That Red Dress Started It...! Ch. 08

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Stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me!
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Part 8

"Well hello there " he said beaming, moving up close and putting a hand on my bare thigh. "So nice to see you again."

Again? Hell!

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The professor moved closer to me - and kissed me! His hand was on my thigh. I was suddenly very worried indeed.

"Henry, really. I can never take you anywhere."

I looked up as Professor Kingsley backed off from me, smiling in a rather self-satisfied way. The speaker was his companion, a woman of about fifty who was obviously 'dressed up' for a night out. Not dressed up in the way I was, but in an attractive way. Wearing a rather bright yellow dress which, non-expert that I was, I would have described as well-cut but just not quite the right colour for her.

"I must apologise for my husband, he's not to be trusted with a pretty girl, you know. In a minute he's going to make some excuse, usually that he's got his reading glasses on. I'm Amanda by the way, this is Henry."

I didn't really know what to say. I was still rather flustered by the Professor's advances but it was Andrew who rescued me.

"It's OK, Mrs Kingsley, your husband and I have met. He was teaching one of the courses I did at the University some years ago."

I had been right. It turned out that the Professor and his wife were revisiting an old haunt. They had first met at the club - before it became a night club that is - twenty years earlier to the day and had decided to see what it was like now. And despite the music and the crowds they seemed to be enjoying themselves. They asked us to join them, I rather imagine they thought of Andrew as one of the 'oldies'. Most of the crowd seemed to be about twenty or under, I really did feel something of an 'old maid' myself. Which was a ridiculous thing to think for so many reasons.

We sat at their table at the side of the bar, rather away from the throng. Andrew and the Prof. got into discussing 'old times' - maybe five years earlier, something like that. And Amanda and I discussed - girly things! My dress, my shoes, her earrings, stuff like that. I hedged rather when she began to move onto 'relationships' and to ask about me and Andrew. We ended up chatting about the 'youth today', bemoaning the lack of this and the problems with that, and why kids didn't like proper music! And when the DJ introduced MC this and DJ that I commented that there seemed no real merit in modern music, not like in my day when bands had proper names like U2 and REM.

It was when Amanda started to quiz me on what I was doing with my life, was I still at college or what, that I began to become very nervous. I'd had a few drinks by then, fortunately Andrew spotted my problem and butted in.

"Sorry, Mrs Kingsley. We really should be going now, I promised not to keep Bethany out too late you know."

Promised? Who?

We wished them happy anniversary and left. And as we strolled out and hit the night air an amazing exhilaration came over me. I had REALLY been a woman, in strange company, and I had loved it. OK I had been worried at first that the Prof would see through me but it turned out he really had come out wearing the wrong glasses. Hurrah for forgetfulness.

As we left and headed back to the car - I just couldn't resist the temptation - I pulled Andrew towards me against the wall of the club. And kissed him. And this time it was a proper kiss, not like with the locksmith guy. Not even like those with Neil on New Year's Eve. This time I put a lot into it – tongues and all - and I was rewarded in spades.

I felt myself judder with the excitement as I slid my glossy red lips across Andrew's, as we pulled each other close together. I felt his hand slide down from my bum onto my leg and then back up inside my skirt and over my bare flesh towards my panties. I was shaking with anticipation. Something significant was getting very close.

And it was when my own left hand slid down and across, and I felt the swelling inside Andrew's pants, that I knew that time was near. I pulled away.

"Andrew. Drive me home" I whispered in his ear as seductively as I could.

We said very little on the short drive back to my flat. As he followed me in through the front door and I turned to kiss him again, it was Andrew's turn to pull back.

"Bethany. You are a beautiful woman. Really. But - well - there are things you may not know about me and, well, maybe things I am not sure of about you. I need to know. Please. PLEASE!"

I smiled and moved in to kiss his lips very tenderly, not saying a word. And this time my hands did the exploring first, pulling down his trouser zip to snake in and wrap my fingers round his erect penis. And then he followed suit, sliding his right hand up my skirt and towards my panties. And this time I didn't stop him.

"Oh my GOD!!"

His right hand had arrived there. And it had found what it wanted to find. I stopped kissing him just for a moment and looked him straight in the eye.

"All right my darling. Now that you know. What are you going to do about it?"

"Well - er - "

Suddenly Andrew was incredibly flustered. He muttered and mumbled for several seconds, for some reason finally having his thoughts confirmed had sent him into a spin. Or at least had sent his head into a spin, his right hand knew exactly what he was doing. It was feeling round my cock, caressing my foreskin, gently pulling and stretching my already excited member. Maybe Andrew had done something like this before but it was all new to me - I was feeling SO horny.

"Andrew. Darling. You don't know how long I've wondered whether this might happen" I cooed in his ear.

"Er - Bethany. Are you sure? I mean, we don't have to. Not if you aren't sure."

Andrew was uncertain again but I was not. Most definitely not. I really had fantasised about this moment. I whispered in his ear again

"Yes Andrew. We do have to. Take me. Now."

And he did. Our gentle caressing and teasing rapidly got harder and hornier and rougher and tougher. Within a minute we were moving towards the bedroom and undressing each other, almost ripping our clothes off. I was breathing heavily as Andrew reached down and slid off my panties. Needless to say my cock stood out proudly.

Then Andrew pulled his own shorts down, what was staring at me was the largest most gorgeous sight I had ever seen! It was quite long, maybe 9 inches, but it was so thick! The large throbbing purple head was enormous. I looked up at Andrew with surprise written all over my face.

"Andrew, I know I said I am new to this but I can appreciate beauty when I see it, that is so wonderful. So tell me, how are we going to play this?"

"God Bethany, I am so desperate. You look sensational, any man's dream, such a sexy woman - with a cock! Go ahead, please, I need you to..."

It was obvious what he wanted, his cock was only inches from my face and was visibly throbbing. I started gently licking the head with the tip of my tongue, enjoying the pre-cum that was oozing out, and all the while Andrew was groaning and enjoying the experience. As I licked the head, I used my fingers to massage his full and very tight balls. I licked and played with the massive head of his cock and then finally started licking up and down the shaft.

Andrew was groaning so much, he was obviously enjoying this as much as I was. I teased the head of his cock with my luscious red mouth and managed to get my lips around it and slowly start pumping up and down. I could only take him about half way to begin with, but then I wriggled his cock round in my mouth with my tongue until it found just the right position and slid down towards my throat. I felt his pubic hair begin to tickle my nose and I knew it was all the way in!

At which point it exploded. The whole experience was sensational as the thick rod bucked and reared inside my mouth and I felt Andrew's hot juices coursing down my throat. It had taken maybe four or five minutes to reach that stage but it was all over within seconds. I was full - and Andrew was shot! He pulled his cock out and collapsed on the bed beside me. We both were breathing deeply - and contentedly.

"Andrew, that was sensational" was all I could say.

He said nothing, he was still recovering his breath.

I lay back with my head resting on the pillow and closed my eyes for a few moments, enjoying the memory of my first REAL sexual experience with a man. And what a man! Then I looked up, at Andrew smiling down at me. He cupped my right 'breast' through my bra and moved his hand slowly down my body as our lips met once again. He kissed my mouth, my chin, down my neck, his slightly rough face rubbing against my skin.

I lay there feeling just plain wonderful as Andrew nibbled my shoulders and his hand found my breast again, causing me to shiver with delight and he lovingly squeezed the soft 'flesh' there. He brought his lips to my nipple, it made me feel so feminine and content watching him tease it with his tongue. I couldn't really feel it but I could imagine, another shiver went through me. As he was teasing my 'breasts' with his lips his hand found my arse and he kneaded the softness of my cheeks.

His touches were so gentle and sent rivers of goose-bumps through my entire body as his hand moved down my smooth leg and then up the soft skin inside my thigh. I lay back taking in the sensations, sighing expectantly. His long fingers found my hard cock and I moaned and arched my back as he gently squeezed me. He looked into my lust filled eyes and raised his finger to my lips and I licked it and pulled it inside my mouth. He then moved his wetted finger to my anus and slowly pushed it inside of me.

My body tensed as his finger massaged inside my hole. He really was being very gentle and went very slowly. He knew I was a virgin and he obviously knew he was about to 'take my cherry'. Again he kissed my mouth and this time I absolutely devoured his tongue, so turned on was I. He knew that I was his girl now, and his to make a woman.

"My darling, I do so want you - now – please, my lover. Will you fuck me?"

We kissed again. As he began moving his finger in and out of my arsehole I moaned, thrilled at each new sensation I was feeling. I spread my legs and pushed back against his hand as he stroked his finger gently inside me.

"Are you really sure – Bethany?"

"Andrew. I'd really like you to - fuck me?"

Of course the answer was obvious.

I lay back against the cool sheets as he used first one, then two and then three fingers to tease my hot waiting hole. I spread my legs wide for him - he put my legs over his shoulders as he positioned himself over me.

"This will probably hurt a bit to start with, Bethany. I'll go very slowly" he cautioned. "Let me know if it's too much and we can try something else, O.K.?"

I smiled nervously and nodded. I felt my legs pushed apart with his weight on top of me as his cock began to push into me, spreading me open. It was slightly painful but Andrew was very gentle and worked his cock very slowly inside me a little at a time, waiting as I became used to it. It was uncomfortable at first, but soon the slight pain and discomfort subsided and the pleasure took over. It took some time but finally Andrew's full length was deep inside me and I smiled up at him and reached out to touch his face and reassure him. He withdrew slowly half his length and then pushed back into me again, repeating over and over until there was no pain at all, only pleasure.

"Bethany? Are you – OK?"

"Oh God, yes!! It's good, Andrew, it really is. SO good!!" I replied, trying to speak calmly as all sorts of sensations and emotions washed through my mind.

It was good, Really good. Just for a moment I was a little disappointed, sure it felt all right but.... And then I wriggled my arse, just to get a little more comfortable and as I did so that gorgeous monster cock moved in even further. Only an extra half-inch maybe but it made all the difference in the world. I wasn't sure what his cockhead was doing up there but it had hit something wonderful. It total pure pleasure.

Pleasure? Hardly the word for that experience. As the whole length of that beautiful cock slid ever-so-smoothly in, right up to the end, and out again I was in another world, one of pure unadulterated delight.

"Christ Andrew, that's it!" I shouted out. "Yes oh yes!!"

He smiled sweetly and continued to slowly fuck my arse as I stared up at his handsome face, moving my hands firmly round his torso. OK he was no Rambo but in some ways he came close, I could see his muscles rippling as he worked at me harder and harder. I let him know how I was loving it all.

"Oh my darling, it is so good for me too. Bethany, I've never ever been with a woman like you before. I do so want you to be satisfied."

"Fuck me. Andrew. Fuck me! Harder!!" I called out, as the glorious sensations began to overwhelm me.

Andrew started to thrust more quickly into me. I was pushing back in time with his movements and squeezing him with my sphincter muscles as we fucked. It was the most wonderful thing I have ever felt. My 'boyfriend' was on top of me and he was fucking my brains out!

As Andrew screwed me I was gasping and calling out to him.

"Oh yes my love, yes! That feels so good!"

He was now fucking me hard and fast. His sweat dripped down onto me as he pumped his cock in and out of me more and more. Finally I knew we were getting close to a climax.

"Andrew, oh my baby, please come inside me" I pleaded.

I knew I needed so badly now to feel him cum inside my body and I could tell that he was just about to explode.

"Oh God, yes honey" I gasped and then I started to feel him empty his load inside of me.

As soon as I felt him start to come I started coming too, spraying cum all over my own stomach and chest, over and between my tits. His cock erupted inside me, splashing my insides with his sweet semen and dripping from me onto the sheets below me. We rolled and squirmed, wriggled and fondled, grappled and groped for what seemed like ages as that gorgeous hot cock thrust and squirted Andrew's love-juices deeply inside my arse.

I was in heaven, digging my long scarlet nails into his bum, feeling my boobs squashed against his manly chest. Our mouths were pressed together and our tongues jostled with the passion of the moment. I'd had good sex before but this was in another league. Then we collapsed together and I held him in my arms as his cock grew soft. I let him slip from within me after one last squeeze of my well-used muscles.

I kissed the beads of sweat from his forehead and cheeks as our hearts beat frantically together. We both started to laugh, I stroked his head and held him tightly to my breast. He moved up and put his arms around me and we kissed once again. Now I knew I never wanted this moment to end. We drifted off to sleep like that, my head on Andrew's chest and my leg draped over his. Lovers.

I woke at seven as the early morning light shone brightly through the crack in the curtains. I looked across at Andrew, still fast asleep, even maybe snoring a little. Wow, what a night! I lay there for several minutes, looking at my lover's face, a very happy girl.

Then more practical thoughts began to creep into my reverie. What must I look like after all that? Maybe it was OK to not look totally perfect in the middle of the sexual act when we were both a little drunk. But I just couldn't let Andrew wake and find me in any way looking like a dishevelled tranny. I reached up to my chin. No, I could never kiss him, not like this.

I slipped out of bed carefully and suddenly realised. I had no intention of changing, not back to Ben, not now. This morning I was going to for once carry on as I left off, 'being' Bethany. I crept quietly across to the bathroom and shut the door. I looked at my face in the mirror – help! I did indeed look a mess, this would not do.

It only took me ten minutes to re-do my make-up - I was surprised at how accustomed I had become to feminine habits and procedures. OK it's not very feminine to have to take off your wig to have a shower, or to have to be a little careful when washing not to be too rough on the covering cream around your tits - or indeed smoothing your face. But other things, taking my facial make-up off, getting made up again and all that entails, these things were beginning to become second nature to me. Not that it detracted from the thrill. I still even now get excited at the transformation which takes place as I carefully apply my eye-liner and mascara.

OK then, it took me more than ten minutes but it was certainly less than twenty. After which I crept naked back into the bedroom and found clean bra and panties, the lovely silk-like deep purple set I hadn't worn yet. Stockings and heels followed as night follows day, in true tranny fashion. Then Andrew stirred. I moved over to the bed and sat down beside him. He opened his eyes.

"Hi honey" I cooed and kissed him on the lips.

He smiled and a momentary expectation wobbled through my body. Sex? Again? Well, maybe? Did I interpret his smile correctly? I kissed him again and his left hand moved to caress my bum. Yes, he was definitely up for it again.

I reached my hand down under the covers. Up? Yes, big-time. I smiled and kissed him and then had second thoughts. I realised that he wasn't entirely 'free'. OK, I was still a student but Andrew was a working man. As we kissed and caroused I realised something else.

"Andrew. You smell! You are not having sex again with me like that, you absolutely must shower first."

"OK honey, as you want. Hell, is that the time?"

He had just noticed my little travel clock by the bed.

"Bethany, I'm so sorry. I'd warned Kate I might be a bit late today. But - one thing."

As he turned to look me in the eyes I realised he was wanting to be very serious. I waited.

"Look Bethany. About last night." I waited. "It was different for me. And it was oh so good, honest. I mean OK so I've been with guys and with girls before. But I made love to a woman last night so in a sense I'm not gay. But - well - you've got a cock, a beautiful cock so I'm definitely not straight. In fact I don't know what I am."

He was confused. I was – confused – but somehow the previous night had just begun to bring some clarity to me. To my life. To my dressing-up. SOME clarity, I realised I still had some way to go.

"Bethany, I've never been with a TV before. But whatever I am, I love it! So much of what we did last night really was a totally new experience. I don't want this to be just a one night stand. Please?"

I didn't say anything. I just kissed him lightly on the lips and smiled a smile which obviously said 'yes'. Then I slapped his lovely bum.

"So, lover. Get dressed."

Andrew hugged me once more and then disappeared into the bathroom. I slipped on my negligee, I wanted Andrew to see it before he went. I was definitely going to be Bethany all day, maybe even.... But that was for later, first things first, coffee! Absolutely essential first thing in the morning. As I moved towards my small kitchen I heard the chink of bottles outside the door. Somehow in the middle of everything which had been happening the previous evening I had remembered to put my milk bottles out. Today's was being delivered.

A very naughty thought came into my mind. I remembered a scenario so common in films, of the 'housewife' opening the door to greet the milkman while wearing very little by way of clothing. In fact in some types of film the favourite garment was a negligee very much like the one I was wearing. Very revealing, all tit and leg, I wondered just how old Pete would react if I opened the door to collect my milk at that very moment. I peeked through the gap in my curtains, he was bending over to pick up my empties. Dare I? I unlocked the door and reached for the handle.