The image of the Virgin interceding with her breast, often shown as the Virgo Lactans, was held to be a particluarly effective intercessory image. In the case of the pictures shown here, the Virgin does not present her breast to her infant Son, but rather exhibits it in conjunction with the wounds of Her Son.
The purpose is to emphasise the active physical connection between her milk and the blood of Christ, which was rooted in contemporary physiological theories of childbirth and nursing practices.
These are set out in
more detail by Beth Williamson in Apollo Magazine.
Lorenzo Monaco
c. 1400 (tempera on canvas)
The Intercession of Christ and the Virgin
Metropolitan Museum, New York
Originally located in the Duomo in Florence.
To the right of God the Father, the Virgin offers her breast as a means of intercession, while indicating a group of eight diminutive figures who gaze up at her Son.
Christ looks towards his Father, gesturing to his Mother with his left hand, while with his right hand he indicates the wound in his side, drawing a visual parallel between wound and breast as means of intercession.
Christ's insrcribed words read: 'My Father, let those be saved for whom you wished me to suffer the Passion.' The Virgin's read: 'Dearest son, because of the milk that I gave you, have mercy on them.'

Benozzo Gozzoli
1464-65
St Sebastian Intercessor
Nave of Sant'Agostino, San Gimignano
In the upper level, with ancient gestures of intercession, the Madonna shows her breasts and Christ his wounds to the Eternal Father, enraged and bent on hurling pestilential arrows with the assistance of host of angels. Below two pairs of angels are trying to break the arrows. Both Christ and His Mother indicate the supplicant community below.
The arrival of the plague in San Gimignano in the spring of 1464 revived devotion to St Sebastian. The Augustinian community agreed with the Compagnia di San Sebastiano to commission a fresco of Saint Sebastian Intercessor in Sant'Agostino.
The saint, clothed instead of naked and pierced with arrows, stands surrounded by a diverse assembly of devotees sheltering them under his cloak in the manner of the 'Misericordia'.

English, unknown
14th century
Speculum Humanae Salvationis
Pierpoint Morgan Library, New York
Chapter 39 of the Speculum is devoted to the theme of intercession. Illustrated versions show the Virgin exposing her breast to Christ in one picture and Christ, his arms raised in a gesture of prayer, exhibiting his wounds to God (below).
English, unknown
14th century
Speculum Humanae Salvationis
Pierpoint Morgan Library, New York
Christ exhibits his wounds to God.