Girlfriend's Encouragement Pt. 02

Author's Note: Here's the long awaited sequel that no one asked for or expected! I apologize for the lateness- I thought I had lost it but was able to salvage it! This is one of my earliest stories, enjoy!

***

I walked up behind Shelby and gave her a big hug, catching her off guard and hearing her squeal with delight as I pulled her body into me.

"Someone's affectionate," she said, looking back at me and giving me a kiss. "I like."

For the better part of two weeks, Shelby had been closer than usual. This was not coincidental, as my coming out as bi had seemingly brought the both of us closer. Moreover, this seemed to light a spark within my girlfriend immensely as she tacitly admitted to finding the idea of gay sex to be alluring to her.

For the better part of the past two weeks, Shelby had encouraged me to be more vocal about my sexual tastes and fantasies. The more overt I became with it, the more she seemed to revel in the debauchery of it all- this was most evident in how she dressed, wearing less and less around our place. Today she opted to wear a halter bikini top as a 'shirt' while wearing a pair of tight jeans that hugged her ample ass. This owed in part to the hot weather today, which she gladly took as her excuse to dress more and more revealing. She still wore the pearls I had bought her- I suppose she must have really loved them after all. Her tan skin looked smoother and felt softer, her slight belly shamelessly out for my hands to rub. The allure of her brazen trashiness and degenerate sexuality made me more attracted to her, feeling free to not hide behind put upon societal conventions.

I ground my cock into her ass, hands gripping her stomach and digging into her. Shelby sighed softly, taking the initiative to press her ass back into me.

"Been thinking about me or...?" Shelby asked, wiggling her ass rougher against me. I unbuttoned the top button of her pants, hearing her sigh with relief. Shelby slouched a bit into me, completely content with all that was going on.

"Sure why not." I quipped. I had been thinking about Shelby in this instance, but I could go either way. My hand continued to work the zipper of her jeans- so snugly painted onto her body that they remained in place. In spite of this, I wedged my hand into them, rubbing over her pubes and caressing her mound. Shelby sighed once more, tilting her head back and kissing my cheek as she pulled the small triangles that covered her breasts off of her chest, revealing her D cups to me.

We hadn't directly broached any gay talk in the past few days, and I knew Shelby was dying to dig right in.

"How much have you been thinking about Gene?" she asked me in a husky tone. Gene was my old fuck buddy, from when I was still questioning if I was gay or straight. While I harbored no romantic feelings for him, the passionate lust affair we shared was enough to get my cock stiff- I was addicted to his body, but still found it difficult to be completely honest for fear of hurting Shelby. "Have you spoken to him?" she asked.

"A bit," I lied. In reality, Gene and I had reconnected and had been texting one another. Talk had been cordial, if not sincere at first, but quickly became playful and then finally outright naughty. I never bluntly told him I craved him, but the way I talked about his body and how much he discussed his sexual desires, we were barely skirting around it. Gene was a top, but his smooth, hairless body made my cock twitch, causing Shelby to giggle. I wanted to kiss his body all over, to taste his cock once more. "We've been texting." I vaguely told Shelby.

"You didn't tell me that," Shelby said slightly surprised but still rubbing her ass against me.

"Naughty boy."

My hands drifted up towards her breasts and groped them, massaging her ample tits and playing with her nipples.I heard her gasp, my fingertips touching her sizable brown nubs just right. Her hands moved back up and replaced mine, allowing me to go back to rubbing her belly and sliding the other into her pants once more.

"Let me see your phone." she tersely stated. She sounded demanding, but more a consequence of her bubbling arousal rather than anger. "I wanna see."

I reached down into my pants and pulled out my phone, unlocking it and opening the conversation to Gene. Gene was feminine, putting it lightly. He had long hair and I had taken to entering his name in my phone as Jeannie. I scrolled up to the very top of the conversation and handed it to Shelby. Her eyes darted from side to side, reading my innocent advances, with mundane attempts at conversation before things started to get hot. I had asked Gene to send a picture of himself- a request he obliged to, sending one over of his long hair, short shorts and tight t-shirt. My fingers slid over Shelby's slit as she saw my old flame, and the ensuing conversation about calling him Jeannie.

"He's cute." Shelby cooed quietly before groaning, arching her back and head back as if constricted by the spike of pleasure. She turned back and kissed me, planting a wet, sloppy kiss on me lewdly filling the empty room with the bawdy sounds of our lips smacking together. She turned her attention back, mouth slightly open as she read on.

"Dirty boy..." she said with a slight cackle. "You've been naughty behind my back."

My finger penetrated her lips, easing itself into her pussy. Shelby sighed, her pleasured noise turning into a soft laugh. I pressed my hand into her stomach, rubbing it softly as her pants began to peel down slowly as the result of fingering her. Shelby remained mostly silent aside from the odd noise of enjoyment, but those ceased as the conversation between Gene and I grew more and more intense. Openly talking about him being cute, him of how he needed a strong man to satisfy him and a screenshot where he showed me that he changed my name on his phone to Daddy. Shelby's chest rose and fell, reaching her arm around and pulling my head closer to hers so we could kiss and lick one another. She dropped my phone and reached deep into her pants, guiding my hand and pushing me to keep playing with her.

I leaned in and kissed her shoulder, nuzzling my face against her soft, tanned skin. Her entire body was hot, a sweet fruity scent faintly wafting from her body. She was sweating a bit, both from the heat and from being so worked up. I gave the nape of her neck a long lick, ending right behind her ear as she breathed a heavy sigh. Needing no further prodding, Shelby pulled her hand out from her pants and used both to grab onto the waist of her jeans, pulling them down just enough to settle beneath her ass.

Taking her head, I reached down and grabbed her hand, still wet from her juices before shoving the glistening digits into her mouth and making her taste. I nudged her over, towards our sofa and pushed her over the arm, leaving her ass up in the air for me to take.

"Babe pretend I'm Jeannie," she loudly begged.

I grabbed her ass and pulled her sizable cheeks apart, revealing her puckered asshole. It came as no great surprise that she had taken to anal in the same window of time that I had made my revelation of being bi. A coincidence if there ever was one. What WAS a great surprise to me however was how much she enjoyed it, the moment my cock piercing her tight hole was the moment I had heard her scream with such renewed life that there was no going back from it. It had taken her some time to acclimate, but her ass was ready to be pounded whenever I felt up to it.

I penetrated her ass, pushing the tip in and feeling little resistance to me; she had been stretched out enough in recent days to take it all and the raw sensation of my cock filling her was itself its own pleasure. Like a forbidden treat, Shelby moaned at the mere presence of my prick inside of her.

Everything after that was electric, ramming my cock in and out of her while her juicy cheeks bounced against me. Shelby made some very loud, guttural noises- raw and throaty that bordered on savage. It wasn't meant to be more than an open showcase of how much I needed the relief, ignoring her desires completely as I felt her hole tighten on me. Like two wild, rutting animals in heat, I took advantage of the intoxicating, slutty mood Shelby was in and came inside of her ass.

Shelby's pants rested down at her ankles as we both leaned onto the couch. I could feel her kicking and wiggling out of them for a comically long amount of time before stamping my foot down on them, allowing her to pull her feet out.

"I needed that." Shelby said.

"I know."

Neither one of us said much. I felt a further need to say something more, that there was something unsaid between us that needed to be addressed but I wasn't sure yet.

"I know you're not satisfied babe." Shelby suddenly added. "You want Gene."

"I do." I answered truthfully.

Shelby said nothing but pushed off of the couch, as I leaned off of her so she could do so. Completely naked save for her necklace, I watched as my cum ran down her thighs. She bit her lip at how much it tickled her.

"So let's invite him."

***

Friday morning came and with it, so did the end of Shelby's work week. I had the day off, but we had much to discuss before she headed out, necessitating me to wake up at 6AM on my day off.

I had convinced Gene, or Jeannie if you will, to come over for the weekend. He knew I had a girlfriend, seemingly either oblivious to it or assuming that our weekend would be much more platonic- if not a bit playful. Good cheeky fun, pardon the pun. This was great news, and Shelby shared in my excitement, finding it adorable that aside from the sexual desires I felt that Gene was also my friend and that I genuinely felt excited to catch up.

We had to set ground rules, of course, which is what brought me to waking up so early.

"You're going to fuck him." Shelby said after emerging from the shower, dressed in a robe with a towel wrapped around her hair.

"He's not gonna fuck me though." I blythely stated. I was aroused at the idea of fucking him, but not vice versa. It wasn't our style, though I'd be lying if I said we hadn't tried it once before.

"I..um..." I began to trail off.

"What is it?" Shelby asked, removing the towel from her hair.

"I, I don't know. I kinda wanna suck his dick." It sounded so humiliating, my face burning red. My hands gripped the bed.

"Aw," Shelby said facing me. "Babe it's ok. You wanna deepthroat him." She said matter of factly.

"No, no it's not like that." I quickly said, pumping the brakes. "He has kind of a small dick and I don't know, it's fun to, I don't know...tease him and stuff."

Shelby turned on her hair dryer, giving her hair a quick once over and thoroughly getting every inch. Her face was blank, partly half asleep and running on a deeply ingrained ritual of getting ready and partly no doubt imagining what I meant. She flipped forward, hair hanging in front of her as she got the back of her head and giving the long brown length one last run. Turning off the hair dryer, she set it down and began to brush the long mane of brown hair.

"That's hot," she said before pausing, her lips tightly pressed together. There was obviously more she wanted to say. "Did...could I um, could I teach you or help you with it?"

"You wanna teach me how to suck cock?"

Shelby bit her lip and turned to me, a mischievous smile on her face. She couldn't stifle her laughter and quickly blushed.

"SOO BAD!" she said pulling her hair back. Shelby often wore it in a ponytail for work, or when it was shorter, a simple cut that tapered down to her chin before flaring out like something from the 1960's. As she pulled her hair up, the loosely secured robe began to open up a bit, revealing a strip of flesh from her chest down to her pussy. Shelby opted for a high ponytail today, up closer to the top of her head. Doing so resulted in stretching her arms farther up, pulling her robe open more.

"That's another thing," I began to ask. "Did you want to, I don't know, get involved?"

We hadn't discussed it before, and while it sounded awkward as hell to say aloud, it seemed to be something worth establishing right away. I still got jealous, as ludicrous as it sounded, but didn't mind her getting involved in some way.

Shelby grabbed the hair tie off the dresser and began working her long hair into it, the robe now completely open in front and revealing most of her front. I could see her reflection in the mirror, and a hint of nipple caught my eye.

"If you want," she said. "Would that be okay with you?"

I didn't say anything and milled my answer. Shelby sensed my trepidation and walked over to me.

"Hey," she said gently. "I love you remember?"

I sorely needed to hear those words. I wasn't sure how people seemed so easily able to jump into group sex or threesomes, but the reassurance was much needed. There was a reason I was dating Shelby rather than Gene. Sex was sex but Shelby was my rock.

"I love you too."

"I'm not going to leave you for him." Shelby said with an honest tone. "Men on men is hot as fuck but," she trailed off, looking into the distance. Her head bobbed from side to side for a second before looking back at me. "There's no nice way of saying this, but I love a MAN."

"So you don't want me blowing him?" I asked, missing her point. Shelby sighed and looked up with a shake of her head.

"No, listen it's like...ok you want to suck his cock fine. I don't care if you swallow his ball- which you should do- but like, that doesn't define you. You're just...I don't know, you don't go by 'Jeannie' for one and you just look like a man. I don't know. It's hard to explain. But at the end of the day ten times out of ten, I want to be with you."

"I like what I like," I said shrugging.

"RIGHT." Shelby said. "And that's why we're doing this together."

She leaned in and hugged me, holding it for a second.

"I want you to get a little involved yeah. I know that much. And if everything is feeling fine and it's not weird, I don't know maybe a little more."

Shelby smiled and arose from the bed, removing the robe entirely as she walked over to her dresser. She walked with a sexual delight, giving me a great view of her ass as she bent over to pull out her underwear. Before she did so, she reached for her pearl necklace and put it on. I couldn't help but feel happy it was the first thing to go on, even before her underwear.

The rest of the morning was uneventful, as Shelby got dressed. She had a way of transforming 180 degrees, going from trashy and slutty plaything of mine to Shelby the scheduler and receptionist. Her black bra and matching panties were soon covered by her white blouse and long skirt, before her jacket went over that as well. She looked professional despite the lewd thoughts that swirled through her head- despite her facade of looking put together, she continued to glance at my nudity, and didn't bat an eye as we walked towards the door. She opened it while I stood to the side, leaning in and stroking my cock a bit, giving me one last tease before she gave me a goodbye kiss and went on her way. I wondered if me being naked while she was dressed was some kink of hers. Regardless, I went back to bed.

I couldn't easily fall back asleep, my mind racing of what would happen. Was this going to be a one time thing? Was Gene going to be a permanent part of our relationship? I flipped off the sheets, revealing my mostly nude body, covered solely in my boxer briefs. My cock strained against the thin fabric, as I reached down and groped myself. My body was hairy, and unmistakably masculine. I didn't go to the gym much but I had a naturally athletic physique, just with a little bit of fat over it is all. I pulled down my underwear, my long, veiny cock looking back at me. Gripping it, I breathed out and snuggled deep against the bed. I had taken the initiative to trim my pubic hair, leaving my balls hairless and my pubes tidy. A byproduct of htis was how amazing my or Shelby's hands felt on my bare skin. I stroked myself a few times, peeling the skin back on my cock and revealing the tip of my dick. It was so sensitive, as my other hand rubbed my chest.

I rolled over and pulled my underwear on. Soon, I thought. Soon enough it'd be taken care of. I drifted off to sleep not long after, dreamless and waking a few hours later. It was 2PM and even after a shower and eating, it was still barely 2:45PM. Gene wouldn't be here for another hour and a half and I had to continue to fight the urge to touch myself. I debated what to wear before opting for a simple loose tank top and loose shorts. I wasn't exactly Mr. Universe, but compared to Gene I may as well have been, so I wanted to flaunt it as much as possible. I continuously checked my laptop, looking at gay porn and reading gay stories, working myself up a bit. I hadn't been inside another guy in a while, and it seemed a bit daunting at first. I texted Shelby an 'I love you' text to which she replied in kind, but asked me not to do anything sexual before she got home.

Eventually at about 4:30PM, I heard a knock on the door. My heart pounded in my chest, and I nearly shook, feeling my hands and feet grow cold. God why was I so nervous? I stood up and cleared my throat and walked to the door, my legs feeling completely like jelly. I glanced down at my cock, making sure it wasn't too obvious I was horny before I breathed out once more, opening the door.

Gene stood outside, looking every bit as feminine as I remember him being and then some. He was shorter than I, but taller than Shelby- probably about 5'5 if I had to wager on it. Though he was distinctly male, he was on the precipice of androgyny- with soft features, a pear shaped body that was clearly evident through his t-shirt and jean shorts as well as his long brown hair. Just by looking at him I could see how soft his skin was, and his face instantly lit up the moment he saw me.

"Hey handsome," he said shyly before I reached out and pulled him into a hug. He was warm, inviting me to take his body right then and there but I restrained myself somehow. I held him much longer than a normal hug, an eternity having the harbinger of my awakening all to myself while the world around me ignored us. He nearly trembled in my clutches, his lithe form snugly held against me. My heart fluttered. There was a newness to it and distinctly I could tell that while I felt emotions strongly for Gene, it was nostalgic and friendly. I had a slight fear that I would fall for him, but it seemed to be unfounded.

"Hey you." I finally said back, letting him go. Gene continued to smile weakly, as if holding back a larger one. He finally cracked, his lip quivering before he covered his face in his hands, laughing nervously as I grabbed his arm and pulled him in. "Such a drama queen." I said rolling my eyes.

"Am not!" he said walking into my apartment. "And call me Jeannie." He pulled his hands away from his face, bright pink while he bit his lower lip. That must have been on his mind for some time now, and his shakiness told me this obviously took a lot of courage for him to say. Still, who was I to say no?

"Ok boy toy." I told him, causing him to laugh once more and turn around, walking into the living room.

Gene- or Jeannie as he wanted to be called- had a pear-shaped body, as I had previously mentioned. This was never more evident than when he turned around, his slender torso flaring out to a large, thick ass, with sizable hips. His thighs matched, tapering down smoothly free from any hair. He took great care in how he looked and I respected it.

"Have a seat," I said walking into the living room as well as he plopped down on the couch. I should have specified on my lap but there'd be time for that later. "Can I get you anything?"

"I'll have whatever you're having." he said.