May/December Romance Ch. 01

I began to slowly massage the rosebud of Karen's asshole with my finger, spreading the lube over it. My finger produced a soft murmur of pleasure from her. "Just relax," I said, softly. As I felt her beginning to relax, I let me finger slowly begin to slide deeper into her opening. Ever so slowly she opened to accept me.

My finger slid in, and I slowly rotated it, stretching her sphincter muscles. As I squirted more lube on my fingers, I asked, "How are you doing? You are awfully quiet."

"Mmmmm, I'm doing wonderful, what you are doing feels great Lori."

"Good, I'm glad you are enjoying it. Ready for another finger?" I asked. As I talked, I reached up, and with my free hand began to slowly rub Karen's clit. A second finger joined the first, and soon it was buried deep in her bottom. A slight grimace of pain crossed Karen's face but was quickly replaced by a look of pleasure.

“I know sweetheart, it hurts a little, just relax and try pushing out with your ass as I push in. Like you had to go to the bathroom,” I instructed her.

“It’s really OK, I kinda like the pain, and it sorta blends with the pleasure. Your fingers on my clit helps a lot,” she replied.

I giggled and said, “Yea, I know what you mean, been there, done that.”

As I slid a third finger into her ass, I watched her face closely and rather than the grimace of pain I had seen earlier, a look of pure pleasure was evident on her face and a deep moan escaped her lips. I remember recalling that either I’m one heck of a teacher or Karen was a very gifted student. Maybe both, I thought. Whichever was the case, it was clear that Karen was wonderfully anal erotic.

I began sliding my fingers in and out of her ass, fucking her with my fingers. I felt her opening to them, my fingers sliding easier through the ring of muscle guarding her ass. Her excitement was growing rapidly and I knew she would cum soon if I kept this up much longer. I softened my strokes on her clit and heard her moan of frustration quickly followed by the feeling of Karen’s ass tightly gripping my fingers.

I stopped moving and asked, “OK, you are about loosened up enough for the main event, you ready?”
“Mmmmmm, yea, I think so, but what you were doing felt so wonderful.”

I chuckled and said, “I know, but we have something to accomplish here. You can go back to being you slutty self as soon as I get your ass properly stretched. Isn’t that what we were out to accomplish after all?”

“Yea, I suppose so, it just felt so good. Let’s go ahead and get it over with I guess. But first can I tell you something?”

“Of course,” I said, “you can always say anything to me.”

“Well, this is kinda embarrassing but I really like it when you called me a slut. I don’t know, it just made me feel so sexy and hmmmm… nasty I suppose is the word I’m looking for.”

“That’s OK Karen; you can be my little slut anytime you want to. I just want you to enjoy yourself and maybe along the way learn a few things about making love and perhaps even about yourself,” I said sincerely.

I had slid my fingers out of Karen’s ass while we had been talking and had worked at getting the plug nicely lubricated. She watched intently as I had done so. I walked over towards her on the bed and saw the excitement mixed with a little bit of fear on her face.

“Are you ready?” I asked.

“Yea, ready as I’m gonna be.”

“Good, just remember to push out and try and relax. Don’t tighten up. I’ll take it nice and slow, but if you want me to stop or you need to rest let me know, OK?”

“Sure,” she said her voice barely a whisper.

Karen’s eye widened slightly as I approached her with the plug. It was the first time she had really gotten a good look at it. “Just remember to relax and try and push out,” I reminded her again. “It will only hurt more if you tighten up. If it does hurt, tell me and I’ll stop or slow down. Let me know how you are feeling, talk to me. OK?”

“I’ll try,” she said a little sheepishly.

I could see that her sphincter was still slightly open from my fingers. I placed the well lubricated tip of the plug against the opening and she gasped. “Are you OK?”

“Yes, it was just a little cold and surprised me is all.”

“Sorry about that, it’ll warm up fast. Ready?”

“UH HUH," she moaned.

I slowly started to slide the tip in, watching her reaction. Her ass seemed to spread easily to accept the tip and I stopped when I reached the point where the flare of the plug began to bulge.

“You doing alright Karen?”
“MMmmmm, yea wonderful Lori. Please keep going, I like it,” she moaned.

“OK, but this is where it gets a wider, so let me know how you are doing, OK”

“UH HUHhhh!”

I stroked the tip back and forth a few times and was rewarded by Karen’s moans. I began to push in once again and was surprised as I watched her ass relax and almost swallow the bulge in the plug. I resumed stroking her clit as well. Just as I had gotten the widest point in her she said, "stop for a minute please."

I stopped and said, “you are just about there, that’s the widest part.” Karen’s eyes were a little glassy and she was softly moaning. I noticed for the first time that she had her hands wrapped around her legs, holding them against her chest and her hands were once again pulling and pinching her nipples.

“It hurts so good. Do it, shove it up my ass pleeeeze,” she pleaded.

I gave a final nudge and the plug slid into place, almost as if it was sliding downhill. Her ass closed around the thin neck at the base. One final gentle nudge and the base was nestled tightly against the stretched rosebud of her ass.

“Oh GOD! I feel so full, so wide open, so stretched. Its wonderful,” she moaned. I watched as her fingers pulled her nipples almost frantically. I re-doubled my stroking of her clit and her moans turned to ecstatic grunts as her orgasm grew near. I closed my finger tips around the base of the plug and slowly moved it ever so slightly in and out. Her body began to quiver and I pinched her clit with my other hand. That was all it took and she exploded. Her screams of pleasure echoed around my bedroom and her body thrashed against my hands.

Suddenly she fell limp on the bed. My concern immediately grew. I slid up to the bed and checked her pulse, it was strong and steady. While her breathing was still rapid and ragged, it was already beginning to slow. I smiled to myself and realized she had passed out. I told myself that I was just too good of a teacher. I had had lovers pass out on me before, so I wasn't too concerned. I decided some rest was in order and pulled a blanket up over her and let her sleep.

I decided now was good a time as any to get some of that work done that I had brought home from the office. I left her in my bed and headed off to my study.

I snuggled in next to Karen a few hours later and pulled the blanket up over both of us. She snuggled into my embrace and I soon fell into an exhausted sleep. My last thought being how nice it was to have her there next to me.

I awoke to the sound of birds outside, sunlight peaking through the curtains, and the smell of coffee. Coffee? HUH? I rolled over and there was a nude, smiling Karen sitting on the side of the bed. The previous night came back to me suddenly. I quickly became concerned how Karen would react to the night’s activities. A good long look at her told me I didn’t have anything to fear.

“Good morning Lori, I brought you some coffee; I thought you could use it. I wasn’t sure how you take your coffee.” She leaned across the bed and kissed me, softly but with an underlying passion.

“Uuuhhh,” I grunted, “black is fine. At least you could let me brush my teeth before you lay a lip lock on me.”
“Don’t be ridiculous, your lips are sweet no matter what time of the day it is,” she replied.

“If you say so.” With that I got up, grabbed my coffee, and headed for the bathroom. Even in my sleep fogged condition I noticed how Karen seemed to glow. Later I found her in the kitchen, standing over the toaster a butter knife in her hand.

“Would you like a bagel?” she asked.

“Yes sure, that would be nice.”

“I wanted to make you a nice breakfast but this was the best I could do,” she said.

“No, that’s fine. I need to go to the grocery. I’m afraid the cupboard is bare, at least for breakfast stuff.”

I sat down at the kitchen table and she placed a bagel covered in cream cheese in front of me. Seconds later she was refilling my coffee cup.

“Have you already eaten?” I somehow managed to get out between bites.

“Yea, I ate a while ago when I was waiting for you to wake up.”

“OK, why don’t you grab some coffee for yourself and join me in the hot tub while I try and steam out the cobwebs,” I said.

“That sounds like a good idea,” she said, a little too perkily for this time of the morning.

A few minutes later I was beginning to feel human and took stock of the situation. Karen didn’t seem like she was in any serious distress concerning the events of the previous evening. I sat and gave some thought to how I felt about them. I had to admit to myself that it had been a truly enjoyable and memorable experience. Karen was certainly a wonderful lover and had all the potential in the world to become an outstanding one. She was damn cute, had a wonderful body, an exciting attitude, a unique openness to try new things, was an energetic and passionate lover, and most of all seemed to share a lot of common sexual interests with me.

There was just one problem; I was old enough to be her mother. How did I really feel about seducing a girl her age? Wait one minute, I told myself. Who seduced who? In some ways it was her that at least presented the opening. She was the one that came out and made it clear of her desire for me. Besides, it’s not like she is a child. She is a full-grown woman that knew what she was getting into. I ended up coming to the conclusion that the best thing to do was to just table that issue and not beat myself up over it.

I looked at her and noted her warm smile and sparkling eyes and decided that there was no ethical issue to whip myself over. She seemed as happy as I had ever seen her. I decided the time had come for a talk.

“How do you feel this morning Karen?” I asked to get the conversation started.

“I have never felt so wonderful in my life,” she said.

“Did you enjoy yourself last night?”

“More than I could ever hope to express to you,” she replied enthusiastically. “Did you enjoy yourself Lori?” she asked expectantly.

“Ohhh you were wonderful sweetheart, truly wonderful. You are so sweet and giving, and such a tremendous lover.”
“Really?” she asked, genuinely surprised at my response.

“Yes, I meant every word.”
“I just thought that someone like me, you know, so inexperienced, wouldn’t have been that great for someone like you,” she replied.

“Well, you are inexperienced, but your other qualities more than made up for it.”

“Other qualities? Like what?” she asked, a quizzical look on her face.

“Well let see, for one thing you are absolutely gorgeous, adventurous, open minded, passionate, and seem to have an almost inexhaustible reserve of sexual energy,” I said, meaning every word.

“Hey, as I recall, and I don’t recall a whole lot, I was the one that passed out last night, so much for my sexual energy. As for the rest, thank you, that means a lot coming from you. Does that mean there is hope for me?”

“First off, there is no need to be ashamed of passing out after an orgasm like you had last night. I don’t know if I have ever seen a woman have such an intense orgasm as that one. Second, there is no need to thank me, I was just being honest. That’s how I really feel about you. Third, there is no need for hope. You have all the potential in the world, both as a beautiful lover, and as a wonderful woman.”

“Thank you Ma’am, that means a lot to me coming from you. I guess I have always had a little bit of a crush on you, but always thought of you as unattainable, at least until last night.”
“Karen, you don’t have to call me Ma’am. I’m not your mother and after last night I would hope you don’t think of me like you would your mother.”
“I like calling you Ma’am. It’s kinda funny but that is how I have always thought of you. Its just my of showing you my respect for you. I just want you to know how I truly do respect you. Please let me.”

Something clicked in my mind. A lot of things seemed to come together in a flash of insight. A lot of things I found sort of curious about Karen. I decided there was no time like the present to address them and charged right in. I sensed that Karen wouldn’t feel comfortable bringing it up. I think her comments were her way of dropping a hint.

“OK, if you want to address me as Ma’am, that’s alright with me. I do have one question though, would you prefer to call me Mistress?” There it was the thing I felt had been left unsaid. I was out in the open now and I watched her closely as she reacted.

The blush rose in her face almost immediately and her eyes dropped, unable to make contact with my own. I knew it! It all made sense now.

She sat there quiet, not speaking until finally she said almost in a whisper, “Yes, Ma’am, I would love to call you Mistress, I think I want that more than anything else I have ever wanted in my life.”

“You have been reading about Dominance and submission on the internet, haven’t you Karen?” I asked. Knowing that was probably the only place a woman her age would be exposed to D/s.

“Yes Ma’am, it started there and then I found some books on it and it just went from there,” she replied, before slightly more animated.

My curiosity began rise. “What books have you been reading?”

It started with the Sleeping Beauty Series, and Exit to Eden, and then I got my hands on a copy of Story of O,” she said, as if she was talking about the current New York Times best sellers.

“Those books are mainly about slavery, is that what you want to be, a slave?” I asked.

“I’m not sure; I kinda doubt it, at least right now. I have realized I am a submissive, and probably a masochist as well. I know I yearn to serve a Dom or Domme, maybe both. There is so much I have yet to experience and I have been careful to take it one step at a time. I don’t want to get myself in a situation that I regret later on. I have talked with enough subs online to know that is not all that uncommon. I think I have been very careful about the whole thing. I have had more than one offer to meet a Dom that I have met online but never felt comfortable with the whole situation. Most that I have met want a submissive, but don’t really understand what it means to be a real Dominant. They think it’s just about the sex and don’t understand the need a sub has to serve.”

My estimation of Karen went up tremendously as her words sunk in. She may be young, but she was level headed, intelligent, and wise beyond her years. In other words she wasn’t the type of sub that would lead with her ass instead of her head. I had known many of the former type, too many. After I considered her words fully I agreed with her observations and told her that I too had seen what she described all to often.

She sat quietly for a moment, reflecting, and then said, “Can I ask you a question?”

“Sure, you know you can ask me anything. I don’t have any secrets from you.”
“Well, I just get the impression you know a lot more about D/s and BDSM than I do. Am I right?” I looked at her and saw the hopeful expression on her face as she awaited my reply.

I smiled at her and her eyes brightened when she saw my reaction to her question. “I guess its time you learned some things about me,” I said.

I went on to describe a significant piece of my sexual history. A story I had never fully shared with anyone other that Greg, my husband. I started with meeting a former lesbian lover named Debbie. She was not quite a full fledged Domme, but was definitely a top. I told her how we she had incorporated a lot of D/s into our sex life together. I then went on to describe how Debbie had explained to me one night how she liked to be dominated occasionally and had asked me to top her. I asked her if she understood what a switch was and got a nod in response. I explained how the experience was a revelation to me, how natural it had felt to top Debbie and how much it had scared me later.

Up to that point in my life I had always looked for and usually found more aggressive and powerful male and female lovers. It had just felt right with them. I suppose it had a lot to do with how I saw myself as a woman and a lover and even more so about my insecurities. The experience had left me re-evaluating myself, not only as a woman, but as a lover as well.

I went on explaining to Karen how ultimately my newly found power had caused my relationship with Debbie to come to an end. We were just no longer sexually compatible and she understood that better than I did at the time. We finally wished me well and sent me on my way to find other partners with which to explore my new sexuality. We parted as friends and still remained friends. She would occasionally call and tell me of her new lovers and describe the details of her sessions with them. We had even shared a few encounters when her need to be topped had re-surfaced.

Karen sat in stunned silence as I went on to describe the next phase of my life as I went on to explore and learn more of my Dominant side. I told her of some of the submissive lovers I had known and loved, and of one in particular with whom I had shared my life. Her name was Susan and we had lived together for about 3 years until our jobs forced us to separate. It was a difficult and in some ways tragic story. We had remained friends and I told of how she had found a new Domme in Seattle where she now lived and how they now lived happily together.

I stopped the story of my life long enough to refill our coffee cups from the decanter I had brought with us. I then launched into a description of how my Dominant side has affected by my bisexuality. I soon found I was never really happy with sub males. Something about them never reached that point in my personality where my Dominant tendencies lay. My relationships with men were pretty well limited to vanilla encounters or with Doms and their female subs. I explained how these relationships were primarily occasional flings, never long lasting and only with Doms that could accept me as a Dominant equal. I was, in a way, a sort of visiting Domme to those who were usually in a long standing, well-established D/s relationship. I rarely felt the need to bottom to them. However, more often than not, these relationships would end when the Dom tried to exert his will over me and break me into being another sub to serve him.

Karen spoke up, having sat listening to my every word, and asked, “You said you rarely felt the need to bottom to them, what you meant by that.”

I launched into an explanation of how there was still some part of my sexual psyche that occasionally needed the release of bottoming to a Dom/me. There was some part of me that clung to the sub part of me that I had explored with Debbie so many years ago. I described to Karen how I looked at it as a safety valve that needed release occasionally and how much delight I took in the simplicity of only caring for the pleasure of a Dominant. I then went on to explain that I rarely found the strength of personality in a woman to give myself freely. I told her that, for whatever psychological reason, I usually only found this in a man. Perhaps it was due to deep down psychosocial association with the dominance of a male. I wasn’t sure, but knew that it was of who I was and had long ago accepted it as part of who I was rather than trying to rationalize it away.

Karen sat quietly, absorbing what I had to tell her of my life. She had only spoken occasionally, asking short, concise questions meant to clarify my story.