I arrived in Washington State, mid-summer for university. I did not know one person. The closest “friend” I had was Max, who lived three hours away. If you haven’t read my other stories, Max is my benefactor, my occasional lover, and my Sugar Daddy. My relationship with him may sound strange to an outsider, and it is complicated to explain.

I met Max online, and he was the first person to call me and treat me as a “she,” even before I knew I wanted that. He encouraged me to follow my dreams, and he was the first man to take my virginity. Max is married with children, and I know we will never be together, and that hurt me for a long time, but I have grown to understand that it is not meant to be.

Max’s company has given me a full scholarship to the university, and that is amazing, but books, food, and lodging were my responsibility. I found a one-bedroom online, it was a room in a house with a shared bath and main rooms, but it was cheap and walking distance to the university.

I met the landlady, Renata. She was gruff, wore too much makeup, and seemed very conservative. She told me she owned many other properties and didn’t live there. Her brother Barry managed the property and lived in the house, and if I had any questions or problems, talk to Barry. Renata didn’t ask if I was trans, and I didn’t tell her. It wasn’t ideal, but it was the best I could do at the moment.

I found a job as a barista selling coffee at a local coffee shop and got prepared for the daunting task of school.

I didn’t go out much, so I was at the house often. Barry never seemed to leave the house, ever. Barry was tall and skinny and wore too short, cut-off jeans, Birkenstocks, and rarely a shirt.  He had a hairy chest and tattoos of skeletons and dragons on his arms. We got along okay, but I would catch him leering at me whenever I left the room.

One day I was stepping out of the shower, and the door swung open, it was Barry. He apologized but didn’t leave. He just looked at my naked body and especially my cock.

“Jesus, you’re a guy!” He blurted out.

I attempted to cover up, but Barry pulled the towel away. He looked me up and down.

“I have never met a shemale before,” Barry remarked.

“Trans girl,” I corrected him, grabbing back the towel.

“Sorry, trans,” Barry said.

“Is this going to be a problem?” I asked him.

“Not with me, but Renata is a prude, and she won’t let you stay,” he told me.

“Does she need to know?” I asked.

“I can be convinced to be quiet,” Barry said creepily.

“What do you want?” I asked carefully.

“Well, you can start by taking the towel away and showing me your body,” I said.

I reluctantly lowered the towel, exposing my freshly showered and shaved body.

“Fucking awesome!” He said, leering at me and moving forward.

I put my hands up, pushing him back.

“We negotiate first, what do you want for your silence?” I asked him sternly.

Barry was taken aback by my assertiveness. He looked at me, considering his requests. 

“Okay, I get to suck on your cock and lick your asshole. Then you give me a blow job until I cum in your mouth,” Barry stated.

“Cumming on my face, not in my mouth,” I told him.

“Better,” He agreed.

“And nothing else? And you keep quiet?” I told him.

“Sure,” Barry agreed.

“Alright,” I told him.

Barry excitedly pulled off his shorts, and his half-hard cock was covered in thick gray-black hair. He gently moved his hand down my shoulder, examining me, and then lifted me onto the sink, as he sat on the toilet. Barry studied my hardening cock, cupping my balls, and squeezing the shaft. He gave my cockhead a little lick before he put his mouth around it.

I was disgusted, but it felt good to have lips on my cock again, it was over three weeks, since my friend, Greg, sucked on me.  He moved his mouth up and down my cock, rhythmically without much technique, but it felt terrific. He tried to move his head down to lick my asshole, but he couldn’t manage it from this position.

“Get down and bend over,” Barry said, frustrated.

I got down and bent at my hips, touching the floor.

“What a perfect pink hole,” Barry said lustfully.

Barry slapped my ass, the spread my bubble-butt cheeks, and tongued my asshole. He swirled his tongue around my tight hole and even pushed his tongue into it. Again, I was conflicted because it felt so good. Barry pushed a finger, then two into my asshole, and I didn’t protest, but I did try hard to suppress my moans. Barry then stood up and grabbed my hips, pushing his cock near my backside, and I pulled away.

“We said, blowjob, nothing more,” I reminded him.

“Okay,” Barry said, disappointed.

Barry stood there with his hands on his hips, almost displaying his cock or me.

“Go ahead, it’s not going to suck itself,” He said sarcastically.

I folded the towel on the floor and kneeled in front of him. His above-average cock was hard and protruded from the nest of unkempt pubic hair. I decided not to delay and put my mouth around his cock. He had a funky taste but wasn’t as bad as I thought it was going to be. I used my hand to stroke his cock while I licked and sucked on his cock head.

“Let me see you stroke your cock while you suck me,” I said.

I took my hard cock and stroked it back and forth.

He looked down and smiled as he pushed his fingers through my hair and held my head, not roughly but with firmness. He started to move his hips back and forth in a fucking motion.

“Fuck, baby, you’re going to make me cum!” He announced.

I sucked a little more before taking his cock out and jerked his cock. I pulled his cock quickly as I looked expectantly for his cum. Barry then slapped my hand away and grabbed his cock, and stroked it himself. He held the back of my head as he let out a series of grunts, before shooting his thick white cum onto my face.

“Beautiful,” he said, looking down at my cum-covered face.

I took the towel and wiped my face and stood up.

“Thanks, that was great,” he said, “You didn’t cum,” he added.

“I’m good,” I said.

“The least I could do is jerk you off,” Barry offered.

“No, I’m good, thanks,” I declined.

“Okay then, I offered,” he said.

“So, we are good then?” I asked, “You won’t tell your sister about me?”

“Nope, we have a deal,” Barry said.

We left the bathroom and never really spoke of it again, but he smiled at me more and brushed against me more often after that.

----

About a month later, I started full time at the university, it was a lot harder and more expensive than I was ready for. So many books and programs for my computer that it was very overwhelming.

I always thought I was smart, but the people in my classes were next level smart, so I had to work harder than they did. I had to take fewer shifts at the coffee shop, and then at the end of the month, I discovered I didn’t have enough money for rent.

I carefully avoided Barry for the first few days of the month until he barged into my room without knocking.

“Renata just gave me shit; You didn’t pay your rent this month,” Barry snarled.

I turned toward him, picking up a pillow for protection.

“I know, I’m sorry, I just ran out of money this month,” I apologized.

“That’s bullshit,” Barry said, “She wants me to kick you outright today,”

“No, you can’t, I don’t have any place else to go,” I pleaded. “I don’t know what to say. Renata owns the place,” I said, almost crying.

“I’ll talk to her, I’ll do anything,” I pleaded again.

Barry’s face softened, and his mind churned, as I knew I might have said the wrong thing.

“She’s a cold bitch and only cares about money,” Barry explained. “But I might be able to help you.”

“How?” I said, not liking where this was headed.

“I will pay your rent, and you help me out,” Barry said with a grin.

I knew where this was going, but I needed to understand the terms.

“What do you want?” I asked.

“I have sex with you, including blowjobs, whenever I want, and I pay your rent,” Barry stated.

He was so predictable, but I knew that I would need to do something sexually for him, or I would be out on the street.

“We will have sex once a month and one blowjob a week,” I told him.

“Forget it,” Barry said, turning to leave.

“Okay, what? But be fair,” I asked.

“Sex, once a week and two blowjobs a week, and that’s my final offer,” Barry stated.

I thought about it, and at the time I couldn’t think of a way out, so I agreed.

“Great,” Barry said, pulling off his shorts.

“What, now?” I asked.

“Yes, right now,” he said, “Turn over.”

I flipped over onto my stomach, and he pulled off my shorts and my panties together.

Barry slapped my ass.

“Love that ass, we are going to have some fun,” Barry said gleefully.

Barry moved between my legs and started to lick my asshole. Barry was a scumbag, but he did enjoy eating ass, and he was good at it. Barry then got up on his knees and pulled my hips up to him.

“Wait,” I said, as I scurried over to the night table.

I grabbed a condom and some lube from the nightstand.

“Please put this on,” I asked, earnestly.

“Okay,” Barry said reluctantly.

Barry put the condom on and put some lube on his cock and in my asshole. He slowly pushed his cock into my tight hole. It hurt as he went in because I wasn’t relaxed. He started to fuck me, and it got better after a minute. Barry slapped my ass and talked dirty to me as he fucked, which I didn’t mind, but if he were quiet, it would have been easier to imagine Max or Greg fucking me instead.

Barry then reached around and started to stroke my hard cock. Nobody had done that before, and I liked it quite a bit. Barry then flipped me over on my back and pushed his cock back into my asshole. He grabbed my ankles as he fucked me.

“If I’m going to fuck a shemale, I might as well see the whole package,” he said.

Barry grabbed my cock and stroked it to the rhythm of his cock sliding in and out of my asshole. I couldn’t help but moan, which only encouraged his fucking. Then he took my foot and sucked on my red-painted toes, which always drives me wild. He grabbed my legs and pressed them against my shoulders. Barry knew how to fuck.

“I’m going to pound your tight ass,” he said with excitement.

Barry fucked me faster and faster until he announced he was going to cum. He pulled out his cock and peeled off the condom and came all over my cock, stomach, and chest. He came a lot more than he did last time.

Barry then pushed his finger into my stretched asshole and fingered my prostrate.

“Cum for me, baby,” Barry said in a gentler tone.

It didn’t take long before I was cumming on my stomach and chest.

Barry scooped up our combined cum, off my chest, tasting it and offering me some, which I did. 

Barry thanked me and left. I wasn’t sure what to make of this new situation.

Over the next month, Barry was respectful and kept to the deal for the most part. He would often grab my ass, and twice he came into the bathroom and jerked off while watching me shower, but basically, we did what we agreed. 

----

During this time, I was in contact with Max, and we would text and spend some nights in a hotel in the city.

On one Saturday Max invited me to go to a barbeque at his friends in the afternoon. I was excited as I didn’t meet many of his friends. I put on my makeup and got dressed in a cute halter top that nicely exposed my stomach and a short skirt and open-toed sandals. I was just about to leave when Barry called from the living room.

“You owe me a blowjob,” He said matter-of-factly.

“I know, but I have a date,” I explained. “I can tomorrow.”

“A deal is a deal,” Barry said as he pulled down his pants.

I knew there was no changing his mind, I looked at my phone and saw I had ten minutes, so I padded across the floor and knelt between his legs. Barry’s cock was soft, but it hardened in my mouth. I sucked on him vigorously, knowing how to make him cum quickly. Suddenly he grabbed my head and forced his cock in and out of his mouth. He pushed deep into my mouth, choking me a bit. His cock started to pulse as he began to cum. He held my head until he finished cumming, then he pushed me away.

“Have fun on your date,” Barry said with disdain.

I got up and went to the bathroom to spit out his cum and tried to clean myself up. I ran outside to where Max was waiting in his car.

“Are you okay?” Max asked as I got in.

“Yes,” I said quickly.

Max leaned over to kiss me, and I kissed him back. He licked his lips and then looked back at my house.

“Did anything happen?” Max asked curiously.

“No, everything is good. We should go,” I said quickly.

Max looked at me, considering me, but didn’t say anything as he put the car into gear and drove off.

On the drive, Max tried to make light conversation, but I stayed quiet, stoically.  I was ashamed for what I had been doing and angry for letting it happen.

I started to sob involuntarily. Max pulled the car over and asked me again what happened. I broke down and told Max the entire story. I could see Max was containing his seething anger and was extremely comforting to me. I was bawling my eyes out, and my eyeliner was streaming down my face as I cried on his shoulder.

Max asked if I wanted to continue to the party, and I said yes.

We arrived at a lavish mansion far from the city. A valet ran out and took Max’s keys. I was in awe at this beautiful house, wondering who these friends of Max’s were.

As we entered into the front foyer, we were greeted by one of the most stunning women I had ever seen. Max introduced her as Miss Kamiko. She had long flowing black hair, impeccable makeup, and was wearing a green floral print, Chiffon summer dress. She moved with such grace and spoke with only a hint of an accent.

Miss Kamiko kissed Max on the lips and then turned her attention to me.

“This is the one you spoke about?” Kamiko said, “She looks like an angel.”

Miss Kamiko put her delicate hands on my cheeks and kissed me on the lips, sending electricity through my body. She moved back and looked at me.

“Have you been crying, dear?” Kamiko asked.

“I am fine, Miss,” I answered quietly.

“Nonsense,” she said, calling to the next room. “Aya!”

A young Japanese girl about my age came bounding into the foyer. She was wearing a peach schoolgirl outfit and had pink and white dyed hair.

“Yes, Auntie,” Aya, the Japanese girl, answered.

“This is Samantha, why don’t you take her up to my room and help her freshen up,” Miss Kamiko said.

“Yes, Miss,” Aya answered politely.

Aya took me by my hand and led me upstairs to Miss Kamiko’s bedroom.  The golden double doors opened into a massive room. A large king-sized was the main focal point of the room. Off to the left was a large hot tub, and to the right was an extensive makeup and changing area.

Aya guided me to the makeup table and started to remove my makeup. Aya smiled at me as she began to re-apply my makeup.

“You are very pretty,” Aya said, flirting.

“Thank you,” I blushed. “You are so beautiful!” I told her.

“Thank you,” Aya said as she kissed my lips.

Shocked, I smiled back awkwardly.

“So, Miss Kamiko is your aunt?” I asked Aya.

“Not really, we just call her Auntie or Miss,” Aya explained.

“Who are 'we?'” I asked.

“The guys and girls she helps out,” Aya said. “She is like a benefactor.”

“I see,” I answered, but not fully understanding.

“I am a lesbian,” Aya said suddenly. “Do you like girls?”

“I do like girls, and guys, I am bi and…” I started but stopped myself.

“And what?” She prodded.

“Nothing,” I deflected.

“Samantha, you can trust me,” Aya said with her very kind eyes.

“I am trans,” I said softly.

“That’s amazing!” Aya exclaimed.

“What?” I responded, confused.

“I knew you were special when I saw you,” Aya said as she kissed me.

This kiss lingered a bit, and then Aya pulled a little back, we stared in each other’s eyes and slammed our lips together and kissed passionately. The kiss was magical and passionate. Aya brought my hand between her legs, and to her wet pussy, I was happily surprised she wasn’t wearing panties.

I pushed my fingers into her pussy and rubbed her clit. Aya then pushed my panties aside and grabbed my hard cock. We both moaned at the same time as we locked lips. As if we were one being, we drifted to the floor and assumed the sixty-nine position with me on the bottom. Aya moved her mouth up and down my cock with expertise, even though she was a lesbian. I licked her pussy with vigor and enthusiasm. It was only a moment longer, and we were both cumming, first Aya, and then me. It was electric.

We had just finished when we heard a voice from the doorway. It was Miss Kamiko and Max.

“Well I see you are getting acquainted alright,” Miss Kamiko said sarcastically.

We both looked up giggling and smiled at them.

“Aya, are you still looking for a roommate?” Miss Kamiko asked.

“Yes, Miss,” Aya politely.

“Well, Max just told me, Samantha is looking for a place,” Miss Kamiko added.

“Oh yes!” Aya squealed, “Samantha, you must move in with us!”

“I would love to,” I answered quickly.

Aya hugged me tightly. I was overwhelmed with joy and excitement. A day that started out so horribly had turned out to be one of my best days.

The next day, Max and Aya helped move my things, in front of the grumbling Barry. I found out later that Barry lied and didn’t even pay the rent for me, and his sister Renata was going to kick us both out in a few days anyway.

Next, I will be telling you about Aya and my Rainbow roommates.