Category: sissification

Regular

Sissy Thanksgiving Pt. 10

He really wanted to break my virginity… the thoughts rushing through my head were uncontrollable. I had never ever seen a guy naked until recently and all of a sudden I had given one a blowjob and, now, I was in bed with one.

I was nervous and scared about what was going on. I was away from my parents and the only two people here were older guys – horny, older guys.

Mr. Gregory was sat in a chair in the corner with a grin on his face and his hand rubbing the outside of his jean’s crotch.

He nodded to me enthusiastically. He wanted me to do it.

As I lay on the naked stranger, I reached down towards his hard cock. It was so hard. He looked up at my skinny, young body and was practically salivating.

I lifted my leg a little so that his cock could stand upright underneath me. It was big – how could that fit in me? It was at least as wide as my body.

He looked up at my face and said “go on little boy, do as you’re told, put it in that tight ass of yours…”

I moved my thong from my butthole onto one cheek so that my boy pussy was exposed. I let my body rock a little to feel his throbbing dick against the outside of my hole.

It felt good, a tingle inside.

I attempted to push my body weight onto it but I was just too tight. It wouldn’t go in even a little bit.

He started to get a little frustrated so he swung his arm around my back, lifted me, and lay me on the bed on my side. He was now kneeling over me with his cock positioning between my buttcheeks.

I couldn’t let him see how nervous I was. I looked away but, by doing so, was now looking directly at Mr. Gregory. He had a full smile and his pants were unzipped.

I felt the man push his cock harder against my boy pussy.

“Just a little push and we’ll be ready to go, little one…”

Fear had taken over. I was sweating. I was visibly uncomfortable.

He pushed even harder, this time forcing the tip of his cock inside of me.

After trying that for a while, he realized it wasn’t working.

“I need to use my whole body for this. Get on your stomach…”

I slowly flipped my body onto my stomach, my legs tucked under him, his body positioned right on top of me.

He pushed again.

Again, same problem. I was just too tight.

He grabbed at my shoulders for leverage. He yanked my body towards him.

I felt a little more of his cock slide into me. It hurt – I couldn’t do this.

I pushed at his arm with mine and tried to swing my body back upwards.

“What’s wrong, you little slut?”

“I-I-I can’t do this… not now… I need… I need to stop.”

He huffed and slumped off of me. He looked mad.

“Please sir, don’t be angry. I’ve never let anyone get this far. You’re very special. You-you… you’re so handsome and I like you…”

“Well let me make love to you then!”

“I can’t sir… If only I had practise with someone smaller before… I’m sorry…”

He rubbed his face. He couldn’t hide his frustration.

The sweat glistening off of his manly body was still such a turn on though. I reached for his cock and began stroking it up and down slowly at first.

He moved his hands from his eyes and looked back at me again. He still had some hunger left.

I moved my body so that my face was under him. I licked his balls, I licked slowly up his shaft, and I began to suck him again.

He was enjoying it. A relief for both of us. For some reason I really cared that he would be satisfied – it felt like my job.

He eventually rocked his head back and groaned. He gave me no forewarning as the cum bellowed out of his cock like a rocket.

My face was hit repeatedly by the splashes of his warm cum.

“Fuck yes… Ughhh…”, he moaned, “good fucking girl. Now lick it up…”

I did – I already was doing it – and I did it with a big smile on my face knowing I was his “good girl”.

Tune in for part 11 soon!

If you want to recap or read the other chapters for the first time – tap the “sissy thanksgiving” tag at the bottom of this post.

Regular

Any guys in San Fran?

Hit me up on messenger 😉

New posts over on femboyschool.tumblr.com!

New posts over on femboyschool.tumblr.com!

Direct message me for a “text message” story b…

Direct message me for a “text message” story between you and myself as well as you and my stepdad.

He will be your close friend / old buddy who has been living with his new wife for a year or so. I will be his stepson.

You will witness through photos and texts my feminization.

Message me with your Mr. name (e.g. Mr. Collins) and be prepared to reply fast as these stories take a long time to get to the juicy parts.

You will need to supply photos too and I will give you good sources for them.

This one’s a question for my straight follower…

This one’s a question for my straight followers:

If we had to share a bed and you saw me doing this, what would you do?

Hit me in the DMs!

Check out the latest instalment of the Sissy T…

Check out the latest instalment of the Sissy Thanksgiving story (Part 5) on my Tumblr now!

Massive thanks to @crazzypat for buying these …

Massive thanks to @crazzypat for buying these dresses for me for my birthday!! I love them so much, hehe! 😀 

Please reblog if you like and tell me what you think! 🙂

Please reblog my latest story posts (Sissy Tha…

Please reblog my latest story posts (Sissy Thanksgiving Pt. 1-4) and I might let one of the characters use my boy pussy eventually…

Any daddies online? Fill my inbox :)

Any daddies online? Fill my inbox 🙂

DIRECT MESSAGE ME FOR A ROLE PLAY “TEXT MESSAG…

DIRECT MESSAGE ME FOR A ROLE PLAY “TEXT MESSAGE CONVERSATION”.

FOLLOW ALL THE INSTRUCTIONS OR I WILL NOT RESPOND.

What will happen: we will send “text messages” to each other accompanied by pictures. We will build a friendship and you will be firsthand witness to me transitioning from a boy to a gurl.

You will also witness me falling in love with my stepdad and eventually start to want him.

In your DM send me:
- Your Mr. Name (e.g. Mr. Lewis, Mr. Maddox, etc)
- How you know me and my stepdad
- How old you are (be between 40-65)
- How old you want me to be (your choice! Don’t be shy!)

Rules of the conversation:
- you must reply quickly (enough to move it along)
– the convo will last for a number of days
- you must not appear to be interested in me sexually (I will end up hitting on you)
- you should have photos/selfies to send back (find these on hot daddy tumblr pages)

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