Posts in September, 2009

Uncharted Territory

Sunday, September 27th, 2009
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When I think about my life as Cassandra, I can honestly say this is something I’ve stumbled upon by chance.  I’m not a woman trapped inside a man’s body.  I have no need to be a woman just to have sex.  But OMG!!!  Dressing up and having sex with men whom I would have never imagined to secretly love [...]

Hot Date… Part II

Sunday, September 20th, 2009
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He rode my cock. He just went and sat on it.  It went in so smoothly.  My theory is that your asshole is directly proportional to the size of your cock — the bigger your cock, the bigger your rectum.  But Mr. Skinhead with his gigantic pink cock had a perfectly tight hole.  I could [...]

A Pretty hot date

Tuesday, September 15th, 2009
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While looking over my latest blog entries, it occurs me that it’s been a while since I told a good sex story.  So, unzip your pants.  Get your poppers.  Take your dick out and start stroking it. This story is HOT.  I hope you shoot multiple loads while reading it. This guy had been responding to my [...]

Tie-Me-Up Some More…

Wednesday, September 9th, 2009
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Tie-Me-Up has been such a devoted regular, even though I have yet to fuck him.  [I wrote about him in an earlier post, so if you are not familiar with him you may want to click on the link to get his story.]  His sexual fantasy is to be kidnapped and then raped.  And when [...]

BLT or Grilled Cheese?

Monday, September 7th, 2009
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Sandwich Guy came back yesterday to buy some more weed and some more Cassandra. He’s a really cool guy but he says the same corny line every time I fuck him.  Cassandra, you massage that prostate so good I never have to worry about passing my prostate exam! He says the same line.  Every time. Usually when straight guys come [...]

Go Bears!

Thursday, September 3rd, 2009
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This is the year we’re going to the Rose Bowl.  This year, the California Golden Bears will not choke.  We will start off the season by avenging our loss to Maryland last season.  Without the East Coast heat and humidity, coupled with a starting time when our players are wide awake, we will crush the Terps.  [...]

Just Shoot Me

Thursday, September 3rd, 2009
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By now, you’ve probably read about the guy who went on a killing spree at a women’s aerobics class.  He was lonely.  Isolated.  Deprived of sex for over 18 years.  Angry at the world.  He blamed women for his sexual frustrations. Dan Savage wrote an excellent column addressing this incident.  [Please, please, please click on the link [...]

Maybe, Maybe Not.

Tuesday, September 1st, 2009
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Silver Fox came back from vacation yesterday.  (It’s not a real creative nickname, but he has a salt and pepper moustache, and I think Silver Fox sounds better than S&P Moustache.)  He spent the past two weeks in South America.  I spent the last two weeks dry and barren.  Silver Fox is my single most steady customer.  Through my many [...]