Story Details

Caught in the rain

Sydneyspikes 1290 days ago on Sissy Stories

It was a rainy day after my summer school class, I was 18 going to prep before college. I got a lift to my tutor, an amazingly cheerful woman, late 40's; she always made my day with her smile and always surprised me with how deliciously intriguing she was to me, even though we had decades between us.

The woman that gave me a lift was an unconfident driver, and would not pull down the driveway of the tutors house. She was convinced the rain would make it impossible for her to get back out of the driveway...so I got out in the down-pour. I wasn't going to argue with her...she was my nanny, and now, sole caretaker, after the accident. The rain soaked my clothes, which consisted of a pair of khakis and a black t-shirt, both of which were sticking to me. As I made my way to the front door of the tutors place she could see me through the window and ran to the door, opened it, she widened her eyes and grinned, showing her remarkably white teeth, frantically motioning for me to come inside with haste.
I came through the door and she stood there looking at me with a "what the hell?" smile still on her face. We both laughed and I took my book-bag off and put it on the welcome mat.

"Im going to get you a towel." she said and ran off to her laundry, just off the office. I kicked off my shoes and waited. Standing there, I could feel the moisture seeping deeper into my clothes and into my underwear... my underwear, Is a story in itself. It was a tad a-typical. My nanny had been the one to give me a pair of Jockey string bikinis she grabbed from Walmart. She mistakenly thought they were normal underwear. I wore them and liked them...she never said anything about it or attempted to correct the mistake. They would just appear clean in my drawer, folded nicely. So when it came time to get new undies, I would go online to order new ones in the same fashion. Over time, I tried different brands and styles and had a little collection of fun undies from string bikinis to very sparse and revealing pouches with a g-string back. I occasionally would wear normal boxers for sporting events etc, but for the most part, stuck to the bikinis. The tutor came back from the laundry and tossed me a soft warm towel.

"Jeeze, you got soaked." She said as she watched me attempt to dry myself from top to bottom. I only stopped the dripping and the towel was at capacity, I stood there still in clothes that appeared to be fresh from the washer. It was hot out, and the AC was on, making my body feel like it was wrapped in tin foil.

"Thanks!" I said and handed her the towel back.

"You look so uncomfortable..." she said with a chuckle.

"It's not great." I muttered in agreement. She studied me for a moment and then hung the towel on the coat rack.

"I'll throw your stuff in the drier while we are working, ok?"

"It's ok." I said bashfully, knowing I'd have to be well...naked for this plan to work.

"Keep your skivvies on, and I'll get you a blanket." She said as she walked again into the office and grabbed a blanket off the love seat.

"Ok hand em over." She said as she held the blanket out, mantling me like a make-shift curtain. My cheeks flushed and I could feel my blood turn to ice as I realized I would be wearing bikinis today, no sports, no locker-room.

"Honestly I'll be ok..." She interrupted me

"No, you're not sitting on my furniture soaking wet kiddo." She said as she smiled a matter of fact smile at me.

"Ok...I um"

She sighs; "You got nothing I haven't seen before kiddo, just take the wet stuff off and wrap up." She said now staring and waiting.

I took off my shirt with some difficulty, it skidded across my skin and made a tarp like sound as it passed over my head. She grabbed it, and one side of the blanket fell, as she now didn't have enough hands. I then unbuttoned and slid down my pants, clumsily, hopping around for a moment, trying to be quick. I was hoping to just hand them off and have her not notice my rain-soaked, bikinis. I could feel the air hit my body like a cold nebula. The thin, cotton string-bikini I wore was damp and clung to my package; it looked heavy and created a scalloped pattern of tension waves, starting at the head of my cock and splaying out to the strap that held up the pouch.

I'm not going to lie, it looked magnificent, and the light baby-blue color when wet, made for a rather transparent carapace. I straightened up and gained my balance. She grabbed the pants and I could see her eyes dart across my groin. She put her arms down at her sides and did not give me the blanket as I thought she would. A huge smile struck across her face, blushed a bit and nodded.

"Those..." She said as her smile widened to almost a laugh "Those are cute!" She said as she then made eye contact. I had no idea what to say, I just stood there, I had a feeling of a weight being taken off my shoulders, a huge weight, which gave way to a little twinge of arousal.

Before I could say anything, she tossed me the blanket and walked to the laundry with my clothes. "Ok let's do this," she said, ushering me to join her in the office.

I wrapped myself in the blanket and grabbed my books andheaded for the office. It was a quaint and cozy place. She and I were side by side as with most tutors, and she and I would labour away on whichever horrible math assignment I had for the day. As the session went on, I became less and less aware of the blanket, and the front of it would start to part open, revealing my torso and groin, and I would pull it back together as we tried to find X, or solve for Y. At one point she leaned forward to grab her TI-83 and her t-shirt was pulled up. A white silky line was revealed for a moment, tracing her hip as it peeked out of her jeans. My eyes scanned the strap back to where there would usually be more fabric, but saw barely any as the panties disappeared into the crevice at the small of her back and into her cleft.

She spied me looking and smiled. "Hey kiddo. up here." I acted like I had been looking elsewhere and got distracted from my math problem. As per usual, I found tangents to talk about and ways to distract from the work at hand. She would humor me and listen intently then steer me back to the task. During one such tangent I gesticulated and the blanket fell to the sides completely revealing my body, and my package gingerly resting on my thighs, shrink-wrapped in the thin cotton and displayed in a nice bundle. She once again darted her eyes to my groin and left them there for a tad longer than before and then got her business face on.

I started to reach down and grab it to begin bundling myself again

"Alright, forget about the blanket, no more distractions, lets plow through this before our time it up ok?" I did as she said. And I started to work.

"And so, if this is the only variable this is the...?" She asked.

"I can't remember, crap..." I said leaning on the desk with my elbows.

"You are so funny" she said as she reclined for a moment folding her arms. "you remember everything, but this stuff..."

I sighed and leaned back; "yeah I know... I just hate it." I said, turning my head to look at her.

She bites her lip; "I feel like with the proper motivation you'll get this." She said matter of fact. She reached down and undid her button on her jeans. "You like sexy undies right?" I said nothing, eyes wide.

"Yours are really cute, don't get me wrong, but mine are pretty killer too." She locked her eyes on me and arched her back coyly, as she slowly pulled her fly down and revealed the front triangle panel, bright turquoise, slack with the fabric having been displaced by the friction of the jeans on the obviously not very secure panties. She pulled up the panel a bit to make it peek out, revealing two slivers of her pelvis on either side, where usually there would be pubic hair, but on her, it was clean and smooth.

"What do you think?" She said, smiling at me. My cock immediately responded by filling my bikinis a tad, giving me a half-mast erection.

"I...those are hot." I said back trying to gain some conviction to my voice.

She smiles again, that mouthwatering smile and giggles "Tell you what" She leaned forward resting her chin on her hands, "I'll show you more if you can get these next couple problems."

I smiled, "Ok." We then resumed the session as if nothing had happened, me laboring over the problems and she perched on her elbows inches from me pointing and guiding my mind through the work. All I could think about was how the rest of her panties would look on her.

"Nailed it." She said making fist and a celebratory gesture over her head. As she leaned back she arched her back against the back of the chair and stuck her finger in the belt loops of her jeans.

"Now you get to have a better look." She said, straining a bit as she pulled the jeans down and off her body. She sat there in her t-shirt and panties and some socks that came to her calves.

"Aren't we a pair?" She said with a giant smile and a chuckle. Her panties were tiny. The white straps were spaghetti thin, and the fabric was a polyester silk blend that when she pulled them up and adjusted them, pulling the partial coverage of the back out of her cleft, made a beautiful pouch, as if her pussy was just painted a different color and texture. I stared and became aware that I was getting fully erect. My cock was now pulling, no raging against my pouch with such fervor, that it was starting to pull the fabric away from my body, showing a little bit of the flesh beneath.

"Ha! You do like them!" She then plucks the strap on my bikini like a guitar string, gazing like a daydream at my cock jostling around in the cotton hammock. She brings her fingertips as if about to caress the head through the fabric, when as if being ripped out of a wet dream, the drier buzzes and she looks at the laundry room door, then at me for a moment and shrugged. "Your clothes are ready." I was visibly unhappy by this revelation.

She meditated for a moment; "But tell you what, we ain't done yet." She said and slid her chair back to the desk. "I think we can finish all this work before you ride is here, but we'll need to step up the pace a bit." She reaches for a jar of something that was tucked behind the pencils and nick-nacks. It's a small jar of Vaseline, I had seen her use it religiously on her lips, I assumed she was grabbing it for this purpose.

"Ok kiddo slide back a moment." I studied her face, totally normal grin, I slid back my chair and she looked down.

"Just delightful, my god, and those undies are unreal, little wet bikinis on a giant ..."

She covers her mouth as if she has let the cat out of the bag. I chuckled, it wasn't news, I knew I had a big dick...

"Thanks..." I say with a grin.

"Ok I got an idea, slip that hog of yours out." She says as she pops the lid on the Vaseline and uses an index finger to get a dime sized mound of it scooped up.

"Ok" I say in a dreamlike voice...a hot flash washes over my entire body as I look down at my straining bikini, my hands go to my waist and I grabbed the front of my pouch and pulled it down, peeling it away, the head caught in the fabric cohesion, it let go only when it has enough force to launch the entire shaft like a catapult; it came springing out, resting, slightly slouching to the left towards the tutor. She looked at it endearingly and shifted her body forward to get a better purchase and then tapped the top of my cock, at the base of the head just below its swollen, pink, fleshy helmet, the Vaseline sticks like a dollop of cool whip.

"There" she said with a laugh and returned her jar to its place. She then gestured for me to push myself back into the table and I did. We began to work again. I finished the problem correctly and I looked at her with anticipation. She didn't look at me and turned the page to the next problem, when I turned my attention back to the book, I felt her hand grab the shaft of my cock under the table with her right hand, warm, firm yet delicate, and and she began massaging the Vaseline into the head of my penis.

"Good, next one." She said again not looking from the book, no acknowledgment of the actions under the table, just her shoulder shrugging slightly from her gripping, rubbing and kneading. It was hard for me to concentrate completely, but I managed to get another problem solved. Again no engagement, just a nod and then her fingers flipped down, fanned out, dexterous and experienced, she flicked the elastic band of the pouch down, you could hear a fluttering snap as she quickly released my balls, they poured out and sagged, now they came into play. It was almost too much, and I started groaning, threw my head back and involuntarily pushed my chair back an inch or two.

"ah ah ah, we're not done yet." She said.

I brought myself back from my pleasure cruise by adjusting my posture and sitting upright, but she didn't miss a beat, I could see her hands since I moved back, her right still gripped and rubbed my cock, her thumb and forefinger applied pressure just as they skated over the crest of the head and stopped to twirl and dip into the urethra for milliseconds. Her left hand was now gently massaging my balls and playing with the fabric holding my package up in an offering, making my cock and testicles appear to be their own entity. She began to get more into the process, she leaned forward into her work and her thighs enveloped her panties. I could see her modestly plump and sexy curves as they mingled with the straps of her panties, and the now lightly bunched silky front panel seeping into her pussy.

"I...I can't." I pout.

She stopped everything and looked at me with a bit of despair. I involuntarily gasped. She got up from the chair and turned, her beautiful ass is barely covered by the back of the garment, purposely too little to cover her peach like ass. She knew they were too small. When she got dressed that morning, she had a similar rush as I did, knowing how sexy she looked under her clothes. She pulled out the fabric that had snuggled into her cheeks and placed it back daintily, arching her back again as if a subject of a painting, and pouting her lips as if to say it was improper to have it slipping into her cleft, creating a glorious little waterfall of shiny fabric into her flesh. She then grabbed the book off the table and walked seductively, her hips and frame iterating every step with a carnal giggle, and sat down on the love seat.

"Ok then, I'll finish this work for you tonight." She says as she nestles into the couch and leans back. snatching the paper and pencil from between the pages and popping the pencil in her mouth.

I just looked at her sullenly.

"But under the condition that you finish me." She said, spreading her legs and leering at me from behind the book.

Her panties were barely on her, they had pulled tightly against her body and rolled up a bit from "getting comfy" rocking on the couch. The pouch that held her pussy, which she had gloriously displayed for me before, now darkened with moisture and slipped into the gentle slopes and gullies where legs became crotch. She pointed to it with her pencil.

"eat up." She commanded.

Then went about doing the work I was supposed to finish for tomorrow.

I got up from my chair and walked over to her eagerly, my cock wagging in the air as I walked, glistening with pre-cum and vaseline. I fell to my knees and tucked my face into the warm and cozy area where her thighs gently coaxed my face to her turquoise triangle. I could smell the sweet, clean smell of laundry sheets and body-wash, then the faint aroma of her body as I pushed my mouth into her, silky and wet and electric. I arched my back to get leverage, pushing from the balls of my feet, to start sucking, tonguing and playing...slurping and pulled on the panties with my right hand to keep them from interrupting me. She worked diligently for minutes, occasionally warped her body as if waving her pelvis into my mouth and joyfully cooed as she flipped through the pages.

Then she clapped the book shut and made little pouting and cooing noises and muttered whispers of approval between quick gasps as I flicked at her clit with the point of my tongue... I knew she was close. She came with her eyes roll back for a moment, her body no longer contoured itself to me, it no longer cared about me pleasuring her, it was in a full throttle orgasm that was sending tremors through her entire body, enraging her mind sexually and making her chase the chemicals in her body with an animal-like ravenousness. Her thighs clamped tightly around my head as she leaned forward and grabbed my bikini, pulling the back of it up into my ass and bared down, gritted her teeth and seethed as she tugged on it like a leash. She reeled herself forward and smothered me as she convulsed driving and grinding her pussy against my mouth so hard it pushed my lips away and her clit grinds against my teeth. She relaxes and the panties snap forward from their strained position, and she jumps a little as her now sensitive spot its spanked by the returning fabric. She Sits up and laughs as I come up for air, wiping my mouth.

She sighs and lets out a long descending "Hoooooooo!"

"Atta boy, I think we've hit a stride here kiddo." She said as she took off her panties and hung them on my still erect cock.

"Thats all for tonight...Let see if next time you can complete your assignment, like you just did me."

There was the faint smell of honey...

END

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