The Humper Game Pt. 02 Ch. 15

Molly said, "I probably can fix it with your monitors, but that's not a good way to do things. But any of us could go to your room, or one of your young ladies'. They're not off limits to us. It used to be pretty common, after the seniors' week, for some of the kitchen and housekeeping girls to spend a night now and then in some boy student's room. I admit I was looking forward to seeing her get her cherry popped, but if you tell her where to go she can join you. Girls' wing would be better, though."

I answered, "If that's so, why don't you all come? Although I shouldn't invite you to Jenny's or Sam's room, I think Jenny's in this case. I've, well, I've entertained more than one girl, one at a time of course, with more than this looking on. So it would be up to you and to Jenny and especially to Ginny. If she wants to wait or to call it off, there's no point."

Ginny said, "No, I want you to do it. Tonight. I admit I'm kind of scared." She looked at Jenny.

I said, "Scared is one reason it may take a lot more time than you expect. But Jenny?" And I looked at her, too.

She said, "I guess I've kind of committed myself to this. Let's Sam and Phil and me go get out of curfew troubles. If Ginny shows up, she's on unless she changes her mind. If she shows up, any of the rest of you may as well too. It will be crowded, but we'll manage."

We hurried, and we made it to the monitor's desk with more like five minutes to spare than the ten I had offered Ginny. I was checked in for Jenny's room. We stopped by the lavatory on the way. And of course we still had to wait a bit. They probably took turns with the lavatory in Molly's room, and of course they all had to get dressed.

There was a knock on the door, and it was Ginny. She slipped in and went back next to me. I gave her a hug and a brief kiss. When the door opened next, it was for Mary and Janet. When the door was shut, one of them said, very quietly, "She'll be here in a minute."

It was several minutes, but Molly did come to the door. I had improved the time by kissing Ginny at greater length, but she wasn't responding very well. She felt tense and twitchy to me.

When Molly was there, I said, "Are you changing your mind?"

"No, but like I said, I'm kind of scared."

So I told her, "Well, take off your clothes and sit down on the bed, and then we'll see what we need to do." I undressed myself and sat, too.

I put my arms around her and kissed her gently and pretty briefly. "So, talk to me. What is it you're afraid of?"

"I don't know it all. I know it's going to hurt, and I'm scared of that, but beyond that, I just feel scared about it."

"All right, let's talk first, and then see what we need to do. I'll talk, I mean, and Sam and Jenny may stick in a few words.

"I have kind of a lot of experience with this. And one girl, the second intact virgin I had sex with, and only my third in all, she was scared about the pain, too. This was in the game, and she wasn't on close terms with me, as well, but the rules said I could screw her, so she was willing, but she was very scared, of the pain and some other things I won't tell you about. And here's what we did. Remember, I was still very inexperienced,

"I didn't know this then, but one reason she was so scared was that she had heard her mother and her older sister comparing notes on how awful their first times had been. But anyway, she didn't want anything to do with me romantically, kissing or anything like that, because she didn't want to be on such terms with me—me or anybody. But I thought, it really was going to hurt her a lot. Not losing her cherry. I'd done that a little while earlier with someone else, and she assured me that it wasn't really bad, and also I knew what it felt like to my, um, pretty sensitive parts when I broke through. But because she was so tense, her body wasn't preparing in other ways. And I told you she was my third, and my first had been maybe an hour earlier, but, well, I knew from the others, as well as from book learning, that a girl's body produces lubrication when she's aroused and wanting. And this girl was miles from that. If I went in, tore through her membrane, and then shoved myself around up in there when she was completely tight and dry, that would hurt a lot more than the first part of it. When I popped that other girl's cherry, I was instantly in where it was warm and quite wet, and it was wonderful for me and very good for her.

"Well, she didn't want affection from me, but I asked her if I could at least eat her pussy some. I told her what I was thinking. It wouldn't make her want me, the way it did Janet and Molly earlier, both because she was scared and for other reasons. But I said I hoped it would help her body relax and maybe lubricate some, and that at least the saliva would provide some lubrication. And she let me do that.

"Anyway, when I pushed in, she was wet enough that it didn't hurt any more. One of the girls, maybe her, said it was a little tender where things had torn. And she definitely almost laughed, and she said, things I have to do in gym hurt worse than that, all the time. In the end, she was happy and ready to take steps toward friendship. I had taken something she thought would be horrible and painful, and made it into something pretty good, you see. The pain was very brief, and less than pulling a muscle in gym or something.

"And I'll tell you about one other girl. This is a little different, though. I told you about that one just to try to reassure you about the pain of your membrane tearing. Every single girl whose cherry I popped, and for a few days there were kind of a lot, said that it didn't hurt worth mentioning.

"But this one, I'm telling you to help you trust me a little. In our week, one day was spent doing anal sex." I looked at her to make sure she understood. She nodded. "I don't know whether for some reason she went in really afraid of it, or what, but whatever her instructor did, it hurt. A lot.

"Now, she was already good friends with her partner, and he's just the right kind for this. He cared about her, he didn't want to hurt her at all. And he's patient and gentle anyway, and I'm proud to be his friend, after all this was over. But anyway, he hurt her a lot, too, try as he might, and they were both really discouraged about it. They really do love each other, and they had to do this together, and it was OK for him but totally miserable for her.

"Well, at supper that day, several of the girls we sat with, all of them I guess, were saying how much they hated doing anal sex, how just plain nasty it was. Not like the girl I told you about, but nothing to like in it. So Jenny here spoke up and said, well, it wasn't something she was crazy about, but a lot of it she had enjoyed. She made it clear that I had worked to make it that way. And I'll add that Sam didn't say anything, but she was there at the time, and I did it with her too, and the same was true. On the whole, very pleasant, not really painful, but with some yucky parts. Is that a fair summary, girls?"

Jenny stood up and came over and gave me a long, kind of steamy kiss. "I'd sort of forgotten, with everything that's happened since," she said. "The only thing wrong is he's being too modest. It was better than just 'on the whole, very pleasant,' way better in fact, in spite of a few yucky parts. And it was because Phil was so patient and caring, and that's flat." And Sam put in, "That's exactly right."

I went on, "So this girl heard about Jenny's having said this, and she was a very close friend of ours, Jenny's and mine. She was working on being friends with Sam, too. She and I had had sex several times, and I had in fact popped her cherry, and we were, and are, very close. But anyway, she and her partner showed up that evening, and they wanted to check out what they'd heard. Having done that, they asked me to do it again, with her, in the hopes of getting through it at least OK, not painful and awful with cramps besides. And I said I'd try, as a favor to this girl I also loved. We don't see her so much now, but she's still one of our favorite people. For all three of us.

"At any rate, she knew me, she knew I cared a lot about her, and she trusted me. But she was so tense and scared that she couldn't relax and really trust me. So I just put anal sex, or any sex, on the back burner, and did everything I could think of to help her relax. The biggest thing was a massage, really just a back rub. And I took a long time at it. And she finally told me to quit it, if she relaxed any more she would fall asleep.

"But not all that long before, even though I told her nothing at all was going into her ass without warning, every time I got anywhere near it, her whole ass would just go into spasms, enough to cramp her. So I kept at it and at it. And, as I said, she finally said she couldn't relax any more because everything was totally relaxed.

"And at that point, I said, I promise you I'll stop in my tracks if you go into spasms, and just wait it out. And I'll stop where I am if you tell me to. And if you tell me to give up entirely, I promise I'll do that, too. And then I asked her, do you trust me? And she said, 'Phil, with you, anything.' That is one of the proudest moments of my life!

"So anyway, we started off the same way, but way, way slower. I won't go into that, anal sex isn't the point. But I did what I had promised. When I touched her anus, when I put a fingertip in, and so on, her body would go into a spasm. And I waited it out. And she knew, really knew, that if she said to quit, I would, any time, even if I was in her ass about to come, so the spasms got smaller and fewer. And it turned out to be very good for her, too. Some of the yuckiest parts I offered to let her skip, and she decided to do them, just to prove to herself that it really wasn't so awful after all. Molly can tell you what the yucky parts were, later, if she wants.

"So I'm going to try to relax you, first of all. And I promise you, if I sense something wrong, I'll stop, pause I mean, until it's resolved. If you tell me to stop, to pause, I will. I guess if I'm inside you ejaculating, all I'd be able to do would be to come out and spray all over us, but short of that. You can tell me to give up and quit at any time. I won't poke anything at all into your body orifices without telling you first, and asking if it's OK. One exception: I may put my tongue in your mouth when I kiss you."

I knew I had gone on way too long. Partly I'd wanted to be clear and get the details right—a long-standing bad habit of mine—but partly I was hoping to give her time to stop feeling so afraid.

"Are you willing to trust me? Probably not really, now. But let's try to get you to relax now, and then we'll see. So please lie down, face down."

She did it, and I straddled her. I've already told you about the massage I gave Ellen, and this was about the same, except I moved on just a little faster at each point. And as with Ellen, I eventually felt the tension just drain out of her.

Finally, I bent over her and kissed the back of her neck. I asked her, "Will you trust me not to hurt you more than just one short pang, with maybe a faint ache left behind?"

She said, "I think so. I'm not quite ready for, 'Phil, with you, anything,' yet, but please, please make love to me, Phil."

"Then roll over, please. And we'll take it slow where we can. And if you need me to pause, or to quit, say so, and I will. That's really all you need to trust me for."

She rolled over and spread her legs apart. I told her, "Eventually probably like that, but that's not what I meant for now." I moved to lie next to her, and put my arms around her, and kissed her. This time she kissed back with passion. Her tongue came into my mouth first, and she pointed this out to me. "You see, you did put your tongue in my mouth, but I did it first to you."

After a few leisurely minutes, I said, "I'm going to start touching your body now, mostly your breasts. Tell me if you need me to stop." She just kissed me a lot more intensely, so I began. She gasped and twitched whenever I rubbed across her nipples. I cupped her ass as well, and traced the outline of her waist and hips.

"I'm going to touch your pussy now. Let me know if there's a problem. I probably will put a finger inside you, more than once. It's a finger, not my cock, and it shouldn't tear anything at all. And I'll stick to just one finger."

She laid her head on my shoulder, except that we were facing each other, lying on our sides, so I wasn't actually carrying any weight. It was just a gesture, but it really meant a lot. And indeed, she then said, "Phil, with you, anything. I mean it." I thought my heart would burst.

So I played with her pussy, taking it slow. She was quite wet at this point, on the outside I mean. I put a finger in, and she said huskily, "Oh, you're wonderful, you feel so good." I pulled out as much as I could of the thicker lubrication that was inside, and spread it around. As I touched the critical places, she flinched and gasped. "Please, you're going too slow, please do it, whatever comes next!" she begged me.

So I told her, "Watch out, then, I'm going to move you," and moved her legs around. I got down on the floor between them, and teased the insides of her thighs a little with my tongue, and around the perimeter of her pussy. I said, "My finger is going back in," and put it in, and licked around a few places. Then I zeroed in on the most sensitive areas, and her hips thrust away and back again, with moans and gasps. Her thighs came up to imprison my head, and she thrust back and forth a few more times, and came with loud cries.

When she was done, and had released my head, I moved her legs around and got back into bed with her. I told her, "Now is the moment of truth. Shall I proceed?"

"Please," she said. "I want you so much, I never knew I could want anything that way."

So I moved on top of her, and positioned myself to come in. She opened her eyes and looked at me and nodded. I took my hand and parted her labia, and began to go in. Immediately I was stuck. I said, "Here's where the pain comes. Shall I go on?"

She pulled my head down for a kiss. "Yes, please, now!" So I shoved through, and everything felt wonderful. She was kind of tight, but very, very wet.

I just held still. "I'm through, and that should be the last of any real pain. You're tight yet, so I'm waiting to go ahead. I'll warn you, or you can tell me when you think you've adjusted."

"You're wonderful, you feel completely right, go on in!" I still went slowly, but I pushed until I was all the way in. I waited another moment or two, then began thrusting in and out, trying to hold myself so that I rubbed where I most needed to. After half a dozen or so strokes, she was moving with me, and I sped up. She grunted and gasped and whimpered. I sped up a little, and her urgency increased. I carefully did not distract her by trying to kiss her. Her eyes closed, and she panted and gasped. I sped up a little more, and she came again. I was close myself, but managed to ride it out.

She opened her eyes and looked at me, pulled my head down for another kiss. "Is there more?"

"Well, I haven't come yet. Fourth time tonight, sixth since early afternoon. I'm going to try to come now. I just hope I don't get you close and then abandon you."

I tightened myself up, and thrust in and out, in and out, trying to get ready. Mary said, from somewhere out of view, "If you'd like me to try sucking you, I'm still pretty eager."

"No, we're going to finish this way." I felt another orgasm building in Ginny's body, and tried to push ahead. Then I was there, unable to say anything to warn her, and I thrust in hard all the way, beginning to come. And after a moment, as I ground against her, she came too, intensely and loudly.

I completely collapsed onto her. I had been holding so tight, trying to come, that I was having trouble catching my breath. She was still moaning at top volume, as I struggled to sit up enough to breathe better. Finally she was done, and I just pulled straight out and swung over next to her and collapsed onto my back.

And abruptly someone was sucking on my cock, cleaning me off. I looked down, and it was Mary. Ginny said, "No! Stop that! If anyone does it, it's me!" as she moved down to the scene of action. I decided to keep out of this one unless someone's teeth or nails came into play. I thought Sam could knock their heads together if she needed to, with no help from me.

And, indeed, Sam's voice said sharply, "Mary, she's right. You let her do that." Then more quietly, to Ginny, "You're cleaning him off, not trying to get him going again. That would take way too long, now. He had trouble this time. Which benefited you." So Ginny finished the job, and then looked up at me.

I said, "Jenny, I just thought. Every other time, it's been outside on grass, and I've barely noticed. But there's probably blood on that sheet. Can you do something about it?"

Molly said, "Leave that to me, but leave it lie a minute. Ginny, you get a wad of tissue between your legs and get your underpants on." She did so. "Jenny, do you have a change of sheets, or is someone going to have to go get one?"

Jenny produced sheets, and Molly stripped off the used, bloody—blood-speckled, really—one, rolling it up, and then quickly and efficiently made the bed. Ginny and I both got dressed. I kissed her and said, "Either that was really good, or you are the world's best actress ever."

She kissed me, but then said, "It's really late, and I have to get up. Thank you, more than I can say, but I'm going to run away now. Maybe some other time, soon." Sam opened the door and looked up and down the hall, then shooed her out. I noticed she turned away from the hallway to the monitor's station. Sam closed the door.

The other two came and kissed me, too. Mary told me, "Bill was a clumsy oaf, and I never realized it. I wish my first had been a tenth that good. A hundredth. But you kind of made up for it tonight, with Janet and with me and now with Ginny. And I think we all have to get up, so Janet and I will run off too." Sam checked the hallway again, then they left.

Molly said, "I really doubt you want to kiss me after all that with those young beauties, but you're going to have to." She put down her bundled sheets and came up to me with open arms. I didn't hesitate to hug her and give her the biggest kiss I knew how. At this point, somehow her fat troubled me a lot less. The white hair and wrinkles never had bothered me a bit.

I said, "Thank you, it's due to you that I had a spectacular evening. But I know you have to get up early too, and I really should. But I think I'll skip running tomorrow, Jenny. If you're willing, you can try running flat on your back. I should be recovered by then.

"But Molly, or maybe it's Miss Macgregor again now, you had us set aside this evening and tomorrow evening both. Will you tell me what your plan is? Except that I'm afraid I need to ask that it not include as many as four. Much as I enjoyed all of you."

"I had a couple more in mind, but I'll have to think on it. Maybe them, maybe these three again. You won't be wanting me, next time."

I said, "Why do I have to keep saying this? If it's in your room, you come first. Period. Maybe even if it's somewhere else, since you're the one setting it up."

She looked at me. "You do mean it, don't you. I thank you, even if I think you're daft. I'll let you know about tomorrow. Schedules may be a bit harder to change around."

She kissed me again, and she too was slipped out the door.

And finally, Sam kissed me. "I won't take even two minutes more of your time. We all need to get to bed right away. I may see you in the lavatory, but that's it." She did take one of those two minutes for a long kiss. And, I'll add, I ambushed her before she left the lavatory for one final kiss. She didn't bother checking, this time, she just walked out, letting the door shut.