Sissy Dolan

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Mistress Diaries entry August 17, 2006.
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A common misconception about men who commit to serving a Mistress is that they are weak. A black and white distinction that slaves are weak and Mistresses are strong is a foolish assumption to make. Mistress Donna had to admit that many a slave has gained her respect by his unflinching loyalty and devotion, despite painful and traumatic circumstances. Only slaves strong enough to sacrifice much of their personal lives deserved to serve Mistress Donna.

For instance, her Irish Sissy Dolan, had suffered with a jealous and vengeful wife for his devotion of service to Mistress Donna for close to 8 months now. His wife having caught him in the act of serving his Mistress Donna had forced him into domestic slavery for her own wicked pleasure. Unlike Mistress Donna his wife was a cruel and hateful Mistress, her main focus was to make Dolan suffer as much as possible. Little did she realize that this only fueled the fire of desire her husband hid deep in his heart for his Mistress Donna.

Each day he endured the torment of endless housework, cooking, and cleaning in various humiliating outfits under the watchful eye of his Wife Mistress. When she dared nap or venture out of the house, Dolan would beg to serve Mistress Donna. Enjoying another woman's husband had always been a turn on for Mistress Donna, but enjoying another woman's Husband Slave Slut? Now that was to die for.

It wasn't that he was an extraordinary man by main stream standards. He was an average irshman with an average build. But his willingness to submit and to give himself to her... it compelled her time and time again to accept him into her service. What his service lacked in consistency, was well balanced with his ever burning devotion to her. He was unable to serve her often, but when availalbe, she enjoyed him immensely.

She knew it was cliché to say she had fallen in lust with his voice. But the way he spoke, the soft soothing way he called her Mistress.. the way he rolled his 'r's.. the inflection- made her melt inside. The fact that he often wore dresses did not turn her on nor repel her. Unlike other slaves that wore women's clothing, his body did not attract her in the frilly clothing .. not as the other's did. But knowing he enjoyed wearing them, she encouraged him to show up in his favorite pieces. She did not allow him to wear the clothing for long once in her presence.

Tonight he had arrived in a fancy beaded white dress suit. His hairy chest poked through the top of the dress, the heels he wore looked clumsy on his large feet. He wore a hat with modest netting on the front.

He glanced at her through the netting, his blue eyes twinkling. He smiled, averting his eyes and fell to his knees with a dull thud. He struggled with the skirt, then bowed forward, his face flat against the floor, his arms up pointed towards her.

She shook her head at his large shoulders hidden in the white jacket. Her long dark night gown fell towards the floor as Mistress Donna approached him, holding a thick black collar. She stood above him staring down at his back, his round ass in the skirt up in the air for her. Dolan's Wife Mistress did not allow him to have sex with her. An unending punishment that made his ache for Mistress Donna grow, the ache that brought him here time and time again.

She knocked the hat off of his head, it skitted across the floor. His reddish brown hair felt good imbetween her fingers as she jerked his head back. His eyes were closed, a huge smile of delight across his face. His adam apple protruded suggestively making his Mistress want to bite it. But with control she delighted in yanking his head forward a bit. He grunted at the pain and she opened the collar, clamping it around his neck. She tightened it, making sure to make it a bit uncomfortable. She wanted him to feel this later when he was home with his Wife Mistress.

"Where is she?" she asked. Suddenly Mistress Donna was tearing at his clothes, ripping at the jacket, knocking him over on his side.

"Asleep at home, Mistress." He gasped, limp as she ripped the jacket halfway off of him. "Mistress, I missed you so much." She continued to rip the clothes from his body, the look on his face was one of pleasure and pain, a sweet mix that made her pussy start to warm. When he was completely nude, she said, "Open your eyes, slave."

As he did, she let her hair down. The brown hair fell to her shoulders and over to her breasts. His cock was rigidly hard and as she sat beside him on the floor, she pinched his left nipple, lightly at first. He moaned, his hands curling into fists. "Mistress," he whispered, "please, let me be your slut. Let me make you cum, Mistress Donna."

She felt her heart flutter as he said her name, the emphasis on the O, Dohna. "No," she heard herself saying, "bend over I'm going to show you what a bitch deserves." He hesitated for only one second before he was bent over in front of her, his ass inches from her face.

Mistress Donna began by rubbing his asshole. She licked her fingers and slid one in, working it slowly back and forth. His back quivered, his feet curled. He moaned, "Thank you Mistress. Ah God thank you." As she worked his asshole with on hand she began to stroke his cock with the other. Precum oozed from the head, making her pussy drip under her nightgown. By the time she had worked in 2 fingers she could smell how hot her pussy was.

"Mistress," he muttered, "Mistress, you know I can come more than once." His plea made her start to finger fuck his ass faster.

"Is that right?" she said forcefully. "I bet you want a cock in your ass don't you slave? You are the biggest sissy I know." She spat a few times at her fingers as they worked in and out, lubing his asshole.

"Yes, Mistress," he screamed, "I want your cock in me Mistress!" He was bucking against her fingers, his cock was pulsating in her hand.

"You sissy bitch," she growled, starting to work 3 fingers in. "You fucking disgust me." He moaned his knees almost buckling as he moaned, "Let me squirt, please Mistress, oh God please."

Mistress Donna pumped her fingers into his asshole hard, feeling him clench. "Squirt now you dirty whore." With a yelp he was spraying cum all over the floor and her hand. He bucked haphazardly against her hands, his front collapsing with defeat on the hard floor. She slowly slide her fingers out of his ass, still pumping his spasming cock. "What a good little slut you are." Mistress Donna purred and wiped the last drop of cum off of his cock, and without him seeing, licked it quickly off of her finger as she got up taking her position on the chaise lounge, propping herself up with the hand stitched throw pillows.

"I should send you home," she taunted as he still shivered on the floor.

"Oh, Mistress. You'd not do that to me would ya?" He panted, his well muscled chest still heaving from his orgasm.

She pulled her nightgown up, turning over, in a mock position of his earlier pose. She quickly tapped her ass. Without a verbal command he was quickly behind her, licking her black underwear, making the thin material wet. Underneath the material her ass hole was sticky wet. She bucked against his tongue saying "take them off of me, slave." He quickly slid them off of her, his hands sure and firm.

He spread her ass cheeks, his tongue diving between, licking her asshole. He flicked his tongue harder the louder she moaned. Eventually he was sticking his tongue out as far as he could and with a quick head jerk was fucking her asshole with his plump wet tongue. The stubble from his goatee raking across her sensitive skin. Mistress Donna jerked about, and moaned as he tongue fucked her ass harder.

"My Mistress," he panted, "please Mistress." His voice thrilled her and her pussy dripped with anticipation.

"Lay down you fucker," she said quietly. He was instantly on his back, his tongue still sticking out of his mouth wagging with anticipation. She positioned herself on top of his face. Squatting lower and lower until his tongue touched her wet pussy. "Grab my legs," she ordered and as he did so, she lowered all her wet onto his face. He tongue fucked her hard, her pussy pouring juice onto his face. He pulled on her legs forcing her down harder on his face.

After a few minutes, Mistress Donna started to life her pussy up, to give him a breath, but her slave clasped her thighs hard, the mixture of his strength and her body being overwrought with pleasure kept her steadily in his grasp for his splendid tongue fucking.

As his grip began to lessen, she leaned forward, breaking the hold he had, he licked and panted catching his breath and trying to swallow any juices that had ran down the corners of his mouth. "Mistress you taste so good Mistress," he purred and started stroking his hard cock. "Mistress I can't control meself." His legs jerked as he stroked, "Please Mistress, please cum on me face Mistress. I need to taste you again."

The butterflies batted at her ribcage, Mistress Donna leaned back on the chaise lounge, and spread her legs wide. She tapped her pussy and he was instantly upon her again still stroking his cock while he ate her out. She squirmed for an eternity, the tension building. Just as she came she heard his cell phone ringing.

"Please let me cum," he begged, the annoying ring still in the air. "I don't want to leave until I can cum Mistress." His face was wet with her juice and as she smiled down at him she nodded and he squirted all over his hand and stomach, jerking hard against his pumping hand. Finally the phone stopped ringing. A moment of silence passed as Mistress and slave lay quietly, touching each other.

Then the phone began to ring again.

"Mistress?" he said quietly. Mistress Donna sighed, "You are dismissed you sissy fucking girl. You have to always go when your bitch ass wife calls you. You disgust me."

She roughly unbuckled his collar tossing it down to the floor beside him. As he dressed quickly in his ripped and tattered dress he did not look up. He paused at the door, his head still down. Mistress Donna had a wave of emotion wash over her. She knew that what waited for him would be only more torment and rejection without the pleasure or satisfaction of having done a good job serving his Mistress.

"Wait," she said forcefully. She walked to him and stood in front of him. She grabbed the back of his head and forced his lips upon hers. He kissed her as passionately as she would allow, until she felt he was hard again against her, she pulled him against her, pressing herself flat against the door.

"You will tell her you were attacked," she said huskily. "And that she should not force you to wear this clothing when you leave the house."

"Yes Mistress," he said quickly, staring into her eyes. "You will accept me when I can come again my Mistress? Please tell me you will, Mistress." Many times she had seen the look of need in a slave's eyes, but the married ones, the ones who lived day to day with the deep longing she fulfilled... those were the eyes of her favorite slaves And this man, this Irish Sissy of a man was one of many who satisfied her womanly yearnings.

"Please forgive me Mistress, please forgive me," his voice made her quiver inside then she smiled up at him. "Yes slave. Do not stay gone from me for long." She opened the door for him, and he was off into the dark night.

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