Richard Ball was put behind bars for 18 months during a hearing held at Sheffield Crown Court on Friday, after the 24-year-old pleaded guilty to five counts of sexual assault of a child at an earlier hearing.
The court heard how when the incident took place on February 24 last year, Ball was aware the two girls, who were then aged 12 and 13-years-old, had been drinking.
Judge Michael Slater told Ball: "You made overtures towards each of these girls, who you recognised had been drinking that night."
Ball provided each of the girls with alcohol, before sexually assaulting them over a prolonged period of time.
The two girls, who cannot be named for legal reasons, initially 'suppressed their thoughts' and did not tell anyone what had happened, but later came forward and reported the incident to the police in May last year, said Ian West, prosecuting.
When interviewed by police in May 2017, Ball admitted to being with the girls on the evening in question, and to asking them questions about their sex lives but denied committing the sexual assaults.
In victim impact statements provided to the court, one of the girls said the incident had a 'profound impact on her,' while the other said Ball's actions were 'always on her mind' and had resulted in her isolating herself from her loved ones.
She continued by saying the two girls, who were previously 'inseparable,' had fallen out as a result of what happened.
Ball, of Crescent End, Thurcroft eventually pleaded guilty to the five sex offences on the first day of his trial when both girls were present at court, expecting to be called to give evidence.
Defending, Clive Smith, said: "The defendant, by his guilty pleas, accepts the fact that the sex assaults took place as alleged, and he himself had been drinking. What ever happened on this night he is totally ashamed of."
He added: "It's very unlikely that this defendant will ever see the inside of a court room again."
Despite Mr Smith's mitigation, Judge Slater said the level of Ball's offending was such that the only option available to him was an immediate custodial sentence.
In addition to jailing Ball for 18-months, he also banned Ball from contacting either of his two victims for the foreseeable future by granting restraining orders.