Jack and Jill Pt. 03: Anna

The next day Jill was at work in her office, a parcel had arrived for her and when she opened it to her delight she saw it was a double ended dildo. She had ordered it some weeks ago so she could use it with her sissy husband. It was longer and thicker than she imagined and she felt heat between her legs at the thought of what she would do with it. She was sat on the edge of her desk admiring it when the door opened and her secretary Anna walked in. Anna was a big girl, attractive and very curvaceous, Jill knew Anna had a crush on her and things had gotten very flirty at the Christmas party. She saw Anna's eyes dart to the dildo and then back to Jill.

'Anna...' Jill started.

Before she could say any more Anna had crossed the space between them and kissed Jill hard on the mouth. Jill pulled back and leaned back across her desk, her legs spread in the recoil motion, which Anna must have taken as encouragement because she pulled Jill's skirt up over her buttocks, exposing her stocking tops and the fact that she was not wearing panties. Before Jill could react in any way Anna had her face down between her legs. It was all happening so quickly Jill didn't even finish her sentence, she chided herself for not wearing panties, she was planning a night with her sissy bitch and liked to put her strap on on before she got home, that way she could fuck him hard up against the hallway wall. These thoughts flew through her mind until she felt Anna's tongue circle her clit and then she went blank.

'Ohhhhh god!' She cried unable to control herself.

She gripped her desk and spread her legs wider. Anna's tongue was exploring her slit and she could feel she was already soaking wet. She lay back on her desk, her legs splayed. Her mind floating away as Anna's tongue alternately massaged her clit and entered her sopping hole. She began to buck against Anna's tongue wanting it harder against her greedy pussy. She reached into her blouse and grabbed her own nipple squeezing hard, her other hand on the back of Anna's head pulling her in deeper.

'Anna, Anna, Anna...' she cried out as she came hard in Anna's mouth, grinding into Anna's face.

She held Anna there for a few moments the pleasure still tingling through her before releasing, she leaned forward, intending to regain control of the situation, but Anna pulled her into a tight embrace, holding her close and sliding two fingers up Jill's juicy cunt. Jill inhaled hard, she could feel Anna's fingers inside her, sliding down the front wall of her vagina in a beckoning motion. It was right on her g spot, she lost control, sinking into Anna's embrace, she felt herself gushing over Anna's hand. Hot pussy juice was flooding her legs, her desk, Anna's skirt, everywhere, but all she could do was grind on Anna's hand, wanting more. Knowing she was going to cum soon. Jill clawed at her blouse, opening the buttons, exposing her breasts, Anna leaned out and took Jill's nipple in her mouth, sucking hard, she increased the ferocity of the fingering. Jill couldn't take anymore, squirting and shaking, she came, hard her wet snatch spasming, squeezing Anna's fingers and pulling them deeper in.

'Anna... wait..' she started.

Anna was not going to be swayed, she had obviously waited a long time for this and she wasn't stopping know. She flipped Jill over onto her front and grabbing the double ended dildo. Jill heard her sucking it and then felt it part her lips and enter her slowly, it filled her a couple of times before it was removed and she felt the other end enter her. Suddenly Anna's tongue was in her arse, she squealed, but pushed back into the tongue. God it felt good, she loved having her arse licked out. She liked it best when her sissy skit was licking Jeans hot cum out of there. But this, this was hot, Anna was taking her, having her and she decided there and then to let her. Jill's arse felt very wet and Anna rubbed pussy juice all over it for extra lubrication before sliding the dildo in. Jill gasped and wiggled as the first end penetrated her anal passage, it was a shock but she quickly got used to it, she was an anal slut after all, just like her husband. Once she was comfortable and pushing back on the dildo, Jill felt Anna press the other end against her pussy, mmmm, double penetration, her favourite. Who new Anna was such a dirty bitch. Jill relaxed and bore down on the both ends. Filling her hungry holes to the brim. Anna was holding the u-bend of the double ended dildo and began to pound it in and out of Jill furiously. Jill spread herself, pushing back against the onslaught, her holes being fucked hard and fast, she reached between her legs and rubbed her clit, she felt Anna pull the other arm up behind her back and push her face into the desk. Jill was helpless, attacking her clit with furious enthusiasm she came hard, her whole body trembling, but Anna didn't stop, she upped the pace and fucked Jill even harder, Jill thought she was going to pass out and then she came again and again one more time before Anna released her. Jill felt the dildo leave her ruined body and she lay there for a while her holes gaping in the cool office air. When she rolled over she saw Anna was now naked apart from her stockings, her thighs moist from her dripping pussy and the nipples on her ample breasts rock hard. Jill pushed off her own skirt removed her blouse and bra and taking Anna's hand led her over to the sofa. Anna sat down, her legs parted and Jill got down on her knees, leaning in she kissed Anna's moist labia, running her tongue between her lips, locating her clit and pushing her tongue up inside Anna.

'Oh Jill!' Anna cried.

Jill went to work licking her secretary's soft fleshy folds, her hands moved up finding Anna's nipples, caressing and squeezing them it didn't take long before Anna came in Jill's mouth. Jill picked up the dildo from the table and sucked the end provocatively before thrusting into Anna's waiting pussy.

'Mmmm' Anna cried 'Oh fuck yes' she began to grind hard on the long rubber cock, Jill thrusting it hard into her until she came again the wet patch in the sofa growing with every thrust. Jill joined Anna on the sofa and slid the other end into her own still gapping slit. She bore down on it, every movement causing pleasure at Anna's end. Jill slid down onto it as far as she could as did Anna until they had engulfed the lot and their cunts were grinding against each other. Jill came hard, Anna came hard. The two of them ground against each other for an hour before they were too exhausted to continue fucking. They dressed quickly and returned to work. Jill spent the remainder of the afternoon thinking about her lesbian adventure, the sweet taste of Anna's pussy on her lips...

He got home early and began his preparations for the evening, he douched and shaved, lubed and plugged himself and tucked and tied his cock. He put on his prettiest pink panties, stockings and his mesh mini dress. He slipped on his heels and minced around the house waiting for Jill to return. He loved the wiggle his tucked cock gave his walk and the smooth profile it gave his under carriage. He was feeling like a real sissy girl and was looking forward to being dominated and pleasing his mistress. His plug felt good buried in his pussy and he was beginning to stretch very easily now, his hole experienced in taking big black cocks for hours on end. He heard her car pull up and he felt a shiver of excitement run down his spine, he wiggled over to the front door to greet her. Hoping she would be wearing her big strap on cock. He was in luck, when she opened her coat she was wearing only stockings and her strap on cock! She pulled him close and kissed him hard on the mouth, her tongue in his throat, he melted allowing her to take control.

'Get down on your knees slut!' she ordered.

He got down obediently his arse high in the air.

He felt cool lube being applied and his butt plug twisted and pulled in and out.

'Mmmm...' he moaned, pleasure radiating out from his greedy pussy.

He felt his arse open up as she pulled the plug past its widest point, holding it in place for a minute to stretch him fully. Then it was gone, he felt empty and needed to be filled. He fingers were soon inside him, adding her more lube to his slippery pussy, then the head of her cock was pressing into him, it penetrated him with ease and he felt her thrust balls deep into him. He grunted with pleasure, pushing back on her cock like a good sissy. She had trained him well. She leaned over his back and whispered into his ear, telling him all about her adventures with Anna as she thrust deeper and deeper into his slutty arse. He loved the story, the thought of her with another woman, he thrust back against as hard has he could, riding her big rubber cock like the anal white he was, panting he began to cum anally, hime could feel his tucked cock dripping as he allowed himself to be milked. It started deep in his bowels and radiated our through his whole body until he was shaking with ecstasy, gripping her cock hard, before pushing it out on climax. He had no time to recover, she quickly pushed it back up his gaping hole and fucked him hard again, telling him to imagine he was being gang banged by a group of black men, he hoped one day he would really be gang banged by black men. He came again, she resumed fucking him again, over and over until his arse was totally ruined and hanging open and he had been fucked by at least ten guys. He remained on all fours panting, knowing that she wasn't done and that the next part of his sissy training would be her fist in his arse. He braced himself and sure enough he felt four fingers enter him, followed by five, twisting and stretching him until he could feel a whole fist inside him, he felt full, he felt submissive and helpless, he relaxed and allowed her to open him up, soon both hands inside him, double fisting his insatiable man cunt. He felt his limit when she turned her hands and pulled him wide open.

'I could easily slide a champagne bottle in you,' she smiled 'my dirty girl.'

He submitted, allowing her to abuse him, loving being abused by her, his pussy taken to its limit. He could feel his anal lips swollen and proud when she released him, he enjoyed the sensation, it felt like he had a real pussy.

He winced as she pulled his tucked cock firmly back into position and pulled his panties back up, his undercarriage smooth and feminine again. Still on his knees he opened his legs so she could rub him and feel his smooth profile. He got to his feet with her help and she led him to the bedroom, once there she took out a double ended dildo and a double penetration strap on dildo...

She pulled the harness up over his legs and secured it tight, his tucked cock was nicely out of the way and his smooth front was the perfect base for the double dildo strap on. She though back to earlier in the day when Anna had been penetrating her in both holes and she shivered, it was so good, she wanted more.

'Do you want to please your mistress?' she asked.

'Oh yes,' he replied 'very much!'

'Good,' she said 'I want you to fuck me good and hard with your strap on, like a good lesbian sissy.'

'Yes mistress.' he agreed.

She took off her strap on and got on the bed on all fours. She was very wet and eager for a repeat of this afternoons pleasure. She felt the cool lube, followed by his fingers enter her slutty arse, it took no time at all for him to open her up, four fingers buried inside her moving in a circular motion.

'Mmmm...' she moaned as she gyrated back into his hand. He reached underneath with his other hand and began to rub her clit.

'Oh!' she cried out, gyrating harder now, enjoying the pressure on her throbbing clit.

She found herself panting hard, pushing back onto his hands, her orgasm was building, she was going to cum, his fingers continued to work her expertly until she released. Her greedy arse gripping his fingers tight as waves of pleasure washed over her. She felt his hands withdraw and then replaced with pressure against her anus and vagina simultaneously. Her wet lips parted easily and the dildo entered her pussy slowly. The big anal dildo took a little longer to work its way through her sphincter, she bore down on it, pushing out to open herself up and allow it to pass through her barrier, with sudden relief, it was inside her, the two dildos filling her abdomen in a single thrust, she grunted, a deep animalistic noise as she accepted the violation of her body. She paused for a moment adjusting to the intrusion and then began to rock back and forth on the dildos, building up pace, feeling them rub against each other through the thinnest of membranes. Her nerve endings were on fire, the sensation of friction against all her inner places driving her crazy.

'Oh god baby, fuck me,' she cried out 'fuck me, fuck me, fuck me!'

She pushed back against him, eager to fill every corner of her greedy holes. She felt him respond by picking up the pace and power of his thrusts, burying both dildos up to the hilt inside her. She was panting, breathless, she thought she might pass out from the overload of sensation. She spread her legs further, reached between them and began to rub her clit, she felt his hand reach around and grab her nipple hard, it was too much, writhing and thrusting and gripping, she came hard, g spot, clitoral, anal, all at the same time. She was shaking like a leaf, she collapsed onto the bed, gasping for air. She felt him lie with her, remaining inside her, she felt his weight on her back. As she recovered she felt him slowly push into her, the dildos moving inside her, she responded slowly. She smiled he was making love to her, she moved slowly with him savouring the sensation, climbing slowly to her next orgasm, he reached under her and took control of her clit, his weight on her back and his hand under her made her feel safe. She came again, a long drawn out, amazing orgasm that radiated through her body for several minutes, her holes full and satisfied...