Sandy's Journey

By J J

Published on May 9, 2024

Transgender

STORY CODES: M/F/CD Oral Anal Romance

AUTHOR'S FOREWORD: This is now officially a romance, and that's what this chapter starts with. 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 helt 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 swiveled 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.

Separating her pussy lips with my fingers, I opened her up wide and pushed my tongue inside.

"Oh, you are a good cuntlicker," Jeanie said. Her hands came down and playfully tousled my hair, then she took my head in them and pulled me deeper into her slit.

She was very wet, and I sucked up her juices as I licked inside her. So sweet! I continued licking inside her, then sliding my tongue up to her clit. Jeanie moaned softly, indicating her pleasure. I sucked her protruding clit into my mouth, holding it with my tongue and softly sliding my sharp upper teeth across it, and her hips jerked.

"Keep going, baby girl," she said, "suck me and lick me, and I'll cum in your mouth. Grab my clit again, I really like that."

I concentrated there for a while, taking long licks across her clit, nibbling at it, opening the hood further with my fingers to touch every part of it with my tongue and my teeth.

"I bet you'd like to lick my asshole too, wouldn't you," she said. I looked up at her face and nodded, my tongue still welded to her clit. She smiled down at me. Reaching around her hip, she grabbed the butt plug and pulled it out.

I put my hands under her ass, raising it from the table. I looked over for a moment to see Dave and John. Dave was naked from the waist down, seated on the table. John had lost his shirt and was sucking Dave's dick. "Party on," I thought, then bent back to the task of tongue-fucking Jeanie's ass.

It wasn't gaped, but certainly had been fucked before. I had no trouble pushing my tongue through the outer ring of muscles, licking the inside of the rim. Jeanie moaned softly, then said, "Just a minute." and pushed my head away.

Standing up, she turned to face the table. She unbuttoned her blouse and let it fall. I helped her with her bra clasp, and that fell away too. She was a very attractive mature woman, with the same sort of gym-toned body Judy had. Naked, she spread her legs and laid forward onto the table.

"Okay, cutie, back to work," she said. Reaching back, she pulled the cheeks of her ass apart. I pushed the chair back and got down on my knees on the carpet. Once again I pushed my tongue inside her ass. I ran my fingers down to her clit and rubbed her there.

Then I heard a door open. I'd almost forgotten about Billy, absorbed as I was in pleasuring Jeanie's wonderful cunt.

"Well, you selfish bastards started without me," I heard, in a softer voice than the one Billy had introduced himself in.

Turning my head, I could see a transformation had taken place. Billie was a crossdresser too, and a lovely one. A perfectly combed brown wig and flawless makeup made for an absolutely feminine appearance. Below that she was a vision in white, a bustier on top, matching lace white panties, and white fishnet stockings.

Dave looked at her and it was his turn to whistle. "Dive in anywhere," he said, "the water's great."

John smiled at her and went back to sucking Dave's dick.

"I guess I'll start by introducing myself to Sandy," Billy said, and sashayed over to where I was sucking on Jeanie's asshole. Kneeling behind me, she pressed herself against my back. Her hands started at my shoulders, gently massaging there, then slowly moved to my chest. My sheer robe was getting in the way, so she gently took it off my shoulders, slipped my arms out, and tossed it to the side. Then one hand returned to my chest, squeezing my flat breasts through the silky bra. The other slid down my belly to my panties, massaging my cock. It had gone down when no one paid attention to it, but now it quickly began to harden again.

"Oh, oh, finger my pussy, Sandy," Jeanie moaned, "I'm about to cum."

I kept my mouth plastered to her asshole and slid two fingers into her cunt. Fairly dripping as she was, no lube was needed. I curled my fingertips and began fucking in and out.

I glanced over again and saw that John and Dave were completely naked now. They were on their sides on the table, engaged in a 69. From my angle I could see John's dick sliding into Dave's mouth. It was long and slender, and I looked forward to having it in one or both of my holes.

I felt Billy's dick grow in her panties, pressed against my lower back. It felt nice there. Three dicks and a great pussy tonight. I was a wealthy man.

"Jeanie, would you like some cock," Dave said softly. I looked over and could see that John continued sucking him while Dave cupped John's balls.

"No, I'd like a lot of cock," Jeanie said, laughing, "But yours will do for a start. Better hurry -- your little sweetie here is about to get my first cum"

Dave got off the table and walked around to us, his hard cock leading the way. Billy and I stepped back. She turned me to face her. She was taller than me. Taking my face in her hands, she kissed me, then said, "You're as lovely as Dave said. It's very nice to meet you." She kissed me again, her tongue entering my mouth. She hugged me around the shoulders. My hands went around her waist, then down to find a very nice ass. I squeezed it while Billy pressed back against my hands.

I heard Jeanie moan, "Ohhhhh, gimme more, Dave."

Looking over my shoulder, I could see Dave's big cock sliding between her pussy lips. She had her hands on her breasts, kneading them. She wiggled her ass and Dave pressed forward until his hips met her ass.

Billy led me a few steps away, then turned me until we were side by side, facing the table. John was still sitting on the other side.

"Hey, sailor!" she said, "Looking for a good time?"

John got up and came to us. Billy arranged me to his front while she stood behind him. She reached around and held his prick in both hands pointing at me. Nobody needed to tell me what to do. I got down on my knees. Billy surrendered John's cock to me, and her hands went up to pinch his nipples.

My first impressions of John's cock had been right. It was long, maybe 8", but slender. I started out by ducking under it to lick his shaven balls, then down the shaft to the tip. He was circumsized, something I'd come to prefer in my limited time as a cocksucker. I took him in my mouth, getting about half his length inside before he hit the opening to my throat.

Billy got on her knees behind and nudged his inner thighs. He spread his feet apart and she spread his cheeks with her hands, diving in to go after his asshole.

"Oh, my, ladies, don't stop," John said. He took my head in his hands as if to start fucking my mouth, but he had to stay still to keep Billy's tongue in his ass. I fucked his cock with my mouth instead. I sucked him like a vacuum cleaner, pulling him as deep into my mouth as I could. I took his shaft and balls in my hands and swallowed him like he was he last cock on earth.

My own rod started tenting my panties, so I reached down to pull them to the side and release it. I kept one hand on John's shaft, pumping it into my mouth, and began stroking myself with the other.

Behind me I heard Jeanie moaning as Dave brought her to orgasm with his big dick. "Dave, Dave, fuck that pussy. I'm so glad you brought this big cock to visit me."

John said, "Alright, ladies, who wants to fuck?" and Billy and I both nodded our assent, mouths full of cock and ass.

"Alright then," John said enthusiastically. He laughed slightly, then said, "Let's use the couch."

Billy and I rose and walked the few steps to the couch. As we did, she took her hand in mine. We both knelt on the couch cushions, our elbows on the back, our hips touching. John came up behind us and stripped our panties down below our asses. From somewhere in her costume Billy produced a small bottle of lube and handed it back to him. Billy put her arm around my back and turned to kiss me. Our mouths locked together as John poured lube down the crease of each ass and worked it into our holes with his fingers.

Then he was fingerfucking us, one hand on each ass. I felt one finger penetrate my hole, then a second. Billy and I continued kissing.

Behind me I heard Jeanie still moaning her pleasure. Then she said, "Dave, honey -- look what they're doing. Should we join them?"

I felt Jeanie's weight on the cushions next to me, then her naked hip touch mine. Then I felt the tip of John's cock against my hole and I stopped thinking about anything else.

His first push was hard, forcing his way through my rings. Then the mushroom head was inside me. It felt amazing. There was plenty of lube, and he just pushed forward slowly, piercing my rectum. His slender rod just eased forward until I felt his hips against my ass. Only Bob had gotten that deep.

"Do my ass, Dave, like they are," Jeanie whispered next to me. Then she reached under me and grabbed my cock.

"Ahhhh, yes," Jeanie said. I looked back over my shoulder and saw Dave leaning into her, apparently driving his big prick up her ass.

John started to move inside me, taking long slow strokes up my boy pussy. Next to me Billy moaned softly, John's fingers still inside her. Her hip moved as she pushed back against his hand.

John took about a dozen strokes in me, then withdrew. I felt him move over to Billy's ass, then I felt Dave's fingers replacing his cock.

"Kiss me, new girl," Jeanie said, and I turned my head to her. Our lips met, and she fairly devoured my mouth and tongue. Her hand was still stroking my cock. Next to us John drove his dick into Billy and began fucking her hard. I felt the shock of each thrust through our hips.

"God, I'm gonna cum," Jeanie said, "I'm gonna cum from this cock in my ass."

Dave began pounding into her, and both their voices raised to a higher pitch as they fucked to an orgasm.

"Fuck my ass, Dave. Cum inside me," Jeanie said.

"Yeah, yeah, oh," Dave moaned behind her. He pulled his fingers out of my ass to grip Jeanie's hips as he pounded her.

Jeanie's hand squeezed my cock hard as her body trembled in pleasure. Dave continued to slam into her. Then they were both still, but crying out their joy as they came. At the same time John pulled free of Billy and he stepped over and rammed his long dick into me again.

"I need to cum too," Billy said. "Sandy, suck my clit." She got up off the couch. There was a small space behind it, and she eased in there. Her panties were gone and she stood in front of me, her hips in front of my face.

She had called it right. What she had was really more of a clit than a cock, another new experience for me. Not more than an inch long and slender. Only the slit in the front and a small sack below proved it was a penis. I took her whole package in my mouth, sucking on it. My lower teeth were behind her balls, and I used my tongue to tease the shaft and head.

Beside me Jeanie and Dave had slipped away. John kept up a long slow fucking rhythm into my ass while I pleasured Billy's small organ.

Billy took hold of my head, running her hands through my hair. I made love to her 'clit' with my mouth. John started moving faster and harder, driving me against Billy with his thrusts. He began to moan softly.

I was loving all the feelings -- the cock in my mouth, the much bigger cock in my ass. My own prick was hard, but not near coming.

Billy held my head, pulling it hard against her belly. My nose pressed deep into her as she made sure every millimeter of her sex was inside my mouth. I gripped slightly with my mouth, pressing my teeth into her perineum. I licked the shaft inside me with my tongue and sucked hard. Then she was coming, her juices pouring into my mouth. It was a lot of cum for such a small generator, but I swallowed it all. Hey, I didn't want to leave a mess on the couch! She trembled in orgasm as she came, then stood still. I kept sucking her genitals, getting every drop of her spend, swallowing it all.

Behind me, John pounded my ass even harder. Then he was coming too, filling my ass with his hot juice. I could never feel cum in my ass like they said in porn, but I felt his dick swell and tremble in orgasm, spurting inside me. Then he eased himself out. Billy withdrew and stepped away. I stayed still, my head hanging over the back of the couch, my recently-violated ass in the air.

Jeanie came over with a towel and began wiping the lube and cum from my asshole. "Good job, little girl," she said softly, "You fit right in with this crowd."

John went into Dave's bedroom to clean himself in the bathroom. Billy took a second towel from Jeanie and sat on it next to me.

Dave was standing at the bar smiling at me, and I smiled back. "Drink, Sandy?" he asked, raising his own to me.

"I think so," I said quietly "Vodka rocks."

The suite had been properly set up, with plenty of liquor and ice. We were having a VIP orgy.

Dave poured my drink and brought it to me, then lay down a towel and sat next to me.

"How you doin'?" he said, "Glad you came?"

I laughed. "Well, I haven't come yet, but I'm glad I'm here."

"I'm sure we'll take care of that very soon. Any one of us would be happy to help." With that he reached down and grabbed my cock, stroking it softly.

Jeanie heard what was said and chimed in, "Oh, yeah. You won't get out of here without me tasting you."

The chat was general as we recovered. John and Billy talked by the bar, stopping occasionally to kiss and caress each other's parts. Jeanie sat on the other side of me, and talked about San Francisco. She started with restaurants and tourist attractions, but eventually slipped over to talk about sex.

"I just moved here for the sex," she said, "I love my work, I love my house, but it's the wild variation of genders, cocks, and pussies that keeps me here."

Dave said, "Judy and I come out here once a year for a few days. Good food, wonderful hotels, and a lot of fun."

"I'm really sorry you didn't bring her tasty cunt with you this time, Dave," Jeanie said.

"Well, this was sudden, and she couldn't get away."

"That's okay. Give her my love. In the meantime Sandy here is proving to be quite entertaining."

She got up and knelt before me, taking my dick away from Dave's hand. "Time for the taste test," she said, and leaning forward, she took my cock into her mouth. Oh, she was talented. She immediately went right down to my balls, and I could feel the tip entering her throat.

Billy and John wandered over to the coach and stood by the edge, watching Jeanie display her oral skills. I could see that both of them were beginning to get hard. It wasn't long before they decided to join in. They kissed each other for a minute, then Billy went over in front of Dave. Getting to her knees, she took Dave's cock in her mouth. John knelt behind Jeanie, lifting her ass up. In a moment he was balls-deep in her pussy, fucking slowly in and out.

Dave turned and looked at me. "Is this a great life, or what?" he said, and we both laughed.

Jeanie pulled up off my cock for a moment, continuing to masturbate me with her hand. "You pass the taste test, little girl," she said, "Your prick tastes wonderful." Then she went back to sucking, fucking my whole cock with her mouth.

Given all that I'd done, my cock was ready to explode, but once again Jeanie surprised me.

"I'm going to be very selfish now," she said. "I want to be airtight -- all three holes full. Dave, you're the biggest, you go in my cunt. John, you're the longest, you go in my mouth. Sandy, with all your youthful energy, fuck me in the ass."

Billy looked crestfallen for a moment, but Jeanie continued. "I most certainly wouldn't forget you, Billy! I get three dicks. You get three mouths and six hands. Try them all."

It didn't take long for her to orchestrate this arrangement. I was certain they'd done it before. Dave lay on his back on the carpet. Jeanie got on top. She kissed Dave, and while her face was engaged, she took his cock in her hand, wiping it between her labia to gather lubrication. Then she came upright and slowly sank down on his meat.

Dave moaned softly at her internal grip, his eyes closed. It was just a soft "Ahhhhhhh"

Jeanie bounced on him once or twice, then leaned forward, her hands to the sides of Dave's shoulders. John knelt in front of her, his knees to the sides of Dave's head, and offered her his long, slim prick. Jeanie hummed as she took him in her mouth, softly vibrating his rod. She went straight down to his balls, and glancing in from the side I could see her throat bulging where the head of his rod ended up.

It was my turn to mount, and it brought a mixture of feelings. I hadn't done anything with a woman since that night at Dave and Judy's house, and I was mostly subservient there. Other than that, it had all been cocks -- in my mouth, in my ass, cumming everywhere. I'd enjoyed every bit of it, and now I was being asked to be a man again.

Jeanie had an amazing ass, though, and looking down at the puckered hole between her cheeks was definitely giving me a rise.

All of this passed through my head in about 2 seconds, then I was down on my knees moving forward, my hard cock in hand.

Billy brought over the lube, something I'd forgotten. She poured some on Jeanie's asshole, where I started to work it in with two fingers. She poured some on my dick and spread it with her hand. I leaned over and kissed her by way of thanks.

Then she was pulling me forward by my cock, aiming it into Jeanie's ass. She brought the tip right to the opening, then put her hand on my ass, pushing me forward. The head of my dick pierced Jeanie's ass. Her back stiffened a little at the intrusion, then she wiggled her ass and sighed.

I put my hands on Jeanie's hips and drove relentlessly forward. I went all the way in, my hips against her ass, my balls resting on Dave's below me.

Getting into a rhythm wasn't that easy, but Jeanie took over, moving herself back and forth. Dave couldn't move much, and John and I didn't have to. Jeanie fucked herself back and forth on the pricks in front of and behind her, down on the two between her thighs, then forward to drive John's cock back into her throat.

Billy stood over Jeanie's back, a foot on each side, presenting her clit for me to suck once more. Again I took her whole package in my mouth, laving attention on it with my tongue and teeth.

Jeanie moaned softly as she fucked herself on three cocks at once, driving back and forth. She took hold of John's hips, pulling him roughly to penetrate her throat, putting her tongue out to lick his balls with each thrust. Her asshole would spasm every few seconds, strangling my prick inside her ass. Looking under her, I could see Dave had taken possession of her tits, pinching the nipples and caressing the soft flesh.

Then Billy turned around and bent at the waist, sticking her ass into my face. She reached back to hold her cheeks apart, and I licked her there, starting down at her balls and up to her rosy little opening. She pushed back against my tongue and I was able to get just the tip inside her, wriggling it to tease her.

A few minutes passed with only the occasional moan as soundtrack. Jeanie's ass was tight and beautiful. She was working very hard for her pleasure, and a thin sheen of sweat soon covered her back and ass. My cock was throbbing in joy. I knew then that women were still an object of serious sexual desire for me. I started thrusting forward to meet her motions, driving my cock deep into her back door. My balls swung against the point where Dave pierced her increasingly wet cunt.

"I want you all to cum inside me," Jeanie panted. She took John out of her mouth and lifted his cock to lick his balls for a moment. That stopped her hips, but my dick wouldn't be denied, and I took the opportunity to drive into her with long hard thrusts. I could feel the shape of Dave's cock through the flesh that separated us.

"Oh, you guys feel so good back there," Jeanie moaned. She took John's rod back into her mouth and began pushing back and forth again, impaling herself at both ends on stiff male cocks. Billy pulled away from me and moved forward to offer her clit to John. He met her halfway, diving onto her clit like a starving man at a banquet. I kept one hand on Jeanie's hip. With the other I separated Billy's ass cheeks and pushed two fingers inside her boy pussy.

"Oh, I'm cumming, I'm cummmmmminnnnng," Jeanie moaned, and her asshole squeezed me so tight I thought I'd be driven out, but I pushed hard and drove back deep into her rectum. I felt my balls become wet, and knew that Jeanie had squirted, wetting Dave's balls and mine with her juices.

We kept fucking Jeanie's holes for another ten minutes or so. She came again once, then twice. I fingerfucked Billy's ass while John sucked her clit. Then Jeanie hit one more orgasm, and apparently a wall. She stopped moving, so John and I took over the action, matching our forward thrusts into her mouth and ass.

Finally John said, "Cumming, cumming!" He gripped the sides of Jeanie's head and drove his cock down her throat one last time, her nose buried in his belly as he pumped his cum directly into her stomach. He fell back onto the carpet, and Billy quickly took his place, pressing her little clit into Jeanie's mouth.

All of the motion was now up to me, and I fucked Jeanie's ass like it was the last one I'd ever see. Nothing soft, all hard thrusts deep into her bowels. I held her cheeks apart to allow the deepest possible penetration.

My motion drove her up and down on Dave's cock, still going strong in her pussy. He pulled at her nipples, twisting them, hoping to force Jeanie into one last orgasm.

"Soon," I gasped out, "I'm gonna fill your ass with cum....soon."

"I'm with you," Dave said. He grabbed her waist, his hands near mine, and we plunged into her bottom holes together.

Billy moaned and stiffened, and I knew she was cumming into Jeanie's mouth. She thrust her little cock forward, once, twice, a third time. Then she got down on all fours and kissed Jeanie. Their tongues swapped Billy's cum back and forth between their mouths.

That was it, I needed to cum, right......"NOW!" I exclaimed. I pounded my hips against Jeanie's ass, filling her with my cream.

"YES!" Dave replied, and I felt his cock surging below mine, his balls tightening as he filled her cunt with his seed.

We took several more hard thrusts up Jeanie's holes. Then I regretfully pulled my cock out of her ass. My hips and knees were tired, I was out of breath. Like John I fell back onto the carpet. Jeanie rolled off of Dave, his soaked cock slapping onto his belly, and lay on her side panting next to him.

"What a magnificent fuck," Jeanie panted. She turned her head to me. "And you," she said, "you fuck incredibly well for a little girl." She smiled to take the sting out of her statement.

I smiled back at her. "I still really like women too, and speaking of magnificent, your ass fits the description perfectly."

"And that mouth," John added. There were smiles all around.

It was getting late by then, and we had a morning flight home, back to the chain gang. Everybody helped clean up the wreckage of our presence, gathering up the strewn clothing. Billy pulled a can of air freshener out of her backpack, which may or may not have erased the pervasive odor of bodily fluids in the air.

Jeanie and Billy went into Dave's bathroom for a quick shower together. Dave, John and I used my bathroom. John grabbed both of our asses while we scrubbed ourselves with soapy washcloths. "Please tell me I'll get to see you both again," he said.

"You got that right," Dave replied, and I smiled and nodded. His long thick cock fit me perfectly, and I wanted more of it.

I went back in the main room, found my panties, and put them back on. My now-soft organ made for a very sexy bulge in the front. Dave stayed naked, while John gathered up his street clothes and got dressed. We gathered at the bar, where John poured us a nightcap.

In a few minutes Jeanie and Billy came back out, Billy zipping up his male pants and buckling his belt. Once again I was amazed at the transformation from Billy boy to Billy girl. If you put pictures of both together you'd never realize they were the same human being.

Jeanie and Billy got a drink and we stood around the bar joking and reliving the high points of our orgy.

Jeanie hugged me, gave me a quick peck on the lips, and grabbed my package through my panties. "You are a lovely little girl who fucks like a real man," she said "Next time bring Kim with you." I hadn't thought that she knew Kim, but I guess she'd been out here with Dave too.

John and Billy hugged their way around too. Billy told me, "You're a magical clit sucker. Next time I want to find out how you fuck."

The trio trooped out the door with backpacks and a briefcase, talking of the 'meeting' results. Dave and I did a final cleanup of the main room, said goodnight and went into our own bedrooms. I had worn my panties to bed and was just about asleep, when the door opened, and I felt Dave's bulk slide onto the bed behind me. I just said, "Hi. Another nightcap?"

"Yup," and that was all he said. My blanket and sheet got pulled down, then the back of my panties. There was a cold drizzle of lube, which Dave worked into my hole with his fingers. Then I felt the head of his cock there. I moaned softly, just to give explicit acceptance of his plan. Then his cock stabbed inside me. It only hurt a little as he stretched the entrance. Then with a few more strokes he was all the way inside me. I was completely comfortable, just allowing him to lazily fuck me, almost like it was a simple goodnight kiss.

Dave held my hip as his speared my insides. He started fucking me, long and slow. I was so tired and relaxed I just lay there enjoying the sensation of fullness. He really didn't take very long, not more than 5 minutes. I relished the girlishness of my position. Then he pushed me onto my belly, still inside me. He lay on my back and started to move with increasing speed and ferocity. He didn't keep that up very long either. Within a few minutes he made one last slamming thrust, and I felt his cock twitching inside me.

"Ahhhhh, ahhhhhh," was all that came out of his mouth.

Then he withdrew, and pulled my panties back up over my ass. He gave my butt one quick slap, then said, "Goodnight -- again." I heard the door open and close, and fell asleep just like that, on my belly with cum dripping into my panties.

AUTHOR'S POSTSCRIPT:

It's Sandy's story, not mine, and he's not done. There will be more to it. There will be a backstory for Kim -- someone suggested it, and the idea interests me. If you like my stories, drop me a comment here.

Next: Chapter 12


Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate