The School Slut

Story Info
My journey from jock to sissy slut.
1.5k words
4.08
183.4k
72
6

Part 1 of the 3 part series

Updated 10/30/2022
Created 04/17/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

At the start of my transformation I was a young guy in Cornwall a rural county in the UK. I played a lot of sport and was considered one of the 'cool' kids, I was kinda small and petite and had a feminine figure but that didn't matter I would go from girl to girl whenever I wanted.

But then it all changed, by 'accident' I clicked on a gay porn link and watch a guy getting fucked by another and it got me thinking that maybe I could try that, so I joined a gay dating site.

I met this guy called Tristen he was around eight years older than me so wouldn't know anyone I did so I was playing it safe. I met him outside a McDonald's and he drove us back to his, he was a little taller than me and bigger to with jet black hair and olive skin he started slowly as I told him this would be my first time with a man. He lent in for a kiss and I went for it... It was incredible my senses were swimming his musky smell the taste of him his brown eyes looking into mine... this was something special.

He took off his shirt followed by mine kissing each other's bodies all over making me moan slightly with every new touch. He found his way to my cock which sprung to live since the kiss and he started massaging it, I did the same to him and we then stripped each other naked and started kissing passionately on his bed he then turned away and came back with lube three dildos of various sizes starting small not much bigger than my index finger, then getting bigger to what was around the same size as two fingers and around six inches in length and finally a cock sized dildo that was nearly nine inches long he lubed my hole up and slipped a finger in.

I squirmed a little when he did this but it started to feel good and I started to moan, he then put the first toy in and then the next but instead of putting the final one in he put my legs over his shoulders spat on my hole then his dick using it as lube. He pushed the head against the opening and applied pressure until it popped in. The feeling was incredible he was incredible he started to thrust a little, then some more then some more until he was all inside me thrusting as hard as possible making me scream with pleasure. he then took the final dildo from before and pushed it into my ass whilst his dick was in there it my ass go on fire!

But then the pain then it came over me the pleasure was unbelievable it felt so amazing stretching my hole in that way! I was loving every second hoping it would never end but it came over me, the orgasm better than any other I had experienced it was explosive at that moment Tristen came inside me I felt as he filled me up with his warm cum. He thrusted back and forth until his dick went limp and fell out, he then got up got changed told me I should the same so I did.

In the car journey home i could feel his cum leaking out from my used ass and when I walked to my house I felt it trickle down my leg. I went up to my room straight away stripped off and caught whatever cum i could in my hands, I even scooped it out of my hole and then I drank it, and it tasted so good... I was hooked on cum, I was hooked on cock and I was hooked on anal.

By this point me and Tristen had been fucking a lot and it was great, but one day he asks me if I wanted to try a threesome? He told me that it was a buddy of his and he wanted to show me off to him so I thought why not it should be fun! And fun it was... George was his name 6"4 a giant of a man made me look tiny in comparison.

Tristen told me to wait in the bedroom and do exactly what he said, I nodded obediently, he whispered in my ear maybe i should slip this little toy in and handed me a butt plug I again nodded, and fetched the lube and slipped it in. I waited for around 5 minutes until Tristen and George walk in naked, dicks erect ready for action.

Tristen barked at me, "Get on your knees slut you got a job to do."

I dropped to my knees and started to suck at both their dicks, Tristen was an average 6.5 inches whilst George had a mammoth 8.5. Tristen moved away to get something and told me to take all of George's cock down my throat or I would be punished, so i tried my hardest but couldn't do it before Tristen came back with handcuffs and a whip.

He ordered me to stand up and put my hands behind my back and he cuffed me, pushed me on the bed and told me to go on my back and put my head over the edge of the bed which i did, he then said because I lacked effort swallowing George's dick it will be forced down me by him face fucking me.

He told me to open wide, George stood over me his balls resting on my forehead. He then shoved his dick down my throat violently fucking my throat until it was all the way down, Tristen clapped saying well done but I still need punishment which was me gagging on George's cock to near suffocation. George jammed it in hard as ever but once I swallowed it all up he held it there, meanwhile Tristen was whipping me on my stomach and legs.

I started to gag, it felt like it was there for an eternity when George pulled out I gasped for air, Tristen looked at me and said "now aren't you going to try harder next time slut?" I just nodded. I was flipped over by George and uncuffed. I stood up but got pushed back onto the bed Tristen glared at me. I realized I was nothing but his little slut to him... A trophy to show off and abuse... And it turned me on so much.

Tristen then told me to show George my toy, to which I presented my ass to him in a doggystyle position. George chuckled to himself and grabbed my hips and pulled me closer to him. He then grasped the butt plug that was nestled inside me. He twisted it and slowly pulled it out of me, it made me shudder with pleasure.

He then pushed it in slowly then pulled it out quickly. He then slipped his finger inside of me, then another. He then said to Tristen 'she' has a good ass hasn't she? He called me a girl... I dunno why but it felt right... it felt good, it felt right...

Before I could react George took his fingers out of me and pushed his big 8.5 inch cock inside me, oh my GOD it was perfect! His cock was perfect smooth and slick, long and hard, thick and strong. He took me by my hips and trusted deep inside me, reaching a point never touched before and it felt so good!

He pounded my ass hard and fast making me moan louder and louder. He then flipped me over so I was on top in a reverse cowgirl position he started thrusting deep inside me. This is when Tristen stands in front of me dick swinging and a big grin on his face.

He then says, "I hope you have room for one more in there... One more?"

I could barely fit George inside me let alone Tristen as well! But I didn't care I just wanted this to continue so I nodded at him. He came over, lubed up his cock and squeezed it, my eyes bulged I tried jumping up but George pushed me back down, then Tristen popped in, he pushed deeper and deeper until he was completely in.

Then both George and Tristen started fucking me together, the sensation was incredible! Feeling both of these two strong men pressed up against my body, calling me a slut and their whore, feeling so overpowered and helpless. At the same time I felt like I was a princess I felt so girly, I felt so sexy and it felt so right!

Soon George erupted inside me followed quickly by Tristen. They pulled out, George threw me to one side.

Tristen said, "Are you just going to let our gift go to waste? Eat it up slut!"

I immediately started scooping their cum out of my gaping ass and eating it up. They both chuckled to one another and gave a cheeky wink to me.

They both left the room and started talking, I couldn't hear much but what I did was how George knew some guys who could release my potential for a certain fee... What this was about I had no idea, but I was soon to find out...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
6 Comments
AnonymousAnonymousalmost 10 years ago
why is that even here?

1) why call it a school slut so the guy is in school still its not like you made more than one vague reference to that.

2) what has this got to do with transsexuals/crossdressers?

3) and seriously put a little imagination into a story don't just outline your own fantasies.

AnonymousAnonymousalmost 10 years ago
a verse comes to mind!

ba-da-RUMP-BUM BUM

ba-da-RUMP-BUM BUM!

Gonna JAM that PENIS

Up his RUMP! BUM BUM!

AnonymousAnonymousalmost 10 years ago
Wrong section, Sherlock!

This is in the wrong session. The buttfucker section is a bit different from the crossdresser shemale section. Aside from the story being lousy apparently the dumb-ass author doesn't know any different.

AnonymousAnonymousalmost 10 years ago
sucked alright

This should have been in the gay section .

AnonymousAnonymousalmost 10 years ago

How sweet, you stupid slut. Now get over here and suck me off

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Party Slut Never fall asleep at parties!in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
The School Tramp From Nerd to Bad Bad Girlin Transgender & Crossdressers
A College Sissy Ch. 01 Freshman is feminized, used by male roommate and girl.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
More Stories