May/December Romance Ch. 01

I went on to explain the care that should be exercised in anal sex, going into some detail into the fragile nature of the tissues involved and the potential for infection if you weren't careful to clean up afterwards. During this entire lecture Karen slowly thrust her fingers in and out of my ass while listening intently, taking it all in. I struggled to maintain my concentration as her fingers evoked pleasure from me while at the same time I tried to carry on something resembling an intelligent discussion about the care and fucking of my bottom.

"OK, I guess that ends the lecture portion of our lesson," I said jokingly, remembering her reference to me as prof. "Its now time to move on to the lab part of your instruction. Do you have any question Karen?"

"No, I don't think so," she replied. "You are such a wonderful teacher, I've already learned lots. I do have one ummm....., not exactly a question, ahhhh.... more like a request.

"OK, go ahead, what is it?" I asked.

"Well, not right now, but maybe later, do you think, uummmm...., this is sorta embarrassing. Do you think you could do this to my ass? Maybe with something bigger then a finger?" she said. Then before I could reply, she went on, "You know, aahhh.... like maybe with one of those?" she said, tilting her head to indicate the toys on the night stand.

"Yes Karen, I don't see why not. I take it that you want me to take your anal cherry, is that it?"

"Yes, that's exactly it; I want you to fuck my ass. There I said it. I've been curious about what's its like for a while now and after hearing you talk about it, I'm even more curious. Like I told you, I've used my own fingers back there and stuff, but I want to know what its like to be really full."

"Well, we'll take care of that later, are you ready to have some fun? I sure know that I am," I said with a laugh and a broad grin.

"OHH YES, definitely. What do you want me to do?" she said enthusiastically.

"Well, let’s see. Why don't you do whatever you want to do? After all, this is your first time. Don't worry about me; I'll help out with a few hints when you need it. I'm pretty tough and I doubt you are capable of hurting me over my threshold for absorbing it, and I'm not that hard to please either. Just relax and do to me what you think you would enjoy or what you think or know I enjoy and you'll do fine. Just go with your intuition and what feels natural? Just remember the two most important things about having sex."

"OK, I'll bite, what are the two most important things about sex," she said smiling.

"Just relax, it should never be work, and most importantly, have fun, OK?"

"I think I can handle that!" she replied excitedly.

"OK, are you ready? Here goes nothing."

She had continued to slowly saw her fingers in and out of my ass during our discussion and it was having an effect on me. I put my legs up over her shoulders, raising my hips to her mouth and allowing her fingers better access to my asshole. My mind was starting to cloud over again and my body was more then ready for some serious pleasure. I knew that she had everything it takes to be a great lover, and that now was the opportunity to show me, and more importantly herself, what she was capable of.

Karen's head descended towards the junction of my thighs and I felt her burrowing deeper into my ass, producing an unconscious groan from me. The conscious part of my mind quickly faded out of focus and I gave myself up to the sensations that she was beginning to produce in my body. I felt her lips on the soft flesh of my thighs as she slowly, teasingly kissed her way toward my pussy. Her tongue was licking up the generous juices that had become smeared across my thighs. Then I felt her tongue bashfully lick my swollen labia, tentatively, haltingly slide across them, up one side to near my clit, then down the other.

I groaned loudly at the sensation of her tongue on my sensitized flesh and it seemed to reassure Karen. I felt some of the rigid stiffness in her body begin to melt away and she was soon licking happily away at my cunt. She began to suck my labia between her lips, flicking her tongue against them. Her tongue worked its way between the engorged fullness of my lips and I felt it pushing into the depth of my cunt. My pussy was flowing heavily and her sucking and kissing produced a wonderfully erotic sound as she ate her first pussy. Her tongue was now buried deep and her mouth sucked up my juices thirstily.

The feel of her tongue deep in my cunt rapidly pushed the last bits of concern for Karen out of my mind. I had completely surrendered to her and what she was doing to me. Suddenly I realized my hand was intertwined in her hair, pulling her mouth deeper into my gushing womanhood. I realized the cries of lust filling the room were my own. All the while she was tongue fucking me; her fingers were continuing to fuck my ass, their pace and stroke length increasing as she went on.

"Aaaahhhh, yes sweetheart, so good. You are a natural pussy eater," I said, meaning it. Her style may have been somewhat indicative of her inexperience, but it showed a definite talent. Karen merely moaned into my pussy in response to my praise of her talent.

"Why don't you lick my clit now Karen? I'm ready for more," I requested. Her mouth quickly moved to my pleasure button and she took the hood ring between her teeth and pulled on it gently. That was enough to render a loud groan from me and she looked up at me, obviously concerned that she had hurt me.

"Did I hurt you Lori? I'm sorry," she asked, clearly upset.

"No Karen, it felt great, I liked it, go on."

Her look of concern was rapidly replaced with a smile and she returned to work on my hard clit. She began to lick my clit, tentatively at first, with broad slow licks. Soon her tongue was flicking rapidly against my clit like the wings of a butterfly driving me higher and higher, closer to my peak. My hands were pulling her head tight into my cunt, wrapped in the tendrils of her hair. My legs were contracting as well, raising my hips and forcing her mouth against my feverish pussy. For the first time I noticed that Karen's free hand was buried between her own thighs, a blur of frantic activity as she frigged herself.

"Aaahhhh!!!!" I moaned loudly. "YES! GOD YES! That's it... lick my clit..., fuck my ass, harder, faster. I'm close Karen..., so close. Suck my clit, bite it. Make me cum, make me cum so goooodddddd," I heard myself screaming.

Her lips were suckling at my hard, throbbing clit, her moans causing a wicked vibration against it. She was alternating nibbling on it and flicking her tongue rapidly across its exposed tip. Karen's fingers felt like a blur as they flew in and out of my anus. I felt a sharp bolt of pleasure/pain from my chest and somehow in my delirium of passion I realized that it was from my own hands, pulling sharply on my nipple rings. I was on the ragged edge of release, posing on the precipice of orgasm.

"OH FUCK YEA!!!! I'M CUMMING, CUMMING ALL OVER YOUR FACE, I screamed."

In a flash of pleasure, my climax peaked and I flew over the edge into blissful release. My clit seemingly exploded between Karen's lips and my asshole contracted tightly around her fingers. My fingers clamped tightly around my nipples, intensifying and stretching out my orgasm. The pleasure rolled through me, over and over, one wave after another crashing across me. My entire body was contracted in a tight bow, Karen's head clamped tightly between my thighs.

"OH LORI, LORI, CUMMINNnnnnn TOOoooooo," Karen's cries of pleasure mixed with my own as she came also.

As I began to float down from the velvety heights of my climax, I looked down and watched as Karen twitched through the final stages of her orgasm. Her hand was clenched tightly between her muscular thighs.

Finally Karen's eyes came into focus and met my own. Her face was covered with my juices and a broad smile. "That was wonderful, I would never have imagined that going down on another woman would be such a turn on," she said.

"I know what you mean Karen, I felt the same way my first time too," I replied. I took her hand and pulled her up next to me, then proceeded to lick and kiss my juices from her face and lips. We finally settled in together, snuggling and sharing occasional kisses as we individually reflected on the evening’s events. Our bodies relaxed and molded into each other and I could feel the taut softness of her breast pressed into my arm.

"You know the only thing I miss? I mean making love to a woman instead of a guy," she said, finally breaking the quietness of our thoughts.

"What's that sweetheart," I asked.

"Well don't get me wrong, I loved the things we have done and the things you have shown me. Its just that I sorta miss that feeling of a hard cock inside me, filling me, you know what I mean?"

"Yes, I know exactly what you mean Karen. I feel the same way sometimes. Being with another woman will never replace my love for men, or being fucked for that matter. It’s just different; it’s great in its own way, but different."

"Mmmmmmm, yea. I see your point," she stated.

"However, I do have at least a partial solution. If you are interested, that is," I said, smiling.

Karen's eyes and face lit up and she said, "What's that, tell me." Her enthusiasm and energy were quickly peaked again.

"Well, I do have my trusty strap on dildo sitting over there," I said, nodding toward the neglected selection of toys on the bedside table. "It may not be as good as a hot throbbing cock attached to a nice, hard male body, but I think it has some advantages in its own right."

"Like what, Karen?" she asked enthusiastically.

"Well, for one thing, it'll never cum when you are right on the edge and just need a few more thrusts to cum yourself. It never has a problem getting a hard on after a few too many drinks with the boys. It’s always there when you need it, and besides, I think the feeling of a hard cock attached to a soft feminine lover is unique and wonderful in its own right. Besides who knows more about how a woman likes to be fucked then another woman," I responded.

Karen grew pensive for a moment, clearly considering what I had said. Then suddenly her eyes met mine and quite seriously said, "Aaaaahhh, Karen, would you and your toy over there please fuck me. I really need it. I know you understand."

I smiled at her and said, "Sweetheart, it would be my pleasure." I rolled across the bed and grabbed the strap on from the nightstand. Karen watched, fascinated as I put it on and strapped it tight to my hips. Just for the record, it had a leather harness to which I had attached a vibrating egg that rested against my clit and provided some stimulation to my partner’s clit. The dildos were interchangeable, and I had a medium sized 7" dildo attached at the moment. I also had another small plug shaped dildo attached to the crotch strap that went inside me. I could attach another for my ass if I wanted but decided it wasn't worth the trouble at the time. Karen was anxious to be fucked and I have to admit it, so was I.

Karen sat watching intently, silent, as I prepared. Her nipples were hard again and I could see her excitement as she waited for me to begin. I rolled over to her and we kissed in a passionate embrace, our breast pressed tightly together, our nipples digging into the soft flesh of each other’s breasts. I felt her wet pussy as it straddled my thigh, softly undulating against it. She was still very wet from her previous orgasm and I knew lube wouldn't be necessary.

My lips left hers and traveled to her nipple. As I began to suck, I felt her body shudder and heard her moan. My hand traveled to her other nipple and I pinched it, rolling it between my fingers. Her hand traveled down to the dildo, holding it, feeling its hardness. I knew she would be thinking about what it would feel like buried in her, anticipating the sensation of being filled and stretched along its length and girth. I couldn't help but smile.

Finally, Karen's anticipation had grown past the point of being bearable and she said, "Please Lori, I'm ready, take me. Fuck me with your hard cock. I need it so bad." The need and passion were clearly evident on her face.

"OK baby, here we go," I replied. I moved between her thighs, which she spread. I rubbed the tip of the dildo across the moist flesh of her labia, splitting them and letting the tip slide between them. A soft moan escaped her lips. I wiped some of the juices from her pussy and applied it to the length of the rubber phallus.

I looked up at her and smiled as I place the tip in the furrow of her womanhood once again. I squatted back on my haunches and gripped her thighs with my hands. Suddenly, I thrust forward with my hips and simultaneously pulled back on her thighs and half of the dildo slid into her easily. Her breath whooshed from between her lips and her fingers flew to her nipples as she felt the dildo pushing inside her.

I started a slow rocking motion, teasing her with the dildo as it slowly moved deeper and deeper inside Karen. Her hips thrust back toward me, trying to capture more of it inside her cunt.

The motion of Karen's body grew more frantic a she tried to push herself up onto the dildo. I continued to deny her the fullness her heated mind and wet pussy wanted so badly. Finally she cried out, pleading, "Pleaaaaasssseeeeee! Please give it to me. I need to be fucked Karen, give it to me. I'm about to explode!"

I smiled at her and calmly replied, "Oh, is that what you want Karen? All you had to do was ask." I drove the dildo hard into her and felt a satisfying lurch as our hips slapped wetly together. My own pussy contracted around the small dildo inside me, and the pressure of her pubic bone pressed the egg against my clit.

"Aaaaahhhhhh, yessssssss," she hissed, "that's what I want, what I need. Give it to me. Fuck me the way you know I want to be fucked Lori. Fill my pussy with your cock, deep and hard."

The shy, reserved woman I had known was suddenly gone, replaced by a woman thoroughly engulfed in the passion and lust that she was experiencing. The change was a surprise, but one that I enjoyed. The needful tone in her voice was quickly replaced with that of someone totally involved in the pleasure that was now enveloping her. Karen's fingers tightened around her nipples, pinching them tightly, with more force than I would have suspected that she would have enjoyed. It was another surprising revelation about this young woman. It was starting to look as if we were alike in several ways.

I was driving the dildo deep into her now, stretching her wide, filling the void of her cunt. The more I gave her, the more she seemed to want. She had no limits. My thrusts resulted in a noticeable wet, squishing sound as I slid in, her pussy was soaked. I recall thinking this is how sex should be, pure passion, all out, with no limits, hot and wet.

Karen's moans and groans and cries for "more... harder" soon degraded to a series of unintelligible grunts and screams as her passion rose to a peak. My own concerns and observations of my new lover soon dissolved as I allowed myself to merely experience the sensations, smells, sights, and sounds of fucking Karen. Somehow, I realized that my own sounds of building lust had joined hers as I began to strive for my own release.

Karen's eyes flew wide open, staring at me as she screamed, "YYYeeeeeesssss!!!! OHHH Gooodddddd YESssssss!!! I'm cummmmming...." I continued to drive into her, as her hips thrust up to meet me and the dildo. My own inevitable orgasm was rushing onward.

An electrical charge flowed through my body and my screams of release rose from my lips to join Karen's as they began to trail off. I drove the dildo into her one last time and ground my hips into her, both our pussies feeling the respective dildos deep inside and both our clits enjoying the vibrations from the egg. This final action set Karen off into a second orgasm while I enjoyed the after shocks of pleasure rippling though my body from my first.

We both lay there, enjoying the warmth of each other; our wet bodies pressed closely together, our labored breathing slowly returning to normal.

Karen opened her eyes and looked into mine deeply, smiling. "That was so wonderful, you were wonderful Lori, better than any guy I have ever been with," she said.

"Well, that probably had more to do with the guys you were with than my talents," I replied. "I'm sure that the young men you have been with are probably just a little short on experience and stamina. That will change, with time. Believe me, its gets better."

As I rolled off her, the wet dildo still jutting out from my hips slapped her thigh and we both giggled. I summoned the energy to pull the harness off and turn off the vibe. Karen helped out, loosening the harness buckle on one side.

That done, we snuggled back together under the blankets; enjoying the after-glow from the pleasure we had shared. "Ummmmm, Lori? Can I ask you a question?" she asked timidly, seemingly unsure of herself.

"Sure sweetheart, after what we just shared I don't think there is anything you can't ask me," I replied.

"OK, well I was just wondering, well, you know, whether Greg is a good lover? I hope you don't mind me asking."

Of course I don't mind Karen, and the answer is yes, he is a wonderful lover, the best I have ever had. He is sensitive, imaginative, has a great cock, lots of stamina, and never fails to leave me satisfied."

"Mmmmm, he sounds wonderful," she replied, "it’s just that I've never been with an older, more experienced man."

"Well, maybe we need to do something about that," I said, smiling at her, our eyes meeting.

"Are you saying what I think you are saying?" she asked. "That you wouldn't mind me being with him, you know, him fucking me?"

"I don't see why not, we have shared several lovers over the years. Besides 3-somes are a special treat for us, and I know he would love being with you. Maybe not right away, I think I'm going to be selfish and keep you to myself for a while," I said, smiling

broadly. "Besides, there are a lot of things you want to learn and explore about sex, right? Maybe I should save Greg as a graduation present."

"Ooohhh, that sounds exciting, I like presents," Karen replied. "What would you suggest as my next lesson Ms. Professor?"

"Hmmm, let's see. Well, you did say you were interested in anal sex, right?"

"Yes, but I've never really had anything in my bottom other than my fingers,” she stated.

"I think we can do something about that if you are game. You're gonna need some practice at relaxing and stretching before you are ready to take Greg's big cock up that beautiful bottom of yours," I replied.

Karen's face lit up in anticipation as she said, "Sure, I'm game for just about anything, what did you have in mind?"

"Well, I think I might have the perfect toy for this purpose, just relax for a minute while I get it," I replied. Some time ago I had bought a set of three anal plugs that contained a small, medium, and large sized plug. They were part of what was sold as an “Anal Training Kit” that I had gotten for just such occasions when I was playing with a lover that was new to anal sex. I retrieved the smallest of the three and a tube of lube from the nightstand.

As I returned to the bed, I instructed Karen to pull her knees up to her chest. I went on to explain that anal penetration is most commonly done with a woman in doggy position, but that with her on her back and legs up provided a better position and straighter angle into the rectum. She quickly did as I instructed as I applied some lube to my fingers. I couldn't help but pause for a moment and admire Karen's tight, muscular ass. I found myself really looking forward to introducing her to the pleasures of anal sex. The role of teacher was beginning to grow on me, I suppose.