Pleasing Mr. Wilson Pt. 04

After Stan's truck disappeared down the driveway I stood on the veranda of the cottage slightly dazed. The taste of his cum lingered in my mouth and my new blouse was covered with cum and saliva that had dribbled out of my mouth, his load was so big and his orgasm so energetic.

I was glad I decided to give Stan a blowjob. He was handsome and cute and appreciative. I wondered if he had a girlfriend. I wondered how her cocksucking skills were. I had a feeling Stan didn't get many enthusiastic blowjobs like I had just given him.

And I wondered how James would react if I told him. I hoped it would turn him on and not make him angry.

James would be home soon so I had to get ready. First I took two steaks out of the fridge and seasoned them. Then I sliced potatoes into strips to make home fries. Finally I washed some greens for a salad. Now I could relax knowing supper was started. Of course I was still wearing my cum-drenched blouse and some of that cum got on the apron I was wearing. I felt like a very slutty housewife and enjoyed the feeling.

In the bathroom I opened the enema kit and read the instructions. It was pretty easy and I stood in the shower and did the enema - twice. My bottom was definitely clean after the second round and I felt very presentable from the bum-hole perspective.

Then I had a shower and shaved my legs, and pubes. I used a fragrant lavender soap on my body and coconut scented shampoo. Stepping out of the shower, my body was a smooth curvy canvas for women's underwear.

I opened Mrs Wilson's lingerie drawers and, for the first time, spread out my own lingerie collection on the bed. I wanted to dress more in my own clothes rather than Mrs Wilson's. Picking out what to wear is nearly as much fun as wearing it!

I selected a very lacy black garter belt and plain black stockings. I paired those with transparent black high-back panties that would show off my cock and bum crack. Then I added a vintage-style black bra with lots of lace and large cups that would hold my big fake silicone titties securely. For outer wear I chose my new skirt (navy) with a thin black belt, and one of Mrs Wilson's white billowy blouses (My blouse, still covered in splats of semen, was in the clothes hamper).

I put on all of the clothes feeling very horny from the blowjob I just gave and excited about playing surrogate wife for James who could arrive any time.

I put on a little blue eyeshadow and mascara. I didn't have the time or skill to do more. But simple eyeshadow and mascara does wonders for a girl's looks. I felt ready for James so I went to the kitchen and and washed the cum off the apron then put it back on. My little cock was sticking straight out inside my panties and even pushing out the apron. My cock really wanted to cum. "Down boy," I thought to myself.

I got busy working on supper. I put the fries in the oven to bake and made the salad with a scratch salad dressing. I'd start the steaks on the BBQ after James got home.

Before long I heard James' car approaching. He got out of the car clutching a bunch of flowers.

"Thank you for the flowers James, that is so thoughtful," I exclaimed.

I put the flowers on the counter, put my arms around his neck and gave him a passionate kiss. Our tongues made love and my stiffie poked into James' hip.

"I can see you missed me, Diana!"

James held me in his arms and kissed my eager mouth. He reached one of his hands down to feel the plumpness of my bum then further down to the hem of my skirt. This was the first time I had worn a skirt in front of James and it was a thrill to feel him lift the skirt and slip up high in the back to reveal my panties. He felt my bum through my panties with both hands and pushed his big bulge against me.

"Oh James," I said in his ear, "do you want to enjoy my body right away or would you like to start with a drink?"

"Well, since we have all the time in the world why don't you make me a whisky and soda, and one for yourself of course."

I broke away from his embrace. "I'll be right back with the drinks!"

I could tell that my skirt didn't fall back down when James stopped fondling me. I ignore it hoping it would add a bit of spice to James' view of me making the drinks.

"Here you go darling," I said as I passed James his drink. I sat down on the couch beside him holding mine. I made a gin and tonic for myself.

"You look absolutely beautiful Diana."

"Thank you James. I really want to look good for you. I'm wearing mostly my own clothes today. I brought them from home this morning. And I stopped at the thrift shop on the way and bought more sexy things. I also picked up an enema kit and I used it this afternoon so my bum is fresh and ready for you."

"Wow, you really are trying hard Diana. And I like the sound of a fresh bum," James laughed. He put his drink on the coffee table and turned toward me. With one arm around my shoulders James pulled me to him and began kissing me deeply. I stopped to put my drink down then resumed kissing James while he shoved his other hand under my skirt and slip and into the gusset of my panties where his fingers played with my bum hole.

I thought James was going to fuck me then and there, but he pulled his hand out of my panties and picked up his drink.

"I meant to tell you that there was supposed to be a service call today for the water conditioner. Did anyone turn up for that?" James asked.

I snuggled up beside James and told him about Stan coming by this afternoon.

"Ah Stan - a good looking boy as I recall."

"Oh yes, he's quite cute."

"So you met him?"

"Yes, I happened to be outside hanging out the laundry when he arrived. I was a bit embarrassed that he saw me dressed but at least I had a skirt and blouse on so didn't look too out of place. He was very nice and if he thought I was a crossdresser he didn't say anything. In fact he said he thought I was pretty."

"He told you you were pretty, eh? How did you respond?"

"Well actually, I was going to tell you, he kissed me in the shed and I ended up giving him a blowjob. I hope that's ok, James."

"Let me get this straight - you're living in my cottage and a stranger arrives and within a half hour you're sucking his cock. Is that right?"

"Yes, I guess so."

"You 'guess so'? sounds like you have no self discipline at all, Diana. I'm afraid I'm going to have to give you a little discipline."

I was shocked. James spoke plainly with a straight face so I thought there was a chance he was joking.

"Diana, lay on your tummy across my legs. I'm going to give you a spanking. I hate to have to do this but I have no choice if you're going to continue living here and working for me."

"James, you can't be serious," I began.

"Be quiet and lay across my lap," he said sternly.

I slowly got up and repositioned myself across James' lap.

James began to feel my bum cheeks through my skirt while pushing a finger in my mouth. I sucked his finger vigorously hoping to please him.

Smack! He hit my bottom hard with his hand. I was stunned.

"You're a naughty gay faggot sissy slut who needs guidance and I'm going to give it to you." Smack!

"That hurts James," I cried.

"Quiet! I'll let you know when I'm done!" Smack!

"Get up and take my pants off - now!"

I jumped up and undid his pants and pulled them down. James nodded at his briefs and I pulled them off too. He had a huge erection!

"Remove your skirt!"

I unzipped my skirt and let it fall to the floor around my feet.

"Lift up your slip and get back on my lap."

I did as I was told. By now I had a very stiff hard-on too. I lay across his lap with my stiffy against his legs.

He resumed spanking me - smack! Smack! Oh, that hurt on my panty-covered bum.

James rubbed his hand over my panty-bottom while sticking fingers in my mouth which I sucked as eagerly as I could.

James, with his hard-on, was clearly enjoying spanking me which gave me some hope it wasn't going to be a serious painful ordeal. I started to relax and gently move my cock against his legs.

"You really are a total slut, aren't you Diana? You're trying to pleasure yourself even while I punish you!"

"I'm sorry, James! You do want me to be a slut, don't you?" Smack!

"You listen to me! A boy who dresses up like a girl so he can have sex with boys is a sissy faggot cock-sucking slut! And that's you!" Smack!

"My bottom was getting really sore now and every smack of his hand hurt a lot. The game, if that's what it was, was quickly losing it's appeal for me. Still, I wanted to be obedient so I just took a deep breath and waited for the next smack.

Then James positioned his cock under my tummy near my cock and he pulled my panties down. I'm sure my cheeks were bright red as James felt them.

"I think that's enough for now. Put some lube in your hole and bend over the arm of the couch."

I got up on wobbly legs with my panties around my thighs. I squirted a big glob of lube on my hand and worked it between my bum cheeks and into my love hole. My cheeks were burning as I bent over the arm of the couch.

James got behind me and spread my cheeks with both hands. "I'm going to teach you a lesson Diana," as he pushed his cockhead against my bum hole. Then with a big shove his cock was inside me. The sudden entrance was very uncomfortable but I knew it would get better.

James started to fuck me hard right away. No gentle lead up this time. He was fucking me like an animal. He had never been like this before. I grasped a pillow with my hands and let him have his way with me.

As he fucked me, he called me names like "whore" and "slut". I just took it, relieved to be getting fucked instead of getting spanked.

James put his head close to mine as he pounded me. "From now on I tell you who you are going to suck or fuck - do you understand?"

"Yes, I understand, sir."

"You're going to contact that boy and tell him you're a crossdressing faggot with a cock and fake tits."

"Yes sir", I stammered.

"If he still wants to see you then go on a proper date with him and let him do whatever he wants to you - do you understand?"

"Yes, of course, I understand."

"When you get back from your date you're going to tell me every detail. Do I make myself clear?"

"Yes, I understand, sir."

Suddenly James started bucking and grunting like a wild animal. It seemed like his biggest cum yet as he pumped his load into me. Then he collapsed on top of me putting all of his weight on me. It was over. I realized that both of my fake tits fell out onto the couch while he fucked me. That was annoying.

"Well I enjoyed our little discipline session, Diana. I'm your daddy now and I may have to give you some 'guidance' once in a while. But it's all in good fun. I don't mind that you sucked that boy's cock today. The thought of it turns me on."

"Oh James, that's such a relief! I thought you really were angry with me. You scared me."

"Sorry darling, you played along beautifully but I didn't mean to frighten you." He kissed my neck then got off me.

I stood up too. My legs were wobbly and my bum cheeks and hole were both sore. Cum was dripping down my leg.

James held me and kissed me. "Do you agree that I'm your daddy and you'll do as I tell you, Diana?"

"Yes, if that means I'm like your substitute wife, I'd love you to be my daddy. Oh James, you know I'd do anything for you, anything!"

"That's a good girl. I knew we'd come to an understanding."

"I'm going to give you some money to order pretty clothes and toys online. There's still lots of time to enjoy them before my wife returns. Then you can keep everything for your collection. You never know when you'll need to dress up!"

"Thank you, James. That's very kind. Let's look at clothes together tonight. I want to make sure you really like what I order!"

"Sure, but you can surprise me too. And I'm going to order a few things to surprise you."

We sat down on the couch again, cuddling and kissing. The late afternoon sun flooded the living room.

"I would like you to get in touch with that young man to see if he wants to take you out. I'm sure after that blowjob you gave him, he'll want more no matter what!"

"Okay, if you're sure James."

"Yes, I like the idea of sharing you around. I don't want to keep your mouth and boi pussy to myself, that would be greedy. So let's start with that clean-cut young man and see where it goes."

I was upset by the way James spoke to me as if I was nothing more than a "mouth and boi pussy". And the suggestion that he might farm me out to numerous men made me nervous. Yet, I trusted James to take care of me so if he shared me with other men that he selected I guess I could come to enjoy that. Perhaps I'd totally love sucking and fucking all kinds of different cocks. I liked the idea of experiencing different shapes, sizes and colors of cocks, and the different fucking styles and taste of cum of different men. The more I thought about it the more I liked the idea of letting James share me with whomever he chose and I'd just do my best to give pleasure and live up to James' expectations. That's what a proper sissy cocksucker does!

James reached down and stroked my cock. My panties were still pulled down and my cock was stiff as wood. James bent his head down and, for the first time, took my little penis in his mouth. He sucked it nicely and in only two minutes I came. He pulled his mouth away from my cock at the last minute and directed my cum at my tummy. When I stopped spurting, James put his head in my lap and swirled the globs of my cum around with his finger. And I could feel cum oozing out of my bum hole onto the couch. I'd have to clean that mess up.

"So, what's for supper, Diana? I'm starving!"

"BBQ steaks and home fries."

"Well you better get a move-on while I read the paper. But keep your panties just like that. I want to watch your red spanked bottom and pulled down panties while you work in the kitchen. Don't forget to bend over a lot!"

I kissed James again then got up from the couch, my ass and tummy dripping cum. I walked to the kitchen with my panties pulled down to my stocking tops knowing James was staring at me the whole time.

I was already looking forward to calling Stan tomorrow to arrange a date since that's what my daddy wanted me to do.

To be continued...