Girlfriends Encouragement

Editor's note: this story contains scenes of gay male sexual content.

*

I was lucky, for a number of reasons.

I had a gorgeous girlfriend, one who stood 5'3 and had a slender build but having been such a strong emotional support for me, she was much larger than that. Shelby had dark brown hair on tanned skin, piercing green eyes that were always full of life. She was hot, I couldn't stress that enough, with two large D cup breasts and a plump ass she was never afraid to flaunt. Shelby had a soft, slight belly but her confidence in herself and outgoing personality never let her down. She was an open minded girl and this was perhaps her most attractive quality.

This was important because I had told her I was bisexual. For many girls this had been a deal breaker, and telling her had been one of my greatest anxieties. I wasn't attracted to men romantically- my heart belonged to Shelby- but the raw sensuality and powerful lust I felt wasn't limited to just women. Pleasure was amazing in any way, and I had never been under the impression that my sex life was anyone else's business. I liked what I liked.

Yet after 4 breakups because of it, I was worried.

I couldn't have picked a worse time to do so, on Valentine's Day just a week earlier. The entire weekend leading up to it had been nothing but progressively emotional activities that while cheesy, were bringing us closer. I had even gifted her a pearl necklace- though truth be told, that was half for me, I just loved how they looked on her. So it came as no surprise that the sex we had on Valentine's was charged, full of passion and the best we had had in quite some time. Not that that was lacking, we fucked often. 'I'm your slut,' she had once told me 'so why not do it a lot?' It was a very classy statement from my special lady, and I was all too ready to grant her wish. Shelby offered me her ass and I had fucked her anally, as was our custom, before she started rubbing my ass cheeks.

I instantly tensed up before the soothing feel made my heart race.

"Shhh," she whispered to me. "Just relax babe." she finished with a kiss on my cheek.

I moaned slightly, instinctively spreading my legs and ass for her use. Shelby chuckled, squeezing my ass tighter and closer to my tight hole.

"Good boy," she added, making me blush as I pushed my ass out towards her. "Oh, someone REALLY likes this!" she added with a giggle, pressing her index finger against my asshole.

"Oh God!" I moaned. A wild and devious look flashed on her face, both amused and captivated by my easy acceptance of what she was doing. As such, she had no qualms pushing her finger into my hole which let her penetrate me, allowing her to go in deep. "Deeper," I breathed heavily, rubbing my chest and letting my girlfriend toy with me.

"Good, take it boy." she whispered to me, pushing her finger into me. My body needed more, aching for release and she gladly acquiesced, as a second, then a third finger probed me.

She was silent now, eyes wide and completely lost in my behavior. I couldn't tell if she was disgusted or shocked, but her intensity didn't die down for a second, even after I reached for my hard prick and started jerking myself off. I eventually erupted, shooting a torrent of thick, ropey cum all over my chest and hers. Shelby eventually climbed on top of me and rested her head near mine.

"You really loved that didn't you?"

"God yeah," i instantly answered, so quickly and enthusiastically even she raised an eyebrow.

"Shelb, you love me for who I am right?" I asked, suddenly compelled to regurgitate everything about my sexuality to her.

"Duh silly." she answered with a smile.

"Even if I wasn't...straight?" I asked. This time Shelby looked at me quizzically. In retrospect, it was most likely obvious to her by now but I had to make it harder on myself.

"I...I'm bi." I finally said after an eternity of silence.

Shelby merely looked at me deep in the eyes before leaning to me and kissing me as hard as the first time I had told her I loved her. We held that kiss for another small eternity before she told me again she loved me no matter what.

Since then, life was pretty uneventful. Granted it had only been two weeks, but I was on edge. I loved talking about sex and the topic of me liking both men and women hadn't even been broached. I held my tongue out of respect figuring she didn't want to hear about it and grow jealous.

Today we sat on the sofa, I on my laptop while she idly watched the television. Being a pair of perpetually horny 20-somethings, we found ourselves in minimal clothing; I was wearing a pair of short black gym shorts without underwear while she was wearing some of what she had worn out today- a pair of tight white short shorts and a baby blue button up shirt, completely unbuttoned with no bra underneath. Around her neck was her pearl necklace I had bought her for Valentine's Day.

Shelby played with one of the pearls on her necklace, half paying attention to whatever reality TV she was engrossed in when she looked at me. I had been scrolling through a thread on a messageboard and had paused at one image of a particularly feminine guy about my age. He was totally slender, hairless and with smooth flawless skin. The slight tone of muscle was accentuated by his pump ass and the slight bulge in his cutoff denim shorts. I licked my lips staring at it, imagining my hand running down his chest and planting kisses on his nipples.

"Looking at gay porn?" Shelby asked with a wide grin and laugh. Her words caught me off guard, causing me to open and close my mouth stupidly like a fish. I instantly scrolled away, pretending to be admiring a photo of a shiba inu.

"No, uh, I was looking at a cute dog, he's a good boy!" I blurted out in rapid succession.

"Oh I think you were looking at another boy," Shelby snickered.

I sighed. There was no use in fighting it. I scrolled back down and opened the picture of the twink once again.

"Yeah, I was. But it's not porn." I added.

"Oh he's cute," Shelby said, leaning forward. The sides of her shirt parted, revealing her tits and the large areolas dotting each one. "But he's not really my type." she added looking at me with a soft smile. We planted a soft kiss on each others lips which mellowed me out a bit. I had no idea why I was so on edge, but Shelby was quickly calming me down.

"Is he yours?" she asked looking back at the photo.

Instantly I was struck again by her bluntness.

"I uh, I don't know, he's cute." i sputtered meekly.

"Oh yeah?" Shelby asked, lowering her voice just a bit. "What do you like about him?" She leaned in and kissed me again, much wetter and lewder this time, her hand resting on my chest. Any more fo where my heart was and she'd have it just about ready to jump out of my chest.

"I don't know..." I began. I looked back at Shelby who had a much softer, lustful look on her face. She looked so sultry, but at the same time welcoming, inviting me to divulge my inner most desires. Her wonton flagrant display of her body as well as her genuine curiosity about his sexual tastes made me weak and unable to resist. "He's...feminine, I guess. And I don't know, it's cute."

I looked harder at the picture. Relaxing myself a bit more and letting my imagination continue. I imagined my hand reaching into his shorts and fondling his cock and balls, squeezing them gently and feeling his soft cock grow hard in my hand. It made my heart leap and gasp slightly with a sharp inhale. Shelby moved forward, her face near mine as she planted small kisses on my cheek and neck. A wave of goosebumps ran down my body, chills wrapping around me as my nipples stood hard. Her tits rubbed against me, gently touching against my arm and chest, the tips of her nipples hardening while her hand on my chest rubbed softly on my sensitive skin.

My mind spun imagery of me reaching around himi and tugging his shorts down, revealing his hard dick and feeling around his hairless balls, fondling them while I kissed his slender, supple shoulder. Shelby responded in kind, kissing down my chest and making sure to lick and suck on each of my nipples, lightly nibbling and letting out a playful chuckle that turned into a low growl.

"You thinking about his cock babe?" she asked, pressing up against me while her hand rubbed my belly down to the waist of my shorts. I could feel her nipples, now hard as diamonds, rub against me, lightly sending shivers on my body. I labored my breathing, feeling uncomfortable and uneasy. Wearing shorts felt wrong to me, the urge to shuck them off growing each passing second. I wanted my cock out, I wanted to openly stroke myself. I could hear Shelby breathing hard as well, swallowing and pursing her lips wet for a second. "You...love cock babe?" she asked finally.

I groaned, hooking my thumbs into the elastic waistband of my shorts, pulling them down and revealing my small neatly trimmed patch of pubes. The base of my cock was visible, hard and pressing against the front of the soft fabric.

"Yes," I whispered softly at first. "God yesss..." I moaned. Shelby finished the job, pulling down the front of my short and letting my hardened cock spring to life, bouncing up and down while the tip begged for any sort of stimulation. "Oh Jesus fucking fuck!" I growled. I grabbed the fabric of the sofa in my hands, clenching it tight and gritting my teeth. Shelby's soft fingers wrapped around my throbbing dick, jerking me slowly.

All I could focus on was the twink's round ass, perfectly snug in the too-small jean shorts he wore. The bottom swell of his ass peeked through the bottom opening, tempting me to lick and kiss each cheek of his perfectly round globes. I imagined parting his ass open as he presented himself to me, the thick musk of his quivering arousal inviting me to plunge my prick into his ass, to penetrate him and fuck him hard.

Shelby had begun stroking me harder, going so far as to kiss and lick the length of my shaft. Her own hand had disappeared into her shorts, rubbing her mound. She took one long lick from the base at my balls, swirling it around to the tip and lightly sucked on it. She knew just how to tempt me so, and pulled away before I could burst.

"What do you want to do with your boy toy?" she asked longingly, her shirt hanging off of her shoulders, her fingers playing around her clit.

"I want to pound him!" I barked, desperate to get off. "I want his ass! Oh my God baby," I said, glowing in the pleasure of being so lewd and debaucherous. "Babe I want his cute ass! I want his tight boy pussy! Ughhh fuck I love cock holy shit!"

Shelby took this as her cue, swallowing my dick into her mouth and sucking me with such ferocity that my hands went straight for her head, pushing it down and stroking her hair, completely loving everything happening to me physically and mentally.

"GENE!" I yelled, holding Shelby's face on my dick while I erupted in her mouth. She gaged a little at first but greedily lapped away at my seed, licking my dick up and down completely clean. Her mouth was filled with my cum and she swallowed most of it, letting some of it drool out of her onto her chin. We kissed in a loving embracing, my tongue tasting the familiar tang of cum. I couldn't help but smile as Shelby flashed one of her innocent, cute smiles at me despite being half naked and with a mouth full of my cum.

"Babe get that cock hard again!" Shelby teased half jokingly. She grinded her pussy against me, stradling over me. "Hope you like my ass as much as you love Gene's." she added wiggling her ass for me. We both chuckled as she wiggled it again.

I stroke her hair and we looked into each other's eyes with genuine warmth.

"Babe who's Gene anyway?" she asked with a sly smile.

"Oh!" I said realizing what I had blurted out. "He's uh, a friend of mine."

"Gene? Gene the Queen?" Somehow Shelby remembered my old boyhood friend and the loving nickname I had given him. "He's gay?"

"Yeah..." I began, a bit nervous. "We uh, we used to have a thing. Him and I. Before I got with you." I quickly added to reassure her. "Like..."

"Fuck buddies?" she pipped in.

"Yeah..." I answered back unsure how she would take it.

"Oh," she said looking away and nodding in acknowledgement. She leaned in and hugged me once again while I kissed the top of her head. We were silent for a few seconds, the faint aroma of her perfume wafting into my nose. It was a familiar scent that hypnotized me, making me hug her tighter which she appreciated with a sweet giggle.

"So wait why'd you stop fucking him?"

I looked down at her shocked, her sly grin back on her face.