Five Dates Ch. 06

She nodded and pushed my boxers slowly down, inching them down my hips and over my butt, delaying exposing my cock. She finally pushed them down enough to free my hardon, leaving them around my thighs, which was as far as she could reach. She let her hands clasp around my hard shaft and then stood there, as if waiting for something.

"What now?" she whispered.

I stepped back to the sofa and sat down, pushing my boxers down to my ankles as I did. I held a hand out for her and drew her to me. It took a moment to coax her onto the sofa, facing me, her knees splayed on either side of my hips. I pulled her chest to my face and gently kissed her right breast and nipple. I worked to kiss across her chest to the left, and then kissed around the hard little button before opening my mouth and drawing the whole front of her breast into my mouth.

"Oh my," she whispered as I teased her nipple and areola with my tongue. She moaned softly as I switched to her right nipple and sucked it in as well. If she hadn't been with a man in that many years, she clearly wasn't going to be ready for a quick fuck. No, I was going to have to take my time. I let my hands slide up and down her back, working slowly down further until I was stroking under her firm little butt cheeks. I continued to suck and kiss her nipples and breasts as I let my fingers tease down under her and find her lips. She had a small amount of inner labia sticking out of her firm, round, outer lips. I stroked my fingers back and forth across them until I could feel them growing wetter at my touch.

"You sure?" I asked softly, breaking the kiss and looking up at her.

"No, but yes."

I nodded and shifted my hands to grasp the inside of her thighs. I gently coaxed her back from me slightly, leaving her kneeling with her knees almost against the outside of my thighs. I pulled her thighs, spreading her knees apart and lowering her pussy toward my hard dick as she pushed them apart. I felt my head brush her lips and shifted my right hand to guide me to her lips. "Ohhhhhh fuck," she moaned softly as I stroked my head between her lips and across her hard little clit. She spread her knees further of her own accord, lowering herself down until my head was pushing slightly into her. She felt the pressure on her vaginal entrance and lowered further, allowing my mushroom head to spread her body and push up into her slightly.

I lifted my arms up to her back and pulled her tightly to me, leaving my head stuck in her about two inches. I rolled us to the side, laying her on the sofa mostly on her back, but partly on her side, with me lying in front of her with my legs between hers. I slid my left hand down to her firm butt and pulled her toward me, forcing my dick slowly into her pussy. I let her body expand around me as I worked my hips slightly, pushing in and out of her only an inch or so to work her moisture out to lubricate her lips and my shaft as I worked deeper into her.

"Ohmygod," she whispered as my fat shaft pushed almost all the way into her, the end of her vagina pressing against my head. I started to rock slowly, sliding my dick in and out of her, working ever so slowly several inches of my shaft in and out of her depths. I shifted my left hand, no longer needed on her butt, to between her legs. She felt my fingers and lifted one leg in the air, allowing me to stroke my fingers from where my dick stuck in her to the end of her slit and her hard clit it hid. In and out I stroked while I worked my finger across and around her clit.

The reaction of her body was all I needed to know how much I was pleasing her. Her hips started to rock in time with my strokes and she was helping push herself faster onto my shaft. In only a few short minutes she was humping wildly toward me as I pumped my shaft just as wildly in and out of her. "Oh god. Ohhhhhh god. Ohhhhhhhh god I'm gonna come," she moaned loudly as we pumped against each other, my finger driving her even more wild.

Her body suddenly stiffened and I could feel her pussy climaxing around me. I continued to stroke and tease her clit as I worked my shaft more slowly in and out of her now spasming pussy. She groaned deeply as her pussy eased its grip on me, her eyes open once again to look at me.

"You haven't yet, have you?"

"Not yet," I said softly, still stroking my hardon in and out of her.

"Do you want to?"

"Oh yeah."

"In me?"

"I don't know, should we?"

"I haven't in a long time," she whispered. "I'd kind of like to feel it again."

"Is it safe?"

"No. As horny as I am today, I'm either ovulating or close to it. But it can be, if you want it to be."

"Then relax and let me give you that feeling again," I whispered as I started to stroke into her harder again. I pumped more quickly, driving my dick hard into her with each stroke, feeling her pussy clench around me periodically as her climax was teased into renewal again. I groaned deeply and felt my body buck hard, driving my dick into her and pumping a gush of cum into her depths. I lay there, panting and jerking as I emptied my balls into her hot, wet vagina, listening to her moan and sigh softly.

"I'd forgotten just how special that can feel." she whispered as she tried to pull us together more to keep my softening dick from slipping out of her. Unfortunately, it eventually did, letting a drool of our combined cum leak onto her thigh and the sofa. She leaned her face to mine and kissed me softly. "I have to say, you did a very good job of making me feel like a woman."

"Thank you."

"No. I don't think you understand. Thank you!" she said with a smile. "If I happened to show up in your office, naked, some morning. Would you take me like this again?"

"Nope. I'd lick your pussy until I made you come, and then I'd fuck you like this."

She smiled and giggled. "I might have to try it, just to see if you really would."

"I would."

"I suppose we should clean up and get back to work."

"We should," I agreed.

We disengaged from each other. I stood and pulled my boxers and pants up while she sorted out her clothes. She was about to pull her panties on when I stopped her. I took her underwear from her and her bra and tossed both at the trash can by her desk. "But I need those."

"No, you don't. What you need is something much less grandma and much more hot, sexy woman," I said. "And if you need help picking, just let me know. I'm an expert."

She grinned and collected her dress. She stepped into it as I put my shirt back on and after I buttoned and tucked my shirt in, I zipped her up. I was about to put my tie on when she reached out and took it from me. "I'll keep this as a souvenir," she said quietly.

"If you want."

"I do."

I nodded, stepped against her and wrapped my arms around her. I pressed her lips to hers in a soft kiss.

"A good bye kiss?" she asked softly.

"I think if you're close enough to fuck, you're close enough to share a kiss. Not goodbye, but maybe later?"

She grinned and kissed me back. She broke the kiss after at least two minutes. "Um. Wow," she whispered. "You can kiss too. I'm so wet I think I might have to have you again." I chuckled in reply. "Um. One more thing."

"Yeah?"

"Well, two actually. Can we keep this on the down-low? I have a reputation to keep up."

"As the frigid bitch?" I asked with a chuckle. "I'm not sure how well it's actually deserved now, but yeah. I can." I grinned. "And the second?"

"Elizabeth. Don't say you don't know what I mean. I heard her in the ladies room telling a friend that she was falling in love with you. I know what she went through with her ex husband. I don't want to see her hurt again."

"I don't want to hurt her."

"Good. If you two need a few days to go off somewhere and sort out your relationship, you both have plenty of vacation. I think maybe you two owe it to yourselves to figure things out before they go to far."

"You care about her?" I said in surprise.

"I do. I'd known for years how she was being treated. I tried to get her to get out of the relationship and she finally did get out. I don't want to see her get hurt like that again."

I leaned down and kissed her. "Hardass, my ass," I whispered with a grin. I let go of her and headed to the office door. I walked out and the three girls, including Julia, were trying to look down and look like they were working, but I could see them trying to hide the smiles as I walked past.

I headed back to my office, having expected to make the trip no longer having a job, and now feeling just the opposite. The frigid bitch was actually a pretty sensitive woman. I walked past Darleen, who got up and followed me into the office, closing the door behind us.

"So?"

I settled in my chair and looked over my desk at her. "How much do you and Julia talk?" She looked at the floor and paused before admitting that they were actually fairly good friends here at work. "So she knows about the five dates thing my wife requested of me?"

"Yeah."

"Who else have you told?"

"Not too many people. Lizzy of course knows. She caught me in the ladies room one day and quizzed me until I finally told her all the details I know."

"Who else was there?"

"I don't know. Why?"

"Could there have been someone in one of the stalls?"

"I suppose, but why?"

"Because I just had the most interesting meeting with the head of HR. Seems she's heard about you and me, and me and Liz and I don't know how many other women who have expressed an interest in getting into my pants. In addition, she knew about Julia. Apparently, she called Julia into her office and she spun some yarn about my wife making a last request of me to have sex with thirty women I know in four months."

"Ohmygod," she mumbled as she sat in the chair across from me. She looked up at me. "What happened?"

I sat and stared at her for almost a full minute, making her squirm in her seat, probably dreading the worst. "I didn't get fired. I got propositioned."

"Propositioned!?" she exclaimed in surprise. "By the ice bitch?"

"By the ice bitch. She wanted to be included in that thirty-count. She wanted me to do to her what she understood I've shared with you, here in my office."

"So? What did you do?"

Again I sat quietly, watching her watch me. "At first, I said no. After we talked some more, I agreed to have sex with her. No one can know. She's not going to take any action against either of us for our illicit relationship, at least for now. She's also not going to investigate any reports she gets about me having sex with other women in the company during company time or on company premises. She admitted that she's been alone for seven years and wishes her husband had made some similar kind of request of her to force her to move on with her life, which she apparently feels she hasn't done. While what we did was not tied to any of this, she wanted me to know that she was going to support my attempts to meet my wife's final wish. The only problem is, that wasn't her final wish. So now I'm stuck with the five dates issue AND fucking thirty different women in the next couple months."

"That doesn't sound like a bad problem to have," she said with a grin. "I can get a line started out here if you want."

"That's not funny."

The smile disappeared from her face. "No, I suppose it's not."

"The whole idea of the dates was my wife wanted me to realize that I could still feel things for other women and that doing that wasn't cheating on her or her memory. How am I supposed to work on relationships if I'm fucking every pussy that walks in my door?"

"Well, at least you'll get plenty of practice," she said, trying to grin again, and failing when she saw the serious look on my face.

"I feel like I'm painted in a corner. If I don't try to follow through she might get the idea that she'd been had, and that could cost me my job. If I do, I might damage the one relationship here that I think might have some potential."

"Lizzy?"

"Lizzy," I agreed. "I need to talk to her."

"I can look at her schedule online and see when she has time."

"Do that. Set something up for this afternoon if you can. A private meeting in my office. I gotta let her know what's happening."

"Okay. I'll take care of it. I'll make it look like a business meeting."

"Thanks. Now scat. I need to think," I said, logging myself back into my computer. I sat for a long time, staring at the screen, trying to figure out what I was going to do. Having sex with other women wasn't a big deal. I'd had enough sex with enough women already in the last few weeks that I could do that without feeling too guilty, unless of course what I was feeling for Lizzy was real. Rose brought up a good point. Was what I felt love for her, or love for what she represented? I logged into my banking app and checked my account. I stared at the screen in dismay. It took me a few moments before I picked up the phone and dialed a number I'd long since memorized.

'Hello Michael.'

"Hey Trish. How are you this morning?"

'I'm doing alright,' she answered quietly, even though she didn't exactly sound alright.

"What's wrong?"

'Who said anything was wrong?'

"I know you. What's wrong?"

'Nothing I want to talk about. You wanted something, or you wouldn't have called.'

"Alright. Down to business. Because that's what this is, a business call. My bank account. It has too much money in it."

'How do you figure?'

"I've done two dates. But I can see four ten thousand dollar deposits."

'That's right. I'm bending the rules a little on how far apart the dates should be. But I count four.'

"How do you figure?"

'Well, our first date, that was one. The overnight you spent with Donna going to the club. Yes I know about that. I asked her. The overnight date before going to the river. Yes, I know about that too, and also about what you told her after. I've had to keep up on what you're doing to tell the lawyer.'

"Even so, that's three. Not that I care about the money. I just want to know what you think was four dates."

'Number four was last night. True it was only pizza at your house, but you clearly enjoyed it and you did have sex and she did spend the night. So it counts as a date in my book.'

"Wait. You know about Rose? How?"

'I couldn't count on you to tell me everything. You'd be afraid you were hurting my feelings. So I installed a nanny cam I can access. It shows me your living room when there's motion. And there was plenty of it last evening.'

"Oh shit Trish."

'It's alright. I could tell by how often you didn't call that, well, I wasn't going to be the one to fill that space.'

"And you figured that out on your own?"

'Oh god Michael. Didn't you pay any attention to how you looked with that woman last night? Rose, you said? You didn't have sex with that woman. You made love to her like you made love to me. You could see the connection in both your faces.'

"You're wrong. I just met her yesterday. I helped her change her tire and she came over to have pizza with me. We're just friends."

'If you want to tell yourself that, that's your business. But it looked a lot more intimate to me than that. Especially when she asked you to come in her.'

"You could hear what we said?"

'Of course. Nanny cams let you hear when the baby is awake.'

"So you also heard what we talked about?"

'Yes. I did,' she whispered. 'It's alright. I know I was a long shot anyway. But I can understand how you feel. My problem is I look too much like my sister. At least I got a chance to have you love me for a while.'

"Trish. I don't know that it's over between us. Not that way. I'm still trying to figure out what I feel about who."

'Which is why I haven't completely given up, and if you call and want me to be there, I will be. But I'm just preparing myself for what I expect to happen. The sooner we get the five dates over with the sooner I can stop trying to keep track of your sex life. It'd be best for both of us if I wasn't, if I didn't know about every woman you make love to.'

"You're right. It would be better. I appreciate that."

'I presume your planning another date? A longer one if you're looking at how much you have in the bank.'

"I am. I want to try and sort out what I feel for Liz. I don't want to lead her on if she isn't. If I'm not. If we aren't."

'I understand. You don't have to explain. Just let me know when you'll be gone so I can have him do the final one and then release the rest of the money to you.'

"Trish I don't give a shit about the money!"

'I know. But the sooner I get this over with the better off we'll be. Have a good trip Michael. You know where to find me if you want me,' she said before hanging up.

I sat staring at the phone. I'd planned on having a talk with her about it all and trying to let her down easy, but instead she got it the hard way, hearing me explain my feelings to Rose. But her comments about Rose? That I had feelings for her? We were just passing friends sharing a little sex. Did it feel good? Oh yeah. But feelings for her? I didn't know much about her. But then when I started with Donna I didn't know much either and look how that turned out. Sometimes life was just too complicated.

I was browsing the web thinking about what kind of a trip to take Liz on when Mark walked in. "Hey boss. How's it going? I heard some rumor that you got called down to the ice queens palace."

"Yeah, I did."

"Hope it wasn't too bad. I've heard stories of her unloading on guys for the smallest infraction."

"Yeah, she found out about me having sex in my office."

"Ouch. That must have been awkward. But you're still here. Just a reprimand?"

"Something like that," I answered.

"Well, that's something anyway. So, you coming to dinner tonight? Lulu asked me to check and see if you were bringing a date or not."

"I haven't had time to think about it."

"Well, she said she'd love to have you over, just you if you're feeling up to it. She hasn't had a chance to spend any time with you since, well, since the funeral."

"Yeah. I can come." I nodded with a deep sigh. "She probably wants to quiz me on my social life."

"And who you were banging in your office," he said quietly with a chuckle. "She keeps asking me if I know and I keep telling her that she's gonna have to get it out of you because I don't have a clue."

"What if I don't want to tell her?"

"Lulu?" he asked with a laugh. "You think you can outlast her trying to find out? Good luck with that. I never have been able to."

"I'll be ready to repel borders then," I answered with a smile. I'd been on the hot seat with her once before and she could resort to some very, um, stimulating, methods of getting information out of me. So much so that I had to give in before my wife found out just how far she had already gone and lord knew how far she might have gone. She seemed to be from the same school as Darleen: fuck a man until he tells you what you want to know. I doubted it would go that far in front of her husband, but hell, I wouldn't put it past her to tease the shit out of me to get me to talk.

"See you after work then," he said before turning and heading back out of the office.

I wasn't very productive all morning. I spent most of it trying to figure out where to take Liz. I wanted it to be somewhere where we could have sex when we wanted, how we wanted, but still have things we could do. We needed to share some experiences and spend a lot of time talking to each other, in private. This was only going to work if we could both open up about our past relationships and what we wanted for ourselves for the future. I thought Rose was on to something about me being more in love with what the relationship meant than the person herself. I owed it to both of us to be able to find that out.