Jaime Becomes a Woman

I'm a man in his late 50s with a beard and a dad bod. I also happen to have an especially active libido and pool, so, I tend to have a lot of guests.

One day, Jean, a neighbor from one street over, called to mention her pool pump was broken and asked if my offer was still good for her and her kids to use my pool?

I told Jean it certainly was and encouraged all of them to come on over.

Jean thanked me and said they'd be there in a bit.

Jean was a single mom in her mid 30s. She is quite petite with brown hair, small but firm boobs, a delightful round ass, and perfect, full, cock sucker lips! She is the text book soccer mom, pretty, spunky, and always on the run with her kids.

Jean arrived about 1:30pm with her twin 13 year old boys (John & Jim) and her 19 year old daughter (Jaime) all in tow carrying towels and a cooler. Jean and I talked and sipped lemonade as the kids splashed around in the pool.

About 2:00pm Jean got a phone call. Apparently there were two last minute cancellations for some premier, week long soccer camp her boys had been trying to get into. Camp started tomorrow and the twins could now go, but only if she could drive them as the bus had already left. It was a few hours away but Jean seemed happy because she could stay with her sister who happen to live near the soccer camp. Jean explained she could make a fun mini vacation of it.

I congratulated Jean and her boys as they scurried about trying to get out of the pool and gather their things. That's when I heard the soft grumbling.

Jaime said disappointedly, "Mom, why do I have to go now? We just got here. I'm not going to camp. I just got out of work and haven't been able to use our pool for nearly two weeks."

I empathized with Jaime and told Jean cheerfully, "You know it's really no problem for Jaime to stay as long as she wants. If she doesn't want to walk home when she's done swimming I will gladly drive her her home. In fact, with my kids grown, Jaime can even stay here until you get back. I've got plenty of food and plenty of room... not to mention the pool!"

Jean agreed, thanked me profusely, gave me a quick hug and kiss, and raced out the door with the twins.

Jaime was somewhat soft spoken and quiet around me. Not in a nervous way, I'm guessing it was probably just due to our big age difference.

Jaime smiled and said, "Wow, that was pretty cool. I really didn't mean to be a bother, it's just so hot."

I assured her it was no bother at all. I went on to say I thought it'd be quite fun getting to know the young adult Jaime.

Jaime replied with slight disbelief, "Really?"

I told her confidently, "Absolutely! When I first met you years ago, you were something of an awkward tomboy. But now you're all grown. I think I'm gonna enjoy getting to know the talented, hardworking, beautiful young woman you have become, Miss Jaime."

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 gorgeous. Jaime is centerfold material. She is petite, with long brown hair, big brown eyes, a golden tan, shapely hips, and perky, full breasts that stand-up firm and high.

Jaime joined me in the pool, and little by little, she warmed-up to my quirky sense of humor. In no time at all I had Jaime talking freely about work, dreams, family, friends, and even boys.

After nearly two hours of talking and playful splashing about, I asked if Jaime wanted to get out and have something to drink while I started trying to come up with plans for dinner.

Jaime followed me into the kitchen. I tried to be subtle but I know I was definitely ogling at her wet bikini clinging to her beautiful full breasts and her nipples poking prominently through the thin material of her tiny top!

As Jaime was sipping her Dr Pepper, she lowered her head, as if in deep thought.

I asked, "Are you okay, Jaime?"

Jaime lifted her eyes slightly and timidly replied, "Yeah, I was just thinking. Well, earlier you, um.. you said, ah... I'm pretty. Do you actually think I'm pretty?"

Somewhat shocked by her question, I replied confidently, "I most certainly do! I'm surprised you even have to ask! I happen to think that you are actually gorgeous, Jaime! But I have to imagine that a woman like you must hear that often!"

Jaime blushed as she sheepishly smiled and shook her head, no.

Responding to Jaime's body language I said, "Oh come on now! A girl, sorry, woman, like you, with your dazzling smile, long hair, golden tan, sultry eyes, seductive lips, and sexy curves? That spells, gorgeous in my book! Why, I bet you must have to beat-off a mile-long line of guys every day just to get out your front door!"

Jaime giggled and said, "Well, ah, yeah, there are several boys who wish I would... um... beat them off! They sure pester me enough about it as they try to look down my shirt or grind their crotches against me. Seriously, though, most of those boys are just gross. They're interested only in themselves. And none of them have ever once called me pretty."

I laughed and told Jaime that those boys were clearly idiots.

Jaime's eyes lit-up and she laughed heartily!

I then shared, "Oh, and by the way, THAT is the difference between men and boys! A BOY only about thinks about seeing one of your tits and getting you to help him cum. A MAN is different! A man understands that he can see a woman's tits and encourage her to not only help him cum, but to cum more often and with much more intensity because he focuses on helping her to feel pretty, special, and helping HER to cum first!"

Jaime blushed, perhaps a bit shocked by my language but seemingly very appreciative of brutal honesty. She laughed long and loud, shaking her head in affirmation.

I smiled and told Jaime, "I can't speak for all those silly boys, but, if you want a man's opinion, you are special, gorgeous, and sexy. Now, whether or not you believe it, well dear, that is up to you!"

Jaime smiled, hopped up from her chair, threw her young arms around my neck, and gave me a huge hug as she whispered a soft, but sincere, "Thanks!"

I hugged Jaime back, kissed her forehead as I briefly enjoyed her hard nipples pressing against me. I said, "No need to thank me, I am just telling you like it is. I'm guessing from your bright smile and warm hug, you believe me!"

Jaime shook her head, yes, as returned to her chair. When she turned to sit, another smile flashed across her face as she pointed to the lump of my semi-hard cock in my swim trunks and quietly but emphatically said, "Seeing is believing. And from what I see, I definitely believe you!"

Embarrassed, and caught slightly off guard, I stammered as I tried to apologize while attempting to rearrange the bulge in my swim trunks.

Jaime interrupted me and said with seductive conviction, "I want to see it. Several of my girlfriends have tried to tell me that men's cocks were better. Now I want to see for myself!"

I paused to think of a reason to say no, but after seeing the sincerity and conviction in Jaime's eyes, I simply shrugged my shoulders, smiled and said, "I guess I inadvertently opened this can of worms. Okay, Jaime, as you wish!"

Jaime bit her bottom lip as her sultry eyes opened wide with excitement.

I told Jamie to keep seated as I stepped directly in front of her and slowly lowered my swimsuit. My thick, hard cock sprang free and nearly slapped her delicate chin as it bobbed in front of her face.

"Wow! It's beautiful! So big! So thick!" Jaime purred excitedly!

I tenderly asked, "Are you a virgin, Jaime?"

Jaime silently but emphatically shook her head, no, as she slowly stroked my hardness with her tiny hand.

I then asked, "Are you on the pill?"

Jaime smiled wryly and affirmingly shook her head, yes, as she continued to caress my shaft and balls.

I asked, "Do you want to suck it, Jaime? Do you want to suck my mature cock?"

Jaime excitedly said, "Mmm Hmm! You are way bigger than my last boyfriend! Your cock is so thick... I'm... ah... not sure if I can get it all in my mouth, but I definitely want to try!"

I told Jaime that she could take as much time as she needed as I said encouragingly, "I have confidence in you, sweetie, so relax and just have fun. You can have my cock however you want it and wherever you want it. That includes changing your mind, Jaime. If you want to stop, simply stop. I'm used to jerking myself off most nights, so there is positively no pressure. If you want to experiece a man, you have to agree that this night is all about you. Understand?"

Jaime leaned forward and slowly started taking my cock into her sweet, small mouth as she let out an affirming, throaty, "Mmm Hmm... Mmm Hmm!"

"You're a good woman, Jaime. Such a good and sweet, sexy woman. Your pretty mouth feels good on my cock!" I told her affirmingly.

As Jaime continued to suck me, I smiled to myself to realize this was not her first blowjob.

Jaime slowly bobbed up and down multiple times, taking about half my cock into her petite, sexy mouth. Jaime sweetly purred as she slurped, "Mmff... Mmff... Mmff!"

I encouraged Jaime to also use her small hands to stroke and caress the rest of my shaft as she sucked my thick, hard, cock. I also explained that if she wanted to try, she could use her tongue to lick up and down the length of my shaft. I elaborated that licking my shaft would not only increase my pleasure, but also might help her be able to slide more of my cock farther into her mouth if she was interested in trying to suck me more deeply.

"Mmff, okay... okay!" Jaime purred to show her understanding. She was a good student and her passion to please me was delightful.

I lovingly stroked her thick, long hair, and tenderly stroked her cheek with my finger as I told her, "Mmm, you're a good and beautiful woman. You are making my mature cock feel so good!"

Little by little Jaime's technique improved. Within a few minutes she successfully managed to get nearly three quarters of my shaft into her petite, young mouth.

Jaime softly cooed with delight.

I asked, "Can I work on pleasing you soon, Jaime? Would you like me to caress and kiss your beautiful breasts? Would you like me gently touch and lick your beautiful pussy?"

Jaime withdrew my cock from her mouth and breathlessly said, "Yes! Oh, yes!"

"Do you want me to help you cum?" I asked in a low tender voice.

"Yes! I do! Oh, I do!" Jaime panted!

I took her by the hand and led her to my large king sized bed. Once in my bedroom, I adjusted the dimmer switch to a soft, low light level as I spun her gently to face me. Taking her petite face in my hands, I kissed her deeply and then, ever so slowly, began to run my fingers up and down her trembling body.

After several minutes, I slowly undressed her, then myself, before I bent to nuzzle and kiss her ears and neck. After several moments, I began to slowly work my way down the center of her beautiful, heaving chest, being deliberately careful to avoid touching her firm breasts and erect nipples.

Jaime's breathing grew increasingly more ragged as soft, barely audible moans poured from her tiny mouth, "Ahhhh... Ohhh... Mmm!"

I guided Jaime slowly to the bed, placing her on her back as I began to use my hands to slowly trace up and down her thighs while continuing my kisses from her chest to her stomach.

I deliberately took plenty of time, slowly edging her thighs wider apart without actually touching her pussy. I then repositioned myself to lean over her from one side so I could nuzzle and lick her other ear. As before, I gradually edged lower to her neck, shoulder, and the upper center of her now heaving chest.

In this position my thick cock would occasionally drag against her side. Without prompting, Jaime reflexively grabbed it and ever so slowly, gently stroked it in the most tender motion.

After several more minutes, I straddled Jaime's hips, forcing my pre-cum ladened cock to press firmly against her lower abdomen. I pinned her arms upward to hold them as I began to drag my tongue all around the outside and bottom edges of her beautiful perky breasts, still deliberately avoiding her taut nipples.

Jaime gasped and her panting increased as her moans became louder and more pronounced. I could feel her legs and tiny stomach flutter beneath me.

Taking cues from Jaime's petite, curvy body, I swooped in to drag my tongue around her right nipple.

Jaime's body spasmed.

Twirling my tongue around and around her stiff nipple, I flicked it firmly with my tongue several times and then sucked it fully into my mouth. I then began gently pulling it upward as far as I felt it could go without hurting her.

Jaime moaned loudly and thrust her head wildly back and forth as I felt her lithe young body writhe beneath me.

A few moments later, I repeated the process on her left nipple. Her vocal and body responses grew exponentially more pronounced!

I then released her hands to help me slowly ease myself down her trembling torso. I used my mouth and tongue to slowly nibble and lick my way from the center of her chest, down her abdomen, to the top crest of her pubic hair. This caused my throbbing cock to briefly slap against the outer edge of her pussy before dropping below it.

Jaime thrust her now free hands downward to grab my hair tightly.

I inched my way downward, kissing and licking the sides of her pelvis as close as I could without touching her pussy.

Jaime writhed intensely as I continued my decent to the tops and inner sides of her tanned, toned thighs.

My warm breath danced across her pussy as I briefly paused to appreciate the visual of her beautiful, glistening labia.

Jaime let out long, soft, pleasurable sounds.

Sensing the time was finally right, I slowly used my strong fingers to spread open her labia before plunging my tongue and bearded chin up and down her pussy while I systematically flicked her clit with my tongue. I licked, flicked, sucked, and lightly nibbled her clit causing her petite body to burst into wave after powerful wave of juicy orgasms!

Jaime twisted, shook, and screamed, "Yes! Yes! I'm cumming!"

I found her purity and passion to be both sweet and highly arousing!

Jaime clenched the sheets tightly with her tiny fists and breathed deeply in and out for several moments before nearly knocking me off the bed as she bound up to dive face first onto my cock!

"Wowza!" I explained at her youthful enthusiasm!

"Mmff... Mmff... Mmff!" Jaime moaned as she sucked my cock like a woman possessed!

"Easy, dear. Easy. You're going to make me cum!" I proclaimed!

She pulled her mouth off my cock just long enough to yell, "Good! That's the point! My girlfriends say if you make a man cum early, he can stay hard longer when fucking you. And I definitely want you to fuck me"!

I couldn't argue with her logic or her passion so I told her, "Okay, sexy woman, I'll tell you when I'm getting ready to cum so you can pull off if you want to."

Already energetically sucking my cock again, Jaime pulled off with a loud pop as she said, "No way, mister! I want to taste your manly cum!"

I moaned with approval as this sexy, 19 year old nymph zealously sucked my mature, hard, thick, cock.

Jaime passionately continued her oral assault on my shaft.

Feeling the pressure in my balls mounting, I grunted, "Get ready, Jaime! I'm going to cum!"

When my blasts began erupting in her mouth and throat, Jaime gasped and gagged a little, undoubtedly not prepared for the volume or force. Jaime's cheeks puffed as my cum seeped out of her mouth and nose but she was a real trooper and just kept sucking and swallowing!

After allowing Jaime to briefly catch her breath, I then placed her on her back and bent her knees to lap her pussy before entering her while my cock was still hard. She was tight so I inched in slowly. I dragged my bulbous head back and forth several times across her clit causing her to writhe with another orgasm.

"Yes! Yes! Oh, yes!" Jaime delightfully squealed!

I reached down and held her legs up as I inched myself forward for a better angle to begin plunging my mature cock deeper inside her tight, tender, 19 year old pussy.

Jaime huffed and her beautiful breasts bounced with each thrust. I was being careful not to hurt her.

Jaime screamed, "Deeper! Oh, yes! Harder! Deeper and harder!"

So, I picked up the pace and incrementally drove my cock in and out of her barely legal cunt deeper and harder!

I then suggested that maybe a change of position would be fun. So I rolled onto my back and directed Jaime to bend down and suck my cock several more times (under the guise of helping to keep it lubricated but also to observe what, if any reactions she might have about tasting her own juices co-mingled with my copious amounts of pre-cum).

Jaime mused, "Mmff... Mmff... Mmff! You taste even better than before!"

I smiled realizing, that just like me, Jaime enjoyed the taste of her juicy pussy!

I then directed Jaime to squat above my cock and ease herself down onto it.

Jaimed said, "I have not tried fucking in this position before."

"It's called the cowboy position. Use your beautiful legs to control your depth and tempo." I said encouragingly.

I held Jaime's sides as she got started. It did not take her long to find her rhythm. I then slid my hands upward to cup and fondle her succulent breasts. I positively loved watching them bounce as I toyed with her puffy nipples!

As Jaime's confidence and tempo picked up, I wet one finger and used it rapidly massage her clit while she rhythmically impaled herself onto my cock. She threw her head violently backwards, arched her back and cried out as she exploded in another tremendous orgasm! It was breathtakingly beautiful to watch her petite body wriggle and writhe!

Sensing her fatigue, I told her to climb off and swing around into a 69 position with me. I lapped her sweet, juicy pussy and she purred loudly as she once again enthusiastically sucked my throbbing cock.

Her tight, tiny ass looked so inviting but I didn't want to push things too far for our first sexual encounter.

Jaime began quivering in a series of small orgasms and soon began begging me to cum again for her. Jaime purred passionately, "I want you to cum for me! I want to feel your powerful hot cum flood my pussy!"

I told her it would be my pleasure as I repositioned her onto all fours to fuck her doggy style. I plunged in slow and steady. As I picked up the pace I pulled her head back using her thick, long hair. Feeling her body tremble, I told her to lower her head and chest onto the bed as this angle would help her take me deeper. I growled for her to snake a hand underneath her body to finger her pussy while I fucked it.

Jaime moaned unintelligibly but musically as she shuddered to another orgasm.

I told Jaime I was getting ready to cum! I shouted for her to lay on her back so I could see her beautiful face as I pumped my cum into her!

Jaime screamed, "Yes! Yes! Oh, yes! Give me your cum! Fill me with your mature cum!"

I tossed her short legs over my shoulders and slid inside her well-lubricated pussy with a single thrust. I loved how tight she was! I pumped and pumped several more times before feeling my balls tense-up. I yelled to Jaime and timed it just right to where I was nearly bottomed out inside her when my cum began rocketing into her. I held myself in place as best I could until my last squirt jetted inside her. I then maintained that position a few moments more to ensure her pussy had stopped spasming before pulling out and rolling over beside her.

"You are becoming quite the sexy young woman, Jaime! Wow! You pussy felt great wrapped around my thick cock!" I said as I struggled to catch my breath!

Jaime panted gleefully, "Mmm Hmm! You helped me feel so great too!"