The Mistress and the only time I had gay sex Sex Stories Cool – Y2-Stories

In NYC for a few months, I went to a mistress who turned my world around. But never did it again

When I was 20 I was in New York for several months for work. I wanted to try to see what it would be like with a woman in total charge. I answered ads for domme women and selected Kara. She was tall, about 5ft. 9in, beautiful face, really tight body, and DD cup boobs that she made me nurse on while in our first interview. She didn’t just get paid to domme, she was in it fully as a lifestyle, and wanted to know everything and all boundaries before getting started. My big thing was that I wanted to be able to see my mistress tits, pussy and ass. Other than that I had very few limits i guess.

Soon I was being dressed like a woman, cleaning the apartment like a woman, even changing her pads and tampons. During her period I had to wear a tampon in my butt and a pad in my panties. She had me wearing panties all the time, sometimes with garter and stockings. Once she went out with me in her normal street clothes and me in a thin tee shirt, really tight pants that showed my panty lines and a bra that showed through the thin tee. We went to a movie and dinner, all with people looking at me. It was her way of taking my humiliation into everyday life. That night she had me stay the night with her, I ate her as I did always, if she was satisfied she’d let me jack off, but always had to eat my own cum. On a good day I could jack off on her ass and lick it off. While staying that first night, me wearing lingerie and her wearing gym shorts and nothing else. She started massaging my back and moved to my ass. She was using a lotion and it felt good for a change. Then she got on top of my back and reached down, pulling her shorts down and I felt something at my asshole. She had a strapon cock that even though soft so it didn’t show in her shorts it was hard enough to penetrate me. It wasn’t too large and she fucked me 3 times each time 30 to 40 minutes. In the morning when she fucked me again it was easy this time. Then I had to take off the strapon and wash it thoroughly and then eat her to get her morning started.

Gradually it got to be bigger and bigger strapons and dildos. Part of my regular punishment was bending over her lap and taking paddlings, from her or other mistresses some just regular woman who got a laugh out of it, then they would watch her fuck me with bigger and bigger dildoes or strapons. Finally she had to two biggest. “If you can take both of these I and mistress charly have a surprise for you, one you’ll really like. ” I took them both for 15 minutes each. Then Mistress Charly went out and came back in two minutes with a naked man. Not just a naked man, a naked man with a 10 inch cock that was as thick as a damn can of pringles. It was the biggest thing I’d ever seen. My mistress made me get on my knees and ask him if I could honor his cock by sucking it for him. He agreed. In front of these two woman and this strange man I was sucking cock. I’d never had anything to do with another guy before. I sucked and he came filling my mouth, my mistress told me I’d better swallow every drop and I did. Quite frankly I hated the taste.

Then she had me dress and do my makeup, and come out as a girl in sexy undies and I ate both mistresses, by then the man was recouped. My mistress told me he was tested and disease free, so I had no worry. They watched us get into bed and I sucked him hard at their orders, then my mistress lubed me and his cock, then they watched me get fucked. After I had his sperm in my ass and my ass gaping open, they both left us. He had me for the entire night and the next morning. After getting fucked again in the morning I made him breakfast still in my lingerie. My mistress came in, I made her breakfast, and the man left, just as naked as he came in the night before.

“Did you take care of your husbands needs last night?” she asked
“Yes Mistress I did, four times” I said
“Good, one of these days you’ll make someone a good little wife”

I never went back to her, and in a couple of weeks I was done with my work and went back home. I started dating a girl I knew in high school, got her pregnant and we got married and have been ever since. I’ve only had m2m sex with one guy for one night in New York, and I never tell anyone. Looking back I guess the next morning with his fresh load deep inside me and cooking him breakfast, I felt really like a wife. I look at mine in the morning at the breakfast table and know that I am very familiar with what she’s feeling.