Chicago in June

Business trip for a couple of days and visiting old friends.  Need a companion.  It has been so long since I traveled with someone and I kinda miss it, actually.  Travelling with someone and playing tourist is one of my favorite things to do. Also waking up in the middle of the night and having sex, and then going back to sleep is one of my favorites as well. Getting up in the morning getting some juice and sitting casually by an outdoor cafe together ranks pretty high up there as well.

On this topic, how does one travel with a SD or SB? Well the SD would have to give the cash, the SB reserves a plane ticket on the same flight, this way preserving her anonymity. Or if she feels comfortable sharing her full name and date of birth, the SD can do the bookings.  The next question then would be: do they share the room for a couple of days or do they get split rooms?  I remember when I offered my old friend Tina to take her along on a trip from Houston back to New York and get her a separate room she said: ‘Why? You have already seen me naked’.  Good point.  I guess that’s a good rule to follow. If one has seen the other naked, then get the same room.  There is a friend I wouldn’t mind taking with me, even though we have not seen each other naked…

I always offer to get them a separate room, just to make them feel comfortable. Usually they turn it down. And many have made the same comment: ‘David you are quiet when you sleep, and you stay at your corner’.  One actually said ‘You looked like a little kid all curled up like that. You turned your back though.  Were you defensive?’ What a thing to say to someone you just spent the night with. Weird…Incidentally I was not defensive. I sleep on my side that’s all.  I just remembered sleeping next to a snoring sugar baby once. That was a ‘great’ experience, as I didn’t get to sleep all night. Not because we had a wild night, but because she was snoring! I just can’t sleep when someone does that.

But anyway, just having a ‘sleepover’ with a new acquaintance is something I always liked.  The wheels in this brain of mine are turning. I don’t think I have done any blogs on travelling sugar but I should have one.  The next post will be on some rules/regulations/expectations.  I already solicited the opinions of old sugar acquaintances so will include those opinions as well.

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3 Responses to Chicago in June

  1. V says:

    My friend just had a crazy week in Chicago whilst on a business trip. Poor girl got propositioned by her lesbian line manager and later got an offer for a threesome whilst having a drink in the hotel bar, the guy was not really selling it as he said ‘It won’t take long’.

    Maybe it is the wind? :)

  2. Nice. I am getting excited about Chicago already. Always liked it there anyway..

  3. Travelgirl says:

    I love meeting people when travelling, and i LOVE being someone’s companion during their business/holiday,etc… So, you tittle ”Chicago in June” remind me of my travel to Chicago in July :) (What a coincidence :) ) and that i use to think next month is coming, i want to go somwhere..but ”who with”

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