Jenna

Story Info
Jenna always gets what she wants.
7.6k words
4.76
107.1k
223
25
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

After a long day of work, I was happy to be on my way out the door and heading home to my apartment. I was exhausted to say the least, as it was 11:00 at night, and I had just finished closing the store. As a night janitor, it was my duty while closing to get rid of all trash and cardboard throughout the departments before the end of the night, and clean things up for the opening crew in the morning.

It was a dirty job, but it put money in my wallet, and that was all I cared about in the end.

It was about a fifteen minute drive from where I worked, back to my apartment. Arriving home, I made my way upstairs and unlocked the door. Stepping inside, the living room was quiet... but like most nights, once I reached the hallway I could make out the unmistakable sounds of my roommate having sex with yet another of her new pets. I laughed silently, shaking my head.

I lived with a transsexual woman by the name of Jenna, who I had met on the internet about a year ago. We found out we lived nearby, shared a mutual interest in video games and most manly activities, and as luck would have it, we both needed a new place to stay. Jenna told me right off the bat that she was a transsexual, and looking back on it now, I was surprised she hadn't tried hooking up with me then.

Jenna liked 'fishing', as she called it. She was very much a dominant person, and also didn't have any intention of having SRS, or sexual reassignment surgery. She loved her penis, and loved to make use of it. She liked going out, hooking up with guys who had no idea what was between her legs, bringing them home and fucking them senseless. Not just typical guys though, she liked to break down the macho, stereotypical straight guy and show him that... in her words...

"Pussy is not all it's cracked up to be".

I wish I knew how she did it, because she seemed to be great at getting these guys who swore they were straight, to stay the night with her even after they found out what she had between her legs. I made my way to my own bedroom, firing up the computer and then walked out to the kitchen to grab myself a beer. I sat down at my desk, to check my mail and Facebook...all I could hear coming from the next room was Jenna and whatever guy she brought home, going at it.

And were they ever going at it! I laughed again, as I heard the loud moaning and panting and the sound of her bed shaking. After a few minutes, the sounds finally came to an end, and the apartment fell oddly silent. Save for the sound of the fan inside my computer.

At around 12:30 I shut the computer off and decided to call it a night. Normally, I was up a lot later than this, but tonight I just felt really tired. It had been a particularly busy day at work and so I figured I just needed the extra bit of rest.

I woke the next morning, and rolled out of bed, making my way to the bathroom to take a piss and grab a quick shower. I had the day off from work today, and was hoping to hit the gym for a few hours and then maybe just relax afterwards. When I came out of my bedroom, after showering and drying off then putting on some new clothes, I found Jenna was awake and in the kitchen, brewing some coffee.

"Morning," she called out, as I came down the hallway.

"Morning to you too," I said, with a knowing grin as I sat down at the kitchen table. "Sounded like you had a lot of fun last night."

She laughed, turning around to face me and leaning against the counter behind her.

"Yes, it was quite a lovely night. I met this guy named Jimmy, at a bar. We danced for a while, then we did the dirty."

"I could definitely hear you doing the dirty... another 'straight' guy take the news better than expected?"

"But of course," she replied, smiling, "you know by now it's pretty damn rare for any guy to say no, even after he finds out that I have a bigger cock than he does."

I laughed, as she handed me a cup of coffee. But as I took a sip and set it down on the table, my grin turned to concern, as I did occasionally worry about her doing these sort of things. Hell, all of our friends worried about her doing this shit. Guys can be assholes, and a lot of people were afraid that she could get the shit kicked out of her by someone for being who she was and not telling them up front. Fact of the matter was, Jenna was no pushover.

She worked out, lifted weights almost daily, and she knew a bit of mixed martial arts, too. If anyone ever tried to hurt her, well... they'd be in for quite a surprise, I was pretty sure of that much, but I still worried about her.

"You know, I'll never stop wondering how the hell you do it," I said curiously. "I mean, all these guys swear they are straight and they aren't interested. But somehow you manage to get in their pants anyway, every single time."

"What can I say," she asked, giggling and pulling out a chair as sat down across from me, "I have a magic dick... or magic cum... one or the other."

I'd heard all about her dick, and at one point I had even seen it. She had bragged early in our friendship about how big she was, supposedly standing nearly 11 whole inches when fully erect. I mean, I have to admit, I didn't believe it when she first said it to me, but it was after we moved in together that I found out she was definitely bigger than average. I accidentally walked in on her coming out of the shower one day, drying herself off with one foot on the side of the tub, her cock just dangling between her legs.

It wasn't erect mind you, so I couldn't say exactly whether or not it was 11 inches, but even soft it looked to be at least 8 inches. I found out later that the bragging was true when I happened to once again walk in on her. This time in the middle of having sex with some other guy. I was surprised to see that, at least from the glimpse I caught, she had to be about the size she claimed while fully erect. That cock was huge!

"I won't lie," I said. "God blessed you with a gift, to have a cock that big."

"Yes, well, some people are just lucky I suppose,"

she replied wistfully. "So, what're you up to, today?"

"I'm heading to the gym. Probably just going to lay around the apartment and relax when I get home. How about you?"

"Well, I was going to hang out here for a while... but I think I might head to the gym with you, if you don't mind."

I shrugged my shoulders, "Doesn't bother me. I'm leaving in about fifteen minutes. Where's your new friend from last night?"

"He left early this morning. Woke up and of course, the whole confusion thing set in, so he made his way home to 'clear his head' like they all say."

I laughed at the sarcastic grin on her face. Jenna always tried to act like she knew what every guy was going to say the morning after. Nine times out of ten, she was right... but I also knew she liked to pretend it didn't bother her. None of those guys ever came back. A couple of them did, but not for what I knew she really wanted.

They had a tendency to come back for a second round, and then disappear after that. Not that Jenna didn't like having another go with them, but I had this feeling that she wanted more than just casual sex. Maybe at one point she had been content for just sleeping around, but there was something in her eyes lately whenever this would happen that told me she was growing a little more mature. She wanted something deeper than just sex.

Jenna got up from the table after finishing her coffee, and went to her room to start getting ready while I stayed behind to finish mine. When she came back out of her room, she was ready to go, so I grabbed my car keys and out the door we went.

We got to the gym around 10:00 that morning, and both started out running the treadmill just to warm up. After that, we moved on to some of the weight machines, and did a series of bench presses. We spent about an hour and a half there in total, before deciding that we were both done for the day.

We made our way back, stopping briefly to grab something to eat before returning to the apartment. We went into a local burger joint in a mini-mall near our apartment, I took note of the game store next to the restaurant. Sitting in the display window was a game called Final Fantasy Type-0, that I had been wanting for a while now.

It came out in March, but with bills and rent I hadn't been able to put anything away to pick it up myself. I really had been wanting it though.

As I stood there looking at the game through the window, Jenna came up and put a hand on my shoulder, startling me a bit.

"You ever going to buy that damn thing, or are you going to just keep staring at the display and watching videos on YouTube for it," she asked.

"I can't afford it, I have to much other stuff to take care of."

"Oh c'mon Jake, cut yourself a break for once," she sighed.

She knew me better than anyone, and we both knew that when it came to spending money on anything other than bills or necessary food items, I was like a locked vault with my money. She was always telling me to give myself a reward, that I deserved it... to some degree, I felt like she was right. I just couldn't override that part of my brain. We left the restaurant after finishing our meal, and drove home in silence.

When we got back to the apartment, we walked upstairs and I plopped down in the recliner, turning on the TV. Jenna walked into the kitchen for a few moments, and then came back out. She stepped in front of me, blocking my view of the television, hands on both hips and a big lopsided grin on her face.

"Jenna... I can't see, what are you doing," I asked, a little annoyed.

"I have a proposition for you, if you'd like to hear it."

"Um... okay?"

She cleared her throat, moving one hand from her hip down to her sweat shorts and over her groin, rubbing her cock through her pants. I was a bit surprised, and wondering what the hell she was doing, when she spoke up finally.

"How badly do you want that new game, Jake?"

"Um... pretty badly... why?"

"Well, just what exactly are you willing to do for it?"

I took a deep breath, starting to get an idea of where this was going. I was hoping she was just joking around with me though.

"Almost anything... apart from stealing it anyway."

"Good," she said, smiling. "What if I said I would buy it for you. As long as you're willing to do something for me?"

"Well... um... what do you want me to do?"

She motioned down with her head, and I knew I was right. I knew what she wanted me to do in exchange for that game.

"One blowjob, and that game is all yours baby,"

"Oh c'mon Jenna," I said laughing. "You can't be serious?"

"I am Jake, I'm totally serious. You suck my dick, and I promise as soon as we're done I'll drive straight to the game store and get Final Fantasy Type-0 for you. I promise!"

I laughed, leaning forward in the chair and trying to convince myself that she wasn't seriously trying to get me to do this right now. After knowing each other for an entire year, she hadn't once tried to get me to hook up with her. Now, here she was offering to buy me a video game if I sucked her dick?

"Jenna, I'm straight!"

I regretted saying that a moment later, when I remembered just how many guys she had hooked up with in the past, had said exactly that before they bent over and let her plow them from behind. But I really was straight, that was the difference.

"Well, you did say this morning that you were curious about how I always get what I want," she said, reminding me about our conversation earlier that morning at breakfast.

"Yeah... I did say that," I laughed, nodding my head.

"So? Why don't you let me show you what all the boys love? C'mon, one blowjob and that game is all yours."

I bowed my head, trying to figure out if this was really a good idea or not. Jenna didn't wait for an answer anymore. She backed away from me, across the living room and stopped in front of the couch. She hooked her thumbs on the sides of her shorts, and slowly pulled them down. I could see the bulge in her panties from her cock, and I watched as one hand slipped under them and started stroking herself.

The other hand slid up under her shirt to tease her breasts, while she continued stroking her cock for me. Then, she slowly pulled down her panties as well, stepping out of them and parting her legs. Her massive cock sprang free, standing at full attention and she grasped it again, stroking it a little faster now. She sat down on the couch and winked at me.

"It ain't gonna suck itself baby," she said seductively.

Finally, I caved... I couldn't believe it... but I caved. I stood up from the recliner, and slowly walked across the living room towards the couch. Nervously, I got down on my knees in front of her and took a deep shaky breath.

"Don't be so nervous," she said, "you're gonna love it."

I leaned in close, and could feel the heat coming from her shaft against my face. I inhaled the musky aroma, and felt myself getting a little harder now. I opened my mouth, and she grabbed my head, forcing my mouth down over her cock. I gagged as she hit the back of my throat and started moving my head up and down over her dick.

In and out of my throat, her giant dick slid, causing me to gag and slurp. Spit ran down my chin and over her balls and Jenna moaned loudly as she fucked my mouth.

"Oh, fuck baby... that's nice," she said softly.

She let go of my head, and allowed me to take control. Struggling to overcome my gag reflex, I started sucking, bobbing my head up and down and slowly managing to take more and more.

"So how does it taste Jake?" she asked.

I backed off, gasping for air and looking up at her. I took hold of her dick and started stroking, as I tried to think about what I was actually doing at the moment.

"It's... um... good," I admitted.

"Yeah? See, what did I say? You were going to love it!"

I leaned in, taking her back into my mouth and started sucking again. This time, I managed to move all the way down, taking her entire length deep into my throat. I was impressed with myself, but as I was about to come back up for air, her hand moved over my head again and forced me down, keeping me there. I gagged, and then she grabbed my nose and pinched it keeping me from breathing for a few moments. When she let go of my nose, I pulled up for air immediately, and gasped. Spit running down my chin, my eyes watering; I must have looked like some slutty girl in one of those really crazy porn videos.

I moved back in, taking her in my mouth for the third time. This time, she allowed me to work it on my own again. I picked up the pace, sucking faster and stroking at the same time. Jenna started to moan, louder and louder and I could feel her cock starting to get bigger in my mouth, if that were even possible.

I knew what was coming... well... SHE was cumming.

"Jake...oh, Jake...oh FUCK!"

She cried out, pushing my head down again and lifting her ass up off of the couch cushion. Her balls pressed up against my chin, and her cock exploded deep in my throat, pumping what felt like a gallon of thick, warm cum down my gullet.

I swallowed it all, barely managing to taste any of it and she sighed, letting herself sink back into the cushions again as her orgasm started to slowly fade. Once she had finished, her dick started to go flaccid, slipping out of my mouth. I sat there, breathing heavy, my face flushed and a bit sweaty. Jenna gave me a pat on the head and leaned in to kiss me on the lips.

"You did really good Jake, I'm very impressed."

"Thanks," I said, still just a little out of breath.

I moved over, and Jenna stood up and stretched. She walked to the bathroom, leaving me there to think about what had just happened. After she emerged from the bathroom, she walked back over towards me, her giant cock swinging back and forth between her legs. She leaned over me, her cock right up in my face again, to breathe in her scent once more. She grabbed her panties, and slipped back into them, followed by her shorts.

"Well, a deal's a deal. I'm going to go get you that game now."

"Holy shit... really?"

"Hell yeah, I mean... I promised, didn't I?"

"Yeah," I laughed. "I just sort of thought you were only saying that to get me to suck your dick... I didn't know you-"

"Jake, I was horny and yes I definitely wanted to get off. But I keep my promises. I'll be back in about half an hour," she said, walking towards the door.

Once she had left the apartment, I pulled myself up onto my feet and stretched, as Jenna had just done. I walked to the kitchen, and grabbed a bottle of water, washing down the taste of her cock that still lingered on my breath. I sat down at the kitchen table, and started thinking about what had just occurred... all for a damn video game, too. I pondered the fact that I had actually been pretty turned on the whole time I was going down on her. That my own dick had been as hard as hers. That I had actually come to realize that I was pretty good at sucking dick... who would have ever thought that about me?

What did it all mean though... what did it make me?

I brushed it off, deciding not to obsess over it too much longer. That wouldn't get me very far anyway, even if I did. I told myself it was only a blowjob. Just one blowjob. But the problem was, I had liked giving it and part of me wondered if it was going to remain a onetime thing or not.

I decided to take a shower, and try to forget about it all. I stripped out of my clothes, went into the bathroom and turned on the shower water. After letting it warm up, I got inside and relaxed.

Ten minutes later, as I was getting out of the shower, I could hear movement in the living room... Jenna must be home.

Excited for the new game, I reached for my towel to dry myself off when the bathroom door swung open, and there was Jenna. She had a full view of my totally naked body, dripping wet from the shower, and I just stood there shocked that she had walked right in without knocking.

"Hey there sexy," she said, obviously impressed by what she saw.

"Uh... Jenna... do you mind?"

"Hm?"

I held up the towel, trying to indicate to her that I wanted a little privacy, but she just laughed, leaning against the door frame.

"Your game is on the kitchen table," she said, reaching her hand into her shorts again to stroke herself.

"Right," I said, wrapping the towel around myself.

"Thank you... I really do appreciate you doing that for me."

"Oh? Well... why not show me how much you appreciate it?"

I chuckled, thinking maybe she was kidding, but, I could tell by that familiar look on her face that she was serious. Standing there staring at me seductively, biting her lower lip in anticipation.

"Take your pants off," I said, barely even realizing what I had just said, until the words left my mouth. I was shocked at myself, but it was too late, as Jenna slid out of her shorts and panties once again.

I sat down on the toilet, after putting the lid down, and Jenna moved further into the bathroom until she was standing over me. Here I was, getting ready to suck her cock... for the second time in the same day. What was happening to me? I was really starting to come under her spell.

I leaned in, taking her dick right in my mouth without hesitation, and started deep throating right off the bat. She groaned, running her hands through my hair as I sucked and stroked. I reached up, under her shirt and started to tease her nipples. She moaned louder, as I gently pinched them and massaged her tits, all the while continuing to work her cock with my mouth.

It didn't take her very long, before she was moaning and panting, thrusting in and out of my mouth.

Her cock swelled up once more, and she pulled back slightly this time, before exploding. Since she had pulled back slightly this time, it allowed for me to actually taste her cum this time whereas before it had shot straight down my throat. It was a little salty, but almost tasted sweet too if that made any sense. It was actually surprisingly good.

12