I’d just finished showering, running my fingers down my clean-shaven body, and enjoying the silky feel of soft skin on my smooth legs. I always felt incredibly feminine after a shower, pampering myself with creamy lotions and sweet-smelling perfumes.
I’d already laid out what I intended to wear, sitting down on the bed excitedly and reaching for the sheer black stockings. Rolling them up with my fingers one at a time, curling my toes inside and trembling as the nylon material slid up over my velvety smooth legs.
I shivered with titillation, looking down and admiring my long slender legs, gorgeously wrapped inside the sexy stockings. I’d always felt a deep appreciation for ladies’ lingerie and such an intense devotion to the transformation process.
Next to me was a large full-length mirror that faced the bed, allowing me to admire my reflection while I adorned the shiny black padded bra, luxurious garter belt, and matching micro-bikini style thong.
Glancing back in the mirror I twirled and swayed flirtatiously. Enjoying the overwhelming sense of gratification. My body looked much more feminine now but there was still much to do. I thought, waltzing across the room and sitting down in front of the vanity mirror to apply some make-up and don my gorgeously long black curly wig.
After touching up my make-up to accentuate my delicate features, I tiptoed back across the room, relishing in my transformation. As I moved, my long hair swayed across my shoulders, making me feel especially girlish and dainty. The gold satin ruched bodycon dress laid neatly on the bed, shimmered in the light, enticing me with its lascivious look.
Carefully, I picked up the dress, slipping it on and zipping it closed behind my back, feeling it stretch around my slender frame. I reached obsessively for my strappy gold pump high heels, sliding my feet inside joyously, then quickly standing up and teetered over to the full-length mirror.
My eyes widened, my body tingled with eroticism as I twirled and flirted with my reflection. I gazed lustfully at the pretty girl staring back at me in the mirror. Sexiness radiated from her as she danced and swayed seductively, rubbing her hands over her body.
The phone vibrated on the bedside table breaking my concentration for a moment as I hurriedly reached over to read the message.
Hey babydoll, just waiting for my Uber now. See you soon hun. Cheyanne xxx
I felt a nervousness creep across me, sending shivers down my neck and along my spine, increasing the sensitivity around my body. Cheyanne was my bestest friend in the world. We’d met a few years ago online, and she was the first person I’d opened up to about my crossdressing. She was also the first trans-girl I ever met in person and was the reason I had begun to adventure outside of my comfort zone.
There was something about going out dressed en femme that both excited and worried me simultaneously. I continued getting ready, picking up my cute little gold mini shoulder bag before heading out to the door, albeit somewhat anxiously.
By the time I reached the club, my nervous energy was almost paralyzing. I could feel peoples’ eyes on me as I stepped towards the entrance, passing the leering bouncer on my way through the door.
Once inside, I tottered past the dimly lit bar, desperately searching for Cheyanne. My heart fluttered nervously in my chest as the loud music echoed around the building, bouncing off the walls and sending vibrations through my body.
“Hey, babydoll!”
I heard a shrill voice screaming at me from across the room, turning to watch as Cheyanne strutted confidently towards me in her thigh-high-heeled boots.
I gazed at her gorgeous figure, swathed by the slinky off-the-shoulder split mini dress that clung tightly to her skinny frame. It was as if the room parted for her. Creating a perfect divide, her body moved in slow motion as she approached, diving into my arms and embracing me tightly.
“God, you look so gorgeous babydoll!” She screamed in my ear.
Without hesitation, she grabbed my hand, leading me over to the dancefloor, confidently strutting and moving her body in time with the music, encouraging me to follow her lead.
Cautiously, I started to sway and move my body effeminately, building my confidence and slowly letting go of my inhibitions. Our frolicking began to attract attention from a group of nearby drunken men.
One of them pushed into me from behind, shouting in my ear and placing his hands lightly on my hips.
“Hey, sexy! Wanna dance?”
I moved away apprehensively, trying to create some distance between us. Cheyanne quickly took control of the situation, confronting the guy and stepping in to warn him about his behavior.
In truth, I loved the attention. The way it made guys act around me when I dressed like this, and the sense of power it gave me, knowing how turned on it made them.
We continued to dance uninterrupted, our bodies pressing together, gently moving in time with the music. As she moved closer the smell of her perfume engulfed me, turning me on as we swayed in the darkness.
Time seemed to melt away and before long, Cheyanne reached for my hand, escorting me back towards the bar area for a drink. It was quieter here, which made it a little easier to talk. Cheyanne found an open table by the end of the bar and sat down next to me, leaning in to talk.
“I’m serious, babydoll. You look so pretty tonight. I can’t keep my eyes off you.”
My face turned bright red, blushing with embarrassment. She knew exactly how to get me flustered, her hand resting on my knee and gently smoothing her fingers over my stocking tops.
Cheyanne was herself, incredibly gorgeous. She benefitted from being dual ethnicity, her father reigning from Scotland, and her mother Malaysia. Which made a compliment from her seem all the more flattering.
“What would you like to do after this?” She asked inquisitively.
I looked at her timidly, knowing the answer to her question, but not feeling intrepid enough to answer her honestly.
“I don’t mind. Whatever you want to do?”
She looked deep into my eyes, a sparkle of naughtiness twinkling in her pupils, “mmm, whatever I want huh?” She smiled wickedly.
Her subtlety wasn’t lost and I knew exactly what she meant. Cheyanne had been with guys before and was quite open about her bisexuality. On the other hand, I was still a bi-virgin and incredibly vanilla in the grand scheme of things.
I’d been with several girls in the past, prior to embracing my crossdressing, but not in female form, and never with anyone from the same sex. The thought intrigued me and I kept finding myself wondering what if?
While we were talking, an opportunistic, and conventionally handsome guy approached our table. Cheyanne continued to rub her fingernails along my stockings, looking up and smiling at him.
He looked down his chest sheepishly, “sorry, but I just have to ask. Would it be OK if I joined you?”
Cheyanne glanced over at me, trying to gauge my response. I shrugged reluctantly.
“I guess”, she replied, motioning for him to sit down.
She was acting coy but her body language said otherwise, arching her back and leaning flirtatiously towards him while she played with her hair.
He seated himself and made some introductions, “I’m Marcus by the way.”
“Cheyanne, this is Mimi.” She replied, pointing at me.
As he started to talk, it became obvious that he was interested in getting to know Cheyanne more intimately and his bravado just oozed out while he spoke. Making it crystal clear what his intentions were.
I remained timid, quietly sipping on my drink and leaning in closer to Cheyanne for protection while the two of them talked.
It always made me feel self-conscious, being around men while dressed as a girl. Cheyanne didn’t care at all. She would often flirt with guys, teasing and toying with them, making them lust for her until they were bursting for more.
Marcus shifted forward, leaning in closer to Cheyanne, then whispered something into her ear that I couldn’t quite make out. She bit her lip in response, her expression changing dramatically.
There was a look of lust wavering over her face and she giggled bashfully, clutching my thigh tightly as she wiggled in her seat. Marcus said nothing. He just smiled back at her, reaching down under the table, taking her hand, and sliding it between his legs.
The situation made me feel super uncomfortable, shifting back in my chair and trying to look away as Cheyanne began stroking his cock from underneath the table.
I looked down, noticing his hard cock throbbing between her tiny fingers, mesmerized by the sight of it. I looked away, repulsed by how attracted I was in the presence of a real cock. Shifting uncomfortably, then quickly standing up, and walking away from the table.
Cheyanne immediately followed, grabbing my arm and stopping me.
“Hey babydoll, are you ok?”
I looked back at her sorrowfully with watery eyes. My heart filled with jealously, my head all dizzy and confused. I couldn’t process my feelings.
“I just want to go home”, I replied, my voice cracking with emotion.
“OK, let’s go then.”
She grabbed my hand and comforted me as we exited the club. I could see Marcus staring at me while we walked away, a wicked look of envy in his eyes.
Once outside, Cheyanne quickly escorted me away from the busy entrance and accompanied me into a quiet side street.
“What’s wrong, babydoll?”
“Nothing.”
She pulled me closer, wrapping her arms around me, her beautiful brown eyes locking with mine, her soft lips just inches away.
“It doesn’t look like nothing. Why don’t we go back to my place and we can talk about it together? Just the two of us.”
I looked up, a flicker of hope and optimism came rushing through me, nodding eagerly in agreement. A warm and comforting smile lit up her face. Cheyanne quickly pulled out her phone and ordered an Uber.
Within an hour, we had arrived at her apartment and sat down together on the couch. She opened a bottle of wine, poured us both a glass, and curled up next to me.
“Feeling better now hun?”
“Yes, thank you.”
Our glasses clinked and we spent the next hour or so just sipping wine and chatting. We talked about our favorite clothing, films, music, and make-up techniques, and before long I’d almost completely forgotten about being upset.
After several more glasses of wine, Cheyanne, slightly tipsy now, leaned over with a sincere but inquisitive look on her face.
“Can I ask you something? When you’re all dressed up and girly, do you ever think about boys?”
Her question stunned me into silence. Not knowing how to respond. Cheyanne quickly picked up on my insecurity, interrupting the awkward silence.
“Because I do. I can’t help it. I just start thinking about cock and it makes me so horny for it. Haven’t you ever wondered about that?”
She reached down, casually rubbing her fingers up my stockings and along my thigh, causing my penis to throb tenderly inside my thong. Cheyanne noticed the small bulge appearing under my dress, smiling widely and shifting her glance back up at me.
“Do you know what I mean?” She asked, waiting patiently in anticipation.
The truth was, I had thought about it, on numerous occasions. It was something I’d been struggling with for years and I still wasn’t sure how I felt about it. After a short silence, I finally replied.
“I’m not sure?”
Cheyanne stared deeply into my eyes, completely motionless. Just peering into my soul as we both continued to sit in silence. After what felt like an eternity, she slowly leaned forward, pressing her soft lips against mine.
I instinctively kissed her back, deep on the mouth, my tongue slithering against hers, tasting her lipstick as we passionately french kissed for several seconds.
Suddenly I pulled away, reluctantly.
“I’m not gay!” I professed, petrified of my true feelings that I’d been suppressing for all this time.
“Oh babydoll, you’re so confused aren’t you? I know how hard it is to accept it, but trust me, you’ll feel so much better when you finally do.”
“But, I don’t like boys! I’m not like that.”
“Then why are you so turned on baby?” She replied, pointing down at the erection protruding through my satin dress.
“I don’t know”, I cried out, sinking onto her shoulder and beginning to accept the truth as my internal dialogue raced to confess inside my head.
‘I do like cock, especially girly cock, and I can’t stop thinking about it! What it would be like to try it for the first time. To allow her to penetrate me, to suck and fuck me while dressed as a girl. Maybe I am gay or maybe I just love cock. I’m so confused!’
Cheyanne stroked my head tenderly, brushing the hair out of my face, and comforting me as I sobbed pathetically in her arms. After a few moments, she lifted my head, grabbing my hand and helping me back onto my feet.
“Come with me. Everything is going to be OK, I promise.”
I followed sheepishly behind, holding her hand like a lost child, allowing her to lead me into her bedroom. She gently guided me onto the bed, then began lighting candles around the room, improving the ambiance and making it feel all warm and cosey.
I watched in awe as she began seductively removing her dress, allowing it to drape off her body and fall onto the floor. Revealing her sexy corset and stocking combo. Her tiny penis was tucked safely away, hidden inside the silk panty-thong.
The small bulge under my dress began to throb in excitement as a thousand naughty thoughts ran rampantly through my mind.
‘Oh my god, just look at her. I can’t believe how sexy she is with those dainty legs, that slender waist, those curvaceous hips, and delicate soft features. She’s so much hotter than any girl I’ve ever been with!’
Cheyanne ran her hands down over her corset, sliding her fingers inside her thong and pulling gently at the thin side straps.
“Do you want to see it?” She asked, teasingly.
I nodded back, too lovestruck to speak.
“Not yet babydoll. First, I want to see what sexy lingerie you’re wearing underneath that stunning dress.” She said, pointing down at my body, and motioning for me to undress.
I stood up in my heels and reached around my back. Cheyanne moved closer, assisting me with the zipper, and helping to remove the dress, watching as it slid off easily exposing my lingerie.
Her mouth opened and her eyes lit up at the sight of my slender body, wrapped up gorgeously in the padded bra, garter, stockings, and micro-bikini thong. My tiny erection throbbed uncontrollably inside my panties, the shape clearly visible through the delicate material.
“God, you’re sexy babydoll. You have the most amazing body. Seriously! Look at those sexy legs and delicious bum.”
I looked back over my shoulder emphatically. Closing my eyes and parting my lips flirtatiously, eagerly hoping for her to kiss me again and trembling blissfully when she did.
Our tongues lashed at one another lustfully. Her hands explored my body, rubbing her fingers over my soft skin, and sending waves of euphoria all over me.
My cock grew harder inside my thong, poking out the silk material, making the elastic stretch around my waist. Cheyanne guided me back onto the bed, kissing me once more passionately on the lips, then stepped back, clutching the sides of her panties.
I watched thirstily as her fingers slipped inside the side straps again, slowly sliding down her panties and exposing her tiny she-cock. Time stopped, my eyes dilated, watching intensely as it dangled freely just inches in front of me.
Cheyanne stood confidently, her hands on her hips, posing in her thigh-high boots, corset, and stockings. She exuberated self-confidence, standing proudly, so self-assured as she admired herself, looking down at her sexy body.
“So, what do you think, do you like what you see?” She said teasingly.
“You look beautiful Cheyanne. So incredibly beautiful.”
Her expressions softened and for the first time since we met, she blushed.
“Thank you, sweetie.”
I watched tentatively as she approached me, my focus fixating on her tiny soft penis, dangling between her legs while she walked. I shifted over, making some space on the bed, and stared gingerly at her as she sat down next to me.
“What should we do now then?” She giggled, jovially.
I looked up nervously, staring into her alluring oriental-shaped eyes, enamored by her stunning beauty and angelic energy.
“Whatever you like.”
She let out a long and raunchy high-pitched woo, that let me know just how naughty the thoughts inside her head were.
“Anything?” She said, crossing her arms and tapping a finger on her chin. “Well then, how about you show me yours? I mean, you’ve seen mine now haven’t you.”
“OK”, I replied, anxiously reaching for my thong and sliding it down slowly over my thighs, watching as my cock popped out and stood to attention.
“Mmm, such a pretty looking clitty. May I give it a little kiss babydoll?”
I nodded. Watching attentively as she slowly bent down between my legs. Running her tongue up my thigh, and staring up at me intensely. My body shuddered uncontrollably.
“Does that feel good?”
I nodded again, more quickly, eager to show her my admiration and gratitude.
She flicked her tongue gently along the side of my penis, making me tremble with pleasure. My whole body began to shake nervously while she licked the tip of my cock, rolling her tongue around the head tenderly.
“Oh, Cheyanne!” I cried out. My moans increased as she caressed my balls, sliding her tongue over my penis affectionately. She sank quickly, swallowing my penis entirely and sending an overwhelming sensation throughout my body.
I looked down in wonderment. A haze of euphoric contentment washed over me as I watched this beautiful girl thirstily please me in ways I had never experienced before.
For several minutes, she caroused my penis with her tongue. Stroking and salivating while she worked to pleasure me with her soft lips.
I was about to come, pulling back abruptly.
Cheyanne looked up, bewildered. “What’s wrong?”
“Nothing, I just… I don’t want to come yet.”
Cheyanne placed her hands on my legs, gently lifting herself back up onto her heels, allowing her soft penis to dangle freely in front of my face. I opened my mouth, cupping her shaft with my hand, and leaned forward to try my first taste of cock.
Carefully, I poked out my tongue, guiding her inside my lips and exploring the texture of her delicate flaccid cock with my mouth. Surprisingly, there was no distinctive taste. Only the sensation and the amazing feeling of having a real cock in my mouth.
Cheyanne winced, “Careful with the teeth honey.”
It was obvious I was a novice. But after a little practice, she began to moan with pleasure. Offering encouragement as she instructed me further.
“Yes, like that, use some more tongue. That’s it babydoll, keep doing it just like that.”
Her words inspired me, driving me to deepthroat her cute little she-cock, swallowing all four inches of her tiny stiff clitty.
After a few more minutes, she pulled out slowly, her cock covered in my saliva, dripping as she moved back, wobbling in her high-heeled boots.
“Was that OK? I asked.
“Oh yes baby, that was lovely, but…” she paused. “I really want you inside me now.”
I nodded feverishly, my heart pounding with anticipation. I’d never done anal before, not even with a girl, and the arousal filled me with excitement.
Cheyanne grasped a small bottle of lubricant from the bedside table, then gently guided me back onto the bed. She squirted a large amount of lube into her hands, then began applying it generously to my stiff cock. Causing a tingling sensation that made me quiver all over.
“I want you so fucking badly!” She begged, climbing on top of me and positioning herself just inches above my throbbing cock, reaching down and guiding it gradually towards her pink hole.
I clung to her hips, enjoying the feeling of her boots rubbing against my stockings as my penis slowly entered her boy pussy.
“Oh, Cheyanne!” I moaned compassionately as my stiff cock slid inside her, feeling the incredible sensation of her ass tightening around my penis as I penetrated her.
She leaned forward kissing me deeply on the mouth, her eyes wide open, pressing her body against mine, our delicate lingerie rubbing together.
“Fuck me!” She pleaded. “Fuck me like a slut.”
I lifted my pelvis, gyrating my hips, and thrust into her determinedly, making her moan loudly. She arched her spine, leaning back and grabbing the tops of her boots, bouncing faster on top of me.
“That feels so fucking good”, I mumbled softly.
“Yes baby, keep fucking me like that!” She squealed, thrusting her groin towards my stomach and taking every inch of my five-and-a-half-inch cock deep inside her.
We continued in this position for a while, my hands exploring her body as she bounced on top of me, moaning girlishly and talking dirty while we fucked.
“You feel so fucking good inside me! Do you like my pussy baby? Mmm, your cock feels so good. Please! Fuck me harder. Yes, just like that!”
My body began convulsing and my balls clenched as I began to come hard and deep inside her. “Oh fuck, oh fuck!” I groaned loudly, while my body shuddered and shook, clenching her ass cheeks and filling her up with my hot sticky load.
I clung to her tightly, holding her body close as the last few squirts of come burst out of my cock, shooting inside her ass.
“Did you come, baby?”
I looked up at her, hazy-eyed and lovestruck, “yes, I couldn’t help it. You just felt so fucking good.”
“That’s alright babydoll. Is it OK if I come now?”
My eyes widened curiously, bemused by her question. I nodded assuredly. “Of course, I want to make you come too.”
“Roll over then sweetie”, she said, sliding off my cock and helping turn me over onto my front. She grabbed the bottle of lube. Slathering it between my ass cheeks and around my virgin hole. The cold liquid made me flinch as she applied a generous amount of lubricant onto my naked ass, positioning herself on top of me.
Her tiny stiff cock, slid between my legs and in between my cheeks, causing me to quiver.
“It’s alright babydoll, I’ll be gentle. I promise.”
With that, she eased the tip of her cock into my tiny tight hole, making me yelp softly into the duvet covers. Gradually, she slid the first few inches inside, penetrating me softly and taking my sissy virginity.
I felt so girly, letting her dominate me in this way. Her hips slid against my bare bum, slipping her cock quickly but gently into my virgin ass.
“I’ve wanted to fuck you for so long babydoll”, she confessed, grinding her body against my slippery ass, easing herself further inside me. “I can’t believe it’s actually happening!”
I closed my eyes, trying desperately to enjoy the new and bizarre sensation of being fucked in the ass by her tiny cock. Little by little, she slid further into my tight hole, until all 4 inches were fully inside me.
She began to grind faster, gripping my waist tightly as she fucked me from behind. My fingers clenched the duvet, and my body recoiled instinctively as her balls slapped against my ass, sliding her cock in harder with each thrust.
“Oh Mimi, your ass feels so good!” She screamed, pounding herself inside me and pinning me to the bed.
After several painful minutes, she screamed loudly, “I’m going to come! Please, baby, tell me to come!”
I lifted my head off the mattress, taking a deep breath, then howled loudly, “come for me, baby.”
“Say my name and tell me to come!”
“Please Cheyanne! Please, I want you to come for me.”
Her body quivered and her tiny cock trembled inside me, spilling load after load into my virgin hole.
I could feel her fingernails digging into my sides as she grunted and moaned behind me. Squirting out every last drop, deep into my ass, before finally flopping on top of me, no longer able to hold her weight.
We lay there together, exhausted, her penis gradually softening inside me before slipping out on its own accord.
Cheyanne rested her head on my shoulder and kissed my neck softly.
“Are you OK baby, how does it feel?” She asked sincerely.
“It feels a little sore, but it felt nice too.”
“That’s good. You’ll get used to it. It always hurts a little the first time.”
She carefully rolled over beside me on the bed, her leg draped over mine as she stared lovingly into my eyes.
“Would you like to try it again with me sometime?”
I looked back at her, feeling an overwhelming sense of love and gratitude. My body still trembling ecstatically.
“I think I’d like to try it again with you tonight!” I said, smiling widely and kissing her passionately on the lips.
