I Finally Had Anal Sex And It Was Incredible

So I have a medical condition preventing me from having vaginal sex. I can't even get my pinky inside without serious pain. So for years my sex life was extremely minimal. Strictly outer course and oral or vibrators to the clit.

And for years I was... well not ok with it but I accepted my limits. And it's not like a vibrator or oral induced orgasm is bad. Well I met my boyfriend 2 years ago. And he's frankly kinder than I can describe. A very traditional manly man kinda guy but so sweet and caring. And he's obviously been disappointed he couldn't have real sex with me and that children was basically out of the picture but he's never pressured me or made me feel bad about it. And he's been fairly happy with our sex life as have I. Lots of oral and toys and hand stuff. At least once a day. Thank God I can deep throat lol.

But finally, I built up the courage to do something I've wanted to do for years. Anal sex. I was scared. It would hurt or be gross or that it just wouldn't ever feel good. But lately I've been watching a lot of anal porn. Its just easier to relate to something that's actually medically possible for me to do ya know?

And I finally did it. Got an enema kit and cleaned myself. Got a couple little plugs and secretly trained myself to be able to spread a bit and then got some sexy backless panties for my bf and surprised him.

I've never felt him so hard, and he was so gentle, and he started with his mouth which I was super grossed out by until his tongue hit my little back hole and then I couldn't think of anything but to hump back against him.

He made me cum twice by rubbing my clit while he picked and kissed back there which... OMFG such a weird kind of orgasm feeling but soooooo good.

Then was sex time. He's probably only a bit above average in length but the thickness is impressive and we had to go slow. It was really intense and I could tell he wanted to really fuck me but he went slow for me. At first. Once I adjusted and asked him to move faster he just kind of took over.

It was the best 20-30 minutes of my life. As good as it felt I think the excitement and emotional situation was the biggest reason I came so much. Like 4 or 5 times before he came. But god it felt incredible and I never wanted it to end. I was crying, cumming and telling him how much I loved him and his cock. How much I loved anal and how I wanted this every day.

I finally felt like a WOMAN! I was being FUCKED! FINALLY! My hands hands on my hips, pulling himself into me, grunting as he pounded me. And it kinda hurt but it felt so fucking good and RIGHT. When he finally came I locked my legs behind him and held him inside me.

I kissed him and rocked my hips up and down his cock as he came inside me and I was just a crying happy mess. He went to pull out but I begged him to stay inside because I was so emotional.

He stayed there and eventually got hard again and fucked me again. Just as good as the first time but he lasted a bit longer.

I know I have to be careful so I don't get super loose or any medical issues from too much anal but I'm doing what I can. That doesn't stop me from using a dildo back there daily now and having him inside me most days and his mouth back there every day. I love it. I love FINALLY feeling like a real woman and FINALLY being able to have actual real sex. Like I can finally give my man the pleasure and sex he deserves and I just love this.

I'm just so excited and don't have anyone to share with so I came here to share. I'm just so fucking happy!!!

Comments

Anonymous

by Anonymous on Aug 29, 2025 at 8:48 PM

There's a lot to unpack here.

I'm glad you and your boyfriend enjoyed anal.

That getting fucked in the ass made you feel like a woman is odd. You don't need a man to validate your womanhood. You don't need a man's penis in your ass to validate your womanhood. It just sounds as if you got carried away in the moment.

Does your medical condition prevent you from conceiving? From carrying a pregnancy? Have you considered having your eggs harvested, fertilized in vitro, and then engaging a surrogate to carry your pregnancy? If you're able to carry a pregnancy, but you can't have PIV sex, have you considered just letting your boyfriend shoot his semen into your pussy? It's highly erotic and potentially effective for insemination. You could also try a turkey baster, the method preferred by lesbians.

Enjoy, and good luck!

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Anonymous

by Anonymous on Aug 30, 2025 at 8:00 AM

I felt like a true woman the first time I had anal sex also, unfortunately my hard cock gave me away.

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Anonymous

by Anonymous on Aug 30, 2025 at 12:24 PM

^ That at least makes sense. For a man, taking cock is a feminine activity, so it would be a new feeling for you.

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