Almost three weeks had passed since Kristy gave me a blow job in her car – the ‘car job.’ It was a very pleasurable experience, and the good news was, aside from a smirk and wink the next time Kristy saw me, things weren’t awkward between us. That night in her car, she had expressed interest in wanting to repeat what we had done. However, Kristy never said anything else about it.

On Tuesday morning, roughly three weeks after our first encounter, Kristy texted me in the morning as she arrived at her regular nine to five job. We hadn’t exchanged numbers because she already had my cell number from when I would work customer service and ask her to take an open shift after her regular job or come in on the weekend.

“Morning, Jack! Are you awake?” Her text read.

“I am awake. How are you today?” I responded.

“I’m good. Wondering if you’d like to meet me before you go to work?”

“I’d be happy too. Did you have somewhere in mind?”

Kristy’s response to that was a GIF message of a MILF blowing a cock. Then she sent three “hand covering mouth laughing” emojis. Kristy wasn’t the traditional porn MILF type, but she certainly was a mom that nine out of ten men would want to fuck. She was in her mid-forties, a petite five-feet-nine, with large A-cups or small B-cups. She was a brunette with short hair just below her ears.

“Now I see what you want… what time should I be there?”

“Be here at noon! And bring two Cokes!”

“Okay. See you then. Don’t forget your lipstick 'winking emoji,'” was my reply.

Kristy responded with eggplant and kissing lips emojis.

~~~~~~~~~~~~~~~~~~~~~~~~~~

Kristy worked as a secretary for a low-level executive at a security firm. While on my way, I texted her how to get in. She gave me directions on how to find her. I had the two Cokes in my hand when I saw her sitting at her desk.

“Hi, Jack!” She said as she stood and greeted me. Now, based on what I had seen her wear to go shopping for groceries after her nine to five job, she was definitely dressed up for me. Kristy was wearing a dark grey pencil skirt that ended just below her knees and a powder blue buttoned blouse, which was short-sleeved.

“Hello, Kristy. What are the Cokes for?” I chuckled.

She smirked and said, “Well, they helped you get in, and they are for after.” She winked before taking them from me and instructed me to stay where I was. “I’m going to put these in my boss’s refrigerator in his office. I’ll just be a second.”

When she emerged from the office, I asked her, “Where is your boss… and everyone else for that matter. There aren’t that many people here.”

“St. Louis. Big convention for the company,” she replied as she handed me a few manila folders. “For your cover,” she smiled and grabbed her own stack. “Now, follow me. I know a place we won’t be disturbed.”

As we walked through the hallways, Kristy’s heels clicked. I thought to myself that I’d never seen her wear heels. I also took notice of how well the skirt flattered her figure, particularly her butt. It was way more flattering to her than the jeans or slacks she had to wear to work at the grocery store.

The walk seemed to take forever, but it was probably just a couple minutes when we approached a door labeled “Records.” Kristy took out two keys as it was a deadbolt and a handle lock.

“No one should come in here,” she said as she opened the door and shut it behind us as we entered. “But lucky for us, the right spot is way in the back. So that’s even better.”

The file cabinets were roughly five and a half feet high. The room itself wasn’t that wide but had a room in the middle for examination with more isles of cabinets on the other side. In the back right corner was a cove, and that is where we went. I set my folders and jacket down on the table, which was there, and Kristy did the same. She turned and looked at me, slowly walked to me and put her hands on my shoulder. Our lips met for a gentle kiss.

“I’m happy you agreed to visit me today,” Kristy smiled.

“I’m happy you are still interested. I was starting to think you found someone else,” I joked, and Kristy smiled back. She knew I was only teasing.

“Well, there is someone else. Two actually. But you are the only sub-forty cock this forty-eight-year-old is interested in,” Kristy said. Okay, so maybe she was late-forties. I didn’t know before. Now I did.

Kristy then placed her hand on my crotch and rubbed her hand up and down softly. “Would you be interested in hearing about these other two men?”

“Would you be surprised if I said, ‘yes?’” I replied as my hands took hold of her butt.

“Mmmm, yes,” Kristy moaned at the feeling of my hands on her and my interest to learn about her other sexual exploits. Kristy guided me to a chair where she sat me down. My arms rested on the arms rests, and my eyes never left her. Unfortunately, I didn’t know the position of the chair, and Kristy didn’t realize where she had guided me to sit. Neither of us knew we were slightly exposed.

“Who should I tell you about first?” Kristy said as she spun around and began to lift her dark grey pencil skirt to her waist. She wore nude stockings and wore a thin, black pair of panties. She glanced over her shoulder and easily could tell I was interested.

“I think I will start with Mark,” she smiled and leaned back down to lower her stockings.

“Mark is the father of one of my daughter’s friends from high school,” Kristy said as she lowered her left stocking. “He has been a widower for eight years, but I’ve only been seeing him for about six years. Basically, since our daughters have been out of high school.” With both her stockings lowered, she revealed a pair of legs that didn’t look forty-eight years old. Kristy was both lucky and had kept herself in very good shape.

She spun around, facing me, and asked, “Well? How do I look so far?”

“Gorgeous,” I said. “Those are the legs of a thirty-year-old.” That may have been sweet talk, and she knew it and corrected me.

“Thank you. You are so sweet, but they are more like a thirty-year-old. At least ten years younger than they should! Thank you nonetheless. Now, where was I?” Kristy walked to me and spread my legs and squatted, balancing herself on her heels.

“Mark is fifty-two and like me, isn’t sure if he wants to remarry,” she said as she began running her hands up my thighs. “He loved his wife very much, and I think he is afraid to have another wife. Plus, marrying your daughter’s friend’s mom is a little weird. But that doesn’t mean we can’t have fun.” A big grin swept across her face when she said the word “fun.”

As Kristy started to unbuckle my belt, she continued, “Now before Mark, I had only been with four men, and before you wonder, I’ve never been with a woman.” Now unzipping my pants, she said, “The four were my ex-husband, and three men I dated before him. All of whom fucked me.”

With my zipper down, Kristy pulled my slacks down to my ankles. “But Mark,” she continued, “was the first man to make me cum with his cock in my pussy.” Her hands ran slowly up my legs and thighs. “I bet you are wondering how big he is,” she said with a smirk.

Usually, I wouldn’t be all that curious, but her voice made me so. I nodded that I did want her to tell me.

“Five and a half inches,” she whispered and grinned as her hands found my hard cock through my boxer briefs. “It’s all about how a guy uses it and the sexual attraction between you and the person you are with.”

“My ex was six inches, another guy was six, too, and the other two were a little smaller than Mark,” she began. “All were great in bed, once we learned one another, but I think my attraction to Mark is the highest I’ve ever had.”

Her fingers grasped the hem of my boxer briefs and pulled them down like my slacks, revealing my hard cock to her. Kristy smiled ear to ear.

“Mmmmmmm,” Kristy purred. “A big young cock just for me,” she said as her fingers grabbed the base of my length, making me twitch.

“Mark and I fuck at least once a week, and he makes me cum nearly every time,” she shared. “In fact, he fucked me last night, but he doesn’t keep himself groomed like you. But I like both,” she giggled. I kept myself trimmed and balls smooth.

“Now the other guy, Chris,” she said just before licking my cock. Shivers rocked my body as her tongue ran from the base of my cock to my tip.

“Chris, I met him two years ago while shopping with my daughter in Cincinnati,” she said, stroking my cock slowly. “He wanted my opinion on a few dress shirts he was buying. He is forty-two, a very nice guy, and like me, divorced.”

Kristy’s left hand stroked my cock slowly as her right hand started to unbutton her powder blue blouse. Some of her short hair fell into her eyes, and I brushed it back behind her ear. “Thank you,” she said as if she was shocked, I did so.

“Now, I only see Chris and his little over six-inch cock,” she giggled, looking into my eyes, “when I visit my daughter in Cincinnati every three or four weeks.” Kristy unbuttoned most of her blouse before she pushed it to the sides of her breasts, giving me a perfect view of her bra covered chest.

“Do I still look gorgeous?” Kristy asked.

“Yes, you do,” I whispered because that’s as loud as I could speak.

Grabbing her breasts with both hands, she complained, “I wish these were bigger. That’s what the push-up bra is for,” she shrugged.

“Your breasts are beautiful, and the size of a woman’s breasts don’t matter to me,” I smiled, brushing her hair back again.

“You are too kind, Jack,” she replied. “Now, where were we? Oh, yes!” Her right hand took ahold of my cock. Some precum was leaking out, and she spread it all over my length. “Now Chris has only made me cum with his cock while fucking me twice,” Kristy said. “He is better with his mouth than Mark is, but Mark is still pretty good,” she smirked.

Leaning into my crotch, Kristy kissed my cock multiple times from its base to the tip.

“Now since you’ve been such a good boy, and we agree size doesn’t matter,” she looked up at my eyes and kissed my tip, “I’ll share with you the only other guy I’ve been with sexually.”

Kristy licked my length, getting plenty of saliva on my cock before returning to stroking as she shared, “This guy, Chad, I met him after Mark, and I hooked up the first time so about four years ago but he only lasted a few months or so.”

Her eyes stared at her hand as it slowly stroked my entire length, up and down. “Chad was eight inches long and a little thicker than you,” she began. Then her eyes met mine, “Remember how I said I guy needs to know how to use it? Well, Chad didn’t.”

Kristy sighed and kissed my tip. “He didn’t know how to read a woman’s body, and he was clearly only with me for my tight pussy – his own satisfaction,” she exclaimed.

Blushing, she realized what she had said, “Sorry, that was a little too much.”

“No, it wasn’t,” and I smiled at her.

“Thanks. And anyway, so Chad didn’t last long. He was just honestly too big, too uncomfortable, and he didn’t know how to use it right to try and make it enjoyable for me. So, size matters a little bit but not the way most think.

“He was thirty-six at the time and was the reason I instituted a rule that you must be forty or older to fuck me. And that is, in a nutshell, my sexual history. So, you are cock number eight. But I’m not really counting.” Kristy chuckled and gazed up at me once more and said softly, “I’m considering breaking my must be forty rule… but not today.”

She rested patted my arms resting on the armrest, instructing me not to move my arms – in a playful, yet serious way. Kristy rested her arms along my thighs, leaned down, and rapidly consumed my entire length into her mouth.

“Fuckkkkkkkk, Kristy,” I moaned from overwhelming joy. Her lips were locked around my cock and completed three slow bobs before we heard the all too familiar unlocking noise of a door.

Kristy’s eyes were bulging out of her head. She then realized where we were positioned. She realized where she had seated me, but it was too late. My cock fell out of her mouth as she peeked around the corner. We heard a man and a woman’s voice. Luckily for us, they didn’t come too far back into the room.

For the next few minutes, the pair chatted about some records and then left.

“Phew!” Kristy said in relief.

“Yeah,” I nodded nervously.

Then she noticed I was still hard, even after zero attention and the fact we were nearly discovered. “I can’t believe you are still hard – fully hard even.”

I shrugged and said, “I mean, I was looking at you the entire time.”

Kristy blushed and smiled at me, then caught her breath before she resumed her position between my legs with her arms on my thighs. After looking at my throbbing cock for a few seconds, she leaned in, opened her mouth, and tongue slid out. Kristy licked my balls and up along the underside of my cock. Once Kristy got to the tip, she accepted my hard-on into her mouth inch by inch.

When she had devoured my entire length, her eyes shot up to mine. With our eyes locked, Kristy slowly withdrew off my cock to the very end where just her lips were touching my head. Once she had paused for dramatic effect enough, she lowered herself once more. But this time, the bobbing didn’t stop. It grew until her head was bobbing up and down rapidly. Her eyes left mine as she concentrated on my cock, opening, and closing sporadically.

“Oh, my gawwwwwd,” I moaned as my cock repeatedly touched the back of her throat. Kristy moaned as she gagged on my cock. With her arms still resting on her thighs, her fingers gripped the bottom of my work polo.

She popped my cock out of her mouth long enough to get some air and say, “God, I love this big young cock,” before taking my shaft back into her mouth and returning to sucking it.

I was lost in the pleasure I was receiving from her mouth and tongue, watching Kristy bob up and down as she moaned and purred. She gagged on my cock, and her saliva and my juices made “slurping” noises as my cock entered and exited her mouth. Both of us were too far distracted, that we didn’t hear the door open for a second time and the sound of heels clicking.

“Kristy!” A female voice blurted.

My cock popped out of Kristy’s mouth, with an exaggerated popping noise, and she said, “Oh, hey, Cara.”

I instantly began to edge as I nearly popped. Thinking to myself, 'You are not going to cum like this.'

“I thought I saw somebody back here,” Cara began. “Who is this, and what are you doing?”

“This is Jack, and have you never seen or given a blow job?” Kristy retorted.

“I know what a blow job is, Kristy. My husband gets them from me frequently, thank you,” Cara responded smugly. “But what are you doing?” she stressed.

“I’m having lunch with a friend,” Kirsty said sternly.

Cara loosened up a bit. She stood about twelve feet away and crossed her arms, and pushed up her breasts through her blouse. Cocking her hips, she said, “Hmmm, looks like a good lunch from here.”

Kristy cocked her head to the side, pressed her lips against my hard shaft, and planted a long kiss on me. However, while she kissed my hard-on, her eyes never broke contact with Cara’s. My head had fallen backward, and I stared up at the ceiling, edging, as Kristy kissed my cock. The next thing I heard was a zipper and the recognizable sound of clothing crumpling up on the floor. I turned my head to the left to find Cara’s skirt on the floor and her left hand in her panties.

Cara wasn’t bad looking herself. She was about five-foot-ten, in her early thirties, and I later found out she had three kids. Her hair was jet black and hung to the middle of her back. She was curvy but not overweight and had D cups on her chest.

Kristy grabbed my chin and turned me back to face her. “Eyes on me, sweetie,” Kristy smirked. Since I was stuttering with my breath, Kristy gave me a few more moments to recover before she welcomed my cock back into her mouth.

When she finally slid my length to the back of her throat, Kristy exaggerated her moans of pleasure to tease Cara. She held herself down on my shaft, rocking and spinning her head back and forth. She was twisting her tongue around me, too. It was driving me so crazy and to the edge that I gripped the armrests so hard that I thought I was going to break my fingers.

My hips began to squirm a bit as my orgasm approached. Kristy pushed down on thighs with her hands to keep me still as she bobbed on my cock, continuing to twist her tongue as she did. Behind me, Cara moaned just loud enough for me to hear through the sucking noises Kristy was creating.

I glanced down at Kristy. Her hair swayed, and eyes were locked on my crotch. It was like she felt me staring at her because her lips formed a tighter suction than ever. A puff of air escaped my mouth as I said, “I’m going to cum,” all in about one syllable.

Kristy sucked my cock harder and faster. I felt an immense pressure on my shaft as I came when my tip hit the back of her throat a final time. Once the initial sock of my orgasm ended and a few spurts of cum later, Kristy resumed sucking and cleaning my shaft. Our eyes met, and while I stared into her eyes, Kristy swallowed every drop of my cum.

“Mmmmmm,” Kristy purred. “Just what I hoped for from your big young cock.” Her tongue fell out of her mouth and gave my balls and softening shaft a long slow lick. Her left hand grasped my cock and gently stroke my cock as a tease.

Kristy and I remembered who was in the room with us. We both turned to look at Cara, who released a moan of approval. She removed her fingers from her panties and licked them clean. She seductively bent over to pull up her skirt. Once her skirt was zipped back up and blouse tucked back in, she walked over to Kristy and me.

“Thanks for letting me watch you eat lunch…” Cara said to Kristy teasingly.

“You are welcome. I think you enjoyed it in your own way,” Kristy responded.

“Indeed, I did. I’m going to go home, fuck my husband good, and try for baby number four,” Cara winked at Kristy. “And you,” she said as she directed her attention towards me. Cara softly placed her fingers on my cheek and said, “Thank you for the look you gave me. I needed that confidence boost. I’m still working off baby weight number three.”

I smiled at her, “You are welcome. I would never have guessed you have three kids.”

“Oh, you are too kind,” she patted my cheek before dropping her hand to her thigh. “If I weren’t so loyal to my husband, I’d invite you over so I could test drive your – what did you call it Kristy? Oh yes, big young cock.”

Then Cara leaned down to Kristy and my level and whispered, specifically to me, “Just remember that thing is bigger than you think, so be careful with those little petite college girls.”

I was a little shocked by her statement. I nodded in acknowledgment. Cara winked at me, then Kristy and strutted her way towards the door. Kristy and I both stared at her as she exited the room.

“That was a tad more than what I expected for lunch,” Kristy said.

“I don’t mind. Do you?” I responded.

“No. Not at all. Now before I button back up…” Kristy said as she stood up and leaned her breasts into my face. “You can give them a kiss if you’d like.”

I didn’t hesitate to give each of her breasts a kiss. When I leaned back, she quickly buttoned up her shirt with the biggest smile I’d seen on her face.

“Oh, my!” She exclaimed. “I almost forgot!”

Kristy took a quick step over to a file folder she had carried in and removed a roll of lipstick. She applied it to her lips before smacking them together. Stepping back between my legs, her left hand took hold of my cock, which had remained relatively hard through her stroking and Cara’s complements. Kristy moved forward and planted a big, long kiss on the side of my cock, leaving a red outline of her lips.

Looking back up at me, she asked, “Was that what you had in mind when you told me to remember my lipstick?”

“Better,” I responded.

Kristy smiled and blushed as she stood back up and rolled up her stocking. I didn’t want to smear the lipstick mark on the side of my shaft, so I gently tucked myself into my boxer briefs and pulled my pants up. We smiled at each other as Kristy rolled down her skirt and did her best to rub out the wrinkles.

As I stood up to zip and buckle my pants, Kristy kissed my cheek, leaving a lipstick mark.

“I knew this would happen,” she laughed as she pulled out a tissue from a folder. She wiped the mark off my cheek and started walking towards the door. I grabbed my jacket and folders I brought with me and followed her back to her desk. She retrieved both Cokes from her boss’ refrigerator, and we stood at her desk for a minute or two, gulping our drinks down.

“Thank you for the invitation, Kristy,” I began. “That was a lot of fun. I enjoyed it,” I finished as I glanced up and down her body.

“The thanks goes all to you. You made an old woman very happy today. In fact,” she leaned in and whispered, “I’m going to have to change my panties.”

My brow raised, and she smirked. “Now you better get going to work, young man,” Kristy lovingly demanded.

“Yes, ma’am,” I said and winked.

We both exchanged smiles, and I left. A few days later, at the store, Kristy thanked me once more. I thanked her back and complimented her on her beauty once again, which made her blush. Over the next month or so, she would share stories of Mark and Chris with me.

She wouldn’t get into super detail, but it was enough to make me jealous I was only getting head. Yet, I was content because I also knew I made her happy at the same. It took one story about Mark for her to extend another invitation to me around Christmas.