profporkrind
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BASED ON a true story...
It was summer time. I was 18 years old in Long Island, New York with my father for a week’s vacation. We tried to travel up north from Virginia as much as possible so we could spend time with my grandparents. When we visited, we always stayed in the basement. I loved that basement because my grandfather put his old big screen TV down there. It had a huge king sized bed and a nice sofa as well. When I wasn’t swimming in their pool, one of our favorite family activities, I was usually downstairs enjoying the warm, quiet, extremely private basement with a gigantic television perfect for video games and watching baseball.
My parents divorced when I was five and I chose to stay with my mother. She had primary custody but I still saw my dad on the weekends. The divorce drove my dad to work a lot more. He did so for both financial and emotional reasons, I assume. As a result, our trips to New York became less and less frequent. In fact, we hadn’t made the trip in four years, the longest drought of my lifetime. We used to visit at least once a year. I was only 14 years old the last time we I saw my father’s parents, when my mother and father were still married.
Now I had I just turned 18, and this visit to Long Island was slightly different than the rest. My father remarried his new wife Misty when I was 15, and this was the first time she would be meeting the family. She was welcomed with open arms by everyone. Well, everyone except me that is. I was a momma’s boy. I loved my mother and the thought of this new woman in the Long Island home that I had so many fond memories of my perfect family angered me.
While I may not have particularly cared for Misty, she was something nice to look at. She stood about 5’9. I would guess she weighed about 145 pounds. She was in her late forties. She had nice big breasts, hips to die for, thick tone thighs, and a perfectly pump and beautiful bum. She was a workout freak; she spent 6 days a week in the gym after work and got up at 4am everyday to run on the treadmill before she started her day. She had a very pretty face and a slight southern accent that was very cute. Her hair was brown with very few strands of gray, but I didn’t mind. In fact, the gray hairs somehow made her even sexier to me. Something about older women aroused me. The only negative in my eyes was that she tanned too much and you could tell it wasn’t natural. It showed in the color and texture of her skin, but she was still a fine grown woman who refused to let herself go. I admired her for her work ethic when it came to keeping her body in shape, but she was no fun. It was like every aspect of her life was a job and she never let her guard down. This bothered me about her. She was a confident, sexy, intelligent, and independent woman but she seemed to never let her hair down. Work, dinner, sleep. That was the routine. Never did she and my father go out dancing or to the movies. I think he married her because she was a trophy wife and he was lonely from the divorce.
Right before the trip Misty and I got into an argument. My father and I had a big fight about my grades (senior in high school) and she chimed in, something she had never done before. I snapped at her, “Don’t you EVER tell me what to do. You are NOT my mom and you will NEVER be my mom.” A week later we were on the road and cooler heads prevailed. We were all "getting along" as if the fight never took place.
From day one, Misty really wanted to be close to me. She knew that my dad really loved me and I think that pushed her even harder to create a motherly relationship with his only child. Of course, my cocky teenage attitude, raging hormones, and bitter jealousy never allowed her to gain an inch. I was cordial with her, but she was NOT my mother. We got a little better once I became a senior; but that was because I was always out with my friends so we barely saw one another, not because we improved our stepmother/stepson relationship.
During the vacation she made one of her greatest attempts to get close to me. Maybe it was because we had the fight, maybe it was because she was trying to impress the family, or maybe she just wanted us to be close now that she was officially a part of our family and we were about to spend a whole week together. Whatever the reason, she laid it on thick with slews of compliments about how handsome and intelligent I was, offers to get me something to drink or eat throughout the day, letting me have the TV remote, sticking up for me when my dad got in one of his moods, you name it. I of course was disinterested. I wasn’t being a wickedly moody bastard child, but I definitely gave her the cold shoulder as much as possible. I don’t know exactly why. Maybe it was because I didn’t WANT to accept her as a good person, maybe I was searching for her flaws, maybe I was just being a stepchild who loved his real mother, or maybe I just felt like she was trying too hard. Nonetheless, I was obviously unaffected, unimpressed, and unmoved by her desperate attempts to become closer.
On our third night of the vacation, the adults left the pool area and got ready for coffee and cards. As always, I elected to stay in the water with the pool lights on and keep swimming. I loved swimming in my grandparents pool. Misty, while loved by the family didn’t really participate in all of our favorite hobbies. She didn’t know any of the card games they played so she just sat by my dad and had fun exchanging conversation as they played poker, hearts, spades, etc. But, she didn’t know how to swim! This really irked me because I had never met anyone who couldn’t swim. My entire family could swim, and loved swimming. I practically grew up in that pool.
As I continuously tired my paper thin, 5'7 100 pound body by diving, jumping, and doing laps around the pool I noticed Misty step outside. She was alone and surprisingly still in her swimsuit, a white bikini that was one of my favorites. The top was very classy but still couldn’t hide her perfectly round boobs and the bottoms had two gold rings at her hips which the fabric was attached. They hugged her lower half beautifully, highlighting her incredibly delicious hips, thighs, and bottom. She went to the shallow end of the pool and walked down the stairs. I continued my routine, ignoring her for a good 5 minutes until she finally spoke,
“Frankie, I want to learn to swim. You are such an incredible swimmer; I’d love it if you could teach me.”
Annoyed, I responded,
“If you don’t know by now it’s going to be real hard to learn.”
She persisted,
“Please. Can you at least try?”
“Fine.” I replied.
I proceeded to explain briefly the basics of how to swim freestyle. Her first attempts in the shallow end were miserable failures. I held her up by her sides and instructed her to “kick, kick, kick.” She flailed her legs wildly making more noise than progress. “Stop, try this” I said, as I gave her a demonstration on how to doggy paddle. She seemed to be able to mildly execute the doggy paddle, in the shallow end. I said, “All right, you can doggy paddle. It’s a start.”
Then I instructed her to paddle from the edge of the shallow end to the diving board and back. She took off. I swam by her side just in case. Then, she realized that she couldn’t touch the bottom and panicked instantly. She started grabbing for me violently. I took her arm and dragged her to the diving board. By then, scared shitless, she had her legs and arms wrapped around my body. Her breasts pressed firmly against my back and I could hear her heart racing at the rate that could have rivaled a bumble bee's. If a hard on were possible while in the pool, I would have had a rocket in my pants. Her thighs were so soft and juicy; they were real thick but very strong and silky smooth. I looked down and it looked like one of her thighs was as big as my torso, but I was one skinny ass kid. Her tits felt like the softest tits in the universe as they rested on my back and shoulders.
I liked having her in this position. My heart was racing as fast as hers.
“Sorry” she said, sounding nearly ashamed and embarrassed while more exhausted and fearful than anything. “I got nervous and panicked.”
“Kick, kick, kick, kick, kick! Jesus, I told you. Just relax and keep kicking. You have to use your legs and stop grabbing hold of the invisible flotation device if you want to learn how to swim.”
We went back to the shallow end and tried just kicking again. Now, that she had failed, and I pulled her to safety, I felt in complete control, almost like she was my little water puppet ready to obey my every command. I liked that feeling of control over her, a lot. Instead of holding her sides this time, I put my hand on her belly and/or hips while she kicked. This wasn’t helping her learn any better, but it was a way to get my hands on this vulnerable woman’s nervous body. I took more chances, once she started wildly flailing her legs around (I knew she would fail again, I was doing a horrible job teaching) I would touch her butt or graze her thighs, but I could write it off as an accident that happened trying to control her kicking chaos. I even squeezed her sides one time to while she was kicking out of control. She let out an “AAAGH!” and I felt her muscles tense. Her butt cheeks clinched together sucking in some of the white bikini bottoms into her ass crack, right in front of my face. Neither of us mentioned it. Again, it was written off as accidental but it tickled her! I knew it immediately. I was so horny and excited it was too much for me to handle.
“You’re hopeless” I said, “I’m done swimming.”
I hurried out of the pool a horny mess trying to act as if I was just frustrated with her. Truthfully, I was ready to burst open with the discovery of her ticklishness by my steady hand. For years my tickling fetish often brought about fantasies of my older stepmother. A stepmother whom I would love to have at the mercy of my fingers for reasons beyond her gorgeous body, but control over the woman with whom I often argued, battled for attention, and had a strong distaste for.
“Thank you so much for teaching me hun, I had a good time. Maybe we can practice more tomorrow.”
“Yeah… Whatever” I replied, and then went inside.
That night I thought about her more than usual as I visualized her spread eagle with me viciously attacking every inch of her body with my fingers. I thought to myself, I tickled her. I actually tickled her! The mystery was over, she's ticklish. The scene of her screaming as I slyly squeezed her sides and the image of her butt cheeks clinching tightly together kept me up almost all night long.
The next day after breakfast I was downstairs in the basement watching the Mets game. My dad yelled down and said that he was leaving to help my grandparents run some errands and help get some materials together to remodel their bathroom. “All right, see you later” I yelled back as I continued to watch the game. About 10 minutes later I heard the basement door open and down came Misty. Why was she still here? I thought, maybe they were going to be doing a lot of work at my grandfathers office and running around town so they just left her here to rest and relax so my dad could help his parents while he was in town. It didn’t matter to me; I was still excited about last night and actually very excited that she came to the basement. Still, I ignored her presence and kept watching T.V.
As I said before, Misty was a fitness freak. She owned tons of pairs of workout tights and wore them around the house on lazy afternoons. I fell in love with every pair she owned; they made her look so sexy. Today was no exception; she took a seat beside me on the bed wearing a pair of light green tights that ended just below her knee. She wore a blank tank top and no shoes or socks while I was lounging around in my pajamas, gray sweats and a white wife beater, it was a very lazy afternoon.
“Whatcha watchin’?” she asked.
“Baseball” I replied.
“Who’s playing?” she asked cheerfully.
“Mets” I answered.
“Who’s winning?” she said.
“Mets” I again replied, dully.
After our exciting discussion full of one word answers we sat in silence staring at the TV screen. I kept thinking about the pool, glancing at her body. I was nervous, very nervous. Finally, I made a move, a move that took her by surprise. I turned towards her and lay down, placing my head on her lap. Her legs were straight out so I put my ear on her upper thigh so I could still see the TV, although I was solely focused on her legs and pretty red toenails. She began stroking my hair and rubbing my back as a mother would do her son. I noticed in the mirror that she was sporting a smile from ear to ear. I finally was opening up to her; I was finally letting her in. While I was consumed with thoughts of her body and the feeling of her juicy soft thighs on my ear I did find myself feeling safe and comfortable with my head in her lap. It made me feel warm inside to see her smile. In fact, I actually WAS opening up to her, even if I did not intend on doing so.
“The Mets are getting killed. You can change it.” I offered in a cheerful voice, something more rare than the Mets NOT getting killed.
“No it’s okay. I like baseball” she lied.
I couldn’t hold out any longer, I extended my arm and tickled her bare foot.
“Hehe, you little…” she yelped as she pulled her feet back.
“Ticklish?” I inquired, as I flashed her a rare smile.
“Naw, just caught me off guard. I ain’t really very ticklish.”
She was lying. Maybe she hated being tickled, I thought. Maybe she really doesn’t want me to know about any of her weaknesses. Whatever the reason, I could tell she was trying to hide it. Now that I had finally showed her some love I knew she was in a happy place. I mean, she had been catering to my every need all week long. That, coupled with my appetizer of tickling in the pool the previous night made me realize I had to do something to make one of my fantasies come true. It was time to grow some balls; it may be my only opportunity. Without saying a word, I placed my left hand on her right shoulder as I reached across her chest and touched her left armpit with my right hand. Her face was strained as tight as her ass was the night before; her whole body was intensely clinched with her eyes closed, mouth shut, and her breath held. I gave her pit about four light strokes but got no reaction. Her armpit was smooth, but completely firm because she had tightened her muscles so much. It felt almost as if her armpit was retreating towards her shoulder, it formed a concave curve towards her body. I stopped touching her, but left my hand inches away from her underarm, waiting.
She exhaled and said, “See, I’m not really that… Wellllll…”
Just as she stopped holding her breath and tightening her body I gave it another shot. I barely touched her now relaxed, almost saggy armpit skin and I got an immediate reaction. Her eyeballs nearly doubled in size and her nose wrinkled as her body again tensed, this time involuntarily.
“Hmm hmm hmm hmm hmm” She laughed with a closed mouth. Trying as always not to look too foolish. Trying so hard to stay reserved and perfect in a moment where she was approaching helplessness and vulnerability.
My hand was firmly in her armpit now, being held in place by her arm that she dropped and held tightly to her side. I could tell that she assumed I would stop and that this was just a playful tickle that would be short lived, she was wrong.
I wiggled my hand faster and harder into the depths of her pit until her mouth burst open with laugher, “BWWAAAHAHAHAHAHAHAAA” she sang with a deep hearty laugh.
“HAHAHAHA HUUUULP HAHAHA HUUULP HAHA HULLP HUUUUULLLP” she continued laughing and began to produce extremely cute high pitched gasps for air. Then, she made a half ass attempt to tickle me with her free hand by barely stroking my chest with her fingers. Between her hearty giggles straight from the gut, her high pitched gasps for oxygen, and now her silent laughter, she managed to spit out the words, “I don’t want to hurt you with muh nails.”
“Oh really, you don’t wanna hurt ME? How thoughtful of you, Misty”
I dug into her other armpit and turned her body so that was now lying flat on her back.
“I can’t thank you enough for your concern.” I said, mocking her.
I was in the zone. The dialogue was just flowing off my tongue perfectly. I loved every second.
“But I don’t think you’re in a position to be doing a lot of hurting right now. What do you think?”
She began to lose it.
“HOWWWWW AAAAAAAA HAHAHAHAH… HEEEE EEEEEEEEEEYAAAHHAHAAHAHA… HO… HO… HO… MY… BWAHAHAHA…”
"Well, WHAT do you think? Did someone find some ticklewish pitty poos?" I said with a highly exaggerated baby voice.
She just laughed. Alternating between silence and loud bursts of laughter straight from her gut. Her mouth was wide open and her body was shaking.
"Say, not my pitty poos Frankie" I teased.
"ah... ah... ah... bwaahahahahhaa... nahhhhhaatt. myyyyyy. pittttty pooooooos... oooooooooooh godddddd!!! ohhhhhhhhhhhhh waahahaahahha..." she hollered
.
Her feet started to buck wildly underneath her, sometimes together sometimes one at a time. She kicked so hard sometimes her butt and small of her back would thrust completely off the bed and come crashing back down. I glanced in the mirror more than a few times to enjoy the view of her thighs and bootie jiggle in her sexy green workout tights.
“OOOOOOOOH. Nooooow you want to listen huh?” I teased, right before I chanted “kick kick kick kick kick”
She just laughed and laughed while I began to demand things from her.
“What’s the most fundamental building block of a good swimmer Misty? What do you have to do in order to swim?”
“Aahaha haha haahahaaaha. KICK… hahaaaa haaha” she yelped.
“What was that… how do you become a good swimmer?” I teased some more.
Her laughs suddenly changed. It sounded like a desperate, high pitched squeal. No longer was she able to laugh from her gut. She completely lost it.
“Bwaaaaaahaha... (silent laugh)... eehehehehehehe... heheheheheeeehehehe... hehehehehe... KIIeehhehee... KIIIIIEHEHHEEHE...”
"KIIIIIIIIIIIIIIICK" she finally screamed.
"Goooooood girllllll." I said, again in a baby voice.
After a few more precious seconds, I slowed the pace and eventually stopped completely. Out of breath and sweaty, Misty lay on the bed exhausted as I stared at her with the biggest smile of my life. She hit me in the face with a pillow and I lightly tossed one right back at her. We were laughing and play fighting now. I couldn't believe, and neither could she, what just happened. And we were actually bonding! I was having a good time, obviously.
"Why I've never been tickled like that in my life! I didn't even know I was that ticklish! I can't believe you DID that!!!" she said.
I was pretty much speechless. I could not help but just smile, smile, smile.
About thirty minutes pass and Misty gets up to get a glass of water from the kitchen. She asks if I would like one and I respectfully answer, “No thanks”. She returns in a few seconds and sets the water on the end table near the sofa. I’m in the process of remaking the bed I wrecked by tickling Misty when suddenly I’m lifted clear of the ground by the seat of my sweatpants and the collar of my shirt, then hurled face first on to the king sized bed. I try to push my self up with my arms but I am met with two hands pressing down hard on my shoulder blades. Then, I feel two soft, round, butt cheeks land directly on my own. I swear one of her cheeks was bigger than my whole ass.
At this point I'm completely freaked out. I knew she worked out and I knew that I was skinny as hell but she was a girl! There was no way she was man handling me like this. And to make matters worse, it didn't seem that she was even trying that hard, but it did seem like she was very serious, VERY serious.
She grabbed a handful of my hair and pulled it back towards her. She leaned in and whispered in my ear. "Baaaaaaaaad boy..."
I gulped. It sounded like she was hot for me, honestly it did. Millions of thoughts raced through my mind. It felt like she planned the whole thing almost, like she was steps ahead of me, like she hustled me into being in this desperate position, it even felt like she knew that for 3 years I fantasized about her and wanted her so badly, and that she was turned on as much as I was by the stepmother stepson thing and wanted to prove to me and herself that she could handle a young, healthy, 18 year old man with no problem.
"I hope that was fun for you." she slowly cooed in my ear as it sent chills down my spine. "But you made onnnnne biiiiiiig miiistake... you let me get up."
As soon as she said that she let my hair go, quickly positioned herself in front of my body so we were face to face, grabbed my head and stuck beneath her armpit in a wildly strong headlock, and went to town on my ass.
Whap! Whap! Whap! She whipped my butt with her bare hand about three or four times while saying, "Frankie Frankie Frankie. So mean. So disrespectful. Now I gotcha and aint nothin you can do or say..."
She then surprised me and let me go. I popped up and regained my train of thought and rose to two feet while she was still on the bed, standing straight up on her knees.
"C'mon skin n bones. Whatcha gonna do now?" she said threateningly.
I could tell she was turned on now. She loved every second, but a big part of her was also letting some frustration out her asshole of a stepson of 3 years.
I lunged at her with all my might, grabbing her shoulders as she grabbed mine. At this point I felt like I could have her at my mercy again. No longer had she caught me off guard. We were on an even playing field and I was a grown man! Then, I realized just how wrong I was...
I got her in a headlock and started talking shit... "GOTCHA!" I said, sounding pretty cocky.
She proceeded to stand straight up, lifting me off the ground entirely with my tummy on her shoulder, and she slammed me on the bed. Then with my legs spread towards her as I lay on my back she grabbed my ankles and yanked my body towards her. My butt slid on the bed and wrinkled the sheets I just neatly placed on the bed and when she let go of my ankles I pushed her away and turned around on my hands and knees.
"And just where ya think yer headin mister?" she said in a cute and playful little southern accent that she greatly exaggerated.
She jumped on my back and dug her hands into my armpits. I shook violently beneath her as she straddled my back. Teasing and torturing me like she was a pro.
"You messed with the wrong woman there sonny, now it's time you learn your lesson!"
"ahhhaahhahahhahahahhhaaaaaa. IM SORRRYYYY!!! hahahahhah AHHAHAAH hahahah HAHAHAAHAH... MIIIIIIISTYYYYYYYY..."
"Sorry aint cuttin it honey buns." she said as she pinched my left butt cheek. "Now, tell me who the boss is skinny mcskin skin..."
"YOU ARE... HAHAHAHAHA. MIIISTY IS..... HAHAHHAAHAH AAAAAAAAAAAAAAAAAAAAAAAAAHH HAHAHAHHAHAHAHAHA... MIIIIIST IIIISSSSSSS!"
"Misty is whhaaaaaaat?" she teased as she switched to my inner thighs while sitting on my back to hold me down so she could face my feet.
"THE BOSSSSSSSSSSSSSSSSSS... AAAAAHAHHAHAHAHHA!" I was loosing control. "I'm gonnnna peeeeeeeeeeeeeeee..."
"Now you better not wet this nice bed there young man, mommy taught her little boy better than that..."
That one stung. The mommy comment, she knew, would get me going.
I started to fight hard to get up, almost knocking her off my back but she re focused quickly and easily neutralized my best efforts. With me pinned down she said... "Boy, you know how much I work out. You think you can do anything. All 50 pounds of yourself? We aint in the pool big boy. Time for you to start kickin tho..."
As soon as she said that she did the unthinkable. she pulled my sweats down so that my bare bottom was showing. "WHHHEEEEEW WEE! LOOK AT THING!" she hollered. "Why I've never seen such a tight pair of honey buns in my forty some years! Let's see what Franky spanky thinks of my ten little friends here..."
She rapidly raced her fingernails all over my ass. Over the cheeks, over the crack, in between my legs, even towards my balls. I just went absolutely ape shit!
"OOOOOOOOOOOOOOOOH OOOH OOOH OOOH OOOH OOOOH OOOH AH AAAAAH AAAH AAAAAAH AHHHAAAA HAAAAAA HEEHEEEEEEEE HEEEE HEEHE HEEEEEEEEEEEE YOOOOOOOO WWWWAAAAAHAA. OOOOH MY GOD... MISTY MII MII MISTY..."
"Oh Misty Misty Mi Mi Misty" she mocked.
"PLLLEAAAAAAASE. HAHAHAHAHAHAL... PLEEEEEASE.... I... CAAAAANT... BREEEEEEATHE..."
She paused. "What's muh name there honey?"
"Miiiiisty!" I screamed.
"MOMMY" she said. "You ask Mommy nicely and we'll see okay?"
Then she continued, except now she was grabbing both of my ass cheeks with her hands and squeezing them until I began bucking wildly. She also discovered that if she squeezed the area where my leg meets my butt that I would go crazy.
"MOOOOMMMMMY... MOMMY NOOOOO. STOOOOP IT PLLLLEEHEHEHEHEEEEHEASEE HEHEHEHEHEH... OOOOOOOOOOOH SHSIIIIIIITTT..."
"Shit? Mommy taught you better than to talk like that. You never say that word to me again understand?"
"OOOOH YEEESSSS! HAHAA IM AHAHAHA OSOOOOOOO... IM SOOOO... HAHAHALHAHAA... IM SO SORRY..."
"You pwomissssse" she said in a baby voice.
"YEEEEEESSSS YEEEESSS. PLLLLESASSSSE MOMMY PLEEEEEASE..."
"Yes what?"
"YEEEEEEEEESSSSS SMAAAAHAAHHAHA AHHAHAAH MAAAAAAHAHAHA"
Just as I tried to say yes "MAM" she stuck her finger up my buttcrack and wiggled it with the quickness. It was like she had the perfect touch for all my spots, never could someone have hit all my spots as well as she did. I couldn't believe what was happening. I was in tears at this point...
"MAAAAWWAHAHAHAHHA HAHAHAHHAAHHAHAH AAAAAAAAAAAAAAAGGGHAHHAHAHAHA. HAHAH... YEEESSSS. AHAA... YESSSS... MAAAAAAAAAAAAAAAM!!!!" I finally got it out and she stopped.
"That's a good boy. Now get yourself dressed and ready for lunch. I'm making turkey sandwiches and I'll even let you have some Pepsi if you're a good boy." she said, one last time in the baby voice before smacking me hard in the ass and walking upstairs to the kitchen. But before she left she stopped, came back, leaned over my shoulder. ran her finger up my butt cheek one last time causing me to go "aaaaaagh" and shake my body like I had been struck by lightening, and kissed me on the cheek.
"I love you Frankie."
It was summer time. I was 18 years old in Long Island, New York with my father for a week’s vacation. We tried to travel up north from Virginia as much as possible so we could spend time with my grandparents. When we visited, we always stayed in the basement. I loved that basement because my grandfather put his old big screen TV down there. It had a huge king sized bed and a nice sofa as well. When I wasn’t swimming in their pool, one of our favorite family activities, I was usually downstairs enjoying the warm, quiet, extremely private basement with a gigantic television perfect for video games and watching baseball.
My parents divorced when I was five and I chose to stay with my mother. She had primary custody but I still saw my dad on the weekends. The divorce drove my dad to work a lot more. He did so for both financial and emotional reasons, I assume. As a result, our trips to New York became less and less frequent. In fact, we hadn’t made the trip in four years, the longest drought of my lifetime. We used to visit at least once a year. I was only 14 years old the last time we I saw my father’s parents, when my mother and father were still married.
Now I had I just turned 18, and this visit to Long Island was slightly different than the rest. My father remarried his new wife Misty when I was 15, and this was the first time she would be meeting the family. She was welcomed with open arms by everyone. Well, everyone except me that is. I was a momma’s boy. I loved my mother and the thought of this new woman in the Long Island home that I had so many fond memories of my perfect family angered me.
While I may not have particularly cared for Misty, she was something nice to look at. She stood about 5’9. I would guess she weighed about 145 pounds. She was in her late forties. She had nice big breasts, hips to die for, thick tone thighs, and a perfectly pump and beautiful bum. She was a workout freak; she spent 6 days a week in the gym after work and got up at 4am everyday to run on the treadmill before she started her day. She had a very pretty face and a slight southern accent that was very cute. Her hair was brown with very few strands of gray, but I didn’t mind. In fact, the gray hairs somehow made her even sexier to me. Something about older women aroused me. The only negative in my eyes was that she tanned too much and you could tell it wasn’t natural. It showed in the color and texture of her skin, but she was still a fine grown woman who refused to let herself go. I admired her for her work ethic when it came to keeping her body in shape, but she was no fun. It was like every aspect of her life was a job and she never let her guard down. This bothered me about her. She was a confident, sexy, intelligent, and independent woman but she seemed to never let her hair down. Work, dinner, sleep. That was the routine. Never did she and my father go out dancing or to the movies. I think he married her because she was a trophy wife and he was lonely from the divorce.
Right before the trip Misty and I got into an argument. My father and I had a big fight about my grades (senior in high school) and she chimed in, something she had never done before. I snapped at her, “Don’t you EVER tell me what to do. You are NOT my mom and you will NEVER be my mom.” A week later we were on the road and cooler heads prevailed. We were all "getting along" as if the fight never took place.
From day one, Misty really wanted to be close to me. She knew that my dad really loved me and I think that pushed her even harder to create a motherly relationship with his only child. Of course, my cocky teenage attitude, raging hormones, and bitter jealousy never allowed her to gain an inch. I was cordial with her, but she was NOT my mother. We got a little better once I became a senior; but that was because I was always out with my friends so we barely saw one another, not because we improved our stepmother/stepson relationship.
During the vacation she made one of her greatest attempts to get close to me. Maybe it was because we had the fight, maybe it was because she was trying to impress the family, or maybe she just wanted us to be close now that she was officially a part of our family and we were about to spend a whole week together. Whatever the reason, she laid it on thick with slews of compliments about how handsome and intelligent I was, offers to get me something to drink or eat throughout the day, letting me have the TV remote, sticking up for me when my dad got in one of his moods, you name it. I of course was disinterested. I wasn’t being a wickedly moody bastard child, but I definitely gave her the cold shoulder as much as possible. I don’t know exactly why. Maybe it was because I didn’t WANT to accept her as a good person, maybe I was searching for her flaws, maybe I was just being a stepchild who loved his real mother, or maybe I just felt like she was trying too hard. Nonetheless, I was obviously unaffected, unimpressed, and unmoved by her desperate attempts to become closer.
On our third night of the vacation, the adults left the pool area and got ready for coffee and cards. As always, I elected to stay in the water with the pool lights on and keep swimming. I loved swimming in my grandparents pool. Misty, while loved by the family didn’t really participate in all of our favorite hobbies. She didn’t know any of the card games they played so she just sat by my dad and had fun exchanging conversation as they played poker, hearts, spades, etc. But, she didn’t know how to swim! This really irked me because I had never met anyone who couldn’t swim. My entire family could swim, and loved swimming. I practically grew up in that pool.
As I continuously tired my paper thin, 5'7 100 pound body by diving, jumping, and doing laps around the pool I noticed Misty step outside. She was alone and surprisingly still in her swimsuit, a white bikini that was one of my favorites. The top was very classy but still couldn’t hide her perfectly round boobs and the bottoms had two gold rings at her hips which the fabric was attached. They hugged her lower half beautifully, highlighting her incredibly delicious hips, thighs, and bottom. She went to the shallow end of the pool and walked down the stairs. I continued my routine, ignoring her for a good 5 minutes until she finally spoke,
“Frankie, I want to learn to swim. You are such an incredible swimmer; I’d love it if you could teach me.”
Annoyed, I responded,
“If you don’t know by now it’s going to be real hard to learn.”
She persisted,
“Please. Can you at least try?”
“Fine.” I replied.
I proceeded to explain briefly the basics of how to swim freestyle. Her first attempts in the shallow end were miserable failures. I held her up by her sides and instructed her to “kick, kick, kick.” She flailed her legs wildly making more noise than progress. “Stop, try this” I said, as I gave her a demonstration on how to doggy paddle. She seemed to be able to mildly execute the doggy paddle, in the shallow end. I said, “All right, you can doggy paddle. It’s a start.”
Then I instructed her to paddle from the edge of the shallow end to the diving board and back. She took off. I swam by her side just in case. Then, she realized that she couldn’t touch the bottom and panicked instantly. She started grabbing for me violently. I took her arm and dragged her to the diving board. By then, scared shitless, she had her legs and arms wrapped around my body. Her breasts pressed firmly against my back and I could hear her heart racing at the rate that could have rivaled a bumble bee's. If a hard on were possible while in the pool, I would have had a rocket in my pants. Her thighs were so soft and juicy; they were real thick but very strong and silky smooth. I looked down and it looked like one of her thighs was as big as my torso, but I was one skinny ass kid. Her tits felt like the softest tits in the universe as they rested on my back and shoulders.
I liked having her in this position. My heart was racing as fast as hers.
“Sorry” she said, sounding nearly ashamed and embarrassed while more exhausted and fearful than anything. “I got nervous and panicked.”
“Kick, kick, kick, kick, kick! Jesus, I told you. Just relax and keep kicking. You have to use your legs and stop grabbing hold of the invisible flotation device if you want to learn how to swim.”
We went back to the shallow end and tried just kicking again. Now, that she had failed, and I pulled her to safety, I felt in complete control, almost like she was my little water puppet ready to obey my every command. I liked that feeling of control over her, a lot. Instead of holding her sides this time, I put my hand on her belly and/or hips while she kicked. This wasn’t helping her learn any better, but it was a way to get my hands on this vulnerable woman’s nervous body. I took more chances, once she started wildly flailing her legs around (I knew she would fail again, I was doing a horrible job teaching) I would touch her butt or graze her thighs, but I could write it off as an accident that happened trying to control her kicking chaos. I even squeezed her sides one time to while she was kicking out of control. She let out an “AAAGH!” and I felt her muscles tense. Her butt cheeks clinched together sucking in some of the white bikini bottoms into her ass crack, right in front of my face. Neither of us mentioned it. Again, it was written off as accidental but it tickled her! I knew it immediately. I was so horny and excited it was too much for me to handle.
“You’re hopeless” I said, “I’m done swimming.”
I hurried out of the pool a horny mess trying to act as if I was just frustrated with her. Truthfully, I was ready to burst open with the discovery of her ticklishness by my steady hand. For years my tickling fetish often brought about fantasies of my older stepmother. A stepmother whom I would love to have at the mercy of my fingers for reasons beyond her gorgeous body, but control over the woman with whom I often argued, battled for attention, and had a strong distaste for.
“Thank you so much for teaching me hun, I had a good time. Maybe we can practice more tomorrow.”
“Yeah… Whatever” I replied, and then went inside.
That night I thought about her more than usual as I visualized her spread eagle with me viciously attacking every inch of her body with my fingers. I thought to myself, I tickled her. I actually tickled her! The mystery was over, she's ticklish. The scene of her screaming as I slyly squeezed her sides and the image of her butt cheeks clinching tightly together kept me up almost all night long.
The next day after breakfast I was downstairs in the basement watching the Mets game. My dad yelled down and said that he was leaving to help my grandparents run some errands and help get some materials together to remodel their bathroom. “All right, see you later” I yelled back as I continued to watch the game. About 10 minutes later I heard the basement door open and down came Misty. Why was she still here? I thought, maybe they were going to be doing a lot of work at my grandfathers office and running around town so they just left her here to rest and relax so my dad could help his parents while he was in town. It didn’t matter to me; I was still excited about last night and actually very excited that she came to the basement. Still, I ignored her presence and kept watching T.V.
As I said before, Misty was a fitness freak. She owned tons of pairs of workout tights and wore them around the house on lazy afternoons. I fell in love with every pair she owned; they made her look so sexy. Today was no exception; she took a seat beside me on the bed wearing a pair of light green tights that ended just below her knee. She wore a blank tank top and no shoes or socks while I was lounging around in my pajamas, gray sweats and a white wife beater, it was a very lazy afternoon.
“Whatcha watchin’?” she asked.
“Baseball” I replied.
“Who’s playing?” she asked cheerfully.
“Mets” I answered.
“Who’s winning?” she said.
“Mets” I again replied, dully.
After our exciting discussion full of one word answers we sat in silence staring at the TV screen. I kept thinking about the pool, glancing at her body. I was nervous, very nervous. Finally, I made a move, a move that took her by surprise. I turned towards her and lay down, placing my head on her lap. Her legs were straight out so I put my ear on her upper thigh so I could still see the TV, although I was solely focused on her legs and pretty red toenails. She began stroking my hair and rubbing my back as a mother would do her son. I noticed in the mirror that she was sporting a smile from ear to ear. I finally was opening up to her; I was finally letting her in. While I was consumed with thoughts of her body and the feeling of her juicy soft thighs on my ear I did find myself feeling safe and comfortable with my head in her lap. It made me feel warm inside to see her smile. In fact, I actually WAS opening up to her, even if I did not intend on doing so.
“The Mets are getting killed. You can change it.” I offered in a cheerful voice, something more rare than the Mets NOT getting killed.
“No it’s okay. I like baseball” she lied.
I couldn’t hold out any longer, I extended my arm and tickled her bare foot.
“Hehe, you little…” she yelped as she pulled her feet back.
“Ticklish?” I inquired, as I flashed her a rare smile.
“Naw, just caught me off guard. I ain’t really very ticklish.”
She was lying. Maybe she hated being tickled, I thought. Maybe she really doesn’t want me to know about any of her weaknesses. Whatever the reason, I could tell she was trying to hide it. Now that I had finally showed her some love I knew she was in a happy place. I mean, she had been catering to my every need all week long. That, coupled with my appetizer of tickling in the pool the previous night made me realize I had to do something to make one of my fantasies come true. It was time to grow some balls; it may be my only opportunity. Without saying a word, I placed my left hand on her right shoulder as I reached across her chest and touched her left armpit with my right hand. Her face was strained as tight as her ass was the night before; her whole body was intensely clinched with her eyes closed, mouth shut, and her breath held. I gave her pit about four light strokes but got no reaction. Her armpit was smooth, but completely firm because she had tightened her muscles so much. It felt almost as if her armpit was retreating towards her shoulder, it formed a concave curve towards her body. I stopped touching her, but left my hand inches away from her underarm, waiting.
She exhaled and said, “See, I’m not really that… Wellllll…”
Just as she stopped holding her breath and tightening her body I gave it another shot. I barely touched her now relaxed, almost saggy armpit skin and I got an immediate reaction. Her eyeballs nearly doubled in size and her nose wrinkled as her body again tensed, this time involuntarily.
“Hmm hmm hmm hmm hmm” She laughed with a closed mouth. Trying as always not to look too foolish. Trying so hard to stay reserved and perfect in a moment where she was approaching helplessness and vulnerability.
My hand was firmly in her armpit now, being held in place by her arm that she dropped and held tightly to her side. I could tell that she assumed I would stop and that this was just a playful tickle that would be short lived, she was wrong.
I wiggled my hand faster and harder into the depths of her pit until her mouth burst open with laugher, “BWWAAAHAHAHAHAHAHAAA” she sang with a deep hearty laugh.
“HAHAHAHA HUUUULP HAHAHA HUUULP HAHA HULLP HUUUUULLLP” she continued laughing and began to produce extremely cute high pitched gasps for air. Then, she made a half ass attempt to tickle me with her free hand by barely stroking my chest with her fingers. Between her hearty giggles straight from the gut, her high pitched gasps for oxygen, and now her silent laughter, she managed to spit out the words, “I don’t want to hurt you with muh nails.”
“Oh really, you don’t wanna hurt ME? How thoughtful of you, Misty”
I dug into her other armpit and turned her body so that was now lying flat on her back.
“I can’t thank you enough for your concern.” I said, mocking her.
I was in the zone. The dialogue was just flowing off my tongue perfectly. I loved every second.
“But I don’t think you’re in a position to be doing a lot of hurting right now. What do you think?”
She began to lose it.
“HOWWWWW AAAAAAAA HAHAHAHAH… HEEEE EEEEEEEEEEYAAAHHAHAAHAHA… HO… HO… HO… MY… BWAHAHAHA…”
"Well, WHAT do you think? Did someone find some ticklewish pitty poos?" I said with a highly exaggerated baby voice.
She just laughed. Alternating between silence and loud bursts of laughter straight from her gut. Her mouth was wide open and her body was shaking.
"Say, not my pitty poos Frankie" I teased.
"ah... ah... ah... bwaahahahahhaa... nahhhhhaatt. myyyyyy. pittttty pooooooos... oooooooooooh godddddd!!! ohhhhhhhhhhhhh waahahaahahha..." she hollered
.Her feet started to buck wildly underneath her, sometimes together sometimes one at a time. She kicked so hard sometimes her butt and small of her back would thrust completely off the bed and come crashing back down. I glanced in the mirror more than a few times to enjoy the view of her thighs and bootie jiggle in her sexy green workout tights.
“OOOOOOOOH. Nooooow you want to listen huh?” I teased, right before I chanted “kick kick kick kick kick”
She just laughed and laughed while I began to demand things from her.
“What’s the most fundamental building block of a good swimmer Misty? What do you have to do in order to swim?”
“Aahaha haha haahahaaaha. KICK… hahaaaa haaha” she yelped.
“What was that… how do you become a good swimmer?” I teased some more.
Her laughs suddenly changed. It sounded like a desperate, high pitched squeal. No longer was she able to laugh from her gut. She completely lost it.
“Bwaaaaaahaha... (silent laugh)... eehehehehehehe... heheheheheeeehehehe... hehehehehe... KIIeehhehee... KIIIIIEHEHHEEHE...”
"KIIIIIIIIIIIIIIICK" she finally screamed.
"Goooooood girllllll." I said, again in a baby voice.
After a few more precious seconds, I slowed the pace and eventually stopped completely. Out of breath and sweaty, Misty lay on the bed exhausted as I stared at her with the biggest smile of my life. She hit me in the face with a pillow and I lightly tossed one right back at her. We were laughing and play fighting now. I couldn't believe, and neither could she, what just happened. And we were actually bonding! I was having a good time, obviously.
"Why I've never been tickled like that in my life! I didn't even know I was that ticklish! I can't believe you DID that!!!" she said.
I was pretty much speechless. I could not help but just smile, smile, smile.
About thirty minutes pass and Misty gets up to get a glass of water from the kitchen. She asks if I would like one and I respectfully answer, “No thanks”. She returns in a few seconds and sets the water on the end table near the sofa. I’m in the process of remaking the bed I wrecked by tickling Misty when suddenly I’m lifted clear of the ground by the seat of my sweatpants and the collar of my shirt, then hurled face first on to the king sized bed. I try to push my self up with my arms but I am met with two hands pressing down hard on my shoulder blades. Then, I feel two soft, round, butt cheeks land directly on my own. I swear one of her cheeks was bigger than my whole ass.
At this point I'm completely freaked out. I knew she worked out and I knew that I was skinny as hell but she was a girl! There was no way she was man handling me like this. And to make matters worse, it didn't seem that she was even trying that hard, but it did seem like she was very serious, VERY serious.
She grabbed a handful of my hair and pulled it back towards her. She leaned in and whispered in my ear. "Baaaaaaaaad boy..."
I gulped. It sounded like she was hot for me, honestly it did. Millions of thoughts raced through my mind. It felt like she planned the whole thing almost, like she was steps ahead of me, like she hustled me into being in this desperate position, it even felt like she knew that for 3 years I fantasized about her and wanted her so badly, and that she was turned on as much as I was by the stepmother stepson thing and wanted to prove to me and herself that she could handle a young, healthy, 18 year old man with no problem.
"I hope that was fun for you." she slowly cooed in my ear as it sent chills down my spine. "But you made onnnnne biiiiiiig miiistake... you let me get up."
As soon as she said that she let my hair go, quickly positioned herself in front of my body so we were face to face, grabbed my head and stuck beneath her armpit in a wildly strong headlock, and went to town on my ass.
Whap! Whap! Whap! She whipped my butt with her bare hand about three or four times while saying, "Frankie Frankie Frankie. So mean. So disrespectful. Now I gotcha and aint nothin you can do or say..."
She then surprised me and let me go. I popped up and regained my train of thought and rose to two feet while she was still on the bed, standing straight up on her knees.
"C'mon skin n bones. Whatcha gonna do now?" she said threateningly.
I could tell she was turned on now. She loved every second, but a big part of her was also letting some frustration out her asshole of a stepson of 3 years.
I lunged at her with all my might, grabbing her shoulders as she grabbed mine. At this point I felt like I could have her at my mercy again. No longer had she caught me off guard. We were on an even playing field and I was a grown man! Then, I realized just how wrong I was...
I got her in a headlock and started talking shit... "GOTCHA!" I said, sounding pretty cocky.
She proceeded to stand straight up, lifting me off the ground entirely with my tummy on her shoulder, and she slammed me on the bed. Then with my legs spread towards her as I lay on my back she grabbed my ankles and yanked my body towards her. My butt slid on the bed and wrinkled the sheets I just neatly placed on the bed and when she let go of my ankles I pushed her away and turned around on my hands and knees.
"And just where ya think yer headin mister?" she said in a cute and playful little southern accent that she greatly exaggerated.
She jumped on my back and dug her hands into my armpits. I shook violently beneath her as she straddled my back. Teasing and torturing me like she was a pro.
"You messed with the wrong woman there sonny, now it's time you learn your lesson!"
"ahhhaahhahahhahahahhhaaaaaa. IM SORRRYYYY!!! hahahahhah AHHAHAAH hahahah HAHAHAAHAH... MIIIIIIISTYYYYYYYY..."
"Sorry aint cuttin it honey buns." she said as she pinched my left butt cheek. "Now, tell me who the boss is skinny mcskin skin..."
"YOU ARE... HAHAHAHAHA. MIIISTY IS..... HAHAHHAAHAH AAAAAAAAAAAAAAAAAAAAAAAAAHH HAHAHAHHAHAHAHAHA... MIIIIIST IIIISSSSSSS!"
"Misty is whhaaaaaaat?" she teased as she switched to my inner thighs while sitting on my back to hold me down so she could face my feet.
"THE BOSSSSSSSSSSSSSSSSSS... AAAAAHAHHAHAHAHHA!" I was loosing control. "I'm gonnnna peeeeeeeeeeeeeeee..."
"Now you better not wet this nice bed there young man, mommy taught her little boy better than that..."
That one stung. The mommy comment, she knew, would get me going.
I started to fight hard to get up, almost knocking her off my back but she re focused quickly and easily neutralized my best efforts. With me pinned down she said... "Boy, you know how much I work out. You think you can do anything. All 50 pounds of yourself? We aint in the pool big boy. Time for you to start kickin tho..."
As soon as she said that she did the unthinkable. she pulled my sweats down so that my bare bottom was showing. "WHHHEEEEEW WEE! LOOK AT THING!" she hollered. "Why I've never seen such a tight pair of honey buns in my forty some years! Let's see what Franky spanky thinks of my ten little friends here..."
She rapidly raced her fingernails all over my ass. Over the cheeks, over the crack, in between my legs, even towards my balls. I just went absolutely ape shit!
"OOOOOOOOOOOOOOOOH OOOH OOOH OOOH OOOH OOOOH OOOH AH AAAAAH AAAH AAAAAAH AHHHAAAA HAAAAAA HEEHEEEEEEEE HEEEE HEEHE HEEEEEEEEEEEE YOOOOOOOO WWWWAAAAAHAA. OOOOH MY GOD... MISTY MII MII MISTY..."
"Oh Misty Misty Mi Mi Misty" she mocked.
"PLLLEAAAAAAASE. HAHAHAHAHAHAL... PLEEEEEASE.... I... CAAAAANT... BREEEEEEATHE..."
She paused. "What's muh name there honey?"
"Miiiiisty!" I screamed.
"MOMMY" she said. "You ask Mommy nicely and we'll see okay?"
Then she continued, except now she was grabbing both of my ass cheeks with her hands and squeezing them until I began bucking wildly. She also discovered that if she squeezed the area where my leg meets my butt that I would go crazy.
"MOOOOMMMMMY... MOMMY NOOOOO. STOOOOP IT PLLLLEEHEHEHEHEEEEHEASEE HEHEHEHEHEH... OOOOOOOOOOOH SHSIIIIIIITTT..."
"Shit? Mommy taught you better than to talk like that. You never say that word to me again understand?"
"OOOOH YEEESSSS! HAHAA IM AHAHAHA OSOOOOOOO... IM SOOOO... HAHAHALHAHAA... IM SO SORRY..."
"You pwomissssse" she said in a baby voice.
"YEEEEEESSSS YEEEESSS. PLLLLESASSSSE MOMMY PLEEEEEASE..."
"Yes what?"
"YEEEEEEEEESSSSS SMAAAAHAAHHAHA AHHAHAAH MAAAAAAHAHAHA"
Just as I tried to say yes "MAM" she stuck her finger up my buttcrack and wiggled it with the quickness. It was like she had the perfect touch for all my spots, never could someone have hit all my spots as well as she did. I couldn't believe what was happening. I was in tears at this point...
"MAAAAWWAHAHAHAHHA HAHAHAHHAAHHAHAH AAAAAAAAAAAAAAAGGGHAHHAHAHAHA. HAHAH... YEEESSSS. AHAA... YESSSS... MAAAAAAAAAAAAAAAM!!!!" I finally got it out and she stopped.
"That's a good boy. Now get yourself dressed and ready for lunch. I'm making turkey sandwiches and I'll even let you have some Pepsi if you're a good boy." she said, one last time in the baby voice before smacking me hard in the ass and walking upstairs to the kitchen. But before she left she stopped, came back, leaned over my shoulder. ran her finger up my butt cheek one last time causing me to go "aaaaaagh" and shake my body like I had been struck by lightening, and kissed me on the cheek.
"I love you Frankie."
