Oscar's Cuckolding free porn video

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Hi, my name is Tony and I’m about to tell you a tale of tail that has unfolded over the last year or so.

We often meet at the Club de Mar Almira for drinks. I live on a sailboat in the marina in the Spanish coastal city of Almira. This day Oscar was in a foul mood. He was almost finished with his favorite Soberano brandy before he opened up to me, the best friend he had.

“I’ve thought for a while that my wife was fucking around on me but now I know for sure,” he complained.

I looked concerned, ordered another brandy for him, and asked, “How did you find this out?”

“That woman made me wear a condom last night for the first time since I had my vasectomy six months ago. We used to use them for birth control on her fertile days and I thought we were done with them. When I asked why she looked me in the eye and said she now had a lover and he didn’t want her to be messy for him. Isn’t that shitty?

“Earlier in our marriage I talked to her about fucking another guy for our fun and she wouldn’t hear of it so I quit. I wondered what had changed her mind so I asked her. That slutty new friend of hers from work, Angel something-or-other, convinced her that I wasn’t enough for her and she should try out some other guys to prove that she was right. Irene found some stud with a big dick and she likes it a lot. She made it very clear that if I want to keep her as a wife I’d better cooperate. Damn!”

I knew Angel. She was what I called a “boat-slut”. She’d fuck anybody who would take her out on their boat. Sort of a “ride for a ride”, I guess. I heard that she spent one weekend with a friend of mine and two work mates and she fucked all of them non-stop the whole time. Not for me. I like quality women.

Now for a little more background to this problem my friend was having.

I’ve known Oscar for about five years because we worked together for a while. He’s forty-three and I’m thirty-five but we hit it off. I was married when we met, no kids, and we would get together with their two young daughters or just as couples. My wife ran off with another woman and I just date now. I have no desire to buy a book when the library is nearby. Chicks like sailboats so I get enough pussy, even though I’m fussy.

Oscar’s wife Irene is the same age as Oscar but only had sex with him before marriage, unlike her husband who had a few prior experiences. Her head is adorned with reddish brown wavy hair down to her shoulders. She is 160cm (5’3”) feet and has nice exciting and full curves. She’s “ample” after two children at 69kg (152 lbs) but carries it well.

Oscar, at 177 cm (5’ 10”) and “a little” overweight at 105kg (231 lbs) has short brown hair and big brown eyes. His main concern is his genital size, below average at 11.5 cm (4.5 inches)

I am the same height as Oscar but much trimmer at 79 kilograms (175 lbs) because of my sailing and better diet. Maybe getting more sex helps too. My equipment measures 19cm (7.5 inches) long and 6 cm (2.5 inches) wide just behind the head which is not covered with a foreskin, unlike Oscar’s.

This revelation from my friend didn’t surprise me at all. My first hint that Irene was changing happened on a recent sailing outing. It was a warm day so we’d anchored and gone swimming. Here in the Mediterranean topless is very common so Irene and the daughters all swam that way. Seeing Iren’s bounteous curves uncovered and bouncing around made a bulge in my tight, brief swimsuit. She smiled when she noticed me ogling her body and her eyes went to my crotch. I need to mention that my first piece of ass was an older woman with plenty of curves too, and she made good use of them the many times she was naked with me. That is my favorite body style.

We were getting back late and the daughters and Oscar fell asleep below in the cabin. It was cooling off so Irene snuggled up to me at the wheel and put a beach towel around us. She had enjoying being topless all day so hadn’t put her upper suit back on. I put my arm around her and when my hand accidentally brushed her breast she hummed, clearly not concerned, so I reached down to cup it and she hummed louder. I felt her hand reach for my growing bulge and she stopped humming as it grew and the head protruded when she adjusted my suit to let it escape. After a few moments of touching it she said, “It is magnificent but I’d better stop before I go too far.” She went below and got dressed then back under the towel, not mentioning what had just transpired.

Two days later Irene called me and asked to have a drink on my boat after work. I offered her some sangria and let her take the lead. She opened with, “Maybe you know that I have had sex only with Oscar. That is what my Catholic parents expected. I have suspected he is a bit on the small side and my friend Angel assures me his size certainly is. The other night I was startled at how big your organ got. Is it uncomfortable for a woman?” I reassured her that no one had ever complained although a few had to adjust a little bit.

She took a big drink of wine, gathered her courage, and begged, “May I see it in the light?”

I stood up, undid my pants, and there it was, in all its limp glory.

She gasped, “My God! It is bigger soft than Oscar is fully hard. May I touch it?”

“Only if you want to see it stand up for you,” I quipped, adding, “It might like a kiss too.”

That was the encouragement she needed. Kneeling on the cabin floor she used both hands to hold and rub the shaft and cup my big hanging balls. My pride and joy filled before her eyes. Remembering the last thing I had said, she tentatively kissed and sucked it a bit too.

“The head is not covered up with skin like Oscar’s!” She exclaimed.

“That is called a foreskin which gets trimmed in a circumcision. You don’t have to roll it back.”

She tried it for herself and commented, “I always wondered what circumcision was. Does it feel any different to a woman?”

I couldn’t resist that lead, “I guess you will just have to try it to find out.” She sucked on it a little harder as I continued, “Some women say they can tell.”

I poured her another glass of wine. “It doesn’t seem fair, I am showing you my parts and I can’t see any of yours.”

“Oh, you can’t possibly think that a fat older married woman like me is sexy. I’ve seen some of your dates.” I knew she wanted to be persuaded.

“You are on board my ship and I’m the Captain so what I say must be obeyed.” Her sudden grin told me I was on the right track, giving her orders. “I want to make an inspection so remove your clothes immediately.”

She immediately complied, still standing. I walked around her and reached out to touch her nipples and buns. She shivered when I touched then. I could soon smell her arousal. I leaned over and put my hands under her full breasts, raised them up a bit, and then bit her already hard nipples. She writhed and moaned.

“Undress me completely and pleasure the Captain’s cock,” I ordered. She made quick work and her mouth got full of my organ. I hadn’t been laid for a few days so I was rising to an ejaculation. I ordered, “Get ready to taste the Captain’s seed.” Oscar said she didn’t like to give head and had never tasted his cum but she was compliant for me though, and swallowed like a champ.

She seemed disappointed as my cock wilted so I asked, “Was there something else you wanted?” She nodded and replied shyly, “I wanted to see if your big penis would fit in me.”

“Oh, in that case just keep pleasuring it with your mouth and it will soon be ready to impale you.” It didn’t take long as I thought about bouncing on her well-padded body.

As Irene laid back and opened her thighs as an invitation, I asked her, “So you are willing to let me, a friend of your husband, put my penis into your married pussy and shoot my sperm there. What if you get pregnant?”

She looked back at me and answered in a quivering voice, “I just have to try that big thing you have. I’ve never had any sperm in me but my husband’s so that will make me wicked, but I will live with that. I won’t get pregnant because this is a safe time so shoot away. It will be an excitement I’ve never had.”

Placing the point of the spear just millimeters from her moist pussy lips I commanded, “Tell me again what you want!”

“I want you to fuck me!”

Pressing firmly against the opening I ordered again, “Tell me exactly what you want!”

She was beginning to pant with desire and her voice quivered, “Stick your big cock in my cheating married pussy and fuck it and shoot your sperm where my husband does.” That was what I wanted and I began small in-and-outs that kept getting gradually deeper. She struggled to hold still as the sensations of her stretching pussy got stronger and stronger.

Finally, our pubes met and she clamped her legs around me. “Push with your hips when I go into you. Bump your clit on me.”

This was new to her and her excitement built until she had her first orgasm just from cock alone. She shook and cried out her pleasure and then laid back limp, exhausted. I kept moving inside her until I felt my pleasure hitting its peak.

“Here is the cock-juice you wanted!”, I exclaimed as the first of many hot spurts erupted inside her. She moaned with each one, saying how wicked she was. From the tone of her voice, it wasn’t a very bad “wicked”.

We rested briefly and she showered and kissed me as she left. Nothing was said about a next time but I knew there would be one. I rested up. I had a hot date tonight.

Two days later she was trying out my meat again. This time she wanted to be on top. That made her breasts a lot easier to enjoy and let her try things her way. I didn’t need to give any orders. She knew what she wanted.

A few days later we had a sail outing planned. I had invited my favorite girlfriend before Irene had come on to me. I couldn’t just un-invite her. Plus, it might keep our affair in balance. I sure didn’t want Irene’s sexual explorations to destroy her marriage.

It would be interesting to see how this newly-cheating wife would handle the situation.

The daughters were with grandparents so I could really push things. Oscar had told me over drinks that Irene was acting differently. She had refused him sex for the first time ever. He would be quite horny for what ever happened.

Irene handled Yolanda’s presence reasonably well. She could not directly compete with the taller, skinner, younger blond, so she didn’t try. I did get a glance that would have killed if it could have even though I explained the circumstances.

Captain’s orders were topless before we got underway and bottomless when we reached the anchorage where we would spend the night. THAT was going to be interesting, I knew. While sailing Oscar got up on the front deck and was chatting with Yolanda so Irene had a chance to talk to me.

“Do you fuck her?” was the first thing out of her mouth.

“Of course and for more than a year. She has other boyfriends too and is not jealous of any I have. She will fuck your husband if I ask her to”

“Absolutely NOT!”, came the quick reply showing her double standard.

Then another one from Irene, “Do you like her better than me?”

“You are very different so it is not a matter of better. Is that not true of me and Oscar?”

She looked pensive at that question, “I have not let him in me since we started out of respect for you. He is so much smaller I may not feel him anymore.”

I looked at her and gave an order, “He is your husband and lover for many years and is my friend also. I want you to sex him when you want but we will eventually make him wear a condom. But perhaps it would be exciting for you if he went in bare when it was right after I had inseminated you. Two juices in you at the same time would be hot like it has been for my girlfriends. Yolanda has fucked another boyfriend just before doing me.”

Irene said she’d think about that.

We reached our anchorage in early afternoon and swam and ate and drank. When thigs slowed down I asked Yolanda to take a nap with me. You must realize that sailboats are small and nothing is hidden so I knew they would hear and feel as we screwed. Irene and Oscar stayed in the cockpit but made no comment when we returned except for Oscar’s small erection. I’m sure he wished he could fuck her too.

We had a late dinner and watched the sunset. I fucked Yolanda again at bedtime but heard nothing from the other couple in the bow cabin. Yolanda had been drinking a lot and fell asleep after her orgasm. I went up to the cockpit and could hear Oscar snoring.

Irene came quietly, wearing a light robe. Without a word she bent over and, with hand and mouth, urged my manhood to the condition she wanted. When it was ready she turned her back to me, pulled her robe aside, and sot down in my cock. I reached around to tease her tits the way she liked while she rode me. Her fingers were fluttering on her clit.

As drained as I was, it took a while for me to cum but she got hers twice. There was no kiss as she simply got up and, without looking back, went to her berth. A short time later I felt the boat moving rhythmically. Oscar was getting seconds but unbeknownst. I’d left much less semen than usual so he probably thought it was her natural lube. Smart girl.

Irene played it cool the rest of the outing and found another time to get some of my cock too. We talked on the sail back and I told her I was pleased with her behavior. My schedule only allowed her two turns with my cock each week so she’d have to use her husband the rest of the time. She told me that her fertile period was coming up and I’d have to use condoms.

“I don’t use condoms with any one,” I emphatically replied, “You will just have to do without.” I bet that she would “take a chance”, and I was right. The subject was never mentioned again. She was now under my control so time to take the last step.

“Irene,” I said, after we had screwed one afternoon, “You must tell Oscar that you have a lover, but not who it is. Now is the time to mandate wearing a condom unless you have just been laid. I think it will excite him to fuck in another man’s cum. That is a special treat. For me it is especially erotic to feel the silky slipperiness, knowing how it got that way. For the woman it is wicked and very female to welcome different seed. Oscar will be humiliated because it is his wife being promiscuous and unfaithful. He wants that.

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Fat wife fucking with cuckolding

I was surprised to get a reply from the ad I placed on the net looking for a women who wanted to fuck in front of her husband. I had requested a woman aged from 35 to 50, over weight and not uncomfortable with it. The reply was short requesting a meet in a hotel in London, I had said when I would be visiting London etc. and the meet was arranged. When I walked into the hotel bar I saw her straight away sitting at the bar, she was dressed as she said she would be in a knee length skirt, white...

4 years ago
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A bulls experiences with cuckolding

In 2012 I answered an ad on craigslist by a married woman looking for something on the side. I’ll call her Ginger. She was in her mid-40s and I was 27 at this point. I love older women so the age difference was an immediate turn-on for me (I love being the young stud who satisfies the older established woman with a lacking sex life, it’s a very hot dynamic to me). We exchange a couple of short emails before I’m given a phone number. Turns out that it was actually her husband who posted the ad....

1 year ago
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As We Prepare To Go To Vegas My Wife Steps Up The Cuckolding

The Tuesday after Memorial Day when I got home from work Terri was in the kitchen preparing dinner. I walked in there and said, “Let’s talk about the last few days and what direction we want to see things go from here.” Terri responded, “I think that is a great idea, what are your thoughts?’ “Terri I am going to be honest with you, thinking about what has happened recently excites the hell out of me and makes me feel younger than I have in years,” I said. She said, “I am so glad you feel that...

3 years ago
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338 coastal cuckolding

Part 5Well, she had had anal, and he knew that until he got some sort of lube, he was never going to taste those delights himself, thus it was that they went shopping on a Saturday, something he hated, or at least avoided normally. They were on the return journey when he dragged her into Scrooges shop, walked boldly up to the owner, there being no others in and announced, “Ah Richard, as we are apparently sharing my lady, perhaps we can agree a few things.” By now Scrooge was both red and a...

4 years ago
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Facts about my cuckolding

It's absolutely true that my wife has sex outside our marriage. I'd like to think her stepping out is all due to my encouraging. Within a year of our wedding I noticed the sex wasn't all that. I'm not very well endowed and I'm a premature ejaculator. My wife was always extremely understanding and played it off that she was ok with it. I begain telling her about how I would like to have sex with her after she had been made love to. She was a good wife and continued to play that off as it was...

2 years ago
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How me and my wife got into Cuckolding

Things had been strained between my wife Clare and I lately and she wasn’t into having sex, at one point my mind drifted to thinking maybe she was having an affair. I could only think the best thing to do was to be party to this if I wanted to keep my wife. I suggested we look into swinging and wife swapping but she refused. Anyway time went on and then one night we met this guy and there was obviously sexual chemistry between the two of them and though my heart was sinking I did pull my wife...

3 years ago
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my first cuckolding

So the night arrived and i found her getting ready for her young black stud. she is in her late thirties and a very hot woman. big boobs lovely legs a peach of a bum and a sexy gorgeous face. she has always liked black men and is a bit of a cougar for the young bulls in her area. when i got their she was getting ready for omar a mid twenties black guy who she had found very hot. she had met him the previous day and he had given her a good fucking. she had texted me after he had gone that he was...

4 years ago
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RebelChapter 77 Cuckolding

The colonel's lady was a beauty, a stately woman of fine proportions and haughty grandeur. And she was a terror in bed, nearly insatiable and wholly satisfying. My job was to guard her, ride with her as she visited kinfolk and friends in the various camps during her stay with the army. She was from Virginia, and, we were told, the wealthy Northern Neck, indeed a very dear friend of Martha Washington and the whole Custis family. She was visiting her husband, a rather self-important staff...

3 years ago
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Wifes talk about CuckoldingPT2

On Sunday Jan called me and wanted to know if we were still having brunch. She sounded tired but very happy. I had to ask! Well did you do it?”She laughed and said I would have to wait until we were at brunch. My husband wanted to know whom I was talking to and what did she do?I told him it was my sister Jan and she was trying some new sex thing with her husband John. Bud just laughed and said to my surprise, “John have a boyfriend?”He laughed and I realized he was joking. How little he knew...

4 years ago
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334 a matter of costal ccuckolding

CRASH, THEN A TAIL OF RUMBLING, just seconds after the brilliant lightening had lit the darkening sky. Leaning from their attic bedroom window they clung together 5 floors up above the usually busy promenade, watching the blue-black clouds of an approaching heavy storm threateningly approach across the English Channel approaching from the French coast as they knew it would. They had been warned, the radio full of the destruction this storm had caused as it rampaged across Europe, the sea...

4 years ago
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Oscar MeyersChapter 30

William Redman Carter looked at the check and then across the patio table at Oscar. He was impressed by the size of the check. Raising an eyebrow, William asked, “How did you manage to win so much in Las Vegas?” “I was seeing the future,” Oscar said gesturing to the sky with an open hand hoping that William wouldn’t think he was insane. “You were seeing the future?” William asked leaning forward in his seat. His curiosity had gone into overdrive on hearing that Oscar was seeing the...

2 years ago
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Oscar MeyersChapter 5

Georgia was trying to act calm and collected while waiting for Oscar to show up at the house. She was anything but calm; she was horny for the little guy. Over the past thirty minutes she had tried on three different outfits trying to determine which of them would turn him on the most. She had considered being naked, but after he had spent more than a week surrounded by naked women she figured that he would react more to a clothed woman. She settled on wearing an unbuttoned shirt and nothing...

3 years ago
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Oscar MeyersChapter 31

Following a yellow robed young man with a shaved head, Oscar entered the temple and looked around. The highly polished wood gave the room a rich luxurious feel. The scent of incense filled the air. The low chanting of Monks in another meditation area carried into the room. The effect was to create an ambiance of peace and contemplation. The young man pointed to an elderly man seated in the lotus position. The elderly man, despite being shaved bald, had gray bushy eyebrows. He was wearing the...

2 years ago
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Oscar MeyersChapter 8

The first year dining room was crowded, but exceptionally quiet for lunchtime. Finals for the second quarter were approaching and everyone was thinking about the upcoming tests. The waitress had just delivered lunch to Oscar and his roommates. Lisa asked, “So where are Debbie and Georgia?” “Not sure,” answered Oscar as he eyed his tuna fish salad sandwich. He lifted a slice of bread and saw the pile of onions laid across the tuna salad. He nodded in pleasure when he saw that they had added...

2 years ago
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Oscar MeyersChapter 12

“It’s simple. He wasn’t allowed to talk about it,” said Cole in a quiet authoritative voice. The volume of his voice was just loud enough to overcome the background noise of people eating, but not loud enough to carry beyond the table. “He still should have told us,” argued Lisa. She looked over at Sharon hoping that her roommate would support her. The tall thin woman looked as if she had something else on her mind. “Did it hurt anyone for them to hide that from us?” asked Gabby. “I’m...

3 years ago
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Oscar MeyersChapter 16

“You’re kidding?” “No, I’m sorry. That’s how the assignments worked out,” answered Oliver. He had said that phrase a dozen times to a dozen other students. He expected to give the same answer a dozen more times before the day was over. “This is ridiculous,” declared Oscar frustrated beyond belief. They had just returned from the visit with his parents and had learned of their room assignments. “You can’t have Debbie as a roommate. She is rooming with another Chemistry major,” explained...

2 years ago
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Oscar MeyersChapter 35

Returning to their dorm room, Debbie noticed that Oscar’s name had been removed from the name plaque beside the door and had been replaced by We Gahe Sukawaka. She thought about mentioning it to Oscar, but unpacking from their trip to the great plain drove the thought form her mind. Of course, Oscar didn’t help by making jokes about how much gear she had taken on the trip. After unpacking, the trio went to find some food. On the way, one of the students nodded at the three of them. It took...

2 years ago
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Oscar MeyersChapter 6

A naked Oscar stepped out of the bedroom and stopped as he stretched feeling the muscles tighten and then relax. He was feeling exceptionally good that morning. Last night Jennifer had been a wild woman, claiming that it was a goodbye fling. She had worn him out with her sexual energy and he had slept very well. Georgia, seated on the couch, watched him with a feral intensity as he stepped into the living room. Her eyes drank in his body and her body tingled in its desire for him. He sat...

3 years ago
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Oscar MeyersChapter 10

Oscar settled into position on top of a building situated halfway down the street from the house occupied by the Chief of State. He waited for another fifteen minutes before he saw Ed and Penny take advantage of a sudden lull in foot traffic to enter the home. They didn’t knock. Filled with tension, he expected to hear gunshots, but their entrance was greeted with silence. Almost at once, the street filled with men walking along the length of it. They weren’t pedestrians, but guards and...

3 years ago
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Oscar MeyersChapter 4

In the middle of the night, Oscar drove the car across the Iran-Iraq border. They passed the border checkpoint without stopping. It was as if the border guards could not see the white Mercedes. After they had driven a mile past the border, Georgia let out the breath she had been holding and then said, “That was strange. Why didn’t they stop us?” “The Powers That Be do not recognize the borders imposed by men,” Oscar answered. National boundaries were a construct of men, not Gods. “You’re...

3 years ago
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Oscar MeyersChapter 9

It was the middle of October and the air was definitely cool. Turkmenistan in the middle of October was supposed to have high temperatures in the low seventies, but that day had only seen temperatures in the low fifties. The dry barren landscape didn't have grasses of any kind. Afghanistan in comparison looked like an oasis. It was hard to imagine how such a land could support life, but there were people here. The transition from desert to town had been rather sudden. One minute they had...

2 years ago
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Oscar MeyersChapter 12

The news services were going crazy trying to film Oscar. Hordes of reporters staked out churches, mosques, and synagogues in the hope of catching him entering one. No matter how many places they watched, Oscar turned up at the one they had missed. They lined the roads in hope of finding him, but he drove past unnoticed. The best anyone had managed was to film him after leaving a holy site. Of course, as soon as Oscar was gone, the reporters descended upon the last place he visited like...

1 year ago
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Oscar MeyersChapter 7

The month dragged by so slowly that Oscar thought he was going to go crazy. Two buildings had been erected in the middle of nowhere. One building contained the office and Oscar’s sleeping quarters. The other building contained the communications gear. The troops were left sleeping in tents when they were fortunate enough be in camp. Oscar looked over the site, quite pleased with the progress. The men from the regular army he had been training were on their first real mission. They were to...

2 years ago
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Oscar MeyersChapter 2

The four roommates stepped out of their room still in the throes of sexual tension. By the time they had recovered from their initial shock at being naked, insufficient time remained to take care of their tensions. At least the tears had stopped and everyone was walking a little more naturally. Looking at the other groups of students emerging from their rooms, it was clear that their group was the most relaxed of them all. Three pairs of eyes looked over at Oscar in shared thanks. Smiling at...

2 years ago
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Oscar MeyersChapter 14

The first year dining was a large hall with tables well spaced apart. The spacing of the tables allowed students to talk or study without interfering with individuals at adjacent tables. There were a few tables capable of seating twelve, more tables capable of seating eight, but the most common tables were capable of seating four. The tables for four were often paired up to create seating for six. Given that the same people visited the same dining room three times a day, Oscar found it...

4 years ago
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Oscar MeyersChapter 26

Several days later, the Rabbi glanced at the clock and said, “It is almost dinner time. Go while I think about your questions.” Oscar rose and left the Rabbi Teitelbaum to his thoughts. The elderly man considered Oscar while stroking his Star of David. He knew that Oscar wasn’t trying to convince himself to believe in God and he wasn’t trying to disprove the existence of God. Not once had Oscar even suggested that the Jewish God didn’t exist. It went further than that. Oscar wasn’t willing...

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