She pulled out something big and purple and a bottle of something. The purple thing was big with weird ridges on it. He knew what it was but he tried to keep his mind calm. He knew he had made his choice and now had to give in to her. Still it terrified him as she made her way back to him.
"You are lucky she has lube too" as she put down the bottle and purple dildo on the night stand. He was sure it was a cruel joke placing them right in his view. "Maybe not so lucky on the size" as her hands were rubbing his back again. He wanted to turn his head back into the pillow so bad, just to avoid seeing the whole situation in front of him.
"Does make you wonder about Bonnie, she really loves her men big" the little laugh coming out of Annalise sounded like the Annalise he knew, even in this bizarre situation she was cracking a sinister joke.
Her hand had returned to his ass again, rubbing him over the sore spots. He didn't want to look at the items anymore so he decided to try looking at Annalise, maybe he could try and convince her not to do this. When he found her eyes she was staring straight at him. Had she been looking at him all this time. He tried reading her face but it seemed void of emotions
"Spread your legs" her hand had traveled down and she softly padded the back of his left leg. When he didn't respond she started to push a little. "Don't make this to hard on yourself, just relax and do as your told" her voice was suddenly so sweet and understanding. Her face suddenly an understanding smile on it. He took a deep breath and slowly started to part his legs. She kept pushing against his leg till she was satisfied.
"Good boy" she had started to rub the inside of his legs and the little praise send another electric pulse straight to his cock. He was so happy she couldn't see his body response right now. Her hands were back on his ass patting him softly
"This won't be easy if you don't relax and keep breathing" She bend forward and grabbed the items from the night stand "not that it won't hurt but it will go quicker if you just give in"
The words didn't comfort him. His mind was again a mess, he couldn't take this. He saw her open the bottle and squeeze some lube on her hand and he just couldn't look her way anymore. He turned his head back into the pillow and squeezed his eyes shut.
A warm hand returned to his lower back and suddenly something cold and wet was being rubbed between his cheeks till it hit his entrance. He wanted to buck and his muscles tensed as he felt pressure
"Shhhhh" the warm hand on his lower back rubbed circles. "Don't fight me, you wanted this"
He didn't, he really didn't but then again he couldn't walk out of her life either. She kept the pressure on his asshole the whole time. Her hand on his lower back moved to the back of his head rubbing his short hair. Strangely that felt very comforting, it made him remember she wouldn't hurt him if he just did what she wanted. Slowly his muscles started to relax and he could feel himself opening up to the pressure. The pain wasn't that bad, it was more a soft burning feeling and he relaxed more. But as the dildo was pushed further in the burn became a sting and it didn't help when his muscles involuntary started to squeeze in protest.
He had expected her to keep pushing but she slowly started to move the dildo up and down. The pain became less and returned to the burn he felt earlier.
"There you go... you are being so good right now" yes he was insane, he was sure now. Again the praise had made his cock stiffen while he could feel the dildo slide further in with every push. Annalise repositioned herself, taking her hand of his head and making it easier for her to control the dildo she was using. Her left hand was on his ass softly pushing his cheeks apart.
"That's a good boy" she praised him but he just wanted to cry. The whole situation was so absurd and now his body had started to respond to her praise but also the feeling of the dildo moving in and out was sending signals of pleasure. She suddenly angled the dildo differently and as she trust in, it hit something inside. Sending an overwhelming electric pulse to his cock. He couldn't keep quiet as a groan escaped his lips. She pushed in again hitting the same spot making him groan again. Something cold hit his asshole as she had squeezed some lube next to it. Putting the bottle down she started to really pound the dildo into him hitting the spot every single time. He couldn't keep from moaning the whole time, he had started to rub his now rock hard cock against Bonnie's sheets for some friction.
"You like this, don't you?! You always wanted me to do this, take away your will. Use you, like the way you use those girls!" The words did register but he couldn't process them. His mind had gone blank and the fog was clouding everything. He felt his body coming closer and closer. Every time he came close she would slow down a little, teasing him.
"Pleeease" he muttered under his breath. His voice was muffled by the pillow.
"Look at me and ask properly what you want" it took him a few seconds to respond. He turned his head looking her in the eyes
"Please... ma'am...let me... cum" he panted.
She smiled at him, he could see victory in her eyes as she started really pounding him. It only took a few strokes and he felt his muscles contract. He came hard, moaning loudly in the pillow.
She sat quietly next to him, watching him come back from the bliss. She pulled out the dildo and threw it next to him on the bed.
He felt empty without it but his mind was worse off.
"Now you know how it feels to get fucked by someone you trust!" The words stung, he was scared to show her his face.
He felt her get up from the mattress and walk towards the door.
"I'm sending Bonnie a text in five minutes that she can come back. You better clean up quick if you want to keep this private between us" she closed the door behind her, leaving him broken on Bonnie's bed.