The Lottery Company Ch. 01

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Younger woman turns his world upside down.
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Part 1 of the 2 part series

Updated 09/22/2022
Created 06/11/2006
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Walking from the beach to the hut, I was watching Leslie's silhouette. We passed into a copse of trees between the water and our quarters. I couldn't help it. I absolutely loved her body. The way her curves just flowed from one to the next made me sweat. So, this time I reached out and caressed her right hip while she walked. I sidled up to her and wrapped my arm around her form and cupped her belly. While I slowly moved upwards toward her breast, Katy hissed into my ear, "Fuck her. Go on, fuck her right here. I'll help you "

Leslie heard the remark and giggled. Sometimes I can't stand that little cunt, Katy, but she does have her moments. This was one of them. I tugged at Leslie's bikini bottoms and felt myself growing hard in anticipation of burying myself balls deep into Leslie's wetness and reacquaint myself with the reason why I loved her body so. Katy was also getting into the mood. I could tell because I could hear her breathing becoming labored. She is such a sex hound and that's why she's here. She doesn't care how her sex is arranged, male, female, or any combination thereof. Katy would fuck Leslie or I, then she would blow whomever she didn't get to fuck. She's amazing that way.

Theses two vixens are what kept me away from the world's population. Here we are on a tropical island and we're alone. Well, not really tropical but it's close enough to it and all three of us fantasize that it's somewhere like Fiji or Tahiti, so for us it is tropical. Food and other stores are dropped off for us every week by a "local" from the mainland. We've been living here for the past three months and I don't miss the world in the least. From all outward appearances neither did Leslie or Katy. Let me tell you this story from the beginning.

Nine months ago I met Leslie when I was being discharged from the hospital and she came to escort me to the front door. Standard hospital protocol and I knew it but since I was being sprung, I went along with the crap. I went along until she walked in the room. I was captivated immediately. I couldn't take my eyes off of her. She was as tall as I was, at about 5'8", but what held me enthralled was her face. It was beautiful! No, what got my attention was her body! At about 18 years old she was the epitome of sensuality. Just pure sensuality is the only way I can describe her femininity. It wasn't her breasts...although they were perfect, not large but perfectly shaped and perfect for her frame. It wasn't her ass...although it was also perfect for her body. It wasn't her waist, either, but it did seem to perfectly mediate the junction of her torso and her legs. Her legs seemed to flow from that perfectly shaped ass. Nor was it her natural olive skinned color, what we call a Mediterranean color. In fact, it wasn't until later that next day that I could focus enough to realize that it wasn't any one attribute that stood out. It was the sum total of all of her feminine attributes and the way that they all seemed to fit together that fascinated me.

While she and I waited for my daughter to come and bring me home, we talked. She was a very pleasant and friendly person. She told me about her boyfriend and how he was older than she was. It turned out that he was 21 years old and she was hiding that fact from her parents. She seemed pretty proud of the fact that she was hiding his age, too. During the conversation we realized that we lived only about three blocks from each other. I'll admit I made a big deal of that fact.

Well after I got home, I couldn't get her out of my mind. I mean, I didn't stalk her but I knew that I was getting to the point of obsession. About 2 months later, I went into the hospital for a colon operation due to the condition. While I was recuperating at home, I went for walks to get my strength back to par and one day I ran into Leslie. I knew this was my one and only opportunity so I shot the moon. I caught her eye and said hello. When she smiled at me I asked her if she remembered me. Well apparently she didn't so I told her who I was and where we'd met. Her eyes lit up in recognition and she admitted that she did remember me from the hospital. We talked for a few minutes and with my heart in my throat I told her where I lived and that she'd be more than welcome to visit while I recuperated. We left it at that and I went on my way and she to hers.

For the rest of that week I made sure I was home at around dinner time as that was roughly the time that we'd met on the street. Well, it took about a week and one day I noticed Leslie saunter up the apartment house driveway. I went outside to meet her before she could chicken out. I asked her upstairs to my apartment. She followed me inside and looked around my studio apartment while I turned on the stereo and found a jazz station. After she accepted my invitation, I got her a Coke to drink and we made small talk until she decided that it was time to go home. That whole time, I didn't make any moves on her because I didn't want to spook her. This is how things went for the next three or four times that she visited.

Then one day I noticed that she was pretty comfortable with me. I steered the conversation this time by asking about her boyfriend. I mentioned that she told me that he was 21 years old and that she was hiding that fact from her parents. Her remark totally stunned me when she declared, "He turned out to be a real asshole. All he wanted was for me to blow him. Whenever we were alone, all he did was try to get me to take his dick out and suck it for him. He hardly ever touched me but he sure wanted a blowjob."

So surprised was I that all I could manage was, "Wow that must have really sucked, huh? Doh, no pun intended!" That made her laugh and broke the ice. The conversation then took another unexpected turn when I told her that sex was meant for the enjoyment of both partners. She blushed at that. I surmised that she was a virgin. Maybe she had some experience but she was a virgin. I had opened the door for her and she walked right through. Her questions were thoughtful, direct and honest so I responded in kind. I especially wanted to be honest and make the conversation light and humorous so that she could be comfortable asking whatever she needed to know. My guess is that it worked.

The next time Leslie visited, she seemed even more comfortable with my company so I again took advantage of that fact and started to rub her shoulders in a gentle massage. After a while I leaned over and kissed her on the back of the neck while I moved lower on her back. Then her breathing became more labored as I caressed her back and moved to her sides and belly. She turned around so that she was looking me in the eyes. I asked her if she was comfortable kissing me because I was so much older than she was. Her reply was to lean forward and kiss me in a very suggestive and hungry kiss. She was all tongue and at the same time she sucked my tongue into her mouth. This began a tongue dance the likes I've never experienced. I mean, she was pretty worked up but I was purely boiling because of the kiss. I wanted to take this further and I did. I kept up the kiss while I caressed her face. Slowly I trailed my hands to her shoulders and moved further down to lightly caress her arms. Then I trailed kisses along her jaw to her neck and gave little butterfly kisses along her neck and upwards towards her ear. As I did this I moved my hands to her torso right alongside her breasts and held just on her ribs but very near her spectacular tits.

I don't know, nor do I care, which maneuver made her elicit slight sighs that told me everything I needed to know. Her breathing quickened and got deeper. I could almost feel her temperature rise accordingly. Her arms went around my neck in a tight embrace and that's when I made the first sexual contact. I slowly and deliberately moved my hands to her breasts, first feeling their heft and shape. Lightly caressing these most feminine attributes made Leslie's sighs become quiet low moans. It seemed so sexy to me to hear these quiet moans of pleasure. If anyone else were in the room, I'm sure that they would not have heard her pleasure and that seemed to fuel my own desire.

I continued to feel her breasts and I wanted to maximize the experience for her. Gradually I made the caresses harder. No, not harder, really. Maybe I should say I made the contact firmer. I fondled her tits through the blouse and bra that she was wearing but I also began to include her nipples. When I first tweaked her nipple, her reaction was like I shocked her little nub with electricity. Not only did her torso jump slightly but her legs did a kind of a hop at the same time. I've heard some women relate that having their nipple pinched made them feel the sensations shoot right to their pussy. Well, Leslie just showed me that it's true. I've never had a woman demonstrate the phenomenon so deliciously!

I knew that things were going along fine, so I upped the ante by sliding my hands inside her blouse, raising it so that I had unfettered access to her breasts. I hadn't expected Leslie's response. The little darling just raised her arms in an invitation to remove her blouse the easy way by sliding it over her head. I took the hint and after removing her blouse, I continued to explore her neck nearby her ear. As I continued to plant kisses around her throat and massage her tits and nipples I eased her to lie down while I feasted on her body. When I finally got her front clasp open I slowly maneuvered my kisses to those luscious tits. They aren't large; in fact they're small at about a 34 and probably a B cup. However, what really turned me on while eyeing her little tits is the fact that she has tiny brown nipples. That's fine with me though because I just adore itty bitty titties. After she admitted that she was embarrassed because they were so small I told her that small tits are sexier. I made sure that she understood that not all men are so awestruck by huge knockers. In no uncertain terms I told her that I prefer women with petite breasts. I then proceeded to show her just how much I liked small breasts. I kissed, licked and fondled her breasts until I thought she was going to cum just from the stimulation.

I knew I had to move further if I was to get to my ultimate goal but I was unsure of how to proceed without alarming her. I mean, I wanted to either fuck her senseless or have her suck me into a coma. I realized that she was probably a virgin so how could I get to her sweet pussy without scaring her? I wanted her to feel comfortable. If she wanted to keep her virginity I would eat her pussy until she passed out. So what I did was to move down her torso until I was nibbling at her navel and then started to unbuckle her belt. I got the expected response. Like a bolt of lightning her hands clasped mine and held them from undoing her belt. Keeping my hands at her belt, I slid up until I could look into her eyes and lightly kiss her lips. Then as I held her gaze I said, "Les, I think that you're a virgin and that's ok. That's your decision to stay that way and I'll certainly respect that. I want to make you feel things that you probably haven't ever felt before. I'll never force anything on you that you don't want. Trust me, ok?"

I could see the wheels turning in her eyes. She had to make a decision but she wanted her safety, too. "Trust me and I'll never make you regret what happens." That's all I said.

"What are you gonna do?" she asked.

Still holding her belt with both of our hands I told her "I'm going to kiss you in places that you've only dreamt about." With that I slowly slid downward trailing kisses while I held her gaze. I couldn't help smiling to myself as I did so. She had a puzzled look. I think she realized what was in the wind after I paused at her breasts, then continued further south. The look of understanding was precious! Her face just exploded in recognition of what I intended. She kept hold of my hands but allowed me to open her belt and jeans while I nuzzled at her belly button.

Once I had her trust, I knew that I was free to enjoy her body. I didn't want to just slake my own thirst, though. I wanted her to want more. I wanted her to seek further encounters, with me as the central character. I'm not a fool. I wanted to ravish her and for her to ravish me and desire more.

After opening her pants, I grabbed both her pants and panties by the waist and slowly slid them down her hips and legs. As her pubic hair came into view, I moved to kiss her mound with my lips and made her aware of my purpose. When her things had been removed from her legs, I began to caress her lower legs. After placing small chaste kisses to her pubic hair, I moved to caress her upper legs. I concentrated on her inner thighs while moving my kisses to where her legs met her mound. This seemed to get Leslie really hot because she started to breathe rather heavily. She held her thighs very tightly together, protecting her treasure. It took me some work and physical encouragement to get her to yield. But when she did open her thighs to my eager kisses and tongue, I knew that she wanted me to give her the best that I could.

Leslie's pussy opened to me when she opened her legs. I played it cool, though. I knew that just diving right in would be extremely pleasurable to her. I didn't want that, though. I wanted her to experience nothing short of earth shattering. To that end, I began giving light butterfly kisses to the inside of her opened thighs, close to her pussy. I wanted to tease her for a short time. I trailed kisses just to the juncture of leg and torso and moved back and forth between both legs. I skimmed kisses across the lips of that delectable pussy as I moved from one side to the other. When her moans turned to whimpers, I gave in and planted a long deep lingering wet kiss to her sloppy cunt. I loved it. I loved her wet tangy taste. I loved her aroma and I loved the fact that she tried to capture my entire face with the lips of her pussy. I hadn't even touched her clit or her vaginal opening, yet.

All I remember was her enthusiasm for me to eat her pussy and her eagerness to slake my hunger for her sex. After she had come and calmed down, she tried to return the favor. I didn't let her. I just held to her naked body and "pillow talked" to her. The first thing I said to her was, "Christ, I love the way that you enjoyed that."

"That was the most amazing thing that I've ever felt."

"And you were worried that I was gonna make you do something that you didn't want to do, huh?'

"Yeah, well my past experience with men have usually been one sided, you know."

"I'd like that to change and I want to be the one to change it."

"Oh you have and you will. The only other satisfying relationship was with my best friend and we were just kids, back then."

I didn't say anything right away. I though I knew what she was saying but I just had to confirm it, you know? Since Leslie was so straightforward about her admission, I thought I'd just take the same tact. "What do you mean?"

"Well, as I said, we were kids, about 15 or 16 years old and I was way beyond curious about boys. Neither one of us had even been kissed and we were dying to learn. We made a pact that we would learn how to kiss from each other. So we did."

I knew, or rather felt that there was more so I probed, but I was a little more indirect. "You sure learned the lesson well, Leslie. Did you learn anything else from her?"

"Yeah", she said while blushing a deep red. "After a few 'lessons', Katy, that's her name by the way, hugged me tightly and our breasts rubbed against each other. God, I never felt anything so sexy. My pussy got so hot and wet from the contact and I think hers did too because she started to breath deep and fast, too. Then she really floored me when she started to rub my breast. I couldn't believe how hot that made me. I was so hot that I didn't try to stop her. In fact I never wanted her to stop and I broke the kiss to tell her. I think telling her that made her get hotter because she went under my shirt and bra to rub my bare breasts."

"Jesus, you're making me hot. Is that all you did?"

"No, after a while she told me to do it to her, too."

"Did you do it?"

"Yeah", she said while turning a deeper shade of red (if that was possible). "I did and I couldn't believe how much hotter we both got. I mean it was amazing how her boob felt. It was totally hot and I couldn't believe that my coochie was soaking wet. Even when I touched myself down there I didn't get that hot or wet. After awhile, we broke away from each other and just looked at each other. We didn't say anything for a minute and then she said that she'd better get home for dinner. After she left I couldn't think about anything other than what we'd done. In fact, while my family had dinner, I couldn't think about anything else. After dinner, I said that I had homework to do and went to my room and closed the door and touched myself all over just trying to make myself feel those feelings all over, again."

"Wow, Les, did you and Katy do it again?"

"Not right away. We kind of avoided each other for a few days. Then she saw me in school and asked if I wanted to hang out after school. I didn't want to completely avoid her. I mean, she is my best friend, so I told her yeah, meet me in front of school and she could come over and listen to my new CD. When we got to my house we said hello to my Mom and we went to my room. After I put the CD on I turned around and she was right there. She started to kiss me and I just melted in her hug, rubbing our breasts together. She then began to caress my beast with her hand, again. Then she broke the kiss and looked at me and asked if anyone ever touched me 'down there'. Now, she knew that I hadn't and when I didn't answer she moved her hand to rub me through my jeans. I got wet instantly and moaned because it felt so good. I didn't have to be told to do it to her, this time. I exploded and then when she had an orgasm, we broke apart. She broke the ice when she said that she wanted to do that since the last time she was over here. Then she said it felt better then when she did it to herself. I burst out laughing and told her that I felt the same way."

"Again we didn't see each other for a few days. Then a couple of days later, she just came over after school and I knew what we were going to do. I was hoping for her to come over and when she did, we just fell into our game. We'd rub each other and have an orgasm and she'd leave to go home. We did that four more times after the first time then just stopped. It felt weird but it felt awesome at the same time, you know? The last time we did it to each other was about 2 months ago."

"Wow, do you miss it?"

"Well, I did until today. Does that make Katy and me lesbians?"

"No, but if it did is that a bad thing?" I asked.

"I don't know but I never told this to anybody and I wouldn't want anybody to know, ok? People would make fun of us and I don't know if I could take that."

"Don't worry about that, Leslie. It doesn't mean that you're a lesbian. And if you were, that's ok because that would just be you being what you are. Being yourself isn't a bad thing it just means that you are what you are. Do you know what I mean?"

"Well, I wouldn't want people to think I was a freak."

"Being a lesbian doesn't make you a freak, Les. DOH, I wasn't calling you a lesbian, you know?"

That made her laugh and it broke the proverbial ice. Then I told her that if she desired both men and women that wasn't bad either. But her story mad me want to eat her again. So I did. I ate that cunt until she cried out her orgasm and fell into a heap while I tried to tongue dance her to just one more. She would have none of it, however. She pushed me away from that sloppy warm wet hole and frantically undid my own belt and zipper. Without removing my jeans, she gained hold of my hard cock and blew me into another dimension.

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