January 26, 2017 Friday
Report #1 The Trainer
12 noon Heading out
I left my office and drove to Framingham. It was quick and easy, so I was wicked early. I parked near the TGI Friday’s at Shoppers World, sent the “meet info” email I’d forgotten to send to Hubby and Sis, scrolled through Facebook and re-read his profile until I got his email saying he was here!
I checked my look in the mirror, then walked across the parking lot. The temperature was not too bad, but the wind was bad. I hurried to get out of the cold!
1 pm Meeting at Starbucks
I strolled into the Starbucks inside the Barnes & Noble bookstore, looked to the right and saw him immediately. He stood up to greet me and we had a lovely long hug! He’s cute! He reminds me of the comedian Jim Gaffigan – tall, cute, fun, great hair for an older guy, and in good shape, with a sly smile.
Jim Gaffigan
He had picked a great corner table in the back corner near the bookcases and next to the window with no one next to it. I sat opposite him and he took my hand. There was something both comfortable and exciting about that. He looked me up and down and then stared into my eyes. I stared back and smiled.
We chatted a bit, talked about how easy it was to get there, how he knew me immediately even though he had not seen a photo. We kept staring into each other’s eyes.
He had assigned me homework to do and bring with me to our first meet – a list of my five likes and five dislikes. I had written them out on a little piece of paper. I gave it to him and he read it.
Likes
1) The taste of warm lobster with a little butter
2) Hearing David Wilcox singing “Rusty Old American Dream”
3) Feeling a man’s hands on my face as he kisses me
4) The view of the beach at Trunk Cove, St John, VI
5) Watching figure skating competitions live in person
Dislikes
1) Dealing with mean people
2) The taste of green peppers
3) Pain
4) Not being able to fix what is making someone sad
5) Cancer
2 pm Lunch at Olive Garden
We discussed our options and decided to go to lunch. He had already eaten but humored me. So we strolled over the Olive Garden. He stopped me on their front steps as we were going in and pulled me in for our first kiss! Wow… he is so romantic, and talented with his lips! He pulled away pretty quickly. Later he admitted he couldn’t go on or he’d never stop! Awww…
We got a corner table for two and I pulled the aisle chair around so he’d be close to me. He peeked at the menu and rubbed my knee. Mmm…
We had a tall, dark and handsome waiter who set off my gaydar in a good way. I ordered my usual – sausage soup with spaghetti with meat sauce and two sausage. He got the shrimp scampi appetizer. I ordered a peach bellini iced tea and he had a diet coke. We had a wonderful conversation as I munched on my food and teased him under the table!
He apologized, said he has not planned beyond Starbucks and didn’t have cash to pay for lunch and didn’t dare charge it. I told him I was fine with paying this time and he could cover next time. He seemed quite relieved.
3 pm Canoodling in the Car
We walked out to his car and sat in the front seat canoodling! He is a very good kisser – slow and sensual! He had parked in a bad spot, right in the middle of a lot of other cars. He suggested we move to the back seat. I suggested he move the car to a more protected remote location, over by my car. He drove over there then put down the middle seats and we crawled into the back seat and cuddled and kissed. It became clear pretty quickly that we were ready for much more.
4 pm Taking the next step
We decided to go to a hotel! He seemed surprised and happy that I had scoped out the best options around. He was quite embarrassed that he had not dared hoped for that, and that we didn’t talk ahead of time about money. I told him not to worry about it. I got on my phone, found a great low rate and made a reservation, got directions and he drove us over to the Crowne Plaza in Natick. I checked in while he parked. He met me in the lobby and we went up to the 7th floor.
4:30 pm Hot in the Hotel
We had a gorgeous view of the Natick Mall as the sun set. I stood in the window, glancing out and watching his reflection as he took off his jacket and came up behind me. He put his arms around me and nibbled my neck. Mmm… I melted back into him, felt him hard against my ass. He unbuttoned my top and put a hand on my breast, squeezing it with his hand outside my bra. He glanced over my shoulder and whispered, “It’s really Sassy!” because that view matches the photo I sent him!
I giggled and nodded.
He turned me and hugged me close and he kissed me deeply. It went on and on! I put my hands on his face and rolled with his masterful use of his lips and tongue – nibbling, sucking, probing, twisting my head this way and that. Oh my!
He said, “You know that long, romantic email I wrote about our first slow, sensuous time?” I nodded. “And how it ended?”
“Yes… with us throwing off our clothes and shagging like rabbits,” I answered. “That seemed like a much more likely scenario.”
“Will it be okay if we do that?” He asked, being ever so nice.
“YES! PLEASE!” I consented. He started unbuttoned his shirt and I did the same. There was a pile of clothes and two naked people standing beside the bed in short order! I have never seen such a gorgeous cock! It was bigger than I had expected based on the rest of his body, but there it was… longish, thick and perfectly formed with a sexy mushroom crown. He was very hard. Oh my. I am probably not going to be able to deep throat this guy but we’ll have fun trying!
He pressed me back against the bed with my legs over the edge. He stared for a few moments, touching my nipple, my belly button, and smiling. My first impulse was to be shy, but I fought it, smiling back and winking! He chuckled… “You sassy gal!”
He put his face between my legs… mmm… he licked and pulled my lower lips with his teeth, ever so gently. Then he slowly slurped inside, up and down around my clit. Wow… this guy knows what he is going! My hips bucked up to meet his mouth. Oh! He paid attention to my reactions, repeating things that made me squirm. He pressed a finger inside and moaned….”so wet… mmmm.”
He stood up and started teasing my clit with his cock. “You ready?” He asked.
“Oh yes please….” I replied enthusiastically. He grabbed a condom from his pants pocket on the floor, and I heard that magic sound of foil tearing. He rolled it on and returned to teasing my slit with his cock until it was very wet with my juices.
“I may not last long this first time,” he apologized. “I am so keyed up and it’s been so long and I want you so so much!” Wow… way to give a gal confidence. It made me feel so sexy!
“I understand completely,” I assured him. “I want you!” And he pressed slowly into me. Oh, there is nothing like that first thrust deep inside! Being filled after being empty for so long! He held my hips and moved in and out… in and out. I lost rational thought very quickly… thrashed back and forth, pressed forward to meet each thrust. I was making a lot of noise… moaning, sighing, squeaking! So so good. I felt like I was floating… then soaring!
He started to shudder. He said, “I’m going to lose control. Cum very soon.”
“Do it. Fill me,” I told him. He pressed very deep inside me and my inner muscles pulsed around him and his face contorted and he was still. He took four deep breaths, then opened his eyes and smiled the most beautiful smile!
He turned me around on the bed, went to the bathroom to dispose of the condom, then joined me. We rested for a few minutes, then he started making little circles with his finger on my right breast. I stared into his eyes and he smiled, tweaked my nipple and squeezed my breast.
“Is this the rogue one?” he asked.
“Yes… see the scar?” He stroked the two inches of it. “Can barely tell,” he told me. He leaned over and kissed the scar. So sweet. Then he sucked on my nipple and I felt a big twinge lower down!
I reached down to check on his cock. It was already hard again! Nice! I leaned over and kissed his left nipple, then his belly button.
“May I taste you now?” I asked. He nodded, then realized I might not see that and stated a firm, “Oh yes please!” I got between his legs and looked up at him, then took his cock in my hand. He moved up on his elbows so he could watch me. I blew on it. He shuddered. I kissed the tip and smiled up at him. He moaned. I licked from bottom to top and around the crown. He moaned again and closed his eyes. I took him all the way down my throat as far as I could. There was still about a third of it… no getting my nose on his stomach with this guy!
I reached down to stroke his balls with one hand while I made a circle around his cock with my other hand, pressing him in and out of my mouth and making fun sucking sounds. His hips rose to meet me and it pushed him deeper. I gagged and he backed off. I assured him it was fine and dove back down on him. He moaned and his eyes rolled back in his head! Ha! I looked up at him while I sucked him in and out and he stared into my eyes with the hottest look! Perfect.
“I don’t know if I can cum again,” he signed.
“Still feel good, yes?” I asked.
“Absolutely!” he exclaimed. I smiled and went back to licking him and stroking down below. I twisted him and pressed him back into my mouth and sucked. He moaned and I went faster, in and out… he put a hand in my hair and helped me set the tempo.
“I am going to cum again…” he marveled, warning me like a good man should. I hummed around him and went extra deep and started swallowing and BOOM! I tasted several shots of cum! Ah… I adore helping a man do what he doesn’t think he can do and making us both feel so good!
I went back up to cuddle with him. He kissed me deeply… nice he can taste our juices mingled together without being squeamish. I put my head on his chest and played with his chest hair. We were quiet for a while. A comfortable silence.
He turned on his side so we were facing each other, and stared into my eyes.
“I thought you were going to be good,” he said. “But I was wrong. You are terrific!” he crowed. I smiled at him.
“This is my best first meet EVER!” I assured him. I meant it. Each hour had been a treat from the original comfort to the easy conversation over lunch to the incredible sex! I hoped I was not tempting fate and dooming myself never to see him again by thinking and saying that!
As if he could read my mind, he said, “Awww… you know so many ways to make me feel special,” he told me. “Please tell me I can see you again, and soon!”
“I’d like that,” I answered, marveling on how we were on the same page.
“I’m driving to Pennsylvania tomorrow, family get-together, so I may not be in touch much. But I will check in on Sunday and we’ll talk more next week and make a new plan, right?” He asked.
“Yes. That sounds perfect,” I told him. He sighed and kissed me. And then kissed me more.
We talked about his upcoming trip, his job and my job, how we met our spouses, his kids and my cats and… I adore those afterglow conversations when we’re so mellow and open and comfortable!
About 7:45 he looked at the clock on the nightstand and sighed.
“I should go. Don’t want to but it would be smart if I do,” he said. “Come talk to me while I shower?”
We rolled out of the bed, and he dashed to the shower. I relieved myself and chatted with him, then pulled back the curtain a bit to kiss him while he rinsed. So comfortable being with him!
8 pm Heading home
We dressed. I left a tip for the maid and we headed out. I got a bottle of water from the shop. We went to his car and he drove me back to his car. It was easy! He walked me to my car, gave me one last hug and a quick kiss and walked away.
He tapped on my passenger side window – “Do you know how to get home from here?”
“Sure!”
“Okay. Text me when you get there?”
“Of course.”
“Good night!”
“Mwah!”
I texted Hubby. No answer. So I called him. No answer. So I called again! He finally picked up. We conferred about a dinner order. I went in to Olive Garden, placed a take-out order and sat at the bar shipping a kiwi melon limonada while they made my dinner. I replayed the afternoon, smiling like a loon.
9:30 pm Home
I made it home easily. I sat in my car in the garage and read his email to me. Good man, to email right away! I emailed him right back.
What a day! Best first meet ever!
=====
From: TimmyTim
To: Sassy
Date: Fri Jan 27, 2017 at 8:54 PM
Subject: WOW
Sassy,
Brain no work! But I got home safe!
All I can say: “you are awesome!”
Will write more, maybe quote Latin, ask dirty questions, see how your Saturday went on Sunday! Till then let me know you drove home safe!
Real hugs with real groping!
Take care,
Tim, John Henry and even The Trainer
Sent from Yahoo Mail for iPhone
=====
From: Sassy
To: TimmyTIm
Date: Fri Jan 27, 2017 at 9:30 PM
Subject: Re: WOW
Hiya T,
Wow indeed! With an extra crispy bucket of woohoo!
I got take-out from Olive Garden for Hubby and am home now. My mind is whizzing with so many marvelous memories! Thank you.
Safe travels. I’ll be thinking of you. And John Henry!
-S
Sent from Yahoo Mail on Android
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