Here is a little back ground to bring you up to date Ricky and Karen had been together since collage and because he had a 4½ inch dick she refused to take his virginity away and instead took lovers and cuckolded him on his 19th birthday she locked him in chastity and he watched in person her fuck another man with a bigger cock and eat his cum from her pussy. In the early days Karen allowed Ricky out of chastity once a month to wank and complete a throughly strict hygiene cleaning she would allow him to cum but only under her supervision and then he has to swallow the spilt cum.
After collage Ricky got a very good job enough to keep him and Karen happy over the years he had several promotions but in their personal lives he was a caged cuckold only using his mouth and toys on her to please her she made it known his pleasure didn't matter to her, she also had children with other men which Ricky raised as his own know one knew he was a virgin cuckold even on their wedding night she kept him caged as he watched her lovers consummate his marriage filling his wife with cum for him to clean up.
Ricky had never had sex or felt a woman's mouth on his cock and started to wonder what it felt like when he told Karen she restricted his release to twice a year. RICKY loved Karen but things were not right so he sat her down to talk and she said she understood and would make it up to him on his 35th birthday which she made plans for.

Now for how a 35 year old virgin lost his virginity Karen had planned everything she explained if he didn't obey her and do as he was told her gift of him loosing his virginity would not happen and without question or hesitation he agreed so she sent the children to Ricky's parents for the night and explained she needed him to shave all his body and facial hair off to lose his virginity which he did as he entered the bedroom Karen was already dressed and on the bed was panties stockings padded bra all matching a cocktail dress heels and wig she explained that he was going to be a woman to lose his virginity because with a cock as small as his he wasn't a real man who deserved to have sex like one as she giggled he lowered his head and said of course my love she said tonight call me Mistress K or Miss K he agreed and got dressed she then put make up on him and he looked like a very convincing woman she then took snap shots on her phone.
She led him downstairs and outside Ricky complained that people would see she told him of course they were going out to celebrate his birthday with a meal and a drink but she would be addressing him as Rita infront of people and as long as he kept quiet no one would know he was a man he reluctantly got in the car and drove into town they parked up and went into a restaurant where they were shown a table he was very nervous and scared but no one said anything and treated him as just another woman this made him feel better after their meal they went into the bar when Ricky seen his Co workers Hunter and Harvey he told his wife she just giggled and said its OK they won't recognise you your Rita remember and led him to the bar and ordered 2 glasses of wine they sat and chatted for a while and he asked if he was still going to loose his virginity she said of course but I thought I'd make this night special and more memorable for you by doing things differently he agreed it was different.
Harvey and Hunter walked over to them Ricky was scared they then spoke to Karen asking where Ricky was and who was the beauty she was with Karen introduced Rita as her best friend and said Ricky was out having fun for his birthday she said she had given him a free pass so if he pulled he could have sex without feeling guilty the guys laughed saying she was too kind the wine flowed and the flirting started Harvey kissed Karen and she responded he then slid his hand up her thigh and she didn't stop him next he was fingering her at the table and took her panties off Hunter took guidance from them then leaned in to kiss Rita Karen looked at her and said go on enjoy yourself we won't tell anyone in fact I insist then as Hunter kissed her Ricky Rita kissed him back Hunter slide his hand under her dress to find a chastity cage pulling his hand out sharply said oh my God Rita your Ricky and everyone laughed hysterical as Ricky felt humiliated Karen motioned for the bill and they Got a taxi back home.
Both couples kissed passionately in the taxi then they got home Karen sat on her favourite chair looked straight into Ricky's face and said its time for you to lose your virginity my love she then looked at both men and said turn my husband into the fucking slut she's dressed as and just like my first time Rita needs to feel what it's like to be used and ruined and filled with cum both men laughed the shocked look on Ricky's face was priceless and when both men started to man handle him stripping him to his underwear he was trying to refuse but they just kept on groaning him then he was pushed to his knees andcwas greeted by 2 massive 8 inch plus cocks in his face forcing him to suck both in turn gagging on the cocks Karen encourage Ricky to make the men happy and she encouraged the guys to abuse the slut he was bend over and felt something pushing into his arse he started to scream with pain Harvey didn't let up he just rammed it in hard and xxxxxxxxxx the monster inside Ricky's male pussy he looked over at Karen and said God this bitch is so fucking tight you wasn't joking about her being a virgin then Hunter shoved his cock back in his mouth and Rita got her first spit roast after a while they swapped positioned and now he had taken 2 cocks in his arse Karen kept encouraging the guys to use her a sissy husband like a whore after a while Ricky stopped screaming and started moaning then he was begging them not to stop and actually wanting them inside him soon he forgot who he was sucking and who was fucking him and heard I'm going to cum yes oh yes not knowing why he screamed out yes yes fuck me fill me with you thick warm cum I beg you oh God yes give it me and a load of warm cum shot deep in his arse one after another after another he then felt the cock removed he felt empty and beg for more cock this time he hardly felt the cock enter him but it wasn't painful it felt great he then opened his mouth took the softening drippingbcock in his mouth and tucked it clean Karen got up holding her phone and got closer to video Ricky face and arse dripping cum the guys kissed Karen and left saying thanks that was great next time you can join us.
Ricky lay on the sofa exhausted as Karen said Happy birthday Ricky you just lost your anal virginity to 2 men did you really think your cock was getting uncaged she then cupped his balls and he shot his cum right into her hand still caged she xxxxxxxxxx him to lick it clean as she said you don't need a woman's pussy or mouth when you cum from getting fucked in the arse by real men your now an official sissy cuckold cock whore and if you even think of yourself any differently I have photos of the entire night and videos because my sister has been with us the whole time recording your birthday celebrations even in the restaurant and bar and with that Sally her sister walked into the room saying I have copies of everything we own you now slut and left..


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