Chapter 5

Boy was I looking forward to the next day! On the way home I read Eileen's note. It said, "Dave, I urgently need to speak with you about Cecily. Please meet me at my home at 4 pm tomorrow—I'm counting on you."

I laughed to myself. I knew she'd think of some pretext, and that was as good as any.

Thinking about Eileen Arnold, I realized that she was the main reason her daughter Cecily was so stuck-up and unkind. It made me feel much more forgiving of Cecily, and ready to let her down easy rather than make her life painful. Eileen would be doing the suffering...

So the next day after school I sat down with Cecily on a bench and we talked—or rather I gave her some new instructions. I told her that after our conversation, she'd think that she had broken up with me—told me that she liked and respected me and always wanted to be my good friend, but that she didn't think we should be boyfriend and girlfriend anymore. I'd agreed to that, and wanted to be her friend, too, so she wouldn't feel guilty.

And I also told her that she'd learned a lot from me about being more sensitive to other people's feelings. She'd realized that popularity was not so important, much less important than kindness and generosity towards others. And she was looking forward to treating people in a new way, and grateful to me for this insight.

I added one final touch: that from now on, every Monday and Thursday she'd arrange something to keep her busy, so that she didn't go home before 6:00.

When I was done Cecily smiled at me and said, "I'm so glad you feel the same way, Dave. Even though we're not going to go out any more I feel so close to you! I want us to always be friends." And she kissed me on the cheek.

"I feel just the same way, Cecily," I smiled back at her. And then she told me she was headed to the library for a while, to work on a project. And I sauntered off towards her mother's house!

I got there about ten minutes early, and just for the hell of it I went around the back to see if I could catch a glimpse of Eileen. To my delight there she was on the living room couch. She was wearing a pretty bathrobe and, under it, a very sexy negligee. The robe was open and the negligee pulled up to her waist. Eileen was lying back with her legs spread wide, energetically masturbating! I couldn't hear anything but I could see from her open mouth that she was breathing hard. It was unbelievably sexy.

Boy, was I looking forward to this! I went back around and rang the front door, and in a moment she appeared, looking disheveled and flushed, the bathrobe neatly closed around her.

"Hello, Dave, I'm so glad you came," she said, drawing me inside with a hand on my arm. The aroma of her sexual arousal nearly overwhelmed me.

She got me a soda (after offering me beer or a glass of wine, amazingly enough) and sat me down on the couch, perching close beside me, half-turned to me so her knee just brushed against my thigh. After some hemming and hawing, she told me the ostensible reason for asking me over.

Simply put, it was that she didn't think Cecily was right for me. She was just too young and immature, not really ready for a relationship with a mature young man like me.

She knew I thought Cecily was very pretty, everyone did, but she was sure I'd be better off with someone experienced in matters of love—and sex.

As she said this last part she leaned closer, and her hand stroked up and down my thigh.

"I don't know, Mrs. Arnold," I said doubtfully.

"Please, call me Eileen," she breathed.

"Okay, uh, Eileen, I really really like Cecily, and I—"

"Is she fucking you?"

"What?" I replied, feigning shock.

"Is she fucking you, Dave? And is it satisfying for you?"

"Eileen, I—"

She stood up and pulled her robe off, revealing the lavender negligee. It was silky, and thin enough that I could see the shape of those great big tits, as well as her trimmed pubic bush.

"Dave, trust me on this. You need a woman who can satisfy all your manly needs, and that's not Cecily. That's ... me."

I jumped up, as if to run out of the room.

"Mrs. Arnold, you can't be serious! You're old enough, well, old enough to be my mother! And Cecily is my girlfriend!"

She pulled me hard against her, kissing me and slipping her tongue into my mouth. I could feel those gorgeous breasts pressing against me, and Eileen slid one hand down my chest to fondle my cock, which was already hard in my pants.

I pulled back, looking shocked. She had a look on her face like a hungry tiger staring at a trapped gazelle. "I can give you what she never can, Dave. Just give me a chance, please!"

And she pulled me close again, for another kiss and more fondling, while I tried to decide how long I'd make her suffer before I gave up.

She gently pushed me back down on the couch, then quickly stripped off my shoes.

"Please Dave, let me show you." She got my socks off, then overcoming my mild resistance she pulled my pants and boxers off too. And within a moment she had dived for my rigid cock, getting her hands around the base and the rest of it right into her avidly sucking mouth.

"Mrs ... Eileen!" I protested, lying back and enjoying the sensations. After Cecily's inexperience at giving head, Eileen's obvious expertise was a gift from heaven.

She was certainly Meghan's equal, in skill and above all in enthusiasm. Eileen made love to my cock with lavish efforts of her lips and tongue—taking it deep, then backing off to caress around the head. Pulling off to suck gently on my balls while stroking my cock, then starting the whole thing over again. And she never took her eyes off my face, watching to make sure I was feeling all the pleasure she was giving me.

When I started shuddering and bucking with my impending orgasm she grabbed my hips and pulled me into her throat, and I think I screamed as I shot into her—it was that intense.

Eileen kept her mouth on me, swallowing all of my load, and when I sagged back in exhaustion she licked and sucked without pause until my cock was clean as a whistle. Then, smiling, she lay her head on my thigh, looking up at me adoringly.

"How was that, baby?" she asked in a loving voice. I didn't reply, just looked back at her, trying to appear disgusted.

"A blowjob from my girlfriend's MOTHER? Are you out of your mind, Eileen? What kind of slut would suck off her own daughter's boyfriend?"

I pulled my pants up and started to put my socks on. "Wait!" she cried, looking horrified.

"Honey, you—"

"Eileen, that was so wrong!" I started to reach for my shoes, and she pulled them away from me.

"Dave, I—I need you now! There's something about you, I just ... please, please make love to me!"

And with this she pulled the negligee over her head, revealing those unbelievable breasts. I could see that her pussy hair was blonde and neatly trimmed.

"Eileen!" I reached for my shoes again and she yanked them away from me, running for the stairs.

"You'll have to catch me, Dave!" she cried eagerly, as she disappeared towards the bedrooms above.

When I found her she was lying on the bed in what was obviously the master bedroom. She was naked, posing seductively on one side, her head propped up on her bent arm and her legs spread wide apart.

"If you want your shoes, baby, you'll have to fuck me first."

"Eileen, this is ridiculous. I can't fuck you!"

"Why not?" she asked, licking her lips and cupping one breast with her hand.

"Well, because ... because you're not slim and beautiful like Cecily. You're kinda fat, actually." This was a lie, of course, but I could see my words strike her like a blow. Her face fell and I thought she was about to cry. And then, she seemed to get even more aroused and more determined.

She crawled off the bed and came to me on her knees. "But baby, I can do things to you that Cecily never dreamed of. Trust me, Dave," she crooned, and she soon had me out of my pants and boxers again. Even after my earlier blowjob, all this game-playing had me more than ready to fuck her.

She sucked me again, more energetically than before, until I was rock-hard in her mouth. And then she pulled me down on top of her. I was beyond fighting her--I wanted to be fucking that pussy!

As soon as she felt me in position, Eileen guided my cock into her. Her pussy was steaming hot, and I groaned as I sank all the way inside her on the first thrust. She wasted no time wrapping her legs around my hips, and began rocking and humping hard against me. She was absolutely wild for it.

Eileen started to come within a few strokes, and I just held on for dear life, plunging hard down into her as she writhed and cried out. It was totally wild, the most exciting fuck I'd ever had. I kept pushing hard, she kept crying out for more, and within about two minutes I heard myself shouting as I shot my cum into her.

I rolled off her onto my back, breathing hard, and as I lay there with my eyes closed she snuggled up next to me, gently stroking my cock and balls. Clearly she was hoping to get one more fuck out of me, and from the way her hand felt she was likely to succeed.

I knew we had plenty of time, so I relaxed and lay quietly while Eileen worked on me. She murmured quietly as stroked my chest, slid her other hand up and down my thighs, then shifted so she could rub her tits across me. I let her do all the work, knowing that before too much longer I'd be pounding her again.

After a few minutes I started getting more interested, and I let my hands roam over her. Eileen really had a fabulous body--lush and curvy and padded, completely different from the hard teen bodies I was used to. Her breasts were both soft and firm, and they felt fantastic in my hands. What's more, Eileen was incredibly responsive, so that every touch and caress made her groan and push herself towards me.

I wanted to touch every inch of her, slide my hands all over her back and her legs and her voluptuous ass--and I did. She loved everything I did and responded in kind, and soon I had another great big hard-on.

Eyes glowing, Eileen said, "oh, I want that big thing inside me again!" and started to pull me down on top of her. But I stopped her, brusquely saying "no, turn over," and pushing her away.

In no time she was on her hands and knees, arching her ass back up at me. I said, "I'm not sure I can do this--your ass is so fat." But as I had programmed her, rather than being offended she was only more aroused by this. She slid her ass back so it rubbed against me, and she said, "you'll love this, baby--it'll be so good!"

Feeling my way forward, I slid my dick into her, right up to the balls, my groin pressed against her ass, and sighed with the pleasure of it. She was so hot, and I could feel her working her vaginal muscles to caress me. I closed my eyes and just soaked in the sensation of being inside her.

Then I began to pump her. I knew it would be a nice long fuck, having come twice already, and I was going to try to drive Eileen totally berserk. In the first ten minutes or so she came three times, clamping me tightly each time with her pussy, her groans and sighs getting louder and deeper and more frequent.

After that I started to insult her, and each time it raised her arousal further. I said, "your ass is too fat," and smacked it, and she started a little, groaning. Then I reached around to hold her breasts, caressing the nipples, and I said, "and your tits are too big and floppy," and I smacked her ass again.

You get the picture. "Your thighs are too flabby," "your pussy is too loose," and so on, each time smacking her butt. Eileen's excitement level went through the roof, until she was gasping and moaning and wriggling her ass around so I could hardly stay in the saddle.

I worked myself up towards what was going to be a volcanic climax; then I pulled her back hard towards me by the hips, over and over, and said, "you're such a disgusting cow I can't believe I'm even fucking you!"

She cried out as another orgasm washed over her, and as she bucked and trembled I slammed into her a few more times and cried out as I came, as hard as I've ever done in my life. We humped frantically against each other until it was done, and then she collapsed flat down on the bed with me on top of her, my dick still buried up to the hilt.

I was virtually asleep. After a few minutes I was vaguely aware of her gently rolling me off her, and getting up off the bed. Soon after that she returned, and I felt her tenderly cleaning my cock and balls with a warm washcloth. I must have fallen completely asleep after that.

I awoke with a start, suddenly worried about the time. Eileen sat on the edge of the bed in her bathrobe, gazing at me affectionately. My shoes were sitting next to her.

"What time is it?" I said in alarm, and she replied, "it's 5:35, honey. Time for you to get ready to go."

"I can't believe I let you do this to me," I grumbled as I got dressed. "You're almost old enough to be my mother."

I headed down the stairs for the door without looking back, with Eileen trailing behind me.

"Dave, can you come back on Thursday?"

"What for?" I said rudely. "I'm not doing this again, Eileen."

"Well, then ... just to talk," she said. "About Cecily."

"I'll have to see," I said, and headed out the door without another word. I knew I'd be back, even if Eileen didn't!

Thursday was a repeat of Monday, with a few new wrinkles. I'd set up Eileen to feel more and more aroused the more I insulted her, so I knew I had to keep coming up with cruel things to say. She was as eager to get me into her bed as the first time, but when we got there I acted as though I didn't want to fuck her.

"Please, Dave," she said. "Wasn't last time good for you? I'll do anything you want."

"I don't know, Eileen. You're not slim and beautiful like Cecily, are you? Sort of big and saggy and--over the hill, I guess."

I could see my remarks stung, but they also made her flush with excitement.

"Honey, I'll do anything you want. And I mean anything."

"Okay," I said, acting reluctant. "Maybe if you closed the curtains and turned all the lights off--that way I wouldn't have to look at you."

If you've never had sex in total darkness you're missing out on a treat. The lack of visual stimuli is a little like being blind--it heightens your other senses. Touch above all, but also hearing and smell, and even taste.

I lay on the bed and had Eileen massage and stroke me all over. I told her I wouldn't put a hand on her until she'd gotten me totally relaxed and then totally excited. And it took at least a half hour of pleasure before I was so aroused I couldn't hold back any longer, before my dick was literally throbbing.

By that point I was lying on my back. I pulled her forcefully down on to me, pushed her knees on either side of me, got her pussy lined up and stabbed forcefully up into her. If she hadn't been so wet I'm sure it would have hurt a lot.

She rode me energetically and fast--spending all that time working on me had gotten her excited too. We bounced and thrust and bucked against one another, while I played with her nipples. I could feel her pussy clutch me whenever I pinched them. When I was ready to come, I pinched and twisted both of them at the same time, and she howled! Her cunt grabbed me tight, and I shot my cum far up into her.

After we rested, she wanted to turn the light back on but I wouldn't let her. Instead I told if she wanted me again she'd have to lick my ass first (no one had ever done that to me before). I got up on my hands and knees and she slid in behind me.

It felt kinky but wonderful. She licked both my butt cheeks, went teasingly up and down my crack, and finally circled in on my asshole with her tongue. I made her keep it up for at least ten minutes, instructing her to use her hands to caress my cock and balls at the same time, and you can bet by the end of that time I was hard enough to poke a hole in the wall.

So I turned around and sat up with my back to the headboard and had her blow me, telling her she had to make me last for at least ten more minutes before I came or I was never coming back. The result was a slow, teasing, controlled blowjob; by the time she finally got me to explode into her mouth I was about ready to beg for mercy.

She wanted to fuck once more after that but I turned on the light, got dressed and left, telling her it was sickening what she'd made me do. I reluctantly let her persuade me to come back on the next Monday, with vague promises of pleasures I'd never experienced before. It would be fun to see what she came up with!

The weeks I spent fucking Eileen were very pleasurable, if a bit demanding. I constantly had to raise the level of her humiliation, to insult and degrade her more and more, and it stretched my imagination to the limits.

The third time we were together I told her that her pussy was too loose and sloppy, and I'd only fuck her ass that day. It turned out she'd had anal sex with her husband and liked it, so the idea didn't bother her. But I made her loosen up her own ass for me, using one of her vibrators while I watched, occasionally pinching her nipples for my own amusement. When I did fuck her ass, she was so deliciously tight and responsive that I didn't last very long. But I vowed we'd be doing that again!