Surprise Birthday Pleasures

There's only one girl in this threesome...can you guess which one?

Believe it or not, this is my slightly more condensed version. There were some concepts that I had originally wanted to include in this caption, but ultimately decided to leave out to to length issues. As you can see however, it's still quite long. I originally contemplated splitting it into two panels, but I only had one picture, thus, I decided to settle on this magazine style layout (inspired by Cosmo).

And before you ask, I'm not back yet, but sometimes I just have these ideas that need to be written down and elaborated upon. This was one of them. You can probably look for a few more captions from me in the future, but I'm not sure what my output will look like for quite some time.


Transcript:

“Do you like this?” my girlfriend Chelsea cooed as she stroked my engorged cock with her expert hand. “Do you like being my sissy?”

My makeup smeared and hair tussled, I nodded vigorously.  Any verbal affirmation would’ve been utterly unintelligible through my enthusiastic moans. 

On all fours, I rocked back to meet the cock burying itself deep within my ass; Adrian was a male escort Chelsea had hired for the night. Between the raw, carnal domination of my posterior and the fine, delicate manipulations of Chelsea’s hands, my cock had been on the edge of exploding for hours, but Chelsea had been careful not to let me. I wanted to cum so bad. I was desperate. Just a little more sensation and then…oh there it was…I could feel it building, the tensing, the ignition, and then—

Thwack! I inhaled sharply. The sharp sting across my face was nothing compared to the sudden clench on my balls. 

“Tut tut dear, you aren’t allowed to cum until I say so. Your cock is mine!” Chelsea smiled wickedly and added another agonizing squeeze just for emphasis.

Who would’ve guessed Chelsea could be so kinky? For two years we’d been a fairly normal couple, but all that was shattered six days ago, when Chelsea found some fantasies on my laptop that I thought I’d been careful enough to cover up. In her defense, she’d only been trying to find out what to get me for my upcoming birthday, which as it happened, was also in six days time. 

Today was my birthday. I don’t remember much of what happened this morning, only vague impressions of being injected with some sort of sedative and Chelsea explaining calmly that I shouldn’t worry and it was all part of the surprise. And some surprise it was. With the hair extensions and the makeup, I couldn’t recognize myself when I first woke up. It also didn’t hurt that Chelsea had completely depilated my entire body. My skin hadn’t been so smooth since I was born. But that was only half of the surprise. 

Adrian arrived a short while later and against my protests, treated me to an afternoon in the city while Chelsea kept watch close by. I was horrified to be out in public. Yes, I’d fantasized about situations like this before, but there were people I knew on the streets: friends, coworkers, and bosses! I couldn’t tell you how relieved I was when the ‘date’ finally finished. I thought the surprise was finally over. How wrong I was. Turns out the ‘date’ wasn’t the only thing Chelsea had hired Adrian for. Adrian had also been hired to initiate me into the throes of womanhood!

I was terrified at first. How could I not be? But Chelsea was insistent. She’d shelled out good money for my first time and she wasn’t about to let some nerves get in the way. I might’ve yelped when Adrian slid into me for the first time, but soon I was fucking him like a first class whore; Chelsea intended it as a compliment. I felt like a dirty bitch too, the way I let Adrian take me, and it felt good to be free to be nasty slut. I would’ve came several times already if Chelsea hadn’t been attentively denying me that pleasure. I didn’t know my balls could ache so badly until now. She’d been flirting with my sanity for hours. 

“Well now sissy, you’ve been a very good little girl, and good little girls get rewards,” Chelsea stroked my matted hair as she spoke. “Now I know you’ve been dying to cum—ooh, I can’t even say the word cum without making you quiver—so on the count of three, I am going to let you squirt your hot massive load all over me. Consider it your birthday present.”

 

“One,” her electric touch excited my throbbing member.

“Two,” she began to stroke faster and faster.

“Three!” My whole body convulsed, hot seed spilling all over Chelsea’s stomach. 

I collapsed on top of her in exhaustion, limp and utterly drained. I felt her arms wrap around me in a gentle embrace. It was a rare peaceful moment, her and I, resting in each other’s arms, basking in post-coital bliss. 

“Happy first birthday, slut and may you have many more like it to come.”