College Sissy Pt. 03

All parties involved are over 18 years of age, all acts described are between adults.

"Wait what? Why do I have to do your laundry now? I get the blanket, but all of it? I didn't agree to that."

My setup with Sir had been going on for a few weeks now, without any major breaks.

"Cuz you're the one getting good dick, makes sense for you to pay for it."

Couple times a week. Which was nice, honestly.

"But you're getting off too, more often than I am..."

Half of which were now at Sir's request.

"But you really think mine are as good as yours? I'm not the one having sissygasms, because I'm not a sissy. And I'm not the one making a mess."

I blushed.

"Okay...but..."

"And I know I'm not making a mess because everytime I cum you take it."

I got even redder.

"Plus I go to classes and workout and play for the school. I have less time, I want this done, and you have time, you get what you want, and I can find someone else who will happily do it."

"No, I mean I can..."

"And you're a sissy. Don't you enjoy doing laundry?"

"Well, I don't really..."

"That settles it. It's all in that hamper. Fold it, too. Like the blanket."

"Sigh, right, Sir."

It wasn't that much of an ask, I guessed. I already had been doing the blanket with my laundry for a bit. I used to think people would notice how odd it was that I was on the wrong floor, or constantly doing laundry, but mainly people kept to themselves. They were so caught up in their own college experience that they couldn't see the small things.

While doing the load, I was on my phone, waiting to finish the laundry. Since I had been seeing Sir, I hadn't been checking to see if I had anymore responses to my ad, and since it was over a couple months old, I didn't figure there would be any. But, to my surprise, I got a notification. I had been ignoring most of them since I had been seeing Sir, but getting one so late I was curious.

"Hey, sissy.

I will be in your town in about a week. I'll be at a hotel, and definitely will need some entertainment that night. You should come on by. I know what it's like being a student, and I can make it worth your while."

I felt similar to the way I did when I read Sir's message, but was conflicted. I mean, for sure it was different, this was an older man, and at a hotel no less, sounded kinda sketchy. But it's a one-and-done, I guessed, since he was traveling. The sissy comment, I didn't know if I just hated that, or it was a good sign, only the men who used the term seemed to be able to give me what I wanted. Then, did I even want to? I didn't really like the setup I had with Sir, he was a pain, but he was reliable. And lastly, what did he mean worth my while? I figure he means he can deliver on a sissygasm, but was that it? He mentioned being a college student... so was he willing to pay? I didn't need money, my expenses were taken care of, but spending money would be great.

What's the harm in responding? I don't have to go.

"What brings you to town, sir? What did you have in mind?"

I sent a response. As soon as I did, my laundry finished. I probably made an audible gasp when it went off, I had been so deep in thought. Thankfully I was alone.

As I went upstairs, I thought more about what I did.

What the hell is wrong with you? You didn't want to do this in the first place! You like girls, and the only reason you are doing this is because you just like getting your g-spot touched by a pro! You have someone who can do that and who is in the same building! Now you're thinking about meeting a stranger in a hotel? For what? Did you call him Sir???

It seemed to be happening so fast, when in reality it wasn't. Time with Sir had been over the course of months, and I hadn't gotten a response from this traveler. I just wasn't really sure who I was at this point. I was getting what I wanted, yes, the sissygasms were amazing, and I still couldn't replicate them on my own, but what about all the other parts that came with it? I was at the beck-and-call of a guy. I did chores for him. I actually sucked his cock. And, to him I was just a "sissy". I called him "Sir" for God's sake. But I kept coming back. What was going on? I was straight. Or, I mean was I? It was the 2020s... if I wasn't I guess that's not the end of the world, but calling him Sir? Being such a bitch? Did I really like what he was doing or did I just put up with it for the sex? Or...did I know how to get out? Confusing enough to feel like it was happening at the speed of light, when really nothing was happening at the moment. Until I got a response.

"Nice to hear from you, dear. I have business in town. Don't worry, nothing to do with your school. I know your ad was all about discretion, and I respect it. Although you can't be the most discreet when you name drop the school, lol. I was thinking you could come over, we can have some fun, and you could leave with more than you came over with? How about that?"

I blushed. Did that a lot back then.

Dear?

I had mentioned where I was studying so I could be clear on location, but in hindsight it was a little reckless...

What he was asking for wasn't THAT different from what I already did...but still. And the thought of getting paid. Exciting? More for the money than the act. I never thought I would be in that position. It was all kinda gross...but I wasn't sure. Did I really even want it?

"Thanks for the discretion, sir lol. I...uhhh havn't done much like that before, a little, but not a lot...How much more would I leave with...?"

Still curious, nothing committed.

"It's alright, dear. Since you haven't done much like it before, I promise it'll be grand ol' time. That work?"

A grand???

At that time, a grand was more money than I had ever had at a time. Even today I don't have that on hand. As I folded Sir's laundry I kept messaging the traveler, seeing about more details and such, condoms, etc. He said this I felt everything was hashed out.

"You've done makeup before, right? I know you are inexperienced, so what are your sizes? I'll have something for you to wear at the desk. You can put it on in my room before I get there, then we can have some fun, dear."

I froze.

What the fuck? I do NOT do that. I am NOT a crossdresser! I am not some kind of tranny wtf!

I was speechless, I hadn't even committed, Just seeing what it would look like. In reality, I didn't say I wasn't making plans either, I was more or less interested, just I was pretending with myself that it wasn't real. But that? I couldn't do that! But... a grand? In private? I didn't know what to do. I put the phone down and thought.

No way. Absolutely no way.

I finished the last piece of laundry, and without thinking I texted Sir it was done. He said to come drop it off. I didn't want to look him in the eyes knowing what I was up to, even though it's not like I was in a relationship. I sighed, and picked it all up to go upstairs.

I went upstairs and knocked. Sir opened the door, clothed, which was a rarity.

"Come in, I'll show you where it all goes, sissy."

I sighed and put it all away, as directed.

"Good, now I have to be somewhere soon, but go ahead and get on your knees."

"Sir...I uhhh..."

Sir was undoing his pants already.

"What?"

"I uhh had a question...there's this..."

"There's what?"

Sir had his hand on my shoulder and was pushing me down. I was kneeling now. Not the first time he did that, it took a few times for me to get used to sucking.

"Someone messaged me about my ad? They offered to pay me...it's just a scam, right? You wouldn't be comfortable with that, right?"

"They messaged you? Give me your phone."

"Oh uhhh..."

"Open it up, show me your messages, now."

I wasn't expecting that reaction. I quickly got my phone out and opened it to the messages. I held it up, but Sir just took it and started reading. I was so nervous, I just stayed there, on my knees.

"Suck, bitch." He said without looking away from my phone.

I was flustered but I started sucking the cock in front of me.

"Hmm...He's traveling in?"

His other hand was behind my head, forcing me to take him into my throat.

"Wow, sissy. He really does want to pay you., doesn't he?"

Sir was making me gag, something I said was difficult for me, but he wasn't concerned.

"At the hotel...he'll have something for you to wear! Won't you look purdy..."

He kept speaking like he had questions...I'm guessing he didn't expect me to answer.

"And you were thinking you were gonna go, bitch?"

I kept sucking Sir's cock. I figured that was the best thing to do.

"Hmm..You should go, sissy."

My eyes lit up.

"Yeah, you're gonna go, sissy. He'll wear a condom, for sure, and you're gonna give me some of the cash, got it?"

I choked up a bit, but Sir kept moving my head for me.

"Yeah, that works. Sissy will go, get fucked, and give me some of the profit. I mean if it wasn't for me, you wouldn't have even responded in the first place, I bet."

Sir came in my throat, and I struggled, but swallowed.