Girlfriend's Encouragement Pt. 02

I wandered into the kitchen, opening the fridge and pulling out two beers. I walked back to find Jeannie looking at a framed photo of Shelby & I. I wasn't sure how he'd react, but he didn't seem to mind.

"Gross you kissed a girl," he said miming sickness. "Gay."

I took a seat next to him and handed him the bottle before grabbing the photo and looking at it. It was a photo of Shelby and I at the beach some time ago. I looked at Shelby, dressed in a two piece and baseball hat. Her bronzed body from the sun and wide hips and tummy resonated with me, appealing to another part of me that I didn't feel with Jeannie. It was weird, having two distinct appetites, but I suppose bisexuality was a complex thing. I set the frame down and turned back to Jeannie.

"Does she know you're having a boy over? Do you need to put a sock on the door?" he asked, still acting in his typical fashion. I wondered what he thought was the plan for tonight.

"She's at work," I said shrugging. "She'll be home later." A half truth. Shelby would be back later, if you considered about 40 minutes to be later rather than sooner. It would be enough time to butter him up and pry him open sexually- I could have jumped on him right then and there, but the prolonging would drive him crazy. "So tell me what you've been up to." I asked, taking a sip from my beer.

I knew Jeannie, and I knew he couldn't resist talking nonstop. It's just how he always was, for as long as I could remember. So he went on and on, talking about how he had started going to the gym, how he dated off and on and how he was living a more lowkey life. When I mentioned the girly look he sported, he blushed. He made it clear he was still a man first and foremost but liked to feel cute.

"Not all gay guys are like this mind you," he said abrubtly. "I just like to look cute. You would have no idea my roommate was for example, or you!"

I nearly choked on my beer, his comment catching me off guard before I laughed it off. I was on beer 3, while he was on his 2nd. Neither of us were particularly buzzed, but we were certainly feeling more relaxed.

"I'm bi," I said after clearing my throat. "Girlfriend, remember?"

"Oh so you're willing to admit it now?" Jeannie said with a wide grin. I hadn't ever admitted to it before, only going far enough to say I was curious. My face burned, feeling a bit bubbly admitting it to him. It was freeing in a way, tearing down a wall I had put up.

"Yeah, I am." I said quietly. I didn't know what else to say.

"Coulda fooled me how often I rode you!" he continued, laughing more wildly now.

"Hey if you're going to throw it in my face like that you won't get another chance to."

Jeannie stopped and looked at me, coy grin on his face. He couldn't tell if I was serious or not.

"Is that an offer?" he asked slyly. I said nothing, instead letting the silence grow. The tension was thick, and I could tell he was clearly angling to take his chance now. He was sprawled out on one end of the couch, legs spread wide as he reclined against the arm. Despite our familiarity with one another's bodies, it usually began in clandestine fashion and never something so overt. We both wanted it and jumped at the chance to- so now, confronting the clear outcome, it seemed so much more intense.

Before we came to a conclusion, however, we both snapped our heads around to the sound of the front door unlocking. Jeannie spun around, sitting more traditionally as Shelby walked in. She looked a bit tired, but still dressed in her work clothes and with her hair up. She gave both of us a cursory glance before smiling wide.

"Hey!" she said setting her bag down. "You must be Gene!"

Shelby walked over, just as Jeannie stood up. Jeannie looked calm but a bit surprised at Shelby's surprise entrance. Still, there was little to suggest our conversation had been anything but normal just moments before. Shelby pulled him in with a tight, affectionate hug, her hand rubbing up and down his back.

"It's actually Jeannie!" I called from the couch. Jeannie looked at me with a wild look, presumably embarrassed by his cute nom de plume, but alas, Shelby was already aware of his alias.

"Ohh, I love it. It's cute." she said looking Jeannie over. "Like you." she said teasingly before giggling to herself. Shelby took off her jacket, leaving her in her skirt and dress shirt as she walked over to the kitchen. Jeannie looked at me blushing, obviously unprepared for how affectionate Shelby would be.

"She seems fun." he said with a soft smile. For all his boldness, he could be shy in front of new people- it was adorable. I reached out and placed my hand on his knee, giving it a tight squeeze.

Shelby returned with a bottle of cider, taking a long swig. As she approached the couch, her hand lightly touched Jeannie's arm.

"Jeannie darling you're our guest but you're in my spot!" she said without a hint of malice.

"Scoot!"

Jeannie looked towards me, my only reaction being to shrug.

"Better do what the old ball and chain says." I said in a comically exasperated tone. Jeannie seemed a bit lost but indeed scooted over, bringing him next to me as Shelby plopped down where he had been. She wriggled around in her seat- normally, Shelby disrobed when she got home from work, but present company indicated she had to remain clothed for now. Still, I could see her clearly chafe under the forced modesty, having to wear her snug dress shirt far longer than required.

"Wait you have cider?" Jeannie said looking at Shelby's bottle then back at me. "You didn't tell me you had cider!" he said, giving me a playful slap. He was relaxing, which made me feel more at ease. I didn't want him to be too uncomfortable.

No sooner had he chastised me than Shelby in turn returned the favor.

"You gotta finish that beer first!" she said, moving her bottle over and dinking the bottom of it on the top of his, with the beer beginning to foam and errupt out of the neck of the bottle. Jeannie managed to spill beer on himself first, dousing his shirt with it before sipping the surging suds from the tip. I laughed at the entire scene, taking a long swig of my beer.

"That's not how you do it!" Shelby said, taking her bottle and opening her mouth wide. Without provocation, she deep throated the neck of the bottle, easily, getting the entire length in and bobbing her head up and down. The pantomime blowjob made Jeannie finally laugh, his face red as he set the bottle down on the coffee table in front of the couch.

"Aw, look at you," I said as his shirt became translucent.

"You got a towel?" he asked, not too particularly upset. Jeannie was a good sport about the entire ordeal, raising his arms up. He looked at me, flashing me a curious look. He wasn't exactly sure what was going on, but he clearly let me know he was going to let things continue.

Rising to action, I set my beer down as well before reaching over and grabbing the hem of his shirt.

"Let's get this off, c'mon." I said pulling the thin shirt up off his body. "Arms up." I commanded to which he did without much resistance. His smooth, flat tummy came into view, a far cry from Shelby's softer, curvier figure. Jeannie had visible hip bones, along with a line running down the center of his stomach. He was lean, and my curiosity began to grow wondering just how he felt as well.

"Are you serious," he said with a laugh, pretending to be flabbergasted with it all. "If you wanted me out of my shirt you could have just asked." he finished, turning towards me with his shirt pulled up over his head. I finished the job, pulling it off with a quick motion and leaving him shirtless in a pair of short shorts.

"I've got a pair of shorts just like those," Shelby quipped. "I don't think I fill em out that well though."

Jeannie blushed, part of him wanting to take the compliment and run with it, but the fact that it came from Shelby clearly made him nervous. He probably didn't anticipate Shelby to be so forward. I on the other hand, was loving every minute of it.

"What a waste of good beer." I said shaking my head, looking at Jeannie's glistening body. He turned back towards me and offered me a quiet, but sincere, 'sorry' before looking down on the couch, biting his lower lip at the slight stain on it. Shelby looked over as well.

"No worries, this one's a bit wild still- not 100% house broken, we can blame it on him," she said pointing to me. "I'll just need to crack the whip more."

Jeannie laughed at Shelby's dry quip, but I decided to throw caution to the wind and leaned over to his shoulder and gave his collar bone a lick. Instantly his body tensed up, looking down at me with an open mouth, in utter disbelief. I got a taste of beer, but just a hint of Jeannie.

"What? I'm not letting beer go to waste!" I said shrugging as though it were no big deal. "Babe back me up on this." I said to Shelby.

"Yeah I think you missed a spot," she said pointing to Jeannie's chest. "C'mon be a good host."

I turned Jeannie towards me and licked his smooth, soft chest. He sighed, a quiet whimper coming out of him. If memory served me correct, his nipples were particularly sensitive, and the two small areolas- dotted with hardened nipples- were completely open to me. I continue to press my tongue onto his body, slowly dragging the warm, velvet touch over his supple body. Jeannie moaned louder this time, enough that he couldn't mask it as anything else. My licks turned smaller, before becoming small kisses, planting one on one of his nipples, teasing it with a flick of my tongue.

"Well if being shirtless is an option I'm in," Shelby said as she began to unbutton her top. She worked quickly, revealing first her cleavage and a hint of the black bra before it came fully into view. Not that Jeannie was paying too much attention, looking down at me and trying not to succumb to his lust. Shelby pulled off her top, leaving her in her skirt and black bra that barely contained her breasts, spilling out the sides.

"Babe I think it ran down a bit," she said, getting comfortable sitting on the arm of the couch before taking another swig of cider. Shelby had cleared up enough space leaving all three cushions free to use and free for Jeannie to lie back on. I took this cue and eased Jeannie down to the couch, sitting him down as he looked over at Shelby, then back at me. He seemed to comprehend what was going to happen and gave me a small nod.

"Y-yeah," he began. "I uh," he said looking down at his waist.

"Here just lie down," I said grabbing his shoulders and pushing him down onto his back. Jeannie lie there, looking up at Shelby who offered him a knowing grin. She watched intently, saying very little and drinking even more. I leaned forward and begin to kiss his stomach. I could feel him clench it, his hands grabbing for the couch cushions for a better grip. I moved over and spread his legs open, positioning myself in between them.

Shelby rubbed her free hand against her thigh, moving it up and down, pulling her skirt up and exposing her thigh. I could see her dig her fingers in, before grasping the bottom of the skirt and manhandling the fabric in her hand.

I finally reached the waistband of Jeannie's shorts, feeling the warmth coming from underneath them. He licked his lips before looking up at Shelby.

"Shhh, it's ok, it's ok." She told him softly. "Relax baby." Shelby had a way of sounding so gentle yet in charge, it made my cock twitch at the sight. That's my girl, I thought.

I unbuttoned the top button of Jeannie's shorts, hearing him gasp quietly as the zipper too gave way. He lifted his ass up a bit, enough for me to grab ahold of his shorts and pulled them down. He brought his legs together, allowing me to guide them to my side and easily slide his shorts off, taking liberties in how much I stroked his thighs. His pear body was even more evident now that he was close to naked, with only a pair of tight booty shorts preserving his modesty. He had wide hips, and an even bigger butt. The man was clearly meant to be taking it from bigger, stronger men like me. Even Shelby looked on in approval, Jeannie shyly trying to downplay the large bulge in his boyshorts.

My hand grasped his cock and balls, feeling how stiff he was and how small he was in relation to my hand. The gesture was not lost on Jeannie who looked at me pleadingly.

"Don't you think you should, I don't know, check my ass?" he asked, knowing where his best asset was. His hands continued to clutch the seat cushion, now gripping them for dear life. I didn't answer him, determined to show Shelby his small penis. I got a hold of his shorts, necessitating me to paw his as body, hooking my fingers into them as I pulled them away from his body. I watched as he tried to remain covered as long as possible, as I pulled the stretchy black fabric off of his body and slowly pulled it down. Jeannie gyrated his hips with the base of his cock exposed. He had shaved his pubes, though that hardly seemed like a special choice made for me.

The shaft remained visible, as he crossed his legs and looked up at Shelby. For her part, she had turned to her side to work her skirt down her thighs midway to her knees. One hand resided on her mound, while the other reached down and stroked Jeannie's cheek. Shelby traced a finger down it, tenderly soothing him with her touch.

"Shhh," she shushed again. "Just lie there and take it." she said as she ground her fingers into her mound, watching him look up at her.

I pulled down slowly, the entirety of his shaft visible with only his head remaining covered. He squirmed and wriggled a bit, whimpering and making other small cute noises before I gave his boyshorts a quick tug, revealing his cock in its entirety to both Shelby and I. Jeannie groaned, his entire body a soft pink as he went limp, making it simple to strip him down completely. His cock was indeed small, a good four or so inches longer, and it looked smaller once I spread his legs open. He had cute balls, hairless as well. Shelby's eyes were likewise glued to it, and while my cock wasn't particularly mastodonic, it was almost twice as long. I didn't find cock to be particularly pleasing, but watching Jeannie's reaction made him look so vulnerable, so ready to be used. He looked down at me, whimpering again with a quiet "oooh". I reached over and grabbed a hold of his prick, playing with it and pulling the skin back. He moaned even louder, as the slick tip of his cock glistened. It was now or never, and I dove in, giving his cock a small lick. Shelby's hand now found itself in her panties, and I could hear her rubbing it hard against her patch of pubes while her free hand traced a finger over Jeannie's lips. I twisted my tongue around, feeling how slick and smooth the tip of his cock was before placing my lips on it and sucking.

"That's so fucking hot babe," Shelby said, transfixed. "He has a cute cock, oh my God..."

Jeannie breathed out as Shelby's finger continued to caress his lips. He tried his best to make it look smooth, but his attempts at sucking on it were transparent to both of us. Shelby didn't mind, however, and let him suck on it. I moved in and swallowed his entire length, nearly gagging at first at how alien it felt before easily adapting to sucking cock. His prick was warm against my lips, and I was determined to take it slow and easy, making sure not to fuck things up. It was simple enough, and I eventually got my tongue involved as well. I simply imagined what I would have wanted and began to try to do it. I could hear Jeannie groan and moan, alternating between loud bellows and firmly sucking Shelby's finger as if it were a cock.

I then moved my mouth off of him and kissed his shaft a few times, a bit unsure about decorum and just going with what felt right. His balls looked so small, and my kisses found their way to it shortly, making sure to plant one on each. I don't know what exactly came over me, but I used both hands to pin down his thighs, holding his legs spread as I began to suck on his balls. This came much easier to me than sucking dick, a naturalness to it as I circled my tongue slowly around his sack. Jeannie moaned loud and long now, rising up from the couch cushion. Shelby took the opportunity to reach back and unhook her bra, discarding it without a second thought as her skirt now plummeted to her ankles. Dressed in her skimpy panties as well as her pearls, Shelby used the finger Jeannie had sucked on to play with her cunt while the other groped one of her breasts. She rocked back and forth softly against the arm of the couch, pulling on her nipple and twisting it roughly.

I could have spent ages sucking on Jeannie's balls, never once feeling like the submissive one in that situation, but alas, I moved on, pulling them out of my mouth and moving off of him.

"Flip over," I said, giving his thighs a tender squeeze. "Show me that ass."

Again, Jeannie looked over at, and then, Shelby. I had began to play with my cock through my shorts while Shelby continued to pleasure herself at the sight of her man taking on a gay lover, getting progressively hornier. Jeannie eased himself up, before turning over and presenting his ass to me. I gave it an approving smack, making it jiggle while his small cock and balls hung beneath him. Shelby plunged her fingers into her slit, uttering a deep, low growl.

"Oh babe," she said. "This is so fucking hot, this is so fucking hot! Go in raw!"

I didn't like my position, so I rose up from the couch and shucked off my shorts as I did so, going to the end of the couch and grabbing Jeannie's thighs. I easily pulled him half off the arm, letting his ass hanging up in the air while his legs kicked a bit beneath him. Shelby, not one to be away from the action, settled onto the couch proper, near Jeannie. Jeannie, for his part, could only sit there bent over and take it, his long, flowing brown hair hung in front of his face. Shelby stroked the mane back, playing with it and comforting him. Shelby was never a dominant woman, but there was a clear superiority she felt in relation to Jeannie; he was a fuck toy, fun for both of us. Jeannie had made up his mind as well, content to let both of us take charge.

I spread Jeannie's ass, eyeing his asshole. He breathed out, as Shelby pressed her forehead against his. She whispered quietly, but I could make it out.

"You're gonna take it ok?" she said to him. "You're gonna take it because my boyfriend wants it and what he wants he gets ok?"

Jeannie nodded weakly, looking at Shelby and uttering an almost inaudible "uh huh". If he wanted to play with us, he'd need to know his place. Shelby leaned forward and gave him a kiss, a gentle one before kissing his forehead.

"Good boy." she said before looking at me. "Fuck the shit out of him." she said, her hand continuing to play with herself idly.

I acquiesced, pressing the tip of my cock against his hole. Instantly Jeannie groaned, lifting his head up and gritting his teeth. Shelby stroked his neck up to his chin with a single finger, holding it there as if keeping his head up. Jeannie's ass was tight, much tighter than I expected it to be, but I could slowly feel his body give way to me, his legs spreading out wider to accommodate me. My hands gripped his hips, dragging my fingers down to his meaty, bubbly ass. I dug them in, before spanking him.

"He's so big he's so fucking big!" he groaned to Shelby.

"Take it you fucking slut!" she yelled at him.

As if by some magic incantation, I felt Jeannie's ass give waymore, his hole widening and allowing my prick to penetrate into him. I heard him moan a long, throaty howl before the tip of my head nestled between his cheeks. The rest came easy, as I filled his ass up. Just like old times, I thought.

Shelby kissed Jeannie again, and the two made out. Their tongues twisted, open tongue kissing as if passing along their shared experience as my play thing like a schoolyard secret. Jeannie moaned in an ecstasy only Shelby could understand. I felt a bit of jealousy, but it was mostly superficial. Watching them kiss openly felt like watching two girls kiss, but I still felt an intrinsic desire to punish Jeannie, so I pounded his ass nice and hard. Shelby bit his lip as he tried to pull away, silently screaming as I rubbed my thick organ rough against his hole.