Jogging Partners Ch. 05

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Experimenting.
4.5k words
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Part 5 of the 8 part series

Updated 10/24/2022
Created 01/29/2013
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I woke the next morning with Lauren still wrapped in my arms under the blankets, our warm bodies pressed together. Memories of our first time together from the night before came rushing back; it was no longer just a fantasy of mine. Now it was reality, now I really was more than just a friend of Laurens. It felt good to be able to say that though, because I had wanted this for a while now and it' also stood as proof that my days with Jennifer were officially in the past.

Lauren groaned and shifted in my arms and I held her closer not wanting to let go, but I knew in a few minutes she was going to wake up and we would have to start our day at some point. Slowly, she opened her eyes and smiled sleepily up at me then leaned in and gave me a kiss. "Morning," she muttered.

"Morning; you still seem really tired."

"Mmm...I guess I' kind of am. Last night was...fun,"

I could tell the details were a little hazy to her as they had been for me at first but she continued smiling and I knew it was okay.

I noticed the dark bruise under her right eye and instantly remembered that she had come home from her date last night rather upset and had explained to me that the guy' she had gone out with pretty much assaulted her. She had also told me about her history with her ex-boyfriend Marc and' how he used to abuse her as well. I felt the sting of anger as I thought about the guy' she went out with last night and how he had done this to her; if I had only been there I would have torn him to pieces.

I kissed the bruise and she flinched but relaxed and I continued to hold her.

"How about that trip down the park," she asked. I laughed remembering that as we had been drifting off she suggested we take our bikes down the park today.

"Sounds good to me," I replied. "Guess we should take a shower."

"Probably, or we could wait; we'll be all sweaty when we come back from the park."

She sat up and the blankets slid off' of her as she rolled out of bed and stretched, turning around to smile down at me. I smiled at the sight of her cock dangling between her legs and felt my own beginning to stiffen underneath the sheets. I got out of bed as she started walking towards the bathroom and followed her through the door as she grabbed her toothbrush and turned on the warm water in the sink.

I wrapped my arms around her, my cock pressing up against her ass and she laughed as I ran my hands down her thighs and moved my right hand over her penis and started gently stroking. I kissed her neck and she groaned softly and leaned her head back; I could feel her cock stiffening in my hand.

"Now, now," she whispered. "There's plenty of time for you to experiment after we get done down at the park," she moaned again.

I wasn't' hearing it though, I was still aroused and as long as she did not show any signs of serious protest I wasn't going to back down that easily. She set her toothbrush back down on the sink, but forgot to shut the water off in the process; she turned around to face me and our lips connected in a passionate kiss.

Our tongues entwined we started caressing each other's bodies.

As she kissed me she leaned back to shut off the sink and our lips parted. I slid down onto my knees and started kissing her inner thighs while stroking her cock, which was fully erect at this point. I leaned in close and wrapped my lips around her, moving down until I had taken her entire length all the way.

I amazed even myself at how well I seemed to be doing as I started bobbing my head, her hot cock sliding in and out of my throat and her warm balls pressing up against my chin. I grabbed her by the ass and pulled her deeper into my mouth and she groaned as her head began to swell.

Before I knew it, she started calling out my name, gasping and moaning in pleasure and I felt a stream of hot sticky cum shoot down my throat. I took it all and swallowed every drop but started choking a little; she was Cumming so much and it was a bit hard to keep up with her.

When she finally stopped, she sighed in relief and I pulled her cock from my mouth and stood up to kiss her again.

"Someone's becoming a real cock sucker," she said and we both laughed. She kissed me again and grabbed hold of my own dick, which was now hard as a rock and gave it a gentle squeeze.

"Now it's your turn,"

She turned around and leaned over the sink and I got the point right away. I grabbed hold of her hips and pushed my cock against her asshole, which was still a bit loose from when I had fucked her the previous night. I slid in without much difficulty and she moaned as I started thrusting slowly at first.

As she gripped the sides of the sink I started' fucking her harder and faster and we both started breathing heavier as we grew closer to our orgasms. I came first, delivering a few more of my strongest thrusts driving into her and burying myself balls deep in her ass. I exploded, pumping my' cum deep into her rectum and she groaned as she started to shoot her own load in the sink. Laughing as we both recovered from our orgasms, she turned the sink on again and washed her semen down the drain as I pulled out of her and sat down on the toilet seat to catch my breath.

"Morning sex," she whispered. "It's always so much fun."

"You can say that again," I agreed.

When all was said and' done, we cleaned up, got dressed, grabbed our bikes and made our way down to the park. I felt refreshed and relieved from our morning session together but Lauren was still giving me seductive glances as we rode our bikes; I had the feeling she was still very aroused. As we rode further down the bike path deeper into Pennypack woods, I started thinking about everything that had happened in the past couple of days.

It started with the big fight with Jennifer, then I left and moved in with Lauren and only the next night we hooked up and now here we were riding our bikes through the park as though everything were completely normal.

Not that it wasn't normal; but I think at this point maybe it was starting to finally dawn on me that I had crossed a line, so to speak as Lauren warned me. I had spent time fantasizing about sex with her even though I knew she was a transsexual; but those were fantasies and this was real.

I could not help but think to myself, what did this mean for me? Was I gay; was I anything less than a straight heterosexual male now that I had hooked up with a girl who not only had a dick but she happened to have a bigger dick then I had? It was all so fucking weird; but then I remembered why I had allowed any of this to happen in' the first place...I was attracted to her,

In the end, you can't run from who you are attracted to because there just is no running from who you really are; if this is what I'm interested in then that's just how it is, it doesn't matter what it makes me.

I realized then that I just did not care; I loved Lauren, she had become my best friend since we first met and now she was my best friend and my lover at the same time. Being able to say the person you are in love with is also you're' best friend is so rare these days, I knew better then to ignore the call.

About an hour into our run, Lauren pulled her bike over to the side of the path and after putting' the breaks' on she jumped off and leaned it against a tree. I came to a stop as well and followed her confused as she made her way down into the woods away from the path. What the' hell was she doing, I wondered as I sped up trying not to lose her in the process.

When I caught up to her, I realized we were now standing alongside Pennypack Creek and it was a really' beautiful spot she had picked. I laughed realizing what she had been doing this whole time. She turned and smiled at me motioning for me to step closer to her and as I did' we embraced each other and shared a kiss.

"So what's the plan here," I asked.

"Nothing special; I just thought we could sit by the creek and relax for a while. Its' really a nice day out and this is a nice spot. What do you think?"

"I like the idea," I said as we both sat down together. It was indeed a beautiful day out today, not to hot and not to cold either, just perfect.

"So," she said suddenly. "Anything you want to talk about?"

I shook my head slowly, "Nothing in particular; why, what's up?"

"Well it's just that; you've taken a huge step in the last couple of days. Jumping from a relationship with a genetic girl to a relationship with a transsexual; I would understand if you were a bit confused or had any questions you wanted to ask."

I was a bit surprised she was bringing this up, especially when it had just been on my mind no more than a few minutes ago. I was hoping she did not think I was going to change my mind about being with her; because that was far from the truth if she were thinking that way.

"I don't know; it's not a big deal to me. I was a bit confused at first obviously, but I'm over it; I know that I love you and that's all that matters."

She blushed and then laid back so that her head was on my lap and she was smiling up at me. The way the sun shone on her face made her beauty really stand out and I smiled back at her.

"I do have one question myself," she said. "Are you really okay with...you know. Doing certain things with my manly parts down there?"

"I don't think that's a big deal," I laughed.

"Obviously if it were I never would have done what I did last night and this morning, right?"

"I know; I'm just not use to that. No one's ever really been okay with giving me pleasure, they always just wanted me to give them pleasure and that was that."

"Well," I replied. "That's not how I am; it works both ways. Which brings up one thing I am thinking about...do you...do you want to um...you know,"

I gave her a certain look, trying to tell her what I was getting at without actually saying it but it did not seem to be working. "What," she asked sounding rather confused and I sighed and looked up at the sky. I cleared my throat a little trying to think of how to say it without sounding weird.

"Well I mean...it's just that I gave you oral sex. And' then I fucked you in the ass; I was wondering if you know...if you want to-"

She started laughing, "Stick it in your bum?" I could not help but crack up realizing she had remembered me telling her about Jen's words. We had made a real joke out of that incident when Jennifer had used the exact words "she wants to stick it in your bum,"

"Yeah, that's one way of putting it," I said.

"I don't know," she said. "I never met anyone willing to let me do that to them either."

"Well...is it something you want?"

She seemed to be thinking and' I felt my stomach doing turns and flips as I waited for her to give me an answer; what if she did want to do something like that. I wasn't' entirely against the idea or anything, I just worried about whether or not it was going to hurt, whether or not I would even be able to take her size like that.

"I don't want to make you do anything you don't want to do," she said finally.

"Well I mean...I wouldn't mind trying. I'm just concerned about pain,"

"It always hurts the first time," she said. "But' that's why it helps to have someone who is willing to be patient and gentle and not forceful."

"Well I guess I'm lucky to have you," I replied.

She smiled and reached up, running her hand through my hair.

"I love you," she said softly. "But you don't have to do this to make me happy. I want it yes, but only if you do too."

I sighed, weighing it over in my mind. I had a lot of trust in her for sure, but I was extremely nervous about the idea,

I decided though that I did want to see what it felt like. I wanted to see if she could hit my prostate gland just the right way, just like' I had done to her the night before. I recalled how much she had loved it when I fucked her, how intense her orgasm had been and I wondered if it were possible for me to achieve something that felt that good as well. If it really felt as good as she made it seem like it did, there was no question I wanted to experience it myself.

"I want to try it," I said before I even realized the words left my mouth.

"You're sure,"

"Yeah...I think I'm pretty sure."

"Okay then. When,"

I hesitated for a moment, then' looked around at our surroundings; we were in an area where it would be pretty' hard to see from the main path. Of course' our bikes were still' parked up by the tree but we could drag them down here with us if we wanted. The only real concern would be the other path on the opposite side of the creek, but we could always move to another area further down where there were trees blocking the view.

"How about now," I said.

"Now; like right here? Are you sure?"

"Yeah, I mean if it's okay with you."

She smiled seductively, "Someone's got a kinky side."

She stood up, reached down and helped me up to my feet leading me down the sand bank we were on to an area where we could duck almost completely out of sight from joggers and bikers. She pushed me up against the tree behind me and kissed me forcefully, tongue sliding into my mouth and hands exploring every curve of my body through the fabric of my clothes.

I groaned, kissing her back, both of our cocks throbbing in our pants as we got each other nice and worked up for what was to come. She slid' her sweatpants down along with her panties, her erect penis popping free and motioned for me to get down on my knees. I obeyed and went to work sucking her cock and playing with her balls at the same time. She instructed me to remove my own pants and I did as she asked before continuing my oral attention to her cock.

While I did, she slid' her hand down my back to my ass and started lightly tracing her fingers over my virgin asshole.

When she felt satisfied with my blowjob' she told me to stop and stand up and face the tree. I leaned against the tree and she got up behind me running her hands up and down my chest and over my hips. I could feel her cock, nice and wet from my mouth, pressing up against my asshole and I braced myself expecting her to push in to me right then and' there. But' she wasn't' ready just yet I realized, as she dropped down to her knees behind me and I felt something wet and warm against my hole.

I quickly noticed it was her tongue; she was giving me a rim job, something I was definitely new to but I had to admit it felt pretty' good, As she licked my asshole, I also felt her trying to work one of her fingers into me and I was a bit shocked at how easily it slid in without much effort. It was obvious that the point of the rim job was to lube me up since we were out in the park and did not have any real form of lubrication to use.

Better something then absolutely' nothing I figured,

After a few minutes of finger fucking and licking my ass, Lauren finally stood up and kissed me on the neck. I sighed as she pressed her cock against my hole again and wrapped her arms around me in a soothing comforting way.

"Are you sure you want to do this?"

"Yeah," I replied. "Just be gentle okay?"

"You have my word."

Then I felt it, her big mushroom head pushing into me, parting my hole and easing its way deep into my ass. She was gentle and slow at first just as she had promised me she would be, and I bit my lip trying to grin and bear the pain. It was a sort of burning sensation, quite intense, but not too much that I could not handle. I gripped the sides of the tree, still biting my lip as she continued pushing her dick into me, inch by inch until I could feel her hips against me and I knew she was all the way in.

"You okay?" she asked me, sounding very concerned.

"Yeah...I'll be okay,"

She waited a few seconds for me to adjust and then started to pull about halfway out of me. When she pulled halfway out, she thrust right back in and I jumped in surprise. She froze and waited for me to give her a sign that I was okay. I took a deep breath and told her to continue and so she did, She started thrusting a little faster and harder now and the more time that passed the more' I noticed the pain beginning to subside. As she picked up the pace, I could feel a strange pressure in my cock, which oddly enough wasn't' even erect at the' moment.

There was a burning in the tip that I did' not really know what to make of, but it felt strangely good to my own shock.

When she realized I was starting to feel pleasure, she let down the restraints and started really getting into the routine of pounding me with really hard and long strokes. The sound of flesh smacking flesh was easy to be heard and I worried that someone up on the main path might overhear and come investigating; I did my best to put those thoughts aside though.

Soon enough we were really going at it, both of us making noise as she fucked the hell out of me and I loved it; it felt incredible. The way her dick slid in and out of my ass, rubbing up against what I could only assume was my prostate gland, it was the most intense feeling I had ever experienced. Sex had never been this good with anyone I had ever been with in the past,

Her thrusting was becoming more intense now and there was a slight hint of pain in my rectum, but I was able to put up with it; it still felt really' good. I could feel her cock starting to swell up, hear her breathing becoming heavier and I knew she was getting close; any moment now she was going to cum.

I decided to try something; I tightened my rectal muscles around her cock to increase the pleasure and it seemed to work. Lauren was having trouble keeping quiet as she started whispering my name in my ear and finally she buried herself inside of me. With a grunt, she began pumping me full of her cum like' a car being pumped full of gas.

She buried her face in the crook of my neck and moaned, biting me and licking as she emptied her balls completely. When it was over, she pulled out and sighed in relief; my asshole felt so empty now which was a strange feeling to say the least but I felt as though I weren't' entirely satisfied. My cock was still quite hard, leaking pre-cum and I knew I still needed to get off.

I turned around and she kissed me on the lips before getting down on her knees and wrapping her warm wet lips around my dick, taking me deep to the back of her throat. I groaned, leaning my head back against the tree; this was all it would take, I knew, for me to reach that feeling of pleasure I had been waiting for. I almost felt disappointed though, even as I started to cum shooting down her throat; I had wanted it to happen while she had been fucking me in the ass.

I had wanted to achieve the same sort of mind blowing, body trembling orgasm that I had given her the night before.

That was not the case though, unfortunately, When I had finished and she had swallowed every drop, she came back up and kissed me on the chest, licking and sucking my nipples which were rather sensitive now' then kissed me on the lips and I could taste my own cum on her breath as she did.

"That felt great," she said leaning her head against my chest.

"Yeah...it really did," I agreed.

We fixed ourselves up and' made our way back up to the path to our bikes and stood there a few minutes both of us exhausted. When we felt ready, we climbed onto our bikes; my ass was quite sore and sitting on the padding made it even more uncomfortable. I decided to just walk and push the bike with me; Lauren laughed, well aware of what the problem was but she did not make any sort of jokes as I expected.

In fact, the entire walk back to the apartment was a bit silent; neither of us seemed to have anything worth talking about which was strange. I thought she would have something to say and I'm' sure she thought I would have something to say as well.

When we got back to the apartment, I collapsed on the couch and she went to the kitchen to get us both a glass of water. She sat down next to me and I sat up, we both drank our water slowly and I tried to think of a way to break the silence. She beat me to it though, clearing her throat and sitting her glass down on the coffee table in front of us.

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