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Gay Male / 24

Unexpected Age Gap

I started to have sex with a 66 year old I met on Grindr. Being a bottom I definitely attracted older tops. They obviously love a younger tight bottom.

What I thought would be a one time hookup turned into a regular fwb. We had sex a few times a week. This went on for 5 months

He has the perfect size dick for me and he’s grooms well.

Then 2 months ago after finally letting him go bare while giving him some hot birthday sex he asked about dating. I figured why not. So we made it official

Telling my parents was the awkward part but both didn’t care. They liked him. What’s funny is secretly one day when I was with my mom she asked how the sex was and how big his dick is lol. My mom is a very sexual person.

Sex is still strong two months into dating and the great thing is he always cums in me now. No more condoms.

5
# 79013 - by Nathan / May 15, 2025
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Comments

Anonymous

by Anonymous on May 15, 2025 at 8:59 AM

I absolutely love bottoming and hate condoms. For this reason, I have three regulars and that’s all I sleep with.

(4)  (0)
Anonymous

by Anonymous on May 15, 2025 at 10:39 AM

I’ve always had better experiences with older men. My situation is a bit different though. I have a major fetish for wearing stockings or pantyhose. I’m your basic 20’s smooth twink. I’m submissive but the men I see are looking for me to submit to them by kissing me, groping me, tickling me, stripping me down to my pantyhose or stockings and then rimming & sucking me till I give them my cum. Some of them also want head. Some of them want to shoot their cum all over me. I haven’t taken it up the ass yet. Just younger and fingered on occasion. Most of them are married, divorced or widowers. All of them want to be called daddy and have me prance around in my nylons and whatever else they like to see me in before I must submit.

(5)  (0)
Anonymous

by Anonymous on May 15, 2025 at 4:44 PM

Barely 18 I was weirded out having accepted a date with an old guy in his 60's. I'd only made out with other boy's because I felt safe with them because I knew them forever so we never had to practice "safe sex" all of it was safe. Now an "adult" though I don't feel any different men of all ages get that twinkle in their eyes when I say that I'm eighteen. Even mom's and dad's friends from their work have suddenly become more interested in me after my eighteenth birthday. I've submitted more times than I probably should have kinda making me kinda slutty for sure but they're all so different than the boy's my age. I look good in cute panties and that's so exciting for them and me but this old guy Jim loves me because I get so excited like, squealing n wiggling as he tears at my panty wrapped boipussy. It's better than ever and I want to be with him even though he's old enough to be my grandpa???

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Anonymous

by Anonymous on May 16, 2025 at 5:07 AM

To anon1 and the confessor: limiting sex to specific partners can't protect you from HIV and STIs, because we can never control what our partners do. PrEP, doxy-pep, vaccinations (for Hep A, Hep B, HPV, Mpox), and regular testing and treatment, will protect you.

To the confessor, beautiful love story! I'm glad your parents are accepting.

Do you suspect your mom listens in when you and your boyfriend stay over at your parents' place for the holidays?

Do you ever worry that if you get pregnant, your child might have only one dad by the time he graduates from high school?

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athensgold124

by athensgold124 on May 17, 2025 at 2:20 PM

Its nice that you found someone that you care about and he cares about you. Do you have common interests also? He is my age and we tend to be a bit old-fashioned, well anyway best wishes and hope your relationship endures for many years.

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