Aunt Jo

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Boy has a shameful introduction that his Aunt Jo is TS.
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stories55
stories55
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He was getting ready to go off to college when his mother said he would be boarding with his Aunt Jo and save the money on the dorms. She said she would feel more comfortable with him under aunt Jo's watchful eye. It created a bit of disquiet in him. While he liked to have his way with women; the way his Aunt Jo had looked at him made him feel differently. In fact it conjured these most erotic nightmares. Often he woke up in shameful that such thoughts came to his head, and even more shameful when he then took matters into his hand and had an orgasm from it. He wandered into her room a few times when she visited them and put her worn panties to his nose a few times, glad she never caught him. He began to fantasize about other women treating him that way. He wondered if that was why he was a bit more aggressive with women, proving his manliness maybe too himself more than anyone else.

Like his date with Suzy Johnson last weekend. She kept saying no, but after a good finger fucking she was wet. And it took just a little coaxing with a hand behind her head when he brought his cock to her lips, he just worked it in and out of her mouth till she got the hang of it. He figured she liked it as she was moaning, heck she was wet. But he hated all the drama, besides where else was he supposed to cum. I mean the bitch needs to learn how to swallow eventually. I mean if she just swallowed it wouldn't have run out of her mouth an on to her blouse. What was with the tears and the pout? Like the others, the little bitch would suck him off again rather than have him pass it around school what she did. Worked like a charm, always did. The thoughts rode through his head.

Why couldn't they all be like the women at the strip club He loved the way that one straddled him and ground her ass on his crotch. After a few dances like that he called Suzy. But bitch wouldn't take his call. He sure would have loved to dump a load in her mouth again. That was what ran through his mind as he took a shower after getting to Aunt Jo's house. After he got out, he dried off and then wondered where his clothes where. The suitcase was gone, everything he wore. He wrapped the towel, though small around his waist. It wasn't big enough, he had to hold it. He opened the door and yelled "Aunt Jo where are my clothes??"

Down here bill, she said. I'm washing them

Could you bring them back up?

No response, he waited 5 minutes, so he walked down to get them himself.

My, our little man has grown up, she said as he extinguished the cigarette and walked over to him. You didn't give your aunt Jo a hug and a kiss when you came in. When I avoided it she grabbed me. Her hands on my ass and then pulled the towel down. Her tongue was in my mouth and her hand on my cock. She then pushed me on to the chair and sucked my cock. Taking me to the edge, stopping and doing it again. Then she stopped. I stood there shocked

Bill do you know what I do for a living? I didn't answer. I am a therapist. I used certain techniques to deal with men that have a problem treating ladies properly. I've had some bad reports on you and we are going to deal with it.

I know how to treat women I said indignantly, probably with a smirk on my face.

Are you a virgin?

No

And did the women enjoy the sex with you

Sure

How did you know?

They got wet, I heard them moan.

You use foreplay?

Yes

Like what?

I use my finger

So you finger fuck them to warm them up?

Yeah, they like it they are excited?

I just sucked your cock, do you have them do it

Yeah, foreplay is a two way street.

So you don't think there is anything wrong with it, it isn't demeaning.

No...once you push them a few times they get over their modesty

Ok, and I know that you have used strip clubs and I heard a little story that you lost your virginity with a prostitute

How did she know this I asked myself? Aunt Jo I'm feeling uncomfortable here can I have something to wear?

Good...she brought over a pair of women's panties and handed them to me. Recognize these?

No

She hit a button on her laptop.

She had a video of me in her room sniffing the panties and jerking off. Bill, I have a surveillance camera in my travel clock. Now why don't you put those panties on

No way I said red faced. She slapped my face. Be nice now; maybe I should put this on YouTube for your friends to see. Look here I have it attached and here is your high school contact list. Should I hit send?

No..No Please

There you go put them on. Do you enjoy wearing them?

No

We will change your mind. Come sit next to me on the sofa. As I did she rubbed he front of the panties getting me hard again. I closed my eyes as it was so shameful especially when she looked in my eyes. Click. With her phone she took a picture of me, face and all in the panties with an obvious erection, another with just the panties and erection. I'll add this to your distribution list.

She took my hand and put it on her thigh and had me rub encouraging...telling me...to go higher..to get her excited or she would send it. I reached up to her panties. Oh shit you have a, co...

Bill it is a clitoris, a big clitoris. Now put your hand back and pleasure me.

No I don't do that. I'm not... In my mind it certainly wasn't a clitoris.

She hit send... There now everybody has the picture. It was the one without you face. So a few hours of damage control and you can say it was a picture you where sending around.

How can you do that? I almost cried. What would I say to everyone?

Shall I send the next? My hand went back up her skirt. I felt it grabbed it, stroked it. She seemed to enjoy my trembling hand. She held out the phone and took a pic. She showed me. It had both her faces and my hand clearly on her...Oh god, I'm dead.

Bill you don't look like your enjoying yourself. Do you want to stop that?

Yes, ma'am...

Oh look some manners. She stood. Ok remove my skirt. which I did. She stood there in her bra and blouse, panties, hose and in her heels. Now William, I saw you enjoying yourself sniffing my panties, go ahead and sniff them now. She grabbed my head and pulled it to her crotch. She ground my face into her panties. Bill I want to hear you moan like you did in the video of you sniffing my panties and jerking off

Louder bitch. Click the picture caught the side of my face and her panties with the bulge. Bet the boys and girls can figure it out who's who with this one.

Please, no Aunt Jo...please

She reached over and hit a button on her lap top. I guess now you're going to have to explain that picture with your face and you wearing the panties in that picture. Click. Another picture, Click, with my tongue out lowering the panties and the clitoris slapping my face.

As I lowered them she put the clitoris to my mouth. Now bill I am going to change you name to Suzy. I am going to use your mouth like you did Suzy's. She pushed it to my lips. Bill should I send a video? Or would you prefer is send this new pic. Everyone is probably waiting. There probably all texting each other wondering about what a sissy boy you are. I am sure everyone in the school knows now.

I opened my lips, and she filled my mouth. Working it in and out. Eventually I was gagging. She pulled it out. The gagging cased my eyes to tear. Oh look tears of joy. Do you enjoy wearing panties and sucking on my clit?

I was quiet and nodded my head no. She spent another few minutes working her clit in and out of my mouth. She stopped and asked the question again. I started to beg her to stop and it wasn't the answer she wanted and she did it again. Now what did your friend Suzy have to do to stop having her mouth fucked? Remember; she started sucking enthusiastically and you would ease up a bit. So show me how enthusiastic you can be, and at least you should stop gagging

I soon started sucking on my own. Ok anything to get this to stop, I thought to myself.

You're going to need a lot of practice Suzy. But I must say you are getting me excited. She pulled her clit out and had it on the front of my face. She stroked it a few times till the fluid began to build on the tip. Are you excited about tasting it? I nodded no. Oh dear that little thing between your legs might be telling another story.

Oh I bet no one taught you to swallow? Come with me, she said. This should help with your attitude as well. She let me into the bathroom and had me kneel in the tub. She put her clit in my mouth supporting it with one hand and the other on the back of my head. Let's learn to swallow, she said. I felt a blast that surprised me. It was her piss. As my face pulled away hard it shot all over my face and filled my mouth. She put it back in my mouth and put one leg over my shoulder and both hands on the back of my head. "Now if you swallow and don't fight I'll go easy. She let the stream come, I tried to swallow but it filled my mouth and ran out. I coughed as I swallowed too much. She didn't let her clit out of my mouth and gave me more as I composed myself. I felt degraded and humiliated. She laughed. Have we picked up a few pointers on swallowing. I know it might not taste the best, but a face full of cum is going to be another picture you are going to have to explain.

Now we are going to have to give you some more swallowing practice later today. We will continue until you learn to be a little cum slut understand? Now clean up, take a shower and meet me in the bedroom.

When I arrived back in the bedroom there was a slutty outfit waiting. "Suzy I want you to get dressed and we are going to give you the skills of those girls in the strip club. I'm thinking as soon as you get it down I'll invite a few guys over, maybe make me a little spending money. I remember you had a thing for prostitutes, so let's see how you like it.

Now, get over her and grind that little ass of yours on my clit. Pretty soon you're going to learn why I'm going to call it a pussy. Oh that is cute, but I think it will be even better if my clit is wet. Get your mouth on it and get it good and wet. One day you're going to sit in my lap and I have something for you to sit on. My legs straddled hers as she sat on the edge of the bed. My ass ground into her clit to the beat of the music. Work it bitch, she said. I bet you would prefer a load on those ass cheeks than between your lips. He had her hands on my hips, she would grind the clit against my ass cheeks. She held her hard clit in her hand and pressed it against my asshole. If you want to take it now, it will save a nasty taste in your mouth later.

She had me stop and had me lie on the bed on my back. Aunt Jo straddled me with her ass over my face. She had me open my mouth telling me she wanted her clit sack sucked. Then she had me spread her ass cheeks and lowered down on me wanted me to tongue fuck her ass. Eventually she wanted 69. She told me that if I could get her to orgasm before she did, she would let me fuck her that night. But if not she had some very nasty things that I would be doing. It didn't take long and I had a hard orgasm. It bothered me I came so hard with her clit in my mouth.

She said she would give me ten minutes to suck her clit to a juicy orgasm. Or she was going to get over me and fuck my mouth. I sucked as hard as I could. But she said time up. She put a pillow under my head and with her legs on either side of me fucked me till I tasted her load. She didn't take her clit out of my mouth. She wanted me to use the cum in my mouth to swish around on the head of her clit. She laughed saying the look on your face is precious, your mouth is stuffed and you can't swallow it all.

She stopped and told me to hold the load in my mouth. She said she wanted to wash it down and took me to the tub again where I tasted her piss again. Now until I hear you tell me how much you love the taste of cum and want more, I'll keep washing your mouth out.

Suzy it is going to be a long summer. My guess is that they will hardly notice you at school in the spring and you're going to be a popular girl.

stories55
stories55
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AnonymousAnonymousalmost 2 years ago

Looking for an old story of similar topic but much more developed. Boy goes to live with aunt and she has a stable of workers in the house and land that are also transgender. Any help, please

AnonymousAnonymousover 3 years ago
Great start

Love to see how summer develops

AnonymousAnonymousover 3 years ago
Confusing?

This whole story was confusing and it feels like a mashup of stories put down in a rush.

Please go back and edit this. You had a good story idea but it was hard to read when your mind is trying to make it work and or correcting it while reading it.

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