Rajeeve Gupta Fulbright scholar from India has won the 'Smallest Penis' crown at second annual sausage show held at the Bushwick's Kings County Bar in Brooklyn. According to the New York Post the 28-year-old said that while expressing his happiness that now he might meet someone because of this News.com.au reported. Aimee Arciuolo bar owner said that lots of contestants take part in the contest but at the last minute they pull out but Gupta was definitely the littlest big winner. (Read: Penis enlargement methods do they work?) Should you really worry about penis size? Men are obsessed with size.