Pleasing Mr. Wilson Pt. 07

I awoke before James and got up to make coffee. It was another beautiful day at the lake - the morning sun was streaming through the kitchen window and there was mist over the water.

We developed a routine the past couple of weeks where I get up first and make coffee. Then I serve James coffee in bed and cuddle up with him, usually leading to me stroking his morning wood and giving him a nice blowjob before he goes to work.

I'm always eager to perform all sexual duties promptly and professionally. I always dress nicely, I always swallow James' cum (unless he wants to cum elsewhere) and I always clean up after our love-making. James is a fit older gentleman who allows me to live my fantasy of being a kept woman and being a dutiful substitute wife. I am very luck to be James' sissy cocksucker.

I just turned 19 this summer and don't have much sexual experience. I like girls and had lots of dates during high school, but it seemed like such an investment in time to get to the point of making out with a girl and then she might only let me feel her tits. It was always a disappointing experience which left me jacking off in my bed after the date.

I have a slight build and blond hair which helps my femme look. I was never into sports so my features are soft and a bit androgynous. I let my hair grow fairly long and styled in a 'bob' that looks trendy for a guy but can look very femme when I'm dressed up like a woman. I even have slightly wide hips for a guy which I can exaggerate with the appropriate lingerie. I've been getting better and better at dressing and acting femme.

The girls in my life may have been a let-down but men, that's a different story. I haven't had much trouble connecting with 'straight' men who can't get enough of my mouth and love hole. My confidence has grown to the point that I feel like if I could get any straight man into bed, I'd be able to give him total oral and anal satisfaction. So far three men have enjoyed my pleasures and I was keen to experience more.

With those naughty thoughts in my head, James interrupted me. "One of my suppliers, Syd, will be at the store this afternoon. I know him quite well and since it's Friday I invited him to come to the cottage and spend the night with us. I already told him about you and he's keen to meet you. How would you feel about welcoming him with all those wonderful things that you do?"

I was taken by surprise. James was offering me to a buddy, and right here in the cottage with James! I wasn't sure how I felt about it but my instinct to please kicked in and I replied, "Of course if that's what you want James, I won't disappoint you."

"That's my girl," James said as he stroked my hair. I noticed that his cock had sprung to life so I could see that the idea of another man enjoying me turned James on. I curled up on my side next to James with my head on his tummy. My mouth was next to his cockhead and his scent was intoxicating. I stuck my tongue out to lick the tip of his cock. There was already a drop of precum at the opening. I licked it up.

"That feels good, Diana. Are thoughts of being fucked by another man turning you on?"

"James I don't know what to think. Of course I'll do whatever you want me to do with your friend but I'm shy about meeting new people, especially men when I'm dressed up. What if he doesn't find me attractive?"

"Diana, I know he will think you're beautiful. I get a hard-on every time you walk into a room and I know it will be the same for Syd. Believe me after your first blowjob I won't be able to pry him away from you!"

I licked James' cock again and took the head into my mouth for a little suck. "What does Syd look like?" I asked.

"Hmmm, well Syd's no athlete that's for sure. He's shorter than me and has a bit of a belly. He's getting pretty bald I guess. You'll see. He's very nice, though."

The description of Syd didn't fill me with hope of enjoyable sex. But at least doing my duty is enjoyable so I had nothing to complain about. I turned my attention back to James' cock and started sucking it in earnest. I like to make lots of sloppy wet sucky sounds when I give head and I like to moan and slurp too. James went quiet settling down for his morning blowjob.

I cupped his big ball sack in one hand while grasping the base of his cock with the other. I learned that a good firm grip on James' cock when I suck him really gets him off. I know he appreciates a quick blowjob in the morning as he has to go to work.

After a few minutes my neck was getting sore but I could tell James was getting close to cumming. I gently caressed his balls and hung on tight to his cock while pushing it as far down my throat as I could and moving my tongue in overdrive. Suddenly James pushed my head down on his rod with both hands and spurted his spunk into my throat.

I kept his cock in my mouth for a minute until I felt it beginning to get soft. Then I swallowed the cum that remained in my mouth and looked up at James, my sexy older gentleman. My daddy.

"That was great as usual Diana," James said. "Thank you for a great start to my day. I've got to get ready for work now. How about you rustle up some breakfast for us while I get ready?"

I swirled my tongue around the inside my mouth finding the last of James' load, "Of course James. I'll fry us up some eggs with toast."

When I got to the kitchen I found a large gift-wrapped box on the table. How on earth did that get there without me knowing?

"Oh, there's a gift for you in the kitchen. I hope you like it!" James called from the bathroom.

"Can I open it now?" I replied.

"Of course! I hope you will wear it this evening so you can show it off to me and Syd."

James had never given me clothes before so I was anxious to see what it was. I untied the ribbon and gently unwrapped the box. Inside were several garments starting with a white bustier corset. I had never worn a corset before but was excited to see if it would make my waist smaller and emphasize my hips and bum. It was a lovely garment, shiny satin with lots of lace, a big bust and pretty garter straps hanging from the bottom.

Next was a yellow 1950s-style sundress with a daisy pattern. I held it up against my body. The dress was pretty. It came to about my knees and was quite modest in that it was high in the front with big yellow buttons. No cleavage would be visible. The bust was pleated which meant that the dress would emphasize my big fake boobies. I couldn't wait to try it on!

I folded the dress and put it on the table. Next was a white crinoline to wear under the dress and make it flouncy. This was very pretty and very sexy. It was thoughtful of James to think of it.

Finally, at the bottom of the box was a pretty white bra in my size, a pair of tan stockings and a pair of white full-back panties that were sheer and semi-transparent behind and lacy in the front.

Wow! A complete set of sexy vintage women's clothes! I was so grateful!

"Well what do you think," asked James as he entered the kitchen.

"Oh James, I love it! I can't wait to try it all on. I'm sure everything will fit fine," I said as I put my arms around his neck and kissed him on the mouth. "Thank you darling," I said as I put the panties on the table. "I'll look my best for you and Syd when you get home from work - you'll see!"

I kissed James good-bye as he left for work then I cleaned up the kitchen. I was so excited about trying on the new clothes that I took it all to the bedroom to start. But first I had a shower and shaved myself all over. Then I did an enema to clean my love hole. I literally saw gobs of Stan's and James' semen go down the drain. What a slut I am!

I was super excited to try the corset but first I put on the bra because I need it to hold my titties in place. I inserted my big silicone tits in the cups. My bust looked wonderful with the pretty new bra.

Next I put on the corset. It had lacing in the back to adjust the fit and a row of clasps in the front. It took a long time fiddling with the lacing to get a snug fit that made my waist smaller. Finally I was satisfied and looked in the bathroom mirror. I was amazed with what I saw - a young woman with a feminine figure looked back at me. My narrow waist emphasized my bum, hips and bust, just as I hoped! The cups of the corset fit nicely under my bra and helped hold up my titties. And between my legs was my erect little penis, shaved and ready for stroking.

Next I rolled the new stocking up my legs and attached the tops to the clasps of the corset. Then I pulled the new panties up over the stockings. I prefer to wear panties on the outside of stockings and garters so I can pull them down to pee. And men like to be able to haul my panties off easily when they want to fuck me.

I bought a pair of white high-heel shoes at a thrift shop that fit me reasonable well. The heels were only two inches high which was as high as I wanted to go as I don't like to be taller than my man. I like to look up at a man when he's kissing me, just as I like looking up at him when I'm on my knees with his cock in my mouth. The shoes would look good with the dress.

Finally the moment arrived when I got to try on the dress. I held it up against me. It was so romantic of James to think of me and buy me this dress, one that he thought I would look sexy in. I unzipped the back and stepped into the dress. I pulled the top up over my boobs and arranged the bust. A busty 1950s housewife looked back at me from the mirror. She was young and inexperienced but willing to learn how to please her husband. There would be a new lesson tonight when James got home with Syd. I couldn't wait!

But something was missing. The dress hung limply over my hips. I reached for the voluminous crinoline and put one foot inside the waist band. Then the other foot and I pulled the crinoline up my stockinged legs high up under the dress. After a bit of adjusting the position of the crinoline I fluffed it out and did a little twirl in front of the mirror. It made the dress puff out in all directions which was a very sexy feminine look. I turned around and bent over looking back at the mirror. The crinoline looked pretty peeping out from under my dress and if I bent over completely my stockings and panties were clearly visible under the crinoline. So tempting for a man's big rough hands to feel. God I was getting horny!

After I calmed down and my cock was soft again, I quickly put my chastity on. I considered pulling down my panties and jacking off in front of the bathroom mirror but decided to suppress my urges and allow the men to decide what pleasure I should have and when. My cummies were always more intense when they're with James' approval.

It was still only midday so I had hours to go before James and Syd arrived. I hoped that since it was Friday that they would knock off early. I knew they would be anxious to see me dressed up and to enjoy my body in all sorts of ways.

I did housework for the rest of the afternoon, cleaning the kitchen, vacuuming and making the bed. There was always laundry to do as well. I wanted the men to see a nice clothesline of panties and bras swaying in the breeze when they arrived.

I had to prepare for dinner too. On the menu tonight was thick sirloin steaks on the BBQ rubbed with homemade steak seasoning and butter mixed with fresh herbs and garlic. I'd serve grilled corn-on-the-cob with the steak. James had already brought home some cans of craft beer and a good bottle of red Australian wine. After a few drinks the guys would be all over me!

Once I had dinner lined up I went to Mrs Wilson's makeup table and prettied myself up. I had some new false eyelashes that I put on to good effect. I batted my eyes in the mirror then winked and blew myself a kiss. The eyelashes were working their magic!

Dark blue eye shadow with sparkles gave me a sultry but young look. A little bit of rouge on the cheeks and bright red lipstick completed the look. Then I sprayed a few little puffs of one of Mrs Wilson's perfumes on my neck and cleavage. There - ready!

I was resting on the swing chair on the veranda when I heard James' car coming down the driveway followed by another car I didn't recognize. I got up and waved.

The two cars parked near the cottage and two men got out. James smiled and waved back at me. beside him another middle-aged guy with a bald spot and a paunch waved and said hello.

I came down the steps and greeted James with a hug and a kiss. I turned to Syd and held out my hand - "You must be Syd. I've heard so much about you!"

"Pleased to meet you Diana - I've heard a lot about you too," replied Syd. "All good things for sure!"

"Guys, please come in. There's cold beer waiting!"

The men followed me into the cottage. "Why don't you make yourselves comfortable and I'll get the beer," I offered.

"I'm going to have a quick shower first," James said. "You can keep Syd company while I'm in the bathroom."

I was immediately nervous being left alone with a strange man so soon. "Of course dear, go freshen up and I'll hang with Syd."

I gave them each a can of beer. James took his to the bathroom and Syd cracked his open and took a long draft.

"You're even prettier than I expected Diana," Syd said.

"That's very kind of you to say Syd, I'm flattered."

Syd stood up and came over to me. I leaned against the kitchen counter facing him. Syd moved toward me to kiss me. I knew that James wanted me to make his friend feel 'welcome' so I stood there and allowed Syd to kiss me. Syd wasn't very attractive and his kiss was rough. He immediately stuck his tongue in my mouth for me to suck. I did. Then he ran his hands up and down my legs then moved a hand between my thighs, under my skirt and crinoline, all the way up to my panties.

Syd gave my chastity a little tug through my panties. "I like 'girls' like you," he said as he slipped his other hand around to my bum and began squeezing it through my panties.

"I'm glad you find me attractive Syd," I fibbed.

"Oh I do and I plan on enjoying you tonight. James told me all about your skills."

Syd pulled his hands out from under my dress when he heard James get out of the shower. "More of that later," Syd said with a smirk as he pulled away. I was flustered by the encounter and had to check my lipstick - I was sure it was smeared from the way Syd kissed me.

I passed James on my way to the bathroom to check my makeup. He gave me a knowing look. I heard the men chatting in the living room and then they both laughed. Were they laughing about me?

The men stopped talking when I walked past them on my way to the kitchen, my dress and crinoline making a satisfying 'swooshing' sound. Syd reached out and squeezed my bum as I walked by. "Nice ass," he said to James.

"You have no idea Syd," James replied. "Wait till you see her naked, well actually Diana doesn't like to take off all of her clothes cause her boobs fall out." Big laugh.

I got the food from the kitchen then went to the veranda to start the BBQ. I decided that Syd was a pig and I didn't like the way James behaved while Syd was around. It was going to be a long night.

"Guys, I'll have supper on the table in about half an hour." "There's lots of time for you to have a shower too, Syd," I said hopefully.

"No I won't bother Diana, I'm enjoying my beer too much"

Just as I expected. Syd wasn't into prepping for sex. I'm not into stinky cocks but I knew I'd soon be on my hands and knees giving his cock and balls a 'shower' with my mouth. Ugh.

I came into the kitchen to grab some utensils and Syd rushed up behind me and lifted up my dress and crinoline and pulled my hips against his crotch. He rubbed his big lump against my panty clad bottom. His lump did feel big which caused my wee wee to tingle. But it was held firmly in my chastity and was not going anywhere.

"Oh Syd, you're so horny! You'll have your opportunity soon enough!" Then I pulled away from him and scampered back to the BBQ.

I set the table and served dinner. The steaks were perfect and the men were pleased. "She certainly is a good cook James," Syd observed.

"Yes, Diana's cooking has improved a lot in the couple of weeks she's been here. And her cocksucking and bum fucking skills have really taken off too."

"You don't say," Syd replied talking past me as if I wasn't even there.

I kept refilling the guy's beer glasses and they got into an excited conversation about business and baseball.

"Speaking of balls," said Syd, "Mine could a little attention."

"Well, you've come to the right place Syd!" James exclaimed. "Diana, finish up those dishes then come to the living room and give Syd a blowjob."

"I'll be there in a sec - almost done the dishes," I replied. "So here it comes," I thought. I'll be on my knees between disgusting Syd's legs taking his filthy cock and balls in my mouth. But I needed to develop a better attitude. Better to get in the mood to enjoy the job than be all fussy about whether a fella's cock was freshly showered or not.

When I got to the living room James and Syd were sitting on the couch. Syd's legs were splayed waiting for me. I swished my way over and stood in front of Syd, rustling my dress and crinoline a bit with every step.

Without a word I got down on my knees in front of Syd. I moved a few inches closer on my knees and spread my dress out nicely on the floor around my legs. My shoes stuck out behind my dress. I smiled at James and then at Syd as I unzipped his pants. He raised his bum so I could pull his pants and underwear down to his ankles.

Syd's cock was cut, short, but big in girth. I could smell a faint scent of urine and crotch sweat. "Nice," I thought sarcastically.

"My you have a lovely cock Syd," I gushed.

"Thanks, now get a move on and suck it," Syd replied, winking at James.

James sat there watching me as I lowered my head down to Syd's crotch. I did the usual tonguing the balls and shaft before taking the cockhead in my mouth. My goal was to make him cum as quickly as possible. With the smell, the experience wasn't great. But as I licked his cock and balls they did become cleaner and smelled better, and eventually the smell didn't bother me at all. I was a human cock-washing robot. I knew I was doing a good job.

The girth of Syd's cock made it hard to take much of him in my mouth but I did my best. Syd pushing my head down with both hands didn't help as it only made me gag, slowing down making him cum.

I fondled Syd's balls with both hands and bobbed my head hard up and down on his dick. I used my tongue as much as possible around his cockhead. Rolling my tongue over his slit I could feel precum oozing out. I picked up the tempo and suction and before I knew it Syd was hanging on to my head and bucking his cock back and forth in my mouth as he grunted out a half dozen big spurts of jizz.

I held my position until Syd relaxed and his orgasm was over.

"I'll be damned, that's got to be the best blowjob I've ever had," Syd said to James. I let Syd's cock out of my mouth and sat back on my haunches. I managed to swallow Syd's load save a small dribble out of the corner of my mouth.

"Well what do you say Syd?" James asked.

"Thank you very much Diana for the great blowjob. It was the best ever!"

"You're welcome Syd," I replied, relieved it was over for now.

I could see that there was lump in James' pants. "Would you like a blowjob too, darling?"

"Well," James replied. "I was going to wait but I'm so horny after watching you suck off Syd, yeah I think I could use a nice blowjob right now."

I held up the hem of my dress and my crinoline and shimmied over to James on my knees. James lifted his bum and pulled his pants down in anticipation. His cock stood straight up. Syd's cum still tasted strong im my mouth as I lowered my head onto James' cock.