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The second week was a bigger success than the first. Not only did we run out of food each morning, generating $300 of extra income each day, but I also booked 6 more private clients. To my liking, the clients were 3 pretty women, 1 woman that was grossly overweight and 2 men who were fairly overweight. I definitely wanted the challenge of getting people into shape and mixing in a few babes kept things interesting for me.
There were a few guys flirting with Jessica and while she was flattered at first, she got annoyed after a while. She was also annoyed by my friendly interactions with our female clients and after watching me work with them hands-on for a few days, she locked the doors for lunch on Wednesday, pulled me to the weight room, pulled down her yoga pants and lubed her pussy with her own spit.
“Fuck me Don,” she hissed and handed me a condom that she kept in her pocket. It didn’t take me more than half a minute to get hard and the condom in place. Jessica used that time to rub her clit and add a few more rounds of spit to her private area. With both hands leaned against the wall-to-wall mirror, she was now ready to be fucked from behind.
At least so I thought. Despite her best efforts to get herself wet, she was nowhere near being able to take 8 inches of throbbing cock. I got on my knees and tried to ignore the musky smell of her ass and pussy when I tried my best to get as much saliva of mine near her entrance. When I finally accomplished my mission, I stood back up and slowly pushed my way into her.
“Fuck me Don. She’s ready,” she ordered.
I didn’t waste any more time and started fucking her mercilessly. She had yet to be able to take me that way up to that point. Watching her face fighting back the discomfort of my cock splitting her in half was a huge turn on. I couldn’t believe I was ready to blow my load within a few minutes. Just as I was about to cum, I slapped her ass hard with both hands and squeezed her entire hip as I was driving my prick deeper into her than ever before. It felt like I came harder than the prior weekend and I didn’t have to ask if she needed to be taken care of when she simply pulled up her pants, adjusted her shirt and walked into the bathroom leaving me standing there with my deflated cock.
I was unsure how this whole set-up would continue. I had no emotional feelings for Jessica despite her being that sexy vixen of an employee. The nearly 15 years of age difference just didn’t allow my heart to get too attached to her. I found sexual interest in 8 of my clients and I was ashamed to admit to myself that if any of them made a move on me, I would allow things to progress. ‘What were Jessica’s expectations?’ I asked myself repeatedly. I would find out the answer to that question soon enough.
After the second week since we opened our doors, things were going far better than expected. I now had a waiting list for people wanting sessions in the mornings and I was tempted to extend my hours from 9 pm until 10 or 11. I also added a few hours for Saturday morning and afternoon. I knew that sooner or later I would have to hire help but wanted to speak to Teresa and Don first. I was afraid that at some point they would turn off the financial faucet and any new expenses would be my responsibility.
The final numbers for week 2 were $13,700 and even though I had another grocery trip planned, I was able to use a lot of the non-perishable items that were purchased the week before. While I wasn’t quite ready to calculate my hourly pay with all expenses included, I did realize that by the time I had prepared the food Sunday night, I had put in 75 hours that week. I was mentally and physically exhausted.
To my dismay, Jessica said she had plans for the weekend so my pressure gauge in my balls was approaching the red zone again. I fell asleep after downing 2 Heinekens and woke up grumpy and still exhausted due to the 5 hours of sleep I got. Heather was my first appointment at 6 and for some reason, I wasn’t sure anymore about how to take her slightly inappropriate comments she occasionally threw out there.
“So last week, whose bag were you grabbing half naked?” inquired the voluptuous MILF.
“I had female company staying the night, if you really need to know,” I answered somewhat annoyed.
“Let me ask you something,” she added while starting another set up single leg presses on the machine, “are you afraid that you could get yourself in trouble again with a job that actually forces you to be touching women?”
“What the hell are you talking about?” I asked shocked.
“I know why you were fired a few years back. Your name sounded so familiar. My ex told me about a story of a successful sales person getting fired for messing with the VP.”
“Where are you going with this?” I inquired.
“Hey, I get it. My 44 year old MILF ass might not get your engines running as fast as Jessica’s teen ass, but there are plenty of asses for you to look at and with your history…I don’t know how you control yourself.”
“First off, nothing almanbahis happened with that VP. It was a complete misunderstanding. Second, if women like yourself wear tight clothes, don’t be offended if men around you take a second and third look.”
“I am not offended. I am just wondering if your history would be a concern to some of your clients,” she said.
“You tell me. I feel like you are about to blackmail me or something,” I said getting increasingly nervous.
“Don, please. I really like you and wouldn’t want to mess with your success.”
“So why are you bringing it up?” I asked.
“There were more stories about you,” she added.
I didn’t even say anything as she switched to leg curls next.
“Rumor has it that your fiancé had a pretty open relationship with you and that you guys did some crazy things,” she explained.
“Who the hell would start sharing that kind of crap?” I asked but knew that my friend Dave had a big mouth and liked to brag about the things we had done.
“Is it true about your big cock?” she asked as she was grunting through a tough set of leg curls. Her ass was as tight as ever as she squeezed and flexed every muscle below her waistline.
“Wow. I cannot believe where this is going,” I just said.
She sat up and turned towards me. “Listen, I don’t want you to take this the wrong way and if you do, I apologize. I am not looking for a relationship or anything, but this woman (she said pointing at herself), needs a good fuck every once in a while and it has been a long while. Those toys keep me level-headed but I really need a big cock to take care of me.”
“And that’s where I come into play?” I asked and essentially answered the same question.
“Don’t say I said it first. I want you as my trainer and I love how much you have been able to push me. Call it a bootycall or whatever, but I’d be more than happy to tip you for your services with services of my own,” she explained.
It now made sense why she dressed herself in the tightest leggings she owned, washed her hair before working out and covered her large tits with a tight shirt that barely covered over half of her cleavage.
“Fuck it. I have a break at lunch between 11:30 and 1. Why don’t we eat lunch at your place and see where things go?” I suggested.
“I will make sure they go the right direction. What turns you on?” she asked.
“That’s a loaded question,” I answered.
“Hey, I am not stupid. You fuck a girl half my age so I want to make sure I can compete,” she explained.
“Don’t sell yourself short. You are sexy woman,” I said trying to encourage her.
“Well, thank you. Do you like lingerie, costumes, toys, bondage?” she asked.
“What the hell do you have upstairs?” I wondered.
“Just a few items but I do have a few hours to go shopping,” she explained.
“Not sure. Anything is fine,” I said.
But she insisted: “Don’t be shy. Call it your wish list.”
“Alright, I must admit. I have seen you in your work outfit when you go out and show clients some homes. Maybe something in that direction?” I thought out loud.
“Ah, some role playing. I like it. Tell me more. What exactly would you like me to wear?”
“Some high heels of course, 5 inches minimum. Stockings and garter too of course and a skirt that barely covers any of it. For the top, anything you don’t mind getting ripped.”
“Mmm, so you are the aggressive type. I like it,” she teased. “I think I know where to go from here. I can’t wait,” she said and as if we just got done talking about the weather, she was starting her set of side lunges.
I had the hardest time not getting a boner for the next 4 hours. Jessica seemed a bit standoffish which made things a little easier even if her boy shorts didn’t.
When it was time for me to head upstairs, I decided to not waste any time and left a few items out that I usually put away. Just as I was about to head to the elevator, there she was standing in her sexy outfit.
“Don, right? I cannot wait to show you this condo. It is great to meet you,” she said walking towards me in her platform high heels causing a loud clanking sound in the hallway.
“Heather, right?” I played along.
“The pleasure is all mine. The agency should have prepared me for sending a beautiful agent like yourself.”
“Oh stop it. When I heard that it was a personal trainer that is looking to buy this place, I insisted on being the one to service you and I am glad I did.”
During the short elevator ride, I took a closer look at her. The skirt was barely covering the top hems of her fishnet stockings. I am sure there were a couple of people that had just walked through the hallway before I got there. She also wore a blue button up shirt that left the top three buttons undone and with that, showed off part of the black lace bra.
Once inside, she actually gave me a real presentation. Except for bending over to show me extra outlets or stepping on the kitchen counter to show me almanbahis yeni giriş the recessed lights, which gave me a clear upskirt view.
“The place is great, but the price might be a bit too steep,” I said even though there was no price mentioned.
“Listen, Don, I really need this sale and I am willing to do whatever it takes for you to make me one happy woman today,” she said stepping within inches to me.
“Let me ask you something,” I said and grabbed her left ass cheek through the skirt. “Do you always dress this slutty when showing homes?”
“Only if I want to make a deal with a hot guy,” she teased back.
I stuck my tongue out to be immediately met by her stretched tongue. We swirled them around each other with our lips barely making contact.
“I tell you what, you deepthroat my cock and we might have a deal,” I said.
“That will be the easiest sale yet,” she said and dropped to her knees in the middle of the kitchen. She fiddled with my belt and zipper until she finally freed my raging cock from its constraints.
“Shit,” she said as she laid eyes on it for the first time. “This might be harder than I thought.”
“Actually, he can still get harder,” I teased her.
She started with a gentle kiss on the tip followed by licking me underneath the entire length before she licked my balls. “This is fucking big. What if I get most of it down my throat?”
“Balls deep. I want to see my balls rest against your chin,” I explained.
She then took my in her mouth, her tongue swirling around the head the same way she did with my tongue. Three inches, 4 inches, 5 inches disappeared in her mouth after she opened her throat for me. She didn’t quite get to about 6 before she pulled back and gagged. “Damn it,” she said frustrated.
She repeated the same steps just to finish a couple of inches short. My cock had finally grown to full strength which made the last attempt even harder. I grabbed the back of her head and held her in place when 5 inches were surrounded by her mouth and throat. To my amazement, she just let me hold it there. I think she found a way to breathe through her nose and I just moved about a centimeter back and forth and she simply held onto my hips. About two minutes passed before I realized that she was getting too uncomfortable.
After telling her how amazing that was she sat up on the kitchen counter and propped her heels on the edge to open up her legs wide. She wore no underwear exposing her hairless cunt causing me to look surprised.
“Hey, you didn’t say anything about a thong or anything. How do you like my laser hair removed pussy?”
“I didn’t even know that was possible,” I said surprised.
“All things are possible if you really want it. Right now I want you to eat my pussy,” she hissed.
I don’t know what she did to her pussy, but it tasted amazing. Somewhat fruity and she had no issues producing juices that soon collected on the counter and the edge of her skirt.
“Fuck yes, keep going,” she said while pulling my head closer to her.
I was eating her out until my tongue grew tired.
“Left drawer,” she said suddenly.
“Get my dildo out of the left drawer,” she ordered and in my confusion I opened the drawer that was underneath the kitchen island. Inside of it, amongst a few kitchen items was a dildo about 6 inches long and as thick as my cock. “Fuck me with it, while you lick my clit. I promise you I will come within seconds,” she said while rubbing her clit.
She scooted to the edge of the counter leaving her ass half-way in the air. She used the pots rack above her to hold herself in place. She was right. As soon as the dildo disappeared inside of her and my tongue made contact with her bundle of nerves, she started shuttering.
“I’m cumming, fuck me hard. Fuck me harder, yes.”
I did just like she asked and almost felt like I was punching the toy into her abdomen. She finally let go of the rack above her and nearly fell off the counter. She gathered herself and tried to deepthroat my cock again immediately. She still was a few inches short which seemed to frustrate her.
I grabbed her by her shirt to signal her to stand up. Once she was standing, I grabbed each side of her shirt and ripped it open. A couple of buttons fell off and instead of ripping off her bra, I pulled the lace cups over it causing them to push her tits higher. I squeezed both of them hard and Heather showed no sort of resistance so I squeezed them even harder. She just returned the grip with a lustful look.
“Fuck me already Don,” she said aggressively.
I spun her around not caring about the lack of protection and went straight for her wet pussy.
She briefly cried out due to being filled by me and said: “Wrong hole.”
Under any other circumstance, I would have been confused but it dawned to me that I could tell that her ass was lubricated.
“There is lube in my bedroom,” she said and grabbed me by my cock. She was barely able to walk straight almanbahis giriş in her 6 plus inches of heels and quickly sat on the bed once we arrived to her room and grabbed the bottle that was placed on the nightstand.
She applied more lube to me while I was standing in front of her and leaned back to bring her legs in the air. She stuck a lubricated finger up her ass and she soon told me she was ready.
“Please be gentle,” she begged as I got into position. The first try at poking through her rosebud resulted in my cock sliding up towards her labia. The second time I grabbed the top of my cock to just leave half and inch sticking out so I could use more force to penetrate her tight ass.
To call it tight was an understatement. I worked on it for a good minute before she finally relaxed enough to allow any sort of penetration.
“When was the last time you had anal sex?” I asked her.
“I used to do it all the time. My ex was an anal freak. I thought it would be easy as in the past…ouch. Shit that hurts,” she whined.
After another minute or two of allowing her to get acclimated to my prick, she poured more of the lube on the top of me with a generous amount dripping on her skirt below. I leaned forward to kiss her lips for the first time and she bit my lower lip in response.
“Is my MILF ass tight enough for your big cock?”
“Hell yes. Ready to be fucked yet?” I countered.
“Go for it,” she said and grabbed her fishnet clad calves and pulled them back behind her head. I love flexible women and Heather was far more flexible than a majority of women she could be a mother to. The next thing I remember is my cock balls deep inside of her and the combination of by swollen balls, her tight ass and her stretched legs beneath me got me closer to climaxing than I had wished.
I kept fucking her deep and with each stroke I felt myself getting one step closer to the finish line. Thoughts were running through my mind that I was possibly disappointing her considering the stories she heard. Before I could decide to pull out to prolong the inevitable she squeezed her ass even tighter and I pulled my cock out just in time before the first shot erupted. I soiled parts of her skirt before showering her bra covered tits with my cum. My body shook uncontrollably as I jerked my cock through the last spasms. It took me a few seconds to catch my breath and gather my thoughts.
“Sorry, I came too soon,” I said.
“Are you shitting me, I was praying you would be done sooner. My ass is on fire. Next time, we might just have to stick to my vagina. Damn, that was a lot of cum. So you want this place?” she joked continuing the role playing.
“I will need to stop by a few more times. Can I insist on you being the agent each time?”
“You bet. I will tell the agency that there is a good chance you will come again.”
I washed my cock with hot water and soap and was about to hurry out the door to grab some lunch when Heather let in the pizza delivery guy.
“Pizza? I thought we had aggressive goals to meet,” I said referring to her 1 pound weekly weight loss goal that included a 1,600 calorie food intake daily.
“I had an extra workout today,” she said kissing me right in front of the young kid before handing him some cash. She put on a jacket but didn’t bother covering up her soiled skirt or sexy leg and footwear before she opened the door.
When I returned to the gym with my stomach filled and balls drained, Jessica caught me off guard.
“You left a fucking mess around here,” she hissed.
“Hey, hey. Watch your language. I had to run an errand. I will clean it up,” I said.
“Too late, I already took care of it,” she said a little less aggressive.
“You ok?” I asked.
“I am tired,” she admitted.
“Are the two jobs and school too much for you?” I asked.
“It’s, it’s everything. The job probably the least of it, kind of,” she hesitated.
“What do you mean?” I asked right as my next appointment arrived.
“Hey Michael, I will be right with you,” I said. “Let’s talk about it later, Jessica.”
Michael’s workout went well. I actually met someone that was superior in a lot of physical areas to me. He pushed through a customized circuit training session that consisted of a total of 80 pull-ups in 50 minutes. He could barely lift his arms at the end and actually motivated me to give more at my next workout. Jessica and I didn’t get a chance to talk until the evening when she called me after work.
“What’s up?” I asked her casually.
“Alright, no more b-sing around. I am not sure what to think about us,” she admitted.
“Not sure what you mean. Like if we are dating or not?” I probed.
“Well, that’s the thing Don. I have been dating someone off and on for a while,” she said.
“I thought you broke up with your boyfriend months ago.”
“I did. But there is this guy who has been a really good friend of mine since Middle School.”
“Okay,” I responded confused.
“And when my ex and I broke up, he was there to support me,” she said and I could sense some emotions arise.
“That’s fine. You don’t have to explain yourself. We can keep it completely professional. I really need you to work at the gym though,” I said concerned.
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