Assisting a Friend
I walked in thinking it would be a pretty okay day. I helped out at my younger brother’s school by being a teacher’s assistant. So did Courtney. Courtney and I had been friends since we could walk, and it hadn’t been until recently, in college, that I noticed her as a girl. Was a head shorter than me with brown hair. She had a nice ass and perfect breasts. C-cup, soft, and delicious. She would wear low cut shirts and I could just imagine burying my face in them.
We had this competition between me and her since the beginning of the year. I had found a small sticker and had tried to toss it down her shirt. She had laughed it off and said “If you get it in, you have to take it out.” I’m not sure she realized what she was saying, but ever since, I had been trying and trying. For the past couple weeks she hadn’t worn low cut shirts, so I hadn’t had much luck. She insisted she was forgetting and that I should call her the day before (we only worked one day a week) to remind her. I remembered at 9 the day before and called her. Now she had no excuse.
That day I watched her walk down the hall towards me. She had worn a shirt with four or so buttons in the front that didn’t actually unbutton. However, the top button came almost to the top of her breasts, and there was major cleavage to be seen. Imagine the most revealing top one could wear at a school without being spoken to. I knew that day was the day.
We played at it for a little bit, always trying to do it surreptitiously when the kids and teachers weren’t looking. One close call came in the storage closet while she was reaching up for something. I tossed (more like placed it because my hand was less than an inch away) the sticker in her shirt and it stayed. She stepped down from the step stool and it fell out.
“That doesn’t count, it’s cheating.” I said.
“It would have fallen out anyways,” she said, eyes rolling, “Besides, you’ll never get it in there anyways.”
“Care to make a wager?” I suggested.
“What’s the wager?” she asked.
“Like you said: I get it in, I get it out.”
She giggled, “Okay.”
“But here’s the deal: if you cheat one more time, I get to look around in there until I find it.” I said.
“But the sticker won’t be in there.” she pointed out.
“Well, we’ll work it out if we get there.” I said.
I tried more than a couple times. Twice, I had it in and she ‘happened’ to pick it out. She denied cheating. Finally, I grabbed her hand and held it away as I placed it in. It stayed. Her eyes got wide and I smiled. When I let go of her hand, she pulled her shirt out towards me (I got a very nice view) and the sticker fell out.
I was happy and angry at the same time “Now that was blatant cheating.”
“That was was more than cheating, I won the game, and you cheated. We’re going to have to come up with something really good.” I said.
“What do you have in mind?” she asked, skeptically.
“Well, how about a three minutes in your shirt, and three minutes in your pants.” I suggested, “After all, you did cheat three times and I won.”
“No way! That’s not happening!” she cried out. I had been expecting this, but played it up.
“Come on, you can’t break a bet and a rule now.” I said sternly, “You broke the rule and lost the bet, now you have to pay.”
She suggested thirty seconds apiece. We settled on a minute and a half each, and she would flash me at the beginning. However, time had run out that week, so she said it would happen next class. No week had ever gone by so slowly.
When I arrived, she was already there. She was dressed in a lower-thigh-length skirt and a top much like the one last week. We began as usual, saying hello and tutoring for the first hour. When we were switching classrooms, she stepped into the storage closet, and I followed.
The storage closet is more like a storage room. It’s large enough that there was a space in front with shelves and such, a wall of boxes, and then a space behind for junk/obsolete stuff. We stepped behind the boxes. She had her watch on.
“Okay: ninety seconds. Say when.” she looked at me.
“Are you wearing a bra?” I asked.
“Take it off”
“What? That wasn’t part of the deal.” She protested.
“How can I get in there if you have a bra on?” I asked.
“Well that will count as my flash.” she said.
“Only for the top.” I reminded. She groaned and took her shirt off. I ogled at her boobs spilling out of a small, low cut bra. She reached behind herself and unclipped it. She took it off and I saw her breasts for the first time. They were everything I’d dreamed of and more. Firm and soft, with perky little nipples. She slipped her shirt back on.
“Okay, go.” I said. Before she even started the watch, my hands were up her shirt. I gently squeezed both breasts and began kneading them. She let out a quiet moan. Massaging them gently, I worked my way down to her nipples. I pinched them and she inhaled sharply, arching her back and bringing her breasts forward.
“60 seconds...” she breathed.
I began alternating between massaging one breast and tweaking the other’s nipple. I could feel her nipples getting harder and harder.
“30 seconds...” she moaned.
Trying to commit her tits to touch-memory, I began feeling them all over. Cupping them, jiggling them, squeezing them.
“Times up.” she said. Reluctantly, I slid my hands out from under her shirt, giving each nipple one last pinch.
“Do you want a break?” I teased. Her breathing had become heavy and she was flushed.
“No, just go on.” she said.
“Are you wearing underwear?” I asked.
She flushed some more. “No, see?” She lifted her skirt. She was clean shaven except for a small landing strip. Her engorged lips were clearly visible.
“Turn around.” I commanded. Turn she did. I savored every moment of that fine ass. Round and beautiful, she gave it a wiggle, then turned back around.
“Start...now.” she started the timer.
I slipped my hands under her skirt. I could feel her damp lips quivering at the touch of my cool hands. She was so warm and so wet. I felt her mound for a few seconds and searched for her clit. When I found the hard nob, I gave it a little tug. She gasped out loud and I continued. I worked my way into her pussy. Before long, I had two fingers in there.
“60 seconds...” she reminded me, breasts heaving with every breath.
As I finger fucked her I worked her clit with my thumb. I could feel her begin to tense up. I suddenly pulled out and went to work on her ass. By now the skirt had long since risen up over her thighs. I grabbed a handful of ass, feeling her cheeks. I pulled them apart and pushed them together.
“30 seconds...” she said.
I moved back to her kitty, bringing her back to the brink of orgasm. Just before she came, I dipped my finger in her pussy and trailed it back to her butthole. I gently began pushing it in.
“No wait!” she gasped. “Not that!”
“Hey, it’s whatever I want for 90 seconds.” I reminded her, applying more pressure.
“Wait, I’ll do anything.” She begged.
“My one and only offer: this can happen whenever and wherever I want. Anytime and anyplace.”
“The flashing too?” she asked hopelessly.
“The whole nine yards,” I said, "and I get to make you cum now."
“I don’t know...” she began. Suddenly, I pushed my finger in up to the first knuckle. She gasped and almost chocked on her own saliva. “Okay, okay! Deal.”
I pulled my finger out and re-inserted it into her pussy. I worked it in and out of her soft folds until she came in gushing waves. She actually blacked out for about ten seconds, in which time I rubbed most of the liquid onto her ass and asshole. When she came back, she stood up and stepped back. Her hair was askew and her skirt was bunched up around her waist. She turned around and bend down to retrieve her bra (I got a great view there), stood up, and we went back to class.