What Were You Thining?

AN: This is a work of fiction, these aren't real people so there's no reason to get your panties in a bunch...

My name is Jake, I'm 25, 5'11" and 180 pounds. I keep in shape and have since high-school. I swam in college, and typically stay active these days via a combination of running, cycling, and swimming whenever I get the chance. I'm not a hairy guy which is fine with me. I've had several lovers over the years that had been fans of shaved balls, and after a while I just started doing it for myself, and keeping my pubes neatly trimmed up above my smooth balls. The rumors are true, your dick looks bigger when it's not buried somewhere in a hair jungle.

No, I don't have a nine inch cock, that's as thick as a beer can,

I'm probably considered 'slightly above average' at just over seven inches, and I like to think I'm thick enough to give the ladies that happy-full feeling. I lost my virginity at sixteen, and since that time have been with a total of eleven women, which includes 2 serious relationships that lasted several years.

At the end of the day, I suppose I'm just a regular guy, with regular guy looks and happy with where I am in life.

Things changed when I accepted a new job in the post-pandemic world that required a move across quite a bit of the country. I had grown up in a small northern California town, but had been living in the Midwest since graduating college. This move would land me on the east coast for the first time in my life, and I thought of it all as a great adventure. I had planned to reinvent myself, create a new circle of friends, meet an attractive woman, and maybe settle down and do the family thing.

Life had other plans.

The new job had transitioned back into a 'pre-COVID' system that required the employees to be in the office, and not sitting at home in their PJ's in front of their laptops. It was refreshing in that it would give me some exposure to the local culture, meet some new people and jump-start this new version of me. The office was roughly 60% men, and the women ranged from smoking hot, to grandmother-types.

I'd heard the saying 'you don't shit where you eat' countless times and it made sense, but as I'm a normal red-blooded guy, I couldn't help but to flirt a bit here and there.

Jessica is an 'administrative assistant' and the first time I saw her, I immediately wanted to have sex with her. She's older than me, thirty-something and while she always wore professional attire, her outfits were always perfect and hugged her athletic body closely. She wore skirts daily, and moved with the grace of a cat in her heels. I loved the sound they made as she moved through the office. Her tits were always conservatively covered, no plunging necklines or cleavage peeking through her blouses, but they were clearly perfect, not too big, not too small and I'd guess she was a solidly in C-cup territory. Her ass filled her skirts as if they'd been sprayed on, her confidence cast a spell on me, and I imagined pushing my dick into her warm, wet pussy and fucking her senseless, but it was just a fantasy, Jessica was very, very married.

Flirting was okay though, nothing over the top. I'd chat with her daily, she shared what she did over the weekend, and talked about upcoming plans she had with her husband. I listened intently, and the more I got to know Jessica, the more I realized she was almost perfectly what I was looking for. A sexy, intelligent, confident woman. I had been masturbating while fantasizing about her for almost a month by this point, and one Friday during one of our little chats, she looked at me and gave me a sideways grin, and made a show of holding out her hand and waving her wedding ring for me to see.

"You know Jake, I'm a married woman." she said in a tone that sounded almost like she was admonishing me.

We'd been talking about local places that had good coffee and I played back everything I'd said in my mind. Nothing I'd mentioned could have been confused as possibly asking her out. I was baffled by her comment, and she clearly knew that I realized she was married.

"I know that Jessica, I hope you didn't hear something I said the wrong way?" I knew I hadn't given her any reason to say that.

"It just almost sounded like you wanted to ask me out for coffee." she said, and watched me with an easy smile. Her grey eyes watched me carefully and a finger rose to move a bit of her light brown hair away from her face.

I hadn't been angling to ask her out for coffee, but she put it out there.

"So I guess getting a coffee is a no-go." I said back to her, and kept my eyes on hers.

"We'd better get back to work." she said with a grin, and then turned and walked back to her side of the office and I was absolutely certain that she was swinging her perfect ass a bit more than she usually did.

'Fucking tease!' I thought to myself. Then got back to work, and figured I'd back off a bit. I imagined people on the east coast were operating on a different frequency, and maybe I was coming on too strong, although I certainly didn't think so.

Over the weekend I continued to explore the area, I biked around near my apartment and stopped at a sandwich shop to grab a light lunch. The woman behind the counter was cute, with incredible pouty lips and prone to grinning in a way that suggested

(to me anyway)

that she was a fun person to be around. I asked for her number, and we made plans to grab lunch the following day.

Lunch was fine, but sitting down and getting to know Trish turned out to be less than fantastic. Her outfit showed more of her body, and her body exhibited what I sometimes call 'random doodling' or just what looks to me like pointless tattoos everywhere. Don't get me wrong, I don't have a problem with tattoos, on men, or women, but I'm sure you've seen plenty of people that look how I'm describing, a strange little tattoo on their wrist and then something else random on their forearm and so on and so on, just all over. As cute as she was, the tattoos everywhere were more than I could easily handle and while we shared a few kisses at the end of our date, I gave it some thought and decided that I probably wouldn't call her afterward.

Monday came and I was feeling pretty good, I'd met someone, been on a date, and felt like everything would start falling into place now that I'd cracked the code of the east coast. I was in our kitchen area at work and poured myself a cup of coffee and Jessica walked in, I heard her coming via her telltale clicking heels. I turned and saw her, smiled and looked at her shining beige-colored pumps and shook my head and told her she'd never be able to sneak up on anyone.

She grinned and told me she was perfectly content knowing people could hear her approach. There was something about her dark red lipstick, it made her lips seem fuller and was a type that almost absorbed the light in the room. Not glimmering, shiny and moist, her lips seemed coated with a dull primer, but I wanted to taste them in the worst way.

I thought of something to say, but remembered she had made a show of reminding me she was married so I asked how her weekend had gone.

"I told my husband that you almost asked me out for a coffee, that was an interesting conversation." she said and grinned at me.

"I almost asked you out?" I asked her with a grin of my own. "Trust me, I don't almost ask anyone out."

"He said I could have a coffee, that it wasn't a big deal." She explained. "He knows he can trust me."

"Let's get a coffee for lunch." I asked before I took any time to think about it.

She smiled for a moment longer, and then turned and definitely wiggled her ass as she walked away.

---

"You have that look." Jessica said as she sipped her coffee.

"What look is that?" I asked and scooted my chair closer to our small table at the coffee shop.

"The look someone gets when they want something they can't have." She watched me for a moment and then added "Do you want something you can't have Jake?"

"Who says I can't have what I want?" I figured why not, it wasn't like I had my tongue in her mouth.

I may have been imagining it, but I could swear Jessica's face flushed. She took another sip and watched me silently.

I reached out and took her hand, extended her ring finger, and then watched her.

"Just coffee." she said quietly.

"You sure?" I asked, trying hard to stay in 'guy really wants to fuck you ' mode, instead of 'aw, come on!' mode.

"Jake." she almost whispered, and kept her eyes riveted to mine.

It felt impossible to pull back from, but that's what I did. I lightened things up a bit, and eventually let go of her hand. We finished our coffees and walked back to the office. I imagined her being mine, looking as incredibly sexy as she did. It was difficult not to start getting hard.

As we rode alone in the elevator, I decided I'd try to kiss her, and as soon as I turned to face her, she said "I liked having lunch, let's do it again tomorrow."

I agreed, and when we walked back into the office we went in different directions and I toyed with the idea of jerking off in the men's room, but it seemed like anytime I'd ever been in there, a steady flow of guys coming and going would have made that difficult.

That night, I searched the web for porn that included a woman that looked similar to Jessica, the closest I found was a woman named Penny Barber. I watched her in a few scenes and finally jerked a huge load into a tissue. I imagined Jessica had a neatly trimmed bush like Penny had, and tits that were a bit smaller, but incredible.

---

"My husband said he thinks you're trying to seduce me. I told him we had coffee, and you held my hand for ages." she said quietly in the coffee room the next morning.

I watched her, and decided that saying anything would be pointless. It was obvious I wanted her, badly, in spite of her being married.

"Lunch today?" she asked.

"Someplace else?" I wanted to see if she was interested in something more substantial than coffee.

"Maybe coffee is best." she said with a voice that didn't sound convinced.

I nodded, and watched as that perfect ass of hers swayed from side to side as her heels clicked on the tiled floor.

I wasn't able to get anything accomplished all morning. I played out a number of scenarios in my head, and the one that I wanted the least was for Jessica to just tease me. It felt a bit like that was what she was doing, but the other scenarios included her talking to her husband, and either one, or both of them being excited by the idea of someone in the office attempting to seduce her.

Lunch came and as we walked to the coffee shop, I struggled not to reach out, and take her hand. I wanted to in the worst way, just to see if she'd let me, and then more, to make my intention absolutely clear without having to verbalize it. We sat with our coffees and didn't say much, but we watched each other intently.

"Do I still have that look?" I asked.

She nodded, "I think it's worse today."

"It is." I agreed, and made a point to look at her wedding ring.

"Jake, how old are you?" she asked, and fidgeted with her ring.

"Twenty-five, I figure you're my age, maybe a year or two difference." I said, lying.

"I'm thirty-six years old, that's a lot older than you. But thank you." she said. "I've been married for twelve years, I love my husband very much, and I would never leave him under any circumstances, I'm going to grow old with him, Jake." she explained, making it clear this wouldn't turn into anything more than what we were doing.

"You're lucky, finding someone you want to grow old with must be incredible. He's a lucky man." I admitted.

She smiled and sipped her coffee.

"Does it make me a horrible person?" I asked. "Having this look for you?"

"It excites me." she said quietly. "We've talked, my husband and I.."

"About us?" I asked, and looked at her wedding ring again.

She nodded and her left hand moved toward the center of the table.

"A few years ago, we discussed possibly seeing other people, you know, swinging, but I think we both got too nervous that it would damage our marriage." she said.

My hand covered hers, and I nodded "I can see how that might be a problem."

"I want you to know that this thing we have, has added some spice to my marriage." She was trying to maintain her confidence, but not doing so well.

"What exactly is this thing we have?" I asked, and prayed that my hand covering hers wouldn't start shaking uncontrollably.

"It feels like the start of.." she glanced around for a moment and then lowered her voice and said "an affair."

My dick was harder than I could recall in quite a while. But the question was, did she just want to carry on this way, having cozy lunches, simple contact, longing stares?

"I've got to think about what I want to say next, because the last thing I want to do is cause problems for you." I said honestly.

"Jake, have you ever been with a married woman before?" again, her voice was barely a whisper.

I shook my head "Never."

"What happens next?" she asked, and her fingers moved and then intertwined with mine.

"I want to taste you, I have since my first day in the office." I figured the best thing was to be honest, without saying too much.

"If this happens, you have to know it can't ever be more than a physical thing." she said with a bit of a warning tone.

"I don't want you to wreck your marriage." I said as I squeezed her hand.

"This can't affect our working together." She was covering her bases.

"It won't."

---

The next day, Jessica pulled me aside near the mail room and said "I can't do lunch today, but I spoke with my husband, we're both excited about this. What do you have planned for Friday night?"

"Spending it with you." I answered automatically.

She nodded quickly, and then walked off.

Friday night would take a hundred years to arrive, at least it felt that way. We had coffee once again during the week, and talked more openly about what we were going to do. She told me that she had no idea if this would be a one-time thing, or if we'd make it something that regularly happened. She said that she had mixed feelings about her husband possibly finding a playmate for himself, but that there was no denying that both of them were of the opinion that their marriage would be fine, and that they had been together long enough that they both felt they could separate love and sex.

Friday finally arrived and during lunch, Jessica told me that her husband had reserved a room at a local upscale hotel. She said she couldn't promise to spend the night, but that we could arrange to meet there directly after work.

That evening I sat in my car and called her, to let her know that I had arrived, and if things were still fine. She just said everything was good, and that I should come up to the room. In a strange moment of guilt, I wondered if this was a good idea. Sure, Jessica and her husband had talked about this, but what happens afterward would be anybody's guess. I didn't want the burden of causing stress in someone else's marriage, and I briefly thought of just calling the tattooed woman I'd kind of ghosted and seeing if I could make it up to her.

The hotel room door opened a few moments after I knocked, and Jessica looked incredible. She had changed clothes, although still wearing professional attire, this was a decidedly sexier look. Her white silk blouse was partially unbuttoned, revealing a bit of cleavage, she wore a gray pencil skirt that came to just above her knees, and dark nylons that disappeared into shiny black leather open-toe stilettos that allowed her painted toenails to peek through. Her makeup was a bit more dramatic, her eyelids held an almost smoky grey color and her cheekbones seemed more angular, but it was her glistening lips that finally broke me.

We came together and her lips melted into mine, her body felt like it was wound tight, her small waist seemed tiny in my hands and I wasted no time in trying to undress her. She giggled playfully, and stepped away from me and twirled around, asking if I liked the outfit she wore for me.

"Jessica, I can't ever remember a more beautiful woman that I've ever wanted more desperately." I admitted.

"Hearing that makes me feel so strange, not in a bad way. I love that you want me." she said and pursed her lips.

I wanted to taste every square inch of her body, I promised myself I'd know all of it before the night was over.

Her clothes came off in an agonizingly slow pace, and by the time she stood before me wearing only a black lace garter belt, stockings and her heels I was nearly panting. The neatly trimmed bush I'd imagined was in fact a narrow runway of curly black hair. Her tits were incredible, and her nipples quickly responded to my lips. The more time I spent tasting her, the more I realized I'd never be happy with this happening just once.

We collapsed onto the bed, and I moved between her legs, and traced my fingers along her pussy lips. Surprisingly, I discovered that she had a small silver piercing that ran vertically through the hood of her clit. I'd never been with a woman with such a piercing, and I briefly imagined it must have been incredibly painful to have that part of the female anatomy experience a needle poke.

We had time, and so I struggled to go slowly, although all I could think of was filling her with the semen that had been collecting since hearing that we'd have this evening to ourselves. She kissed better than any woman I'd been with previously, her body was more expressive, anything that felt good resulted in body movements and soft moans, and her eyes cast a spell on me that I knew would be hard to to break. I needed more than a night, I needed weeks, months, maybe years. I wanted to learn everything that would give her pleasure and take all of the time in the world to accomplish that, but somehow my dick had found its way to her swollen pussy lips, and then I felt her fingers on my shaft as she fed it into her hot, waiting entrance.

She was tight, and felt hotter than other women, it was like pushing into a damp velvet glove that had just emerged from a hot oven, a tight glove. When I was fully inside of her we stayed like that for a time, passionately kissing as Jessica's married pussy squeezed me, and caused shivers to race down my spine.

"Do I feel okay?" she asked quietly.

"You're incredible, I don't have words."

"You fit me perfectly, there's no room left inside of me." she said smiling.

"That's girl-speak for a guy with a small dick." I chuckled.

"Honestly, your dick feels like it was made just for me." she said as she opened her mouth, and my tongue met hers a moment later. We stayed in the missionary position like that, kissing, and making love. This was love-making, but I had every intention of fucking her, really fucking her before the night was out. I'd love to tell you that I ground against her like that for hours, but I'm a regular guy, and soon enough I knew that unless I took a break, I was going to cum and it was way too early in the night for that.

I rolled off of Jessica and lay on my back as she climbed on top of me and took my cock in her hand once again and I watched her face go all dreamlike when she sank down onto me. Her eyes focused on mine and she smiled and told me how good I felt inside of her as she began riding me. We stayed together like that and Jessica lay forward and our mouths were joined once again as she ground herself against me, this was great because there was plenty of sensation for me, but it must have really been working for Jessica because she became louder, and her body seemed more needy, when her first orgasm came, she cried out into my mouth, and I held her as the little aftershocks of her peak continued for a time.