The Landlady

"I have always thought you looked so fuckable," she whispered.

"Seriously?"

"Mmhm...ever since the day you turned eighteen, I have been dying to get my hands all over you. Don't tell your mother that I said that, though."

We both laughed a little, as she continued running her fingers through my hair. I have to admit, the way she was looking at me at that moment, was really making me feel a certain way. That look of lust, like she wanted me so badly; it was a look that nobody had ever given me before. Even when Melissa and I were having sex more often than now, she never looked at me that way.

Susan stepped back after a moment, hooking her thumbs around the elastic waistband of her panties, and pulling them slowly down. Out popped at least ten inches of thick meat, already half erect, and a set of very heavy looking balls. My eyes went wide with surprise; God, Susan was fucking huge! Looking at it, I wondered if I would even be able to fit it all in my mouth.

Susan wrapped her hand around the shaft and started stroking until it was fully hard. She stepped closer to me again until her dick was mere inches away from me. "Well," she said, with a grin. "It's not going to suck itself, baby."

Here we go, I thought.

To start, I leaned in and kissed the tip of her dick. That earned a giggle from the beautiful woman, standing above me. Then I opened my mouth and took just the head, between my lips. My tongue slid across the head, tasting and teasing, earning a soft moan from Susan.

First impressions?

It wasn't all that bad, actually.

Taste-wise, it was a bit salty, with a faint hint of piss, indicating that she must have been in the bathroom recently. It wasn't a very heavy taste though, and certainly not repulsive enough to make me want to quit.

I stayed focused for a while, on just sucking on the tip and using lots of tongues, as Melissa had suggested. It seemed to work for a while but, Susan grew tired of the teasing after a bit. She grabbed my head and started pushing it down, my lips sliding further down over her cock until I was gagging and choking.

I could feel her balls against my chin, and my nose was buried in a patch of thick, red pubic hair. Susan held my head in place, preventing me from pulling back for a while. With my face mashed against her body, it was difficult to breathe through my nose. I could feel my cheeks starting to flush when she finally let up and allowed me to pull back and gasp for air.

There was already some spit running down my chin, and my eyes were blurry from tears, due to my all the gagging and choking. Susan looked down at me and laughed. "You look like such a dirty boy, right now."

Then before I could respond, she grabbed my head and shoved it back down again. I gagged again, trying to take all ten inches of her cock. Susan pulled at my hair, bobbing my head up and down, fucking my throat raw.

"Good boy," she whispered softly. "I'm going to let you do it by yourself now, okay?"

With that, she moved her hand away from my head, allowing me to take control of the situation. I willingly continued to bob my head up and down, sucking and slurping, as I tried to deep throat. Little by little, I seemed to be getting used to this. I was able to relax my throat enough, that I managed to overcome my gag reflex. As I adjusted, I bob my head faster and faster.

"Mmm, that's great," Susan moaned.

"You're getting better at it...you are doing a great job. Such a dirty little cock sucker, you look so cute down there."

The dirty talk seemed to be doing something to me; it wasn't just that, though. It was the thought that Susan actually wanted me so badly, it was the dirty talk, it was the taste of pre-cum that was covering my tongue now. My own cock was hard as a rock...this was turning me on.

No, that's not right!

Alarms immediately started ringing in my head. I wasn't supposed to be enjoying this, I was only supposed to make sure that Susan enjoyed it. I couldn't deny though, no matter how bad I wanted to, that I was having a good time. I tried to ignore these thoughts, pushing them to the back of my mind and focusing on Susan. I could feel her cock starting to throb. She was breathing heavier, and even sweating a little now; I knew she was close.

"I'm gonna cum," Susan announced.

She was gasping for air now, twitching and convulsing, her legs trembling beneath her as her cock began to pulse in my mouth.

"I'm cumming!"

The first shot landed on my tongue, giving me a taste of her sweet juice; it tasted great. The second shot was much stronger than the first and blasted right down my throat. The next several ropes of cum were released with such force, I thought I wouldn't be able to swallow it all. She filled my mouth to the brink with her cream, and I could feel some of it running down my chin.

When it was over, I gulped down every last drop and pulled back, gasping for air. Spit and cum running down my chin, I looked up at Susan and she reached down to wipe the sweat from my forehead. "That was great," she said, still breathless.

"You did very well, for your first time...took a few minutes for you to adjust but, the end result was well worth it."

I excused myself to the bathroom, checking my reflection in the mirror. My eyes were dilated and the vision was still very blurry. I washed my face in the sink, then returned to the living room, where I found Susan sitting on the couch, smoking another cigarette. "How do you feel, Alex?"

"I'm alright," I replied. "Are we good now?"

"Mmhm...a deal is a deal, my friend. I'll excuse the rent for this month again but, you will have to pay me next month, in one way or another."

She said that last bit, with a sexy grin; I knew what she meant.

I wasn't sure if I wanted to do this again, even though some part of me had really enjoyed myself. Melissa had agreed to it this one time but, I didn't think she would be okay with it being a repeated thing. So, I was going to have to find a way to pay the rent, if I wanted to avoid sucking Susan's dick again, next month.

When December came around, we actually managed to pay Susan with cash. She seemed a bit disappointed, to tell you the truth. Melissa had asked her parents for a loan, which I wasn't too happy about; they already had problems with me. The last thing I needed, was for them to look at me like a total bum. Then came January, and again, we were borrowing money from her parents. I really felt like shit about it, this time.

Things between me and Melissa were becoming more and more complicated.

The worse our financial situation got, the more we found ourselves arguing. Our sex life had not improved either. In fact, the last time I'd gotten any kind of action, had been two months earlier...and it was with Susan. The only way I could get any sexual relief, was to relieve it myself. I found myself jacking off quite a bit, whenever I was alone...and the subject of my thoughts always happened to be Susan. Sometimes, I would look up porn on the computer or through my phone, and it was becoming more and more often, that the content would be transsexual porn, instead of regular porn.

I wanted another chance with Susan; there was no denying it.

February rolled around, and Melissa was prepared to ask her parents for help, once again. I wasn't having it this time though...

I didn't want to give her parents' any more reasons, not to like me. As far as I was concerned, I would rather sleep on the streets then keep asking them for help; all it accomplished, was making me look really bad. Melissa did not seem to understand my issue though, and of course, it led to another argument.

"What else do you want me to do?" She asked, angrily.

"My parents are the only ones, that can help us!"

"Yeah, I get that; but they've helped enough. I know they're constantly talking trash on me, trying to convince you to leave me...I'm not stupid, Melissa."

She sighed, obviously feeling bad about what I had just said. Melissa knew it was true; her parents did not want us together. As much of a bitch as she could be sometimes, I did believe that Melissa still cared about me.

She perked up suddenly, as though she'd had an idea.

"Why don't you go suck her dick, again?"

I looked up at Melissa, surprised by her suggestion. "Seriously?"

"It worked last time," she shrugged. "Plus, I don't have any better ideas...it might be the only choice we have."

She was right about that, we didn't have any other options. Plus, I had been wanting this for the last two months, anyway...I just hadn't said anything about it, for obvious reasons. Melissa had to keep thinking, that I was only doing this for our well being. If she found out that I actually enjoyed it, that would cause problems. I decided to go for it, and made my way upstairs, knocking again on Susan's apartment door.

When Susan opened the door, she smiled, leaning against the door frame; she knew what I was there for.

"What's up, Alex?"

"Can we talk?"

She nodded her head, stepping aside and I brushed past her. Susan closed the door and we both stood in the middle of the living room, neither of us speaking a word. She was waiting for me to say something but, for some reason, I was too nervous to talk. "Let's get to the point," Susan started for me.

"I'm guessing, you can't afford the rent again this month?"

"Yeah, that's right..."

"I see," Susan said. "And, how do you plan to deal with that?"

I took a deep breath, stepped forward and dropped to my knees right at her feet. Susan chuckled, as she started pulling her shorts down and I could already see the bulge of her hard cock through her panties. I leaned in, smelling her scent through the soft white fabric; my own cock was already as hard as a rock.

"You seem much more eager, then the last time," she said softly.

"I have to pay you somehow..."

"True; but, that's not the only reason, right?"

Susan knew full well that she had me right where she wanted me. I reached up and pulled her panties to the side, her hard cock sliding out for me to wrap my lips around. I started sucking, bobbing my head up and down, cradling her heavy balls and massaging them for her. I had spent the last two months watching transsexual porn, with guys sucking dick, and getting fucked in the ass; I mimicked everything that I had watched them do in the videos. Susan seemed very impressed, moaning in pleasure, as I displayed my deep throat skills.

Everything was going great, when Susan suddenly stopped me, pulling her dick from my mouth and stroking it slowly.

"What's wrong," I asked, slightly confused.

"Nothing at all," Susan replied. "I just had a great idea."

Susan reached down and took me by the hands, helping me back to my feet again. "Take off your clothes."

Still not sure what she had in mind, I wasn't opposed to doing what she said. I pulled my shirt over my head, throwing it to the floor and then slid out of my jeans.

"Boxers too," Susan said.

She wanted to see me fully nude...

A few seconds more, and there I was, fully nude in front of my mother's best friend. Her eyes traveled up and down my body, taking in every part of me and groaning softly, as she continued to stroke her wet cock. "Turn around and bend over," she instructed.

"I have been dying to see that cute little ass of yours, for so damn long now."

I slowly turned around, once again thinking about how it made me feel to know, that someone actually wanted me in a sexual manner. I had a general idea, of what Susan was probably planning next; it made me nervous. At the same time though, I was pretty turned on and excited, too. I bent over, touching my toes and showing my ass to Susan, who was still stroking her dick. "That's great," she whispered.

I felt her come up behind me, using one hand to grab my ass and give it a firm squeeze. She began caressing my ass cheeks, admiring the sight before her and chewing on her lip.

"I think, I'm going to have to raise the rent."

"What?"

"I'm raising the rent," Susan repeated.

"If you want to continue living in this building, I'm going to need more from you, then just the occasional blowjob...I want to fuck this sweet ass of yours, Alex. I want you so bad..."

At this point, we both knew this was no longer just about paying rent. I wiggled my ass a little for her, and Susan giggled, spreading my cheeks and rubbing her cock along my ass crack.

"You want this, don't you...admit it."

"I-I do," I nodded.

"You do what?"

"I...I want you to fuck me in the ass."

"Mmm, good boy..."

She stepped around in front of me now, motioning for me to stand up straight again. "I'll be right back."

She walked off into her bedroom, leaving me there waiting for her to return. When Susan came back, she was carrying a bottle of lube in her hand. She instructed me to lie down on the floor, flat on my stomach. I obeyed her command, getting down on my hands and knees and then flattening myself out.

Susan knelt down beside me, giving me a hard smack on the ass. It stung but, I liked it. She smacked me a few more times before I felt her spread my ass cheeks, and she began lubing me up.

I felt fingers sliding in and out of my tight hole, stroking my insides and trying to loosen me up enough, for the main event. Susan spent a good few minutes doing this and even managed to work a whole five fingers into me. There was a very intense feeling of pressure; it was a little uncomfortable but, not very painful.

Once Susan felt that I was prepared well enough, she withdrew her fingers from my ass and climbed on top of me.

I felt the tip of her dick pressing against me. She pushed forward, applying just a tiny bit of pressure, and popped right into me.

I gasped, instinctively pushing back against her, my ass swallowing all ten inches in one shot. My eyes nearly popped out of their sockets, and she knocked the wind out of my lungs. Grabbing me by the hips, Susan did not waste any time. She started plowing my ass, with long hard strokes. Our bodies smacked together, and she reached up with one hand and grabbed a fistful of my hair, pulling hard at it.

I gave a low grunt, followed by a moan, as she pushed as deep into me as she could get. My dick was completely flaccid, swinging back and forth between my legs and dripping pre-cum all over the hardwood floors. The harder she started fucking me, the louder I started to moan and groan. Susan shoved my head down against the floor, and I worried that Melissa might actually hear all of this, from downstairs in our own apartment.

"Your ass is so fucking tight," Susan grunted.

"F-Fuck, it's just like I always imagined!"

Susan was having the time of her life. After all, she had already admitted that she'd wanted to do this, since the day I turned eighteen. I had been sex-starved for quite some time now, thanks to Melissa...I was dying for a good lay. I didn't think it would involve me being on the receiving end but, I was loving it! Who knew that getting fucked in the ass, could feel so good?

Eventually, Melissa turned me onto my back and continued fucking me in missionary now. She leaned in close and pressed her lips to mine, kissing me, as she thrust in and out of me. I dug my nails into the floorboards and started crying out in pleasure...there was no way in hell, Melissa wouldn't hear that.

My cock suddenly surged, swelling up and pulsing, as it began spewing cum all over the place. Several long thick ropes shot high up into the air, and Susan ducked her head back and laughed as one of the shots nearly hit her in the eye. That was at least eight long months worth of jizz, that I had been saving up...plus, the pressure being put on my prostate by Susan's cock made things even more intense, then they already were.

"Look what a mess you made," Susan said seductively.

"And you came before me! How dare you."

"S-Sorry," I said, panting and sweating heavily.

"Hmm, we're not done here. The rent is not paid off, until I get to dump a load of my own love juice, deep in this tight little butt."

That was all fine with me.

Susan continued ramming my ass, well after my own orgasm had subsided. In fact, she was able to make me cum more than once, that night. It was like one huge rolling orgasm, that seemed to never come to an end. I just kept shaking and convulsing as she fucked me, cumming again and again, all over myself.

Finally, Susan buried herself balls deep in my ass and erupted, pumping her seed into me and painting my insides white. Then she collapsed on top of me, her breasts pinning me to the floor with all of her body weight.

"Now THAT'S what I'm talking about," Susan laughed, as she rolled off of me and onto the floor.

I couldn't say anything. I was just coming down from that intense orgasm, the greatest feeling I had ever experienced, and my whole body actually felt numb now. Susan propped herself up on one elbow and smiled down at me, kissing my forehead. I loved the way she looked right then, her skin glistening with sweat and her cock still semi-hard and wet with lube and cum.

"You alright there, sweetie?"

"I-I think so," I said in a weak voice.

"You look so tired."

Susan helped me stand on shaky legs, and put my clothes back on. I crept back downstairs to my own apartment and went straight for the shower. Melissa was asleep; or at least, she looked like she was. Little did I know, she was just pretending. The girl had heard everything that had happened upstairs, and it was definitely weighing heavy on her mind. I showered, washing the cum out of my asshole and rinsing away Susan's scent. I climbed into bed and as soon as my head hit the pillow, I was knocked out cold.

When I woke the next morning, Melissa was sitting up next to me, enjoying a cigarette. She glanced over at me, blowing smoke in my face and looking away. She looked irritated, though I wasn't quite sure why. "You alright?" I asked.

"Sure sounded like you had fun last night," she said softly.

Fuck...she'd heard us!

I had gotten pretty loud, while Susan was fucking me. I tried to keep my voice down as much as I could but, once I started cumming, I just lost complete control over myself.

"I thought you were just going to suck her cock?"

"I-I did...that's all that we did."

"Bull shit," Melissa laughed. "God, all I could hear was you moaning like a total fucking bitch; it was pathetic. You actually enjoyed getting fucked in the ass by a tranny, didn't you?"

SLAP!

Melissa smacked me right across the face; I was stunned!

"Answer me," she demanded. "Did you like being fucked in the ass, you fucking cock sucker!?"

"Knock it the fuck off," I shouted at her, as she tried to slap me again, and again. We ended up grabbing each other and rolling around on the bed, as she tried to wrestle me into submission.

We both stopped, with Melissa on top of me now and it was only at this point that I noticed, she hadn't been wearing any panties this whole time. She was chewing on her bottom lip when she started slowly grinding against me; what was happening? Soon, she was humping me and my cock was starting to get hard. I could feel her wet pussy, sliding over my dick...Melissa had a look in her eye, that she had not had in a very long time.

Neither of us said anything, as Melissa reached down and grabbed my dick. She lined it up with her pussy, sliding it deep inside of her and started slowly riding me.

Fuck, she was so wet!

I reached up under her shirt and started fondling her breasts, as she bounced up and down, riding my cock like a horse. We both moaned, Melissa, leaning in and kissing me on the lips, her tongue sliding into my mouth. She pulled away after a moment, then removed her shirt, throwing it to the floor. I pulled her close and started sucking on her tits, as she started riding me harder and faster. My cock was starting to pulse, and I knew that I wasn't going to last for much longer.