'Jenny' & 'Mike': A Day Out

"Haven't you ever fantasized that you were a character from a movie or even just someone else?" she asked.

I could tell that 'Mike' was not going to let this go. I had never been more happy to see a waitress at that moment.

"Hi, my name is Melinda, and I'll be serving you today. Have you decided what you would like?"

"Um, no not yet. Could you give us a few more minutes?" said 'Mike'.

"Whenever you guys are ready, wave me over and I'll be back to take your order."

'Mike' continued to fix me with the enquiring stare she treated me to before the waitress interrupted us.

"What?"

"I'm still kind of waiting for my answer."

"Well, I mean I used to fantasize, but not really about being a movie star or anything..." I let the sentence trail off.

'Mike' leaned in closer, looking into my eyes as if trying to pry my secrets out of me.

"But there was someone you fantasized about, or someone you fantasized being?" she prompted.

I could feel my cheeks heating up as I blushed. I knew I had been caught.

"You didn't fantasize about screwing her, did you? You fantasized about being her," 'Mike' grinned. "Come on, tell me!"

"No..."

"Oh, come on. I accept you for who you are James. It's okay. You can tell me."

"No. Now let it go, please." I made eye contact with the waitress, and gestured her over to our table.

"You have to tell me. Maybe we can even do some kind of role-play and get you off," she teased, grinning.

I knew Michelle well enough to know that she would not let this go. And if I told her she probably would end up making that fantasy come true. But I didn't want to tell her.

"So, you're ready to order?" the waitress asked.

"Yeah. I'd like to start with a drink first. A rum and coke please," I said hastily, welcoming the interruption.

"And for you?"

"I'll have whichever beer you have on tap, please."

"Okay, great. I'll be back with your drinks soon."

'Mike' scooted next to me in the booth.

"Tell me. Come on. You know I'm not going to let this go."

"Just leave it, please."

"James, please. Tell me. I have accepted everything about you. I am not going to judge you. This far into our relationship, you don't trust me?"

"It's not about trust. It's just kind of embarrassing."

She looked a little puzzled. I could see that she was trying to figure out why I was so reluctant.

"The maid who came my parents house twice a week. And the head cheerleader at my old high school." I was mortified.

'Mike' burst out laughing.

Just then the waitress came over with our drinks. Thank god she didn't linger. I almost downed most of my drink in one go.

"What's so funny?"

"Because, fantasizing about the maid and the head cheerleader is such a cliché!" she said, trying to contain her incredulity.

I couldn't hide my annoyance. I sat drinking quietly and studying the menu.

"Sorry. I shouldn't have laughed, baby." She moved even closer to me, squeezing my thigh. "I'm sorry, baby. Really." Michelle knew I found the cute puppy dog eyes she was making just then hard to resist. I relaxed and smiled, and was rewarded with a quick kiss on the lips.

"Aw, you guys are so cute!" We were so preoccupied that we didn't see the waitress who had come over to the table to drop some nuts. She grinned at us, and walked off again.

'Mike' smiled and gave me another kiss on the cheek. We sat in silence for a few minutes sipping our drinks and studying the menus. 'Mike' suddenly looked up at me in excitement.

"I have an idea," she said with a naughty grin.

"What?"

"What if we spend tomorrow fulfilling one fantasy of each of ours?"

"You want us to role-play our fantasies when our roles are already reversed like this?" I gestured to us in our carefully-selected attire. I couldn't help smirking

"Why not? Look, we have already switched places. You can't deny that last night was hot. Amazingly so. Why not spice it up a little bit more?" she asked.

"You're really serious!" I exclaimed, draining my glass.

"Yes, I am! We can make either one of your fantasies come true. Sort of."

I could tell she was getting into this now. She suddenly put down the beer she'd been nursing and grabbed her bag and handed me some money. I was confused.

"Go to the sex shop. Get whatever outfit you want. Once you're back, I'll go out get an outfit for you to wear to make my fantasy real. I'm sure Carmen would be happy to help you out," she said with a wink.

I thought about it for a second. Although we switched gender roles from time to time, we hadn't ever done any kind of role-play. It did sound hot. And it would be fun. To my surprise, I had already begun to develop some ideas about what I wanted from the experience.

"Okay," I nodded, smiling. I grabbed the cash, leaving 'Mike' at the restaurant.

Within a minute or two, I was back at the shop. I seemed to be the only shopper. Carmen had just come from the back of the store as I walked in. She was all smiles.

"Back so soon?"

"Uhm... uh... yes. I actually need your help with something."

"Sure, shoot!"

"This may sound a little weird." I said softly, and cringing with embarrassment. "Do you have any special role-playing outfits?"

"You're looking for something for yourself?" she asked, not batting an eye.

"Ummm..."

She could tell I was nervous.

"We have some nice plus-sized costumes. I am sure we could find something for you."

She took my elbow and guided me towards racks and racks of different kinds of outfits that seemed ideal for fantasy play. The selection for men was sparse - just one rack. But there were several racks of costumes for women to choose from! Carmen went to stand in front of one of them.

"These are samples of the costumes I told you about. I'm sure you'll find something here."

Before I knew what was happening, pulling items off the racks. They looked like fun, but nothing like what I was looking for. And then, just as I was losing hope, she had the outfit I wanted in her hand.

"Umm... could I take a look at that one, please."

She looked at the item in her hand, and smiled.

"This one just came in yesterday. It's one of our larger plus-sized costumes and should fit you perfectly."

I was skeptical.

"Is there any way to check whether the size will fit?"

"Oh these are all free sizes and should fit you just fine. I've helped quite a few couples with similar requests and have never had any complaints or returns."

How could I not buy the costume.

When I got back to the restaurant, 'Mike' was sipping on what seemed to be a fresh pint of beer. I sat down and put my purchase down on the seat between us. I smiled at her. She grinned back, and then got up and left without saying a word. I ordered another rum and coke, and watched her rush out.

'Mike' certainly took a lot longer than I had. After 40 minutes I became very curious about what could be taking her so long. I was famished, and wolfed down a ham sandwich while I waited.

'Mike' walked in and scooted into the booth just as I was biting into the second half of my sandwich. She had a similar bag to the one I had walked in with almost an hour earlier. We were both smiling from ear to ear. There was no need for words.

"Shall we order?" I asked as she settled down.

"No, I'm not really hungry," she said, moving closer to me. She kissed me on the cheek and started nibbling on some of the fries that had accompanied the sandwich. We continued eating in silence. Then, out of the blue, I felt her lifting my dress slightly, and moving her hand up between my legs. I gasped as she began caressing my panty-covered cock.

The little tease continued munching, while pretending as though nothing untoward was going on. I, on the other hand, couldn't concentrate on food because of what she was doing to me. I couldn't believe when she pulled my cock out of my panties, and started stroking it. I was becoming rock-hard.

"Aren't you going to finish your sandwich?"

"Uhm... uhhhhhh... no... I feel kind... of... full..." I managed, as she jerked me off.

Keeping a straight face was difficult. I quickly scanned the immediate surroundings to make sure that no one could see what was happening at our table. No one seemed to notice.

'Mike' nonchalantly drank some of her beer as she edged me closer to orgasm. I grabbed hold of the table as I got closer. And then, just like that 'Mike' let go of my cock, and stuffed it back into my panties. She removed her hand from under the table, and waved to get the waitress's attention.

"Check please!"

I couldn't believe it. She had gotten me so close, and then... denied me my release.

She looked at me innocently, as she drained the last of her beer.

"What's wrong?" she asked with a grin as the waitress handed us the check.

We had reached home by 3 p.m. The drive home was quiet; we didn't say a word to each other all the way home. 'Mike' parked the car in the driveway. She unlocked the front door, dropped her bags on the floor and pushed me against the wall without much warning. She grabbed my hands and held them over my head, pinning me to the wall. She began kissing me roughly. I could only try to return her kisses.

Once she had had her fill of my lips, she turned me around. She began grinding her crotch against my behind, while her hands were holding mine above my head and against the wall. I could feel her hard-on pressing against my ass as her hands moved down slowly to caress the sides of my breasts.

Soon her hands were under my dress. Before long I felt a hand inside my panties, squeezing my ass cheeks. After paying some attention to my ass, I felt her moving away slightly and lifting my dress. I gasped loudly as I felt her hand smack my ass hard! She gave a couple of more smacks before I heard her unzipping her pants. She began to smack my ass with her cock and after a few more smacks she pulled my panties down over my knees. Her teasing of my hole with her cock soon had me whimpering and moaning in heat.

I moaned in disappointment as she stopped her ministrations to pull me roughly away from the wall. I watched in silence as she pulled up her boxers and pants before leading me into the kitchen. Before long I found myself pushed face down on the kitchen table.

"Mmmm, look at that nice round ass." And then she landed another smack on my behind. "Do you like that, baby?"

I could only manage a moan. She kicked my feet wider apart. "Do you want to get fucked?" she whispered into my ear.

"Yes, please."

She began to grind her cock against my hole. My own erect cock twitched as she moved against me.

"Please don't tease me, Mike," I pleaded, getting into character.

"Then tell me how much you want my cock, you whore."

"I want your cock so bad. Please, please just give it to me!"

She laughed and released her grip. "Stay!" I heard her walking out of the kitchen and up the stairs towards our bedroom.

She returned a minute or so later, and soon after I felt the cool lubed head of her cock pushing against the puckered entrance to my hole. She applied a little pressure and the head slipped inside easily. I moaned and whimpered as she went ahead and drove the entire length in in one thrust.

She began pounding me really hard. I could feel her pants smacking against my thighs as she fucked me nice and hard. Soon I heard a familiar buzzing sound. She must have hidden the vibrator, which sounded like it was now pressed against her clit, in the harness's pouch.

"Fuck yeah! Take my cock," she screamed, smacking my ass at regular intervals.

"Oh fuck... yeah... fuck... fuck ... fuck..." I screamed as she rammed into me like a wild animal in heat. I had fucked her just like this on many occasions and I guess she was returning the favor. The vibrator continued to buzz as she too began to gasp and moan.

She slowed down as she began to orgasm. Just as the final wave of pleasure coursed through her body, she gave one last hard thrust.

Once she'd recovered some of her composure, she leaned into my back.

"Did you cum, babe?" she asked into my right ear.

"Not yet."

"Let's remedy that, shall we?"

She began pounding into me once again. I reached down between my body and the table and grabbed my cock. I began jerking off. Each pound of her cock was hitting me like a thunderbolt. I began to jerk off faster and faster, until my balls began to twitch.

"Fuuuuck..." I screamed as cum spurted from my cock like hot lava from a volcano. I felt like it would never end.

"Yes, cum for me baby," 'Mike' groaned huskily into my ear.

I continued to jerk my cock until it released the last drop of cum. 'Mike' sensed that I had finished and still leaning against my back, gently kissed my shoulder. I felt empty when she lifted herself off me, and pulled her cock out of my ass. When I turned around, my knees felt like Jell-O. I almost collapsed on the floor. Luckily 'Mike' was there to hold me up, albeit laughing.

"What the fuck was that?" I asked her, grinning.

"I don't know. I suddenly felt the need to fuck you hard, I couldn't control myself."

"Well whatever that was, we need to do that again."

'Mike' continued to laugh as helped me get my bearings. She straightened her pants and gave me a smack on my bottom as she walked out of the kitchen.

Around 7 p.m., we shared another shower. It was not as sexier as our earlier one, but felt well deserved after the morning's excitement and our afternoon nap.

For our evening outing, 'Mike' chose a black button-down shirt, a pair of blue denim jeans and a leather jacket. I went for a pink pleated top, a black skirt and beige four-inch heels.

As we got ready, 'Mike' got the new harness out of its packaging. I watched her put it on, and adjust it to fit her snugly. When she was satisfied with the fit, she strapped on the Bandit eight-inch dildo.

But for the slightly thicker girth and longer length, the dildo wasn't much different from one she had used the night before, and earlier that morning.

"Why are you putting that on?"

"Because we're going to be in character, silly."

The new harness definitely looked much sexier on her. It looked like a Jock strap and she had inserted the dildo through the O-ring from the inside. It took all my will power not to jump her right there.

She caught me admiring her new appendage.

"What?"

"You look so sexy in that," I answered, with a shit-eating grin.

She grabbed her cock and began stroking it.

"Yeah? You like my new dick?"

"Oh yeah!"

"Well, we will have plenty of time to try it out later tonight," she said, slipping on a pair of boxers and treating me to another of her naughty grins.

We agreed to have dinner at the same restaurant we had gone to earlier that day.

Unlike earlier that afternoon when it was quite quiet, the place was buzzing with the evening crowd. The same hostess who had greeted us earlier that afternoon, was till on duty.

"Welcome back," she said.

"Could we have a table for two, please?" asked 'Mike' as I held on to her.

This time she guided us to a booth in the back where we would have a little more privacy.

A different waitress walked to our table as the hostess left us.

"Hi, I'm Ellie and I'll be serving you tonight. Would you like to know tonight's specials?" the waitress asked us as we settled in the booth.

"Shoot!" said 'Mike'.

"We have Mushroom and Spinach ravioli in chive butter sauce, Spaghetti Al Tonno prepared in a Tuna sauce and the Farmers fresh pizza prepared with organic vegetables."

'Mike' chose the spaghetti and a pint of beer. "And what about you, babe?"

"I'll have the ravioli and a glass of white wine, thank you."

"Can I get you anything to start with? Perhaps some soup or a salad?"

"None for me, thank you," said 'Mike', before glancing in my direction. "What about you, babe?"

It was a bit weird, but for some reason, her calling me 'babe' in front of the waitress was turning me on.

"Nothing for me either, thanks." I smiled, and turned to look at 'Mike' as the waitress gathered the menus.

"What?" she asked, as the waitress moved off to place our order.

"It felt good when you called me babe in front of the waitress..."

She touched my hand tenderly, and lifted it to her lips for a kiss. "You are my babe."

I moved in closer for a kiss. There were people everywhere, but I didn't care. Besides, it looked like no one in the place cared either. Everyone was just so busy in their own little world. I held her face between my palms as the kiss became more passionate.

"What was that for?"

"For being you."

She didn't say anything, but the look on her face told me all I needed to know. I couldn't resist and pulled her in for another kiss as the waitress approached our table.

"You guys make such a cute couple," she said as she placed our drinks on the table. "I'll be back with your food shortly."

I blushed. 'Mike' just smiled and I interlocked my hand with hers.

"So, is this the only time you will come out as 'Jenny' or can 'Mike' expect to go out with 'Jenny' a lot more now?"

"I haven't thought about it. This afternoon was great. Right now is great. So, yeah, maybe we could do this more often. But to places like this, of course."

"Oh, of course. I've wanted to explore this path a little more. And not just in the bedroom. I've been considering how best to bring it up again given how you felt after our last experience. I really thought the odds of us going out like this ever again were slim."

"I thought so too, but I'm having a good time now. It feels great to have these moments alone together."

"I love you, babe."

"And I love you too.

All through dinner I thought about how far we had come. I had never been happier than I was at that moment. Marriage is all about loving one another and compromising to see each other happy. Michelle had done just that by accepting me for who I was. I felt like the luckiest person in the world to have someone like Michelle.

After dinner, 'Mike' paid for the meal and we headed to the movie. 'Mike' bought tickets to back-row seats on the balcony level. Only two other people, a lesbian couple who were making out in the front row, were present. It seemed we would have considerable privacy.

We took our corner seats in the back row, and waited for the movie to start. As the movie went on, I could see why Michelle loved it so much. Ingrid Bergman was absolutely heavenly.

Halfway through the movie, 'Mike' began to put the moves on me, just like she did the night before. She snaked her right arm across my shoulders and began to fondle my right breast. Because of the armrest between us, she couldn't pull me closer.

"You're getting awfully frisky," I whispered, turning my head towards her slightly.

"The movie kind of calls for it, don't you think?"

I smiled as I felt her grab my breast again. I leaned in for a deep kiss. Soon her hands were under my skirt and caressing my thighs. This was the second time in two days that she had me feeling like a high school girl. She got bolder and began running her fingers over my panty-covered crotch.

As I grew more and more excited, I started caressing her thigh. Finally, I snuck my hand higher to press against the crotch of her jeans. The bulge I felt there nearly drove me wild.

'Mike' pulled away, undid her jeans and released her cock. While guiding my hand to her cock, she pulled me in for another kiss. I began to stroke her as our tongues intertwined. Normally, I would have been petrified of behaving like this in a public place, even one that was nearly deserted. But the thrill of me jerking her dick in such a public place, and the possibility of being caught was turning me on like crazy. I was hard as a rock.