Grabbing Dinner

Cute Waitress Isn’t His Type

Uptight Reggie Relaxes

Reggie isn’t the most daring of my girlfriends. I can’t even recall the last time I saw her kiss her boyfriend in public. She’s the type who blushes trying to say “penis” in conversation. So, when she called me up and said she wanted to share a story with me, I was curious but I also didn’t expect much heat.

She asked to meet at La Bella Signora, a little Italian place known more for affordable wines by the glass than its food or service. I assumed that meant Reggie wanted a little wine to help her tell the story. It turns out, there was another reason she wanted to meet at La Bella Signora. An extremely cute reason.

Reggie arrived promptly at noon, wearing natural beige linen slacks and a thin light blue blouse. There was definitely something different about her. It was more than the hot, humid weather giving her a rosy glow. She slid into the booth and looked about the restaurant.

“I never thought you’d — ”

“Call you to share something I did?” Reggie interrupted. “I know. Weird, isn’t it?”

A gray-haired waiter approached the booth. We ordered two salads (it was lunch after all) and a bottle of wine.

“I’ve told you before that Mark thinks I’m a little… uptight.”

“We all think that, Reggie,” I admitted.

“What if I told you I did something daring? A little risky. And it was fun.”

Reggie went on to tell me that she had always envied the women whose stories I collected. I reminded Reggie that most of the women who contacted me with adventures they felt compelled to share were like her. They had fantasized about taking a little risk and adding a bit of play to their sex lives. They were finding their sexual freedom, within loving romantic relationships.

What usually happens is that we reach a point when we simply let things happen. We go with the moment and enjoy it. The thrill of not being good little girls and embracing the fact we are sexual women is hard to quantify. Sharing helps. Reggie nodded in agreement. We are taught to care for others, even within our intimate relationships. We need to assert ourselves more.

As we ate and drank, Reggie shared the following adventure….

Reggie’s Story

That Thursday had been one long, lousy day at the office. Angry boss, backstabbing coworkers, and a customer who was too busy undressing me with his eyes to hear one word I said. Apparently, some assholes can’t see and hear simultaneously. I am definitely the hardworking, good little girl. It was almost nine when I finally stacked the folders on my desk and said to hell with it. I was tired, bitter, sweating, and starving. When I arrived home, I was in no mood to cook or reheat anything.

“You’re taking me out,” I told Mark before I had even dropped the laptop bag to the floor. “Five minutes, and we’re out of here.”

Mark is always more than happy to let someone else deal with cooking and cleaning. Plus, he could tell this wasn’t a discussion. Five years together and he knows when I’m in no mood to talk. I headed straight to the bedroom. I kicked off my shoes, dropped my wrinkled dress pants to the floor, and searched for a skirt and sandals. I tossed my blouse aside, leaving a simple black satin v-neck cami — not an ideal tank top, but I was too hot to give a damn. To hell with the bra straps or anything else. I just wanted peace, quiet, and good air conditioning.

“It’s late,” Mark called out from the bedroom, where he was changing into khakis and a polo shirt, the uniform of the bland people we have become. “What’s open at this hour?”

I knew La Bella was open until midnight on weeknights, mainly for a handful of old regulars who sit around drinking at the bar. It wasn’t a plan or anything; it was the only option that came to mind quickly. Plus, I wanted a few glasses of their cheap house wine. Maybe the whole damn jug.

When we arrived at the restaurant, we were seated immediately by the hostess. We were led to one of the back corner booths. The corner booths are a rounded “L” of overstuffed worn red leather with dark wood. The colors make it seem even darker than the corners already are. La Bella isn’t dimly lit for atmosphere, though. I think the owners are simply too cheap to update the lighting. I didn’t exactly mind the dim light, either. I hadn’t touched up my makeup and didn’t care if the skirt matched my blouse or not.

Jeanine, one of our regular waitresses, approached. She has shoulder-length light brown hair walked up to us before we had even finished inching into the corner booth.

“Can I get you something to drink?” she asked, smiling a perfect smile.

“Hell yes,” I answered, not even thinking about my language or attitude. I definitely wasn’t myself. Mark was amused, but he didn’t dare say anything.

We ordered a bottle of the house red wine, and Jeanine darted off towards the bar. Mark tried not to watch too obviously. Of course, he couldn’t hide his occasional glances in her direction from me. It was cute that he thought he could. He watched her whenever she happened to be working. Suddenly, I wasn’t so angry that a customer had stared at me. I wasn’t thrilled, yet Mark’s glances were reminding me that men can’t help themselves at times. They’re men.

Jeanine returned with the bottle. Mark stared at her as she peeled back the foil seal and removed the cork. I studied her, too, looking for any clues to how aware of Mark’s eyes she might be. A good waiter or waitress exploits being attractive. Somehow, that’s more acceptable than a serious businesswoman using her appearance to get a few more line items added to a deal. Darn it, I was starting to think too much. I needed wine and lots of it.

Jeanine could tell I was thirsty, and frustrated, and she poured my glass first. The wine was half gone from my glass before Mark’s was poured. He wasn’t watching the wine fill the glass. He was looking right past the glass to Jeanine. I wasn’t going to let that go unchecked. Might as well exploit his wandering eyes.

As he took his first sips of wine, I moved my hand to Mark’s inner thigh. I placed the tips of my fingers over his dick and felt it twitch through his khakis. I knew it needed a good stroking. Maybe it was because I was tired, maybe it was because I was frustrated. Until we got home, teasing it would have to do. Teasing in public makes me nervous, but I know he loves it. The payoff is always fun. Still, I worried that people might see us, and I’d get into trouble. Sure, it’s silly, but I don’t do things like that very often. Not that I don’t want to, but I don’t dare to.

Dammit, I thought, it’s late and there’s nobody here. I looked around to determine how private things were in this corner booth. The waitresses and waiters in their black pants, white shirts and white aprons rushed about the dimly lit restaurant. There seemed to be fewer wait staff every minute. The few people remaining in the restaurant were chatting quietly, the volume matched to the classical music.

Jeanine, still holding the wine bottle, looked at me and definitely took note of the fact I had one hand under the table. I pulled my hand away, placing it back on the table as if to declare, “See? I’m not doing anything!” I felt my face redden. If that didn’t give away what I was doing, nothing would. I might as well stand on the table and announce that I was rubbing Mark’s dick through his pants.

“It’s a very private booth,” said Jeanine as she shook her head and smiled. “Lots of couples request it for some reason.” She opened her eyes wide and nodded to me.

I cautiously placed my hand back on Mark’s leg.

“Yeah, I guess it’s just a romantic booth,” she said. I swear she had mischievous grin as she said she would give us some time to look over the menu.

“Jeanine is kind of cute, isn’t she?” I teased.

“I suppose.” Yep, a twitch. Mark was definitely nervous, in the good way. “What do you think you’ll have?”

“Probably the citrus salmon,” I answered, grabbing his dick to let him know my first preference.

Mark studied the menu, holding it with both hands while I teased with each twitch. “I’ll go with a seafood Alfredo,” he whispered, exhaling slowly.

“I’ll be right back,” I announced, rising. Mark started to stand, something I was unaccustomed to, but he paused and sat quickly. It was adorable to see him trying so hard to be polite and romantic. Either that or he simply needed to adjust his dick when he sat down again. I rose with my clutch in hand.

I headed towards the restroom, which was conveniently by the servers’ station. Jeanine was keying in an order, which was why I had excused myself. I wasn’t sure how this was going to go, but it was worth a try.

“What’s up, Reggie?” Jeanine asked. “Is something wrong? Do you need anything?”

I stumbled, feeling my face blush a little again. “I wanted to ask you….” I trailed off a little, unsure of myself. This was nothing like a business meeting, where I know exactly what to say. I had no clue what to say, much less if I should even be thinking what I was pondering. My heart was ponding so hard I was sure Jeanine could see my blouse move. I briefly pondered waiting to talk to Jeanine until I had most of wine bottle in me.

Jeanine looked curious, not at all concerned. She was so relaxed I could feel my pulse slow. “What?” she whispered to me, like we were the closest of friends. “Just ask.”

I took a deep breath. “I want to tease Mark. A lot. You sort of know what I, well, you know. What I mean.”

She looked at me, smiled, and leaned towards me. Maybe it was my nerves causing me to feel warm all over. I told myself it was the wine finally working. “Go on,” she whispered. I shivered. “Ask me.”

“Do you think I can I tease him, especially when you’re at the table?” I opened my clutch near my waist, to avoid being obvious, and took out a couple of bills. “How much can I get away with?”

She took the bills from me right at waist level and slipped them into her apron pocket. “As far as you dare to take it.” I could feel her breath on my neck. “You’re such a cute couple. I love watching you,” Jeanine said with a sly smile. “Most nights, you stick to flirting. I kept waiting for you to so more.” She stepped away from the station as another waitress approached. Jeanine took a couple of steps before turning slightly back to me. Bubbling with enthusiasm she asked, “Mind if I help?” My heart was racing again and I was breathless. I had to swallow to catch my breath. “I have some ideas that might be fun for both of you.”

“Uh, well.… okay. Sure,” I finally answered, entirely uncertain of what I had agreed to. Her flirting with him seemed fun, if a little more than I had anticipated. “He’ll be a little stunned, but I think he’d like that.”

“Would you like it?” I nodded, unable to express how much I liked the thought of Jeanine teasing us. I mean Mark. She was going to tease Mark, right? “Anything you need, just let me know,” Jeanine whispered into my ear. “You’re deliciously cute.” And then she walked away towards the kitchen.

I darted into ladies room and looked in the mirror. I touched up my cheeks a little and took a few deep breaths before returning to the table. This was going to be interesting, especially since I had no idea what Jeanine might say or do. She was nothing like me. Maybe I needed a little prodding to relax and have fun. It’s not like I don’t realize I can be… well… bland.

When I returned to the table, Mark was staring at the desert side of the menu, so I knew we’d have a full four-course dinner and plenty of time to play. He stood while I slid into the booth. He was being wonderful. I leaned into Mark and intertwined my right arm around his left. “This is going to be a great evening,” I told him.

When Jeanine returned she placed a basket of warm bread on the table. She was radiating warmth, too. She smiled at me and then at Mark. “Are you ready to order?”

Mark looked to me. I placed my order for salmon, with a salad, and thought I was done. Jeanine leaned in slightly, as if she was about to tell something just to me.

“I love your top,” she said, just quiet enough that both of us could tell Mark was leaning close to hear her. “I love how it reveals just the right amount of cleavage. What type of bra?”

Mark was enthralled. He couldn’t avoid listening to us talk about our bras. I was incredibly hot, knowing Mark was thinking about my breasts.

“Black demi.”

“Oh, I love a nice demi with a scoop front. Drives me wild.” Thoughts of the bra certainly were making Mark squirm. “Or a cupless shelf. That’s sexy. Only thing better than that is no bra at all, if the top can handle it.” Jeanine giggled. “So, can that top it handle it? Or them?”

I wanted to rip my bra off right there. Instead, I shrugged. “I don’t know. It’s really just a satin cami.”

“So it would show everything.” Jeanine giggled. I looked down at the cami, and she anticipated my concern. “Oh, nipple shame?” she asked.

“They would be obvious through satin,” I said, more to myself than Jeanine or Mark. “Plus, I never tried it without the support.”

Jeanine looked closely at my chest as she continued to lean across the table. “You should try it. Why not lose the bra in the ladies room?” Jeanine smiled deviously. “If I lose mine, you have to lose yours.”

Jeanine straightened herself and looked at Mark. She was definitely going to tease and leave ideas hanging for him to ponder. He couldn’t hide the fact he had been super attentive to her words, and my tits, but he tried his best to look calm and relaxed. He ordered his pasta with a salad in a nervous, higher-pitched voice than normal.

Mark watched as Jeanine slowly walked towards the servers’ station. His eyes focused on her black pants, which clung tightly to her ass, revealing no panty lines. I put my hand back on his inner thigh and felt his dick pulse. He needed even more focus, I decided. Maybe he didn’t realize how smooth her ass was.

“No panty lines,” I whispered. “I bet she’s a thong girl.”

“Oh, I have no idea. I was just….”

“Looking at her ass,” I finished his sentence.

He looked down and took a sip of wine. “Maybe,” he said, a mild confession.

When Jeanine returned with the two small salads, I didn’t hesitate. “Are you wearing a thong tonight? We were noticing you can’t see any lines.”

“Yes. Nice little black thong,” Jeanine admitted. “I’ve thought about going without for fun, but I only do that with a dress or skirt. More comfortable, somehow. What about you?”

“Bikini style tonight. They match the demi.” I smiled and looked at Mark. “Without isn’t a bad idea, though. What do you think, Mark?”

“Yes, what do you think?” Jeanine asked him, smiling seductively.

Mark put a fork in a small cherry tomato and sucked it off the prongs. “Without is amazing, yes.”

Jeanine leaned close and smiled. “So, take them off. Who would know? Just us.”

I nodded and started to slide out. Jeanine moved to the edge of the round booth. Blocking my exit, Jeanine leaned to my ear and whispered, “Here. Take them off here. That little evening clutch could hold them.”

I slid back into the booth. I gave Mark a quick kiss on the cheek. I rolled up my skirt slightly and then reached under the thin cotton. Thankfully, it was knee-length. Jeanine stood at the end of the booth, grinning ear to ear. I lifted myself slightly and slid my panties to just below my butt. I sat down and lowered the panties to my knees, while Mark and Jeanine watched. With the tablecloth covering me, I pushed the panties over my knees and let them fall. Then, I slid my left foot out of my sandal, lifted my leg with the panties around my ankle, and sat down on the leg. We all know the one bare foot tucked under is adorable and men can’t resist it.

Jeanine quickly reached over, took the panties, and tucked them into her apron pocket. “You might get these back when I get off tonight.” I was slightly taken aback, but she was too irrepressible not to like. “Or, maybe I’ll keep them to remember this night.”

I couldn’t believe how much I enjoyed Jeanine teasing with us. I was damp. Okay, I was wet, my appetite whetted… and we hadn’t even started to eat.

Jeanine left us to our salads, which allowed me to tease Mark. I mimicked how he had swallowed the little tomato. I made it very clear I wouldn’t mind sucking him the same way. It was amazing to sit there, no panties, wanting Mark. I had to resist the urge to touch myself, and that wasn’t easy to resist. As we finished the salads, I placed my hand back on Mark’s dick to keep him hard and ready.

When Jeanine returned, something was definitely different. She stood to Mark’s right, and leaned over him to put my salmon on the table. Even with her button-collar Oxford and black tie, it was clear her breasts were free. She made sure to bump into Mark, in case he hadn’t noticed the change.

“Oh, my gosh!” I couldn’t control myself from saying.

“You think I’ll get better tips from the old guys tonight?” Jeanine teased. “Yeah, breaks the rules, but you think anyone will be an ass and tell the manager? The shirt’s pretty thick cotton.”

There was no question you could tell, even in the dim light. Her nipples were larger than mine, and far more obvious.

“Now, it’s your turn to lose the demi.” She went about her duties, leaving Mark pondering her young, small breasts. I knew he would be thinking about those tits for days, even if he didn’t get to see them. To make sure of it, I massaged his dick more during the main course.

“I wonder what they look like? Obviously firm and perky,” I commented. “When we get home, you can see mine and play with them. Or maybe you’ll get to see hers when I get my panties back.”

“I really want to fuck you right now,” Mark sighed. “Damn. Wish I could see her tits…” Mark said, trailing off as he thought about Jeanine. His words sent a bolt of electricity through my body. He’d never said something like that in front of me. Sure, he obviously enjoyed looking at women, but it’s not the sort of thing we would have talked about. Couples keep quiet about looking, I guess.

My pussy was soaking wet and my nipples were begging to be sucked. “I’ll be right back.” I excused myself and headed straight to the ladies room. As I rushed towards a stall, I heard Jeanine’s bubbly voice.

“I’ll take the bra for you.”

I opened the stall and motioned for her join me. I don’t know why.

I turned around, instinctively, to remove my bra. Before I could reach back, Jeanine had unhooked my bra for me. She gently kissed my neck, something no woman had ever done. I turned around to see Jeanine holding my bra and staring at me. She wasn’t smiling or giggling. She was simply, silently, looking at me.

“Sorry,” she softly apologized. “I — .”

“Show me yours,” I said. “I want to see those nipples out of curiosity.”

“Really?”

I reached into my clutch and pulled out my phone. “Actually, I’d really like a pic of them. For Mark. He’d fuck me all night if he got to see your breasts.”

Jeanine reached under her black tie and unbuttoned the white dress shirt. “You mean my tits, right? Breasts are what you call them in art class. Tits are what make you want to fuck.”

“Yes,” I whispered. “Your tits. You don’t mind?”

“Does it look like I mind? I want you to see them.”

In the bright lights of the restroom, it was hard to miss the dark circles of her raised areolas. She held the shirt open as best she could, the tie falling between her breasts. Her breasts were smaller than mine, almost flat, though her nipples stuck out at least a quarter inch. I wondered if they were inconvenient, until I remembered the effect they had on some men when they were that obvious.

I snapped a pic with the phone’s camera. Jeanine buttoned her shirt and then put out her hand, signaling it was her turn.

The thrill of being flashed in the stall was making me hotter and hotter. I lifted the camisole exposing my own tits.

“Puffy, aren’t they?” Jeanine observed. Yes, my tits have those little puffy circles. And they can be really sensitive, too. The areolas have always bothered me a little. Jeanine seemed curious, though, so I let her study me. She looked closely, and I stood there quietly. Damn, I wanted her to touch them. “I can’t wait to suck those tits.” She stepped towards me to whisper into my ear. “I’ve got a crush on you.”

She stepped back. It seemed like hours before Jeanine took the picture. Once she did, I turned around quickly. If I hadn’t turned around I would have begged her to suck my nipples. I can’t believe I had that thought. Yes, I can. Who wouldn’t have wanted someone so young and beautiful. So eager to play! I turned back around, slowly.

“So you’re not flirting with Mark, are you?”

Jeanine stepped closer and I could feel her breath as she whispered, “No. You know who I’m noticing. You’re so fucking hot.” She kissed my neck, and I leaned my head back. “I’d be kneeling on the floor, licking your pussy, if I could. I bet that would get his attention.”

I exhaled and rushed to the sink to splash cold water on my face. When I turned around, Jeanine was gone.

When I returned to the table, Mark was intently staring down at his phone. He’d received the pictures, obviously. Jeanine wasn’t at the table, thankfully, or I would have collapsed. My legs were so weak I could barely walk. As I sat down, I nudged Mark and whispered, “My tits are free, now and want to be seen.” I squeezed his dick for good measure and added, “She does have beautiful tits.”

“So do you,” he said. I noticed on the screen was the image of my slightly sagging breasts, not the small perky tits of Jeanine. I hadn’t felt so much passion in his voice in months. My breasts aren’t large, but they hang slightly. I never liked them, but it was clear Mark did.

Mark looked at me, my little nipples poking through the black cami. I leaned so the front would bunch just enough. He stared for the longest time, making me feel wanted in ways I hadn’t imagined. No panties, no bra, and all desire, I wanted his dick in me like never before. I imagined leaning over the table, skirt hiked up, getting fucked right there in front of people. I shivered. And then I thought about what Jeanine had said. Oh, god, I was shaking.

As we finished dinner, Jeanine returned with the dessert menu. To our surprise, she sat down right next to Mark. She reached across with her left hand and placed it right on top of my right hand. Mark inhaled as I squeezed his dick with Jeanine.

“You really should finish the cream during dessert.” Jeanine stood again. “I’ll bring you the chocolate explosion. It’s a soft pudding filled cake with ice cream in the middle. You’ll enjoy it, even if it takes until closing to finish.”

I kept rubbing and massaging Mark’s dick while we waited for the dessert. When it arrived, it was huge. Jeanine had three extra napkins. She bent down and placed one over my hand. She then pulled the tablecloth over Mark’s lap, as well. “Cream can be messy,” she whispered.

Jeanine walked around the booth to my side and slid in next to me. “Go for it,” she whispered. “Everyone is on dessert by now.” With my right hand, I slowly unzipped Mark’s slacks. As he inserted his fork into the cake, my hand reached into his boxers and grabbed his throbbing dick. Jeanine nudged me. “Pull it out!”

“You can’t do that here!” Mark weakly protested. That only encouraged me more.

Setting Mark’s dick free, it popped out of the napkin briefly. He was throbbing, the top of his dick glistening with clear pre-cum. Jeanine giggled and then stood up. “You have to finish him or you’ll never get it back in his pants. Too bad you can’t suck him here.”

I covered him quickly, and then for added privacy made sure the tablecloth was over his lap.

At that moment, I quivered as Jeanine’s hand landed above my knee. As I stroked Mark, her hand moved back and forth, with each motion traveling a bit further up my leg. Marks dick throbbed, dripping cum. He was breathing hard, looking forward.

“My fingers are sliding into Reggie’s pussy,” Jeanine announced. The words caught me off guard. Before I could process them, I felt her finger exploring. They were only inside for briefest moment, but the sensation remained with me.

“I’ll be back. I really wish I could help more, though.” Jeanine stood and looked down my cam. “Damn, I want to lick your pussy,” she sighed. She headed off to finish serving the remaining few diners.

“You’d fuck her if you could,” I said, taking a bite of cake with my left hand while teasing the tip of his cock with my right.

“I’ve got you,” he answered, but his dick told the truth.

I started stroking, slowly, while Mark tried to eat and remain calm. I started to pump, before realizing that was way too obvious for my comfort. I’d have to be slow, firm, and tease him to orgasm. As Jeanine approached our table again, Mark’s dick throbbed and twitched while he tried not to notice her.

“How do you like it?” she asked, being a good waitress.

I curled my left hand, motioning for her to lean in.

“He’s going to cum soon. I can feel his muscles tightening. You know what I mean?”

“Oh, yeah. The moment when the cock pulls back right before cumming all over. I love watching a guy cum during a good handjob.”

“Maybe we can arrange it.”

Jeanine leaned towards Mark. “My nipples are really sensitive right now. It’s all the rubbing against this shirt. Wish I could take off the shirt and let you cum all over my tits.”

Mark swallowed and took a drink from his ice water. I pumped him hard, not caring anymore if anyone could see. He came into the napkin forcefully; I could feel it getting soaked with his cum. I tightened the napkin around his dick to catch it all.

“I know you’re cumming,” Jeanine teased Mark. “I’m dripping wet. Maybe we’re thinking about the same things.” Jeanine was nearly bouncing with excitement.

“Do you think Mark was pondering sucking your tits?” I asked.

Jeanine looked at me intently and I felt my own muscles twitch. “I was thinking of sucking yours.”

I trembled again. She was so hot, I was close to begging her to take me. I sat the cum-soaked napkin on the bench beside me, shoved Mark’s dick back into his pants, though it was still twitching. I tried to think of a response to Jeanine. Really, there was only one.

Her white shirt wasn’t that thick, or my eyes had adjusted to the dim light. I could see her erect nipples and make out the small dark circles around them. “Yes. Definitely, yes. And I’d love to suck your tits,” I said, and I meant it.

Jeanine left to get the dinner check. Mark fumbled with his wallet, not saying anything. When she returned, Jeanine placed the black leather receipt board on the table. There was an extra slip of blank receipt paper and a pen. Jeanine had scribbled on it, “I’d call you.”

Mark didn’t even look at the receipt. He placed a stack of bills on the table, shaking his head.

I scribbled my cell number and email on the extra slip and turned it over. Did I really do that? Had I just given my number to another woman? Was that a horrible thing to do? I saw her smile at us, at me, from across the room. And then Mark and I headed home for some cuddling.

Needing a New Friend

I had listened to Reggie’s story, which she told with increasing excitement. I hadn’t seen her so alive in a long time. It’s easy for us to fall into routines, and that’s what had happened to Reggie.

As we finished our salads, I noticed a young woman in a white dress shirt headed towards us, a tie in her hand. It was one of the waitresses coming in to get ready for the evening.

“Hi, I’m Jeanine. You must be Teresa. Reggie says I should get to know you,” the waitress said as she slid into the booth next to Reggie. Their hands briefly touched.

“I know that look,” Reggie said with a giggle, surprising me. “We’re not fooling around or anything behind Mark’s back.”

“Not yet. But we do flirt a lot,” Jeanine added, elbowing Reggie playfully. “At least you know you have options!”

None of her friends had managed to help Reggie find the freedom she wanted. We had tried to push her to be more daring, to take more chances, but it was a total stranger who was able to break through the inhibitions.

The smiling and laughing Reggie was an unexpected surprise. Sharing changed her for the better.