Sandy's Journey

By J J

Published on Apr 28, 2024

Transgender

AUTHOR'S FOREWORD: There's some mushy stuff here at the start, so those of you who already have your zipper down, be patient. I think you'll like what you find. DON'T FORGET: This place runs on your donations. I've just put four hours into writing and editing this chapter. I can't collect your money, but Nifty needs it. Pay them.

CHAPTER 12:

We'd worked up quite an appetite, so I suggested a steak house a few blocks away where a couple of my college friends worked. I was hungry, and I kind of wanted to show Kim off. It was still a little early for the Saturday dinner crowd, so we were seated immediately. The hostess was one of my friends, a girl named Connie. She stood next to our table for a moment catching up. Richie and Connie were a team, a couple from blue-collar backgrounds who'd met in college while he was studying business and she was studying restaurant management. They married right after college and were working up to opening their own place. Connie gave Kim a visual going-over, to make sure she was good enough for me. She complimented Kim on her blouse, the signal that she approved, then she had to hustle back to seat the next customers.

"She's kinda cute," Kim said, watching Connie's butt wiggle back to the desk, "Old girlfriend?"

"No, just a class buddy. She studied restaurant management, and we had several classes in common."

"So I don't have to be jealous?" Kim smiled, and kicked me under the table.

"Nope, I swear, I didn't even kiss her. She only had eyes for my friend Richie"

"In that case, I'm sure I could find someone both of them would like -- maybe you." Kim said.

"You lecherous demon!" I said, "Trying to drag all of my friends into your world of sin."

Kim laughed and kicked me harder.

The waitress came and took our drink orders. Kim had a light beer and I ordered a scotch. We pored over the menu and were ready to order when she came back.

"You've been dragged into my world of sin," Kim said when the waitress left, "How do you feel about it?" Her lips smiled, but her eyes were serious, and I answered the serious.

"I don't know," I started, and then paused to collect my thoughts and get the phrasing right. "The one thing I know is that I'm very glad I met you, and I'm stunned and delighted that you find me attractive for some reason."

Part of the serious went out of her eyes. Reaching across the table, she took my hand in hers.

"I do, and it's not because the sex has been amazing, and it has been amazing." She looked down for a moment, gathering her own thoughts. "It's you. You know, I saw you around the office before that night at Tom's, and I thought you were cute. I guess I formed some kind of idea of you before we spoke, and.... well.... as a person, you're even more than my long distance impression. I really like you, I really like being where you are."

"Me too," I said. Our eyes locked to each other's. Both of us smiled, and she squeezed my hand.

"You're completely out of my previous experience," I said, "And everything we've done has been so far out of my wheelhouse.... But, you know, I look at you, and I know I can trust you. I felt that the first night, when we were in bed together. Wherever this takes me, takes us, I know you won't hurt me. That probably sounds pretty corny to you, but even wearing panties, I'm still old fashioned in some ways, and those feelings are important."

She smiled and squeezed my hand, and as she was opening her mouth to reply, my friend Richie interrupted. "Hey, there, dude, good to see you! Introduce me to this lovely girl!"

Introductions were made, and Richie kissed her hand and complimented her on her choice of men.

"He is special," Kim replied with a smirk. "You don't know the half of it."

"Somebody bragging about Sandy? Will wonders never cease?"

We joked for a few minutes and talked about getting together for dinner some time, and Richie had to get back on the job. They were two great people, completely dedicated to each other and their dream.

We ordered, and talked between ourselves, oblivious to anything or anyone else. Richie sent a champagne split to the table with his compliments, and we toasted our nascent relationship.

"He's cute," Kim said with a wicked smile. "Did you ever see him naked?"

"Once. I stumbled into the wrong room drunk one night and fell on him and Connie while they were having sex."

"Did they invite you to join them?" Kim asked.

"No, she jumped up and covered herself, and Richie and I were too busy laughing."

"Does he have a big dick?" Kim asked, almost whispering.

"Yes, he does, but I think Connie would kill you if you saw it. They really are a solid unit."

"Ah, too bad. I had these visions of you sucking it." Kim said, running her foot up along my calf.

I smiled and probably turned a little red. I'd come to love sucking cock, but Richie had never been a dream of mine.

We spent the rest of dinner talking and teasing. I paid the bill, and Connie gave me a big hug on the way out, telling me not to be such a stranger. Kim held my hand as we strolled back to my car.

"Do you have any plans for tonight," she asked as we got in. I told her I didn't.

"Well, now you do. We're going to my place, and I'm going to make mad, passionate, toe-curling love to you."

She kissed me as I started the car, then dropped her hand into my lap, where she teased my cock all the way to her apartment. We must have looked like newlyweds trotting up to her apartment, already unbuttoning things before we got into the door, a huge bulge in my jeans.

Once inside, she glued herself to me, kissing and sucking my tongue, kissing everywhere on my face and neck. Her hands pulled me against her, then reached down to squeeze my ass. I was ahead of her, my hands on her ass the entire time.

In rapid time we stripped each other naked, throwing clothing in every direction. Then we were bare, her small tits pressed against my chest, our cocks held tight between our bellies. She put her arms around my neck and hopped up on me, her legs wrapped around my waist. My fingers went down her crease to her hole, and she moaned as I teased her there.

We couldn't stop kissing. It was like we were each trying to absorb the other. I could feel her heart beating in her chest as she pressed against me, and feel that same pulse in her prick through my belly. I held her there as I walked into her bedroom and fell on top of her on the bed. She pushed and rolled us over until she was on top of me, her knees at my sides.

Rising up, she took my head into her hands, kissed me long and hard, then backed away, looking into my eyes. "This is only the second time I've had you all to myself," she whispered, "and I want to give you everything. I will sometimes share you with others, but I want there always to be a part of you that is all mine, and mine alone."

Then she kissed me again, and there were no more words for a very long time. We were perfectly attuned, two instruments playing a duet. Each could feel where the other was headed, and we would meet there in equal ardor.

First, she wanted to kiss all of me, starting at the top of my head and ending at my toes. She stopped to lick around my neck, then kissed her way down my arms. She held each hand in turn against her cheek, looking into my eyes with a smile. Then the smile would turn wicked, and she would suck each of my fingers like a tiny slender cock.

She massaged my body as she kissed her way down my abdomen, stopping to suck on each of my nipples, then lightly bite them. She looked up at me and giggled as she stuck her tongue into my navel.

Then her hands reached my cock.

I spread my legs to improve her access. She just lightly touched, fingertips and nails, around the head of it, then up and down both sides, top and bottom. Her nails scratched over my balls, then under and around them, as her tongue retraced the lines on my cock that her fingertips had made. Then her fingers massaged and pushed in on my perineum while her lips kissed my cock softly, up and down, all around, then back to the tip. Taking just the head into her mouth, she sucked on it hard, like she was drinking through a straw.

Then she went on, leaving my dick standing straight up, every nerve ending in it straining for release. She licked the insides of my thighs, then on down to my calves and feet. She lightly bit each toe. Then her hands on my hips signaled me to roll over, and she reversed course.

She ran her tongue up the sole of each foot, then kissed her way up my calves and thighs. Her hands followed her lips, massaging the muscles of my legs, relaxing me in some unfamiliar way. How can my legs be so relaxed, I thought, when my cock feels like a piece of rebar?

She reached my ass, kissing both cheeks, then her hands gripped them, her thumbs descended into the crease, and she and pulled them apart. My boy hole had recovered from the pounding Penny had given it, but it was still sensitive.

She teased me more with her tongue. Starting at the top, she took one long lick downward, but lifted over my pussy hole and continued down onto my perineum to the back of my balls, where she planted a long loving kiss. Then she licked up the sides of the crease, again missing the one place I so wanted her to land. Finally she went in directly. Using both hands to open me up, she dove into my asshole.

I was still a little stretched, and I felt her tongue spear into me, inside my hole. She licked it, kissed it, then pushed her two index fingers inside me. I thought she would finger-fuck me, but she used her fingers to stretch me open further and once again pushed her tongue inside. I almost came just from that.

I was somewhat surprised to notice I was moaning, and probably had been for some time. Then she stopped. Her fingers and mouth withdrew, and she continued kissing her way up my back. As she did, she massaged my back as she had my legs. It was so soft, so sensual. If my cock hadn't been screaming to cum I might have fallen asleep. It seemed that was the only muscle in my body that wouldn't relax.

As she kissed and massaged her way up my back, she started to lay down on me. By the time she reached my neck, her cock was nestled in the crack of my ass. Her hips moved gently. Her cock, slightly lubed by the saliva she'd left there, slid up and down, once again teasing my hole. For a few minutes she lay on my back, fucking the crack of my ass as she kissed my neck and the side of my face.

Then she rolled off of me, and eased me onto my left side. After a long deep kiss on my lips, she eased around until her face was near my cock. She lifted my top leg, then took one long lick from the tip of my cock all the way around to my asshole, where she once again planted a kiss. Then she took my balls in her mouth, one at a time, gently sucking them and exposing her teeth to pull them into her mouth.

Her cock was in front of my face, but she laid at an angle, so it was well away from my mouth. I started to move towards it, but she reached up and held my shoulder to keep me in place. Still, I got one hand onto her. I watched my hand as it stroked and caressed her genitals. I played with her balls, holding and squeezing them like a sack of marbles. I held her shaft in my hand, teasing the tip of her prick. A small drop of precum appeared there, and I used one fingertip to rub it around the head. That was the first moment she moaned.

Kim released my balls and made her way to the tip of my cock. Opening wide, she slowly took it all in. Her tongue rubbed across my shaft as she took it deeper and deeper. I felt the tip hit the back of her mouth. Then she swallowed and her throat seemed to open. The top few inches made its way into her throat. Taking hold of my balls again, she pulled me back and forth, fucking her throat with my prick. She'd take a few strokes that way, then back off to breathe, then swallow me whole again.

My body was going crazy. I could feel my toes curling as Kim had foretold. My balls screamed for release. And all the time my hand held and stroked Kim's cock. My eyes focused on nothing but that, and I thought it was the most beautiful thing I'd ever seen.

Kim sensed that I wouldn't last long fucking her throat, and she wasn't done with me yet. Pulling free, she moved down to my knees and eased me onto my back. Throwing an arm and a leg across me, she began crawling up my body, her chest rubbing my cock, then sliding onto my belly. Her lips led the way, in a long line of kisses, until her face reached mine and our lips met again. I felt her hard cock pressed against mine. Her hips wriggled, stroking our tools together while she kissed me hard and long, her hands holding my head and her fingers weaving their way through my hair.

Then she put her legs inside mine and pushed my thighs apart. She sat up and her hands grabbed behind my knees, pushing them up against my chest. She lay on top of me that way and we kissed some more. I felt her hand reach out to my right, then I heard the pop of the lube container.

It took what must have been gymnastic training, but Kim managed to lube up her stiff cock without ever taking her lips from mine. I put my arms around my legs and around her, pulling her to me as the tip of her rod touched lightly against my open boy pussy.

She started to push inside me, and we both moaned into each other's mouths. It was one long slow push. I reached down and held her ass with one hand while the other went to the back of her head, holding her lips to mine.

Finally I felt her belly up against my balls, and I knew she was completely inside me. Can I say that I really felt I belonged here without sounding corny or mushy?

Usually when you're kissing like that your eyes stay closed, but ours opened at the same time, locking into each other's gaze. I felt like I was falling, falling into this woman, connecting on a level I'd never known.

Kim pulled her hips back, then went forward again, slowly. Her eyes closed as she felt the sensations from her prick, of its desire to breed, to fill me up. Our hands went everywhere, holding each other close, caressing, urging, wanting to join as those two parts down below had.

It was long, slow lovemaking, and I couldn't understand how Kim kept from cumming. Just the heat of her belly on my tool had me close. With each stroke her body ground against my balls and my prick. Our moans became pretty much constant. Kim pulled her head away from mine and once again our eyes locked. Suddenly she pulled almost all the way out, then rammed hard into me, shaking my whole body, perhaps a reminder that she was just as big and strong as me.

A fierceness came into her eyes, then into her whole face. She wasn't just giving me all of herself, she was taking possession of me. I wasn't conscious of my own expression, but I know part of it was welcoming, part of it was happy. Probably another part of it was a man who just found something he didn't know existed.

I pulled her against me again, her head on my shoulder, mine on hers, as she began moving more rapidly inside me. She wasn't pounding me into the bed, just speeding up. Long strokes, then short ones. She wriggled her hips as she pushed forward, moving her cock around inside me.

Then she pushed away, and I felt her hand, still slick with lube, grab my cock and start stroking. Her face was about a foot above mine. I didn't need any words. I saw in her expression that she was ready to cum, and very much wanted me to join her. Looking at me, she knew I understood. Then her eyes closed, her head went back, and her mouth opened. A long, quiet note, almost musical, came out of her mouth. Her cock started pounding down into me. Her hand flew on my rod, stroking it in time to her thrusts.

My eyes closed too at that point, and everything we both had concentrated at those points where cocks moved down between us. Reaching up, I grabbed her shoulders, squeezing as she fucked me, deep, hard, reaching places inside my body and inside my soul.

Our final noises were more feral than poetic, but I felt my balls squeeze up against my body as I started to cum. Kim pushed hard against my hole slamming down as if to get every fraction of an inch inside my ass. Her cock swelled inside me and I knew she was cumming too.

My ass squeezed her cock as I came. Ripples of muscle contractions bound us to each other. My cum sprayed up across my belly and chest. Every drop of hers stayed down there inside me. We stayed like that for a few moments. Kim continued stroking my cock slowly and softly, while taking short slow strokes into my ass, like she was willing the last few drops of semen to emerge where we were joined.

I opened my eyes, and she was looking down at me. She smiled, and I saw a face both happy and triumphant. She had done what she said she was going to to, given me all of herself.

In my own act of gymnastics, I rolled us over without letting her cock leave me. My knees were on both sides of her hips. Her hands sought out my shoulders and pulled me down against her. There were more kisses, this time interspersed with deep breaths. I felt her heart pounding to match my own.

I squeezed her cock some more with my sphincter, seeking to give her one last bit of pleasure.

We were quiet for a while, just holding each other. Fingers stroked shoulders. I squeezed her torso with my knees while my hands held her head for another kiss. Kim's softened cock fell loose. I moved to my side and pulled her against me. I wanted to feel every part of her body against every part of mine. Both of us felt hot from our exertions. We kissed some more.

I wanted to say something, but I didn't know what. Flippant would be stupid. Funny would be wrong. Too serious would be too dangerous. Finally I found what I hoped were the right words.

"I think I'm yours." I said.

Kim moved her head back slightly, looked into my eyes, smiled -- then just nodded. Yes.

We wrapped ourselves around each other and fell asleep.

AUTHOR'S POSTSCRIPT:

You know, I didn't really plan for this to turn into a romance, but something sent me that way when Sandy and Kim met. There will be romance in the following chapters, but there will also be more wild multi-partner, multi-gender sex. If you like my stories, drop me a note. Even if you don't like them, hit the donation button. This only works with my writing and your donations.

Next: Chapter 11


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