It was a rainy day after my summer school class, I was 18 going to prep before college. I got a lift to the tutors, she was an amazingly cheerful woman, late 40's, 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 showed her remarkably white teeth grinning as she 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 its self. 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 successfully stopped the dripping and sopping from getting worse 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 accords 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 area. 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 make 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 kiddo let's do this," she said ushering me to join her in the office.
I wrapped myself in the blanket and grabbed my books and got ready on 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 which ever 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.