Chapter 3

                                    

                                          
Lena moves back to the cart to return the wand and strip out of her vest. She casually unbuttons her shirt but leaves it on. Lena takes a deep breath to steady herself. She tries desperately to come up with another solution, anything other than what she was about to do. She doesn't come up with anything. For a split second, she thinks that maybe she should just claim she is having a performance problem, stage fright, but that would leave Kara in the hands of these pompous pigs. At least if Lena goes through with it, she can prep Kara properly. At this point, all she can do is damage control. So, she clenches her jaw and grabs the lube.
At this realization, Lena slowly goes back to her best friend tied across the bench, shiny slick all over her tanned thighs. Lena's cock twitches eagerly at the sight. Lena unbuckles her belt with shaky hands and tugs the zipper down. She wishes she could cover Kara up least, feeling guilty that she isn't totally disrobing. She slides the front of her boxes down to release her hard shaft from its confines. Precum oozes from the tip. Lena squeezes a generous amount of lube on herself and on Kara. Lena wishes she could have prepped her more. Three fingers was hardly going to be enough for her girth. She strokes herself to spread the lube completely. Kara shoots forward at the surprise contact of Lena massaging the lube around her hole.
"I'm so sorry," Lena's voice breaks. "Use the signals."
After Kara carefully shakes her head to indicate that she understands, Lena sinks to her knees behind the blonde and lines herself up to ever so slowly pushes forward. Kara can't hold back her groans. Lena feels a tear slip behind the mask as her tip pops into her best friend's asshole. Lena immediately sees Kara putting her hands flat on the ground. Lena halts any forward pressure and wraps an arm around Kara's waist to play with her clit for a few breaths. Kara brings her hands back up with a moan of pleasure, and Lena starts to push forward again. Kara's hands shoot to the ground again. Lena knows that she can't just stop. It pains her, but the audience and Roulette are expecting her to be ruthless. Being too careful with Kara's wellbeing will reveal more than she wants.
"I'm so sorry, Kara. I'll go as slow as I can, but- but I have to. I'm sorry."
Lena keeps pushing her cock deeper into the tight warmth. Every so often, she slightly pulls out to slide back in a bit more than before. She is trying to be as careful as she can without getting them into further danger. She can hear the crowd behind her getting excited at seeing Supergirl's undoing. Kara's moans get louder. Lena bites her lip to try to surprise her own. She does not want Kara to think she is enjoying this. Lena is trying to keep her biological response separate from her emotional turmoil. She is cramming everything she feels into tiny boxes. She knows that this is the only way she is going to be able to go on.
Lena is only about 3 inches deep when Kara starts knocking. The crowd hoots and hollers at the perceived struggle. Lena looks down and immediately understands. The widest part of her member is just outside the stretched hole. Lena takes her time rocking in and out, telling Kara to keep struggling for the image. In reality, Lena isn't going any deeper. Lena globs on more lube without breaking her strokes.
"Kara- I need you to hear me. I can keep going like this, but the next people aren't going to be so gentle with you. Or I can work myself all the way in. Clench your fist for the first, spread your fingers for the second." Lena is panting. She can't even hide the arousal in her voice as she is urgently whispering to Kara. She has to remind herself to keep everything in boxes.
Kara spreads her fingers. Lena lets out a shaky breath. There is no easing this part, and Lena knows it. On her next stroke, she thrusts the last 4 inches at once. She stills immediately once she can feel Kara against her hips. She reaches back down to stimulate Kara's clit to try to get her over the pain as quickly as possible. Kara screams out in pain. Her breath is ragged. Lena sits still. She can hear the crowd jeering, telling her to plow the Kryptonian harder.