Gloria's Hole

At nineteen years old, Jack was a normal college student. He had just finished his freshmen year and was planning to return in the fall. Jack was never a ladies' man. Despite his above-average looks and short blonde hair, he was too much of a mama's boy to spend time with women. He had never lost his virginity. Being a mama's boy, his dates were few and far between. When not at college, Jack lived with his single-mother. Even though her son was blind to her looks, Gloria was a very attractive lady. The thirty-sever year old's strawberry-blonde locks and slim six foot one inch figure seemed to enlarge her large 34 DD chest. Jack had never seen his mother have much of a social life. Since he could remember, she was always busy with work. Gloria always was out of the house on business. She made very good money. As a single-mother, Gloria and Jack lived in a large expensive house and owned two sports cars. Jack loved his mother and appreciated her sacrifices. She would return from work exhausted and often having lost her voice. Jack's mother worked hard as a realtor, or so he thought.

Jack was always close to his mother. They would often spend their days together until his mother left for work. Their favorite past time was sitting together in their living room to watch a movie and order a pizza. They were doing exactly that when it all began.

Jack and his mother Gloria were watching their favorite movie "Titanic". The movie had just begun and the pizza was on the way. Gloria sat stretched out on the couch, her feet resting on Jack's lap. She was wearing her low-cut t-shirt and a tight fitting pair of shorts. Gloria turned toward Jack.

"Honey, can you get the cash to pay the delivery man. It's in my purse upstairs."

Jack stood, careful to remove his mother's feet. He quickly traveled up the staircase to his mother's room. He knew this room well. When Jack went through puberty, he had often spied on his mother from his bedroom across the hallway. Those thoughts were far from his mind now, but they would soon return.

Jack easily found his mother's purse. While shuffling through it to find the cash, a small white business card fell to the floor. Jack examined the card. It read, "THE GLORY HOLE" and followed with an address.

What the hell! "thought Jack. He had never heard of The Glory Hole before.Was it some kind of nightclub? Why would his mother have this card? Jack knew he had to find out.

Jack grabbed the cash and carefully returned the card to the purse. He returned to the living room and spent the rest of the night in deep thought. Tomorrow while his mother was at work, he would go to The Glory Hole and find out why his mom had the card.

Gloria left for work shortly before three o'clock. She always left around that time. Today she was wearing her sexy, but business style black suit. Jack wished her goodbye then quickly hurried to his room. He dressed nicely. If this was a club, he knew he had to get in. Jack dressed quickly, too quickly. He was in a rush. He was fully prepared by three-fifteen, much too early if it was a nightclub.What the hell, Jack thought,I guess I'll drive by it and check it out. Jack drove by the location. The location consisted of a large plain-looking building with two double doors.A club, Jack thought. To his surprise the club seemed open. There was no one waiting to get in, but a single bouncer stood at the doorway. Jack made his decision, he was going in.

As Jack approached the doorway, the large overweight black man stepped in his way. "How old are you, kid?" the man commanded.

Surprised, Jack responded to the question, "nineteen."

"Got two-hundred bucks?" the guard asked.

Jack hesitantly responded, "yes?"

"Good," the man responded. "It's one hundred to enter."

Shit one hundred bucks. This better be worth it. Jack handed the man the money and he entered. The guard had one last strange comment. "If your into women to go to the left. If you like men, the right."

What? Jack thought as he stood in a hallway. It branched both left and right. Hesitantly, Jack headed left down the hall. The hall took a sharp right turn. Jack found himself standing in a large open area. This place had once been a club of some sort, but now it stood empty. Empty, except for a gorgeous women standing near a doorway.

The woman was a tall brunette of Hispanic descent. She stood around 5'7 in her four-inch heels. The woman wore a tight-fitting red dress that actcentuated her large 34 C breasts. On her dress was a nametag "Mary."

Mary turned toward Jack. She smiled politely and said, "Good evening, my name is Mary. Is this your first time visiting?"

Jack was stunned that this women existed, much less was speaking to him. "Um, yeah," Jack quietly answered.

"Just walk through the door on my right." She pointed to the door. "Inside are the booths. Just slip one-hundred dollars into the slot and stick your dick through the hole." Jack was astounded that she could say such a thing so calmly.

"What?" Jack was stunned.Why would his mother have a card for a place like this?

"Oh, don't worry," she said. "For an additional five-hundred, you get a fuck."

"Um"

"Right this way." Mary opened the door.

Jack cautiously walked through the doorway. Inside he saw several white booths. Inside each booth was a door with an eyehole in it, but the eyeholes were way too low. Behind it was a curtain that could be closed for privacy.

Mary pointed to the first booth. "Only Jewel is in at this time," she said. Jack approached the booth. On the left side was a slot for money.Why would mom have a card for this place? What am I even doing here? She probably got the card by mistake. Then again, I could lose my virginity right now. Why not? Jack thought as he removed five twenty-dollar bills from his pocket.

Jack pulled the curtain closed behind him and slid the money through the slot.He would lose his virginity tonight. Jack dropped his pants and carefully inserted his nine-inch penis into the hole. It seemed like forever as a hand slowly reached up and began caressing his cock. Within moments, he could feel the warm breath of a mouth near his penis.Oh God, Jack thought. Then it hit, a tongue reached out and playfully licked his head. It felt good, but Jack knew this was just teasing. Slowly, the mouth teased her way around the sides of his cock until finally engulfing it. Jack couldn't last long. Within moments he was cumming. His warm seed filled the awaiting mouth.

Jack wasn't done. He wanted more. He pulled the rest of his money from his wallet, five hundred dollars and slipped it through the slot. Through the door, Jack heard, "Alright, honey if you want more." The voice sounded familiar.It couldn't be. The door swung open and on the other side stood Gloria is mother. Both Jack and Gloria stood in surprise, a look of shock on both their faces. Jack turned and ran.This couldn't be. He had to escape. It was impossible.