Raffle Girl
Copyright© 2025 by Lorn Skye
Chapter 5: Meet Olivia
BDSM Sex Story: Chapter 5: Meet Olivia - Dr. Sam White was not lucky. He had never won a single thing in his entire life. His colleagues at work had convinced him to attend a fundraiser for some cause that he knew nothing about. And suddenly, he won. The prize was not at all what he expected! Join Sam as he journeys from confirmed bachelor to the luckiest man in the world with a bevy of beauties surrounding him. ~43000 words
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa Slavery MaleDom
Eve’s apartment was typical for a student apartment. She shared it with another graduate student and Eve had called ahead to let her know we were coming.
Where Eve was more bronze colored with her dark red hair, her roommate was a classic Italian beauty with dark olive skin, long dark lustrous hair, and large breasts on a petite frame. Eve introduced her as Olivia as she led me back to her bedroom.
Olivia followed along behind us and I wondered how much she knew about what was going on between Eve and me. Eve had mentioned that she had a safety contact and I wondered if it was Olivia since she had no real family.
Eve immediately went to her closet and grabbed a suitcase that had seen better days. She opened it and went to her dresser. “Will I be needing any panties, Master?” she asked in a coquettish manner.
“Only sexy ones that I can rip off your body!” I answered and Olivia laughed.
“You might have found someone as brash as you!” Olivia added. “This one might be a keeper!”
“Oh, it isn’t up to me,” Eve replied, “I’m his until he throws me out. I sold myself to him for at least a week, and given how many times I’ve had an orgasm in the last twenty-four hours, he will literally have to throw me out!”
Olivia blushed and laughed nervously, but I could see that there was a lot of curiosity in her eyes, and a ton of unasked questions. Eve just smiled sadly as she left the room, and when I started to say something, she just shook her head and motioned for me to be quiet.
“Now, as for clothing, Master, what were you thinking?”
“I think around the house you’ll need all the lingerie you own, particularly robes and sweaters, that you can wear over the two harnesses we just got you. A few sets of comfortable clothes are a good idea as well. You will need a couple of nice dresses as I plan to take you out and show you off. However, I plan to take you shopping after this, and we will get those then. But hosiery, garter belts, and the like are all welcome.”
“My lingerie collection is rather limited,” Eve said quietly, her face again downcast. “It wasn’t really something I could afford with my limited funds.”
“Then we will have to make a stop for that as well. And since I really don’t want to have to stand there while you decide, why don’t you ask Olivia to join us. Then, you can show me what you have selected and I can settle the bill.”
Eve perked up at that thought and ran into the front room to ask Olivia if she wanted to join us. I added loudly that she could expect to get a couple of outfits as well and suddenly, I had two nubile young women hugging on me.
Now that they were properly motivated, Eve managed to quickly pack up her suitcase while Olivia got dressed for shopping. I mentioned that she looked fine, but that just got me a look that said I was a stupid male. What did I know?
A few minutes later, we were back in my car and headed toward Michigan Avenue and the upscale shopping in downtown Chicago. Traffic was of course terrible, but Eve and Olivia were in the back seat whispering to each other and giggling like little girls. Periodically, I would catch Eve staring at me in the mirror. She was smiling and seemed genuinely happy. Olivia was also sneaking glances at me, but they were much more of a curious and furtive manner.
We eventually made it downtown and I found some parking nearby. The girls were excited, but when I went to give them my cell phone number to call me when they were ready for my review, I was appalled that they both had badly outdated phones with cracked screens. So, we immediately detoured over to the Apple store where I got them both the latest model of iPhones, as well as Apple watches.
Since they already had data plans for their old phones, and while the girls were looking at cases, I had the guy at the counter upgrade them to the biggest data plan and I prepaid it for the full year.
It is amazing how fast sales people can get stuff done when they see a big commission. With two new phones, watches, cases, chargers, and the big data plans, I was sure this guy was going to be in for a nice commission. He made sure we were happy and, on our way as fast as he could get the system to work.
I dropped the girls off at a nice lingerie boutique with specific instructions on garter belts, stockings, and lingerie that was suitable for a slave girl at her Master’s beck and call. I also instructed Olivia that she was to get at least two sets of lingerie that were more expensive than the cheapest set Eve selected. I then made sure that the saleswoman knew I would be picking up the bill and headed to the coffee shop, where I was hoping to get a bit of reading and work done.
In less time than I expected, my phone chirped with a text that they were ready for me. I settled my tab and headed back to the shop, where the saleswoman had prepared a small fashion show for me in the back of the store near the fitting rooms.
Once I was seated, the two girls came out in matching teddies with garter belts and stockings, looking very much like fashion models. Eve then came and sat on my lap while Olivia went to change into her second outfit. Olivia had been in a gorgeous blue set, while Eve, who seemed to be squirming in my lap, had on a forest green set.
When Olivia returned, she was wearing a black body stocking that hid absolutely nothing. Eve giggled when she felt my cock lurch at my first sight of her roommate’s naked body. Olivia was blushing, but she strode over to me using her best model walk, then turned so I could get the full effect, and strode back to the door. Eve kissed me on the lips and then scampered into the fitting room with Olivia.
The saleswoman was standing off to the side and when we were alone, she walked over closer to me. “You are a very lucky man,” she said in a husky voice. “Those two are beautiful, but all that energy would about kill me!”
I looked over at her and realized that her nipples were erect and she was flush from the show. “Only Eve is mine,” I said to her, “Olivia is Eve’s friend and just here to help Eve with her shopping.”
“Olivia would scamper to your side if you just said the word,” she replied with a knowing look. “I suspect that she is even more of a submissive slut than your Eve, but she has some trauma in her past that prevents her from trusting people. And not just men, she definitely gave me the cold shoulder when I tried to flirt with her.”
Eve came out then in a fishnet version of the body stocking that Olivia had worn. While Olivia’s was transparent, Eve’s was more, ‘not there’, than it was, ‘there’. But unconcerned about who might see her, she strolled out and posed for me, turning this way and that. Then she propped one foot on the chair beside me, opening herself to my view, and anyone else who might be looking.
“Do you like this one?” she asked. “I thought it might be good for wearing around your condo when all the curtains were open and the neighbors might see.”