Crossdressing & Pegging Fantasies: 4 Kinky Confessions

At Kink Lovers, we love Kinky Confessions from our readers. We receive many confessions that revolve around femdoms, crossdressing, and pegging fantasies. Enjoy these four stories!

Crossdressing and Pegging Confessions

Femdoms – The More the Merrier

“I’m a straight single white male who loves to wear lingerie and makeup. I have an old fantasy about getting caught dressing up. Could be by a girlfriend, but what I dream about the most is being caught by any woman and being feminized. I am alone, dressing in lingerie, when I am caught by a dominant woman.

She teases and humiliates me a little, then says that she is gonna really make me a girl. She makes me into her personal femboy, sissy, bitch, servant, girl toy. She dresses me in sexy lingerie, silky stockings, makeup, and makes me wear thigh high boots (which I LOVE).

Then she ties me up and blindfolds me, and uses my face and tongue. She then shares me with her friends, taking turns facesitting, using strap-ons in my mouth and ass. I have no idea who is there, but I obey all their wishes. I am taken shopping, and they choose what I am to wear.

Now, mind you, I am NOT gay. But I am forced to learn how to suck a cock like a good little bitch. By the way, everyone is clean and smooth shaved, as I just LOVE to lick smooth, hot, wet, pussies, lick nipples, and rim asses while being pegged.”

Read: Forced Feminization and Sissification Kinks


Satisfying All Sexual Sides

“I live rent free in a two-story building owned by my boss. I’m on-call technically, but I get the good end of that deal. The floor I live on has three apartments, but I am the only tenant and will be until we remodel everything. This sweet setup makes my current sex life a thrill!

I developed a LOVE for crossdressing over the past two years. It’s so much fun, and I sometimes feel so sexy in my feminine clothes. It adds to my already amazing sexuality and is so perfect for me. I look good too, lol, both as a masculine male and as a more feminine male.

I have loved cock and pussy all my life but love cock so much more now. Pussy is nice, but women’s sexy feet are all I need. With men, I need cock and sex. I live as regular me in one apartment, as a sexy feminine man named Lucille in another, and as a sexy and femme character I call Ami in the third. I have three dildos of different sizes and styles and just love this aspect of my life right now.”

Read: 5 Sexy Dildos to Try with Your Kinky Lovers


Three Women with Strap-Ons

“The first time my wife surprised me with a new strap-on, we were on ecstasy. As she was leaving our bedroom, she pulled up the hem of her black silk and lace nightie, giving me a quick glimpse of her new blue cock. She said, ‘When you’re done showering, I have another surprise waiting for you on the bed! It will make tonight so much more fun! Trust me, you’re gonna love it!’

Quickly, I finished my shower and toweled off. As soon as I flipped the lights on I saw my surprise! Pulling on the big pink bow, I opened the box, and was a little shocked by what I saw. Because my head was full of thoughts of all the fun awaiting me, I awkwardly but quickly put on the stockings, garter belt, g-string panties, cropped corset and padded-cup bra. To finish off my outfit, I put on a pair of spiked-heel lingerie slippers, complete with faux pink fur.

What I found in the living room made my head spin, my face turn bright red, and my dick poke straight out. There on the sofa was my wife and her two best girlfriends. Except for the color, each was wearing the same silk & lace outfit as my wife, with each noticeably tenting at the crotch. Just like me, in my panties, except theirs seemed quite a bit larger. In the end my wife was 100% right, my new outfit did make the night more fun and exciting.”

Read: Femdom Pegging: 15 Ways to Supercharge Strap-on Sex


Open Marriage BDSM Exploration

“Several years ago my wife and I started experimenting with domination and specifically strap-on play. Over the years we progressed further and further into this domination play and larger and larger strap-ons until both my wife and I were able to orgasm from strap-on domination—me from penetration and my wife from the feeling of power and domination.

This led to some changes in our sex life. She didn’t want exclusive sex anymore, so we started swinging as well. She enjoyed being a power top and sexually empowered, so she loved multiple lovers at the same time. And although she didn’t mind me having sex with other women in front of her, the sexual arousal for me was not as great as seeing her with multiple men or me being used with a strap-on.

Read: Kinky Sex Ideas: 40 Ways to Have Kinkier Sex

So more and more, we asked women to take me with strap-ons, rather than engage in vaginal sex. This led to another fantasy from my wife and that was to have me dress up as a woman during these sessions with a latex face mask and latex boobs, like a human doll.

The first few times were exciting. She would have sex with guys, and as a woman I was being used by their wives wearing strap-ons. We both were being gangbanged, but one night things went a different direction. My wife said she had an extra surprise… instead of just couples, she invited six extra men!”

Read: Femdom Ideas: 38 Ways to Dominate Him

Do you fantasize about crossdressing or being pegged by a dominant woman? Do tell!

Kinky Confessions is a special feature at Kink Lovers. We want readers to share their tantalizing tales of kink, fetish, and fantasy. SUBMIT YOUR STORY HERE! These stories don’t have to be real, they can be fiction that you’d like turned into reality.

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