Role Playing is Such "Hard" Work

My partner and I often enhance sex through role-playing. Sometimes one of us has a fantasy that just has to be satisfied and other times we'll kind of fall into a "game" and see where it leads. Both of us enjoy acting out our roles, especially when they are opposite to our normal personalities.

I am a senior executive for a large candy company. Last week we launched the latest thing in sugar free confections, and to celebrate my company threw a party on Friday night for its employees and their significant others. Naturally I attended, taking Valerie, the woman of my life and live-in lover, as my date. Val works as principal designer for a well-known intimate apparel chain. She's in her mid-50s, is fairly tall and has dangerous curves in all the right places. She has a beautiful expressive face with large eyes and full lips. She's always full of refreshingly filthy thoughts and ideas. I'm about 5 years younger than Val, tall, reasonably fit and also in possession of a truly dirty mind. At the party we mingled with other couples, drank, ate, danced, fucked in the executive conference room, danced some more, ate, drank a bit more, fucked in the women's restroom, drank a bit more; well you get the idea! When the party came to an end, my company gave each one of us a "goody bag" with samples of the newest products as well as some of the old standards. Little did I realize the role candy would play in our sex life!

It was about half-past midnight when we finally got home. I had a buzz on and was pretty tired and told Val I really needed to get some sleep. Val was pretty tipsy herself and would welcome 7 or 8 hours of uninterrupted rest. I asked her what she wanted to do later that day. She looked at me with a wicked smile and said she brought work home. I'm sure my face lit up in delight! Val designs women's intimate clothing, a.k.a. lingerie, a.k.a. "fuck-me" clothes! When Val brings work home, it means she'll be modeling her latest creations for me in order to gauge my reactions. We use an informal, but foolproof rating method; if my dick stays limp, then that article of clothing is a loser; if it reaches half-mast, then there are possibilities for that piece; if I get mostly (at least 3/4) erect, she's got a winner; and finally, if my cock gets super hard to where it won't go down, then she's created a sure thing. In fact, Val has hired me on as a paid consultant to run satisfaction surveys for her firm because my rating system is amazingly accurate! Val's company earns boodles from her creation, and she and her subordinates get nice bonuses every time sales of a new product exceed a minimum dollar amount (that happens pretty often!), and I get paid for staring at a scantily clad hot woman and letting my cock make all the "hard" decisions. It's the perfect win-win-win situation!

I awoke shortly before 10:00 AM. As I rubbed the sleep out of my eyes I tried to decide if I wanted to get up. The smell of fresh brewed coffee and the sizzle of something frying in the pan was enough to get me on my feet. I didn't bother putting anything on as I padded into the kitchen. There I saw Val sitting at the table dressed in a nightgown, sipping coffee while reading the newspaper. She heard me come in and looked up.

"Well, good morning sleepy head! Did you have a good rest? Did you have any interesting dreams?"

As a matter of fact, I did have an interesting dream in which Val and I were vying against 4 other couples for the gold medal in the Kama Sutra Olympics. We were evaluated on every position described in that reference and the winning team would have the most points. At the time I awoke, we had completed maybe the first five positions.

I guess my penis stirred as I recalled my dream. Val noticed and said with a hint of mischief,

"Ooooh, I think you DID have a nice dream! Was I in it?"

I nodded a "Yes".

With that question answered she reached for my manhood and brought it to her lips. She looked up at my face with her big eyes. Then she gently kissed the tip.

My cock stiffened a bit more.

"Do you want me to do that again?" she asked.

I just nodded "Yes".

She smiled and kissed the tip of my cock once more. Then she took a mouthful of coffee right before sucking in my hardening dick. The feeling of my cock bathed in the hot liquid was quite shocking, yet very stimulating. Val watched my face as she moved her head back and forth over my engorged cock. After about a minute she let it slip out and swallowed the rapidly cooling coffee. Val had me sit on the table with my legs as far apart as I could get them. Once again she took a mouthful of coffee, but instead of sucking my shaft, she bent down and took both my balls into her mouth. My God, did THAT feel great! I love it when she does my nuts, but the heat of the coffee just heightened the sensation. Val swirled her tongue around and between my balls and she gently sucked on them separately and together. I my mind's eye I could see my sperm production going into overdrive! The coffee in her mouth soon cooled and she let my balls plop out. I told her I was sure I would come soon. She considered taking the remainder of the coffee, but then had a better idea. Val started sucking on my prick with great gusto. She wanted to finish me off. I figured I'd pop in her mouth, but just before I shot off, Val brought her cup up to cock level. Spurt after spurt of thick pearly semen ended up in her coffee cup. Eventually, I ran out of cum. Val put her cup down and licked my cock head clean. Then she reached for her coffee cup and peeked in.

"Wow, I thought I'd have a little cream with my coffee, but I guess instead I'll have a little coffee with your cream!"

She showed me the contents of her cup. Thick globs of cum had sunk to the bottom, while the remainder of her coffee floated with the more liquid components of my cum on top. She swallowed the coffee mixture, being careful to leave the thick clots of cum behind. Then, with great ceremony, Val titled her head back, opened her mouth, stuck out her tongue as far as it would go, and let the cum flow onto it. One, two, three, four distinct globs transferred from the cup to her tongue. Val straightened her head and turned to face me. She showed me her tongue. It was completed coated with my sperm. Val closed her mouth and made a big production of swallowing it as well as the remains of cum she had scraped from the inside of her cup with her finger.

When she finished she said,

"That was nice! You taste really good with coffee. I'll have to have more tomorrow! Now go have some breakfast and take a shower. Remember, I brought work home and I need you to help me with it!"

As soon as my erection had finally gone down, I took her advice. I had a piece of fruit a fried egg and some toast and washed it down with a couple of cups of strong coffee. Then I did the morning ritual of the 3 S's (shit, shower and shave) before returning to our bedroom. Val asked when would be a good time to get started. She said she had four outfits to show me. Past experience suggested that each very good or definite possibility would require at least an hour of close scrutiny (maybe "screw"tiny is a more accurate word!). It was now approaching 11:00. I thought we should start in mid-afternoon. That way, we could do something outdoors and I'd have a chance to replenish my supply of jism. She agreed and suggested 4:00.

Val and I got dressed and went to a local park. We walked through the park and sat by the lake watching kids play and people stroll by. We also kept an eye out for the birds and squirrels, watching them do what they do best. After an hour or so, we walked into town and did some window shopping. At about 2:30 we stopped for some lunch at a local coffee shop. While we ate, Val began hinting at the sexy lingerie I'd get to review, letting my imagination run wild in anticipation of what was to come. She did this to heighten the suspense and get my dick a-twichin'. We finished lunch and walked back home. Val's mind games were very effective and there was a definite tenting in my pants. I didn't care who saw me; I just want to go home and get to "work"!

Once home, the role-playing began. With each sexy outfit, Val would construct a small drama with us as the actors. The outcome of the play would help decide whether that bit of lingerie would go into production or not. Before we started, I opened a bottle of wine and poured two glasses. We sipped the wine, talked a bit and kissed deeply. I could feel Val trembling. She must have some really hot stuff to show me!

It was now 4:00 PM. Val got up and told me to get ready for the show. I went into the living room and she went into our bedroom. I moved around some furniture to give her more room to maneuver and then stripped off all my clothes. I sat down on the couch and had some more wine while I waited for Val to come in.

About ten minutes passed. I idly wondered if she'd fallen asleep or forgotten about me. I was about to get up to check on her when loud, rhythmic music filled the room. The bedroom door flew open and in swept Val. She had on a low-cut black bra that just barely covered her nipples, a black garter belt and very skimpy black panties. All three items had bright red piping as the only trim. On her legs she wore ultra sheer black stockings, and on her feet she had on black stiletto heels. She was incredibly sexy looking in that get-up! Val was in full vamp mode, taking long, purposeful steps as she strutted around the room. She walked up to me and bent forward at the waist, squeezing her breasts and jiggling them in my face. Then she turned around, spread her legs and bent down, wiggling her ass at me. The panties seemed to hardly be there as her pussy and butt crack were quite visible. She straightened up and again turned around. Val stood over my left leg and slowly lowered herself. On contact, she began sliding her crotch forward and backward over my leg. After a couple of minutes, she rose up and took a step back. Val lay down on her back and opened her legs wide. The crotch of her panties had effectively become transparent. The details of Val's vagina were so clear that I had to reach out and touch it to convince myself there was any covering at all! My cock reached about 95% of vertical. Val smiled and gave it a big wet kiss. This little outfit was a winner!

Val stood up and sashayed into the bedroom. At the door she turned her head to face me and stuck out her butt. She took off the panties and tossed them to me giving me a great big smile before closing the door. The thumping music stopped. I took hold of the panties and inhaled deeply of Val's sex. Soon I placed them on the couch next to me and thought dull thoughts. Eventually my dick began to deflate. I had a bit more wine and sat back, waiting for Val's next offering.

After about ten minutes, can-can music from the movie "Moulin Rouge" came on. Val opened the door and timed her entrance to the music. She ran in and began dancing the can-can. She had on a green, frilly, one-piece outfit. Most of her tits were exposed as were her thighs. She had on green stockings and high heels. A feathered headpiece and a Japanese fan completed the ensemble. Val danced, kicking her legs high into the air. As before, she turned her back to me and bent down giving me a good look at her ample bottom. She twirled, arched her back, and did splits. I really enjoyed her routine, but the outfit didn't do that much for me. It was a half-master at best. Val ended her routine and saw that my cock wasn't as impressed with this item as with the first. She made a pouty face and mumbled something to my penis about not knowing a good thing. She stuck her tongue out at my prick in a show of displeasure, avoiding contact with the head. I tried to reassure her that even though the clothing didn't do it for me, I sure did enjoy her dancing and wouldn't mind seeing it again and again! Val scrunched her lips and said,

"Well, alright. But I can't believe you didn't like that can-can outfit! Everyone at work thought it was the best thing we'd done in a long time!"

I replied,

"Well, it isn't bad, but it's just too frilly for my tastes. And that part covering your bottom looks like something a grandma might wear. Why don't you chalk it up as a 'maybe'?"

She agreed and left the room. The movie soundtrack ended. My cock became totally limp as I awaited Val's next scene.

Soon the sounds of people talking and bells dinging came on. Val reentered the living room and swept past me into the dining room. She had on a blue waitress' uniform, complete with a white blouse, white stockings and scuffed white shoes. She even had a nametag pinned to her blouse. From the dining room I heard,

"Table for Joe, party of one."

I stood up and ambled in, my dick jumping from side to side.

"Joe? Table for one? Please be seated. I'll be with you shortly."

I sat down and made myself comfortable. I couldn't help but wonder what Val had in store. I didn't have long to wait.

"Hi! I'm your hostess, Val. Is there anything I can get for you from the bar?"

I asked for a glass of the house wine.

"Very good, sir. I'll be back in a minute to take your order."

She quickly turned around and walked toward "the bar" to get my wine. It was only then that I noticed her uniform only covered her front and sides, kind of like an apron. Her backside was completely exposed! If she'd really been a waitress, Val would have already earned a very generous tip! My cock began stiffening for the third time that afternoon. I moved my seat back a couple of inches to give it room to grow. Val came back with my wine. She asked if I was ready to order. I said I couldn't decide and asked if she would suggest something.

"Of course, sir. The pie is very good today! Would your care for a taste before deciding?"

I agreed that was the prudent thing to do.

Val asked me to move my seat back a foot or so. I did and she hopped on the table, lying back with her legs spread. Her freshly shaved "pie" was before me.

"Please, help yourself!" she urged.

I licked my lips and dove in. I'm afraid I had much more than a single taste of her "pie", but Val didn't seem to mind! It took a minute or so before she shuddered in orgasm. I sat up, my face covered in her sex goo and Val stood up, straightening the front of her uniform. She gazed down at my full erection and remarked,

"Sir, you have quite a handsome penis! May I take a closer look at him?"

I responded that she could look as closely and as long as she wanted. She touched my cock, running her fingers over the flesh. I enjoyed every moment of her attentions. Then she took it into her mouth and kept it there, pressing her tongue on the bottom and head of the shaft. Soon, she released my prick and said,

"That was very nice, sir! Unfortunately I have to get back to work. My boss doesn't want us becoming too friendly with the customers."

I asked her how much I owed for the delicious "pie". Val said it was on the house and not to worry about it. I started to protest, but she shushed me and gave my cock a parting squeeze. She swayed her butt from side to side as she walked away to wait another table.

The waitress outfit was a definite winner!

I returned to the living room. I thought we had reached the high point of Val's modeling. I was wrong, and I couldn't have been happier.

"Joe, where's the candy from yesterday?"

"Look in the closet. There should be two small bags."

"Oh, I found it. Thanks!"

What was that about? Maybe she needed a little pick-me-up? I didn't know and I soon forgot about it.

The bedroom door opened to the sounds of a kiddie TV program. Out skipped Val, wearing a dark red babydoll with sheer red panties, knee socks, bunny slippers and a barrettes in her hair. In her hand she had a big red cylindrical lollipop. The lollipop made the whole scene more believable. She skipped around the room. Her tits, butt cheeks and thighs bounced as she moved. Suddenly she stopped in front of me. In a little girl's voice she asked

"Hi! Do you want to be my friend?"

She looked at me with an innocent little-girl look as she licked her lolly. Jeez, I wanted to take her right then and there! She looked so hot!

"Ye-, Yes, I want to be your friend! What's your name, little girl?"

"I'm Valerie, but you can call me Val. What's your name?"

"I'm Joe. I'm happy to meet you."

"Joe, why don't you have any clothes on?"

"It feels good. I just like it."

Val looked me over and fixed her gaze on my cock.

"What's that?" she asked, pointing at my prick.

"Well, I'm a boy and that's my pee-pee."

"I have a pee-pee, but it looks different from yours. Your's sticks out, and mine doesn't. Do you wanna see it?"

Oh shit, how long could I stand it?

"OK, if you want to show it to me, I'll take a look!"

Val gave me a wide grin and moved the crotch of her panty aside.

"See? Mine's kinda flat. There's a hole there where pee comes from. Can you see it?"

"Yes, I see it. I think it's very pretty! Can I touch it?"

"You want to touch my pee-pee? Eeeew! I don't know 'bout that!"

"You know, Val, when you get older, that part of your body becomes much more than a place where pee comes out of. It's the most special place a woman has."

She stared at me doe-eyed.

"Wow, really? Is my place special now?"

"Yes it is, Val. As you grow you'll find you'll get great pleasure there. When you have boyfriends, you'll let some of them play there. I'm sure you'll like it a lot and they'll like it just as much. And, when you're ready and have a special man in your life, you and he will start a baby there and it's where it'll come out when it's ready to be born."

Val's face showed complete wonderment. Then the spell was broken and she started giggling. She pointed at my cock and said,

"Guess what! Your pee-pee is sticking up. It kinda looks like my lollipop!"

She placed her lolly next to my dick and giggled some more.

"My lollipop is long and you pee-pee is long. My candy has gum in it. Does your thing have anything in it?"

"Well, yes it does. There's a cream filling. But I'm not sure you're old enough for it!"

"Why not? I'm almost ten! Isn't that old enough? Can I have some of your cream filling, pleeeeease?!"

This was a dirty old man's greatest fantasy and I AM a dirty old man!

"OK Val. But it'll be our secret."

"OK, our secret. What do I have to do?"

"You said it looks like your lollipop. Pretend it IS a lollipop and do what you always do with a lollipop!"

She looked at me and shrugged. Val moved her face toward my cock and gave it a little lick, then another and another.

She looked up at me and asked

"Am I doing it right? It doesn't taste like candy. It's not sweet at all. How long before I get the filling?"

"You're doing fine. Don't you like the taste? Maybe if you put it in your mouth and sucked on it just like your pop you'll like it better."

She followed my instructions. This little girl was a natural cock-sucker! Before long, her eyes were rolling up into her head and she was moaning. I warned her,

"Val, I'm ready with the cream filling. I think it'll be better if you try a little bit first. Some girls don't care for the taste."

But Val was too-far gone to care about what I said. The first streamer of spunk fired into her mouth, followed by several more. Val's mouth kept a tight seal around my prick as my balls emptied into it. She kept the suction up for about 30 seconds. I begged her to let go as the sensations in my cock were getting to be too much.

"Your stuff feels funny! It's like Jell-o, but it tastes real salty and Jell-o isn't salty at all. But I kinda liked it anyway! What's it called?"

I gasped as the waves of orgasm subsided in my groin.

"It's called cum. I don't know why. But most grown up girls and women like it a lot. I'm glad you liked it."