Sissy Finds a Friend

Andrew likes to wear women's clothes in the privacy of his home. He finds he's more comfortable dressed as a woman, and wearing frilly clothes makes his cock stiffen up nicely.

He's been married to Wendy for ten years now. She discovered his fetish by accident six months ago and has come to accept his need to cross dress. When she returned home early one day and found him en femme she was a little surprised although there had been occasions in their marriage when she had wondered about his eccentric behaviour. She'd asked herself if Andrew could be bisexual. He's small in stature and has difficulty buying clothes to fit him. He'll buy jeans and other trousers from the women's section of a department store and he loves Hawaiian shirts or flowery patterned tops with lots of fabric in them rather like a woman's blouse. When he cooks for her he always puts on one of her pink flowery aprons.

"We'll talk about this later." she said frowning, trying to suppress a grin. She'd come in the house unexpectedly. His face was scarlet and she could see he was frightened about her reaction now that his guilty secret was out in the open. As she changed out of her business suit into something more comfortable upstairs in the bedroom her quick mind was calculating what to say to him. Looking around she saw Andrew had left his male clothes on the bedroom floor. He can't change out of my things she realised. I've got him on the back foot. He'll be anxious to please me, more amenable to go along with some of my more daring plans. Her pussy moistened a little. Perhaps there's a way we can improve our sex life. She tried to work out when they last fucked deciding it must have been about a month ago. It's no wonder I'm so horny all the time. She almost said the words out loud.

Wendy finds sex with her rabbit vibrator unsatisfactory. She prefers the real thing. She loves Andrew but over past months has been responding to the attentions of two or three of her male colleagues at work without actually breaching her marriage vows. She's always been the kind of attractive woman that men can't stop lusting after. The men flirt with her as a matter of course without expecting to get anywhere. Just lately she's flirted back. It's given her thoughts to help her when she masturbates. There's one particular member of staff she's often fantasised about. She began thinking about him, her face heating up and her hand moving to her pussy. She was still just in her bra and panties. Moving to the full length mirror she stroked herself as she considered how she could turn Andrew's cross dressing to her advantage. Ideas were popping in and out of her head one after another. She smiled to herself having made her decision. She put her casual clothes on and went back downstairs.

Andrew stood up as she entered the living room and moved towards the stairs.

"Stop right there. You can stay in my clothes for now."

"Pull up your skirt sweetie let's see what you're wearing underneath." Andrew complied looking rather sorry for himself.

"Those are my best panties. The ones I wear with that micro mini skirt. I can't possibly wear them again. I'll be thinking about you in them. In future you'll buy your own things. Is that clear? And whilst you're in the shop you'll get me an adequate replacement for those knickers you've got on."

"Yes of course Wendy, Erm, do you think I could send for them on line? I'd find it embarrassing paying at the till."

"Certainly not. If you're going to be a sissy shop assistants should be able to laugh about it. I expect you'll get a stiffy if the girl at the check out smiles knowingly. Isn't that true dear?"

"I expect so." Andrew said. He's a little uncertain but can't deny the idea is arousing him. "You won't tell our friends will you?"

Wendy grinned as she saw his penis rising inside her best panties.

"Not right away darling. I might mention it to my best friend Joanna. She's usually good at keeping secrets. If I know her she'll want to see you in all your frillies. I think you might enjoy that. You like Joanna don't you sweetie? Don't deny it." Andrew's penis stiffened at the thought of Joanna seeing him dressed.

"Yes, Joanna's very nice. I think she might understand and not judge me." His voice is soft, almost feminine.

"Joanna's got a soft spot for you. She always said you were too pretty to be a man. Maybe she was right."

"Switch the TV on and I'll start on the meal. I'll want you to do more of the domestic chores from now on. I expect you'll prefer it that way won't you?"

"Yes Wendy."

"Keep the outfit on until we go to bed. I need to get used to the new you. I'll admit the kinkiness of it is quite intriguing. No wanking when I'm out of the room. I'll want to give you a good rogering tonight sweetie so I'll want your cock nice and stiff."

Andrew was astounded by Wendy's accepting attitude. He'd always assumed she'd kick him out if she ever discovered what he thought of as his dirty little secret. He couldn't concentrate on the television so went through into the kitchen and began to wash and peel the vegetables for dinner. Wendy was tired after a busy day at work and soon allowed him to take over preparing the whole meal. Flopping down on the settee she moved her bottom back and forward rhythmically causing lovely sensations in her sopping cunt. This time she avoided using her fingers. She was looking forward to putting Andrew into one of her nightdresses later that evening.

For his part Andrew was also anticipating their upcoming intimacy. He considered the words she'd used as if SHE'D be fucking HIM. He knew he was submissive by nature and wanted Wendy to take a more dominant role. And not just in the bedroom.

"I've laid out three of my nighties I don't wear any more. Choose one and put it on." They were now in the bedroom and Andrew was standing in front of her in just the panties. He went for the short baby doll one in pink.

"Lay on the bed on your back sweetie." Quickly pulling down the panties her hubby was wearing and removing her own she lowered herself slowly onto the cock as it stood up nicely for her squishy pussy.

"I've had second thoughts darling. We'll go shopping together. If I'm going to feminise you I'd like to choose your outfits. I can have fun with the staff in the store. They'll enjoy having a sissy as a customer."

Andrew loved having Wendy on top of him as she began riding him, moving slowly up and down on his cock . He could hardly object to her offer to shop with him. He wished he'd been honest about his interest in cross dressing. He found his penis maintaining stiffness helped by her comments. Did he hear right? Did she say she is going to feminise me?

"Of course sissies just love to lick their wives' pussies don't they dear? You want to fully embrace the lifestyle don't you?"

"Er, yes, I guess so." He answered a little doubtfully.

"Well we'd better start today. My cunt will be rather smelly and full of your cum after you've spurted. But I want you down there licking until I've had at least two orgasms." She increased the speed of her thrusting thinking with satisfaction that hubby's cock was stiffer than usual.

Andrew generally turned to face the other way and go to sleep after spurting. Until Wendy found out about his dressing up they always fucked under the duvet. Like most men his cock usually goes flaccid immediately after his climax leaving him with no further interest in anything sexual. There was a strange thrill being ordered to do something he didn't want to do. Wendy wasn't usually so forceful but female clothing made him feel more submissive. Yes he had to do it but he didn't like the idea. The expression on his face would have been obvious to Wendy had she not been riding him cowgirl style.

"I'd like that dear." He lied.

"Good girl. Think of it as a test sweetie. Sissies must please their mistresses at all times." At the mention of the word 'sissy' and 'mistress' Andrew squirted into his wife grunting and jerking, his body momentarily out of control.

Without further prompting he knelt in front of her as she perched on the edge of the bed, her legs splayed wide. She grabbed his head and pulled it forward onto her dripping cunt, holding him there roughly as he tried to lick inside her folds.

"That's it lick your sperm out of me. Savour the taste of it. You'll soon get to love the taste of cum."

It wasn't so bad after all. Andrew particularly enjoyed Wendy taking charge. It excited him, and he realised he'd always craved it. She was using him purely for her own satisfaction, not his. He redoubled his efforts to please and excite her and she was soon bucking and thrashing through her first orgasm.

Their trip the next day to buy him his new outfits was also very exciting for him. He loved walking through the area selling panties, isles of them in all shapes and sizes.

"I expect you'll prefer the pink frilly ones sweetie. Am I right?" Andrew nodded looking around to see if her words had been overheard. He saw another shopper turning towards them. She met his gaze and smiled. He felt his cock stiffening. Wendy noticed the woman and approached her.

"I'm helping my sissy husband buy some female clothing. I caught him trying mine on yesterday. I decided he needs some of his own."

The woman grinned, nodding. "Very sensible", she said. Andrew saw her walk towards a man hovering near the edge of the women's clothing section. She whispered something in his ear and they both laughed. He felt his erect cock jerk.

They picked out seven pairs of frilly knickers then moved over to the bras, skirts and blouses. After finding suitable items Wendy spotted a dress she thought would suit a sissy.

"We'd better use the fitting rooms. You'll need to get the right size darling. Hang on whilst I explain to the attendant."

It was quiet in the store. The member of staff agreed deciding to close the fitting room area for a short time ushering them in. Andrew's belly sticks out just a little. They found her choice of dress in the right size but with a slight bulge in the front. Wendy asked the advice of the attendant.

"I expect you were planning to buy her a suspender belt?" she said grinning.

Wendy smiled, pleased her husband is being referred to as she. "Yes, she'll need stockings of course."

"Well in that case could I suggest a girdle instead? It'll bring her tummy in and make her feel more girly. They come with fasteners for the stockings."

"Excellent idea." Wendy said ignoring Andrew. She was right in assuming he would go along with the suggestion but he thought she might have asked for his opinion. He had noticed his drop in status since Wendy found out about his cross dressing. When he thought about it he realised he was okay with it. There was a sexual component to his feelings.

They came out of the store laden down with their purchases. Two girdles and five pairs of stockings completed their items..

"From now on you'll wear panties and stockings every day sweetie. You can put your male clothes over them when you're at work or out of the house but I'll expect you in your feminine things around the house. Okay?"

"Yes dear."

Wearing stockings and panties all the time kept Andrew in a state of constant arousal. And sexual play with his wife was far more frequent than before. The focus was on Wendy's pleasure rather than his own so quite often she'd climb off his cock after she was satisfied leaving him with a raging hard on. She'd often turn over in their bed fully aware of his frustration.

"Rub it like you do when you're watching porn," she'd say with her back to him. She'd giggle when she heard him cum.

"Good girl," she'd say then fall asleep.

Increasingly though she'd insist on his tongue between her legs. This was often with him lying on his back, sitting on his face. Sometimes she'd give him a hand job rather than penetrative sex. On other occasions she'd leave him to his own devices.

____________________________________________________________________

It's now six months since his cross dressing came to Wendy's attention. Andrew is reasonably happy with his life. He loves it when Joanna comes around for a meal. She's so kind to him and he's always en femme when she calls. As far as he's aware none of their other friends are aware of his secret. Joanna approves of Wendy's new attitude saying that women are superior to men and it's only right that they should be in charge in any marriage.

One day at breakfast Wendy mentions something that's been on her mind.

"Andrew, there's a guy at work, he's called Jonathon, I'm feeling a bit sorry for him. He's been split up from his wife for a few months and seems to be taking it badly. Do you think we could invite him round for a meal one evening. It might cheer him up. He doesn't seem to have many friends."

"Okay dear, it's kind of you. We don't entertain guests as much as we used to. I'll put some male clothes on for the evening."

"Yes dear, I think you'd better," she says. "How about this Friday night? There's nothing in the diary."

"Perfect."

Wendy doesn't know Jonathon very well. He hardly ever speaks to anyone in the office, just gets on with his work. He does look unhappy at times so her concern for him is genuine. There's something about him that makes her nervous but she can't make out what it is. She's always had a kind nature and has decided to do what she feels is the right thing in spite of her reservations.

Jonathon arrives later than planned full of apologies. Wendy notices he's made an effort to spruce himself up a bit as he often looks scruffy around the office. The conversation centres around him, he seems to enjoy talking about himself but is less interested in their lives.

"Yes me and Mary split up." He says offhandedly. "My fault I'm afraid. She didn't like the way I bullied her nor my tom catting around. She won't speak to me now. I'm okay with it. My motto is, there's plenty more fish in the sea."

As he says this he looks directly at Wendy. Their eyes meet for a second but she turns away. She's surprised about what he has just said. He's not the person she thought he was. Does he have designs on me she wonders? I hope not, she decides. I'm not attracted to bullies. There's a pregnant silence.

Wendy searches around for something to say, she hates silences. Then she blurts out.

"I was bullied when I was fifteen. She was in the form above me."

"An older girl? What did she do to you?" Suddenly Jonathon is showing an interest.

"Oh, you know, the usual sort of thing. Name calling, isolating me from the other girls. Remarking on my clothing and my appearance. I was overweight then."

"What name did she call you?"

Wendy wishes she hadn't revealed this part of her past, but feels it would be rude not to answer.

"Nothing original, Fat slag was one name. The strange thing was she'd behave like that with the other kids there but if we were alone together it was different."

"How was it different?" Jonathon is like a dog with a bone. Andrew keeps quiet. Wendy hasn't spoken about that part of her life.

"She'd be all pally pally, sidling up to me, stroking my hair, whispering things, stroking my knee. She wanted to see me after school but I always said 'No'. I couldn't trust her. It's like she had a split personality."

"But you wanted to go didn't you?" Wendy shakes her head. "Didn't you?" Jonathon says this louder.

"Yes."

"Because you were sexually attracted to her weren't you?"

"No, certainly not." She's red in the face now.

Both men realise she's lying. Andrew is surprised, he's not seen Wendy's submissive side. Wendy leaves the room saying she needs the toilet. Jonathon has affected her. She'd never had a conversation like that with a man. Her panties are soaking and she can't work out why.

When she returns she pours herself another glass of wine, her third, and takes a big gulp. They finish the meal, the conversation returning to less controversial comments. Jonathon offers to help them clear away but they say to leave it. They move into the living room, Andrew and Wendy on the settee, Jonathon in an easy chair opposite.

The conversation starts off light hearted mostly between Jonathon and Wendy. Then they get on to talking about different characters in the office and Andrew feels left out. He notices that Wendy's miniskirt has ridden up her thighs and Jonathon is staring at her lovely legs. He finds Jonathon's attitude and behaviour arrogant but is soon distracted thinking about what the man can see up Wendy's skirt. The conversation takes a new turn. Jonathon says;

"You've got very attractive legs."

"Thank you." Wendy readjusts the skirt pulling it back towards her knees.

"Don't do that, I was enjoying the view. Do you like showing off your body?"

Andrew rouses himself from his reverie. He's disappointed she's pulled her skirt down but decides to keep quiet.

Wendy blushes. "Sometimes."

"Your hubby liked you showing a bit of leg. He thinks your panties might have been on display."

"Don't be silly." Wendy feels her face getting hot.

"Well I'd like to know their colour."

"Pale blue."

"Let me see." Wendy shakes her head. She can't look at Jonathon.

"Hubby doesn't mind. Do you Andrew?"

Andrew shrugs. His penis overriding his better judgement. It's no big deal he rationalises, men have seen her in a bikini after all.

Wendy looks at Andrew. She sighs then hitches up her skirt showing her panties. Andrew is aware of a stiffening.

"There that wasn't too difficult was it?

"No" Her legs are slightly open. She puts her knees together.

"No, don't close your legs. Move them wider apart."

Wendy opens her legs wide. She's feeling flustered.

"Matching bra?"

"Yes." Andrew has had a fantasy on similar lines to this for a few years now but in his imagination he would be telling Wendy to show herself to another man. This man he doesn't know is in charge and somehow it feels even even more arousing.

"Show me."

She unbuttons her blouse halfway, opens it up for him.

"Undo all the buttons."

She does, opening her blouse fully for him

"Do you want to see more?" Wendy says.

"Yes, of course" They both look towards Andrew.

Andrew can't trust himself to speak so he just nods. He knows he's in dangerous territory but Wendy seems to want to show more and it's what he wants too.

She unfastens the front clasp of her bra and pulls the cups off her breasts exposing them to both men.

"You have beautiful tits. Your nipples are standing proud aren't they? Are you cold Wendy?"

"No, I'm hot."

Jonathon smiles broadly. "Touch them for me." He watches her squeeze and stroke them making them even bigger.

"Good girl. Now slip out of your panties and touch yourself there."

She's gone beyond seeking Andrew's approval. Her thumbs slide inside the elastic waist and she lifts her bottom off the settee pushing them down around her ankles. She opens her legs wide for him.

"I see you don't shave."

"No, I just trim it occasionally."

Her finger slips inside her folds. Looking up she sees that Jonathon has taken his cock out. Her eyes are glued to it as she strokes herself. She's so aroused at being instructed in this way and is soon on the brink of orgasm.

"Release your cock Andrew." Jonathon says.

Andrew unzips. His prick feels like a rod of iron in his fingers.

There's a ping from Jonathon's phone. It's a text message telling him his taxi is waiting outside. His smug smile never leaves his face. He zips himself up and walks to the door.

"Finish her off for me Andrew there's a good chap."

As he closes the front door Wendy points to the floor in front of her.

Andrew kneels for her and gets his tongue to work. It doesn't take long for her to have the best orgasm she's had in months.