Seren's Secret Admirer

Note: all characters depicted are purely fictional and over the age of 18.

I've never been the type of person who had a ton of friends, a few guys I grew up with that I'm still close to, but I'm not super outgoing or social and I just haven't been good at striking up new casual friendships. I was hoping that moving to a new city would be a chance for me to change that. When my long-time girlfriend got accepted to a prestigious medical school and the decision was made that we'd both move to New England, I initially imagined myself seizing the opportunity to break out of my shell and show myself that I could be one of those guys who can go out to bars alone and talk to anyone, make friends, be the life of the party. However, it certainly did not turn out this way. Eight months into our new life and my girlfriend's first year at school, I had gone out to zero bars alone, made zero friends, and been the life of zero parties.

When an upcoming break in my girlfriend's hectic schedule was approaching, she and a couple of her childhood friends decided to plan their annual "girls' weekend," a trip they took together every year since they had graduated high school. For two nights they would go to New York, or Virginia Beach, or the countryside and get dressed up to go out to nice restaurants, get wine drunk, and talk about their lives.

Of course, for me, this usually meant two nights alone. Occasionally, one of my close guy friends would happen to be free and we might do a little trip of our own -- camping or the casino, or whatever guys are supposed to do. But they were all newly minted attorneys and finance guys now, or recent fathers, and tended to be busy. Which was the case this time around.

"Sam, why don't you reach out to Zach and see what he's doing?" My girlfriend suggested in the days leading up to her trip. "Sarah said he might be going out to party with some of his guy friends."

Zach and Sarah were a couple that my girlfriend had decided we would be "friends" with. Sarah was her classmate whom she met on her first day of med school. The two of them had grown close through the months of all-night study sessions and lab work. So close, in fact, that my girlfriend invited Sarah to come along on the girls' weekend.

Zach was Sarah's jock boyfriend. We'd gone out to dinner or drinks a few times with them, and the girls had hit it off wonderfully. Zach and I, not so much. My few attempts to talk movies or books landed flat, just like his attempts to talk football or college basketball. Our professional interests didn't line up, either. He obviously could care less about my work as a remote college writing instructor, and when he first told me what he did for work it was so boring that I don't even remember what it was. I'd spent the last few of our encounters pretending to know what he did for a living, nodding along as he droned on about it.

Zach wasn't offensive in any way, or rude, he just wasn't exactly the type of guy I ever have been or ever would be friends with. He was tall, good looking, built, confident, probably the captain of his high school lacrosse team. I was shorter, thin with wide hips, long hair almost to my shoulders, someone who I'm sure Zach and his high school lacrosse team buddies would have called a "fag" or "girly." Needless to say, the idea of reaching out to Zach and spending time with him and his friends was very unappealing for me.

The truth was, I looked forward to being alone for those few days. Since we'd moved and my girlfriend started her demanding school schedule, I'd found myself alone more often than not, and I'd used this alone time to further explore something I had always been drawn to. Or, rather, someone. You could call Serena a hobby, I suppose, but I thought of her more as a part of who I am. Another version of myself, more accurately, someone I kept secret from everyone, including my girlfriend. Well, almost everyone.

As I watched my girlfriend rush around the bedroom, pulling clothes from the closet and her dresser and throwing them into her suitcase for the weekend, all I could think about was the trunk that I kept hidden in the crawl space behind our closet. In it were clothes, Serena's clothes, all of the sexy pairs of panties, bras, lingerie sets, leggings, high-heels, and cocktail dresses that I'd bought over the past several months. Clothes that, during those long stretches when my girlfriend wasn't home, I pulled out from their hiding place and relished in putting on strutting around the apartment in, posing in, touching myself in, and dreaming up stories in.

As I said, Serena was a secret to everyone I know. However, my alter-ego does have a presence online, where she publishes erotica under the name SerenaXO on a popular erotic literature site and forum. The stories, fantasies that I've dreamed up during my countless hours as Serena. The first story I ever wrote as Serena was the 100% true story of how I first discovered Serena.

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Serena had first emerged several years ago, before I ever my current girlfriend, when I lived in a small apartment with several roommates during college. One of my roommates, Michelle, had once dared me during a drunken, late-night game of truth-or-dare to put on her underwear and walk around the apartment. I protested at first, but under the harsh berating of her and my other roommates I relented and went into her room to get naked and slip on a pair of purple satin panties I found in her drawer.

I've always been nearly hairless naturally, and as I slid the silky fabric up over my legs, the sensation sent instant shivers through me. I posed for myself in the mirror, turning to admit and admire that my plump ass looked fucking hot in the women's garment. 'I'd fuck me,' I thought as I turned and practiced arching my back and positioning my legs to accentuate my naturally feminine form -- a form that I'd always hated and resented about myself, but which I suddenly felt very secure in.

"What's taking so long?" Michelle's voice came through the door.

"Uh, yea hold on." I stammered and set about desperately trying to stuff down the swollen erection I'd grown as soon as I put on my roommate's panties.

When I finally got myself under control, I emerged from the room and stepped out into living room in front of a suddenly silent audience. I glanced around at Michelle and my other three roommates -- Josh, Aiden, and Tom -- their eyes locked on me -- on my body -- smiles on some faces, open-jawed shock on others.

"Wow." Josh said in a hushed whisper. It was the only noise in the room and it hung there in the air.

The effect I had on them sent a flourish of joy through me. It was a feeling I'd never had before. I felt sexy. I felt powerful. I felt...was this what confidence felt like? I did one lap around the room, strutting like a caricature of a showy runway model, accentuating the motion of my hips, and headed back towards Michelle's room. The show lasted all of thirty seconds, but honestly, if asked, I would have done it all night.

"Dammmmmmnnnn! That ass is fire!" I heard Aiden yell as I closed the door behind me and changed -- begrudgingly -- back into my own clothes.

After that initial experience, I snuck into Michelle's room once or twice (or three or four times), when all my roommates were out or at class, to slip into her panties. The last time I did, just before the end of the school year and we were to all move out, I found a matching black lace thong and bra set. I clasped the bra on and looked at myself in the mirror. As I slid the thong between my round ass cheeks, I locked eyes with myself in the mirror. Only, it wasn't myself, it was Serena. She smiled back at me, as if to say, 'nice to finally meet you.'

"Wow." I heard Josh's voice, as if an echo of that first night.

I whipped around to see my roommate standing in the doorway with that same slightly agog, slightly smiling look on his face as he read every curve of my body with his eyes. I looked from his face to his crotch, where he was showing a visible bulge in his gym shorts.

"You can't tell anyone." It was the only thing I could think to say or do.

I'd had an initial urge to cover myself with my hands, or hide, or slam the door in his face. But, for some reason, I did none of these things. I just stood there for him to admire, after a few seconds that felt like minutes, I realized...was I posing for him? In hindsight, I absolutely was. It was the look on his face. It was that his eyes were so deadlocked on me as Serena. It was that he obviously liked, even wanted, what he saw.

"Why shouldn't I?" He said, finally looking me in the eye. I started to sink a little. During those initial thrilling moments, I'd felt a strange confidence and arousal, but now that he was clearly going to bully me that fell away.

"Come on," I pleaded weakly. "Please?" I had no leverage, nothing to offer, nothing to give him. Or, so I thought.

"I can keep a secret," he said and bit his lip before finally saying..."but you need to do something for me in return."

"Wha..." I started to ask but then it hit me what he meant. The look in his eye. The bulge in his shorts. "Josh, really? You're not...neither of us are gay."

"Look at you." He said. "You're not a guy right now."

I turned and caught sight of myself in the mirror. I involuntarily struck a little pose, pushing my ass out against my hand. He was right, I had to admit. But, sex was another thing entirely. At this point, I didn't know exactly who or what Serena was...she didn't even have a name yet...but I knew I was sexually attracted to women.

"You don't want...sex." I was shaking with nerves, I could hardly speak.

He stepped into the room and sat on the end of Michelle's bed.

"Sit on my lap," he said.

I hesitated for a moment, but ultimately swallowed what little pride I had and did as told. The feeling of his body against my bare ass felt so foreign. When he put his hands on my thighs, I shivered and tried to stand up, but he grabbed my hips and pulled back down against him.

I could feel his solid cock against me, cradled between my thonged ass cheeks. And in that moment, I was turned on. That I had that effect on him, I felt like his erection was mine. I made it. It belonged to me. I sat still for a moment and felt his breathing heavy against the back of my neck, sending a tingling down my spine. I closed my eyes and felt his hands on my thighs. They were shaking ever so slightly. That's when I realized, he was nervous. He'd mustered up the courage to try to bully me and now the real Josh -- softer, self-conscious -- was showing.

I slowly started to move, gyrating my hips side-to-side, forward-and-backward, slipping the cradled of my ass across the length of the rod under this shorts. When he moaned softly, my own cock throbbed to attention in the panties. I picked up the pace of my movements, dry humping him, giving him an ass job through his shorts. I placed my hands on his thighs for leverage and moved faster. Until he stopped me, pushing me off his lap to sit on the end of the bed next to him.

"Did you..." I said after a moment of him catching his breath.

He just shook his head, no. But I could tell he came close, and it had freaked him out.

"I'm sorry," he said. "I shouldn't have made you do this."

He started to stand up but I grabbed his hand and gently pulled him back. He sat again next me, but further away. He refused to look at me.

"It's okay." I said. What the hell was I doing? I don't really remember what went through my mind, only that what happened next seemed natural, inevitable.

After he finally looked at me, looked me in the eye, I placed my hand on his bare thigh just below the hem of his shorts. I set it there gently, resting against his warm skin. I was so nervous, and could tell he was too. Our breathing and pounding of our hearts was all I could hear.

After a moment, I began stroking his thigh softly with my fingertips, playing with the soft hairs on his leg, feeling the goosebumps form on his skin. On each consecutive pass, I ventured my touch further and further up the inside of his leg, eventually reaching the lower hem of his gym shorts halfway up his thigh. I stopped with my hand there.

I stared his face. He bit his lip, his eyes locked on mine. When I saw him give the slightest, almost imperceptible nod, I slipped my fingertips under the hem of his shorts. He gasped my hand ran slowly up the inside of his thigh and I felt the tip of his semi-erect cock. I drew my hand back slightly. I'd never touched another dick before. The second I touched it, my own cock throbbed, but it still scared me a bit.

I left my hand there a few seconds as he breathed heavily, willing me with his eyes to go further. I obliged by gathering my own courage and furthering my reach up into his shorts, lightly feeling the length of his quickly hardening mass in my hand. His skin was warm around the the flesh of his cock, and I could feel it pulsing with blood in my grip. When I got to the based of his shaft I found a trimmed nest of pubic hair.

"Oh, Sa..." He gasped and closed his eyes. That he was unable to complete sentences while his cock was in my hand drove me nuts.

"Serena." I whispered into his ear. I have no idea where the name came from. Michelle was a big women's tennis fan and often had matches playing in the living room, but I don't know. It just came to me as if it were who I was.

Unable to do much more with my hand up the leg of his restrictive shorts, I let go of his shaft and pulled my hand back out. He opened his eyes and looked at me as if disappointed. But, before he could even think, I put my hand on his chest and pushed him gently back onto the bed.

As he laid on his back with his legs hanging off the edge of the bed, I lifted his t-shirt and ran my hand down his chest, across his stomach, and slipped it under his wasteband. Through his pubic hair and down, I found his now rock-solid stiffness waiting for me. Still somewhat restricted by his shorts, I used my other hand to work them down his legs. He got the point, and eagerly helped by pushing them down off his ass and to his thighs.

I stared enthralled as his waste band lowered, exposing first that patch of trimmed dark hair, then the veiny length of his cock. When the shorts were down over the head of his prick, his cock snapped up and pointed directly at my face. I wasted no time grasping it in my hand, stroking the length of it up and down, getting to intimately know my first cock that was not my own. It was not super large, bigger than my own embarrassing four-inch penis, but not so big as to scare me away. It felt a little foreign to my hand at first, but as I spent more time stroking his, feeling its veins and the rim of its helmeted tip, it felt just right.

I looked up to his face, his head pressed back into the bed with his eyes closed in agonizing pleasure. Josh wasn't the cutest guy, he was pretty average all around, and like me he wasn't the most confidently outgoing guy socially. I was guessing that this was likely one of the only handjobs he'd gotten so far during college. I doubted if he'd even had his cock sucked.

It was then that I truly felt Serena's power. I had the power to pleasure this person. To give them this gift. I owed it to him to share this gift that I had, and I wanted to spoil him.

So, I lowered myself down, laying cross his stomach, my face inches from his cock. I stroked him a few more times in my hand, and watched as a drop of pre-cum oozed at his tip. I opened my mouth and pressed the tip of my tongue to his tip, tasting the delicate saltiness of his pre-cum. He moaned loudly, maybe loud enough for every other apartment in the building to hear.

Savoring every moment of this new experience, I swirled my tongue gently around the supple head of his cock, letting my saliva wet him and run in drops down his shaft where I used it to stroke him with my hand. When I felt ready, I opened wide, slid the head slowly up my tongue, and wrapped my lips over the top half of his cock.

I don't know what I found more unbelievable, that I had another man's dick in my mouth, or that it drove me so wild. With each stroke of my tongue and mouth up and down the length of his length, my own small prick pulsed against the black lace. Several times I felt like I might cum, and I wasn't even touching myself.

As I adoringly worked his cock into and out of my mouth, pausing to run my tongue down the underside of his shaft and around his balls, I felt Josh's hand on my head. He dug his fingers into my hair, then slid his hand down my back. The feel of his hand against my skin was amazing. His firm touch, massaging the small of my back, encouraging me as I pleased him. I almost didn't notice -- and I certainly didn't protest -- when he sent his reach further down, over the curve of my ass.

He gripped one of my meaty ass cheeks firmly, the tips of his fingers pressing just inside my ass crack. Then he slapped me, hard. The sudden pain surprised me and I yelped around his cock. I think he felt alarmed because he pulled his hand off my ass. But, when I wiggled my ass for him, it returned. This time he ran his fingers straight through my ass crack, a roving pressure against my asshole beneath the lace thong.

He did this several times, seeming to probe a little further each time, wiggling his index finger under the thong strap and finding my virgin hole. I responded by pressing my ass back against his touch, begging him to explore further. I pulled his cock from my mouth.

"Give me your finger," I said.

He put his hand to my face and I sank his middle finger into my mouth, sucking it like it was his cock, getting it soaking wet with my own spit. When I'd done a good job, I removed his finger from my mouth and replaced it with his cock, rolling my tongue around his now purple head and sinking it into my throat as far as my then un-trained gag reflex would allow.

I felt his wet hand reach to my ass, his finger soaked with my own saliva under the strap of the thong. When the tip of his finger reached my hole, he paused, and pressed gently but steadily until his fingertip was inside me.

It was my turn to moan this time, and I took to his cock with a voraciousness. I wanted to please him so badly. I wanted to please him like his finger inside me was pleasing me. I tightened my lips around his shaft and sucked long and fast.

"God yes," he moaned breathlessly. "I'm going to cum if you keep going."

I kept going. His hand firmed up between my ass cheeks. He pushed his finger deeper into me, as far as it will go, probing parts of me that had never been probed. The pressure was intense, painful but in a delightful way. He backed his finger out and again sank it in.

"Fuck yes," I moaned as I stroked his cock.

He fucked my ass with his finger as I stroked him, watching his throbbing, impossibly purple cock head. I worked my hips, backing myself as far as I could into his probing hand, feeling his finger deep inside me until...

I came. Not just my cock but my entire body throbbing, seizing, tingling electric. I felt myself ooze into the lace panties, and in my heat I plunged his cock back into my mouth. As deep as I could gagging as I rammed it into my throat.

"Oh, god, yes...." Josh let out just before his body stiffened, his free hand gripped the back of my skull and his cock spasmed and gushed heaps of thick, salty cum into my mouth. I tried my best not to choke on it, letting his cock pulse into my mouth until it was full, then swallowing, and collecting more. I managed to swallow most but not all his juice, and felt some drip down his shaft where it was slimy sticky on my hand.

When he was done pulsing his body relaxed and his cock started to soften in my mouth. I used my tongue to lick clean his cock, balls, and pubic hair, then slid his shorts back up his legs.