Help from the neighbour
23-Feb-26 21:38
Richard is a 50 years old widower he hasn't had sex or been with a woman in 5 years since his wife died he keeps himself to himself and only has a few friends and some acquaintances and has no interest in finding anyone new that was until his favourite kink got him into trouble you see Richard like to lock his 4inch cock in a chastity device dress up as a woman and use his late wifes dildo on his arse to have a dry orgasm then once he has a orgasm from anal he removes the cage and wanks to completion he has done this once a month since his late wife passed away she made him promise her he would only cum after being caged and dressed and fucked in the arse she made him swear to her on her death bed and has done it ever since now back to the story.
Richard was going through his monthly ritual when just as he was about to dry orgasm and he cramped up and fell off the bed this lead him to not being able to move as he was in pain his neighbour heard his screams and came running to his aid only when she entered his bedroom she was greeted by him fully dressed caged with the dildo still inside him she gasped loudly and asked if he was ok he told her he was fine but couldnt get up she helped him back on the bed and said Richard I must ask what were you trying to do he hung his head in shame and explained his promise to his wife his neighbour Trudy smiled and said she was proud that he had kept his promise but he couldnt be trusted to do it alone so she asked Richard if he would like her to help he hung his head again and said he didn't want to betray his wife she said its ok the offer was there for the future and she left
The next month Richard built up the courage to ask Trudy if she would help him she smiled and took him upstairs after around 2 hours he looked amazing and more feminine than ever his make up was perfect his dress was amazing but his erection stood out Trudy asked him to fetch the cage which he did after placing ice on his erection she put on his cage she looked at Richard and said I think you need a smaller cage he asked why she said to flatten the dress not thinking he agreed Trudy put the key in her purse and led Richard downstairs he asked what they were doing she said we going to get you a new cage come on I know just the place Richard refused to go saying no not as a woman he couldnt go out dressed as a woman Trudy said what would your wife say and pulled him by the arm the next thing Richard realise was he was in her car being driving into the city center.
Trudy pulled into a carpark and took Richard by the hand leading him into a private sex shop there was a young guy behind the counter Trudy didn't hesitate she looked the guy straight in the eyes and said we need a flat pussy shaped chastity cage with catheter and belt it's for my sissy neighbour here it's her first time out in public. Richard couldnt look around he was too embarrassed he felt so humiliated degraded why was Trudy doing this she then took him by the hand and led him to a back room where she lifted his dress and removed his panties the guy came in with 3 different devices she unlocked his larger cage and his erection stood out Trudy laughed causing Richard to go red with humiliation after trying different ones the settled on a flat pink pussy with catheter and belt all lockable once it was attached Tudy called the assistant back and told him Richard would be wearing it home she then also asked the assistant for strapon dildo and again he brought different ones when he asked who it was for she told his about Richards promise to his late wife the young guy then said oh if that's the case I have the perfect size cock for him Trudy was wow really Richard looked on a little shocked the guy the asked Richard to bend over and with Trudys help they held him on his knees the assistant pulled out his 7 inch semi hard cock and grabbed Richards head demanding he suck it Rihad no idea what to do he was scared frightened but his cock was straining against his new cage he took the cock in his mouth and started sucking it it grew another inch or so the guy then lubed up Richards arse and entered him from behind he took the cock easy but it felt strange with a real cock he couldnt relax but as the young assistant pushed all the way in and started fucking him Richard started to respond breathing heavy moaning groaning then begging more harder more faster it felt great to be fucked then in a few minutes Richard had his first dry orgasm normally he would stop now but Trudy instructed the guy keep going the Richard felt another and another soon he couldnt stop how good it felt the the guy fucking him let out a huge moan and screamed im cumming Richard didn't care Trudy encouraged him to fill the sissy arse and he cum load after load inside him Richards knees buckled and shook then he felt his own orgasm and he shot his load through the chastity caged he was wearing there was cum dripping everywhere The guy tidied himself up Trudy handed Richard His panties And told him put them on he did in seconds the were soaking wet the returned to the shop Trudy paid for the cage the assistant asked if they needed anything else to just pop in he's there everyday as Richard and Trudy walked back to the car Richard said how did you know I'd go through with it she turned and said because I know men and by the way I will be holding your chastity keys you don't need to take it off you just cum in your cage he turned and said yes Trudy she said call me Miss T because from now on just like your wife wanted your going to be a sissy cock loving slave Richard questioned her what she ment with that comment she turned and said before she died she asked me if I would take you on as a slave and abuse you I asked her why she said if he's still single in 5 years he needs to realise he's a sissy and will need someone to teach him how to be a woman If I wasn't dying my husband would be a full time sissy caged slave obeying my every comand if I cant do it I want you too Richard looked at his watch today's date was the 5 year anniversary of his wifes passing he just broke down crying saying yes Miss T of course anything you desire .
Richard was going through his monthly ritual when just as he was about to dry orgasm and he cramped up and fell off the bed this lead him to not being able to move as he was in pain his neighbour heard his screams and came running to his aid only when she entered his bedroom she was greeted by him fully dressed caged with the dildo still inside him she gasped loudly and asked if he was ok he told her he was fine but couldnt get up she helped him back on the bed and said Richard I must ask what were you trying to do he hung his head in shame and explained his promise to his wife his neighbour Trudy smiled and said she was proud that he had kept his promise but he couldnt be trusted to do it alone so she asked Richard if he would like her to help he hung his head again and said he didn't want to betray his wife she said its ok the offer was there for the future and she left
The next month Richard built up the courage to ask Trudy if she would help him she smiled and took him upstairs after around 2 hours he looked amazing and more feminine than ever his make up was perfect his dress was amazing but his erection stood out Trudy asked him to fetch the cage which he did after placing ice on his erection she put on his cage she looked at Richard and said I think you need a smaller cage he asked why she said to flatten the dress not thinking he agreed Trudy put the key in her purse and led Richard downstairs he asked what they were doing she said we going to get you a new cage come on I know just the place Richard refused to go saying no not as a woman he couldnt go out dressed as a woman Trudy said what would your wife say and pulled him by the arm the next thing Richard realise was he was in her car being driving into the city center.
Trudy pulled into a carpark and took Richard by the hand leading him into a private sex shop there was a young guy behind the counter Trudy didn't hesitate she looked the guy straight in the eyes and said we need a flat pussy shaped chastity cage with catheter and belt it's for my sissy neighbour here it's her first time out in public. Richard couldnt look around he was too embarrassed he felt so humiliated degraded why was Trudy doing this she then took him by the hand and led him to a back room where she lifted his dress and removed his panties the guy came in with 3 different devices she unlocked his larger cage and his erection stood out Trudy laughed causing Richard to go red with humiliation after trying different ones the settled on a flat pink pussy with catheter and belt all lockable once it was attached Tudy called the assistant back and told him Richard would be wearing it home she then also asked the assistant for strapon dildo and again he brought different ones when he asked who it was for she told his about Richards promise to his late wife the young guy then said oh if that's the case I have the perfect size cock for him Trudy was wow really Richard looked on a little shocked the guy the asked Richard to bend over and with Trudys help they held him on his knees the assistant pulled out his 7 inch semi hard cock and grabbed Richards head demanding he suck it Rihad no idea what to do he was scared frightened but his cock was straining against his new cage he took the cock in his mouth and started sucking it it grew another inch or so the guy then lubed up Richards arse and entered him from behind he took the cock easy but it felt strange with a real cock he couldnt relax but as the young assistant pushed all the way in and started fucking him Richard started to respond breathing heavy moaning groaning then begging more harder more faster it felt great to be fucked then in a few minutes Richard had his first dry orgasm normally he would stop now but Trudy instructed the guy keep going the Richard felt another and another soon he couldnt stop how good it felt the the guy fucking him let out a huge moan and screamed im cumming Richard didn't care Trudy encouraged him to fill the sissy arse and he cum load after load inside him Richards knees buckled and shook then he felt his own orgasm and he shot his load through the chastity caged he was wearing there was cum dripping everywhere The guy tidied himself up Trudy handed Richard His panties And told him put them on he did in seconds the were soaking wet the returned to the shop Trudy paid for the cage the assistant asked if they needed anything else to just pop in he's there everyday as Richard and Trudy walked back to the car Richard said how did you know I'd go through with it she turned and said because I know men and by the way I will be holding your chastity keys you don't need to take it off you just cum in your cage he turned and said yes Trudy she said call me Miss T because from now on just like your wife wanted your going to be a sissy cock loving slave Richard questioned her what she ment with that comment she turned and said before she died she asked me if I would take you on as a slave and abuse you I asked her why she said if he's still single in 5 years he needs to realise he's a sissy and will need someone to teach him how to be a woman If I wasn't dying my husband would be a full time sissy caged slave obeying my every comand if I cant do it I want you too Richard looked at his watch today's date was the 5 year anniversary of his wifes passing he just broke down crying saying yes Miss T of course anything you desire .
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