Five Dates Ch. 05

I could feel her hand coaxing me closer and closer to climax as I watched her face and body respond to her own ministrations. In and out the pink dildo moved, making me imagine that it was my dick sliding in and out of that incredibly sexy pussy. I tried to hold my hips still as the urgency built inside me, the warmth and tingle radiating out from her hand as she rubbed it over my engorged mushroom head.

"Oh god. I'm going to come," she moaned, her strokes on my shaft growing slightly irregular. She looked up at me, looking right into my eyes as she stiffened and shuddered. I let go of her breast with my right hand and reached down between her legs. I stroked my finger up and down her lips a couple times and then pressed the tip of my finger between them. I felt her hot wetness as I searched out her clit and found it. "OH FUCK!" she squealed in surprise as I stroked the tip of my finger back and forth across the hard little nub. She held my dick with almost a death grip as she pushed her hips up toward me, her whole body jerking as she tried to push her pussy to me.

I continued to stroke up and down across her clit as she closed her eyes and moaned loudly. "Ohhhhh god damn!" she gasped as she slowly lowered her butt back to the sofa, pulling it away from my stroking finger. "Ohhhhhhhh god that was intense."

"Glad you enjoyed it," I said as her now-eased grip allowed her to start stroking me again, this time looking at my dick. She pulled the dildo from her pussy and rubbed her fingers up and down her sopping wet lips a few times before reaching for my dick with it. She rubbed her fingers around my engorged head, lubricating me with her own juices before she wrapped both hands around me and went back to stroking it, aiming it right at her face as she stroked me.

"You know. I've often gone shoe shopping without any panties, teasing the shoe sales guys. Sometimes I sit in the car after and play with my pussy and imagine that they stand in front of me and let me jack them off like this, coming all over my face and tits. Come for me. Come all over me, please?" she asked quietly, staring at my dick rather than my face.

I didn't have to say anything, I was so close already that I was going to be shooting all over her in a few moments anyway. She must have felt my cock swell, and she leaned closer to me, putting her feet on the floor with one leg on either side of mine. "Uh!" I grunted as my body spasmed and the first shot of cum lanced out of my head and splattered on her face. Two, three, four, five powerful shots rained on her face and upper chest before my cock reduced to drools of cum dripping out the tip. She leaned closer to me and let my dick leak onto her tits, trying to pull me down toward them. I squatted down slightly and let her rub the tip of my head around her nipples, smearing the remaining cum leaking from me around her nipples and areola. She squeezed and milked the last of my cum out onto her tits before letting go of me and leaning back.

"You might not believe this, but that's the first time a man has ever come on my body. My husband wouldn't, he said it was dirty. I know we just met, but thank you. I always wondered what it would feel like," she said as she leaned to get one of the towels she had brought out and started to wipe my cum from her face and chest.

"You're welcome. Thank you for sharing your climax with me."

"I wasn't expecting you to touch me, just watch, but it was so, so, oh damn. It felt so good to have you touch me."

"It was a lot nicer getting you to do it than if I'd have done it myself."

"I suppose you have to do that a lot? Do it yourself?" she asked as I turned and sat down hard on the sofa next to her. My mind suddenly filled with thoughts of Donna. "I'm sorry. Painful memories?" she asked, twisting to look at me, her bare leg pressing against mine.

"Actually, no. That thing with my wife making me date? Well, I met someone. We had a lot of sex. The only problem was that she wants to have sex with lots of men and I just don't know how to handle that. I've always been a one-woman man, and expected her to be the same."

"You care for this woman?"

"A lot more than I want to admit."

"I'm sorry," she said, twisting even more next to me. She reached out and wrapped her arms around my shoulders, pulling me sideways toward her a bit until she could hug me against her. I felt her soft tits pressing into my arm and felt her lean her head toward mine before giving me a soft kiss on the cheek. "I didn't mean to make things painful," she whispered softy as she held me.

"It's alright. It's my problem, not yours. Your problem is a flat tire. I guess we should finish fixing that," I said, forcing myself to straighten up in her grasp.

She let go of me but continued to sit twisted to look at me. "I get the feeling you're a very sweet and caring man. I hope you find what your wife hoped you would," she whispered, still not moving away from me.

"I do too, but it seems like I have feelings for the wrong sorts of women."

"Women plural? More than just the one?"

I chuckled. "For a one-woman man, somehow I've gotten myself tangled up with three."

"And you have feelings for all three?" she asked in surprise.

"Yeah."

"You do have a problem. That's not fair, I'm sorry. Sometimes trauma in our lives can lead us to find things that aren't really there." I looked at her curiously. "What are the chances of falling in love with three women at the same time?" she asked me with a serious look on her face.

"Nonexistent, or at least I thought so."

"Maybe it isn't love so much as desire to have that connection you had with your wife. If you miss it that much, maybe it's coming out as what you think of as love for these other women."

"You aren't a shrink or something, are you?"

"Me? No. I'm just a receptionist. I've just had the chance to overhear a lot of really good conversations with people that have had the kind of loss you have." I looked at her curiously. She chuckled softly. "My boss is a shrink."

"Ahhhh," I answered with a nod. "That makes sense I guess. What does he think of your little game you play?"

"She. And she thinks that it's a healthy way for me to express my desires."

"Maybe it is. Healthier than what I'm doing."

"Tell you what. Let me put some clothes on and we can go finish fixing my tire and maybe we can talk a bit more?"

"Analyze me?"

"No. I'd like to think maybe more of a dispassionate observation? Maybe even friendship? You sound like you could use one."

"I think I could. So far all the friends I've been leaning on through this are trying to get into my pants."

She looked at me, surprised, and chucked a soft feminine chuckle. "I think this is going to be an interesting conversation." She pushed herself up and walked to the kitchen and picked up her discarded clothing. She walked to her bedroom and came out a few moments later while I was still putting my shirt back on. She was wearing a tank top and a pair of shorts instead of the skirt she wore to the store, though I was pretty sure she hadn't put a bra on under the shirt.

We walked out the door of her apartment together and headed down to my truck. It didn't take long to get the tire filled and head back to the store. I had to park in the middle of the aisle to work on her car, but I got it taken care of in only a few short minutes, most of those minutes spend with her squatting like she had before, unfortunately no longer showing me her pussy.

"So, I interrupted your shopping. Would you mind if I helped you do yours?"

"I'm just getting a few things," I said with a shrug.

"Still wouldn't mind."

"If you want," I accepted. I parked the truck and walked into the store with her. It only took a few minutest to get what I wanted.

"Looks like depression food," she said, reaching around my waist to hug me sideways to her. "I suppose dinner was some kind of carry out? Pizza maybe?"

"Actually, yes."

"Want some company for dinner?"

"You want to be around someone that's depressed?"

"For someone who's depressed, you do a good job of hiding it."

"Lots of practice in the last few months."

"I'm still game."

"Alright," I agreed. I gave her my address and said I'd pick up the pizza on the way home. She of course beat me to the house and was sitting in the driveway when I got there. I parked in the garage and invited her inside. She wandered around the house oohing and ahhing the work I'd put in over the years. We sat next to each other on the sofa, eating pizza and drinking beer while I explained about the five dates and about Trish, Lizzy and Darleen. I finally explained about Donna, which seemed to be the hardest. It was good to be able to talk about it to someone that I wasn't emotionally invested in.

"I think your wife put you in a very hard position," she finally said. "Your sister-in-law being in love with you makes things even harder. You may actually have feelings for her, but I'm willing to bet that what you feel for her is more about what you felt for your wife, because they look so much alike. Let me guess: when you're in bed with her you frequently dream about your wife?"

"Yeah, a lot."

"Relationships with sisters after a loss happen, but they are usually not what they seem."

"This happens a lot?"

"More than one would think. A sister and husband help each other through the loss and end up in love with each other. They generally don't end well down the road."

"I had someone else tell me something similar. Same person that said that Donna and wouldn't ever work out for me."

"Sounds like she was probably right. If you can't get past what she does, how do you not feel betrayed when she has sex with other guys?"

"I don't think you can."

"That's right. You need a woman that is a one-man woman."

"Well, Trish is. Darleen is. I think Lizzy is."

"True. But do you love them, or do you love what you think they bring to you? Contentment, commitment, stability, companionship and most of all, intimacy, not sex, but emotional intimacy?"

"How the hell am I supposed to figure that out?"

She laughed. "If you figure it out, let me know and we can both be rich!"

"That doesn't help."

Her face turned serious. "No, it doesn't. What I can tell you is you should take your time. Don't jump on something too fast. You might regret it later."

"From experience?"

"Me? No way. I haven't even made it to date one yet," she said with a laugh. "No, that is what my boss would tell you. She's pretty smart about relationship stuff."

"Seems like you are too, even though you're wrong."

"Wrong? About what?" she asked, looking at me curiously.

"Not having made it to date one yet."

"But I haven't."

"Yeah you have. Pizza and beer with a guy counts as a date, even if I didn't get you drunk enough to get your clothes off."

She blushed. "You didn't need to before. You think you need to get me drunk to get my clothes off now?"

"I don't know. If I asked, would you take your clothes off again?"

She sat quietly for a few moments. "I might, if you asked right."

I thought about it for a few seconds and then stood up and held my hand out for her. She took my hand and stood up as I gently pulled on it. I stepped toward her and wrapped my arms around her waist and pulled her gently against me. I moved my face toward hers, giving her plenty of time to object. She didn't. She tilted her head to the side and closed her eyes, waiting for my lips to touch hers. It was a gentle brush at first, just letting our lips touch before we each pressed ourselves more firmly together. Not just our lips, but our bodies. We stood there for I don't know how long, softly kissing each other, teasing each other's lips and tongues before I moved my hands to her waist. I pushed her shorts down slowly, inching them down over her butt, again giving her plenty of time to object. She didn't. Her shorts slid down her legs and I felt her step out of them. I could tell by the bareness of her butt that she hadn't chosen to wear underwear.

I moved my hands back to her waist and slowly started to drag her shirt up her body, peeling the snug tank top up her stomach and then over her big, soft tits. She lifted her arms and moved her face from mine only long enough for me to pull the shirt up over her head and arms, and then her arms circled me again and her lips returned to mine. This time she didn't kiss though, she just held them there, breathing with me, letting our breath mix with each other as our lips almost brushed each other.

"I can't have sex with you," she whispered so softly that I almost didn't hear it.

"I know," I whispered back.

"I want to," she whispered, even softer.

"So do I."

"If I take your clothes off, can I trust you not to?"

"Do you want to? Trust me?"

"Yes," she whispered, her lips brushing mine again. "Very much."

"What if you change your mind?"

"Don't let me?"

"I don't think I can do that. What I can promise is that I won't do anything you don't tell me I can do."

"I guess that'll have to do, because I want to feel your body against mine, without clothes on. I want to feel your mouth on my nipples and want to feel your strong arms around me when I climax."

"What would your boss say?"

"That I'm being impulsive. That I'm not thinking things through. That I'm putting myself in a compromising situation. I don't care. I want it."

"Then do it. I'll stand here and let you do what you want."

She stepped back slightly, only far enough to get her hands between us. Button by button she undid my shirt and then pulled it out of my pants to reach the last two buttons. She pushed the shirt off my shoulders and I let it slide down my arms as she pressed her bare breasts to my now bare chest. I felt her hands work between us, finding my belt and undoing it and then the front of my pants. My dress slacks slid down my legs and her hands moved to my hips. She hooked her fingers in the waist of my boxers and then paused, almost as if she were considering not going further. I stood there, not touching her, feeling her heavy breathing against my lips. She began to slowly push the waistband down. She pushed as far as her arms would allow and then she slid down my body, pushing them down as she dragged her hard nipples down my chest. I felt my hardon press between her soft tits as she pushed her body against mine and continued to squat down, my hardon finally stroking across her face.

She moved her hands to my shoes and untied them, not moving her face away from where my hardon now rested against her cheek. One foot at a time she took my shoes and socks off and worked my pants off, leaving me completely naked in front of her for the first time. She looked up at me as she reached for my hardon with one hand. She grasped it in her hand and, looking up at me, pulled her head back enough to move her face in front of my dick. She opened her mouth and closed her eyes as she closed her lips around my head. I felt her hot mouth engulf me, her tongue teasing tentatively around my head as she seemed to explore my mushroom head with it.

I groaned softly as she licked and toyed with my head in her mouth, her eyes now open and looking up at me almost as if looking for approval. I suddenly realized that was exactly what she wanted. Approval that what she was doing was good. I wondered if her husband ever had her do this to him and guessed he didn't. I moved my hands to her short-cropped blond hair and gently stroked it. "God that feels good," I said softly, drawing a smile from her around my hard shaft. I let her lick and suck on me for several more minutes, her strokes on my shaft growing longer as she became more confident of her actions. I let my hands leave her head and leaned down, reaching for her arms.

I gently gripped her arms and coaxed her back, pulling her face off my dick. I gently pushed her back until she could no longer balance on her high heels. She fell back heavily onto her butt, but I held her arms firmly enough to keep her from falling backwards. I knelt down in front of her, easing her back until she lay flat on the carpet. I lifted her left foot, slipped off her high heel and gently set it aside before kissing her calf, planting several soft kisses on her leg below her knee. I moved her calf to rest on my shoulder and then lifted her right leg. I removed that shoe as well and gently kissed her leg below the knee. This time though, I continued up her leg, kissing inch by inch up the inside of her thigh, spreading her legs and leaning over further until I was kissing inches from her glistening pussy lips. I turned my head and gently kissed her lips, tasting her wetness and excitement, drawing a long deep moan from her.

It didn't take long for me to work my tongue between her lips and start to tease up and down the length of her slit. She was incredibly excited and tried to use her legs to lift herself toward me. I gently moved her legs further apart, letting her put her feet on the floor, opening her pussy lips further for me while also allowing her to lift her pussy toward my face. I licked and teased and searched with my tongue for her clit. I felt her jerk and heard her gasp as my tongue flicked over her hard clit the first time. I concentrated on her hard nub, teasing it with the tip of my tongue as I worked a finger into her hot depths. I pushed it deep, curling up behind her pubic bone, searching for that sensitive spot I knew most women had.

"Oh fuck!" she gasped as I stroked my finger across it the first time. I smiled to myself and stroked and licked her clit while fingering her pussy, her hips lifting and pushing toward me as she moaned and panted about how good it felt. Her hips lifted and lowered as her moans grew louder. I knew I had her close to climax but I wasn't sure if I wanted her to climax yet. I knew what I wanted and where I wanted to be. I also knew that if I asked her now she'd say yes. I closed my eyes and steeled myself for the disappointment I knew I'd feel, but it was my choice.

I shifted my finger slighty, pushing deeper and drawing an even louder moan from her as I concentrated my tongue all the more on her hard clit.

"OH FUCK!" she screamed into the room as I pushed her over the edge, coaxing her orgasm to the very pinnacle of her climax. I could feel her pussy leaking around my finger and smell her excitement as her pussy clenched around it. Her whole body shook and trembled in orgasm. She reached down with her hands and tried to pull my head from between her legs. I knew what she wanted.

I pulled my face and my fingers from her pussy and began to kiss my way up her shaved mound, feeling the little bit of soft stubble there with my lips. I kissed up her stomach, her legs loosely wrapping around my body as my kisses tickled her soft stomach. I found the bottom of her right breast and began to kiss it softly, working around it as I slid my body up hers further. I felt my engorged head press against her wet lips. I so wanted to just push forward and force myself into her hot wet depths, but I held back, just holding my head against her lips. I kissed around her breast until I had made my way to her puckered areola and hard nipple. I sucked it into my mouth and teased it with my tongue, flicking over and around it.

She moaned loudly and then I felt her legs shift. She dug her heels into my butt and tried to pull me toward her. I could feel my head spreading her lips, the one thing she had asked me not to do.

"Fuck me. Put it in and fuck me, please. Just don't come inside me. I want to feel you in me."

I let her pull me deeper, my head spreading her lips apart and her body stretching around my girth. I felt my hard shaft push slowly into her as she moved her legs to plant her feet on the carpet. She used her feet for leverage to lift and lower her butt off the carpet, working my dick an inch or two in and out of her pussy and pulling herself toward me until she had me fully inside her.