From Sales to Gym Ownership Ch. 08

"Ready for my big cock up your tight ass?" I said after removing my tongue from her sphincter.

"Give it to me baby," Destiny begged lustfully and got busy rubbing her clit.

I tried penetrating her for a little while but with my cock not lubricated enough I found it too difficult. I quickly grabbed the lube while Destiny remained in her ready position. Once I rubbed in the Shibara lubricant I tried again. This time, Destiny was also more relaxed, and to my surprise, I was able to push my way into her with a steady pace until I penetrated her half-way.

"Holy shit," she gasped when she realized what she had just accomplished. "Take me slowly, ok?"

"Of course," I said and just from what the one penetration felt like, I knew I had postponed my orgasm long enough. I applied a little more lube on my cock when I pulled back the first time and put some extra in my hand. With my hands lubricated, I smeared some over her ass and immediately fell in love with her glistening ebony skin.

I tried to get a good grip on her by holding onto her fishnet bodystocking but it started stretching and ripping as soon as I pulled on it too hard. I decided to rip apart the material that was covering her tits and before she knew what happened, I held onto her tits as I started to pound her slightly more aggressively.

"Fuck, that's a little too much baby," she whined and moaned.

"I am so close babe. Arghh, shit that's tight" I moaned as my member was approaching its limit of inflation. I felt rock hard as her anal canal grabbed me with all its might. I knew I pinched her nipples slightly too hard while I was grinding my body through an overly intense orgasm. I cummed deep inside of her bowls and collapsed to her side as soon as the last drop exited my member.

I was still inside of her ass and held her close while I was spooning her. I felt her rectum contract around me and I started slipping out of her.

"That was painful," Destiny admitted.

"That was hot," I said lightly. "I am really thankful for you doing all of this. I am sorry it hurt."

"You clearly liked it. I'll see how I feel later but I want to make sure I didn't injure anything down there," she said.

"Let me take a look," I said and started pulling out carefully. She remained on her sides with her legs staggered as I made my way south. There was lube reside all over her tight skin and when I spread her cheeks, I noticed that her entrance looked slightly irritated. I rubbed my thumb over it and she quickly jumped up.

"Crap, that hurts?" I asked concerned.

"It actually tickles. It is sore though," she said.

I ended up drawing a bath for her and looked up some post anal sex pain remedies. I couldn't believe what stories I found about fissures and prolapsed anuses and other horrific injuries. I was certain that she was just sore without any serious injuries. There were suggestions about different creams when I ran into an article that talked about coconut oil mixed with some essential oils.

We actually had everything we needed so I prepped a quarter cup full of homemade ointment for her. By the time I returned to the bathroom, she was just getting out of the tub. I quickly got turned on again watching the white foam contrast against her brown skin. She just chuckled when she saw the bulge in my boxer briefs.

"I have an offer for you since I kind of hurt you a little bit," I said.

"This better be good," she said smiling.

"So I got this remedy for your sore butt here and I was thinking to myself why not give you a full body massage," I offered.

"Hmm, sounds intriguing. I got an idea. Start a fire by the fire pit and bring the massage table out. There are some smooth rocks around it so maybe you can try giving me a hot stone massage.

Destiny poured us some more wine and cut up some chees, strawberries and other snack items while I got things ready. I wanted to make this massage special. I have massaged her a few times before but it was usually as part of foreplay and neither one of us could wait more than fifteen minutes or so before we jumped on top of each other.

The fire pit was run by gas which made things easy and after some quick research I figured out to fill a crockpot with warm water and let the stones warm up for a while. The pit was decorated with the perfect kind of rocks and a nearby outlet kept the crockpot warm. I lit up a few candles and an outdoor heating tower to make sure she would be as comfortable as possible. I also set up my phone to play a playlist of tranquility type music. There wasn't a cloud in the night sky and we could see far more stars in Hawaii than in Seattle. Destiny came out carrying the last few snack items. And once she removed her robe, she lied on her stomach.

My massage oil of choice was the coconut oil and she asked me to lather up her entire body before starting up the massage. I started at the bottom of her feet and by the time my hands made contact with her hamstrings, I had another raging hard-on. Her legs were not only as toned as ever but the entire combination of her muscular but slender legs, the glistening oil and shimmering reflection from the fire made them to die for.

I didn't lose any of my lustful energy when I covered her butt cheeks and spent a good minute making sure I got every skin cell moisturized. I was proud for paying the same amount of attention to detail on her back and shoulders. Before starting the actual massage, I put some of the homemade ointment on my index finger and gently massaged it into her entire crack.

"How is that?" I asked.

"Feels good. I hate to say that it turns me on slightly as well," she said softly.

"That a girl," I simply responded while pushing a little of the ointment past her sphincter. It was definitely still nearly as tight as an hour ago but somehow Destiny seemed a little more comfortable and hence relaxed while have a foreign object penetrate her.

Once we were done with that, I placed the warm rocks all over her body. Then I went to work on her shoulders and neck. I really wanted to make sure that I spent an equal amount of time on each body part so I looked at the time on my phone. I decided to spend a good ten minutes on each major area and by the time I arrived at her butt twenty minutes later, my hands and especially my thumbs were already sore. I pride myself in knowing that I have big strong hands which have always been a positive trait when it came to massaging women but no massages usually last too long.

I ended up using my elbows to get some pressure point located deep inside her butt cheeks. Since I was bending over further during that process, my face was much closer to her sex as well. Even though the smell of coconut and essential oils dominated the air I was sure I smelled her sexual desires as well.

After giving my hands a much needed break, they got to work again and went from her hip bones towards her inner thighs in repetitive motion. With each stroke my hands got closer to her vagina until the finally made contact. She was soaking wet but did a good job hiding her excitement otherwise.

I soon left her erotic area and got to work on her legs. I noticed the material of my underwear started to get soaked by my ever increasing excitement. Even though I was ready to massage her tits, sexy abs and quads, I spent an excessive amount on her feet. Since she was a few days away from running a half-marathon, I wanted to make sure I would help her recover from the run earlier in the day and the fact she wore heels for me.

We removed the rocks from her body and placed them back in the hot water. By the time she turned around, she was ready for a quick break and grabbed the nearby snacks and glasses of wine.

"Sir, I don't think this is very professional of you," she said pointing at my bulge.

"Sorry ma'am. I think you know you can't really blame me. Aside, your nipples are rock hard and you are soaked between your legs and I have yet to get to any of those areas," I countered.

"I guess you are right. Is it permissible to have the masseuse be naked as well?

"I don't think management will have a problem with that. Could you remove it for me please, my hands are too greasy," I said.

She took one last gulp of the wine and pulled down my briefs. She ended up dipping her hands into the jar of coconut oil and applied a small amount to my hard cock before giving me a quick handjob. I reapplied some more oil on my hands as well and massaged it into both her firm tits. Our tongues were making out while we were stimulating each other as well.

She was the one who broke off our increasingly intense moment and told me she was ready for round two of the massage. I massaged her for the next thirty minutes and in addition to my hands, my back started to ache as well. After massaging the top of her feet, I ran my hands along her long legs towards her love triangle.

Since the oil is completely safe to use on and inside of a female's sex, I massaged her labia in detail before moving onto her clit and beginning parts of her pink flesh. She was pushing her hips against my hands and moments later, she was overcome by a minor orgasm.

I was reminded that not too many things including massage tables in this world are made for people over six feet. Having bent over for the past hour definitely bothered my back. I finished the massage by running my fingertips all over the front of her body. She jumped a few times but was overall very relaxed but still aroused.

"Thank you babe," she said while exhaling after a big sigh. "Does he want to be thanked personally?" she asked referring to my member who was pointing into the sky asking for attention.

"Sure," I simply said.

"Can you get me a bottle of water first please?," she asked. When I returned she drank the entire bottle at once and then scooted her head back until it started to hang down the edge of the table. "People use their mouths to say thank you, right?" she teased and opened her jaw.

As I got into position, a drop of precum dripped on her cheek. The head was met by an outstretched cold tongue and like a slip-and-slide, my cock slid along her wet tongue towards the back of her mouth. At first, I wasn't sure how deep she wanted to or was able to take me so I barely pushed my way forward. I increased my arousal by running my hands over her sexy abs and past her bony hips.

After taking a deep breath in Destiny grabbed my hips to force herself to deepthroat me. I was busy admiring her toned body with my eyes and hands and just let her control my hips. Aside from a few gagging sounds, Destiny seemed to be in full control. When I finally stood straight up again, I noticed that she managed to take me deep enough for my cock to bulge her throat slightly.

As soon as I saw the bulge I grew even harder. When I learned how deep she was comfortable taking me, I bent my knees to push my cock more upwardly. The head of my rod quickly pushed her throat up further. I was so turned on by the sight and feeling that I felt an orgasm approaching. She helped me get turned on even more when she bent her legs back so I could hold onto them while forcing my way down her throat.

My sexy vixen was bent to the point that her feet were parallel to her head and I just kept fucking her throat. For some reason it was the perfect angle for me but especially her as she managed to take a good 6 inches of me without struggling too much. What followed next was my exhausting and desperation type of orgasm. My cock was achingly rigid when I spewed down her throat whatever cum had been reproduced since my last orgasm. However much it was, Destiny automatically swallowed it in its entirety.

"Just when I thought things couldn't get any hotter," I said exhausted and knelt down to kiss her on her wet lips.

"Well, my pussy is wet again so it's time to return the favor," she said and spun around. She wasn't lying about her wetness when my tongue tried to scoop up the liquid that had accumulated. It only took a couple of minutes of targeted tongue movements to make Destiny come again. We were spent completely sexually when we cleaned up.

"How much do you make with your enhancement pill business again?" she asked. "This stuff ceases to amaze me. My clit is still tingling."

"I don't advertise it at all anymore and still have a few thousand dollars' worth in orders per month. I just don't have time to fulfill them anymore," I explained.

"This stuff works and I think with the right business plan, you can hire someone part time and make some more play money," Destiny suggested.

"Maybe it can be someone that we can introduce to our new agreement," I teased referring to her open relationship earlier.

"See, I knew you'd think in those terms going forward," she played off my suggestion.

I ended up in the hot tub trying to get rid of my own sore muscles and Destiny decided to read a book she brought on this trip in bed.

By the time I got back to the bedroom, she was already asleep and it looked like she drank another bottle of water. Our conversation about the pills completely reminded me of the fact that that was one part I didn't plan my absence for. Since I fully trusted Heather and she was aware of the pills, I sent her a quick email asking her if she could fill some orders that have collected in the last few days.

It took me a while to fall asleep and I spent the majority of the time watching Destiny as she seemed to rest with full contentment.

I woke up and immediately regretted not having copied Destiny by drinking some water before going to bed. It was 8:45 already and by the time I realized that I was alone I saw a lovely note from Destiny telling me she went on a run. The note was held up by a pair of black high heels and a black thong tied the two shoes together. ¬

She didn't note what time she left but when 10 am came around, I started to wonder. I was doing some pushups and sit-ups when she finally arrived. She showed off her body again in some tight running shorts and sports bra and both pieces were soaked. She wasn't breathing hard however.

"Hi hottie," I said and squeezed her sweaty ass before kissing her equally sweaty mouth. "How long were you gone for?"

"2 hours and 10 minutes. I walked for a while before running to make sure my breakfast shake was digested enough and then I walked for a good twenty minutes in the end," she explained.

"I am sorry you couldn't finish," I said honestly.

She quickly punched my upper arm. "Who said I didn't finish?" she challenged me. "I ran the 13 miles in less than 2 hours."

"Wow, nice job," I said giving her all the props she deserved. I was definitely jealous considering that she barely trained for it and could put up a good time. She was in that good of shape.

I made her a protein rich breakfast while she took an extra-long shower. She came out in a sexy bikini set and a beach towel.

"Let's go to the beach after brunch," suggested Destiny.

An hour later we found ourselves at the beach that wasn't too crowded yet. We had lathered up each other in sunscreen at the house so we were able to relax right away.

"You should be happy to know that my butt felt fine this morning. I put some more ointment on just in case but with the amazing massage last night my body felt amazing. I think that made it easier for me to run this morning," she told me.

"That is a relief. I wouldn't mind giving you a massage every day leading up to the race," I offered.

"I'll take it. And I don't have to tell me that this body of mine is yours," she said and stroke her glistening thighs.

"Thanks for the reminder. I'll be sure to remind you of that later tonight," I responded.

"Let's go into town and do some shopping and sightseeing," she said.

We agreed to have lunch in town and after hitting our limit of lying in the 90 degree sun we went back to the house. I was pleased to see Destiny come out of the bedroom wearing the mini-skirt she wore to the beach the first night along with a halter top without a bra.

"I hope you don't mind that I am not wearing anything to cover up my privates. I think fresh air helps my butt feel better faster," she explained.

We spent the next couple of hours eating, shopping and laughing but aside from a few flirts and thigh rubbing remained fairly PG. It wasn't until we got onto the escalators when Destiny's short skirt got her into trouble. She forgot her lack of undergarment when she raised one leg on the higher step causing her skirt to ride up a little. The bottom part of her ebony ass came to view for anyone at an eye level or lower. By the time we got to the top, at least a dozen men looked at her from the bottom floor. One of them even tried to get a picture with his cell phone.

When we walked by a jeweler and shortly after by a nail salon I quickly decided to let her get a pedicure, manicure and facial package so I could get time to myself. She quickly accepted the offer and I ended up at the engagement ring counter. A blonde female sales clerk in her fifties helped me and after a few different options, she helped me settle on a princes cut that came with the center diamond that was over a carat large and a bunch of tinier ones around.

I had no idea about ring values but before I dropped $12,000 on it, I made sure it was comparable to prices I saw online, which it seemed to be. It turned out that Destiny had the default size for rings or at least something close based on my quick measurements so I was hoping she could wear it right away.

When I was greeted by my elegant soon-to-be fiancé, I kept my hand in my pocket for most of the time afraid it would fall out. We had a great time the rest of the evening and ended up eating dinner at a small local eatery.

"So what would you like to do tonight?" I asked.

"I got it all figured out. I just need you to be at the house fresh and clean," she responded.

"Well, let's skip dessert then if that's the case," I said.

"We won't need to be there until 8," she explained.

"So we have an hour," I concluded.

"Well, let's go find a place I can suck your cock and if I get wet enough you can take me real quick," she flirted and put her hand under the table. "Never mind, I am already wet."

I quickly paid the bill and we made our way back to the car that was parked a good 10 minute walk away. At first we were surrounded by a few other shoppers as we walked through the beautifully landscaped path. I didn't waste any lost opportunity by lifting her skirt and rubbing her naked ass when no one was around.

We turned the corner and there was a bench a good 50 feet away from the main path overlooking a pond. I threw Destiny over my shoulder and ran towards the bench causing her to shriek and laugh. I didn't have to tell her what to do next. After we sat down, she opened my fly and pulled out my semi-erect penis. After only a few licks and kisses it was fully erect.

She also wasted no time and started deepthroating me until her lips met my shorts. I sat back and started playing with her moist sex and looked out for anyone who might see us. She was getting really into after a few minutes and the gagging and slurping sounds started echoing around us.

"Fuck baby that's perfect," I groaned and held her head in place with my right hand right after she descended on my rod again. I quickly rubbed her clit while keeping her head in place. I finally let go of her when she coughed a little while my cock was nestled in the top of her throat.

"Let's get out of here. I got some prepping to do when we get home," explained Destiny.

"Just one second," I countered and grabbed her by her hips to lift her on top of me. Her wet entrance ended up right on top of my raging cock and she plunged downward when I let go of her. She rode me ragingly for the next minute until we heard voices in a distance. To keep up the sexual energy, Destiny licked me clean on our short drive home.