It all started the day before graduation. Cyndi and I were in my bedroom getting ready to go to the rehearsal when she started crying. I put down the dress I had been getting out of the closet and put my hands on her shoulders. “Cyndi, what’s wrong??”

“Nothing is wrong, I’m just so happy! (sob)”

“Cyndi!” I put my arms around her in a nice, comforting hug while she shook, the sobs eventually dying down.

“It’s just – well, you know my stepfather.”

I nodded. I knew her stepfather only too well. Cyndi’s father had left when she was 11 and her mother had married this arrogant bastard in less than a year after that – probably out of loneliness and needing to pay the rent. “Go on” I said.

“Well, he is always telling me what a loser I am. That nothing will ever come of me and that I might as well become a prostitute or a phone sex actress! Now here I am, about to graduate high school and I’m going to college in the fall. I did it all on my own – but your emotional support has been what’s pulled me through when I didn’t think I could do it.”

I smiled at Cyndi and we sat down on the edge of my bed. She really had come a long way. She was smart, funny and beautiful in such an innocent way – because she didn’t even know she was beautiful – probably because of her stepfather undermining her self-esteem all the time. But *I* knew she was beautiful. I gave her another hug and inhaled the fragrance of her. Before I knew it, I felt her breathing get heavy as her hand slid so slowly and gently under the strap of my bra in the back.

I sucked in my breath, but didn’t move. I immediately felt the blood rush to my crotch as I realized what Cyndi was doing. I was shocked but not unhappy – I had often fantasized about Cyndi when I was alone and under the covers at night. I just never knew she felt the same way about me.

Her hand moved, under my bra, around to the front and slid up . . . slowly . . . until the fabric was moved up over my breast, and her hand now covered where the fabric had been. My nipple was growing hard, as she began to carress and knead. She began to say something when I covered her mouth with mine in a long, slow, tounge-teasing kiss.

She broke away and just looked at me, wild-eyed! Then we both ripped off our bras and embraced again, this time it was she who kissed me, and pushed me back on the bed. She continued to kiss me as her hand found my right breast and fully explored it. Cupping, carressing, kneading – and then pinching my nipple gently between her thumb and forefinger and just rolling it so exquisitely that it just drove me insane!

My hips were beginning to writhe a little by this time and she slipped her hand just under the elastic in the waist of my panties. I let out a slow, involuntary moan as her hand slid further under my panties. I felt her fingers slip over my mound and stop just above my clit . . . my pussy lips were already open and my panties were soaking wet.

I began to feel her breasts, too, her nipples were rock hard. It seemed to turn her on just as much fingering me, as it turned me on to get fingered! She started carressing her middle finger over my clit, rubbing it in little circles. Lightly at first, and then harder and harder. Until she was pressing against it so hard that the juice from my pussy made her finger slip off and then she’d do it again! Over and over – faster and harder! My hips were bucking against her hand, as I sucked on her tounge and clutched at her breast.

I heard Cyndi moan, a lustful and whimpering moan, and that was more than I could take. My orgasm shook my body and the bed and my thighs clutched her hand to my crotch as wave after wave swept over me. I fell limp against the bed when I heard a knock on the door!

We both jumped up and went to opposite areas of the room, quickly putting on our bras and dresses as I said, “Yes!”

“Are you girls almost ready? It’s time to go…”

“Yes, Mom.”

“Ok, I’ll wait down in the car. Hurry up, you two.”

I grinned at Cyndi and she grinned back at me, both of us knowing that her turn would come later.

Tonight she waited in line at the Torque Round club, fanning her face with her ID and wondering what kind of trouble she would have tonight. She’d never been to this club before, and decided to give it a try. It was a hot night, so she was wearing almost nothing. A mini skirt that barely did the job; a white, scoop-necked t-shirt that gapped, showing off her smooth, flat belly and dainty pumps that showed off her long, shapely legs.

At the same time, a tall, dark fellow worked his way to the front of the line, stopping to chat with this person and that. He finally stopped and talked to Hannah. He introduced himself as Mark, and said he could get her inside without her having to wait in line. She was suspicious of this older, but distinguished-looking guy, but welcomed the thought of getting into the club without an argument.

Mark smiled to himself when she consented to go in with him. “Come with me,” he said. He looked at her appreciatively, admiring her long, dark hair as he took her hand and led her to the front of the line.

“Hi Dirk,” Mark said as they neared the front. The bouncer nodded them in and they entered the dark, smoldering atmosphere of the Torque Round. The insistent beat of the music pounded their senses and Hannah looked around, wanting to take it all in. Mark pulled her along with him as he made the rounds; saying hi to people he knew, ordering them drinks, and making his way to a table in the back.

“Thanks for getting me in,” Hannah said uncomfortably, wanting to go off and explore the club herself.

“Sure, no problem for a lady as lovely as yourself.”

“I need to use the restroom.” It was a lie, but she figured if she could get away from, she could sneak back out of the restroom without his noticing and blend in with the crowd.

“Come with me, you can use the restroom in my private office,” he said, to her chagrin. Apparently he was the manager or the owner or something. ‘Well, this is turning out just great,’ she thought. ‘Now I’m stuck with this guy for the night.’

“Ok, thanks.”

She followed him back to the door marked “STAFF” and followed him through. They went down a long hall and up some stairs, then down another hall and into an office. “It’s over there,” he said, pointing at a door at the back of the office.

“I’ll be right out.”

When she came out, he was stretched out on his couch. “Come over here. What’s the matter? Do you think I get underage girls in here without an ulterior motive?”

“I’m not underage,” she said. “I have ID.”

“Yeah, so does half the population of the 18-20 year old demographic around here; that doesn’t make them legit. 18-20 year olds are not allowed in establishments that serve liquor. But I will let the occasional hottie in if I think she can prove she’s worth it.”

“Well, like I said, I’m not underage.” She was getting kind of nervous now, this guy was really creeping her out with this talk. But in a weird way she was getting turned on. She could tell he was used to getting what he wanted and that kind of power attracted her. Still, she couldn’t let him know that.

“I said come over here. Or I’m going to have to call the police and have you removed for being underage. What’s it going to be?”

Playing along, she walked over to him, trembling but excited. He motioned for her to sit down near the middle of the couch on the edge. He was stretched out across the couch, but kind of propped up on the arm.

He took her purse out of her hands and set it down. “Just relax. You’re going to like this, I promise.”

He slid his hand up under her shirt and began carressing her breasts. Softly at first, one then the other. Then he began pinching and rolling her nipples, which were already hard. “You like this, don’t you?”

“Yes.”

“You’re a very nasty girl, aren’t you?”

“Yes,” she said, closing her eyes with shame and lust; wanting him to corrupt every inch of her body.

He took her hand and put it on his bulging crotch. She instinctively pressed against it and began rubbing it with her palm. He let out a slight groan and ran his hand up the inside of her leg.

“Yeah, you like that a lot.”

He reached up under her skirt and pushed the crotch of her panties aside. She was already moist and his finger slid easilty between her pussy lips.

She let out a soft, breathy moan when his finger found her clit and began slowly circling it. She unzipped his fly and freed his hard cock, which was bigger than she’d seen in her limited experience. “Oh my God!” She was a little surprised and a lot excited.

“You’re a nasty little bitch aren’t you? You knew why I got you in the club so easily and you know you wanted it. I should punish you for acting so coy.”

“Yes! No! Please don’t punish me. Just fuck me!”

“Ok, get undressed and I’ll let you get on top. You can do the fucking, since you are the shameless, nasty whore.”

Hannah couldn’t figure it out. She’d never been like this. Had never been turned on by nasty, degrading talk. But here she was stripping her clothes off in a frenzy and as horny as she’d ever been.

When she was through undressing, she saw he was seated upright on the couch, right in the middle. He pulled her over to him and she straddled him, one knee on each side of him on the couch.

He grabbed her ass, one flank in each hand, and gripped tightly. He held her just over his cock and moved her hips around slowly and excruciatingly. She was in torment. She was in the position of control, yet he was really in charge; physically overpowering her desire to impale herself on his cock.

Soon, she was looking for any stimulation she could find and grabbed his head, pressing his face to her breasts. He began licking and sucking, flicking and devouring. When he could hold out no more, he yanked her body down on top of his, impaling her in one swift and sure movement.

She screamed as his cock filled her and he began raising and lowering her over and over. She grabbed the back of the couch for balance and ground her clit against his pubic mound as he pulled her down again and again. She soon realized that he had removed his hands, and that it was SHE who was humping against him like a wild animal; screaming and pushing his face into her breasts.

Soon, she felt the head of his cock expand and then explode, sending her over the edge into her own orgasm in a gale of pants and moans.

After it was over, she sheepishly got dressed while he watched.

“Come back when you’re 21. You’re comped.”

He smiled as she walked out the door, drained and confused.

“What the hell just happened?” she asked herself, as she took her place among the zombies at the bar.

“Barkeep, I’ll have a rum & coke.”

My mom is a bit of a socialite, she works at a bank and drags her friends from there home all the time, expecting me to come and talk with them, no matter how mundane the conversation. It was just such a situation when my mom invited Mrs. Pearlman, the new register lady home for some lunch. When she and my mom came home I opened the door to let them in, “Hi Jeffery, I’d like you to meet Mrs. Pearlman, she’s new at the back, Sarah, this is my son, Jeffery” my mom chirped. Mrs. Pearlman looked remarkably young and sunny, she had a broad flashy smile that practically illuminated the room, sparkling eyes, a pointed nose and soft brown curly hair that just touched her exposed shoulders. “Hi Jeffery, how’re you?” she said, extending a long thin arm to shake my hand. “Fine, it’s nice to meet you”, I reached over and shook her hand, smiling back. As I did she, just as non-chalantly, lightly grabbed my forearm with her other hand. “What a nice looking young man!” she said to my mother and we all let out small, fake sociable laugh.

We sat down to eat lunch, my mom and Mrs. Pearlman talked about the bank, Mrs. Pearlman asked me the usual generic adult questions: “how old are you?” “18”, “where do you go to high school?” “Riverford High”, “what’s your favorite class?” “Either history or English” Etc…

In the middle of lunch there was suddenly a phone call, my mom left to go answer leaving the two of us alone. There was an awkward silence, though we could hear my mom talking in the background. When she came back she seemed sort of panicked, she looked at me, “dad got in an accident downtown, he’s alright, but I’m going to right now.” She then glanced at Mrs. Pearlman, “Sarah, so you mind?” She shook her head, “no, not at all,” my mom looked back at me, “take care of Mrs. Pearlman while I’m gone, okay? I’ll be back soon. Bye!” My mom flew out of the house and drove away with the wind at her heels.

Mrs. Pearlman wasn’t that tall, maybe 5’4”, a good 5 or 6 inches below me. She had a very slim body though, her thin long arms were completely bare and her simple black dress revealed just the top of her shapely breasts.

“I hope your dad is alright, car crashes can be pretty scary” Mrs. Pearlman remarked.

“Yeah, my mom seemed a little frantic, but she said he was alright and all.”

“Are you going to learn to drive soon?” she asked.

“I’ve already got my permit, but I still have to do all the driving instructor hours and everything.”

“Well, I learned how to drive when I was 20, just a late bloomer I guess.” She laughed. There was a little silence, then, “can you guess how old I am, Jeffery?” she leaned over the table a little, smiling.

“25…26?” I answered.

“No, no, I’m flattered though” she laughed, “I’m 33, as of this July.”
I was honestly surprised, she definitely looked younger. “Wow,” I said “you really don’t look 33.” She smiled and sat up straight again, “you just have to take care of your body, but you know that, you’re a strong, healthy boy.” Then, I felt her leg up against mine under the table, she looked me right in the eyes, smiling even more broadly.
“I really like you, Jeffery” she suddenly said. Placing her head in the palm of her hand, gazing at me. Now her leg was going up and down against mine. I started getting nervous and flushed, she giggled a little and took her leg back.

“Someone young like you needs to have more fun though,” she said. I was completely silent; this was a woman who knew how to go from a pretty and nice to just about steaming hot in seconds. I was getting more flustered, practically dizzy. She got up and slowly walked around the table over to me, “you need to learn how much fun you can have.” She was now standing right in front of me; her breasts were practically in my face, she was looking down smiling. “Mrs.Pearlman…” I started, but she stopped me, when she reached out and took my hands, now looking me in the eyes, no longer smiling, her mouth just a centimeter open, she put my hands on her shoulders, and rubbed them around on her warm flesh. I breathed in deeply, she kept rubbing, down her shoulders, to her chest, and then to her warm, supple breasts, she let out a little sigh, then smiling again she whispered to me, “see how much fun we can have Jeffery?”

I couldn’t believe what was happening; my hands felt around her breasts, they were unbelievably soft, she threw off the top of her dress and began feeling my arms and chest, running her hands up and down my muscles achingly. She was leaning over me in my chair, unbuttoning my shirt as I continued to feel her body. I was breathing heavily with excitement as she threw off my shirt and ran her hands down my bare chest. Then she drew face closer to mine, I closed my eyes, feeling her cheeks, nose and lips up against mine. I could feel her tongue trace itself along my lower lip and the warmth of her breath on my face. My arms were wrapped around here, exploring the curves of her backside. Then as her hands slowly moved down, down my abs, past my naval and to my thighs, I felt her hand grip my hard cock through my jeans and a shiver of pleasure went through me. It felt so good that my hand tightened on her ass and she let out a surprised laugh and I gasped in shear bliss.

Suddenly, she dropped to her knees, in front of me, “have you ever had a blowjob, Jeffery?” she asked. “Uh, no, I haven’t” I stammered out.” “Would you like one?” she said with a seductive little laugh, pushing my legs apart with her hands on my knees. “I… yeah, sure, please.” “Okay then,” she said reassuringly. Mrs. Pearlman then undid my jeans and pulled them down past my knees. Then looking me straight in the eye with a great big smile, she took my cock out and began licking it with her tongue, up and down along the shaft. “Good, huh?” she laughed. She quickly put my cock into her warm mouth, the whole thing, it felt absolutely amazing, my dick was simply sucked into an incredible, blissful state. She moved her mouth up and down my cock, rubbing and licking me masterfully. I groaned in satisfaction, it was so good, I had never felt what it was like to have a beautiful woman give herself fully to pleasuring me like this. A huge shudder went through my whole body, I just about gasped, and suddenly white, viscous fluid flew everywhere, all over Mrs. Pearlman’ sexy small mouth.

“Mmmm….” She sat down on her legs, smiling, “that was good,” she said licking the cum from her lips while whipping off the rest. She stood up over my still throbbing body. “You know where I want it now, Jeffery?” she said, looking me straight in the eyes again. “ I want it in here,” she said, unclasping her skirt and letting it fall to the floor. Her hand ran down her stomach to her waist, a single finger touching her panties. She sat down on the table, he legs bent in front of her. I stood up, unsure of just what to do; she smiled seeing my nervousness and raised her legs up above her head to take off her panties. I grabbed the underwear and pulled it up, right off of her legs, she was biting her bottom lip, giggling. I felt her legs, her long thin shins and warm firm thighs and worked my hands along them, until I spread both legs apart and felt her warm, wet pussy. She moaned and threw her head back, I took my hard dick in my hand and let it slide into her hole. It felt like nothing I could have ever imagined.

It was a warm soft feeling, like she had wrapped me into her flesh; it was so tight and good. I moved back and forth inside her, “oh God, yes” she whispered as I began to pump faster and harder. I was holding onto her thighs and she grasped my arms in complete lust. We rocked back and forth on that table, knocking over the glasses and dining ware. She called out for me to do her as hard as I could and I pounded into her, my flesh rubbing against hers, my balls audibly whacking up against her ass. She threw her head back up, looking at me in the eyes in wild enthusiasm, laughing, “God, you can fuck, oh yes, oh God.” Again I felt a shudder run through me, this time larger than before. I came inside of her, letting go a gooey mass of warm cum into her smouldering pussy, I let out a deep breath. She groaned in delight.

I removed myself from her and for sometime we just both sat in silence, breathing hard. “Ah, that was really good, Jeffery,” she said, then smiling broadly, “a lot of fun.” I said it was great too, “but I never thought my first time would be with somebody 16 years older than me.” “Well, experience counts”, she said leaning forward teasingly, “stay right there, I’ll clean this mess up” she said referring to the now completely wrecked lunch out on the table. We put our clothes back on, now rather crumpled, and I helped her clean the table. We sat and talked, now much more relaxed, until my mom came back.

I saw Mrs. Pearlman many other times after that, but we never had an encounter like the one we had that afternoon. Chemistry remained, but it was obvious that we could never have any real relationship, all things considered. Not too long afterwards in fact, she married a man 10 years older than her, sticking true to her motto that “experience counts”.

“I’ll walk in front,” she said, a sparkle in her hazel eyes, “that way you can look at my bum.” She giggled. I was quite surprised at that because until then she’d never seemed tarty in anyway, but I did as she said. She was wearing baggy jeans which were quite tight over her beautiful firm butt, her long dark brown hair swinging above it, and a chequered short-sleeved shirt.

We walked and talked for fifteen minutes or so as she lead us further and further into the trees and plants. Eventually we came to a heavily vegetated area, without any visible path through it. Julia crawled under a bush on her belly and I followed. About 7m along we came to a huge wall of vegetation. She forced some branches apart and we squeezed through. Beyond there was a small moss covered clearing. At the far end there was a muddy area and a stream. The whole clearing was speckled with shade. Julia threw herself down on the moss and I lay down beside her.

“Did I shock you then?” she laughed. “I’m not normally like that you know. But I love you, so it seemed natural. Like masturbation.” she laughed again as I went wide eyed at this admition. “Yep. I masturbate about four times a week, and I bet you do too. But I wouldn’t admit it to anyone else but you. Do you masturbate?”

“Yes,” I answered, still a little shell-shocked.

“Thought so. Do you love me?”

“Yes,” I replied and we kissed. Julia put her lips to my ears and whispered: “I want you to break my hymen.”

I looked at her. “Now?” I asked. She nodded, and we kissed again. Then she stood up and began to take her jeans off. I undid my shirt and then took off my shoes, socks, trousers and pants, without once taking my eyes off her. She pulled her knickers down exposing her pussy and took off her bra letting her beautifully rounded breasts come into full view, then flung all our clothes in a pile before lying down beside me again.

I was already hard, but I decided to explore her a bit first. I caressed her thigh and gently squeezed her buttocks, then licked and sucked at her nipples. She fondled my balls and penis for a while. I moved my head further and kissed her navel, then she spread her legs and I inspected her vagina, caressing her small patch of pubic hair and exploring her cunt’s tight circumference and her clitoris. Her vaginal juice was practically pouring out now, and she was panting with anticipation. Suddenly she sat up and leant over me to give my cock a quick lick and a mouthful of spittle, which she smeared all over it.

Julia lay back with her legs still spread wide and I climbed on top of her, supporting my weight on my elbows and knees so that the tip of my dick rested on her entrance.

“Ready?” I asked, and she nodded.

I slowly moved my hips forward, forcing my penis into her tight pussy, enjoying the smooth lubrication of spittle and pussy juice. Her head had gone back and her mouth was open in the intensity of the feeling. Then I felt the slight resistance of her cherry and pushed just a little bit extra. Julia let out a little scream. I entered her all the way and then kissed her gently on the lips.

“Are you ok?” I inquired.

“Yeah, I’m fine,” she replied. “It was just a bit of a shock. Let’s do it properly now!” and she put her arms around my back and we kissed as I slowly half-withdrew from her and then entered again. As I moved on top of her I could feel her breasts with their hard nipples rubbing back and forth on my chest.

We were both breathing heavily now, and her hands were rubbing hard into my back. I started to enter her a little more steadily rather than the slow way I had been. I pushed myself up from her onto hands and knees and she slid her hands down to my buttocks which she gripped and massaged. Her eyes were half-closed now, and her cheeks had gone bright red. I began to grunt with the wonderful pleasure of my cock sliding in and out through the tight tube of lubricated flesh of her vagina.

I bent my head forwards and started to suck and lick at her nipples, beginning gently but becoming rougher and rougher with my tongue. Soon she began to grunt as well, getting louder and louder. I started to go even faster, coming right out of her and then forcing through the tight hole, her skin caressing the head of my dick. Julia was crying “Oooh! Oooh!” and I was nearing orgasm, but I managed to withdraw and collapsed on top of her, my tongue somehow finding her mouth.

After a good long snog, Julia looked up at me puzzled. “Why did you stop?” she asked. “Neither of us have come yet.”

“Yeah, but how long have we been going?” I replied.

“About four minutes.”

“Well then, there’s no point in rushing this is there. We need to make it last as long as possible. I mean, we can only lose our virginity once can’t we?”

“Ok.” she conceded. “But I want to go on top this time.”

I nodded in agreement and rolled off her. I lay back with my legs bent so my knees pointed up to the sky. Julia knelt up above me, her legs either side of me, leaning against my thighs. She spat on her hands and began mixing her spittle with her juice and my precum, rubbing my penis until it was fully erect again. I put my hand on the top of her slim hips and felt her ass. Then she held my dick in both hand and placed it so it touched her twat.

“Ready?” she asked me. I nodded, and she lowered herself down. Her flesh slid tightly over my cock, down, until her cunt had completely swallowed my penis. Then she lifted herself up again so I almost came out of her, then down again. She got a steady rhythm going, and then leaned over on top of me, squashing her tits against my chest. She kissed me as I moved my arms up around her back, and she began to push her hips backwards and forwards in the same rhythm, so the fantastic sensation continued on my dick.

Then she pushed herself up again, her hands returning to my pelvis. I gripped her breasts and massaged them gently. Her rhythm started to speed up and I held her breasts even harder, squeezing them. We were both breathing hard again, letting out little grunts and moans. Julia speeded up again and began shouting: “Ooooh! Aaaah! Ooooh!”. Suddenly as I neared ejaculation, she pulled my arms away, collapsed on top of me, and pulled me on top of her.

Her cheeks were very red, and we were both slippery with sweat. I held myself above her so her nipples just tickled mine, and started penetrating and exiting her for the last time. Going faster and faster, the friction between her vagina and my cock getting really hot, shouting and grunting, Julia screaming as we neared orgasm.

“I’m there, I’m there!” she cried approaching her climax. I could feel the familiar warm feeling in my abdomen as orgasm approached, and pressed myself hard against her, kissing her violently. I withdrew and then penetrated once more, and then ejaculated, with long hard spurts, the warm semen filling her.

After a few seconds our bodies relaxed, and our kisses became more gentle as we rolled on to our sides.

“That was amazing” she said, and snuggled up into my arms. I buried my face in her beautiful silky hair and we both fell asleep. We woke an hour later, washed a bit in the stream and went home.