Crossing the Line
  • Author - Neil Sanddriver
  • Rating -   
  • Site Rank - 2056 of 2955
  • Story Codes - F-m, M-f, consensual, analplay, bondage, cross-dressing
  • Post Date - 8/5/2017

Author's Note: Dedicated to a friend of mine, she knows who she is. Also I am dyslexic so bare with me, have done as best i can with spell check etc. Thanks


Cath lay in bed looking at her phone screen, or rather the background screen . It had been nearly half an hour since he last massaged and she wondered had he gone to sleep. Her phone was the only thing lighting the room as she otherwise lay in complete darkness. She was waiting for her friend Neil to message back. She had known him a few years now and they had worked together for most of that. She had always liked him but never really acted on it as he was in a relationship. However he had recently revealed that he fancied her and had always done so, but for obvious reasons never acted on it. Neil was still unfortunately in a relationship but after a lot of talking with Cath they had discovered something about themselves, never once raised in their years of friendship. Neil had told Cath he was very much into bondage and as conversations progressed it became obvious Cath had a fascination with this to and they had begun to share their inner most fantasies with each other. They both realised that nothing could ever come of this and had agreed as long as it stayed as conversation it would be treated as a bit of fun and they would both just enjoy this new if not slightly forbidden experience.

Neil was not what would be deemed a very attractive man, he was average looking and average build, but there was something about him, he brought out this side of Cath she had never shown and she loved the excitement. Cath was in her 40's and neil was in his 30'S, Its safe to say Neil was slightly more attracted to Cath than vice versa, but she loved the fact a man in his 30's was offering her this kind of attention. Suddenly her phone vibrated and she noticed straight away it was a photo, she thought it may be the old cliche dick pick and was not particularly intrigued. As stated Cath was a women in her 40's and although had not been with too many men was very much above the old penis picture. When she opened it her heart raced, she had to look at it several times before she believed it.

there was her friend laying on his bed with stockings on knee high boots and a leather skirt and corset, gagged and his hands in cuffs. She knew he had a taste for cross dressing and bondage, he had been completely honest with her, but she never thought she would see it.

She looked intently at the picture, without realising her left hand sliding in her knickers and she began to massage herself. they had joked the previous night about him wearing her clothes and she unexpectedly became turned on by the notion. Now she could actually see it and it made her horny, not just horny, she felt a sense of power and excitement she had not known before, imagining she was there and he was made to do it.

She realised she had not messaged back and promptly did so, explaining how turned on she was and even advanced the conversation to what she would like to do to him if she was there.

For the sake of the story i will move things forward a few weeks to the main event. By this point the two friends had bared all to one another and they had some very explicit conversations about what they intended to do to each other given the opportunity.

Cath was just getting into bed and getting comfortable awaiting her message from Neil as they had previously arranged. As if she had set an alarm her phone pinged exactly at 9:30. "Hey gorgeous, are you in bed yet ?" She messaged back "Yeah hun, just, all ready for you to message" Then her phone pinged again "Thats a shame " She sent back "????" then the reply, like the photo message she first received, she had to read it several times. "Because you will have to get back up and come let me in, I am outside ". She nearly fell out of bed and went to the window and pulled the curtain back, he was stood there patiently waiting. She had that cut feeling of excitement and nervousness all in one go. She thought quickly and stripped her fleecy pyjamas off grabbed a silk nightie out of the top draw and matching silky red knickers and pulled them on frantically in the hope he would think this is what she always wore to bed. She grabbed her dressing gown and raced down the stairs and flung the door open. " what you doing here, come in quick before the neighbours see you". He stepped in and shut the door behind him, placing a hold all type bag on the floor. "I want to see you, I want us to have a play, even if you dont want sex, thats fine but talk is not enough for me anymore". She looked at him and instantly knew he was serious, "come upstairs you mad bastard. Cath led the way and was almost shaking with nerves and excitement, this is it she thought, oh well you only live once.

After some conversation and time for Cath to compose herself she was finally ready, she slipped off her dressing gown and lay suggestively on her bed.

Neil took his coat off and his jogging bottoms to reveal his pvc vest and pants, Cath run her hands all over it, loving the feel and realising she had never had a man dress up for her before.

He took her wrist and placed a handcuff on it locking it securely then forcing her back onto the bed, he then locked it around the bed frame in the corner. He took her other wrist and locked it to the other bed post with another set of handcuffs. Cath was getting damp just by him doing this, let alone anything else. He then tied each of her ankles firmly to each corner of her bed so she was spread eagle. She pulled on her restraints and it was quite obvious she was not going anywhere. He lent over her and kissed her softly, she kissed back instantly, arching into him. He had one knee between her legs as he was leaning over and she felt it pressed into her, the pvc of the pants rubbing against her pussy, she started grinding on it and was getting so turned on. He pulled away and before she knew it she had a rubber ball gag between her teeth and fastened tightly behind her head. This all felt strange and she tried to talk as she had never been gagged before, the fact that only muffled noises came out turned her on more. She started thinking to herself, i couldn't stop him now even if i wanted to, but this only excited her rather than worried her. She watched as his lips made their way down her neck kissing her so gently, he then slid the top of her nighty down and releasing both her breasts, he circled her nipple with his tongue. She groaned gently into her gag and lost herself in the moment. After a little while he stopped and climbed off the bed, leaving her a little confused. He returned almost instantly with what she knew to be a magic wand, she knew this because he had shown her in a picture, weeks previous and explained what it was and did. She watched as he tied a rope around her waist and under her crotch securing it tightly against her, so it dug in slightly to her pussy. He then placed the wand quite firmly against her pussy and used the rope to hold it in place. She knew what was coming and in a matter of seconds, it was switched on and it went through her body like waves of extreme pleasure. She pulled at her cuffs and at her ropes and groaned heavily as the wand went to work on her . She looked up at Neil who was standing over her watching, quite clearly erect beneath his pvc pants. She groaned louder through her gag and fought her bonds as she got closer, she realised she was helpless. She looked him dead in the eyes as her back arched up like she was posessed and she orgasm'd violently before sinking into the bed.

Neil Knew she was a first timer to the wand so he switched it off after her orgasm as it can become uncomfortable for her. He untied the crotch rope and sat next to her on the bed looking at his new slave, he grinned as he plotted his next move.

He un cuffed and untied her but left her gag in before she had time to do anything else her forced her face down on the bed. She resisted initially but didn't really put effort in, in a matter of minutes she was re cuffed and re tied exactly the same way but on her front. She felt her head being pulled up sharply by her hair, this hurt her slightly and she yelped a little through her gag, then he whispered in her ear "your mine and you will do as your told, you fight me and you will be punished, understood". Cath was shocked and knew the normal feeling should be scared, but why wasn't she scared? She could not believe it herself but this turned her on more. "Understood" He said a bit louder, she muffled yes through her gag. "I am going to whip you now and i want you to say thank you every time your whipped, if i dont hear it you will be whipped more". Before she could react she felt the sharp leather strands of the whip on her silk covered bum and jolted, "Thank you" she yelped. Neil grinned as he whipped her again "Thank you ". As this continued the small pain became pleasurable and Cath found herself extremely turned on by this whipping, It was like this guy knew exactly what buttons to push and she was almost annoyed when he stopped.

She was then lifted slightly off the bed and several pillows where forced under her mid section forcing her bum to stick up in the air and making her feel very exposed. She felt something cold and wet running down her bum cheeks and felt his finger rubbing into into her anus, she guessed straight away it was lube and before she could protest something cold and metal had breached her bum hole and slid up inside her. She deduced this was an anal hook and then she felt a chain being secured from the anal hook to the strap of her gag at the back of her head. Cath was getting wetter and wetter and soon realised if she moved her head forwards the chain would tighten and the anal hook would move in her bum. She lay there helpless but enjoying it, she felt him on the bed behind her and knew what was next on the cards. She groaned as he entered her sliding in as deep as he could to her already very wet pussy.

She panted almost like a dog as he slid in and out slowly then gradually speeding up, his hands on the small of her back as he fucked her doggy style against her will, the hook sliding in and out of her bum in rhythm with him.

The pressure built and she heard him getting louder with his breathing, she couldnt hold on any more and violently tugged at her handcuffs and with a final tensing of all of her muscles felt him explode inside her as she cum all over him.

He withdrew and knelt there for a minute catching his breath, before slowly untying her ankles then very gently removing the anal hook, then finally her gag and cuffs came off.

She lay there in his arms and they talked a while, mostly joking that the friendship was ruined. After an hour or so Cath said "Ok its my turn now, i get to do what i want with you" Neil grinned, "never thought you would ask". Cath jumped off the bed and disappeared into her wardrobe before turning round with a some items she placed on the bed. "Put them on and don't give me any shit, after what you have just done to me you have nothing to be embarrassed about, I am going to get a drink, i want you ready when i come back. When Cath returned she was pleased to see he had squoze into her denim skirt red lacy knickers and tube top. She made short work of placing him in handcuffs and picking his bag up and leading him down the stairs. Once in the hall she pushed him face up against the banisters and walked halfway back up the stairs. She reached through and grabbed his wrists unlocking one handcuff she fed it through the banister spindle and locked it back round his wrist so he was now cuffed with his arms above his head to her stairs.

She rummaged through the bag and took out a spreader bar, smiling to herself she kicked his legs apart and fastened it to each ankle forcing his legs to stay open and his bum to stick out. Finally she slid off her silky knickers which had been on all night and stuffed them in his mouth before tying her dressing gown belt between his teeth so he couldn't spit them out. She looked at her handy work and was very pleased with herself, she could not understand why a man in her clothes excited her so much, but she just enjoyed it and stopped worrying. She informed neil he was going to be whipped and was to say thank you mistress with every strike.

He did as he was told and Cath found herself trying to masturbate whilst watching his poor bum get whipped repeatedly, she had never had this sort of power over a man and it was like nothing she had ever felt.

With difficulty she managed to get him to turn round and face her and took great pleasure in looking at her strung up slave hanging there helpless. She gripped his nipples and tugged on them watching him flinch and groan, but knowing it was turning him on as the bulge in the skirt was not going away. She thought she may never have this opportunity again and decided to make the most of it by grabbing him by the throat and holding him there. Again looking down at his denim covered cock, this seemed to be enjoyable for her and she smiled to herself. She un cuffed his wrists from the banisters but then re cuffed them behind his back and left the spreader bar and gag in place . She made him hobble over to her dinning table and forced him face down bent over it before placing him in a collar then chaining the collar to the other end of the table forcing him to stay in that position.

Neil presumed he was in for a further whipping but he could not be more wrong. Cath disappeared then came back a few minutes later, he felt her walk up behind him and the familiar feel of lube on his arse. He knew he was getting the anal hook and he relaxed and braced himself. He felt it enter, but it was not cold and was slightly more uncomfortable. He tried to turn his head but the chain held him down. He felt it go in further it was like rubber, then he realised as he felt Cath's crotch touch his arse, she had a strap on, holy fuck, where did she get that he thought.

She slapped his arse as he groaned "you wanna know what its like to be fucked, your gonna find out". He panicked slightly but realised he could do nothing and embraced her as she entered him again, in and out slowly, then picking up the pace.

Now it was his turn to pant as he felt her fucking him harder and felt his cock rubbing violently against the inside of the now tight denim skirt. She kept smacking his arse as she fucked him, he pulled on his cuffs and groaned loudly into his gag, she grabbed the waistband of his skirt and pulled him into her as he shook violently and exploded on himself. She withdrew and unchained him from the table and helped him sit on the floor, but she left him tied up sitting in his own mess and went upstairs.


The End
The author has indicated there will be no future updates



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