Revenge gone... good?

Just to tease him a bit I leaned there and kissed one of his balls. Wow, such a weird thing for a guy who was straight all his life. But well, being drunk helped me to cross the... taboo line.

Should I go bold and touch him in front...?

I spent some more time licking over his cute small pink entrance, thinking about my next move, but I was so fucking tempted... Almost like something was pulling me there, I was so FUCKING curious how it would feel to touch another's guy dick. I really don't know why. Stupid idea? Maybe not so stupid.

Fuck, fuck, fuck. I squeezed my eyelids.

Okay! We live only once!

And I slowly moved my hand around his hip, directing it toward his dick.

Yep. It was there. My first feel of another man's intimate part. A bit scary, but exciting.

Ryder made a small exhale, the moment I skimmed over it.

It was still hidden under the front part of the thong, so I didn't touch naked skin, but it was enough to feel he was fully hard, dick sticking up, pressed to his body by the tight thong.

It was a small dick, as he said earlier, and I was so excited about that because it seemed more... femboyish that way! But even more exciting was the thought - that all my caressing on his ass had visible, tangible results. He was hard because of me. I got him aroused. And it... made my own arousal even stronger.

I gently stroked him through the layer of satin. A shy, delicate gesture.

"Kneel by the couch..." I whispered.

Ryder obeyed. He kneeled there, his skirt still up, his pretty ass bared for me to admire.

"Fuck, what a nice ass you have..." I added, patting it a bit. It was covered in my hickeys. I squeezed and wiggled it. "So pretty," I muttered.

And then very slowly I moved my finger along the crease, grazing over his pucker.

Ryder held his breath for a second. It was a border I couldn't just cross without his consent.

Leaning down over his head, that was covered with a curly blond wig, I whispered into his ear,

"Will you let me inside?"

I waited for his answer excitedly. The moment he nodded, he simultaneously turned his palm up to me. He had a small tube of lube in his hand. Wow! Ryder was so far ahead of me. I also held my breath for a second. Was it going to happen for real? Fuck. My dick throbbed in my pants eagerly, obviously being on board with the idea. Crazy! Crazy! Maybe I shouldn't drink that much?

Fuck that. I was gonna go for that, that's for sure. Experiment of a lifetime.

Straightening up, I squeezed the blob of lube to my hand and applied it to his entrance. I kinda knew what to do as I had had anal sex with women, so I started with one finger.

Wow, he was pretty tight. How was I ever gonna squeeze inside with my fat dick? I ogled his ass, he had narrow hips, not much space to fit in. Well, but nothing was gonna discourage me from trying!

I decided to take my time, the view itself was pretty nice, seeing my fingers disappearing in his tight channel, the weird feeling of power took possession of me. I actually realized I was enjoying doing it. Stretching Ryder, preparing him for me...

There was something exciting in this how he literally let me do everything, touch him in this most intimate place. Even more intimate than the dick. Dick is regarded more as a part that is... just very frequently touched. The attention is on it - more often than on an anus.

So, it was an even more private and sensitive area of the body. Kind of a secret! The amount of submission required from a man to offer himself in such an intimate act... had my blood boiling and was making me see red. I wanted to accept his offering so much, the invitation to penetration was so clear - his ass jutting out, legs spread - that I had trouble with my breathing.

Plunging my two and finally three fingers inside his pliant body, made my dick almost constantly throb, small waves of blood kinda pushing down, filling it, making it jerk. I fucking needed to fit there! Into this super tight, hot place... YES!

"Gonna go in..." I murmured tersely and quickly pulled out my stiff dick, kinda scared he was gonna back out. Fuck, when was the last time I was so hard? I felt like I had a real bone inside my shaft.

I lubed my dick very generously and added even more on his ass to ease the entering.

And I pressed my dick head to it. It looked crazy big! His small ass was much smaller than any girl I ever had. Such slim hips that I stroked in amazement.

"Brace yourself..." I whispered and... pushed.

My dick breached his muscle ring, and he made a small cry, or maybe just a very loud exhale?

I stopped and tried to regulate my breathing as it was pretty sped up. I wanted to ram into him right away, and bottom out, but I knew I still had a long road ahead. I glanced down. His poor hole looked super stretched, the muscle rim looked like a pink rubber band.

I felt stupid for a moment. Fuck, was I torturing the guy with my thick dick? This couldn't possibly feel good, could it? Just to check what was going on I lowered my hand under his pelvis.

Yes, his dick flagged down a bit, but not totally. Could I maybe help him a bit?

Swallowing, I pulled his thong finally down. His dick almost fell into my lubed hand. Fuck, it was warm as my own, but in a way nicer to touch, more silky than my own, which felt more veiny and meaty.

Kinda awkwardly, slowly, I started to stroke it - very shyly at first, almost clumsily. But I was patient, wanting him to adjust to me and that he still had some pleasure out of this endeavor. My whole dick head was inside, but I wasn't moving my hips, only slowly jerked him off.

He soon regained his hardness, which prompted me to ask, "Can I try to go a bit deeper?"

He nodded again. For some reason, he didn't answer me with his voice, maybe didn't want to spoil this for me speaking in a low, manly voice? Was it supposed to be an experience of fucking a femboy, not 'a-real' man? Maybe he intended that?

But even in my drunk state, I knew he was a man. And it didn't take anything away from this experience, if anything - it even added to it.

Super-slowly I pushed deeper... really, really unhurriedly... stopping from time to time, allowing him to breathe through it. It took quite a time, but I didn't forget about his poor dick and continued to stroke it, keeping it alive. Finally - no idea how long after that - I felt like I'm kinda pushing into something even tighter, and something inside him is literally rearranging itself to accommodate me. As I bottomed out, my pubes pressed on his ass cheeks.

"You did well, Ryder..." I whispered using his name, to acknowledge I wasn't that deluded (or drunk) not to know I was fucking him. I stayed in that position for some time, patiently stroking his dick, giving him pause. But I also wanted to say something nice to him, to encourage him... to endure a bit more!

"I've never been in anyone so tight, Ryder. It may end very quickly..." I added with a lower voice and... I felt a slight throb in his dick! Was this arousing him? I tried even harder, "So tight, so fucking tight, gonna flood you with my cum, such a narrow, hot hole..."

A bit of awkward dirty talk never killed anyone, right?

His breath seemed even a bit quicker. Yep. It worked!

"Can... move?" I didn't care, I was speaking in sentence fragments, my pulse spiking high.

Gladly, I heard his quiet whisper, "Yes..."

So, I started to move. Very carefully - because he really was so fucking tight. I had an impression that something held my dick in a very strong grip. Almost squeezing me. It was not a good prediction of how quickly I was gonna unload, but... on the other hand I was still drunk, and that always helped me to hold on a bit longer.

So, not stopping with the jerking off, I started to thrust inside. His breath became louder and deeper, I just knew he was balancing on the edge of pain and pleasure. I sort of pushed myself into that mindset - I either die or make him cum! I couldn't think of fucking him and just leaving him behind. So, I focused on working on his dick, leaning down into a position that was not super comfortable, but I had to endure that.

Tirelessly, I fucked him and jerked him off, minute after minute... or so I thought. I had no idea how long it took before he suddenly made this weird, gasping sound and his dick started to spit under my fingers. It was so... unreal! Another man cumming in my palm!

Sooo... interesting, though. Even satisfying!

I was now free to act. I could take care of my own pleasure. I grabbed his hips and quickened my pace. Fuck! It was pure heaven! Tight, godly tight tunnel, holding me like a vice.

Moving inside his body was an absolutely, perfectly pleasant feeling. Blissful!

I tilted my head back, and fucked him, making all kinds of wild sounds, sinking deep in the ecstasy, our skin slapping.

"Gonna..." I managed, and my body just shivered, my hips pushing forward, hammering in his tightness, feeling such an immense delight, climaxing, unloading in him, filling him with my sperm.

"God! Fuck! Dammit!..." I mumbled under my breath, jetting in him like a high-pressure hose.

I leaned my forehead on his nape.

His wig smelled like Chanel Allure perfume. I had this weird thought that it didn't originally belong to him... but I didn't pay attention to it.

My knees were bothering me more and more on the hard floor, so in an odd impulse I grabbed him by the waist and... stood up! I walked toward his bedroom, carrying him and we both kinda fell on bed...

But by chance, he fell on his back, not on his stomach, so suddenly we were face to face!

I froze, being propped over him on all my fours, his face clearly visible in the light of a nightstand lamp.

For the first time since the moment I started to fuck him, we saw each other faces. He had pink cheeks, and lips painted with red lipstick. His makeup was pretty bold, but not very professional, so he probably wasn't doing it often enough to become proficient. His eyeshadow was as dark brown as his eyes, and he had mascara on his thick lashes.

The silence was awkward but also... somewhat sweet. I really don't know why, but I smiled.

His pink lips responded with a similar shy smile. I wanted to say something nice, so he would remember our interesting endeavor as something pleasant - but not only on a physical level.

"You know what, Ryder? Donna's stupid. Your dick is dope, man!"

He blushed and giggled. "Thanks..."

I hesitated. We stared at each other for a while and I slowly lowered my eyes to his lips, that parted immediately. I took it as an invitation, and I went for it. We kissed, shyly at first, cautiously, but soon the intensity increased. I had never kissed a guy before, but it wasn't really much different, so I found a blissful pleasure in it. My left hand kinda roamed over the smooth plains of his hips and caressed the round bubble of his ass. And my fingers... found his lubed pucker.

The moment I slid my finger there, Ryder made a sudden exhale, breaking the kiss. Our eyes were now almost glued to each other. I started to gently fucking him like that. His mouth slightly opened, he started to pant at a quicker pace. My dick - magically - went hard again! What the fuck? When have I ever gotten hard that quickly?

"One more time?" I asked, and he blushed even more, but pretty eagerly nodded...

So, we did it one more time. And soon after that... the third time.

Yep. It was a very enlightening night.

***

I was awakened by some voice speaking something almost directly over me.

"Ryder?! What the fuck!"

Still kinda half asleep, I made an effort to open my swollen eyelids. Blinking almost as if light-strucken, I noticed a woman standing right above me.

I did know her that well, but I was aware of who she was. It was Donna, Ryder's ex-girlfriend. Much slimmer than the last time I saw her, her hair purple-pink and her nose pierced. She definitely looked more edgy. The shy, overweight girl - gone, replaced by... her new persona.

She stared at us with a shock in her eyes.

So, I looked around. I was lying flat on my back and... something heavy was on my arm.

Did I actually sleep with Ryder in my arms? Well, that was a bit unexpected, to say the least.

This "heavy" thing was his head, and he still had the blond wig on! My arm was around his shoulder, almost like we were tender lovers.

Her voice awoke him too, and Ryder sat up nervously coughing.

"What are you doing here?!" he snapped out, throwing away the wig in a frustrated gesture.

Donna blinked dumbfoundedly.

"What are you doing in bed with your coworker?"

Ryder snorted and laughed sharply.

"None of your fucking business!"

"He has no pants!" she almost screamed.

Only then I realized I really had no pants. But it wasn't the worst part of my realization...

I also didn't have my briefs!

Fuck! She was staring right at my morning wood! I jerked my body and the first thing I found under my hand was the wig... So, I covered myself with it.

"That's my wig!" she yelled in panic. Fuck. So, I threw the wig toward her and... tried to pull out the duvet from under us, but to no avail, as we were sitting on it, so ... I grabbed Ryder! Yep. And moved him toward me, so he was on the line between me and Donna, between my spread legs.

The silence after that became pretty awkward.

"Did you fuck him?!" Donna asked in a raised voice.

Ryder almost growled.

"What's it to you? Once again, it's not your fucking business!"

"I beg to disagree! I don't want you or anyone fucking in my maid costume, and in my wig, idiot!"

"Fuck you! You left it!"

Okay, I was convinced that this conversation couldn't end well. I wasn't going to be there to see it anyway. So, I jumped up from the bed and stormed toward the living room, where my pants should be.

Dressing, I cursed under my breath. What a mess, what a mess... Subsequently, I ran away from Ryder's condo, still hearing their back and forth coming from the bedroom.

Being outside already I realized with even more panic that today was NOT Saturday, but Friday! And it was already 9:30AM! So, I was 30 minutes late as of now.

Not that our boss, Professor Callahan, would care too much, but it was better not to cross him.

So, I quickly headed toward my part of the teacher's condominium. I was prepared to meet Stacy because her work started at 11AM, but I was surprised - the apartment was empty.

I took a super quick shower, changed my clothes and drank half a gallon of milk.

Feeling confused, I stormed outside, hoping to be at my post around... at least 10AM.

As I opened the door and entered the room where Ryder and I usually work - I froze.

One surprising thing - Ryder was already here! So, he was even quicker than me, probably having Donna screeching over his head was an even better motivational factor. His curly brown hair was still a bit wet.

But that wasn't the most surprising part.

There was somebody else sitting in the room... in my own seat!

Stacy.

Fuck, what was wrong with these cheating girlfriends? Why did they both have to pick the same day?

I clenched my jaws, as she leaped to her feet.

"Lane. Hi!"

Wincing, I crossed my hands on my chest.

"Stacy. What are you doing here? And where's your... new fuckboy?"

Stacy grimaced. "Lane... can we speak somewhere privately?"

I snorted. "Nope. Whatever you want to say, you can say it in front of Ryder."

Ryder snapped his head up, tearing his eyes from his laptop screen and looked at me with surprise.

I smirked.

Stacy closed her eyes. "Lane, it was...a misunderstanding. He's my ex, we had a couple of beers, it was nothing, it meant nothing..." she started to explain, while I tilted my head with an invidious grimace.

Ryder's face was also pretty hostile, when he glanced at her.

Yep, he understood me sooooooo well!

"Pack your things, Stacy," I said, forcing myself to speak calmly. "I don't want to see you in my condo when I'm back from work. The key you may leave... under the mat," I instructed her in a matter-of-fact tone of voice.

Ryder chuckled, and, curiously, blushed lightly.

She glanced toward him, obviously not understanding what was going on.

"You can't be serious Lane, it was just a stupid, one-time thing..."

Clenching my jaw, I took one step back. "Stop lying Stacy, you did it before. But so you know. I also slept with someone last night. So, we're almost even. But it's over between us, anyway. I have a very simple policy: Either you're in 100%, or you're out. There's no in between. Pack your things and get the hell out of my life."

Stacy tightened her lips, obviously annoyed. "Tell me at least, who is she..."

Ryder chuckled loudly, and I only shook my head.

"None of your business, Stacy."

But she just couldn't stop...

"Do I know her?!"

I narrowed my eyes. She was getting on my nerves.

"Do you really want to know so much? Okay. It's not her. It's him."

The silence was almost deafening. She gaped at me, her eyes round, the state of pure shock on her pretty face. I hoped it would discourage her once and for all.

It was unnecessary to prolong it for both of our sake.

My policy truly was 100% or 0%. I was a simple guy.

"Get out..." I repeated, speaking slowly and pointing toward the door with my hand.

This time, she didn't say anything. She just snorted and ran toward the exit like there was a fire in the room, leaving me and Ryder alone.

He stared at me, while I shrugged innocently.

"So that was obviously the end of my relationship with Stacy."

"Yep. I saw it." He winked and stood up to come closer to me.

I felt my heart quickening. He wasn't wearing a maid costume now, but there was still something sweet about him. Cute and femboyish. I don't know how I missed it before!

We were now standing in front of each other. But this time the silence wasn't unpleasant. It was kinda... exciting and nervous at the same time. I felt like I had pink bubbles going crazy in my chest - the feeling so intense, I was almost afraid I'd start floating. I was weirdly happy, but had no idea why.

So I just smiled.

And he smiled softly in response.

"So... are you by chance free this evening?" I asked, biting my lip.

He tilted his head in a bit of a flirtatious way.

"To be honest, I am free. And why do you want to know?"

I cleared my throat.

"So... I was about to pay a visit to a shop I know, with some interesting costumes. And after that, I would gladly repeat some nice... activities that I happened to discover lately and liked very, very much. But also I can just go for a movie, if you are... a bit too sore. That works for me too. So... Are you in?"

He giggled and winked. Yep, he really had long eyelashes! So cute...

"Oh, yes, Lane. I'm in. 100%!"

The end

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Thank you for reading my story!

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Thank you dnsontn for your quick and smooth help with editing!