This story dates back about a year and a half.  He saw my ad on an escorting website and wrote me an email:

Him: Hi. Your profile is intriguing and I’d love to see some face pics. All Best, *****

Me: Sure, they are attached!

Him: ****** — Do you have a hairy chest and legs?  Could not tell precisely from the photo on the website.  Your face pics are adorable and sweet. –*****

Me: Thanks! i do have hairy legs, and right now some lighter hair on my chest/stomach… i sometimes shave but it’s half grown back now!

Him: Don’t shave!  Let it grow naturally.  = )

Me: haha i definitely am now, don’t worry it’s not all back, but it’s def a good amount.  i shave every once and a while to change things up, but i’m getting a little tired of it…  which i guess is lucky for you!

Him: yes, lucky for me.  =)
do you think you would be available to meet today or tomorrow?

Me: I miiiiight be able to! I have a friend who may be coming into town tonight…  or might not be haha…  i think he won’t at this point.  But how long/what time would you be looking for?

(I don’t exactly remember, but I think my “friend” just was an excuse in case I didn’t feel like working, or if I got a bad vibe from this guy.  Clearly it ended up panning out!)

Him: Just left you a voice mail on your cell.  Call me — maybe it will be easier to talk on the phone.

(We talked on the phone and he seemed very nice.  As usual, it seemed like he had been drawn to my ad because of the focus on conversation and chilling as opposed to just sex.  We decided to meet for an hour or two, and he sent me an email after we got off the phone.)

Him: Hi ******.
Confirming 3 pm on Wed.  My address is ***********.
Subway directions: *************.  As you head out of the station steps, and go through the turnstiles, you’ll see two sets of exits (one to your left and one to your right).  Exit through the stairs on your RIGHT.  I’ll meet you on the sidewalk.
Please be clean, ready for conversation, and be as sweet as you sounded on the phone.  =)
Please confirm receipt of this e-mail.
Best,
****
PS: If, for any reason, you are delayed or need to cancel, please call me on my cell (***-***-****).

I ended up running late because of the trains.  When I finally got there, he was standing in the rain.  He was a plump man that I guessed to be in his early thirties, and he was holding a giant umbrella, the kind that annoys me on crowded sidewalks (unless it’s covering a family of four) but that he probably got away with in his less crowded neighborhood.  He told me that he had almost given up on me and gone home, and I’m supremely thankful he didn’t because it turned out to be a very profitable night.

We started the walk back to his apartment, and I noted how nice his neighborhood was.  Very cute and brownstoney.  I could tell right away that he was smart, and seemed warm.  Maybe a little formal?  Or maybe that was my impression by the end of the night.

We reached his apartment building (surprise, a brownstone) and climbed the stairs up to his floor.   The inside of his one bedroom was cute, although a little crowded.  Boxes here and there, but a nice space.  Living room, bedroom, kitchen, bathroom, and probably a couple closets.  My shoes were already off, as his apartment had a no shoe policy, but he asked me if I wanted to take off my pants, and soon I was sitting next to him in my shirt and underwear.  He put his hand on my leg, felt my leg hair and smiled, casually mentioning again that he loved body hair.  Too bad I had trimmed my chest and stomach hair a bit already.  I don’t want him to seem at all lecherous, feeling my leg hair while we sat and chatted, because he really seemed sweet.  He was very into theatre, so that opened our conversation, and we soon realized we probably had some mutual friends.  It was even possible that we would run into each other at some point.  I really wasn’t worried about it, though.  He seemed very nice and discreet, and clearly wouldn’t want anyone to know about our arrangement for the same reasons I wouldn’t.  Even if we ran into each other at some point, it would be totally plausible that we had met at some friend of a friend’s party.

After 30 or so minutes of conversation, we started kissing some and moved to the bedroom.  As his clothes came off, I realized that he really was about as all around unattractive as I would have guessed.  He was chubby (or maybe just fat), and his dick was small, his public hair wiry, unkempt, and longer than I would have guessed for someone who was generally smooth on other parts of his body.  We made out, although his kisses were very soft, in a tentative way.  Almost just pecks at times.  Every time I went down on him, he pulled me off pretty quickly.  I think he didn’t have very much endurance.

The strange thing about the whole hook up was that he kept on asking me if I was ok.  We would make out, and he would pull away and ask me if I was ok.  I would always smile and say yes, absolutely.  But I think what was really happening was that he wasn’t sure if he was ok.  Or, maybe he wasn’t sure how he was doing, and his defense mechanism kicked in every time he doubted himself.  Which was every time we did anything sexual.  Which happens a lot during sex.  Although, he definitely was seeming to veer away from anything anal, at this point.

Side note: With some overweight clients, I can’t always tell what they want in terms of attention paid to their upper bodies.  If I’m hooking up with a hot guy, I’ll touch his abs/chest, lick him, etc… general hot hook up stuff, nothing crazy.  But with an overweight client who may be self conscious about his body, I at times feel like I’m drawing attention to and/or emphasizing his flaws if I do those things.  But I also don’t want to IGNORE it and have them be self conscious in that respect.  I also don’t want to deprive them of a hotter experience, if they’re into that.  For the most part, clients are easy to read sexually.  But with this man, he was so tentative that it was hard to tell what he wanted…  I got the impression that he didn’t want me to pay attention to his upper body, but also that he wasn’t confident enough to let me know what he wanted.  I’m still not 100% sure how he feels.

He suggested we move to the shower after 10 or 15 minutes, and we continued with the touching/kissing.  He ended up blowing me until I came in his mouth, and he spit it out.  “That’s the best thing about doing it in the shower,” he said. “No extra cleanup!”  I realized as he said this that I think he’s a little OCD.  I apologize to any true OCD sufferers out there, but he was very strange about touching/kissing/blowing during the whole hook-up.  At the time I wrote this off as inexperience… but I think he actually found it all very hot, while at the same time, not wanting to get “dirty.”  He seemed like a very particular person.

We finished our shower, and we headed back out into the living room, where he proceeded to show me his extensive stuffed animal collection.  I shouldn’t call them stuffed animals, they were actually all very artfully crafted, expensive collectibles – literally thousands of dollars worth – but yeah, they were stuffed animals.  Some were on shelves, some still in boxes stacked against the wall, all around the room.  He had a story for each one, and had even gone to conventions to sell and trade.  It was kind of endearing, really.  It really brought him joy!

At this point, he asked me how much it would be to spend the night.  I told him my rate was 1000, which made him hesitate, so I offered 800 (which is a rate I’ve accepted before.  I don’t like negotiating, but it’s a little better if I aim high and still end up with a solid number.  Without a steady stream of income, sometimes I have to bend my rules, as much as I would warn against it to other escorts).  He felt bad, though, and didn’t want me to have to lower my prices.  I insisted it was fine, but he offered 900 to ease his conscience.  So my little afternoon turned into a sleepover!

This is where the night took somewhat of a turn.  This requires a little back story, but I’ll be brief. Months before this meeting, I had met a guy at a bar from Mexico who was on a business trip.  We hung out and slept together the couple days that he was here, and then kept in contact in the following months.  He ended up flying from Mexico to visit me for a couple days over the summer, and one night while we were drunk, we had unprotected sex.  Now, I’m writing this over a year after the fact… I honestly don’t remember the exact details or order that everything happened.  However, the facts that I know are these: I had an std, gonorrhea.  I don’t make a habit out of having unprotected sex, but I believe I got it from someone I trusted at the time.  I gave it to the guy who was visiting me before I realized I had it, and soon after had some symptoms, took antibiotics, but had my initial tests come back negative, so I assumed I actually didn’t have it at any point.  I was not seeing clients while I was unsure of my std status.  However, my Mexican visitor’s discovery of the fact he had gotten it, and our initial discussions about it, started this night while I was with my client.  Hope that makes enough sense.  But again, I know that on this night I had taken antibiotics and it was gone.   It’s kind of embarrassing to write about, but it happened, and it’s done.  And of course, I’m so thankful it wasn’t something client related, and it wasn’t anything worse.

So, we decided to go to dinner, and as we were walking to the nearby restaurant, I got a voice mail from my Mexican man that said he really needed to talk.  But I really didn’t want to be rude while I was being paid for my time, so I had to sit through dinner, knowing that I had personal matters that really had to be taken care of.  Also, keep in mind, this guy that had visited me was someone I really cared about.  I was planning on visiting him in Mexico in the coming months, and was even considering taking Spanish lessons for the trip.  It was really eating at me that I couldn’t talk to him on the phone at that moment, and I think he was feeling the same way, as he kept calling me throughout the meal.  It was a struggle, but I managed, making conversation and forcing myself to eat the excellent food that my client was buying for me.  Apparently I did a good job, because he clearly enjoyed himself.  As we walked back, though, I knew I had to call this guy.  It was going to be less rude than how distracted I was going to be with my client if I didn’t call.  When we reached the apartment, I told him my friend had been calling me all night and asked if it would be alright if I chilled outside for a second and returned his call.  Thankfully, he was totally ok with it.

I found out that my Mexican man had been diagnosed, although not fully tested yet, with what looked like Chlamydia.  I truly felt awful, but ironically, the first thing he said to me in his good (but occasionally broken) English was “Are you still my friend?” He was just as worried as I was about the others reaction to the news and the stigma that stds carry, even if I was a part of it.  After about 10 minutes of discussion, my client called from inside his apartment to make sure I was ok, and after switching back I wrapped things up.  By the end, it was clear we were more worried about being on good terms with each other than the std itself (which sucked, but could be dealt with), and I was able to refocus my night on my client.

I went back in, and apologized for taking so long.  He just wanted to make sure I was ok, and asked what was wrong.  Clearly I wasn’t about to tell a client about my std troubles, so I avoided the topic by saying it was discussion about money owed by a friend (that had to be discussed tonight, for whatever reason), and left it at that.  He was very concerned and sweet.  We moved on to listening to some various musicals from his excellent CD collection (New York Philharmonic recording of Sweeney Todd, highly recommended).  Then he realized he had to leave some feedback for a hotel that he had stayed at during a recent visit to Vegas.  This is when I realized the extent of his semi-OCD qualities (again I use that term loosely).

Apparently the lobby of this hotel was disorganized, and part of my client’s NYC job (to be very general) was about organizing groups of people.  He proceeded to spend about an hour drafting an email to this hotel, telling them about their poor customer service, and how (very specifically) they could improve the flow of their hotel lobby.  While a little bizarre (I would usually assume this kind of behavior is reserved for older, senile people with nothing to do), I have to admire how well thought out his arguments were.  I’d never been to this hotel, but I’m sure he was right!

At this point it was getting late and it was time for bed.  Nothing else sexual happened, which is always interesting to me, as I think of the high price of escorting as directly relating to the sex.  Also interesting, he didn’t need me to sleep in the bed.  He insisted I take the couch in the living room, because he snores.  Double score!

The next morning, I left relatively early, as I had some place to be (or maybe just said I did, don’t really remember).  He didn’t have all the money, but gave me the first half before he got more from the atm.  He said he “hated this part” while he counted the money.  We really had connected over the course of the night, and I think he didn’t like the feeling that it was in exchange for money.  Or, maybe he just didn’t like the fact that he was hiring a prostitute.  But again, it made him sweet.  He implored me to be careful, and I assured him that I didn’t do this often.  He still gave me his worried face though.  He was very much a mama bear.  A particular, worrying mama bear.  After he walked me to the atm and gave me the rest of the 900, we parted ways.

The story of this client has a much more recent part 2, which will be titled “the 40-year-old virgin”.  I’m torn between writing that and writing part 1 of my coke head  client saga.  Look for one or both in the coming weeks.

Thanks for reading!
-B

I’m posting this solely so that my last post isn’t the first thing that new visitors read when they find my blog.  I tried to choose my words carefully, but I see how it easily could be misread as me hating escorting but feeling pressured to do it.

I’ve gotten a lot of hits in the last day from someone who posted my link in a forum.  One of the responses to that posting was:

“I really try to avoid guys like this who’re escorting just to pay the bills, but seem to hate it. I seem to run into this mindset more with the higher priced guys (maybe priced to get over their squeamishness), so I have yet another reason to avoid them. A few insightful questions and a keen intuition work wonders to filter this type out.

My favorite type of “hobbyist” is a guy who’s just a naturally gifted “people pleaser” who’s great with the banter, genuinely loves interacting and getting to know strangers and has an “everybody deserves some affection” frame of mind.”

Now I think a “hobbyist” is one who hires escorts? Haven’t really used that term, not sure if he’s talking about the escorter or the escortee here…  but either way, in terms of the excerpt from his reply, I am TOTALLY the latter.  I don’t find escorting demeaning, soul eroding, hateful, etc etc etc…  and I think I’ve communicated that in previous posts.  I wouldn’t be doing this if I thought it was an awful thing.  In fact, I almost always walk away feeling validated.  As I said in a reply to a comment on my last post:

“My point isn’t that I hate myself when I do this… it’s that some days, I don’t feel like heading into the office!”

I also should have clarified my comment about trying “everything else” besides escorting every time I need money.  I don’t do this because I despise escorting.  It’s that every time I escort (especially with someone new) it’s like jumping off a small bridge.  It’s a little scary!  And yes, someday I’d like to move on from it.  Not because I hate every second, but because I’m an actor first and foremost, because escorting has its risks, and because escorting isn’t socially acceptable.

that is all. carry on!

-B

Escorting has such a push and pull for me.  Most of the time, I want to be done with it.  Socially, most people I know would be upset or appalled if they found out I escort on the side.  I would like to avoid the stress and danger.  And I’d like to only have sex with hot people.  On the flip side, it’s SO profitable, and once I’ve found a client, it’s relatively easy.

When I’m running low on money, I consider all my other options before escorting. I hem and haw with my roommate, seeing if it’s possible to overdraft my bank account for the 10th time, juggling credit cards and paypal accounts.  What can I sell on craigslist?  But this time, I’m about $200 or $300 short, and that will be easy enough.  I realize this may seem in contrast to many other entries that are so pro-prostitution, but there is a fair amount of stress associated with this job for me.  I woke up a little late (2:30…  maybe I shouldn’t have stayed up until 7am watching The Walking Dead) and realized today is a working day.  I’m not really in the mood, but the universe has decided.  ah well.

I guess everyone has those days they don’t want to head into the office!

-B

I have a couple updates I should post, but this one is about my latest encounter.  The one before it requires a little back story, so this one was easier to bang out.

As has often been the case throughout my escorting career, rent time became business time at the end of last month.  My roommate and I thought we would have enough money to cover our bills, but as the first approached, it became apparent that our combined cash was evaporating, and we clearly would not have enough to pay our rent.  So, on the last Saturday before the first, I jumped back into the world of craigslist, looking for a gen (‘generous’) guy who wanted me to spend the night.  While it could be argued that I needed money enough to make multiple hour meetings, I really didn’t want to.  I wanted to find one guy who have me over for dinner/drinks/sex/whatever for about $800, which was more than I needed, but what I feel is fair for me.  Most guys stopped responding after I told them the price, but I was able to negotiate a couple down a bit.  Here are (most of) the email exchanges with the man who became my (pseudo) client:

Him: Hey guy,
Bored masc 35yo on the UWS, looking for something fun to do tonight. A cute/hot boy sounds appealing.
Tell me about yourself (face pic, what you get into) and such!  (I’m 5’10, 180#, white/jewish, clean/neg, chill…)

Me: Hey!  Attached a couple pics.  Into whatever really, nothing too crazy. Looking for 200/hr or 800 for overnight (which is preferred, or at least more than an hour). Let me know if you’re interested!

Him: Thanks for the quick response.  And cute pics.  I’m not a “hi let’s fuck” kind of guy so wouldn’t want an hour.  8 is kinda high so need to think though.
What’s fun for you?  What were you thinking of for the evening?

Me: Oh whatever really! Like I said, nothing to crazy.   I’m down for movies, wine, conversation, chilling in bed, etc.  Would be up to you, really!

Him: LOL, ok. I’m on up at ********.  When do you think you could make it up here?  7-8?

Me: Yeah I could do 8pm.  And you’re down for 800?

Him: I’m thinking about it.  Do you smoke?  Party?

Me: Nah I don’t.

Him: Cool.  So you sound great, and I’d likely have a good time, but I can’t justify it, so I’m going to pass.   Sorry guy.

Me: No problem.  Let me know if you change your mind.

(About 30 minutes later, I decide I maybe should adjust my price, which I hate doing, but I’d backed myself into another corner with my rent being due in days)

Me: I could be willing to down some on the price.  What would you be willing to pay?

Him: Hey *******,
Sorry for the delay I was offline cooking.  I appreciate the offer but I’m kind of hesitant to throw out a number.  I thought about making a counter-proposal but didn’t want to insult you by saying you were worth less than what you were asking for, or if you accepted be worried that you’d be unhappy/subconsciously resentful of the bargaining throughout the course of the evening which would suck for both of us.
That said, if you’re suggesting I throw out a number, things are different, but I’m not exactly sure how.  God I wish I didn’t think things through as much as I did.  It’s a truly annoying habit.
So now that my brain is grappling with this, it need like 5 minutes to process.  This would be much easier if i were at least slightly less sober — which I suppose I would be if you were here.  And given that you send your e-mail like an hour ago, this all may be moot.
So while I’m pondering in the next 5-10 minutes, let me know if you’re still looking and what your favorite TV show is and what kind of foods you especially like and/or hate.  And do you drink?

Me: haha it’s all good! I understand!  I am still looking, but take your time.  TV wise, I loved lost, and I’d say my current favorite is weeds.  I enjoy dexter, but I’m still catching up on it.  Very open with food!  Maybe a little less fond of seafood?  But I still like it. And yes, I definitely do drink!

Him: So I’ve thought about it, and I’m still not sure where to go with it.  I think I’d still be worried that you were unhappy/resentful about taking less.  Which would lead to me having less fun, etc.
I know this is weird, but sorry.

Me: I understand! But you really don’t need to worry.  It was my choice to ask if you’d offer less, and you also seem like a great guy that I’d actually have a fun time with, which is pretty appealing from my end. Would you be willing to do 600?

(at this point we IM’d through gmail chat, and while he might have met for $600 earlier in the night, he felt like we’d wasted some of our time together hashing out details, so a different night would be better. We settled on meeting on Monday night for dinner/drinks/whatever, sleeping over included.  I was a little nervous, as I absolutely needed to pay my rent by Tuesday, so a couple hours later I emailed him again)

Me: Hey!  Just wanted to say, please let me know ASAP if you think monday won’t work for whatever reason!  Like I said, I’ll be telling my landlord to hold off for a day, so it would be bad if I didn’t know until monday that it wasn’t happening.  That said… I’m also very much looking forward to it!

Him: Definitely

(and then, on Sunday:)

Him: Good luck at the new job tomorrow!

So, I was planning on meeting him on Monday night.  I was a little nervous, as I was starting rehearsals for a show, and to have to also worry about my night job was extra stress…  but at that point, it was necessary that I have his $600 by Tuesday morning.  So, during the day on Monday we emailed/texted some to confirm, and around 7:45 I arrived outside his Upper West Side apartment.  I called him, he told me his apartment number, and I was buzzed up.  It was a nice building.  No doorman, but an elevator.  He met me at his door.  He was very average, but not TERRIBLE looking.  Maybe a little dorky?  Big nose.  Not a great body, but not particularly overweight.  We shook hands, I got his name, and I repeated my fake one.  He asked if that was my real name, and I said no, and told him what it was.  I don’t know why, but I’m so bad at lying about my name if someone asks, even though it’s not a great idea to tell.  From here on out, I won’t.  That’s a pact I’m making with myself, with the internet as my witness.  This is partly because after I said I didn’t mind him knowing my name because I could tell that he was “normal guy,” he replied with, “Not completely normal.”  I don’t think he was about to kill me…  but I’ll just take that as a sign that someday some sketchy guy may stalk me.

We chatted for a minute by the door while I scanned his apartment.  It was nice!  Classy furniture. A white sofa with claw feet.  I don’t remember many details.  Clearly he was making some money, as he had a spacious UWS apartment with nice things.  I had told him I was starting a new job that day (which was true, I was rehearsing for the show I mentioned earlier) and I told him it was a children’s theatre tour.  A lie, but I wanted to be a little vague.  I asked him a question (I forget what, maybe something about what he wanted to do for dinner?) and he stumbled a little on the answer, and then apologized and said he had a migraine.  In fact, he said we shouldn’t do anything that night.  But, because he had promised a meeting, he would pay me now and we could meet another time!  That’s right.  He paid me, a random escort that he met on craigslist, in advance.  I mean, THAT is a generous guy.  And normally I wouldn’t feel comfortable doing that, but I really did need the money ASAP.  I didn’t have another option, and I was very upfront about that.  So, he walked me to the atm, making pleasant small talk along the way, took out $600, and we parted ways with plans to maybe connect later in the week.  I thanked him PROFUSELY as I said goodbye.  Really, I still can’t believe he did that.  I also texted him before I got on the train, saying, “Seriously, thank you again for your generosity.  It speaks volumes about you! Be in touch ”

Side note: As I was on the phone recounting this story to my friend a minute later, I said something along the lines of “I can’t believe he would trust me like that. I’m just a random whore!” and a homeless man in a sleeping bag on the sidewalk shouted at me “We’re all whores!” Thanks, God, for that touching reminder.

The real kicker of this whole thing is that it happened on the first of this month.  It’s now about three weeks later, and this guy hasn’t contacted me.  I feel like he must be pussying out, or maybe wasn’t interested in me once I showed up but then felt obligated to pay me? Or maybe he’s just been busy and will still contact me later.  But it seems strange that he hasn’t written ANYTHING for three weeks.  I feel like I should write and say something like “hey sorry, been busy, but let’s make plans soon, ok?”  But really, the ball is in his court.  He’s the one who paid!  I guess we’ll see.  If he never writes me, I’ll have made $600 in about ten minutes.  Around $60 a minute?  Not too shabby.

-B

This entry is the equivalent of a drunk text. I could have waited until I had written something with a little more content… but my friend jim beam recommended I let the world know I’m alive. So…  fyi, i’m alive. and writing again soon.

Sometimes this blog feels like I’m vomiting into the sea of the internet…  but most of the time, I feel like I’ve created something worthwhile that not enough people (in the business or outside it) are reading.  I hope you (dear reader) feel the latter.

-B

PS – odlfkjgs;orbo;seirmg;kdfgl;ksmw4o;imvea

I got a comment today that said this blog was in a dire need of an update.  i agree! And I apologize for those that have been checking back recently, because I should have posted this earlier.  Remember the job I was talking about in my last post?  Well, I got it, and I’m no longer in NYC, at least for the moment.

SO.  for now, little dream came true, don’t need to escort.

Now, i do have a couple updates left that i could do while i’m off doing this job…  i don’t have the time to do that right now, but i may in the coming months!  And i may even have the time to make a new website, as i had planned before.  So it’s worth checking back…  and I will still respond to emails and comments if i can!  and i’m not sure i’m done ‘doing this’ forever…  which in terms of the life of this blog is really the most important thing, isn’t it?

Thanks for reading.  Whatever happens, I’ll keep you updated!

-B

i got a call last week from a show that it truly would have been a dream for me to be a part of…  man i sooooooo wish i could write details, but just know, it would have meant i was leaving the city for months, and i would been making (very relative) bank.  at least enough to cover all my expenses AND save a little bundle.

Said dream show said they had a place for me, IF this guy left (and for whatever reason that seemed likely), and if that happened, I would be on a plane in days.  I was ready for a whirlwind! and ready to leave this blog to mold a bit out in cyberspace….  which would have been a shame, because it really is important to me, AND because:

I have plans to redesign this whole thing…  i want my own domain name(s) and my own site design, and maybe an expansion (and/or reorganization) of content. This is partly because I want more people to read it, partly because i think i could be used as a resource, partly because i wonder if my writing could go onto bigger and better things than my own little blog, and partly because i think i could generate some revenue, especially if i can get my hits into the higher numbers (which is totally possible).

BUT of course, all those plans were about to crumble… until i got the 2nd phone call telling me that it was a false alarm, and for now, they didn’t need me.  so, i’m going to stay here, and hopefully soon, you’ll see a pretty new page (but the same quality content you’ve come to expect).

Have some appointments set up (and a pretty ridic story that i haven’t told yet) so check back!

-B

Easiest guy ever!  I was in and out in 45 minutes, and he gave me an excellent tip, bringing my total to $300.  That’s $6.67 a MINUTE.  I have a friend who was recently excited to have found a temp job for $10 an hour. what what?  And really, this was so straight forward and easy.

I buzzed in and went up to his apartment, where I was met by him, two cats, and a dog.  He was Asian, mid 30s, not a great face, but fine, average body.  He was SUPER nice.  As I walked into his living room from the front door, he stopped me and asked me to take off my shoes, which I quickly did.  I started kissing him, and he stopped and asked if I wanted to take a seat.  I had asked him via email if he was interested in more than an hour, and he said he wasn’t, so I was surprised that he wanted to sit around and chat.  We sat on the couch, my arm on his leg, and talked about his pets (originally owned by his ex), his work (pharmaceutical something or other) and his piano playing.  His two cats were all over us while we talked…  more than he was on me.  He seemed a little hesitant.  Finally we started kissing, and he asked if I wanted to move to the bedroom.  We made out by the bed, got undressed, kicked the smaller cat out, closed the door, and had a pretty vanilla hookup.  Kissing, I blew him some, he blew me for a second…  He clearly was into massage and touching, which he had mentioned in our emails but reaffirmed with his deep rubbing of my shoulders while we made out.  Finally I flipped him over and gave him a pretty good massage…  I could have done better. And the one he gave me a couple minutes later was to diiiiiie for.  Could have been longer and a little more intense, but he clearly knew what he was doing, and pulled some excellent moves out that felt AMAZING.  He also was a little vocal through the whole hookup…  telling me what felt good, and how cute/beautiful I was.

He had mentioned a couple things in his emails that he liked doing that didn’t happen.  Namely, he didn’t ‘rim my jockstrapped butt’ (forgot to mention, I wore a jockstrap, which he had requested), and he didn’t top me.  A key part of the short length of the meeting was the fact that I don’t think he had much endurance…  he pulled me off a couple times as I went down on him. It ended with me on my back, and him cumming on my chest.  The whole this was just… fine.  He got me some paper towels to clean up with and we got dressed.  Our hour definitely wasn’t up, so I asked if he wanted me to stick around a bit, but he didn’t seem to want to keep me.  We made a little small talk as I headed out.  He told me that his dog had cost $700 originally, but later needed surgery that ended up costing $15,000.  Ouch! But gimme some of that cash? He paid me, I said my goodbyes to him and his animals (who I kind of wanted to steal and take home with me) and left.

Forty five minutes betch!  i’ll take it.

-B

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

I should have written this entry right after I got home from my appointment with my now 66-year-old man (his birthday was over the weekend).  Maybe I went out after?  But clearly i didn’t update, and now, a week later, this entry will be headed in a totally different direction.  It’s a little unfortunate, as I feel like I walked away thinking “oh man, I have some awesome things to write about!” but now really can’t remember for the life of me what conversations/events occurred that were anything new and exciting when compared to past meetings. ah well.

We set up a meeting via email (as always).  In our emails back and forth, I tried to bump up our usual two hours (meal/hookup, which he paid $450 for in the past) to an overnight for $1000.  He said, “_____ is my birthday, yes __/__/4(4).    It would have been a great birthday present to myself to have you sleep over, but right now it’s not financially possible.  So, how about 9:20 Thursday night, and we’ll have some fun………………”

So I went over planning on the usual.  Dinner/hookup, which equals two hours. (<—- important plot point)

He had asked beforehand what I wanted for dinner, and I said thai, not realizing that I was going to have thai for breakfast/lunch with the boy i’m sort of seeing (see previous entry) and chinese food as an early dinner with friends.  So I was excited when I got there and he had goat cheese salads for us.  I killed the salad, thankful that he hadn’t gotten the thai…  and then he made a joke along the lines of ‘haha what if this had been all i’d gotten us to eat?  you know you’ll always eat well here’ and pulled out the other eight courses.  pad thai, some sort of shrimp/curry thing, rice, vegetables, rice chip things… ugh.  So I pretty much stuffed myself, especially because I wanted to drag the meeting out to make sure that it ended up being two hours so I could get my four fiddy. (<—- important plot point)

We are getting much more comfortable with each other.  He had requested that I bring something to ‘spice things up’ in the bedroom at our last meeting, so I had a blindfold with me.  He was excited about that, and showed me the ice cream he had bought for the bedroom (if we so chose).

side note: If you got ice cream for a sexual encounter, wouldn’t you get plain vanilla or chocolate or strawberry or something?  Cause he got two kinds: some sort of fudge/rocky road and girl scout samoa.  Really?  Is this the norm?  I picture ice cream play as sensual and cool and smooth…  drops of pure, chilly, sexy snow that melt on your body and in your mouth….  not the dirty, sandy gravel snow that the plow pushes to the side of the road and that lasts until spring because somehow all the gritty shit from the street preserves it.  Mmmm, yeah, plop some of that frozen sandpaper milk on my penis.  gimme somoa that.  If I’m sucking ice cream off a dick, I shouldn’t have to chew a cookie in the middle.

So we ate and talked (this is where i’m forgetting some things that I thought were important before).  We made out in his kitchen, and I paid special attention to his back, which as I’ve said before is SUPER sensitive.  He ended up bending over and sucking me for a bit.  Again, I dragged this out as much as I could.  Finally we moved to the bedroom, where we got undressed and reclined.  Most of the hookup was him sucking me off.  The ice cream/blindfold were left behind.  I hate to say it, but I’ve stopped paying as much attention to his nether regions.  He said one of the reasons he appreciated me was i wasn’t afraid of the fact that he couldn’t really get it up…  but I am a little over it.  There just isn’t much to do with it!  Also, one of the things that can turn me on about a guy that I’m not especially attracted to is his dick…  most dicks are hot!   cum is hot.  But his just doesn’t really do anything, and because of it, through this meeting and the last I spent most of my time ‘on him’ absent-mindedly jacking it off.  I think he’s fine with it/hasn’t really noticed.  He enjoys giving me attention.  And again, he fingered me at the end until i came.  The cumming feels good, but I really dislike being fingered.  i really think i would rather get fucked than fingered.  I don’t know why but it’s always more painful.  And for some reason the way he does it is more uncomfortable than usual.  ah well.  I’m really just lying back, so it’s hard to complain.  I showered after we finished.

I forgot to mention this in my last entry about him, but last time I was over he noticed that my underwear was in rough shape…  had some holes and stuff.  He didn’t straight up say that, but he mentioned that if I wanted, he would give me some underwear that he wasn’t going to use.  Brand new. oops. time to upgrade my wardrobe!  They weren’t very cute, though, and when he reoffered them after my shower I politely turned him down.  He also gave me a can of spray deodorant, because I had mentioned to him I’d never used it before.  I don’t really like it, but I’ve been using it some because I ran out of my usual stuff and have been lazy.  oh and he gave me a little floss thing because we had eaten.

We were saying our goodbyes, but i hadn’t been paid yet, so I brought it up, and he sort of yelled at me (jokingly?  can’t always tell…  wasn’t mean though) and said that it was in the same place it always was, on his dresser.  He’s handed it to me in the past, but I guess from now on I should pick it up myself.  It does make it easier (and keeps the illusion of me just coming over to hang.  While he doesn’t try to avoid discussion of ‘what we are,’ i think he still might not like the actual moment of payment.  understandable!).  I grabbed it, and before I left took a picture with him so he could show his son what I look like.  I found out later, after asking him, that his son knows I exist but doesn’t officially know I’m paid.  I’m just his dad’s boy toy.  He’s told a couple other family members, too, but I believe only his closest friend knows that I am an escort.  I’m sure everyone else is assuming i’m getting some sort of sugar, though!

After I left his apartment and exited the building, I realized that i had been underpaid.  I assumed i was getting $450, but I ended up with ONE hour, $250!  I wasn’t sure what I was going to do…  This was a semi-regular client that I genuinely liked, and I didn’t want to cause drama if he truly thought that’s what he owed me.  Of course, this is non-confrontational me, and of COURSE, I needed to get that money.  I have my best friend/pseudo-pimp to thank for talking some sense into me.  We had our usual meeting of usual length, and he underpaid!  So the next day I sent him an email saying:

“Hey!  Hope you are gearing up for an excellent birthday!

I’m sure this was totally unintentional, so really don’t worry about it, but we spent two hours together yesterday and I only got $250?
No need for stress, and I know you enough to know you aren’t the type to do that on purpose. If you are still looking to have a future meeting we can deal with it then!  Or if you thought it was less this time for whatever reason we can talk about that too, but I just wanted to write you before I forgot about it.  Have an excellent bday tomorrow, I wish I could have joined you!”

To which he replied:

“I have brunch plans Saturday, but plan to be finished around 1-2 in the afternoon.  And plans again at 6, so if you’re free the in between time, call me to double check and you can pick it up at my apartment.  Sunday, I’ll be home in the early evening, if that works.  Just let me know.”

So I met up with him on saturday, right before he headed out to his birthday dinner.  He handed me another $250 and said that NEVER wanted me to feel like I was being taken advantage of or being put out.  He thought that in the past, dinner hadn’t counted and we had spent two hours in the bedroom (not the case, but I believed he believed that) and that in the future we should spell out exactly what/how long we are doing.  Which is right, we really should do that.  I felt a little bad that I was stopping by on his birthday to collect cash, but I spent a little time chatting and having a drink (water).  I made him a little late to his birthday dinner, but I think that was really his fault for letting me stay.  We left the building together, and I wasn’t anticipating it, but I think he was a little embarrassed to pass his doorman with me, even though I’m SURE his doorman didn’t think I was an escort.  I would bet ‘grandson’ was guessed, but who knows.

Skip ahead 24 hours, when my throat is a MESS from some sort of infection.  During our second meeting, he had reminded me that he was a pharmacist (owns his own pharmacy, in fact), and said if I ever needed anything I should come to him (with the exception of narcotics; then he would never speak to me again).  Well, my insurance just ran out with the end of the year, and walk-in clinics are slow and relatively expensive (not to mention a prescription), which sucks because I was pretty damn sure I just needed a basic antibiotic and I’d be set.  So, I emailed him to see if the offer was still standing:

“Hey!  Hope you had an excellent bday, and I know I don’t need to say it but thanks again for yesterday.

I just wanted to write you because you had mentioned in the past that if I ever needed anything prescription-wise I could come to you, and was wondering if the offer is still standing?  Late last night I noticed something going on in my throat, and when I woke up my throat was pretty swollen.  I know we kissed a little, I’m assuming you haven’t noticed anything?  I hope you’re feeling fine, like I said nothing started for me until late last night.  I feel like it’s some sort of infection. It’s not really acting like a cold, and reminds me of a throat thing that I tried to wait out once before and took a couple weeks.  I’m pretty sure I need antibiotics.  But when you said you could help out I’m not sure if you meant I would still need a prescription…  I know self diagnosis is a little sticky!  So if the offer is still standing, 1. do I need a prescription?  And 2. if so, do you have a recommendation on a good walk-in clinic?  I looked up a couple, and am planning on going tomorrow, but didn’t really have a good way of sorting them out!  If you can’t help at the moment for whatever reason, clearly it’s fine, but figured I should ask.   Hope your dinner was excellent!”

He called about 30 minutes later, went through a couple of my symptoms, and offered me a z-pack (azithromycin).  When I went over to pick it up the next day, he also gave me a bottle of vitamin C.  I only spent a couple minutes there this time, but really, I am so grateful that he did that.

I wrote him afterwards:

“Hey, just wanted to let you know… clearly i still have to finish out the 5 days, but it definitely was some sort of infection. My throat is already MUCH better!  From the time we’ve spent together I’ve known you are a great guy, but actions speak way more than words and impressions… and you’ve been really kind to me this week.  So again, thank you. talk to you soon-”

Really, I meant it.  He has been so kind and understanding this week, and we have definitely gotten closer because of it.  DO NOT read: I’m falling in love.  Please.  I just mean he walks the walk, and I appreciate it.  I’m a hooker, and while he may be falling for me a little bit, he easily could have explained his way out of paying me for the extra hour, and he was under no obligation to give me free antibiotics.  He really is a good person.  And I think all of this has officially stamped him as a regular.  No future meeting is scheduled as of now, but I’ll be truly surprised if I don’t hear from him again… At the VERY least we’ll keep in touch.

8pm meeting tonight with the “famous” new guy.  I’ll be moving in the next couple days, but I’ll try to post about it asap!

-B