Playdate

Trish - I work in a restaurant, home cooked is better. It's only fair. You treated pizza.

Me - Ok, I would like that.

Trish - Good. I wasn't going to let you say no.

Me - I guess it's settled then.

Trish - I've still got stuff to do tonight. Will I see you tomorrow?

Me - Count on it. I look forward to seeing you. 😉

Trish - I can't wait. Goodnight. 😘

Me - Goodnight Beautiful. 😘

I was like a teenager again. I sat there playing the afternoon through again in my mind. This woman had activated something deep inside me that I had neglected for too long. She was sexy, playful, and fun. I went to bed imagining her with me. Touching, tasting, exploring I came hard letting my imagination run wild.

The next day Cole and I went through our routine as usual. I asked what he thought about Trish - Mary's Mom and he didn't let me down. "She's really pretty, Dad. You should marry her."

I almost choked on my coffee. "Marry her?"

"Yes, then Mary and I could have playdates all the time!" He stated, matter-of-factly.

"How about we start a little slower, bud?" I countered.

"Ok, as long as I get to play with Mary again. She's more fun than other girls." He acquiesced.

We finished getting ready and I dropped him off at school. Trish and Mary were just walking in as I was leaving and I had to turn sideways to let them in. Mary said hi to me and bounded into the classroom while Trish turned away from me and quickly pressed her ass into my groin as she entered the room. I let out a slight groan as she did it and I could see a smile on her lips as she turned again. I walked slowly back to the parking lot. Trish called my name as I made it outside and I turned to look at her. She was wearing a dark blue zip up hoodie and dark purple yoga pants today. "Hey handsome." She said.

"Hello beautiful." I returned.

She walked up beside me and I reached for her. "Not here, what would the PAC think?" She chuckled as she lightly ran a finger along my palm.

"Ugh, what are you trying to do to me?" I groaned.

"Don't you worry. Can we talk at my car for a moment?" She asked with a smile.

"Sure, where did you park?" I asked, looking for her car in the lot.

"Just over there." She gestured past the trees to the side parking lot. "This one was filled when we got here."

We walked around the corner and she grabbed my hand. "Sorry, I don't want any of the gossips knowing about us yet."

"Us?" I teased. "We haven't even been on a date yet."

"Dinner, a beer, and talking. What would you call it?" She stated.

"Ooohhh, that means Sunday will be date number two then." I stated with a smile. "I might try to kiss you then." I said as we approached her car.

"You'd better!" She said turning to me.

She lunged at me and grabbed my head to hers, giving me a ferocious kiss. It took me a moment to realize what was happening and I returned the kiss with the same passion. Our lips and tongues were locked in a mortal battle. I grabbed her ass with my right hand and pulled her to me. She was grinding into my leg. I slid my left hand over her right breast it was so soft and I could feel her nipple hardening in my fingers. I released her mouth and kissed along her jaw to her neck and felt her shuddering against me in pleasure. My cock straining against my zipper, pressing into her.

"I am so horny right now." She whispered into my neck. "But I have to go. My shift starts in half an hour. I just wanted to say good morning."

We kissed again with me grabbing her ass with both hands against her car.

"I think this qualifies as Great morning." I said, releasing her.

"Goodbye James. See you at pickup later?" She asked. Getting into her car as I held the door.

"Yes, but I don't think it'll be like this." I grinned.

She smiled. "I don't think it will." I was about to close the door and she reached out and drew her index finger along the outline of my cock. I hissed in surprised pleasure. "Have a great day!"

I closed her door completely dazed, giant grin on my face and went back to my truck. I have never been so wound up about a woman before so quickly.

I had a busy day of groceries and meal prep for my work week, so I was surprised when I got a text from Trish and saw it was just after 1pm.

Trish - Sorry, I didn't want to leave you in such a HARD spot this morning. I don't know what came over me. 😲

Me - I would take that torture from you every day.😁

Trish - I'm not usually so aggressive but that was fun.

Me - I'm almost glad you stopped it when you did. I might have tried to take you right there against your car.

Trish - Don't tease me like that. I might have let you.

Me - Now who's teasing? Imagine the gossip if we were caught doing that!

Trish - Mmmm scandalous!

Me - You are a handful.

Me - No, two handfuls.

Trish - Your hands seem big enough. 😉

Me - They are.

Trish - Did you take care of yourself after?

Me - No, cooking and preparing my lunches for the week. Had to prioritize. I might have lost the day just doing that.

Trish - Ooohhh. Maybe you should wait and let me help on our playdate.

Me - Talk about making it HARD on me.

Trish - I'll wait too, it will be worth it.

Me - Whatever you want, Beautiful. I'll hold out.

Trish - I might torture you a bit more. Is that ok?

Me - More? Are you picking Mary up in lingerie only?

Trish - I have to go. Breaks over. Here 😘

Her next message is just a picture of her bra clad breasts and her smile.

Me - Damn! Beautiful smile.😘

I made it through the rest of the afternoon with busy work and picked up Cole. I saw Trish picking up Mary and she gave me a wink and pulled her shirt down a little to show me her bra a bit. We waved goodbye and that was it. Cole and I packed up the stuff he brings back to his Mom's and we had supper. I'm always a little sad when I have to drop him off, but that's how our life has shaped up.

Lauren and I always do a ten minute debrief at 'changeover' as I call it. I told her about the Mary playdate and meeting Mrs. Hess. She asked me about Mary's Mom and I was vague. Lauren has been dating someone from her work for a while now and although I'm happy for her, I'm not ready to tell her about Trish.

I head home, get my work stuff ready, and head for bed. I text Trish. She doesn't respond so I tell her goodnight and I'll see her in my (wet) dreams.

The next morning I'm up at 4:35am for work. I check my phone and see that Trish sent me another picture. It's a mirror photo of her ass in some very sexy red lace boy-short panties and her text says 'have a great day at work. My morning shower is very difficult to not jerk off in.

Work is uneventful no phones are aloud in the refinery except at lunch, so I sit in a corner of the lunch room and turn on my phone. I have a couple messages from Trish.

Trish - Did you sleep well?

Trish - Did you like my picture?

Me - That is the sexiest ass on the planet! I just want to bury my face in it.

She doesn't respond so once my break is over I continue my day.

Once my 12 hour shift is over, the first thing I do is head to my phone. Another message from Trish.

Trish - Now who's a tease?

Me - Not a tease, a promise.

As I get home I get a response.

Trish - Sunday can't cum soon enough. 😘

Me - No it can't. I'm scared your pictures will send me over the edge without me doing anything.

Trish - I'm sure you can handle it. You're a BIG boy.😘

Me - We'll see...

Trish - I have, and felt.

Me - I just hope I can live up to your expectations.

Trish - You already have. I have to go. Mary's bedtime. Talk later?

Me - Of course.

I unwind from work, have supper and prep. for the next day. Trish texts me.

Trish - Hi.

Me - Hello Beautiful. How was your day?

Trish - It was OK. Can we talk?

Me - Sure, give me a call.

As I waited for the phone to ring, I wondered what she would say. Did she meet someone else? Was she terminally ill? Did she have cold feet? Did she have to cancel for some other reason? I tried to prepare for every possibility.

I answered on the first ring, trying to be calm. "Hello."

"Hi." She responded. "I don't know how to say this."

"What is it? Are you guys ok?" I asked.

"Yes, we're fine. I'm just worried." She replied.

"About what?" I said.

"Do you think I'm a slut?" She asked.

"What? God no." I replied starting to feel relieved. "Why would you think that I think that?"

"Well, we only met a few days ago and we've pretty much decided we're going to have sex in a couple of days. I've done things with you I'd never normally do." She said, her voice cracking a little through the phone.

"I know, it seems a little crazy doesn't it?" I replied. "I'm not going to lie, I am feeling a little overwhelmed myself, but in a good way."

"Really?" She asked.

"Yes. I felt something the first time that I saw you that I've never felt before. At first I thought it was just how amazingly beautiful you are. But as I got to know you, the more I wanted to get to know you." I confessed. "I'm not a kid anymore. For the first time in a long time, I know what I want and that is you. I'm not promising a ring or anything but I want to see where this could go. You excite me. I had thought that my previous marriage failing was my fault, maybe we just weren't right for each other. You feel right." I stopped to take a breath. Surprised at the truth I had just confessed to Trish.

"Wow!" Trish replied. "You really laid it out there, didn't you."

"I even surprised myself there. I hope I didn't scare you away." I told her.

"No, I want you even more now." She said, very calm now. "Did you mean all of that?"

"Every single word." I replied.

"You are something else, James. Most guys wouldn't be so open about their feelings." Trish said.

"I'm not afraid to tell you how I feel. I'm not in highschool wondering what people will think. The only people right now who's opinion matters to me is you, Mary and Cole. By the way, Cole thinks you're really pretty. So he's on board." I said with a chuckle.

"He's sweet. Just like his Dad." She giggled. "Mary thinks your a gentleman, I'd say she's on board too."

"I'm very glad to hear it. I think she's wonderful." I replied.

Aware of the time I had to be up, she got off the phone with a breathy goodnight and kiss through the phone. I laid in bed for a while thinking about what I had confessed to her. I was carrying a load of guilt I didn't need to. I drifted off to sleep thinking about Trish.

Saturday was a very average day at work. At lunch there was only a single message from Trish.

Trish - I'm so excited for tomorrow night. What should I cook for you?

Me - I'd be happy with peanut butter sandwiches as long as they're with you. 😘

I finished my day and on my way out to my truck, I checked my messages.

Trish - I'll make you something nice.

Trish - I can't stop thinking about you. Mary has been catching me daydreaming a lot today. 😍

Me - I have been pleasantly distracted all day as well. Can I bring anything?

Trish - Just yourself... and a healthy appetite 😘

Me - Deal 😀

Trish - What time will you be here?

Me - 7:30 ok?

Trish - Why so late, don't you get off at 6?

Me - I've got to shower and change after work. I get stinky when I work hard.

Trish - Mmmmmm... you could shower here. I could wash your back.

Me - God. You are amazing! I guess I'll be there around 6:30 then.

Trish - Yay! I'll see you then. 😘

Me - Yes. 😘😘😘

I went home, shaved, and showered. Did my prep and tried to unwind. By this time tomorrow, I'll be alone with Trish. I was starting to wonder if I'd be able to live up to the image she had in her mind. I have been with a total of three women in my life. One was a drunken bar hookup 15 years ago and the other two were long term. I do know how to pay attention to a woman, I love to explore, and use all of my senses for her pleasure. I was the first man to make Lauren cum but it took weeks for me to learn all of her intricacies. Would Trish afford me the time? Would I disappoint her? I haven't released myself in days, and it's been more than two years since I have pleasured another woman. I was rusty and wound up.

I figured I should head to bed, so I sent Trish a message to say goodnight.

Me - Goodnight Beautiful. I need to get my rest. By this time tomorrow we'll be together.

Trish - I can't wait. I've never been this excited for anyone before. Have a great sleep.

She sent me another picture, a mirror selfie again. Showing me her beautiful face and her arm covering her breasts and all she was wearing was black lace panties that barely covered her pussy.

Me - Words can't even come close to saying how beautiful you are.

Trish - Thank you. I love how confident you make me feel.

Me - You are making it very difficult to not relieve myself.

Trish - I know. 😘 Goodnight.

Me - Goodnight.

It took me a while to calm down enough to get to sleep. I had the most vivid dreams of making love to Trish every way my brain could imagine. I woke up to my alarm with my cock as big and hard as it has ever been. I had a quick cold shower that turned into a long cold shower before I was able to get dressed. I packed a light duffel of a change of clothes, grabbed my lunch, and headed to work.

It was the longest day of my life. Like your last day before vacation but ten times longer. I had no issues in my area at all and it was smooth sailing. All I had to do was think about Trish and tonight. When lunch finally came around I checked my phone to see no messages from Trish. I sent her a quick one telling her I was thinking of her and went back to work. The minutes ticked away like hours. I was almost frantic when I was able to leave. I stopped by a flower shop and got a bouquet of Lilies for Trish, a nice bottle of wine, and even thought to get a box of condoms at the convenience store. It was the first time in ten years I had to get those.

I made it to her house at 6:31 and knocked on the door. She opened the door and my jaw dropped. Trish was wearing a silky black robe that was loosely tied at the waist. Her amazing tits were on full display in a red and black lace patterned bra. Her hair was down, slightly curly at her shoulders. She watched me drink her in. Her eyes sparkling with mischief, biting her bottom lip as she looked at me.

I was transfixed. "You- you look amazing" I stuttered.

"Thank you. I felt like I should dress up. Would you like to come in?" She giggled.

"I brought you these." I said remembering the wine and flowers.

"They're beautiful." She said, eyes moistening. "I love lilies."

I dropped my bag inside the door after I closed it. I reached for her. She set the flowers and wine down and we embraced.

She smelled so good. Like flowers and honey. We started to kiss mouths open, tongues fighting for dominance. I grabbed her ass pulling her to me. Squeezing and massaging the soft yet firm globes. Running my hands under her robe. She moaned into my mouth and pushed herself into me. I was groping her ass and sliding my fingers under her panties. I broke our kiss to lick and kiss her jaw, her neck, her earlobe, and her collarbone. She pushed me back. "I recall someone needing a shower." She panted.

"I do." I said catching my breath.

"Follow me." She said. Walking towards the stairs. I grabbed my bag and started to follow. As she was climbing the stairs, she untied her robe and let it drop off of her shoulders to the stairs. She had matching red and black lace thick waisted thong panties. Leaving her beautiful ass only inches from my face. I dropped my bag and reached for her ass. With my thumbs spreading her cheeks and circling the seam of her thighs. She stopped climbing and started moaning, with her head lowered. I could feel that she was wet, absolutely soaked through her panties. I was just starting to push my thumbs under her panties as she pulled away and kept going up the stairs. I grabbed my bag again and follows. My eyes were glued to her gently shaking cheeks every step she took. We entered her room and I tossed my bag to the side. She turned to me and reached for my shirt, she pulled it over my head and tossed it aside. She ran her fingers down my chest to my belt. I was in a trance watching her slowly release my belt and undo my fly. She let my pants drop to the floor and gently caressed my cock straining through my briefs. She leaned up and kissed me lightly on the cheek a reached out my hands and started stroking from her shoulder blades to her waist and back up.

She whispered in my ear. "You don't smell stinky to me. You smell like a man who works." And she licked my earlobe. I moaned and pulled her tight to me again. Kissing her passionately. Backing her up towards the bed. I undid the rear clasp of her bra, and rubbed the bare space where the material was. She released my cock and stepped back to let her bra drop to the floor. "Amazing!" I sighed. Then grabbed each one in my hands. I leaned over and worshipped her breasts. Kissing, squeezing, licking, biting her nipples tenderly. She was moaning and grinding against my thigh stroking her fingers along my sides. I could feel how wet she was through her panties on my bare leg. She pushed off of me and fell to her bed. Looking up at me with her eyes sparkling and a slight smile on her lips, wearing only a sexy pair of panties. He soft feminine body flushed with heat. Her nipples standing straight up. Her thighs slightly wiggling against each other. I took a moment to appreciate the view. "Are you alright?" She asked her face showing concern.

"Trish, baby. I am more than alright. I am in complete awe of you." I said and her smile returned.

I knelt down at the side of the bed, caressing the outside of her legs. Sliding my knuckles up from her ankles to her hips and then dragging my fingertips back down. She was shaking. I pulled her closer to the edge of the bed and breathed in her scent. It was strong and made me salivate with lust. I started to pull down her panties and dragged my fingers along her legs as I pulled them off. "You don't have to-" she was starting to say. "I want to, I need to." I cut her off.

I ran my thumbs from the back of her kneecaps to the top of her ass. I started to kiss the insides of her thigh slowly down to her pussy but only breathed on it gently as I crossed over to the other thigh and started back up. She was moaning and panting my name "Oh James!" I kissed back down her thigh and kissed above her pussy. She was grinding up trying to get my mouth where she wanted it. I slowly kissed and licked my way down. I took one finger and gently stroked along her wet glistening lips getting it nice and wet. I made my way to her clit, it was already protruding a little and I teased it with my tongue gently. Trish gasped. I licked it again, a little harder and Trish gasped again. I started to circle her clit with my tongue as I pressed a little harder with my finger along her lips. She was moaning more now. I started to slide my finger into her and at the same time I sucked her clit between my lips and started sucking. As my finger went deeper, I started to curve it up to hit her G-spot. Once I made contact with her G-spot, she went rigid and came. It was amazing, Trish started to scream and then went silent. Her juices flowed out and soaked my hand and chin. She was gasping for air, she had lifted her ass off of the bed and was pressing into my face. I was alternating between sucking and her clit devouring her juices. Wiggling my finger inside of her. I used my other arm to keep her close to me as she rode it out. Trish was starting to come down and I slowed my attack on her pussy as she did. "That... that... that was AMAZING!" She said hoarsley. "I have never had an orgasm like that, ever"

I smiled at her, impressed with myself.