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Tears: the sure sign that your femme-boi is loving his job.
Humiliation: all closeted sissies crave it. Make sure to let everyone in your neighborhood aware of his new situation!
Social Security: doesn’t pay to tip your hooker.
Spicy Sex Life: I think Brad’s about to see some in action.
Bridesmaid Dresses: There should be a law or something.
Just say no to frumpiness!
Maybe if she went and put on that giant strap-on she just bought for no apparent reason, her message might get across.
Act Like I Want It? Is this a trick question?
Fucked with progressively bigger dildos, by a machine that never tires, while your girlfriend watches on? Can it get any better? Probably, but enjoy this while you can. The real stuff is next.
Backstory? It’s the truth!
A Deal is a Deal
A woman with proper priorities.
Some guys get all the luck.
Kevin, you insanely lucky bastard!
Maybe Kevin would enjoy it more if he help her get ready, dressing his wife up for the soul purpose of getting fucked by anyone that’s not him.
Life will never be the same again – thank god!
Things like this usually turn out for the best… riiiight. You’ll never be referred to as anything remotely masculine again, little cock slut.
Well, someone just hit the jackpot! By the way, two hours of straight fucking? I guess I know how that smile got on her face.
I’m right there with ya, sister.
Isn’t it fun to tease your girlfriend’s father?
It’s date night!
Isn’t modern technology great? No more awkward conversations with your sissy husband. Now you can arrange it for him to come out of the closet on your schedule. Take your sissy by the balls today!
Make sure to hide all of your crossdressing lingerie where it can be easily found by your sexually adventurous wife. Then sit back and enjoy the ride… or enjoy being ridden, whichever.
When women really understand, it’s a beautiful thing.
Reblog for all your vanilla women out there. They need to think about the advantages and not just react stereotypically, mad that their bois got into their favorite lingerie. Their lives would be so much easier in the end.
Motivation: more than enough.
First night jitters at a new job. Don’t worry; it’s like riding a bike, except there’s cock instead. So, it’s like riding cock!
Just wait until your new mom enrolls you in that all girls school and you get to wear a sexy school girl outfit for the next three years!
Well, it’ll definitely be a nice romantic evening for everyone involved! I hope she brought egg rolls.
You never know who is watching, so make sure to always put on a great show!
Don’t pause. Don’t think about it. Just hand her the key to your cage, put on your lingerie, and set up that fucking machine. I have a feeling you’re in for a really long night.
Pick your caption: A. Look what I caught today. B. I said a striper - not a stripper! C. Is her real name Annette?
werenotadulting: Little girl was caught being naughty…. ~18 , please don’t delete caption~
I hope she doesn’t make him masturbate while wearing ladies’ clothes.All chars. 18
xxx tumblr
Busted riding BBC!
sissyjustbitch: humiliation sissy bitch captions My gf just caught me I just wish she was more of a dominatrix time will tell
*accidentally opens your door as you masturbate* “I-I wasn’t watching I swear ! …I just heard sloppy sounds and moans coming from your room. And then I saw you masturbating vigorously and moaning out loud your love for cocks… It made me so hard
tonyd1509:a-wank-and-a-nap: Love! I’m not a fan of captions, but this one caught my attention. Who’s who in this conversation? Would it matter? Sounds hot as hell to me either way.
tricias-captions: When my daughter Brandy and her friend Carmen snuck into our liquor cabinet, they didn’t know I’d put a NannyCam up. I caught them red-handed pouring Cuervo into their slushies before the party. So, there’s no party for them.
tricias-captions: Mrs. Lewis hired me to clean house and cook. It was a good gig: I had a room and I was pretty sure she wasn’t going to turn me over to the ICE. Then she caught me on her computer surfing porn. She pretended to be shocked to find that
tricias-captions: My neighbor, Mrs. Creighton, caught me drinking beers in the woods behind our houses. She could tell my mother, she explained to me, or I could do some things for her. It’s still better than telling my Mom. She would beat my ass purple.
tricias-captions: When my boss, Stacey, caught me one day at the office going commando — don’t ask how — she told me that from that day on I wasn’t allowed to wear panties ever again. And she enforces it with inspections. I never know when its
tricias-captions: Heather didn’t think she was going to get along with her Junior Year roommate, Justine. But one day Heather caught Justy sniffing her dirty panties and they realized that they had a lot of the same interests.
rraicleach:all caught up!full set available on my onlyfans do not self promote or remove my caption
Anonymous said:can we get a caption where a virgin masturbator gets caught jerking his tiny penis to pictures of his crush on facebook? and maybe she laughs at him, humiliates him, and gives him some lotion to help him out? thanks
sissy-panties said:Will you make a caption of a guy getting caught in his sisters panties by his sister
Goddess Lindsay owns your dick now
Threesome Thursday: You’re a chastity slave to college girls now
Crossdressing Caption - Caught in a Trap
Your wife had left a message for you at work.You had gotten it late because your secretary did not return from lunch.Your wife asked you to meet her at an address you had never been to before.You arrived to what seemed an empty studio. Then you heard
jadenkaiba: “We can explain~!…”Camila and Hinoka got caught by Sakura and Elise(Just for fun, you can place captions on what they are saying )OTHER VERSIONS AT PIXIV ENJOY! :) ——————————————————————————————————-
leatherlacedbass: ✨🎄Christmas Kitten caught in the lights🐾✨ Please keep caption
chien-espagnol: Caught myself a new toyWith Violet & tumblr-less hottie ~please leave caption
leatherlacedbass: Daddy caught a Christmas Kittycat!!🐾🎄🐾Collar on sale Here from @littleqsoddities💖✨Please keep orig caption✨
tricias-captions:“Yeah, George’s Aunt just reached in and copped a feel while we were in the bathroom. And when I didn’t complain, she started to make out with me, but we almost got caught when some waitress came in. I think I’m gonna like that
