A Tail Of Changes And Twists In His Life

Ben was a security guard in a pretty impregnable place, he'd been working their near on 5 years in a locked vault watching cctv monitors.  His girlfriend Samantha was the love of his life & today's the day where she brings him a special lunch to celebrate that 5 years passing with a stable well paid job..  A Lunch.... Like Never Before.
(but we shall get back to the anniversary in a short while)

Samantha and ben have been together almost a year now, so this lunch is a double celebration for both of them. Not long after they met (around 3 months) Samantha found some internet history and realized ben had a few fantasy's he'd never shared, this upset her a little and also turned her on...

Now she had plans, but she also loved him and decided to enhance their relationship.  One night over dinner she let it slip that she used to watch porn with her room mate in college, ben was all ears for once... Samantha also spoke about how seeing 2 girls going at it really turned her on back then and she'd often fantasized about dildos but had never had the guts to order one.  The sex that night was amazing and the next day ben set his own plan in motion.  He order a couple of dildos for her birthday as a surprise, but the surprise was she logged into the website and changed the order. The two dildo's arrived as ordered but also apparently included a toy called the bed over boyfriend (a purple strapless strap-on) Ben figured o well their loss and thought she'd love its size and a freebie is a freebie right?.

You can assume bens thinking at some stage a 3 some is on the cards and he'll get to see 2 girls live in his own bed...  But its him she loves and its him she wants to be with.
On her birthday night he says i got you a special extra present and hands her the box, when she opens it she grins and her face is as red as a rose, he takes her by the hand and leads her to the bed room.

I forgot the batteries he says and pops down to the car, when he returns she is laying on the bed with the 3 sex toys in a row, shes wearing black hold up stockings, a g-string and a black bra.
Next to the 3 toys is a clump of silky looking material.

Ben returns with the batteries and Samantha gets him to sit on the bed, he feels her stocking top as she kisses his kneck then she asks would he make the fantasy complete?  yes he says, then she hands him the silky clump and points to the bathroom... but but ben says as he realizes what she wants. she puts her red painted fingernail to his lips as she whispers.. I want to feel your stockings glide against mine, to feel the silk on my skin as you always do.  Ok ok ben says with a reluctant smile and heads into the bathroom.

Ben exits the bathroom in the dim light and slides onto the bed, their legs wrapping round together as they kiss passionately. Shes never been this full on with him before and her hands have never roamed over him this much.. and he loves it.

With ben on his back and her leaning over kissing him she reaches for a dildo, she feels them blindly while kissing & chooses her first weapon of sissyfication.... she leans back from ben and brings the dildo into his line of sight... Im so happy you bought me this as she blushes, it feels so big and vainy (wow contain the excitement ben thinks to him self, after all im not that much smaller) Would you like to see me suck him Samantha says while gliding a finger along his stocking and over his fleshy thigh as she traces his knicker line and his waste up to his bra... (she referred to it as him for a reason) Then as she ran her tong along its whole length from balls to tip she came hard..  Yes mm gawd yes ben said as she then wrapped her lips around it, going up and down and up and down, holding the dildo in one hand and bens hand in her other hand, gripping his hand tighter as she sucked it deeper and faster, gasping for breath she said. I NEED HIM INSIDE ME PLEASE GAWD as she fell back on the bed still slowly sucking on it.

Do you want to see me take HIM inside me she purred.. HELL YES ben said, as she slid it from her mouth and held him at her entrance and lay her head back, she let out a moan as it touched her clit. She guided bens hand to the toy and looked him in the eye.. Then Samantha said... If i am going to take a cock that isn't yours (then bit her bottom lip provocatively)  you need to tell me... tell me you want me to take THIS cock inside me.. tell me you want HIM to fuck me... and then guide HIM into me....  Bens mind was racing, this was foreplay like he'd never experienced before, he wasn't even fully hard anymore yet he was more horny that he'd ever been in his life...  I want you to take him, i want you to enjoy him.. ben shouted shivering in his bra, panties & stockings, he'd almost forgotten how silly he felt dressing like a girl after hearing the pleasure it was giving Samantha, ben had even forgotten it was no longer a TOY, it was no longer a DILDO.. it was HIM.. a HE...  Ben started taking her faster and harder, then slowing down with long lingering strokes from head to hilt.. long slow veiny strokes... Lick my pussy while he fucks me... she moaned.... Ben got between her legs and started licking her and sucking on her clit, she grabbed him by his hair pulling him in.. grinding her self on HIM and bens mouth.. She was moaning and screaming like he'd had never heard in his life...

He'd always been straight and couldn't believe just how much this foreplay was turning him on... (the internet history she saw was every day girl on girl porn, so that fooled you didn't it readers OR did it)

 He slid the second toy into her and she let out a moan like he'd never heard before to, it sent more shivers up his spine hearing her moan like that, she mumbled oo yes.. fk me oo my gawd hes so much bigger and better than y...y...you..  just then she bit down on a pillow she pulled over her face.. ben loved it and thrust the dildo deeper and harder and faster, egging her on. Is he big baby.. is he hard and fast.. fk yes came the muffled voice under the pillow.. take me she said i need to feel your cum inside me.. fk me... he climbed on her and she reached between her legs to grab him, he wasn't even that hard anymore.. so much so she regretted pulling out the toy..  with evil in her mind she raised the toy to her own lips and said Taste me.. he looked puzzled as she wiggled his cock against her soaked entrance, moving her hips back each time he tried to push into her.. TASTE ME she said in a more demanding tone... as she put the toy to his lips.. he opened his mouth and started to suck on that cock that had just brought her so much pleasure... their eyes met as she placed him inside her as she whispered... your reward for tasting me...  He came as soon as his useless shaft was inside her.and then he held on to her like a new born baby... This was it she thought.. now i get better foreplay but he doesn't last as long, she wrapped her self around him, knowing full well he wanted to strip, she made sure he slept-ed in what he was wearing...

The next few times they had sex the toys where always a part of the foreplay, but she only begged him to dress once in a while and every time she did he always came to soon and was much softer inside her.
One night she decided to skip the toys and the dress up so he'd be harder, but during sex she'd whisper things like, do you wish you where guiding him into me?,  do you wish you could taste me on him?,   one night she even said don't you wish you could taste him inside me, he came at that point, and so she found she could bring him off faster when referring to her being fucked by another cock....  OMG my boyfriend is a cuck... mmm ideas ideas.. the freedom to.. mmm this is going to be so much fun she thought to her self...

On his birthday she gave him a strappon harness and said now you can look me in the eye when you make me take his big hard cock.. Samantha fitted it on him and then tied him to the bed.. and to keep you eager i got you this,,, and she swiftly fitted a CB-6000 to his cock.
She locked the padlock then showed him the necklace with the key and she fastened it around her neck.
She said ive been reading up on the internet about all the ways to make a guy cum... but first i wana feel HIS big hard cock inside me.. she looked down at him and wore an evil grin as she lowered her self onto the dildo strapped to him. As she rode it hard and fast bens confined cock strained and made him moan, this just made her grind down harder and faster on the dildo, she loved being in control and having him at her mercy... She rode him for at least 30 minutes then she sat on his face and ground down hard smothering him.. she came more and more as he struggled to lick, suck and breath, his moaning was so intense, i bet that cage hurts like hell she said as she giggled and ground down harder on his mouth, then she got back onto the dildo...
This went on for almost 2 hours.., ben was wriggling under her like a sex hungry slut, his cock trapped looking up at her and seeing the lust on her face...

After a while she climbed off and tied bens legs above his head, she grabbed the lube  and lubed one single  finger, poor ben looked almost traumatized as she massaged around the entrance to his ass, as he started to say no, she unhooked the dildo and whispered taste me.... and slid it in his mouth... Samantha slowly began to fuck his face as she teased his ass.  Ben tried to raise away from her finger yet found him self also wriggling and searching for it.. he was unconsciously trying to guide it to his virgin entrance, she slowly slipped in then out,  he let out such a sissy moan, as she did it again and then again.. making sure as to spread lube deeper each time. when she was sure she'd lubed him enough she searched for his prostate as he wriggled on her finger, she new he was close, she took the toy from his mouth and placed it inside her, moaning in unison with him, as she licked the precum from the tip of his cock through the slit in his cage... Samantha then took the toy out of bens mouth an placed it under his trapped and limp cadged cock...

As she teased him more with her finger, he had a strange sensation as cum oozed from his cock all over the dildo and her hand, she licked her finger then leaned over and kissed him, his tong searching for more of that taste and she new it...  she started moving her finger faster now, no longer interested in his prostate, this was a fingering girl on girl style and he moaned like such a slut.. she stopped and said i want you to taste us and guided the dildo covered with his and her cum to his lips, he tried to move his head but she held him by the hair and said please!!! i want you to taste me and you together!!! like i do when i taste your last few drops!!!    Ben opened his mouth and she guided it in gently at first, then started fucking his mouth with it, the more he gagged the more it turned her on and the faster and harder she fucked his face.... as her other hand went back to taking his ass...  she figured next time hes tied to the bed shes going to forcibly break him in with that big fat purple Bend Over Boyfriend....  But for now.. lets get him used to eating cum....

Valentines day.. bens had to work the last 2 years, so this is a valentines night Samantha's been waiting for...  Ben has no idea but Samantha has booked a table and bought some new clothes.. tonight she has plans and its been 3 months since bens been in his cage so she figures with a little teasing he'll do anything she asks him to for release...  Hi honey she said kissing him on the cheek.. while gliding her hand over his crotch (making sure hes not tried to cut off his cage) Ive laid your clothes out on the bed, remember our reservation is at 7pm, go get dressed then ile inspect you she said with a giggle.. then sipped her wine while motioning with her hand for him to go hurry up..

On the bed ben found a pair of stockings, a thong, a waist clincher,  a corset, small black pencil skirt and a jacket,, all in black. he looked puzzled because he thought... we are going out for dinner, maybe shes joking about going out he though..

So he though i will play along.. So he slipped on the stockings, then he slipped on the thong, trying to make his cadged cock comfortable... then he slipped on the skirt, it confined his legs and made him take much shorter woman like foot steps, the squeezed into the waist clincher and then the corset, then he slipped on the jacket and walked down the stairs. with a glint in her eye she said.. OMG baby you look stunning... Samantha handed ben a 5 & half in pair of black heals and a hand bag then told him to sit in the chair in the kitchen...

while She did his make up ben tried to calm him self with wine, the cage was burning like hell and he so needed release.  Samantha did his foundation, eye shadow, eye liner, mascara, blusher, lipstick, the sh sprayed him with perfume.. Ive never smelt this one before ben said... Samantha smiled and said this ones just for you.. its yours, then slipped the perfum and lipstick in bens new handbag...

She reached into a carrier bag and pulled out a wig, it was long and very blonde almost bleached... she stood next to ben as they looked at each other in the mirror.. ben could of exploded right their..
Samantha said your going to need a name.. i cant call you ben tonight, he just looked dum struck.. jesus she said, its true about blonds isn't it hahah.. i shall call you Nickie its short for Nicola Samantha said.. With that samantha pulled her phone out and rang a taxi.. we'll be drinking hun so best not to drive hey...
All this time.. ben was still staring at himself and Samantha in the mirror....

As the taxi pulled up ben was still speechless as Samantha led him out the house into the taxi... Going anywhere special the cabbie said as he eyed up sam and ben/nickie...  where off into town to see what meats available Samantha said as ben looked really shy and blushing.. your friend doesn't  look like shes up for a night out on the town is she ok said the cabbie to sam.. yeah shes fine said sam, just a little shy, shes a virgin..  OMG the taxi driver said.. a virgin looking like that.. fucking wow...

Sam teased.. are you single.. she could do with a nice guy for her first time.. sorry love im married he said, but that said a blow job isn't really cheating right? Samantha laughed as she said.. if you skip the fair im sure Nickie would be willing to taste her first lover...  The taxi pulled into a side street and the driver got into the back.. Samantha kissed him while he groped her, then sam undid the drivers belt and told nicki to take him in her mouth.. Ben sank to his knees and undid the guys button and zip.. the cock that sprang free was massive, he saw the glint in sams eye as he started to suck on the guy.. she kissed the driver while his hands explored her all over, ben saw 2 fingers enter his girlfriend as he got a mouth full of cum.. sam pulled ben up to his feet and kissed him as her tong explored his mouth... Mmmm good girl Samantha said.. you swallowed him all, ben was still trying to come to terms on how he looked in his compact mirror while trying to fix his lipstick as as they stumbled into the first of many clubs...

Sitting in a corner booth.. she told him.. I love you ben and i want to spend my life with you as we are now.. but you must understand that as a woman i need a man.. a real man.. I need to be taken.. .. taken hard.. fast and deep.. you saw how i enjoyed the size and the feel of the new toys.. and you understand your not as big or last as long as they do... Tonight i want us to find a man between us.. or one each she said with a giggle... look at their crotches.. who do you think could give the girl you love the best night of her life.. maybe i should mingle, grind against some guys dancing.. start feeling packages.. that's what girls do hunny..  Go the bar and get us 2 drinks, maybe you will attract some guys, if they ask if your alone say no and point to me.. sure enough.. 2 guys offer to buy me a drink.. almost fighting over me.. then they realize im with Samantha..and they both follow me back to the table.... Its not long before sams hand is under the table and shes kissing this total stranger.. the guy next to me held my hand and kissed me,  do be shy he whispered.. your so pretty.. as he placed my hand on his crotch.. my hand moved swiftly and instinctively to this mans belt.. he beat me to it.. my hand moved to his zip.. he beat me to that to.. as i was kissing him and stoking his cock under the table.. samantha looked out the corner of her eye and knocked my handbag off the table.. as i knelt to get it i slipped down onto the floor and she pushed her heal under my skirt.. actually penetrated me with her stiletto as she pushed me towards his crotch.. before i new it i was sucking a guys dick.. while she fucked me with her six inch shoe heal,,, he tasted so fucking amazing.. i kept squeezing for more pre-cum, i never thought someone else cum could taste so amazing.. he reached down between my legs.. before i had chance to stop him he felt my cage, he looked over at samantha and laughed.. then started sucking on one of her tits while his friend was kissing her and fucking her with his fingers.. right now i new when we left this place.. she was gona get fucked by 2 guys....

Back home i ended up on the couch for almost 3 hours.. before she called me upstairs...  when i enter our (i mean HER bedroom) she was laying on the bed looking so lost and used.. her skin glistened in the lamp light, she spread her cunt lips and pointed.. both guys lay either side of her and laughed as i started to clean both of them from her.. one guy got behind me and put a hand on my hip and my shoulder... well shes no sam he said.. but shes really cute.. may i he said...?  Shes a virgin samantha said.. so you'll have to be gentle.. at least at first she giggled...

Both guys tag teamed ben for 3 hours, while his face was pushed between her legs...  See why i like real cock she said... she said i love you Nicki.. more than ben.. but as you can see and feel.mm baby.... A girl needs a hard cock.. a rough man.. a strong man.. ben bit his bottom lip as cum oozed from his locked up sissy clit while he could taste all their cum on sams clity lips....

Back at work and bens anniversary.... She arrived with lunch.. she only had a shopping bag.. she made ben strip down to his underwear.. which was stockings.. knickers and a bra,, she sat the bag on the table and then sat her self on the edge and opened her legs.. clean me she said...Enjoy your lunch... ben knelt before her and began to lick her.. she tasted different today... he looked up at her and she just called him a good girl and pulled him deeper into her pussy... Just then the door opened.. ben panicked as he saw his boss standing their.. Its OK Nicola sam said.. as she moaned each word she spoke...  that's right baby.. samantha said,, guess whose cum your eating...  sam pushed ben away from her clit and reached around handing him the bag.. your clothes she said... he looked inside and it was a white blouse with a very fem looking tie and skirt, heels, handbag  and jacket.. your now my personal assistant bens boss said.. welcome to the 28th floor Nicola... i like coffee at 10, and a blow job at 10 past.... he laughed.. but ben later found out.. day in.. day out.. he was very serious...
Samantha hugged ben and said "make me proud my love" and left him/her with him....  ben got dressed and it wasn't long before he was bent over the desk...he reached around and teased his lips with pre-cum on his fingertip for a while as bens hips made his sissy snatch search for his bosses cock.. suddenly he entered ben.. now truly a Nicola and held her shoulders pulling her back onto him deeper and harder.. Samantha smiled at ben as she closed the door behind her.. bn didn't know where she was going, i guess he see her at home.. until then.. he had no choice but to take the boss deep inside him until he was done....

24 hours later...
Ring Ring.. Hello this is Nicola how may i direct your call... its the bosses wife,, you could spill the beans right now.. but instead.. your jealous because tonight he'll be in bed with her and not you...
your goal in life now is to win him over.. so you can move in with him and be his girlfriend....

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