A First Time for Everyone

This story is not exactly a sequel, but one of the characters was developed in my earlier stories “Social Sex Ed” and “The Night Before;” I wrote this one to stand alone, but the other stories will add depth if you are interested.

When she climbed into my lap, it was the first time I had ever touched a woman other than my mother or sisters — and far more intimately. I probably shouldn’t have been so surprised — we had just gotten married and were in the traditional ten minutes of privacy that follow a Jewish wedding, alone together unchaperoned for the first time since we had met seven months earlier — but somehow through all the preparations for marriage, it never got through to me that we would actually touch.

My heart was racing as my mind leaped ahead to what would come later that night. I could feel the sweat start to build under my skin, dark imaginings clouded my thoughts, and I felt a familiar embarrassing tightness in my pants. Deborah, on the other hand, looked perfectly calm, her black curly hair piled high above her pale face. She was so petite that her whole body fit easily on top of my lap, her head just slightly above mine; but her body curved in ways that would never let you mistake her for a child. Looking at her, I marvelled that a dress could cover nearly every inch of her body, from ankles to wrists to neck, and still look so alluring.

“Benny,” she whispered, smiling, “I’m going to kiss you…” Involuntarily, I closed my eyes as she leaned in close. I felt her lips, soft and cool, press against mine, and then they parted and her tongue slipped between them and into my mouth. It touched mine and by instinct I reached back with my tongue. She pulled her tongue back into her mouth and mine followed, probing the warm, wet recesses. Deborah moaned and pressed her body against mine, her breasts full and firm under her dress, the skin of her neck and face hot against mine. I ran my hands up and down her back, feeling the satin and lace and imagining what her bare skin might feel like. The idea that we had to leave here in a few minutes for a reception that would easily go for five hours or more seemed suddenly cruel; I wanted to grab her and make a run for the hotel before our guests could stop us.

When the kiss ended, I said, “Well, that was worth waiting twenty-six years for!”

Deborah giggled. “The nice thing about being younger is I didn’t have to wait as long.” She ran her hands through my short brown hair. “Thank you,” she said.

“For what?”

“For making me the happiest girl on earth,” she replied.

“In that case, thank you as well. I love you.”

“I love you too.” She leaned in so that her lips were practically touching my ear, and I almost jumped when I felt her hand on my pants leg, slowly inching up toward my crotch. “Be patient,” she whispered into my ear as her hand grazed the hard lump in my pants, “There’s a lot more fun to be had later.” And then she got down from the chair and started to smooth out her dress.

My mind was spinning. This was not how I expected my bride — who until this very moment had seemed modest, demure, and innocent — to behave, even in private. So forward! And to my shame, I had given in to my own base desires with her, had enjoyed her groping. And yet, despite myself, I found something distinctly arousing and enticing about her brazenness, something unnameable that made me hunger for what was to come that night.

There was a knock at the door, indicating that our alone time was over — at least for now — and it was time to join the reception. But even as we danced, her with the women and me with the men, and mingled with family and friends, my thoughts kept returning to her weight in my lap, the softness of her skin, the slightly sweet smell of her hair, the tender but insistent pressure of her lips against mine. I was practically staring at her all night, and every time she caught my eye she smiled in a way that only fanned the flames of my passion for her.


“Would you unzip my dress, please?”

I stood there, mouth hanging open, like an idiot.

“So I can change? It would be a shame to ruin such a beautiful dress by sleeping in it.” Deborah turned around.

I walked across the hotel suite to where she was standing. I’m just at the upper end of average in height, 5’10”, but I was nearly a foot taller than my new wife. Hands practically shaking, I unhooked the clasp at the top of her dress and slid the zipper down. In the narrow “V” it left behind, I could see the white band of her bra running across her back. Holding the front of her dress against her body, Deborah turned to face me.

“Go take a shower and wash up,” she said, giving me a pat on my butt that made me jump, “You’re all sweaty from dancing. By the time you’re out I’ll be ready for bed.”

When I got out of the shower, Deborah was sitting cross-legged on the bed, in gray sweatpants and a soft-looking blue t-shirt with the name of her high school on it. Her hair was down now, and her makeup gone; she must have used the second bathroom in our hotel suite. This was the first time I had seen her in anything other than a skirt, the first time I had seen her arms above the elbow, and I took a moment to survey the unfamiliar sight. Her chest looked different, and it took me a moment to realize she must not be wearing a bra under the t-shirt. Deborah smiled at me again, that same bewitching smile, and motioned for me to sit opposite her on the bed.

“I want to talk to you about something that’s on my mind,” she said. I nodded. “I want you to know, first and foremost, that I love you completely and I am so excited to be married to you. I’m also…” she looked away.

Taking a chance, I reached out and touched her hand with mine. She jumped a little and then, as if remembering we were now allowed to touch, turned her hand over and held my hand in hers, looking back at me. “I’m nervous about… being… with you… as your wife, for the first time. Being— intimate. I’m…” She motioned up and down her body. “I’m small, and I don’t know… I’m afraid it’s going to hurt and I just don’t know if I’m ready to…” She took a deep breath. “I don’t know if I can have sex with you tonight. Right away.”

I must have done a terrible job of hiding my profound disappointment, because she touched my cheek and said, “Oh, Benny… sweetie, don’t worry — soon.” She pushed me back so I was reclining onto the pillows, and sat astride my legs. I felt the now-familiar tension in my pajama pants, and I started to worry that she might see a bulge. “Besides, there’s other fun to be had…”

She smiled that smile again, and before I could process what was happening her hands were pulling on the waistband of my pajamas, sliding it down to my thighs, and without warning her small, delicate hands were touching my penis and balls, rapidly coaxing my shaft to a hardness I had never before experienced.

“Deborah—” I said, not sure what else I might say but feeling desperately out of control, not wanting her to stop but feeling like she should. Deborah didn’t answer; instead, she closed her lips around the tip of my member and then slid most of it into her mouth. My eyes drooped closed and I let out a loud groan. I had no idea what she was doing with her mouth and hands, but it was quickly overloading all my senses. It was as if my whole being had condensed into my loins, an explosion of heat, moisture, pressure, and motion. I had never experienced anything like this, not when my hands lingered a little too long while washing in the shower, not even the panicked dreams that left me in need of a change of sheets; it felt as if my manhood might burst entirely. My balls grew heavier and heavier, as if they were anchors holding me onto the bed, keeping me from flying off into the heavens. I’m going to die. She’s actually going to kill me. This is what the end is like.

And then something did burst in me — wave after wave of the purest, most intense pleasure I had ever felt. The muscles near my butt started to clench and spasm, and I felt an odd sensation — like peeing, if it came in discrete, thick pulses. I was vaguely aware that I was making all kinds of noises, that my hands were gripping the sheets, that my feet were flexed so dramatically I thought my toes might break.

Just as suddenly, the feeling subsided, and I felt cool air on my crotch. Opening my eyes, I looked down to catch a glimpse of my small, shriveled member, glistening wet, before Deborah lay down on top of me, pulling the covers over us. My eyes were only half-open — the best I could manage — and she looked directly into them as she whispered, “I love you so much.” Her breath smelled crisp, with a hint of salt, almost like the ocean. Leaning in, she kissed me with passion and force, and this time I could taste something fresh and salty on top of the other tastes I remembered from our earlier kisses.

Reaching to the side, she clicked off the bedside lamp. “Sweet dreams,” she whispered.


I awoke in the morning wracked with guilt. What had we done? I had spilled my seed in vain, a vile sin; and worse, in the process I had defiled my bride, polluted her innocent mouth. How will I face her? How will I look my father, or my rabbi, in the eye again? Where did she even get the idea to do a thing like that? Will we still respect each other, after behaving like animals? Should I have stopped her?

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As my thoughts swirled, I became aware that I was alone in the bed, and that it was late enough in the morning that sunlight had filled the hotel room. Looking around, I saw Deborah sitting in the corner in a chair by the window, a magazine in her lap. She was wearing something the likes of which I had never seen before. I could tell, intellectually, that it was a nightgown, but not like any I had seen when my mother hung up the laundry. Trimmed with lace, and as black as her hair, it looked like midnight against her white skin. It was short — indecently short, really — probably not covering more than her hips if she was standing. At the upper end, the nightgown barely covered half of her breasts, and something was pushing them up and together as if they might overflow their bounds at any moment. Her shoulders were completely bare, except for two small ribbons that ran onto her back. When she saw that I was awake, she smiled. “Good morning, sunshine.”

I sat up in bed. “Deborah… I feel like we should talk about what… happened, last night.”

“What’s on your mind?” She set her magazine on the coffee table.

“We…” I took a deep breath. “What we did wasn’t right. We sinned. I—”

“Stop.” The smile was gone, replaced by an intense stare I had never seen before. In a commanding tone I had never heard from her before, she said, “Let me make myself very clear about something, and this goes for the rest of our lives: when we’re alone together like this, when we’re intimate, you and I are going to do and say and share absolutely whatever we want, and I don’t give a damn what your teacher once told you, or you read in a book you’re supposed to do or not do. I intend to be satisfied, sexually,” she leaned heavily on the last word, “In our marriage. Not negotiable.”

“But I—”

“Not negotiable. And let me be very clear about what I mean by that: if I do something for you, or ask you to do something for me, that makes you uncomfortable, we’ll stop. But just because someone told you it was naughty, or you’re afraid of what someone might think, frankly I just don’t care. Sex is between us, and only us. No one else’s business. If it feels good for you and it feels good for me, if it gets us excited, that’s all that matters.”

“But God knows what we do, even if we hide—”

“I should hope God has bigger fish to fry than what you and I get up to behind closed doors. If it feels good for both of us, why hold back?”

“But I spilled—”

“Your ‘seed’?” The smile was back. “I have a hunch there’s plenty more where that came from.” Despite myself, I could feel the stiffness coming back into my loins.

“But what we did last night was so degrading!” I protested.

“Degrading to whom?”

“To you!”

“And whose idea was it?”

I paused. “Yours…”

“And did I look ‘degraded’ to you, afterward?” I shook my head “no.” “In all honesty, I had a damned good time, and I intend to do it again sometime soon.” Sometime soon! My member twitched at the thought.

“I… don’t know what to say.”

“I don’t want you to say anything.” The commanding tone was back in her voice. I watched, in disbelief, as she slid down lower in the chair, her knees spreading apart. I knew I shouldn’t look, but I couldn’t help myself. There, between her milky-white thighs, was a black triangle of satin covering her womanly treasures. I watched in disbelief as she slid a hand down over her panties, caressing herself.

“I can see you’re getting hard,” she said. I blushed. “Touch yourself.”

I shook my head. Deborah pressed her hand hard against her underwear and closed her eyes. She moaned gently and reached her other hand up to cup her breast. “Touch yourself, Benny,” she whispered to me. She opened her eyes and looked right at me. “Please…”

“I— ” I swallowed, hard. “I don’t know what to do.”

“I find that hard to believe,” Deborah replied, running her hand in circles over the fabric covering her crotch. My eyes were glued to her hand, amazed at her boldness and longing to see what lay beyond the soft cloth. “You never pleasured yourself?”

“No, it’s— I was always told it was a sin.”

“So was I but…”

“But what?” I asked.

Deborah moaned again and smiled. “You want to know how I learned to masturbate, don’t you?” I nodded, still staring at the hand between her thighs.

“It was the summer before my junior year of high school. I was working as a day-camp counselor and it was an exceptionally hot summer and by the time I got home at night I was beat. Sometimes I went to bed at eight o’clock, just because I was so tired. One night my bed is covered with assorted clothes, and I’m too tired to deal with it so — at my laziest — I just lay down on top to go to sleep. As I’m moving around trying to get comfortable, I start to feel something funny: there’s a balled-up t-shirt right in the middle of the bed, and it keeps bumping up against my privates, and each time it does I get a little jolt of pleasure. So I start rubbing against it intentionally — forward and backward at first, then side to side, until I figured out to move in a circle on top of it.”

Deborah’s breathing was getting heavier as she told the story, and I noticed that somehow, without my realizing it, my hand had slipped into my pajamas and was touching my hard penis.

“Take it out,” Deborah said, nodding toward where my hand disappeared into my pants.


“Take it out and let me see you stroke your cock,” she said, smiling as she said the last word, enjoying her ability to shock me. I hesitated. “If you want the rest of the story — and there’s more to come — I want to see you stroke yourself. Pants off.”

I felt awkward about showing her, but I didn’t want her to stop the story. After another moment of deliberation, I took off my shirt and slid my pajama pants down. My penis — my cock, she called it — sprang upright. It had been hard before, once or twice a day at least in the years since started developing, but I couldn’t recall ever really looking at it. Now, though, I was staring right at it — we both were. It looked to be six or seven inches long, and maybe an inch or two in diameter. There were some puffy veins running the length of it, from the wiry hair at the bottom up to the top where I had been circumcised as a baby; that part was turning a shade somewhere between red and purple.

Deborah made an appreciative moaning sound; when I looked back at her, I saw she had slid her hand inside her panties where it continued to move around. She made a “please start” motion with her other hand, and I dutifully wrapped a hand around my rock-hard shaft. I sat there for a minute, feeling my penis throb under my hands, until Deborah made an “O” shape with her hand and started to move it up and down. I mimicked her movement and groaned loudly as an intense wave of pleasure emanated out from my manhood.

“So there I was, rubbing myself in circles on this bunched-up shirt, when I get a feeling like the biggest head-rush I’ve ever had,” she continued.

“Like what I felt last night, when you…”

“When I sucked your dick?” The vulgarity again, I thought. It sounds so wrong, and yet it does something to me, makes me desire her more.


“Yeah, more or less like that. And of course, like I said, it’s about a million degrees that summer so I’m sweating and panting as I lie there on the bed, and I can feel that my panties are kind of wet and I wonder if maybe I peed myself or something, so I reach down to check and I notice two things: first, that they’re more damp than wet, and I definitely didn’t pee; and second, as soon as I touched my underwear the same feelings came right back again.”

“So what did you do then?” I could feel tension spreading through my groin; I found that if I squeezed my shaft hard, I could slide the outer layer of skin up and down, a dry version of what I had felt last night in Deborah’s mouth.

“What do you think I did? I think I rubbed myself to maybe six or seven orgasms that night.” I gasped. “I was exhausted the next day, and my arm was so sore I had to swap shifts with another counselor to avoid tennis.” We laughed together.

Deborah closed her eyes. Her hand was still moving inside her panties, but the motion was different. I couldn’t work out what she was doing, but there was a wet, squishing sound and a sweet, thick, musky scent was beginning to filter over to me. Without meaning to, the pace of my stroking was increasing.

“I kept that up for about four years, maybe five,” Deborah went on. “I tried not to do it too much after that first night — I guess I also felt guilty, dirty, about it, even though I was pretty sure that the other girls I knew were doing it also.”

“How,” I practically moaned.

“You hear things at sleepovers,” she said. “Some girls fidget a bit too much in their sleep, or they get carried away and moan. It’s like everyone agrees not to talk about it. For whatever reason, even though I would still get myself off somewhat regularly, I didn’t try any other ways of doing it until college, when a friend tipped me off…” Deborah’s forearm tensed and she scrunched her eyes closed, then her hand shifted and I could tell she was making those circles again. My hand was in constant motion now, up and down, and my other hand was lightly tugging on my balls as Deborah had done the night before.

“A friend tipped me off that you could get a finger inside without breaking your virginity, and that was a whole other world. I was a whole other kind of feeling good,” again she paused to take in her sensations, “and I was hooked. A couple times a week, daily sometimes—”

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I let out a loud grunt that interrupted Deborah, and without warning I felt that same flood of pleasure and the pulsing feeling — only this time, in the light of day and without Deborah’s mouth covering me, we both watched as five globs of thick, white goo shot out the tip of my cock and landed on my belly, hand, and in my pubic hair. Deborah moaned loudly as it happened.

“Come here,” she said with a strange mixture of demand and pleading. I looked at my sticky right hand, unsure what to do about the mess I just made all over myself. “Come here, just like you are.”

I walked over, feeling it start to drip downward. Deborah pulled her hand out of her underwear and lifted my hand. Without breaking eye contact, she brought my hand to her mouth and sucked the goop off it.
“I love the taste of your cum,” she moaned as she leaned in to lick my belly. “Now sit.” She motioned toward the floor below her chair. Lifting her hips, she wiggled out of her underwear. Breathless, I stared straight at her feminine treasures. The musky smell was stronger now, pungent, and beneath the dark patch of hair I could see some wrinkled pink skin, glistening slightly.

Deborah sat back down in the chair and resumed rubbing herself. This time I could see everything — how she cupped herself in her hand, pressing all four fingers against her crotch; how she rubbed her fingertips in circles over the small button in the center of her pubic hair; the way the glistening skin parted as she slid two fingers inside herself.

“I want you to eat me out,” she said, using both hands to part her hair and spread herself, revealing a slender opening that was shiny, pink, and somewhat swollen. She touched the button at the top of her slit. “This is my clit — clitoris,” she said. “Lick me here, gently at first.”

This was well beyond anything I had thought to expect — not that I had put all that much thought into it — but I leaned in, sinking into the damp, thick aroma of her sex. Gingerly, I reached the tip of my tongue toward her clit. Apparently unimpressed with my first attempt, she grabbed my head with both hands and pressed my whole mouth onto her. “Lick me,” she said. “Eat my cunt, get me really wet so I can put your cock in there.” I wasn’t shocked by her language any more, but it still had a substantial effect on my hardness. “Touch me,” she moaned.

I slid my hands up and down her thighs, caressing her legs and reaching up to stroke her belly under the fabric of her nightgown. Remembering what she had said about liking circles, I started to swirl my tongue around on her clit, and she responded by rocking her hips back and forth against my face.

“Don’t— stop— but put— a finger— inside— me,” she gasped.

Unable to see, I groped around with one finger until I felt an opening. It was warm and wet and my finger slid right in. Unsure what to do from there, I held it inside her. “Turn your palm to face up,” she told me, panting. “Curl your finger like you’re saying, ‘come here.'”

I started to bend my finger and felt something rough and slightly bulging inside her. As my finger grazed along it, she screamed and grabbed my hair. I started to pull back, sure I had hurt her, but she held my face against her crotch. “Don’t fucking stop!” she yelled, before she fell into a wordless moaning. I curled my finger again, with the same results. “Make me cum,” Deborah moaned. “Oh, I want to cum, make me cum.”

I pressed my finger rhythmically against that spot inside her as I flailed at her clit with my tongue. She pressed my face into her harder and harder — it was starting to hurt, a little — for maybe a minute or two more and then, all at once, her taste changed, the walls of her vagina felt a bit looser around my finger, and she released her grip on my head.

“No more,” she panted, pushing me away. “Go up on the bed and lie down.”

I did as she instructed, my penis more than halfway hard again. Deborah climbed up on the bed on her hands and knees and sucked me into her mouth. Her head bobbed up and down quickly, but without much suction — a far cry from last night. After a few rounds she sat back up, stroked my shaft a few times to confirm that I was hard, and swung a leg over me, straddling my hips.

“We’re going to do it now,” she said, “But I make all the moves this first time. You lie still and let me control the pace.”

I nodded, unable to speak on account of the anticipation. She grabbed my cock in her hand and lowered herself down, rubbing the tip of it up and down her dripping slit. I felt her position the head at the same soft opening my finger had slipped into earlier, and then she settled down slightly. The head was suddenly enveloped in the softest, warmest, slipperiest sensation I never could have imagined, and we both moaned simultaneously.

Deborah lifted the hem of her nightgown so that I could see where the very end of my dick disappeared inside her, then reached further down to rub her clit, her fingers grazing my shaft as they made their circles. As she rubbed herself, she rocked her hips back and forth.

“Touch me,” she whispered. I reached up and placed one hand on her breasts. “Untie me,” she said, breathlessly, “In back.” I reached behind her nightgown and felt a set of laces. Tracing up to the top, I found the knot and opened it. The whole nightgown loosened, and Deborah stopped rocking for a moment to pull it off. I gasped: there she was, completely naked on top of me, our most private parts linked together in intense pleasure. Her massive breasts, freed of all restraint, hung down toward me, dark red-brown nipples at the tip. I caressed one gently, and Deborah moaned. “Harder,” she whispered, rocking her hips again. I squeezed her breasts, one hand on each, and she rewarded me with a loud groan.

Bracing her hands on my chest, she looked right at me. “I’m going to get you all the way inside me now,” she said. “I don’t know if it’s going to hurt me, or how much, so follow my lead, and no matter what — ” She dropped her tone to a whisper, “I love you and I want this so badly.”

With that, she took a short breath in and pushed her hips sharply down until her butt was resting on my thighs, her chest pressed against mine. She cried out as she buried her head in my neck, and I felt hot tears. Unsure of what to do, I lightly caressed her back as she trembled against me.

Sitting up slightly, Deborah resumed rocking her hips; now her clit was grinding against my pubic bone. She smiled down at me, a few tears still running down her cheeks. “It’s done,” she said, “You’re all the way in me.”

She started to slide up and down now, a little bit at first but soon she was traveling all the way up to the top, so that only the head was inside her, before plunging back down. My shaft was glistening with her wetness, together with some thicker white cream and a few streaks of bright red blood. Deborah was panting now, breathing in as she lifted up and then back out as she pushed down on my cock. As she pumped away, I felt the now-familiar tension building. “I think I might cum soon,” I managed to croak.

Deborah smiled her biggest smile yet. “Good,” she said, “I want you to fill me up with your cum. Can you do that for me?”

I nodded, but Deborah was clearly not done. “I want you to pump me full of your seed.” She groaned and reached down to rub her clit yet again. “I want you to do me like this every day until I’m pregnant with your baby… I want you to cum inside me over and over until you get me knocked up and then— ah!” Deborah’s body started to shake. “And then you’re going to fuck me hard while I’m pregnant, too. Every. Fucking. Day.” She was staring right into my eyes as she said those last words, and I completely lost it. I clutched her hips as hard as I could and pulled her down onto me as I felt the cum shoot out of me, four, five, six blasts, as deep into her as I could manage. Trembling, practically convulsing, Deborah collapsed on top of me.

We stayed like that for a moment, and then she whispered into my ear, “Best… orgasm… ever,” and kissed my cheek. She rolled down onto the bed next to me. Looking down, I saw my now-soft dick covered in both of our cum and a fair amount of her blood. Rivulets of cum seeped out of her slit, mixed with more blood — blood that meant we would not touch again for the next seven days, as Jewish law dictates. Deborah must have been thinking the same thing because she pressed her warm, soft body against mine and said, “The seven days don’t start until we get out of bed, right?”

I reached my arms out and pulled her in tight, and that was all the answer she needed.

Updated: April 16, 2018 — 3:18 AM

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