger made its way inside of me. I had seen enough girls on porn videos take it up the ass to know what to do so I pushed out as each finger entered me.

Soon, he felt I was ready and pulled out his fingers leaving me with an empty feeling but not for long.

He placed the head of his cock at what was soon to be my pussy and began to press inward. It hurt like I knew it would but I just laid there and took it. He took forever to get balls deep inside me and I had this feeling that he was robbing me of my last shred of manhood.

I cried out a couple times from the pain and he responded in the most tender way by going slower and cooing me like I was a little girl. When he was satisfied that I was ready, he began to fuck me.

In and out, ever so slowly. Like he was a saw and I was the board, He was sawing me in half. I loved it, I was humiliated by it, I wanted more of it, I wanted to run away.

On and on he fucked until at last he tensed up and rammed his cock in me real hard a couple times and then I felt his warm seed enter my body stealing the last vestiges of masculinity I had left.

When he was done, he lay next to me for a good long while basking in the afterglow. When he got up, he grabbed a fresh diaper out of my diaper bag and proceeded to diaper me. He paid me a full three thousand dollars for the nursing, wearing a dress, sucking his cock and letting him fuck me in my ass.

That was more money than I ever had in my hand at one time in my life.

I took off the yellow sundress and he offered to let me keep it so I put it in the backpack with the extra diapers. I then got dressed. Before we got in his car to drive me back into the city, he handed me some weird looking thing.

"I want you to have this. It's called a breast pump. The more you use it the more milk your breasts will make." he said.

I looked at the thing and wondered if I would feel nearly as good using it as when he nursed on me. We got in his car and again he held the door open for me even calling me a lady again. Before I got out of his car when we arrived back at the stripmall where he picked me up, he gave me his number and I gave him mine.