Sandy's Journey Pt. 05

AUTHOR'S FOREWORD: This story has turned into a romance, and there's some of that in the first part of this chapter. The second part is a full-blown orgy. Enjoy.

CHAPTER 13

We didn't wake up until about 9 that night. Feeling pretty sticky, we climbed into the shower together. There was a great deal of kissing while we were in there, and we cleaned each other very thoroughly. After a snack smorgasbord from the fridge we snuggled under a blanket on her couch and watched an old film noir on TCM. Still naked, we bundled into bed. I'm not going to say we were too tired for sex, but at that moment it didn't seem as much a priority as intimacy was. Kim snuggled her back up against me, and spooned like that we fell asleep again.

I woke up to a wonderful feeling, and found my erect cock bobbing in and out of Kim's mouth. I lay still, pretending to sleep on for as long as I could get away with it, but then Kim said, "I know you're awake, doll," and gave my balls a gentle squeeze.

I lifted my head and smiled down at her. "I am, but don't let me interrupt." Then I just lay back to enjoy.

Kim had other ideas, getting up on all fours and swiveling around until her cock hung over my face. I wrapped my arms around her ass and pulled her down, sucking her deep into my mouth. Her small tits brushed across my belly as she went back to pleasuring my cock. Reaching down with one hand, I felt each mound, then teased each nipple with gentle pinches.

She moaned softly at my pinches, then took her mouth off my cock for a moment to masturbate it, using her saliva for lube.

I wet my fingers in my mouth alongside her cock, then spread her cheeks and began teasing around the edges of her hole. Finally I eased two fingers inside her, fingering her ass to the same rhythm of her cock going in and out of my mouth. It wasn't very long at all until she was fully hard, poking into the opening of my throat.

I felt it was time to move. I wanted something different this morning. I pushed up gently on her hips, and she swivelled sideways, coming to sit next to me. I sat up and kissed her for a while, then lay back down and pulled her around on top of me. I pulled her legs outside my hips and she got the idea.

Bringing her legs up so she sat astride my hips, she reached back and took hold of my hard cock. With my prick and her hole wetted by spit, we had just enough lube. She wiped the head between her cheeks a couple of times, then pressed it against her hole and sat on it. She began a gentle up and down motion with her hips, taking more of my cock inside her with each stroke. We held each other's hands, interlacing our fingers. Her eyes closed and her mouth opened as she took long deep breaths.

Finally I was all the way inside her, her balls laying on my belly as her stiff prick stood straight up above. Letting go of my hands, she put hers on the bed behind her for leverage as she began to fuck up and down on me.

I took charge of her pleasure, grabbing her cock and masturbating her as she rode me. Her moans rose, then changed to unintelligible noises as she sped up, fucking me with her hole. I kept changing rhythms on her cock, squeezing, then softly holding it; moving quickly up and down, then slowing. Finally I settled on matching her speed and depth as her hips rose and fell on me.

"Oh, Sandy, oh baby," she whined, her voice high, "God, you feel so good! Keep stroking -- I want to cum with you.

I smiled at her and she smiled back, now rising and dropping hard onto my cock. She squeezed me inside with her sphincter muscles each time she rose. It felt like her ass was sucking my rod.

"I'm gonna cum soon," she rasped. I began thrusting my hips up to meet her as she fell, pounding into her asshole.

"Me....too," I answered, pounding out the words as I pounded up into her. I squeezed her prick hard and sped up the strokes of my hand. I felt her begin to swell, felt her balls draw up against her, and saw the first spurt of cum rise up out of her and fly up onto my chest. Her asshole squeezed with each eruption, pulling my own load up out of my balls and into her ass. She finished cumming and went still, her ass still in the air. I pounded into her, squeezing out the final loads of my cum into her rectum.

Kim fell forward onto my chest, rubbing her cum onto both of our chests. My cock slipped out of her ass and nestled between her cheeks. We were both breathing hard, silent but for the gasping. Her head lay on my shoulder. She turned and kissed me on the cheek, then I turned my head to meet her lips and kissed her deep.

She put her hand on my cheek, and we looked into each other's eyes.

"I think I'm yours now, too," she said, and smiled at me.

"Good," I said.

We lay like that for a few minutes. Realizing we'd once again become a mess, we rose and slipped into the shower together. I soaped her chest heavily, then pulled her to me and used her to scrub my chest while I scrubbed her back. She laughed and kissed me. We got out and towelled off, and Kim handed me a new toothbrush from a drawer.

"I knew you'd need this eventually," she said. We finished washing up. I watched as she dabbed a little perfume on herself, thinking I might have to learn to do that. Kim threw on a robe, while I wrapped a towel around myself, and we went into the kitchen in search of sustenance. I made coffee while she threw some ham and a couple of eggs into a frying pan. It was a quick, but satisfying meal, and the company was the best I'd ever eaten with.

Afterwards, I dressed while Kim sat in her robe with a second cup of coffee and watched me. We had to be at the office tomorrow, and I needed a little time to collect myself. We talked about the week ahead, making tentative plans to get together several evenings. She said we might go out one night with some friends of hers, and I felt a tingle in my ass remembering the previous afternoon with Penny.

I liked that it wasn't scheduled down to the minute, that we both knew we'd find the time to be together and didn't worry about it. She followed me to her front door, and as I turned to kiss her she threw her robe open, pressing her naked body against my clothed one.

"Now anybody who comes near you today will smell my perfume," she said, and kissed me long and hard. Then we hugged for a long moment.

"I'll see you soon, love," I said

"That's a scary word," she whispered in my ear.

"Yeah, but not as scary as it was a few days ago," I whispered back. "As we've said, let's just see how it goes."

She pulled her head back and smiled at me, then kissed me again. Then I was out the door, into my car, and headed home. I smiled all the way there.

I spent the rest of the day doing lots of little things -- straightening up the apartment, doing laundry, paying bills, yada, yada.

Kim called about 9, and we flirted and teased for a few minutes. I told her I'd see her at the office the next day, and we spoke about keeping things quiet there for the time being. The only thing worse than office gossip about a relationship is office gossip about a relationship that ends up not working out.

I got to bed at a decent hour. I lay awake thinking about Kim, about myself, and about the future. I decided I wanted to go back to Bob's and shop for some more lingerie. I wasn't sure about outerwear. I didn't know if I was really interested in appearing dressed in public as Kim and her friends did. I was also thinking about another shot at Penny's prick.

I thought about Kim and my heart swelled. She was pretty, she was smart, she was funny -- everything I look for in a girlfriend. And she had a cock -- something I never dreamed I'd consider a plus in a woman, but Kim without a cock, just wasn't Kim. She was a whole package somehow. I searched my feelings about her and decided they were real. I was falling in love with somebody who was born male.

And the sex! I'd had sexual relations with more people in the past week and a half than in the 5 years previous, most of it in ways I'd never considered as an option. Two weeks ago I'd been a straight white guy. Now I was a bisexual crossdresser, approaching a reputation as a cum dump. I didn't want a slutty reputation, certainly, but I'd never again reject the idea of sucking cock out of hand. That made me think of Kim's cock sliding into me -- it felt so perfect, especially missionary, with her face hovering above mine delivering her delicious kisses.

I fell off to sleep with those visions in my head, awakening Monday morning to the hated sound of the alarm. Up and at 'em. I toyed with the idea of wearing lingerie under my office wear, but it wasn't a chance I was willing to take. If I got hit by a bus, there'd be questions at the hospital. All masculine, I hustled down to the office, found some coffee, and settled in at my desk.

Kim came wandering by with a few other people, flashing me a quick smile when no one was looking. I went about the company's business.

About noon I got an email from Dave Candell's secretary inviting me and several others to attend a meeting in Dave's office at 2. The subject was an issue with one of our suppliers, one I'd dealt with several times. Five minutes early is late, so I was waiting at his door at 1:50. My boss and a couple of others showed up, and at 2 exactly the door opened. It was Kim, who shepherded us into the office and invited us to the conference table.

It turned out the issue was a misunderstanding of the specs we'd given them. The delivery schedule was tight, so corrective measures were required immediately.

"Sandy, I think you need to go out there," Dave told us. It's a contractual issue, so I'll go with you to handle that end."

My immediate supervisor looked a little sad at that, but Dave had ruled. I could understand his disappointment -- the supplier was in Silicon Valley, just down the road from San Francisco.

Dave told Kim to set up the travel arrangements. We'd be leaving on the first flight out the next day, with the first meeting scheduled for 1 p.m. Pacific time.

As most of the crew shuffled out, Dave motioned me to stay. We talked a minute about the meetings, then Dave said, "Dress for all the companies out there is casual, so no ties." Then he lowered his voice a little and continued "and we'll have some time to ourselves, so you might want to bring some pretty things for the evenings." Of course I understood, and he winked at me to make sure I had.

I had dinner that night with Kim, and we talked over the trip. As his assistant, she'd visited this supplier before.

"Dave has some wild friends in San Francisco, so I'm sure you'll have some fun," she said. "I wish I was going with you."

I told her I'd love that too, but maybe we'd take a trip out there ourselves just for a little vacation.

"I have friends there too, she said with that wicked little grin. "I'm sure you'd be very popular with them."

"I'm sure I'd like that," I told her. Under the table I rubbed my foot up her calf.

"I'm going to keep you to that," she smiled. "This must be a rush job -- usually Dave takes Judy when he goes to California. You can expect some play time. Just be careful, and be sure to get enough rest so you can work,"

I packed that night, casual clothes for day, sexy lingerie for night. I thought about packing a dildo, but I didn't think there'd be any shortage of cocks. I did make sure I had lube and condoms, just in case.

Then it was early to bed, early to rise, Uber to the airport, and meet Dave in the airline VIP lounge. Coffee and a Danish and onto the airplane. Dave was in first class, I was in tourist. We met up again at San Francisco airport and picked up a rental car. Straight down the road to San Jose and into another nondescript office building.

The meeting that day was long and tense. The supplier wanted to blame us, Dave stuck by his guns about contractual requirements. Finally we got around to fixing the problem. The engineer doing the work and I discussed the issues while the high-and-mighties glared at each other. It turned out they had ignored one of the documents in the spec. Surprise, surprise. Problem solved. Dave pointed out the provisions of the contract pertaining to late delivery, and they shuffled out with their tails between their legs.

"Nice job today, Sandy," Dave said as we pulled out of the parking lot. "You saved our asses, finding that document they missed." I was doing the driving while he relaxed.

"Thanks, boss."

"Off-duty now, Sandy, so it's Dave. Especially since you've seen me naked," he said with a laugh. "So I'm thinking a celebration is in order tonight. But I want to ask you first whether you want to participate or not. We had that one great evening at the house with Judy and Kim, and I know you've been spending time with her, but I don't have the right to commit you to anything further without your permission. So, do you want to celebrate with me and a few friends tonight? If not, no pressure, no consequences."

He looked over at me, and I could only grin. "Would you prefer me in pink lingerie tonight, or black?"

His eyes widened slightly, and he said black would be great. "If it gets too wild for you, you can just excuse yourself," he said.

"Okay, Dave. Thanks. We'll just see what happens."

With that Dave pulled out his phone and dialed a number. After a pause it was answered.

"Hi, this is Dave Candell. We have reservations for two rooms tonight, but it looks like we'll need some meeting space. Is one of the suites available? Okay, great. We'll be there in about 15 minutes."

Dave pulled up the car's nav system and put in the hotel address. I nodded and started following its guidance.

Then he made another call. "Billy, hi.. Yes, we are on tonight. Oh, Jeanie's coming? I'd love to see her. About 8? Just the three of you, right? Great. I have somebody with me, and I think you're really going to like her."

I caught the "her" and knew what his plans were for me. I was a little nervous about coming out to people I'd never met, but I trusted Dave. He'd taken good care of me so far.

We got to the hotel, checked in and went up to the suite. It had two bedrooms, each with its own bath, with a large living area between them. The hotel staff had set it up for a meeting, with a conference table and chairs. I hoped we wouldn't leave any nasty stains on them.

Dave and I had dinner in the hotel restaurant. All business, discussing the day's events, what needed to be done back at the office. It was "Mr. Candell" for me all through dinner, working to give the impression this was all business.

When we got back up to the suite it was about 7:10. "I'm going to get comfortable, Sandy. You do the same, Dave said, and went into his bedroom. I went into mine and opened my suitcase. I was excited and still a little nervous, but looking forward to seeing what sort of fun Dave's friends would bring.

I laid out the silky black thong panties and bra I'd brought, along with some thigh-high black stockings and a see-through robe that Bob had stuffed in with the things I'd bought at his store, thinking I had to remember to pay for them. Stripping naked, I went into the bathroom. I'd brought an enema bottle to clean my pussy, then I jumped in for a quick shower, paying special attention to my backside. I wanted everything to be nice and clean for our guests.

I slipped into my panties, wriggling them up over my hips. They felt so soft and snug at the same time. I put on my bra, then sat to pull my stockings on. I stood and looked at myself in the mirror. Damn, I looked good. I'd fuck me. I thought that if I was going to continue with this, I'd need a wig, some makeup lessons, and some shoes. I had a warm, wonderful thought of shopping for these things with Kim, probably at Bob's again. Given just what I'd seen, he must have everything I'd need. I slipped on my robe and gave myself one more look in the mirror. Mmmmmm.

Softly easing my door open, I stepped into the living area. Dave was seated at the head of the conference table, a rocks glass with liquor and ice in front of him. He was wearing jeans and a polo shirt. He took one look at me and whistled.

"I knew you could look hot, but damn!" he said. He pushed his chair back and patted his thigh. "Sit here."

I wriggled my butt over to him and sat on his knee.

"I think you'll like my friends, and I hope you enjoy yourself," he said, "but even if they don't show at all, I plan to bend you over this conference table and fuck you silly. Does that sound like a plan?"

I smiled at him. "We could do that right now," I said.

"Don't tempt me," he growled.

I reached down between his legs searching for his dick. It was already half hard, and I began massaging and stroking it though his pants. Somewhere around the time I pulled those stockings up my legs a switch went off in my head, and once again I wanted a mouth full of cum.

While I teased his cock to full hardness, there was a knock at the door. "Go over by the bar," Dave said, "I'll answer it."

I padded on over to the bar, trying my best to look demure in full slutwear. Dave opened the door, and in trooped two men and a woman, dressed in the same sort of business casual clothes we had worn earlier. One carried a briefcase, the other two computer backpacks. All three stopped and looked me up and down.

It was the woman who whistled. "Well, hello, Sandy" she said, "Dave was right about you. I'm Jeanie" The two men introduced themselves as Billy and John.

"Sandy, could you handle the bar for a minute?" Dave said, and I started going through the cabinets to see what there was. Billy took his drink and asked Dave which bedroom was his. Dave pointed, and Billy took his backpack and closed the door behind him. Dave hugged Jeanie, giving her a long hard kiss, then he and John took their drinks to the conference table and sat talking.

Jeanie stayed by the bar, telling me how much she loved my outfit. "A little makeup, and you could pass quite easily, Sandy," she said. Taking my hand, she held it over my head and had me do a little twirl, but stopped me when I was faced away. "And that ass. No wonder Dave likes you."

With that she grabbed both cheeks in her hands, kneading the flesh of my bottom. My cock began to harden in my panties. Jeanie came up against my back. Sliding her hands around from my ass to the front of my panties, she grabbed it, squeezing my rod and reaching down to cup my balls.

"I'm definitely having some of this before the night is over," she whispered in my ear. I could see Dave and John smiling at us.

Jeanie drained her glass in one gulp and set it on the bar. "But that's later," she said. "Judy told me you could really eat pussy, and I need to try that first."

With that she took my hand and led me to the conference table. Kicking off her shoes, she quickly stripped off her fashionable slacks and panties in one swipe. Then she sat up on the table and lay back. Her legs came up wide, and her wet cunt was right there for the eating. Below it I could see the jewel on the end of a butt plug inserted in her asshole.

"Come on, little girl," she said, "Eat me."

Pulling a chair around, I sat between her legs. Putting my hands behind her knees, I pushed her legs down onto her chest. The position was perfect. I started with my tongue, taking one long lick from the bottom of her opening all the way to her clit. Her inner lips stuck out a little, and I gently nibbled my way down one side, then up the other. Back at her clit, I tongued open the hood and sucked it into my mouth. Jeanie moaned softly at that.

I used one hand to tease her ass, softly pulling on her butt plug until the head started to open her back hole, then releasing it to slide back in. I twisted it back and forth, then wiggled it side to side. I could feel her ass clench at the sensations the motion produced.