Philadelphia Sin

I mentioned I was heading to Philadelphia next week for a few days.  I do enjoy that city.  The men are quite kinky.   Hoping to get some Mommy/son role play time in with one of my regulars and it will be fun to make the acquaintance of new men too.

There is an excitement in getting ready for your date – picking out the lingerie you think he would, the feel of the garters underneath a silky dress. I never wear panties and am completely bare so I often wonder what he can see…

Turning 37

Another birthday is a few days away..I will be working in Philadelphia.  I’ve taken a few days off to figure things out – where I want to be next year, in 5 years and who I might want to be with.

There are a few things I know…

 I love my chosen career and I truly get pleasure from it.

 I don’t want to do this forever and want to be a legitimate and successful entrepreneur.

 There will always be a slave in me whether or not I have a Master in my life.

 God will never give me more than I can handle.

Just when I think I am getting ahead there is a challenge to face.  The challenges will never go away it is just how we deal with them that will change.  As I get older I aspire to listen more than talk. To be more empathetic and to open myself up and to be vulnerable.   Vulnerability was never my strong suit and instead of trying so hard to fake it til I make it…I am just going to be.

And driving a Lamborghini Gallardo is a good start..

your kinky courtesan xx

Deja Vu

Tonight it had a date.  We went to Fig & Olive, one of my favorite restaurants in the city.  I enjoy it for the great wine selection, fabulous raw bar and light mediterranean fare.   The irony, was that we were were seated at the v. same table were I had another first date that took place many, many months ago and ended v. different than this one.  

The guy was attractive and kind.   He needed to unload and he did – about his life, his past and what he wanted for his future.   He is a submissive and I could have lots of fun with in bi-fantasies with him as he wants badly to be taken by a man.  I imagined his cock 7″ and nice girth…all I care about is girth anyway..    I listened empathetically and asked questions.

 However, I couldn’t help but have a flashback to the original dinner I had sitting in these chairs – all the wine, the intimate conversation, the stolen flirtatious looks and afterwards going to his office and fucking over his desk – two crazy kids…

Ah..the memories…time to create new ones..

your kinky courtesan xx

Songs That Get Me in the Mood..

Its hot and sticky out…I am on deadline for the sex site I freelance for, launching on Monday.   I’ve got a date tonight so with all this activity, thought I’d share my play list of songs that get me in the mood and these are in order of my favorites..

All available on itunes of course..

1.  Jersey Girl.. Bruce Springsteen.. (well that is where I grew up)

2.  In and Out of Love  – Armin Van Buuren

3. Adagio for Strings – Tiesto

4. Don’t Stop – ATB

5. Lady is a Tramp – Frank Sinatra

6.  In My Memory – Gabriel & Dresden

7. Slow & Low – Beastie Boys

8.  Beast of Burden – Rolling Stones

9.  Brilliant Disguise – Bruce Springsteen

10.  Skills to Pay the Bills – Beastie Boys

11. O Soava Fanciulla (La Boheme)  – Andre Boccelli

12.  Someone Like You – Adele

13.  Blue Dress – Depeche Mode

14.  Set Fire to the Rain – Adele

15.  Im on Fire – Bruce Springsteen

Songs to motivate you, fuck to, drive to….

your kinky courtesan xx

Birthday Wishes and Wet Dreams…

My 37th birthday is a week away.  In anticipation I am having lots of fantasies lately.  My sex drive is in overdrive.  Last night I had this dream about a stranger.  He was British, v. sexy and v. dominant.   I was at the Mayfair hotel having a cocktail and he was wearing a gorgeous Paul Smith suit and Hermes tie (its a talent to be able to spot an Hermes from 150 feet away). He was wrapping up a business meeting and it was clear he was in control.

We made eye contact briefly a few times and each time, I quickly looked away, blushing.  There was something unsettling about his presence in this plush hotel bar at 5 in the afternoon. I wish I had worn panties.

The next time I looked up he was alone.  All alone. My instinct?  Get up and go to the loo. As I walked by I could feel his eyes burning through me.   I secretly hoped he would follow me.  The bathrooms at the Mayfair were perfect for intimate moments and big enough to do v. dirty deeds. I was certain that I had to taste him.

As I walked out of loo, he was standing there.  Funny that in a marble bathroom, I hadn’t heard him enter.  He didn’t smile.  Didn’t say a word.  I walked up to him.  He grabbed the back of my neck and forced me to my knees.  Oh God, that bulge.  I began to suck, lick and swallow like it was my favorite ice cream cone.   His hardness said it all about how he was feeling.  Unexpectedly, he pulled me up, yanked my skirt up and began to fuck me again that marble sink.  It was a love match – my cunt and his dick.  It was so creamy it didn’t need his finger or tongue.  He unhooked my garter belt and shoved my stocking into my mouth to make sure I wouldn’t make a sound.  All I could do is cling on to his shoulder as if on the precipice of a mountain.

Over and over, he fucked me.  He turned me over suddenly and turned the faucet on shoving my face in the cold water while letting my ass get the royal treatment.  My ass was hot and filled with him while my face and neck were cool under the cold water.  

As quickly as he began, he suddenly stopped, zipped himself and walked quietly out.  Never was a word exchanged.  A light kiss was planted on the back of my neck and there, bent over the sink, at the Mayfair Hotel with a stocking in my mouth, I received the fuck of my life from a stranger.

your kinky courtesan xx 

Independence for Independents

How was your 4th of July?  This Independence day was probably the best one yet.  It was low key but I made some new friends and that made it special.     It turns out that the girl I went out with twice, makes a cool friend.

We started out at the Cubbyhole first, which is the hottest lesbian bar in NYC.  The drinks aren’t great but the company always is…What is fabulous about this place is the ambience – small and cozy – filled with colored streamers hanging from the ceiling and awesome music – a mix of 80’s and pop.

One of the women is a chef on movie sets and so it was fun gossiping about Hollywood and getting the inside scoop about how “alternative” these actors really are. Let’s just say that there are some v. big name actors that love cock.    Eyes Wide Shut should of really been a  Knowing this, I have a new found respect for some of these well known thespians.  That is just so hot.

Dinner at Extra Virgin in the West Village.  Highly recommend.  This is one of my top 10 now.  Fabulous food, reasonable prices and intimate atmosphere.  Who cares if the service is just ok when everything else is so great and champagne bottles are so reasonably priced?  lol   My friends picked up the tab in honor of my bday which really touched me.   It was just a great time to hang out with such cool, interesting people who are gay.  Did I mention that?  I don’t have many gay friends so its nice to finally met some women who can allow me to explore that part of myself a little more..

Watching the fireworks on West St I was reminded that we live in a country that people are dying to get into.  Where the possibilities are what you make it. Nothing is stopping you but you. Our fore fathers had tremendous foresight, determination and courage to fight for fundamentals that we may now sometimes take for granted.   I know I have been guilty of it.  I am v. thankful to live in a country where I am not persecuted for my choice in profession or beliefs.

your kinky courtesan xx

Battle with BackPage

Its the down and dirty version of an Eros Guide.   The interface is simple, its dirt cheap and traffic to your website is guaranteed to triple, averaging 322MM page views and 27MM uniques monthly according to the latest site data.  Now, bear in mind that this is backpage as a whole.    However,  reports indicate that the revenue produced monthly from the adult section alone is somewhere in the neighborhood of $2.5MM.   

Looking at it from the cost/benefit perspective, it can’t hurt to put your ad up because the exposure is incredible.  If you can position your copy right, you can still avoid time-wasters and getting in trouble..

Last night I got lucky.  A gentleman from backpage who wasn’t opposed to be being screened and didn’t balk when I told him my hourly rate, requested a date.

He showed up, polite as can be, casually dressed, a v. stocky guy.  We immediately relaxed with one another and the conversation just seemed to flow..3 hours later he found himself completely relaxed to the point of almost falling asleep..Simple conversation and a couple of oral interruptions in between, we agreed that the pleasure was definitely mutual.

your kinky courtesan xx

Tales on the Metro North

I often ride the Metro North to Stamford to see clients. Tonight the energy was different. It could of been the train was filled w commuters or maybe it was the unintentonal heat being passed between myself and a gentleman sitting across from me.

What made this encounter, if you want to call it that, so “storybook” is that I never even got his name. He just kept making me smile and I used the thoughts about what I wanted to do to him to get me hot to see a new client. It should be stated that we were not in the Bar Car and he was chatting with his friend about golf but I kept wetting my red lips and undressing him with my mascared-eyes and I could feel his eyes on me.

We didnt get off at the same stop but that kind of flirtation hasnt happened in a long time and my loins were off and running…I even briefly thought about posting a ‘missed connection’ ad on Craigs List. Just thinking sbout where that could go….

My client was a gem btw….,

Your kinky courtesan xx

A Note of Appreciation

I wanted to thank everyone for the positive feedback and notes of appreciation that I have received over the past few weeks in regards to the Office Shenanigans portfolio.  I am really glad that you enjoyed them and I am set to do another photo shoot in the next couple of weeks, which will be different but equally as stay tuned for a sneak preview…

Every day I put myself out there- in my job and in my musings on this blog.  I truly enjoy the time that I spend with my clients and sharing a piece of who I am with you.  I realize that this is a discretionary service so I am always humbled and excited whenever I have a date, regardless if I have seen you 5 times or if it is our first time…

I especially appreciate the support I have received through the survey.  The learnings are invaluable and will only help be able to better understand and cater to your needs and desires.  
In the next couple of weeks you  will be seeing changes to my site. I don’t want to get into too much detail at this time..I am v. excited though and I think you will be v. pleased..
Thank you again for being loyal and generous with your time and compliments.  This business has its ups and downs but the clients are what make it special.
your kinky courtesan xx


Every time I travel somewhere new I like to share my experiences with my readers. After my disasterous Raleigh trip, i wasnt really sure what to expect from Boston, although culturally they are different.

On Tuesday, I arrived in Waltham, a suburb about 15 minutes from Boston, and well known for being the technology and defense hub. I realized my first appointment wasnt until the next afternoon and so a night out with my Irish uncle was in order. The only beer I drink is Guinness and over a couple of pints at a pub in Boston, my trip started out on the perfect note.

Let me just say that the men here are amazing! So kinky! They really bring out my twisted side. Lol I love to talk dirty, kiss and maintain eye contact. The real treat was getting to “snowball” two men in one night….i had never tried that before with anyone but my Master and found it highly erotic.

I am in town until Saturday so i look forward to hearing from you…

Strap-On Sexy

I answered the door in my uniform- corset, stilettos, stockings and garter belt…oh and my strap on. The glitter dildo, affectionately known as Glamazon, greeted him at the door and immediately we sprung into action. How sweet he was to remember I enjoy French white….

As a switch, I go with flow so when he clearly showed signs that he was taking control, I allowed it. We just stood there in the dimly lit hotel room, lip locked, his hands fiercely grabbing on to all parts of me. Our tongues were tireless. The hardness of that silicone cock pressing up against us was an ever present reminder of the naughtiness that would take place later. Finally it was time to flip the switch.

It is important in tease and denial, to refuse a man at least one of his senses – sight, touch. As i wrapped the blindfold around his eyes, I sternly instructed no touching and no kissing. Then, forcing his mouth open with my tongue, he let out a giant moan…he knew this was going to be torture, a slow sensual investigation.

In all different position we played, never on one position for too long and I was careful to let my tongue linger for just the right amount of time. We even laughed a little at how randy he was.

His ass was so compliant. It was so much fun to probe,massage and finally fuck his taut round ass. We both enjoyed ourselves immensely as I grinded my hips against his, slowly and deliberately.

Your kinky coutesan xx


Today is the Gay Pride Parade.  I was supposed to be walking in it with my Lez Factor Meetup group but I opted to go to 11 am Solemn Mass at St. Ignatius instead.   It is the only time of the week where I can really meditate and quietly reflect into the past week’s events, actions and my reactions into situations, etc..After mass I always light two candles – one for my Master and one for my family and I leave church feeling renewed. 

I give of myself physically and emotionally every day.  As a slave and as a whore your boundaries are pushed but I wouldn’t be in that position if I didn’t want to be.  I get asked often by my vanilla friends how I have the stamina to give so much and don’t I just crave a normal life with a regular job?  No way!  A label doesn’t define you.  A lesbian or TS is more than just their sexuality.  Yes, sometimes I get physically and emotionally tired but then I go to church and I thank God for being there. or I call my 4 year old niece or do something nice for myself and I am replenished again.  
I am a slave. I am a whore.  I am bisexual.   First and foremost, however,  I am just me. Olivia. Lexy. However you know me.  
your kinky courtesan xx

Etiquette for the Discerning Gentleman Caller

I’m coming up on the 6 month anniversary since I left my vanilla corporate life behind for a less conventional career.   I thought it might be nice to offer some basic rules of Etiquette so we can ensure a more accommodating experience..

1.  When calling me, please state your name as if you are speaking to a friend.  You are looking to make a new friend after all.  I am v. relaxed and approachable.

2.  The sexiest thing a man can do with me is make me laugh. A great sense of humor gets my engines roaring.

3. Screening is MANDATORY.   You must trust that I am discreet and have your best interest and safety in mind.  Please be prepared to give a reference or your work information.

4.  I believe in reciprocity and seek to show appreciation to loyal clients.   My time is set at a certain value  and therefore is not open to negotiation.  Please be sure that you check my rates before you call.  You can also check my specials page as I am currently running a Father’s Day promotion.

5.  Good hygiene is critical.  My pussy is always waxed and bare and is nice and fresh so I expect that if you haven’t arrived freshly showered, you will ask to take a shower…

6.  While I cream for a man in a suit, feel free to express your own sartorial style..

7.  Remember our time together is just that.  Our time.  A time for pleasure, relaxation and release..however it happens..

your kinky courtesan xx

Play Group Playtime

Every so often I am called up to be the “Cruise Director” at the DDevious Delights midweek playgoups.  What is my Ddevious Delights and what is my responsibility? Well, as a private swing group for lifestyle couple, it is my job to make sure the one or two single men that are invited are assimilated well into the group.  That assimilation includes everything from chatting and making introduction, to taking their clothes off at the appointment time and well, getting on my knees (blush…) 

This particular Thursday I was excited though because it had been awhile since I had played with the organizer, Cat, who also happens to be the co-organizer of our Executive GBs.   She is pretty shy and me being the exhibitionist I am was enjoying the idea of fucking her with my strap on in front of a room of 30  people.  The excitement and curiosity int he room was palpable.  I was dress in a garter and stocking and I had a pink shiny strap on around my waist with a silicon cock ready for penetration.

Cat has v. soft lips so it is always fun to make out with her.  We definitely gel well together and feeling her get wet as I pressed my fingers inside of her was a huge turn on.  Pushing myself inside of her with Glamazon, my silicon dildo, felt so good as I fucked her doggy style.  It seemed as if the room stopped playing and all eyes were on us…We were live porn for them…had these couples never seen a girl with a strap on fucking another woman? Surely, my reality can’t be the norm…

Once she realized, all eyes were on her, Cat became self conscious and happy to have gotten some playtime time in went back to ensuring that the wine was flowing and the condom bowls were refreshed.

your kinky courtesan xx

The Art of Giving

Warning:  This blog post is intensely personal and should not be ready by people with hard hearts, unempathetic spirits or Grinch-like behavior.

In my daily, I am always giving pleasure.  Giving pleasure to my clients, finding ways to please my Master,  and trying to accommodate family and friends. I have forgotten along the way about taking care of my spirit. 
We all are guilty of it.  The business of our daily life often takes precedence over the things we need to do for ourselves, even in the smallest of ways.  Some of us use the gym as a way to get back in touch with ourselves, others use meditation, or reading or birdwatching, whatever it is that helps refocus themselves when they are feeling off kilter.
My job is to provide pleasure as a service and I LOVE my job.  I find something special to enjoy about the experience with everything client and each experience, whether they are a regular or not, is special.
What I have realized is that I need to create more balance in my own life.  It started this morning with quiet meditation for 5 minutes. then this blog post and soon a nice walk along the East River.  Taking a little time for me in the morning, will only make me more capable for receiving pleasure from others.
Remember, it is ok to be good to yourself.  Martyrs are generally not pleasant people to be around…
your kinky courtesan xx