“So Ash,” Kara said, stirring her drink with a straw. I knew Kara well enough to recognize this as a sign that she was winding up to ask me something she thought I was inclined to say no to.
“Yes?” I said, prompting her to continue. She spent another moment poking at the lime wedge in her glass with the end of the straw, no doubt plotting how to subvert my reluctance to whatever it was she wanted.
“I know you said you weren't interested in dating right now, but I have this friend…” I sighed and leaned back in my chair, but Kara stopped me before I could object. We had split up amicably three years ago, and Kara kept trying to set me up on dates with her friends. But I let her go on. “Hear me out. I know you don't want a full blown relationship. But I have this friend. Andi. She's… sort of in the same boat I was in back when we first started dating.”
That had been seven years ago, when I was 23 and Kara was 21. I'd been her first real boyfriend and she'd started out very timid around the idea of sex. Hyper religious upbringing, hadn't even seen a dick before I'd taken my pants off the first time, but by the time we realized we weren't after the same things in life, she had a voracious appetite and a very adventurous spirit for sex.
“You remember the way I was back then, right? ‘Oh my goodness, is that really all supposed to fit inside me? It's so much bigger than I imagined!’ and all that.”
“You still do a remarkably good impression of the sweet, innocent preacher’s daughter,” I said.
“Twenty one years of practice, Ash,” she said.
“And then I corrupted you with my worldly ways,” I said. “And you want me to corrupt another sweet young preacher's daughter, is that it?”
“She's not a preacher's daughter,” Kara said, “though she’s about as sheltered as I was back then.”
“Like I said, Kara, I'm-”
“-Not interested in a relationship, I know, I know. Neither is Andi. But she's starting to come out of her shell a little bit and she's really self conscious about the fact that she's still a virgin at age 24.” I raised an eyebrow. “Don't worry, it's not because she's unattractive! She's actually really hot. Big perky tits, nice round butt… I know how much you like a plump, round ass, Ash…”
“That's not my hesitation,” I said. “For starters, I'm six years older than her. Even with you I felt a little weird about being older and more experienced at first. And I'm only two years older than you.”
“Yes, but six years when you're thirty is a lot less significant than six years when you're twenty three,” Kara pointed out. “And you're really good at taking it slow and being respectful, like you were with me. I've talked to a lot of my girlfriends and their first times were… well, let's just say I have a renewed appreciation for your approach. Andi is a sweet girl but she won't stick up for herself, and I'm worried that if she doesn't have someone like you there, she's just going to be traumatized by her first time.”
I sighed. Kara really knew how to work me. “Does she know about this plan of yours?” I asked.
“I've talked with her a lot about sex already, trying to make her feel at ease. Trying to help her recognize when a guy is hitting on her, for one thing. She's totally oblivious to that, unless the guy is being a gross creep about it. She wants to have sex, she's just nervous about it, and I told her how nice it was having you as my first, and I may have mentioned you weren't dating anyone and asked if she wanted me to approach you about it. And she said yes. She thinks you're hot, by the way. I showed her pictures.”
I opened my mouth to object, but Kara again jumped in. “Not those pictures, of course. Those I deleted when I started seeing Josh. Except for the one where you've got me upside down and your face is cropped out, and the one with the- never mind. I didn't show her any of those. Just your Facebook pictures. She's hot for you, Ash. She's checking you out right now.” Kara nodded over towards a small table across the room, where a short, redheaded girl sat. She blushed and quickly looked away as I turned towards her, but I caught enough of a glimpse to confirm that she was, in fact, very cute.
“So what do you say, Ash? Can I call her over and introduce you?”
I should have been annoyed with Kara at the way she'd set this up. There was no way for me to decline at this point without hurting the poor girl's feelings, or at least embarrassing her. But truth be told, even though I wasn't interested in the commitment of a major relationship, I was feeling starved for touch and intimacy. And she was cute. “Fine,” I said. “Introduce us.”
Kara got up and went over to Andi's table. I couldn't hear them, but I saw Kara nodding, and Andi’s face broke out into a wide grin. She looked my way, and this time didn't shy away when I looked back. I raised my glass and winked at her, and she blushed and waved back.
*****
Kara had stayed only long enough to introduce us, and to wish Andi luck, and to whisper in my ear that she'd kick my ass so far up my own ass if I was anything less than a perfect gentleman. I guess she didn't think I'd need the good luck, though to be honest I was a little nervous about the assignment. Assuming this all went according to plan, she'd owe me big time. Andi and I spent another hour at the bar chatting, and I actually found her charming, if a little socially awkward. She was a student of astronomy at the University, which took up most of her time, and like me she wasn't interested in a major relationship commitment. “I just feel like I'm missing out on this vital part of being a young person,” she said. “I don't care if I never get married or have kids or anything, but… sex sounds really fun, and at this point I feel like I need to just rip the bandaid off and do it. So, um. Wanna come back to my place?” She laughed nervously.
I put my hand on hers and said, “Yeah, let's get out of here.” I felt her tremble at my touch.
I hailed a ride from my phone app, and we left the bar.
*****
We sat on the bed in Andi’s room. For all her eagerness, I could tell from her body language that she was still feeling nervous. She sat with her legs tight together, her fingers fidgeting in her lap. She wore a bright red shirt with a print of Saturn on it, the planet bulging out realistically from her tits. Kara hadn’t been kidding - they were big. She wore blue denim shorts that left most of her thighs exposed, revealing pale, subtly freckled skin. “So, um… I guess I need to give this to you now?” She fumbled in the drawer of her bedside table and pulled out a condom in a blue wrapper. She held it out to me, nervously looking away as I took it from her. “Kara told me about… why you two broke up.”
“She wanted kids, and I didn't,” I said. “And she was mad that I went and got a vasectomy without talking to her about it.”
Andi nodded. “So I know that you can't actually get me pregnant, but still… are you ok to use a condom anyway?”
“Of course,” I said. “This is all about your comfort. I still enjoy sex with my dick wrapped up, don't feel the least bit bad about being careful.” I took the condom from her hand. I noticed it was shaking.
“Before we get to needing this,” I said, “tell me a little bit about what you're familiar with. Have you ever kissed a guy before?” She nodded. “Ever had a guy touch you somewhere intimate?” She shook her head. “Ever seen a man naked?”
“Not in real life, but I've watched some porn videos.”
“Listen, um… sorry if this is stating the obvious, but did Kara, or anyone else, ever talk to you about sex hurting the first time?”
“Because of the hymen,” she said, nodding. “Don't worry. I took care of that myself a while ago. Kara helped me pick out a dildo and I, uh, popped my own cherry.”
“Have you used it since then? Do you like it?”
Andi nodded. “Yeah, I've practiced some.” She laughed nervously, her hands fidgeting furiously. “Can I kiss you now?” she asked. I nodded and reached out to cradle her head gently with one hand. I drew her close to me. She trembled again as our lips connected. I let the kiss linger, then released her as I felt her begin to pull away. “You smell really nice,” she said. “Masculine.” Her hands continued to fidget, and I closed my hands around hers, again holding her gently.
“You smell nice too,” I said. “Feminine. Can I kiss your neck?” Andi nodded, and I leaned in again, planting a kiss just below her jawbone. I heard a quiet sigh escape her mouth, and I moved down her neck, kissing again and again, until I reached her collarbone. I pulled away and came back up to face her. “Before we go any further,” I said, “I want to make sure you know that we can stop at any point. Pick a word, something you can remember easily, and that will be your safe word.”
“A word like… stop?”
“Make it something you wouldn't normally say during sex, something I can't mistake. I don't want to stop if you're telling me, ‘don’t stop’. Something like…” I looked down at her chest. “Saturn,” I said, touching the planet. My finger sank into the soft flesh below the shirt and she trembled again.
“Ok. Saturn means stop. Got it.”
“You can say that at any point you don't feel safe,” I said, “and I'll stop what I'm doing and check in. Ok?” Andi nodded. “You can also ask for anything you want me to do,” I said. “Or that you want to do to me.”
Andi looked at me. “Can I see you naked?” she asked. I stood up and shucked my shirt, taking my time. I took good care of myself, and I knew I had a trim body. I planned to let Andi enjoy it. She reached a hand out and ran it through the hair on my chest. I let her feel me as I started to undo my belt buckle, but her hands came down and stopped me. “Hang on. I want to do this part. But first,” she said, “this feels a little unfair.” She pulled her shirt up from below, her tits bouncing in her bra as the hem of the shirt cleared them and lifted over her head. Then she reached behind her back and undid the clasp of her bra. It fell away, freeing her magnificent, massive breasts. She flung the bra aside then cupped one breast in each hand, bouncing them to show off.
“Andi… you have fantastic tits,” I said, without a shred of exaggeration.
“Why don't you play with them a little while I work on this,” she said, returning her attention to my belt buckle. I needed no extra encouragement, taking a breast in eaxh of my hands and gently squeezing them, letting my fingers brush against her nipples. She gasped as I gave one of her nipples a gentle pinch. “Ooh, yes. Like that. But a little harder,” she said. I pinched both nipples this time, and Andi let out a little squeal of delight.
“Just wait till I get my mouth on these,” I said. Andi’s eyes closed and she tipped her head back, her breath quickening and quivering at my touch. She'd unfastened my belt and this point, but had stopped working on my pants, her attention thoroughly diverted by the sensation of the nipple play. I knelt down and placed a kid on one of her nipples, which elicited a soft moan of approval. I flicked the bike with my tongue, then pinched it between my teeth and lips. That drew out a louder moan. I gave her other breast the same treatment, and when I glanced downward I noticed that she was grasping at her crotch through her pants.
Suddenly she gasped, and I pulled back to see her, flushed red in the face, starting at the hand that she'd been massaging herself with. “Sorry, I got carried away there for a moment,” she said.
“Don't apologize. Do what feels right,” I said. Her gaze traveled down my chest, down my belly, again to the belt line of my pants. She undid the button and pulled the zipper down, then she grasped my pants and underwear, pulling both down until my cock was free. It sprang right back up to attention, inches away from her face, and her eyes went wide for a moment.
“That's… bigger then my dildo,” she said. “Surely that can't all fit inside me, can it?”
“It can if you want it to, I promise,” I said. Kara had reacted almost the exact same way the first time she'd seen me erect. “Are you sure you want that? Never too late to stop,” I said.
“Be honest, is that going to hurt?”
“I can't possibly say for sure,” I said, “but every other woman I've been with has enjoyed it quite a bit.”
Andi held my cock in her hand, stroking her hand up and down the length of it. “I can't even fit my fingers all the way around it,” she said. “Can I lick it?”
“Absolutely,” I said. “And I'll return the favor if you want.”
“Hmmm,” Andi said, and gently touched her tongue to the tip of my cock. She gave it a gentle kiss next, then let her tongue explore a bit more. Ahe finally opened her mouth and took the tip all the way in, closing her mouth around it.
“Oh fuck yeah,” I groaned. “That's good, Andi. Suck that dick.” She placed her lips right at the tip and then-
“Oh, that's just an expression,” I said. “What you were doing before was perfect. You don't need to literally suck on it like a straw.”
“Oh.” Her face went red again, “I didn't know that.”
I knelt down to bring my face level with hers, and kissed her again. “That's what this is about,” I said. “Learning. You did that really well for someone who's never held a dick before. Do you want do more of that, or have me use my mouth on your pussy?”
“Actually,” she said, “I think I'm ready to do it. Sex, I mean. How do I - I mean, what's the best position for me to-”
“I'll give you three options to start with, you choose from those,” I said. “First one, missionary. You on your back, me between your legs. Second option is called cowgirl. I lay on my back, you straddle me and ride. Puts you in control. Third, you on your hands and knees, butt up in the air. I'm kneeling behind you. That's called doggy style.”
Andi laid down on her back. “Like this, I think,” she said. “At least to start.” Her eyes flicked down to her shorts, the only thing she still wore. “Wanna take them off me?” She lifted her hips up as I slid her shorts down, toasing them aside. She wore sheer pink panties below, thin enough for me to see that she had shaved her mound bald. I pulled those off as well, leaving Andi laying on the bed before me, completely naked.
I could tell she was still a little nervous. She kept her legs closed and squirmed a bit, uncertain of where to put her limbs.
“Andi,” I said, “you are the sexiest woman I've seen, by far. Don't tell Kara I said that, but it's true. You are unbelievably hot. We're going to take this nice and slow, ok? I won't go inside you until you say you're ready.” Andi nodded, and let me push her knees apart. I felt her legs tremble, but she pulled them back further on her own, baring her wet, swollen slit to me. I spread her lips apart with my fingers, opening her up, the skin below such a deep shade of pink it was almost red. I grabbed the wrapped condom from the bed, then scooted my knees right up into her thighs, holding her wide open for me. I moved to rip open the condom.
“Wait,” Andi said, holding a hand out. “I… changed my mind.”
Well, shoot. And here I was, all ready to go. I had considered the possibility that she'd get nervous at the last minute earlier on. And if she wanted to stop, that was that. I resigned myself to rubbing one out at home with nothing but the mental image of Andi laying on the bed like this. But I was in for another surprise. Andi took the condom from me and tossed it back in the direction of the bedside table. She didn't seem to notice that she missed it completely.
“I don't want anything between you and me,” she said, and took my cock in her hand again, stroking it as she half spoke, half moaned. “I want to feel this skin against mine. Dragging against me as you fill me up.” I ran my finger up the inside of her slit, along the ruby-red flesh up to the point where her lips met. I found the bud of her clit there, pressed my finger into and along it. “Mmmmmmmmmm…. Start out slow, but then I want to feel you all the way inside. And then I want you to finish inside me, too,” she moaned.
“Are you sure?” I asked.
“Very much so. Don't you want it too?”
“I've never wanted anything as much as I want to fuck you raw and blow my seed inside that virgin pussy,” I growled. I brought myself up so my cock rested against her slit, and I started using it to massage her clit. “Whenever you're ready.”
Andi let her head roll back, riding out the feeling of my cock tracing the length of her slit, back and forth, for a few moments longer. Then she pulled her head back up and looked at me greedily. “Do it,” she said.
My cock came to rest at the entrance to her cunt, ready to be the first one ever to plumb its depths and fill her. Our eyes met as I slowly leaned in, pushing the tip of my cock into her. Her eyes went wide then, in surprise at first but then quickly moving to delight. She inhaled sharply, holding her breath as I slowly slid my cock inside her. I paused halfway in, withdrawing slowly to give her a chance to react to the sensation.
“Was that… all the way in?” She asked. I shook my head.
“Do you want it all the way?” I said.
“Not yet. Do it again like you just did. Ohhhhhhhhhhhh…” she moaned again as I slowly slid back in. I drew right back then pumped in again, still only going about halfway in. I fucked her as slowly and gently as I could. Andi let out a cry with each push in. “A little deeper now,” she gasped out. I obliged and her moaning grew louder and sharper. “It's so big,” she said, “but so good. Give me more, give me all of it…. OHHHHHHHHHH!!”
Her eyes went wide again as I filled her up as full as I could. I held myself there, allowing her to savor this feeling as well. She cradled my head in her hands, locking her gaze on mine, then kissed me. Slowly, gently, I drew my hips back, then thrust in deep again. I felt the distant tingle of orgasm begin to build, not urgent yet but drawing nearer. I could keep myself at this point for a while longer, as long as I stayed slow like this, pumping in, drawing out, over and over.
“I want to turn over,” she said. “On my hands and knees, like you said.”
I pulled out and helped her up. She rolled over then raised her ass up. She reached under her belly with one hand and stroked her clit. I positioned myself right behind her and thrust myself back inside her. I'd truly intended to stay at the same slow tempo, but the urgency of sheer lust got the better of me, and I plunged in swift and deep.
“Oh yesssssss….” Andi moaned. “More of that, come on baby…”
That was all that lust needed to hear. I grabbed her by each hip and thrust myself in again, and again, her ass cheeks bouncing each time my pelvis slammed into them. Suddenly, Andi began to cry out, and I felt her clench down hard on me. Her body wracked with convulsions for several seconds. She collapsed onto the bed at my knees.
“Oh my… I think I like doggy style,” she croaked out. She twitched as an aftershock of the orgasm hit her nervous system. “Did you come as well?”
“Not yet,” I said, though I'd been very close right when she’d collapsed. My cock remained rigid, a bead of cum forming at the tip.
Andi rolled over and was on her back again, her thighs spread wide. Her pussy was absolutely slathered in frothy sex juices. “Come on then,” she said. “I want to see your face when it happens. Once more I drove myself deep inside the heat and wetness of Andi’s swollen cunt. I looked her right in the eyes as I thrust again, the orgasm I was so recently denied jumping right back to the forefront. She felt even tighter after the orgasm, and cried out, “yes! Come on! Give it to me!” On the fourth thrust I let it go, and my cock throbbed as my seed burst out. Andi's legs wrapped around my lower back and held me in place, my half-flaccid but still thick cock still buried to the hilt.
I kissed her again. “So, how was it? Everything you expected?”
“I think that just did a hard restart on my brain,” she gasped out. “That was the… I guess it doesn't mean much if I say it was the best sex I've ever had,” she said, “but that one's going to be hard to top.” After a brief pause, she went on. “Wanna try again tomorrow anyway?”
“Tomorrow, at my place this time,” I suggested.