Tim's Transforming Weekend Ch. 02

Jean smiled affectionately. It had been hard acting this dominant woman that wasn't really her character. She had loved it. "I think that's enough for you this evening. You need a shower. Relax. And I know you and the girls are out tomorrow evening, and planning to take Tim with you. I might not see you in the morning - out early to see my mother! Goodnight."

Tim didn't notice the next few moments. They were planning to take him out? Normally Melanie and her three "Saturday evening" friends just ignored him. They were hot, all of them, but would never take him out. Now they were taking him out. How? Why?

Melanie was preparing Tim to go out on the town "with the girls." She had given him clothes to wear. Not what he would normally wear. Black fishnet stockings, panties, suspenders and bra. Pink mini-skirt. Pink blouse. She had given him a black wig which looked pretty realistic, as the hair tumbled over his shoulders. She was applying his make-up. Eyeshadow, blusher, bright red lip-stick. He had been embarrassed when she had tied a pink ribbon in a bow around his cock and balls, tying it into his pubic hair so it wouldn't slip off, but she had done it almost dispassionately, despite his cock twitching as she did it. As he sat on the stool in front of her dressing table mirror he pondered the evening before, which Melanie seemed to have fully recovered from before. He had watched his mother "fist" and make her submit to the most incredible orgasm he could imagine.

Then his mother had simply taken him to bed and they had fucked. Until the previous weekend he had never even dreamt of fucking her. The previous weekend had given him the dream, the night before - and earlier this morning - his dream had become a reality. He had caressed her pussy, licked her pussy, and three times filled her pussy with his cock and his cum! She was an amazing fuck, and she had left to visit her mother early, leaving his balls aching, but his mind yearning for more! However it wasn't to be - she had gone from her mother's to join her husband Keith for the night at his golfing hotel, leaving Tim in Melanie's hands.

Tim looked at the mirror - he looked like a girl! A woman. He had been transformed. He was a cross-dresser. Properly. He was a transvestite. His mind couldn't think what the difference might be.

"Okay, Tammy, you're ready. Taxi will be here in a few minutes." Tim noticed the "Tammy" - so that was going to be his "girlie" name. Somehow he felt so excited. He was going out "with the girls," and this evening he was going to be one.

Tim - Tammy - was terrified as they left in the car, but noticed the taxi driver look him up and down appreciatively. They had picked up the other three, and with a lot of giggling they had spent some time in a pub, before going on to a club. Tim - Tammy - had stayed very quiet but had enjoyed the company and the laughter. There had been one moment he had to think through when he needed a toilet, but ended up as discretely as possible going into the ladies, and no-one seemed to see anything out of the ordinary.

After the bar, they decided to take in a club. Again, no problem, allowed in, bought drinks, enjoyed dancing. As they were standing between dances a group of men in suits moved to them, asking for a dance. Tim, Tammy's heart banged and began to race with nerves. Then the music started, and Tim was dancing with one of them, finding himself separated from the others. The guy was getting friendly. Told Tim he was pretty, then told him he was sexy. At one stage Melanie came up behind the guy and mouthed "You okay?" and Tim nodded, so she moved back into the crowd.

And then the slow track started. The guy moved in, put his arms around Tim, and pulled him in to him. On one level Tim was excited, but also terrified. They danced closely together, and Tim felt the man put his hands on his ass. He then felt the man whisper in his ear: "You are so hot, hope we can get really close in a bit, hope we can have some hot fun..." Tim wasn't sure, nervous, then he felt the guy kiss him, pushing his lips to Tim's, pushing his tongue into Tim's mouth. Tim responded, although not sure what he should do.

For a moment the man released the kiss and whispered again in Tim's ear: "You are so hot I wanna fuck you, get my cock in your cunt..." He kissed again as they danced on wrapped around each other.

For a couple of dances they kissed, as the man played with Tim's ass. Then he felt the man put hand between them, then gently lifting the front of Tim's miniskirt. Then he felt the man grasp his cock through his panties...

The man let go and jumped away. "YOU'RE A FUCKING MAN" he screamed. "I'VE BEEN KISSING A FUCKING MAN!" The man swung a punch which caught Tim on the head, knocking him to the ground. As he hit the ground Tim covered his head with his hands as the man swung again at Tim, then tried to kick him in the stomach as others pulled him off. Within seconds the security guards had grabbed the man, and pinned him to the ground. Tim wasn't aware of this - he was semi-conscious, his arm in pain where a kick had landed.

The next few minutes were confused, although Melanie and her friends had made Tim comfortable. The police arrived to take the guy away, Tim was taken away in an ambulance.

The next morning Tim woke in a bed. At first he was confused as he looked around, then began to remember the previous evening. A nurse entered the room. She was perhaps in her late forties, smiling, friendly. She was pretty, but maybe had a "motherish" look, with her uniform and shoulder length black hair. She said she was called Anne-Marie, then explained he was concussed, that he had a broken arm, that it was about six in the morning and he was in a hospital room having come into casualty. She explained that he would probably be in hospital a couple of days, that the police would want to talk to him. Then she paused, looked slightly coy, before speaking. "You are not, um, dressed as you would expect. Do you want me to get some wipes to remove your make-up, get you some hospital clothes instead of, um, what you are wearing?"

Tim glanced to the mirror in single room where his bed was. He looked a state. Make-up smudged. Wig missing. "Yes please." Ten minutes later she had removed the make-up and cut away what was left of his clothes, handing him a hospital gown. Tim had helped as he could, but was still feeling groggy from the concussion, but in ten minutes he was a normal patient in a normal bed in a single hospital room...

"Um, do you want me to remove the bow?" Anne-Marie had spoken hesitantly. Tim was confused. Bow? What bow? It took a few moments for him to realise what she meant.

Before Tim could reply Anne-Marie had told him to lie back on the bed, and was looking at how the bow wrapped around his cock was fixed in place and tied to his pubic hair. She smiled again: "It's very cute!" Tim went bright red as she grasped his cock and lifted it so she could see under, and under his balls where there was a knot.

"Your mind might not be working properly, but other parts of you are!" Anne-Marie had said it with a smirk. Tim was mortified - his cock had twitched and begun to grow. This woman looking at his cock. Commenting on it. Holding it. Almost playing with it.

Anne-Marie seemed to almost ignore what was happening, and cut the bow away and threw it in the bin. "You'd better rest, and get some sleep. I've got other patients to look after. Might not see you again today, but I'll be on tomorrow night. Will see you then.

Tim did sleep, and then spend a day in the hospital, although by the afternoon he was feeling much better and his head clearing. His arm had been put in a plaster cast which hampered him a little. Jean his mother and Keith did come to see him, as did Melanie in the evening. The police came and talked to him briefly, and arranged to see him later in the week. The Doctor told him he could go home the following morning - another night's sleep would clear his concussion, and there was nothing that would help a broken arm in a cast. Tim felt sort of lucky it was his left arm that was broken - being right handed.

About 8pm after Melanie had left, the nurse - Anne-Marie put her head around the door of his room. "Still here? Hoped you would be - perhaps I'll get a few minutes with you after lights are out. Something I wanted to ask.

Tim got ready for sleep - which was a bit challenging with only one hand, but he was managing. He looked at his phone - nearly 11pm. A minute later Anne-Marie had come into his room and asked if he was happy to chat for a little - she had a blank space for a time.

Anne-Marie told him, with a smile on her face, that he was an unusual patient. Not often did they have patients dressed like him! Especially in his more private areas!

Tim blushed. "Can I ask a question?" Anne-Marie was looking slightly uncertain as she asked, but Tim nodded. "Why do you do it? Is it sexual? Or what is it?"

Tim wasn't sure why he did it, but over the next ten minutes he told Anne-Marie about how his life had changed over the last two weekends. About what he did with his step-father. With Melanie. Even mentioned that he had experimented with his mother.

After he finished Anne-Marie was again hesitant. "Tim, I've asked for a reason. I've been divorced for ages now, and have been bringing up Harry on my own. I thought things would go easier after he was growing up, and beyond his eighteenth birthday. But they aren't. I found a pair of my panties in the wash covered with, um stains. Then looked on his computer and he had been, um, photoshopping - and he had put my head on the body of a woman being, um, taken from behind. Then I looked in his wardrobe and found a couple of pairs of my panties and a bra I thought I had thrown out. Is it right for a boy to be, um, thinking about his mother and playing with her things. But there's more..." Anne-Marie paused.

Tim was trying to say what he thought, but she hadn't allowed a pause until now. "Dunno. But that's what boys are like, and you are a very sexy woman..." It was Anne-Marie's turn to blush, and threw Tim a glance...

"As I said there was, um, more. I thought I should be horrified, but I liked the thought of him thinking like that about me. I've wondered what it would be like having sex with him. That's so wrong." She paused, then moved on. "And then I was confused. I saw his diary where he said "I am a twink. I am a sissy. And a selfie of him wearing my panties."

Suddenly Anne-Marie stopped - realising what she was doing, noticing that Tim's blanket was tenting. They sat looking at each other, then Anne-Marie reached her hand slowly under the blanket from the side of the bed, and Tim felt her hand resting on his cock. He gasped. She was grasping his cock, wrapping her hand around it. She was smearing his precum on his cock so her hand slid easily up and down. She was wanking him, and his breathing was getting harsher.

For a few moments Anne-Marie slowly jerked him, but then got a little quicker. Tim was thrusting his cock up to meet her, but suddenly was aware of where he was. He knew he had to do something before he got to the point of no return. "Please stop, I'm going to make a mess. People will see it."

Anne-Marie stopped, suddenly realising what was going to happen. She paused, then pulled back his blanket, leant over his bed and took his cock showing through his boxers in her mouth.

It felt amazing, as she sucked his cock, caressing it with her tongue, squeezing his balls with her fingers. She was sliding her mouth up and down, letting Tim fuck her mouth. "I'm gonna cum..." he managed to say, but then was shooting his cum into her mouth, into her throat. Anne-Marie swallowed hard, not wanting to spill any to make a mess. She had forgotten how much cum a young lad can pump, but at last he came down from his orgasm, slumping and gasping for breath.

Anne-Marie smile, and when Tim had recovered spoke softly. "Can I bring Harry to see you? I think we would both find that helpful. Be nice to chat with your parents too..."

Tim pondered for a few moments. "Keith my stepdad is picking me up in the morning. Need to arrange it with him. Next week would be good."

Anne-Marie was gone, turning out his light as she went. Tim slept well. He had breakfast. Keith arrived to pick him up. He saw him talking to Anne-Marie, and then they were in the car - more recovery at home...