Julia, Ben and Lisa Ch. 18

Ch. 18: Friday

A few quick notes:

1. this is the eighteenth chapter of a longish story, a novel in many chapters

2. everyone is 18+

3. there is no safe sex here - cause it's a fantasy, not an instruction manual

4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned

We, Harry and I, were in the elevator but still hadn't said a single word to one another. In the lobby we had awkward-hugged and then Josh kissed my cheek. Julia kissed Harry's cheek, and then Josh and Julia shared a nicer kiss, a real kiss. We had to do small talk but I let Julia do mine. Our drive down (was nice), how their meeting had gone (Josh: "super-great"), what had happened with that other account (Josh: "shit storm", Harry: "we fixed it") when they were leaving for home (next day.) The two guys discussed dinner plans. Josh was taking Julia to some fancy sushi place. Harry and I were going to have a drink and then decide, probably eat at the hotel. The four of us would regroup in the lobby around 10 for us girls to leave for home.

Alone in the elevator, Harry finally looked at me and said, "So how are you?"

"Fine. And you?" I had a kind of in between voice, not sure what was right.

"Fine." He laughed somewhat nervously. "Fine. At least I think so."

Harry key-carded us into his room. I was surprised not to find the kind of suite we'd shared with Josh and Julia the first time. It seemed to be a single room, sizable enough, but only a queen bed, a desk with a hard chair and one easy chair facing the bed from the opposite wall.

Harry motioned me to the chair and I sat on the cushion edge, ladylike, knees together and turned slightly to the side. He went to the mini-fridge to get us drinks. I was sticking with water. Harry poured himself a beer and sat with it on the end of the bed facing me.

He took a small sip. "You look...I guess just the way I remember you. I mean...you look nice."

"Thank you." I channeled Mona. There was no other way to do this, so now I used her voice.

We both looked around, as if something more interesting might be happening somewhere else in the small space. The corporate art work on the walls was slightly depressing. But the wallpaper was nice.

"And, umm...I like your skirt and blouse. I really do. They're very pretty."

I'd worn the blue skirt just as Julia had planned, the cream Peter Pan collar blouse was very teenagery. Blue bikini panties and the matching bra I'd got at VS that day.

"Thank you," I gave a cautious smile. It really does matter when guys notice the trouble we go to to look nice for them. Harry was being nice, is nice.

"Can I ask? Like, how do you pick that stuff out? I mean the outfits? How...?"

"Julia took me shopping."

"Julia...hmmm...OK...I guess...just makes me wonder what she's all about in this..."

"She's my cousin. I love her to death." I said it with an attitude and he heard it. I was fine explaining things to him, it's why I'd come after all. But no one, not Harry, not anyone, was going to blame Julia for what I'd done.

"I guess it just amazes me. I would never have thought..."

"I know. I'm sorry."

Harry waved off the apology and asked, "Do you want to talk about it? Tell me how?"

Well, I didn't really, but knew I had to. I looked down at my feet, realizing I was a girl who had never advanced beyond a single pair of Italian sandals. "Tell me how," Harry had said. I knew this was why I was here, knew that this was what I owed him. The truth.

I gave him the story, lots of stops and starts, but I gave it to him. Pretty much all of it, but only pretty much. Cause I left out everything about Mona and Donnie and Dolores. About our sex party, about sucking off Donnie and later Jerrod, about how Jerrod ended up fucking Mona and about how Dolores fucked my ass. That I left out. But everything about me stealing Julia's panties, about her figuring it out, her suggesting I'd be a cute girl, and the two of us playing at dress up and girl training. About how I'd been Juliet. About shopping for cute things. About getting my tits. Even about Charlie, which made him smile, and about going to Franklinville just for shopping. About how I'd been slightly freaked out when I knew two guys were checking us out. About how much I liked him, being with him, hearing his stories, seeing how he would treat a girl. About how he was nice, about how handsome he was. About being so nervous, about not knowing how. About how I'd fantasized about sucking cock. About wanting it, needing it, knowing it was the right time.

About me wanting both girls and boys, and about how the boy dreams would always end me on my knees sucking dick. But about Angela too, cause I'd already spilled the beans on that. About us making love. Not the details but about how amazing it was and how I was definitely not just about guys or cock. About how I might even be in love with her, about how wonderful she was.

Harry was nodding throughout, serious looking, interested, and asked only a few questions. He seemed not to like the part about me being with Bobby's girlfriend, but he agreed Bobby had been a dick. And he seemed happy that I liked Angela so much.

Harry asked, "So...aaah...I guess I was your first? Your first time?"

I blushed and nodded.

"It didn't freak you out, blowing a guy? Blowing me for real, not just a fantasy?"

It was difficult, but I had to tell everything. "A little I guess. At the start especially, why it took me so long to get started. But then...you know I just got into it, and you were being so nice, letting me take my time, letting me learn. I mean you said 'slow suck', remember? Which was perfect and then you like came in my mouth and by then I was so hot for cum." I paused to giggle, looked at him and said, "By then it was like drinking a fruit smoothie I wanted it so bad. Then I sooo wanted to blow you again, but that thing happened with your customer."

"Yeah. Me too, believe me. I was just getting ready to..."

"Mmmmm. Woulda been nice."

"But...I gotta ask. You get turned on blowing a dude, doesn't it get you hard? Did you cum while you were...you know?"

"No. No I didn't cum while I was blowing you. And yes it is difficult. But that's what I had trained for, like it stays soft and tucked up under you know? And the panties are tight and if you really focus, you know on pleasing the man, on pleasing you, then it can stay nice and soft back there and...it's kinda like...kinda you know like having a pussy."

"Fuck! A pussy?"

It was mega-embarrassing but I had to tell him.

"I just wanted...sooo wanted...to have a cunt then for you. Especially after you came, cause then I could give you something new for the second one, could give you a cunt."

It had come out in a burst, and now we got awkward again, looking around and wondering where we would go next.

Finally he asked, "So what now? You've got Angela. Are you still going to go out looking for guys?"

It pissed me off a little, or I guess more than a little. So unfair. "Hey. We weren't looking that day. It was the two of you."

He grinned and said, "Maybe." He chuckled but then saw my face and said, "Anyway, don't get mad. I didn't mean it like that."

I tried to calm down and sip my water, my eyes on the floor. The blue on my toenails looked just right. It made me smile. I guess I couldn't blame him for thinking it. He had every right. After what I'd done. Still it made me nervous, him thinking I was a slut. I was just trying to be honest, and it was going to be a lot harder if he judged me like that.

We went back to silence. Harry flicked on the TV, some news program, but kept it muted. Neither of us had moved from our perch. He pretended to watch. I mostly kept my eyes down, afraid of what I might see. Maybe I'd gone too blue there? A shade lighter? Still it looked nice in the sandals.

Harry turned off the TV and I glanced back up. He was smiling at me, relaxed now. He had finished his beer so I asked if he wanted me to get him another. He smiled his great smile again and trained those deep, rich blue eyes on me. Oh gosh! Ping! Girl-time! Ping! Just like that. Blink of an eye and it was girl time! I wondered if he could tell.

Harry said, "Sure" and I wobbled my way up to serve, smoothed down the front of my skirt and walked slowly, modestly, just right.

"Hey, Lisa. Let me ask you?"

"Yes?" I was bending in front of the fridge, aware of his eyes on my ass, that feeling a girl gets. I was searching for more of his brand.

"Serve me in panties?"

I snapped up, beer can in hand. "In panties?"

"Yeah. You don't have to. Nothing's gonna happen. But I thought...well, this is what I can't get over. I mean what does it look like there? Is it really like a pussy when you do it?" He sort of laughed at the end.

"I'm...it's just...tucked." Mona was back full time in my voice.

"Like no dick?"

It was getting weird, weird-good somehow, him accepting me, but still weird. Serving him in panties? Was he going to? You know? But those blue eyes would melt any girl. Oh-my-God he looked so handsome right then. Was he asking me or telling me?

"No. I have...I mean...I do have a dick. It's just kind of tucked up underneath so...you know in front...there's like no bulge." It sort of vibrated softly out of me. The cold beer can began to slip through my fingers and I had to juggle it to keep it from falling.

We grinned at each other.

"Like a pussy would be, like an actual cunt." His words were like the final magic, taking me back to that other room in this same hotel where I'd wanted so much to be that for him. To be a girl, a good girl, a girl who would always do what those eyes told her to do. To be Harry's cunt. There was no way I could stop this.

I froze, just for a second, then placed the beer on the desktop above the fridge. I turned to face him head on, to make sure he could see. I could feel the heat on my face. Some things never change. My fingers went nervously to the clasp on the side of the skirt. I fumbled with it, tried again and it stayed stuck, nervous the first time I was undressing for a man. Thinking every girl has her first time doing it. I tried a third time and it came undone. I held the skirt there and searched out his eyes. They told me what to do and I let the skirt slide down my legs. I stepped out of it.

I stood modeling for him. He nodded appreciatively. So nice. He asked me to turn. I did. Then front again and then back again. He had me bend over at the waist. "Your ass is incredible," he said. "And the front...like nothing there."

"I...I wished that day...we could have done it with me just in panties. So you would have seen this." I cunt-forwarded just a bit, showing off, showing him the empty slit space, all sugary now just for him, showing him my sexy V, proud of having a cunt. Proud thinking he might want to use that cunt.

He gave a small wave, telling me to come over. He was Harry, he didn't have to command, what he wanted was my command. He said just, "Lisa" in a voice strangled and husky. The beer was forgotten, everything but pleasing his dick was forgotten; I went to him.

"OK if I feel your tits this time?" He surprised me. I giggled, nodded and he took them in his big hands, squeezed them gently, treating them like real. He leaned in and kissed my tits over the blouse, thumbed over and then kissed my nipples. He was looking up into my eyes now from his seated position, fondling my tits softly, making me want him. Making him, I hoped, want me cunt or no cunt.

He ran a hand down from under my breasts, down slowly over my abdomen and to the smooth blank space under my panties. I pressed that blank into the palm of his hand, letting him feel nothing there and how happy nothing made me. He did it three times before he believed it. Three times just like Julia, my coach, had done days earlier. He looked up, caught my eyes, cupped my breasts again, smiled and said, "I'd swear there was a cunt under there."

He turned me now, his plaything, handled my ass hard over the panties and let his fingers run below to my hidden dick. It was all I could do to stay soft and limp and demure and feminine, to stay pussy. But he could feel it then, ran his hands and fingers along my dick right over those delicate panties. I knew it and worried it would stop everything. But when he turned me back and looked into my eyes I knew.

"Do you want it?" was all I could say.

"You were kissing my thigh that day. Say it now. Say what you want. Don't tease."

"I need it."

"Say it Lisa, say it for me."

So fine and lovely and kind and Harry of him. To let me, to make me, which was the same anyway. So lovely to be the girl and get to say it.

"Harry. Can I suck your cock? May I please blow you?"

I was panting with lust by now, my tongue useless for anything other than his cock, nervous not about him but about me, and it came fast, came out sak-yu-cak and plis-bol-oo, came out nice, just the way a girl should say it, the way he wanted it and I wanted it.

His answer was to lay back on the bed, arm folded over his eyes. I'd seen him do that once before. I knelt and got his lovely trousers and boxers off. His cock was stiff and thick and gorgeous, just as I remembered it. Pointing straight up to the ceiling. I leaned in and pressed the hard cock to my breasts, letting him feel my hard nipples on the underside and the head of my sexy master. I ran the fat head all over my face, kissing and smooching at whichever part of him presented to my lips and mouth. Then, I just couldn't wait, my little pussy eager for the real thing, I licked around the head once, twice, tasting him, tasting his flesh and the little bubble of juice on his slit, not able to contain my excitement, my hand cradling both sperm bloated balls. Then licked from his balls all the way to his little slit. I knelt up higher to get my mouth over the head and began lapping, soft and submissive. My tongue wet and happy, like meeting an old adored friend. The best friend a cunt could ever have.

I knew Harry liked a slow suck, but I wasn't sure that was what he wanted right now. It definitely was not what I wanted. He was so nice. He was Harry, and let me have my way, let me suck as I wanted, which was happy, wet, fast, slutty. I began the game of measuring my lipstick trail up the fat pole.

Suddenly he pulled out of my mouth and jumped off the bed. His eyes were glazed with lust (ping!) and he said, "Lisa. On the bed. On your back. In the middle." I jumped up and obeyed (ping!), nervous but ready. Was he going to fuck me now? Did Harry bring me here to fuck me? Would he know I wasn't a virgin there?

Harry pulled off his shirt, naked again for me as he had been days before. He climbed up over me, his big thick dick a swinging metronome. He straddled my chest, his hard ass over my tits and began to feed me dick. It's a difficult position for a girl, even a girl as friendly to the idea as I was. The neck. It's difficult. But he shifted up, his hands grabbed the top of the fancy headboard and his dick drilled down into my mouth from directly above. And, Oh-my-God, Harry was fucking my mouth, deeper and deeper, making me moan and gag and slobber as he attacked my throat full force, as I opened cunt-like to the flaring head. I raised my arms up and out and flat on the bed, wrists up, in surrender. But he was Harry, and he knew just how, how to treat a girl, and how to mouth-fuck a girl correctly, how to make it delicious for the girl too. I couldn't count the red smears from my back, but I could feel it when his pretty balls slapped against my chin.

I became, for only the second time in my life, a pretty toy for my man, a real living, breathing cunt. More a cunt than most the cunts alive.

Harry hit my gag three times fast and then he came. There would be no juice for my face this time, he wanted all mouth, all throat-pussy, wet and tight and completely open for him. My swallow didn't have to be pretty, it just had to keep me alive. Once, twice, three times and I had all of his smoothie in my belly. His cock came out of my lips with a pop, he let his emptied balls rest on my chin, let his lovely, slimy cock rest along my nose and cheek. He looked at me from above, down at me to inspect my work. I knew it was good. Still, I searched my lips with full tongue, making sure none of him was left there. It wasn't. I'd been a good girl. Harry let me kiss his dick twice, then rolled off beside me.

He got up without a word, went and retrieved my water and brought it to me. I wanted the taste, the taste of his semen, the taste of being man-owned, wanted it to last in me forever. But my man wanted this. So I swirled it into my mouth and swallowed twice as Harry crashed down on the bed beside me.

So nice then. Quiet and he reached for my hand. We rested together. This time I thought there really might be a round two.

Harry's fingers went underneath me. I turned over to let him have my ass. He draped his arm over me and kissed me on the cheek. I was afraid then but turned into him and we were kissing wildly, his tongue everywhere inside my slutty, used mouth. Now he was grabbing my ass hard and my tongue was fighting to get into his mouth. Henry and his two round little friends were still tucked, but started to speak and churn. I'd just told Harry how I'd trained to be a cunt, and I so needed to be that cunt for him now. He pinned me down and kissed me from above then turned me over and started spanking my ass over the panties. Hard, stinging, lovely slaps of my pretty ass.

"Take them off." This was it. Harry was going to take me, take my ass. I would be fucked again but this time full of real man-dick, and if I could make him cum in me there, full of real man-juice too.

I jumped up and stripped the panties off as he watched. It was hurting then but I stayed tucked so all he could see was a sugary nothing there.

"On the bed." Harry's cock was full mast again, angry and sweet looking. How could it ever fit in me? I prayed he had lube somewhere nearby.

I got back on the bed gingerly, cautious, trying to keep my little pussy pretty and discreet. Wanting Harry to think I was as pretty and as fuckable and as willing as any girl he'd ever had, or ever would have. I flopped face and tummy first to the middle of the bed. But old Henry was done speaking, was beginning to roar, was growing, a needy, willful bitch. Fuck! The hard-on was going to kill me if I didn't let him loose. I spread my legs just a bit and let him unfold up under me. Maybe it would be OK to have him hard but invisible under me as Harry did my ass, as he made me his pussy. I ground my tummy and swollen balls down on the sheet and presented to him, pretty and submissive. If he lubed it just right, I could be his little cunt.

But no. He turned me on my side, kissed me, and then moved me to my back.

"Spread your legs. I want it." Oh fuck! Alarms were going off. Harry wanted...my dick?

Harry's big fist went down and circled Henry, put him in a little choke-hold, and, Oh Fuck!, but he was touching me nice. Choked him, let up and just grazed it with a loose slippery hand, and then more. And more. Henry loving how tight and hard he was held; Henry being a girl and a dick at the same time. Harry's thumb pressed hard against the glans or I might have cum in the first second. It hurt, but hurt nice, and was for my own good. I glanced down. I was in shock, which seemed to get Henry even more excited. The only lube needed was my precum, streaming down my dick and over his hand. Harry was jerking me. I would have protested, have begged off, have begged to be just cunt again, begged him to fuck me in the ass, but Harry's tongue was too deep in my throat for that. I had to lay there and take it.

When I came about 15 seconds later the cum shot higher than I could have believed, higher than it had with Sandra on prom night, higher than when Julia and I sucked cock together in her bed, higher maybe than when Angela and I fucked. High and arcing and landing in big puddles all over my belly and all over Harry's hand, and still he stroked, still he kissed me. Till finally I had to wriggle away from his hand before Henry had a heart attack.