Turning Sissy - Week 01

ATTN: All characters are purely fictional. All characters are over the age of eighteen. This story contains elements of reluctance and non-consent.

I was always a curious guy. By the time I had begun college I hadn't lost my virginity yet but it wasn't for lack of trying. I had flirted and even kissed girls at clubs and parties but things never seemed to progress. I was on a few dating apps as well, and aside from some chatting things never moved to the next level. By the end of first semester I had downloaded Grindr. I wasn't into guys, but I did have a thing for trans girls, and liked to lurk their profiles. It was a pretty liberal college town and there seemed to be a lot in the area. The downside of having an account meant I also received messages from men despite my profile saying I was only interested in trans women.

One guy in particular leveraged this and would send me porn links and pictures. It was enough to not block him immediately and over the weeks we began to build a rapport. He was in his 50s, bigger, maybe 280, both fat and muscular, and had a grey beard like a biker. He would occasionally try to get me to visit him but I insisted I wasn't interested. He also implied more than a few times I'd have better luck if I was looking to bottom. I ignored this as frequently as he brought it up.

One day he sent me a picture of a crossdresser I had seen online quite often. It wasn't a picture from her profile and it was much more explicit than anything she posted. She was almost naked and sucking a dildo provocatively. He told me that he had been talking to her but she wasn't into older guys. If I was interested, he'd talk me up and connect us. I had already tried to start a convo with her but was ignored, most likely because I didn't have any pictures of myself on my account. He asked me to send a picture he could forward to her and I hesitantly obliged. It was a basic picture of myself fully clothed so there wasn't much that could be used against me if this was some sort of ploy. As it turned out, she wasn't interested and the biker said he'd keep an eye out for someone else for me.

I had made a habit of only using the app in the library as it had location features and I didn't want anyone to be able to see what form I was in while I was using it. I always turned the location feature off when I was done. One day while studying for exams, some friends approached me in the library and I minimized the app quickly. They invited me to lunch off campus and away we went. Partway through lunch I excused myself to the bathroom. It was a single bathroom, with a locking door. As I opened the door to leave I saw him. The biker pushed his way in and shut the door behind him.

"About time you left campus" he said quietly.

"What the fuck du-" he cut me off.

"Those your friend your sitting with? You wouldn't want them knowing you have a Grindr account would you?" he asked, hypothetically no doubt.

He began unbuckling his belt and before I had a chance to say anything he had pulled them down to reveal his considerable bulge under his white underwear.

"Okay two options boy. One, you walk out that door and I follow embarrassing you in front of your friends. Two, you get down on your knees and kiss my bulge."

I weighed the options carefully. He had a crazy gleam in his eye and I knew he wasn't bluffing. Based on his pictures he was out and proud in the kink community so nothing was holding him back. I didn't want to deal with my friends thinking I was gay or it getting out and hurting my chances with the girls in our classes. I had one important question.

"Your underwear is staying on?"

"Of course boy."

I got down on my knees and closed my eyes. As I leaned forward I felt fabric on my lips and warmth beneath it. I smacked my lips to complete the kiss and pulled away. I stood up abruptly and he moved aside so I could leave. My friends were still on the patio and hadn't missed me. A couple minutes later the biker walked out and past us, winking at me as he walked by.

When I got back to my dorm I opened up the app immediately. I intended on deleting it but saw that the biker had left me messages. The first was a picture. It was me on my knees, lips pressed against his package. Why did I close my eyes? I thought to myself. The second message was his address. He was offline, which was unusual. I ignored it and went about my business hoping to forget the incident. My curiosity got the better of me the following night and I checked the app again. This time from my dorm as opposed to the library. He was still offline but something else caught my eye. Near the top of the list, where I usually found the biker, there was a new account named collegecutie. The profile pic was me kissing the bikers bulge. I messaged immediately.

*Dude wtf is this, take this down*

The reply came fast.

*Come make me*

I didn't hesitate. I needed the picture down asap in case anyone gay or bi on campus saw it. I got an Uber to his house at that moment.

He answered the door wearing a bathrobe and welcomed me in.

"Take that picture down, please.'

"I had to get your attention somehow. I'll take it down, but I'll put it right back up, maybe even use it on a tinder account, unless you agree to my terms."

"Terms?" I asked hesitantly.

"You come over, once a week and spend 3 hours doing whatever I want. I'll even pay you, let's say $100 per week, for 6 weeks."

"Whatever you want? What the fuck I told you I'm not gay"

"You don't have to be gay. If that picture stays up it won't matter because it's what everyone will assume. I'm not a rapist, you don't have to have sex with me if you don't want to. You just have to do what I say." he reassured me.

"I don't know man, what does that even mean?" I asked.

"It's the deal, if you accept, it'll start now and you can find out. Take it or leave it." he held his hand out.

I didn't feel like I had many options. I had a sinking feeling that I was making a mistake as I answered.

"Fine" I said and we shook on it.

"Okay great, first things first" he led me to his bathroom and handed me shaving cream and a razor. A whole lot of protesting and some threats involving the picture later I was carefully removing all of the hair from my body. An hour after that, I was as smooth as the day I was born and begrudgingly enjoying the smooth feeling of my thighs rubbing together. Upon exiting the shower my clothes were gone. A pair of pink panties remained and I reluctantly put them on. I walked out to the living room and he laughed as he saw me.

"Thought you might enjoy those."

"Real funny" I said, "Where are my clothes?"

"That's one of the terms, you wear what I say." he explained patting the spot next to him on the couch.

I sat on the couch and he began to go over ground rules with me. I felt completely exposed sitting in only skimpy underwear and as he spoke he would occasionally put his hand on my leg, making me uncomfortable. The rules were simple, 3 hours a week for $100 and he could have me do anything. The only thing off the table was sex of any kind including hand jobs, blowjobs, and of course anal. Everything else was fair game but he assured me our contact would be mostly limited. I couldn't help but suspect there being a catch to this but I figured I could put up with anything for $33 an hour as long as it wasn't too sexual. I was after all a poor student and money wasn't very easy to come by in my college town.

He had me do his dishes dressed like that and despite the humiliation I genuinely enjoyed how smooth it felt to walk around with shaved legs. I even considered keeping it up after the 6 weeks. While I washed, he came up behind me and began playing with my hair. I felt an elastic pulled on one bundle and then the other and realized he had my long brown hair in pigtails. I felt a hand gently squeeze my left cheek before he walked back to the living room. Embarrassingly enough the body contact gave me a bit of an erection that was hard to hide under the panties. By the time I had finished, I had to wait until it went soft to go find him.

I found him in the living room again and this time he had me dust his television stand so I was down on my knees, ass in the air in front of him. I was blushing as I cleaned knowing he was staring right at my ass. My last half hour, he had me sit next to him on the couch with his arm around me, occasionally stroking my arm. Twice he had me grab him a beer and both times he slapped my ass. The second time he noticed my bulge had increased slightly.

"Enjoying yourself princess?" he asked, causing me to turn red in embarrassment.

Eventually I was permitted to leave, $100 in hand, the account deleted, and wearing my clothes again. He insisted the panties stay on underneath them though and told me too wear them on my next visit.

I went home to my dorm confused about what he was getting out of this. I was half expecting things to get sexual or for him to try something but it was reasonably tame. I saw that the account and picture had been deleted but told myself the $100 a week was too good to pass up so decided to honour the deal. Besides he could easily put the account back up if he suspected I wasn't going along with our agreement.