Raleigh to Houston for a business trip with a planned hook-up.
Raleigh to Charlotte occasionally to see a “friend”.
Madison to New York City, but the sex wasn’t the point of the trip. Watching Broadway shows was the point of the trip. A girl has to have her priorities.
Absolutely charming answer.
OCS-You’re only about 1245 from me. I didn’t count the 240 times I circled the block…On foot. Incognito with a grocery cart. Smelling vaguely of lavender and moth balls. A picture of you, superglued on like a tramp stamp. Fond memories, babe.
Ever how far it is from Danang to Honolulu.
Drove about 180 miles on a Friday evening specifically because I had a horny woman waiting for me at my destination; we got naked when I arrived, had sex throughout the night and the next morning, then I saw her off to work Saturday morning and hit the road, 180 miles back home. Good times.
300 miles. Santa Cruz to Weott, CA. Worth it at the time!
From Southern California to Everett, Washington for a sure thing, for a long weekend long ago.
Cincinnati to Malmo Sweden, 4300 miles, several times. I dated a Swedish girl for 2 years while I was in college. So to all the Swedish Dopers: “Hej.”
It didn’t work out… but then I met this nice American girl; fewer frequent flier miles but so much more convenient.
Bromont, Quebec to Burlington, Vermont. Was over there for three months training with IBM and moving between two plants quite a bit.
Met the girl in a bar in Burlington but was traveling to Bromont very early in the morning so went back to the hotel early. She was cute and very sexually aggressive and left me with a kiss and a whisper in the ear “Come down here this weekend and I’ll fuck your brains out”.
I did. She did. Great girl. Had some good times in VT with her. Stayed in contact for a while but distance made it hard. Eventually the communication got further and further apart until it stopped. Shame but that’s life 
ETA: The whole Irish thing worked REALLY well in the States. Wasn’t too shabby in Canada either actually 
I’ll bet.
Oh, I was pissed beyond belief. Before I met her boyfriend, who was also called Jim (handy for her), I saw his resume, which indicated he liked Kung Fu, kickboxing and power wrestling or whatever, so then I resolved to be calm. Which I found quite difficult, especially when I met him and found he was built like a brick shithouse and kept giving me suspicious looks. Turns out she’d never mentioned to him that they were on a break while she was boffing me, which made me even less calm. I walked on eggshells for quite a while and tried not to shake too much with fear when he was in the apartment.
Come to think of it, he was from Chicago too. Your name’s not Jim too, is it? ::Quakes in boots::
Well, I did try it on with her roommate, who was way cuter, but the roomie wasn’t interested, and then the ex found out and hit the roof.
It was an interesting trip all round. Part of life’s rich tapestry of learning.
What are we defining as “sex”?
Fourteen hundred and fifty miles, from my hometown to Toronto, taking the biggest risk I’ve ever taken in my life. It turned out very well. He even still thought I was cute, after I’d been up for almost twenty-four hours (traveling to the airport, the flights, and the flight delays) and had frizzy hair and a stuffed-up nose from forgetting to take my allergy pill.
I do not recommend this course to anyone, but it worked out well for me.
840 miles to sleep with someone. Note that “sleep with someone” does not include “sex”. No, I’m not lame :rolleyes:
Okay, there was a party involved, too, but I could have almost as much fun in front of my TV drinking Sapphire and juice and watching britcoms.
Six miles. I was in the area anyway.
[nitpick] Tinley Park is it’s own town, South of Chicago, near to where I grew up. How WAS the Holiday Inn, by the way [/nitpick]
Chicago to New Jersey, Florida and St. Louis.
oh what fun Jersey was. I wonder if she ever recovered.
A guy flew here (USA) from England to lose his virginity to me—does that count? 
From Lisbon to Washington, DC and back again. Oh, and once I went from Guam to California, and my ex once came to Japan from CA. What do I win?
Does it count if the trip wasn’t planned? I met a woman on a flight from Minneapolis to Fort Myers, Florida; we were together for a couple of days and I’ve never regretted it.
Minneapolis, MN to the western suburbs of Chicago, IL, or around 400 miles.
Every other weekend for two years. It was a long-distance relationship with me in grad school, so it wasn’t just for sex. We’ve been happily married for years so it was worth it both at the time and now.