Chapter 11

I woke only slowly, an early morning ray of sun making it through the curtains and lighting up the far edge of the bureau. Sherry’s bureau, itself covered with make-up and jewelry, bits and pieces of modern womanhood I could happily now claim as a part of my life. Yeah, you can read smug satisfaction in that statement. Waking up in Sherry’s bed with a very naked Sherry lying next to me gives me that privilege.

With one hand I was able to reach out to touch the naked form lying next to me, the woman’s firm breasts a good two sizes larger than Jennie’s. My hand dipped down between the woman’s thigh’s, her sparse pubic hair no impediment to my fingers as they felt out the small silver ring that punctured the upper edge of her labia. Wet, the inner folds full of moisture, their feel making me smile with anticipation.

Sherry had groaned and turned away, but I followed, my own naked body nesting into her back as I bit her neck and breathed in her scent. At that moment life was wonderful, and Sherry was at the very heart of my feeling of great contentment.

It had been three weeks since Jennie’s great disclosure, filling me in on her hidden past and then coming clean with her mom about what she had been up to. I stayed out of it, letting Jennie gloss over details and simplify events as she saw fit while trying to explain herself to her mom. No mention of the harem of guys at Sam’s house or of Bob or any of that. Just Jennie and the one true love she finally dumped me for. And who was that? Troy.

Of course. Even I could have guessed it. Jennie coached me on what to say to her mom should Sherry grill me for details, which she did. Just me and Jennie as high school lovers until the handsome and much older Troy came her way. I practiced that story a dozen times, happy to lie for Jennie’s sake, but also for my own. Given that Sherry had welcomed me into her arms and between her legs on a nightly basis I really didn’t care. Jennie could move into Sam’s place and do whatever she wanted with the entire bunch of guys and all I’d do is shrug. With Sherry actually expecting me to follow her into the bedroom every night, I was in heaven.

Well, almost every night. A couple of times Sherry had come right out and said, “Listen, Taylor, I need some sleep tonight. You go on home and maybe I’ll see you tomorrow. Okay?”

It wasn’t so bad. After all, what guy doesn’t like it when the hottest MILF on the block is complaining that he’s keeping her up all night? On those nights it was hard to walk past Jennie on my way back to my dad’s, her smirk making me want to drag her into her bedroom and remind her what I could do. But the next day I was sure to have open access to a revitalized Sherry, and if anyone it was me who needed the sleep.

In just a few weeks I’d gone from newbie apprentice to Sherry’s sexual needs to absolute master lover. At least that’s how I felt. She wasn’t at all shy about letting me know what she wanted, what would excite her and what she’d put up with. Just running it all through my mind made my cock boner-up, even after a night when I’d emptied myself twice into Sherry.

First off, she was real particular about kissing. Mostly just before and during our merging of bodies, but not so much after. We had our best kisses while my cock was pounding into her, her mouth sucking my tongue in just as her pussy climaxed and sucked my cock dry.

Of course she really enjoyed me kissing her body, tits and ass and neck and mouth, but after giving me a lesson in female anatomy, she came to really appreciate what my mouth could do between her legs. Sure, Jennie was always happy to have me go down on her as a part of our foreplay, making sure she was wet and willing before I pushed myself inside of her. She liked it nice and long and gentle, and as long as I wasn’t forcing my cock down her throat, Jennie was up to riding my tongue half the night.

Sherry was different. She liked it hard, with my teeth and lips grasping her clit, sucking in and roughly licking her oversized nub as hard as I could. Jennie could take a half hour of my gentle sucking before having an orgasm, but Sherry wanted me chew on her clit and bring her to an orgasm within five minutes, which I’m proud to say I’ve done. She was a lot wetter than Jennie and a lot less apologetic, simply crushing my head between her thighs as she rolled around on the bed, then laying back and letting me know she wasn’t done with me yet.

I’d also gotten to know what she wanted in the way of lovemaking. Or, in my mind, how she liked to fuck. Even after drowning me while climaxing with my teeth wrapped around her over-sized clit, she liked me to push into her slow and shallow before building to a hard hip pounding fuck. I do mean pounding. Sherry was looser than Jennie but she could take my entire length and still ask for more. As she rose to an orgasm she liked it deep, her legs up and waving with our bodies slapping together even louder than the creaking of her bed.

She wasn’t as flexible as Jennie, but Sherry could hold her legs up and out, even wrapping her feet around me as I pulled her ass out and ground my cock as hard and deep as I could. After five minutes of love making, of kissing and tender caresses, Sherry was up for a long hard fuck like I could never give to Jennie. Jennie always wanted me to hold back, happy with just my first few inches, but Sherry was good for an hour-long fuck that would literally have my balls pressing into her ass. I’ve never experienced anything like it and, according to Sherry and her very wet bed sheets, I was doing a good job of making her a very contented woman.

So, here I lay, spooning the naked ass of a woman I’ve very much enthralled with. Weeks of sex behind us, and in my mind with many more to go. What made it even better was remembering that it was my birthday. Eighteen, a legal adult, and though Sherrie was still well over a decade beyond me in age, I felt as though my childhood was now behind me and I could start being more of a man to her, an equal partner in a real relationship. I wasn’t thinking marriage or anything, but I was obviously taking my connection with Sherry pretty seriously. I felt like I had moved on, about to graduate from high school and taking on more responsibility with a woman I couldn’t get enough of. Hell, I was even coming to think of her family as my own. Kind of weird to imagine Jennie as some kind of daughter to me, especially after everything we’d done together, but that’s the way it was. It kind of overwhelmed me.

My birthday, my adulthood, was in mind as I moved a little closer to Sherry, my manhood pushing into her ass, one hand moving over to massage her nearest breast as I kissed her neck. I was expecting some special present, a moan of pleasure with her legs opening and her already cum-full cunt making itself available to me for a morning run. That was on my mind, but after a pat on my thigh and a quick “morning Taylor,” Sherry rolled away and up and out of the room. Not totally unusual, but I really had been hoping for her to show some appreciation for what I’d done for her the night before. And besides, it was my birthday.

Jennie and I had school. Taking a sack lunch and walking off with a bag of books kind of ruined the whole “Today I am an adult” thing. Even a little embarrassing as Sherry stood in the doorway and waved us off. I played it all down with my friends, plenty of guys lining up to give me a shot in the arm, but I got through it and was pleasantly surprised when Jennie insisted on walking with me all the way home. I enjoyed that, just talking out stuff with her, and it gave me another chance to ask about Troy. Or more importantly, Troy’s coming face to face with Sherry.

That had happened a week before. I had been busy trying to memorize the feel of every bump on Sherry’s left nipple with my tongue, trying my best to unsnap her shorts when she casually mentioned that Troy was going to come over the next day. It was the kind of thing Jennie should have told me about, but she was still a little miffed about the private time I was spending with her mom and had been doing her best to make sure I knew she was ignoring me.

Of course I wasn’t part of the meeting. I had work and I wasn’t asked. Sherry kind of filled me in, like letting me know she approved of Troy but not the relationship. No doubt she had a lot of worry about her under-age daughter doing a lot more than just dating a guy who was in his early twenties. Sherry asked me about him and I told her the truth, but only the most rigid version of the truth. Nice guy, really into Jennie, seems kind of straight and law abiding, and that I’d trust him if he ever promised to do something. Totally true. Sherry wanted more but I played dumb, which wasn’t hard given how little I really knew about what Jennie and Troy and various others had done over at Sam’s. Sometimes ignorance can be a wonderful thing to hide behind.

Sherry knew Jennie and Troy would be hooking up but decided she couldn’t do much to prevent it. Otherwise Sherry talked out her worries, her pain at being a mother to a young girl with far too much experience behind her, and tried to see the bright side of Jennie not trying to hide her relationship with Troy. I still wanted to know more about that meeting and walking back home with Jennie on my birthday gave me a chance to pull some details out of her.

“Sherry told me a little about what you guys talked about, you know, with Troy. Mostly she’s just unhappy that Troy is even around but she doesn’t know how to stop you from seeing him. What went on?”

“You mean my mom and you didn’t talk it all out, like give you all the details of what we said? No surprise there. She’s not that into sharing. Get used to it.”

“She’s just not as talkative as you are,” I shot back. “Give it. What happened? I know she’s not going to call CPS but she’s also planning on keeping you on as short a leash as she can. How’d it all come down when you guys met?”

Jenny shrugged and showed her poker face for a few steps, then broke out into a smile that I only rarely got to see. She looked almost radiant as she recapped what she and Troy and Sherry had talked about.

“Troy was, like, real polite, but he never apologized. He just sat down and explained that he knew how young I was and how nervous mom probably was and everything. Troy even offered to show her his work receipts and his mom’s telephone number. I think mom liked the idea that he still lives with his mother. Mom was bursting, like red in the face and her hands clenched in two fists. You could tell she wanted to blow, but she just sat there and asked questions and Troy answered with me sometimes chipping in.

“In the middle of it all, Troy kind of lost it, but in a good way. Mom was essentially asking what his intentions were, meaning she was wondering if he was just going to knock me up and leave me stranded, but Troy interrupted her and said ‘Oh, no Mrs. ***. I really like Jennie. Being with her is the closest thing I’ve ever come to loving someone. She’s everything to me.’”

I could swear Jennie’s voice broke, her eyes staring down at the ground, but then she raised her head and looked at me with what seemed to be tears in her eyes and said, “It was the most romantic thing I’ve ever heard. Almost kissed him right there in front of mom. Stunned her too, but her fists kind of melted away and she seemed softer after that. We talked a little more, just about stuff, but then we all got up and Troy left and that was it. No shouting or anything. Major stress though. Don’t want to do that again.”

To be truthful, I was hurt when Jennie mentioned Troy being so romantic. All my overtures and attempts to get her attention seemed to have just been pushed aside and forgotten. It hurt, but I just shrugged and forced myself to move on. She seemed radiant when talking about Troy and I didn’t want to come off as some kind of sore loser.

“So, she’s OK with this older guy seeing you. I mean, like taking you home, maybe spending the night and stuff?”

Jennie punched me but in a playful way and seemed happy to answer. “You know, they never talked about what we were all thinking, about what we do every time he picks me up. Mom did ask me later about birth control, but she’s done that before. But no, no spending the night at Troy’s. And that whole Sami thing is gone too. She didn’t come right out and say it but I’m pretty sure she knows Sami was code for spending time with Troy.”

Then Jennie stopped and touched my arm and said something that came hard for her. “Thank you. You could have put me through some real shit with mom but kept it all to yourself. Troy is willing to let my past stay that way. Glad you’re there too, at my back.”

Pretty serious stuff, so I of course had to lighten the mood. “So, about Troy coming over to visit. I’m not sure your little bed is big enough for his much larger frame. It hardly fit the two of us.”

“Shut it Taylor,” but Jennie was smiling when she said it. “I’m sure mom told you that Troy isn’t allowed any visiting rights. And sure as hell no key to the front door like you had. I’m pretty sure she’s going to nail that window shut too.”

“So, she really thinks she’s just going to keep you under house arrest? I know for sure she’s assuming you guys are going to be getting together every chance you can.”

“Oh, yeah. As long as I’m home before 10 on any given night, she won’t complain. No visits by Troy unless she’s there, but she knows that Troy picks me up from school a few days every week.”

“Which reminds me. Thanks for walking with me today. Nice to talk with you.”

“Happy to hang with you, birthday boy. Just don’t expect me to do it all the time.” Jennie even let me hold her hand for the last block of our walk home.

So, back to my birthday. Total surprise for me when people started showing up about five. Dad’s little barbeque turned into a major cookout, with him doing burgers and ‘tater tots, but otherwise having friends bring in a bunch of other take-out food. Jennie and Sherry and even Tim showed up, along with a few of my dad’s friends and a couple of my classmates that Jennie had talked to. I was blown away. Didn’t even know what to say when my dad handed me the keys to a well-used car he and a friend had been fixing up on the side. Seriously, my own car. Totally awesome.

Felt good to be friends with Jennie again. I’d really missed her. There she was, singing happy birthday to me but then under her breath she joked about how now my ass could be hauled into court for statutory rape if I ever snuck into her bedroom again. I would have brought up the names of a dozen other men but her smile told me she was just trying to get to me. I think that was when I realized Jennie was first and foremost my friend, maybe my best friend, and that made me really happy.

Then right across the table from me was Sherry, acting polite with my dad and talking with a couple of his friends while seeming to ignore me. She had on a standard one-piece dress, but it showed off everything I loved about her. Sexist male pig that I am, I loved knowing I was the only one in the crowd with the right if not expectation to rip the dress off of her later in the evening. Only one of the friends Jennie had invited over knew anything about me and Sherry. I was busting out with pride because he was there and checking out Sherry while knowing what I had done with her in the bedroom.

As it was all winding down I tried to help with the clean-up, but my dad just pushed me off while saying, “Go ahead Taylor. I’m sure Jennie’s waiting for you. But you be careful with her in your car. No messing around. Don’t want to hurt a little thing like that.”

It struck me that my dad had no idea what had happened between Jennie and me, or what was going on with me and Sherry. No way I was going to break it to him either. Tell my father that I’d finished screwing around with the next door girl and had moved on to sleeping with a woman who could almost be my mother? Not going to happen. Not yet anyway. I knew I’d have to slip it into a conversation sometime, but I didn’t know how.

Walked over to Sherry’s. Oddest thing was that it felt as much like my home as at my dad’s, the little house where I’d grown up. Tim was there doing homework with an extra piece of cake at his side. Sherry was preparing our lunches for the next school day, and Jennie was in her room. All was well with the world, and I couldn’t have been happier.

Until that night of course. Sherry was uncharacteristically frisky. She likes sex, of course, but apart from being a little coy, she’s pretty straightforward and even in my face demanding of what she likes and how she wants it. So this playing around, like coming at me on her knees with only a pair of lace panties on was totally unusual for her, and boy did I show my appreciation. Straight out of fantasyland and best birthday present ever.

I knew it was an act, but just for me and I enjoyed every minute. Pulling me into the bedroom and kissing me, like a real long loving kiss. Not something I normally get from Sherry unless we’re entwined on the bed and she’s about to clench her pussy around my cock and let loose with a bed-wetting climax. This time she kissed me as though she really cared, then pushed my jeans down, pushed me onto the bed, and crawled up between my legs with a fun little growl. Seriously, she just doesn’t do stuff like that, but on that night she did it for me.

As she went down on me, and we’re talking deep-throat ball diving here, I was able to lever her hips over so my face could plunge into that wet river canyon of a pussy I had gotten to know and love so well. It depended on her mood, but on this night she locked her knees around my head and ground down on my tongue as hard as her own head was sucking on my dick. Even without her attempt to suck me into ecstasy, I was always happy to drink her down. She had let me help trim her fur once, at my request, and wound up showing me all the ins and outs of what made up those layers of flesh between her legs. After that graduate level kind of training, my tongue was pretty good at bringing Sherry to a fast boil.

I almost lost it first, Sherry knowing even more than I did about how to get a cock to rise and explode in under a minute, but she held back and just played with me. Five minutes of giving her clit a hard sucking tongue lashing and she sat up, grinding down on my face, essentially masturbating on my tongue and teeth. While my head was trapped between her thighs, she began giving out this series of staccato grunts I’d come to know as a signal that she was about to climax and death to anybody who got in her way.

Sherry’s orgasms were nothing to joke about, especially when it was my face she was smothering. If it was my cock up her hole and me pounding down from on top it was wonderful, Sherry’s twat twitching in joy, almost clenching my cock and sucking my dick into a climax while she experienced her own very liquid release. This time she let out a low wail, her hips jerking back and forth on my face double time as her climax was made evident by a flood of secretions. I was happy to suck the river of love juice down and swallow what I could, even proud in the knowledge that I was the cause of her release.

I knew I had done good when Sherry finally collapsed down onto my chest and groaned out into the darkness, “God but I love a man who eats bush. I needed that.”

She only rested for a few seconds, opening her legs to give me a chance to breathe and then turning around, straddling my crotch with her still dripping twat and slowly impaling herself on my very frustrated cock. She didn’t mind licking her liquid excess off my face either, something Jennie never cared for. We went slow, kissing in a way she didn’t always get into while slowly stretching her vaginal canal out with my more than eager pole. Five minutes on and she was ready, pounding down onto me for a minute before holding me tight and grinding up and around, her pussy seeming to be unquenchable as Sherry demanded ever more from me.

I had to disappoint her that first time, my balls letting loose before she was able to reach a much anticipated second climax of her own. She’s cursed me out before, but she also knew what I was capable of. As I softened Sherry pulled herself off of me and crawled backwards and did something she had previously shown a dislike for. Probably with my birthday in mind, she sucked my wet and cum slathered cock into her mouth, sucking and tonguing and swallowing down a good portion of what I’d just blown inside of her. Jennie did this as a matter of fact, like a normal part of our love making, cleaning off my cock while getting me nice and hard for another run through her twat, whether she wanted it or not. Not Sherry, not normally, but she did this time.

Five minutes on my cock was not only clean but hard and ready for another round and Sherry was more demanding of my skills than simply willing to put up with my being a randy young man. She rolled over and pulled me on top, wrapping her legs around my waist and waiting for me to do my duty. Happily. With my balls a good couple of ounces lighter than when we had started, I was able to push my hands under her ass and hook my chin over Sherry’s shoulder and get to business. She had her legs up high and wide at first, pushing her hips up and sucking in my long length of cock as though she couldn’t get enough. Five minutes on, maybe more, and she had another climax, her cunt almost sucking a second release out of me. That’s when she slowed, her legs on the bed and light kisses to my face as I pressed on. When I rose to the golden moment and moaned out her name she kissed me, like lips to lips and tongues entwined, as though she really loved and needed me. That was probably the most special moment of the night. That was the best birthday present, Sherry acting as though she really loved me.

Which I knew she didn’t. I was no love-addled kid, but I did kind of hope she’d eventually come to appreciate me and depend on me and somehow make me an indispensable part of her life. Instead it was me who had made Sherry and her family a part of my life. I was the privileged one, getting to share Sherry’s bed, enjoying having a younger brother like Tim, and getting ever closer to Jennie. It was a second family, shared in ways I knew I was lucky to know, but I also knew it wasn’t something that could last.

I knew it, even thought about it early the next morning as I reveled in the scent and touch and sounds of Sherry sleeping beside me. I did what I always did, roll into her, snuggle into her backsides and awaken her with my hardened cock slipping along her slit and through her thighs. She normally grunted and demanded more sleep, or more likely rolled out of bed and told me to knock it off, but in a rare gesture of caring she opened her knees and welcomed me in.

I was lusty and in need but tried to take it slow, moving only halfway in before pulling back, kneading her breasts and biting and kissing the back of her neck. Sure, I tried to give some back, like with a hand down to play with her clit, but Sherry pushed me away, using her own hand to stimulate my cock to an even faster rise to climax. Which means she had other things on her mind, other things to do, but was willing to let me unload my lusts inside of her more than generous pussy.

For me it was a wonderful moment, calling out her name and pulling her close as my balls pulsed out a dozen streams of jism, literally filling her pussy to overflowing and making her mine. Yet just a minute later she was up and out of bed, talking about work and some school activity Tim had brought up just the day before. There she was, throwing on a top to hide her magnificent tits while I lay there focusing on the long line of semen running down her inner thigh. The dollop of viscous goo seemed intent on escaping from Sherry’s thick feminine pussy lips, gleaming in their wetness, all while I was wishing only to disappear back up inside of her thighs. I couldn’t understand why life couldn’t be more simple, more full of the basic pleasures of life.

Then I dragged myself out of bed and readied myself for yet one more day of meaningless high school. One day down, another dozen to go. Most of us seniors could hardly wait for it to all be over, but I’ve got to admit to enjoying the simple pleasures of (almost) always waking up with Sherry at my side and having a kind of family to come home to. Sherry’s home had become my home, so much so that I hardly ever saw my dad anymore after my party. I even had to kick myself and make sure he knew when my graduation ceremony was.

The week-end before the end of my last year, the end of Jennie’s freshman year, Sherry had a birthday celebration for Tim at a local pizza place. She mostly held it there, away from home, because Tim’s dad wanted to attend. Didn’t see him much, usually from across the bleachers when he found the time to attend one of Tim’s little league games. This was the first time I’d be sitting with the guy, face to face, having to make small talk while knowing way too much about what he had done to Jennie. Sherry had also warned me that Tim had told his dad about her and me. In the end, we mostly ignored each other and Tim seemed to be totally unaware of all the strain going on under all the fake smiles. Sherry kept Jennie on the opposite side of the table from her dad, right there safely seated between me and Sherry. Sherry pretended politeness, Jennie pretended to be a little girl, and Tim seemed oblivious, happy to eat pizza and open presents.

As the party broke up, the dad and I never even bothered shaking hands, just nodding and going our separate ways. That night Sherry wasn’t interested in doing anything, turning her back on me and wishing me a good night, but then turning back over and holding me. She tried meeting me half way by giving me a hand job, but I pushed her off and somehow whispered out that I loved her. First time and I really meant it. She didn’t return the sentiment but she did kiss me and we did fall asleep in one another’s arms. That was good enough.

Of course graduation changed nothing. Got more hours of work, more responsibility, a few more dollars a day, but nothing to brag about. I tried using my extra time to turn Sherry’s place into my real home, like starting a late spring garden and painting the laundry room. Sherry appreciated the effort, so she said. Then I went a little too far, inviting her to a friend’s blowout party by the river, illegal drinks and drugs and who knows what else. A fun time for everyone, right? It didn’t go as I had expected.

“You want me to go to, what, a high school graduation bash by the river?”

“Yeah. It’ll be fun. We don’t have to stay too long. Just hang out.”

“Right. Girls, boys, booze, and hanging out. I get that Taylor, but, you know, I’m kind of over that. I really don’t think I’d fit in. You understand that, right?”

I knew but I didn’t really want to admit it, just like Sherry didn’t want to comment on what I was hoping to get out of her being my date at a party full of teenagers. Yeah, I’d imagined having Sherry walk around in her tight shorts and halter top and make all my friends explode with jealousy. Sherry knew it, I blushed, and she turned away simply saying, “Get real Taylor. Go if you want.”

Still, those first few weeks after graduation were a sweet time, me pretending to be a newly minted adult, with a job and a home and a woman to satisfy my every need. I enjoyed pulling Sherry in for a hug, a hand up to weigh one of her breasts, a kiss to her neck with the hope she’d moan and tell me there was no need to wait until bedtime. Playing catch with Tim, a video game with Jennie, helping with the dinner dishes. Life seemed full and complete, something I hadn’t had since my sister had left many years before. Then reality set in, taking both of my beautiful women away.

First and I suppose most important was Jennie. She’d been bending the rules since the end of school, sometimes leaving the house early to be with Troy and once not coming home until late the next day, causing Sherry to growl and threatening Jennie with mandatory summer school and a chastity belt. Then it happened again, Jennie not coming back one night, not answering her phone and Troy pretending he had no idea where she was. Sherry was as stressed and angry as any parent could be and as she was leaving for work she pretty much laid it on my head to find Jennie and lock her in her room.

I knew where Troy lived but followed my instincts and went to Sam’s place first. Found Troy and Sam arguing in the back bedroom, and you know who about. As I walked into the middle of their argument, Troy rounded on me and said, “Who invited you?” and then turned to Sam, saying “Did you tell him?” and finally back to me with a blunt “Shit. You wanna come? Fine. Let’s get moving.”

Didn’t know what Troy was talking about but I had the brains to know this all had something to do with Jennie. I just followed Troy outside and to his truck without any of my normally stupid questions. I got in, he started driving, and not until we were on the highway did I finally ask a question that made no assumptions that I knew what I was talking about.

“You know where Jennie is? What happened?”

“Didn’t she text you? Well, you wouldn’t know anyway. George. Grabbed her yesterday and took her up to a place of his, a friend’s, up in the hills. Must have taken her phone but she somehow got to use his phone this morning. Sent me a message saying she was up in some dump up in the mountains.”