7. Linda's New "Family" Pt. 05

I scheduled Bill for Thursday night. I knew he was shy, at least in the sense that he got flustered and a bit clumsy around me. And he had proposed to me, the last of the five proposals I got last week. It was an awkward one. He was almost tongue tied and blushing and fumbling with his words. I knew he wanted me, but he was very insecure about the whole thing. I was hoping that I could build him up a bit in his self-confidence. There is nothing like having sex with someone to make you feel good about yourself. Or make you feel horrible about yourself. I might either destroy Bill or stand him on his feet. I know that is true of women, but I hadn't realized how insecure some men are.

Bill did not eat very much at dinner. Every time someone would look at him, he would blush. And if anyone asked him a question he could barely do more than a monosyllabic answer. He was on kitchen clean up and I thought it might help if I pitched in with the washing up. But it didn't. He could barely look me in the eye. If he hadn't proposed I would have thought he didn't like me at all. I was getting a little nervous about the night. Had I misread him completely? I would soon know.

As soon as we were done, he just said, "Well, I guess I will see you soon," and went up to his room. It didn't exactly sound like the nervous anticipation of a night of wild sex that I had expected. He actually sounded scared. I did know he was self-conscious about his weight. So he was a little over-weight. Not badly, just a little on the pudgy side. I had thought it was only women who worried about their weight. True, the other guys in our little family were thin. Not all of them were athletic, but they were all good looking. Anyway, I was working on a project with a dead line so I went up to my room to get some work done first. I figured that nine o'clock would be a good time to go down. It would give him a little time to unwind, maybe relax a bit. Or tense up. I didn't know how to judge the timing exactly.

And he had been relaxing, sort of. I saw three empty beers on his desk. He had a mini-fridge in his room. Too much alcohol can make you pretty incapable of sex, but I thought three beers was really pretty moderate. Bill wasn't a big drinker. No hard liquor that I knew about. I guess for Bill, three beers might be making him feel a little less nervous, but if so it wasn't completely working. For me even one beer might knock me out, but he was used to it. As soon as he let me in he offered me a beer.

"No thank you, Bill. Those things put me right to sleep and I don't want to sleep through what we are about to do." I smiled an encouraging smile, but he just swallowed hard. "You doing OK?"

"Oh, yeah. Yeah. Sure. Sure. Me too."

"Look, Bill. It is natural to be nervous your first time. It is all going to be fine. I am going to try to make it unforgettable." I smiled my most seductive smile, but I think it may have made him more nervous.

His shoulders slumped and he sort of grunted. "I guess it is obvious that I have never done this before."

"Nothing wrong with that. Everyone has a first time. I will show you all you need to know. Think of me as your tutor, your guide to the mysteries and delights of sex."

He didn't respond and I wasn't sure what he was thinking. I walked over to him and put my arms around his waist. He had his back to me and when I did he stiffened up. "Relax. There is nothing that can go wrong. You'll feel a lot more relaxed in a few minutes or the fault is mine." I let my hand drift down slowly to where his penis was also pretty tense. I just let my hand rest on him. His breathing was pretty ragged. I realized I would have to take charge of the proceedings. Bill was too embarrassed to know what to do.

"Now turn around and face me." He took a deep breath and did. I stepped away from him about a foot.

"I want you to unbutton my shirt now." He reached up hesitantly and began to undo the buttons. They were not hard to undo, but his hands were shaking. When he had undone the last one, I said, "Now slide my shirt off me. Let it fall to the floor." This time I was wearing a black bra. It had a snap in the middle, right between my breasts, and it was strapless. If he unbuttoned it, it would just fall to the floor. It was also pretty tight. It made my breasts look larger than they are. I'm not insecure about having small breasts; they're not all that small, butut I know some men like breasts the larger the better. I wasn't sure about what Bill liked, but I was what he was going to get. If he preferred women with big boobs that would be for him to find for himself. But this was his first time so I figured he wouldn't complain..

"The only thing holding up my bra is that little snap, right in the middle, between my boobs. When you unsnap it, my bra will fall to the floor. So unsnap it now." He swallowed hard and with hands that were shaking he unsnapped it and it just fell by gravity to the floor. And there were my tits for him to stare at. I bet it was his first time looking at a woman's tits, unless he watched porn that is, which is not quite the same thing at all. You can't touch the tits you see on a screen, but he could touch mine.

"Look at my tits, Bill. Stare as much as you want. You can touch them if you want." After a minute or so I took his hands in mine and moved them up to cup my breasts. "Well, I want you to feel my tits, Bill. It makes me feel good for you to look at them and touch them." He was blushing and looked awkward. "Don't be ashamed of what you want or how you feel. I like thinking about you looking at my tits and wanting to fuck me." He was embarrassed because he wanted me. I realized he was afraid that I would not want him. He felt insecure about his own body. I had already had sex with three of his housemates, and he was wondering how his body would compare to theirs, how I would compare his body to theirs. He was afraid I wouldn't find him attractive, that I would be disappointed. I know of women who torture themselves that way, and who are tortured by men that way. It makes me angry.

"I will unbutton your shirt now, OK. It's only fair, right." He gulped but he didn't try to stop me. I got his shirt off and started caressing him all over his chest, his stomach, his nipples. I wanted to make him feel attractive. I stared at him too, looking over his chest and waling around him and letting my hand glide over his skin. When I got all the way around, I turned my back to him. "Now Bill, reach your hands around me and take both of my tits in your hands and play with them. Play with them any way you want."

He took both of my breasts in his hands and just held them, squeezing each one gently. I reached up and took his right and off my breast and took his thumb and forefinger and put my nipple between thim. "Squeeze my nipple gently. Roll it between your fingers. Now do the same thing to my other nipple with your other hand." He did hesitantly at first but then like he was really enjoying it. "It really makes a woman feel good for a man to play with her tits this way. Remember that when you go out into the world and find another woman."

"Are you standing close enough that you can looks over my shoulder and see my tits in your hands."

He moved in closer and whispered, "Yes." Then I took his right hand and moved it down between my legs and pressed it into my crotch.

I turned around then and he stepped back a bit. "Now, unfasten my pants and pull them down." I was wearing blue panties, dark blue, almost black. He was staring between my legs. "Have you ever seen a woman's pussy, Bill? Not on a computer screen, I mean." He just shook his head. "Well, now you are going to see my pussy, Bill. Pull my panties down."

When he had them pulled down I just kicked them away. Again I just stood there and invited him to stare at me. He was staring at my pussy like he was in awe, like he couldn't believe this was happening to him. It made me feel hot. It made me want to just fuck him right then. But this needed to be slow. I pushed him to a sitting position on the bed and stood out just past his knees, so my pussy was right in front of his face. "Now you are looking at a woman's pussy. I am pretty typical, maybe bushier than some. Get your eyes full of me. It makes me feel hot to see you looking at me. It makes me want to throw you on the bed and just fuck. But take your time and just look at my body." I opened my legs a bit and raised my hands over my head so that I was stretched out full length in front of him. When he had stared at me a while, I took his hand again and pressed it against my mound. "Feel it, Bill. That is my pussy"

His mouth was open and he was breathing hard. "You need an anatomy lesson now. Let me show you where to touch." I opened my legs wider so he could see my clitoris between the labia. "Here are the labia, my pussy lips, and my vulva, and here in between the lips is this little button. That is my clitoris. Put your finger right here." I showed him exactly where. "Now move your finger over my clitoris, but gently."

It was so good. He could tell he was making me feel good. I let myself moan out loud with pleasure. I wasn't faking it at all. "If you are very nice to my clitoris it will give me an orgasm, though it might take a while. When you do find another woman you want to fuck, be nice to her clitoris and she will give thanks she found you." I let him touch me for a while and then I moved his finger down to my vagina. "This is my vagina, where your penis will go. I want you to slide one of your fingers inside my vagina." He pushed his finger in very tentatively. "You can go a lot further than that. Push further in. That's good. If you get in far enough you will find my G spot and I will go wild. Touching my clitoris, touching my G spot, I won't be able to say no to anything you want to do to me. I don't think any woman would want you to stop. But we will save the G spot for future lessons."

After just a minute, I said, "Alright Bill. I showed you mine, now you show me yours." He slid his finger out and stood up. "I will take your pants off now. I really want to see you naked. Especially your cock."

I unsnapped his pants and unzipped them. He was sucking in his stomach. He wanted me to not notice his weight. I pulled down his pants. His erection was well under way by this time. Again, he put his hand in front of his penis like he was embarrassed to have an erection but his hand couldn't hide that one. "You're dick looks like it needs to get out of there. Show me Bill. Show me your dick." I moved his hand away so I could see him without obstruction and gently pulled his briefs over the bulge his dick was making. He was blushing.

I looked at his dick for a while, letting him see me looking at him, letting him see how much I wanted him.. Looking at a man's penis makes me horny as hell, well six out of six times I have gotten to look at a man's penis. His penis was average size, very stiff and curving up slightly. It was beautiful. "I love the way your dick looks Bill. Don't be shy about it. You have a great dick." I kissed the tip of his dick and he shuddered. I was thinking that if I took him all the way in my mouth he might cum, so I would save that for another week. Then I remember my night with Ken. He hadn't even lasted till I got him naked. Bill didn't seem on the verge of cumming yet, but I didn't want to risk it. "Are you OK, Bill? Hold up OK? Are you getting close to cumming?"

He swallowed. "Uh, no, I am OK. But I might be close."

"Let me know if I am going too fast or making you feel too good. I want to savor having sex with you as long as I can make it last. But if you do feel like you may not be able to control yourself, let me know so I will know what to do. OK?"

"Yes. OK."

So I looked at him a while, without touching him -- no sense in rushing things if I didn't have to. It was pretty clear that he wouldn't last long when he started to fuck me. That was all right. He'd do better in the future when he knew what to expect. It was his first time, after all. If I taught him well we'd get to the point we could fuck all night long. OK, maybe that is setting my sights too high.

I had him lie down on the bed. "I am going to straddle you and lower myself onto your dick. I have never done that before, but I want you to be looking at my body while you fuck me. I want you to see the whole thing, how your dick goes in and watch how my body is going to take you in. OK?"

I got over him and knelt above him with my pussy just above his dick. Then I put the tip of his dick right against my vagina and slowly lowered myself down on to him. He watched as his dick slid in to me, all the way in. He gasped as he felt his penis enter me, and when I was completely impaled on his dick his eyes rolled in pleasure. "Look at how far you are inside me, Bill." I had lowered myself all the way down. "Where do you think your dick comes to inside me? I think you come in up to here." and I touch the spot on my stomach that was just in front of where I thought I could feel his dick. "When you cum, Bill, this is where your semen will explode into me."

Having never done this before, I wasn't sure exactly how to move my pussy around his dick. So I opted for simply moving up and down, letting him slide all the way in and then nearly taking him all the way out. It was good enough, apparently. Before many plunges, I could see by his face he was close. I had nearly let him all the way out when I could tell he was about to ejaculate so I pushed quickly all the way down and felt him cum inside me. I moved out a short way and down quickly to catch the next ejaculation, and then the next, until he was done.

Then I sort of fell over on him and rested my head on his shoulders with his dick still most of the way inside me. He was breathing very hard, as was I. I had not had an orgasm, but I had not expected to. I figured Bill couldn't last long enough to give me one. But I meant what I had said to him about being his sex tutor. Every Thursday I could give him another lesson. I would teach him all I knew, which wasn't all that much, but still. By the time a few months had past he would know everything I knew about fucking.

I sort of rolled off him and laid down beside him. "That was really good Bill. You felt perfect inside me. I am already looking forward to fucking you next week."

"Was it really? Good I mean. For you."

"Yes."

"As good as with the other guys?"

"Well, some of them have a lot more experience than you do. You were absolutely great for your first time, and every week will get better and better. I bet none of them were as good as you for their first time."

"Really? You're not just saying that?"

"I am not just saying that. When I am done with you, you will be an awe to every woman you fuck. You have all the potential for great skills in sex. Any woman will be lucky to be fucked by you."

After a few minutes of silence and just lying next to each other naked, I said. "How about me? Were you disappointed in me? I wanted your first time to be spectacular."

"Oh. It was spectacular. I am amazed. I had not even dreamed how good it could be."

"So you enjoyed fucking me?"

"Yes. I enjoyed it."

"Enjoyed what?"

"i just want you to say it out loud."

"Uh, what do you mean?"

"I want you to not be shy about what we just did. I want you to say out loud, I really like to fuck you Linda."

It was hard for him. He took a deep breath. "I really like to ... to ... to fuck you Linda."

"Now say 'fuck' again."

"Fuck."

"Cause that is what you did to me. You fucked me. And you fucked me good. There will never come a time when you have not fucked me. That can't be taken away from you forever."

"No. It can't."

"Now say 'pussy' for me."

"Pussy for you." He giggled.

"Good. Pussy. You have now looked at a woman's pussy, you have touched a woman's pussy. That will never not be."

"Yes, I have enjoyed your pussy."

"Good. Now let's turn off that lamp and go to sleep."

"Uh, sure. OK. I am not sure how much sleep I can get with a naked woman lying beside me though."

"Well, if you can't sleep in the middle of the night, I know things we can do. Just wake me up if you need to."

He was exhausted and relaxed in a way he had probably never been since puberty. I don't think it took long for us both to fall asleep. I rolled over onto my side and let my head rest on his shoulder and my left hand and my left breast on his chest. It wasn't long before I drifted off. Sure enough, I woke at about 5 to see his penis erect and him wide awake.

"You should have woken me when you did." I reached down and wrapped my hand around his dick. "Let's fuck the usual way. You on top. Take me again." I rolled over on to my back and he lifted himself up to kneel at my feet. I opened my legs for him and he leaned over and put his dick right back in where he had been. He was slower this time. He was fucking me for fully five or ten minutes before I could feel him suddenly push as far in as he could and ejaculate inside me. His technique did not bring me to orgasm but it felt damn good just to be fucked. There were not as many ejaculations this time, of course. Once it was done, he sort of collapsed on top of me and we lay there like that.

"No point in going back to sleep now. Let's get up and take our showers and get our day going early. No one else is awake yet. I might even risk walking up to my room naked."

"But then the guys would know..."

"What? That you fucked me? I bet they will figure that out whether they see me or not."

I got up and gathered my clothes. Before I left I turned to him and said, "You did that very well, Bill. I am going to look forward to Thursday nights. Think about what you want to do next Thursday. I will do anything with you that you want. And I have some ideas myself." I started to leave. "Oh, by the way, do you ever masturbate?" He blushed.

"Yes."

"Don't be embarrassed. You should. Next Wednesday night take time to masturbate. It won't spoil anything for Thursday night and we can last longer when we have sex. OK?"

"Yeah. OK."

Then I did walk out of his room naked. I went up to my room slowly. I almost hoped someone would be up early and see me, but no luck. I felt pretty good about the evening. And Bill did too. Week by week his confidence built up and he was a lot less shy. I also noticed in classes that he was a lot less awkward around other women. I felt good about what I had done. I had used sex as a way of healing a damage ego. And enjoyed it immensely. Every week will Bill was better than the one before.