I have learnt that Lord Buddha was initially reluctant to ordain females but after a lot of convincing by his step mother Buddha started ordaining females. Why was he initially reluctant? If not for his step mother would there even have been a chance for Buddha to ordain women?
I once listened to the same question being answered by a monk. And here are the answers. (Not the exact words but the long story short.)
Lord Buddha never said that Males are better than Females. But as this is India that we are talking about Buddhism had to face some major issues when bringing equality to a country that was dominated by a cast system that was directly attached to the religion which later on formed Hinduism.
Lord Buddhas take decisions taking Past,present & Future into equation. When Lord Buddha himself first visited his own relatives they did not worshiped Lord Buddha. So Lord Buddha had to show miracles to get them out of their ego of cast and royalty. This was the kind of socio-political landscape that Lord Buddha had to work with.
Buddhism had to do things very carefully because any wrong move would have caused a bloodbath between Buddhist kings and non-Buddhist kings over the new found religious democracy.So Lord Buddha had to face some difficulties when handling social issues.
A good example can be found in the situation that unfolded when Lord Buddha allowed Prince Rahula (the son of prince siddhartha who later on became our lord Buddha). Lord Buddha's father came and pleaded for a new law that forbids the acceptance of people who come to become monks without the approval of their parents. This law is valid to this day and the only way such a person is going to become a monk is either waiting till his or her parents die or threatening to suicide if the monk-hood is not granted. (I personally know a great monk who became a monk by the threatening.)
As you can see it is not fair but it was necessary. Now lets see why this happened.
In the era of Lord Buddha women were right next to animals, more tools or breeding machines than equals with men. Lord Buddha had to fight centuries old traditions and beliefs. (sadly to this day Indian government has to issue advertisements via all forms of media saying "Your daughter deserves education too").
It is in teaching that Lord Buddha refused to accept Female monk hood three times and after the third accepted it. But the Female Monk hood disappeared from many countries and even today female to male ratio of Buddhist who would consider monkhood is not satisfactory. Maybe that was the reason it disappeared.
Lord Buddha gave a certain set of rules to be followed by female monks so that they could avoid any harm that could come from the society that was genuinely "Masochist".
there's an alternative point of view suggesting that if the Mahapajapati's story is indeed authentic, it postdates the first acceptance of a woman into the Sangha, who could be Bhadda Kundalakesa, and that reluctance of the Buddha concerns specific circumstances of that particular episode and not wholesale refusal of women entrance into the order
Bhadda Kundalakesa Therigatha (Thig 5.9)
I traveled before in a single cloth,
With shaven head, covered in dust,
Thinking of faults in the faultless,
While in the faulty seeing no faults.
When done was the day's abiding,
I went to Mount Vulture Peak
And saw the stainless Buddha
By the Order of Bhikkhus revered.
Then before Him my hands in añjali
Humbly, I bowed down on my knees.
"Come, Bhadda," He said to me:
And thus was I ordained.
Debt-free, I traveled for fifty years
In Anga, Magadha and Vajji,
In Kasi and Kosala, too,
Living on the alms of the land.
That lay-supporter — wise man indeed —
May many merits accrue to him!
Who gave a robe to Bhadda for
Free of all ties is she.
the issue is dealt with at length in the Ven Sujato's book "White Bones Red Rot Black Snakes" (free)
the history behind the issue appears very misty to me, where the truth probably won't ever be found out
If you look at the actual story in question, Mahapajapati wasn't asking the Buddha to ordain women in general, but was only asking about herself, and the Buddha was reluctant. I should note that some modern scholarship seems to suggest that this story could be fabricated.
Even if the story is true, the reasons for his reluctance couldn't have been because he didn't want there to be a Bhikkhuni order, because the Vinaya has a section that describes Mara trying to convince the Buddha to pass into Parinibbana, and the Buddha kept giving reasons not to, and once he said that he wouldn't because he hadn't established the Bhikkhuni order yet, so it seems that the Buddha intended to have an order of Bhikkhunis from the beginning.