For the past few weeks I have been having a torrid affair with the 24 year old crossdressing son of one of my closest friends.

Comments

Anonymous

by Anonymous on Mar 16, 2018 at 4:27 AM

I have been the younger crossdresser in a relationship like this... It was amazing sex and I loved every moment of it. Best sex of my life, and god I love hearing my friends dad grunt as he emptied his balls into me.

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Anonymous

by Anonymous on Mar 16, 2018 at 6:06 AM

Does your best (close) friend know that your bisexual?

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Anonymous

by Anonymous on Mar 16, 2018 at 8:34 AM

My friend has no clue that I am bi. Until I started fucking his son I had only gotten a couple of blow jobs from s guy.

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Anonymous

by Anonymous on Mar 16, 2018 at 9:12 AM

I've never had a female suck my dick like a man. I think females do it out of obligation and a man does it because he wants to - the enthusiasm and enjoyment is very evident. My only complaint: I was 38 before I let a man suck my dick.

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Anonymous

by Anonymous on Mar 17, 2018 at 9:13 AM

One of my dad's friends walked in on me trying on his daughter's stuff when I was thirteen and spending the weekend and he's been having sex with me ever since. It's really okay too!

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Anonymous

by Anonymous on Mar 17, 2018 at 9:21 AM

I'm in college and last fall I caught my kid brother's best friend trying on my younger sister's panties. He was spending the night and got so embarrassed I didn't have much trouble fucking his barely pubescent perfectly tight little eighth graders ass. The problem is I can't keep him off of my dick. Ya, it's hot but he was totally virgin when I did it and I've turned him into the cutest little boyslut, and kind of feel guilty about it!?

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Anonymous

by Anonymous on Mar 18, 2018 at 4:10 PM

I'm 67 years old and married for 31. Through the years I've had young girlyboys on the side. My neighbor, a 36 year-old father of two boys, regular takes my dick up his ass wearing his wife's finest lingerie, make-up, wig and all. I love that!

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Anonymous

by Anonymous on Mar 19, 2018 at 8:22 AM

#7- That's pretty cool. I've been been getting fucked by my dad's friends for some time now. My dad's been wearing my mom's undies for some time, Mom either doesn't know, or does and pretends not to. Two years ago when I was thirteen one of them that I saw with my dad started talking to me at the mall. He said that I was a really cute boy and invited me over to watch a movie. I told um that I'd seen him with my dad and knew what was going on and it was kinda weird. We joked about it because he admitted that me and my dad look similar in a cute girlie kinda way. I got embarrassed like and he said that like to buy me some girl's clothes if I'd try um on for him. I'd already been trying on my sister's stuff and I got excited and said okay. We went to the department store and I even tried stuff on. My hair's longer and the sales lady actually thought I was a tomboy girl. It was so much fun, I got panties, even a few training bra's, lol. Short skirts, tops and lace camisoles that even matched my panties. I was so grateful that when I tried them on for him we fooled around, and I even sucked him. It was the first time for me. I'd seen him fucking my dad, so I was really embarrassed, blushing and everything when I asked him if he wanted to do that to me. He said "Of coarse! Fuck the most gorgeous little ass I've ever seen, who wouldn't!?" I couldn't believe that I was doing what I was doing. I had on a short really cute skirt and lacie panties. I was willingly laying on my tummy with my skirt pushed up, my legs were wide apart and he was rubbing his penis against my panties harder and harder. He pulled um down in the back and squeezed something, I guess it was KY cause that's what he used after all the next times. He started trying to push his penis inside of me but it wouldn't go in. I got kinda scared and said "Stop, don't, it's too big!" He kept pushing anyways, then it happened, he started squirting sperm and that's how he got into me. It was really warm and kinda nice feeling and he was kissing me on my neck and the side of my face and his penis just went in, it went all the way in too! My dad doesn't know I fool around with his friends, but he does know I wear girls stuff. He said " don't worry your mom won't find out." I know he knows that I fool around with the older boys in the neighborhood but he doesn't know how far I've gone though. He said "there's nothing wrong with a cute younger boy such as you are being curious about other boys. The older boys in the the neighborhood I grew up in found me really cute too!" He smiled and said "When you get ready for sex, talk to me first." LOL!

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Anonymous

by Anonymous on Mar 19, 2018 at 8:25 AM

#7- That's pretty cool. I've been been getting fucked by my dad's friends for some time now. My dad's been wearing my mom's undies for some time, Mom either doesn't know, or does and pretends not to. Two years ago when I was thirteen one of them that I saw with my dad started talking to me at the mall. He said that I was a really cute boy and invited me over to watch a movie. I told um that I'd seen him with my dad and knew what was going on and it was kinda weird. We joked about it because he admitted that me and my dad look similar in a cute girlie kinda way. I got embarrassed like and he said that like to buy me some girl's clothes if I'd try um on for him. I'd already been trying on my sister's stuff and I got excited and said okay. We went to the department store and I even tried stuff on. My hair's longer and the sales lady actually thought I was a tomboy girl. It was so much fun, I got panties, even a few training bra's, lol. Short skirts, tops and lace camisoles that even matched my panties. I was so grateful that when I tried them on for him we fooled around, and I even sucked him. It was the first time for me. I'd seen him fucking my dad, so I was really embarrassed, blushing and everything when I asked him if he wanted to do that to me. He said "Of coarse! Fuck the most gorgeous little ass I've ever seen, who wouldn't!?" I couldn't believe that I was doing what I was doing. I had on a short really cute skirt and lacie panties. I was willingly laying on my tummy with my skirt pushed up, my legs were wide apart and he was rubbing his penis against my panties harder and harder. He pulled um down in the back and squeezed something, I guess it was KY cause that's what he used after all the next times. He started trying to push his penis inside of me but it wouldn't go in. I got kinda scared and said "Stop, don't, it's too big!" He kept pushing anyways, then it happened, he started squirting sperm and that's how he got into me. It was really warm and kinda nice feeling and he was kissing me on my neck and the side of my face and his penis just went in, it went all the way in too! My dad doesn't know I fool around with his friends, but he does know I wear girls stuff. He said " don't worry your mom won't find out." I know he knows that I fool around with the older boys in the neighborhood but he doesn't know how far I've gone though. He said "there's nothing wrong with a cute younger boy such as you are being curious about other boys. The older boys in the the neighborhood I grew up in found me really cute too!" He smiled and said "When you get ready for sex, talk to me first." LOL!

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Anonymous

by Anonymous on Mar 20, 2018 at 4:23 AM

Do you fuck him while he I wearing ha dress

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Anonymous

by Anonymous on Mar 20, 2018 at 8:44 PM

I have fucked him naked, fully dressed in makeup and heels, and during one quickie he was in a business suit.

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Anonymous

by Anonymous on Mar 23, 2018 at 1:44 PM

I've been fucking my girlfriend's fourteen year old sons sissy ass for some time now. He looks better in his mom's panties then she does. That cute little ass of his takes it all too.

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Anonymous

by Anonymous on Dec 9, 2018 at 6:42 AM

#8/#9 is often on here giving lying comments. His posts don't always make sense - he's supposed to be having sex with his dad's friends but there's only one friend mentioned here - and for some reason he spells "them" as "um".

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