My Journey Ch. 02


This is the second installment of My Journey. Although not necessary, this story will be more appreciated if you read Chapter 1 first. Thank you to all who read my first submission and provided feedback. Chapter 1 was a blend of real life experience and fantasy. This chapter is (unfortunately) entirely fantasy.

I hope you enjoy the story.


I rarely dream.

That's not entirely true. Everybody dreams, I suppose I do too. It would be more accurate to say that I rarely recall my dreams. There is no history of wet dreams in my past, either.

This morning was different. I was vividly dreaming that a beautiful woman was playing with my hard cock. I could not recall the last time I had such an erotic dream.

My eyes opened, struggling for focus, and my mind fought to determine where I was and what was happening.

Once my surroundings came into focus it took only a second or two for me to realize I wasn't dreaming, and that a beautiful woman was in bed with me and she was slowly tugging on my very erect cock. Her head was propped on her right arm, and she gently bit her lower lip. I couldn't tell if it was a look of anxiety or excitement.

"Good morning, Baby." she cooed, in slightly more than a whisper.

"Good morning." I replied, my voice barely there.

Her lips eased into a smile. She moved her arm and slid it under my neck, scooting herself closer to me and pressed her shapely body into mine. Her left hand released it's grip on my cock as she moved her arm over my body, pulling us close together, and pressed her lips to mine in a tender kiss.

"Thank you for last night." she breathed. Our foreheads were pressed together and the tips of our noses rubbed against each other.

"The pleasure was all mine." I said. We were looking into each other's eyes, hers flashing in joy.

"I don't know about that. I had some pleasure too." She was smiling broadly now, and again moved her mouth to mine, this time for a more passionate and sensual kiss. Our tongues began to play in each other's mouths, darting in and out, and I instinctively began to thrust my hips against her, my cock rubbing against her erection.

"I could get used to waking up like this." I thought to myself.

Trish also began to slowly roll her hips, causing our cocks to piston against one another in a fleshy dance of mutual desire.

Our gentle kissing and touching continued as we teased each other, neither of us in any hurry to abandon the closeness we were sharing. Trish broke our kiss only to move so she could kiss and lick my neck and ear. She obviously remembered how I reacted when she loved my ear last night, and this morning was no different. A raspy moan escaped from my throat when I felt her hot breath in my ear. My hands moved down her body until I was cupping each of her shapely ass cheeks and pulled her pelvis tightly to mine. My legs instinctive spread and I lifted my right leg over her thigh, wanting to envelope her completely.

"Mmm. That really turns you on, doesn't it Baby?" she whispered rhetorically in my ear, the actions of my body clearly indicating how much I appreciated what her mouth was doing to me. She returned her attention to my ear, kissing, licking, probing.

Trish and I continued to make out in her bed, pelvises bumping, fingers gently stroking, and hands touching each other's nakedness.

With my leg over her body, Trish took advantage of my position and rolled me onto my back and she positioned herself between my spread legs. She lay on top of me, her form stretched out over my body, her perfect breasts crushed between us as we continued to enjoy our closeness. Trish continued to pleasure me with her mouth, alternately driving me wild with her attention to my neck and ear, and kissing my lips and mouth with her talented tongue.

My legs were spread wide, knees bent, giving Trish total access to my body. I was willing to let her do to me whatever she wanted, yet she seemed to be content with the foreplay we were currently engaged in. I wasn't complaining. I was slowly sliding my erection against hers, our pre-cum mingling and creating a slick region between our bodies. My hands cupped and massaged her ass, intermittently touching her rosebud with my middle finger. Trish liked it when I did that. She would push her ass back toward my finger, attempting to get it to slip into her tight ring. I made it a point to not allow that, teasing her to an increased state of arousal.

"Tease." she giggled in my ear. "Come on, stick your finger in me." she moaned, her voice thick with desire.

"I'd rather do something else."

Trish thought I wanted to fuck her so she began sliding her body up mine. As she worked her way up, her breasts fell in my face. I let go of her ass and placed a hand on either breast, halting her 'Northward' climb. I immediately began suckling her, marveling at the size and shape of her mammaries. They felt natural in my hands, like they belonged there. I squeezed her tits together so I could mouth both of her nipples at the same time. I licked and sucked those beautiful nipples for all I was worth. Trish must have enjoyed my ministrations as she threw her head back and arched her spine, forcing her breasts into my face. While she was in this position she moved her legs from between mine and placed them along side of me. Trish was now straddling me with my cock pinned between the bottom of her ass cheeks and my stomach.

She reached behind her and grabbed my dick while raising her hips slightly. Trish proceeded to rub the head of my cock against her asshole and started to lower her weight onto my hard stick. This wasn't the "something else" I wanted so I quickly rolled her onto her back. Now I was positioned between her legs, and I repositioned my cock so it was rubbing hers again. Our eyes met and I saw a flash of excitement in hers. Perhaps it turned her on that I was being aggressive and that I was going to take her in the missionary position. I had other plans.

I closed my eyes and kissed her deeply, my tongue probing her mouth as far as I could reach while I ground my crotch against hers. Trish passionately returned my kiss, the tenderness of the previous foreplay beginning to wane and our actions becoming more primal. I fought the urge to fuck her gorgeous ass right then.

Trying to keep my cock in contact with hers, I lowered my head and again feasted on her bosom. With an orb in each hand I clamped my mouth over her right breast, sucking hard on the rubbery flesh at the tip while massaging her left. Her areola contracted and hardened, the nipple already swollen with desire. I repeatedly flicked at her nipple with my tongue. I sucked it into my mouth, gently chewing and nibbling the firm rubbery flesh. Trish was making nearly inaudible mewing sounds, telling me my efforts were effective and appreciated. I switched breasts and performed the same assault on her other tit.

I couldn't take much more. Hearing how much she enjoyed what I was doing was driving me wild, and I had other things that needed to be done. I abandoned her breasts and kissed my way down the rest of her torso. I felt the head of her cock on my chin as I lapped at her navel. Trish's hands were on the top of my head and she pushed me down. The cock that brought me so much pleasure the night before brushed against my lips, and without thinking I opened my mouth and took the head of her cock in my mouth. Grabbing her shaft with my right hand I pumped her penis while applying industrial strength suction to the head causing her to take in a breath that sounded like a hiss.

"OOOHHHH!" she exclaimed in surprised pleasure.

Trish's hands grasped my head and tried to force it down on her cock, but my hand wrapped around her shaft prevented any further movement. This wasn't what I wanted either.

I pulled my mouth off of her engorged cockhead and released her shaft. Placing a hand under each of her thighs I lifted her hips slightly. Trish allowed her legs to splay open, exposing to my eyes to that which I desired. There before me, in all of it's perfect glory, was her pretty little puckered hole.

(I have always loved the site of a woman's asshole. Penthouse magazine could always be counted on to have at least one close-up shot of a model's dripping pussy and crinkled hole. Invariably I would masturbate to this shot. Once I discovered the world of shemale porn I became an educated consumer of assholes, and Trish's was as good as any I had seen on any model.)

It was a flesh colored sunburst, with wrinkles and creases radiating from the contracted core fading into the smooth skin of her ass cheeks and perineum.

With my tongue slightly extended, I lowered my face to her bottom and made tender contact with her ass where the wrinkles disappeared. I made sure to avoid the center of her anus hoping to further heighten her arousal. My lapping was slow and intentional. I could detect each crease, each wrinkle as my wet tongue glided over her flesh. I circled her hole repeatedly being sure not to contact her core.

After flicking at the top of her hole, I pressed my flattened tongue against her perineum, covering all of the sensitive skin as I licked up to the side of her scrotum. I repeated this action on the other side of her balls. Grasping her shaft with my left hand I lowered my mouth on her cock and took as much of her length in as I could. I lifted up, leaving only the head of her cock in my mouth and swirled my tongue around it.

Completely releasing her from my mouth I went back to her ass and began to make sweet oral love to her puckered hole. Again I teased her, rimming her brown eye, reveling in the feel of her on my tongue. I glanced up to see Trish languidly playing with her hard on, her hips just slightly thrusting. My attention was again turned to her hole and I licked her, slowly decreasing the distance between the tip of my tongue and the opening of her ass. It was obvious to me that Trish was enjoying this, but not as much as me. My cock was impossibly hard and throbbing, and my mind was swimming in the satisfaction I felt knowing I was giving great pleasure to my shemale lover.

I could take no more. I needed to plumb the depths of Trish's asshole. Pointing and stiffening my tongue, I placed the tip at her entrance and pushed. I felt her tight sphincter yield to my probe as I entered, her smooth, tight ring collapsing around my tongue. My penetration brought a moan of pleasure from Trish's throat, which in turn caused me to smile (well, as best I could with my tongue in her ass).

Her approving moan spurred me on and I began furiously fucking her asshole with my tongue. "I could do this all day." I thought to myself. Trish began thrusting her hips more noticeably now, trying to get as much of my tongue inside her as possible. I could hear her hand stroking her cock now, her pre-cum lubricating her erection.

Time seemed to stand still as I continued to penetrate Trish's bottom. I have no idea how long I licked her like this, my mind focused only on pleasuring her. My tongue twisted and flicked inside of her trying to touch every reachable millimeter of tender flesh.

"I love the way you eat my ass. You're driving me crazy!"

I was brought out of my sexual trance by her words. I needed more. Removing my tongue from her depths I again rimmed her, my tongue alternating between "barely there" kisses and crushing licks. Again I licked up her perineum around the side of her balls. I could feel the heat radiating from her cock on my cheek as I kissed and licked her pubis.

I crawled up her body until my face was at her breasts. With a hand on either side of her torso, my knees between her spread legs, I sucked her left nipple into my mouth flicking the rubbery nub with my tongue while my cock gently brushed against hers. Tilting my ass up in the air, my cock pointed at her glorious asshole. I reached down with my right hand, grabbed my shaft, and rubbed the swollen head against her loosened bud. I pressed forward slightly, feeling her asshole begin to give way to my insistent cock.

And then I pulled back.

A disappointed groan escaped from her lips.

Again I pressed against her opening until I felt her body begin to yield to my intrusion. I wanted to be inside of her so bad, but something kept making me stop. I wanted to complete our union. I wanted to give her what she so desperately wanted.

Again I pulled back.

"Oh Baby. Fuck me. I want you to fuck me. I need to feel your cock inside of me." I couldn't tell if she was pleading or ordering me to fuck her. It didn't matter. I knew that the time wasn't right and that our final act of union would wait.

Instead, I quickly moved up her body and straddled her hips. I raised myself up, grabbed her cock and positioned it at the entrance of my rectum, and slowly lowered myself on her well lubricated cock.

"Ooooohhh!" we both cried. It may not have been the penetration Trish had wanted, but she was enjoying it.

As I bottomed out on her shaft, our eyes locked, and I could feel the lust passing between us through our gaze.

I began rolling my hips. As my ass rose a little, my cock and balls would press into Trish's abdomen, and as I lowered them it stuck out hard and swollen. I rolled my hips, I rotated my bottom, always trying to get more and more of Trish inside of me. Having her inside of me like this is one of the greatest physical pleasures I had ever felt.

Trish's hips weren't motionless either. Her hands had a firm grip on my ass cheeks as she pressed her cock into my receptive ass.

I lowered my body to hers, pressing her breasts against my chest and kissed her beautiful lips. I let Trish take control of our coupling and yielded myself to her, letting her pleasure me with every thrust of her wonderful cock into my ass. With my body pressed to hers and her relentless pistoning of my ass, there was enough movement that my erection was sliding back and forth between our bodies. We kissed lovingly while she gave me a royal screwing.

"I love being inside you." she whispered as she momentarily broke our kiss.

"I love having you inside of me." I replied.

We resumed our kiss, our bodies tightly pressed together as Trish mercilessly fucked me.

The sensations got to be too much for me. The aching behind my balls told me my orgasm was close. I wasn't going to be able to hold out much longer. I broke our kiss, nuzzled her ear and whimpered "I'm close."

"I am too! Just a few more seconds Baby. Cum with me!" Trish drove her tongue into my ear.

That was it for me. My cock burst. Jets of hot white cum shot from the end of my very hard cock between our bodies. My asshole pulsed around her shaft as I came.

That set her off.

I felt her cock swell in my ass as her thrusts became more urgent and powerful. "I'm cumming!" she exclaimed as she exploded inside of me, ropes of her honey splattering against the walls of my rectum.

And we were kissing again as Trish arched her back, burying as much cock in me as she could, pushing her juice into me as far as it would go. I was pushing back against her, wanting more of her beautiful member inside of me. I could not get enough of this sexy woman.

We continued to tenderly kiss, enjoying the post-coital glow. I began to buck against Trish's cock as it began to slowly soften, hoping to keep it hard. I didn't want to let it out. I wanted to her to stay inside of me.

But nothing is forever, and after a few moments her flaccid cock slipped out of the confines of my ass and I was empty again.

I clamped my ass tightly. If I couldn't have her cock in me, I was going to keep her cum in me.

I lifted my right leg over Trish's body, and rolled to my left. I lay on my side, gazing into Trish's eyes as she positioned herself on her side to face me. Our legs instinctively entwined and we wrapped our arms around each other in a loving embrace. We covered each other's cheeks and lips lovingly with tiny little kisses. I could feel her heartbeat against my chest as her hands stroked my back. Her tongue found my ear again, and my hips pressed against her pelvis. She pulled away and looked at me with a huge smile on her perfect face. I could tell she was thinking about how I reacted to her tongue in my ear. It amused her immensely.

"That was beautiful." I told her.

"I think so, too."

There was a pregnant pause as we continued to gently touch each other. Trish had a look of concern on her face. Her eyes were cast down, looking at nothing in particular between our bodies. Something was obviously troubling her.

"Don't you want to fuck me?" she meekly asked, clearly feeling vulnerable.

Her eyes sought an answer in mine, darting back and forth, searching

"Oh, honey! I want to fuck you so bad!" I kissed her deeply, hopefully reinforcing my desire for her. "For some reason I feel like the time isn't right. I don't know if I can explain it. I have this notion that before you give yourself to me there needs to be more... I don't know.... romance maybe? I don't want it to just be a 'heat of the moment' thing. I want the circumstances to be 'just right'. I want it to be special."

I paused, searching her face for understanding and my mind for the words to convey my feelings.

"I want to seduce you. Does that make sense?"

"I thought the circumstances were pretty good this morning. After the way you ate my ass? I was so ready for you to be inside of me."

She kissed me lovingly, her tenderness telling me she understood, and was honored that I wanted this to be something to remember.

"I think I like the idea of being seduced." The smile on her face betrayed the fact that she really liked the idea.

We continued to cuddle on the bed. Kissing. Touching. Embracing. We were just enjoying being together and growing closer as the minutes passed.

I awoke to the sound of running water and the realization I was alone in bed.

My bladder was full, so I quietly rolled out of bed and headed toward the bathroom. Trish was washing her hair, the spray from the showerhead drowning out any noise I might be making. I relieved myself as quietly as possible hoping to surprise my lover when I joined her in the shower.

With the pressure off my abdomen I quietly stepped into the shower stall. Trish was under the stream of water, her head thrown back as she rinsed her hair allowing the water to cascade over her luscious body. I stood quietly and let my eyes drink in the form of this sexy woman. With her head back, Trish's body was arched toward me, her position accentuating her breasts and erect nipples. My eyes wandered down her body to her crotch and the cock that had been inside of me minutes ago. It was smaller, I suppose because of the cool air and the water, but it looked perfect on her. It looked so right. It just 'fit'.

Unable to resist for another second, I leaned in toward her, being careful not to make contact with anything but my tongue on her nipple.

"OH!" she chirped, startled. With her eyes open now, a broad smile crept across her lovely face as she extended her arms to me and we embraced. "I was hoping you'd join me Baby." she breathed in my ear.

"Why didn't you wake me up then?"

"You looked so peaceful and content, I didn't want to disturb you."

She kissed my lips, seductively licking them with her talented tongue before plunging it into my mouth. Our tongues waged war against each other as our hands roamed one another's body under the falling water.

"Would you like me to wash you?" I asked.

She smiled at the idea and quickly turned to grab some items out of a rack on the wall of the stall. Trish handed me a bottle of shower gel and a scrubby. I applied some of the gel to the scrubby and switched positions with her so she wasn't directly under the shower. I turned her around so her back was to me and began to wash her body with the flowery scented gel. Moving the scrubby in circles I washed her neck while I kissed her shoulders. Her head hung forward as she enjoyed my gentle touch and the intimacy of another person washing you. My hand moved the scrubby around her neck and gently washed the front of her neck and throat. Trish arched her head back, tilting it toward me so she could kiss me while I washed and caressed her neck.

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