Halloween Pt3

My enthusiasm waivered a little once his crotch was in my face. I could see his cock straining against his sweat pants. But, I considered the alternatives: He was horny, and he was expecting relief. We were in his frat house. And he was much bigger than I was. And, I was dressed like a young woman hot for the D. If I told him no, he could easily beat the shit out of me. And then tell everyone he was fooled. God knows what his frat b*****rs would do.

Besides, he'd sucked my cock. How bad could it be? Women liked giving blow jobs, and obviously some guys did too. It's not like anyone would know. He probably wanted things on the down-low too.

So, taking a deep breath, I reached to the waistband of his sweats, and pulled them down a little; just enough to release his big, black dick.

It looked huge, but in all fairness, it was right in front of me. 7? 8 inches? All I knew was there was very little likelihood of me deep throating that thing. I grasped it gently, and leaned in, to kiss the base. The musky scent didn't kill me, and the sensation in my hand felt oddly enticing.

After a few nibbles on his actual body, I pulled back, and kissed the tip. And again. And again, this time, letting my tongue slide across the head. He moaned softly, and I felt encouraged. So, here I went. I opened my lips and took the head in.

It felt warm on my tongue. I took him deeper. The shaft passed my lips. It felt hard, and yet, at the same time, soft. I took him deeper. And deeper. I opened my eyes, and realized he was halfway in. And then I realized something else: I liked it. I liked the feeling of his erect penis in my mouth. I liked the little noises he was making. I liked the gentle touch of his hand on the side of my head. Cocksucking wasn't bad at all. Matter of fact, I wondered why I hadn't done this sooner. Everyone should give blowjobs! They're wonderful! Most of the world's problems would probably disappear if we could all just relax and suck a dick every now and then!

I pulled back, dragging my lips over the pumping veins as I moved. He groaned again. Moving forward, I eased him a little deeper. Draw back, slide forward. This felt good. I'd been on the receiving end before, as recently as 2 minutes ago, and I have to say, I think I may enjoy this half of a blowjob more.

But then, disaster.

I went too deep, and triggered my gag reflex. Forcing back a choking cough, I fell back, and he felt out of my mouth. I was embarrassed, and I hoped to god I didn't offend him, or nick him with a tooth. Looking up at him, all I got was a big smile of encouragement. He didn't say anything. He didn't have to.

Back to, I hesitate to call it "work". But this time, I knew my limit. Like I thought earlier, there was no way I was going to get all of it in my mouth. Maybe with a little practice. Practice!?! Was I planning on doing this again? Oh, yes, I was. All doubts were leaving my mind as I sped up the back and forth, in and out.

He placed his hand on the top of my head, and I felt my wig shift. I froze. Would that ruin the moment if it came off? But his hand, gently again, shifted it back into place, and I continued, glancing up every now and then, to make sure he was pleased.

Every time he had touched me, it had been gentled. For such a big guy, he moved so carefully, gracefully. The way he held me, kissed me, guided me. He made me feel safe, and desired.

And now, I felt his body seize up. Stress locked his muscles, and I knew what was coming. But I hadn't thought about it before. Was I going to swallow or...

Too late to think about it now, as he erupted in my mouth. I felt the first spurt hit the back of my throat, and instinctively I pulled back a little. The next landed on the back of my tongue, the third on the front. I felt like I couldn't breath, suddenly, with his dick in my mouth, and all other available space filled up with my saliva and his cum. He pulled out, and I felt something wet and hot land on my forehead.

I wouldn't say the spell was broken, but I was suddenly shocked at what had just happened. A man I'd never seen before put his dick in my mouth, and then ejaculated. In me, and on me. I guess I almost froze. I thought about this taste in my mouth, and how it almost made me gag again, but also tasted kind of good; like cantaloupe with a lot of salt.

He pulled back, took a deep breath, and I watched as his dick fell limp. "Damn, girl. You're good!" He tucked himself back into his sweatpants, and started toward the door. "I dunno about you, but I need a drink." He said something about keeping the door closed, and his roommate, as he walked out into the hallway, pulling it closed behind him.

So, on top of me giving my first blowjob to a complete stranger, while in drag, I'd apparently been used. Used and tossed away. Like a cheap tramp. Was it always like this? If I did decide to suck more dicks, was I always going to be treated like a quick plaything? Is this how women felt? Had I ever done that to a girl? I was pretty sure I had at least once, and now I felt like a complete dick. Was this karma? My penance? I was sentenced to a purgatory of wanting dick, but only getting it on the run? And did I want to live that way? What the fuck was happening to me?

I was starting to feel rather emotional and vulnerable, and I was thinking, quite seriously about crying, when the door opened again. There stood a gorgeous redhead in a tight white dress. Colette. My roommate, Todd. She looked shocked.

She hurried over to me, closing the door behind her. Her. I was thinking of Todd as "her". Of course, I couldn't judge. I had some guy's cum starting to slide down my forehead.

Colette pulled a tissue out of her bosom, and dabbed at the mess on my face. "Omigod, are you okay? Did he hurt you?"

"No," I heard myself say in a flat voice. "I did it of my own free will. I sucked him off, because I wanted to," I looked up at her, looking for reassurance. "He got off, and left."

"Yeah, he does that," she answered. Todd was still using the Colette girly-voice, I noticed. But I also noticed what she said, and not just how she said it. I gave her a questioning look.

She sighed, deep and heavy. "Okay. I'm sorry. This is all my fault. I should have been more honest with you."

"This is not my first time dressing up. I guess you probably guessed that by now. I've been dressing up for years. Since grade school. Usually in secret. On weekends, when you go home, I get dressed up. And until this summer, that was all I did."

Another sigh.

"I got lonely this summer, when you were gone. And I'd fantasized about being with a man. So, I put an ad on Craigslist, and he answered. We chatted for a week, and then exchanged numbers, and texted for awhile before I got up the nerve to invite him to the house. We had a few drinks, and things... happened. And then he left. And I didn't hear from him again.

"When I saw him tonight, I didn't know what to do. Especially, when he ignored me, and went right to you. I freaked out a little and ran. I shouldn't have done that. I'm sorry, especially because..."

I waited for her to finish her thought, but nothing came. "Because what?"

She looked at the floor. "Because I thought maybe you and I..."

I said nothing, as the implications hit me. "You and I... what?"

The words came pouring out. "That night we got high, and I suggested this? I suddenly realized I had a crush on you. And I thought maybe you'd be interested too. And, and maybe if I made myself hot, and made you hot, we could do something tonight. It's stupid, I know. And now, you probably hate me, and oh god! I'm sorry!" Colette seemed on the verge of crying.

I was dumbfounded, but I suddenly knew this wasn't the place for us to be discussing it. "We should go, and... talk about this at home." And I was again, lost in thought. Todd/Colette wanted me. Todd was Todd, but Colette was pretty hot. And I did just gain an appreciation for performing oral sex on penises.

Colette had pulled herself together while I was daydreaming, and stood up, helping me to my feet. Her hands were soft.

"Come on. We need to clean you up before we go anywhere. You're not walking out of this frat house looking like you just got hosed." She removed the cum from my face, careful not to smudge my eyeshadow or disturb my false eyelashes. Pulling a tube from my purse, she fixed my lipstick, and said "Let's get the fuck out of here."

As we walked in the empty hallway toward the stairs, part of me wanted to stay. Part of me wanted to be defiant, and hang around, showing him, him! I didn't even know his name! I wanted to show him I wasn't just some tart who he could use and throw away. That I was a woma-... er, a person, with feelings.

But, I wasn't a woman. I was a guy in a dress. And I'd just let another man soil me. If I were a woman, it'd be trampy enough, but I was a man. In heels. What the fuck happened to my masculinity? My pride? My self-worth? Apparently, I'd swallowed it, long before I swallowed his sperm.

Any thought about hanging around had left me before we reached the ground floor. And unfortunately, we had to walk through the kitchen to get out. Colette whispered, "Look confident, and we'll be okay."

I steeled myself, praying to god that anyone looking at me couldn't see what was in my head, and in my belly. Praying that they couldn't tell my the look on my face what just happened. Praying that I could escape without any humiliation, or without seeing him.

No such luck.

He was in the kitchen, holding a red Solo cup in each hand, and talking to another guy.

Shit. He saw me...

(Part IV to come.)

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Posted by TransContinental
5 months ago    Views: 1,534
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5 months ago
Great story. Love to read Pt.IV
5 months ago
Excellent little series, intriguing and enticing. I look forward to part iv!
5 months ago
well this keep getting better and better