Preface
Reading the "Salesman Enjoys Trip Of His Life" series prior to this series is strongly recommended.
*****
A few years back, I got fired from my job as a very successful IT salesperson due to a sexual harassment claim made by my superior. My world came crashing down not only because I found myself losing a six figure income, but the fact that it was such a public debacle right before Christmas caused my fiancé to leave me. She wasn't only the love of my life but also the only person I could see myself growing old with.
I know I screwed up that night of the holiday party but to call our interaction sexual harassment done by ME was absolutely ridiculous. The HR VP clearly had 2 drinks too many and just couldn't keep her hands to herself and my ass was one target of hers. In my stupidity, I posed for a co-worker of mine to take a picture while I was mimicking fucking her from behind when she was leaning over to talk to another colleague that was sitting down. I didn't even make contact with her as I was humping the air between us but since that moment was burned into eternity with my buddy's iPhone and his subsequent Facebook post (that idiot!), I was completely screwed.
Sara definitely broke my heart when she broke up with me three months later. I was in such a dark place and lost a ton of weight and let my health go to waste with binge drinking nearly every night and skipping a day or two between showers. And with no income to speak of, she looked at me like the biggest loser and moved out leaving me with an expensive place in a Seattle high-rise.
The past few years went through my mind. I had group sex more than once with Sara and she had seen me flirt with other women all the time but the combination of everything in my life collapsing must have been the straw that broke the camel's back.
Fast forward a couple of years and the only thing consistent in my life is change. I have changed jobs three times since I was let go with the most recent termination being due to another downsizing at a major corporation.
What also changed was my physique. I have been a fanatic when it came to getting back into shape after Sara left me so I find myself at some sort of gym 6 times a week. I even bothered getting a number of different personal trainer certifications in addition to getting an online degree in nutrition and attending different seminars that teach you about pressure points, stretching and posture movement therapy.
At one of the conferences, I met a guy who was a successful online entrepreneur selling supplements online, most of which have to do with weight loss, energy boosts and mental clarity. I usually think that people get ripped off with these things and since there is no FDA oversight, the stuff that he was mixing together might as well been powdered sugar. I shared with him the supplement I found while cruising the Caribbean that gave me the strongest boner and allowed for one sexual adventure after another.
As soon as I mentioned the brand name to him, he could immediately list all of the ingredients to me and explained that they cost nearly nothing. When I asked him why he didn't sell those, he just said it wasn't his "thing" but after further discussion, it seemed that his wife and business partner was against anything sexual. What I walked away with was a ton of information, wholesale contacts, and an inspiration to start my own business.
'We regret to notify you that due to recent changes in...' was the only thing I needed to read in my email to know that I didn't make the cut during the latest downsizing. Or since I did get laid off, I must have made the cut?!? I felt worthless since management didn't even bother calling me or having me come into the office to let me know about the news.
Either way, here I was with my savings account needing to be depleted again and no one to get laid with. I telecommuted most days and that day was no different. It was Friday and based on the text responses I got, all my friends were going on some sort of date.
Since a majority of my friendships were made with Sara, I either lost some friends or couldn't fit in when by myself.
I closed my Outlook and started browsing the web when next thing you know I ended up at some classified website where instead of selling goods, women were selling their services to men in 30 minute increments.
I was horny as hell and when I saw an ad of a slender brunette who promised an unforgettable date, I made the insane decision of hiring an escort. She was to come my place at 9 pm and her only request was that I was freshly showered and if I want oral without a condom, to be "neatly trimmed" down there. Since it's been months since my last one night stand with a random girl, I wanted to get as much out of it as possible.
Starting at 8, I spent the next 30 minutes in the shower grooming myself. Since I took an enhancer pill right before and the fact that I was anticipating what was about to happen, my cock was rock hard the entire time. The escort called herself Monica and my only request for her was to wear something sexy like a miniskirt, stockings and heels.
Monica rang the bell downstairs at 8:45 and apologized for being early and didn't want to wait in the cold. When I opened the door, I understood why. The petite wore a mini dress that didn't cover her shoulders nor anything below her mid-thighs. She didn't wear heels nor stockings so I was a bit disappointed despite her amazing cleavage and angelic face.
"Hi, I am Monica. Don, right?" she asked.
"Yes, nice to meet you," I responded.
"Don't worry, I got the heels and hosiery in the purse. I was already pushing the envelope with this while on the bus," she said referring to her skimpy outfit.
"I agree. Feel free to use the bathroom. I left your gift there for you," I said referring to the $250 I was about to spend on this date.
She walked off and closed the door behind her. She was gone for about 5 minutes and when she finally walked out, my boner immediately poked up again.
"You have a nice place here. I love your oversized bathtub. And the view, wow!" she said in amazement.
"Thank you. I have lived here for the past 5 years and am not planning on moving soon," I lied knowing that I probably couldn't afford this place for another 6 months.
"So you must do well for yourself," she inquired.
"Well, I got laid off today so I need someone to pick me up," I responded honestly not believing myself I was this up front with her.
"I am sorry to hear that," she said seemingly empathetically. "So what can I do to pick you up, stud?"
"Well, I was hoping we could start with a nice blowjob and take it from there," I explained.
"Would you prefer telling me what positions you want us to try now or just go with the flow?" she asked.
"I am not sure. I have never done anything with a hook... escort before," I responded.
"I have extra thick condoms to help you last longer if you think you might cum too quickly," Monica said nonchalantly.
"Uhm, wow. Ok, I guess," I stuttered since I was caught off guard. I knew I could fuck with the best of them when I am sexually active but this last period of abstinence might have affected my stamina. Even if it didn't, a thicker condom might allow me to be more aggressive with her. I really needed to get my frustration out.
"You are a good looking guy so I don't think there will be any issues with sucking your cock without a condom. Would you like me to take off my dress now?" she said sounding very transactional.
"Why don't you get on your knees and suck my cock. You can leave everything on," I said changing the tone quickly.
Monica followed me to the French doors leading to the balcony and I just leaned back and watched her finding a comfortable spot for her knees on the hardwood floor.
"Just squat baby and in a little bit, straighten your legs so I can see your sexy ass in the mirror," I suggested.
Once her face was inches away from my crotch, she finally saw the outline of my 8 inch member and I wasn't sure if her reaction was positive or negative. She just pressed her lips together and raised her eye brows. She fiddled with my belt at first and then with my zipper. Once she pulled down my jeans, my cock sprang out and hit her in the face. To her demise, it was covered with a ton of precum that smeared all over her forehead.
"Shit, wow," she cursed angrily at first but she knew she was there to do a job which she started skillfully. She rubbed the remainder of my juices down my shaft and started to slowly suck me.
After a couple of minutes of a pretty impressive blowjob, I build up more confidence and held onto her head to force more than a few inches into her mouth.
"Can you deepthroat?" I asked.
"Not that size, sorry," she said and looked up at me for the first time. I had removed my shirt so I was naked with the exception of my pants wrapped around my ankles. "You are fucking hot," she said before touching my abs and chest.
"Any special offers for a good looking guy?" I asked jokingly. "This must be easier for you than some fat, hairy old guy," I said trying to not sound too conceded.
Monica didn't say a word but instead stood back up and with her 6 inch heels tried to get her 5'3" frame close enough to my height to kiss me on my lips. Before our lips made contact, she whispered "I have never French kissed a client before."
I didn't care if she told me the truth or not but the kiss that followed was amazing and gave me goose bumps all over. I grabbed her ass through her thin fabric and before another drop of precum came out of my rod, she stepped back and leaned forward to continue the blowjob.
Watching her ass wiggle in the mirror made my hip thrusts more aggressive. She actually tried to take me deeper but simply couldn't. Seeing her sexy opaque stockings from behind wanted me to get show to the second act.
"Where is the condom? I am ready to fuck your sexy little body," I moaned as she continued the blowjob.
I didn't look where she got it from but all of the sudden she took her mouth off and ripped the package open. The condom was not only thick but probably meant for a cock one size smaller as it quickly squeezed the hardened flesh. She spun around and leaned over the couch.
"Do you need any lube or should I eat you out so you can get wet?" I wondered.
"Trust me. She is wet. Take it easy at first though please, you are not the smallest cock out there," she said.
"So I only have to be gentle at first, meaning I can get rough in a little bit?" I asked while I pulled her black thong aside.
"We will see about that," she said which meant nothing to me.
Her pussy was definitely wet when my latex covered dick made contact with her labia. I didn't waste any time going all the way into her.
"Fuck. Gentle please," she begged.
So I just started slowly and despite her pussy being fairly tight and very hot and wet, the extra thick condom definitely took a lot of sensation out of the equation. I just took her slowly from behind for a few minutes. She was either good at faking her pleasures or actually enjoying herself as she moaned out loud.
When I finally pulled out, my cock was now as hard as ever.
"Take off your dress," I demanded.
Monica turned around and unzipped the top of her dress to allow it drop to the ground showing off her sexy ass.
"Now your thong." I ordered and she slid it off while bending forward causing my cock to twitch.
She turned around and presented her sexy body to me with only a lace bra, garter belts, stockings and heels - all of which was black - covering her body.
"What do you think?" she asked as if she was my girlfriend needing my approval.
"Sexy as hell. 34C?" I asked referring to her tits.
