Five Dates Ch. 08

The sun was up when I woke, finding the bed empty. I sat up and rubbed the sleep from my eyes and looked around, finding Liz sitting on a lounge chair on the little deck overlooking the ocean. She was sitting, just staring out at the ocean. She must have heard me stir and looked over to see me. She smiled and came back to bed, crawling in and pushing me back to lie down again. She snuggled up next to me, her body pressing to mine and her head resting on my shoulder.

"Just let me lie here like this a while," she whispered. "I don't know how many more times I'll be able to do this."

I hugged her tightly to me and twisted my head to kiss her forehead. "Why? You think I'm going to stop wanting to hold you like this?"

"When you find out about me, probably," she whispered.

"Okay, so tell me."

"I'd rather not. Not until I have to."

"And when is that going to be?"

She looked up at me. "When you make me."

"Why? Why is this making you so scared?"

"Because I've had a chance to see what it's like for someone to care for me, to see me as a person and care about what I feel and what I want. I don't really wanna lose that now."

"And you think you will because?"

"Of my past."

"You already told me about your abusive ex and your daughter. Unless you're a serial killer or something I don't see a problem," I finished with a chuckle.

She looked at me seriously and I stopped laughing. "It's not funny," she whispered. "I haven't ever told anybody. Not even my best friends know. I've told so many people my fake story that it's almost like telling the truth, but as bad as it is, reality is a lot worse."

"Okay, so tell me."

"I don't know if I can."

"Look, this trip is about learning about each other, right? Trying to see if we can be what we both think we're seeing in the other. So, let's just share. You tell me how you met your husband and I'll tell you all about mine."

"Okay, you go first."

I opened my mouth to object and then closed it again. "Okay. I met my wife, Nancy, in college. I wasn't exactly a virgin, but I also wasn't the most experienced at sex. We kind of met accidentally at a party. She was dating someone else, as was I. Her date had too much to drink, as did she, and he was starting to get pushy and was trying to undress her out on the back deck of the frat house we were at. She didn't want to have sex with him and, being the kind of guy I was, I butted in to help her. I got slugged for my trouble, but that didn't stop me from taking her home, to her house, not mine. She had a little two-bedroom apartment she shared with another girl. Anyway, I took her home. Her dress was torn and when I walked her into her apartment, still fairly drunk, her roommate tore into me thinking I'd done it. She was screaming at me and threatening to call the police and everything. Nancy finally got her to calm down and explained that I'd rescued her, not attacked her.

"I helped her roommate get her to her room and onto the bed. Then I got ready to leave while her roommate tried to undress her. Apparently Nancy puked all over the two of them before I made it to the front door. I heard the roommate shouting at Nancy and headed back to her bedroom, only to find the roommate, naked, her puke-covered bathrobe held out by one hand. She took one look at me and then at herself and dropped the bathrobe and ran past me with one arm over her boobs and the other over her pussy. I took one look at Nancy and felt sorry for her. I sat down and used the bathrobe to wipe the puke off her face and went to find the roommate, who refused to come out of her room. So, I went back and undressed Nancy and carried her to the bathroom. I showered her, wearing my clothes of course, and carried her back to her room and put her to bed. I was going to leave when she woke up enough to grab hold of me, not wanting me to leave for some reason. I sat down on the floor next to her bed, still soaking wet, and held her hand while she went back to sleep. I guess I fell asleep too, and woke up a couple hours later, sitting on her bedroom floor, naked, with her roommate riding my dick.

"Of course, I let her finish, and enjoyed it. I mean Nancy wasn't anything to me at that time, just someone I was helping. Well, the roommate had undressed me enough to have sex with, and after we both came, she helped me undress the rest of the way and hauled me off to her bedroom for more sex. Somewhere along the way I fell asleep with the roommate. When I woke up in the morning I was lying in the roommates bedroom, both of us naked, with nothing to wear. My clothes were in Nancy's room. So I snuck in to get my clothes and while I was getting them, she woke up to a strange man, naked in her room, holding his clothes. You can guess what happened next. More shouting and screaming and accusations until the roommate came in, still naked, and told Nancy that I'd brought her home all messed up. She didn't quite believe that I'd undressed and showered her at first, but finally believed that I hadn't done anything to her other than clean her up, and that it was her roommate that had initiated the sex. With everyone finally calmed down I got dressed and left. A few days later Nancy looked me up and asked me over for dinner to thank me for taking care of her. It was a nice dinner, until her roommate came home and talked the two of us into having sex with her to thank me for everything, as she put it. Nancy wasn't a virgin, but she hadn't had much sex and I guess she and I hit it off. We became a thing and a year later I asked her to marry me. I hadn't had sex with another woman since that night, until this stupid five dates thing."

"You need to explain that. Donna tried to explain it to me, but it didn't make sense."

"My wife got diagnosed with a fast-moving cancer. She was going to die and she knew damn well that as close as the two of us were, I'd just sit and let life pass me by. She was right. For the first six months, that's what I did. Then, on the six month anniversary of her passing, the lawyer that was helping with her will called me and her sister into his office and played us a video she made before she died. In it she asked me to have five dates with anyone I wanted, but I had to have fun and I had to have sex on each date. She knew I wouldn't refuse her anything. I never had. Nothing she ever asked of me did I say no to, and sometimes she asked some hard stuff to do. So here I am. Having sex with a bunch of different women because my wife asked me to."

"So why not just say no if you didn't want to?"

"She asked me to. I loved her too much not to try."

"So you never had sex with anyone else after you met her? Never?"

"Not until that camping trip where I met Donna."

"So who were you taking?"

"Her sister, if you can believe it. That was her request too. Give her sister a shot."

"I wish someone would love me that much. To want to just have sex with only me and me alone. You never messed up?"

"Oh, I messed up a lot. I just never let it get that far. One time I did play with one woman's pussy until she came. That was as close as it came."

"Who was that?"

"Her friend. I went over to fix a pipe under her sink. It only took a minute, but when I slid out from under the sink, there she was, standing over me without any underwear on. I knew what she wanted. She'd made enough hints over a few months that there wasn't much doubt what she wanted me to do. But I couldn't. she started crying, and I think you already know what happens when a woman cries on me. I finally agreed to let her pull my pants down and suck on me while I played with her pussy."

"Did your wife ever find out?"

"Oh yeah. I told her as soon as I got home. I couldn't ever keep a secret from her. She always knew when I was trying to."

"Was she mad?"

"At me? No. At her friend? A bit. But they made up and she promised not to try and cheat on her husband with me again. Didn't stop her from flashing me everything she could any time we were alone, though. I think she still hoped I'd fall off the wagon."

"But you never did."

"Nope."

"She was so lucky."

"Okay, your turn."

She sighed deeply. "If you don't want anything to do with me after I tell you this, I understand. I can sleep in the chair or something until we go home."

It was my turn to sigh. "Would you please stop telling me what I'm going to think?"

"Okay. Here goes. Part of what I told you was true. I met my husband at school, and I WAS a virgin. He pushed and we had sex and I got pregnant. His parents made us get married, but he never really loved me. The first few years were hard. I knew he was cheating on me, but I didn't want to leave him because of our daughter, and I guess because I did sorta love him. Later I wished like hell I had left."

"Why?"

"We were saving up for a house and then all of the sudden we were out of money and barely making our bills. One day he came home with the landlord and took me in the bedroom and told me I had to suck the landlord's cock because we didn't have enough to pay the rent and he'd agreed to let me do that to make up the difference. It was that or get thrown out on the street. I reluctantly agreed. I sucked his cock until he unloaded in my mouth. I was disgusted, but what could I do? The next month we were short even more. I had to strip and give him a lap dance, naked, and then suck him off. I suppose you can guess what happened the next month."

"He wanted to fuck you?"

"Yeah. And every month after that for almost two years. Then it got worse. My husband started bringing strange men home, people I didn't know, telling me if I didn't have sex with them they were going to hurt him, bad. So I did. One of the guys got mad because I wasn't enthusiastic enough, and told me that if I didn't at least pretend I was enjoying it that he'd break both my husband's legs. What could I do? I pretended I was loving it. At first it was just once in a while and then it got more and more frequent. One day he came home and told me I had to get naked and go somewhere with him. I wore a bathrobe to the car and then put on my blindfold so I wouldn't know where we were going. I wasn't allowed to talk or complain or take off the blindfold.

"We got out of the car and he took off my bathrobe and walked me, out in public, as far as I could tell, to some house or something. I could hear lots of people inside when we walked in. I could hear a football game in the background too. He led me to a room and bent me over a bench. Someone put some kind of strap on my wrists and ankles to keep me bent over the bench with my legs spread. It felt like at least ten guys fucked me. Some in my pussy, some in my ass, which I'd never done before, and some in my mouth. I even had some women sit on the bench and make me lick them. One of them got out a vibrator and used it on me until I came in front of everyone. All I could do was to lie there and take it.

"After that, I didn't much care any more. He brough home all kinds of guys to fuck me. I finally figured out that he was gambling, and he used me to pay off debts and charged money from some guys to make more bets. This went on for years. He'd use me to let guys fulfill fantasies, from group sex, to couples swapping, tying me up, lap dances that went all the way, just about anything. I was always supposed to be the playful slut any time he brought anyone home, teasing them and trying to coax them to have sex. It was degrading, but I also knew I had to pretend it was the best thing in the world."

"God, I'm sorry Liz," I whispered, holding her.

"One day I came home and found him having sex with my daughter and her friends. Three of them. She was just eighteen. I had a fit and was going to call the cops. I don't know what he'd been telling her, but she accused me of being a prostitute and that she was only doing for him what I should have been doing. She said if I ever tried to hurt him that she'd never speak to me again.

"A couple weeks later he took me to a jogging trail. He waited until three men came and then he left, telling me he'd meet me by the car. I was supposed to struggle some, but not too much. They took me into the bushes and gang-raped me. Two of them would hold me down while the other fucked me. They took turns. The third guy started slapping my tits, hard. I cried out and he slugged me, nearly knocking me out. He said if I did that again that my husband would end up six feet under. I lay there and let them fuck me for what felt like an hour. Then they left, leaving me lying there bruised and naked. They even took my clothes with them. I guess they wanted to demean me more by making me walk back to the car naked. I must have looked like hell when I got to the car, but all he did was say 'let's go'. Didn't want to see if I was okay or anything. He never had sex with me anymore, never touched me or anything. I guess I was too dirty for him then. Just at tool to be used.

"The next day at work Allissa saw my bruises and demanded to know if my husband had hit me. I said no, but she didn't believe me. She called the police and I finally had to tell them how I got the bruises. They went and arrested him. When my daughter found out, she left. She hasn't spoken to me since. She thinks this was all my fault. So you see, I can't even tell you how many men I had sex with. I was for all purposes, a prostitute that my husband pimped out for his gambling habit. For the last twelve years I've been someone else's sex toy, faking enjoyment even if I hated what they were doing, pretending that they were the best sex in the world, even if they had a tiny little dick that barely felt like anything.

"Now you can see why you don't want to be with me. I don't know how to be anything but a sex toy. I don't know how to love or be loved. I don't know how to be what you need," she said, her voice quavering slightly moments before she broke down into huge sobs like the night before.

I held her for what felt like an hour, stroking her, letting her halfway lie on top of me as she cried it out. When she finally started to subside, I wasn't sure what to do. I reached for her chin and lifted it, reaching my face to hers. I softly kissed her lips and then whispered the only thing that made sense to me, "Why don't we find out together what it is to be you? What you like and what kind you want your life to be? Then let's worry about how it fits with what I want. Just be you. Do what feels good to you."

"You don't hate me for lying to you?"

"How could I?" I asked softly. "Is that what all that stuff on the plane was about? Trying to do the kind of things your husband would have expected?"

"Pretty much. I wanted you to have so much fun on this trip. I wanted you to not be disappointed."

"I'm not disappointed, and I'm not afraid to be with you. So stop worrying and let's just enjoy the time we have alone. Who knows, maybe you'll find out I'm not what you want."

"I don't think that's possible," she whispered as she rolled over onto me. She slid down the bed until her face was over my crotch and grinned at me before gently lifting my cock and closing her lips around it.

"Ohhhhhh yeah," I whispered softly as she teased my dick in her mouth, getting it to start growing. It didn't take too long before she was sliding her hand and lips up the full eight inches of my cock, slurping loudly and eagerly. I closed my eyes and let my head lie back as the sensations started to work on the rest of my body. I was momentarily disappointed when she stopped sucking my dick, but smiled when I looked down and saw her climbing up my body. She settled her pussy against my dick and started to rub it with her wet lips, grinding herself into me. I watched my head appearing and disappearing between her lips as she worked herself back and forth along my rock hard shaft.

"Is this good?" she asked with a soft whisper.

"It is. Is it what you want to do? Or what you think I want you to do?"

"It's what I want to do," she moaned. "I want to see you come. I want to see you squirt your cum because I made it happen."

"Well, it's gonna pretty damn soon," I groaned softly. "Really damn soon at that."

She grinned at me and continued to stroke her pussy along my shaft, grinding her clit hard into my shaft and pushing her own orgasm closer and closer to climax. It was a race to see who was going to last longer. I could see the concentration in her eyes, trying hard to make me come, while at the same time I could see from the puffiness of her areola that her own climax was only moments away.

"Oh shit," she moaned, trying hard to keep stroking. "Oh damn. I'm gonna come. I'm gonna come!" she cried, her voice rising at least two octaves by the time she got done announcing what was obviously overtaking her. She shuddered and sat rigid for seconds, her body shaking, her eyes closed, her sexy chest heaving as she gasped for breath. I wondered when the last time was that she made herself climax for her own enjoyment.

"Your turn," she panted, starting to stroke along my shaft again as her climax started to fade somewhat. "Come for me sweetie. Come for me." Back and forth she stroked again, renewing my race to climax and teasing her own along with it. I felt the urgency building and was nearly there when we heard a loud rapping on the front door. "Oh shit! Not now!" she moaned in frustration as she stopped stroking. She shook her head in irritation as she lifted off my lap, my dick and her incredibly sexy pussy glistening with her juices. She walked to the door, panting, sweat running down her face and chest. She opened the door, clearly not caring who was on the other side. "What the hell do you want?" She snapped at the young woman on the other side of the door.

"Room service?" the young woman on the other side of the door said meekly. "Breakfast?"

"Ohhhhhh shit. I forgot. I'm sorry," Liz apologized contritely to the young woman, opening the door all the way to let the young girl in. She couldn't be more than twenty at the most, if that, as with the girl the night before, was topless, wearing only a thong bikini bottom, her entire evenly-tanned ass and body naked except for the tiny triangle on her pussy and three thin strings. The orange thong bottom did little to hide her pussy, but drew more attention to it that anything. She walked toward the table, staring at me lying on the bed, my rock-hard cock bouncing with each beat of my still-pounding heart.

"I didn't mean to interrupt," the young woman apologized as she set out breakfast out on the table, never quite taking her eyes off my hardon.

Liz grinned a very naughty little grin at me, and stepped behind the young lady, stepping so close her tits almost touched her back as she finished unloading the bag of Styrofoam containers onto the table. "God that looks good doesn't it?" she said softly as she reached her hands to the girl's hips. She stroked her fingers up and down the young woman's smooth tanned skin, letting her fingers trail all the way op to the sides of her perky C cup breasts. The girl froze in place, standing stiffly while Liz worked her fingers slowly, stroke by stroke, around the front of her breasts until she was teasing her fingers up and down across the young woman's rock hard nipples, her chest heaving with excitement as Liz's fingers bounced across those hard nipples. "Would you like to sit on that?" Liz asked in a whisper, just loud enough for me to hear. "Just climb right on it and ride it until you explode?"

"Oh my. Yes I would, but we're not allowed," she whispered back, staring at my hardon.

"Come over, let's look closer." Liz coaxed the young island girl, gently guiding her with her hands on her hips. She moved around the table and walked tentatively toward the bed, short little hesitant steps until she was looking through the hanging mosquito netting at my rock- hard cock. I saw Liz's hands slide down over the young woman's hips and realized she was pushing the tiny thong bottom down, exposing her the rest of the way to me. She pushed all the way down, squatting down behind her as she worked the tiny thong to her ankles, to my surprise, er lips reaching out and kissing the young woman's butt and hip softly. I saw her fingers trace up her legs, teasing the soft skin between her legs until Liz was stroking her fingers across the girl's tanned pussy lips. Liz reached out and pulled the bottom of the netting up and stood back up, lifting the netting up over both their heads and then dropping it behind them so that they were now on the inside of the netting tent.