This isn´t as easy as he thought. Matt had the idea that as soon as the right woman came up, it would be obvious who to pick. But it seems, he´s got three women who seem to be about right.

They are nice, attentive, charming. He had to make a really good choice. Because he´ll be this woman´s couple until she decides the opposite.

He´s at his room, one he will soon have to say goodbye to. Right now, he´s two days away from his deadline. The decision he has to make is not easy. Therefore, he decided to write down all of the pros and cons about each woman.

“Ok, let´s see, what do we have so far?” He said as he looked down at three sheets of paper, all with details about all of these women. “Let´s start with… Katy.”

The paper was like this:

KATY

Pros:

A very nice, attentive lady. Pretty, loving, caring.

She´s a Dame who protects men.

Cons:

She´s really maternal.

Probably she also falls on the over-protective side.

Plus, she said she was not so sure how she will manage her time.

He wonder, how could his life be if they became a couple? He was certain she was lovely, a nice couple. But he was afraid she became ultimately bossy in their intimacy. He can tell, by the way she handled things the other day, that she has a very strong character. What if he makes her mad?

She was so lovely, but what if there was a dark side on this gentle soul?

Or, what if the lack of time spent together leads to uncertainty? What if she doubts they are a good couple? What if she leaves him?

Perhaps, the life of a Dame was too busy to have a couple. How many Dames out there have one? He decided to check on another option. Zoey.

Zoey, who has been his best friend ever since he stepped inside that bar, but was that real friendship or was it just her maternal instinct screaming she needed to look after him. It really tells much when a woman is not on the side of his man, looking after him in this very unleveled world.

Did Zoey really liked him or was she just playing the role of his babysitter?

Her page was something like this:

ZOEY

Pros:

Nice, kind, attentive.

Knows a lot about his life, cares for him.

She´s always been there, and she´s always willing to help him.

Cons:

She had this maternal side she´s kept hidden for so long. She even said she was not really one he would want to date.

What type of maternal woman was she? She had clothes, lactating pills and a lot more things on her house.

But if he was fair, all maternal women had those pills at their house. It´s like a starter pack or something.

Both of the past options are women who fall on the maternal side. Something he doesn´t like. Another bad thing about these women was the fact that they often deprive men from their freedom. It´s not like men had much freedom nowadays, but maternal women are often bossy.

However, they are often sweet and tender women. Caring, nurturing, putting their man as a priority. But he cannot picture himself in such relationship.

This all leads to his last, and maybe the best, option. Hannah.

Hannah Scott was a powerful woman. Not like the type of power a Dame has, Hannah was a wealthy woman. The owner of a successful company, pretty, authoritative. She could really be intimidating. However, he knew she had a different side. One not so business-like.

HANNAH

Pros:

Kind, nice.

She´s looking for a couple, a real one. In the prospect of getting married.

She´s offering more than a couple, but a job. A purpose in life. (Even if it was just as her assistant)

He can live a life of luxury.

Cons:

He´s not sure if she will be too demanding.

If she ends up their relationship, goodbye to his job.

Another good thing was that, even if her position and power was utterly intimidating, she was still learning. Hannah was a wise woman, she didn´t made it to the top just because. But that was in business life, in her normal life… she was still figuring that one out.

She had no idea what it was to have a couple. She does have a small idea, but she´s still new to the idea of romance.

This was an open window for him to create a real, lovely and solid relationship with a woman. And that´s why he´s sending her a request right now.

He sent her a request, with a message: “Greetings! I´d love to meet you at your earliest convenience, on a date. I´ll be waiting for your reply.”

He tried to sound sort of professional and confident, but it just felt kind of… forced. So he added a “<3” at the end. But that may be a little weird.

And what if she was working? Or, what if he was not supposed to message her after business hours.

Could she get mad if she feels he´s a little… careless?

He sat on his bed for a moment, wondering if he just messed up. He had something important to tell her, but he wanted it to be in person, not through a message on the app.

However, she replied, and fairly quick.

“Hello, Matt. Hope you´re doing well.” So far, professional.

“I´d love to meet you, but I´ll be out of town for business tomorrow. Maybe we can meet on Sunday? It´s my free day. Would you like that?” At her house, the giantess was hoping he said yes.

Matt was in trouble; Sunday was his last day to look for a couple. If things don´t come up well with Hannah, he won´t have enough time to look for a couple. A week seemed like a lot of time, now, it doesn´t look like much.

“For sure! We can meet up on Sunday. Would you like to meet up early?” he wanted to have, if everything failed, the rest of the day to look for a last-minute couple.

“Early sounds great! I usually wake up a little late on Sundays. Is 8:00 am ok?” There´s no doubt she´s a business woman. “Late” must be after the sun comes out to her.

He knows that if they become a couple, there´s a chance he will struggle a little to adapt to his new lifestyle. But it will be totally worth it.

Now, Matt had another date with Hannah. But not on the schedule he would´ve wanted. This date was two days apart from now.

He was nervous about that, he can´t deny it. His main question right now was, what to do tomorrow? He had nothing planned for tomorrow. That was preoccupying.

What is he supposed to do? Date? Take the day off? Have some rest? He has to think things straight, he´s running out of time. Maybe the most viable option is to take it easy, but not stop doing what he´s supposed to.

He kept thinking on it for a while, and then came with the right idea. It was around midnight when it came to his mind. What about spending a day with the other ladies? Not a full day, of course. Just follow them on their regular routines. Not a date, per se, more like following them on their day-to-day.

Of course, only if they agree. But they will certainly would.

Matt grabbed his phone, unplugged the charger and wrote, to both Zoey and Katy. Who will be the first? Well, whoever replies first.

He wasn´t sure, Zoey worked at her bar until late night hours, she´s most likely to see the message first, but that´s only if she´s not too busy. If she is, then she will reply by the end of her shift.

On the other hand, Katy was most likely asleep by now. She wakes up really early to go to work. Probably she´s been in bed since like two hours ago or so.

He decided to leave this to the odds. Whoever replies first will be his morning date, and whoever does after, will be the later one.

This may seem weird, but it´s more common nowadays. There´s some men who arrange a single date with their best options and then discuss who´ll be the winner. Same thing would happen on the other end, but women are not in a hurry to have a couple, it´s men who fall on that.

He sent the message, to both, and just closed his eyes. Tomorrow was going to be quite a day. He had already been with both women before, but not like this. Maybe this is interesting?

Matt woke up, stretched and yawned as he sat on his bed. Saturday morning, a new day. But he had to remember one thins.

“The message!” He fell asleep before even knowing what was going to happen today. He needed to check.

He soon found out both women had already replied. It made sense, it was 8:00 am already.

The first one to reply was Katy. At 5:00 am? She really wakes up early. And then, about half-an-hour ago, Zoey replied. He had to be fair, Katy replied first, so she´ll be the first one to hear from him.

He thought his message was kind of weird, now that he read it, well rested, he found it a bit strange. For a dating message, of course. He wrote:

“Hi! I would like to meet you, but not on a date, at least not a conventional one. I was thinking and I´d like to see, if we were to be a couple, how would our relationship be? I hope this isn´t weird or anything but, could I spend the day with you at work?” Hoping it wasn´t weird? The message was like asking for a couple-trial. It was weird, but none of them cared, at least not much.

Katy replied:

“For sure! No problem, honey. If you wanna spend the whole day with mommy, I don´t see why not. I´ll pick you up at your unit, just send me the date request and I´ll be there in a sec ;)” That was nice, in fact, he sent the request right then.

After that, he read Zoey´s reply:

“Ok. You wanna be my little helper at the bar? Sure. And don´t worry, I won´t exploit you. Just give me a heads-up before, ok?”

Both women agreed, this was awesome!

The first thing he did, after sending the request to Katy, scheduled at 9:00 am, was to take a shower and get changed. And by 9, sharp. She arrived.

He opened the door, just to meet Katy´s long, sexy legs at his door. She then bent and said: “Good morning, sunshine, ready for our date?”

“Yes! Uhm… wanna come in? I need to put my shoes on.” He was still barefoot.

“Oh, I´d love to, sweetheart, but I´m afraid these little doors you use are not… women-friendly. I can´t fit my boobies through them, and neither will my hips, hehe.” She was right.

Katy was 20´2”, even if she was a giantess of a slim complexion, her dimensions were still humongous when compared to men ones. It was move viable to make a whole on the wall than to get her in. Or he could step outside, that was even more convenient.

The first thing she did when he came out was to pick him up. He hated it, women, for as big as they are, should not carry men. It´s demeaning. But at least he was close to those massive breasts of hers.

“I´m so glad you texted me, honey. But you could´ve just sent the request, you know. I will always make some time for you.” She kissed him, right on his forehead.

Making out would´ve been better, but he knew the type of woman she was. She showed some real affection, but mostly maternal. Which is totally fine. She´s lovely, and sweet.

Her embrace feels so warm as she´s carrying him in her arms. Maybe this makes it easier, right?

However, they didn´t have to walk much; well, she didn’t. Olga, her Dame partner, was waiting for both in the car.

“Look who´s here, Olga. It´s our friend, Matt!” Katy was excited, but Olga was not the same.

“Yeah. Matt.” She turned at him, as Katy entered the car and placed him over her lap. Then, Olga just rose an eyebrow. She´s not friendly.

“Uhm… good morning?” He waved, but he knew she didn´t appreciate him being there.

Olga was not like Katy. She was kind of… mean. Taller than Katy, standing at 20´10”, her body was thick, hefty. And her face authoritative, a total contrast with Katy´s friendly smile. She wasn´t very polite either.

“Are you sure you don´t want to sit him at the back?” Asked Olga as Katy fastened her seat-belt, with Matt sitting between her massive thighs.

“I´m sure. He´s safer here. Right, Matt? Besides, we´re on a date. He wanted to spend the whole day with me. I think he needs to able as close as possible, don’t you?”

“Whatever, just hold him tight.” Olga rolled her eyes.

“Oh, I will.” Katy surrounded him with her loving hands. And then, they drove off.

He wanted to spend the day with Katy. But Matt completely forgot about Olga. Maybe she will make things a little less, pleasant? And even if he won´t admit it, she´s kind of scary. Her staring is threatening.

Matt may feel a bit uncomfortable for sitting on the same car as Olga, however, she shouldn´t matter. He´s on this sort of date with Katy.

Sitting between her thick thighs, feeling the warmth between them, the softness of her crotch. Thighs that rose at the same level as his shoulders. He may not see the road, but he wouldn´t pay attention even if he could.

Katy was the tallest woman he knew, a giantess, sexy, and really top heavy.

He wasn´t tall enough to feel the enormity of her bosom, bouncing all over him. Making a comparison of a woman´s body with a man´s would be insane. She´s a little over four times his size, everything in her is enormous. And so hot.

The whole time there, sitting in front of her groin, Matt was aroused. He could feel his member getting harder and harder. He tried to cool it and pay attention to this routine, but she was just so sexy.

Her large hands, placed smoothly on his shoulders, massaging him gently.

“So cute…” she whispered.

Katy was having fun too, but she wasn´t aroused like him. She loved it, but for other reasons.

Katy loved her duty, she found herself as a men´s protector, well that´s the main reason why she picked the job. It was easy to decide, she had the height, the skills, and what´s more, the love for justice.

However, she was afraid she´ll become a lonely lady. This work requires time, a lot of it. And she works all these long shifts, gets to her house only to get ready to sleep. She doesn´t feel like she´s fulfilling all of the maternal dreams she had.

She had a dream, that one day, she´ll find a man to take care of. Maybe someday she´ll save a man and he´ll fall for her. Or that´s what she dreamt of. And somehow, it seems this dream became true.

There he was, Matt, sharing the seat with him. Was he grateful she´s saved him a couple times? Thankful because she was such a lovely lady? Is this his way to say thank you? Or maybe the perfect way to propose to her?

Whatever it was, she was ready. She had a surprise for him…

The rest of the day was pretty much the same, and whenever they got off the car, she carried him in her arms. He would´ve minded, or tried to protest, but he was so turned on by her body.

Sitting between her thighs on the car, and laying in front of her bouncing boobs while walking. She was titillating him with her body. Even when she wasn´t trying.

At some point, he even forgot he was hungry… but they didn´t.

“Mmmm… so tasty…” Came Zoey´s voice as she finished a huge sub, a turkey one.

“I know, these store makes the best subs in town…” Added Olga, who was half-way through her second sub, both meat lovers. She was a big lady, well bigger.

Matt just sat there in silence, he wasn´t really hungry yet. His lunch was at a later hour, and women eat way more than men. But that´s expected, they are gigantic beings who burn calories like a furnace. He stood there, quietly as they ate, noting the time, at least he had to write something down about this woman´s routine.

While sitting there, he could feel a small bulge that had grown inside her, a whole three-foot sub, and three gallons of soda. However, that was not the only thing in schedule.

“Well, Olga, I think our friend here needs some food too… do you mind?” Said Katy as she used the car to point Olga to get out of the car.

“Ugh, but I´m still eating…” she complaint.

Katy had a pill right before, and it was already kicking in.

Olga looked down at her breasts, and could see two wet spots on her blouse. Of course, Katy couldn´t hold it.

“Fine.” Olga grunted as she opened the door and got off, without forgetting her drink.

“Tell me, Matt. Are you ready for your lunch?” Katy asked.

“Oh, well, I´m… I´m really not that hungry.” He said. But he ignores Katy wasn´t asking.

“Aww, how cute. Listen, dear. Mommy already had her lunch, now, it´s time for you to eat something too, we can´t have you go on with an empty stomach all day long, right?” she wasted no time, before he could protest, she was already placing him sideways over her lap. He was eating, whether he was ready or not.

“Don´t worry, mommy knows best…” she said as she unbuttoned her blouse and revealed a pair of swollen breasts. Her bra was already stained with milk.

Maybe this is what he doesn´t love about maternal giantesses like Katy. Before he could say anything, she had already undone her bra and exposed her engorged nipples. Hard, dripping nipples.

“K-Katy… uhm, you know I… I´m really not so… I had a large breakfast and…” he didn´t want anyone to see her at the parking lot, feeding him straight from her tit inside the car.

“Shhh, shhh, relax. Just close your eyes and take this big, fat nipple in your mouth. It´s full of vitamins…” she cooed as she inserted the nipple inside his mouth.

Matt kicked in for a second, but she just pressed him a bit harder against her tit. He closed his eyes hard; his whole face was pinned against her mammoth-sized breast.

The milk was creamy, thick, tasty. He hated it, but he liked it. This wasn´t his idea of a meal, but the more he drank, the sweeter it tasted.

He wasn´t counting on the fact that Katy will take this as a chance to breastfeed him. But he should´ve seen that coming.

“So precious. Drink up, Matt. Because we´re just starting.” She was right. If he agrees, all of his days will be like this. Spending all of his time pinned against Katy´s body; feeling Olga´s anger falling over him, at least her contempt. But most of all, his only meal would come out of that huge, soft, and swollen tit.

He hated the fact that the milk was tasty, but being a grown man, fed by her like this, it felt wrong.

“Drink up, dear. Drink to your hearts content.” She cooed from above.

He couldn’t resist. Even if he wanted, he was on a trance now, sucking, swallowing. Creamy milk filling his stomach. There´s a huge chance he´ll be knocked down by the time he drinks both of her titanic breasts´ milk.

He was already feeling sleepy. Why? Besides, another question came to his mind, had he told her this was not going to be a full day? That this date was only until… 2:00 pm, maybe 3:00? He hadn´t schedule a date with Zoey, not yet. But, had he explained this to Katy?