The Night Before

This is something of a sequel to my earlier story, "Social Sex Ed," but written so that you can hopefully understand it even if you haven't read the earlier story.

*

The elevator doors opened and we stared at each other in shock. We stood there for so long, both stunned, that the doors started to close and I quickly put a hand in to stop them. She stepped off the elevator and the doors closed behind her.

"Deborah?" I asked, still not entirely sure it was really her. "Do you live here?"

It had been about a year since I had seen her, but she looked pretty much the same. Her thick, black, curly hair was longer but her basic build — extremely short (at 5'3", I had at least four inches on her), with massive boobs, a thin waist, and wide hips — was unmistakable. Suddenly, memories of the last time I had seen her came flooding back, and despite myself I felt a damp heat in my groin.

"I... Rachel, hi..." she sputtered. "I— my brother lives here, with his wife, they live here, on the third floor, and I was just— I was just visiting them." She sounded decidedly nervous; was she also remembering that night? "I live on the Upper East Side," she added.

"I was so surprised — I mean, surprised in a good way — to see you. Here. I live here. I... well, it's been a... long time," I said, and blushed. I guess I was also nervous.

Deborah was fidgeting with her hands, and I pointed to the diamond ring on her left hand. I remembered that Deborah was a very Orthodox Jew, and had said she'd likely be married soon after finishing college. "You were right about getting hitched so soon after graduation," I said. "What's his name? When are you making it official?"

"His name is Benny, and the wedding's in three months," she replied with a broad smile. "What about you and Aaron?"

I held up my own left hand. "We're getting married next summer," I said. Aaron and I had dated all through college, and he and Deborah had become friendly when he lived one floor above her our senior year. "Aaron got a Rhodes Scholarship, so he's in England for the year."

"I heard that, it's amazing."

We stood for a bit in awkward silence, and then I asked, "Are you headed somewhere? Or do you want to grab a bite to eat and catch up?" Deborah and I hadn't exactly been friends in college, but we had a few classes together and knew some of the same people, and I had always liked her. And there was that one night toward the end of my senior year, her junior year...

After a moment she said, "Sure, I'd love to."

We headed a few blocks down Amsterdam to one of the kosher restaurants. Over lunch, I asked, "How did you and Benny meet?"

"We were set up," Deborah said somewhat sheepishly. "Benny's sister is married to one of my brother's friends."

"That's great," I said, in part to reassure her that she shouldn't be embarrassed. "It's like someone you trust is vouching for him, right?"

She smiled. "Exactly."

"What is he like?"

"He's older, 25, and a lawyer. From Brooklyn originally. Very funny — that was important to me — but also really kind, and smart. And..." Deborah paused.

I looked over at her with a questioning look.

Deborah lowered her voice, as if afraid someone might overhear. "We were always told not to think this way, but I feel like I need to admit it to someone."

"What?" I whispered.

"He's..." She took a deep breath, and whispered back, "Hot!"

I laughed, hard.

"What?" She asked, somewhat indignant.

"It's cute that you're so embarrassed to say so. Good for you. What's hot about him?"

"Well, it's just that a lot of the guys — most guys I would get introduced to spent the better part of the last decade indoors, sitting and studying, and their... physique, if you will, shows it. Benny is different — he rowed crew in college, and he goes hiking twice a month with some of his guy friends. He's fit, which I like, and looks muscular. Manly."

"He does sound hot," I said, smiling. "Good kisser?"

"How would I know?" Deborah said, rolling her eyes. "I've never even held his hand!"

"What?"

"Not until after the wedding."

"Not even holding his hand?"

"Not even," Deborah said, with mock exaggeration. "What kind of girl do you think I am?" And then we both burst out laughing.

"Shhhh," she hushed me, looking around suspiciously, and we both laughed harder.

Deborah turned serious. "In all honesty, I am a little weirded out about the wedding night — we've never touched each other, and in theory we've never touched anyone else in that way either." Right, in theory, I thought. "But I do think I'm less anxious than I would have been... otherwise, and I suppose I have you and Aaron to thank for that."

"It was my pleasure," I said, and only then noticed the double entendre. We both fell into a fit of laughter again.

Walking out onto Amsterdam, I said to Deborah, "This was great — I'm so glad I ran into you."

"Me too," she said, smiling. "We should do this again sometime."

"Agreed." Deborah started to walk toward the 86th street cross-town bus, but I stopped her. "Do you want to give me your number, or should I just sit in the lobby and wait for you to visit your brother again?"

Deborah laughed. "Stupid me, right?" We swapped cell numbers and I waved as she walked toward her bus.

*******

I called Deborah a few times that Fall to hang out, but it never quite worked and eventually I figured maybe she wasn't all that interested in getting together. So I was surprised when, a week or so after Thanksgiving, I saw Deborah's number come up on my caller ID.

"Hi," I answered, but all I heard on the other end was sobbing. "Deborah?" More crying. "Deborah, sweetheart, take a deep breath and compose yourself and tell me what's going on. Please."

"I—" she broke off sobbing again. "I—"

"Forget it, just tell me where you are, and I'll come over."

"Marriott— Midtown—"

"What room?"

"21—" She took a deep breath. "2114."

Five or six minutes by cab. "I'll be there in less than ten minutes," I said, and hung up the phone. I checked my wallet for cash, threw it in a bag with my cell phone, and grabbed a jacket. At the last minute I went into the kitchen and grabbed a corkscrew and two bottles of Shiraz — I am not as religious as Deborah, but I keep a kosher kitchen and knew the wine would be OK — and headed out the door.

*****

The cab pulled up just before 8pm. I handed three five-dollar bills to the driver and, without waiting for change, dashed through the rain and into the Marriott. Once inside I walked briskly through the lobby and toward the elevators marked "15-24." I pushed the button for the twenty-first floor.

When the doors opened, I headed directly to the number Deborah had given me and knocked gently. I could see the peephole darken briefly, and then the door opened. Deborah must have been standing behind the door because I didn't see anyone in the room. I walked in and Deborah closed the door behind me.

I turned around and caught a glimpse of Deborah's petite, curvy body in nothing but a short white satin negligee and matching lacy panties before she threw herself into my arms. I set my bag down on the floor and held her. She smelled like shampoo and tears.

Looking around, I saw that she had a suite and we were in the living room. I led her over to the couch and we sat down. My eyes were immediately drawn to the swell of her cleavage under the thin satin fabric — I'll admit to checking out the other girls from time to time, in the locker room at the gym or wherever, and Deborah's breasts, which were big to begin with, looked massive on such a small body — but I forced my gaze higher. Her face was red and puffy and her cheeks were streaked with dried tears.

"What's going on?" I asked.

Deborah finally seemed calm, or at least calm enough to talk. "My wedding," she said, and started to sob again. She took a deep breath and then continued. "It's tomorrow afternoon, and I'm nervous... and I'm... especially nervous about... tomorrow night. After. The wedding. When we're... together, and there was really no one else I could call who I could trust. I'm so glad you're here."

"Of course," I said. "Whatever I can do to help. Speaking of which," I got up and pulled the wine out of my bag, "I thought this might be a good start."

I saw Deborah smile as she recognized a familiar kosher brand. "Maybe just a little to calm my nerves," she said.

"Attagirl," I smiled back, and started to open one of the bottles as she walked into the other room.

"All I have are plastic cups," Deborah called from the bathroom.

"They'll do just fine," I called back.

Deborah sat back down on the couch, curled her legs under her, and pulled a blanket over her lap.

I lifted a glass, as if making a toast. "Nice undies."

Deborah blushed almost as red as the wine. "Shut up, I'm getting married tomorrow," she said. "Necessary equipment."

We sat without talking while Deborah finished her first glass, and as I refilled her cup I asked, "So tell me what's on your mind."

"Here's the thing," she began, "Benny and I... we've never... well obviously. We haven't 'done' anything. And now I'm all worried — what if he's not good at... it. What if I don't..." She took a long drink of wine. "What if I don't cum with him?"

I smiled in a way that I hoped she would find reassuring. "Sex — I mean, not just intercourse, but being sexual with someone — is a learning process," I said. "It's going to take time, and you'll need to be able to talk openly with each other. Even with a guy who had been with other girls before, you would still need to tell him what feels good for you specifically. It's no different for you and Benny, except he'll probably be easier to train than a man who had been with other girls before and might be thinking about what they like. Talk to Benny about it tomorrow night — tell him you're nervous, and ask if you can take it slow. Then keep talking, so you can both learn what feels good together."

Deborah nodded.

"Also, the first time make sure you're on top — you can control things better that way. And make sure he eats you out first, so that you're really wet before you start.

"That's the thing — I'm also worried—" She drained her glass and refilled it. "I don't want to be too forward — I mean, for all he knows, he assumes I've never... you know, anything, before. So what if I ask him to do that for me, or I if touch him in a certain way, and he starts to wonder how I know about that, and then..."

"And then what?"

"And then he suspects something. That maybe I haven't been as... pure, as pure as he thinks I was supposed to be."

"Would he care?"

"How would I know? I mean, I would hope not, in general he seems like an understanding kind of guy, but maybe he would care. Maybe he would lose respect for me, if he knew..."

I poured more wine into my cup. "Do you want to know what I think?"

"Of course I do, that's why I called you!"

"Look, I am not much more experienced than you," I began, and when Deborah looked surprised I explained, "Aaron and I met when we were 19. I had messed around with one or two guys before him, but always with our pants on if you know what I mean. So I've done a lot, but virtually all of it with Aaron. Still, I am reasonably confident that as long as it feels good for a guy, he's not going to give a rat's ass how you figured out what to do as long as you keep it up."

Deborah laughed.

"Anyway," I continued, "Doesn't anyone talk to you about sex at any point before you get married? Your mom?"

"Oh God no, please not my mom!" We both laughed at that. "There's class for engaged girls, the rabbi's wife teaches it, but she doesn't give us much detail about doing stuff in bed."

"But there's other girls in the class."

"Three or four others."

"So if Benny does get suspicious about where you picked something up — which I am pretty sure he won't — you can tell him that after class one night the girls all went out for coffee and one of them, who had a more... 'questionable' past, shared some tips. It takes the heat off of you, and he'll probably get super horny trying to figure out which of the other girls was a secret slut."

Deborah laughed again, and then sighed. She stretched her leg out, brushing my arm, and without thinking I caressed her calf. "You shaved your legs," I remarked. The one time before this that I had seen her undressed, in college, she was completely unshaven, bottom to top.

"You... inspired me," she said, blushing. "Your body looked so elegant, that I started shaving too... I hope Benny likes it."

"You're beautiful and sexy, no matter what you do with your body hair. You'd better have that talk with him before you change for bed if you want him to pay any attention."

Deborah blushed a bit, and made a quiet humming sound as she closed her eyes. With a jolt, I noticed two things: first, that I was still caressing the smooth skin of Deborah's leg, and second, that it suddenly felt like the room was getting hot.

Despite myself, I set my wine down on the coffee table and slipped my other hand under Deborah's blanket, searching for her other leg. I found her knee and slid up to her thigh, warm and soft. Deborah moaned, still with closed eyes, and set her cup down too. She interlaced her hands behind her neck and slid down lower on the couch.

Her feet and calves were now in my lap, and I suspected my hands would reach well past her waist if I tried. I kneaded her thighs, testing to see how much touch she was willing to accept. Deborah adjusted her hips so she was laying flat on her back, and spread her legs slightly. Okay... I thought.

I massaged my way up her thighs, feeling her heat build as I approached her crotch. Not wanting to push things too far, I kept my hands on the outside of her hips as I felt lace and satin slide under my fingers. Nice undies, indeed. I slipped my hands under her negligee and lightly dragged my fingers over her flat belly.

Deborah moaned — it was definitely a moan this time. I froze for a moment when she put her right hand under the blanket, thinking she was going to stop me, and I was stunned when she bypassed my hands entirely and pressed her fingers against her panties instead. She moaned again as she rubbed herself over the soft fabric, and I resumed caressing her belly with one hand while I slid the other back to her thighs — the inside of her thighs, this time.

Her breath was deep and ragged, and her full lips parted slightly. I slid out from under her legs as she continued pressing her fingers against her crotch, and hovered over her for a moment before I closed my eyes and pressed my lips against hers. Her soft lips opened and I gently probed her mouth with my tongue, settling down on top of her. Through the blanket, I could feel her hand moving and settled my pelvis against hers so that the back of her hand was rubbing my clit as her fingers pressed against hers.

Without warning, Deborah turned her head away and put both hands on my shoulders, pushing me back. "No."

I sat up, wanting to respect her space.

"This is wrong."

"Wrong how?"

"Wrong like you're engaged to Aaron and I'm marrying Benny tomorrow and we're cheating on them."

"It's not cheating," I said, maybe a little defensively. "It's not like that between us. I wouldn't leave Aaron for you, and you're still going to marry Benny tomorrow, right? Tonight, you're feeling anxious and lonely and, frankly, it's been a little too long since my last trip to see Aaron at Oxford, and I could use a nice safe outlet myself. So we're just friends... a certain kind of friend, I guess. It doesn't need to involve anyone else."

Deborah was quiet for a long time. I looked away, not wanting to pressure her, but I couldn't help rubbing my crossed thighs together. If things stopped here, I was going to need to pick up some extra batteries on the way home.

"Rachel." Deborah stood up and held her hand out to me. I lifted my gaze slowly up her smooth legs, toward the panties that stretched over her hips, showing just a sliver of butt-cheek, and the thin satin nightgown that clearly showed her hard nipples, up to her face framed by that impossibly black hair. "Come," she whispered, and took me by the hand.

She turned off the living room lights and we passed into the dark bedroom, lit only by the glow of Times Square through the thin curtains. At the foot of the bed she turned to face me, put her hands on my cheeks, and pulled me down to kiss her. This time she was more insistent, her tongue darting in and out of my parted lips.

As we kissed, she brought her hands down and cupped my breasts. They're basically tiny — 30A — and even Deborah's small hands could more than cover them. I moaned into Deborah's mouth, and she ran her hands down to the hem of my cashmere sweater. Gently, she raised the fabric up, breaking our kiss to pass the sweater over my head. I hadn't bothered to wear a bra — generally unnecessary with my size — and she quickly sucked one of my nipples into her mouth. I closed my eyes and savored the sensation, my hands stroking Deborah's back.

Then Deborah sat on the edge of the bed and, looking up into my eyes, unbuttoned and unzipped my corduroys. The pants dropped around my ankles, and I kicked off my shoes and socks and stepped out of them. Deborah had slid up the bed and was laying back against the pillows, rubbing her pussy over her panties as she looked me up and down. Two can play at this game, I thought, and slipped my right hand into my underwear. With my left hand, I lightly pinched a nipple between my thumb and forefinger and started tugging on it as I ran a finger over my pussy lips. They were slick with arousal, hot to the touch. I slid my index finger into my silky tunnel, then brought it up to touch my clit. I couldn't help moaning as I ran the wet fingertip over my engorged bud. The whole time, Deborah and I were staring straight at each other.

With a curled finger, Deborah beckoned me onto the bed. I crawled on my hands and knees until I was hovering over her body, then laid down on my side next to her. She turned to face me and we embraced, our lips locking again. Now, shirtless, I could feel the heat of her body through the soft satin of her lingerie. Our hips pressed together and our legs intertwined and, as if on cue, we started rubbing our pussies against the other's thigh. Waves of pleasure rippled out from my clit through my whole abdomen and down my legs. I felt Deborah's mouth on my neck, biting and sucking and licking with abandon, and made a mental note not to leave any marks on her body — that would be hard to explain to Benny!

Deborah's breathing was speeding up, and I increased the pressure of my thigh against her pelvis. Reaching behind her, I unlaced the back of her negligee and released her enormous boobs. Sliding my hands between us, I slipped under the fabric and, pushing the underwire out of the way, laid my hands on her mounds. Deborah gasped and then moaned loudly as I kneaded her heavy flesh, still grinding my hips against hers. I could feel her body stiffening as her breathing and moaning grew louder, and then she buried her face in my neck as her orgasm broke. Panting, she pressed her body against mine and shuddered as wave after wave of bliss rolled through her body. As her orgasm subsided, Deborah pressed me onto my back and straddled my slender hips.

"Your turn," she said with a smile, and lifted the nightgown over her head. Completely freed at last, her heavy breasts splayed out to the sides as she arched her back and stretched. Leaning down, Deborah kissed me again, full on the lips, and then slowly moved her mouth down my body. She lavished attention on each of my small mounds, sucking and biting my nipples until they stood at attention. She kissed every inch of my stomach, tonguing around and inside my belly button, stroking my thighs all the while. When she reached the hem of my underwear, she tugged a bit at the elastic with her teeth. I lifted my hips off the bed and, with a smile, Deborah pulled my panties off.