Carolyn's First Gangbang
by Jessica Princess
Copyright© 2025 by Jessica Princess
Erotica Sex Story: A young woman feeling out of place at college, is invited by her roommate’s boyfriend to a 24-hour bookstore, and so the erotica begins...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Mult Reluctant School Gang Bang Group Sex Anal Sex Double Penetration Exhibitionism Masturbation Oral Sex Public Sex .
Carolyn didn’t really fit in at college. She’d been excited to go for weeks beforehand. She thought she was ready for a new adventure. High school had been so confining, so strange. College was where she would make some real friends, read some good books, really explore the world.
But two weeks in, it was turning out to be a real dud. No friends really, except for her chatty roommate, Rachel. No good books yet, just a bunch of freshman crap that one had to read. And all anyone wanted to do was to drink and do drugs and party, all of which was not her scene. Carolyn was a quiet girl. She wanted to have fun, but not to be so drunk that she couldn’t remember it the next day.
Carolyn had grown up in the country, in a conservative little town. She was cute as a button, with long blonde hair that went halfway down her back and soft features that made her look younger than she actually was. No one would mistake her body for a child’s, though. She was only 18, but she had the curves of a woman, such that when she wore her favorite outfits, most of which were low-cut cotton dresses that stopped just above the knee, she had heads turning.
But all she really wanted was someone to understand her. She didn’t want the attention of guys. She usually didn’t even notice. She’d had a boyfriend in high school who she’d fooled around with, even had sex once or twice, but it was short-lived. It wasn’t her thing.
The problem was, she didn’t know what her thing was. She was dying to find something that she loved doing, something that would bring her together with other people. But at college, that just seemed hopeless.
“I don’t understand why you don’t just hang out and have a beer like the rest of us,” said Rachel.
Carolyn just nodded. She was tired of having this argument. Rachel was sitting across the room, on her boyfriend Chad’s lap, alternatively cooing in his ear and offering Carolyn her unsolicited advice.
“It’s okay, Rachel. Really, all I want to do tonight is read or watch a movie or something. Anything that I don’t have to think too hard about.”
“What are you reading?” asked Chad. He was a senior, and Carolyn thought he was nice. Not dimwitted like some of the other guys who lived in her dorm.
“I just finished The Unbearable Lightness of Being,” Carolyn said. “It was wonderful.”
“Oh yeah? No kidding,” said Chad. “I love that book. It’s one of my favorites.”
Carolyn smiled. “You have good taste,” she said.
“I like books too!” said Rachel. “I’m almost through the first Harry Potter!”
Both Carolyn and Chad nodded, then rolled their eyes when Rachel looked away.
“You really should come to the party at Chad’s frat house later,” Rachel said. “It’s not so bad. There are other people there who don’t drink.”
Rachel was being sweet, even if she was a little dim. Carolyn smiled at her. “It’s really not my thing, Rachel. But I appreciate the offer.”
“Oh come on,” said Chad, “You really should come. I tell you what, I’ll make you a deal. If you agree to come to the party tonight, I’ll buy you any books you want.”
Now here was an offer worth considering, Carolyn thought. She really didn’t want to go to the party. She loathed such things. But any book she wanted ... Na, he had to be pulling her leg.
“Oh really?” said Carolyn. “And I suppose I wouldn’t get to pick this book until after I went to the party tonight? Nice try, Chad. But I don’t think so.”
“You don’t think I’m being legit?” he said. Then he gently moved out from under Rachel and stood up. “Put on your sandals. I’ll take you to the bookstore right now.”
Carolyn hadn’t been expecting that response. She was speechless for a second. Then she looked at the clock on the wall.
“It’s 11:00,” she said. “No bookstore is still going to be open at this hour.”
“Ah,” said Chad, “this is when it pays to be an upperclassman and to know the area. I know a great little bookstore that’s open twenty-four hours.”
Now Carolyn was intrigued. “24 hours? Are you serious?”
“Only one way to find out,” he said, holding open the door.
Carolyn couldn’t think of another objection, so she agreed to go. He kissed Rachel goodbye, told her he’d meet her at the party later, and then escorted Carolyn out the door.
It was a warm and breezy night. Carolyn was glad she’d picked a southern school where she knew she’d be able to wear her favorite cotton dresses right up to December. She clung to Chad’s arm as they walked, talking about the novels they’d read. She trusted Chad. She wasn’t sure why, but she did. He got something about her that other people didn’t, something beneath the surface.
It was about a fifteen-minute walk, but they finally made it. The store looked a little seamy from the outside. But Chad insisted this was the place. They went inside, and sure enough, there were shelves of books, mostly classics, lining the walls. But this was clearly not the store’s main purpose. A door in the back with a metal detector overhead led into a much larger room where Carolyn could just make out what appeared to be a large “XXX” written on the wall. A man was sitting behind a desk just past the door, presumably there both to ring up customers and to check IDs.
Carolyn pulled away from Chad, horrified. “You brought me to a sex shop!”
“No,” said Chad, “I brought you to a 24-hour bookstore. The other half is the sex shop. And we don’t have to go into that part if you don’t want to. Just pick your book, and we can go right now. Or don’t pick your book, and we’ll go straight to the party. Your decision. Either way, I’ve held up my end of the bargain.”
Carolyn was fuming. She couldn’t believe that Chad would bring her here. But he was right. He had held up his end of the deal. She agreed to peruse the books and pick one.
“But as soon as I pick a book, we’re leaving!”
“Fair enough,” Chad said.
The books were all in pretty good shape, some used and some new. Carolyn picked up a few and flipped through them. She tried to concentrate, reading through small passages, looking for a story that grabbed her attention. But she was distracted by the slight sound of moaning she could hear from the other room.
“Let me know what you pick,” said Chad. “I’m going to go check out movies in the other room.”
“What!” said Carolyn. “You can’t leave me out here. How will I get your attention when it’s time to check out?”
“Just yell to me from the counter,” he said. “I’ll hear you.”
Before Carolyn could protest, Chad had disappeared around the corner.
After a couple more minutes of searching, Carolyn found an old copy of essays by Thoreau that she decided she liked well enough to own. She stepped up to the counter. The man in front of the register had fallen asleep. She tried to call out to Chad, who was on the far side of the room. But he didn’t hear her, and she didn’t want to wake the man up for fear of what he might think seeing her there. She wasn’t quite sure why she cared what others thought, but she did. She always had. It kept her out of a lot of trouble.
Finally, after five minutes of trying to get Chad’s attention, she placed the book down gently on the desk and walked to the back of the store, trying not to touch anything along the way. She could still hear the sounds of moaning coming from the far left wall, behind a curtained door where light could barely be seen flashing overhead. The sound intrigued her, but she decided to be resolute. Whatever was going on beyond that curtain, it could only bring her harm.
“Find a book?” Chad said as Carolyn approached him.
“Yes, can we go now?” she asked.
“Sure thing,” said Chad. “Let’s go.”
They started to move, but another flash of light caught Carolyn’s eye and she stopped for a second.
“There are movie booths back there,” said Chad.
“What’s that?” Carolyn asked.
“Just little spots where you can watch porno movies. You put in quarters in a machine. The rooms are private. It’s fun. You wanna look?”
“No,” she said quickly. “Of course not.”
“Alrighty then,” said Chad. He started to walk towards the register but Carolyn didn’t follow. She just stood there, staring at the curtain to the room with the booths.
“I’ve never seen a porno,” she said.
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