Rob Fulfils His Sissy Fantasy

Rob had always been fascinated by ladies underwear after he picked up a pair of his mum's and sniffed them. He also loved the feel of the material against his body. When he found his older sister's panties he was soon wearing them and pleasuring himself at the same time.

As he got older he would look at underwear as he walked round shops and was soon buying some for himself. He would put it on and stand in front of a full length mirror and admire himself while he wanked.

In the town that he lived there was a shop that was owned by his mum's best friend. Her name was Sally and as he was growing up he would call her auntie Sally.

The shop that he walked or drove past most days sold second hand clothing. Most of it was women's but also some men's. The window display was always women's which fascinated Rob.

He would sometimes see her outside the shop having a cigarette. He was always fascinated by the bright red lipstick she wore. Even though she was about the same age as him mum he fantasised about kissing her.

Eventually he braved up to go inside. As he browsed around Sally said, 'hi Rob, how are you, is there anything that you're particularly looking for?'

Rob felt very embarrassed as he said, 'I'm looking for some ladies clothing.'

'May I ask the age and size of the lucky lady. I may be able to help,' she replied.

Rob was suddenly unable to talk. Eventually he said, 'it's for me.'

'OK, that's fine, what have you got in mind,' she replied.

Before Rob could answer another customer came in and Rob said, 'I'll wait outside.'

After a few minutes Sally went outside and as they chatted she lit a cigarette. Rob was mesmerised as she put the cigarette between her scarlet red and sucked on it. Rob's mind was elsewhere.

She asked, 'do you just want a dress or a full sissy make over including make up and underwear?'

He replied, 'well to tell you the truth, I'd love a full makeover but please don't mention it to mum.'

'Of course not, your secrets safe with me,' she replied.

'Well I close at 1 o'clock why not wait until then, you don't really want people walking in and seeing you,' she said.

Rob waited patiently and as he went in on time she locked the door and pulled the blind down.

She said, 'I think you'll like these undies.'

She showed him a pink pair of panties which was fairly small and would barely cover his naughty bits but he like that idea. Next was a bra.

She said, 'I've got some padding that will look like you've got big tits.'

He embarrassingly stripped off in front of this woman he had known since he was a young lad. Even more embarrassing was that he was semi hard.

Sally said, 'the thought of this is clearly arousing you, don't worry about it.'

She asked, 'do you want to be dressed as a normal lady or as a sexy slut?'

'Oh, a slut definitely,' Rob replied.

Sally went into a back room and came out with various items of clothing. She said, 'as you'll be wearing stockings you need a suspender belt first.'

She slipped it around Rob's waist and fastened it then took a pair of fishnet stockings and said, 'sit down and I'll put them on for you.'

Sally knelt down in front of Rob and slowly pulled the stockings up his legs. She couldn't take her eyes off his fully erect cock which was now poking out the top of his pink panties.

She said, 'you know how when you were younger you called me auntie. Well I'd like you to call me auntie now.'

Rob replied, 'of course, auntie I like that.'

She made Rob stand up and still kneeling she reach up and clipped the suspenders to the stockings. She could feel herself getting aroused.

He sat down again and she put some red, high heel shoes with ankle straps on them. She helped him to his feet and said, 'parade in front of auntie, walk up and down, then look at yourself in the full length mirror.

As he did this Sally was getting even more aroused. Even though she had a good sex life with her husband the thought and sight of a virile young cock had her mind doing overtime.

Rob loved the sight of himself and his cock was clearly visible through his panties.

Sally then put a silky grey blouse on him and helped into a short skirt.

All it needed now was a wig and make up. A short blonde wig looked good on him. As she was about to put the make up on he said, 'can I have the same bright red as you as whenever I look at your lips I want to kiss you.'

'But I'm old enough to be your mum and you want to kiss me,' she asked.

'Yes, definitely, you have very kissable lips,' he replied.

'Well let's wait and see,' she replied.

She thickly applied the lipstick and some smoky grey eyeshadow.

Finally it was some padding for the bra. She said, 'my husband bought this for me, we were going out to a glamorous party and wanted me to exaggerate my tits.'

She pushed the filling into Rob's bra. He was now a sissy. She said, 'I think we both know what we need to do next,' pointing to his erection which was visible through his skirt.

'First I need a cigarette. I'm going outside, you can either come with me or admire yourself in the mirror. If you join me outside when we go back in I might let you kiss me. First of all I'm going to put some more lipstick on.'

Rob was reluctant to go outside dressed like he was but the thought of seeing auntie putting that cigarette between her kissable red lips was too hard to refuse and he warily followed her out.

She gave Rob the packet of cigarettes. He took one out and as she parted her lips he put it between them. She handed him the lighter and he lit the cigarette for her. Rob loved watching the white smoke blow out through her red lips.

As he stood there just looking at her smoking a woman came up to her and said, 'hello Sally, I didn't think you opened this afternoon.'

'I don't, I'm doing some stocktaking and my niece is helping me,' Sally replied.

The woman turned to Rob and said, 'hello.'

Rob nodded and smiled at her. Fortunately a minute later she moved on and Rob was pleased when Sally finished her cigarette and they went back in and locked the door.

She asked, 'so do you still want to kiss auntie?'

'Definitely,' Rob replied.

She had a quick inhale of breath freshener. Her lips were still lovely and red.

They held each other as their lips touched. Soon their mouths were open and tonguing each other. Rob's cock was throbbing under his skirt and then she reached for it. She loved the feel of it through his panties.

They stopped kissing, she knelt on the floor and pulled his skirt up and panties down. His large erect cock was in front of her face. She didn't hesitate and opened her mouth and took it in. They were both enjoying it when she stopped and said, 'auntie wants to pleasure you while you admire the sissy in the mirror.'

Rob stood in front of the full length mirror his erect cock sticking out in front of him. He felt auntie's hand grab hold of it.

He looked at his sissy self as she wanked his cock. It excited her too and she really wanted more than just wanking him.

He asked, 'can I feel your tits?'

She replied, 'first you just wanted to kiss me now you want to feel my tits, next you'll be wanting to fuck me, won't you.'

She replied, 'you want to feel auntie's tits then?'

'Yes, are you going to let me,' he asks.

Sally hesitates and then says, 'you can feel me, but nothing more.'

Rob feels her tits through her blouse and asks, 'can I take your bra off?'

'Well if you're going to feel them you might as well,' she replied.

In reality, as she rubbed his erect cock she wanted even more but couldn't possibly suggest it. She is a very happily married woman, why ever would she want a well endowed young man to fuck her!

The trouble was, her husband wasn't here but Rob was.

She felt her nipples hardening and getting wet between her legs.

She said, 'why don't you feel auntie's pussy, it's very wet. You'd better take my panties off so you can feel properly.'

Rob couldn't believe what he was hearing but happily did as he was told. He was shocked when he felt her.

He said, 'I didn't expect you to be shaven down there. You're very wet.'

Sally replied, 'my husband likes me shaven for when he licks and sucks my pussy.'

'And do you like him doing it to you?' Rob asks.

'I love it,' she replies. 'Why don't you taste me."

Rob couldn't believe what he was hearing. Here was this attractive woman old enough to be his mother and asking him to taste her cunt juices.

He put his head between her legs, he could see straight away how wet she was and as he got closer to her he could immediately smell her.

'Wow, your pussy smells wonderful,' Rob said.

She replied, 'call it auntie's cunt. I prefer that word. Now slowly lick up and down auntie's cunt lips.'

Rob couldn't believe what she was saying. At the same time she was rubbing his cock. He knew he was leaking precum and amazed he hadn't cum. But Sally knew where she wanted his cum and it certainly wasn't over her hand.

He started licking up and down her very wet slit. He loved the smell and taste of it. She stopped rubbing him, put her hands down below and held her cunt lips open and said, 'put your tongue inside me and lick me clean.'

Rob loved it as he licked inside her. He loved the taste of her juices as they seeped out and soaked his face.

She knew she was about to cum and as she put her hands round the back of Rob's head and pulled him tight against her she called out, 'auntie's cumming, suck my clit, oh fuck it's wonderful.'

She kept grinding her cunt against his face until she was empty. His face was saturated and she kissed him and licked her cum off his face.

She said, 'there's only one way for you to cum now and that's in auntie's cunt. So fuck me and don't worry if you cum straight away I just want to feel your cum spurting deep inside me.'

She was right, it wasn't long before he spurted deep inside her. He loved it.

Rob put his ordinary clothes back on and before Sally wiped his make up off she kissed him very passionately on the lips.

As they were about to leave Sally said,' same place, same time next week?'

'Yes, definitely Rob replied.