The Ballad of Jaimie and Vera Ch. 03

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Act 2 Part 1
6.1k words
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Part 3 of the 10 part series

Updated 11/01/2022
Created 05/26/2014
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AwkwardMD
AwkwardMD
1,317 Followers

After the 'Establishing Shot', Vera and I hit the road. We rented an RV and set out cross country. Vera called it "Jaimie Bradley's Sexual Awakening Tour 2013: Coming to a city near you!" The plan was to go around and find people I could have sex with, have them sign a release, film it, and put out a DVD. Or start a website. That part of the plan was fuzzy, but we knew that the footage was an important part, and it was certainly the part we were looking forward to the most.

So we hit the road. Over the next six months, we rambled from city to city, hitting lots of college towns and a ton of hotels in between. In all, we recorded about 55 encounters. What follows are our favorites.

Hal, the virgin. #53

This scene actually happened very late in the trip, but we both agreed it should be the first one we released, or showed, or whatever we were gonna do with it.

We were in Ann Arbor, Michigan (Go Wolverines!!), crashing a frat party. Vera was using a little minicam she had hidden in her purse. She'd thought that sometimes the pick up, long before the sex began, was worth filming. Even if all we did was trash it later, at least we'd have it. I trusted her opinion. As with most of our encounters, we didn't try to seek out anything in particular. We let whatever might come our way happen and made the best of it. So far, that had produced more than a few gems.

We milled around for a while, eventually finding our way to a bar set up in the basement. When I pushed my way through to a seat, a gawky guy next to me looked back, saw that I was with someone, and moved out of our way with a polite smile. Vera got her Rum and Coke, and I got an Appletini.

"You know, despite having the most impressive package in this place and a set of balls to put anyone to shame, you drink like a little girl!"

"You don't know it's the best," I scoffed, sipping my drink. "You're just buttering me up. I see through you."

"Oh. OH, you think you have me all figured out, don't you?" She handed me her drink and purse, and stepped to the side into a little space in the crowd and started dancing. It was disjointed and it didn't quite line up with the music, but her moves were fluid. It was kind of hot to watch her go, and a crowd opened up around her while she burned through some routine she'd clearly mastered. I stare open mouthed, in amazement. After a minute or two, she petered out. The crowd around her roared with approval.

"I had no idea you had any dancing talent at all," I said, or rather shouted over the noise. "I concede the point!"

"God damn right you do," she said, snatching her drink back and taking a long swig.

Suddenly, the gawky guy from before came up from behind Vera and tapped her on the shoulder. Once I got a better look at him, I saw he was less a guy and more of a late teen.

"Um, excuse me," he started, voice cracking. "Was that from Napoleon Dynamite?"

Vera threw her head back and laughed. "Guilty!"

"It was still impressive," I said.

"It was spot on," the kid exclaimed. He started to say more, but two larger guys shouldered past him rudely. At first, they were going to pass right through our little conversation, but then they both came to a stop and grinned at us.

"Well well well, Who do we have here?" The first guys voice is so deep, I feel it in my chest.

"I'm sorry, but I was-"

"Fuck off, nerd," the second one said, giving the kid a shove. He disappeared from view into the crowd. Vera looked at me, and I nodded.

"We were talking to him!" Vera yelled.

"C'mon, seriously? That dweeb?" Vera threw her drink in his face without a second thought, and stormed off. I shook my head at them and followed.

We had to wander around the party for a little while before we found him again. He'd found a loud and crowded corner to hide in. Once he spotted us, he pretended he hadn't made eye contact and tried to look away, but Vera walked right up to him.

"I'm sorry about those guys. They had no right to do that."

"No, they kinda do. I'm rushing this frat. I pretty much have no claim to talk to anyone tonight."

"That is the dumbest thing I have ever heard."

"I don't really want to be here," he said. "I'm only rushing because my Dad was Theta Lambda too."

"Will he be pissed if you don't make it?"

"I'm a legacy. I'll make it no matter what."

"Well," I said, speaking up for the first time. "If you're gonna make it no matter what, then why are you taking it?"

He looked at me like I was stupid. "Those two were both twice my size. What else was I gonna do?"

"You could leave."

"And go where?"

"Our hotel room?"

That stopped him down.

"My name is Jaimie. This is my friend Vera. Would you like to get out of here?"

He just blinked at me for a minute. Then he looked at Vera. Then back at me.

"If this is more hazing, it's not cool..."

"This is totally on the level," Vera said.

"...ok."

Vera turned to head out. I nodded my head at her and he followed, and then I brought up the rear. Vera gave the two larger guys from earlier the double bird on the way out. It was too loud to hear what they said back, but I'm sure it wasn't pleasant.

"I'm Hal, by the way."

"Pleased to meet you," I said, stepping up to walk beside him once we get out onto the sidewalk.

"Are we going far?"

"No, we can walk there. We're at the Ramada over by rt 110?" Hal just nodded. "It's actually better that we can walk, because we need to talk to you a bit."

"O...k?"

"First of all, I need to ask you if you'll sign this," Vera said, pulling out our release form and a pen from her purse.

"What is this for?"

"We're going to film this."

"I'm going to be in porn?!"

"Yes, although there's no guarantee that we'll use any of the footage in the end. Once we get that squared away, we'll contact you later about payment. Is that ok?"

"Are you kidding me? Of course!"

Now Hal was maybe 5'8", and if he weighed 140 lbs wet, I'd be shocked. He had horn-rimmed glasses, shaggy black hair, and the least amount of muscle definition of any guy I've ever considered taking to bed.

"I do have one question though."

"Just one?" Vera laughed. "I'd have a ton, but go ahead."

"Why me? Those two guys were way bigger than me."

"What can we say? We like underdogs."

Hal nodded. He scribbled his signature everywhere we had highlighted, and Vera grinned broadly as she shoved his form into her purse. The hotel we were at was only a few miles, so we were there pretty quick. Hal was sweating quite a bit, and wasn't that hot.

We got inside the room, and Vera looked to me for direction. I was a little unsure of how to handle this one, so we both puttered about for a few seconds, waiting to see what Hal did. Once the door shut behind him, Hal stops dead in his tracks and stared at us wide eyed.

"Hal?" I said. "Is everything ok?"

"Yeah...I" We both stop down to look at him. "I. Um."

"Hal, is this your first time?"

"Um. Yes?"

Vera subtly made a fist and pumped it. She loves breaking in virgins.

"Ok," I said. "Well, it's guys choice. You can do whatever you want with either one of us, or both of us. I should say, however, that if this is your first time, you should start with Vera." She turned and looks at me. "What, I can't be the cameraman?"

Hal turned and looked at Vera. She stared at me for another minute before shaking it off and nodding. She kicked off her boots, unbuttoned and dropped her jeans, and flung off her shirt with a queried look at me. Hal just stared in amazement, and I can totally relate. She had (and still has) a fantastic body. Even though we'd been on the road, she still made time to jog, or something, every day. I brought the camera out in the open instead of tucked into the spot in her purse where the hole was.

Vera walked across the small room to stand right in front of Hal. She smirked one more time over her shoulder at me, and then turned to give Hal her full attention. She closed her eyes, rolled up onto her toes, and leaned forward. Hal seemed like he could barely believe this was happening, but he didn't skip a beat in leaning down a hair to kiss her. It was tender. Just the lips.

Without looking, she reached out to grab his wrists, and placed his palms on her tits. He whimpered a little in the middle of their kiss, but once they were in place, his hands went to work. They were nearly the perfect size to hold her breasts.

After a minute or so, she leaned back, although she held his hands in place. Once she was certain he wouldn't let go, she moved her hands down to undo his belt. Hal's hands did stop as he stared wide eyed at what she was doing. She bite the side of her lip, and her hips squirmed a little. The fact that he couldn't keep his focus was a huge turn on for Vera. Once his belt was undone, she dropped down to her knees, undid his button, dropped his zipper, and pulled out his cock. Hal was pretty average, but it had a nice thickness to it. Vera tilted her head back just slightly to stare up at him while she took his semi-rigid cock into her mouth.

Hal inhaled sharply, making a kind of whining sound. His hands sorta floated in the air, as he clearly has no idea where they were supposed to be or what he should have been doing with them. Vera kept his dick in her mouth for a while, leaning her head from side to side. When she finally backed off, it was considerably harder but not much larger or longer. She gently wrapped her lips around his head, and with great slowness, proceeded to take his entire cock into her mouth and back out again. 10 seconds in, 10 seconds out, and then she backed off completely.

"Hal, if this is your first time, you're gonna cum soon. Don't worry about that," she said, smirking up at him. "But we also don't want it to be just from a blowjob, so..." She got up, and dragged him to the bed by his cock. Just as she climbed up onto it she let go, and he took the moment to strip off the rest of his clothes. She flipped over onto her back, and as soon as he was free, Hal climbed up on top of her.

When he finally got face to face with her, it was really beautiful. She ran a finger along his cheek with just the tiniest hint of a smile on her face. Hal looked down for a second and grunted, but Vera only stared at him. When he finally entered her, her eyebrows went up and her mouth opened wide. There was no more kissing. Just two faces three inches apart, staring.

Vera's prediction was pretty accurate. It only took a minute, at most, before Hal's momentum was completely lost, and his wiggling on top of her slowed to a stop. For her part, Vera handled it like a champ. Once he was done, she leaned up and kissed him again, this time slipping in a little tongue. Hal crawled off of her after a while and flopped down onto the edge of the bed. I let him have a minute to reflect. Vera started fingering herself softly.

"Hal," I said, "we're really hoping you'll be able to join us again, so we're gonna mess around for a while. You can just watch us, or you can direct us, and whenever you're ready, you can join us."

I sat the camera on the tripod facing the bed, and got down in between Vera's legs. I immediately started licking up the cum that was flowing out of her pussy, and Hal gawked next to me.

"That's fucking hot," he said.

"Just wait," I said, winking at him before turning my attention back to Vera's pretty pink pussy. Some of her own juice was mixed in there, adding that unmistakable, if indescribable, flavor I'd come to love.

"Can I, you know, do you next?"

"You can..." I said, smirking. "Although maybe you should wait just a second more." I turned back to Vera's pussy again and attacked her clit.

"Fuuuuuuuuuuuuuuuuuck! Fuckin Fuckin Fuckin Fuck!" Her hands feebly pushed down on my head, and her legs kept trying to come up over my shoulders, but I swatted them away. She wanted me to spend more time on her pussy. She didn't want to cum too soon, but I wanted her to cum very, very badly.

"Fuck!! FUCK!! FUCK!!" It didn't take long before her hands stopped pushing and started grabbing hair. When I heard her voice drop, I lightened up. I wanted this orgasm to be gentler than her usual thrashing. It was really musical when she came, sing-song-y and beautiful, although no less profane.

"Just do it," Vera said while looking at my pants, happily writhing around on the bed in the moments after.

I sat up, smirking at her, and pulled off my t-shirt. Hal made an "awwww" sound, and his eyes were glued to my chest as I reached back and popped off my bra. I let my biceps and elbows push my tits up and together, and Hal was dumbstruck and fascinated all at once. I beckoned him forward with one finger, and as he crawled over the bed towards me, I laid down on my back.

Hal settled in next to me and immediately latched onto my right tit. His eyes closed as his tongue began massaging the nipple, like a hand forming clay. Pressing but not pushing, shaping without redefining, and stroking. Good lord, the boys tongue could stroke. After a minute, Vera settled in on my other side, one of my tits in each mouth.

"Damnit, that feels good..."

My hands slid along their necks... fingers lacing into their hair... nails along their spines... Veras hand slid across my stomach and grabbed Hal's wrist. He let his hand be guided over my abs and down between my legs. My cock was down in my left pant leg, and after a little bit of searching, she laid his hand down on it. At first, it just laid there on top of my cock, unaware. The suspense was driving my crazy, and although I wasn't hard before he got there, I was hard pretty soon after.

Still no reaction from Hal.

Vera, her hand still over his, started sliding his palm up and down over my jeans. The friction made my cock jump a little, and finally, Hal reacted.

"What the what?!" he said as he jumped backwards and off the bed. Vera didn't move, she just kept slurping away at my tit. I'd stopped lactating almost as soon as we got on the road, a fact which Vera had been extremely disappointed about. She'd really come to enjoy sucking on my tits though, and my nipples had gotten much more sensitive since the surgery, so it was win win.

"It's not a flashlight in my pants, Hal. I'm just happy to see you..." Vera coughed a little, fighting not to laugh.

"Those are real!" He squeaked, pointing at my tits. "I swear those are real!"

"They most certainly are," Vera purred.

"You're a girl!"

"She most certainly is." Vera was slurring her s's again. Damnit, she knew what that did to me. I reached both hands down to unsnap my jeans, arched my back up so I could slide them down, and my cock sprung out. Slowly, I laid myself back down. My cock was sticking nearly straight up, and Hal just stared at it.

"I've never seen... Usually, shemales... huh."

"mmm," Vera took one last slurp, and sat up a little. "Since she started off female, she thinks term dickgirl is probably more appropriate, although I prefer futa."

"Foo-ta?" I'd never heard the word before.

"Look it up some time. I think you'll enjoy it." With that, Vera dropped back down to my tit, although she had one hand on my shaft and was lightly stroking it up and down. I looked over at Hal, and he was still just staring distractedly. His dick, however, was at full attention.

"Hal..." He kept staring until I repeat myself. "Hal! You don't have to do anything with it if you don't want to."

"No, I..." Man, he just kept STARING at it! I love this reaction. I'd gotten it before, but this was one of the most satisfying renditions.

"Here," I said, scooting over to the edge of the bed. "Come over here." Hal got up and came around to stand in front of me, but his eyes were glued to my cock the entire time. I tucked my legs up over me and pulled back my balls. He stared equally wide-eyed at my pussy...

"Holy Fucking Shit! How is that even possible?!"

"Remember. You don't have to do anything you don't want." Hal seemed pretty intent when he finally stepped up. Of all the people we fucked, Hal was the most hesitant about it, but once he got there, between my legs, his hesitations subsided. I couldn't believe he was hard and ready to go again... well maybe I can. Vera and I are pretty fucking hot together.

Hal gripped his cock as he stepped up, and pushed the head up and down between my lips. In no time at all, he was fully lubricated and pressing in against my poor overlooked pussy. It'd been a little while since I'd been fucked there, so it was pretty tight when he started pushing. I didn't have to fake the deep breaths, the gritted teeth, or the grunts. His dick felt great, but all he could stare at was mine, and with just the slightest hint of awe now.

"Do you want to touch it?" I licked my lips, hoping. Hal didn't respond, but one of his hands moved from my thigh down to my cock. It spasmed at his touch, which made me clamp down on his dick involuntarily. We both whimpered a little.

Suddenly, Vera crawled over me to start sucking on my tit. I watched the skin stretch around my nipple as she pulled it up and into her mouth, but only for a moment. Then her hand grabbed my head and turned it so that I could see that one of her tits was hanging right above me. One of her perfect little tits... 69 tit sucking. I'm surprised we never thought of this before.

I reached up and grabbed her tit, squeezing it and forcing the nipple down into my mouth. My tongue flicked rapidly back and forth, and then my lips closed around it. Gently sucking, pulling it down. Her other tit, perfect and pink, dangled beautifully just out of the corner of my eye.

Hal began stroking my cock slowly, which started a whole chain reaction. I grunted and bit down gently on Vera's tit. She gasped, dropping my nipple out of her mouth for the first time in what felt like forever. She lightly spanked my sideboob before picking it back up again. My feet curled around Hal's back, interlocking at the ankles. Once my legs had that leverage, I really started to tighten down on his dick. He started to cry out a little with each thrust. He didn't stop stroking my cock though, which makes the feedback loop get just a little bit stronger.

It was good that Hal had already blown a load in Vera, because he lasted much longer this time. After a few minutes of that, I was dangerously close to cumming, but I was holding it back for now. I had an idea.

"Slide down," I said. Vera wasted no time crawling further down. I felt her hand take over for Hal's. His amatuer touch had a certain exhilarating appeal, but Vera was a pro. She worked the top half in and out of her mouth, while she stroked the bottom half lovingly.

I returned to her clit. Vera's clit is her easy button. It's ultra sensitive, and if you work it just right, she'll orgasm extremely quickly. She, of course, is not a fan of that, but she rarely stops down during sex to say so. The angle was in my favor. My dick is so long, she had to start further back to get to the front of it. I started slow, keeping constant swirling pressure. I have this routine down so well, I probably do it in my sleep. Switch directions, always keeping contact. Up and down, but pressing firmly and dragging the clit with me as I go. Slowly, my arms reached up around her waist. I could reach one hand across her back to my other elbow, which was good, but for now I just held her closely.

Hal, meanwhile, was picking up steam. His cock felt so thick inside me, and it was wonderful to be able to stretch those muscles around him. So wonderful and full. I had to let go of my balls to get my hands around Vera's waist. They fell to rest on and around Hal's dick. Each time he pushed in, he bumped them with his lower abs. Vera got a little further in on my dick. Felt like she was getting most of it in there now, and her hand was marking the spot her lips could reach. Nearly there. I felt myself getting ready to cum, so I acted.

AwkwardMD
AwkwardMD
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