The Hen Night Ch. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Squeeze my lips together...hmmm...just there, yesss," she sighed.

Gradually she let my middle finger slide between her lips and my other fingers either side of her inner lips, applying gentle pressure to them. She seemed to enjoy the attention given to those lips.

I was desperate for my own release, so started rubbing my finger up and down her wet slit, swirling round her clit and down to her entrance. I tried to stick a finger into her.

"No, not yet, I'm not ready....when I say now, I want you to cross your fingers, then twist them into me ... NOW!"

She was shaking, her face and upper chest were very red, as I twisted my crossed fingers in and out of her. She was racing to another screaming orgasm. Her legs clamped round my hand.

As her breathing calmed, she draped a leg over me, "I want you in me, put it in," she whispered.

At last I thought, as I slipped into her. Unfortunately, I'd been so close to cumming for so long, that I came after only two or three thrusts.

Turning to present her cum filled vagina to my face, she said, "I'm not sleeping in a wet patch. You'll have to clean me up."

I wasn't sure about that, but I wasn't given any choice as she glued her vagina to my mouth. I'd never tasted male cum, let alone my cum, before. I'd heard stories of women swallowing male cum, so if they could do that, it couldn't be so bad. I resigned myself to the task, soon forgetting about tasting my own cum, I tongued her to another orgasm.

I awoke to the sound of buzzing and panting. Opening my eyes I saw Kelly sat in a chair, legs spread wide and playing with a vibrator. I sat up, sometime during the night I must have lost my lingerie. Taking my erection in hand, I slowly masturbated, while watching her.

We were watching each other when, "OOHHH...YES...YES...YEEESSS," her thighs clamping together as she turned off the vibrator. I stopped what I was doing, that was awesome, never had I seen anything as magical. Her eyes opened, she looked across and smiled.

"Do you want me to help you with that?" she said, as she took over where I left off.

"We don't want to make a mess do we?" She licked me and took me in her mouth.

Nobody had ever sucked me until that moment. This driving me crazy, I wanted more.

"I'm going to cum," I warned.

She didn't stop till after I came, she swallowed it all then licked her lips.

6. Feminisation

"Lets clean up, it's getting late. We'll go out for some lunch."

It dawned on me that I only had the dress I'd worn last night, "I don't have anything to wear!"

"We'll find something, I'm sure I have something that'll fit."

"But you only have women's clothes."

"Well you wore a dress last night, and you seemed to enjoy it."

She was right, despite some unwelcome attention, I had enjoyed it, I'd enjoyed being a woman. I just hadn't envisaged going out again in a dress.

In the bath, she said, "one of your boobs is coming away, I'll stick it back on when we dress. Oh you better shave that stubble as well."

Back in the bedroom, I lay on the bed while she lined up and reattached the errant breast.

I tucked myself in, as she past me some clean panties and bra. I picked a white polo neck sweater and a black and white check mini skirt. She handed me some black opaque tights to go with it. She did my makeup. As she finished her makeup, I was admiring myself in the mirror, admiring the shape and feel of my breasts.

"Stop playing with yourself. Lets go eat."

Kelly got annoyed with me at one point, nonetheless I was really enjoying being dressed and people assuming I was a woman. I felt unexpectedly different and relaxed.

"STOP THAT! People will think you're flaunting yourself and that might bring unwanted attention."

In the evening she drove me back to my place.

Monday morning in work, I was Paul again, but I'd kept the painted toenails. I was teased by the lads, but the girls soon put them in their place. Kelly kept calling me Paula, only mouthing the last 'a' if we were in company.

On the Tuesday, Kelly and I went to a cafe, for lunch. As we sat down she handed me a little package, "I want you to wear those tomorrow, and I'll check."

I reached into the package and pulled out...new pink panties! quickly putting them back, hoping nobody else had seen. "I can't wear those."

"Why? You've been wearing panties and more all weekend."

The following day, at lunch time we went for a walk by the canal.

Down a passageway, between the old warehouses, she said, "show me."

I unzipped my fly, her hand reached in. I was instantly hard, as she started rubbing. She undid the buttons at the waist to expose the panties. I tried to get my hand under her skirt, but was batted away.

She started to masturbate me, saying, "lets see how far you can shoot."

That was the start of a journey I willingly let her lead me down. After the panties, it was a gaff and panties. Weekends, dressed en femme and going clothes shopping. We sometimes met some of the girls from work, they acted surprised to see Paula, but I had a feeling they weren't really. I was becoming more feminine in work, a bit of makeup, nail varnish, nobody made any comment. One day all my buttons fastened up the other way, I was wearing a blouse and jeans belonging to Kelly. That was the first day I used the Ladies in work. I hadn't stood at a urinal since wearing panties and once I was wearing a gaff, it was just easier to pull everything down and sit. The girls had seen me on our Hen Night in the Ladies, so I didn't foresee any problems.

The only comment made was, as I was washing my hands, by Naomi from accounts coming out of one of the cubicles she said, "Paula you do know that the management don't like us wearing jeans or trousers."

That was all the encouragement I needed. The next day I stuck my breasts on, a skirt, a blouse and tights. Nobody batted an eye, I was just one of the girls.

I now had an excuse, as if I needed one, to go out with Kelly and buy a whole new wardrobe, out went all my male clothes. I was a new person, I needed new clothes.

I bought a sleep bra and sleep breasts. Bras with pockets that would take my breast forms, so I didn't have to keep sticking them on, and my skin would have chance to breath. I only stuck them on if we were going somewhere special and sometimes at the weekend.

7. Living together

I sold my place and moved into Kelly's flat. I'm not sure, but had a pretty good idea of what the neighbours thought about us. After all we did tend to get a bit noisy and vociferous when making love.

We loved to masturbate, either watching each other or masturbating each other, either way was a turn on. Kelly wanted at least two orgasms before we had penetrative sex.

If sometimes she thought of me as her lesbian lover, or she thought of me as a 'chick with a dick.' I had no problem with that, as sometimes I thought of myself as inhabiting a woman's body. So when I was caressing her breasts, tweaking and sucking her nipples, I imagined it was my breasts and nipples. When I played with her vulva, her labia or I had my fingers in her, it was happening to me. Penetrative sex, it was my vagina that was filled.

The day came when, I was on my back, legs back and open. She was lubing me and her strap on. The tip was teasing my hole, I was nervous and afraid. I was an anal virgin.

"No you mustn't."

Too late, she pushed in. She was so quick I didn't have time to register any pain or discomfort. We lay there looking at each other, while I got used to this new feeling. She started to withdraw, I crossed my legs behind her, holding her in.

"Don't take it out, it's nice."

I was soon rocking against her, she quickly responded, in no time we were meeting thrust with thrust, hips pounding against each other.

I started gibbering, "no...no...no...yes...yes...yes...yeess!"

I had a mind blowing orgasm, that started in the pit of my stomach, and spread all over my body from my toes to my head. Who even knew that was possible, why had nobody ever told me? If that was what it was like, I wanted more.

I hadn't even realised that I'd also cum on my chest and stomach, till Kelly started to slide her body in it. We did like our sex wet and messy.

8. What Next

In the bath after, the inevitable question came. I suppose it was only a matter of time.

"Paula, do you wish you were a woman? Do you want a sex change?"

"No...I like my tackle, I like it being inside you...Fantasising about being lesbian, doesn't mean I want to change my sex...I can't imagine sex with you if I had a vagina...Proper breasts would be nice though."

"Phew, I'm glad, I thought we might have pushed you too far... I like it inside me as well...You could have breast implants."

Implants sounded like a good idea, no more worryi...wait, pardon!

"What do you mean...did you just say WE?" I shouted.

After a lot of shouting, mostly by me, Kelly admitted that it was all a setup.

"Why ME?"

I stormed out and barricaded myself in the bedroom, without waiting for any explanation. What was I going to do? I couldn't stay here. I'd sold my place. Where would I stay? I couldn't go back to work. I didn't have anymore male clothes. I sat on the bed and cried. One little word had changed and destroyed everything.

Kelly was crying and banging on the door, "It wasn't my idea...they put me up to it... Let me in...please... I love you, I always fancied you...let me talk to you....Paul."

I wouldn't listen.

I had loved Kelly, I had loved being dressed, how could she, how could they all have conspired to feminise me?

I packed an overnight bag.

Kelly was on the phone to Pam and Chris asking them for help in persuading me to listen.

The breasts, bras and gaffs were slung into a corner.

I pulled on some jeans and a T-shirt.

I was going to wait till all went quiet, then make a quick exit.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
bent16cabent16caover 2 years ago

Great story. Please continue . Would like to read more .

DianeRedfernDianeRedfernover 5 years ago
So wet!

This is one of best beginning to a story series here ever. Paula is so lucky. And Kelly too. Paula is sure to come soon, er...come around soon.

The experiences are so vivid. So hot and wild. I am so wet.

xoxo,

Di

AnonymousAnonymousover 5 years ago

keep it coming good story

Dawn191270Dawn191270over 5 years ago

you believe I am English sheeesh if you love someone you run really .. Think that is better

Dawn191270Dawn191270over 5 years ago
i cant wait to see the way out .

If you ovesomeone run really ;-) , still you needed the plot move I do get it

Show More
Share this Story

Similar Stories

Straight Crossdresser Guy dresses as a girl on Halloween & ends up performing as one.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
One of the Girls So you want to join the girls for a night on the town? in Transgender & Crossdressers
Girls Have It Easy My girlfriend teaches me what it's like to please boys.in Transgender & Crossdressers
Obey Thy Neighbor Sexy neighbor discovers his crossdressing.in Transgender & Crossdressers
More Stories