Halloween sissy chapter 1
29-Oct-24 03:34
Richard has been crossdressing in private for years no one knew his secret not even his late wife he was embarrassed at the thought of anyone seeing him dressed as a woman and if they ever found out he fantasies about being caught used and dominated he thought would ruin his life and it was just a fantasy to wank too not hurting anyone.
Then a woman he worked with one day asked him out on a date knowing Richard was shy she took the lead and they started dating the sex between them was good but not great but Lisa thought there was always something different like he was holding some secret he couldn't share over the next few months Lisa and Richard became more serious and they started to talk about the future but Lisa was sure Richard was hiding something.
Then one night after sex Richard went for a soak in the bath when his phone went off when she picked it up there was a notification from a group called crossdressing sissies she was curious and intrigued so decided to have a look that's when she found Richard profile as Reba the sissy she read his profile which said he liked the idea of being caught and xxxxxxxxxx to be a sissy then xxxxxxxxxx to wear a chastity cage and serve women or men as a sex slave totally under their control she also found photos that he had posted of him dressed as a woman a French maid a nurse and a school girl also photos of him sucking dildos and fucking himself and wanking Lisa was gobsmacked shocked and unsure what to do she closed his profile and put his one back confused and shocked Richard came to the room and they kissed but she made an excuse to leave.
That night Lisa phoned her best friend Kayra and confessed everything to her they agreed to meet up and chat about what she should do next that's when they came up with a plan to use Richard kink to their benefit Halloween was in a few weeks it was the perfect time, at work everything was normal until a message came from management say everyone must dress up for the Halloween party but men had to dress as female people and women as men and a reward of £100 to those who did it and the best cos would get £1000 and a full weeks paid leave it was the talk for weeks Lisa told Richard she was dressing up as neo from the matrix and she told him he should go as a naughty school girl or a French maid as no one would expect that from him Richard shy and embarrassed said no he wasn't going to gosh both her and Kayra decided to convince him it would be OK and they wouldn't leave him because they understood how he felt after weeks of convincing and nagging Richard agreed to go as the French mail.
On the night of the party Lisa looked amazing as neo all in black PVC Kayra was dressed as cat woman when Richard came down stairs in his uniform complete with Stockings heels make up and wig the women were speechless as they approached the door to leave Richard became anxious and scared and didn't want to leave but after 30 minutes he calmed down and they left in a taxi.
Then a woman he worked with one day asked him out on a date knowing Richard was shy she took the lead and they started dating the sex between them was good but not great but Lisa thought there was always something different like he was holding some secret he couldn't share over the next few months Lisa and Richard became more serious and they started to talk about the future but Lisa was sure Richard was hiding something.
Then one night after sex Richard went for a soak in the bath when his phone went off when she picked it up there was a notification from a group called crossdressing sissies she was curious and intrigued so decided to have a look that's when she found Richard profile as Reba the sissy she read his profile which said he liked the idea of being caught and xxxxxxxxxx to be a sissy then xxxxxxxxxx to wear a chastity cage and serve women or men as a sex slave totally under their control she also found photos that he had posted of him dressed as a woman a French maid a nurse and a school girl also photos of him sucking dildos and fucking himself and wanking Lisa was gobsmacked shocked and unsure what to do she closed his profile and put his one back confused and shocked Richard came to the room and they kissed but she made an excuse to leave.
That night Lisa phoned her best friend Kayra and confessed everything to her they agreed to meet up and chat about what she should do next that's when they came up with a plan to use Richard kink to their benefit Halloween was in a few weeks it was the perfect time, at work everything was normal until a message came from management say everyone must dress up for the Halloween party but men had to dress as female people and women as men and a reward of £100 to those who did it and the best cos would get £1000 and a full weeks paid leave it was the talk for weeks Lisa told Richard she was dressing up as neo from the matrix and she told him he should go as a naughty school girl or a French maid as no one would expect that from him Richard shy and embarrassed said no he wasn't going to gosh both her and Kayra decided to convince him it would be OK and they wouldn't leave him because they understood how he felt after weeks of convincing and nagging Richard agreed to go as the French mail.
On the night of the party Lisa looked amazing as neo all in black PVC Kayra was dressed as cat woman when Richard came down stairs in his uniform complete with Stockings heels make up and wig the women were speechless as they approached the door to leave Richard became anxious and scared and didn't want to leave but after 30 minutes he calmed down and they left in a taxi.
If this thread breaks our
rules please