Pleasing Mr. Wilson Pt. 05

James and I had a lovely evening like happy newlyweds. We watched some TV, snuggled and went to bed. Of course James fucked me after we turned in - he wanted to fuck me as often as he possibly could before his wife returned in less than three weeks. I didn't mind. I was loving playing at being James' substitute wife while she was away.

In the morning I gave James a quick blowjob then made him breakfast before he left for work. "How many wives would do that," I wondered.

Alone at the cottage I did the dishes and gazed dreamily out the window to the lake. Another beautiful day as a kept woman or should I say kept sissy faggot cocksucker. It was all fine with me. I was having a wonderful time keeping house for James. James' wife was quite attractive and I felt a bit jealous of her. It was one reason I enjoyed wearing her clothes so much.

I did some laundry. There was always laundry to do as we seemed to be spraying cum all over our clothes, underwear and bedding. I was constantly cumming in my panties. And today I had to wash cum dribbles off the couch where James fucked me so hard last evening.

After hanging the wash on the line I summoned the courage to call Stan, the young maintenance guy I sucked off yesterday afternoon. James wanted me to try to go out on a date with him.

I was nervous as his mobile rang. I had no idea how the start the conversation. "Hello?" Stan answered.

"Hi, it's Diana. We met yesterday."

"Wow, I never expected to hear back from you Diana, but I'm glad you called."

"I was thinking about your offer to take me on a date, perhaps show me around."

"I'd love to Diana. I can take you out tonight if you like."

"That would be lovely, Stan. But there's something you need to know about me. I'm not what I appear."

"That's no problem, Diana. I sort of wondered if you were trans or something. I'm cool with it."

"Well, I'm not exactly trans, I'm a guy who enjoys dressing in woman's clothes. I hope you're not upset to know that a guy gave you a blowjob yesterday."

"I see..." Silence on the line. "I'm definitely not into cocks. If you were a tranny I think I'd be okay with it. But a crossdresser? I mean you look really nice, as pretty as most girls I mean. Anyway, you gave me a fantastic blowjob yesterday and I'd love to have another one, so yeah I guess I don't mind."

"I think you can count on another blowjob if you take me out, Stan."

"I'd definitely like that! How about I pick you up at 6 and we'll go for a drive. I'll show you some nice places."

"That sounds lovely, Stan. And I'm not used to being dressed in front of other people so I don't want to meet anyone while we're out and I don't want to be in a public place."

"That's no problem, Diana. I'll just keep you to myself."

"Okay, sounds good, Stan. I'll see you at 6."

I hung up and put my phone on the kitchen counter. I was tingling with nervousness but also very excited. I was going to meet this hunky young stud again and I was going to let him fuck my brains out. Tonight. Through the kitchen window I could see the shed where I sucked his cock yesterday. I was getting a little boner thinking about it.

I sent James a text to tell him Stan would take me out tonight. He replied, "I'm sure you'll do me proud! Good girl. And good timing as I have a gift for you. see you at supper time." I wondered what kind of gift James was talking about.

I had all day to decide what I would wear and how I would look. I had lots of lingerie to choose from but I didn't have a lot of choice of outer clothes. I decided to take a closer look at Mrs Wilson's closet to see what I could find.

I was relieved to see a few outfits that would work. Mrs Wilson was fairly tall and slim so some of her clothes fit me well. I decided on a pair of embroidered denim capris with a silky cream-colored sleeveless top. One of her pearl necklaces looked great on the blouse. My fake tits would put a strain on the blouse which is a look I like.

For lingerie I settled on a white set with tan stockings. Of course it's silly to wear stockings under pants but wearing stockings makes me feel very sexy and the sexier I feel the better I perform. And if Stan takes my capris off then he's bound to like the sight and feel of my garter and stockings. The panties were full-back style with a transparent behind and an opaque panel of lace in the front. I didn't want my cock to be too obvious since Stan wasn't into cocks. The bra I chose had very lacy cups to match the panties and lacy straps around the back and shoulders. I would fasten the bra at its tightest fit to make sure my fake tits would stay in place. And I like the feeling of a tight bra so I can't forget that I'm wearing one.

I wanted to do a better job on my makeup this time so I spent an hour watching videos about how to apply makeup. And I learned a lot. After a shower and an enema, I sat down at Mrs Wilson's makeup table.

I started with blue eyeshadow and applied a lot which looked very sultry. I added sparkles which made me look like a teenage girl, then I applied mascara. My eyelashes looked very feminine. Finally I darkened my eyebrows with eyeliner. I looked pretty good! But I didn't bother to apply foundation and makeup to my face. I had shaved very closely in the shower which makes my face very smooth and soft. I don't have much facial hair and it's blonde, so it's easy for me to have a smooth feminine face.

As I got dressed I realized I had nothing to wear on my feet. Mrs Wilson's shoes were too small for me. I'm 5' 9" so I wasn't keen on wearing high heels anyway. I didn't want to be taller than my man. Around the cottage with James I usually wore stockings but without shoes or maybe wearing crocks which weren't sexy but were at least were casual and easy to kick off when he threw me on the bed.

For my date tonight I decided to ditch the stockings (but I kept the garter belt on just for fun) and would wear flip flops. They were casual and would go with the denim capris. And I wouldn't be taller than necessary.

I was putting the final touches on my outfit as James' car pulled into the driveway.

"There you are sexy! Wow, do you look hot!"

"Thank you James," I blushed. James came to me and held me in his arms and kissed me. As usual his bulge was sticking into my tummy which immediately gave me a hard-on.

"Oh James," I breathed in his ear. "It's so good to hold you! You're making me so horny already but I think I should save myself for my date with Stan."

"Yes, I want you to give Stan everything you've got so I'm not going to fuck you now. But when you get home I'm going to give you a proper fucking while you tell me all about your date. Your holes are going to give a lot of pleasure tonight!"

"I can't wait, and I'm so glad you encouraged me to go out with Stan. I think he's really hot for me."

"After getting one of your marvelous blowjobs yesterday I'm sure he's eager for more."

Then James pulled out a small gift-wrapped box. "This is for you Diana, just in time for your date."

"Oh thank you James," I said as I took the gift and began to unwrap it.

At first I didn't know what it was, then it dawned on me that it was a chastity device. It was plastic and pink with a little gold lock and two keys.

"Thank you James," I said tentatively. "It's nice but what's your idea?"

"I want you to wear this tonight on your date. It will help you concentrate on pleasuring Stan and not be distracted by your own urges. Take one of the keys and give it to Stan. He will unlock you if he wants you to cum too. But if he's straight he will probably be happy that your little wee wee is ducked away inside the chastity. Either way it will give him a better sexual experience with you."

I didn't like it when James spoke of me like I was an asset that only existed to pleasure men and who may not get any satisfaction herself. But then part of me loved just that - doing my very best to satisfy men's urges, making each blowjob better than the last, thrusting my bum hole on a fella's cock harder and faster than the last time, making a man cum as many times as possible. Yes, the chastity device might be just the thing to improve my cocksucking and bum-fucking performance.

I threw my arms around James' neck, "Oh James you're so considerate! I do want to be my best for Stan and for you afterwards. I love the way you're teaching me to be desirable. I'm so happy!"

"You're welcome Diana," he replied.

"It's almost 6 so time for you to get ready for Stan. What did you make me for supper?"

I had forgotten about James' supper! Oh, no! I hoped I wouldn't get another spanking over it. My bum was still sore from the spanking he gave me last night.

"Darling, with all the excitement today I didn't have time to make a dinner from scratch but I'm going to put on the oven right now so you can heat up a frozen pizza."

"That's fine Diana. I know you have a hard time concentrating when all you think about is cock. And I see you've been working on your makeup. It looks really nice. I hope your lipstick doesn't get too messed up tonight," he said with a laugh.

"Oh I think my lips and lipstick will get a good workout tonight!" I replied with a wink.

"That's my girl! Go get ready," as he patted me on the bum.

I went to the bathroom and put the chastity device on. It took a while to figure out how to do it. I thought James could have at least helped me with it. Anyway I got it on and put one key on the bathroom counter. I put the other key in my pocket for Stan. Then I used an applicator to squirt some lube into my love hole. I didn't put any between my bum cheeks because I don't like the feeling of the lube squishing around between my cheeks when I'm walking or sitting. And a big stain of lube on the back of my panties is unbecoming. I popped the lube bottle into my purse.

Then I touched up my makeup and adjusted my clothes and hair. I was taking a final look in the mirror when I heard Stan's pickup truck coming down the driveway. Right on time, I thought. Stan wasn't going to miss a minute with me.

"Come on in," I heard James call out.

When I came into the living room, both men stopped and stared at me. I did a saucy little twirl.

"Do I look presentable gentlemen?" I asked.

"You look great Diana," Stan replied.

"Yes, I'm sure Stan will be proud to have such a pretty girl on his arm tonight" added James.

"Where are you taking my niece Stan?"

Stan cleared his throat. "Oh, I was just going to take her for a drive in the country to the west. Just show Diana around, you know."

"Sounds good Stan, but don't keep her out too late."

"Don't be silly James, I'm 19 remember!" I said.

"You're in my care Diana and I want you back her by 11PM at the latest," James replied.

"That's no problem Mr Wilson," Stan said. "I'll have her home well before 11".

"Great. Well you kids have fun tonight."

"Thank you Mr Wilson. Ready to go Diana?"

"I'm as ready as I'll ever be - let's go, Stan."

I grabbed my purse and followed Stan to his truck. "Bye," I waved to James. "Don't wait up for me."

Stan led me to the passenger side of the truck and opened the door for me. I was impressed that he was treating me like a lady, and that showed that he was already thinking of me as a young woman, not just as a cocksucking crossdressing faggot. I felt tingles in my cock but it wasn't going anywhere locked up in the chastity device. Not being able to have an erection was actually a nice feeling given that I knew Stan wasn't into cocks and the chastity device would prevent inconvenient poking and perhaps turning Stan off. So I settled back in the seat and relaxed.

Stan had a nice truck, a Ford F150. I was surprised he could afford one at his age.

"Oh this is my dad's truck," Stan explained. "He lets me use it for my summer job."

I waved at James as Stan turned the truck around and drove down the driveway. I felt excited and a bit scared being alone in a vehicle with someone I hardly knew. But I was pretty sure Stan was a nice guy who would take care of me. And I was certainly willing to take care of him!

We took the highway away from town. it was a warm evening and the low sun was in our eyes as we drove.

"Does Mr Wilson know you are a crossdresser?" Stan asked.

"Actually he does, it's my mom who doesn't know. I mean I dress in boy clothes most of the time but I dress like a girl whenever I have an opportunity. For the next couple of weeks I'm staying at James' cottage and I dress up every day. I happened to be outside hanging out the wash when you came by yesterday otherwise I would have hid in the house."

"I'm glad you didn't hide in the house! That was the most incredible blowjob you gave me yesterday. I jacked off twice last night thinking about it!"

"Well, I love feeling like a woman and pleasing men is the way I feel most feminine. I'm glad we met too."

We travelled down the highway past fields, barns and farm houses. I could see that Stan was the quiet type, shy perhaps. And he was a very hunky young man. Big broad shoulders, blond curly hair, muscly arms and legs, and a big package between his legs.

We turned off the highway onto a dirt road. We travelled a long time up a gentle slope until we turned off again onto a narrow track. We were isolated but I felt safe with Stan. Soon we came to the end of the track at an opening with a view of the whole lake. I thought I could see James' cottage on the other side.

The sun was low now. It was a very romantic setting and I was feeling romantic. I hoped Stan was too.

"Let's go for a little walk and enjoy the view, Diana".

We got out of the truck and walked down a gentle slope in a meadow of tall grass. The view of the sunset and of the lake and mountains in the distance was beautiful. The breeze was gentle and warm.

"Let's sit down for a bit," I suggested.

"Sure, here's a nice spot. But wait a sec." Stan ran back to the truck and returned with a small bundle. It was a blanket.

"Here, help me spread out this blanket."

"That was thoughtful Stan," I said, impressed with this young man.

We sat down together on the blanket and I leaned over and put my head on Stan's shoulder. I could tell he was nervous and I wanted to find a way to calm him.

"I can't wrap my head around the fact that you're a guy because you look absolutely beautiful, Diana."

"You're so sweet, Stan. That was a very nice thing to say," I said as I snuggled down closer to him.

"I have something for you, Stan."

I reached in the back pocket of my capris and pulled out the little chastity key.

"What's this for?" Stan asked.

"Well when you told me you weren't into cocks, I locked my penis in a chastity device so it won't get hard and won't get in your way. If you want to let me cum later you can use the key to unlock me, but only if you want to."

"Wow, I've never heard of such a thing, Diana. You're introducing me to lots of crazy stuff."

"I thought it would be the best thing to do for our date." Then I moved my head up to his and gave him a big wet kiss on the lips. Stan responded as I hoped by putting his arm around me and kissing me back. Another straight guy kissing me!

"Stan, you're such a good kisser! I love it!"

"Do you have a girlfriend?" I asked.

"Yeah, her name is Cindy."

"How's your sex life with Cindy?"

"Um, well we love to make out and she has great tits but she doesn't really like giving head and I've never fucked her, at least not yet."

"Well that's something I can help you with, Stan. I love giving head and I love getting fucked too."

With that I moved my hand to his shorts and slipped it inside to his cock. I hoped to find it soft so I could feel it getting hard in my hand but it was already big and hard!

"Maybe I should let your big beautiful cock out for some fresh air." And I began to unbutton his shorts and pull down his zipper. His huge bulge was making that difficult but I succeeded.

"Stan, lift your bum and I'll pull your shorts down." I got his shorts and underwear off and he sat there on the blanket looking at me with his gorgeous big cock sticking straight up like a fence post between his athletic legs. I was past the point of no return and repositioned myself on my knees and started to massage his cock with my hands. There was already lots of precum and I swirled it around his big knob with my fingers.

"That feels so good, Diana."

I moved one hand down to fondle his balls while moving the other one up and down his shaft. He started to moan.

I got a little closer and started licking all around his cockhead. It tasted wonderful and the fragrance I smelled told me that he had taken a shower just before coming to get me. A real gentleman! I was liking this young man more and more.

I took my time with oral stimulation. There was lots of time to pleasure him with my mouth and he could still make love to me after if he wanted to. I hoped he would enjoy my love hole tonight.

While I sucked his cockhead Stan reached down to play with my tits. I loved the way every guy would squeeze my tits even though they knew they were fake. And I loved having them squeezed. It just seemed so right for men to enjoy my tits.

My mouth strokes were slow but gradually getting deeper and deeper until I couldn't take any more.

Stan reached one hand down to play with my ass. I moved up to crouch on my knees with his cock in my mouth and my ass close enough that he could easily play with it.

"Jesus Diana that's fantastic!"

"Don't cum yet big boy, I want this to last."

"I can't last long," he gasped.

I loved the effect I was having on this young stud. My mouth going up and down on his juicy cock made him shudder at every stroke. I started to unbutton my capris with one hand, hoping that Stan would take the hint and help me remove them.

Stan slid a hand inside my capris and inside my panties to feel my bum. I interrupted my cocksucking to say, "you can play with my love hole, it's fresh and clean for you."

Stan pushed my head down on his cock with one hand and slide the other between my bum cheeks to my hole. He teased my rosebud with a circular motion of his big finger. It felt wonderful.

"I'm going to cum!" he exclaimed.

"Just pretend I'm Cindy and cum in my mouth." Then I started pumping faster with my mouth and stroking his shaft with both hands.

Stan's cock erupted in an enormous load. He spurted at least five times making it hard to keep my mouth on his bucking cockhead. But I hung on and somehow made room in my mouth for all of his cum and his cockhead until his thrusts subsided and I could focus on swallowing his delicious seed.

Finally I let Stan's cock slip out of my mouth and I rested my head in his lap. I hadn't spilled a single drop of Stan's load and I was proud of the great blowjob I just gave him.

"God Diana, that was incredible! I didn't think about Cindy at all, just about you and how sexy you are."

"I'm so glad you're satisfied, Stan. It makes me feel wonderful to please you."

We both stretched out on the blanket and held each other, my big titties squeezed between us. I felt like Stan's girlfriend. I wished I could meet Cindy and teach her about sex, about the joy that comes from satisfying a man, the fulfilment of giving a good blowjob. The poor girl didn't know what she was missing!

The sun was on the horizon now but the evening was still light and warm.

After a few minutes lying together quietly Stan started kissing my mouth. I took his tongue in my mouth and sucked it while one of his hand was trying to get my capris down.

"Here let me help you," I offered.

I sat up and undid my belt and unzipped my capris. Stan helped me pull them off while leaving my panties on. The panties were pretty and lacy in front and my chastity bulge was hidden between my legs. I knew Stan was thinking that I looked like a woman and it turned him on.