An Actual 40 Year Old Virgin

"OK, you have to promise not to say anything or ever let on that I told you this."

My wife Shannon had just come in from a lunch with one of her closest childhood friends, so I can only imagine she has some kind of hot small-town gossip that I couldn't care less about, but I played along.

"I'm sworn to secrecy, dish."

She was still taking off her jacket as she dove into the story. " So Kelly has a date tomorrow night, and she was saying how nervous she was. I'm like, Kelly, you're 41 years old, this should all be pretty standard by now." We both knew that Kelly never really had a boyfriend, and she never really talked about dating, but... again, we're all in our 40's, dating is old hat (or, in my case, having been married 8 years, a distant memory).

"So she says to me, 'well, actually....' BABE! Kelly is a VIRGIN!"

I actually was, for once, shocked by one of my wife's stories. As I said, for as long as I'd known Kelly she'd been single but she has a really active social life, is always out with friends, I just assumed some casual sex or something was mixed in there. And it's not like she was ugly -- she was actually really cute. Athletic but petite, and a very young face. Legit, she still gets carded when we go out together. A virgin? Can't be. We've all heard the phrase "40-year old virgin", or seen the movie, but you never think....

I dug in. "Wait, like, a real virgin? Is she saving herself for marriage?"

"No, nothing like that, it's just... she grew up so religious that sex was a big taboo in her teenage years, and even though she isn't religious any more she just never got started and then she said it always seemed too late or too awkward, so she just gave up trying. But now so many of her friends are married with kids she finally started dating for real, but every time she mentions the virgin thing they bolt!"

I guess I could see that but I was still kind of shocked that no one tried to take advantage of her. LIke respectable guys looking for a relationship are probably going to flee immediately finding out they're dating a virgin at our age, but a million guys would hear that and take it as a personal challenge to introduce that girl to womanhood, claiming their territory. It's gross but also somewhere in my lizard brain I get it.

Even just mulling over what my wife told me, I'm kind of turned on by the idea of going where no man has gone before, but it's so much less creepy when you're not talking about some 18-year old. She is my age, but doesn't look it and apparently is pure as fresh-fallen snow. It's not like I've never checked her out before, like I said, she's cute as hell, and while not as... buxom as I usually prefer my women, she had curves where it counted, especially on her small frame, it worked. I needed to get back in the moment here, before I start chubbing up thinking of throwing that spinner around the bedroom.

"... don't even know what to tell her, can you even imagine?" I had tuned back in mid sentence but was pretty sure I got the gist.

"I really can't. So... wanna go celebrate not being virgins?" I was pretty horned up from daydreaming, might as well go for it.

My wife laughed and started unbuckling her pants. "I had two wines at lunch, you're goddamn right I do."

++=-=-=-=-=-

A few days later I had mostly forgotten about the Kelly situation, when my phone dinged in the middle of the day... and it was Kelly.

Kelly and I had known each other since I met my wife, and all three of us were really close, so it wasn't super odd for her to text me, but still felt pretty weird. We usually only spoke with my wife as part of the group, we weren't really one-on-one friends.

Hey, are you free tonight? I could use a hand.

My mind immediately popped back to the virgin conversation and I mentally chastised myself while still half-thinking about giving her more than a hand.

Yeah sure, Shannon is staying at her parents tonight so I'm solo anyway. What did you need?

I had planned on just staying in and taking a gummy by myself or something, so why not?

Her reply was immediate.

Just strong guy stuff, need some help moving things around the apartment.

No one would look at me and say "strong guy" -- I"m no slouch but I'm a middle-aged married guy who doesn't hit the gym all that often... or ever really. I've luckily not completely let myself go by any means but definitely not someone's first thought when they think "strong guy." So I appreciated the comment but was skeptical why I was her first choice. Or maybe I was only the first person to say yes....

What time?

I was working from home but it was a quiet day and already 3:30, so I was about ready to get out whenever.

I'm home now, so whenever you can get away ;-)

A winky face?

Cool, be there in like a half hour then.

I decided to take a quick shower, grabbed a four-pack of a local beer from the fridge, and headed out. Kelly lived a ten minute or so drive from our house, so I showed up almost exactly a half hour after our last text. I got up to the door of her apartment and raised my hand to knock and the door flung open. Was she just standing there waiting for me?

"Hey! Thanks for coming by on such short notice." She seemed a little flush and eager, which fit with her personality but still struck me as a little off. I smiled and leaned in for a hug. She gave me a big squeeze that seemed to linger a bit longer than normal... maybe I was imagining things.

"No problem!" I said as I pulled back from our hug, giving her a quick glance up and down. She was wearing essentially pajamas -- a set of yoga pants and a loose-fitting tee shirt. I guess if we were moving furniture and stuff it made sense, I just wasn't used to seeing her not in jeans. The yoga pants looked damn good on her trim frame though, I must say....

"You want a beer?" she asked as she gestured for me to enter and closed the door behind me. "I may have had a couple already..." That would explain the flushed cheeks and slight out-of-breathedness. Who am I to refuse such an offer?

"Sure, I brought a few of my own to replenish your inventory after." I'd like to replenish her inventory right now, if you know what I mean. Stop it! I immediately gave myself an internal smack for my stupid jokes.

We sat at her kitchen table and drank a beer for a few seconds, neither of us speaking. After about half my beer was gone and I was feeling looser, I broke the silence.

"So, what do you need from me anyway? If it's just a drinking buddy that's more than OK" I gestured in a 'cheers' motion and took another swig.

She was staring down at the table, all of a sudden seeming much more timid. Maybe she really was just lonely and needed a beer with someone? "You OK?" I asked after she didn't say anything or look up for several beats.

She still didn't look up but said "have you and Shannon talked about me at all?"

My heart stopped for a second. Had she found out that Shannon blabbed to me (of course she knew she would, we're married) and gotten upset and brought me here to chew me out? It's not even my fault! And besides you wouldn't want to come face to face with someone who knew something you were embarrassed about....

"Sure we talk about you sometimes." I decided to go with vague and noncommittal. "You're our friend, we care about you." Maybe schmaltzy too.

She finally looked up and rolled her eyes at me. "I think you know what I mean."

Fuck it. "Yeah. She mentioned it."

She almost looked relieved, like her whole body relaxed a bit when I said that. Maybe it was comforting to get her big secret off her chest?

"It's not a big deal, I know there's the stupid movie and it's a bit of a punchline but everything is a punchline, I wouldn't worry about it."

She half smiled. "Thanks. I'm not 'worried' about it per se, but it's really hampering my dating life, and last night I had a thought."

Where was this going? Why was she telling me this and not Shannon? "What's that?"

"Well, no one cares how much sex you've had, only that you've had it, right? I mean, sure people argue about their 'number' but that's a much smaller conversation than 'you're not a virgin are you?'"

I nodded, she made a good point but I had no idea where this was going. I finished my beer and waited.

She guzzled the last of her third beer (assuming she was telling me the truth about her intake prior to my arrival), and looked me in the eye. "So I just need to fuck someone and get it out of the way, right?"

I swallowed hard. Again, why was she talking to me about this? And since when does Kelly say stuff like that so casually? Don't get me wrong, she had a dirty mouth and could joke around and talk like a sailor like the rest of us, but she would never say sexual stuff about herself. It came off as very out-of-character. And hot as hell.

"Sure, I mean, I guess that makes sense."

That mischievous smile turned up a notch. "So whaddya say?"

My face got hot when it suddenly clicked what she was asking me. "You mean like... Kelly, you're my wife's best friend. I'd do anything for you but...." Was this really happening? I felt like I was in an elaborate prank.

She stood up. "I know, but I just don't know that many guys that I would trust with this, and obviously I'd never say anything to Shannon, and I've always kind of had a crush on you so it just made sense....." She had taken a few steps towards me while saying this, and I stood up to meet her.

"Kelly, listen, being a virgin isn't' a big deal, it's just this outdated milestone, you don't need to do some drastic thing just to lose your virginity, it'll happen when it happens." I felt like some other guy was standing next to me saying those words. I don't think I'd ever in my life been directly propositioned for sex by someone I wasn't dating already. And for it to be a close friend.... Who I happened to be thinking about sexually quite a bit in the past few days...

She was only a foot away from me at this point, and barely spoke above a whisper. "I know it's not a big deal, but I just need this so I can be normal around guys and actually get past the second date. Please, I need to get out of this slump and I've been thinking about it and you're the only one I trust" she grabbed my hand and stared up at me.

I couldn't believe I was in this position. Sure I concocted these kinds of stories in my head when going at myself but shit like this doesn't happen in real life. I took a deep breath and looked into Kelly's eyes, which had a sheen of tears on them but also an eager, hopeful look to them. It felt like minutes passed with us just standing silently, her holding onto my hand, and us staring into each other's eyes. Her waiting for me to say something, me going through every scenario of how this would play out and none of them being good. But another part of me... a part of me that had been steadily growing in my jeans, in particular... was thinking this was the chance of a lifetime.

I felt a feeling I hadn't felt since I met my wife. That anxious, pre-first kiss feeling, where you're pretty sure it's going to happen but the excitement of something new just flooded your head. And the extra taboo of me being married, and this being my wife's best friend, and her being a virgin to boot, amplified that ten times.

Fuck it.

I leaned in the last few inches and pushed my lips against hers, which she eagerly pushed back, opening her mouth slightly in rhythm with mine. I briefly wondered if she'd ever even kissed someone like this before, but when I felt her tongue pierce my lips I decided she must have done at least this before.

My arms wrapped around her back and pulled her tight into me as our makeout got more urgent. She almost felt like she was trembling with nerves as my hands roamed across her back, moving down towards her tight ass. The heat of the moment fully washed over me and my hand reached its target and pulled her crotch tight against mine, and she made a light squeaking noise of surprise into my mouth and pulled away. Her eyes were filled with pure lust at this point, and she was all but panting as she grabbed my hand and pulled me towards her bedroom.

We reached her bed and she sat down and looked up at me, suddenly a bit of fear back in her face. "Please take it slow..." I just smiled and nodded and leaned down to her, kissing her again as I shuffled her body further back onto the bed and climbing between her legs. The heat from her was almost unbelievably intense, and my hard-on was straining against my pants, begging for release.

Once I had her laying on the bed I slowed things down a bit, taking our feverish makeout to a slower pace, and started running my hand down her side. Slowly stroking her side until I reached her pants, then moving lower and rubbing the outside of her leg. My thumb working its way around her thigh as, on each slow stroke along her, my hand slowly rotated towards her inner thighs. Taking things slow and keeping my distance so as not to scare her away, but making it clear that that was the goal. My thumb was fully on her inner thigh now and I was massaging her leg, getting lighter as my hand rose up, teasing her and building anticipation. On each pass I felt my hand getting closer, the heat literally building, until finally my thumb lightly brushed between her legs, and she gasped but did not pull away.

I smiled and more quickly moved on to rubbing along the outside of her lips, barely brushing against her tight yoga pants that were covering her waiting pussy. Then rubbing a little harder, brushing up and down, her hips beginning to move in time with my strokes. She had her eyes closed and her head raked back, any hesitation gone as she gave in to my steady rubbing, now completely focused on her pussy, slowly increasing pressure. She moaned and was really pushing back against my hand now, so I decided to go for broke. I pulled my hand away, and reached up and grabbed the waist of her yoga pants, hooking my fingers around her pants and underwear and slowly but firmly pulling them down.

She hesitated for a half a second before eagerly raising her hips so I could get her naked from the waist down. As soon as I threw her clothes aside I leaned between her legs and resumed my rubbing, this time my fingers directly against her flesh, careful not to enter her, as I began to kiss my way up her inner thighs. I could see the moisture starting to flow out of her as my face got closer, and I finally pulled my hand away and replaced it with my tongue. She squealed in pleasure and I felt her hand on the back of my head. I suddenly wondered if she even masturbated herself before as she began humping against my face as I pushed my tongue between her folds and into her. I had barely started but she sounded like she was nearing orgasm already. And right on cue she yelled "oh, oh my god, I think I might be... is this.... Oh God.... OH GODDDDD" My tongue was working as fast as it could as I felt her clench and squeeze me tight, a deluge of fluid flowing out of her as she wailed in pleasure. I held her hips and let her ride out her orgasm, slowing my tongue as she slowed her movements, and finally giving her one last kiss and pulling away.

She had her arm covering her eyes and was just panting. I rubbed her thighs lightly and waited for her to come out of the haze. She finally looked up at me.

"I didn't know I could feel like that.... That was incredible." Her eyes were wide with excitement, and I felt a swell of pride. She eventually sat up and pulled her tee shirt over her head, revealing she hadn't been wearing a bra and was now completely naked before me. Any shyness from earlier was long gone, and a pure animal lust was on her face now. "Get your clothes off"

I jumped up and quickly stripped down to my boxers and then paused. She was staring at the tent in my underwear, waiting for me to finish undressing. I assume she had seen dicks in movies or whatever but was this really the first time she'd seen one in person? I felt a little bit of self-consciousness about having to be the guidepost for penises for the rest of her life -- I'm no slouch but also not Dirk Diggler -- but hormones got the better of me and I pulled them down, my cock springing up in anticipation. Kelly jumped back a bit and giggled, then leaned forward and reached directly for my cock.

She started slowly rubbing it, looking up at me in anticipation. I was as turned on as I had ever been, and even her inexperienced exploratory rubbing felt amazing. I began to leak pre-cum, and she squeezed me lightly to get more to come out. She finally looked up at me and nodded. "I think I'm ready." She let go of me and scooched back on the bed, laying back and spreading her legs while staying propped up on her elbows to watch me. Her body had a light sheen of sweat and I could see the quick rise and fall of her nervous breathing as I stepped forward and climbed between her legs.

"I'll be gentle, just say the word and I'll stop." She nodded and I leaned forward, my cock making contact with her soaking wet sex. I held it there and rubbed up and down, and her head fell back as she moaned in pleasure. I made sure I was as lubricated as I could be before lightly pushing forward. While she was a virgin, she was also 40 years old, so I certainly didn't expect a hymen or anything, and indeed with that first easy push I sunk an inch or so into her. She gasped and gripped my forearms. "Are you OK?"

She just nodded, opening her eyes and smiling at me. "Just a new sensation, keep going."

I pulled back a bit and then pushed a little further, repeating that a few times, each time sinking another inch into her virgin canal, each time her making soft mewls of pleasure as new territory was explored. As I neared bottoming out in her she began to slowly gyrate her hips along with me, and I finally pulled all the way out and held just the tip at her entrance, feeling her body try to pull me back in, her eyes closed and face frozen in anticipation and pleasure. After waiting a few more moments to build the tension just a bit more, I finally pushed slowly and firmly into her all the way, our hips finally meeting and a small gasp escaping her lips.

I held in that position, almost imperceptibly grinding our joined hips together, feeling my cock move inside her, and for the first time since we started my own pleasure started to build. I had been so focused on giving her this experience and making it as good and memorable for her as I could that I had been kind of ignoring my own, but instincts and sensation started to take over, and my gentle grinding started to become a less gentle pumping. Kelly let out a soft "oh!" at each of my thrusts, her hips rising to meet mine as our pace increased, the urgency of her voice also increasing. Her hand reached around and grabbed my side right above my ass, clawing at me, pulling me into her on each thrust, her hips rising further from the bed. I could feel her orgasm approaching as she began to tighten around me, and I realized my own was not far off, and somehow only now realized I had no condom on, and doubted a virgin would be on birth control. I had been married for years and never cheated and my wife was on birth control, condoms hadn't even entered my mind in ages. I was about to say something when Kelly's entire body went rigid and she screamed out in pleasure, pushing hard against me, her cunt squeezing me an almost unbelievable amount, pushing me over the edge along with her.

She felt the first spurt of my cum jet into her and her eyes shot open and stared into mine, but she didn't' stop her hips and inner muscles from milking me as what felt like a never ending series of bursts erupted from me and into her. We both finally started to slow, and I eased myself down on top of her, kissing her breasts and then falling to the side. My rapidly deflating cock popped out of her, and she gasped. I lay back, catching my breath for a few moments, before propping myself up on one arm to look over at her. She had her eyes closed, trying to catch her own breath and probably processing what had -- finally -- happened. I let my eyes travel down her naked body, and when I got to her pussy I could see a mixture of our fluids slowly leaking out of her onto the bed. My anxiety ramped up a bit and I broke the silence.