Harold loved looking at butts. He didn’t care much in what form they came. It was not really the pair of human round watermelons situated at the lower behind of a person that he was interested in, but it was what’s in-between those two human watermelons that he was attracted to. There were various kinds of holes and passages that awaited him to explore. He always preferred having anal sex as opposed to the regular sex. First of all, any woman could be laid by him. He had no preferences. All butts are round whether the woman is skinny or heavy. It was only if the woman liked it or not and would allow him to do it or not. That was where the ‘choice’ came in. If the woman did not like anal sex, that was the end of the relationship. They would only remain as friends. To him, love was allowing him to have anal sex with him in various positions. He had stories to tell about his relationships with real heavy women and stories to tell with very thin women – and nifty sex stories about his relationship with conservative well-known women that nobody knew about.
Harold, a six-foot three good looking and well-built Caucasian man in his thirties, worked as a window salesman for a company during the day and to make ends meet, he took the job as an on-call freelance masseur during weekday evenings and on weekends. He distributed his masseur business cards to all of the window clientele he visited. Sometimes, when he had no sales for a few days or for a week or so, out of desperation, he offered a free one-hour session of whole body massage per client. This tactic helped him increase his window sales after his window client received a free one-hour massage session with him. And this free offer also introduced his skills in massage that brought him more business as a freelance masseur. Often times, these free one-hour massage sessions turned out not just a massage session especially when the client was well-to-do. Yes, as expected, sex got in the way extending his one-hour massage session into a one and a half to three-hour massage-sex session. The window client would ask how much he charged per session and they would double or triple the service fee if he extended his time and have sex with them. This was because they loved his dick, his appearance, his voice and his smell. He was quite a handsome, vibrant and energetic man that looked like he was twenty-one years old but he was actually thirty-five years old. These were offers that he would never refuse especially, he would be enjoying, too anyway.
One wealthy forty-three year old woman who was single and lonely was one of these clients who paid well and who became Harold’s regular customer in his small massage business. She owned a mansion that she inherited from her grandparents and several other buildings, farms and business companies that she inherited from her parents who met an accident when they were flying to one of their lands in the country. They did not make it. Their private plane was unrecognizable after the crash. She was their only daughter; therefore, she inherited everything. Meredith was too rich to marry anyone because they were only interested in her riches and not in her as a person. Being rich and having a doctorate degree in actuary from a very prestigious university, she was often invited to be a guest in TV shows.
Friday night was Harold’s reserved night for Meredith. It all started when he was assigned to sell windows to Meredith who wanted to change all her windows to something different, bright and new. The design of the mansion was an old design that she wanted to add a touch of the cyber era to the place. She was a big client who was very picky, very meticulous and very particular with her choices. Being a perfectionist, she even discreetly inspected all her guests from head to toe. Harold was the seventh window salesman from the seventh window company, who gave her a visit. If the salesman did not look good, Meredith did not bother even listening or looking into their brochure; and just let the salesman leave her home. Her neighbors called her “The Old Maid” because she acted like one. And she found Harold to be the perfect salesman; thus, she eventually changed all her windows in that mansion to the windows Harold was selling.
When Meredith found out that Harold was a masseur, she did not waste time to invite him to come on a Friday night outside work. She greeted him clad in a robe with nothing underneath. When Harold was ready to give her the massage, she removed her robe in front of him teasingly. Harold tried not to look, but could not avoid noticing how beautiful her body was at that age of forty-three. Meredith brought up the conversation,
“You like my body?”
“Yes, Ma’am. It’s beautiful,” he said politely.
“I will let you have it if you massage it well,” Meredith proposed with a kinky smile.
“Well, Ma’am … I will try my best,” smiled Harold who went along with what he thought was a joke because he knew that no rich woman would even think of ever touching or be touched by a man from the opposite side of the world of wealth and financial stability.
Meredith laid her body in her bed and Harold massaged her back with great expertise that Meredith felt horny. Harold could not help eying her butt and Meredith did not miss a single movement of Harold because she had mirrors all over the place. She had observed that he kept on looking at her butt.
“Do you love those pair of behinds, Harold?” teased Meredith.
“Mmm, yes, Ma’am,” Harold replied honestly, trying to make her happy by praising her bodily assets. And besides, he was almost sure that he would never have them, especially her asshole.
He just continued with his massage on her. When his hands reached her butt, she reached out for them.
“I will let you use them and enter in-between, if you like. I will even pay you for doing so and also pay you triple for your time. How about that?”
The proposition was very tempting. Harold, at that very moment, didn’t know what to say or do next. He was speechless. Meredith turned around and helped herself removing Harold’s clothes, Harold not budging. Meredith saw Harold’s erection, to which he flushed red in embarrassment.
“See? I was right. Come on, don’t be shy,” she turned and bent over. Harold’s weakness was facing him there and then.
“What are you waiting for, Harold? Come and get it!” commanded Meredith. “Don’t you worry about the time extension, I will pay for everything. Name your price and I will double or triple it.”
With that, Harold took a condom from his pants’ pocket, clothed his dick with the rubber and took the K-Y jelly that Meredith handed over to him and entered his penis into her asshole.
“Man! This is so erotic and nifty!” Harold thought. “Man! I’m having sex with one of the richest women here in this country!” He was so excited to please her and he was also surprised that she let him fuck her from behind.
“Do you really love my ass now, Harold?”
“Yes, definitely,” Harold replied.
“Then, FUCK me HARD!” she commanded.
Harold did as commanded. Then, by instinct, he turned her to her side, lifted one leg vertically up and continued fucking her asshole.
“Yes! That’s it! I knew you were the perfect one! uuUmmm… AAAhh!” she just could not add any more words. The fucking was so good!!!
Harold turned her to the other side and pumped hard. Both of them were panting really heavy. It was their first time to have sex together that both got extremely excited that they both came sooner than expected.
That was the very first Friday massage-anal sex session Harold had with Meredith. He was paid very handsomely. Since then, Friday evenings from 8pm to 10pm were reserved by Harold exclusively for Meredith doing the same things: massage and anal sex. Furthermore, as time flew, their appointment time extended till the morning and Harold was getting richer each time she extended their sessions. She paid him promptly in cash and in full before he left.
~ the end ~
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