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cutest shemales and ladyboys

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here are some of the cutest, hottest most beautiful shemales and amazing ladyboys. upload the best shemale and ladyboy pics and videos you have ever seen. Gifs with captions are also welccome, Only cute and sexy sluts, you can also upload clips with adventurous Shemales, Ladyboys. Receiving self facials and squirts. Licking, swallowing and covered in their own cum. only want shemales and ladyboys that are cute and sexy that look like women dont post manly shemale it will be removed

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4
Anonymous
@confessions
08 Jun 2012 12:06PM
• 396 views • 0 attachments
[ − ] thread [ 2 replies ]

I confess that I have a foot fetish. and i recently told my girlfiend (shes ok with it) , who's extremely hot as hell every time I pass her I look down just to see if I can see her feet. But she never wears anything that shows her feet. ive been to her place multiple times, but it never really crossed my mind to look at her feet, until one day I walked past her, and she was wearing flip-flops. and I swear she had the best feet I've ever seen, she had a nice light pink nail polish on, and her feet were in the best shape ever. every time i think about how sexy her feet were, i get extremely hard. a few days later i asked her if we can do something kinky, she was fine with that, everything like this: her and i were walking into her bedroom, with her in my arms, i layed her on the bed and slowly rubbed my hand down her legs (she had no pants on which was another turn on) when i got down to her feet, i slowly took her shoes off (they were flats) and her feet were clean, and the nicest feet ive ever seen. so slowly i started sucking each one of her toes slowly, sliding my tongue between each one slowly. i did this for a while, then told her i wanted a footjob, so i took off my pants, my boxers, and started lying on my bed. she brought lube with her, and started rubbing lube all over my cock, and all over her sexy soles, then she started wanking my cock, with it between her toes, she started slowly then went faster, and later i came all over her toes, and when i thought it couldnt get any better than this, she licked all the cum off her toes. that was the best orgasm she ever gave me, (we hadn't had sex yet) so i thought i would return the favor of orgasm, so i fingerred her slowly and slowly, then faster and faster, then she squirted all over the sheets.

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2
Anonymous
@chicks
29 Aug 2022 5:43PM
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[ − ] thread [ 1 reply ]

She makes the best solo videos I've ever seen!

So much squirting and wet orgasms!

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4
TylerRed
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@funny
06 Nov 2024 3:11PM
• 700 views • 1 attachment
[ − ] thread [ 17 replies ]

Best Older Woman Squirt EVER, the look on her face afterwards is priceless...

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10
Anonymous
@confessions
30 Jul 2013 9:20PM
• 4,139 views • 0 attachments
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I have only ever creampied one girl. And it was someone else's girlfriend.

So here's the story: Back when I was a senior in high school, I played football with a guy that wanted to see his freshman girlfriend get fucked by another guy. I wasn't exactly "best buds" with the guy, but we had been teammates for the last 4 years and I guess that was enough to make him feel comfortable asking such a thing.

His girlfriend was the type of girl that was extremely sexy in an innocent, naive type of way. The type that would get hit on because of her sheer beauty (which I will get to in a minute), but the kind that guys wouldn't pursue too hard because her lack of overt sexuality made her seem like a prude, and a waste of time for those looking for a quick lay (which is most of us guys, especially at that age). In fact, you wouldn't even expect her to know the first thing about sex, which actually wasn't too far from the truth. According to her boyfriend, he had only just taken her virginity a few months before, and he was attracted to her for much the same reason as I was in the sense that he loved the idea of corrupting her innocence.

Now back then, this really wasn't something that was as appealing to me as you might think. I had only been with a few other women, none of them were ever that much younger than me, and I felt a little guilty about this plan to "corrupt" an innocent girl. This all changed, however, when he showed me the blurry camera phone picture of his girl sitting up naked, spread eagle on her pink bed sheets with the most embarrassed look on her face. I knew this girl was beautiful before, but considering she never went out of her way to look very sexual or wear anything revealing, I was stunned at the body she had been hiding all this time. The first thing that floored me was the sheer size of her tits. For a girl that hadn't even turned 15 yet, she was 5'2", no more than 115 lbs., and was sporting 34Cs that seemed to defy gravity. Couple that with a tight body; a nice plump, firm ass; and a gorgeous, shaved slit; and I was sold.

In the interest of keeping this from getting too long, I'll skip ahead a bit. But essentially I told him I couldn't do it with him watching, at least not the first time; it would be too weird. He agreed it was fine for us to be alone as long as we video taped the whole thing so he could watch it later. We ended up at her house after school, with the place to ourselves. She seemed very nervous, and started telling me how she hated that her boyfriend wanted her to do this. I immediately felt guilty and said we shouldn't. That I would never want to do anything she wasn't comfortable with. With that statement, she looked me deep in the eyes, jumped on me, and kissed me harder and more passionately than I had ever been kissed before. We made out for what felt like 20 minutes. The kiss itself was so sexual that it was almost satisfying by itself. She finally got up, turned the camera on, placed it on the dresser, and seductively walked back over to me.

"Take me. I wan't you. Right. Now," she said climbing onto my lap and getting closer to my ear in a whisper with each word. With that, I couldn't take it anymore and I ravaged her. Clothes were thrown about; I devoured her perfect, pink pussy; and she sucked my cock like a pro, never very deep, but putting in the effort to gag and continue to try for more. It was perfect. When it finally came time to fuck her, I reached for a condom and she stopped me. She told me to just fuck her without it, she wanted to feel me. I fucked her in every position imaginable and she seemed grateful for every thrust. I finally ended up on top of her, her legs wrapped tightly around my back, and my arm under her lower back and ass pulling her up into me. In turn she was pulling herself up into my cock with her hips and legs. She was working my dick and grinding into me just as much as I was fucking her back in return. I couldn't take it anymore and told her I had to pull out and cum. She clenched me tighter with her legs and begin to buck up into me harder. I thought maybe she didn't hear me and began to panic I wouldn't pull out in time. I reiterated that I was "GOING TO CUM!".

With that, she looked me directly in the eyes and responded, "So do it then." That was it. I began to cum like I had never cum before. Squirt, after squirt, after squirt; I filled her up while her body convulsed and we came in rhythm with each other. With her clinging to my body as hard as she could. Eventually we both collapsed onto each other and lay there motionless for at least ten minutes before either of us moved.

I remember finally sliding out of her and watching my cum pour out onto her pink bed sheets. I was a much better image than the blurry camera phone pic that didn't include my cum dripping out of her and pooling between her thighs. It was beautiful. We jumped in the shower, and cleaned off, and I headed out before her parents got home.

The next day, I got a call from her boyfriend. I expected it to be him telling me how insanely hot everything was and to thank me for helping out. Instead, he was furious, yelling something about how I was never supposed to cum in her, etc, etc. As I came to find out, she had apparently NEVER let him even fuck her without a condom, let alone cum in her. And apparently she wasn't big on sucking his dick either. Could have fooled me based on the exceptional head she gave me.

They ended up breaking up immediately after and she told me that was really her plan. That she was over him and she had fallen for me that night. The rest of the football season was a little tense to say the least, especially since I spent the rest of my senior year fucking and filling this girl with cum AT LEAST 5 times a week until I finally left for college.

We still keep in touch some 8 years later but no longer live near each other (multiple states away). I have seen her a few random times over the years here and there and fucked her, and she swears I am still the only guy that she has ever let cum inside her. Who knows if that's true or not, but what I do know is it is still the most passionate sex I have ever had in my life and she is still insanely beautiful and kept much of her reserved, innocent charm. If we lived closer, I'd probably make her my queen in heartbeat.

Sorry if that story got a little long. I've never retold that story before in such revealing detail, and I guess I got carried away in the memory. I hope you all found it enjoyable.

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5
Anonymous
@confessions
14 May 2014 12:01AM
• 3,347 views • 0 attachments
[ − ] thread [ 3 replies ]

There is this older chick at work who is super into fitness and working out, very muscular but still feminine enough looking to be hot. Its not normally my cup of tea, but she just screams fuck me with the stuff she wears to work.

I just broke up with my GF and she found out, turned up the teasing at work so I said fuck it...why not

I went over to her house after work on Friday. She is very blunt and opened the door naked. Once I came inside we didnt waste any time and went straight to her room. She didnt even have to ask, I was naked in a second.

I laid on the bed and she got on top. I was raging hard but she wanted to give me a massage. I wanted to fuck, but I thought hell I will get a massage and then fuck her. She had a very controlling feel about her, and to my surprise I kind of liked it.

After a few minutes of massaging she started to whisper in my ear how "I was making mommy so wet with my moaning". I wasnt sure if she meant it as an incest roleplay or not but I loved it as Im into incest roleplay.

After massaging every inch of my body she sat on my face and made me eat her out. She was soaking wet and it was the best tasting pussy I have ever had, it was so sweet and fresh tasting.

She kept teasing my cock, slowly, and I was on the edge of cumming and she knew it.
She started squirting all over my face and it seemed like it was never going to stop.

She wrapped her lips around my cock and I instantly started to cum. She got up off my face, turned around sitting on my chest and held me down, and kissed me pushing all my cum into my mouth. I was so turned on I didnt care.

We spent hours fucking, sucking, eating her out until we passed out. She definitely took control the whole time and it was nice being able to let go and be her boy toy.

I was completely drained and slept very hard that night. I woke up with her under the blankets putting a cock cage on me. I kinda freaked out as I woke up, but I wasnt about to tell her no.

She got out of bed wearing the sexiest panties. Black and red lace with strings and...just fuck, they were hot.

I just laid there in bed not knowing what to say as she put on a strapon with an evil grin on her face.

She got back ontop of me and said "If youre a good lil boy for mommy for one week and only cum from me fucking you...you can have mommy for one week any way you want after"

Nothing else was said but we both knew I agreed. She lubed up and started fingering my ass toying me. I strained against the cock cage and it was so sexy. She aimed her strapon for my ass and put my legs around her.

As she slid into my ass she made me beg for more, made me beg for mommy to make me cum.
After about 15 minutes of her fucking me, I had my first 100% prostate orgasm. I had used toys before, but never came just from them.

We have met up every day now and she makes me cum insanely hard fucking my ass...

What should I do with her next week??

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Anonymous
@confessions
20 Nov 2025 6:47AM
• 155 views • 0 attachments
[ − ] thread [ 2 replies ]

I confess one of the best pussies I ever fucked was this 50 year old crackwhore. She had the sexiest shaved pussy I've ever seen, I licked her and ate that pussy until she squirted in my mouth while she smoked her favors then told me I could fuck her raw and she wanted my cum she was so horny. God she gripped me good and fucked and rode me until I blew 2 loads in her back to back.. Fuck I miss that pussy..

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