Raffle Girl
Copyright© 2025 by Lorn Skye
Chapter 14: Graduation
BDSM Sex Story: Chapter 14: Graduation - 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 Anal Sex
As we got to the end of April, Eve and Olivia began to get excited about graduation. They were both graduating with honors and Summa Cum Laude, so they had good reason to be excited and proud of their accomplishments.
While they were busy picking out which dress to wear under their gown, and which receptions and parties they wanted to attend, I ordered a few surprises of my own for their graduation.
So, when the magic day came around, I set out a box for them both on the kitchen table. I then started the coffee, and even made some omelets, while they showered and got ready. I think Eve was a bit surprised when she realized I was up and making breakfast, something that had become her responsibility. Then she saw the presents on the table and she squealed.
Olivia came rushing in to see what was wrong, dressed only in her bra and panties, and when she saw the presents, she rushed over and they ripped open the wrapping paper.
Inside they each found a large remote-controlled butt plug that they would be wearing during the ceremony. When they felt the vibrations, they would know I was thinking of them. In addition, they each got a couple of micro bikinis in coordinating colors, and in their sizes.
But the best present was the small piece of paper in the bottom that was the itinerary for a trip to the Bahamas where I had chartered a boat for a two-week trip cruising around the islands.
I found myself in the middle of a hug between two, very happy women. I highly recommend the experience.
And then to top even that, they each bent over the counter and presented their asses to me, swaying back and forth, and begging me to put in their butt plugs.
We were a little late to the ceremony, given that I needed to check each plug, to make sure it was receiving a signal, and vibrating appropriately. Of course, the only way to make sure it was really working was to turn it off and on while it was inserted, and with my cock in their pussies.
And while the ceremony itself was boring, staid, and traditional, the way Eve and Olivia wiggled in their seats, when I would press the button on the app on my phone that controlled the vibration intensity, was entertaining. I’m pretty sure Eve had a nice orgasm during one long session with it on maximum. Her colleagues on either side of her seemed to be in on the joke, as they were looking all around trying to figure out who was controlling their friend.
When it was over and done, and we were in the car headed home, Eve climbed onto my lap and replaced the plug in her ass with my cock. She rode me to a nice climax while frigging her clit, and when she came down, she slipped off and Olivia took her place.
Eve had to help Olivia to achieve orgasm, because she wasn’t as much a fan of anal as Eve. When she did cum, the tight contractions of her sphincter set me off as well, and I filled her ass with my cum.
When we got to the condo, I told them that they needed to pack a suitcase for tropical weather, and they needed to be ready to go at seven a.m. They got all excited, but I refused to tell them anything else. I did crimp a few of their plans to go to some late-night graduation parties, but they were super excited.
They changed, and I only insisted that they keep on their collars, which I had upgraded to have a chip that I could track, and it would alert me if it was removed. They each gave me a kiss and then they headed out to celebrate with their friends.
They had invited me, but I had no interest in hanging out with a bunch of college kids who were facing the prospect of facing the real world and celebrating one last night of being free from adult responsibilities. In addition, I wanted to double-check all the arrangements for the trip.
To my surprise, Eve and Olivia returned home before midnight. When I asked, they both essentially said that they were ready to move on. They were glad to have gone and been able to say goodbye to their friends, but they were too excited by the idea of a trip.
When I reminded them that they needed their passports, they got even more excited. And while they finished packing their last-minute items, they tried their best to entice me to tell them where we were headed.
“You know that I can just order you to do the very things you are offering,” I replied after a particularly graphic description from Eve about how she would give me a rim job while I fucked Olivia in the ass.
We did eventually make it to bed, despite all the packing and prepping for the trip. And despite all the promises of kinky sex, we made slow, passionate love, first Eve, and then I finished in Olivia, before we all fell asleep in a tangle of limbs.
The alarm at 6 a.m. was loud and brutal, but Eve and Olivia were up in a heartbeat. They quickly showered and pulled on yoga pants and long tops, perfect for traveling. Of course, they had on their collars, and I insisted they wear the lovely butt plugs as well.
My driver was waiting on us in front of the condo. We tossed our bags into the trunk, and then we were headed for the airport.
I had chartered a jet for our flight to Nassau. It would take us a couple of hours to get there, and I planned to join the Mile High Club on the way. I had ensured that the crew would give us some privacy during the flight, and when I had suggested it, the booking agent had just laughed. Apparently, I wasn’t alone in making such requests.
Despite the early hour, it still took some time to make the airport. We were flying out of the executive airport, so there was minimal security, and we just rolled our bags from the car directly onto the airplane. In ten minutes, we were on the plane, and the attendant was closing the door.
Eve and Olivia were excited, so I let them take in the experience. I had flown in a private jet before, but I had to admit it was still very cool. The excitement radiating off the women was a bit infectious, and I was able to enjoy the experience through their eyes as well.
I did appreciate the efficiency of flying in this manner. From the time we pulled up in the car, to the time the wheels left the ground, was under thirty minutes, and that was only because of air traffic control and the airspace around Midway and O’Hare.
Once we were in the air, Eve and Olivia were glued to the window, taking in the sights of the city as we climbed to our cruising altitude. I was watching them, and jumped when the flight attendant, a lovely woman probably around my age, with long black hair, but the palest blue eyes, touched my shoulder. “Would you like some champagne?” she asked quietly, “Or is there something else I can get for you?”
“Actually, some champagne sounds wonderful.”
She nodded, and a few moments later returned with three glasses, handing one to each of us. I toasted the girls, and they each drank their champagne rather quickly, giggling and laughing as they did.
The attendant then asked if we needed anything else, and when I demurred, she let us know that she would be heading up to the cockpit, so, just ring if we needed anything. Before she left, she leaned over, and with a grin, whispered in my ear, “I just wanted to let Sir know that we are now over a mile high.” And with that, she sashayed her way to the cockpit.
Eve had a big smile on her face and I think she suspected what was coming. “I want both of you naked, and the first one to be naked, with my cock in their mouth, gets my cum,” I told them.
There was a split second where Eve and Olivia looked at each other, and then clothes went flying. Eve was the first to get naked and thought she would win, but when she pulled down my boxers, Olivia slammed her face into my lap and sucked on my still tumescent cock.
“You Bitch!” Eve laughed, and then, placing her hand on the back of Olivia’s head, she grabbed her ponytail, forcing her down until my cock penetrated her throat. Olivia gagged but took it like a trooper, even when Eve held her down. She started to rhythmically swallow, as her throat massaged my cock head with each swallow.
Eve then lifted Olivia, and still holding her ponytail, pulled her to her lips and kissed her fiercely. When they came up for air, Olivia allowed Eve to take my cock, and Eve did her very best to make me cum.