The first attack happened around 3 a.m. Saturday on the 1600 block of South 55th Street.
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According to police, a woman was inside her car at a traffic light when a man approached the vehicle, pointed a small black handgun at her, and demanded money.
She gave the man $20 and that's when police say the suspect ordered her to unlock the car doors. The woman was then ordered to drive to 49th and St. Bernard streets where police say she was sexually assaulted.
After the attack, the suspect drove the victim to an ATM where she was ordered to withdraw money.
The suspect was last seen fleeing the area wearing dark gray sweatpants, gray hoodie,and a blue mask.
A second attack happened on the 1100 block of S. Paxon Street around 5 p.m. on Sunday.
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Police say a woman was walking near the 5100 block of Springfield Avenue when she was approached by an unknown man on the 1100 block of South Paxon Street.
The man demanded money from her while at gunpoint, police said.
Police give update on Southwest Philadelphia sex assaults
She was then forced into an alley and sexually assaulted after giving the suspect $25, according to investigators.
"I got up that morning after reading this in utter shock, especially at 5 o'clock in the afternoon in broad daylight on a public street. It's a heinous act," said Captain Margo Alleyne-Parker. "I actually grew up in the area so I was very, very shocked and wanted to make sure this was put out as soon as possible, as we do with all our jobs."
The man fled the area on foot. He was last seen wearing a blue mask, dark pants, and a blue hoodie with a red Phillies hat.
No arrests have been made. Anyone with information on these cases is asked to call police at 215-686-TIPS.