There is not that much information on possible homosexuality in the Estonian Middle Ages. In light of this, a clause stipulated in the agreement signed between the Order and Saaremaa’s islanders in 1255 is all the more unusual:
‘The third [additional legal provision] is that if according to local custom, somebody has to be expelled from Saaremaa for committing an unnatural sin, his heir has the right to his inheritance if he has obtained permission from the landlord.’
‘Unnatural sin’ usually referred to homosexuality in medieval legal documents. If that is the case here as well, we are left to infer that the traditional legislation of Saaremaa’s islanders prescribed exile for homosexual relations, which in society of that time was quite a severe punishment. The agreement of 1255, however, gave the family members of the exiled person the chance to continue to retain control of the exiled person’s land.
In 13th-century Western Europe, punishments for male homosexuality were far more severe, starting from castration and extending to burning at the stake and the confiscation of the offender’s entire property. Thus, the document from 1255 can also be interpreted as punishment that was considerably milder than the usual punishments for such transgressions and hence as a privilege granted to Saaremaa’s islanders.
Võimaliku homoseksuaalsuse kohta Eesti keskajal pole kuigi palju andmeid, seda ebatavalisem on saarlaste ja ordu vahel 1255. aastal sõlmitud lepingus ära toodud punkt:
„Kolmas [lisanduv õigusesäte] on, et kui Saaremaalt tuleb keegi nende tava kohaselt loomuvastase patu pärast välja saata, on tema pärijal õigus pärandusele, kui ta on maa isanda loa nõutanud.“
„Loomuvastase patu“ all mõeldi keskaja ürikutes tavaliselt homoseksuaalsust. Kui see on nii ka siin, tuleb järeldada, et saarlaste tavaõigus nägi homoseksuaalsete suhete eest ette pagenduse, mis tollases ühiskonnas oli üsna raske karistus. Leping andis pagendatu pereliikmetele aga võimaluse hoida maa jätkuvalt enese käes.
13. sajandi Lääne-Euroopas olid karistused meeste homoseksuaalsuse eest palju rängemad, alates kastreerimisest kuni tuleriidal põletamise ja kogu omandi äravõtmiseni. 1255. aasta dokumenti võib seega tõlgendada ka kui tavapärasest märgatavalt leebemat karistust ning saarlastele antud privileegi.