Anal

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 anadolu yakası escort 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. ataşehir escort

“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.

“Right on. Impressive,” she responded. “What would you like to do next?”

“How much time do we have?” I asked.

“Well it’s 8:35 so we have some time,” she responded.

“Do you usually cum during your appointments?” I wondered out loud.

“Nope. Very rarely when I get fucked really good,” she responded.

“Well, that sounds like a great challenge,” I joked.

“Honestly, I can cum very quickly if the guy hits me at the right angle and I play with my clit,” she explained.

“So I guess what I am getting at is that I would love for you to cum for me,” I explained.

“Anything for you stud,” she said grabbing my cock and reaching up for another French kiss.

“Anything, really?” I asked.

“Within reason, within reason. I know what you guys like: Anal, spanking, facials, anything else I am missing?”

“That about sums it up, so which of those are not off-limits?” I asked.

“Ha, you don’t hold back, do you? Let me guess, you were in sales before?” she said.

“You are avoiding the question,” I said light-heartedly.

“So are you. Definitely no anal. You are way too big and I am not clean down there. Feel free to spank my butt, lightly though,” she said.

“What about that facial thing?” I asked.

“Usually I don’t do that and when I do, I charge extra,” she answered.

“How much?” I wondered.

“$50. But nothing straight into my eye and I definitely don’t swallow. I don’t care what people say about HIV not being transmissible through the mouth,” she said.

“Ok. Deal,” I said. “Ride my cock please.”

“Look at you getting all gentleman on me now that you know you will get to cum on my pretty face,” she said.

We made our way to the love seat and Monica wasted no time to grind my cock. She plunged down taking as much of me as possible.

“Fuck, you feel good Don,” she moaned and I felt like she was sincere.

I spanked her ass gently and asked her to fuck me harder and she obliged eagerly. She kept her eyes closed the entire time and I joined her in it as well. My hands went between grabbing her ass to pinching her nipples through her thin bra.

“Fuck baby yes,” she kept moaning and started to take me even more aggressively.

“Fuck my big cock. Fuck me harder,” I egged her on and slapped her ass a bit harder this time.

She finally opened her eyes and gave me a look of disbelief and smiled at me.

“What is it?” I asked moaning.

“You are gonna make me fucking cum,” she confessed.

“That’s it, cum on my big cock,” and before I could say anything else, she started cumming out loud.

“Arggg, fuck. Yes! I’m cumming baby,” she cried out. I just didn’t think she could fake such enthusiasm as she kept going through her orgasm. She finally hugged me pulling herself close to me. I didn’t know what else to do so I kissed the side of her head and stroke her back.

“Sorry about that,” she said pulling back all of the sudden.

“Sorry about what?” I asked confused.

“Nevermind,” she ümraniye escort just responded. “How about some doggystyle?”

“Sure,” I said picking her up while I stood up.

“Fuck me like you mean it,” she said with a smile.

“Be careful what you wish for,” I responded knowing that she had no idea how rough I have fucked women before.

She got her little body into position and I got to work. Our hips quickly started slapping against each other and before I knew it, I was fucking her past nice o’clock. Since she didn’t object, I kept fucking her in a couple of different positions before I couldn’t delay my imminent orgasm anymore.

“Ready for my cum baby?” I moaned as I was no drilling her with her back on the couch and her feet next to my head.

“Yes, cum all over my face,” she challenged me.

I pulled out and quickly pulled the condom off. The freedom my member experienced at that moment even accelerated my end game. Before I could finish the first stroke, a shot of semen hit her between her tits. The next shot went straight into her face and I couldn’t even make out a specific area as it literally plastered half of her face.

She was caught off guard completely and tried turning away when another equally strong shot hit her right side of her face. Another few shots escaped and so did the sexual and emotional frustrations along with it. Monica was a mess and didn’t appreciate the amount of cum.

“Sorry Monica, it’s been a while,” I apologized sincerely.

“Yeah yeah. That was some crazy shit. Nicely done,” she said with sarcasm.

She cleaned herself up and before I knew it, I was another $50 poorer and lonely. To make matters worse, my erection came back to life by 11 o’clock reminding me of the power of the supplements. If I didn’t get out of the house, I would find myself whacking off most likely so I decided to go out on a run.

But it was the typical Seattle fall weather and that meant some annoying constant drizzle that somehow would leave you soaking wet after a few minutes without feeling raindrops hitting you. I grabbed the car keys so I could go to the local gym I have been a member of for the last couple of years.

I was dumbfounded when I arrived at the gym seeing the lights off so I quickly read their hours on the entrance to find out they close at 11 on Fridays.

“Just my luck,” I thought to myself.

When I got back to the garage, I decided to take the stairs to the 35th floor instead of taking the elevator.

When I got to the first floor, I ended up in the retail area that had an insurance agency, a loan office and the management office. The “For lease” sign for the 3,000 square foot office space was still hanging. It has been vacant since I first moved in and when I did the math, I could see why.

The $36 per square foot price meant the place would run around $9000 per month. I was just telling myself that this place needed some sort of gym. Since I was a member on the homeowner’s association board I knew that there were 375 units in this building so if each member paid $30 bucks per month, they could easily pay for and maintain a gym.

“Absolutely not,” said Jeff, the board president. “Those things cost way more and are a pain in the neck.”

I figured I would give him a call to run the idea by him the next day.

“Think about it. Some of us pay over $4,000 per month for this place. What will another $30 bucks do? The HOA fees right now are already at $280 per month,” I pushed.

“I am not for it Don,” was his simple response.

“I am allowed to bring it up as an item during the next board meeting in two weeks, right?” I inquired.

Two weeks later:

“All in favor of letting members vote for a bid on a gym build-out say yes,” said the board’s vice president.

Next thing I knew was that a majority of people were for it. I volunteered my time to do all of the research for it since I had a lot of time on my hand. I was using my free time to continue working on the supplements online store and working out. I was almost ready to launch a website but I definitely had no money coming in yet.

So I spent the next five days talking to equipment wholesalers, contractors and insurance agents. When I added up all of the costs into the Excel spreadsheets, I felt my heart beating through my chest knowing very well that I grossly underestimated the cost. Before I even had the software calculate the amount needed per member, I knew it would be around $2000 due to the nearly $750,000 build out and that didn’t include the ongoing monthly lease cost which I negotiated down to $30 per square foot. I definitely felt beaten and hopeless and decided to go the gym to let out some steam. For some reason, brought up the topic to a girl at the gym I frequently talk to.

Teresa was the sexiest member there in my opinion and if she didn’t wear the tightest boy shorts and top, she painted her ass and legs with the tightest Lululemon pants available in her size 1 or 2. Since she was happily married, I left my sexual advances towards her to my dreams at night.

“I heard of something like that in Miami,” she said. “It’s a really nice place and not only do the condo owners pay for it through their dues, they even sign up for personal training and group yoga classes and stuff that they are willing to pay extra for.

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