Jenna

As her orgasm began to fade once again, she sighed, pulling her dick from my mouth and smiled down at me.

"That was even better than the first time," she said.

"Thanks," I replied, standing up.

"You know... we could make this... sort of like... a long term thing, if you think you might be open to it anyway."

"What are you talking about," I asked, unsure of what she meant.

"Well... I mean, instead of me having to run out and find some guy at a bar when I'm horny, I have you here under the same roof as me. Maybe I could just come to you whenever I need my dick sucked?"

I laughed, but I knew she meant it like always. I thought about it for a minute or so. To say yes, would mean that I really had come under her spell. Even now, after I had sucked her dick twice, I still couldn't understand how I had gone from being so sure of my sexuality to sucking dick and liking it so much.

"I don't know," I said.

"You're right."

I was surprised, to hear her say that and wondered if she was going to back off, that would be totally unlike her though.

"I have a better idea!"

There it was, I thought, laughing silently.

"Now that you've sucked my dick twice... why don't you let me get a piece of that nice tight little virgin asshole."

"Oh," I said, standing up. I definitely didn't think that was something I was going to be doing.

"I don't think so; that's a little too far for me."

"Think so? C'mon Jake, you've already given me head, why not take it one step further?"

"Jenna, I really don't think that's something I want to do."

She sighed, looking a little frustrated now.

"Look... why don't you go sit in the living room.

Let me take a shower, and we'll talk about it more after I come out," she said.

"There's not much to talk about Jenna, I-"

She didn't let me finish that sentence, pushing me out of the bathroom... without my towel... and shutting the door in my face. I sighed, a little annoyed now as I walked out into the living room and sat down on the couch. By now, I had pretty much air dried from my shower, so I didn't really need the towel. I did need to get dressed though.

I stood up from the couch, and my eyes moved over the bag sitting on the table with my game in it. I had almost forgotten that I had earned myself the copy of Final Fantasy, and walked over to the table to take a look at it.

I ran my hand across the case, thrilled to finally have this game in my possession, and it was all thanks to Jenna. Of course, she never would have gotten it for me if I hadn't done what I did for her. Regardless, I was extremely happy to finally have the game I had wanted for so long now.

I heard the bathroom door open, and saw Jenna step out, completely naked and dripping wet from the shower.

"No towel?" I asked, staring at her full nude body.

"Nope... I don't need one, and neither do you."

"Jenna look, sucking your dick... that was okay. I liked it, but I really don't want to-"

"Shh," she said, coming up to me and placing her finger over my lips to silence me. "I have another deal to make you. Well, I'm not offering to buy you anything this time, but I think it will be fun for both of us."

"Okay? What?"

She stepped into the middle of the living room and smiled at me. "Let's have a good old fashion wrestling match... stark naked!"

I laughed, as she held her arms out at her sides for me to come and join her in the middle of the room. We wrestled all the time, in sort of a friendly kind of way, which was funny, since we weren't even dating, but it was always fun. The only thing was we had never done it naked before.

That would explain why she had sent me out here without my towel, hoping that I wouldn't get dressed before she came out.

"Why would I do it naked though," I asked.

"Because, it's so much more fun when you're naked."

"Yeah, but I mean... what's your angle here?"

"Well," she said, walking towards me, and leaning against the fridge. "The terms are this... if you win, I'll return the favor you did for me... twice... and I promise it's going to be the best blowjob you have ever had in your life."

I liked the sound of that.

"And if you can beat me in under two minutes, I'll even let you fuck ME in the ass," she said.

Now THAT was a shock; Jenna was a total dominant top. I figured she probably didn't mind sucking cock from time to time, but I never would have thought she'd offer up her ass.

"And if you win?" I asked, wondering what she thought she would possibly get out of all of this.

"Well, isn't it obvious?" she asked. "If I win, then I get a piece of that virgin ass of yours."

Now I saw the angle she was trying to work. I also realized this was a lose-lose battle for me, most likely. Jenna usually always won our little wrestling matches. For one thing she was taller than me, and though I lifted weights too, she was definitely stronger than me too. Now, that didn't mean that I had never won a match with her; it just meant that generally, she was always the one to win. So, the possibility of me beating her was pretty fucking slim. That being said, did I really want to do this?

"C'mon Jake," she said, for the hundredth time that afternoon. "I know you want a piece of this ass," she said, turning around and bending over for me.

My heart pounding in my chest, I couldn't lie to myself. I had always loved her ass, even though I knew she was a transsexual. Seeing it bent over in front of me, naked, now that was an absolutely beautiful sight. And the idea of being able to have a piece of it? That was even fucking better! It was worth at least trying to win.

"Alright, fine... let's do it."

I felt like I had just signed over my life savings or something. I was going to have to really try hard to win this little match. For one thing, I REALLY didn't know how I felt about her fucking me in the ass. Especially since I was a virgin in that department. On top of that, I REALLY wanted a piece of HER ass.

"Good, let's go then," she said, stepping into position.

Her arms out in front of her, ready to grab, I stepped forward and moved into a similar position. I jumped forward first, which was probably a mistake. In my attempt to grab her, she grabbed me first, spinning me around and throwing me to the floor.

I landed with a thud and she jumped on top of me, grabbing my arms and instantly trying to pin them above my head. I struggled, moving my knees up to push against her and managed to shove her off of me. I got up on my knees, and moved towards her. We grabbed each other this time, both of us trying to push the other off balance.

Finally though, I managed to push her down, pinning her arms at her sides. I smiled, thinking I had her where I wanted her! I was wrong though. She easily found the flaw in my stance, and slid right out from underneath of me, coming up from behind. She put both hands on my back, and pushed me flat down on the floor. She jumped on my back, and I grunted as she grabbed both arms and tried to pull them behind me.

I groaned, trying to get free and once again managed to flip over. Rolling around on the floor for a few moments, our naked bodies pressing against each other, sweating and panting... it was like we were having sex. She was still a little wet from the shower, and now my skin was wet too from rolling around with her. We rolled over again, her on her back, and my back against her... a pretty awkward position as she had me on top of her. I thought I had her pinned, but I realized that in this position she actually had ME pinned.

As she held me like that, lying on top of her with my back facing her, I felt her cock pressing against my ass. I struggled to get free, and this time it was a little more difficult. I was getting tired, my arms hurting a little too. I managed to break out, one final time, freeing myself from her grasp. Breathing heavy, and getting tired, I moved back slightly to put some space between us.

Jenna smiled at me, and I looked down to see that her cock was hard as a rock. She lunged at me, knocking me over and I landed face first on the floor. It was a good thing that the apartment below us was vacant, or someone might have called the cops by now.

Pinning me on the floor, face against the carpet, she once again pulled both of my arms behind me. She hooked her legs under mine, keeping me from moving them and pulled hard on one of my arms. She could let my other one go free; it wasn't like I could move from this position with just one arm.

"Tap out," she shouted.

"Agh... no!"

She pulled harder at my arm and I grunted.

"Tap out," she yelled again, her voice more stern this time.

I still gave no response, and she tightened her grip more pulling harder. It was getting a little painful now, but I wasn't willing to give up just yet.

"Do it," she yelled. "Tap out!"

Still no response.

"Jake... you have to tap out, or you're going to get hurt," she said.

I thought about it, and she was probably right. She had me where she wanted me; I wasn't getting free. The longer I held on like this, the more likely she was to hurt me.

"Tap out!"

"F-fine," I shouted, smacking the floor with my free hand several times. "I tap out, I tap out!"

She immediately released me and my whole body sank into the carpet. She continued to sit on my back though, as I struggled to catch my breath, my arm throbbing. It took a few moments for me to relax, and at that point, I felt Jenna shifting a little. Then, I felt her cock rubbing along my ass crack... reminding me that because I had just lost, that meant she was going to have her way with me now. She was teasing me, rubbing my crack with her dick, probing me gently but not actually pushing into me.

"You're all mine now baby," she said, whispering in my ear.

I shivered, her hot breath against my neck as she started kissing my neck.

She slid off of me, and I felt her spread my ass cheeks. Then I felt something hot and wet touching my hole; it took a few moments to realize, it was her tongue. This was a day of many firsts, now my first rimjob too. She licked up and down my crack, covering my hole in spit, probing it with her tongue. As she did this, she pulled my cock back between my legs, stroking it for me. Then, she moved her mouth down from my ass and I moaned loudly, as I felt her wrap her warm wet lips around my dick.

I was surprised, since I had lost the match, that she was still sucking my cock right now.

She sucked on me for a few minutes, before she started to work one of her fingers into my asshole. She continued sucking, while pushing her finger deep into my ass and started moving it in and out. It was a strange sensation to have anything in there, but it wasn't exactly a terrible feeling either.

I gasped, as I felt her trying to insert another finger, spreading me a little wider. As she pushed two fingers into me, all the way to the knuckles, it started to hurt just a little but still not overwhelming.

"Mm... you know, I have had my eyes on this sweet ass of yours since we first met Jake," she said.

"Really? W-well... why didn't you try to make a move until now?"

She shrugged her shoulders, tilting her head to the side.

"I don't know honey... there was something different about you. All the other guys, they were just pick ups. I got horny, I'd run out and look for someone willing to hook up. I just happened to get a thrill out of picking up boys that claimed to be straight."

"What's so different about me then," I asked, as she continued to work her fingers in and out of my ass.

"I liked you... a lot. I didn't want to do it the wrong way, and scare you off. I didn't want it to be just some random pick up."

I smiled to myself, realizing what she was trying to say. Some part of me had always liked her in that way too, I couldn't deny that. It showed easily too. How we were always getting into those playful wrestling matches, the kinds you would see a boyfriend and girlfriend having. How we were always hanging out together, and how we both felt so comfortable around each other. Sometimes, I'd even find myself feeling a little jealous when I knew she had some guy in the room with her.

"I think you're ready now," I heard her say, behind me.

I felt her fingers slide out of my ass, and she moved over top of me again, laying her body on top of mine. It felt really sensual, to have her bare skin against mine, her big tits poking against my back as she ran her hands up and down my arms. I felt her cock poking at my hole again, and she started probing me, humping me and rubbing it along my crack. I was nervous... very nervous.

She must have sensed that, because she started kissing me on the neck, to try and relax me a little.

Then, she lifted her hips just a little and I felt the head of her cock pressing against me, no longer in just a probing way. I bit my lip, digging my nails into the carpet as I felt her pushing, until finally it popped right into me. I gasped, trying not to scream as she slid the head into my hole and grunted in my ear.

"So... fucking... tight," she said in my ear.

"Fuck... it hurts," I gasped.

"It's okay baby; it'll stop hurting in a minute,"

she said, kissing the back of my neck.

Slowly, and carefully, she started pushing the rest of her dick into my ass. She took it slow, easing her way deeper and deeper into me, inch by inch, going at my pace. She paid close attention to my actions, using them to judge whether or not I was ready for more.

Finally, after what felt like forever, Jenna had gotten her entire cock, balls deep inside of me. I had a feeling of fullness back there, a little uncomfortable but for the most part, the pain was starting to subside.

"You alright," she asked.

"Yeah... I think I'm good now."

"Okay baby...I'm going to start moving now, alright?"

"Go ahead."

She pulled back, just slightly and I could feel her moving inside of me. Then, she moved forward, pushing all the way back into me to the hilt. She repeated this, slowly a few times before she started to increase the speed. Soon, she was moving a little faster, pushing me down against the floor as she thrust in and out of my ass. I was starting to really adjust now, and actually enjoy the feeling of her cock sliding in and out of my ass. I moaned, and she took that as a hint that she could let loose now.

And let loose on me she did. She placed both hands over my head, propping herself up on her feet, and started slamming in and out of me. I gasped, moaning louder as she drove her cock as deep as it would go, fucking me harder and faster.

She dropped down on top of me, and I yelled out. She started grinding against me, humping me. Her cock was deeper now than I thought even possible. She continued like that for a few minutes, before pulling out and turning me over onto my back. She lifted my legs all the way up and slipped right back into me. It was a much easier entrance this time, and she wasted no time as she started pounding my ass. In missionary I was looking right up at her as she fucked my ass, and her tits bounced as she did. I reached up, massaging them and she leaned in close so I could suck on them as she fucked me.

"Oh Jake... fuck sweetie... that feels good," she moaned.

I stopped sucking her nipples, and our lips came together and we started making out. Her tongue slid into my mouth, making this whole thing even more sensual. We continued kissing passionately, as she fucked me harder and harder. I felt her swelling up inside of me, stretching me even further and she buried herself to the hilt and exploded.

There was a feeling of something warm and wet flowing inside of me, it was her cum filling my ass all the way up.

When she finished, she collapsed on top of me and we laid there for a few moments. My body was shaking, my hole still squeezing around her cock, keeping it nice and hard. She pulled out of my ass and before I could do anything else, she thrust back into my mouth for the third time that day. She started fucking my throat, and I could taste myself on her dick.

Once again, she came hard, pumping her load down my throat and I groaned, tasting the thick seed. Finally, she seemed exhausted and collapsed beside me on the floor.

"That, was fucking hot," she said.

"Yeah... it was pretty hot," I said, reaching over and giving her dick a squeeze.

"You have definitely got a magic dick," I said and she laughed.

She looked over at me and sat up, smiling as she noticed that my own cock was still hard as a rock.

"Looks like you're not done," as I followed her look between my legs, "let's fix that, shall we?"

She pushed me onto my back, and leaned in, taking my cock in her mouth and immediately started deep throating. I moaned loud, gyrating my hips and running my hands through her hair as she worked on me vigorously with her lips.

I was just about to cum, when she stopped and smiled up at me.

"I have another idea," she said. "Why don't I let you have a piece of this ass, even though you lost our little match."

"Wait... Jenna... seriously?"

"Yeah, it's actually been on my mind for a while now. I really want to feel you inside of me."

"I mean... okay... if you're sure. Have you ever done this?"

"Yeah, a few times," she said.

"It's not something I like to do often. It has to be the right person... and I think you're the right person in this case."

It definitely felt nice to know that she trusted me enough to let me fuck her ass. I couldn't fucking wait. She wasn't going to make it that simple though, I realized as she suddenly got up and before I could say anything, she was shoving her ass in my face. I breathed in the scent, moaning as my dick started throbbing and leaking pre-cum. I licked her asshole, tongue fucking it like she had done to mine earlier and getting it nice and wet.

Meanwhile, she leaned in and swallowed my cock once again...we were in 69 position, me fucking her ass with my tongue while she got my dick nice and slick with her own spit.

This went on for a few minutes, before she stopped sucking and pulled her ass out of my face. I was almost disappointed, but she made up for it when she turned around to face me. She stradled me, lowering her ass down slowly over my cock until the bulbous head was pressing against her hole.

Jenna's hole was spreading wide for me as my cock pushed deep inside of her. She made a funny face as she worked herself down over my shaft, and my hands moved to her hips.

Once she had lowered herself completely onto me, she started grinding. She was moving up and down, slowly riding me as I held onto her by the hips. Then, she picked up the speed, riding me faster and more rough too. She leaned back, placing both hands on the floor behind her and began riding me like a horse. Bouncing up and down in my lap, her own cock flopping around and slapping against her belly and mine.

"Fuck... Jake... oh yeah... fuck me," she moaned.

I flipped her over onto her back, legs wrapped around me, and started thrusting in and out. She dug her nails into my back, as I slammed in and out, feeling myself starting to get closer and closer. Finally, I slammed deep inside of her, holding myself still and I cried out in pleasure as I erupted, filling her ass with my cum.

She held me close as I emptied my seed into her ass, and we started making out, tongues wrestling and hands roaming freely.

I pulled out, and laid down next to her and she cuddled up next to me resting her head on my chest. We were both completely spent by this point.

"So," Jenna said finally after a few minutes of silence.

"What do you say... boyfriend and girlfriend?"

I laughed, my eyes heavy as I tried to keep myself awake a bit longer.

"Sounds good to me," I agreed.