Personally I'm not so sure Jesus changed everything for women (more than for other groups); at least I can't find a statement hinting at that anywhere in the NT. I do find statements that show everything changed for the Gentiles (Peter's vision in Acts).
I think He did. Ss Paidiske points out, Jewish culture already had seeds of egalitarianism within it, compared to surrounding cultures. Jesus rather pointedly poked holes in some of the remaining major dams. Jesus may have had only males among His apostles--but that might have been a purely tactical matter, in that males were free and able to move in that society but women were not. But He did have women among His disciples, and
that was a big deal for a rabbi to have female disciples. That wouldn't have had too much effect on Judaism, but early Christians could read between the lines.
'There is neither Jew nor Greek, there is neither slave nor free, there is no male and female, for you are all one in Christ Jesus' (Galatians 3:28), but that does not mean there are no believing slaves or slave owners anymore, or that there is no distinction between believing males or females (Paul called for slaves to obey their masters, and for masters to be reasonable with their slaves). Paul has very asymmetric instructions for men and women (e.g. for wives to respect and submit to their husbands), Jesus chose only 13 male apostles (including Paul), we do not read about cancellation of OT laws, etc..
I'm not sure how asymmetric Paul's actual intention was. Paul's dilemma was that the nascent Church had to operate in a social atmosphere that could (and did) become hostile at any moment.
Given the clear symmetry of his declaration, there is no reason to think his concept was not as symmetrical. Scripture is explicit in showing Paul moving forcefully to eliminate the line between Gentile and Jew. But that was safe...only Jews really cared about that anyway...it was not a concern of the Roman empire if Jews and gentiles were buddies.
But Roman thought was still prickly from the Spartacus rebellion (and other slave rebellions like it), so an obvious overturning of slave culture or gender roles would have drawn immediate attention to Paul as a rebellion-rouser and the Church as a dangerous organization that flouted all social order and sensibility. Luke's depositions of his gospel and Acts show Paul taking pains to display Christianity as non-offensive to the Roman empire. Whatever problems Romans had with Christians, lawbreaking and rebellion would not be among them.
Yet, as with Jesus, Paul does give clear statements to indicate that
within the Body of Christ, those other two lines were also abolished. Ephesians 6:9 abolishes the line within the Body of Christ between slaves and masters, turning slaves from being the property of their "masters" to being the responsibility of their "masters." It turns the masters into stewards. And of course, there is that letter to Philemon written for the sole purpose of freeing an escaped slave, which was a bold demand given the Roman laws that required an escaped slave to be severely punished (that Spartacus thing again).
And as well, statements such as Philippians 4:3 indicate a real movement to equalize the roles of women in the Church.
Jesus does behave outside his societal norms speaking to a Samaritan woman with a questionable reputation, letting a 'sinful' woman dry his feet, challenging 'sinless' witnesses to cast the first stone for the woman caught in adultery, etc. but I don't see agenda in that changed the existing OT laws that treated men and women quite differently.
Well, "agenda," no. Christ's clearly stated
agenda was to bring salvation to mankind. But
modus operandi, yes. And that was as true for Paul. Paul's
agenda was to spread the gospel, not to fix the Roman empire.
On the 'penetration' thing, I suspect that is recognised in cultures all over the place. It may be one of the explanations why homosexual acts between men are prohibited in OT law, but surprisingly not between women.
That was also how homosexuality played out within the Roman army. To be the penetrator of either male or female was acceptable. For a legionary have been penetrated, however, drew a death sentence.
There was a Roman army story of an attractive junior officer who was constantly being pressured for sex by his senior officer. Other officers were aware of it, but they were merely watching to see how the matter played out. Eventually, the young man murdered his own senior officer. That would have also drawn a death sentence, but because the other officers were aware of the circumstance, they did not prosecute the young officer...he had taken the more honorable way out. It's unknown if that story is really true, but the fact that it was passed around within the legions indicates their attitude about such things.