The Dilemma

I started pounding her, slamming her into me with my hands gripping her hips, as I thrust for all I was worth. I felt the cum boiling up in my balls then exploded, thrusting like a madman as I came and came and came.

AHHH, OH, OH, OH...ohhhh...mmm," she moaned as she came down from her orgasm.

"Damn, I think you killed my poor pussy," she laughed, then reached for me, pulling me down to her.

We kissed, crushing our lips together. I came up gasping for air as I was still trying to calm down from the intense coupling.

"That was wonderful, baby," she cooed and propped up on her elbows.

When she did, fluids squished out around my cock, making a mess.

"Oh gosh," she laughed, "Guess we have some cleanup to do, and some sheets to wash."

I slowly pulled out of her, and more cum and fluids leaked out and puddled between her legs.

"Let's get to the shower," I suggested, unfolding my cramped legs and gingerly climbing off the bed, then offered her a hand. She took my hand, stuck her other one between her legs, swung them off the bed and joined me, making a beeline for the toilet. I turned on the shower and got the temp set while she drained. When she was done, we got in the shower and cleaned up. After showering and drying off, I slipped on a t-shirt and shorts as Lisa put her bra and panties on, then we went to the kitchen. I got us ice waters and we sat at the nook and talked.

"Sean, that was wonderful, and I know we were supposed to go slow, but, honestly, I didn't want to wait."

"You're right. It was wonderful, and yes, I wanted to...take a slower approach, but I'm not complaining," I said, smiling.

Lisa smiled and took my hand, "Do you mind if I sleep over. It's a little late..."

"No, of course."

"Thank you. I guess we'll need to change the sheets on the bed," she pointed out, giving a light laugh.

"Yes, somebody made a mess...Um, I do have to do something, tomorrow, so..."

"Oh sure, that's fine. I need to go home and get ready for the week. And I do look forward to getting together again when we can. I've had a wonderful time."

"Me too."

We went to bed and I fell asleep almost immediately. I awoke to sounds coming from the kitchen through my open bedroom door. Lisa was up, dressed and making breakfast.

"I hope this is okay. I just kind of helped myself to things. I was hungry and figured you would be, too," she remarked as I entered the kitchen.

"Starving. How can I help?"

"Well, I've got this under control; I found everything I needed to make eggs benedict. I hope you like them."

"Love them. That's a nice treat. I'll set the table, and make coffee or tea if you'd like."

"Coffee is fine."

We got breakfast on the table and had an enjoyable meal. Lisa's hollandaise sauce was excellent, and the eggs were perfectly done. So, that was an indication she could cook. I'm a pretty good cook myself, but it was nice to find out she was, too. After chatting and goodbyes, Lisa left and I called Jan.

V. THE JAN SITUATION

"Hi Sean, how's your morning?"

"Good, I'm good. How about you?"

"I'm doing well, so do you have time to get together?"

"Yep, I'm free. Where did you want to meet?"

"How about meeting for lunch at the deli, say noonish?"

"Sounds good. I'll see you then."

When we met at the deli, Jan surprised me. She had her hair down and gathered in a loose ponytail. She was wearing a white, sleeveless blouse that did nothing to hide her large bosom, and was wearing snug fitting, robin's egg blue capri pants. She looked lovely. We met and she gave me a kiss on the cheek. Something she never did in the past.

"You look good, well rested. I was worried about you after the last few days at work," she started.

"You look great, and yes I'm doing better," I replied.

"Well, that's why I wanted to get together, to talk about things, about us."

"Us?" I thought, as they plated our sandwiches.

We paid and found a table away from others and sat.

"I know you were very uncomfortable with what we did, and I know you're concerned about what it means going forward."

"A little bit," I replied.

She smiled, "More than a little bit, I think...Sean, I want you to know that it was very special for me, helped me immensely. I don't just mean the um," she paused and looked around, then lowered her voice, "well what we did, and being with you, made me feel desirable again. But I wanted you to know, I don't have any designs on you...but that said..."

She sat silent for a moment, then, "Let's eat first, then talk."

"Okay."

After we finished eating, she suggested we go to the office for more privacy. It was only a few blocks away. After she unlocked and let us in, she suggested we go to my office. When we entered, she immediately wrapped me up and kissed me. Jan is a helluva kisser, too. I couldn't tell you who is better, Lisa or Jan. But I was surprised, caught off guard.

"Okay, I had to get that out of the way. Sean, I know we can't be...well, like boyfriend and girlfriend, but I hope we can be something."

"Well, Jan, I am seeing someone."

"Is it serious?"

"It could be."

"Hmm, okay...Well, I don't want to interfere with anything, but I want you to know how much I enjoyed the other night, and...I would like to do that again."

"Jan, I don't know...I mean..."

"Just sex, Sean, no commitments or anything. I know I have to find someone, but until I do...well, since my divorce I have felt very unloved, and the other night did wonders for how I feel about myself. And I can't stop thinking about it, about what we did."

"Jan, it was wonderful, but the thing is, the woman I'm seeing, well, we've been intimate, and I wouldn't feel right..."

"Do I know her?" she asked.

"I think so. Lisa, at the title company."

"The blonde?" she asked. I nodded. "She's beautiful, and she seems very nice," she commented.

"She is. And I don't know where we're headed. But she has expressed a desire for us to become more serious, and I wouldn't feel right, you know..."

"Yes, mm hmm, I see. Okay, I understand...but you slept with me the other night, so..."

"I hadn't progressed that far with her at that time, but this weekend...we became closer."

"Oh, so bad timing. Well, still, if things change, or if you feel like, you know, I'm here. And it would be our absolute secret."

I was uncomfortable with her suggestion. And yes, it was a tempting offer; Jan was a wonderful lover, but I knew I had made a commitment to Lisa, that I had indicated I wanted a relationship with her. This development with Jan was worrisome.

Monday morning came to soon, but when I arrived for work, Jan greeted me with a smile and a 'Good morning, Sean', acting like nothing had happened, last week, or on Sunday.

"Good morning, Jan. You look nice, today."

She did. Of course, she always does.

"Thank you."

She got up and followed me to my office and sat down.

"What's up, Sean?"

"What? Oh, um, didn't sleep well."

"Sean, I'm sorry about what I laid on you. Please forget about it. I'm fine. I'll be fine."

"I hope so. I want you to be happy, Jan. But right now, I can't be what you need."

"Well, please don't let that bother you. Of course, if you ever have a lonely night and..." she grinned.

"Stop it. You're too irresistible. I mean that, by the way. So..."

"I'll play nice," she smiled, and got up and left.

VI. BUSINESS

A minute later, she returned, "Oh, I almost forgot, I made you an appointment for one o'clock. A buyer looking for a ski chalet. You were recommended by a friend of his, a client of yours. The man wants you specifically, and is in town for today only."

"Okay, thanks."

I focused on my paperwork to get my mind off Jan, and to get caught up before the one o'clock appointment. I called Jan.

"Did he say where he was looking or specifically what he was looking for?"

"Oh sorry. Forgot to tell you. He's open. He didn't give a lot of details, just said he was interested a house near a ski resort, and was interested in your opinion and looking forward to meeting with you."

"Okay, thanks."

I pulled up listings for each of the major ski resorts in the Rockies and took a cursory look - there were a ton of them, ranging up to the 30-millions. I refreshed my memory on the differences between each facility and so on. Regardless, this was going to be a big-ticket purchase, so I wanted to be as prepared as I could. Without more input though - price, amenities and such, I could only do so much, but I prepared as well as possible.

When Gordon arrived, Jan called me and I went up front to meet him. He was a tall, handsome man, mid to late-forties, with a commanding presence.

After introductions, I asked how much time he had available.

"I'm yours for the rest of the day. I don't have to catch my flight till tomorrow. How much time do you have?"

"All afternoon. This is going to take some time. We have to discuss price range, amenities, what you're looking for in terms of ski slopes, accessibility, location and so on."

"Well then, let's get to it."

"Good. Well Gordon, at the major ski resorts, decent properties range from four million to the twenties and up, depending on how large a home you want, proximity to slopes, and of course, amenities."

"I don't need large. It will just be myself and my two children. I will need to accommodate a couple guests now and then, so I figure a five to six-bedroom home will be sufficient. It will be a vacation home, but I want it to be a 'home away from home', not a 'vacation cabin', condo or townhouse. I want a stand-alone home, preferably with some decent space around it. I don't want to be butted up against other homes. As far as access, I want a property that has a local airport, nearby. I don't want to drive from Colorado Springs or Denver every time I come up if I don't have to.

"Fine, that narrows the search down quite a bit. How about price range?" I asked.

"I'd like to stay under ten million, but that's not a hard ceiling."

"For the size home you're looking for, that's very doable."

We spent the next hour going over personal preferences, defining exactly what he wanted in amenities. I offered drinks and he asked for coffee. Jan made a couple cups and brought them in.

"Thank you...I'm sorry, I didn't get your name," Gordon said.

"Jan."

"Thank you for the coffee, Jan. That's a lovely outfit."

"Oh, thank you, sir."

"Gordon, please."

"Of course, Gordon, thank you."

After Jan left, Gordon commented, "Quite an attractive assistant you have."

"Yes, Jan is that, and amazing. She practically runs the place."

"Well, off the subject, and maybe inappropriate, but I have to ask, is she married? I didn't see a ring."

"No, she's recently divorced."

"Does she ski?"

"Yes, as a matter of fact."

Gordon, smiled and nodded, "Okay, sorry, where were we?"

"Well, I need a few days to review properties. When will you be available for showings, and how many properties will you have time to look at. They're going to be scattered about a bit."

"I'll be returning to Colorado Springs in three weeks. I'll be in meetings for two days, but after that I'm free for...say two days, maybe three if needed. And what I would like is for you to pick the two best options at the three best locations for me to look at. I will go with your judgement. Don and Sara said you have immaculate taste and great judgement, so I'm in your hands. As far as slopes go, I'm an intermediate skier and my children are advanced beginners."

"Got it. Well, three weeks will give me all the time I need, and I'll go ahead and block out the time for when you return."

We concluded business and I walked him to the door. He stopped and addressed Jan.

"It was a pleasure to meet you, Jan. Thank you for the coffee." He reached and shook her hand then turned to me.

"Sean, I'm looking forward to working with you and you finding me the right property. Call me if you have any further questions. Call the cell number at the bottom of my card."

After he left, Jan commented, "Wow, he seemed really nice. So what's the scoop?"

"He's looking for a place for him and his two children, in the ten mil. range."

"So he's loaded. And no missus?"

"Nope, he's single, lost his wife five years ago. And he was quite taken with you."

"No, really?"

"Yep, he even asked if you were single," I said, smiling.

Jan actually blushed a little, "You're kidding me, right?"

"No, scout's honor. And he'll be back in three weeks to look at properties."

At that moment, my cell rang and I headed back to my office.

"Hi, Lisa. I was going to call you tonight."

"Sorry, are you busy?"

"Nope, just finished with a client. How are you?"

"I'm good. Missing you. Can we get together this weekend?"

"Certainly. Did you have anything in mind that you wanted to do?"

"Another hike would be nice. I enjoyed that very much."

"I'll come up with some place nice to go. Do you want to get together for dinner on Friday?"

"Of course," she replied.

"I'll pick you up; what time?"

"I can be ready by six."

"Six it is."

For the rest of the week, my workload kept my mind off Jan, who really did seem nonplussed over everything; so I tabled that and focused on business. When Friday arrived, I remembered my dinner date with Lisa, and found myself excited and anxious to see her. It had been a while since I felt that way about someone.

VII. ON THE RIGHT TRAIL?

I picked up Lisa, and we went for steak dinner in town, had a great meal and a great time. Afterwards, we returned to Lisa's for drinks.

"Is wine okay?"

"Wine is fine."

She poured us glasses, and we went to her living room. She put on music, and invited me to sit on the sofa with her.

"That was a terrific meal."

"Yes, they know how to grill a filet," I replied.

"So, how was your week? You look a little tired."

"Do I? Yeah it was pretty busy, but I'm okay. How about you?"

"Oh, don't ask. If anything could go wrong it did. We got most of our escrows on track, but a couple are still being problematic. I'm just glad the week's over, and I'm looking forward to our hike tomorrow. I enjoyed that immensely."

"Yeah, me too. I hope you like where we're going tomorrow. It's a little more challenging, and off the beaten trail, so to speak."

"Sounds exciting."

We sat, drank wine, and chatted for a bit, then she pulled me up to dance. We wrapped up in each other's arms and moved to the music. I got lost in the moment, lost in Lisa's arms, her warm, firm body pressed against me. Eventually, we kissed, a long, tender, sensual kiss. I felt myself getting aroused.

"Make love to me," I heard her whisper.

I looked in her eyes, and the wanton, lustful look she gave me left no doubt. I picked her up and headed to her bedroom.

She giggled, "Take me, cave man!"

We undressed and I took in the sight of her, again. She is truly a beautiful woman, with her firm, sleek body, her high, mounded breasts, strong legs, narrow, flat stomach, and her world-class ass. My libido was immediately piqued.

"This time, let me pleasure you first," she said as she threw back the covers and directed me to lie down. I gladly submitted and stacked pillows against the headboard then lay back.

She grasped my erection in both diminutive hands, slipped her mouth over my cockhead and began giving me felatio. It took almost no time for her to get me rock hard. After a minute, she looked up.

I took the opportunity to pull her to me, engaging her in a passionate kiss, then I attacked her breasts, sucking and nibbling first one nipple, then the other, as she wrapped her hands around my head, mashing my face into her firm mounds.

She cooed, "I need you in me," and scooted down, finding my rigid cock and aiming it at her vagina.

"I'm wet, but this may be tricky," she remarked, and wet her fingers in her mouth and slathered my cockhead with her saliva.

Once she had moistened my head, she wet her fingers again and ran them through her lips. Then she pressed my cockhead against her vagina and worked it back and forth, gradually working past her vaginal opening till my cockhead slipped in. She shuddered and paused.

"Damn, that thing is big. Don't move. Give me a second...Ungh, mmm, okay, mmm, okay, there we go," she continued as she gradually sunk down, enveloping my cock in her tight tunnel.

Then she started slowly scissoring her powerful legs, riding my hard pole. I watched, mesmerized by the sight of her vagina sliding up and down my cock, her delicate, distended lips sliding up my shaft, then disappearing as she slid back down. She leaned forward a little and braced herself with her hands on my chest and kept rocking up and down. After a couple minutes, she removed one hand and began jilling herself as she slowly rode me, eyes closed, head bent forward. I reached up and gently fondled her breasts and started tweaking and rolling her nipples. She nodded and began rocking faster as her face and chest started to flush with excitement. She was close.

"Mmm, baby, almost there...get ready to take over...I...I...I'm ready," she squeaked out and stopped rocking, suspended over me, with just my cockhead ensconced in her vagina.

I grabbed her hips and started thrusting up, firmly coming up against her cervix, but not pounding her, yet. She was nodding and jilling herself more intensely as I continued stroking up and down.

"Um, mm hmm, almost, almost...go faster...mm hmm, harder...yes, yes, almost, oh, oh...OH YES, CUMMING..."

I started hammering for all I was worth as she jilled like crazy. Then she fell forward on me and started spasming, cumming hard, clamping down on my cock. I buried it in her and held onto her hips as she jinked and convulsed in a wicked orgasm. When she calmed down, she sat up, face and chest flushed red.

"Whew, that was a righteous climax," she exclaimed, blowing out a breath and laughing.

"You didn't cum, did you?" she observed.

"Huh uh. I was too busy enjoying watching you."

She grinned, "Well we can't have that. What do you want me to do? Use me however you want," she said, lustily.

"Okay, turn over," I directed.

"Oh, doggy," she grinned.

"Sort of," I corrected, then explained, "Here, put this pillow under your hips and lie flat with your legs slightly apart."

"Oh, okay. This is new," she giggled and lay down with a pillow under her.

I straddled her legs and took my swollen, slick member and ran it up and down the cleft of her buttocks, rubbing it against her pucker each time.

"You're not going to try..." she started to exclaim.

"No, no. Just a little stimulation. Relax."

"Okay, I was afraid you were going to try to get that beast in my butt," she laughed nervously.

I worked the head down till I found her slippery wet opening and slowly pushed in.

"Bring your legs together now." I instructed.

"Oh, that feels nice," she replied as I slid all the way in till my groin was mashed up against her tight buttocks.

As soon as I got a good rhythm going I wet my thumb in my mouth then pressed it against her pucker and gradually worked it in.

"Oh, shit!" she exclaimed.

"Okay?" I asked.

"Oh, yes, just wasn't ready, but feels good. Oh fuck, this is nice."

I set up a steady rhythm, firm and slow, then gradually picked up speed, working on bringing myself off. Slapping against her fine ass was having the desired effect. But I knew it was going to take me some time to get off at this point, and I needed a little extra impetus.

"Talk to me, Lisa."

"What? Oh, okay...Sean, I love your big, fucking cock in my tight, little pussy...ungh shit, oh I think you can make me cum again...and your thumb in my butt. That's so naughty. But I'm a naughty little girl and I love you fucking me. Pound me baby...ungh, yes, aghh, fuck...yes, yes...make me cum again. Fill my little cunt up with your...ungh, gonna cum...fill my cunt up with your semen, baby...ah, ah, ah...I'm close, close! Come on, punish me with that, ugh, big fucking cock! Yes, yes, now, oh, oh, oh, GONNA CUM, AH-AH-AH-AHHH!