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Crossdressing lifestyle is ideal

702 words | 3 | 4.56 | 👁️
Richard McKinnon

I love being a crossdressing sissy. Call me a faggot or a queer if you want, I get all the sex I want whenever I want it.

I am only 20 and I have a good paying job, and I live on my own, but I have a big secret. I am a sissy crossdresser. Much of my extra money goes to purchase wigs, shoes, fancy underwear, and women's clothing. If you saw me out in public I would look like any slender young man. But in private, I am a girl named Cheryl, and I have a propensity for doing sexual things that would shock most people. I always knew that I had a high sex drive....wanted to spend every waking moment masturbating. It is still quite common for me to take a bathroom break on the job and watch some crossdressing porn on my cellphone while I masturbate in the restroom stall. I get especially turned on watching older, more mature crossdressers as they suck and fuck and jack each other off while dressed in women's undies. I love the way that old-time stockings look on a man, and even more so I love the way that they feel on my long legs. I have searched the internet looking for vintage women's underwear to purchase, and I have accumulated quite a collection of long-line bras and panty girdles and garter belts. Most of my lovers are older men who share my passion for crossdressing. Some of them even crossdress as a lifestyle...something that I would never be able to pull off. I don't ever try to go out in public as a female, although I am often wearing panties under my pants. In the winter time I sometimes have on pantyhose. My favorite sexual partner is a married man named Gerald. He is British, and like me he loves to crossdress. He also loves to take me over his lap and spank me. Gerald makes a very attractive woman when he has on a wig and makeup, but between his legs is the most beautiful 8 inch cock you can imagine. I love being on my knees and sucking his cock as I lightly squeeze his balls. I can always tell he is getting ready to cum in my mouth when his hips start bucking. I love taking Gerald's hard penis in my boi-pussy. That's what he calls my ass. He bends me over the couch and just humps me until my legs start trembling and my own hard dick is spurting cum halfway across the room. Another one of my lovers is a younger man named Jeffrey. He is a little plumb, and he loves to wear girdles with stockings. Seeing him try to walk in high heels is pretty hilarious, but there is nothing funny about the things that he does to my body. Jeffrey loves to suck my nipples, and that always makes my penis throb with excitement. He loves to sit on the couch and have me straddle him with my knees on either side of his thighs. I can bounce up and down on his cock while he has easy access to my nipples. I love it when he cums inside me. The feel of his hot juice spurting in my boi-pussy almost always makes me spurt too. One of my best friends is a transexual guy named Bobby. Bobby was born a female and still has a vagina, but he has had his breasts removed and he lives as a man. He even has a beard and moustache. Bobby and I have been friends for years, and he comes over to see me when he needs some hard dick. Bobby dates women. He only dates women, and he loves to eat pussy. But once in a while, he likes to be fucked with a real prick, and I try to accommodate him. Men are really my thing and I love hard cocks fucking me, but on occasion I can pound Bobby's pussy until he cums, and he really appreciates that I am willing to do that for him. The chances of me getting married and having children is non-existent. It will never happen. But I am actually quite happy with the lifestyle that I have chosen. I get lots of sex from a variety of partners, and life is very good.

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Comments (3)

  • Longjon: I love dressing up in old fashioned lingerie and having a big cock cumming up my bum and have it dripping down over my suspenders and stockings

    Reply↴ • uid:1e0kgkfx3cpc
  • B.R.I.T.N.E.Y.: OMG Cheryl !!! I have a few vintage girdles and seamed nylon and silk stockings and garter belts to !!! I would love to wear them just for you if you would fuck me !!! I've never been screwed by a tranny before and you sound so hot and sexy !!! Britney

    Reply↴ • uid:1cr5cbcb27n4
    • Cheryl: I love dressing up in my ladies' undies and having passionate sex. Wearing a girdle and stockings makes my clit get so hard. I love masturbating in front of the mirror as I turn and admire my feminine curves.

      • uid:1cqkkcl18y0g