heaven knows, anything goes.

I had my overnight with the “famous” guy last night.  In his case, famous means: well known in his circles, and maybe you’ve seen him once or twice in a magazine or on TV.  In the interests of keeping his identity anonymous, there are some things I would like to say in this entry that I’m going to have to leave out.  He’s an esteemed (according to one description of him that google brought up) antique collector/dealer, or at least enough so that if I mentioned certain pieces/collections he had, someone in the antique world might figure out who he is.  I realize my blog isn’t really at the level yet that he would have to worry, but who knows, maybe it will take off overnight and I’ll suddenly be outing my johns.  I’ll save that for my multi-million dollar, Heidi Fleiss book deal.  Until then, he’ll just be known as “antique man.”

We talked a lot on the phone beforehand.  He was very talkative (on the phone and in person), which I liked.  After setting up our meeting and then confirming a couple times via text and phone, I arrived around 8pm.  He met me at the door with a beautiful bulldog, who seemed very friendly.  He was probably in his 50s (the man, not the dog), but wasn’t terribly out of shape or bad looking.  Just looked his age.  He led me into his apartment, which was beautiful, although a little cluttered, which seems to be the antique collector’s way.  His fireplace was going, which was very nice.  I later learned that the building used to be owned by a famous couple…  who I shouldn’t mention.  I truly wish I could be more specific, but just know, the apartment and the things he had in it were simply beautiful.

We made small talk as he grabbed a bottle of Prosecco and poured us both a glass.  He told me that I looked different from my pictures, which I’ve been told before.  I need to go through all my picture options with my roommate sometime.  Although nobody has been disappointed (they say I’m better in person) I don’t want to misrepresent myself.  He said I looked a little more…  mature?  I also am a little scruffier than my pics make me out to be.

As he came back from the kitchen he grabbed me and went for the mouth.  We made out for a minute, then headed over to the sofa where we lounged, chatted, listened to some music, and fended off his dog, who was pretty nippy.  I think he was jealous of the attention that I was getting that was usually his.  We listened to a lot of music…  jazz mostly.  We had talked on the phone about some hard to find CDs he had gotten that he was excited to play for me.

As a general comment about the whole night, I think he was very excited about the fact that I could keep up with him and his antique/history/music/etc talk.  Not gonna lie, a little of it was BS.  But I was genuinely interested in most of it, and the stuff in his apartment could have fueled WEEKS of conversation.

He got pretty feisty pretty quickly, and after shoes and my cardigan came off, we lit a joint.  I didn’t want to get too fucked up, but I was comfortable with him (and the weed was chill) so I shared some.  Halfway through the joint we headed upstairs for what I can only term as: epic. sex.  If anyone wants to avoid some small TMI moments, skip ahead!  (why the warning? no idea.)

Now, this was a 50-something year old man.  Not a great body, but like I said, fine for his age.  Not anything I would EVER have sex with for free.  But let me tell you…  we FUCKED.  After some more making out and foreplay, and me sucking him off for about a minute, I ended up fucking him for at LEAST an hour.  Possibly longer.  He was a total bottom.  This was the first time I’ve topped a client, PS!  Now, he wasn’t the tightest thing in the world…  I mean, I really wouldn’t expect that of a middle-aged bottom.  I also was a little drunk and high.  But it was definitely longer than most of my sexual encounters.  He was very appreciative.  Some quotes:

“Where/how did you learn this???”

“You make me feel like a teenager getting fucked again.”

“I knew it was going to be good… but I didn’t know it was gonna be THIS good… oooooooaaeeeiiiooooooaahhhhhhhhhh”

We took a couple breaks, although I’m not quite sure why, they only lasted a minute or two.  We cleaned up a little in between, too.  At one point I put a cock ring on, which I’ve never used but I wasn’t staying totally completely hard, so it helped. He had poppers, which to me have always been kind of sketchy seeming…  but of course, they feel good, too.  They were more for him, but I did them too (“we’re such perverts” he said… whoops). I was feeling pretty comfortable with him.  We covered all the basic positions, but he was on his back most of the time, just taking it.  For what it was, it was surprisingly hot.  I was just on the phone with my best friend, saying that in a way it’s like getting a blow job…  you can kind of close your eyes and imagine whatever you want.  A hole is a hole, right?  Excuse the crudeness.  And at times I would think about the boy I’m casually seeing (see my last couple entries), and unfortunately, once again, that did NOT aid in the sexiness.  Got those pangs.  I really don’t think this boy is ‘the one,’ and in that respect, I’m not worried about it getting too serious and interfering…  but that doesn’t erase the possibility of complications down the line.  But! I can’t worry about that now, when I owe my parents money and my bank account is overdrawn.

side note: does that mean I’m being forced to do this?  Am I backed into a corner and forced to make decisions/changes in my personal life because the only way I can pay back this money is if I escort? Or did I plan this?  I’ve said this in the past, but I want to be more regular about working in the next couple months, just so I have a cash cushion.  I still hold the same views about this work…  I just don’t want to be controlled by it.  I’m tired of the end of the month rush to find a client, feeling like I’m forced to lower my standards because I need the money (which I haven’t realllllly had to do, but I’ve felt like I was in that position), and now that it could affect personal life decisions…  it’s time to save some cash.  I could easily make a thousand or two a week if I wanted.  Blah blah blah back to antique man.

He was kind of a wimpy sounding moaner…  loved being fucked.  Very complimentary of my dick, which was nice.  Got another ‘perfect size’ comment, which is nice cause I’ve always wished it were a little bigger.   And I was SWEATING, let me tell you. We came together, me jacking him off while I fucked him until I came inside him (in a condom, of course…  although I feel like he wasn’t going to ask me to put one on?  He got up to grab lube and put on a cock ring, and when he came back I had to ask for a condom.  Kind of weirded me out a little, I didn’t like that…  but maybe it was just an oversight or he didn’t think we were going to fuck right away.  Would anyone really fuck a prostitute without a condom?)

We cleaned up, although we didn’t take a shower, which I would have liked to do.  It was down and dirty sex, and I was covered in sweat…  and washing after sex lowers the risk of STD transmission! fyi!

As we lay in bed together, smoking the last half of our joint, he told me that he had just recently left his lover of almost two decades.  Two decades!  Apparently this guy ended up being a little unstable mentally, and it was all for the best.  He also said that in all those years they never stopped having sex…  2 or 3 times a week.  My longest relationship was 3 or 4 years (on and off), and my sex drive was already way down by the end.  That’s impressive after almost 20 years, no?  Although he also said he never met one member of this guys family, and he could count on his hands the number of times they kissed.  Which isn’t quite as hot.

He gave me some PJs to wear for the rest of the night, and with them he handed me a pair of socks.  Not just any socks…  But the socks that those really distinct sock monkeys are made from.  Like, vintage sock monkey socks.  Would the antique goodness ever end?

I wish I could tell you everything he showed me and told me about, but again, the uniqueness of some of the pieces would make them traceable.  He had an old school record player, the kind that plays wax cylinders, not flat records.  Some of the first recorded music!  And the quality was excellent. I told him that it seemed almost fake.  You know when you watch a movie/cartoon/TV show, and they play “old” music that is clearly a new recording edited to sound like an old, scratchy phonograph?  Well this was the real thing.  I know that sounds silly.  We’ve all heard old scratchy records.  But this really was different somehow… he had cylinders that were in EXCELLENT condition, and his machine played them beautifully (and really was a work of art itself).  Ugh.

About this time of the night, his dog started getting a little extra jealous, or territorial or whatever.  He went from nippy to hardcore bite mode.  I was standing by the record player, and he started attacking my feet.  I reached down to push him away, and he bit my hand.  Unless I grabbed his neck (he had an extra body’s worth of skin…  cutie) or constantly pet him, he legit attacked me, to the point of drawing blood! (well, just a little from my left pinky…  but still!)  And while this was happening, his owner looked on and said things like, “Look, he likes you!” and, “Awww, he’s so cute!”  I’m really not exaggerating, it was actually totally bizarre.  His dog was biting my legs and feet and hands, and he looked on and cooed.  My roommate is bringing his dog to our new place; please remind me not to be that kind of dog owner.

He had some gorgeous, large, intricate music boxes, too.  And paintings and sculptures and all sorts of other things.  He had a fabulous grand piano, and original sheet music to a ton of classic songs.  He asked me if I had friends that could play well, as he would love to have someone over to play some of this amazing music that was sitting and waiting in a box.  It was very sweet of him, but I don’t think I’ll take him up on it.  I’m not sure how to tell my piano playing friends that one of my johns needs a good sight reader.

At that point, we were high and hungry, so he cut up some delicious rolls and melted brie on top.  It was to DIE for.  In his words, we were “pigs.”  Drinking wine, eating bread drenched in cheese…  mmmm.  After the bread and brie, he gave me some AMAZING chocolate caramels that had salt on them.  SO good (I still have one left that I brought home).  The whole night was sensory overload.  Food, music, art, alcohol, pot, sex…  Really, it was a good night.  He was a nice guy.  We eventually burnt out and headed back to bed, where we fell asleep….  Cuddling, I think.

I woke up the next morning around 7, with an awareness that he was already up, even though he was lying next to me in bed.  We started grinding some, and I ended up fucking him in our spooning position.  It was fine, and he cued my cumming much sooner than the night before, which was nice.  I wasn’t really looking for a morning sex marathon.  After I came, he got up to take the dog downstairs (he had spent the night with us in bed…  he was very sweet in bed, not as aggressive) and I tried to go back to sleep, but failed.  Eventually I wandered downstairs and he made me some excellent coffee and a kind of mediocre yogurt/granola/banana mush that I pretended was exactly what I wanted.  We ate at his table and made small talk…  He made it VERY clear that he had an excellent night, and he would definitely have me back again.  Good to know!  He paid me ($860. $10 extra) and I didn’t want to be rude and run out right after the money exchange, so I let him show me parts of an old movie with some singers that he thought I would like.  I also ended up showering there, which at that point I would have rather done at home, but it didn’t really make a difference so I did it to make him happy.  And he really was happy, again giving me some confirmation that what I’m doing with guys isn’t the norm, which is nice.  He also mentioned the possibility of going with him on a trip he has to take to Puerto Rico.  I’m not sure how I feel about that yet…  but why not?  As long as I am actually getting paid money, not paid in ‘fun travel time.’  But we’ll see!

(I had to pay the rest of the rent on the place I just left…  hence the money order. Full cash earning are in the pic at the top of this entry.)

I’m becoming a lot more comfortable walking into different situations; I’m impressed with myself.  Putting aside the fact that I never thought I would be an escort, there was a time in my life when I never would have dreamed of walking into a stranger’s house and striking up conversation.  I was the awkward kid growing up.  I guess most people were, but really, I had embraced the role of outsider.  I never wanted to be a ‘cool kid.’  I know that’s a silly idea… coolness is besides the point, right?  Everyone should just be themselves and be open… which can then make you cool, maybe.  But to think that people find my ads and think, “oh, he’s hot, interesting and desirable,” and then call me up and have me come over, and then find me attractive and impressive and want to sit on a couch and chat about the world…….. it kind of blows my mind.

I don’t mean to make out my escorting career to be some sort of ego masturbation tool, or make it seem like I’m using it to chase some feeling of self-fulfilment that my ‘real life’ leaves empty.  Frankly this blog does those things more than the actual escorting.  Just some observations.  Living life is strange!

-B