Jaime Becomes a Woman Ch. 02

As you may recall, Jean, is a good looking, early 30s, single, soccer mom who moved into my neighborhood several years ago. Jean has twin 13 year old boys, and a 19 year old daughter, named Jaime. Since I've known them, they have standing permission to use my pool. This came into play recently when Jean's pool filter broke.

While visiting to use my pool, Jean received a phone call saying there had been two last minute cancellations for a week long soccer camp she had been hoping to get her twin boys into. That was great news. The bad news was that the camp started the next morning, it was located several hours away, and the bus had already left so Jean would have to drive them.

After a short discussion, Jean accepted my offer for her daughter, Jaime, to stay with me while she took her twin boys to the week long soccer camp.

When I first met Jaime, years ago, she was something of an awkward, gangly, tomboy. Those days were long gone for Jaime has grown into a talented, hardworking, beautiful young woman. In my opinion, Jaime's mother, Jean, is quite pretty, and while Jean and Jaime have some similarities, the one glaring difference is that Jaime is now gorgeous - as in, centerfold material! Jaime is petite, with long brown hair, big brown eyes, a golden tan, shapely hips, and perky, full breasts that stand-up firm and high.

In short order, the once shy Jaime quickly warmed-up to my quirky sense of humor. In fact, within just a few hours I had Jaime talking freely about work, dreams, family, friends, and even boys. I learned that Jaime had dated some and that she was no longer a virgin, but she did confess that sex with boys her age was typically frustrating and unsatisfying (primarily due to the immaturity of the boys).

After seeing my semi-hard cock bulging in my swimsuit, Jaime further confided that several of her girlfriends had told her sex with men was far superior. It was about that same time that Jaime shocked me as she passionately pleaded to further explore her growing sexual appetite with me! I learned that the demure, barely legal, Jaime had a major DILF fetish and a lust for tasting cum when she begged permission to blow my thick cock and swallow my mature cum! Adding to my joy, the nubile Jaime then begged me to fuck her and help her feel like a real woman - which I gladly did!

This story picks up from there.

Following our sensational love making session, Jaime eagerly kissed and licked my cock completely clean. It made me smile to discover how such a petite young woman had such a huge and insatiable sexual appetite!

Knowing I'd need some time to recharge, I asked Jaime to join me in my large, walk-in shower. Like my outdoor shower facility, I have a gas-fired, tankless hot water heater, so there is no concern about taking long showers.

I tenderly took my time to soak and wash Jaime's sexy, petite frame from head to toe. I enjoyed how our height difference allowed me to stand behind her to cradle and fondle her perky, handful-sized titties and manipulating her taut nipples. From this position I also enjoyed dragging my semi-hard cock against her beautiful bubble butt.

Jaime lunged forward to brace herself against the shower wall and bucked her ass hard against me as I effectively dry humped her curvy ass cheeks. While I continued massaging her breasts and taut nipples with one hand, I reached my other hand around to actively masturbate her engorged clit. After several magnificent minutes, Jaime began to shudder, shake, moan, and pant as a series of fluttering orgasms ripped through her lithe frame!

Jaime held this position for several additional moments before she spun around, dropped to her knees and lovingly assaulted my mature cock with her young mouth! She kissed, licked, and sucked me while simultaneously sliding her petite hands up and down my slippery shaft. To my surprise, my wanton, watery, waif succeeded to once again bring me back to full erection!

Jaime then returned to her bent over position as she passionately purred, "Fuck me again! Fuck me hard! I want to feel your mature, thick cock fill me from behind!"

Happy to oblige, I grasped the shaft of my cock and deliberately dragged it up and down the length of her slit several times before plunging the fat, thick head inside her.

Jaime moaned in an affirming, low, passionate, voice, "Oh, yes! Uhng! Mmm, oh, yes! You big cock feels so good inside me!"

I began to slowly, repeatedly slide my thick cock in and nearly all the way out of Jaime's petite pussy! As I had instructed her on my bed earlier, Jaime reached one hand between her legs to finger her clit while I methodically fucked her.

Jaime's panting, moaning, and wailing increased proportionately with her pleasure.

Jaime's ass looked sensational, and now that I was confident that she was sincerely interested in experiencing sex more fully, I decided to explore just how daring she was. As I rammed my cock in and out of her tight pussy, I slowly ran my thumb around her beautiful puckering anus. I told her, "You are such a beautiful young woman, Jaime! Your petite pussy feels so tight and good around my thick, mature cock! And your sweet, round ass, looks extremely sexy. I want to show you how a real woman uses all of her body to help feel pleasure for her and for her man!"

Jaime whimpered, "Uhng! Uhng! Yes! My girlfriends... Uhng! Have told me... Uhng! That anal sex... Uhng! Made them cum... really hard!"

Upon hearing Jaime's sweet, sultry voice confirm her interest and intrigue, I reached to a cabinet beside my shower to grab a tube of anal lube. I poured some on my thumb and methodically eased it past her sphincter and into her amazing ass! Jaime squealed with a delightful mixture of mild pain and pleasure as she felt the double penetration of my cock and thumb simultaneously inside her.

I slowly rotated my thumb as I gradually worked it further in and out of Jaime's ass. About this same time, I began thrusting my swollen cock harder and faster into her petite pussy. Jaime responded to her dual penetrations with another pronounced orgasm!

After several minutes, I withdrew my shaft from Jaime's cunt and my thumb from her ass with a pop! I then applied my anal lube to her ass and my cock. next, I rubbed the head of my bulbous cock head against her anus and slowly began to drive it into her ass.

Jaime briefly cried out and winced with pain as my cock head passed her tight sphincter but she pushed back against me and passionately pleaded, "Ow! Ohh, keep going! Umpf! Fuck my butt! Fill my virgin ass with your beautiful, hard, mature cock!"

I grabbed Jaime's slippery hips and pressed my swollen shaft deeper into her ass. She was so tight but, as with earlier, so extremely passionate and enthusiastic to explore more of her blossoming sexuality!

I grunted as I thrust in and out of her, "Uhng! Oh, Jaime! Your beautiful ass is amazing! Uhng! Uhng! I've fantasized about... butt fucking you... since you graduated... last year!"

Jaime soon bucked and shuddered intensely as she screamed with pleasure! "Umpf! Umpf! Oh, yes! Yes! I'm going to cum! I'm going to CUM!"

I thrust harder and faster as I replied, "Yes, Jaime! Yes! Cum for me! Use my mature cock and hands to help your beautiful body, cum, Jaime!"

Jaime shrieked and squealed, "Oh, mercy! I'm cumming! I'm cumming! Fuck! Oh, fuck! Oh, I'm cumming so hard!" Jaime's body writhed and wriggled in what was by far, her most powerful and prolonged climax yet!

Upon hearing and feeling Jaime's erupting orgasm, I rapidly withdrew my cock from her virgin ass and thrust it hard and full back inside her quivering pussy! I did my best to keep it plunged deep inside her as her petite body bucked and bounced as the waves of pleasure crashed over her!

Jaime's tight ass and pussy each felt fantastic and I wanted to keep banging away until I was ready to cum but I wasn't sure her little body could take it so I waited until her spasming subsided before I withdrew my still throbbing cock from her young pussy. I then gently spun Jaime around, and held her tightly against my chest as she shook, cried, moaned, and panted with unprecedented pleasure!

Jaime planted numerous kisses on my chest, neck, face, and lips, as she said breathlessly, "Oh, thank you! Thank you! Oh, you beautiful, sweet, sexy, man! No one has ever made me feel like such a woman! No one has ever made my entire body explode with such powerful pleasure! I have never wanted to make a man cum as much as I do now! Mmm, let me make you cum! I desperately want to make you cum! Will you let me? Will you please let me make you cum again?"

I smiled and shook my head in an affirming, yes, as I kissed Jaime on the forehead before kissing her fully on the lips as I erect cock smashed against her tiny tummy. I then dried us both off and recommended that we retreat back to the comfort of my king sized bed.

I positioned myself on my back and lovingly told Jaime she may suck my mature cock back into her petite mouth.

Jaime's face illuminated with a blend of love and lust as she devoured my cock! She bobbed up and down, coating my shaft with saliva while her tiny hands worked in tandem to jack me off.

"Mmm, your mouth feels so good on my cock, Jaime!" I said. "I especially like it when you suck me deep into your young throat. Deep throat me, Jaime! Fuck my cock with your beautiful throat!" I cheerfully encouraged her.

"Mmm, hmm!" Jaime eagerly acknowledged. She diligently worked to ease my thick, hard, cock deeper into her mouth and past her gag reflex.

The sounds of Jaime's exuberant sucking, slurping, and occasional gagging and gasping was incredibly arousing! She was as persistent and she was passionate!

After several minutes, I asked, Jaime, "Have you ever had a man fuck your beautiful breasts?"

Jaime, was smiling brightly, but lowered her head somewhat shamefully as she softly answered, "My tits aren't big enough to do that. I've had past boyfriends show me porno videos of women doing that to make men cum but they always had huge tits... That's why I never tried doing that with any of them." Jaime's voice trailed-off towards the end.

I smiled and kissed Jaime fully on the lips before I replied, "Nonsense! Jaime, you are an incredibly gorgeous and sexy young woman, as I'd hope the last few hours have proven. You have lovely, firm, perky breasts and they are perfectly sized and shaped to wrap around a man's cock. Would you like me to help you learn how to use your pretty titties to fuck my cock like a woman? Would you like to see and feel me slide my thick, mature cock between your breasts until you make my cum explode all over them?"

Jaime passionately exclaimed, "Yes! Oh, yes! Teach me another way to please you like a real woman! I want to make you cum again!"

I instructed Jaime to lay on her back. I straddled her petite frame and slid my hard cock to her luscious, dick sucking lips, and told her to suck me several more times, being sure to use lots of saliva to make it real slippery. After she did, I told her to use her hands to squeeze her pretty titties around my slick shaft. I then proceeded to thrust my hips back and forth between Jaime's beautiful, nubile breasts.

I groaned, "Oh, yes, Jaime! That's it! That's it! You're using your beautiful tits to fuck me!" I thrust back and forth repeatedly as I continued to offer Jaime encouragement and praise. Every so often, I'd deliberately press harder to force my fat cock up and out of her cleavage and up against her sweet lips. "Every so often, a good woman will suck her man to keep him well lubricated." I explained. I continued, "Well that, and simply because leaning above a beautiful woman to watch her enthusiastically suck his cock is another major turn-on for men!"

Jaime smiled lustfully and eagerly accepted the opportunities to suck my cock! "Mmff! Mmff! Mmff!" She cooed with a throaty voice as she slurped my cock!

When I returned to actively fucking Jaime's tits, she proudly cheered, "Yes! Fuck my titties! Mmm, fuck my titties! Let me use my titties to make you cum!"

While still somewhat of a novice, I shared that Jaime's raw, innocent ability to talk dirty to me was helping my balls to once again tingle!

I picked-up my pace and told Jaime, You're doing good, beautiful woman! Keep going! Keep going, you're going to make me cum!"

Jaime cheered, "Yes! Oh, fuck, yes! Cum for me! Cum for me! Cum all over my titties!"

I thrust several more times and then reached down to furiously stroke my cock as I cried out, "I'm cumming! Oh, Jaime, I'm cumming! Stick out your tongue, Baby! Open your mouth wide and stick out your sweet tongue! Uhng! Uhng! Uhng!"

Jaime squealed with delight as I pumped spurt after spurt of warm cum across her beautiful breasts, neck, cheek, and mouth! She wriggled and squirmed delightfully trying to capture my flying jets of semen onto her waiting tongue! "YES! Cum for me! Cum for me!" Jaime pleaded proudly!

As I felt my pulsations diminish, I crept forward to edge my cock into Jaime's gaped-open mouth. She needed no further prompting, and reflexively commenced to licking the cum from my cock with great zeal. Again without prompting, Jaime then sucked my cock jubilantly, as she lovingly worked to ensure she had successfully emptied every last ounce of my cum!

Jaime then beamed up at me as she said sweetly and lovingly, "Thank you for seeing past the former, gangly tomboy I used to be long enough to help recognize and celebrate the woman I've started to become! Thanks also for helping me prove my friends right about just how sensationally satisfying it is to experience sex with a mature man!"