Pleasing Mr. Wilson Pt. 03

After James made love to me last night I put my silky nightgown (actually his wife's nightgown) back on and fell into a deep sleep in his arms.

When I awoke in the morning the sun was streaming in the window and James was still asleep. I got up and went to the bathroom to freshen up. I wiped dried cum off of my bra and freshened my body with a fragrant soap. Then I put on a fresh pair of panties, bra and the nightgown and went to the kitchen to make coffee.

I knew James would have to get up soon and go to work. But I hoped he would make love to me again before he left. My bum hole was a bit sore but I knew his cock would feel wonderful again as soon as he pushed it inside me.

I poured two cups of coffee and went back in the bedroom and sat on the bed beside James. He opened his eyes. "Good morning, Diana. I slept well after the nice cum I had. How about you?"

"Oh James, I slept well too. I was so satisfied after you made love to me. And it seems so right that you took my virginity last night. I can't get it out of my mind."

James took a sip of coffee then put the cup on the bedside table. He put his big warm hand on my thigh and gave it a little squeeze. I put my coffee down and spread my legs a little. James took the cue and moved his hand between my legs and massaged my inner thighs, working his way up to my panties and the little cock-bulge. I leaned back and sighed with pleasure.

"Hang on a sec while I go to the bathroom," James said as he pulled his hand out of my panties.

I heard him peeing and then running the water for a long time as I knew he was freshening up his cock, balls and armpits. I lay back on the bed propped up with a pillow. I fluffed my hair and arranged my bra, panties and housecoat. I spread my legs and my stiff little cock was plainly visible through my panties.

I wanted James to make love to me the way I imagined he fucked his cute little wife - in the missionary position.

When James entered the bedroom he was naked with a big hard-on sticking straight out. It was a beautiful sight - an aroused man looking at me to satisfy his needs.

"Oh James, you're so handsome. Your wife is so lucky. I'd love it if you would make love to me the way you make love to her."

"I have to get going Diana, but you're irresistible laying there," he said as he sat on the bed beside me.

James brought his head to mine and kissed me lovingly on the mouth. I kissed him back and opened my mouth allowing him to explore with his tongue. It was heaven. He had one arm around me and he squeezed my big fake titties with his other hand. I loved the way he paid attention to my tits which made me feel very fem.

James grabbed the lube and put a generous dollop on his hand. Then put his hand in my panties, feeling down past my balls until his slippery fingers touched my bum hole. His arm was rubbing my cock while his fingers were massaging my rosebud. Before long the tip of a finger was in my hole and soon there was another.

I put my arms around his neck and kissed him for all I was worth. I pulled the front of my panties down so my cock poked out. Then James started to pull them down all the way. This time my panties were on the outside of the garter so I just lifted my bum a little allowing James to pull my panties off completely.

I moved down on the bed and brought my legs together. I pulled James on top of me and wiggled into position so his cock was between my thighs. He started moving his cock in and out. Some of the lube he put in my bum ended up between my thighs so his cock had a nice warm slippery saddle to enjoy.

I moved my hips to meet James' thrusts. He started building in intensity as I spread my legs. I wriggled my bum into a better position for his cock to meet my hole. Soon his cockhead was knocking on my back door. I tried to push against it while relaxing my sphincter.

"Oh James, your cock feels so good. Please shove it into me and fuck me the way a man fucks a woman," I panted.

James reached down and grasped the base of his cock then slowly pushed his cockhead hard against my hole. Suddenly the sphincter yielded to James' cock and I was being fucked again. James put his weight on me and started to fuck me fast and hard. I held on to him with my arms around his neck and my legs wrapped around his body. He was making a woman of me!

We rocked together hard for a few minutes until James started grunting and released his load deep inside me. After what seemed like a long cum dump we lay there breathing deeply, our hearts pounding, with him on top of me squashing my big fake tits between us.

"What a way to start the day Diana," he said quietly while nibbling my neck.

"Thank you James. I've always fantasized about being fucked like a woman and I loved you doing it to me."

"You certainly make me cum quickly, Diana. With your pretty looks, your sexy lingerie and your tight 'pussy', you're a man's dream come true."

"I'm so glad you feel that way, James. And you're such a good lover! You can enjoy my body any time, you know."

After all the fun James went to the bathroom to shave and get ready for work while I made a simple breakfast of boiled eggs and toast.

We ate breakfast quietly together.

"There's three weeks before my wife returns," James said. "There's no reason you couldn't stay here the whole time. It would save all that cycling back and forth to your house and we'd be together every night. What do you think?"

"Oh James, that would be wonderful! I would just tell my mom that I was staying in the spare room and getting more hours of work while here. It makes perfect sense and she would totally understand. I'd love to!"

"Okay. Let's put your bike in my car and I'll drop you off at home on my way to work. You can pick up a few things then cycle back here. You have plenty of work to do here and I want you to take on additional duties like cleaning and looking pretty and keeping my cock satisfied. I'd love to come home after work today with you waiting for me dressed in something sexy."

"You won't be disappointed James," I said with a wink. "But first I have to change back into my boy clothes to go home."

When I got home my mom had just left for work. I gathered some of my boy clothes to take back to the cottage. Everything had to fit in my backpack so it wasn't much. And I left room for a few naughty items. One was my beginner's makeup kit which I had never had the opportunity to use. I threw in my 7-inch dildo. Finally, I pulled the few items of lingerie I had in my hiding place in my closet and pushed them into my backpack.

I left my mom a note to explain I'd be spending the next three weeks at Mr Wilson's cottage, possibly coming home on the weekends (although I sort of doubted that). Later I called her and explained in more detail that I'd get paid for more hours and I could enjoying fishing and paddling the Wilson's canoe on the lake. It was going to be a great few weeks!

It was a beautiful day and I had a pleasant 40 minute cycle back to the Wilson's cottage. On the way I stopped at a pharmacy to buy an enema kit. I had never used one before. I was conscious that my hole wasn't clean inside when James fucked me. It didn't seem to be a problem but I wanted to make sure I was properly clean for him from now on.

I also stopped at a thrift store which I had visited a couple of times before to buy women's underwear. I was no longer embarrassed shopping the women's section there. The store had just opened and there were no other customers - just a couple of staff who didn't notice me at all.

I found a pretty slip that went down to mid thigh and was very silky and trimmed with a wide band of lace. Then I found a navy skirt to wear the slip under. I also found a cream-colored silky top that was gathered under the bust with a little silver buckle. I knew it would really show off my big fake titties so I grabbed it. From a huge bin of bras I selected two pretty ones and a couple of pairs of panties from the panty bin. Those were the very last items I could possibly force into my backpack.

Back at the cottage I couldn't wait to try on my new things. I took a quick shower then put on one of the new pairs of panties (they were coral color) and did a little twirl in front of the mirror. I felt wonderful alone at the cottage on a fine summer day. I put on a pink bra and a pair of Mrs Wilson's tan stockings. I slid the new slip up my legs feeling the silky fabric against my stockings. My skin tingled with excitement. I slipped my big fake silicone tits into the bra and finally put on the new top. After I arranged the top around my boobs they really looked big and round. The lace of the pink bra was just barely visible through the fabric of the top. I felt incredibly sexy and I think I looked sexy too. I bent down in front of the bathroom mirror and swayed my fake tits back and forth. They had a very sexy jiggle - just what men love!

Now to work! The first order of business was to wash all of Mrs Wilson's lingerie I had been wearing. I hooked the bras and put everything in a laundry bag and put it in the washing machine on the delicate cycle.

Then I made the bed that James had fucked me in twice. I opened the curtains to let the morning sunlight flood the room and I lay down on the bed to catch my breath. I started to play with my stiff little cock but decided not to jack off as I would save any of my cum for James if he wanted it. I wanted to be a good surrogate wife to him, not a selfish slut distracted by her own pleasure.

After the wash was done I hesitated to put Mrs Wilson's dainties in the tumble dryer as I was concerned something might be damaged. So I decided to hang everything on the clothesline. I felt wonderful dressed like a woman hanging out the wash. After a few minutes I admired a clothesline of pretty bras, panties, garters and a basque fluttering in the wind. I felt like I was where I belonged doing what I wanted to do.

Suddenly I heard a car come down the driveway. That struck me as odd as James didn't tell me to expect anyone. Standing at the clothesline I couldn't get back into the cottage without the driver seeing me so I just stood there looking rather over dressed and a bit slutty. I was glad I had my new skirt and blouse on.

The pickup truck stopped and a well built young man got out. "Good morning ma'am," he said with a smile. "I'm here to change the filter in the water conditioner."

"Oh, I see. But I don't know anything about the water conditioner."

"That's ok. I've done it here before. It's over there in the shed with the well pump. I'll just take care of it for you."

He was definitely eyeing me and I think he liked what he saw, even though I looked a prostitute. I was sure he could see my pink bra under my blouse in the bright sunlight. It was the first time I was dressed in front of a stranger and it made me feel very nervous.

"I'm Stan," he said reaching out to shake my hand. "Are you a friend of Mr Wilson's?"

"Oh, I'm his niece Diana," I lied. "I'm visiting for a few weeks."

"I see. It's nice to meet you Diana. Well, I better get to work - they don't give me much time to do these service calls."

"I understand, Stan. Can I get you anything? A glass of water perhaps?"

"Yeah, a glass of water would be nice - thanks!" Then Stan turned to go to the shed.

I went to the kitchen to fetch a glass of water. I put some ice cubes in it. I stood at the sink thinking about Stan. He was very polite and respectful. Surely he knew I was a guy dressed up in women's clothes - or did he? Either way he was kind and I was attracted to him. Stan was handsome, at least 6 feet tall and well built. He wasn't much older than me, perhaps a university student on a summer job. I decided to be friendly and see where it goes.

I went to the shed with the glass of water. Stan was on his knees with some tools in front of what looked like a big tank.

"Thanks for the water, Diana. Just put it on the bench for now, please," and he went back to work.

The door of the shed closed of its own accord and we were both there in the dim light.

"There's a light switch here," I said.

"Thanks, I guess I need the light. Can you turn it on for me?"

I flicked the switch on and stood near Stan pretending to take an interest in what he was doing.

After a few minutes I sat down on the bench and held Stan's water.

Eventually, Stan stood up and brushed his clothes off. He was wearing a tee shirt and shorts with some trendy orange sneakers.

"All done," Stan announced as he reached for the water and took a big gulp. "Thanks!"

"I have to run, but it was nice to meet you Diana. I hope you don't mind me saying that I think you're very beautiful."

I blushed but he probably didn't notice in the light of the single bulb in the shed.

"That's sweet of you to say," I replied.

He moved closer to me and bent to put the glass back on the bench. Involuntarily, I reached out and brushed my hand along his leg. Stan responded by standing directly in front of me with his legs parted in a firm masculine stance. His crotch was close to my face and there was a definite bulge in his pants. I was turning him on and that was turning me on.

I gently cupped his crotch with my hand and felt his manhood swell. I realized that I would soon be sucking this young man's cock. I couldn't think of a reason not to.

Without saying a word I undid the button of his shorts and pulled down the zipper. He was breathing heavily now and he ran his hands through my hair.

"I suppose I have a few minutes depending on what you have in mind, Diana."

"I was wondering if you would like me to give you a blowjob? I love giving head."

"That's definitely worth staying for," Stan replied as he began to hold my head between his hands.

I pulled his shorts and undies down to reveal a wonderful large cock with trimmed blonde pubes. I held his cock in my hands and felt it engorge to an enormous size - bigger than James' and much bigger than my little thing. I was thrilled to be holding this big cock specimen so close to my eager mouth.

With me sitting on the bench I pulled his hips closer to me and kissed his cock. It smelled nice - a bit musky and a bit sweaty but no trace of urine smell which I don't like.

Now his cock was fully erect, displaying a gorgeous big helmet which I wrapped my lips around. Here I was, sucking yet another cock, this time with a stranger in a dimly lit shed. I cupped his balls in my hand and grasped the base of his shaft with the other. I started sucking his cockhead, rolling my tongue around it while slowly pulling the shaft with my hand.

"That feels fantastic, Diana. Please keep going!"

I didn't say anything but started pushing his cock deeper into my mouth and making "glug, glug" noises on each stroke. Before long he tensed up and I prepared to take his load in my mouth like a good girl. But it was a huge load and he bucked so hard when he came that plenty of semen leaked out of my mouth and dribbled all over my clean blouse.

I kept his cock in my mouth as I swallowed as much cum as I could. Then I licked and sucked his cock clean in the proper way an experienced cocksucker does. I was proud of my growing oral talents and I liked to leave my men satisfied with the experience.

"That was amazing Diana!"

"I'm glad you enjoyed it Stan," I replied. "I don't get to suck such a beautiful cock very often."

"Well, I'm glad I bumped into you and got such a fantastic surprise. Perhaps I can see you again and we can go on a proper date?"

"I'd like that Stan. Give me your number and I'll call you if I have time while I'm here. Maybe there will be an issue with the water conditioner and you'll have to come back," I winked.

I stood up. With his pants still around his ankles, Stan kissed my cummy mouth. He was a sweet boy and I thought I'd like to enjoy him more.

"Well, I really do have to run, Diana. I hope you'll reach out to me soon. Otherwise I may have to come back and find something to fix."

"That would be great, Stan. I'd love to see your beautiful cock again and maybe try some other things!"

Stan finally let go of me and pulled up his pants. Then he picked up his tools and walked back to his truck.

I waved good bye as he drove away.

I was definitely getting addicted to giving head and swallowing cum. It just felt so good to pleasure men. They were always so eager and appreciative. Pleasuring men made me feel feminine and whole. I was a guy who liked to dress up in women's underwear and suck men's cocks. Why not?

By now it was mid afternoon and I had to think about being ready for James when he returned from work. I wondered if I should tell him that I sucked a stranger's cock in his shed today? Would he be jealous or would he be proud of me? I would soon find out.

To be continued...