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1.
Love me some cute preppy boys =)
Age: 29 | seeks gay preppy guy dating in Wicker Park, Chicago, Illinois (IL) USA

jerryclaxton

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I am a [email] b0tt0m So lets have some fun. JerryClaxton IS HIV POSITIVE
Age: 57 | seeks gay preppy guy dating in Wilmette, Chicago, Illinois (IL) USA

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5.
I am a clean cut and career oriented preppy guy looking for similar to go out to dinner, movies, etc with. Enjoy hanging out with my friends, going out, working out, reading and movies.
Age: 35 | seeks gay preppy guy dating in North Side-ravenswood, Chicago, Illinois (IL) USA

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6.
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Age: 28 | seeks gay preppy guy dating in Chicago, Illinois (IL) USA

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7.
my top places to shop are a&f and hollister and i pretty much cream my pants when i see a hot preppy guy decked out in torn jeans or surfer tee's...
Age: 18 | seeks gay preppy guy dating in Suburbs, Chicago, Illinois (IL) USA

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8.
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Age: 47 | seeks gay preppy guy dating in Near Midway, Chicago, Illinois (IL) USA

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stormbringer

11.
I've been a prep since high school. I'm most comfortable in khakis and button-down (Polo) shirts. I'm really into other clean-shaven preppy guys as well. Interested? Drop me a line.
Age: 37 | seeks gay preppy guy dating in Oak Park, Chicago, Illinois (IL) USA

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19.
Nice guy, conservative appearance with wild side. Seeking similar in Chicacgo.
Age: 45 | seeks gay preppy guy dating in Il, Chicago, Illinois (IL) USA

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20.
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Age: 18 | seeks gay preppy guy dating in Hydepark, Chicago, Illinois (IL) USA