I lay back on the bed where two men had fucked me that night and pondered how I had got into this position. Despite myself my cock was rock hard in its silk panties stained with my own cum.
3 weeks earlier I had told my wife we were broke and that my business was finished. She had been quite calm and had gone out of the house to think things over.
On her return she had some bags and had clearly been shopping but before I could say anything she looked at me and spoke,
“Do you love me?”
I nodded.
“Do you accept you have been at fault for our predicament?”
Again I nodded.
“Do you agree you need to fix it?”
I could only agree.
“ Do you admit that throughout our marriage you have been wearing my clothes like a sissy faggot?”
I looked aghast. How had she known I cross-dressed? I thought I had been so careful.
Shamefacedly I nodded.
“Well I’ve bought you some outfits and a wig. Tonight I will be setting up your website and you will earn money on your back!”
I started to protest.
“Look you can good money, your sissy secret will not be known to your friends and family and you can fulfil the fantasies you have emailed and chatted on the Internet about. Sexy pictures you send them by the way.”
I went upstairs and put on the clothes. Black thong, bra, suspenders and fully-fashioned stockings a tight red dress and black heels. Nicki had added a blonde wig and came in to look at my outfit. She sat me down and did my make up. I looked at myself in the mirror and was surprised how good I looked. Nicki then made me pose in various ways whilst taking pictures.
2 hours later she called me into the office to show me a website.
“You are now Tara a TV escort. You offer all services apart from pain. You can be bought for a night. I will keep all the money you earn, as you are clearly not to be trusted financially. Oh by the way your anal virginity went on auction. You should be proud we have £500 coming our way tonight.”
A new mobile phone rang. I heard Nicki telling someone that Tara was waiting and directions were given to our home.
I was scared but horny I had dreamed of being with a man for years and now in very unusual circumstances it was coming true.
The doorbell rang and I heard Nicki bringing someone upstairs. The door opened and in walked a guy in his early 60’s a little over weight and looking very horny.
He wasn’t the bronzed Adonis I had imagined fucking me but I was in no position to complain.
He pulled me towards him and started kissing me. His tongue invaded my mouth. He smelt of stale booze. His hands were all over my body. He squeezed my arse and slid his hand up my legs. Within minutes we were on the bed and he was tearing my dress off. He stopped to pull his trousers down exposing a 6 inch uncut chunky cock. He was hard already and pulled my thong aside. His fingers found my virgin hole and started to explore me. Initially I found this painful but son began to enjoy the sensation. As I pushed against his fingers I moaned and whispered.” Fuck me.”
He placed his cock head against me and over the next few minutes got himself fully in me. He was gentle and made sure he eased off when I struggled with the pain. Before long the exquisite sensation of being fucked filled my senses. Nicki had made it clear that the auction had been to bareback me and I didn’t care. My punter started to breathe heavily and then I felt him tense and then cum flood me. He collapsed on me and kissed me deeply. We cuddled for a few moments before he dressed and left the room.
I lay on the bed with cum oozing out of me. I held my hard cock and after 2 stokes came in my thong.
Nicki came in. I sat up on the edge of the bed. She hitched up her skirt and pulled aside he lace thong and pushed her wet hairy cunt on my face. I began to lick her.
“Well slut you made us some money and your already booked solid for the week. This could be lucrative. Tomorrow you have your first all night outcall. He wants you as a slutty school girl, so shopping tomorrow.”
Via: https://www.lushstories.com/stories/cross-dressing/becoming-an-escort