The Submissive CEO - Part 2

Emily heard a tap at her office door to find her assistant holding a large bunch of red roses. “Someone has an admirer” her assistant announced. Emily felt a blush of colour slowly spreading to her face as her assistant handed the roses to her. “I’ll get a vase of water to put these in” her assistant advised. Emily took the card out of the small envelope and smiled as she read the words “High Heels”. If the last time she read these words were just a warmup, she knew it was going to be a night to look forward to.

Emily knocked on Todd’s door at 6:50 pm, dressed in a black dress with a v-line, showing off her cleavage, stockings, suspenders, black heels, her hair back in a French knot and her makeup applied carefully and flawlessly with red lipstick. Todd opened the door, wearing the black suit, white shirt and blue tie. Emily didn’t mind that he wore the same outfit as last time as he looked dashingly handsome in this business suit. He smiled at her in approval and stepped aside to let Emily in. He showed her to the room at the end of the hallway and walked down the staircase with her. “You know what to do. You have 10 minutes to get ready.” He stated before leaving the room.

Emily inspected the outfit he had laid on the bed for her. A black satin strapless teddy with holes for her nipples, black furry paws, cat ears and an opening in the crotch from front to back. She took off her clothes, following the initial rule of leaving the suspenders, stockings and heels, placing them on top of the chest of drawers. She noticed on the chest of drawers a but plug with a fluffy black tail attached to it. She picked it up and inspected it for a moment, turning it around in her hands, before returning it to its place and hurrying to take her position on her knees on the padded bench at the end of the bed and waited. She knew Todd made her wait on purpose to build the anticipation.

Todd stood before her when he entered the room, took off his tie and began to unbutton his shirt. He took his shirt off and reached both hands forward to her nipples poking out, hard and erect, through the holes in the outfit she was wearing. He took her nipples between his thumb and forefinger, applying a firm pressure as he squeezed and twisted them. Emily drew in a deep breath and swallowed as he did this, feeling herself getting wetter. “Don’t orgasm yet, Emily” Todd commanded. “Will I be allowed to orgasm tonight, Sir?” Emily asked. Todd gave her a stern look and replied “If you’re a good girl and obey properly, yes, when I give you permission and not before then.”

Todd let go of her nipples, undoing his belt and his trousers, let them drop to his ankles to reveal a pair of tight silk boxers. Emily was tempted to touch his crotch through the boxers but knew she was forbidden to do anything she wasn’t commanded to do. Instead, she waited patiently. Todd pulled his cock out over the top of the boxers and moved forward to nudge the tip of his cock against her lips. Emily opened her mouth to allow Todd’s cock to slide in over her tongue. She closed her lips around his cock, stroked the shaft of his cock while sucking on his cock. Todd moved his cock in and out of her mouth, reaching down to her nipples again, flicking them with his forefingers as he fucked her mouth before squeezing and twisting them again. Emily moaned against Todd’s cock and he firmly reminded her not to orgasm yet.

Todd pulled his cock out of Emily’s mouth, pulled his boxer shorts back up over his cock and stepped back. Emily was disappointed about the abrupt stop but tried not to let it show on her face. Todd instructed Emily to kneel on the bench with her back to him and bend over with her hands on the bed. Emily obeyed this instruction and waited. She heard Todd walk across the room, open a drawer and return behind her again.

Emily felt Todd’s finger rubbing over her pussy and the opening of her ass, applying a little pressure upon reaching her asshole before returning to her pussy again. She knew she was so wet entering her would be effortless, and, as if reading her mind, Todd slid his cock in her pussy. Emily closed her eyes in ecstasy and a moan escaped her lips. Todd began a slow rhythmic fuck, sliding his cock balls deep in her pussy before sliding it all the way out and re entering her again until, once again, balls deep and continuing this. While fucking her rhythmically, Emily felt something cold and sticky on her asshole and Todd massaged the liquid over the opening of her ass. She could feel him applying some pressure with his finger as he continued to spread the cold liquid, entering the tip of his finger in her ass. Emily held her breath for a moment, feeling a little discomfort and pressure at first but not for long and the discomfort turned into a pleasurable pressure in her ass as his finger travelled further in. He slid his finger in and out while still fucking her pussy and, feeling more cold sticky fluid, she felt a little discomfort again, as if he was widening her ass hole and realised he was adding another finger. Again, she held her breath for a moment until the uncomfortable pressure turned in a pleasurable pressure. She had always been curious about anal play and had never imagined he would introduce her to anal play through double penetration like this, but was glad he did.

After fucking her ass with two fingers, Todd withdrew his fingers and Emily felt more of the cold sticky fluid against her asshole before feeling something cold nudging against the opening. She felt it nudge against her, applying a little pressure and then a little more pressure before backing off. Feeling the nudging back again, she realised Todd had the butt plug and was gradually nudging it in, backing off and then nudging it in a little further each time. After a few times of repeating this action, she felt a firm pressure at her asshole and realised, this time, he wasn’t backing off. She felt the opening of her ass stretching wider and yelped as her asshole gripped the widest part of the butt plug. With one more firm but steady push, the pain ceased as the butt plug completed its insertion, fully immersed in her ass. Todd gave her three hard thrusts in her pussy and Emily cried out. Todd reached forward, squeezed her nipples “Don’t cum yet, Emily!” he commanded and Emily bit her lip as she closed her eyes, took some deep breaths and held back the orgasm that almost escaped.

Todd withdrew from her and recognised Emily’s surprised reaction when her head snapped up. “I know where I want to finish up and it’s not there.” Todd stated. Todd commanded Emily to lie on her back, across the bed with her head hanging over the edge. Emily did so as Todd left the room. She lay there obediently, waiting, getting wetter with anticipation knowing there was more to come.

Emily heard the door open and footsteps down the stairs. There was more than one pair of footsteps and she looked up to see Todd has someone with him. Another man. “Where did I say your head should be, Emily!” Todd boomed loudly. Emily hung her head back over the edge of the bed. She had spoken to Todd about a double penetration fantasy with two men but wasn’t expecting it to be arranged so soon. She lay, nervously, and waited for what was to come.

She saw a pair of legs and an erect cock coming towards her. She opened her mouth as Todd’s companion’s balls were dropped in her mouth, one at a time, and she suckled on each one, rubbing her tongue around each one, until they were lifted out and a cock was being pushed past her lips. In this position, she could deep throat his cock and squeezed her lips around his cock, pushing her tongue against it. She felt a pair of hands on her nipples then a mouth and tongue on one nipple and two sets of fingers working on the other nipple while she felt the crotch of her outfit being pushed open and someone’s, guessing it was Todd, hot breath over her pussy. She moaned, then whimpered, against the cock and, as Todd inserted several fingers in her pussy and felt her nipples being lightly bitten and squeezed and Todd commanded “Not yet, Emily”.

All of this stopped and Emily was instructed to get up. Emily stood, being able to get a better look at Todd’s companion. He was tall, well tanned and good looking with sandy blonde hair and blue eyes. He lay on his back on the bed. "Straddle him and fuck him, Emily” Todd commanded. Emily straddled the stranger, lowering herself over his cock and enjoying the feel of him inside her, feeling full with his cock in her pussy and the butt plug still filling her ass. Moving up and down on his cock, Todd position himself behind her, pushing Emily forward and she felt more pressure on her ass, yelping as the widest part of the butt plug passed the opening of her ass on it’s exit and immediately felt her ass being filled up, before it had time to retract, with Todd’s cock. He slowly slid inside her ass, not stopping until balls deep. Each man had one of her breasts each in their hand, playing with her nipples and fucking the stranger’s cock meant she was also moving against Todd’s cock in her ass, getting a double fucking from both men. She started moaning and panting, not sure how much longer she could hold back an orgasm and feeling as if she was in heaven in the extreme fullness with both cocks filling her. “Emily, cum now!” Todd commanded and Emily had not trouble at all releasing several orgasms at once, like opening floodgates. Moaning louder as her orgasms continued to intensify and both men came inside her, she yelped out as the intensity peaked and she collapsed on top of the stranger and Todd collapsed on top of Emily. All three lay still while they caught their breath. Todd was the first to get up and he helped Emily up. She turned to see the soft, gentle look in his eyes again. They knew a shower would be next before they would get dressed.