Pleasing Mr. Wilson

It was early summer and I had just turned 19. I graduated from high school in June and wasn't sure what I was going to do now. My mom said my choice was simple - go to college or get a job. For now I was looking for a job to get me through the summer. I was willing to do pretty much anything but was hoping for more of an 'office' type job. I had a slight build and didn't think construction or hard physical labor would be a good fit. And I kept my hair fairly long which sometimes made me a target for teasing.

Earlier this year I discovered my powerful urge to feel feminine. It all started when my friend Gordon convinced me to suck his cock so he could experience what it would be like to get a blowjob from a girl. At first I was turned off by the idea but I quickly came around after Gordon got me to dress up in his mom's bra and panties. It was at that moment I realized I loved looking and acting feminine for Gordon and giving him the satisfaction he craved. With Gordon's guidance I improved my cock-sucking skills to the point that I could make him cum in just a few minutes. A few minutes later, I'd suck him again.

It was wonderful pleasuring Gordon in the basement of his family home when his parent were out. But Gordon wasn't comfortable with the arrangement. Perhaps I was too eager to please him, but he made it clear that he wasn't gay. He always closed his eyes when his cock was in my mouth which dissapointed me as I wanted to make eye contact. I wanted to feel that intimacy a woman experiences when she is sucking her man's cock. Instead, Gordon made me feel like a cock-sucking robot who satisfied his fantasies and got nothing in return.

Well, I did get a lot of satisfaction every time Gordon grunted and spurted his load in my mouth. I came to love the taste of his cum and enjoyed swallowing it after every blowjob. But Gordon never pleasured me. I jacked off every night at home thinking about being on my knees with his tasty cock in my mouth.

I had hoped to expand my horizons with Gordon. I got hold of a dildo and was working my bum hole in the evenings in the hopes of getting Gordon to fuck me. But he wasn't interested. "That's too gay for me," he said one Saturday morning, as he shoved his cock back in my mouth. Anyway, everything changed when Gordon moved out of state on a football scholarship. I wouldn't be seeing much of him anymore.

I was going around to all the small business' in town looking for a summer job when the manager/owner of the grocery store invited me to his office for an interview.

"Have a seat Dana," said Mr Wilson. "So you're looking for a summer job. I'm sorry but all the parttime positions at the store are filled. But, if you're handy I could give you a lot of work at my cottage at the lake. I'm kind of desperate for help there. Do you have any experience with carpentry and painting?"

"Actually I do, Mr Wilson. I helped my dad a lot with work on our house. I'm sure I can handle any repairs and painting you need."

"And how are you in the kitchen, Dana?" That question surprised me. Did he expect me to cook? I wasn't looking for a job as a live-in maid.

"Well, if you mean how's my cooking, I can fry an egg I guess but I don't have much experience in that department. Do you need me to cook, Mr Wilson?" I suddenly had a vision of cooking and cleaning in Mr Wilson's cottage kitchen and waiting for him to come home after a hard day's work to a home-cooked meal, followed by me satisifying him in other ways. Mr Wilson was a fairly good-looking man in his 50s and the fact that he was much older than me and more experienced in the ways of the world turned me on. I felt a tingle in my cock. But I snapped back to reality when I remembered that Mr Wilson was married with two kids so he couldn't possibly be interested in a little sissy faggot like me.

"Cooking skills would be handy because I spend a lot of time there in the summer and if you made supper for me before I got back from work, that could be part of the job. Also, sometimes I have BBQs there with friends on the weekend and it would be great if you could help with the food. Of course you'd be invited to join us. I wouldn't want to see you hang back, out of sight like a maid," he said.

"Well, I'm glad you don't want me to wear a maid's outfit, Mr Wilson," I laughed. But part of me was thinking about how I could dress up in ladies underwear while alone at the cottage. I imagined being up a ladder wearing nothing but a bra and see-thru panties when Mr Wilson arrived unexpectedly. "Oops," I'd say, "you caught me dressing up again. Whatever will you do with me Mr Wilson?"

Mr Wilson offered me a decent hourly wage and we agreed that I would start Saturday so he could be there all day with me and show me what to do. I was excited to have found a job and it sounded like I could work all the hours I wanted and earn as much money as I needed. I was looking forward to seeing Mr Wilson's cottage in a few days.

When Saturday finally arrived, Mr Wilson picked me up at my house in his big SUV. He came to the house and had a friendly chat with my mom. My mom knew his wife.

The cottage was small but very nice with big windows looking over the lake and a wood stove in front of a huge stone fireplace. Although close to town it was at the end of a long driveway through dense woodland and there were only a few other cottages visible on the lake so it felt quite isolated, just the way I liked it. Most days I would be cycling to the cottage so I'd be getting some exercise this summer. If it was rainy Mr. Wilson said he'd drive me. My mom worked and needed our car every day.

Mr Wilson gave me a tour of the cottage. "Does your family spend much time here?" I asked.

"Usually they do, Dana. But this summer my wife is using a lot of her vacation to visit her folks out east with the kids so I have the cottage to myself for over a month. I'd really like to get the place fixed up while they're away" Mr Wilson explained.

The master bedroom had frilly curtains and bedspread, and doilies on the dressers and makeup table. "Your wife put a feminine touch on the bedroom," I observed.

"You have no idea Dana," Mr Wilson replied. "Sara loves all things feminine. Just look at this," as he opened the top drawer of a dresser. Inside was a huge number of pretty bras arranged on the left and silky panties on the right. There was every color in the rainbow. I couldn't believe it, and couldn't understand why Mr Wilson would show me his wife's underwear.

"Your wife certainly has pretty undies Mr. Wilson," I mused.

"Do you like this sort of thing, Dana?"

"Oh, I've never paid any attention to women's underwear," I lied.

After outlining all the different jobs to be done around the cottage I started by scraping peeling paint off the eaves. They would all have to be scraped and painted which would take days. I was on a ladder most of the day trying to tuck away a hard-on caused by visions of Mrs Wilson's pretty bras and panties. Sara was an attractive woman in her early fifties who always dressed nicely. She had a 'conservative but sexy' style which was very alluring. I felt lucky that I had glimpsed her sexy under garments. I'm pretty sure Mr Wilson noticed that I had a hard-on up the ladder but he didn't say anything.

At the end of the day Mr Wilson fired up the BBQ to show me how to use it and he cooked us each a hamburger and an ear of corn for supper. After supper and a beer Mr Wilson drove me home.

That night at home in my bed, I jacked off imagining Mr Wilson fucking his cute little wife in her sexy lingerie. I imagined what she would experience with her husband on top of her with his cock inside her pussy. I imagined her panting and screaming as Mr Wilson fucked her. And then I imagined that it was me getting fucked in pretty ladies' underwear. I fantasized that Mr Wilson was using me as a substitute for his wife while she was away, only my blowjobs were more eager and my pussy tighter than his wife's. That's when I shot my load.

The weather was beautiful in July and I started riding my bike out to the cottage every morning which took about 45 minutes. The days entailed a lot of scraping and painting but also repairs and cleaning inside the cottage. I couldn't resist exploring Mrs Wilson's underwear drawer several times a day and having a satisifying jerk while imagining wearing her panties and bras. I discovered other delights too - a basque, garter belts and stockings in the bottom drawer and a few sheer babydolls and negligees in the closet.

"God, she really must love turning her husband on," I thought. I felt a bit jelous of Mrs Wilson being able to satisfy her husband any time she wanted. But was she willing any time Mr. Wilson wanted? Would she do everything he wanted her to do? Not necessarily. And that got me thinking about being Mr Wilson's little cocksucker on the side. I'd be willing to pleasure him any time he wanted, that's for sure. The thought gave me a big erection and I had to jack off immediately.

But how to find out if Mr Wilson was open to me pleasuring him? I was hopeful because he made a point of showing me his wife's panty drawer. Why would he do that except to guage my reaction? And he did ask me if I liked "that kind of thing."

I still didn't dare dress up in the tempting lingerie because Mr Wilson sometimes popped in unexpectedly and I didn't want him to catch me dressed up in his wife's underwear. Well, part of me DID want to get caught. And sometimes I would wear a pair of Mrs Wilson's panties under my shorts, even wearing them all the way home.

One day I brought my big fake titties I got online to the cottage. I kept them in my backpack hoping for an opportunity when I'd feel brave enough to put on a bra with the fake tits and have a quick jerk. This wasn't to be the day however as Mr Wilson came to the cottage unexpectedly midafternoon. "How are things going, Dana?" Mr Wilson called out from the porch.

"Pretty well, Mr Wilson," I replied. "The eaves are almost done and I should be able to wrap it up before it rains. I came down from the ladder to show him what I had accomplished so far today. I felt a bit of a thrill knowing that I was wearing a lacy pink pair of Mrs Wilson's panties under my shorts. I imagined that his hands had already been inside these very panties feeling his wife's pussy. But I had to distract myself with other thoughts to avoid getting an embarrassing hard-on!

"Looks great Dana," observed Mr. Wilson, "but I don't think you'll get it finished before the rain starts this afternoon. It's going to be a downpour - that's why I came home early. Why don't you come in and take a break? Anyway, there's something I want to talk to you about," he continued.

We both sat down on the couch. "why don't you go get us each a beer, Dana". So I got up and got two cans of beer out of the fridge. I wondered what he wanted to talk about.

"I want to ask you something, Dana" Mr. Wilson began. "It's no big deal but I do want the truth."

"Of course Mr. Wilson, go ahead and ask me."

"Well I just want to know if you've been messing around with my wife's underwear?" he asked bluntly. I suddenly felt panic. I was shocked by the question especially while sitting in front of Mr Wilson secretly wearing his wife's panties.

"I, uh, well," I stumbled. "Yes, I did take another peek after you showed me her underwear drawer" I confessed.

"I thought so" said Mr. Wilson stroking his chin. "Like I said, it's no big deal, and I don't actually mind. But I want you to be careful to put everything back exactly how it was. I think you've been a bit careless because I checked her panty drawer a couple of times and noticed things out of place and that there are changes from day to day. That's how I knew you were checking out my wife's lingerie. I sort of expected it because of the way you reacted when I showed you Sara's panty drawer. I did that deliberately to see how you would respond," he explained.

"I'm so sorry, Mr Wilson" I began but he interrupted me.

"Like I said I don't mind. In fact I've always been curious about crossdressers. You do put on some of the things, don't you, Dana?" he asked.

"Well, not really" I started. "I mean I did try on one pair of panties quickly just to see how they would look, but I put them back exactly where they were."

Mr Wilson leaned forward and asked, "Did you play with yourself while wearing my wife's panties?"

"Um, yes, a little" I fibbed.

"A little, eh?" Mr Wilson sounded doubtful. "I can't believe you didn't jack off Dana. It's only natural. But if you get cum on anything you will have to wash it appropriately and put it away. Do you know how to wash lingerie, Dana?" he asked.

"Not really Mr Wilson, but I will learn how to wash it properly, don't worry," I replied.

"And now that we've established that you like to dress up in women's underwear, what would you think about showing me how you look? I've had a thing for trannies and crossdressers for a while so I'm intrigued to see how you look dressed up. With your slight physique and long hair I bet you can look very feminine. Don't worry, no one will ever know that you dressed up for me," Mr Wilson said reassuringly.

I was reassured, and I did have a powerful urge to give him a show. "Ok, I guess I could throw on a few things but I don't normally do this sort of thing," I said unconvincingly.

"That's fine Dana, you only have to do it if you want to. But it sounds like you want to so I'm excited to see how you look," he said as he adjusted a bulge in his pants.

"But I hope you're not dissapointed, Mr Wilson. I don't know how to do makeup and I don't have a wig."

"You have nice features, Dana, and I'm sure you'll look lovely. Go change and surprise me!" he urged.

"Actually, I feel pretty grubby after all that scraping and painting. Do you mind if I have a shower first?" I asked.

"That's fine, Dana. But why don't we have a shower together? I'd like to get to know you better!"

"Oh my gosh, Mr Wilson. I've never had a shower with a man before but I'd love to!" I exclaimed. I couldn't wait to get my dirty work clothes off. My cock was stiff and uncomfortable. We both walked to the bathroom and I started to undress while Mr Wilson watched. I had my shorts half off when I remembered I was wearing Mrs Wilson's pink panties. I blushed when Mr Wilson gave me a knowing look and reached out to tug the waistband of the panties.

"This is exactly what I expected, Dana. You've been enjoying my wife's lingerie all along. If I didn't like it so much I'd say you need a spanking. But for now let's have that shower."

"Mr. Wilson, I never expected that you would be gay," I said.

Mr Wilson started to undress. "Let's just say I've got some repressed 'bi' in me" he said. "With my wife away and a feminine young man keeping house for me, this looks like an opportunity to try a few things, don't you agree Dana?"

"I'll try to be as feminine as I can for you, Mr Wilson", I said as I reached my hand out to touch his erect cock. It wasn't huge but it was bigger than mine which always made me feel more feminine. We moved into the shower and let the warm water run down our bodies.

I moved closer to Mr Wilson, facing him, until our cocks touched. I soaped up my hands and started rubbing our cocks together, something I had always wanted to do. It felt so good squeezing our cocks with both of my hands. Mr Wilson was moaning and moving his hips gently in and out of my hands. Then he surprised me by moving his head toward mine and kissing me. It was the first time I had ever been kissed by a man and it was a thrill. I responded by opening my mouth so he could explore it with his tongue while I increased the tempo of cock-rubbing (I later learned that cock-rubbing is called 'frottage'). After a few moments Mr Wilson broke off the kiss and said, "You better stop that Dana or I'll cum, and I don't want to do that yet."

Mr Wilson got out of the shower while I stayed in and made sure I was clean all over. I washed my hair and gave my cock, balls and bum crack a good soaping. I used my fingers to make sure my bum hole was perfectly clean.

By now the rain had started and it pounded noisily on the metal roof. Mr Wilson put on a warm housecoat and made a fire in the wood stove while I went to the master bedroom to select the lingerie I would wear.

"I'll stay out here by the fire Dana," called out Mr Wilson. "Let me know when you're ready and I'll join you in the bedroom."

"It will just take a few minutes," I replied. A few minutes later I called out to Mr Wilson, "could you bring me my backpack, please? It's in the porch." Mr Wilson brought the backpack and I opened the door just enough so he could pass it to me without seeing me.

"I can't wait to see what you come up with, Dana" Mr Wilson said excitedly. "By the way, I meant to ask you if you have a special name when you're dressed?"

"Um, I never really thought about that Mr Wilson," I replied. "Perhaps 'Diana' would work. What do you think?"

"Diana sounds just fine," Mr Wilson replied. "I'll sit tight waiting to see how Diana presents herself."

I felt pressure to dress quickly and to have a pleasing outfit. I pulled the fake silicone titties from my backpack and looked through the bras for one that would look especially good with them. Luckily Mrs Wilson had a big bust so most of the bras would work. But one white one caught my attention. It was mostly sheer fabric in the cups with lace around the edges and straps, and a pretty pink rose between the cups. I knew this one would show off the big pink aeroles and nipples of the titties. Then I had to find other white items to match. White sheer panties came next. And a pretty white garter belt. I selected a pair of tan stockings with a wide band of lace around the tops.

I quickly put on all of these treasures and twirled around in front of the mirror. I looked pretty decent I thought. Then I went to the closet and selected a babydoll that was light pink and practically transparent, with a short hemline and lots of lace around the edges. It had puffy sleeves which gave a coy air of modesty. I wanted to look demure but fuckable.

Before calling Mr Wilson in, I decided to put on just a touch of Mrs Wilson's eye shadow. I had bought a beginner's makeup kit but barely had a chance to practice with it because I was afraid of my mom finding out. Here in Mr Wilson's cottage, I felt secure and I wanted to look my best for him so I gave it a shot. With pink and white lingerie I went with black eyeshadow, 'Midnight'. I just put on a little and the effect was really nice. My eyes looked seductive and feminine, I felt I looked as good as I could.

"I'm ready Mr Wilson," I called. I positioned myself in the middle of the bed sitting with my legs folded, my hands placed modestly in my lap.

"Oh my god Diana, you look stunning!" exclaimed Mr Wilson upon entering. "And what about your tits? They look really nice. I'd like to feel them."

Mr Wilson walked over to the bed. I could see his cock making a big tent in the fabric of his housecoat. It was a thrill to know his hard-on was for me! He sat on the side of the bed and pulled himself up beside me. "I loved it when you kissed me in the shower", I whispered. Mr Wilson leaned toward me and we started kissing again.

Kissing is such a simple yet erotic act. I was loving being in Mr Wilson's arms with his mouth exploring mine. My stiff little cock was so bound up in my panties that it hurt. Soon I had to change position and arrange my panties.

I sat on my knees on the bed and began to arrange my panties when Mr Wilson said, "How about pulling your panties down a little so I can have a better view?."

I was flattered that a man was telling me how he wanted me to undress. I started to pull the panties down very slowly while swaying my hips and watching Mr Wilson's expressions of delight and lust. When I got to my boner I gave the panties a tug and my little cock sprang out. Mr Wilson seemed pleased as he reached out to touch it. Mr Wilson opened the drawer of a bedside table and pulled out a small tube of lube. Silently he squeezed some onto his hand then spread it on my cock. He moved his slippery warm hands all over my cock and balls. I was totally shaved down there which felt especially nice in his hands. Very quickly I squirted my load onto his hand and the bedspread.