tagTransgender & CrossdressersLost in a Female's Pleasure Pt. 04

Lost in a Female's Pleasure Pt. 04


Synopsis: Damien had been looking forward to a relaxing weekend free from his abusive father, but things quickly take a downward turn when he's kidnapped and wakes up in a confusingly elegant room and learns that his life is about to change forever.

His first training session begins, and he finds himself consumed by unexpected pleasures.

Everyone in this story is over the age of 18. This story contains themes forced feminization, transsexuals and soft non-consensual acts. This story is a work of fantasy.


Chapter 4: Pleasure and Comfort

I stared up at Lain as she slid her hands through the sides of her panties and pulled them down, allowing her penis to spring forth in front of me. It was much larger than my own but not monstrous, maybe seven to nine inches long with a dark pink head and thick shaft. I'd only seen another penis in textbooks so having one directly in front of my face sent anxious shivers through my stomach and I tried to back away, but Selene's hands on my shoulders refused to let me move. A strong, musky scent emanated off the penis and mixed with the aroma of roses from Lain's body, making my head spin as arousal sparked through me.

Fuck! Why was I getting turned on by this? Was I gay? I didn't think so, and Lain wasn't a man anyway. Was that why I didn't find her penis disgusting? It wasn't a mans penis and the body connected to it was far from masculine. Her round hips, accentuated by the black garter belt, were definitely not the hips of a man, nor were her curved thighs covered in thigh-high stockings. Looking up I could see her heart-shaped face flushed with arousal and framed by her golden locks, which were streaming down her chest and resting in her large cleavage.

I shuddered and clutched at the sides of my skirt as the arousal coalescent in my stomach and sent pulses of desire through me. Agh! Why did she have to be so pretty? Things wouldn't be so confusing if she was less attractive, or actually a man. Maybe...

'Relax,' Selene gave my shoulders a gentle squeeze and pressed her lips against the back of my head, 'it's okay to be aroused, to get turned on by this.'

'I don't, uhm...' my voice shook into nothingness, unable to withstand the confusing mesh of emotions crawling through me.

She grabbed my wrist and led my hand towards Lain's penis, making me gasp and try to pull away, but it was pointless. She easily pressed my palm against Lain's thigh, on the sheer fabric of her stockings, and slowly moved it up. The feeling of a warm thigh underneath silky stockings was amazing and as I brushed my fingers against it Lain sighed and stared down at me with large, lust-filled eyes.

'They feel nice, don't they,' she said in a soft voice, 'I can't wait to see you in a pair of your own.'

I didn't reply, unable to think about anything other than how close my hand was to her penis. She and I both let out breath as Selene moved my hand past the stockings and along her skin. There was no hair on her body, not even on her testicles, so her skin was beautifully smooth. I ran my hands up to her hips, marveling at how nice it felt, and Lain's penis twitched just inches from my hand. I blinked and focused back on it, then squeaked as Selene pulled my hand towards it.

'W-wait a minute,' I tried to pull my hand away with more force than before but Selene's hand didn't move an inch, 'I don't wa-'

'Shh,' she increased her grip on my hand until it was almost painful, 'just let me guide you. It'll be okay.'

I didn't have any choice and let out a shaky breath, butterflies raging inside me. Oh god, I was about to touch a...a cock! Calling it a penis seemed way too clinical, too impersonal. It wasn't at all a fitting description for the pulsating thing in front of my face.

My fingers touched its thick shaft as shiver ran down my back, but I didn't try to pull away. The heat coming off of it was intense and I slowly wrapped my hand around its girth, surprised at how hard it was. It felt like I was grabby a fleshy steel pole! I forgot myself for a moment and stared to poke and squish it with both hands, fascinated. It was so much bigger than mine!

The head, the glans, was slightly larger than the shaft and when I ran my hands down its edges Lain let out a shuddering breath and grabbed the sides of my head, making me flinch and pull away.

'Don't stop,' she said in a husky tone, running her fingers through my hair, 'grab it with both hands and jerk it off.'

I swallowed and did as she said, slowly moving my hands back and forth along the shaft. A part of me wondered why I was doing this, why I wasn't recoiling in disgust and resisting, but a larger part was just captivated. I'd never in a million years thought a cock would feel nice in my hands, or that one would belong to such a beautiful woman. This wasn't bad, was it? I didn't think it was...

Lain let out soft moans as I continued to jerk her off and the head of her cock started to glisten, a clear liquid leaking from it. I slowed my hands and stared at it, wondering if she was on the verge of cumming.

'That's precum,' Selene ran her finger through it, 'it means you're doing a good job, baby. Here.'

She put her finger against my lips and my tongue reflectively licked it. A salty, bitter taste filled my mouth and to my surprise I recognized it from when Tegan kissed me last night, her mouth wet from my cum. I swallowed and then froze as I realized something.

I was in the exact same position she'd been last night, about to give someone a blowjob. I was dressed as a girl, kneeling at a woman's feet and jerking off her cock, preparing to suck on it. I wasn't the man in this situation, not dressed and acting like this. I...I was the...

Girl. I was the girl.

That thought sent confusing jolts of pleasure coursing through me and and I imagined how I must look to Lain, a little girl dressed in a revealing school uniform, her large blue eyes staring up at her from a pale face framed by blonde hair. A cold excitement consumed my stomach and I gasped as my penis grew harder than it'd ever been before. I became intently aware of my body, of how the skirt, bra and tight panties felt against my soft skin, and everything seemed to grow more sensitive. Looking down at my feminine body made my heart skip a beat and I let out a shuddering breath. Oh god, why was I so excited, so aroused by this?

I should be ashamed and disgusted but...it was so hard to think clearly...I couldn't get the image of how I looked to Lain out of my head and it made my stomach and groin almost ache with desire.

'Wow,' Selene said in a pleased tone and I moaned as she squeezed my thigh, 'you're rock-hard. You're really into this, aren't you?'

'I-I shouldn't be,' I said in a shaking voice.

'Why not?' she asked and I shook my head.

'I'm not...I'm not a girl, I shouldn't be doing this. It's not right.'

'You're thinking too much,' Lain breathed, 'if it feels good then just go with it.'


She caressed the sides of my head and I stared up into her beaming eyes, 'Don't fight it, sweetie. You're exactly where you should be.'

'Just let go,' Selene said and I shook my head again.


Lain cut me off by pulling my head against her cock and rubbing it against my lips. Lightning tore down my spine and I gasped, allowing her to push the head inside with a pleased groan. I spluttered and grabbed her hips as she slid further into me, her cock sliding along my tongue and filling my mouth. It pulsed and throbbed while I whimpered, feeling its warmth against the back of my throat. My tongue reflectively explored its thickness as Lain groaned again and another jolt of arousal ran through my stomach. She slowly pulled out, her cock dripping with my saliva, but as soon as I took a shuddering breath she shoved it back inside. The taste of her skin and precum permeated my mouth and I gagged, my eyes watering, but despite everything I felt myself becoming increasingly aroused.

I was a girl at the moment...I was sucking a cock like a girl...

I rubbed my legs together and increased my grip on Lain's hips as Selene slipped her hands under my shirt and began to caress my chest, squeezing my nipples and pushing her breasts against my back. I moaned and felt my mind start to become enveloped in a burning pleasure.

'There we go,' Lain said in a breathy tone and increased her hold on the sides of my head, 'this is what I was looking forward too. You're my perfect little sex doll, aren't you?'

I squeaked and spluttered as she moved her cock back and forth inside me, gagging each time it reached the back of my throat. It didn't fit in my mouth completely, only managing to get just over half of its length inside, but it felt like she'd push through the resistance soon and slide all the way down my throat. Her thrusts became more intense and the fear of choking overcame my arousal. Her cock was so thick that I could easily imagine it getting stuck in my throat and cutting off my airways. Oh god! Was that something Lain would let happen? I didn't want to find out!

I forced myself backwards, pushing against Lain's thighs to get the cock out of my mouth.

'W-wait,' I coughed, saliva falling down the sides of my mouth, 'I don't want to choke.'

'You won't choke,' she lessened her grip on my head and smiled at me, 'but...why don't we change positions?'

I rubbed a shaking hand across my mouth and watched through loose strands of my hair as she sat down on the couch, her legs spread so her cock was on full display. Her silken black dress fell on the shaft and dropped down her ass, framing her lower body so sexily that a strong pulse of desire pushed me forward a little, shoving away the fear.

'Come here,' she said in a seductive voice, running her hands down her thighs, 'I want to feel the inside of your mouth again.'

I crawled over and put my hands on her knees, looking up at her with wide, lust-filled eyes. She smiled and leaned forward to kiss me, her hair falling against my cheeks and making me shudder. The feel of her mouth against mine was familiar and I let her wrestle with my tongue, moaning at how erotic it was. I loved how small I felt when she kissed me, with her hands running along my shoulders and back. It...reminded me of when mum used to hug me, but in a...uh...uh...

Huh...that was a weird thing to think of...

'You're a joy to train,' Lain broke off the kiss and brushed my hair behind my ears, then tilted her head to the side, 'but...being with me is the easiest part of all this Do you think you'd be so agreeable if I was a man?'

'No,' I said with absolute certainty and she nodded, letting out a breath.

'Well, like I said before, you're a natural sub,' she patted my head, 'I don't think being with a man will be too painful for you.'

'I don't want to find out.' I said, my arousal starting to fade in the face of such an awful thought.

She laughed and grinned at me. 'You will, and you'll grow to love it just like all the girls here do.'

'Is that true?' I frowned. 'Does every girl you bring here end up happy?'

'I make sure that everyone I bring here is right for this life,' she nodded, 'it takes me a long time to decided, and I do a lot of research on them.'

'But you said you decided to take me as soon as you saw my picture,' I muttered and she laughed.

'That's true, I did,' her eyes shone as she kissed my forehead, 'but I had you monitored for months before bringing you here, just like I do with all the others. Despite how beautiful you are, if your personality wasn't so agreeable then I'd have sold you to another organization.'

My stomach jolted at that. 'Another organization? There's another place like this?'

'No,' her voice became heavy and she leaned back, her eyes not meeting my own, 'this is a unique place where only girls who'll accept this lifestyle belong. If I didn't think you'd fit in here, if your personality was too aggressive or violent then I'd have sent you to a business partner of mine who runs his own organization. He wouldn't treat you even half as well as I do here, and I can't imagine you'd survive for very long under his...care.'

I forced myself not to think about that. 'Have you had to sell any of the girls before?'

'Yes,' she gritted her teeth as her eyes narrowed, 'even I make mistakes sometimes.'

'Really? Why would you even-'

'Now isn't the time for this,' she said in a curt tone, 'you're really killing the mood, Lily.'

'O-oh, sorry,' I said and then blinked. Why was I sorry?

'Come on, let's get back to it,' Selene gently pushed me in the back before I could fully process everything Lain had just said, 'you're going to suck her cock now. Before, when she was standing, you didn't have any control over what was happening, but you will now. Take her cock in your mouth like the slut you are and and have it explode in your mouth.'

I twitched at that and frowned back at her, but she just gave me an encouraging smile and turned me back to face Lain, whose expression was once again full of lust. My eyes fell to her lap where her erect penis was rising between her pink thighs and my fading arousal ignited back to life. It was like being put under a spell and the entire conversation we'd just had burned in the fires of my desire.

I leaned up and forward to grasp Lain's cock, which was still wet from my mouth. As I tried to jerk it off like I had before though my hands slipped off and slapped me in the face, making Lain and Selene laugh. Agh!

'Your hands aren't going to be too useful now,' Selene said as I swore, 'use your mouth, babe.'

I shook my hands and then leaned forward more, feeling my skirt rise up against my thighs and reveal my panties. For a moment I considered trying to brush it back down, embarrassed, but decided it didn't matter and focused back on Lain's lap. An array of tantalizing scents emanated of of it, from the sexy aroma of her cock to the warm scent of roses coming off her body. I shuddered and licked my lips, then leaned down so that her cock was right in front of my face. It was so large...

After a moment I licked it, sliding my tongue along the shaft and up to glans. It was spongy and still wet with precum, the taste sending trickles of pleasure running through me. I shivered as the image of what I looked like kneeling in front of Lain etched itself into my head and warmth flowed down my back. It made me even more aroused and I moved my tongue around the head of the cock a few times before leaning forward and taking it into my mouth, needing to feel it inside me. Lain let out a small gasp and put her hands on my head, caressing me like a kitten.

'Oh, good girl,' she said in a breathy voice, 'you're doing so well.'

Her words reinforced my position and I eagerly explored the shape of her cock's head in my mouth, tracing its edges and top, marveling at how smooth it was. As she moaned I began to suck on it, moving my head back and forth in small motions before taking more of it in. A groan escaped me as it hit the back of my throat and I pulled away, gagging slightly. It wasn't a pleasant feeling but I was getting used to it and after a moment calmed down, taking the cock back in my mouth as Lain rubbed my head.

In the background I heard Selene get up and go to the back of the room but didn't pay it any mind. I didn't need her to guide me anymore, I knew what I was doing.

I fell into a repetitive motion, sucking on Lain's cock as if it were the tastiest thing in the world. My mouth made sucking, slurping noises that made me blush, but I couldn't do anything about them. There was something oddly comforting about all of this, especially with Lain making pleased sounds while rubbing my head. I felt like I was actually doing something good, accomplishing something of worth.

Even when I got top marks at school dad never complimented me or said anything encouraging, just told me to keep it up or else he'd become displeased with me. I'd never felt any sense of achievement or pride in anything I'd done, but here, at Lain's feet, basking in her warmth while she complimented me for sucking her cock, I felt more fulfilled than I'd ever done before. I didn't want to be here and I didn't want to do this for the rest of my life but, for the moment...just for today...it was okay to be comfortable, right?

I just wanted to feel good, just for a while, even if it was while sucking a cock. A small escape from reality...

Reality wasn't so kind though, and nor was Selene. She grabbed the sides of my panties and began to slowly pull them down, completely destroying the moment. I flinched and jerked my head off Lain's cock with a squeal of surprise.

'W-what?' I tried to turn around and glare at her but she was holding me in place again. 'What are you doing?'

'I'm going to find your prostrate,' she said and I trembled as her hands grabbed my cheeks and spread them, 'just try to relax. This will be uncomfortable at first but after a while it'll feel amazing.'

I looked up at Lain with wide eyes. 'Prostrate?'

'It's a gland inside your ass,' she said and caressed my cheek, 'it's what will make you feel good when you get fucked.'

I let out a sharp gasp as Selene rubbed a warm liquid against my asshole and began to massage the area. I tried to twist around again but this time Lain put her hands on my shoulders and gently held me in place above her lap.

'It's okay, I'm just putting some lube in,' Selene explained, 'it's to make sure you don't feel any pain.

I let out a trembling whine and stared up at Lain. 'I don't like this! It feels weird.'

'I know it's scary but just bare with it,' she said but I shook my head.

'No! Make her stop!'

She shook her head too. 'This is one of the most important steps in your training, Lily. Just endure it.'

I whimpered and clutched at her dress as Selene rubbed against my asshole, then slowly pushed her finger inside. A warm fullness filled my butt and I groaned, my legs trembling. I grit my teeth as she pushed in deeper, then began to slide her finger in and out. It admittedly did feel good, especially when she entered and exited my hole, but was such a foreign feeling that I just wanted it to stop.

'You're so tight,' she said and I heard the pleasure in her voice, 'men are going to love fucking you.'

'And so will I,' Lain said and I trembled.

'I do-'

My voice ended in a squeal as a jolt of something indescribable permeated my entire being, with the origin being somewhere inside my ass. My body reverberate with a pulsating euphoria that focused on my nipples, ass and cock, all of which seemed to become a million times more sensitive. I collapsed against Lain and let out ragged breaths, my heart fluttering as my nipples rubbed against her knee.

'There we go,' Selene laughed, 'I found it.'

'S-s-ssopp,' I slurred, my body shaking too much to properly form words. Holy shit...what the fuck just happened? Wh-

My thoughts were consumed by another wave of indescribable sensations as Selene massaged the area again, and a slew out unintelligible words escaped me. I pushed forward and nuzzled against Lain's stomach as my hands grabbed at my chest, squeezing and rubbing against the bra. All my thoughts were devoured by the intense pleasure permeating me and I just wanted it to last forever.

'Now that's the face of a slutty girl if ever I saw one,' Lain grinned and pressed her fingers to my mouth, where I instinctively started sucking on them, 'see? There's no way your a man, Lily. You're in heaven, aren't you?'

'I told you it'd feel amazing,' Selene said and was silent for a moment, 'although you seem to like it more than I'd expect this early on. Fuck you're sensitive.'

'She was born to be a slut,' Lain said and pulled her fingers out to kiss me, sending spasms of lust throughout my body, 'you're such a good girl, Lily.'

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