Jenny's First Time

And as she finished the sentence, I realized that Cindy was now running her other hand lightly up and down my thigh, raising the hem of my dress just a little farther each time. It was as if she wanted to make sure I understood what she meant by "down there."

But before I had time to answer, she moved her tongue lightly over her lips, then leaned in and kissed me gently. My eyes opened wide at the thought of sitting there being kissed by my boss. But I didn't pull away. I was so aroused by the conversation and felt so close and safe with Cindy that it actually seemed quite natural.

My heart was racing as she leaned in and kissed me again, deeper this time. I remember tasting her lipstick and feeling the softness of her lips playing over mine, the tenderness of her cheek. The second kiss lasted quite a bit longer, and it was followed by a third when her tongue gently parted my lips.

I let out a little sigh as her tongue explored my mouth, just as her hands began to explore my breasts. My arms and legs felt heavy, almost as if I were paralyzed. I couldn't seem to move, even though I didn't really want to move. I just wanted this feeling to last.

"Oh my god! I can't believe this is happening," I thought over and over to myself. But with each kiss, each caress, Cindy just sort of took me over.

She must have sensed that I wasn't going to start screaming or run away in a panic, because the next thing I knew, she slipped my dress over my head, leaving me sitting there on the couch in nothing but my bra and thong, which by now had grown quite wet. She released one breast from my bra and began to suck on it gently, as she squeezed the other one through the thin fabric.

I felt her mouth move away from my breast and tasted her lips again as she kissed me over and over. Then her lips moved lower, nibbling and sucking on the tender flesh of my neck.

I had totally relaxed and given myself to her at this point and she must have sensed it, because her right hand moved between my legs. She rubbed me through my panties, running her fingers up and down the length of my pussy. It was an amazing feeling, even though I was a little embarrassed about how wet she had made me.

At this point I was so overwhelmed by my feelings, I just went with them. Cindy removed my bra and panties and tossed them into a pile on top of my dress at one end of the couch.

"You won't be needing these any more, dear," she smiled. As I sat there before her, she looked at my naked body with this dreamy look in her eyes. "You are so beautiful, so sexy, Jenny." Her words made everything feel so right.

She kissed me again, over and over, as her hands played over my now naked breasts. And though it felt so good for her to touch me like that, I remember being a little uncomfortable being totally undressed while she still had her clothes on. But her tender kisses and gentle caresses made me relax again.

"Don't worry, baby, I'm going to take care of you," she whispered softly. "I'm going to take care of everything and make you feel like you've never felt before."

And with that, Cindy slipped her top over her head to reveal her wonderful large breasts that had been tantalizing me all evening. They were round and soft with large pointed nipples, which were clearly erect from her arousal. They pulled her dark areolas tight, hardening even further as she showed herself to me.

Then she slid her tight shorts down her legs and off, revealing to my surprise, that she had not been wearing any panties. The dark hair between her legs was neatly trimmed, and I could see little droplets of moisture glistening in the dim light.

I looked down at my own smaller breasts and realized for the first time that they were covered with lipstick kisses from Cindy's bright red lips. It was one of the sexiest things I had ever seen and I thought I might cum right there from just the sight of it.

But Cindy cupped one of her own breasts in her palm and offered it to me. And I accepted it eagerly, licking and sucking as she had done to me and feeling warmed by her soft sighs and moans. I had never been intimate with a girl before, but Cindy's words of encouragement gave me confidence.

"That feels so good, Jenny," she purred. "Now let me do something for you."

And with that she gently lifted my feet, laid me lengthwise on the couch and spread my legs. She ran her red nails up and down my legs and the insides of my thighs. Then came her lips, licking and kissing up and down, getting just a little closer to my open pussy with each trip.

She was very slow and gentle and spent a lot of time getting me ready for what would come next. By the time her tongue finally reached my pussy, I was arching my back and moving my hips to encourage her. I wanted her to take me.

And did she ever! Her tongue was like a magic weapon on my pussy. She licked, sucked, teased my clit with her tongue, licked her way along the outside, then the inside of my swollen lips, then finally slid two fingers inside filling my tight tunnel to capacity.

When she curled those fingers and pressed what I learned later was my g-spot, I simply exploded. My back arched, my toes curled, and I could hear myself moaning, "Oh god," over and over again. It felt like an out-of-body experience.

I had had orgasms before, some by my own hand and once during sex with a boy. So I knew what was happening. But this one—the strength and intensity--was unlike anything I had ever felt.

But she didn't stop! Despite my moans, my cries and my thrashing about on the couch, Cindy just kept right on. She thrust her fingers inside even deeper and took my clit between her lips. She nibbled and sucked, not so gently this time, as her fingers plunged in and out over and over again until another climax swept over me and I went limp.

Cindy slid her way along the length of my body until our breasts were pressed tight together. Then she began to kiss me, tenderly at first, then passionately until I could taste myself on her tongue, which was again deep inside my mouth. She kissed me, stroked my face and hair and nibbled on my neck, my ears.

The feeling of our nipples touching was just delicious, and I closed my eyes and simply drank in the sensations. We lay almost motionless for a time, except for Cindy's occasional kisses. But soon, I became aware of a subtle movement of her hips. She started making small, slow circles, causing her mound to move subtly against mine.

As she increased the pressure and intensity of her movements, the wet folds of our pussies began to mold together, our juices mixing, our clits touching. Then Cindy began to rock up and down gently, sliding her wet slit upward, then back down and enveloping my swollen clit with her wetness each time.

The thought flashed through my mind that I was truly being fucked by a women. And it nearly took my breath. I knew right at that moment that this was the way I was meant to receive pleasure. I felt myself building quickly toward another climax.

Suddenly, Cindy stopped, making me whimper in protest. I reached down, put my hands on her bottom and tried to pull her to me, encouraging her to give me more of her amazing cunt. But instead, she raised herself on her elbows and looked deeply into my eyes. "All right, Jenny. Now it's my turn."

And with that, Cindy lay back with her head at the opposite end of the couch, and spread her legs. I knew what she wanted. I only hoped I could do it right.

I moved between her legs and realized for the first time how incredibly arousing the scent of a woman can be. Her beautiful aroma almost overwhelmed me as I lowered myself to her. Her lips were puffy and swollen, much larger and more prominent than mine. Part of that was a difference in our anatomies, but part I came to know later, reflected the difference in our ages.

My tongue tentatively traced its way up her wet opening and I felt her damp hair tickle my nose. She began to move her hips a little as if she was enjoying my efforts, so I gained some confidence.

By the time I reached her clit and began to lap at it slowly, she was instructing me with her moans of pleasure. "Ohhhhh, yes. Right there. More, more," she panted.

It seemed to take a long time, but her movements became more frenetic and her moans louder and more urgent. Finally, her entire body stiffened. She gasped and began shaking. It was a little scary, but I wrapped my arms around her thighs and just held my mouth to her pussy until she finally grew limp and quiet.

At that moment I felt so powerful for having made a woman more than twice my age cum like that.

We just lay there on the couch for awhile, Cindy with her head resting on the arm at one end, and mine resting on the inside of her thigh. I could feel her running her fingers through my hair as we just lay there and basked in the afterglow of those wonderful orgasms.

Finally, Cindy broke the silence. "All right, Jenny, there's something else I want to show you." And with that, she took my hand and led me into her bedroom.

She had me lie down on her king sized bed and I propped myself up and watched as Cindy opened the drawer of her nightstand and took out something that looked like an erect penis. I knew what it was, of course, but I had never seen a dildo in person. And I had certainly never seen a leather harness like the one that she began buckling around her waist.

Looking back on it, the fake cock was probably six or seven inches long. But to my inexperienced eyes, it looked HUGE!

"Oh my god!" I kept thinking. "I can't believe she is going to do this! Is it going to fit? How much will it hurt?"

But Cindy methodically attached the cock to the harness, then walked over to me until the dildo was only inches from where I lay on the bed.

"Lick it," she whispered, her voice intense, urgent.

So I began to do my best imitation of the blow jobs I'd seen in the few porno movies I'd watched. And before long, the pink shaft was wet with my saliva. Cindy then took my legs and scooted me over until my bottom was resting on the edge of the bed and my feet were barely touching the floor.

She spread my knees apart and stepped between them, which brought the large head of the dildo just above my opening. She took the cock in one hand and played it up and down my length, pressing it just a little bit farther inside each time.

By the time the head was positioned barely inside my lips, Cindy put one hand on either side of my face and used the weight of her body to drive it deep inside me. The cock was much larger than what I had experienced in my lone sexual encounter with a boy, and I closed my eyes and winced a little as she thrust it home.

But I was so wet and open from my earlier orgasms that it began to feel very good very soon. Cindy pumped it in and out slowly at first, until she was sure I had adjusted to the size and length. And as my moans of pleasure became louder and more frequent, her thrusts came harder, faster, deeper.

Just before I came, I opened my eyes to see Cindy's tits bouncing wildly as she fucked me almost in a frenzy. Her eyes were shut tight and her teeth clenched. Her breaths were coming in short bursts.

"Oh fuckkkkkk," I cried out, as another massive orgasm overtook me. My pussy throbbed and clenched around the cock as I lifted my hips from the bed in rhythm with Cindy's skillful thrusts.

I don't know for sure whether Cindy came. I was lost in the intensity of my own feelings at that point. But she probably did because she finally stopped thrusting and collapsed on top of me. Our bodies were covered with a thin film of perspiration from the exertion.

When she finally recovered a little of her strength, Cindy stood up and the cock slipped out of me with a little pop. It was odd, but I felt as if I'd lost something when she pulled out. But I was on such a high at that point, I felt as if I were flying.

Cindy unstrapped the harness and laid the dildo on her nightstand. Then she fumbled through her purse and pulled out a cigarette.

"I hope you don't mind," she said as she lit it up. "I only do it after sex."

Well, I was in such another world, I couldn't have cared less if she'd lit her hair on fire. But I was too weak at that moment to say a word. Cindy lay on her side facing me on the bed as she took long, slow drags from the cigarette. She caressed my breasts softly, then rolled my nipples between her thumb and finger, making them hard and erect once again.

She kissed me over and over as we lay there enjoying the afterglow of the most amazing experience of my young life.

"Jenny, sweetheart," Cindy purred, "I'd love for you to spend the night. Would you like that?"

"Mmmmmm," was all I could manage right then, as I snuggled tighter against her. "I'd love it, but my mom is expecting me to come home."

Cindy put her lips close to my ear and began to lick lightly, tracing the outline with the tip of her tongue. "Just call her, baby, and tell her we're watching movies. Tell her it'll be late when we finish and that you want to stay over."

I was still a little out of it, but when Cindy handed me the phone, I began to press in the numbers. When my mom answered, I did my best. "Hi, um, Mom? Cindy and I, um, we're kinda tired . . .," I never had been a very good liar.

But Cindy took the phone from my hand and rescued me. "Mrs. Jackson, this is Cindy Hollis," she said in her most businesslike voice. If only my mom could have seen that she was twirling my nipple between her fingers as she spoke.

"Jenny and I are getting ready to watch a movie." She paused for a few seconds while my mother was apparently saying something. "Yes, some chick flick she picked out." I marveled at how glib and believable Cindy sounded.

"It's going to be so late when it's over, I was hoping you wouldn't mind if she stayed over." Another pause. "I have plenty of room. I always keep my guest bedroom made up and ready."

Of course I knew I'd never see the guest bedroom even if I did stay over.

"I'll be glad to drop her off tomorrow. I'm sure she'll want to sleep late, so she'll see you in the afternoon sometime."

Cindy winked at me as she hung up the phone and then leaned in and kissed me deeply again. Then she padded into the adjoining bathroom and in just a minute, I heard her peeing, as she talked to me through the open door.

"Have you ever been with a woman before, Jenny?" she called to me.

"You're my first," I answered honestly.

"Well, you did very well, dear. I haven't cum like that in ages. You're a natural little cunt licker."

I felt my face flush when she said that. I was embarrassed that she had been so crude about something so personal. But at the same time, I was pleased with the compliment.

I heard the toilet flush and Cindy walked back into the bedroom. "But I'm going to make sure you get plenty more practice." She had a devilish look on her face as she hopped back on the bed and pulled me tight to her again.

"Hold on," I said. "I have to go to the bathroom, too." So I retraced Cindy's steps and relieved myself in her spacious master bath. I noticed that it had a sunken Jacuzzi tub and wondered if we might end up in there sometime before I went home tomorrow.

By the time I got back into bed, Cindy had poured two more glasses of wine and we sipped them together while she smoked another cigarette. I leaned my head against her breast as we lay there together and she stroked my hair and occasionally reached down to caress my breasts.

"All right, Jenny," Cindy said as she ground out her cigarette in the ashtray that set on top of the same nightstand where she kept her dildo. "Are you ready for some more practice?"

"Of course," I whispered and slid my body along her thigh until my face was even with her mound. I pressed her knee outward to make a place for myself between her legs and lowered myself to her.

Her thick dark hair was matted and still damp from our earlier activities, and her scent was more pungent. But the smell of her, and the sight of her puffy labia caused a primal response deep inside me. I could feel my own sex moistening again as I watched Cindy's do the same.

I began to lick her once more, very slowly all along the length of her slit. I began just above her anus and finished each pass with a little flick of her clitoris. As her hips began to move with my rhythm and lift slightly upward each time I reached her erect little pearl, I knew I must be doing a pretty good job.

"Oh, baby," she moaned over and over. "Lick it . . . taste me . . . eat my cunt." Her voice was breathy and low. "Fuck me. Use your tongue," she hissed.

Obediently, I pressed my mouth hard to her and thrust my tongue as deep inside as I could reach. I used it like a little cock, making it stiff and shoving it in and out as fast as I could manage.

"Suck my clit," she panted, barely able to get the words out.

I used both hands to pull back her hood and exposed the gleaming little pearl fully. I touched it with the tip of my tongue and her hips jerked at the sensation. Then I took it between my lips and began to suckle gently and listened as Cindy's moans and whimpers grew more urgent.

By this time she was no longer forming words, only sounds—primitive, primal sounds as she was swept along toward another orgasm. Finally, I imitated what Cindy had done to me earlier that evening on the couch and shoved two fingers deep inside her dripping cunt. But she was so wet and open that I could tell she needed more. I added two more fingers until four were thrusting in and out as I nibbled and sucked on her clit.

Her hips began to buck wildly and she grabbed my hair and pulled me tight to her as she tumbled over the cliff. "Ohhhhhhhhhhhhh fucccckkkkkkk! Fuccckkkkk meeeeeeeeee," she screamed. Her back arched and her legs wrapped around my back and locked me to her even tighter.

I didn't know it was possible for anyone to cum like that! She must have moaned and jerked and writhed around on the bed for nearly five minutes before her muscles went slack and she lay very still. In only a few minutes, I could tell from the regularity of her breathing that Cindy was asleep. Or had she passed out?

Either way, I knew we were finished for awhile, so I moved up her body until I could rest my head against her breast. I smiled to myself as I drifted off to sleep.

The next thing I remember was the feel of Cindy's tongue tracing along the outline of my sex, licking the outside of my labia, then the insides as she caressed me with her tongue. I opened my eyes long enough to see that it was getting a little light outside and I knew it must be very early Saturday morning.

But Cindy's expert touch made met forget all about the time, and even about what day it was, as she caressed me, probed me, found places in me that I never knew existed. And as she used her tongue to pleasure my now dripping pussy, she reached upward and took one of my breasts in each hand. She massaged them gently at first, just as gently as she was caressing my tender folds with her tongue.

But soon her movements became firmer, more urgent. She took my clit between her teeth, and at the same time began to pinch my nipples. I can't even describe the sensations that seemed to shoot back and forth from my nipples to my clit, over and over again.

Cindy seemed to know just how hard to pinch and bite, too, because each time the pleasure began to bleed just a little over into pain, she backed off and let me recover, only to bring me right back to that boundary between the two sensations. Finally, I was aware that one hand had left my left breast, but just barely because she continued to lick me faster and faster, knowing that my orgasm would take me at any time.

But just as the little ripples began deep inside me, Cindy thrust her finger into my tight virgin anus and I nearly levitated from the bed as I came and came and came some more. The contractions were tearing through me! The muscles in my ass gripped her finger tight and seemed to be trying to pull it deeper inside, even as my mind told me I should be trying to shove it out.