The Criminal Law Reform Bill will, if passed, change the country's penal code "to ensure that it remains relevant and up-to-date", according to the city state's Ministry of Home Affairs (MHA).
"The bill introduces a new offence criminalising the procurement of sexual activity where consent is obtained by deception or false representation regarding (a) the use or manner of use of a sexually protective device, or (b) whether one is suffering from a sexually transmitted disease," a spokesperson for the department said in a statement.
People convicted of stealthing could be imprisoned for up to 10 years, according to the bill's current text.
Those found guilty could also be caned.
Singapore's government introduced the proposed legislation in parliament on 11 February for its first reading.
If passed unchanged it will also criminalise the act of non-consensually taking an image or recording of a person's genitals, a practice often known as 'upskirting'.
Lawmakers also hope to criminalise revenge porn, including the act of threatening to distribute an intimate image of a person to cause them "humiliation, distress or alarm".
The draft legislation follows a landmark case in Switzerland where in 2017 a man was convicted of rape after he removed his condom during sex with an unconsenting partner.