What Was Your First Time with a Trans Woman Like?

Whether you’re reminiscing over happy or awkward memories, or dreaming of bliss to come, you might be curious about what first-time transgender sex is like for other guys.

Trans-attracted men may have few opportunities to talk about their sexual experiences or sexual desires. What was it like for other men, the first time they made love to a transgender woman?

Well, since you asked.

“I wasn’t as nervous as I expected. With Kayla it felt natural. We went on quite a few dates before thinking about sex. I wanted to make sure my attraction was real and not just novelty, to be sure I didn’t use her. We parked on a secluded road after dinner and made out for a long time, then went back to her place. It was magical. I told her to show me the way, and the whole experience was so brand new that it felt like my actual first time.” – Pete, 41

“My first time with a transexual was pretty mechanical, because I hired a sex worker to show me the ropes. I felt like I wouldn’t know what to do and was a bit scared, and it seemed like that would help. It wasn’t electric fireworks, but she was generous in sharing her body with me so that I could experience love with a trans woman without feeling as nervous.” – Michael, 29

“Honestly, it was so embarrassing the first time. I thought I’d never recover! I didn’t know what to do with her penis, but I was so horny I exploded when she asked me to press mine against her breasts. So that was pretty much it. It’s improved a lot since then because I’m more experienced with different transgender bodies and always ask her what she needs or likes, and make sure the attention goes to her first.” – Dawson, 24

“The first time I made love to a transexual was also the first time a woman let me take her ass. So it was like the entry to heaven at last.” – Shane, 33

“I was a jerk and wish I could take it back. I didn’t know I was with a transgender woman, although I kind of did if that makes sense. I hadn’t come to terms with my attraction, but allowed myself to hook up with a woman I met online. I freaked out when she got undressed, but it was after she’d already gotten me off. It was totally selfish. I wish I could take it back—if you’re reading this L, please know I grew up, and I’m sorry. I have an amazing transgender girlfriend now, but I wish I didn’t treat the first ones badly.” – Desmond, 27

“The first time I was afraid of touching her. I wanted to so bad but I felt like high school, even though I was divorced and already turned gray! She was sucking me and I wanted to rip her clothes off, but I was paralyzed. Finally she took my hand and moved it across her chest and arms, then her waist and thighs and back, sweeping herself with my hand. She put it against her cock and said that even though it didn’t get hard because of the hormones, it felt good to touch. So I played with it. It was amazing and sensual.” – Rick, 56

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