Sandy's Journey Pt. 06

CHAPTER 14 -- Kim's Story

We got up early, grabbed a cup of coffee, and headed for the airport. I felt bad about not calling Kim before I went to bed, so I texted her as soon as we were at the gate waiting for the plane to load.

ME: Morning, beautiful. Sorry for not calling last night. Things happened.

KIM: Thought so. Who'd you meet (meat) (smile emoji)

ME: Jeanie, Billy, and John

KIM: Don't know John. Jeanie's a trip, isn't Billy cute?

ME: Yeah. A good time was had. Billy was beautiful

KIM: So are you. I can make you look as fem as Billy

ME: That would be fun. We could go out as girlfriends

KIM: Come home. Miss you

ME: Me too. Dinner tonight?

KIM: Love it. Tonight...... (kiss emoji)

ME: (10 kiss emojis)

KIM: (big smile emoji)

Then the plane was loading. Dave in first class, me in coach. I used my laptop to write a memo on the previous day's meeting during the flight. When we landed, Dave was waiting for me at the top of the jetway. I rode with him to the office, arriving just after 1. Once there I emailed my memo to Dave, Tom, and the others involved. We had a meeting with them at 2 to go over the issues. Everybody was happy we'd cleared things up so easily, and without delay or additional expense.

The rest of the day was pretty quiet, and I headed for home at 5. I unpacked my bag, stripped naked, and threw in a load of laundry. Feeling a bit too hairy, I applied depilatory cream on my genitals and ass crease (thanks again, Amazon), then hit the shower. There was a text from Kim waiting when I finished cleaning up.

KIM: Pick me up at 7?

ME: Sure thing. Should I wear something pretty?

KIM: Your choice. Just bring all of you.

ME: (smile emoji)

I decided not to go all out, but slipped into a nice black lace thong, boy clothes on top -- jeans and a polo shirt.

We had a nice dinner together - nothing fancy, just a little Italian place near her apartment. We played footsie under the table, ate and talked about work. It felt so comfortable, the intimacy between us playing out in front of all the others in the restaurant. Just another cute young couple. Kim wore a yellow sun dress, nothing too revealing. After dinner we walked back to her place, holding hands, just enjoying the evening.

We closed the door, closed the world out, and went into her bedroom for dessert. It was slow, easy, quiet lovemaking.

I undressed her, knelt down, and paid homage to her cock with my mouth. I looked up to see her smiling down at me. It's hard to smile with your mouth full of dick, but I managed to smile back. She held my head in her hands, softly thrusting forward to meet my mouth as I took her in.

She returned the favor, undressing me and pushing me back to lie on her bed. She paused for a moment to appreciate my panties, then skinned them off me and tossed them aside. She lay on top of me, kissing my lips, my face, and around my neck. Then she turned around and we lay on our sides, sucking each other. There was no need to talk. Gentle moans signaled our pleasures. Hands and mouths expressed our desires. She grabbed my ass and pulled me against her face, taking all of me in, while her fingertips teased my boy pussy.

Then she moved me onto my back and came around to kiss me some more, our hard cocks pressed together. She ground her hips against mine, then sat over me and guided me into her ass. She threw her head back and moaned as I entered her. She began rising and falling on me, fucking herself with my cock. When I was deep inside, she ground her hips against me again, her balls laying on my belly.

I reached down and stroked her rod, and we made love just like that. Her hands came down onto my chest, caressing me there. I surprised her by thrusting up into her as she descended, eliciting a moan and then a laugh. Her face was so beautiful, I wished I could photograph her just like that and keep the picture forever.

It was long and slow. Neither of us hurrying to a climax, just enjoying each other. After a while I knew she must be tiring, so I rolled her over onto her back. Her legs came up against her chest. I sat on my knees, giving her long slow strokes with my prick. I took hold of hers again and masturbated her as I fucked deep into her.

The demands of our bodies grew more urgent then, the need to cum urging both of us forward. She reached out to grab a pillow, putting it under her ass. I kissed her hard for a few minutes, then raised up and took hold of her dick again. My thrusts into her grew fiercer as I sensed her nearing a climax.

She took over on her cock, releasing my hands to hold her hips. I pulled her towards me with each thrust into her. Her eyes closed as she concentrated on her orgasm. I watched the need and the emotions cross her face as I started pounding harder inside her ass. My hips shook her ass with each thrust.

"Baby.....baby?" she moaned, and I could feel her ass squeezing me as she came. I felt some of it hitting my belly, the rest splashing hers. I could hold off no longer, and my cum filled her ass. I fell forward and kissed her hard as the last spasms of my orgasm shook my entire body.

Then I was laying on her. Her legs came down and my softening rod fell out of her. We lay like that for a while, me using my elbows to keep my weight off her chest. We kissed some more. Soft endearments were whispered.

"I'm yours," she said.

"And I'm yours," I responded.

I raised my head and we looked into each other's eyes and smiled.

Finally I rolled off. We lay on our sides facing each other, close enough for our breath to mingle, our hands roaming and caressing each other. I pulled her to me, feeling our sticky juices mixed between our bellies, and we kissed some more.

I was content, but Kim wanted to clean us up. She rose and tiptoed off to the bath, returning with a warm wet washcloth. She wiped away all the residue of our lovemaking, took the washcloth back into the bath, then slipped back into my arms, her head on my shoulder.

We lay like that for a while, talking quietly. Then she said, "I know you're trying to figure all of this out. Let me tell you about me, so you can understand that part."

I said, "I'd like that, but only if you want to. I know enough to know that you're important to me, and right now that's enough."

"No, I need to -- mostly for you, but for me too," she answered.

And this is what she told me -

"I've always known that this is who I am, even as a toddler. My mother tells me everything about me was feminine, other than that penis down there. (she smiled at that.)"

"I was kind of a disappointment to my father. My full name is Kimberly James Stoddard IV. The first was my great-grandfather, a flyer who shot down 8 German planes during WWII. My grandfather flew too. He was killed when his plane was shot down over Hanoi. My father stayed on the ground, in the infantry. He was gone for a lot of my early childhood, fighting in Iraq and Afghanistan. Then he retired and took a job that brought him home every night. That was when it came to him that his son wasn't so much a son."

"He served during the 'don't ask, don't tell' era, so he kind of had an idea that who I thought I was, was real, but at the same time it was clear he'd wanted me to follow in their footsteps, and that wasn't going to happen."

Her face clouded a little at that, and I knew it hurt her too. I stayed quiet and let her continue.

"My mother always understood and supported me, though. I guess that's a mom thing. Of course, this was before little boys wearing dresses to school became a thing, so we kept it at home, and I stayed a boy in public. We talked about it, and I understood. So long as she accepted me, I was okay."

"Through my school years I did the usual kid's stuff, exploring. In high school I was tagged as gay, and I was fine with that. By that time it had become pretty much acceptable, as long as I wasn't too effeminate. I never did anything that would get me a reputation. I didn't do the whole football team or anything like that. I dated a few understanding types. Mostly I just waited for my time.

"In college everything was so much more open. I picked a school far enough away that no one knew me. I could dress more feminine, be more openly gay, date who I wanted. I started sleeping with boys, long-term dating sex and one-night stands. It was fun. I became more girly as I learned more about me and more about sex.

"Then everything changed for me, for better and worse. I met a man, a real man, more than the boys I'd been playing with. He was the dean of students, and I didn't know it when we met, but he had a reputation as a predator of girls like me. His name was Gene. He introduced himself to me one day between classes, and then it seemed he'd turn up near me again and again. One day he invited me to his office for coffee. He said he wanted to talk, to make sure school was going well. He said he was concerned that things might be difficult for a boy like me. I knew he meant my girly side.

I went, and in one hour he completely seduced me. His concern for my wellbeing seemed genuine. He was tall, and handsome, and strong. He managed to steer the conversation from my happiness to my desires. I started feeling hot, like I was going to cum in my pants, and I made some excuses and stood up to leave.

He came over to me and held out his hand to shake. When I took his hand he held onto it while unzipped his pants with his other hand. He took my right hand, and put it inside. His cock started to get hard in my hand. 'That's the real thing,' he said, 'and I'll teach you all about it.' Part of me wanted it, part was scared to death of what might happen. 'Think about it,' he said. We'll get together soon."

"I thought about it a lot. He was quite a man, and I fell completely under his spell. The more I thought about it, the more I wanted him. I wanted to be his girl."

"He arranged things for us to get together. He was really sneaky. He set it up for me to come over to his house one Saturday when his wife was away for the day. He had me come in the back so no one would see me. When I got there he took me to their bedroom. He had laid out clothes for me to wear -- shorts, a top, and really sexy lace panties with little embroidered butterflies. He said to go in the bathroom and change. When I came back, he was sitting on the side of the bed, naked. I couldn't take my eyes off his cock, and as I looked at it it got harder. 'You want to touch me, don't you?' he said, and he was right. I got down on my knees between his legs and took it in my hands. He showed me how to stroke it, and I did that. He said I was a really good little girl, and would I like to put it in my mouth? I did. I couldn't take more than the head, and he showed me how to use my hands and mouth together."

"I sat there dressed as a girl, sucking his big cock, and I loved it. I wasn't playing with a boy -- I was with a man. I tried to get more in my mouth, and I sucked on him. He reached down behind me and slipped his hand into the shorts and panties, and squeezed my ass. Then he had me stop."

"He lay back on the bed and directed me into a 69. He pulled off my shorts and panties while I sucked his cock some more. He pulled a bottle of lube out from somewhere, lubed my hole, and started fingering me. I liked that too. He put two fingers in, and it hurt, but I wanted it anyway. He stretched me out, and soon he was pushing them all the way up my ass. I was being his girl and we were having sex. This was what I wanted."

"He started groaning. I tried to take more of him in my mouth. I stroked his cock with both hands. He used the hand that wasn't in my ass to push my head down on his prick. I felt him tense up, and then I tasted his cum, and I loved that too. I swallowed as much as I could, but a lot ran out around the edges of my mouth. I pulled off him to catch my breath, and he took his fingers out of me. That was my first sex with a real man, and it confirmed everything I thought about myself."

"We kept on for about a year. He was really nice to me once I got over being scared. He bought me clothes to wear when I was with him. Really sophisticated women's lingerie. He'd dress me in bras and panties, stockings, all kinds of things."

"I remember the first time he put his cock in me. He had bought me a red lace teddy and thong panties. My hair had grown longer, and I was starting to wear it in a girlish style. It was another Saturday at his house. I dressed in the bathroom and bounced over to the bedroom, ready to eat some cum. I'd grown comfortable with the whole arrangement, and looked forward to our meetings. I dropped right to my knees and took him in my mouth, working his cock to get it to boil over for me. When he was hard he pulled me up on the bed and had me lie on my stomach. He pulled my panties aside and fingered me for a while, stretching my hole like always. He never would touch my cock, so I had to go home and jerk off afterwards."

"Then he got the lube out again. I couldn't see what he was doing, but then I felt his cock against my hole. I pushed back, begging for it. He pushed the head straight in. It hurt a little, but he slid easily all the way into me. I felt like a woman. I was giving myself to a man, an adult. I spread my legs and groaned my appreciation."

"He lay there a minute on top of me, then he began fucking my ass. It felt wonderful. I was not just filled, but fulfilled. I told him to keep going, to fuck me hard and cum deep in my boy pussy. I told him I was his. He was hitting all the right places. My dick got hard, and it was rubbing against the sheets every time he thrust his prick into me. Then he pulled out and rolled over. I got on top and rode him. I had discovered he had sensitive nipples, and I pulled and twisted them. He started pushing up to meet me. I leaned down to kiss him, something we'd never done. At first he turned his head, but then he accepted, and I stuck my tongue in his mouth. Then I got back up and rode him hard, slamming down against his hips. He grabbed my waist, pulling me down against him. Then he pulled me down hard and held me. I felt his cock spasm as he blew a full load up my asshole. It made me very happy, and I kissed him again. I was ready to explode, and I didn't want to wait. While his cock soaked in the cum he'd put in me, I grabbed my own. It only took me a few strokes before I came, spewing cum out onto his chest. He looked uncertain, but then he smiled. Before he let me go that afternoon, he kissed me again, like a real lover. It was the happiest I'd ever been."

"We did that every now and then for another year. It really built up my confidence as a woman to be so desired. I usually wore women's panties, and kept my hair long and feminine. I stopped dating other students and just waited for Gene to call."

"I finally broke it off. One weekend he said he had gotten a motel room on the other side of town. He picked me up a mile from his house behind a shopping center. I hid until we reached the motel. In the room, he had already laid out a set of white lingerie and stockings, almost virginal, bridal stuff. I dressed in the bathroom like always. I'd learned a little bit about makeup, and I put on eyeliner and lipstick. I came strutting out to show him, and he wasn't alone. There was another man there, about his age, also naked. They were leaning back against the headboard, sipping liquor in plastic cups, looking at me with wolfish grins.

"He introduced the other man as his friend Dan. Dan, he said, could be trusted just like I trusted him. I wasn't pleased, but I was there and I did what they wanted. They fucked me, and fucked me, and fucked me. At one point I had Dan's cock down my throat while Gene slammed me from behind. They took turns on my ass for over an hour. My face and the beautiful lingerie were spattered with cum. My stockings were ripped. They had a wonderful time, and I just obeyed. Nobody kissed me, nobody went near my cock. They just used my holes. Finally they were done with me. They showered and went out for more drinks. Gene gave me money to get a cab back home."

"I cried for a long time lying there in the dark room, then I pulled myself together and went home. The next time Gene contacted me, I went to his house and screamed myself hoarse. I told him I wasn't some kind of slut he could just pass around to his friends, that I never wanted to see him again, and if he caused me any trouble I'd call him out to the university. That was the end of it."

She was near tears again, lying against me. I pulled her to me and kissed her. "I'm sorry, dear," I whispered. She was quiet for a while, then she decided to continue.

"Nobody was going to use me again. I dated a few students, fucked some of them, and kept my own counsel. I was much more careful. I guess being hurt like that was part of growing up. By the time I graduated I was a woman in every sense. I threw away all of my male clothes. The name Kim still fit, so I kept that, but I let go of everything else that was male."

"And most of the rest you know. I moved here and went female full-time. Dave hired me. He didn't hit on me at first. He let me grow into the job and prove to myself that I could handle it well. That was his way of showing he hired me for my abilities, and not for what's in my panties. Then he and Judy very gently lead me into their world. The two things are separate, and I love both. Then I met you, and now here I am telling you everything."

"Thank you," I said, "and I'm glad you did, because I think I'm falling in love with you."

She raised her head, looked into my eyes, and kissed me. "I think I'm yours," she said.

She put her head back on my shoulder, and we laid that way for a long time. I could feel her heart beating. I could feel her chest move as she breathed. I pulled the covers over us and she fell asleep in my arms, while I lay awake trying to figure out who I was.