She Wears The Trousers

I knew that Wendy was a strong willed, ambitious woman when we met. She had been active in a left wing feminist group at University and had landed a good job with prospects after leaving. In contrast I am not a high achiever and dropped out of Uni after a couple of years. Since then I have had a number of low paid jobs and am presently unemployed. To be honest I am rather lazy and cannot understand what Wendy sees in me. I am happy for her to take most of the important decisions in our lives. Just lately she has suggested that I make a few changes to my appearance indicating that it might help our sexual relationship.

We met at a party and it was Wendy who picked me up. Wendy rarely wears skirts and on this occasion had on a smart, well cut jacket and trousers. She is tall and I remember staring at the level of her cleavage as I am a good six inches smaller than her.

I had been persuaded to wear a kilt to the party. Knowing I am Scottish some of my mates had dared me to wear it saying that women find them sexy. I had been on my own for some months and hoped I might find myself a girlfriend. As the night went on I realised it was hopeless as my shyness prevented me from talking to the women who were there. As usual most already seemed to be taken anyway. Wendy was on her own but seemed way out of my league. We made eye contact across the room and she smiled and appeared to be sizing me up. She strolled over and kissed me on the lips as if we knew each other.

"Can I buy you a drink, pretty boy?" She said "I want to know if what they say about Scots men and kilts is true."

She came back with a large glass of red wine (I had asked for a small one).

"Well, what about it?" she asked grinning "Let's go somewhere private and you can show me"

Having had a few drinks I was emboldened enough to say;

"How about if I show you mine you'll show me yours?"

Wendy was amused but just said; "We'll see."

Behind the locked bathroom door I hiked up my kilt to reveal an old fashioned pair of pale blue Y fronts.

"Oh dear." Wendy said "They will never do."

I still had both hands holding my kilt up and she quickly grasped the offending pants and pulled them off. I meekly lifted up each leg as she took them off me completely.

I let the kilt fall to hide my penis which had begun to stand to attention.

"Now you are a proper Scotsman" she said smiling broadly. "Just stay where you are, you can watch me have a pee."

Without any trace of embarrassment Wendy pulled down her slacks and panties and sat on the toilet. A huge flood of urine poured out of her as she sat with her legs open showing off her nicely trimmed pussy. I was entranced and more than a little aroused by her forward behaviour.

"Come over here and kneel in front of me. I want you to lick me please. You can wipe off the piss drips first if you like."

I knelt before her as instructed and paid homage to that wonderful part of her anatomy. This was a new experience for me but I loved the feeling of subservience to such a beautiful woman. My tongue explored inside the folds of her cunt and her clitoris became engorged with blood and rose up from it's hiding place.

"I hope you like my clittie Simon dear. It's quite big isn't it? I'd love it if you gave it a suck. Not too roughly. Be gentle with it like a good boy. That's it. Lovely."

I was able to get quite a lot of her clitoris in my mouth and gently sucked on it. Wendy was moaning with pleasure so I carried on until she orgasmed.

We went back into the party, drank some more and kissed and cuddled on a sofa until the party ended. Wendy insisted on throwing my underpants in the dustbin. She took pleasure in letting other guests catch glimpses of my bare backside as we danced. It embarrassed me but the alcohol helped me cope. I was so happy to be with Wendy and was hoping she would want to see me again. I was not to get a chance to bring myself off with her that night although I masturbated back at my flat to the memory of what had happened. I remembered the part of the night when the others were laughing at my bare bottom and it was a turn on. She had taken my mobile number and said she would ring soon.

She rang me a week later. Apparently she had a live in boyfriend but they had argued a lot and she had just thrown him out. She told me she was looking for a man who would be easier to get along with; someone fairly undemanding. We went out on a few dates and soon afterwards I moved in to her apartment. After the intimacy of our first meeting I expected frequent sexual intercourse but three months had passed and although we were sleeping in the same bed I had yet to achieve penetration of that delectable cunt of hers. I was happy being with Wendy. She was good fun, with a wicked sense of humour and I enjoyed the envious looks of other men when we were out together, so, not wanting to rock the boat, I didn't push it.

As for sex, there was plenty of the kind from our first meeting. Wendy worked long hours and would come home exhausted. I had a part time job and would usually make the evening meal. She loved it that I didn't mind doing household chores. She bought me a frilly apron with flowers on it and said I must be wearing it when she came home. Some days, as soon as she arrived at home she would strip off her power suit, sit on the sofa by the fire and point to the ground in front of her. This was my signal to kneel there and begin cunnilingus. I loved to reach for her wispy panties and pull them slowly down her legs, carefully folding them before putting my mouth to her cunt.

She would talk lovingly to me as I sucked and licked her, stroking my hair which I had begun to grow long as she liked it that way.

One day whilst I was on my knees she said;

"Suck that clittie, there's a good boy. I get so excited seeing you in that pretty apron darling. It gets me all wet. I've noticed how you treat my panties dear. You like them don't you?" I nodded as I sucked. "I want you to wear ladies panties yourself from now on darling. You'd like to do that wouldn't you? Stop for a second and answer me."

"Yes, I would, if it makes you happy my dear."

My answer seemed to excite her even more and she roughly pulled my face back to her pussy, holding it there tightly until her orgasm came.

She threw out all my underpants and we went together to buy my panties. She made me blush telling the shop assistant that they were for me. She would turn up the heating and make me strip off down to my panties and apron in the house. In contrast she would wear men's pyjamas.

It was around this time that I lost my flat. I had neglected to pay rent, gas and electricity bills. Wendy seemed pleased. Thinking back now I think she wanted to be more in control. One night as I was ironing one of the white shirts she liked to wear for work she said;

"Darling, I've been talking to mum about you. I told her that you like to wear ladies panties. You don't mind do you?"

I blushed bright red, but my cock stood up. I was just wearing a thin pair of panties as I had taken off the apron whilst ironing as I had got very hot. Wendy spotted my erection.

"I think I have my reply. Your little pecker has answered for you. You get all worked up if something happens that embarrasses you don't you? I think I'll ask her to come over so you can see the look on her face yourself. She laughed when I told her but I could tell that it excites her like it excites me."

"Yes, you like me to excite you and bring you off but you never do the same for me. Bring me off I mean." I answered petulantly.

"I wondered how long it would take you to bring that up. I do like to get you all excited though don't I? I expect you jerk off when I'm out at work don't you? My mum thinks you would enjoy a spanking. Do you ever jerk off thinking about me smacking you on your little botty?"

Again I flushed crimson. I did fantasise about such things. After a long silence I nodded my head dumbly.

"Mmmm... I think I can help you there. You had better be on your best behaviour from now on. And do all the chores without complaint. As for fucking, we will have to see. To be honest I hadn't thought of you in that way. I don't suppose you've jerked off imagining me with other men have you?"

Once again she was spot on. I hung my head with embarrassment but my penis had leapt to attention once again.

A week after this discussion Wendy's mum Mabel came to stay for the weekend.

She is in her late fifties and divorced. What my mum used to call mutton dressed as lamb but still okay looking. She fixed me with a stern look and from the minute she arrived she ordered me around as if I was a servant. I found her short skirt and low neckline quite distracting.

"Have you got your panties on today Simon?" she said with a smirk shortly after she arrived. "If so I'd like to see them."

Wendy grinned and asked me to drop my trousers.

I'd been expecting this and had put on a dark blue pair with frilly edges. I was hoping she might not notice my erection. Mabel was keen to inspect them closely so my arousal was obvious to her.

"He's quite excitable isn't he Wendy?" When she reached over to touch my penis I stepped back with a jerk.

"It's okay Simon. She won't hurt you." Wendy said. She was enjoying my embarrassment.

"Well you might get a spanking off me if you don't behave." Mabel said. "I just wanted to check your cock out for size." I felt like repeating what my mum used to tell me -- ("You don't look with your hands.") but stood patiently whilst Mabel stroked it through the panties then pulled the panties down.

"You were right about the size Wendy, it's a bit like a chipolata sausage. Still, a cock's a cock when all's said and done. Thanks for letting me have a peak." Mabel addressed this to Wendy as if it was not up to me." I don't see much cock these days. I'll be happy to help with his training."

"You can pull your panties back up again darling. Don't mind my mum. I think she's taken quite a shine to you." I did so; then hid my panties inside my trousers.

Whilst Mabel seemed to ignore me for most of the rest of the evening she was careless about showing herself and I caught glimpses of her knickers from time to time. She was not wearing a bra and her large breasts came into view whenever she bent forwards. She drank a fair bit of wine so that as time went on the glimpses of the intimate parts of her body became more frequent. Wendy had forbidden any "self abuse" for the last two weeks promising something special this weekend. I tried not to look but found I could not resist. Wendy could tell it was making me horny and was more flirtatious than usual. Mabel kissed me hard on the lips as she went to bed, grabbing my willy playfully for a second.

In bed Wendy gave me a big kiss and pushed my head down for the oral servicing she often enjoyed. As we lay together after her orgasm Wendy reached down for my cock and whispered;

"I have to slip into work tomorrow morning. You will be kind to my mum whilst I'm away won't you darling?" She was pulling on my cock as she said this and within seconds my orgasm came, spurting semen all over her hand and body.

"It didn't take much to make you come sweetie pie. I said this weekend would be special. Now lick it all up for me." I did so willingly. "Isn't come tasty darling? I want you to eat it for me every time you jerk off. Will you do that for me, my pretty? You've tasted it before haven't you?"

I had found the taste rather bland but there was something subservient about eating come which appealed to me.

"Never tasted it before. I will if you want me to. But I'd much rather lick it off your body like I did just now."

"Maybe you will dear. Now do you think you could start wearing a nighty in bed from now on? I'd love it if you would. Just think how excited it would get both of us."

How could I refuse such a tempting offer.

Wendy left the house early. I got up shortly after her. I was a little scared of Mabel without her daughter around so I busied myself with my chores to take my mind off her. She was having a lie in. At about 9.30am she came down in one of Wendy's dressing gowns looking a little hung over.

"Get me a couple of paracetamols like a good little sissy. There's something I want to talk to you about."

I fetched them with a glass of water and after gulping them down she looked me in the eyes accusingly.

"I saw you ogling my legs and cleavage last night you dirty little pervert. You've been a naughty boy haven't you? I bet you saw right up my skirt to my panties didn't you?"

I nodded, dreading what was to come, but also strangely excited.

"Bend over the kitchen table whilst I go and get the paddle. You'd better strip off completely first."

I took off all my clothes and bent over the table. Mabel took her time, knowing that keeping me waiting was guaranteed to rack up the tension. I felt a strange tingling in my rear end. It was one of my sexual fantasies about to come true.

"I told Wendy that sissies like to be disciplined. You want me to do this don't you?"

"Yes, please ma'am. I've been naughty and deserve to be punished. Please give me a good spanking."

She laid into me with the rubber paddle giving me about twenty strikes on my bare bottom. I pleaded for her to stop after the first ten and soon after that began to sob. Tears were pouring down my cheeks but I sincerely thanked her at the end.

She became more friendly then and we kissed and hugged for a couple of minutes.

"I think I've got something for you that we both might enjoy." Mabel said, spying my growing erection. "You know Wendy's had a number of lesbian affairs don't you?"

I was taken aback by this but Mabel had left the room before I had time to reply.

"Spanking you has made me randy." She said on her return. "Look what I'm wearing. It's what Wendy uses on her girlfriends."

Mabel removed the dressing gown. She was naked underneath apart from a strap on penis. The contraption was designed so that her cunt was stimulated by the movement of the rubber cock.

"Get down on the floor on your hands and knees Sissy Simon. I want to fuck you up your sissy pussy. Don't worry I've brought KY jelly to help my cock go in. I bet you've always secretly wanted to get a good fucking."

"The cock was of average size and, showing patience and restraint, Mabel finally, after several tries, pushed the rubber todger in all the way up to the balls. She quickly established a nice rhythm reaching round to pull on my willy. She clearly enjoyed this kind of fucking judging by her noisy orgasms and after the first few thrusts I was getting into it as well. It was so strange to be the one being fucked but, with so many things happening to me that were equally strange, I was enjoying it wholeheartedly. I shot my load on the carpet having held on without coming for a number of minutes. Afterwards Mabel became quite tender towards me. She kissed me warmly on the lips and thanked me for her "first proper fuck for a long time".

Wendy was not told about our intimacy on her return home but clearly sensed that something had happened. After I had made and served lunch she suggested that I might like to "get comfortable" and strip down to my girly apron and panties.

Mabel said she had an idea.

"Simon might like to wear a pair of my used ones. How about it, Simon?"

I looked across at Wendy who smiled and nodded. Mabel hiked up her skirt and quickly removed the yellow pair she had on, holding them close to my nose for me to take a sniff. I self consciously drew in a deep breath through my nose.

"You're enjoying this aren't you Simon? I bet you two have been up to stuff whilst I was out haven't you?" Wendy said.

I blushed and Mabel just promised to tell her later. I stripped off in front of them and put on the apron and panties. Wendy and Mabel sat and chatted amiably whilst I tidied up around them, bringing them cups of tea, washing up the lunchtime things and generally looking after them.

"You toddle off and make the dinner. There's something I want to talk to mum about." Wendy said after a time.

As I prepared the vegetables and peeled the potatoes I could hear them whispering in the living room. I dare not eavesdrop as my bottom was smarting after the spanking earlier and I was not in the mood for any more. There was a great deal of laughter, so I knew it was me they were discussing.

Some half an hour later I was summoned through.

Wendy stood up as I came in looking strong and authoritative. She was still in the power suit she wore for the office.

"You like feminine things don't you Simon?"

I nodded affirmatively.

"I'm very pleased with your training so far but want to take things a step further. From now on I want you to dress as a woman all the time. You will have to give up your job at the DIY store but there may be girly jobs you could do. Only part time of course, I need you at home to carry out you wifely duties."

"Wifely duties?" I said, not understanding.

"Yes. Mum says you are becoming a good sissy. I want you to be my little wifey at home. There will be other changes to come but I think you will adapt quite well judging from our chat the other day and what mum has just told me. Well darling? What do you think?"

This didn't seem such a huge change and although I was fearful I knew deep down it was what I wanted. For some reason I became a bit tearful and Wendy gave me a big hug and so did Mabel making me cry more; was it out of gratitude?

"You've settled in well here and it isn't as if you have anywhere else to go, have you?" Wendy said smiling, taking my silence as consent.

Later after dinner Wendy put a very tastefully filmed porno movie on the DVD involving power games between three lesbians. I was soon put to work with my head between, first Wendy's legs and then Mabel's legs. I was happy to service them and was turned on by the idea of mother and daughter being so raunchy and free in front of each other. We stayed in the house together on Sunday, me trying on their clothes, until Mabel had to return home. As we were saying goodbye at the door Mabel dropped her knickers, stepped out of them and pointed to the floor. I knelt and got my head under her skirt licking her pussy a second time as she stood above me. What a weekend!