Shemale Stories

[Boner]

Cool story! I'd like to hear about when you tied Stephanie!

[a9127]

The above story really did happen as I’ve told it. I wasn’t quite as embarrassed as it seems and of course most of my friends thought it was hilarious. For a brief moment I even thought about a career in acting (eat your heart out Tom Hanks… ).

Interestingly, our English teacher never had anyone perform in front of the class again…

Unfortunately, my girlfriend Stephanie found out about it through her friends. I'm sure they made it sound like there was something “going on” between me and the other girl. When I saw Stephanie in History class later that day, she totally ignored me and took her seat across the room. Deliberately avoiding eye contact with me, when we finally did look at each other her normally beautiful and soft blue eyes were pure ice.

When the bell rang she was out of there. I finally caught up with her at her locker. “Well, I heard you and Rosalie had quite a time in Miss Williams class… it’s all over school… Oh I feel like such a fucking idiot!”

“Steph, it wasn’t what you think.”

Looking up at me Stephanie says “So what was it then Andy? From what I heard you really seemed to be into it.”

“Stephanie, Miss Williams wanted us to put on this stupid play, you know how she thinks she’s this great ‘drama teacher’ it’s just that I got hard tying Rosalie up. Sorry, I couldn’t help it.”

“You could have at least acted embarrassed about it or done something else. All my friends say you two were up there laughing about it. Sounds like you really liked it. I heard the class loved it. Now if you’ll excuse me I have to get to my next class…”

A couple of days go by and Stephanie is still mad and avoiding me. Not even looking at me in History class, and not answering my calls or messages. Note: Showing my age… cellphones of the 90’s did not generally have the same “texting” capability we take for granted today. And thank God there were no cameras in phones back then or our little “play” would have probably gone viral on YouTube… .

Suddenly one day I get an instant message on my computer “Hi, it’s Steph wanna talk?”

Since she lives right down the street from me I head over to her house. I’m thinking this is going to be the “breakup” talk. But when she answers the door she says “I talked to Rosalie. She heard about us and told me nothing was going on between you too. It just sort of happened she said. Everyone thought it was funny and thinks Miss Williams is the one who should be in trouble. I’m sorry Andy, I guess I just love you so much I just overreacted. I’ve been thinking a lot about us. I know you’d never cheat on me.”

“I love you Stephanie don’t ever forget that.” Then we kiss for the longest time.

“Why don’t you come in? My Mom made dinner. Maybe we could just hang out later?”

“That sounds good. I’d like that.”

After dinner we go down to her parent’s basement rec room and watch MTV. It seems like the worst is over and we snuggle and kiss like normal. It’s just like old times.

Suddenly Stephanie asks “So why do you get turned on by tying up a girl anyway?”

“I don’t know.”

“I’ve never been tied up but I’ve seen stuff on TV and sometimes it’s exciting. I’ve always wondered about it. Have you ever wanted to tie ME up Andy?”

I can’t lie. “Yeah. But I didn’t think you’d like it.”

“Well what would you do to me?”

“Let me see your wrists.” Taking my belt I tie your wrists together in front of you.

“I kind of like that, Andy. You are such a bad boy” you say giggling. “What if I raised my arms above my head? Like this?”

When you do that your t-shirt rides up exposing your tummy. You are also wearing very short pajama bottoms. Your legs look so sexy and I can see by the small bulge that you must like it too. Of course I’m fully hard now and it shows.

“So you DO like me like this…” you say laughing.

Seeing your exposed tummy, I can’t resist lightly tickling you. “Ohmigod! Andy stop it!!!”

I do and you lie back against the couch with your legs apart. You don’t say anything, you just look at me and smile. It’s pretty clear from your erection that you are turned on by this. We kiss as I run my hand up your thigh and gently rub your cock through your shorts.

“That feels so good baby. I guess being tied up makes it more intense or something. Anyway, whatever you’re doing don’t stop.”

I slip your small but now very hard cock out of your shorts and begin to suck you off. You are not really tied up, just my belt around your wrists, but clearly you enjoy this. Soon you cum. It’s not like it’s the first time we’ve ever made out or had sex but there is something exciting about this time.

As we lie there, you bring your still bound arms down around me holding me tightly. “Now I’ve got YOU sweetie…” you say giggling and smiling at me.

Copyright © 2017 AMS

[not61]

My first shemale experience

I had dreamed it for a long time. Yesterday I got enough courage and I played her number.
The phone rings and she answered, I could not turn back.
Can I come and visit you?
How long do you want to stay?
I think an hour is enough.
OK, when will you come. About an hour. What is the address?
I will send a text message.

I go to the shower and wash myself carefully. I have an hour and I get a lot of excitement.
I'm almost there when she call. Are you coming? I tell her that I'm almost there,
I'll call her is outside the door, and he will be looking for me.
The front room, he asks to take off the jacket and the shoes.

When I turn, she stands naked in front of me. She is small and graceful.
The hemisphere-shaped breasts and a small semi-hard dick.
She is pressed against me, her body is surprisingly firm.
She asks me to undress. I quickly naked, and she pressed me on the bed. She kneels before me and smiles.
She start massaging my feet and moved slowly upward.
She rubbed her hands with oil and rubbed my thighs. My legs spread and feel how my dick begins to stiffen.
Her look is a little surprised when she looks at me between my legs.
Hands massaging the thighs and moved closer to my dick all the time.
Her fingers wrapped around my dick and milking it and my empty scrotum. Can I suck it? she asks with a smile.
I nod, and at the same time my dick is deep in her mouth.
She turned slightly and his thighs to touch my hand.

I raise my knee between her legs, she rubs her dick on it. My hand caresses her thigh
I'll take her dick in my hand. It feels cold and surprisingly firm. I have not touched anyone's dick,
I am very confused about what it feels like. Soft skin like velvet, not hard or soft. I feel her scrotum,
soft skin and inside two small balls like cherries. She moves closer and I pull the foreskin behind.
Smooth glans slides out and I take it gently in my mouth. It does not taste anything, I suck it in my mouth, just down the roots,
I sroke her balls with my fingers, tightly by sucking almost out, back deep into the throat. Slide your finger in the bum she asks.
My finger is playing around her hole, it's slippery and tight. Push inside she asks. My fingers sink deep into the hole,
I find the prostate and rub it and her dick slides back and forth in my mouth. I'm coming, she says.
I'm ready, I am received and suck dick deeper. Her ass presses around my finger and pulses rhythmically,
I squeeze lightly into the testicles and small load sperm injected into my throat. I swallow everything.

She bends again to my knees and rubs a little more oil on dick and scrotum. She milks my cock slowly and calmly.
At times she sucks my cock and empty scrotum. With a smile she looks at me, You have a big cock, goes to the throat, and really hard.
Do not come to my mouth, I want to see when you come. Her hand slips along my shaft, another hand playing with my empty bag
and her finger fights in my ass. She sucking my glans deeper.
I will come, I can hardly to say so.
She squeezes my cock and looks with a smile when the sperm drains on my stomach.

[a9127]

Originally Posted by Boner

Cool story! I'd like to hear about when you tied Stephanie!

Glad you liked it! I combined and edited these and they are on my WordPress Home Page as "Freshman English Class." I've taken some liberties with a few of the details but yeah, this really happened...

[a9127]

Found this on another website. Damn, didn't think she would tell the whole world about it...

I met up with a guy I matched with on tinder and was immediately swept off my feet. We went out for drinks on Saturday and I had a few too many and ended up sleeping at his place. We didn't have sex, but fooled around a little. Enough to learn he could possibly have a micro-penis. He took me to breakfast the next day, held my hand as we walked, and even invited me back to his place after. It was fun and we were hitting it off. I thought things ended really well, with the exception of my makeup and hair looking like beetle juice at breakfast and the loss of self respect because I stayed overnight with him on our first date.

I didn't hear from him after so I decided to text him (minus points I know) on Tuesday. He only responded once and was short with me. I start to become devastated because I feel like I ruined whatever potential we had, but then he texted me on Friday. "How's your day going?" I responded and never heard from him again. WTF??

Question 1: he also told me he was a virgin which could have been a complete lie, but is it possible that he is embarrassed of his size and that's why he went ghost?
Question 2: did I completely ruin my chances by drinking too much and not going home that night?
Question 3: is he just not that into me? :/ p.s. We were texting every single day for a week before the date, so clearly it's not that he isn't a fan of texting.

Sincerely,
Crushed

[a9127]

This may be hard for some to believe, but I'm actually a 35 year old Virgin...

Just too shy for my own good I guess. Never really got involved in the dating scene in school, and now I don't know too many people outside of work. That's fine with me though, I'm very happy pleasuring myself!

I would describe myself as bi-curious, love pussy but wonder what sucking a cock or having one in my ass would feel like. The first time I masturbated I was 9. Often do it 3-4 times a day now. Love to watch myself in the mirror, and fantasize about others watching me. Or being a sex slave to a dominant shemale. I always begin by teasing my nipples as I watch my cock get hard. Once I'm hard I start stroking my cock with K-Y Intrigue Heat. I wrap my hand (I'm a "lefty" ) around my shaft, and start moving my hips like I'm fucking. I try to make things last as long as possible, so I stroke my cock slowly then stop, and wait whenever I feel like I'm going to come. I love the taste of precum. Sometimes I try a load of my cum, which turns me on even more. Especially if I imagine my "mistress" forcing me to eat my own cum.

It's really exciting to post pics of my cock cumming. I hope everyone enjoys them. More people will see my cock in the next day, than in the previous 35 years!