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Carl, Carla and Hannah - Part 5

Carl takes on a bet...
We lay in each others arms for a while and then Hannah raised herself up and got off the bed. She unbuckled the strap-on cock attached to her. It was only as she took it off that I saw that this one was not only slightly bigger than the one she used earlier, it also had a dildo for her. No wonder she'd enjoyed that last fuck as much as she had. She passed it to me, telling me to take it to the bathroom and clean it thoroughly.

"Yes ma'am," I jokingly replied as I swung my legs off the bed and headed with it for the bathroom.

As I crossed the bedroom floor, I experienced a dull ache in my ass. As soon as I reached the bathroom, I went to the toilet and then cleaned myself up. The ache hadn't disappeared, and it struck me that it probably wouldn't for a while. In fact, my whole groin area felt heavy and almost bruised as I cleaned the double strap-on at the sink.

After I dried it, I looked at myself in the mirror. I looked a mess. My wig was askew and my new dress had a stain where my cum had soaked through. My stockings were out of line and my bra wasn't where it was supposed to be. I took a cloth and tried to clean the dress as best as I could. Then I altered the wig to get it looking as good as when Hannah put it on me. After realigning my stockings and bra, I went back to the mirror. Better.

Hannah regarded me carefully as I came back into the bedroom. By now it was dark outside and she'd put the bedside lamps on and drawn the curtains.

"You know, you look quite good as a girl," she said.

I gave an almost derisive snort.

"No, really. With a bit of work, I think you could be quite convincing." She studied me a little more intensely. "I bet, with a bit of guidance and preening, you could pass quite easily as a girl," she said, suddenly warming to the idea.

I didn't know what to say. I didn't particularly want to look like or be a girl, but then again, I seemed to take to the part quite easily. I looked at her loving, smiling face as she looked me over, thinking. I didn't reply as I tried to consider what she'd said. My initial thought was that I would look stupid, just look like a bloke in a dress. Then I thought about how slightly uncomfortable it felt to be dressed like this.

On the other hand, apart from the lingerie shop, it struck me how easily I had been led down this path. The orgasms I'd had thanks to Hannah had been mind blowing. It had definitely been fun, exciting and loving. The more I considered it, the more I thought that dressing up for her was both enjoyable and, well, almost natural. But going outside the bedroom, well, that was a whole new ball game.

"I don't think it would work, I'd just look stupid. Hannah, I love that you like me like this, and it's been great fun, but I really think it should be something we keep to ourselves," I said thoughtfully.

She cocked her head in that way of hers which showed she had a different point of view. Then she said "Okay, I understand. You don't want to be humiliated in public. I can get that. But I disagree. Baby, let me work on you and I bet that in two weeks you can go out confidently as a girl and no-one would know you weren't. Please, for me."

I expressed my doubts, telling Hannah that it would be me who was humiliated in public, not her. She then tried her best to convince me, but I kept up my resistance for as long as I could.

Finally, she said "Okay. Just let me try and convince you. If you give me two weeks to work on you, promise that you'll do as I tell you to and at least try, then I bet you could pass as a girl. If I win, I get to take you out for a night you'll never forget. In return, I promise we will only go out if you agree, and I promise you won't be humiliated. If I'm unable to convince you by the end of the two weeks, I will never mention it again. Deal?"

I couldn't think how she was going to get me to agree to go out dressed as a woman, and the thought that I could ever pass as female was ridiculous at best, so I reluctantly agreed to let her try. "Deal," I said.

And that, I thought, was that.

"Well, no time to get started like the present if I've only got two weeks," she said, getting up.

She led me over to the dressing table and got me to sit down in front of the mirror. After studying my face for a moment, she got out her make-up box along with a few other things.

"Right, for now I'm just going to do the basics. We'll start with some foundation. Now, watch what I do carefully."

Hannah took a bottle out and shook it before pouring some liquid onto the back of her hand. Then she dabbed some on my cheeks and then rubbed it in gently into my face, occasionally patting it in as well. Once she had covered all of it and was satisfied, she took a brush and some eye make-up and applied it gently over my eyelids. I struggled to see this part as I had to keep closing one eye each time she applied it, but I seemed to get the gist of it.

The next step was some mascara which Hannah applied using a brush. She was really careful when she put this on, but I still felt a little uncomfortable with her doing it. I wanted to keep taking the brush off her and do it myself. Once my eyes were done, the last thing was my lipstick. She took two tubes of lipstick and gave one of them to me. She showed me how to twist the tube and the apply the lipstick correctly as I copied her every move.

When she was satisfied, she sprayed some perfume on me and then sat back and told me to look at myself in the mirror. I kind of had to do a double take at first. The image looking back at me was me but, at the same time, not me. I could recognise it as my face, but it looked smoother, softer and more feminine. With my hair tidied up, I had to admit that I was impressed, and said so to Hannah.

"That's just the basics, don't forget. There's a lot more to putting on make-up than that, and we'll have to work on your eyebrows a bit as well. But yes, not bad for starters. Right. Well, I don't know about you but I'm starving," Hannah said, getting up. "What should we do about dinner?" she said.

We ended up ordering a takeaway from a good Chinese place in town that delivered. Hannah told me not to get changed as I was to spend the rest of the weekend dressed and made up to get me used to it. She, however, got changed into a pair of slacks and a white blouse before telling me to get the wine, cutlery and glasses out, ready for the meal. I must admit, I felt a little more at ease moving around the place once all the curtains had been drawn. My only real concern was if anyone came round to visit.

After we'd eaten the Chinese food, we slumped on the sofa in front of the television with what was left of the Chardonnay. The usual Saturday night crap was on, so I suggested we watch a DVD instead. As Hannah was in charge this weekend, she got to choose, and we ended up watching a chick-flick from about two years previous. However, this time was slightly different. Instead of me sitting on the sofa with Hannah curled up on me and my arm around her, we sat the other way around. It felt a little weird, but I didn't really mind.

As I found myself becoming engrossed in the film, I started to enjoy the situation. It felt good to be sat with someone's arm around me, all protective and loving. I curled up on the sofa, straightening my dress almost unconsciously as I pulled my legs up. The film was a bit of a tear jerker, and while those kind of films don't usually do anything for me, I found myself getting emotional for some reason. Somehow I managed to get through the film without actually crying, although the romantic reunion scene at the end nearly had me.

Once we finished the film, we watched a couple of other things on tv. As we watched, I felt Hannah's hand rubbing along my arm, which felt nice. After a while it slipped down to my 'breast', and she carelessly started to rub and fondle it. The warmth and feel of her hand came through the silicone as it rubbed against my chest, creating a tingling sensation in my still sensitive nipple. I enjoyed the feeling as we lay there, and I appreciatively stroked her forearm as she caressed my boob.

A few minutes later, her other hand joined in, taking hold of my other breast. Soon, she was massaging them both, and I have to admit that it felt pretty damn good. I turned to her and she leaned forward and kissed me, her hands still rubbing my chest. I was almost immediately reminded of the fact that I was wearing lipstick because the kiss felt slightly different to normal. I reached a hand up to stroke her face as her tongue danced in my mouth. The fact that it was she initiated and controlled the kissing now was almost accepted as I yielded under her kiss, her passion growing. It was a lovely kiss.

I reached over and took one her breasts into my hand, rubbing it gently in small circles, stimulating her nipple. We explored each other, our hands everywhere at once before I felt Hannah push me down. I understood what she wanted as I undid her trousers, sliding my hand into her boxers.

I looked at her questioningly, and she gave me a wicked smile back. "That's right, baby, you know what I want," she said sexily, pushing me down.

With a little help I managed to pull her trousers and boxers down. Hannah spread her legs as I leaned in and took in her musky scent, my eyes feasting on her beautiful labia. I kissed the insides of her thighs, working my way inwards until my cheeks brushed her moist lips. I licked her slit from bottom to top and then back again a few times, separating the lips with my fingers as I did so. At the top of stroke, I gave her clit a light flick with the tip of my tongue which made her groan. It wasn't long before I felt her hand on the back of my head, pushing me in.

I delved into her moist sex, lapping at her pussy as she held me there, all the while moaning. I felt the telltale signs of a couple of small orgasms as she vigorously rubbed her pussy in my now soaking face. After a while her grip on me relaxed and I managed to get my breath. Hannah smiled, then got up and stood before me, looking splendid and so authoritative.

"Again. Worship me," she said simply.

I knelt before her and started licking her mound again, wrapping my hands around her to cup her bum cheeks. My tongue started to tire as I gave it everything I'd got, trying to delve as deep as I could before concentrating on her clit. All the time she kept murmuring and spurring me on, calling me her girl and her bitch. After a few minutes she told me to stop, for which I was grateful. Then she turned round, presenting her backside to me.

"Continue, slut," she commanded, bending forward slightly so her gorgeous bum stuck out towards my face.

I pulled her cheeks apart and then worked my tongue into her rosebud, making her squeal with delight. I reached round and slid two fingers into her sopping pussy as I worked on her beautiful ass, frigging her vulva gently while I tried to push my tongue deeper. I felt her come three, four then five times as I worked furiously, my lips going numb with the pressure on her arse. Finally, I pushed a finger into her bum and finger-fucked her in both holes until I was rewarded with an ear-shattering scream as she came.

Hannah's legs nearly buckled beneath her, and I had to quickly remove my hands in order to catch her. When she had recovered her composure, she looked down at me and gave a wicked smile.

"Oh baby, look at you! Lipstick all over the place and your pretty dress all ruffled. Mmm, you look so hot. C'mon," she said, holding out her hand, "I've just got to take you upstairs and fuck that pretty, tight pussy of yours."

"Hannah, please, no," I said entreatingly as I took her hand and stood up. "I really am sore down there, angel, and I think I'm quite bruised as well. I might even have been a little damaged. Please, I'll do anything else but please don't use that thing on me again tonight. Maybe by morning it'll be better."

I looked deep into her eyes and she saw my genuine discomfort.

"Okay, baby," she said, stepping in close. "I'll leave your pussy alone tonight. Come," she said, leading me by the hand upstairs as she turned the lounge lights off.

When we got to the landing , she directed me towards the bathroom, telling me to strip down to just my bra and panties and then come through to the bedroom and freshen up my make-up. A few minutes later I was sat in front of the mirror reapplying my lipstick. Hannah directed me to the nightie lying on the bed. Once I had slipped it on, I climbed into bed with her and lay in her arms. Within five minutes we were both asleep.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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