I was sitting at my desk bringing the reports up to date. I teach at a local Massage Therapy College, work that I love. But the paperwork is the part I don't care for.
The last few week's classes have all been hands on, this is where the students practice on each other, or on one of the locals who pay the college half price to get a couple of hours of massage from several students.
I have to watch these sessions closely, because every now and then we get some guy, or even a lady who will try and cross the line. Just last year one guy signed up, and I caught him flipping his erection so that it would stick out the side of the drape. Erections are no big deal, they are all used to that as being normal, but doing it deliberately is too much, so out he went.
He growled and complained some when I told him he was banned, and I even noticed he was sizing me up. But my 6', 220# frame made him think better of that and he left muttering to himself.
I glanced down the line to where Kathy, one of the Daughters from next door was working with a new guy. His name is Clint, a good looking well built young man about Kathy's age, maybe a bit older.
Kathy's sister, Lisa was absent this week. I have to admit I missed her being there, she is always fun to watch. Her breasts swing unencumbered in the soft tops she wears, and her outfits seem to always tend to the risque. I noticed Kathy seemed a little flushed, so I started paying a bit more attention. It hit me that Clint, who was lying on his back was sporting an obvious erection under the sheet, and from the size of the tent he was making, it was spectacular!
Kathy made a couple of sidelong glances at me, the kind I recognize as a call for help. So I got up and went to her table. She was working on his left leg, and she was pointedly stopping way short of the norm. I asked Clint if he was OK, he was blushing furiously, so I reached out and placed my hand flat on his stomach. "Take a deep breath and hold it," I told him. He did, and instantly the problem subsided. I just grinned at Kathy, she gave me a "thank you" look and returned to her work.
Kathy and I get along well, she was at my house when her sister, Lisa, more or less pounced on me. She was also with Lisa when they caught me with their Mom, Donna, not once but twice! *There were a few times they didn't catch us, but that's another story. So Kathy knew me pretty well, but I also knew she was still a virgin. Lisa had been a virgin, too, but I found that out far too late, or I would have resisted. For several weeks I had been avoiding getting into a situation with her, if that makes any sense.
My wife, Lee, is in school doing her internship to become a Doctor, her lifelong dream. Lee and I have a semi-open lifestyle, a partner for sex here and there doesn't really mean much to us, we are completely in love with each other, so that is just fun. Still, knocking off the neighborhood virgins is something this nearly 60 year old man shouldn't be doing! Lee and I had had a long talk about Kathy, and she agreed. But I had never said anything to Kathy, and I knew she was still expecting something to happen sooner or later.
But I also knew it was less about me, and more about the competition of keeping up with her sister, Lisa.
I finished up the class for the day, and as I was heading for the parking lot, I spotted Kathy and Clint sitting in the coffee shop. They were completely engrossed in conversation, I just grinned and went on home.
A couple of days later, I looked up and here was Clint, ready for another session with the class. As I drew the pairs, up came Clint with Lisa for the evening. I saw the dark look cross Kathy's face as I called out the pairs. "Best watch this!" I thought. The class went to work, everything normal for a few minutes. Then I spotted Lisa letting her hands slip up a bit too much, poor Clint was trying to control himself with not much success. Kathy was working furiously on Dan, one of the other instructors who had dropped in for the evening.
I walked over to Kathy's table, got her calmed down before she could draw blood, I could see that she was pissed. I made a mental note to lie about the draws next time, for sure. I looked a Lisa, mouthed "Cool it!" to her. She gave me that wicked grin, but eased up. Somehow we got through that session with no upset, the last thing I needed was a catfight in my class!
It was about a week later, I was outside washing my new z06 Corvette, enjoying the rare sunshine of a cool winter day, when here came Kathy walking up my driveway.
"Hi, Teacher Ted", she said. I nodded, asked her what was up. "I need to talk to you about something" she said.
I finished up, put the Vette back in the garage, figureing I could go buff out the paint later.
Kathy and I went in, she sat in the chair opposite me. "Something is wrong with me!" she blurted out. Then the tears came, I really didn't know what to say, so I just let her continue.
"I dated Clint a few times", she said. "We were making out, and I started to let him....you know!"...
Well, I had a pretty good idea, so I told her that things like that were normal, she just had to work her way through it, all the usual drivel.
"It's so big!" She exclaimed, "It won't....it HURTS me!" More tears.."Now he's...I LIKE him!"...her T-shirt was starting to get wet from the tears.
Hell, I am a massage therapist, not a Doctor, and certainly not a councilor. I simply had no clue what to say or do, so I just hugged her as the sobs subsided.
"Will you check me, see what is wrong?" she asked, looking up at me.
"Check?....Uhhh...Check?" I managed to stammer.
"Yes, my....down there!" she said. "You know about those things."
I thought about it for a second, she was looking at me with those big wet eyes, I realized she was serious. "Well, hell, come on!" I told her, and led her into my massage room.
"Go ahead, get undressed, I will take a look," I told her.
I went back out into the living room, wondering what I had gotten myself into. "Might as well!" I thought to myself, and went and washed up.
Going back into the massage room, Kathy was lying on my table on her back. I lifted the sheet in front of my face and told her to turn over on her stomach. She flipped over, and I slipped the sheet up over her fanny.
"Open your legs some" I told her, she spread them out for me. I reached for my bottle of Almond oil, lubed up my hands, and carefully spread her cheeks. Her lips were already engorged with excitement, and she was obviously moist. "Well, you don't seem dry" I said, as I ran my fingers over her outer lips. Then I pressed my index finger into her, it went in easily, but just an inch or so. Sure enough, I could feel the hymen, and it felt stiff and resistant. "Does this hurt?" I asked her.
"Just a little" she replied. "It's right about there that he..."
I pressed more firmly, and she jumped, an obvious stab of pain. Placing my hand on the back of her leg, I felt the tension. "Let's see if I can relax you" I said.
So I started with her legs, working out the muscles until she began to respond. Up the calves, then the thighs, she softened up almost instantly, just like she did in class. Finally I let my fingertips tease her outer lips, brushing her clit a few times. She let out a quiet moan, so I slowly began to work her towards orgasm.
There was no resistance, if anything, her legs opened even more to allow me access.
It hit me how odd this was, here is a nearly 60 year old guy basically finger-fucking a 19 year old virgin, trying to soften her up so she can handle some other man's oversize penis! Well, a man has to do what a man has to do, and I was starting to have fun. I felt her body go into the first baby orgasm, I slipped my finger inside as she did so, there seemed to be less resistance.
She had another baby orgasm, I let my fingers brush against her clit some more, her hips were making little up and down motions now.
"Let's turn you over" I told her. She rolled over onto her back, it hit me then that she still had her T-shirt on. "I need to make your body respond completely" I lied, reaching for the bottom of her Top.
She looked at me, sat up and quickly pulled her T-shirt off. Laying back, I looked at her breasts, nipples hard as a rock, the lighter lines told me that her top didn't cover much at the beach. Even the upper edges of her nipples were darker, where the sun peeked in from time to time.
This lovely lady had most likely driven the young guys nuts out at the beach!
I leaned forwards and took her right nipple in my mouth, rolling it with my lips. Reaching across with my left hand, I gently rolled the very tip of the other, as my fingers of my right hand explored her pussy, now literally gushing. I slipped my middle finger into her, it went in, deeper and deeper, as she opened up to recieve me. There was no jump of pain this time, her hips simply came up and pressed against me, rotating there.
She exploded into a large orgasm, then another quieter one. I felt her building again, then I realized her arm was pressing against my groin.
Carefully, I inserted two fingers, they went in, snug but no resistance.
"Please" She said. I looked at her, not sure. "Please!!" she said again. I still hesitated, two fingers inside her, as she turned slightly towards me.
She leaned up, I realized she wanted to kiss, I let my lips touch hers. Her mouth worked on mine, her hands came down to the catch on my jeans. Between our crushed lips she moaned "Please!!"
Now she had me free, her tiny hand wrapped around me, "Do it! Get it out of me!" she demanded.
I slipped up on top of her, her legs lay open. "Take a deep breath and relax your lower body" I told her. As she did, I started to insert. "Let your breath go" I told her. As she did, I slid my full length into her. I felt the resistance, she tensed, then I felt a little "pop" and was in all the way!
She let out a long groan as she climaxed without me even taking a stroke. I just held still as she shuddered, then "Don't come!" she said.
I lay there quietly as she adjusted more and more to my size. Finally she relaxed, I withdrew.
Sitting up, she scooted towards the upper part of the table. "Hop up here!" she said.
I did, she reached out and took my 8" erection in her hands. With a smile, she began to stroke me. "Your turn!" was all she said.
Her hands went up and down, I didn't even try to resist, just relishing the moment. In short order, I climaxed, spraying several strong jets all over her breasts, into her face, some even landed in her hair!
Kathy giggled, and released me.
"I think you will be able to handle that now" I told her.
"Yes, I think so" she replied. She was sitting there facing me, both of our legs were draped over the sides of my table. I looked her up and down, from the wisps of pubic hair to her nipples, now softened out to the size of silver dollars.
"I do believe that that is the most erotic session I have ever had!" I told her.
She beamed, and said, "Just wait until I tell Lisa!"....
"Just one thing," I asked. "You told me not to come inside you....?"
"I want Clint to be the first to do that" she said simply. "Then I want you to be second....."
"What about Clint?" I asked, the question obvious.
"I will talk to him," she replied, with another small smile. "I thought maybe we might come and see you someday...and Lee!".......