Sissy's New Gym - His Name is Tyrone

Story Info
Fantasizing about my first lover as I sucked off another guy.
874 words
4.25
6.1k
6
0

Part 4 of the 4 part series

Updated 06/10/2023
Created 08/17/2021
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

Carl - one of the guys that I'd been sucking off for a few weeks - had a 9" cock that reminded me of my first lover's cock. When I mentioned that to him, he surprised me by responding "Oh, you mean Tyrone?" I didn't know who he was thinking of, but when he said he watched Tyrone fucking me and taking my virginity, I knew that was him. I finally knew his name, but I didn't know why he never returned after fucking me. What a relief when Carl explained that Tyrone was a Marine who got deployed again and told him that he wanted to fuck me again when he returned home.

As I took Carl's cock into my mouth, I closed my eyes and thought about when I took Tyrone's bulbous head into my mouth for the second time.

Having sucked it a day earlier, it was already familiar to me. But this time was different. It wasn't his cock that had changed - it was me.

Each time his rigid shaft slipped into my throat, I wondered if his full length would fit so easily inside me when he fucked me. I wondered if my bottom would feel as satisfyingly full as my mouth felt right then.

But I was getting ahead of myself. I didn't even know if he was going to fuck me. And I wasn't sure how to get him to do it. So, I just pulled off of his cock, looked up at him and asked him if he wanted to fuck me.

When he didn't respond, I feared I went too far. A man like him probably doesn't fuck other guys - not even a sissy like me.

Before I could formulate another thought, he was behind me. He placed his hands around me and lifted me up from my waist. When he yanked my panties down, I expected to feel his full length inside me momentarily.

Instead, he gently placed his cock head against my bum and began sliding his saliva-drenched cock up and down the length of my crack.

I gasped each time his man-meat crossed my rosebud. I was aching for him to take my anal virginity, but he knew how big his cock is, and he must have known how tight my hole would be.

He pressed in just a bit, parting my cheeks with his hands as he slowly pushed inside. As his head finally popped in, I felt so stretched and so full. And he still had 8" more for me.

I was so glad I had practiced so much with my rubber dong. But it was nothing like having a real cock inside my bottom. The warmth, the pulsing of the shaft, having a real man pushing it into me. It just wasn't the same.

My eyes suddenly opened wide and I shrieked as Tyrone buried all 9" inside me. With his large, manly balls slapping against my tight little sissy ball sac, he drove his massive cock in and out of me so fast and so hard, I could hardly catch my breath.

After a few dozen deeply satisfying strokes, I thought I felt him cumming, but he kept going. Looking down between my legs, I saw myself spurting on the floor through the tiny tube in my chastity cage.

I ejaculated two more times before he finally grabbed my tummy and pulled me toward him as he grunted while filling my bottom with his seed. I could feel his warm sperm shooting into me.

A minute later, he had withdrawn his cock. I felt so empty - even as his semen began leaking out of my stretched hole and running down my smoothly shaved legs.

Without even thinking, I turned around and dropped to my knees, and thus began my tradition of always sucking a man's cock clean after he fucks me.

He tasted a bit different - with my ass juices mixed in, but that familiar taste of his delicious black cock and his salty white semen made me keep bobbing until he flooded my mouth with another load.

I swished his seed around in my mouth, swallowing a little bit at a time as I watched him push his deflated cock into his underwear.

When he was fully dressed and I had consumed all his delicious offering, he headed to the door and simply stated "see you tomorrow." That's all I needed to hear to make my day.

All day long, I could feel his sperm tingling inside. Everyone in my office surely saw the wet spot on the back of my pants from his semen leaking out of my bum and soaking the backside of my panties.

I kept my damp panties on and replaced my soiled pants with a pretty pink lace nighty when I slipped into my bed that night.

I suddenly snapped out of my daze and opened my eyes to find my face splattered with Carl's semen. He didn't take offense at my obvious preoccupation with my memories of Tyrone; he was happy to just finish himself off on me. Before he left, he suggested that when Tyrone comes back, I ride both their cocks at the same time!

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

READ MORE OF THIS SERIES

Similar Stories

John to Jane, Becoming a Bi Cuck How I became a bi cuck for my fiancé and her bull.in Transgender & Crossdressers
Unexpected Encounter at the Theater Sissy Kristy meets someone she knows at an adult theater.in Transgender & Crossdressers
My Roommate's Maid Pt. 01 College student forced to be their roommate's sissy maid.in Transgender & Crossdressers
Boyfriend Turned Girlfriend Ashley turns Matt into Maddie for the first time.in Transgender & Crossdressers
Sissy College Slut Pt. 01 Alex and his black roommate gets to know each other better.in Transgender & Crossdressers
More Stories