Date Night

I brushed nervously at a piece of lint on my shoulder and tried to decide if I should go with the tie or not. I decided the tie was too formal and went with just the button up shirt with a sport coat over it.

I eyed myself in the mirror and almost gave in to my nerves. I'd been matched with Bonnielass67 at an online dating site and we were set to meet tonight.IfI could get over my nerves.

It had been almost a year since my girlfriend had walked out on me to start seeing one of her professors. I had been so sure she was the one and had even been shopping for an engagement ring. It had taken months for me to get over the breakup.

When I finally decided I was ready to start dating again, I hadn't known what to do. I'm not the kind of guy that can go pick up a girl in a bar. It had actually been my mom who had suggested an online dating site she was trying. She'd had a lot of good things to say about it so I decided to give it a shot too.

It took a couple of days to evaluate me and offer some suggestions. The first few were not exactly what I was looking for but the third one, Bonnielass67, seemed really interesting. Just like me she had refused to put a picture. She felt it put too much weight on the physical side of the relationship and not the mental. Right away, I wanted to know about this woman.

The only drawback was, at forty-four, she was twice my age. I had browsed back through my other matches, but I kept winding up on her profile. She liked a lot of the same stuff as I did and she seemed far more interesting than the other woman.

I decided to message her. It wasn't like I was going to meet my soul mate on the first date. Maybe this could just be a practice date to get the nerves out of the way. Hell, maybe, if things went right, we'd wind up back here, have sex and then I could try for someone closer to my age.

We messaged back and forth a couple of times to get to know each other. The twenty-two year age gap between us didn't bother her one bit. I quickly found myself hurrying home from work to see if she'd messaged me that day.

After almost a month of messages we agreed to meet. I was going to meet her at Tony's, a little Italian place I knew. It was a little small, and a lot pricey, but it was some of the best Italian food around.

If I didn't stop procrastinating I was going to be late. I looked back in the mirror at myself one last time. My brown hair I kept cut short; otherwise it tended to go wild and curly. I'd trimmed my goatee down to a manageable level. I decided to wear a black silk shirt with a black sport coat over it. My ex had said I looked best in black on black and I'd decided to go with what worked.

I stared into my blue eyes, willing my mirror image to turn and walk out of the bathroom.

"You first," I told him. He just stood there staring at me.

Finally, I forced myself to turn and walk out. I grabbed my keys and left my apartment. I got down to my car and headed over to Tony's. It was the longest and shortest drive of my life.

I parked and got out of the car. I stood by my door for a second, one last burst of nervousness running through me. I took a deep breath and let it out. With feet that felt like they were encased in concrete, I walked towards the entrance.

Tony's has a little sitting area in front by the doors. The whole are is covered in fake grape vines and little by little clusters of candles. I loved stopping by, during the lunch hour, to just have a coffee and relax. It was a little too warm for dinner out front tonight but I did see one person sitting out front.

She had her back to me, giving me a chance to get a quick peek at her. She was wearing a bright red dress and had her brown hair spilling down her shoulders. The dress clung tightly to her curves and set them off magnificently. From the description she'd given me, this had to be Bonnielass67.

I walked up and, taking a deep breath, said, "Hi."

She turned to face me and... The whole world went topsy turvy.

It was my mom.

She frowned at me for a moment and then asked, "Tyler, what are you doing here?"

"Umm... I'm meeting Bonnielass67 for our date," I said, hoping that this was just a nightmare and that I would wake up soon.

"But... That's me," She said. "You're Ty216?"

I nodded and we stayed there, staring at each other for a minute before she covered her mouth and her body started to shake. It took me a second to realize she was laughing.

It felt like all of the tension had been taken right out of the night. I started laughing so hard I had to grab the back of her chair to stay up.

A hostess came out and looked at us. We must have been one hell of a sight. Two fools laughing so hard we were both crying.

"Are you okay?" She asked, making us laugh even harder.

I managed to catch my breath and wave at her. "It's okay. We're good. We'll be in in a sec."

She looked at us for a second before turning and going back inside. We got our giggling under control and I said. "Well, this isn't exactly how I thought the night would go."

"Me either," She said, standing up to give me a quick hug. "I was so nervous and now... God, Tyler, I haven't laughed that hard in a long time."

"Me too," I said. "So what now?"

"I don't know," she said. "This is all so weird."

"Yeah, it is," I said. "Well, we're here, we might as well eat."

"Are you sure?" She asked. "I know this place is a little expensive and you weren't exactly planning on eating with me."

"It's okay," I said. "I have plenty to cover it. Besides, I'll be eating with the prettiest lady here so Ican'tsay no to that!"

"Tyler," she said, a small smile pulling at her lips while her cheeks turned a rosy color.

"And that color of red looks good on your cheeks," I said.

"You are such a brat," she said, looking me up and down. "But you always look so handsome in black."

"I've never seen you in a red dress before and, I have to say, you should go with more red in your wardrobe," I said, my eyes taking her in. The dress she wore plunged down between her breasts, showing off a great deal of skin. The fabric covered her flat stomach, clinging to her and not showing an ounce of fat anywhere. I came to an end just above her knees, hiding very little. I found myself feeling a little aroused by how much it showed.

"Stop staring," she said, her face a very solid red. "You're making me feel self-conscious."

I managed to drag my eyes away from her. It was a lot more effort than it should have been but somehow I did it. I offered her my arm and asked, "Shall we?"

She smiled and took my arm. We went in and got put at a small table near the corner of the dining area. The room was kept dark and the candle on our table was just bright enough fro us to read the menu. It was very cozy and romantic.

All the things I had wanted but now could do without.

"This is very nice, honey," my mom said.

"I have good taste, what can I say?" I asked.

"You obviously get that from me," she said, making me laugh.

Dinner seemed to fly by in a swirl of laughter. It had been such a whirlwind of a night; the nervousness, the surprise at seeing my mom and the joy of just being able to relax. It was nothing like what I had expected. It was better.

We shared some tiramisu for desert and then sat in a comfortable silence. I had been meaning to ask her something all night. It was a little personal and I was still struggling with it when she said, "Out with it."

"What?" I asked.

"You want to say something," she said. "You always get this little frown line between your eyebrows when you want to say something and you over think how to say it."

"You know me way too well," I said.

She laughed and asked, "I'm your mother, would you expect any less? Now out with it."

I was glad the room was dim and hoped it hid the blush I could feel creeping up my cheeks. "Well, you set up a date with a guy who's half you age and I wanted to ask you about that."

She took a drink of her wine and said, "When you emailed me, I was surprised by how alike we were. I didn't even look at your profile until you emailed me the second time. When I saw how young you were, I just decided, to hell with it, I was going to go have some fun. Plus, you can hold a conversation and it was nice to talk to a guy that really cantalk."

"If you'd told me your real name instead of just your username I might have figured it out earlier," I said.

"Yeah, but what if you'd been a weirdo?" She asked. "I didn't want some guy stalking me or something."

"We are way too much alike," I said. "That's thesamereason I didn't want to give you my real name."

We shared another laugh and then she asked, "What about you? What's with asking out a woman old enough to be your mother?"

"You were the only interesting one. The other girls seemed superficial and kind of annoying," I said.

She reached across the table and squeezed my hand. "I think that's the nicest thing anyone's said to me in a while."

Her hand lingered on mine for a moment. Goosebumps sprung up all a long my arm. When she slid her hand back, I was surprised at how disappointed I was.

Once I paid the check, we got up to leave and my mom stumbled as she got up and had to grab the back of her chair.

"Whoa," she said, closing her eyes and taking a couple of breaths.

I put my hand on her shoulder and asked, "Are you okay?"

She nodded and said, "Maybe I shouldn't have had that third glass of wine."

"You get drunk on three glasses?" I asked. "You are such a lightweight."

She fired off a glare at me and said, "I am not drunk. I am just a little spinny right now is all."

"Spinny?" I asked. "Is that what the kids are calling it these days?"

"Oh shush," she said, letting go of the chair. She waited a second before making her way towards the door. We got out into the parking lot before she stumbled again.

"Maybe I should drive you home," I said.

"Maybe you should," she said.

We went over to my car and I opened the door for her. Once she was in, I joined her and we headed home.

It was a little weird to be driving my date home to the house I'd grown up in. Of course, whathadn'tbeen weird about the whole night?

When we pulled into the driveway, mom reached for the door handle and I stopped her. I got out and went around to open the door for her. She laughed and let me help her out of the car.

"You're so sweet," she said.

"My mom taught me how to treat a lady," I said.

She smiled and put her arm through mine. I walked her to the front door and stopped. I let go of her arm and turned to face her. She looked at me in confusion.

"Don't you still have your key?" She asked.

"Yes, but I can't just barge into my date's house," I said. "I have to tell her how good of a time I had first."

She tried to fight the smile but lost. "Did you really?"

"Actually, I did," I said. "I got to laugh and have some really good food with the most beautiful woman in the place."

She looked down and said, "I'm not all that."

I cupped her chin and lifted her face. "Yes, you are. You are a knockout both inside and out. I'm glad I had the chance to see that for myself." She took my hand off of her chin and placed a kiss on the back of it. A thrill of pleasure ran through me at the touch of her lips.

"Thank you," she said.

"Did you have a good time?" I asked.

She laughed and said, "Of course, silly. Too bad we don't have more men like you in this town. I'd pry be married again if we did!"

"So any shot at a second date?" I asked, giving her a wink.

She laughed and wrapped her arms around my waist. She leaned her head against my shoulder and said, "You are too much."

"I know," I said, putting my arms around her.

We held each other for a moment before she leaned back and asked, "Now do we go in the house?"

"Well, if we get to my date's porch and I have my arms around her, I normally try for a kiss," I said.

She shook her head and asked, "You never give up, do you? Fine! Give me a kiss so we can get inside."

I froze and my heart tried to slam its way out of my chest. She wanted me to kiss her? The nervousness from earlier crashed back into me and brought some extra along for good measure. How should I kiss her?

Feeling like my head was going to explode if I thought about it much longer; I just bent down and planted a quick kiss on her lips.

She looked at me for a moment before she started laughing. I frowned at her and asked, "What?"

"That's a kiss?" She asked between giggles.

I felt my face burn. My embarrassment overrode my mouth and I said, "Well, if I kissed you how I kissed my normal dates, I don't know if you could handle it."

"Oh really?" She asked, raising her eyebrows. "Just a regular Don Juan, are you?"

"You have no idea," I said, hiding behind my bravado.

She leaned closer to me and whispered, "Show me."

I didn't know how I did it, but I bent close to her and pressed my lips to hers. The softness of her lips parted and I slid my tongue into her mouth. I tasted the wine and tiramisu from dessert as my tongue slid against hers.

I pulled her close and ran my fingers up her bare neck and into hair silky hair. She moaned I felt her fingernails dig into my back. I teased at her tongue one last time before I broke the kiss.

She stood in front of me, her body trembling, her eyes staring at me with such a deep hunger it burned my skin. She gulped a couple of deep breaths and closed her eyes.

"Tyler, please open the door. I want to go inside now," she said in a shaky voice.

I fumbled my keys out of my pocket and managed to get the door open. She brushed past me and went inside. I came in and closed the door.

I followed her to the kitchen. She opened the fridge and pulled out a bottle of red wine. She took out a glass and poured it full. She lifted the glass to her mouth and took a deep drink.

The tension in the air was so thick I felt like I was suffocating. I sat down at the breakfast bar and said, "Mom."

She ignored me and took another drink. In two gulps she had emptied the glass. She refilled it and took a smaller drink.

"Mom," I said again.

She set her glass down and finally turned to look at me.

"I'm sorry I upset you," I said.

Her face fell and tears well up in her eyes. She walked over put her hand on mine. "You didn't upset me, honey. I just... That was just really intense and... I didn't expect it to feel like that."

"I did warn you how good I am," I said.

She looked at me for a second before the laughter overwhelmed her. For the second time tonight, we shared a laugh that broke the tension around us.

She wiped the tears from the corners of her eyes and said, "You are such an ass."

"I get it from my mom," I said, earning a slap on my arm.

She walked back over and took a drink of her wine. I slid my eyes up and down her back. The dress clung tightly to her ass and there was no panty line anywhere to be found. I began to wonder if she was even wearing panties.

I felt my cock harden against my pants. My thoughts were out of control. How would it feel to slide my hand over her dress, cupping those ass cheeks? How would it feel to reach under that dress and feel the skin of her ass against my hands?

My cock had swollen and pressed almost painfully against my pants. I needed to get out of there before I went nuts.

I stood up and, careful to keep myself behind the breakfast bar, I said, "I should pry go."

Mom set her glass down and turned to me. She made a pouty face and asked, "Do you have to? You could always stay in your room."

"Nah, I should pry just get back to my apartment," I said.

"Aww... And here I was hoping my date was going to spend the night," she said.

I paused. "You planned on your date ending up back here?"

She blushed a little and played wit her wine glass. "A girl can hope, can't she?"

She had been hoping to get laid. I had to admit I had too. I hadn't told her that I'd picked her profile a little because of her age. I had hoped she'd be a little lonely and more up to spending the night with me.

"And if my date had kissed me the way you did, I don't think we'd be in the kitchen having a conversation," she said.

She clapped her hands over her mouth and her eyes went wide.

"I can't believe I just said that," she said through her hands.

I laughed and said, "Well, that tiny little dress you have on pretty much tells a guy what you're after."

Her face turned a deep red. "I was just hoping I didn't look like an idiot."

I barked a laugh. "Mom, you worry too much. Yousodon't look like an idiot. If anything, you were the hottest woman in the restaurant tonight."

Tears welled up in her eyes. "Really?"

Forgetting my hard on, forgetting any other thoughts of her, I walked into the kitchen and took her into my arms. She wrapped her arms around me and held on tight. I kissed the top of her head and said, "I was the luckiest man alive tonight. I got to spend the night with the perfect woman."

I felt her body shake as she sobbed into my chest. "Thank you. I was just so lonely and I wanted a man to see me and spend some time with me."

I pulled away from her and wiped away her tears. I stared into her eyes and said, "I felt the same way. I needed tonight so badly and it turned out even better than I'd hoped. Thank you."

I leaned forward and kissed her softly on the lips. I pulled back and stared into her eyes. The look of absolute need in her eyes matched the one in my heart.

I leaned towards her again and pressed my lips to hers. Her mouth opened to mine and again my tongue danced with hers. We kissed deeply, with the embers of a building passion.

I wrapped my arms around her and slid them down her back. The dress was thin and I could feel the heat of her body through it. My hands slid lower and I cupped her ass in my hands. She moaned and ground herself against me.

I needed this woman more than I had ever needed anything before.

I broke our kiss and kissed my way down her jaw. I kissed my way down her neck and softly bit the base of her neck.

She gasped and whispered, "Please, please, please."

I nibbled at her neck while my hands explored the firmness of her ass.

"Sofa," she whispered to me. She grabbed my hands and pulled me into the front room. She pushed me onto the sofa and straddled me. My hard cock pressed against the warmth between her legs.

She grabbed my face and pulled me towards her. Her mouth and mine met and I tasted her again. I grabbed her hips and pulled her tight against me. I rubbed my hardness against her, hearing her soft gasps with each touch.

I let go of her hips and slid my hands up her back to where her dress tied against the back of her neck. I tugged at the fabric and felt the knot give.

I broke the kiss and leaned back. The fabric of her dress slid down and off of her breasts. Her breasts showed no signs of age or sag. My eyes roved over the smooth silkiness of her skin. Her tiny little nipples poked out at me, hard and in need of me.

I kissed her nipple, rubbing my lips against it. I flicked my tongue against it and felt her shiver. I reach up and cupped her other breast. I rubbed it and felt her hard nipple sliding along my palm. I rubbed my finger in tiny circles around her nipple while I sucked at the other.

I eased her off of my lap and onto the sofa. I slid off of the sofa and knelt between her legs. I put my hands on her knees and pushed her legs apart. I looked up at her and saw her eyes were boring into me.

With our eyes locked, I slid my hands up her thighs. She licked her lips and stared hungrily at me. My fingers slid along her thighs until the reached her panties. I could feel her warmth and wetness through them.

I hooked my fingers through her panties and pulled them down. I slid the tiny red thong off of her and dropped it on the floor. I slid my fingers back up her thigh and to her naked pussy.