Chapter 8

Life and love with Jennie didn’t really change with the new year. I was hoping that with school starting back up Jennie and I could work on our acting like a real boyfriend and girlfriend, and maybe the other guys in her life would start on some new year resolutions that didn’t include her in their beds, but no such luck. It was especially embarrassing when Jennie was occasionally picked up after school by Troy, driving off with her in his truck while I stood there with limp dick in hand.

Jennie still liked me, still hung out and talked and did homework and as often as not slept in my bed. So, what’s to complain about? Nothing except that some afternoons and many weekends saw her disappear completely, her mom thinking her classmate “Sami” was to blame and me having to make excuses for her absences.

I could have just whined and cut her off. That would have been the best thing to do, showing some independence on my part. Thing is, I still liked Jennie, still got a boner just sitting next to her while eating lunch at school, even knowing that she was probably going to disappear into Sam’s house with no more than a kiss to my cheek. I just hoped that my spineless patience and need for even just occasional access to Jennie’s garden of wonder would eventually lead her to realizing how wonderful I was.

On her fifteenth birthday she gave me some extra time and attention, and not only because her mother insisted on a small dinner party with me at the table. Jennie was always able to enjoy sex and was especially appreciative when I made sure she matched me orgasm for orgasm. I know that sometimes she just pretended to enjoy me locking her legs open and pounding her into the mattress, grunting in time as I ground my hips into her, biting my neck as she felt me pour my second load into her. I know how selfish my cock can be and I’m sure Jennie put up with a lot from me, but I can say that more often than not she’d fall asleep in my arms with a smile and the sheets wet with a lot more than what I’d just emptied into her.

This birthday night was special because she seemed to want it as much as I did. She had shown some real desire before, but this was about the time Jennie began demanding it right along with me. Not just happy to drop her panties and pull my face between her legs but helping me unzip and impaling her snatch on my pole before I’d even gotten my shirt off. I didn’t know if Lone had given her a special pill or it was just that time of the month, but I didn’t complain.

On that night and true to form, her riding me on top made both of us happy. With my fingers down between her legs, she rode me like she wanted to break the bed in half. Two minutes after unloading inside of her tight little hole Jennie was back at it, sucking my dick clean without me even asking, then seeming to shake with need as she wagged her ass at me and invited me in for a second run through her twat.

It was a level of demand and desire I only rarely before seen in her, and boy did I take advantage. I had her face crushed into the bed as my cock pounded into her from the rear, laying into her for a good ten minutes before flooding her pussy with a second helping of cum. Thankfully she had wet the bed at least once during this second rampage so she didn’t complain when I crawled up and gave her a goodnight kiss.

The next morning was no different, Jennie feeling me up and giving my sleeping cock a bit of mouth action before I even hit the bathroom. I was a little surprised but didn’t stop her. Let me tell you, Jennie was really good at giving head. I still preferred burying my cock deep inside her pussy, but when she felt the desire, she could suck and swallow as through she was born to do nothing else. I was looking forward to pouring a load down her throat, but she suddenly turned around and rolled me over on her, legs wrapped around my hips and pussy dripping wet and hot to go. It was more work for me, and I was a little mystified by the sudden early-morning need she had for sex, but no way did I question it. I pounded away and added another few million sperm to all the rest of me swimming around inside of her. She complained when I pushed in too far, but her loud squeals and bites to my chest let me know I was a wonderful lover, something every man wants to know. As I breathlessly collapsed onto her I prayed that Jennie had these same physical needs every night for the coming month.

When we finally made it out of the bedroom and into the kitchen, her mom was there and I had to blush when her first words to us were, “Well, I see the two rabbits are finally ready to take a break from their morning exercise.” Jennie just threw out a “Mom” and rolled her eyes, but her mother was smiling and treated me as though I was her newly anointed son-in-law rather than the next door neighbor sex addict who had just plundered her daughter’s most sacred spaces. Then her mom mentioned that maybe Jennie’s bed sheets needed to go into the washer. I blushed double that time and the mom laughed.

I would have been a happy young man, my girlfriend suddenly developing an insatiable appetite for what I had in my pants, but of course it didn’t stop with me. I might have had special privileges for her birthday, but Jennie loudly announced plans to spend the next couple of nights at “Sami’s” place, supposedly to study and then walk to school with her fake girlfriend. I didn’t say anything, though her mother did look hard at me for a long moment before turning and saying that she expected Jennie home for dinner Monday night. No way my mind couldn’t imagine the older and more sexually voracious Jennie around Sam or Troy or the other guys. I of course tried to talk Jennie out of leaving, inviting her to a movie and dinner out, but she had her mind and very likely her cunt set on enjoying life in ways my brain could hardly imagine.

Never did get details on what went on at Sam’s, not that Jennie ever told me much about what went on over there. There we were, just a few weeks into the new year, my so-called girlfriend bursting with new-found sexual desire but just as likely to pull other guys into the bedroom as she was to crawl into my bed. I should have gotten mad, but instead of slamming the door in her face, I doubled down and spent even more time in her house, even when she wasn’t there.

I kind of adopted her brother, Tim, and started doing stuff with him like he was my own kid brother. We’d play catch in the back yard or maybe fix a snack before helping him with a science project. It was fun. Some nights I slept in Jennie’s bed even when she wasn’t there, getting up and helping her mom with breakfast and the dishes as though they were my favorite weekend chores.

A few times I brought games over from my house to play with Tim. We’re talking old stuff my dad and sisters and me used to enjoy, like battleship. Even his mom got into a game called clue. Pretty soon every weekend night had us sitting down together to play a board game or watch a game show, with or without Jennie. That’s when things really started to change.

I had long before been calling Jennie’s mom by her first name, Sherry, but mostly just saw her while pulling Jennie into the bedroom or out the door to school. Since December I had started doing a lot of other things with Sherry as though I was her next door friend, Jennie only showing up to do homework or hang out with me every odd day. Sure, Jennie was a little surprised at finding me in her house so often, but she assumed it was only because I was waiting for her.

Which was true. I was seriously trying to get Jennie to see me as her one and only. Any time I saw her at school I’d kiss her or put my arm around her and ask about her classes. I passed her notes, wrote (sometimes stole) bad poetry, did portions of her homework, and even helped in preparing her bagged lunch for school.

On those nights that she was willing to grant me access to her feminine delights while behind her bedroom door, I made sure to suck and lick and caress at least as much as I fucked. More importantly, I stayed awake afterwards and talked with her, discussing everything from her growing tits (wonderful) to what I thought of the school’s pizza (bad). I was intent on being the best boyfriend ever.

Thing is, she knew what I was doing and finally called me on it. Didn’t happen until Valentine’s Day. I had gone all out, first buying a valentine for Jennie, then writing her a poem, then realizing I needed to make one for Sherry, so of course another one and maybe a candy bar for Tim, and finally a simple “love you Dad” card for my father. Nothing elaborate, but still more than anything I’d ever done before, and it went exactly the opposite as I had hoped for. Sure, my dad liked his card and Tim just paid attention to the candy bar, but when I slipped Jennie my card and poem and candy and pressed flower at lunch, she just thanked me, and right there I knew something was wrong.

Walking home from school she laid it on the line.

“I really appreciate it Taylor, I really do,” she said, holding my hand even as I winced in pain at the true meaning of her words. “You’ve been trying so hard to be so nice to me, and you’re just making me feel really nervous, like I want to run away every time you try to kiss me.”

“But, I’m your boyfriend,” I said, as clueless as ever. “I thought you’d like what I do for you. If anything I want to do more, but you keep telling me to cool it. I don’t go around telling everybody about our sleeping together, or yell out how much I love you, or go all whiney every time you disappear with Troy or Bob or all those guys. What else am I supposed to do?”

Did you read that? A pretty sad list, and only a guy as clueless as me could have said it out loud without realizing the truth. Jennie smiled her saddest smile and looked up at me and yet again tried to remind me who she really was.

“And I get it Taylor. I love it and everything you do for me, but maybe you’re trying too hard. Like the card and poem, they’re so sweet, and I’ll keep them forever, really. But I’m afraid you’re just going to get hurt. I don’t know what I’d do without you. You’re my best friend ever, but just not my boyfriend. I mean, if I wanted a boyfriend you’d be first on the list, but not now. My mind is just too messed up right now and I need you to be my friend first. Do you get it?”

I got it, again, and pretended I even understood, but she knew I was hurt. Jennie was nice enough to promise that she’d be home before eight and spend some special time with me. She even kissed me back when we parted, but we did part, Jennie taking off to be with Sam (and others) for some kind of party they were supposedly throwing for her. I could imagine the kind of valentine party Sam would arrange for her but chose to save myself the pain and pushed those thoughts aside. At least Jennie agreed to some time with me later on and I walked on home alone.

I was helping Tim with some homework when Sherry walked in, fresh from a long day of work and looking as nice as ever. I’ve mentioned how hot she looked, shapely, her breasts always prominent no matter what she was wearing, and an ass no pair of skin tights from the flea market could improve upon. Still, she was Jennie’s mom and I made sure to keep repeating that every time we were sitting next to each other.

You know what I’m talking about, right? Like when a hot looking girl has the top half of her tits completely uncovered and sticking straight out and you’re supposed to look only at her eyes. Or when her perfume or some other more earthy womanly odor is thrown your direction and you’re not supposed to say anything. With Sherry it was all that, but also her strawberry blond curls bouncing on her shoulders, the sight of her navel riding high above the edge of her slacks, and the feel of her leg brushing mine under the table. It all drove me crazy. The only thing that saved me was being able to disappear into Jennie’s room and bury myself balls deep into her less sexy but more available pussy.

Don’t get me wrong. Jennie was still my girlfriend, at least in my mind, but her mother was a woman, a really fine looking MILF that made my cock stand up and leak every time she entered the room. I know grown men lust for girls like Jennie, maybe lusting for their smooth skin and tight holes and pert tits. Sure, I get it, but for a guy like me, grown women of Sherry’s age and shape were like sirens in the night.

Still, I played my part as the adopted older brother to Tim and hoped for boyfriend of Jennie and pretended Sherry was just one more mom on the block. Which brings us back to her entering the house while I worked with Tim. We were all very polite and she asked me to stay for dinner (not unusual) while asking if I knew where Jennie was. I lied, told her that Jennie should be back from Sami’s before 9, and offered to help her in making a salad. All very nice.

Then Tim took off for his room and Sherry moved over next to where I was standing and said, “Thank you for the valentine Taylor. A woman still appreciates those little gestures. I hope Jennie does.” And then she leans in, putting a hand on my far shoulder, her hair tumbling down and filling the air with her scent as she kisses my cheek. Not just a peck, but a kiss, a suck in and a tickle with her tongue, and without any thought at all I turned and finished the kiss, my lips to hers, our tongues touching for just a moment, my hand even reaching out to lightly touch her ass before we parted.

That should have been the time that all my fantasies came true, where I levered Sherry down to the floor and pulled her in for a long kiss, or perhaps where she grabbed my hand and pulled me toward her bedroom door. Sadly, reality intervened and we went back to our expected places, though not before her eyes opened wide with my returned kiss, her head turning and her mouth forming a smile of recognition if not invitation for more. I just swallowed and headed for the refrigerator, glad that she hadn’t slapped me and hoping she hadn’t noticed the very prominent boner forcing its way down the leg of my pants. She acted like it hadn’t happened, but it had, and all through the early evening everything I did or said was affected by those few seconds of intimacy.

I breathed a sigh of relief when Jennie walked through the door about 8, giving out apologies and talking about her pretend friend Sami and how they hadn’t eaten anything but cupcakes and how hungry she was. All of that was fine, even normal, but jealous not-quite-a-boyfriend that I was, as she stood talking with her mom my own gaze focused on what she was wearing. No socks, though I knew she had worn pink socks to school, and without the bra she always wore to school, her nipples pushing out through her blouse. Nothing unusual, sad to say. I think Sam had a drawer full of clothing she had somehow forgotten at his place.

What made me steam this night was her slacks, white with straight legs and almost as tight to her ass as Sherry’s slacks often were. The pants looked fine, zipped and fastened with a belt, but with a dark wet stain where they fit snugly into her crotch. Maybe she had been in a hurry, having a little fun with Sam and Troy before realizing the time, pulling on her pants and rushing home without panties or adding a panty liner or even waiting for their loads to drip out and be washed away with a quick shower. Maybe Sherry noticed, maybe not, but it was hard for me not to stare and wonder just how many loads of valentine-laden cream it took to drench the crotch of her pants.

When we finally called it a night and Jennie and I disappeared into her bedroom, I actually found it hard to boner up, to kiss and love and make use of all the rights and privileges Valentine’s Day guarantees lovers everywhere. The thought of her wet pants and what the guys at Sam’s had already blown up her hole made it difficult for me to enjoy any attempt at making love to her.

What finally got me hard and ready to fuck was thinking of Sherry, of the feel of her hair and the softness of her lips on mine, and especially the feel of my hand on her ass. I felt like a liar and cheat, imagining Sherry’s body in place of Jennie’s, imagining a different pair of breasts to suck on, another ass to hold onto as I laid waste to her little girl’s cum-full cunt.

Jennie wasn’t into it, lacking the sexual lust she had shown just a week before when we were alone in my room. I didn’t care, my cock hard at the thought of Sherry being under me, my anger fueling my demand for Jennie to give me what I thought I was owed. I’ve got to admit it was rough, locking her legs out wide, then pushing them up over her head and pounding into her for what I felt was a well-deserved release of all my sexual frustrations in a flooding of her cunt. After a few minutes of rest, I forced Jennie to then clean me off, happy in the knowledge that she was probably sucking down a half dozen different flavors of sperm-laden cream, all ripening in the depths of her pussy.

More thoughts of Sherry got me hard enough to roll Jennie over and do it again, though a little longer and with more care, my guilt at what a jerk I was being forcing me to whisper out how much I loved her as I filled Jennie’s hot little box one more time. She was nice about it, even pretending an orgasm before I softened and allowed her to pull away and drift off to sleep. I was tired but couldn’t sleep, staying up half the night and wondering who I was and what I could possibly be for a woman like Sherry.

I felt like a car doing ten thousand rpm in second gear, my mind screaming at the stress, but I tried my best to act as though everything was normal. I sensed the same with Jennie and Sherry but didn’t know what to do about it. Jennie began making more excuses, spending more nights and long weekends at Sam’s and Bob’s, though I never knew just who she was hanging out with until she let go with some hint about this guy’s lasagna or that guy’s Jacuzzi.

Sherry put up with the lies, pretending to believe all the girly slumber party stories Jennie made up, ignoring the occasional hickey or overabundance of male cologne Jennie brought home with her. Sherry didn’t know what to do any more than I did, so we all just pretended everything was fine, yet all on edge as we waited for the inevitable crash and burn we knew was going to happen.

Believe it or not, it worked itself out, and none of my wild and imagined fantasies matched what really happened.

It was early March, spring not quite there but with flowers already showing themselves in most of the front-yard gardens. I had been helping my dad with his car as he tried to save a few bucks by changing the brake pads on the back of his old sedan. Jennie and I had passed some wonderful hours in the back seat of the car so I had some feelings for it and was happy to assist. We weren’t done until almost eleven. It was a Friday night and after a shower I decided to go over to Jennie’s. I knew she wasn’t at home, probably wouldn’t see her until Sunday night when Bob or Troy or somebody dropped her off down the block. No matter. It would still be nice to sleep in her bed and maybe jerk off into her sheets while breathing in her scent from the bedding and her pillow.

So I pulled out my most prized possession and used the key to open the front door, quietly making my way through the darkened house and into her bedroom. In the low indirect light coming through the window I was surprised to see her form, laying on her bed, back to me but covered and probably asleep. I stripped, not even bothering to keep my boxers on, cursing myself for being a sex hungry teen while begging god to let Jennie wake and pull me in of her own free will.

I slipped under the covers and pulled myself into her, spooning her hot little ass, grinding my crotch in while moving my arm over her shoulder to grab one of her breasts, my face pressing into her hair and kissing her head. That only took a second, and in the middle of that second I was immediately aware that this wasn’t Jennie. For some reason Sherry was there, occupying Jennie’s place and now waking to find some strange guy molesting her in her own house.

I knew what I had done and immediately pulled back, wondering if I should try to sneak out and pretend nothing had happened. As I froze in mid motion, my cock hard and pressing into Sherry’s ass crack, one hand holding a very full and firm breast, my face still buried into her curls, Sherry brought a hand of her own over and put it on my hip, pulled in on my bare ass and whispered into the night. “Taylor.”

It wasn’t a question. She knew and yet wasn’t throwing a shit fit about my leaking cock pressing ever deeper into her ass. I just swallowed, still unsure of what I was supposed to do. Sherry rolled toward me, disengaging my cock but bringing her face even with mine and pulling me into a kiss. After that, all thought vanished and I simply went with my gut, feeling that I had been given a free pass to do anything I wanted with the sex goddess next door. No thoughts or guilt trips about Jennie. Maybe one about what Tim would think, maybe a couple about making sure I didn’t blow it all in a two-minute quickie, but mostly I simply enjoyed fucking and making love to a woman I had been obsessed with for the past many months.

No talking, no explanations, just sex. After our shared kiss, we both acted on a wordless agreement for something we couldn’t speak of. We went at one another with a lustful passion Jennie had only occasionally shown. Sure, Jennie liked sex, had even started demanding it like the hormone-fueled teen she was. Fucking Jennie was the one good thing about my whole life, but Sherry acted as though she lusted for me, demanded me, and she fucked me back as hard as I fucked her. I wanted all of her at once, kissing her, smelling her hair, moving down to try sucking in on one of her tits, all the while thinking of what she must taste like, of how the pussy of a grown woman might smell and feel and taste differently from a barely teenage girl.

I hardly got to suck on her very prominent tits, Sherry wrapping her legs up and around me and pulling my hips down to merge with hers. The message was unmistakable and I was happy to oblige. I moved my hands down to feel up her ass, her most perfect ass, and pushed my straining pole through her wet slit just once before pulling back and pushing deep into her. Let me tell you, Jennie’s hot little hole was tight and warm and wet and wonderful to fuck, but it took a little time and I had to be careful about depth and timing and all sorts of things.

Fucking Sherry was so very different. Definitely easier to push into, but hot and wet and waiting for me, and I could swear her pussy lips sucked my cock up inside of her. Only a half dozen thrusts found my balls pounding into her twat as she fucked me back double time. That was the amazing thing, her pussy seeming to suck at my cock, like a wide open mouth of flesh sucking on the entire length of my rod, sucking me in every time I pulled back, over and over again. And she could take me all in, Sherry’s legs circling my hips and pulling me down, her feet slapping down on my back as I pounded as hard and as deep into her as I could.

I was hardly aware of anything else at the time, just the joy of being able to let go and fuck a woman for the sake of fucking her, but a couple of other things did burn themselves into my memory. Like being able to kiss Sherry while we fucked each other. With Jennie being so much shorter than me, when we were fucking chest to chest, my head was usually up above hers and I had to put up with kissing her head and smelling her hair. But Sherry was taller, perfect for me, and as our hips and groins ground into each other, it was wonderful to kiss her, to bite her lips, to play with her tongue, to listen to her moans and grunts even as I whispered into her ear how long I had waited to make love to her. And the noise, the slapping together of our bodies, wet from sweat and shared secretions, but also the noise of the bed, the entire frame rising and falling on the floor, making me think about waking Tim and a little fearful that the entire wooden frame might break in half. But we never slowed.

It of course ended all too soon, my balls primed and loaded and ready to blow and my mind unable to hold my needs back for more than a half dozen minutes before the riotous fuck finally stimulated me beyond control. I groaned out my intent to cum and Sherry just held me closer and whispered, and I’m quoting here, “Cum in me Taylor. It’s OK. Cum inside me.” I hooked my chin over her shoulder and ground in hard and deep, my balls pressing hard into Sherry’s open legs as they began pulsing out a dozen hard jets of my cream into her.

I groaned out my delight, my hands pulling Sherry’s ass cheeks wide as my cock pushed as deep into her as I could shove it, relaxing my rough physical demand only as the pressure in my balls eased and my torrent of cum slowed to a trickle. I wasn’t forgetting myself at all as I bent in to bite Sherry’s neck, then up to kiss her, to suck in her tongue, then grinding my softening cock into her just a little more as I groaned out loud into her ear, “My god but that was the most wonderful fuck I’ve ever had.” And Sherry just lay there, her legs out wide, her arms encircling me and lightly massaging my back as she kissed my cheek and said, ‘Yummm.” I’ll never forget that.

I can still remember the feel of Sherry’s hair against my cheek, the scent of her perfume, our tongues and teeth touching as we kissed, and even the reluctance of my still-hard cock as I pulled out of her and rolled off of her sweaty naked body. My breath had finally slowed and there we were, legs crossed, hands on one another’s chest, and me totally unable to think of a thing to say. I mean, I’d just had one of the greatest fucks of my life with the hot mom of my girlfriend and I couldn’t think of what to say to her, so I didn’t. Meaning, I just went with something like “Wow, that was great,” and stuck with leaning down to suck in her nearest tit and pushed a hand down to feel up her clit. Seemed better than just lying there in silence, and I sure didn’t want to talk about what Jennie might say.

Have I mentioned that Sherry was a really hot looking woman for being the mom of two kids? I had always admired her tits, had always had to consciously force my eyes away from her chest whenever she faced me, and now it was my duty to do nothing but give them all of my attention. Even laying down on her back next to me they rose up, like perfect ovals with tall hard nipples pointing to the ceiling. As I rose up on one elbow and leaned in to suck in the top portion of the nearest breast, she showed her appreciation with a low moan and a hand on my head.

That’s when I felt her other hand, down to hold the hand I had already pushed between her legs. She took my hand and began rubbing it through her slit, and I knew what she wanted and needed. I had done this with Jennie enough times to know how sometimes a woman needed a bit of stimulation after a man (like me) had made it to the finish line just a little too quickly. I had gotten pretty good at knowing just how to use my fingers to make Jennie happy, though we both still preferred the use of my tongue. As I felt up Sherry and began working on her clit, I knew immediately I wanted to open her legs up in the bright light of morning and get a good look at her twat.

First off, I could feel that Sherry had a huge clit. Jennie’s was barely noticeable unless she was really ready to explode, but Sherry’s stuck out as hard and as thick as one of her nipples. Second thing was that she had something else down there, like a ring or piercing, something I’d only read about. As her hand guided my fingers around and around her upper slit, I could feel her clit even through her bit of bush and her thick cunt lips. Sherry essentially controlled my hand for the next minute, showing me exactly how to rub her off, before letting go and trusting me to carry her to the edge and throw her over.

As she neared her own completion she leaned into me, moaning into my neck, her legs opening and closing on my arm, and then a hard sobbing cry and deep moan as she convulsed and locked my hand and arm in place. For another minute we just stayed that way, both of us sweating and breathing hard and enjoying the hot wet afterglow of sex. Then Sherry rolled back onto her small bit of bed and pulled my hand up, fresh from being drenched down below, and kissed it, sucking in my fingers before then leaning over to kiss my cheek, saying simply “Yeah. That was good.”

I still didn’t know what to say to her, but I knew what I wanted. More than anything I wanted Sherry to go down on me, to slip down and suck in my cock and clean me off. After fingering Sherry into her well-deserved orgasm, I was newly hard and in need. Something in me wanted to see Sherry sucking on my sticky wet cock, and maybe even watch her swallow down a new load. I rolled in, kissing Sherry’s neck and grinding my shaft into her thigh, ready to push her head down and show her what I wanted, but that’s when she made an unspoken demand of her own. Sherry raised a leg and wrapped it over my hips, then reached down and pulled my erect and leaking pole up and began rubbing it through her very wet slit. I got the idea right away and reached down with my own hand, helping her play my cock back and forth through her folds of hot wet flesh before positioning the head of my cock just right and pushing in.