Cheering Up Grandma

These are fictional events. Let me know what you think. It will be continued if I get some feedback. So, let me know what you think.

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Reinhold Hartman, “Reg” to his friends woke up knowing that it was going to be a bad day. He got up late, wishing he had had enough money to go on a spring break trip with his friends. Instead, he was stuck here at his parents’ home with nothing to do. He went to the bathroom to take a shower, stopping to look at himself in the mirror. He was a large guy. He stood five foot eleven, and weighed around two hundred and eighty pounds. A surprising amount of it was muscle, excepting a little bit of a belly. Since he went to a college with no football team, he saw no need to keep up the rather strenuous exercise program he had done in high school. His caramel colored skin was smooth in the morning light. He wore his brown hair in short dreadlocks. His eyes were a rather shocking green. He owed that to his German heritage. He had a rather ponderous heritage. His great-grandfather had moved to Germany from Namibia around 1889. His son Erik had married a native German named Adelheide, whom everyone called Heidi, and moved to the United States well before the outbreak of World War I.

Reg finished his shower, put on some shorts, and went to watch some television. He turned the TV on the news just in time to catch the Lottery’s winning numbers. 17, 24, 65, 9, 18, those numbers sounded familiar. He jumped up and ran to his room to get his ticket. He realized that they were his numbers! He had NEVER been more excited! His first call was too his parents at work and his next was to find a lawyer.

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Two Months Later

The hubbub had finally died down, although it had been quite considerable. It was not everyday that someone won a 324 million dollar lottery. He had taken the money in a lump sum, ending up being worth around 220 million. He had already brought his parents a new house, and cars. He had dropped out of school for a while and brought a couple of toys for himself too, including a stocked Hummer truck. Now he was super rich and with nothing constructive to do with his time. He decided that he was going to do some traveling, but he did not want to go alone. He thought about whom to take for a while. His parents still wanted to work for a while, although they no longer had to. He was not in any kind of relationship with any girls. He had had a couple of one-night stands, but nothing serious. The only other person who he could think of was his grandmother. Grandma Heidi had been depressed and in a low mood every since Grandpa Erik had died last year. He thought a trip around the world might cheer her up, so he called her up and offered to take her. At first, she refused. However, he kept on her and soon his persistence paid off.

He called the lawyer he kept on retainer and told him to set up a trip for two. First he would fly in to pick her up in New Jersey they would take a limo ride to nearby New York for some shopping and then they would fly by chartered jet to Las Vegas. The flight to New Jersey was uneventful. He arrived at his grandma’s door in a stretch black limo with two-dozen red roses and a box of chocolates. When he knocked on the door, she opened it and gave him a big hug. Although happy, she seemed lifeless compared to her former self. Heidi was tall, almost five feet eight. She was a large woman, weighing about two hundred fifty ponds to two hundred and eighty pounds. She had always been shapely, very curvaceous when she was young and slimmer, but carrying the shape well with the added weight age had brought on. She used to be a jollier woman before Grandpa Erik had died, quick to laugh, sing, or dance. She went to get her bag, but Reg told her not to take anything, because he was going to buy her a complete wardrobe for the trip. She started to protest, but he convinced her that it was easily within his means.

They did a great deal of shopping. Heidi picked out many gowns, suits, and casual clothes. She helped Reg pick out a full custom tailored wardrobe including suits in wool, linen, silk, and even three tuxedos. She had impeccable taste. He would never have picked out a wardrobe as good without her. Years spent as a seamstress and then designer for an off the rack retailer had given her an eye for what would look good and what would last. They checked in to their rooms at the W Hotel over Times Square to spend the night. Reg suggested that she get the concierge to help her find a hairdresser and get her hair done, charging it to the room. She left, returning in time to make their reservations at Gustavino’s. They stood in the elevator in their finest. He was in an all black tuxedo, and she in a beautiful green dress. She looked so much livelier after returning from the hairdresser’s. Her reddish blond hair was cut to shoulder length. Her hair and the dress set off her light emerald eyes. He had to admit that she was striking. Just the type of woman he had gone for recently. The green silk dress clung to her curves. He had never seen her in an evening gown and found the effect intoxicating. Her breasts were much larger than he had thought. Heidi was what most people would call fat, although he found her perfect. They walked out to the limo making quite a striking couple, a twenty-year-old black man with a white woman in her sixties.

Dinner was exquisite. They retired early to be ready for the flight first thing in the morning. They made the flight, landing that afternoon and going directly to their suite at the Piazza Suite at the Venetian Hotel. They got to the room only to find that the lawyer had booked a king size bed instead of two separate beds. The lawyer must have thought that these reservations were for a woman friend. Heidi, who seemed to be in much better spirits said it was ok, and that a king size bed was enough for many more people. They had a quiet dinner in the suite, neither feeling like going out and braving the casinos. They decided to turn in early. It was at this moment that Reg remembered that he had not purchased any underwear or pajamas. He did not really like wearing them on his own, and it had not mattered when he had had his own room.

“Grandma Heidi,” said Reg “I have a little problem. I usually don’t wear underwear and I usually sleep in the nude.”

“That’s ok my little king” she said. ‘Her little king’ was her nickname for him, tracing back to the German origins of his name, although she had not called him that in years. “Its all right if you sleep in the buff, I promise I won’t peek too much.” With that, she went in the bathroom to change. When she came out, she was wearing a thin cream silk nightgown. Reg was awed by what he saw. The robe was thin enough so that he could tell that she was not wearing anything under the gown. The first thing he noticed was her breast. They were humongous. He was later to find out that her breast measured in a whopping 65 double J. The nipples stood out clearly, surrounded by large brown areola. The gown hugged her relatively narrow waste, ballooning out to cover her huge 62-inch hips. Through the almost diaphanous fabric, he noticed the abundance of curly pubic hair at her crotch. When she turned to get something out of the bathroom he could not help but notice how tight the silk stretched to cover her enormous ass. When she was done, Reg went into the bathroom. As he took off his slacks and shirt, he could not get the picture of his grandmother out of his mind. Try as he might, all he could think of was the way the cream colored silk hugged her huge breast and hips. He had never thought of his grandmother sexually, but the months of abstinence had caught up with him. He felt his cock start to harden as he thought of her body. He concentrated hard to keep his cock from standing up fully. His cock was about seven inches long, not that much above average, but it was impressive in its thickness. It was as thick as the average person’s wrist. He thought it looked impressive even when it was not hard. Flaccid it hung down about five inches in front of his large testes. As it was now, it was about six inches long, standing up just a little and leaning to the left. When he was sure that it was at least under control, if not getting any softer, he gathered his clothes and left the bathroom. His grandmother was already in bed, under the covers up to her lap.

He walked shyly to the bed and quickly got under the covers, noting how his grandmother’s eyes seemed to be following his bouncing cock. He got in the bed at a little distance from her. “Oh, you can move closer little king, I am not going to bite.” He scooted closer to her, glad that he was under the covers because he had started to harden again. She tuned to him and said “Since your Grandpa died, I have been lonely, I want to thank you for making a fat old lady feel loved and inviting me on this trip” and pulled him into a tight hug. He could feel her breast resting on his lap, his cock was warmly nestled under them, but if she noticed, she said nothing.

“It’s ok Grandma I love that you were able to come with me on this trip. And don’t call yourself fat and old, I love you the way you are” he said.

She broke the hug and rubbed his cheek, “That’s sweet of you to say little king.” He noticed that his cock had left a spot of pre-cum on her breast, but decided to say nothing. She turned out the light and they both went to sleep. Reg awoke a couple of hours later, after having a very erotic dream which he could not really remember. His phallus was throbbing and painfully erect. He turned and looked at his Grandma through the light of the semi open window. The covers had been thrown most of the way off and she was stretched out. Her gown had ridden up her thighs, almost to the bottom of her pubis. One of her breast rested on her chest, the other in the crook of her arm. Reg moved closer to get a better look. He moved to where they were almost touching and roamed her body with his eyes. As he stared at her, his hand unconsciously went to his turgid cock. As he took in her massive tits, he stoked the head and shaft. Before he knew it, he felt a tingling at the base of his cock that signaled an oncoming orgasm. His load shot out forcefully, audibly landing all over her, and the sheets. Enjoying of the most intense orgasm of his life, Reg fell asleep, exhausted, but happy.

The next morning, Reg awoke with morning wood and feeling the first stirrings of guilt. He looked around to find Heidi gone. She must have been in the bathroom. He stood and stretched, his cock pointing at the ceiling. He noticed that the door to the bathroom was slightly ajar. He craned his neck to look into the bathroom. She must have noticed him, because she asked him to come into the bathroom. He went in with a sense of trepidation, fearing she would ask about the large stain on her gown. Surprisingly however, she did not even mention it. She was sitting in the large tub smiling up at him. She asked if he would wash her back. He went up to the tub and noticed that there were no bubbles in the tub and he could see straight down in the water. His eyes were immediately drawn to her plentiful bust and then to her hirsute pussy. He must have had a shocked look on his face because she said “Oh come on, it can’t be that bad.”

“No Grandma, I was just shocked, I thought you were taking a bubble bath.”

“It won’t hurt us to be a little informal,” she said.

“Well then let me tell you that I am enjoying the view Grandma,” Reg said a huskily. To his surprise, she blushed bright red and asked him again to wash her back. He took the soapy cloth from her and washed down her back, not stopping until he had “accidentally” brushed her plentiful backside with his hand several times.

“My little king,” she said, “can you reach and get me the shampoo?” his inhibitions being overridden by his growing desire, he stood, leaning over the shower to grab the shampoo, knowing that his hard, pre-cum leaking cock was right in her face. He heard her gasp when his reached forced it directly into her cheek, but she said nothing when he handed her the shampoo but thank you. He excused himself to the toilet room to take a piss. When he entered the main bedroom, Heidi was coming out of the bathroom wrapped in a towel. Apparently, she was serious about having less formality, because she stripped off the towel and began to slowly and sensuously dry herself. Instantly he began to harden once again, as he watched her silently. When she was dry, she walked over to her dresser. Her walk was a smooth, swaying one that only served to increase his arousal. She bent at the waist to pull a large bra and some pantyhose out of a drawer. He watched, yet spellbound as she pulled on the pantyhose and then the bra. “Well little king,” she said snapping him out of the spell, “you would think you have never seen a woman dress.”

“I’m sorry Grandma, but I really haven’t seen a woman dress before. The only other time I have been naked with a woman, I slipped out before daylight.” They had always had an open relationship, so he felt ok telling her this.

“Well it seems like you got a little enjoyment out of it,” she said with a cryptic wink. “Why don’t you get ready so we can go out to the casinos.” Reg left to take a quick shower. He dried himself in the bathroom and came out naked sporting a huge erection, hoping to incite some sort of comment. However much she watched him pull on the slacks over his hard-on, she said nothing. They left to enjoy a full day of gambling, with modest losses, and enjoyed a show and a leisurely late dinner at one of the hotel's restaurants. They went to bed soon after dinner. This time, Grandma came out of the bathroom, wearing a new white, tighter, and amazingly more transparent silk nightgown. Reg came out wearing only a throbbing erection. Grandma hugged him again, this time kissing him on the cheek and rubbing his chest a little afterwards. She then lay down and was soon asleep. Reg was so worked up that there was no hope of him sleeping. He pulled the covers down to stare at her body. He moved closer until his rigid rested on her thigh. He boldly reached to touch one of her breast. It was huge and as soft as could be. He thought he felt the nipple harden in his palm. He took his hand and placed it on top of her hairy bush. He touched her nether lips through the thin silk of the gown. With his other hand, he reached to touch his turgid cock. He was so excited that it didn’t take much more than a touch for him to explode even more forcefully all over his grandmother, some landing all over her face, tits, and belly. He grabbed a Kleenex to clean what he could from her face and left the rest to dry.

In the morning, they quickly dressed and went to board the hotel’s shuttle to Hoover Dam and the Grand Canyon. They had a great time walking hand in hand and seeing the amazing sites. They had a great dinner at one of the many Vegas buffets and returned to the suite to watch a movie. Reg was surprised when Heidi turned it on a pay for view station to watch an adult movie. They watched the movie all the way through, Reg getting painfully aroused during the process. When it was done, Heidi suggested that Reg go to the bathroom first to get ready. When he came out, nude with a hard-on, she went in, only to return amazingly nude herself. Reg’s hard-on was pointing towards the ceiling, leaking copious amounts of pre-cum, glistening in the lamplight. “Well, my little king,” she said, “We need to talk. It seems that you have been having the wet dreams the past couple of nights. I know because every morning I have awakened to find myself, and the sheets covered in sticky dried fluid. It is not like I haven’t noticed you being aroused all the time when I am around, or am complaining, but I do not want to ruin another silk nightgown, so I am going to make sure that you go to bed tonight with those large testicles as empty as we can get them. So I want you to sit on the edge of the bed and I am going to help you out.”

When he had sat, she got to her knees in front of him. She placed her breast on his knees and firmly grasped his member. She began stroking him slowly, grabbing and massaging his testicles with her other hand. Her strokes began to increase in speed. Reg knew he would not last long. His breathing began to get quicker and heavier. “Oh, grandma, I am going to cum,” he yelled hoarsely.

“Its ok, my little king, cum for Grandma.” Hearing this, his load exploded from him with a perceptible gush, shooting over Heidi’s shoulder, finally trickling and covering her hand. She got up and wiped her hand on a towel, and returned to bed. They snuggled up together, and she lightly kissed his cheek. He reached out to cup her chin, and pulled her into a deep kiss. When his tongue entered her mouth, she did not complain or pull back. Her hands found his still hard cock and began to massage it. When it was fully erect, she lay him down and wordlessly straddled him. After a couple of strokes, she began to shake an orgasm. Soon, Reg felt himself about to cum as well. He let loose with a scream, spilling his seed into her. They collapsed into the bed, both exhausted. Then surprisingly, before he fell asleep, Heidi said, “My little king, rest well for tomorrow, I am going to show you how to give much pleasure to a woman.”

To be continued…