Dr. Ryan

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Just your average fantasy of fucking your boss.
2.1k words
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I remember the day that Dr. Ryan became our new assistant principal like any other major memory. Even more, I had no idea what was to happen a month later.

On her first day, I popped in to say hello and introduce myself. She was on the floor kneeling, which alone woke me up as much as any cup of coffee could. She wore a bright pink pantsuit, dressed for business. Her blonde hair in a tight bun. However, as she knelt deeper under her computer desk, I could see the black string of a thong sticking out of her well rounded behind.

I backed out of the office and lightly knocked.. That shocked her, I could tell. "YES?!" she answered in a fairly sharp tone. I could tell she was frustrated.

I came in again and extended my hand. "Hi, I'm Mr. Gordon, one of your 4th grade teachers."

Dr. Ryan popped her head up and looked at me...all over it seemed...and smiled slightly as she extended her own hand. "I'm Dr. Ryan." We shook and I was impressed by the firmness of her hand. I always preferred a strong hand to a dainty one that so many females had.

Dr. Ryan looked at her computer then back at me. "I don't suppose you know anything about computers?"

"Oh, I've been known to fix a small problem or two. What are we talking about here?"

"Just putting it together," she sighed in frustration.

I nodded. "May I?" Dr. Ryan nodded then got up to let me in. I couldn't tell if it was accidental, but her left hand brushed past my groin, and there was a bump here. If she reacted, I couldn't tell, though her hand lingered just a second before leaving my pants. I got down under the desk and plugged a few things in. I asked her to turn it on and log in. She did and was happy to finally be in business.

Dr. Ryan thanked me with a huge smile. "I wish we could chat more but I am so behind on things already!"

I held up my hands and smiled. "No problem, glad I could help." I moved around to the other side of the desk again. "Hope your first day here goes well."

Dr. Ryan leaned over and extended her hand again. This time I noticed, covertly, that her pantsuit was hiding a voluptuous pair of breasts. I think she leaned purposely so I could get the hint. Gratitude for helping? I shook her firm hand again and I could feel my cock rising like it did before. This woman was a turn on, but I could see the toughness in her and that she was not a person to underestimate.

She looked down and saw it, smiling ever so slightly again, then quickly up without a word, then nodded her head toward the door. "Out!" she commanded.

The next day she was observing several teachers, including me, to get an idea of the hand she was dealt. It was not a planned visit, just a random pop-in. She held a laptop as she sat, typing notes as I taught. After thirty minutes, she placed a note on my student table and left silently. After I got a moment, I walked over and read it...SEE ME DURING PREP! and it was signed only Ryan, no Dr. I swallowed nervously. Having worked with/for many admins over the years, that could mean anything, but I was feeling an urge to please her at least in a professional way. In my dreams the previous night, I'd stroked my cock in thought of her, imagining what those breasts looked like under the pantsuit, along with her thong hiding treats I could only imagine to enjoy. I came pretty quick with those thoughts, and did the same thing in the morning so that I could concentrate on teaching and not Dr. Ryan.

At prep I knocked on her closed door. "Come in, Mr. Gordon!" she almost barked. I entered and took the chair that was offered. Very businesslike,,. Dr. Ryan ran through my lesson, asking me questions about what I did and why, then offered a mix of praise and constructive criticism. I took it all in stride. At the end, she turned and faced me. "You're different form some of the others."

"How so?"

"You listen to me and don't react badly when I criticize, nor do you smile like an idiot when I give you a compliment."

"After 15 years, I've learned how to handle myself in 1 on 1s."

"It shows. Close the door, please."

I did so, then she stood from her desk and walked around to me, standing over me with her commanding presence. Sometime between her observation and this meeting, she'd changed into a long skirt and blouse. I could see the bottoms of her calves, and also a generously round ass that I hadn't captured the first day. "I felt you yesterday. I turned you on, didn't I?"

I gulped nervously. This was a conversation I never expected. I could have lied, but something told me not to. "Yes."

"You turned me on, too. Just watching you today, I felt it. I had to run home and change quickly so nobody could see me wet." She looked down and saw it clearly. She raised a finger to her lips and stared hard into my eyes. I nodded, then she knelt and undid my belt and my pants. She slid my boxers down and took hold of him. Her grip was strong but not strangling. Dr. Ryan stroked a few times, then let her tongue touch my balls and glide up to the tip of my cock. Several times more she did that before taking me completely in her mouth. She was careful not to move too fast and I was grateful, for her mouth held a heat I'd never felt before. She continued to lick and run my cock in and out until she could sense the shudder. She looked at me with a stern silent reminder to stay silent myself, then jerked the load quickly into her mouth.

I beckoned her head to mine and whispered, "What can I do for you?"

"Nothing," she whispered back. "Your prep time is almost over and I have another meeting in 5. I hope you enjoyed this." With that she went back to her desk and sat, waving me away but this time with a smile. As I left the office and saw her next meeting waiting, I kept my cool, hoping I hadn't left any clues about what had happened.

Come a month later, it was a Friday night and I got a call from Dr. Ryan. "Can you pick me up at the airport?"

"Sure. What time?"

She gave me the details and at the appropriate time, I left. Still remembering her sucking my cock, I couldn't help but wonder why she hadn't called a friend, or an Uber, or anyone else but me. I felt like I knew, but had to fight those thoughts in the ugly freeway traffic, even after dark.

At precisely 9:40, I pulled up to the pickup spot. Dr. Ryan was in a shorter skirt and a tee this time. I saw her suitcase and opened my trunk. I came out and put it in for her. She smiled and got in. There was no hiding anything tonight, I knew. She was all there for me to admire and get hard quickly about. Her enormous breasts stretched that shirt to the max. Those shorts came halfway to the knees and I could see those tanned generous thighs, leading to what I imagines was the sweetest pussy one could ever enjoy. I wondered if she was shaven, trimmed, or hairy...and I didn't care in any way, I wanted to taste it so badly.

She looked at me as she buckled in, and read my mind. "Just wait." She gave me directions to her home, which was quite near the school, which explained how she was able to change so quickly a month ago. A half hour later, I pulled into the driveway of a simple ranch tan stucco house. I got out her suitcase and followed her into the house. She invited me to sit on her couch then walked into her bedroom with the suitcase. A few minutes later, she walked out with just one piece on!

For the first time, I enjoyed the sight of this woman in all her beauty. She breasts swung large and free, her taut nipples inviting attention. I looked down past her beautiful belly and saw a skimpy red thong. shining bald pubic mound. After giving me a moment to admire the front, she turned around so I could see her ass. It was perfectly round with a little extra on each cheek. I let my imagination run with me and wondered how her ass tasted. I didn't have to wait long.

She got up on all 4s with her ass and generous thighs facing me. Without any hesitation, I took my hands and spread her ass apart, revealing a butthole that demanded my tongue. After sliding the thing down and off, I ran my tongue up and down her thighs, then her crack, getting it nice and moist, then stuck it in her ass. Her nerve endings spoke her her and she let out a pleasant loud cry. I continued to lick it, enjoying its sweetness, but trying not to assume too much. Gradually, I let my tongue slide down to her already wet pussy and soon found her throbbing clit. This was my favorite position, getting both at once. After a little of that and hearing her cries, I slide my hands up to her massive breasts and let my hands enjoy them in their sexual fullness that had teased me for a month, all the while licking her clit, not letting up for one minute.

After a few more minutes of this, she wrested herself from my clutches. "Off!", she commanded as she pointed to my clothes. I obeyed and she punished me back to the couch. This time there was no gentleness, she just rammed it into her mouth like she had also anticipated this for a long time. She was careful, though, not to make me come so soon. While she put her mouth to work, she reached under the couch and pulled out what looked to be a tubular noose. She let up for a moment as she wrapped it on my cock and tightened it. "You'll see!"

Dr. Ryan continued to enjoy my cock to its fullest, then ordered me on my back. She lowered herself on me, inserting my cock into her hot wetness, and rode me hard! My cock wanted so much to come, but that device kept it all in. After a bit of this, we turned to spooning on the floor, my pelvis banging into her beautiful large ass with each stroke. With that device I could have gone forever, but Dr. Ryan had other plans. "I want it in my ass!"

"Have any lube?"

"Oh believe me, I'm ready!" With that, I took my cock and slowly inserted it into a tight ass and soon found rhythm as I slid in and out of that heavenly tunnel. After a few minutes of her shouts and moans and my letting out a "Oh Dr Ryan ", she looked back at me fiercely but with a bit of love and said, "When you're ready, loosen it, then stick it back in fast!"

I wasn't ready, I was so enjoying the feel of fucking my boss's ass. That was part of the turn on, fucking a woman who could make my life hell if she wanted to. After a few more minutes and having felt her come many times, I unhooked the device and put it back in her ass. Soon I felt the load rush up and I screamed as the come shot up her ass. I pounded a bit more, then I was done.

Breathing hard and sweating up a storm, I laid my hands across her breasts. She turned over and offered them to me. It seemed we were going a bit backward but that was ok. I sucked on both of those erect, perspiration-soaked tits for a while, then she motioned me to let her stand. She stretched for a minute, then looked directly at me. "This was fun...and I enjoyed you in me...but if we continue this, people will know. I'm a tough broad, but when people get to me, it's hard to hide."

I stood and went to her and planted a deep kiss on her lips. "If you went soft on me, I couldn't get turned on. If we do this again, I'll take care of you like I did tonight. If not, I'll remember forever. Win win, you know?"

Dr. Ryan looked at me in thought. "You can handle it?"

"Yes. I'm a big boy."

"Oh yes you are!" She looked down. I was still hard. "One for the road?"

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oldjarhead1981oldjarhead1981over 1 year ago

Not bad, waiting for part 2

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