From Sales to Gym Ownership Ch. 06

Monday - Destiny gets involved

Monday morning was one of the busiest yet with Mike and I running 5 personal training sessions in a row each and the yoga classes were too full for comfort. Destiny decided to wear some yoga pants and a sleeveless halter top shirt. Her toned legs and ass pushed right through the thin material while her exposed arms showed her intimidating bi and triceps. If she added any more muscle to her statue she could qualify as one of the fitness girls but she found just the right balance between being in shape and one hundred percent feminine.

Teresa and Destiny got along well together and went over some details of the business. Meghan was too busy with the bar and front desk that I think she was frustrated that the other two were spending too much time talking. It wasn't until 11 am when I asked Teresa to give Meghan an extended lunch that she could charge the business account for. I also had a chance to take my lunch so we left Jessica by herself while she had a 3 hour break between classes.

The two ladies and I ended up eating lunch together and we strategized about how we can get the business to run more efficiently. Destiny wanted to get started right away and we agreed to add her to the list of trainers and have her give Jessica a few days off the following week. We also added a Zumba class three times a week.

After a few weeks, we celebrated some victories while also facing new challenges. The biggest challenge was Mike. He was starting to become more inappropriate with Destiny and Jessica and even got a complained from a female client who overheard him talking about some client's ass. I was never the confrontational guy but even after 2 separate conversations, especially Destiny didn't feel that he looked at her any differently.

My personal challenge was with Jessica and Heather. I was so busy with everything that was going on that I didn't realize that Wednesday morning came around and Heather hinted towards me coming upstairs for lunch. Destiny had been there for a week and a half at that point and we definitely lived like a dating couple. Since we were so busy, we only spent some quality time and had sex two more times since the first night. We did sleep in the same bed the whole time but gave each other no other indication that we were starting a serious relationship.

Wednesdays happened to be Destiny's turn to cover the lunch hour so I excused myself and headed to Heather's floor. My heart was pumping rapidly as guilt rushed through me even before I rang her doorbell. The MILF didn't allow me any room to retreat when she opened the door dressed in a fishnet body stocking and knee-high stiletto boots. It took me a moment to realize that it was also crotch-less as it was not covering any of her tight ass when she turned around and walked to the bedroom.

While still feeling guilt rushing through my body, so did my blood that was feverously pumping blood into my growing cock. When we arrived in the bedroom, there was a magic wand that we have played with before as well as a new toy.

"I was told that this will for sure make me squirt," she said nonchalantly. "I prepped my little butthole for you so we will have you fuck me there while I stimulate my g-spot. I want you to use the magic wand on me too," she said bossy.

I was used to her leading the way and this sexy MILF deserved all of the authority. She should be proud of herself having lost another 4 pounds the past few weeks and most likely being able to outfuck most women half of her age. She lied down on her back, spread her legs and immediately spread her wet pussy for me.

I undressed completely while standing at the side of the bed and after a quick rub of my throbbing member, she confirmed that I was ready to fuck her. She put the tip of the condom in her mouth and skillfully slid it down my shaft with her lips. The condom reached about half-way before she unrolled it another 2 inches with her right hand.

I climbed on top of her, penetrated her right away and started to fuck her frantically. I am not sure if it was my guilt or passion that drove me to take her as fast as I could. Heather just moaned and cursed in response and tried to dig her nails into my back. I didn't want to have to explain any marks to Destiny so I pinned her hands behind her head with my right hand. I used my left hand to squeeze her tits before grabbing her ass.

I built up a sweat before we decided to execute her plan. I pulled the blonde to the edge and jumped off the bed. She picked up the g-spot stimulator and licked it before sticking it inside her pulsating pussy. I had no issue penetrating her ass after lubricating both ends. With her boots wrapped around my head, I started to penetrate her slowly at first.

With one hand I held onto her left tit while I started to stimulate her clit with the magic wand. I immediately felt her ass clenching around my aching cock and tried to find a pace where I wouldn't fuck myself to an early climax. With the stockings covered babe in front of me and watching my cock disappear in her ass, I was just ready to cum. I couldn't help but pull out of her ass while continuing to stimulate her clit.

When she finally reached her own orgasm, she simply whimpered and bit the pillow that lied next to her. I heard her muffled scream when she pulled her toy out and started to gush. It wasn't as much as I have seen from other women before but she definitely reached her goal. She literally slapped my hand that was holding the wand to indicate she was overstimulated.

When she finally calmed down, she saw my raging pole and seemed surprised.

"I thought you came already," she said exhausted.

"Not yet," I simply responded.

As if she read my mind, she climbed off the bed, stood up on her extended legs, and bent over the bed. She spread her ass for me and my cock soon found its target again. I must have come within seconds as I was turned on by the whole scene that played out in front of me. I disposed of the soiled condom and by the time I was done taking a piss, Heather was already wearing her business attire.

"I have an appointment to rush to. Let yourself out when you are ready," she said and took off.

I ended up sitting on the couch contemplating what the hell I was doing. Destiny is perfect for me and the last time I was even close to doing anything inappropriate with another woman while I was in a relationship, it went south. I knew I would have to have a conversation with her soon.

I went back to the bedroom to pick up my stuff when I couldn't help but look at her opened walk-in closet. I quickly recognized the outfits she had worn for me and they happened to be grouped together. Most of the sexy shoes she owned she wore for our times as well. I was tempted to quickly look through her lingerie drawer but knew it wouldn't help my dilemma.

That night, Destiny seemed to want to get intimate with me but since I didn't return her flirts, we ended up going to sleep. I couldn't build up the courage to talk to her about our situation and with another week going by, things got more complicated with the business when I had to fire Mike. He actually made a move on a young female client which was all I needed to kick his ass out.

Destiny took on a lot of the clients and most of them seemed to appreciate the change. Especially the men, those of which who didn't let their ego get in their way, enjoyed being trained by the exotic babe who made sure that not one of her outfits was too conservative. It was Tuesday night when Destiny and I found ourselves in the bathtub. Tomorrow, Heather would expect me upstairs again and my guilty conscience couldn't take it.

"So, where are we going in our relationship?" I opened the conversation.

"What do you mean?" she asked since I just wasn't the best at choosing my words.

"A month ago, I had no serious relationship in sight and now you are here in my bathtub as if we were married. You know about my past and would hate to do anything to hurt you."

"Then don't," she said quickly.

"So you are saying that we, you know, are only for each other, right?" I said, again not knowing how to use my words wisely.

"You mean as far as being with other people, sex?" she asked.

"Yes, off-limits," I explained.

"I would think so. Don't you?" she inquired.

"Well, yes. I just want to make sure. You tease dozens of men daily with your sexy body and I don't know if you would consider, you know...," she said.

"Uhm. I wouldn't. And I hope you wouldn't either," she explained.

"That is why I am asking. The weeks before you came, I was sexually active you know," I said immediately knowing I put my foot in my mouth.

"With who?" she asked right away.

"I'd rather not," I said.

"I think you should tell me. Do they still want you? Do you still want them?" she pondered out loud.

"Well, I don't know. That's not true. One of them probably still expects it," I said referring to Heather.

"How in the hell does someone 'expect it'," she asked.

"I don't know. There is someone that helped me relieve some stress every few weeks," I tried to justify.

"Ok, ok. If you and I are to live and sleep together, you better not need anyone else for that anymore," she said angrily.

"I agree. I just wanted to be on the same page," I quickly responded.

"Well, looks like we are," I said and with that our conversation was over. I figured the mood was too messed up for the night to get intimate but Destiny proved me otherwise.

A few minutes later she had me sit on the edge of the bathtub and without wiping away the bubbles, started licking my shaft that had been hard since I saw her climb into the bathtub. She gave me an amazing blowjob before she turned around and got on her knees. Her pussy was soaking wet when I penetrated her for the first time since last Saturday.

As I tried to find enough flesh on her ass to hold onto her tight, I asked myself why in the world I would need to fuck anyone else. Her Kegel exercises came to good use each time we had sex. She was as tight as a teenager and the most beautiful woman I knew. That night, she seemed so desperate to be fucked or to please me; I wasn't sure. All I know is that she pushed her body against mine each time I pressed forward.

Even though I have experienced this sexual perfection at least a dozen times since she moved here, my cock couldn't get used to it. I probably came within 5 minutes and I knew she longed for the intimacy of my cum flowing deep inside her body. I don't know if she came but she didn't make any notion that she needed anything else when she climbed out the tub and dried off.

She ended up wearing a sexy babydoll to bed which was unusual for her and the following morning she wore the sexiest workout gear she owned. During my appointment with Heather, I explained what was going on and told her we would need to stop and she simply ended the conversation with "if anything ever changes, I will be here." My respect for her increased a ton when she not only dressed a lot more conservatively going forward but also agreed to start working out with Destiny. The two of them got much closer and I didn't feel like Heather did anything to hint something towards my girlfriend.

I never had to worry about Jessica or Meghan. They both knew Destiny and I were an item and Meghan actually disclosed that she started seeing one of the clients. Mike ended up being replaced by two highly qualified part-time trainers and my life and business were finally getting to a routine that presented less stress. It took until October for me to finally build the courage to go on vacation.

By that point, I was hopelessly in love with Destiny and my sexual engines were running on all cylinders with all the women I was surrounded by. I think Meghan made it a point to schedule the prettiest women with me. And I made it a goal to get all of them in the best shape possible. We created a website with before and after success stories and after a professional photographer took some fitness pictures of our selected clients, we had every reason to be proud.

Leslie, for example, hit her goal of 135 pounds which was more than slender for her 5'9" frame. She continued to wear shorts and sports bra type tops to her workouts and at times, Destiny got a bit concerned about the sexy vixen being up close with me.

A web designer created a beautiful high-end website for a health club that turned out to be one of the best in the city. Our small size made it impossible to grow anymore once we stayed open until midnight and opened at 4 am. Money was flowing in from all angles and I couldn't wait to treat Destiny and myself to an all-inclusive Hawaiian vacation.

"So what kind of fantasies do you want fulfilled on our getaway?" asked my lover while she started creating a packing list.

"Be careful what you wish for," I warned her.

"I am. Here, pick something," she said as she turned the laptop towards me showing displaying an erotic store's webpage. A body stocking clad model immediately caught my attention. I was certain it was the same one Heather wore for me.

"How about that one?" I asked.

"Ha, I knew it. You like what Heather wore for you?" she asked.

"What the hell?"

"She told me everything Don. We couldn't help but talk about that cock of yours," she teased while grabbing my crotch.

"So you aren't mad or anything?" I wondered.

"Nope. I am proud of you for having that sexual woman ready to throw herself at you but you put a hard stop to it. I mean, she seems to have fulfilled whatever desire a woman can provide for you. I know you like anal and you have yet to ask me for it," she explained.

"Well, you made it clear," I said remembering her stance years ago.

"That was years ago, I might be willing to change my mind, but I would probably need something in return," she said.

"What would that be?" I asked.

"Don't know yet. But what better place to lose my virginity than Hawaii," she said. "Ok, what else? We will be gone for a week. I am guessing you will want to probably have sex with me twice a day so that makes 8 days and 7 nights."

"So how much do I get to choose?" I asked.

"Eight plus 7 is 15, isn't it?" she responded.

So I started to click "Add to cart" on the body stocking and kept browsing.

"You should model for this website. You'd be the hottest one on it," I said honestly.

"Admit it, you don't want other men to see me half-naked," she teased.

"I don't know how I feel about that to be honest," I said.

I clicked on the best sellers and selected a jack rabbit as well as some cock rings.

"I have an idea," she said. "How about you choose an item, and I choose an item and we don't look at the check-out details and just order it so we can surprise each other."

"Sounds great. Anything off limits?" I asked not even knowing what I might be referring to.

"Uhm, I might be scared you ask. Worst case, we have to return it," she responded.

She went ahead and grabbed it and within seconds had something selected.

"That didn't take long," I joked.

"Well, I have been browsing for a while now. You know it makes me wet thinking about wearing some of this for you," she teased.

I got the laptop back and looked around a little. She already had some nice stockings and similar sets, but a black camisole set caught my attention. It came along with fishnet thigh-highs that were attached via garters and the blonde model was restrained in some handcuffs. I also added the suggested footwear which were 6 inch black lace platform thigh boots with a side zipper.

I clicked on the home page before handing her the laptop back.

After making her selection, I chose a bronze two piece bikini set for her that specifically said that the material covering the bottom easily slides into the crack if someone was to be that naughty by the pool or beach.

"Hmm, not sure what else you are into," she pondered. She spent a good two minutes before being done. "I am really getting wet just thinking about our vacation."

"Admit it, you are getting wet looking at these half-naked women," I probed.

"Ha, keep wishing," she said reminding me that while she seemed uncomfortable when other women got intimate with her, she definitely didn't completely resist it.

I decided to get this ridiculous set of string bikini where the top only covered the nipples. I knew she wouldn't wear it in public but I just needed her to see her in it.

She was more quickly decisive on the next item and I chose a black mini-dress with a v front type opening that would allow for now bra to be worn. I added a pair of matching designer 6 inch pumps and crotchless panties.

While Destiny was making her next selection, I thought about the fact that if any anal sex was to happen we would need the right items to prep her for it. She swung the laptop around towards me and I immediately typed in 'anal' in the search function to see what came up. The first one was a small purple anal plug which I immediately ordered. A few items down was a cleaning kit. I went ahead and ordered two of them.

I also tried to add the highest rated lube but the system told me that it was already in the cart making me think that Destiny might have already added anal sex related items which gave me an immediate hard-on.

We repeated our shopping turns a few more times and I found another pair of white high-heels for her to wear as well as another set of matching stockings, garters, thong and bra. When it was her last turn, she gave me an evil grin and spend the next few minutes completing the order before shutting down the computer.

"I bet you are horny, aren't you?" she asked me.

"You know it," I said and stood up to walk up to her and immediately went for her leggings covered thighs.

"Not so fast. I haven't showered since yesterday and barely got done with my period. Let me jump in the shower real quick," she said putting a sudden stop to my approach.

"Can I join you?"

"Why don't you just light some candles since you already showered?

She walked off and I just watched her iron ass as it pressed against the black leggings before she disappeared around the corner. Since Destiny had been on her period, we never got around to have sex for a week. It is amazing how horny I could get but also allow my mind be distracted with constant work. I spent a few minutes starting a playlist on the built-in entertainment system and lit a half-dozen candles.

I dressed down to nothing except my grey Under Armor boxer briefs and could see that the material was soaked. I waited another five minutes and just heard the shower run with an occasional item picked up or put back. It seemed like fifteen minutes have gone by when I caught myself stroking myself to keep my excitement going. Then she finally turned off the shower but spent another five minute getting ready.

"Close your eyes," she ordered before I could hear her walking out of the bathroom. "Keep them closed."

She leaned over me and I immediately got a quick sift of her heavenly perfume. "I know you usual preference for my stockings would be wrapped around my legs. Tonight, let's wrap it around your head to cover your eyes."

She tied her silk stockings around me and was then ordered to put my hands underneath my butt. Then she finally kissed me. Gently at first and followed by her tongue licking the entirety of my lips. Whenever I tried to meet my tongue with hers, she retracted hers. That went on for a while and she knew it was driving me crazy.

"Scoot down and stick out your tongue," she said and right after I was in place I sensed her squatting over me. My tongue was met by some smooth flesh that turned out to be the outlines of her vagina.

"I haven't shaven it completely bare in a while. I hope you like it," she moaned. Usually, it would take a while for me to be able to eat her out aggressively but it turned out that she was ready for anything. When I started to wrap my entire mouth around the clitoral area and started to flick her clit as fast as I could, she grinded me harder than she ever has before. She came within seconds and I joyfully drank any nectar that ran into my mouth.