Tasting Caterpillars

Originally posted August 8, 2007

My dedicated line rings, and Mindy tells me she has John on the line. John would like to talk to a slutty young girl, maybe 25, blonde and motherly. I'm confused about the motherly thing. I mean, how motherly can a 25 year old slut be? But whatever, I tell Mindy that John will be talking to Sarah.

"Hey, baby! How are you tonight?" For now, this is my token greeting.
"I'm doing all right," he's soft spoken and he sounds like he's middle aged, "what do you look like?"
I tell him I'm blonde, with big blue eyes, and nice full lips. I'm a natural 38D with a nice round apple butt.

He tells me he's 6 foot something with long brown hair and brown eyes, then he asks me, "What's the craziest thing you've ever done sexually?"

Wow, I have no idea. I'm afraid I'm going to say the wrong thing and ruin this guy's fantasy. So, I tell him I picked up a hot guy in a bar, took him home, sat him in front of a mirror and made him fuck my ass.

"That's hot! You like having your ass licked?"
"Oh yea, baby!" And now he takes over. He tells me that his favorite thing to do is be forced to go down on a woman, rub his face all over her pussy and lick her ass clean.

I make the appropriate, ohh and ahh sounds, and he goes on and on. I realize it really didn't matter what my wildest story was, he was just being polite before he launched into his story.

"I love it so much sometimes I cum while I'm eating a woman's ass. But, I hate when I make a mess in my nightie but I can't help it because cleaning a woman's ass with my tongue is soooo good..."
"Wait, did you just say you were wearing a nightie?" I ask with a giggle I can't quite hide.
"Um, yes," he says very sheepishly.
"You like dressing up in woman's clothes, huh? That's kinky!"
"Well, I really just like the woman's underthings, they're so frilly and it's really silly for a big man to wear such dainty things, isn't it?"
"It is!"
"Yea, I look like a little sissy boy! But, I don't like to wear the underwear, just the nighties so my weenie sticks out when I get excited."
"Oh yay! So, I get to dress you up today?"
"Do you want to? I'd love it if you'd want to dress me up!"
"I would love to play dress up with you...Let's see, I have this cute little pink nightie. It's lacy and see through, and it comes down to just below your ass,"
"Oh, that sounds pretty, then when my weenie gets big it'll make the nightie stick up!"
"Yup, and I'm going to put on some nice thigh highs on you. I like to see the silky thigh highs on your man legs with your little weenie poking though!"
"I like it, I look so silly, don't I?"
"You do! You look funny in your little pink nightie, you're such a sissy boy!" I say laughing.
"Do you think it would be silly if I put makeup on?"
I laugh some more, "Oh yes! Let's put some pretty make-up on you."
"Sometimes I make myself up. I know how to put makeup on so I look younger or older..."
"You do? What do you do to make yourself look younger? We're going to make you look like a young little sissy boy!"
He tells me his different make-up strategies depending on if he wants to look younger or older. "If I'm going to do my make up like a young girl, I put the cream on my face, so it evens out my tone, and makes it look shiny and rosy. Then I put the black eyeliner on a little thicker than I would if I was an older person. I like being dressed up and played with like a little doll."
"Well, good. You're going to sit in my chair, and I'm going to put your long brown hair in two pig tails. Now I'm going to put some black eyeliner on you, with some blue eyeshadow and some bright pink lip gloss."
"I like that, but I like red lipstick better."
"Oh yea? Well, let's put this slutty red lipstick on you, and we're going to put you in some strappy heels, too."
"I love heels! I like to wear open toe shoes so you can see my red toenail polish."
"Of course! The strappy heels are sandals, with your toes sticking out and cute little straps going around your waist."
"Yea, cause when you make me cum I can drip on my toes."
"Of course! You like to see that thick white cum on your bright red toenails, don't you? Now, stand up for me, and put your hands above your head and spin around like a ballerina."
"Ok."

I laugh and clap, and he makes a groaning sound.
"Are you touching your weenie?"
"Yes," he says sheepishly.
"I don't remember telling you you could touch yourself. Did I say you could touch yourself?"
"No, you didn't."
"Well, now you're going to have to spank yourself. Go ahead, spank yourself for being such a naughty little sissy boy!"
And I hear a big loud smack.
"Good, do it again,"
"Awww..."
"DO IT AGAIN!"

So he did! HA!

Then I tell him I'm going to put some jewelry on him since he looks unfinished. And I put a long string of wraparound pearls on him and a little anklet. Then I topped it off with 6 silver bangles on his left arm a charm bracelet that had little bells that tinkled when he moved on his right.

"So you'll know if I touch my weenie again without your permission!"
"You're a smart little sissy boy."
"Is it weird if a guy puts a tampon in his butt?"
I laugh, "Yes, it's weird. You like tampons, too? You ARE a great big sissy boy, aren't you?"
"Yes, I am. I like to put a tampon in twice a month or so. Have you ever seen a guy with a tampon in his ass?"
"No, but I want to. Go put a tampon in for me right now. Tell me how you do it."

He describes how he puts his cute little manicured foot up on the sink, and spreads his "ass-pussy" apart. He described the tampon components properly, so I'm pretty sure he's actually worn a tampon before.

"I like the way the string feels between my butt cheeks."
"Oh yea? Show me. Shake your ass for me so I can see the tampon string wiggle like a little tail." He giggled and I laughed, "Look at you! Such a little sissy boy with a tampon in your ass pussy. Come her so I can tug the string."
"But..."
"Come over here! I'm not going to take it out, I'm just going to tug it, tease your little ass-pussy."
He giggles, and says "Mmm, I do like that."
Then I tell him, "Now turn around and show me how you make your weenie spin."
"Awww..."
"SHOW ME! Do the helicopter dance with your weenie so I can watch it spin."
"But, I..."
"Do what I tell you! Do the helicopter dance. Now."
"Ok." He actually sounded shy and embarrassed. I laughed at him some more.
"Do you think I look silly?" He asks me quietly.
"Yes, you look very silly. A little sissy boy in a pink teddy with that little weenie sticking out so hard."
"My weenie is hard."
"I know it is. But, you're not touching it are you? I didn't say you could."
"No, I'm not touching it. But I want to."
"I know you do. Maybe if you do a good job licking my pussy I'll let you come."
"Oh yes, I'll do a really good job. I used to have a girlfriend who would make me lick her clean, and I'd rub my face in her pussy and mess my makeup all up."
"Oh, you're such a good little sissy boy, aren't you?"
"I am. Her family owned a farm, and they went away for about 6 weeks, so she stayed there to take care of the animals. She used to make me go with her to milk the cows and stuff."
"Did she? Did she make you wear cute little outfits? Little farm girl dresses?"
"Sometimes I wore dresses, but I liked it better when I could just wear a bra and my heels, sometimes I got to wear an apron so I wouldn't make a mess."
"I bet you looked really silly in your bra and heels milking a cow!"
"I did, and she laughed at me. She made me fuck a sheep once too."
"OH! You're a dirty little sissy boy! And you loved it, didn't you? You loved fucking that sheep pussy so your girlfriend could laugh at you. Such a dirty boy."

He goes into some detail about sheep fucking and bridles and the like, but I was saved by my three minute warning beep.

"You know what? I'm sick of listening to you talk, sissy boy. Come lick my pussy for me, and if you do a good job, I'll let you stroke that teenie weenie of yours."
"Oh yes, ma'am."
"Good boy. You've been a very good boy for me today. You go ahead and stroke that weenie."
"You're not being very firm with me."
"What?! I'm being nice to you since you were such a good boy! Do you want to stroke your weenie or not?"
"Yes, I do, very much."
"Then shut the fuck up and come already. Make sure you say my name when you do."
"Oh yes! Thank you Auntie Sarah! Thank you for letting me stroke my weenie. Oh, Auntie Sarah, thank you! Thank you for dressing me up and letting me come for you."
"You're welcome, you dirty little sissy boy. Now shut the fuck up and come for Auntie Sarah."

When he finished, he said, "Thank you so much, Auntie Sarah, I had so much fun today."
"So did I! You're an adorable little sissy boy, and I hope I get to dress you up again."
"Me, too.

How can such a variety of fetishes reside in one body? What does it say about me that I had fun talking to this guy? I mean, it's good that he got off on being humiliated since it would have been hard not to laugh. At the same time, it was fascinating. He mentioned his nightie so casually, almost like he hoped I'd pick up on it, but didn't want to straight up mention he liked women's clothes. I hoped that he really did have ex girlfriends that he was able to play some of these fantasies out with. Aside from the sheep fucking, it's pretty harmless. But, I'd imagine if a guy told a girl he wanted a tampon in his ass-pussy, she'd run screaming.

Am I too open minded or have I just found my calling? Either way, I'll never ever be the same.