tagTransgender & CrossdressersRebecca's First Date

Rebecca's First Date


Please read Chapter 1 first XXX

Chapter 2. The First Date.

Jasmine kissed me on the cheek and went upstairs. I smiled as I watched her pert bottom swing from side to side, encased in her tight grey pencil skirt, as she climbed each step. I turned and walked to our kitchen once she'd rounded the top of them and disappeared into our room. I wondered what she meant by leaving me a present as we were entering new territory in our relationship. When I had originally told her about my transvestism, she had been helpful and supportive but that had dwindled into disinterest over the years. However, with her sleeping with someone else and me getting ready to do the same, our relationship now seemed all fresh, exciting and now I had a present from her, something which hadn't happened for ages.

I thought I would wait until she came out before I went to look. I checked the time. "6:15pm" I thought to myself. In just over 2 hours, I would be meeting a man with the sole intention of getting myself fucked senseless. My legs started to tremble at the vision. The fantasy of going with a man and having him use me for his pleasure was totally divine but I couldn't help worry that maybe reality would be somewhat less of an experience.

Just then, my mobile rang. "Fuck!" I said, startled out of my day-dreaming. I looked at the number, it was Mike. "Oh great, he is going to cancel. That's just fucking typical of my luck. I have a great day, my make-up is perfect, my wife is happy and knows everything and now this!"

I pressed accept call and spoke harshly. "Hi, I take it you're going to cancel tonight?"

"Hi" he said laughing. "Of course I'm not cancelling, although I do have a slight confession to make."

"Confession?" I asked.

"Yes, but don't worry, its nothing terrible and I'm pretty sure you're going to love it!"

"Tell me then!" I said excitedly.

"Well...." He started.

"Oooooh come on babe, don't keep me in suspense. Tell me please."

"Well" he continued. "I've spoken to your wife and she thinks it would be a good idea that, as its our first date, that I should pick you up from your house. She has given me your address and if you are wondering about how I've spoken with her, she rang me and explained everything, especially how you don't clear your chat histories, which is where she got my number. I can tell you though it was a fucking shock hearing from her!" he laughed. "So? What do you think? Pick you up at yours at 8pm? Or do you need longer to get ready?" he said cheekily.

"Picking me up from home would be perfect babe. I cant wait to see you!" I said eagerly.

"OK babe. 8pm on the dot. I cant wait either." and then he ended the call.

I went to the fridge to get myself a beer. As I was just about to open it, I noticed my purple nails. "Silly girl. We don't drink out of beer cans anymore now do we?" I said to myself rhetorically. I put the can back and pulled out a bottle of wine. I poured myself a glass and then thought I should do one for Jasmine as well.

As I reached the top of the stairs, I had a sneak peak into our room to see what the present was that she had left me. It was a box. A pink square box. Curiosity piqued, I decided to leave it for now and went into our bathroom.

"Glass of wine?" I said.

"Mmmmm lovely, yes please."

"Mike rang." I stated as I sat down on the closed toilet seat.

"Really?" she said and then burst out laughing. "Oh sweetheart, you don't mind do you? I thought it would be easier especially as the main reason you were leaving at 8 was so you didn't meet the girls, but they aren't and never were coming."

"Its totally fine." I smiled "although when he rang and I saw his number, I did think he was going to cancel as today has just gone too perfectly, so I was totally happy when he said he was coming here".

"Do you know that I have never seen you happier than you are right now. You really should have done this much sooner Rebecca."

"Really? But how? When you marry someone it's supposed to be for the rest of your life and the last thing you should expect for yourself is to want to go off with someone the same sex."

"Same sex?" Jasmine said surprised. "You still consider yourself male then?"

"Fucking hell! That's a question and a half." I said. "I don't know. I really don't know. There's really nothing about being a man that I like. I guess I just get on with life a day at a time, try not to think about it too much and enjoy my time spent as Rebecca." I was just about to drink some of my wine when Jasmine stopped me.

"Get a straw or you will smear your face. You're shaking like a leaf. I bet you have a thousand conflicting thoughts zooming around that pretty little head of yours don't you?"

"Yeah babe. I've wanted to do this for years and now its finally happening, I guess I am a little overwhelmed. Plus, I'm worried about how this is going to affect us."

"I told you Rebecca, this is NOT going to change anything about us, except maybe for our sleeping partners." She giggled.

I smiled back. "Yeah. You're right. Lets just think of this as the first day of the ...bleeeuuurrrrgh...I hate clichés!" I laughed.

I went to the kitchen to get a straw and when I came back, Jasmine had left the bathroom and was in our bedroom.

She looked at me and excitedly said "Open the box, open the box!"

"Ok Ok OK!" I grinned and reached for the box. "Now, what do we have here?"

I pulled the pink ribbon and opened the lid. Inside, nestled amongst the softest crepe paper, was the black, silk, full length Victoria's Secrets nightdress that I had been after for months.

"Oh my god wow, its beautiful and more perfect in the flesh than in those pictures. You got this from America?"

"Of course. I knew you would love it and there's the silk thong that matches as well. Now have you packed your overnight bag yet?

"Overnight bag?" I exclaimed. "I never thought...do I need one?"

"Of course you do silly, lets do it now and then you can start getting dressed as you only have an hour till he gets here."

Jasmine pulled out our smallest leather suitcase and opened it on the floor. "Right!" she said. "You're going to need a change of clothes to come home in tomorrow. I think a simple blouse and skirt with some low heeled shoes should do and you will need more make-up, brushes, perfume, lingerie..."

"I'm coming home dressed as Rebecca in broad daylight. Are you mad? I cried. "What about the neighbours? What do we say to them? And, when was it decided that I was staying out overnight?"

"OK first things first. Why not stay out all night? You should be free to do whatever you want and if worrying about coming home is an issue, well its not. As for the neighbours, fuck them, its none of their damn business anyway. In any event, I want Rebecca around here more often, possibly full time...." She left that sentence hanging in the air.

"Full time?" I wondered to myself. "Could I do that?" I asked her.

"I don't see why not. We can get you to a specialist to talk about it if you want and see what you want to do. I will support you with whatever choice you make, you need to be happy and true to yourself."

"I'll have to give it a lot of thought." I told her. "Although it will be strange changing from Rebecca to plain old me just to go to work."

"When I said full time, I was including work. We will just have to be open with them. Maybe your boss could do with a new secretary that sucks cock when asked." she laughed.

"Yuk" I grimaced. "Can you imagine me sat under Fat Bob's desk slurping and sucking on his dick, begging him to shoot his jizz down my throat?

Jasmine covered her mouth trying to suppress a laugh. "Oh yes babe I can definitely imagine you doing that. You know he has a big fat long cock don't you? He tried it on with me once at that crimbo party a few years back. I was outside having a smoke and he came out, put his hand up my dress and grabbed my bum. When I tried to smack his hand away, he moved it and my hand hit his dick. The dirty bastard had it already hanging out of his pants!"

"Hahaha" I said. "You never told me that. Maybe you're right, maybe I could suck his dick if it's a big one" I said sultrily.

"That's my girl! Now, enough fucking about! I've left the enema kit in the bathroom, go sort it out. It will take about twenty minutes but if you have any problems, call me but don't expect me to come." She sniggered.

I laughed at her and went to do the dirty but necessary deed. "I seriously need to consider what I eat in future." I said to myself once I'd finished and left the bathroom.

Jasmine had packed my overnight bag and told me that there were a couple of outfits plus all the other items she said I really should take with me. I kissed her on the cheek and then said "OK! Time to get ready."

I took off my white satin robe and then pulled off my panties. Jasmine looked at me and smiled. "There's just one more thing you need to make tonight even easier."

"...and that would be...?" I asked.

"Bend over the bed sweetheart and I'll show you."

Knowing that she was enjoying this as much as I was, I did as I was told. I heard a squelching sound behind me and then a cold wet substance being rubbed gently around and then inside my bum hole. I then understood that she was preparing me for Mike, as she then slid in, what seemed to me to be a fairly large butt plug.

"There you go babe. That should make it less painful for when he gets inside your knickers!"

"Good job I am all clean then!" I said poking my tongue out at her.

"Drink your wine, have a ciggie and finish getting ready. Its nearly time." She said as she left the room.

I went over to the vanity table and checked myself. Everything still looked perfect. Hair and make-up were flawless. "I want to look like this forever." I said out loud. I lit a cigarette, popped the straw into my wine and had a long slurp. I felt calmer. The butterflies had gone and I was now looking forward to whatever lay ahead, both tonight and the future. I reached onto the vanity unit and grabbed my body spray. Alyssa Ashley musk. A totally delicious scent and sprayed myself all over. "Mmmmm I smell like a little piece of heaven."

I got up and picked the suspender belt off the bed. I placed it around my waist the wrong way around to fasten and then turned it the proper way and adjusted it so it sat nicely just on my hips. I then picked up the stockings. These were my favourite brand of stockings. Aristoc with an A woven into the lace. So feminine and sexy and, as I remembered, worn by an awful lot of porn stars. I had to be very careful with them, they were so delicate and sheer that the slightest pull the wrong way would result in a tear.

I then pulled on the waist clincher. With all of my body hair removed, the material tingled and tickled my skin almost causing me to shudder. "God. I love this feeling." I thought as I pulled the laces tight.

I looked at my bra. This was the item that made me feel most like a girl. When I had it on and my breasts produced my cleavage, that's when I became Rebecca. This time, however, when I put it on, I knew I wanted to be Rebecca forever.

The most uncomfortable item was next. I love my gaffe, but even though I have been pushing my testicles up inside me for years, it still felt strange. Pulling my little dick back between my legs and fixing it in position cheered me up as it was now out of sight. "The only dick that should be between my legs, is someone else's." I thought.

My blouse was next and I definitely felt myself shudder as I slid it over my shoulders. As I buttoned up the front, I looked into the mirror and was pleased when I saw my breasts almost bursting out of the blouse.

The satin fishtail skirt was my absolute favourite. I loved how it clung to my bum and the sound it made as I walked when it rubbed against my stockings. I stepped into it, made sure that my blouse was tucked inside and then pulled up the zip at the back. Looking into the mirror I noticed that my blouse wasn't quite even, so I lifted the skirt, adjusted the blouse evenly and as I was about to lower my skirt, I saw my reflection. "Mike baby. I cant wait for you to start getting your hands up my skirt and onto my body."

I pulled my skirt down and reached for my shoes. I hadn't worn these for a while, but despite their height, they were very comfortable and looked amazing on.

I then opened my jewellery drawer and put on my necklace, my drop earrings, bracelet, ankle chain and watch. I was almost ready. I lit another cigarette as the other one had burned down to nothing. Another slurp on the wine followed just to calm the nerves which were almost coming back.

I grabbed my handbag and after refreshing my lips with the gorgeous lipstick the wonderful woman from the salon had given me, placed it inside. I also noticed a purse inside that wasn't mine. "Another present from Jasmine." I smiled as I opened it to find £100 inside with a note saying "Just in case, love you, Jasmine xxx."

I opened my bottle of perfume dabbed some behind my ears, neck and cleavage. I placed some on my wrist and rubbed it against my other one mimicking what I had seen Jasmine do thousands of time before.

I took one last long look in the mirror and whispered. "Tonight Rebecca. You are becoming what you have longed for but have denied yourself for so long. Enjoy and embrace it"

I took my jacket off the hanger, grabbed my handbag, the overnight case and my cigarettes and went downstairs. Time was now 7:50pm.

As I entered the front room I was met with a bright flash. "Smile baby, you're going to want to have these photos as a reminder of the day you became the true you."

"Go on then!" I laughed and began following her instructions on how to pose, pout and tease the camera.

"A total natural" she said delightedly.

The doorbell rang and my heart almost stopped. "Its him!" I beamed.

"Put your jacket on while I go and let him in." she said heading towards the front door. I did as she said and by the time she had brought Mike into the living room, I was ready.

Mike came straight up to me, took my hand and kissed it softly, all the time looking right into my eyes. I could feel myself blush. He smiled at me and said "I knew you were beautiful but how you look now is just ..... perfect. I am a very lucky man!"

"Go on then you two, out out out, go have a wonderful time and Mike please be a darling and put Rebecca's overnight case in your car."

Mike laughed as he picked up my case saying "have you got a months supply of stuff in here?"

"A girl changes her mind as to what she wants to wear. I'm just pre-empting any problems I may have in the morning." I giggled, following him to the door.

"Have fun darling." Jasmine said as kissed me on the cheek. "See you tomorrow." She closed the door.

Mike walked down our driveway, opened his car and placed my case into the boot. I followed him down the path, loving the sound of my heels as they clicked on the pavers. I noticed that the car was parked right under a street light. "This could be interesting for the neighbours." I said with some apprehension. He opened the passenger door and helped me inside. I suddenly realised why he had parked here. It would be very well lit as I sat down and although I wanted to try and be ladylike I couldn't resist conceding to his unspoken desire so I opened my legs to allow him to see up my skirt hinting at the delights contained therein. He smiled at me, closed my door and went around the car and got into the drivers seat.

"I have been walking around in a daze ever since we made this date. I've not been able to concentrate at work and, if you don't mind me saying, my dick has been constantly hard and throbbing just waiting for you." he said hungrily.

"Well, we are going to make that all better for you tonight sweetheart. Now where are you taking me?" I asked.

"That's a surprise!" he said "A man needs to impress a beautiful woman on their first date and I have a lot planned tonight."

"Mmmmm a magical mystery tour. I like the sound of that."

"You look fucking gorgeous tonight! He exclaimed. "I cant wait till I get you in my arms and make you feel like a woman should.

"You don't look so bad yourself. In fact, I would go so far as to say if I was a real woman I would have to take my panties off as they would be soaking wet." I laughed.

He started the car and headed towards the main A38. We made small talk for a little while until he reached over and placed his hand on my leg, making gentle rubbing motions. It felt wonderful so I decided to return the favour and started rubbing the inside of his thigh moving my hand up and down, almost reaching his groin.

"Damn you're a tease!" he said lustfully.

"Tell me what you want babe and I'll do it!" I purred back.

"Get it out and do what comes naturally you bad girl." he said.

I reached over with both hands and started massaging his bulge through his trousers. I was impressed. It was hot, unyielding and felt really thick. I hadn't even realised that this was the first time I had willingly started touching another man's genitals.

Mike was moaning and telling me how good it felt to have my hands on him at long last. I found his zip, tugged it all the way down and reached in until I found his hard throbbing dick. I pulled it out tenderly and looked. It looked perfect, no foreskin and a big purple head that had a wonderful shape.

I began to rub it up and down, mesmerized by the way it twitched. I licked my fingers and then placed them back onto his shiny helmet.

"Oh fuck yeah, that's its, get it all slippery you dirty bitch!" he groaned.

I thought I would go one better than that and undid my seat belt and leaned over and flicked my tongue over it. It had the most amazing flavour. I wanted more but couldn't quite get my mouth over it as the steering wheel was getting in my way.

"Don't worry babe, I'll pull over into lay-by!" he said breathlessly.

I continued to rub his dick and after what seemed an eternity, he turned the indicator on and pulled off the road.

"Now this is a bit of luck!" he said.

"What do you mean?" I asked.

"Its one of those secluded lay-bys and there are no other cars here!"

"Perfect!" I said.

He stopped the car. Turned off the lights, undid his seat belt and pushed his seat back.

"My dear Rebecca, push your seat back and get that wonderful mouth of yours over my dick!"

I didn't need to be asked twice and having moved my seat, I quickly lowered my head into his lap. The manly smell of his dick was driving me wild and I could think of nothing else other than pleasuring him to the best of my ability. I ran my tongue all around the rim of his exposed glans. I loved the taste of his cock, I especially loved licking the clear fluid that was leaking out of the tip.

Mike stopped me and pulled his trousers down. He looked at me, pulled me closer and started to gently kiss me. I felt so vulnerable in his arms and loved the feeling. His tongue entered my mouth and I sucked on it hard, hinting to him that I wanted to go back to sucking him off. He took hold of my head and pushed me down onto him again. This time I could hold his balls. They felt heavy and I knew that he must have not masturbated for a while, saving it all for me. I used my left hand to massage his balls whilst my other jerked him into my mouth. Swirling my tongue around his dick for a few minutes sent him wild until he just grabbed my head and pushed me right down till my nose was tickled by his pubic hair. He then started thrusting hard in and out of my mouth and all I could do was hold my mouth open and use my tongue as best I could.

"So this is what its like to be face fucked!" I mused. "I could definitely get used to this."

I was getting so into it that when his dick swelled in my mouth I almost didn't notice, concentrating as I was on giving him as much stimulation as I could. The first spurt came just as the tip of his dick was coming back into my mouth. My tongue was covered instantly and the taste overwhelmed me. "Cum." I decided, "is going to be my favourite meal from now on."

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byRebeccaTG© 6 comments/ 27282 views/ 11 favorites

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