Born A Sissy I Was A Sissy And Became The Sissy Of An Older Man

I was a sissy sort of and I had no experience whatever with any kind of sex. I worked nights at a hotel, as a nigh auditor. The team were three, an older man and an older woman, and me the one that had to do all the reconciliations. Out front was the front desk, with the two front desk clerks. In the kitchens were the kitchen staff cleaning and prepping, and the night bellman, and the night watchman.

In the bar, there was a bartender named Alfonso. He was some kind of Mexican, but not Mexican. Don't call him a Mexican. He was after me and followed me into the men's room where he kissed me, grabbed my dick in his hand and made me get on my knees and suck his dick for him. He kissed me after I gave him the blowjob and he told me he wanted me to go home with him when I got off in the morning.

I spent the night trying to do my job, but I was so nervous I made mistake after mistake after mistake. He sat in the lobby watching me. When I ran the Room and Tax rate he stood at the counter with me. He made eyes at me, puckered up and made kiss noises. He held his index finger on his thumb, to make a circle, and ran his other index in and out, in and out, blowing kisses at me.

When we got off, and punched out which was in the back of the kitchen he waited for me to get in his car and go home with him. At his apartment, he got out of his clothes until he was standing only in his underwear. He pushed me on the bed and kissed me, and took my shoes and socks off, and my pants and underwear, sucked my dick, and kissed me again and again. He took off his underwear standing over me with only his hard dick facing me. He told me to turn over, and he stuck his finger in my ass with some greasy slippery something, before getting on me and pumping his dick in me.

I stayed with him all morning, we feel asleep and showered when we woke up. He had sex with me again in the kitchen leaning on the table. He sat me down on a chair and I had to suck his dick afterwards. I got kissed over and over. He told me I was his toy boy.

I knew I was a sissy, I suppose I always knew. I was his toy boy, I went home with him in the mornings. I gave him blowjobs during the evening in the basement men's room. I got in trouble because he bragged to the Night Manager, who unknown to me was also a gay man. I had to confess to him, the Night Manager, that I was having sex with Alfonso. He gave me hard talking to, I had to be careful. It's not something you can or want to control, but letting a man like Alfonso treat me like that was unacceptable.

But it continued, until Alfonso got another job and I was lonely. I went home with the Night Manager and he helped me get over him. He kissed me slowly, and he was gentle when he held my dick in his hand, and held me gently when I gave him a blowjob. He insisted on showering before having sex, and always used a lot of lubricants and a condom. He knew to many friends of his who had AIDS. I suppose I was a sissy with Daddy issues, because I was really attached to him.

I went onto college at his request and insistence. I got a degree in Finance and went to work for a bank in the accounting department. I worked there for thirty years, always a sissy. I learned from the Night Manager to always have my fingernails manicured. When he died, he left me everything, his furniture and record collection, his wall art and a small life policy.

Comments

Anonymous

by Anonymous on Jun 30, 2025 at 8:24 AM

Owning a sissy would be so awesome. Someone to hold and love. A sweet young thing to fawn over.

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