This scenario is fiction and everyone is over the age of 18. This story is also intended to (or at least attempts to) ret-con my story Mother in Law's Love into this timeline as well.
Barb Andrews groaned in delight as the hot water cascaded over her luscious curves. Her best friend was getting married and she had just arrived back in her hometown for the wedding after a long trip. She was staying at her friends the Hill's house because her parents were in the process of moving and she didn't want any part of that. The Hill's house had the advantage of being 3 doors from the reception hall, so there were quite a few other people staying there as well.
She briefly contemplated masturbating to scratch the itch between her legs but she didn't want to use up too much hot water. She would find someone to take care of her needs later. That would be easy, she figured. Barb had a body that no one could miss - long black hair, emerald green eyes, shapely legs, round butt, all topped with a large pair of breasts. She used this to her advantage and had long ago lost track of how many men she had sampled.
Sebastian Hill heard the shower start and knew that this was his chance. His best friend had dared Seb that he couldn't find out how big Barb's boobs were. Without pausing to think things through, he figured it would be a simple matter to sneak into the room she was staying in, take a quick peek at one of her bras and be out before Barb was done her shower. There was no one else home, so he figured it would be simple.
She was staying in the bedroom next to the bathroom. It was his bedroom in fact, but he had been relegated to a couch in the basement for the duration.
He slipped into the dark room and looked around, hoping she had left her bra on the floor or bed. To his disappointment there was nothing in sight. Taking a deep breath he walked over to her suitcase and flicked the lid back. It was a jumble but Seb saw a bra strap sticking out from under a sweater. Carefully lifting the sweater aside, he stood staring at her black lace bra for a moment before he reached out to pick up the lacy garment. His hands trembling, he turned it over and reached for the white tag, which to his delight read 36H. Wow, he thought, they are really big.
Suddenly he realized that the shower had stopped. Panicking, he turned to run, only to find a towel clad Barb leaning up against the door frame watching him.
"Now what are you going to do with that?" She asked, pointing at the lacy bra he was still holding.
He dropped it as there was a hornets nest in each of the cups.
Barb stood there with no expression on her face as she let Seb squirm. She knew that she should be furious because he was rifling through her underwear and that was just weird. However, she was very horny and, if he was a normal 18 year old, maybe his little indiscretion could be turned into something that could help quench the need between her legs.
"The question is, what are we going to do with you Sebastian Hill? Going through a woman's underwear. By rights I should tell your parents."
Seb didn't say anything. He just hung his head in shame of having been caught. Barb could see he was turning beet red. This was going to be fun.
"Well, why don't we play 20 questions? I ask you a question and you answer. Truthfully. If I don't like your answer the game is over and I turn you in. Deal?"
Seb just nodded. He was still too embarrassed to look her in the eye.
"What were you holding when I came in?"
"Your bra."
"Why were you holding my bra?"
"You have big boobs and I wanted to see how big they were."
"Why yes I do, thanks for noticing" she replied with a laugh before continuing. "And did you see how big they were?"
"Yes."
"How big are they?"
"36H"
Barb was really getting excited now. Seb was obviously uncomfortable but he was still playing along. She decided to turn up the heat.
"Has a girl ever given you a blow job?"
"Yes."
"Who gave you a blowjob?"
"Bethany."
Ah yes, his ex-girlfriend.
"Didn't you break up with her a few months ago?"
"Yes."
"Did you guys have sex?"
"No. She wasn't on birth control and we were too afraid she would get pregnant."
"I'm on the pill." she volunteered. "Are you with anyone now?"
"No."
"Have you had sex with a girl."
"No, not yet." he sighed
"So I guess that means it's just you and your right hand. And don't tell me that you don't jerk off, you're 18 years old. What do you think of when you masturbate?"
"Girls, sex, you know."
"Do you ever think of me when you masturbate?"
Seb mumbled something that she didn't understand.
"Louder, I couldn't understand you."
"Yes sometimes I think of you when I masturbate." He was looking towards her now but his eyes were glued to the tops of her breasts and cleavage.
She snapped her fingers at him. "Hey, my face is up here! Now, How often do you do it?"
He sighed. "Every day. Usually more than once."