Jamie's WorthChapter 3 free porn video

I was free, or as free as a guy like me could be. The evidence had been destroyed and only Jamie's word remained to incriminate me, and I knew how to take care of that. Trusting young girls to keep a really big secret like having sex with a teacher was a real risk, but a necessary one. Making sure they were happy and hopelessly in love was the key, that and picking a girl not only for her appearance, but much more importantly for her personality. If you know what you're doing, you can tell which girls will keep a secret forever. Lonnie could do it and she would, so long as I never hurt her.

The day would come when she found herself in love with someone else. A boy closer to her own age and all I had to do was wait for it. In her mind I'd be broken hearted, maybe even a little jealous, but more than anything else, I'd be happy for her. That was the important thing. Rewarding the girl for her maturity and respecting her desires would ensure the best possible outcome for both of us. I'd send Lonnie off with a kiss and a small remembrance, a bracelet maybe, or a ring, and she'd be happy, so happy. She'd remember me forever and keep the secret, comparing me with every boy she'd ever date, and usually finding them wanting, I was sure. I enjoyed that part even more than the seduction, I think. The breaking up and I was good at it.

The only one who'd ever broken the mold was Amy, but she wasn't like anyone else anyway and I'd married her not just to keep our secret safe, but because I truly loved her. She'd been the proverbial thirteen going on thirty and that was no joke. I don't think Amy had ever been a child really,

Jamie was a child though and he could keep a secret too, and the boy vexed me. I loved girls, yeah, but if I'm to be honest as I've been, I have to admit I loved what they were, more than who they were. Like Lonnie. I loved her fourteen year old body. I loved her personality too; she was smart and funny, and completely adorable with her soft brown eyes and kinky brown hair. The braces she was so self-conscious of made her deliciously cute. I knew she'd grow out of it though and so I knew I wouldn't love her for more than a year or so. She wouldn't be the same at fifteen.

But Jamie ... It wasn't a thirteen year old boy I loved, it was him. I had no interest in boys before and none now. But he was the one I'd become infatuated with and I couldn't see it ending. I felt confused and unsure of what it meant. There wasn't any rationale for it. I told myself it was because Jamie was a boy, that's what was confounding me. Would I have felt the same if he were a girl though? I suspected I would and that just made it worse. I had plans and plots and ideas in my head, but I didn't know what I was doing, not really.

"Jamie, can you stay after class for a second?" I asked him as the bell rang.

We hadn't really spoken in the few days since I'd visited his home. We saw each other at school and smiled, and I worried that we were being obvious, when in fact I knew there was nothing out of the ordinary for anyone to notice. I was nervous though and so I'd kept some distance between us and Jamie had been waiting for me, patiently for a boy his age, but waiting nonetheless and now his blue eyes lit up as he nodded.

"Hi," he said, standing by my desk as the last of the other kids filed out for lunch.

"Hi." I smiled back at him, barely able to keep myself from reaching for his long golden hair. I wanted to stroke it. I'd been wanting him for two full days. "Hey, I'm picking up that new computer after school today. Can I bring it over to your house?"

"You want to come over?" he asked, and his grin made my heart jump into my throat.

"Yeah," I said. "Is your mom going to be there?"

"Tonight?" Jamie shook his head. "It's Friday, mostly she goes someplace."

"Oh, well..." I wasn't surprised. "She leaves you home alone?"

"Yeah," he said with a shrug. "You can still come over, right?"

"Sure, I just really want to meet your mom too."

"Why?" Jamie narrowed his eyes, maybe worried I would tell her about his dress or something.

"I just don't think it would be good if I came over and she wasn't there," I said truthfully. "What time does she go out usually?"

"After dinner," he replied. "I dunno, like seven maybe."

"Hmmm ... I'll come over early, okay? You can tell her if you want."

"She's gonna think I'm in trouble." Jamie bit his bottom lip.

"No ... Here..." I wrote a note on a piece of paper explaining that I wanted to stop by and drop off a computer for Jamie, an old one I had just sitting in a closet.

"It's an old one?" Jamie asked, reading the note and I chuckled.

"No, it's new," I said. "But she doesn't have to know that, right? It might make her wonder."

"Okay, yeah!" He giggled like a little girl and I took a deep breath. Fuck, that was sexy.

"So, I'll be over about six, okay?" I asked and the boy nodded. "Good."

I went shopping after school and not just for a computer. I had to guess at sizes, but I found a sweet dress that I thought would fit him nicely. It was blue with pink trim, all satin and lace and rather too nice just for casual wear, but oh! it was beautiful and with his pale complexion and blonde hair and those eyes...

I picked out a training bra for him and three pairs of panties in a package, white, pink, and baby blue like the dress. They had small bows on the front. Some ankle socks in assorted, femenine colors, the sort with lace around the top, and a pair of shoes. Again, I was only guessing, but I'd done this sort of shopping many times and I was more comfortable buying clothes for a teenage girl than I was buying my own.

Some cute and inexpensive jewelry, little things like clip on earrings and a gold necklace with a heart locket. Some bangles and bracelets, the sort of things a girl his age would like and look so cute wearing. I bought some pink lip gloss and a purse, hairbrush and comb set, small compact mirror with some blush in it. Bobby pins and perfume, a little body spray. It was fun and my cock was throbbing as I imagined Jamie using those things, wearing those clothes for me.

It had been a good trip to the mall and I was satisfied.

"You must be Jamie's mom." I forced myself to smile at the woman who opened the door.

"I must be," she said with a lop-sided smile. "I'm wearin' her panties."

"Great," I replied under my breath and cleared my throat. "I'm Mr. Valentine, uh, Jack ... and I teach math at...

"Valentine?" She must have been in her late thirties, I supposed, and trying to look twenty years younger. Too much makeup, too much red coloring in her hair, too much alcohol and cigarettes and too much ... Everything.

"Yeah," I agreed, waiting for it.

"I didn't know it was Valentine's Day!" She giggled and gave me what she must have imagined to be a sexy look. "Can you be my Valentine?"

"I'm my wife's Valentine, actually." I held up my ring finger and she waved that away.

"She ain't gotta know," the woman said with a laugh. "I'm Paula. You want a drink?"

She turned and walked away from the open door, so I stepped inside after glancing at my car. I'd left the computer in the back seat and I wondered briefly if it would be okay there.

"No thanks," I said. "I just wanted to bring a computer by for Jamie. I had an old one and..."

"That's sweet." She leaned against a dirty kitchen counter. "I was just getting ready to go out; maybe I'll stay in though."

"Uh, well, I can't stay long," I told her, working hard to seem apologetic. "Is Jamie here?"

"I sent him up the corner for some cigarettes," the woman said. "He'll be back. You sure you don't want something?"

"No..."

"You can have whatever you want," she said in a husky voice, striking a grotesque pose and I started feeling nauseas. "Anything I got, you can have for free."

"That's okay," I said. "Maybe I'll just bring that computer inside and..."

"Yeah, yeah." The woman waved and seemed to have lost interest, thank God.

Jamie returned as I hefted one of the two boxes out of the back seat. We smiled and said hello and I could tell he wasn't real happy I'd been here alone with his mom. I think not finding me fucking her both surprised him a little and pleased him a lot. It earned me some real gratitude in his big blue eyes and I wondered how much hell this boy had been put through growing up.

"That's an old computer, huh?" Paula asked from the bedroom doorway, watching as I showed Jamie how to connect everything.

"It's kind of old," I said. "I bought it awhile ago, but never used it for anything, so..."

"Well, I gotta get to my appointment with a certain gentleman," she said, cutting me off with a smile and I hid my jealousy well, believe me. "His name's Jack too, but you can call him Mr. Daniels."

"Uh, right. Well, I should get going then," I told her and Jamie frowned at that.

"Can't you stay and show me how to use it and stuff?" he asked me. "Mr. Valentine can stay a little, right Mom?"

"I don't care," she said over her shoulder. "Just don't burn the goddamn house down."

"No, I should..." I started getting up.

"It's okay." Jamie smiled at me and lowered his voice. "She's gonna go."

Soon enough the woman did leave and we played with the computer for about fifteen minutes; until I was satisfied Paula hadn't forgotten something.

"Hey, uh..." I dug my keys out of my pocket. "There's a couple plastic bags in the trunk of my car, why don't you go get them, bring them back here?"

"What's in them?" Jamie wondered, taking my keys.

"A surprise." I grinned at him. "Go on."

"Okay. Yeah," he agreed and practically ran in his excitement.

Dressing Jamie was fun.

"You're very pretty," I said, watching him stand in front of me naked. "Don't hide, don't be shy."

"I'm not," he replied softly, but his nervousness was sweet and undeniable.

he had a smooth body with a light complexion. I didn't notice any birthmarks or scars, just a few small moles maybe and none of those could hardly be called a blemish; they only added to his beauty. Jamie was short for his age and thin, and perhaps I liked that the most, but I suspected it was due to a bad diet as much as anything else. How he appeared as a frail angel, with his blonde hair loose and falling around his pretty face. Even seeing his small penis, pink and circumcised hanging against his plump little balls, it was sexy. He was sexy and his tits, those nipples were wonderful and just as swollen as I remembered. I had him turn around for me, so I could gaze upon his wonderfully pert ass. It was perfect to my eyes, as it had to be.

"Put the panties on, the pink ones," I suggested and he nodded quickly. I watched him open the plastic carefully and unfold them, stepping in one leg at a time and pulling them up.

"Like this?" Jamie looked down at himself and there was just a faint bulge, barely noticeable and I smiled.

"Perfect," I said. "Get the bra, I'll help you."

The boy had no idea how to put one on, of course, and I was only to happy to help him. I stood close behind Jamie, fitting his arms through the bra and pulling the soft elastic tight so the soft cups pressed against his tits. I closed the back, the two small hooks, and adjusted the shoulder straps for him.

"It feels tight," Jamie said.

"Turn around, let me see," I whispered and he was there, a foot away in his new pink panties and small white bra and I had to kiss him then.

I pressed my right hand to his breasts, feeling him through the cotton of his underwear and all the while I explored Jamie's eager mouth with my tongue. He was holding me as well and it was a lovely kiss, one of the best I'd ever experienced, and I let him go reluctantly and only because I wanted to see him in the dress I'd bought him.

The dress was satin, as I mentioned, and a wonderful shade of light blue that set off Jamie's eyes like magic. It turned out to be a good fit too and I had a real eye for such things. It could have been a little longer perhaps, but no, it was nice just the way it was. I helped the boy into it and turned him around so I could close the zipper.

"It's beautiful," Jamie said over and over, stroking his dress like a new kitten.

He trembled with happiness and I imagine that for whatever reason, Jamie had long dreamed of having clothes just like this. I'd never been much for the debate on heredity versus environment, but I believed just then, looking at Jamie and his obvious pleasure, that he really was a girl inside. Being born with male genitals was just bad luck and it was another part of the boy's life that I found myself unhappy with. How much rotten luck did any one person deserve, I wondered? Not this much and I found that nothing mattered to me so much as seeing Jamie happy.

"Do you like it?" I asked.

"Yeah." He looked ready to cry and I smiled at that.

"It's okay, you can be happy," I told him. "Put on your socks and shoes."

"Alright," Jamie agreed and I watched him sitting on his bare mattress, pulling on a pair of baby blue socks and fluffing the lace with a giggle. He put on the shoes and I was thankful that I erred on the larger side rather than the smaller. Jamie would grow into them soon enough and he could wear them now anyway. Little Black Betty's with silver buckles and half inch heels.

"That's perfect," I said with a small sigh. "Can I fix your hair?"

"What are you going to do?"

"Oh, I dunno." I shrugged as I'd already started brushing it, finding some of the bobby pins I'd bought.

I decided to pin his hair back on the sides, so that it fell in golden tresses behind both ears. It was simple, easy, and effective. I combed his bangs and promised him I was going to cut them soon, just to straighten them out, but it wasn't bad. I really wanted to bring him to a beauty parlor, that would have been something. I applied some gloss to his lips, just to give them a bit more pink and a soft, moist appearance which he already possessed in any case. Mostly it was just fun, like putting on his jewelry. The heart necklace and some little golden bracelets around his narrow wrist.

"How do I look?" Jamie asked, standing nervously in front of me.

"You're the prettiest girl I've ever seen," I told him and maybe it was true, maybe not, but at the moment I didn't doubt it.

"I am?" He giggled and I could see his little pink tongue.

"Yeah, you are," I said.

"I'm your girlfriend now, right?" he asked and I nodded.

"Are you ready to go outside?"

"Out ... Side?" Jamie widened his eyes. "Where?"

"I don't know," I told him truthfully. "I don't want to stay here though."

Jamie looked around and he nodded.

"Me neither," he said.

"I want to kiss you some more too," I decided, making up my mind as if I hadn't already.

"Okay." Jamie smiled shyly, licking his lips and lowering his eyes.

"Do you know what boyfriends and girlfriends do?" I asked him. "When they kiss? After they kiss..."

"Are we going to do sex?" he wondered in his sweet sexy voice.

"Have sex? Only if you want to, Jamie."

"I do," he replied quickly. "But I'm ... I never did it, so ... Maybe I don't know how?"

"I'll show you," I promised him. "But not here."

"Yeah, not here," he agreed. "So ... Where?"

Room 214 at the Motel 8 out by the airport was a nice enough room and I felt only a little nervous. I'd used this motel before with my girlfriends and it was reasonably safe. I could get a room and drive around to the back, entering out of sight and bringing Jamie up that way. I locked the door behind us and he was shy and compliant, and even getting him to leave the safety of his house wearing a dress had been easy. Jamie trusted me completely and I liked that a lot.

We were on the bed, fully clothed and I kissed the boy again. I couldn't get enough of his mouth and Jamie learned quickly. His small tongue chased mine and I let him lick across my teeth and tickle my cheeks and the roof of my mouth. He took everything slow and cautiously, and so very sweetly. My hands roamed his body through his dress and I felt Jamie's hands doing the same with me.

Making out with Jamie was every bit as good for me as making out with any young teenage girl. I really couldn't tell that he was a boy, not while we were clothed and I was in no hurry to undress him. We'd go at Jamie's pace, that was the rule. If he didn't like something, or if he said no for any reason, I'd stop immediately. That was how it had to be with thirteen year old girls and Jamie wasn't going to be an exception. We were partners in this, he wasn't some sort of love slave or sexual plaything. I just wanted to be his teacher.

Jamie looked sexy as hell too and after probably half an hour or forty-five minutes of kissing and touching each other through our clothing, he was ready to go further. I'd already grown hard as a rock as the boy began rubbing my bulging cock, lightly at first, but then harder as he realized I wasn't going to stop him. Jamie would suck my tongue, moaning into my mouth while his small hand massaged the obvious erection in my trousers.

My own hands were all over the boy as well and Jamie didn't protest at all when I found his own smaller cock with my fingers. He merely spread his legs for me, lifting his hips while my hand cupped the boy's innocent sex through his panties. I squeezed him gently, feeling the small wet stain growing as Jamie's cock was already getting moist with precum. He wasn't so different from a girl, not at all. That was especially true when I pushed my hand lower between Jamie's pale thighs, so that I could play with the crack of his ass through the thin cotton. It felt just like a pussy, hot and tight and sweet, and I was fingering him gently with just his panties to separate my fingers from his virgin hole.

When I finally opened the back of Jamie's dress, it felt like Christmas and I started all over again, touching his chest and tummy, kissing his skin. I played with his bra, loving the way it fit his immature body. I pushed it up, above his tits so I could kiss the boy's nipples. Jamie gasped softly and his fingers were in my hair as I took them into my mouth one at a time, sucking them gently at first, giving him small bites and then sucking harder as they grew stiff beneath my tongue.

"Ummm..." Jamie nodded, smiling with his eyes closed as I started giving him a hickey on his left nipple, biting it and chewing lightly while I sucked.

Several minutes later it looked dark as an over-ripe cherry and his tit formed a nicely pointed cone, a beautiful girlish breast. I did the same thing with the other one, bruising his pale flesh as I drew blood hard to the surface. I slipped my right hand under his skirt and spread the boy's legs, feeling his buttery smooth thighs part easily so that I could rub his crotch like a little pussy. I pressed my palm against his cock and balls, finding him stiff with excitement, and my fingers found his asshole and I loved playing with him there.

I slipped his panty aside and worked the end of my middle finger around Jamie's tight puckered anus, forcing the tip against that soft ring and slowly into him. He was tight and dry and the boy jerked slightly. I brought my finger to my mouth, pausing my kisses around his tit just long enough to get my finger wet with saliva. I pushed harder then, worming my finger inside Jamie's virgin boy pussy, fingering him like he was a little girl, and he rocked his hips, not fighting that new experience at all.

"Open my pants," I breathed. "Unzip me."

"Okay." Jamie swallowed thickly and then laughed; giving me a soft nervous giggle while his fingers worked to free my straining cock.

"Yeah, that's it," I said softly, turning his mouth to mine once more as the boy's hand went into my boxers.

He touched my cock tentatively, exploring it for a few minutes while we kissed, but soon he gripped my manhood tighter and that felt great. I kept playing with him too, keeping my hand between his thighs. I massaged Jamie's balls and hard little cock with my palm while I fingered his tight little ass. It felt just like a pussy, except not as wet maybe and I was working on that too. His small cock, only an inch or two longer than my thumb and about that thick, leaked precum steadily. I rubbed my fingers over the sensitive head repeatedly, bringing that wetness to the boy's asshole and working my middle finger slowly deeper with every little push.

I kissed him hard, still making out with the boy and like all girls his age, Jamie couldn't get enough kissing. Everything I did to him, Jamie would try on me. I sucked his tongue gently and then his lips, nibbling and even biting them because they were so wonderfully soft and full. I pushed my tongue into his mouth, sliding it in and out like a cock while I fingered his ass pussy gently, and Jamie closed his lips around it, sucking my tongue while his delicate hand stroked my cock blindly. He bit and nibbled at my lips as well, playing his small thumb over my cockhead, and wiggled his ass invitingly, hunching my hand with his hips like all girls do when their little pussies are on fire.

We didn't talk very much; we didn't have to, and Jamie sat back smiling and breathless while I undressed completely. He started removing his own clothes, but I stopped him with a smile. His dress was bunched around his waist and his training bra askew and pushed up his flat chest, above those ripe red titties that were beautifully swollen from the love bites I'd given them. Jamie's panties were loose and pulled to the side, exposing his stiff little cock, pink and red and glistening with precum. Between his pale thighs, the boy's hairless balls lay just above his asshole, the sexy crack and sweet pucker that I'd only barely stretched with my finger. Fuck, he was sexy as hell and I didn't want him to move.

I took off all my clothes and found the small tube of KY Jelly I'd bought just for him, like everything else that day, and he was curious, but didn't ask. Jamie was hot and flushed all over, breathing hard and licking his swollen lips. I lay back down on the bed and held out my arms, inviting him to join me and Jamie didn't hesitate. We were lovers now and the boy pushed his body close to mine so that I could embrace him, his mouth pressing against mine with renewed urgency and I stroked his back and then his ass while Jamie's hand found my cock once again. We had a lot more making out to do before we went too much farther and that was fine with me.

"Do you want me to, um, suck it?" Jamie asked me sometime later and he was smiling, looking shy and slutty and nervous and sexy all at once.

"Do you want to?" I asked him, pulling his blonde hair from his eyes and it was a hopeless tangle by then and cute like you wouldn't believe.

"I think so," he whispered and the boy was holding my cock tightly in his small fist, jerking me off slowly and at times I'd had to stop him for fear of cumming.

"Try it then," I said. "Give it a kiss first."

"Okay," he said, and my heart felt ready to burst with excitement, as I'm sure his did as well.

Jamie slid down my body slowly while I watched him, kissing my chest and stomach lightly, wanting to do more but still uncertain of himself. That was the best part for me, one of the reasons I loved girls Jamie's age, they were so innocent and shy at first, wanting to try new things and desperate to please me and afraid of doing something that they perhaps shouldn't. The first time was always the best and seeing Jamie kneel over my erect cock, holding it now with both hands and staring at it with every emotion imaginable crossing his pretty face, was almost unbearable for me.

"Take your time, Jamie," I said, contrary to everything I was feeling just then. "You can do whatever you want. You're beautiful. I love you so much."

"I am? You do?" He looked up at me, smiling and looking so hopeful with those big blue eyes. "I love you too. I want to do it, okay?"

"Yeah," I sighed, staring as the barely pubescent boy gave the tip of my adult cock a tender first kiss.

A long silvery strand of precum connected my swollen cockhead to Jamie's lips for a second and even as it broke the boy was coming back for another. He kissed my cock all over, exploring it slowly with his closed mouth and finally his tongue once Jamie was used to it. It didn't taste bad, his smile told me. It was hot and heavy and throbbing just for him and I told him that. I made sure Jamie understood that he was the reason my cock was so hard. I reassured him over and over, enjoying the way he was licking my cock like an ice cream cone, dragging his tongue along the bottom of the shaft and then around the head. Jamie was losing his fear and gaining confidence and it was just a matter of time before he opened his mouth wide and started sucking my cock like the little girl he was.

"Mmmm ... Baby, that's it ... That feels so good," I told Jamie, resisting the urge to hold his head in my hands and fuck that sweet sucking mouth of his.

He was doing fine by himself anyway, bobbing his mouth up and down on my aching cock slowly and learning how to suck it nicely for both of us. He was able to get the smooth head and just an inch or two more into his mouth before Jamie would gag on it, but that was alright. He'd figured out how to use that soft little tongue of his and the sensation of it wriggling around my cock was driving me a little crazy with lust. I soon had my fingers in his soft blonde air, I couldn't help it and Jamie was okay, he liked that attention and rewarded me with shining eyes filled with pleasure. He wanted to take more of me and he would try every now and again, but the boy's mouth was just too small and he wasn't ready to try opening his throat for it. I wasn't going to force him at all. After a few months of practice, Jamie would get better at it and maybe even learn to deep throat me; that would be really nice.

"Mpphhh ... It's big!" Jamie giggled, pulling his mouth off my cock with a loud wet sound that made me smile.

"No, not too big," I said, stroking his red cheeks with my fingers and admiring the way his chin and neck had become wet with spit and precum. He'd been drooling a lot, giving me a sexy sloppy blowjob and I really wanted to fuck him now.

I had to be patient though, Jamie wasn't finished and I was a little surprised when he started kissing my balls, but I shouldn't have been. This boy was going to be a little cockslut, I thought, much the way Lonnie was. The way they all were once they got used to it. It was amazing how quickly a thirteen year old will accept almost anything so long as it's fun and doesn't hurt. Jamie was licking my scrotum like a kitten and practically purring as my wet cock slid over his pretty face. He was sexy as hell like that, giggling and making muffled moans and sighs. He opened his mouth without any prompting from me and I nodded happily as the boy took one of my balls into his warm wet mouth, washing it carefully, rolling it around with his tongue. He did the other one as well and that was just getting me hotter to break the boy's cherry.

"I want to make love to you," I whispered, unable to contain my desires any longer. "Do you want to try that?"

"Yeah." Jamie looked up at me, licking his lips and nodding slowly. "I want to, but ... Will it hurt?"

"A little," I said, because I'd never lie to the boy. "I'll be really careful though, I promise."

"Okay," Jamie said softly, making my heart ache and cock my throb with anticipation. He looked so beautiful just then, so innocent and trusting and I did love him.

"Like this ... Come here, I have some stuff to make it feel good..." I told him, moving Jamie so he could lay on his back.

I wanted to fuck him like the little girl he was, staring into his eyes and kissing that sweet mouth of his while I took his cherry. Jamie smiled and giggled nervously as I pulled his panties off completely. His smallish cock was so hard it looked almost painful and I knew he wanted to cum. I thought perhaps he'd been trying to ignore it, or possibly Jamie had just been afraid that I wouldn't like his cock because it was proof that he wasn't the girl that he wanted to be for me. It was only slowly that I realized the boy had never had an orgasm in his life. Jamie honestly didn't know what to expect and I shouldn't have been surprised by that, very few of the girls I'd been with had known anything about sex before I'd taught them. Jamie was no different.

"You need to cum, don't you?" I asked him and I was getting my fingers wet with a large dollop of KY Jelly.

"Ummm..." He laughed and gave me the tiniest shrug. "I think so."

"I think so too," I said, pushing his legs up so I could spread the lubricant around his virgin anus. "Have you ever cum before?"

"I don't know," Jamie said. "Maybe."

"If you did, you'd know ... How does this feel?" I asked, rubbing his tight little asshole with two fingers, getting him slick and ready for my cock.

"Goooood..." Jamie sighed as he tried to relax, his sphincter muscles contracting every few seconds so that I could see his pink asshole winking at me. It was cute.