Through the Eyes of Evelyn

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A transwoman and a man swap bodies for an evening.
10.4k words
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The woman sitting parallel to me at the bar wore a short, black dress suspended from her shoulders via two spaghetti straps. It's matte-black fabric clung tightly to her waist, below which it gradually loosened, elegantly curving outward at her hips, seductively concealing her pale, silken thighs, which vanished provocatively beneath its ruffled folds. She had a striking figure--tall and slender--though her outfit did a good job accentuating what little curves she did posses. Two petite, yet jaunty tits hung from her chest like teardrops, gently rippling the fabric of her dress. She turned towards me, tossing her long, auburn hair to one side and delicately tucking the remaining loose strands behind her ear. I could see that she had a strong jawline, and sunken hollow cheeks. Her stunning face was punctuated by two warm, caramel eyes, which seemed to glow in the dim light. Flecks of gold danced in her irises as she flashed me a grin.

"You gonna come talk to me, or are you just going to stare?" She said, cutting the tension suspended between us. My heart leapt in my chest. I hadn't expected her to sound like that. Her voice wasn't exactly deep, but it had a certain husky texture. It certainly wasn't the light, airy voice of a woman in her late 20s. Nevertheless, her slick, velvety words settled in my mind like a warm blanket. I felt inexplicably drawn to her. Returning her smile, I clutched my drink and slid closer.

"I'm Evelyn." She said, extending her hand.

"Mike." I said, taking it. Her hand felt small and delicate in mine. She was soft and warm to the touch, and her creamy skin exuded a faint floral scent that gave me butterflies in my stomach.

"So where are you from, Evelyn?" I asked, releasing her hand after holding her for what was probably a second too long.

"Virginia, originally." She said, lifting her glass and taking a small sip of the dark liquid it contained.

"Ah. Makes sense. So what compelled you to move out here?"

"Family."

"So you've got family here?"

"Nope. I've got family there. That's why I'm here."

Evelyn lifted her glass again, tossing her head back and swallowing the remainder of her drink.

"Amen to that." I said, flagging down the bartender to get as another round.

The two of us made small talk for a while, joking about work, friends and commiserating about how shitty our lives had been lately. Evelyn seemed to get a real kick out of hearing about my ex-girlfriend, who was the reason I was sitting at a bar drinking alone in the first place. As the two of us warmed up to one another, I found that I couldn't take my eyes off her. Everything about her, from the intoxicating timbre of voice, to the slight shifting of her long thighs captivated me. There was just... something about her. Eventually Evelyn caught on to my subconscious fixation with her.

"Mike... there's something I should tell you."

She said, blushing a little as she lowered her eyes to the counter.

"What is it Evelyn?"

"I'm trans."

"Oh. Wow. Really?" I said, trying not to sound stunned as all the puzzle pieces I'd been collecting over the course of the evening collapsed into place.

"Huh. Isn't that something?" I said with a warm smile, gazing at Evelyn until she lifted her eyes, meeting mine.

"Does that... bother you?" She said tentatively, seemingly encouraged by my supportive expression.

"No, not at all."

We stared at each other silently for a few moments, before bursting out laughing, both relived that we'd managed to surpass this awkward pause. As Evelyn's chest rose and fell, I could just barely see the faint outline of an Adam's apple protruding from the base of her throat. I felt a powerful sense of curiosity become ignited within me as I admired the woman laughing before me.

"You know, I've never actually met a transgender person before."

"Really? Well now you have."

"If you don't mind me asking, what's it like?"

"Being trans?"

"Yeah."

"Well, it's just normal for me I guess. I feel like I'm in the body I belong in. I live just like any other woman, and that's what matters. I'm who I was meant to be."

"Huh. That's really great, Evelyn. I'm happy for you."

"Thanks Mike" Evelyn chuckled, probably amused by my sudden, zealous support for her. She went on:

"You know I don't regret it for a second, but there's a part of me that wishes I could go back to being a male for a day. I think it would be interesting to see the world through the eyes of someone like you, after everything I've learned and experienced..."

"Really?"

"Yeah, there's a lot of people I'd like to meet again. I've always wondered how their perception of me would change if I wasn't trans. Especially my family..."

Our conversation shifted, taking a darker turn. Evelyn told me about what her life was like growing up as a closeted transwoman. She told me about the personal turmoil she'd faced, being disowned by her family. She tried to smile through the pain, but could see a hint of sadness in her eyes. One of her hands rested idly on the countertop, the other cupping her drink, which she was staring into wistfully.

"I'm so sorry you had to go through that Evelyn."

I reached out and gently set my hand down on top of hers. I could feel her trembling slightly under my fingertips.

"I wish more people knew what life was like for transwomen. I think there's a lot of people like me who could really benefit from walking in your shoes for a while."

"Me too Mike..." she said, slowly shaking her head.

We stayed like this for a moment, until the soft clink of two glasses being set on the counter snapped us out of our introspective episode. I yanked my hand back, and we both looked up in unison at the bartender.

"Sorry you two, but we're closing soon. This last rounds on the house though" she said with an opaque grin, winking and gesturing to two shots she'd laid out on the counter in front of us.

"Oh, uhh thanks." I said, each of us grabbing a glass as she disappeared into the back. I looked up at Evelyn, who was back staring at me with an expression that I couldn't quite read.

"Cheers?" I said.

"Cheers." She responded with a smile, raising her glass to me.

I closed my eyes and raised the glass to my lips, swallowing the shot in one large gulp.

I expected it to burn my esophagus, but to my surprise had an unusual, sweet taste that reminded me of Evelyn's floral aroma. It tickled my throat, fizzing and bubbling, imbuing every crevice of my core with a relaxing, ephemeral fuzziness. I cringed as the liquid hit my stomach, causing my gut to lurch as a small wave of nausea washed over me. I closed my eyes and took a deep breath to steady myself.

Opening my eyes, I turned and set the glass down in the counter. I caught a glimpse of Evelyn's form moving in my periphery. She looked different. Larger?

I turned towards her and gasped at the sight I was met with.

I knew it shouldn't have been possible, but there I was. A mirror image of my own body, sitting on the stool next to me, mouth agape in shock.

I leaned back in horror, and my body did not move with me. That wasn't a reflection. It couldn't be. I... I... was outside my body.

"Mike?" My body choked at me.

"Evelyn?" I responded, in a voice that clearly wasn't mine.

"Is that...you..."

"Did we???"

I held my breath to stop myself from screaming.

I lifted my arms out in front of me, splaying my perfectly manicured fingers. My skin was pale and smooth, almost like porcelain. My fingernails were painted black. I turned my hands over, watching as the delicate pair of arms tracked my every movement.

I slowly looked down and long, auburn hair tumbled over my bare shoulders, crowding my vision. I pushed a few strands aside, revealing a tantalizing firsthand glimpse of the narrow valley between Evelyn's cleavage. I eased my shoulders backwards a bit, feeling Evelyn's bra straps dig into my back as the lacy cups squeezed my fleshy mounds and her dress pulled taut across my bosom. This drew my attention past "my" tits, where I saw that I was now the one wearing Evelyn's tight black dress. I raked my fingers down my ribcage, feeling the soft material tickling my fingertips. Having worn a dress before, it was an unusual sensation. I felt overly constricted above the waist, where the skin-tight dress adhered tightly to my hips, highlighting the distressingly feminine contour of my body. Below the waist, I felt overly liberated, as my smooth, shaven legs shifted freely beneath my skirt.

An experimental twitch of a certain organ confirmed a question that I'd had but been too afraid to ask. Evelyn did, in fact, have a penis. I uncrossed my long legs, feeling the soft, silky panties I was wearing stretch taut against the crown of Evelyn's flaccid cock. The hairs on the back of my neck stood up, signaling that I was actually enjoying the sensation. I turned back towards Evelyn, shrugging as my long, flowing hair tickled my neck and shoulders. Evelyn was bent across the bar, holding her empty cup up to the light as she ogled at her reflection in the glass. Judging by the look on my, or rather, her, face, she was as freaked out as I was.

"Evelyn. Hey. Eveyln!" I whispered urgently, clearing my throat as I adjusted to hearing her girly voice leave my lips.

"Huh? Oh. Yeah?" Evelyn responded, quickly placing the glass back on the bar and turning to face me directly. She put her hands on her thighs, and leaned in close. My body looked gigantic from this angle, even in the larger-than-average female body I inhabited.

"What the fuck happened? Did you do this???"

"Absolutely not!" She reassured me in her booming, masculine voice. A few of the remaining patrons had caught on to our unusual behavior and were beginning to give us strange looks. I looked around anxiously, feeling as though their collective gaze was burning a hole in my new outfit.

"Let's just... can we go somewhere private?" I asked, blushing profusely.

"Yeah... of course Mike."

As we stood up, Evelyn grabbed me by the hand, helping me to my feet. I wobbled like a newborn deer as I stood up in heels for the first time, gripping her firm shoulder for support.

"Thanks..." I said, blushing an even deeper shade of red as she reluctantly released me. My hand had felt so tiny inside her palms.

The two of us walked briskly to the bathroom, slinking inside as we shut and locked the door. Thankfully the bathrooms were singles.

"Holy shit." Evelyn exclaimed as the two of us approached the mirror.

"This is unreal."

"You're telling me." I responded, gently probing my face with my fingertips. Evelyn's high cheekbones and strong jawline had become my own. I had her face.

"I...I look like... you..."

"Well technically you are me." Evelyn said, turning towards me to examine her old body.

"Let me get a look."

Evelyn paced around me, slowly examining every inch of my--her--body from her new perspective. I stood there awkwardly, feeling her masculine gaze roaming my slight curves. "So this is what it, feels like to be checked out, huh?" I thought to myself.

When she finished her lap, Evelyn stood proudly before me, with a dumb grin on her face. Did I always look that stupid?

"You know I always worried that I didn't pass super well, but seeing myself from this angle... it's..." She paused, her gaze lingering on my bosom.

"It's just... I look..."

"Beautiful?" I said with a sly grin, feeling weirdly pleased by her compliment. Evelyn let out a long sigh in agreement.

"Seeing how feminine my body looks, it just makes me feel..." Evelyn closed her eyes, her hand brushed against her crotch. "God I forgot what it feels like to be so... big..." Her fingertips danced dangerously across the faint outline of my bulge, which was gradually expanding between her legs.

"Woah... Evelyn... are you getting turned on by this?" I laughed awkwardly, trying to suppress my own, sudden, rising desires.

As I watched Evelyn's stiffening prick tent my pants, I felt my own sex begin to stir between my legs. I squirmed a little as I felt my cock straining against my panties as it filled with blood.

"Looks like it's not just me." Evelyn grinned, gesturing to my crotch.

I looked down, and sure enough a thumb-sized imprint had appeared, jutting provocatively through the thin fabric of my dress.

Harboring someone else's erection is a truly bizarre experience. Everything about it was so... intimate. "Holy shit Evelyn." I whispered as I felt her penis throb a little. My body felt warm all over. My face was flushed and a dull, erotic ache had begun to manifest in my tender chest, which heaved with each ragged breath as my heartbeat quickened. My body felt so alien. Every inch of me was hypersensitive, as if I was burning up.

Evelyn instantly detected my arousal. I watched her volatile gaze flicker rapidly between my eyes and my crotch, as two of us grew hornier and hornier. I could sense a certain hunger in her eyes that both scared and exhilarated me. She was openly massaging my bulge through her pants now.

"Do you mind if I check this thing out?" She said, squeezing her bulge.

"I. Oh. Uhhh..."

Evelyn didn't wait for my response. She started to unbuckle my pants as she drifted towards me, positioning herself so that we were both visible in the mirror.

I held my breath as she fumbled around in my underwear for a moment, before tugging upwards aggressively. My former cock sprang free, long and beautiful and curving upward. The big veins on the stalk traced deep shadows along its length under the dim light. When she slid both her large hands along it, the shaft pulsed, growing even bigger. "My god I forgot what that...that... felt like..." she panted, slowly stroking my cock until its length glistened with precum.

Pleasure rippled through my lower abdomen as I squeezed my thighs together, my hands finding their way to my new crotch. I slowly dragged my fingertips across the front of my dress, bucking my hips in response to the pleasurable jolt I felt as they crossed the ridge of my straining, upturned bulge. Soon I was swirling my index and middle finger around the protruding nub of my mushroom-shaped head, panting as I instinctively rubbed my new penis as though it were an actual clit.

As Evelyn became aware of what I was doing, she slowed her stroking, looking at me with a mischievous grin.

"Do you mind if I take a look?" She asked, gesturing towards my cute little boner. My heart was pounding. I bit my lower lip and nodded.

Evelyn slipped her hands into the folds of my dress, hooking her index fingers into the waistband of my panties. Then, in one smooth motion, she pushed them down, past my hips and let them fall to the floor. I stepped out of them, timidly clutching the hem of my dress and slowly pulling it upwards to reveal my new, feminized equipment. The heat of my cock met the coolness of damp bathroom, soothing the numbing ache that had swollen my meat to full mast. I glanced down.

No longer supported by Evelyn's tight underwear, my erection hung limply between my legs, nestled cozily between two drooping balls like an upside-down heart. Her testicles were shrunken, not much larger than marbles, and her shaft was thin and wormy. It couldn't have been longer than four inches. I took my new organ in my hand, gently squeezing it as I winced. In response, my sack tightened with an airy lightness, though my balls felt the ache. "Fuck it's so sensitive." I groaned as Evelyn and I stood side by side in the mirror, examining our new penises.

Even fully erect, my cock felt semi-soft and gummy as I rolled it around in my fingers, tugging on its length. Evelyn watched carefully as I played with it.

"It's the estrogen." She said suddenly, commanding my attention. "That, and the androgen blockers. It causes the male genitals to atrophy. It's why your... err... MY... penis is so small." She gestured towards my crotch.

A warm, bubbly feeling welled up inside my chest, manifesting itself in a gentle smile, as I realized how vulnerable the moment we were sharing was. We were quite literally, stripped bare, analyzing each other through the eyes of a stranger.

"I like it." I said, winking at Evelyn. "It suits your female body."

Evelyn beamed, and another moment of extreme, longing silence hung between us, extending just long enough for our shared desire to bind us to a mutual agreement.

"Can I?"

I nodded.

With that, Evelyn released her inhibition by leaning close, grabbing my face, and bringing it to her mouth. Her tongue assertively pushed its way between my lips, which I was unprepared for, and actually jumped a little. She pulled back and laughed heartily. I can't explain why, but her sudden confidence was incredibly hot and sexy.

"Sorry Mike. Too much?"

"Not at all." I retorted, feeling my competitive side rear its head.

I pulled her back into a kiss and this time I was prepared for it. Both of our tongues met. It was glorious, as I slowly swirled my tongue around, touching and tasting the insides of my former mouth. Evelyn sucked on my tongue and then forced her tongue into my mouth again. She was an amazing kisser and the taste of her mouth was slightly sweet from the shot we'd taken. The fact that I was kissing my own body, a male body, made the whole situation all the more erotic and I realized that I wanted more.

My hands found the bottom of her shirt and hiked it up over her head, exposing her flat, toned chestt. In turn, Evelyn grabbed the fabric around my waist and lifted my dress of me. After I managed to shimmy out of it, she reached around my back and popped the clasp of my bra. I instinctively shrugged the straps off and I tossed the bra on top of her shirt on the floor. I stopped for a moment to admire my topless body in the mirror. My breasts were small but fleshy, with a slightly conical shape. I shuddered as I squeezed the puffy, agitated mounds together. Fuck that felt good.

Evelyn spun me around, my modest breasts rising and falling while I backed up against the sink. She took each puffy nipple in her mouth and teased it, making me gasp in pleasure. I could tell that they weren't implants. Evelyn must have grown real breast tissue with some sort of hormone treatment. She kneaded my tits with her lips, slowly tracing circles around areolas with her tongue until she gently bit down, grinding a nipple between her molars. My knees nearly gave out as I squealed in her chesty voice. She kissed her way down my belly, teasing my navel with her tongue on the way, and then stopped to admire what was between my legs.

"Mike... can I touch you here?" She asked gently.

"Seeing my body from this perspective... my penis looks like the cutest little clit. I just love how feminine it makes my body look..." She placed a soft kiss on my pubic bone, just above it, and I shuddered slightly in pleasure.

In a barely audible voice, I whispered: "Yes."

Evelyn took my semi-rigid clitty in her fingers, massaging it gently. My cock thickened. The swelling was so tangible that I felt every blood vessel in my shaft expand until my chubby girlmeat throbbed from root to tip.

"Do you like me rubbing your clit? Do you want me to keep going?"

"Yes." My eyes were now closed and my fingers gripped the sides of the sink. Evelyn knelt before me, prompting me to arch my back, flexing my hips towards her. I was shaking steadily now, my pale skin flushed with excitement.

She continued to fondle me, slowly stroking my velvety hardness. I was loving how trusting she was.

"This pretty little thing of yours looks so tasty, I'm going to take in my mouth, unless you want me to stop," She teased,

"is that you want?"

My eyes still closed, I shook my head and vehemently pleaded, "NO. No, don't stop."

That was her cue; Evelyn kissed her way from my pubic bone up the brief length of my quivering hardness until she reached the tip. Once there, she opened my mouth and took it all in--it didn't even hit the back of her throat--then she moved her tongue back and forth along the underside. She started off slowly, using her lips to shield my little clitty from her teeth. Having had a blowjob before, the back and forth moment of smooth lips on my organ was familiar, but everything else was different. My new penis was smaller, more sensitive, and it pulsed with deep, aching throbs that were unlike anything my former penis used to produce. It felt like a bundle of exposed nerves.