The Dilemma

"You are beautiful, Jan," I softly affirmed.

She gave a small, nervous smile, then turned her back to me. I understood and unfastened her bra. She stayed turned away and removed the bra, then slowly turned back, hands at her side. Her big, full breasts were beautiful and lay heavily on her chest but were not saggy and held their shape well. They were at least full D's, probably larger, and were capped by large, smooth, dark areolae with pronounced, medium-sized nipples. Her breasts were a sight to behold.

After letting me take them in, she reached for my tie and removed it, then started unbuttoning my shirt. After she helped me out of my shirt, she ran her hands down my arms, then reached for my undershirt and untucked it. I bent forward and she pulled it over my head. When I straightened up, she ran her hands over my chest and down my stomach.

"Pretty awesome, Sean," she remarked.

"My thoughts, exactly," I replied.

She reached for and undid my belt as I kicked my shoes off, then she slowly pulled my slacks down and I stepped out of them. She dropped to her knees and pulled my socks off as I lifted one foot, then the other. She stayed in that position, her face level with my boxers. She looked up at me, and I gave the slightest nod. Slowly, she pulled my shorts down, and my semi-aroused penis flopped out. As I stepped out of my shorts, she whisked them aside, then brought her eyes back level with my crotch and reached a hand for my penis, grasping it, lifting and examining me, lightly running her fingers up and down the shaft.

Looking down at her beautiful body and feeling her warm gentle touch as she fondled me, I became more aroused and began to grow in her hand. To add to the process, she took her other hand and hefted my balls, gently fondling them. I grew more. Next she tentatively pressed her lips to my cockhead for a moment, then gradually parted them and slipped them over the head. I went almost fully erect. The delicate touch of her hands on my balls and shaft, and her warm mouth on my head, were having the effect I'm sure she was after.

Slowly, she slid my cockhead out of her warm, wet mouth, and looked up.

"You're a big boy, Sean...a damn sight bigger than Tom."

I reached for her and brought her up to me, wrapped my arms around her, engaging her in a warm kiss, relishing the feel of her naked breasts pressed into my chest. When we separated, she shyly hooked her thumbs in her pantyhose and peeled them off. Then she pulled the comforter down and crawled on the bed. I watched the muscles in her legs flex as she moved. She arranged a couple pillows against the headboard, then lay back. I observed her vulva for the first time. The thin dark line of pubic hair that extended from her navel lead to a full, thick bush of curly, dark-brown pubic hair.

"I'm pretty hairy, sorry."

"No, no. I love it."

"I'm usually a little more groomed up, but I haven't bothered lately. Tom always wanted me to do the big shave, but I tried that years ago and couldn't stand the all the shaving."

"I love your bush the way it is," I assured her, and crawled on the bed as she reflexively spread her legs.

As I crawled between her thighs, she reached for me to pull me into an embrace.

"Jan, I want to pleasure you first."

"Oh...Not used to that, but by all means," she smiled, "though, um, I may not be too fresh."

I bent down and buried my face in her bush, taking in her earthy, womanly scent.

"Heavenly," I replied, and began.

As I got in position, Jan spread her legs wide, opening her labia, which were nominal in size and somewhat covered in pubic hair. Her inner labia were long, slender, and a light pink. I engaged her lips with my tongue and her hips immediately jinked in response.

"Nice...oh yes, I love it. Tom never, never touched me, except to enter me. Mmm, yes, keep...oh gosh!" she exclaimed as I swiped lower, engaging her pucker.

"That's so um...you caught me by surprise...but I like it," she added.

I kept working her, licking, sucking, probing, gauging her reactions.

"Oh, oh, yes, mmm, mmm...ungh, oh, if you keep...doing that..."

I started licking and sucking around her clit as I worked one then two fingers into her already slippery vagina. When I engaged her clit, Jan grabbed my hair and forcefully pressed my face into her sex, greenlighting me to work it more aggressively. As I did, I replaced my fingers in her vagina with my thumb and pressed my slick middle finger against her pucker and worked it in, then started mini-stroking both orifices. She went nuts.

"Oh fuck, baby, you're going to make me cum...going to... oh, shit, oh...oh yesss, cumming!" she exclaimed as she started jerking her hips, and pulling painfully on my hair.

I hung on like a tick and kept thrusting with my fingers as Jan's climax washed over her.

"Ahh, ahhh, ungh, fu-u-u-uck!...Oh gosh, Sean, oh, oh, oh...thank you, baby."

I wiped my face on her bush, and crawled up to engage her in a hot, wet kiss. She crushed me to her, still lightly spasming from her orgasm.

Breaking the kiss, she urgently exclaimed, "I need you in me, now," and reached between us, searching out my erection, "and, Sean, my tubes are tied."

With that, she grasped my cock, pressed the head against her opening, hooked her heals behind my buttocks and urged me forward. Jan was not tight, but snug, and her vagina was slippery wet and warm. It felt divine as I slipped past her opening and slid into her snug vagina. As I pushed forward, I abruptly bottomed out, mashing my head against her cervix.

"Oh damn, you fill me so nicely, honey," she moaned, as I started thrusting.

I began with a slow, smooth stroke, bottoming out with each thrust. It felt divine for me and she was urging me on with her heals against my buttocks. As I stroked in and out, Jan grunted and moaned, then started urging me to go faster. As I increased my tempo, she started lifting her hips, meeting my thrusts.

"Ungh, oh, mm-hmm, ah, ah, yes, baby..." she groaned and cooed as I started thrusting harder. Hands wrapped around my neck, her head tilted forward, nodding and biting her lip, watching my cock thrusting in and out. Then she released my neck and quickly started working her clit, jilling herself frenetically.

"Gonna cum, baby!"

I started pounding her, hammering her as I thrust harder and deeper, feeling my own climax beginning to build.

"OH-OH-OH-YES-CUM-MING!" she exclaimed, and I unloaded, cumming like crazy, filling her hot tunnel as she bucked and spasmed beneath me. When she stopped spasming, I sat back on my haunches, catching my breath.

Jan was leaking tears, "Sean, baby, that was so...so wonderful."

I pulled her up and she wrapped her arms around me, laying her head on my shoulder, continuing to leak tears, as we sat, coupled together, her legs still wrapped around my waist, my spent, but still firm cock buried in her.

"I can't tell you how I needed that. It's been far too long since I felt like this...since sex was like this for me. Thank you for...for being with me, loving me."

"Jan honey, it was just as wonderful for me, and it's been a long time for me, too."

She leaned back and looked at me, "Are you okay? Are we okay. I know you didn't want to do this...No," she hushed me, "I know, and I understand. But I needed this, Sean. And, I needed it to be you. There was no one else I could...no one I could imagine doing this with. I hope you don't regret..."

"Jan, honey, I don't regret it. But I am worried. I know you said tomorrow will take care of tomorrow, but I am concerned."

"I know. Me too," she said, softly, as she laid her head on my shoulder, pressing her full, soft breasts against me. "But, can't we handle this? Does it have to be a big deal?"

"I don't know. Time will tell."

After showering and dressing, we sat at her dining table and sipped ice water.

"Sean, I know we can't let the others know about this. It would upset things at the office. I know that. So, you don't have to worry. I know we have to be cool about this."

"Yes, I think it's best. Don't get me wrong. I'm not ashamed of what we did - not one bit. It's just...awkward, with our relationship, you being my secretary and..."

She put a finger to my lips, "Our secret...and Josh, I don't expect...I, I mean, you don't have to think you owe me anything...what I'm trying to say is, if you meet someone...if I meet someone..."

It was my turn to hush her, "Understood."

But I really had mixed emotions, sitting here looking at Jan. I could never look at her the same again. I just didn't know, couldn't see how things could continue the way they were before.

III. THE GIRLFRIEND

I went home that night and couldn't fall sleep. I kept playing the evening's events over and over in my head. I finally slept fitfully for a couple hours, awoke at dawn, and went for a run in the crisp morning air to try and calm my mind. After showering and my morning routine, I headed to the office and was dreading it, dreading how it would go.

When I arrived, Jan was already at her desk. As I entered, she looked up and smiled, "Morning, Sean. You had a call from Mark. He's bringing in the seller's disclosure on that problem listing and wants to talk to you about it."

"Sure, what time will he be here?"

"He'll be in at ten, but said he'd get with you whenever was convenient for you."

"Ten's fine. Please let him know, thanks."

I headed to my office. A few minutes later, Jan stopped by.

"I'm making coffee. Like a cup?"

I smiled, "A couple."

"Didn't sleep well, did you?"

"Um, no," I admitted.

"Sean, I'm fine," Jan smiled sweetly, then headed to the breakroom.

Well good. Somebody was 'fine'. Not me. Fortunately, it turned into a very busy day, with me out of the office from lunchtime on. When I returned, it was almost seven, and Jan was gone. I unlocked the door and went in to tie up some loose ends before heading home.

As I was closing up, Sandy pulled up.

"Hey, Sean, I just need to grab a couple folders for tomorrow, thanks."

I held the door for her as she came in.

"Where's Mark?" I asked.

"He's home, hopefully making dinner. I'm famished," she remarked over her shoulder. When she returned, she gave me a look, "You look like you had a rough day. Everything okay?"

"Yeah, sure. Just a busy day."

I felt like I had a big sign hanging around my neck, "HEY, I BANGED MY SECRETARY!"

"See you tomorrow," she said as she headed back to her car, and I locked up.

As I headed home, I thought about Jan, how nonplussed she seemed this morning. Other than being in a good mood, she didn't show any signs of what we did the night before. I went home, pulled out a frozen stew and heated it for my dinner while I caught up on market news. Mountain properties were booming right now, and we were getting our fair share of the action, but real estate markets fluctuate, sometimes dramatically, and I like to keep up to speed on developments, trends and so on. But I found I couldn't focus. I couldn't stop thinking about Jan.

Fortunately, a call on my cell interrupted my futile attempt at research. I pushed my dinner aside.

"Hi Sean, it's Lisa. Got a minute."

"Hi Lisa, of course. How've you been?"

"Well fine, but um, I was wondering how you are doing? I haven't heard from you since we last got together, and so..."

"I'm sorry. Time has gotten away from me. I should have called."

Lisa quickly put in, "I wasn't sure if you, well whether you were interested in getting together again. I thought we had a nice time, but then you didn't call..."

"Lisa, really, I'm sorry. I had a great time. I am sorry I didn't call. I'd love to get together. If you'll let me make it up to you, how about we get together for dinner Friday, or whenever works for you."

"Friday works fine."

"Great. Did you have anything in mind or would you like me to choose?"

"Actually, I was wondering if you'd like to come for dinner? I mean, my place for dinner...if you like?"

"Sounds wonderful."

"It's a date then," she said brightly.

"What time should I be there?"

"How about seven?"

"See you then."

Lisa is an escrow officer for a title company I do business with, and we met when she was processing one of my escrows. Over the course of things, we ended up grabbing a bite together, where we got to talking, which ended up with her asking if I wanted to get together sometime.

I was surprised, but pleasantly so, and we had a lunch date, then a dinner date, and since then, I hadn't called her. Honestly, I'm not sure why I didn't pursue things with her, but I think I was just being a little guarded. Anyway, I figured this might just be the distraction I needed to get my mind off Jan.

Thursday and Friday were just like Wednesday; Jan was pleasant and professional. I started to wonder if I was overreacting to our liaison. But the end of the week couldn't come soon enough, and I was looking forward to my date with Lisa.

On Friday, I left the office a little early, went home, freshened up and changed into more casual attire, then headed to her house. She lives in Manitou Springs, not far from Jan's place. I arrived a few minutes early, but she saw or heard me pull up and met me at the door.

"Sean, good to see you," she greeted me, taking my hands and kissing me on the cheek.

"Good to see you, Lisa. You look great."

"Oh, thanks," she smiled and led me in.

Her home is nice, on the small side, a two-bedroom, around 1400 square feet, but very nicely appointed. As she led me into the living room, I couldn't help but notice her derriere in the snug-fitting jeans she was wearing - medium-sized and very firm looking. Her legs looked like they would be pretty nice to, not skinny, but well-muscled.

Lisa is exceptionally pretty with highlighted blond hair worn long, currently gathered in back and hanging between her shoulder blades. Her sleeveless blouse showed she had well-toned arms, not quite muscular, but firm-looking. The scooped neckline showed the swell of her moderate, but obviously firm breasts, somewhere between a full B and a small C cup. She is average-height, about 5'-6" I think, and slender, probably weighing around 130. She has a slim, oval face, and like me, blue eyes. With an average nose, slightly full lips, and a nice jawline and chin, she is quite attractive.

As she indicated for me to sit, she offered, "Dinner will be ready in about 20 minutes. What would you like to drink? I have a couple wines, iced tea and some soft drinks."

"What are you having?"

"I have a Beaujolais which I'm serving with dinner and thought I'd have a glass of that."

"That will work for me," I replied, and she headed to the kitchen.

She returned and handed me a glass.

"So, I know you've been pretty busy," she started as she sat across from me, "you have several deals in escrow with us, right now."

"Yes, business is good at the moment, and yes, it was a little hectic the last couple weeks, but I'm starting to get caught up. How about you?"

"We're swamped. Of course, this time of year is always the busiest."

We continued small talk until the baked lasagna was ready, and Lisa moved us to the dining table.

While we were eating, she commented, "I remember you said you do a lot of hiking."

"Yes, I try to get out every weekend, but haven't been in a few weeks. I love the physical aspect, the peace and quiet, and of course the scenery in the mountains."

"I used to do a lot of hiking with my dad and my brother, but since I moved here, I've only been out a couple times - nobody to hike with, and I don't like to go alone."

"Well, you shouldn't hike alone, though I do, occasionally, when I can't get together with someone."

"Who do you hike with?" she asked.

"I have a couple friends from my old office that I get together with when our schedules match up. We sometimes backpack and do overnighters."

"Oh, that sounds nice. Maybe we could do that sometime, go hiking, I mean, or even backpacking, though I've never done that."

"Weather's supposed to be good tomorrow. We could go for a hike," I ventured.

"Really? I'd love to."

"By the way, this lasagna's pretty awesome," I commented.

"Oh, thanks - my mom's recipe."

"Funny," I replied, "but you don't look Italian, and I've had lasagna made by Italian friends that was not as good as this."

"Well thanks, and I'll have to pass the compliment on to my mom. She cooked professionally for years. She was a sous chef until I was born."

"Well tell your mom I think her lasagna is the best."

She smiled, "Will do. So are you serious about going for a hike tomorrow?"

"Sure. I was planning on heading to the mountains this weekend, anyway."

"Well, I'd love to."

"It's a date then."

After dinner and clean up, we retired to her small patio and continued to visit as the sun set. Lisa opened a second bottle of wine, brought it out and we settled around the patio table.

"So, where are you planning on going to hike?"

"I was thinking of doing the St. Mary's Falls trail in North Cheyenne Canon Park. I haven't been there in a long time. It's nice, not difficult, and doesn't take too long. We could pack a picnic lunch, take in the falls. Might be nice."

"Sounds wonderful. I've never been there. Where is it?"

"It's west of Pueblo. We'd have to get an early start."

"That's fine, and I could take care of making lunch," Lisa volunteered.

"I think we have a plan. Pick you up at eight?"

"Yes, great...It's getting a little cool. Could we go in?" she asked.

"Sure."

When we got to the living room, Lisa poured us more wine and as I sat, Lisa put on some soft music.

She sat and took a sip of her wine, "Sean can I ask you about...well, your divorce. I mean, I know you're divorced, but..." she paused to let me pick up the conversation.

"Sure. Well, I divorced two years ago; was married eight years; but we struggled after four or five years; busy lives, wrong focus, fell out of love, called it quits. I guess that's it in a nutshell."

"And now...I'm sorry, I guess I want to ask about since you're divorce, you know, has there been anybody serious?"

"No, no one serious. I've dated but haven't really connected with anyone, yet. What about you?"

"Oh, well, yes, about me...um, I think I told you before that I was married for three years, right after college, but it was pretty much a mistake from the beginning. Neither of us was ready to make the commitment we needed to at that point. My ex was starting his career and that was his focus. I was trying to figure out what I wanted to do. Anyways, that was four years ago and since then I've been in a couple relationships, but each time, I felt there were things that weren't right and I was afraid to make another mistake. Then I moved here, and haven't really had much luck in that department, finding someone I liked...I mean until you," she finished, acting a little embarrassed.

"Well, I'm glad you like me, Lisa. I like you, too," I said and smiled to put her at ease.

"Oh thanks. I wasn't fishing, but thanks. I just, well we haven't talked about um, 'us' or anything. I guess I just wanted you to know that I like you, so...well, that's all."

"Likewise, Lisa. I think we have to see how things go. I am a little cautious these days."

"Oh, me too."

She took a sip of her wine, "Oh, I like that song. Um, would you like to dance?"

"Sure, that would be nice," I replied and stood.

Shyly at first, Lisa took my hand and slipped an arm around my waist. I slipped my arm around her and held her close, but not too close. We swayed to the music and didn't talk for a couple minutes. As we danced, I felt her subtly close the distance between us.

"This is nice," she softly remarked, "I haven't danced in a long time...Oh, well, I did go dancing. I went to a club with a couple of girls at work, but that was so not fun. And I never got to the dance floor. I spent the whole time fending off guys. I mean, if one of them had been nice, but they were all jerks. They advertised Thursday as 'Ladies' Night' but should have called it 'Jerk Night'."