Chapter 12

Content Warning: Self-cest. If this makes you uncomfortable, you can skip ahead to Chapter 13 without missing any plot.

I texted Morgan that I was going to spend the night at Daniel’s, then turned off my phone. I still had doubts as I hit send.

I found myself standing at the door to my room - I mean Daniel’s room. The door was open slightly, looking closed to passersby, but clearly an invitation to me. Was I really about to do this? I was both horny and curious, so I pushed the door open and walked in.

The main lights were off, and the room was illuminated by my laptop. 

I let the door close behind me. 

Daniel closed the lid on the laptop and the room went dark, save for a distant streetlight filtering in through gaps in the window blinds.

Am I really going to do this? Sure, he’s my body. Maybe if I pretend he’s Morgan. Or maybe I’ll pretend he’s Jasmine. After all, he’s been both.

His silhouette stood up in front of the window. “Jasmine, we don’t have to-”

Now or never. I rushed towards him and kissed him before he could finish his sentence. Earlier he had planted the seed of kissing yourself. Curiosity got the best of me. As our lips touched, my body instantly went into autopilot and I embraced him as if he were my long-time lover. In a way, he was.

Daniel wasted no time wrapping his scrawny arms around me. Those were my arms not so long ago.

Thankfully, kissing him was no different than kissing any of the girls I’ve had relations with over the past five weeks. I raised my hand to cradle his face, but the moment I touched the familiar grainy stubble that I dealt with throughout my adult life, my hand recoiled. It broke the illusion I was going for. I tried again, this time putting my hands on his shoulders to pull him in tight.

Daniel softly groaned and his hands timidly caressed my back - as if he didn’t know what to do with them. 

This went on for at least a minute or two. We kissed and kissed and his hands didn’t move at all. This surprised me because if he was truly the girl I had sex with four weeks ago then he was far more experienced than me. Either he was playing the part of virgin Daniel, or he was making it abundantly clear that this was my show. After all, I was the one who willingly came back. 

From what I have come to know of Guild members, the answer was likely a little of both. He was playing a part, and he was respecting me as a woman, and respecting me as a Guild member.

The idea he was playing me felt weird. He was awkward and timid and I wasn’t flattered by this portrayal, whether accurate or not. It almost seemed as if he was mocking me.

But, however Daniel behaves, I still have to play my part. I’m Jasmine. I have to lead. This is my story and I get to decide how Daniel loses his virginity. 

I grabbed his hand and placed it against one of my breasts.

He gently massaged it. I felt a tingle, and my nipple began to harden inside my bra.

Two things were swirling in my head. What do I want done to my current body, and what do I want done to my original body? In search of answers, I reached down between his legs and felt his growing bulge. I gently massaged it with my hand and felt it get larger. 

“Fuck,” he moaned as he broke away from our kiss. Through the faint ambient light I could see he had lust in his eyes. Lust for me. 

I unbuttoned his jeans and slid them and his boxers down enough to spring free my old friend. Oh wow, he’s been manscaping. I actually liked it. It made Little Daniel look larger. As I stroked my old penis I reminded myself that this was indeed my penis. It was a little weird stroking it from this angle, but Daniel made no complaints and started to breathe heavier. As I stroked the length of it, I could feel my pussy throb and dampen my panties even more.

He whimpered needily and stood there waiting for my next move.

I slowly walked us over to my bed- I mean his bed. I sat him down and gave his hard cock one more stroke.

He leaned back against the wall looking lustfully at me. It was time to take things to the next level.

“Good boy,” I whispered. I knelt down in front of him and looked at his dick. My dick. My mouth watered as I contemplated what I was about to do. He was right. There were times I wanted to take my own member in my mouth. I was single, and the idea of finding a girl to go down on me seemed like a distant pipe dream. I was curious. What would it feel like on my tongue? What would it taste like? Sadly, my body didn’t contort that way and I nearly threw out my back once while trying. But here was my opportunity. I gently wrapped my fingers around it and stroked it a few times. 

My pussy throbbed some more. I could feel my own juices continue to soak my panties. With my free hand I reached down and rubbed my clit through them. She would just have to wait her turn.

I leaned closer to my former dick. I’ve gotten close in the past, but never this close. I could feel the heat radiating off of it. When it was mine, I was rather proud of it. It’s length. Its girth. I was no porn star, but I felt I could measure up to any of my male peers and make any woman swoon. Sadly, my confidence in my dick never manifested to any other part of my life. In fact, that pride seemed so insignificant now. I felt no remorse or jealousy that it wasn’t currently attached to my body.

Daniel looked at me with a patient smile on his face. He must have known what was going through my mind, and was happy to let me savor this moment, even if it delayed his pleasure.

I stroked it a few more times until I noticed a bead of precum on the tip. I leaned forward to lick it off. The sweet and salty flavor greeted my tongue.

I could do this. I just had to remember what Ella did to me the other week. I grasped his dick around the base and slowly brought it closer to my mouth. I slowly ran my tongue along the underside of his shaft to the base, and back to the tip. Then I slowly traced it around the head, before making another trip down the shaft. 

Daniel squirmed in pleasure. “You’re doing great.”

That wasn’t something I would say, but it was something an experienced partner would say when they knew this was my first time giving head. The expert/novice role reversal gave me a brief pause. I shook my insecurities away and continued.

I swirled my tongue slowly around the head until I found I was taking it into my mouth, wrapping my lips around it. I was actually sucking my own dick. Not something I expected to be doing when I got up this morning.

Daniel grabbed my hair and moaned, “Good girl.”

The out-of-character affirmation should’ve given me another pause, but instead sent a warm feeling throughout my body. I instantly started sucking it, and pumping the base some more. Inch by inch I took more of the shaft into my mouth.

My mind wanted to contemplate the differences between giving oral to a man vs a woman, but I had to remind myself that now wasn’t the time for that.

The more he moaned, the more of him I wanted to take. Before long, I could feel the head of his dick reach the back of my throat and I gagged.

That didn’t stop me and I tried again. With every moan I bobbed my head faster, wrapping my lips tightly against his cock. My cock. Even if it wasn’t attached to me at the moment, It was still mine, and if anyone was going to suck on it first, it was going to be me.

“Yeah, Jasmine,” he grunted. “That’s it.”

As I went faster and faster, I felt him tense up.

“Wait, wait,” he cried, cradling my head.

I took his stiff rod out of my mouth and looked up at him, my eyes begging to let me finish him off.

“I don’t want to cum yet,” he panted, then chuckled. “I don’t quite have the same restraint as your previous partners.” 

I nodded in agreement. He was right. I’m actually surprised he lasted this long.

He patted his lap, and I climbed up to join him. His dick was mere inches from my very soaked and pantyclad pussy.

For the first time, he took the lead and pulled my dress off, then clumsily unclasped my bra. I giggled patiently while he pretended to struggle, but a part of me was growing impatient at his performance, knowing full well that my lover had plenty of experience with putting on and taking off bras. “You’re so beautiful,” he gasped as he took in my naked form.

The compliment pierced through my insecurities. While I didn’t grow up Jasmine, I was Jasmine at the moment, and I felt beautiful and sexy and the compliment made me radiate.

“I’m all yours for tonight. Tell me what you want. I want to serve you, Mistress.” 

“Mistress?” I giggled. Usually that title is reserved for Lauren and-

“I read about your sex with Morgan.”

I blushed. “Oh, yeah. I don’t know what came over me that afternoon.”

“It was hot. I want some of that action.”

OK, well if that’s the part he wants me to play, then I’m going all in. I then arched my back and offered my breasts to him. 

He brought his head to my left breast and started tracing my nipple with his tongue. It sent a familiar electricity through my body. The wave of pleasure hit me and I wrapped my arms around his neck so I could hold him close.

“Good boy,” I said to him.

He clumsily played with my breast, completely ignoring other needy places.

I started massaging my other breast as I found my hips slowly starting to buck. The action was making my ass inch further and further up his lap. Until I reached what I was really looking for. I felt a jolt of satisfaction when my pussy was up against his dick.

His rod was iron-hard now and pressing firmly against my mound. 

I could feel it twitch. I could feel my pussy twitch in response.

He finally turned his attention to my other breast, and I continued to rub my pussy against his dick. All I knew is I wanted it. Hell, I needed it. I needed to feel it against my folds. Honestly, I think I really just wanted him to go down on me. After all, I’ve only ever had lesbian sex. That's all I know. Now I had the chance of a lifetime - to experience sex as a straight woman.

Out of nowhere, he lifted me into the air and laid me down next to him. I had no idea I was that strong. My legs were dangling off the bed and he knelt down in front of me.

Instead of going down on me, he reached up and cupped my breasts. 

I was a little disappointed. He was between my legs but playing with my breasts? I was starting to grow impatient, so I took one of his hands and placed it between my legs.

He gently traced the outline of my slit through my soaked panties, making me shiver. There we go, that’s better. He teased me with his hot breath as he continued to pet it.

Another minute went by and my panties were still on, and he didn’t bother putting his finger under them. Maybe I could reach my phone and check emails while waiting for him to get to third base. “Fuck it,” I muttered. I was getting impatient so I hooked my fingers into my panty’s waistband and arched my back.

“Allow me, Mistress,” he protested.

“On one condition,” I stipulated. I needed us to be on the same page. “I appreciate the role-play, but it’s a little weird. It's almost like you’re making fun of me. Can you just be yourself, and not Daniel?”

“Sorry,” he whispered. “I can be whoever you want me to be tonight.” He cupped my hands still hooked around my panties. I let go, and he slowly continued my panty’s path. He lightly caressed my legs as he took them off. I was so glad I shaved them.

I could feel the cool air on my wet pussy and I spread my legs for him. I coyly bit my lip and instinctively traced my folds with one of my fingers.

He removed my hand and held it tenderly while he brought his face to my sex.

He nuzzled my mound and I let out a whimper. I could feel his stubble on my skin. 

Much like he was Jasmine and I was Morgan, he masterfully peeled my folds away and flicked my clit. I’m glad he dropped the virgin Daniel act. I wanted to have sex with the same person I had sex with four weeks ago, not them pretending to be a timid virgin guy. After all, he knew what I wanted. He knew what this body wanted. Pretending otherwise was just tormenting me.

I balled up the comforter in my hands as wave after wave of pleasure filled me. I wanted to scream my partner's name. I didn’t know their name. All I knew was their body’s name. But that was my name. Would that be awkward? I did it anyway. “Fuck me, Daniel!”

Then his tongue and fingers went into overdrive and I let out a very primal moan. Yes, I remember this from our first time. This is really why I came back here.

“Fuck!” I’m sure the neighbors heard that.

He pulled back and looked at me as I caught my breath. He stroked his dick. “Do you want this? It’s not too late to change your mind, D.”

“That’s Mistress Jasmine to you,” I replied with a smirk.

“Command me, Mistress Jasmine. Make me yours.”

I adjusted myself on the bed so I was lying down. So he could top me. Here it is. I’m about to have my own penis thrust inside me. “I want you to fuck me, Daniel.” I instructed. “Stick your massive dick into my pussy.” Hey, I was stroking both our egos.

He opened his nightstand and pulled out a condom wrapper. 

Yes, I was a virgin at the start of this. I was also the kind of virgin who kept condoms in his night stand - just in case. I just wasn’t imagining this literal scenario where I was the one about to be fucked with one.

When he was done, he climbed onto the bed and positioned himself over me. He held onto his cock and teased my pussy by tracing the sticky wet folds with his own latex-wrapped head.

Slowly he began to push inside. I could feel myself filling up with his girth.

I wrapped my legs around his back as he started to slowly thrust.

My eyes went wide at the feeling of being filled with a dick. It was like no feeling I had felt before.

He slowly pulled out and pushed back in. Every nerve inside me could feel every part of his cock sliding back and forth.

He picked up his pace and my breathing increased. He then paused for a moment and shifted himself. The next thrust he did hit a different spot and I spasmed with pleasure.

“Oh fuck, that’s the spot!” I exclaimed.

He kept pumping and pumping.

“Yes, that’s it,” I said as I was filled with an orgasmic rush. “More, more.” Another orgasm washed over me.

“I’m close,” he grunted. He looked like he was painfully trying to hold it back.

I wanted this to last longer. “Don’t cum yet.”

He nodded and grimaced.

“Pull out,” I commanded. “I want to ride you.”

He pulled out of me. Even that action was pleasurable as I felt the shaft of his penis rub against my opening and the head pop out like a cork.

We both clumsily swapped places and I was now straddling his legs. I wondered how much more he had left in him.

I grabbed his dick and raised one of my legs. I slowly guided it into my hole. We were both covered with my juices so it slid right in and I exhausted a moan of pleasure.

I slowly started to bob on top of him, trying to find the same spot he was hitting earlier. After adjusting a few times I found it and let out a gasp.

“Yeah,” he moaned. “That’s the spot for me, too.”

I pinned his arms above his head and continued to ride him. “I want us to cum together,” I cried as my breathing picked up.

“Yes, mistress,” he moaned.

I continued to ride him as another wave of pleasure built up in me. 

He started to grunt.

I screamed, “Yes!”

As a massive orgasm thundered through my body I could feel his cock rhythmically pulsate and the subsequent hot liquid filling the condom inside me.

Neither of us could move until the orgasmic bliss subsided, nor did we want to. We shared another kiss as I dismounted his cock.

Both of us laid there catching our breath.

He eventually got up and discarded the condom into the trash before returning to the bed and nuzzling up next to me.

We both laid there panting as I draped my arm around him.

“You were amazing, Jasmine,” he whispered as he placed another kiss on my lips.

“You too, Daniel,” I said, returning the kiss.

We continued to make out for another few minutes before I noticed he had stopped kissing me.

“Are you awake?” I asked in a whisper.

He didn’t answer. I looked over and realized his eyes were closed. 

As the postcoital euphoria started to wear off, I started to get a weird feeling. Guilt? Shame? Embarrassment? I tried to push those thoughts out of my mind. I closed my own eyes and drifted off to sleep.