Kinda losing my virginity at 26 [MF]

So, here goes, the slightly embarassing story of how I kinda lost my viriginity.

Naturally, names and places have been changed to protect the innocent (actually, mainly just me). And this still is to the best of my recollection, it did happen many moons ago before iPhones were a thing.

Actually, it might’ve been a year or so before the first iPhone. I was 26, living in a big city, working for a big(-ish) IT company. I’d been working there since I graduated as a consulting/programming type of person.

After a few years out at client sites, I was back in one of the main offices in center of town.

I’m normally pretty punctual, but the previous night was a big one (I forget why), and I had to make a crazy rush to get out the door.

On the train ride in I realized I put forgotten to put a belt on with my jeans. No problem, I’ll just make sure my button up shirt is untucked, and I’ll be fine.

After riding the elevator to my floor, I decided to enter through a side entrance, just to be a little less conspicuous about my tardiness. Still a little hung over, I tried to open the door by lifting my leg and raising my crotch to the RFID reader by the door.

My ID card was in my wallet, and for matters of laziness I thought it’d be easier to do this than take my wallet out and press it against the reader.

“Nice ass,” a chirpy voice said from behind. It was Lucy, our mail room girl.

“Shit. I’m sorry. I was feeling lazy … and ummm …” I trailed off as I realized I was wearing one of my shorter shirts, and my jeans and underpants had slid down to reveal my ass crack.

“Don’t worry about. I’ll get the door for you.”

I stepped aside, and she moved her hip (and her ID card) to the reader to unlock the door for us. I opened the door after it clicked as she was carrying a bunch of packages to deliver.

We exchanged some pleasantries and went our separate ways. Sitting down at my desk I was a little flustered and disappointed. Lucy was (at least in my opinion) the cutest girl in our office, and I had just embarrassed myself in front of her.

She was about 5’4″, had a slightly freckled mouse-like face, and brown shoulder length hair. For whatever reason, she wore the same outfit most days to work: tightish black pants which served to highlight her nice butt, and a reasonably tight white button up shirt behind which seemed to be a small perky set of breasts.

We had more beautiful women in the office, that’s for sure, but she was so damned cute and very personable. Because she seemed obtainable, I always clammed up when talking to her, whereas I got along swimmingly with all the beautiful women I had zero chance with.

I stumbled through the day, and finally made it through to 5pm. Being a Friday, there was usually a crowd of 20-somethings from our office in a bar a few blocks away.

Today, though, there was no-one from our company there. Figuring maybe I was a little early, I grabbed a drink, sat at table, and idly watched some sports on TV while I waited.

During my second beer, I felt a hand on my arm. I look over, and it’s Lucy.

I offer to buy her a drink (a wine), and we start chatting. Probably thanks to the beers, her cheery personality, and the lack of other people around us, we actually have a good conversation.

After a bit, I notice that half an hour has passed. Fearing that someone from work will turn up and take her attention away from me, I suggest that we go out for dinner as I’m “starving”.

This, I might add, is a bold move for me. I was 26 at the time, and still a virgin. In fact, I hadn’t even been on a real date to this point.

Dinner goes well. We’re still having a great time, and we click. She’s a few years younger than me, funny, sassy, smart and knowledgeable about many things.

At the end of the meal, I offer to pay. Lucy turns down my offer, saying she would only accept a guy paying if it was a “first date”, at which point I turn bright shade of red.

Afterwards we go out for one more drink. At this point, I’m not sure how we should wrap up the night. It’s clearly going well, she’s single — she broke up with her ex about 6 months ago — but I’m at a complete loss about what to do.

Finally she yawns, and I offer to take her home for some BS safety reason despite the fact she lives in safe part of the city on the opposite side of town.

Despite the late hour, and the long wait time between trains, we somehow decide this would be a good way for her to get home. I wanted to hail a taxi, but thought it would be too intimate for a not-date. Plus I didn’t want the taxi driver to overhear our conversation — not that we were talking dirty or anything.

The upside was that we got to keep on a talking. Finally after about an hour, we get to the steps of her building.

She asks if I want to come upstairs for coffee. Like a chump who doesn’t want to have the balls to go on a date, less alone lose his virginity, I decline, saying that it’s late and I need to be in some condition to make to make it to my tennis competition in the late morning.

This despite my head, heart and alcohol begging me to do otherwise.

Lucy sits with me on the stairs to her building as we wait for the taxi I booked to show up. During this time we probably could’ve gone to Africa, found some coffee beans, processed them, brought them back, and had a nice cup of Joe.

As I get up to get into the taxi, she says goodbye and gives me a quick peck on the cheek. Unsure of what to do, I run to the taxi and shout goodbye.

When I get home, my head is pounding slightly from the remaining alcohol. I’m buzzed about how well we got along, and a little bummed about how it ended. In a moment of blind bravery, I SMS her if she’s free one day this weekend for a proper date.

After hitting send, it feels as though my heart is about to pound its way out of my chest. Afraid of a “no”, I turn the phone off, put it face down in an inconvenient location, and take a quick shower.

Still too afraid to see what the answer might be, I try to go to sleep. After about half an hour of tossing and turning, I give up, and check my phone.

“Yes, of course.”

The timestamp: almost 50 minutes ago. Oh, fuck.

I quickly text back, asking if she’s awake and making up some lame excuse about showering, washing clothes and packing tennis gear.

We set our date for Saturday night, and again it goes well. At some point during dinner (Italian, if I remember correctly), I admit that I’ve never been on a date before.

This is also one of the first times I’ve seen her wearing something other than her usual work attire. As it’s late spring, she wore a nice sundress.

At some point as we’re walking from dinner to a bar, she initiates hand holding. Expecting her hand to clammy, I’m surprised to find it quite dry. I struggle to think of the last time I held someone’s hand since I stopped holding onto my parents.

Again, I take her home — this time in a taxi, and this time I say yes to coffee, before admitting that I dislike coffee and fixing myself a tea instead.

Upstairs in her apartment, I’m completely at a loss about what to do. While the dinner and bar portion of the date was new territory for me, it was still happening in familiar locations with familiar rules.

What am I to do in a woman’s apartment, alone, close to midnight? After a brief tour — she lived in a 2 bedroom place, but her roommate was almost always over at her boyfriend’s — I sit down on the couch.

“Cheers to good first date,” I say. “Well, at least, I think it was good, well I had a good time, and I hope you did too.”

We clink our cups, and sensing my palpable nervousness at this point, she turns on the TV. Unable to find something good on at this hour, she puts the TV on mute and suggests I pick something out of her extensive CD collection.

A little overwhelmed, I let her choose. She picks a jazz compilation CD. I start a conversation about how awful late night TV. While we’re reminiscing about the TV of our youth, she kisses me on the lips.

In the middle of my best deer in the headlights impersonation, she tilts my head to a slight angle, and we begin to make out.

Trying to process the sensations — the feel of her lips, the texture of tongue, the oddness of exchanging saliva — while trying to keep up with her, and not be a complete fool nearly overloaded my little brain.

At some point she told me to slow down with my tongue as it was “not a joust”, but I struggled against the urge to flick her tongue a million times per second.

After taking a breather, I attempted to restart our make out session, but without tilting my head a little, we rather comically bump noses and teeth.

Over the coming week, we go on a date every single night. Each night, we’d end up at her place making out, and slowly we’d get more handsy, with her making the first move most of the time.

About a week in, we were making out in the kitchen with me pinning her against the wall. She grabs my hand and places it on her bra. Until this point, I hadn’t realized how much padding a bra can have and, presumably, how much visual heft it can add to someone’s breasts.

Not long later, she moves my hand from above the bra to underneath. We stop kissing, as I hold one of her A cup globes for the first time, and she bites her lips, lighting a fire in my loins.

Like with our first French kiss, I move in hard and fast on her globe, and Lucy has to tell me to slow down. Nipples, I learn, are sensitive things.

I start to tease her nipple, drawing ever smaller circles with my index finger. The lip bite returns, and she begins to moan — a sound I had only previously heard when I kissed her neck. My time with her breasts is cut short with the oven timer rings.

We finish fixing up dinner, and eat. Afterwards we sit down to watch some TV, both of use squeezed up on the chaise. I move a little towards the center of the chaise when Lucy disappears for a bathroom break.

On return, she crawls into the slight V between my legs so she can use me as a couch to watch television. For the first time since we’ve started dating, my cock (through my jeans, of course) is pressed firmly against her. During all our kissing sessions I was always conscious of keeping my junk away from her body.

Even though her body was pressed firmly against my dick, it wasn’t much of an issue at first. Thanks to all of our dates ending late, I was pretty tired and I drifted off for a short nap.

Something happened on the show we were watching, and Lucy moved in a startled fashion. Her jolt woke me up. As I was coming to, whatever was happening on the screen caused her to move and wiggle more than she had previously.

This began to have an effect on my member. Perhaps sensing this, she began to wiggle and squirm more, and for no apparent reason. With my hardening cock poking slightly into her back, I tried to reposition myself so there was a little less back-to-member contact.

“You don’t need to move, I’m perfectly comfortable,” she said.

“Oh, ummm, it’s not …” I stammered back.

“Sorry, am I making you uncomfortable?” she asked, turning around with a wry little smile.

“A little.”

She turned around to straddle me. “Is this better?” she asked before she started kissing me deeply, and grinding against me.

My member got harder and harder, and our breathing began more ragged as the friction through our jeans began to turn the heat up.

Initially my dick was pointing down, lying on my balls and facing in the same direction as my legs. So while things were definitely pleasurable, it was manageable.

Somehow during our dry humping, my dick got free and stood up. Through her black pants, and my underwear and jeans, she was now grinding on my frenulum and it was quickly sending me closer to the edge.

I pulled out of kiss, the grinding stopped, and things began to settle down, but Lucy leant in to continue. Unsure how to take a longer pause without admitting that I was really close to cumming, we continued dry humping.

Her up and down motion against my cock, the feeling of the soft fabric of my undergarments, and the heat of my own skin against the head of my member all put me ridiculously close to point of no return.

I started trying to count sheep, concentrate on the TV, remember my credit card numbers. Anything.

But they didn’t help.

Over the edge I went. I tried to hold back, but wave after wave of cum spilled out. I felt the wetness spread across my underwear, onto my pubes, and onto my skin.

The sweet pleasure of ejaculation was replaced very quickly by shame: I had come after only a few minutes of rubbing. Maybe it was only a minute. It felt like an instant.

To cover my shame, I tried kissing more passionately, but I think I just ended up flicking her tongue a thousand times a second.

Lucy pulled away and asked if something was wrong.

“Ummm …. I might’ve become … a … little too excited.” I looked away.

“Did you come?” she asked.

I didn’t answer.

“Oh my god … that’s hot.” She felt my shrinking member through my jeans, and rubbed it. “I think I’m going to join you.”

As I looked at her quizzically, she shifted across so that she now straddling my right leg. She started kissing me slowly and passionately as she began grinding and riding my leg.

Emboldened — and very happy that she hadn’t kicked me out for coming so quickly — I grabbed her butt cheeks as she continued to grind away.

As her breathing and grinding motion became more haphazard, we stop French kissing and she rested her head on the nape of my shoulder, occasionally licking and kissing me there. And then it all stopped with a soft moan and the slightest of whimpers.

While she basked in the afterglow of our session, I try to process everything that’s happened. On the one hand I’m elated and satisfied, but the wetness in my pants caused an overriding feeling shame.

“I think we better clean up,” Lucy said, breaking me out of my thoughts.

Despite my best efforts, it’s impossible to fully clean up the mess, and I go home feeling both satisfied and insecure.

Source: reddit.com/r/gonewildstories/comments/qua13l/kinda_losing_my_virginity_at_26_mf