Stella and Stacy

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A story from the UK. Cross dressing, bi male.
3.4k words
4.45
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1/How it began

My name is Stefan. While I was eighteen and at college I first met Stella. She was so different to all the other girls there, a real force of nature, an amazing smile and beautiful brown eyes. Tall, slim and perky breasts. I fell immediately in love with her and had to be with her, although she was totally out my league.

We got together after meeting by chance in the local record shop. I was checking out a Bowie album when a voice behind me said, 'Oh, you must get that, it's the best.' I turned and there was Stella, looking amazing in a navy blue summer dress, her long brown hair tied in a loose pony tail.

'I would, can't afford it just now, though,' I replied.

Stella laughed, 'No ones looking, just slip it in my bag!' She grabbed the record and put it in her bag and left the shop. I hurried after her and caught up in a lane by the side of the shop.

'I can't believe you just...' I managed to stammer.

Stella laughed, 'Never mind that, what are you going to do for your record?'

'What do you mean?'

'Well you're not getting it for free!'

'I don't know, I've not got much money.'

'Tell you what,' she said, 'show me your cock and you can have it.'

I laughed, embarrassed, 'No way, I can't here.'

'There's no one around, come on, show me!'

I looked around and reluctantly unfastened my trousers. I pulled them down along with my boxers, just enough to show my dick.

'Mmm, nice, let's see it ready for action, though.'

She leaned forward and stroked my cock gently. It immediately leapt to attention.

'Come on, you do it, show me!' she said. She was biting her lip, with a huge grin on her face.

I reached down and wanked myself for her. She watched intently as I pulled on my cock. I leaned back against the wall behind me, wanking harder, forgetting where I was. A drop of pre cum formed on the end of my knob. I massaged the slick fluid up and down my frenulum. Stella continued watching, licking her lips. She lifted the hem of her dress, she wasn't wearing any knickers.

I couldn't help myself now. The sight of her neatly trimmed mound made me cum. I shot a huge load into the air and over the path, at the same time as an old lady came round the corner with her shopping bags.

Stella buried her face into my neck, as the woman passed by. I held her with one hand, while the other still held my cock with my sperm still oozing out.

The lady tutted, 'Disgusting!' as she passed, Stella looked up into my eyes and we laughed and kissed.

2/Fun with Stella

We started going out with each other. Stella had no inhibitions and seemed to know everything sexual. I felt I was part of an experiment, the way she would try something new.

One day, at her house, while her parents were away, we were fooling around in her living room, kissing and fondling each other through our clothes.

'OK, watch this,' she said.

She sat me on an armchair and began to strip in front of me. She finally removed her little white knickers, revealing a freshly shaved pussy.

'OK, I need your help here,'

She got down on her hands and knees, in front of me, with her bum in the air.

'You have to pull my arse cheeks apart...

As wide as you can.'

I got behind her and did what I was told, I couldn't help burying my tongue into her pussy. My cock was ready to burst out my jeans.

'No... Watch,' she said.

She reached underneath herself and rubbed her slit with a finger. She pushed it inside a few times, getting it wet, then she circled her anus with her wet finger a few times, before slipping in a little.

'Oh this is so nice,' she whispered and reached into her handbag, taking out a small jar. She opened it up and stuck her finger into it, then reached back and pushed the whole length in her arse. She eased it in and out slowly, her breathing got heavier. I stretched her more, enjoying the sight. She fingered her arse faster now, gasping for air.

'So good, so good,' she whispered again

'I need more... Run into the kitchen, Stef, get me a banana.'

I did as she asked and brought her a smallish firm banana.

I got back into position, with my hands on her lovely, smooth bum and pulled slightly. Stella took the banana and dipped it into the jar. After a couple of attempts, she had the tip against her anus and pushed. It went in a little and stopped at the point where the banana started to taper. Her eyes were shut tight as she pushed 'Come on, come on,' she said, biting her bottom lip. Then suddenly, the muscle which was stopping her pleasure gave way and two inches of banana plunged into Stella's arse. 'FUCK!' she yelled and began to ease it in and out a little. She rotated it twice, while I watched her little hole grip onto it, then plunged in another couple of inches. She started fucking it in and out, faster, moaning with pleasure, until the banana skin split and the fruit oozed out.

She eased the broken banana out her bum.

'Woo hoo, can't believe I finally did it. I've been trying for weeks. That's the first time I've managed. That felt awesome, you have to try, Steff, you really do.'

'That looked amazing,' I said, 'doesn't it hurt though?'

'At first, maybe. But it's so worth it, come on, let's go upstair.'

With that, Stella jumped up and ran upstairs to her bedroom. I picked up the jar. SILK STROKES, it said on the label. I collected her bag and followed her upstair.

I got to Stella's room and she was sitting on her bed, naked and cross-legged.

'Come on, Stef. Get naked. I want your anal virginity,' Stella laughed.

I stripped off and sat next to her.

'Get that sexy arse in the air for me.'

I turned over and knelt on the bed. I got a playful spank, and lifted my arse higher. Stella opened her jar and poured a little cold fluid on the top of my arse crack. It soon dripped down and pooled around my hole.

Stella spread the lube around my arse. Running her finger in circles before slowly and gently pushing it in. It entered all the way to her knuckle.

'Jeez, Stef. You took that right away. It took me a week to work in a finger. You're a natural!' she laughed.

She pumped her finger in and out for a while then started twisting it round, she pushed in a second finger, plunging it in, fingering me faster.

'Do you love it, Stef. You're taking it well. '

'It's ok, I suppose. Kinda nice.' I replied.

'Kinda nice, you liar, you're cock says different.'

Stella was right, my cock was throbbing, bucking against my belly, a string of pre cum already leaking out. Fuck, it felt amazing.

'You can take more than this. Turn around.'

I flipped onto my back. Stella looked around and grabbed a can of body spray from her shelf. It was long and thin, with a bulge at the top, almost cock shaped.

She lifted one of my legs over her shoulder and pushed the other wide apart. She positioned the can against her mound, shaking it up and down as though it was her penis.

'You gonna take my cock, baby.' she laughed, and spread lube over the can. The thick end of the can spread my hole wide and another hard push plunged it in. The feeling could barely be described, my cock thickened and hardened like never before.

Stella didn't hold back. She fucked me hard and fast. Pulling the can fully out with a pop and plunging it back in. She poured on more lube and banged me harder. She wrapped her fingers round my cock and i couldn't take any more.

'Fuck, I'm cumming Stella, that's so fucking hot.'

My balls tightened and the head expanded and I shot a massive first spurt into the air. It landed on my stomach. Stella let go of the can and pushed my dick into her mouth. Spurt after spurt filled her mouth, then she pulled away. My cock still oozing out sperm onto my belly and down my shaft.

She looked me directly in the eye. A glint her big brown eyes, a dribble of cum hanging on her chin, she made her way up to my face and kissed me full on the mouth.

A full mouth full of my cum washed into my mouth, Stella's tongue searching for mine, stirring the jizz around. She pulled away.

'Swallow it!' she demanded. I did.

She saw the confused look on my face.

She laughed 'It's only spunk, honey.'

She pulled the can out my arse and rubbed the remaining cum into my body. I wrapped her into my arms and we kissed.

3/Reality takes over

Unfortunately my time with Stella couldn't last. She went on to university, I stayed in our small hometown to work. We tried to stay in touch but soon drifted apart.

She came back to town occasionally. I was at a party once and Stella appeared towards the end of the night. She didn't notice me but I watched her meet some guys. They left together, hand in hand with one of them, the other with his hand on her arse. I was so jealous.

Another time we bumped into each other on the main street. Stella suggested a coffee.

We sat opposite each other in the small cafe. She looked as wonderful as ever. She leaned back in her chair, causing her round breasts to push forward. I could see the lace flowers on her bra through her thin linen blouse. A small brown nipple was centred in the flower. I couldn't look away.

'What is it?' she asked.

She looked down and noticed her clothing mishap. With a thin smile, she pulled her cardigan over and folded her arms.

Now I realised things would never be the same.

Through the years I had many relationships. Boring smalltown girls with boring sex lives, stuck in our little town. I couldn't settle with any of them, none could compare with Stella.

Ten years passed and I heard from mutual friends Stella was back. She was opening a restaurant in the nearby city. She was single. I made my mind up to have one last try.

4/Stella meets Stacy

I decided to catch up with Stella on the opening night of her restaurant. I arrived near closing time, hoping there wouldn't be too many people around. I had a small bunch of flowers and stood in the middle of the street trying to get the courage to go in.

After ten minutes standing, I took a deep breath and marched to the door. I threw it open and burst in.

Stella was standing by a table, her hair messily tied up, her glasses on the end of her nose and a pencil behind one ear. She looked totally harassed. Three tables had customers, a few other tables were waiting to be cleared.

'Oh Steff, oh thank christ you're here!'

She flung herself at me and hugged me tight.

She whispered in my ear. 'Please help me, come into the office, let me explain.'

Stella put the flowers down on one of the uncleared tables and we went through to her office at the back of the restaurant. She explained that there was a corporate booking in the private dining room, German businessmen. They were a bit rowdy and her waitress walked out. She asked if I could stand in and finish serving them.

'No problem.' I said, removing my jacket.

'Just one thing,' said Stella, 'could you wear this.'

She pointed to a French maid uniform, hanging on a coat hook.

'You've got to be joking!' I said, 'I don't mind helping, but, no way!'

'Come on Steff, they're expecting a waitress. They're spending a ton of money, do it for me, it'll be worth it, I promise.'

I swallowed hard and took the uniform off the peg. 'Seriously? This'll fool no-one.'

'Look, they're already drunk, they're on the brandy and cigars, the room's dark, you'll be fine.'

I stripped down to my boxers and slid the skirt up my legs.

'That's not going to do.' said Stella. 'Come on, get those boxers off'

She opened up her desk drawer and pulled out a box. She opened it and inside was a variety of lingerie. She took out a pair of black stockings, suspender belt and black lace panties.

'This is what you need, I'll help you get them on.'

I sat there naked and confused. My dick started to stir. Stella pulled the lacy knickers up my legs and tucked my cock into the tight material.

'Behave yourself.' she smiled.

She put the suspender belt on and rolled a stocking up each leg and clipped them on.

She stepped back to admire her work. 'Mmm cute.'

She helped me on with the skirt and white blouse.

'Just one more thing.'

She went back into the drawer and took out a wig. She put it on me, went into her handbag took out some makeup and applied some red lipstick and dark eye shadow.

She flicked her fingers through my now shoulder length hair.

'Perfect.'

Stella wrapped me up in a big hug.

'Oh thank you so much for this. You look so pretty, we'll have to give you a pretty name... How about Stacy?'

Stella put a pair of heels on me and pulled me up and we headed for the door.

I paused as I caught a glimpse of myself in a mirror.

'No time for that.' Stella said.

She opened the door and bundled me in.

'Have fun, Stacy.' she said as she closed the door behind me.

The room was dark, with a dim glow around the ceiling for ambience and a few tall candles on the table. The table was set with a white linen cloth and silverware, it looked very upmarket. Sat there were a group of German businessmen. A tall stout older guy, with thick glasses and beard was holding court to four younger men, probably in their early twenties. They laughed at his jokes and he swung his arms around as he talked, loving being the centre of attention.

He noticed me, hiding in the shadowy room and held up an empty glass. I tottered over on my heels and topped him up with the bottle on the table, then stepped back into the darkness.

He continued on with his stories, the younger ones transfixed by him.

'Might just get away this.' I thought to myself.

The night carried on. I filled empty glasses, the guys got drunker and louder. While going round the table I would get the odd pat on the behind or stroke of the leg.

I stood back and waited in the shadows. I was feeling a bit embarrassed about the way men treated women, thinking they could do as they liked. My thoughts soon turned to Stella, hopefully this favour will help me get back together with her. My mind wandered to her beautiful body and sexy smile and my cock twitched in my tight lace panties.

'Over here, miss!'

The big guy was holding up an empty glass. I sighed and went over and topped him up. A large hand shot up my skirt and grabbed my arse.

'You are not dressed to be a waitress,' he said, stroking my thigh and my stocking tops. He downed the brandy in one gulp and held out the glass for more.

As I went to pour, he moved the glass away, spilling brandy onto the table.

Instinctively, I grabbed the napkin on his lap to stop the flow. I noticed under the napkin, he had his cock poking out of his undone fly. Off balance, leaning over in heels and reaching over, i fell face first into his lap.

A large bear paw hand pushed the back of my head down. He had a short, but very fat dick, with a huge flat mushroom head and he pushed it into my mouth.

I could barely breath as it totally filled me, he ground his crotch forward. He called out to his companions and they crowded round to watch. He thrust his hips forward, his thick cock bulged in my cheek. After a few strokes he groaned and shot a load of thick spunk in my mouth. I had to swallow quickly to avoid choking. He held me like this until his dick went soft, he was giving instructions to his friends.

I was lifted by the shoulders, face down on the table and held there. My skirt was lifted over my bum and hands stroked my arse, legs and stocking tops. My cock hardened at the attention i was getting and my heart raced. My panties were pulled to the side and a hand on each arse cheek, pulled them wide apart.

The older guy took an empty brandy bottle from the table and spat on the end. He lowered it to my arse hole and gently pushed and twisted it against my opening. He spoke in German, instructing his friends and gently inserted the neck of the bottle. He withdrew it completely and spoke to one of his colleagues. I felt a tongue lapping at my arse, getting it wetter. The bottle was pushed in again, and stroked in and out. It was pulled out totally, then plunged back in, my sphincter having no time to close in between thrusts.

'Nice, eh.' was whispered in my ear. And it was. My cock was twitching inside the tight material of my panties.

The bottle was pulled out and i felt someone get in position behind me. After a couple of attempts, a thin, hard cock was thrust into me. He bucked hard and fast into me and quickly shot his load. Another guy took his place, he struggled to get his semi hard cock in. He ended up rubbing it against my arse and wanking his cum out over my bum cheeks, some dripping down my crevice. My left leg was pulled up onto the table and I was spread further. Next guy up pushed his dick against my hole. He was bigger than the others and patiently waited for my arse to accommodate him. The slippery cum already inside me lubricated his cock and it eventually buried inside me.

He fucked me with long, even strokes. It felt so good. My cock was throbbing and I ground it into the table as he screwed me. I couldn't stop myself moaning and pushing back onto him. Another guy shuffled up beside us, wanking his cock, and let go a huge spurt of cum on my arse and down my leg. The guy fucking me grabbed my hips and rode me faster. He let out a roar and plunged deep inside, shooting another load inside me. He stayed inside me until his dick softened and slid out.

My panties were put back in place and I got a pat on my bum. I lay on the table as everyone collected their things and made there way out. I felt numb but invigorated inside. I never thought I'd enjoy this as much. As my senses came back I was aware of the taste of cum in my mouth. I sat up on the table and there was Stella, hands on her hips, standing by the door.

'I see you enjoyed yourself.' she smirked, walking over. My cock had popped out of the waistband of the knickers and was raging hard against my belly. Stella ran a finger over my lace clad balls and up the underside of my cock. She dipped it into a pool of sperm, which had leaked underneath me and massaged it onto my cock.

'Oh, Stacy, you're such a dirty girl!'

She dipped her fingers into the sperm pool again and held it up to my face.

'Come on dirty girl, lick up the cum for me.'

I lapped at her fingers, and she laughed, dipping her fingers more and feeding me more cum.

'It's only spunk, honey.' she smiled.

'Come back here on Sunday, it's my day off, we'll have some fun together.'

And with that, she turned and left.

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wankerholic42wankerholic425 months ago

Nice one! Very horny.

AnonymousAnonymousalmost 2 years ago

Sexy. Loved it.

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