Our [f]irst ti[m]e…

(I’m sorry this ended up long…and isn’t done yet. The real action takes place after the ***….more to come!)

My happy marriage had just blown up, and I had my daughter for our first visitation. I posted a pic of us on Facebook, and it got lots of likes lol. Out of the blue, I get a Facebook message from Samantha (not her real name), a former coworker, remarking on how much my kid had grown. I hadn’t seen her since she had left my company about 6 months prior, after two years of working together…friendly, maybe a bit flirty, but never thought anything of it. I’d teasingly threaten to spank her, then watch her blush, but I was happily married when we worked together.

That first message led to lots of talking, and we finally meet up for a beer after work one afternoon a few weeks later. She’s working for an airline now, and dressed like it, in snug black dress slacks that showed off her retired-ballerina bubble butt and a gorgeous red blouse, emphasizing but not outright showing off her smallish but always incredible cleavage. The long, brown hair she had when we worked together is gone, she’s now sporting a short bob, but it looks great on her. She’s still my adorkably cute friend with the Coke-bottle glasses and slight overbite, but undeniably sexy. But this wasn’t much more than smiling and giggling and catch-up talk. Yet, as I watched her walk out that day, I knew somehow, she was going to be mine.

That first drink led to her asking me to come over and help her build a swing set for her daughter. So I packed up a tool bag and headed over. She was dressed to work outside in the heat, in a white tank top, light blue basketball shorts, and sneakers. She was only about 5’5”, but had incredibly long arms and legs, emphasized by this outfit. We were goofing and joking as we worked, sweat pouring off us. We got to a spot where we needed a tool I hadn’t brought, so she went over to her shed, where she had the tool chests she had inherited from her dad. She started searching through the drawers, then did something I’ve NEVER seen in person. She decided to try the bottom drawer…and to do it, she squatted. But it wasn’t a wide “catcher’s” squat…it was what I’ve since come to call her “ballerina squat”. She had her feet together, then came straight down, in the deepest plié I’ve ever seen. That drawer didn’t have the tool she was looking for, so she stood up then bent over at the waist to get into a slightly higher one. I couldn’t pass this up, so I swatted her.

“Just making good on all those threats,” I said, with a big grin. “I had an irresistible opportunity.”

“Really? Oh my God!” But she was laughing.

“Yes, really…and if the opportunity presents itself again, it might happen again.”

“Oh…OK,” with an eye roll and a giggle…that to me sounded like “Bring It On!” And I did get her a couple more times that day…and happened to catch an unexpected view up those shorts, of some very pretty panties, with a wet spot…but was it desire, or sweat???

We went out together again a while later, this time on a weekend, at night, but still just as friends. We drank quite a few beers, and sang a bunch of songs. At 43, I knew a lot of songs from a lot of eras, but this cute little 27-year-old could not only sing like a bird, but she knew some songs I didn’t. I was surprised…pleasantly so. But, I took her home, and we stopped in the parking lot of the school near her house just to talk for a bit. I could tell there was chemistry…there always had been. I went to hug her goodnight, and was just overcome with the urge to kiss her…so I did…sweetly and gently at first, testing the waters. Her response and encouragement jacked up the heat, so I tried my tongue. I got incredible reciprocation, but I vividly understood how small her mouth actually was.

“We’ve always had a lot of chemistry, haven’t we?” I ventured once I came up for air.

“Possibly,” as she giggled and blushed.

“I always enjoyed the view when we worked together…and I wasn’t the only one. Never thought it’d be me. I was too happily married,” I confessed. Then, I wrapped my arms around her narrow waist and kissed her again. But this time, I slid both hands down and grabbed a double handful of her ass. I remember being in awe of how perfectly it filled my hands. And how both soft and rock-solid muscular it was. “God, I’ve wanted to do that for a long time…never thought it would happen…definitely worth the wait!” I took her home, and drove home wound up, and hopeful.

This led to a time when we would spend all day every workday talking to each other on the phone as we worked (God bless Bluetooth!) We had always been good friends, and we talked about every subject under the sun, for hours. During one of these phone conversations, I confronted the change in our dynamic. (And yes, we actually talk like this…it may not be verbatim, but it captures the essence of the convo)

“We need to address the elephant in the room, so to speak.”

“What would that be?” she asked me with exaggerated innocence.

“Well…I kissed you the other night…and you kissed me back. There’s always been an attraction between us. Hell, I remember catching you looking at me in the office one day a couple years ago like I was a piece of meat and you were a starving lioness.”

“I have NO idea what you’re talking about,” she insisted while laughing.

“Well…the prospect of sex between us has just become a reality instead of a fantasy, has it not?”

“Possibly.”

“Is it a prospect you’d like to explore?”

“Maybe.” (Yes, this girl speaks in code lol)

“OK…so can I ask your birth control status then?”

“I haven’t been on anything since the shot a couple years ago. Haven’t needed it,” with another giggle. “Do you want me to make an appointment?” I knew for sure I was in!

“Ok, I’m now assuming a yes,” I said. “But only once you’re sure. Your pants don’t come all the way off until you take them off…or you tell me to.”

In the meantime, we got together every chance we could. She’d call me late at night and ask me to come over after her kid crashed, which led to some epic makeout sessions, including one where she was in a tank top and panties, and I was just in my boxer briefs. Hands were wandering, temperature was rising, and all signs looked to be that this was the night. I was on top of her, hard as I’d been in years, and I could feel a definite heat between her legs. “It’s still your call, when the time is right,” I said, coming up out of a kiss. She looked at me, both aroused and surprised.

“I didn’t think we were stopping,” she said.

“Only if that’s your choice. You have the control in this. It’s 100% your call.”

“You won’t be mad if I say I’m still not quite ready tonight?” she asked me, clearly not expecting this.

“I’d have to be crazy to make it your call and then get mad if you’re not ready to make that call,” I said chuckling. I laid on my back and pulled her up on top of me, straddling me across my hips. “I’m not calling you a sure thing, but I’m fairly certain it will eventually happen. But when is not my decision. I’d rather accept a hesitant “no” then try to force a reluctant “yes”. Now, having said that…you’ve been teasing me with your tits for 3 years now. Any chance I can talk you out of your shirt tonight?”

“Sure,” she grinned and giggled, and pulled her tank top over her head, finally revealing her gorgeous, perky round boobs, with their pink nipples standing firmly out of their crinkled areolas. I had to reach up and roll each nipple in my fingers, then pulled her closer where I could kiss and suck on each one briefly.

“Well worth the wait. You have beautiful, boobs my dear. I suspected, but now I know,” then I pulled her in for a steamy kiss. “Now…I’d like to sleep next to you tonight, preferably with my arm wrapped around you, maybe between those gorgeous boobs. Maybe I’ll grab a handful of one. But let’s get some sleep.”

***

The very next night, Samantha invited me over again. Again, she was wearing a tank top, this time with some cute pink terry cloth shorts that absolutely hugged her ass and showed off her legs to great effect. We snuggled into the couch and watched TV…ostensibly. I couldn’t begin to tell you what was on. After a few minutes, she asked me if I wanted to join her upstairs. I quickly agreed. Once we got to her bedroom, we both started stripping down. I was quickly down to my boxer briefs again, and she lost her shorts and tank top. We crawled in, kissed and held each other, then came up for air. “You can take those off me.” The only thing she had left on was her panties.

“So, tonight’s the night, eh?”

“Yep…if you want.”

“If I want?” I rolled back a bit and showed her the bulge in my underwear. “What do you think?”

“Maybe.”

“I think I may smack that smart ass of yours again. Bare, this time.” She smiled, stuck out her tongue, and arched back to raise her hips to allow me to slide off her panties. Which revealed the prettiest shaved-smooth little pussy I’ve ever seen. “Bald? I like it.”

“Ballet habit, “ she told me with a laugh. “Ever since it came in I’ve shaved. Leotards. Can’t have hair poking through…or showing! Eww!”

“I can see where that might be an issue,” I deadpanned. As I came back up from her feet, I knew I needed a closer look, and soon, a taste.

I worked my way up her legs from her knees, alternating kisses higher and higher up each thigh. I still didn’t dive right in…I kissed around her pubic bone, then licked straight down her slit, without pushing in, just the outer lips. Then, I increased the pressure as I came back up, penetrating a bit, really tasting her for the first time (DELICIOUS!) Then, I flicked my tongue upward over her clit, kissed it, then focused a bit. As I began that, I inserted a finger…finally getting inside her. Wow, was she tight. Wet as hell, but incredibly tight. Her grip on one finger was something I’ve never experienced before or since. I forced a second finger in, kept going, but there was no way a third was going in. Which I knew was about to be a potential issue.

I know me. Cue the eyerolls and doubt, but I know for sure that I’m not little. Not hugely long…I’m about 7” or so. But I know my girth…3 fingers wide…which measures out to 2.25”. Yes, over 6” in circumference. And yes, I’ve measured it. If I couldn’t get a third finger inside Samantha, this might all be for naught. But I had a secret weapon.

I shave using coconut oil instead of shaving cream. It’s excellent for the skin. So, my travel kit had a small jar in it. It also happens to be an excellent lube. So I jumped up and pulled off my underwear, grabbed my jar, took a dollop, and kept working Samantha over. But I still couldn’t get the 3rd finger inside her. I thought she was as ready as I could get her, so after a bit I asked her if she was ready. She just nodded.

I was on top of her, wanting nothing more than to finish what we started, but doubting it would be able to happen. I tried over and over. I pushed at her, but I kept glancing off sideways. I asked her to flip over to attempt a doggy entry…and FINALLY got a full, naked view of her glorious ass, and her pussy glistening underneath. Between her own juices and the coconut oil, even her tight little asshole was covered in slippery shiny stuff. She looked back at me with a concerned look on her face. But the rear attempt wasn’t any better, through numerous attempts. I could not penetrate her. She was just too tight. I was out of breath. So, I spanked her ass a couple times, just hard enough to get a good smack and leave a faint pink mark, then I flopped next to her.

I found her with a worried look on her face. I kissed her, and said “Little Pig, Little Pig, let me in!”

“I’m sorry…I want to…I really do.”

“I know honey…you’ve been too wet not to. I can’t believe you’re apologizing for having a tight pussy. It’s not like we’re in a huge hurry, right?” She laughed, then hugged me. “I’ll get you, my pretty…it will just take patience and persistence. I’ve waited this long, what’s a few more minutes? This isn’t the first time this has happened.”

“I bet not,” she said with a wry smile.

“What do you mean?”

“I kinda felt you last night, but seeing and feeling how big you are is…Holy Crap!”

I just laughed and said, “I’ve never failed yet. But seriously? I saw your ex when he showed up at work a couple years ago. He’s a large dude.”

“Not everywhere,” with a laugh, “Just like you aren’t small everywhere.” She sat up next to me, down by my hip, and said, “I’m sorry…again…but I know something you might like.”

“Oh really?”

“Yeah.” She then reached her hand out to my cock, stroked it 2 or 3 times, then struck like a snake. She took all of me into her tiny little mouth like it was nothing. After kissing her, I had no clue how she could. But she blew me like her life depended on it. She was just going crazy. Just to see, I pushed her head a bit…and her lips hit my body…a first! After proving too big to immediately be able to fuck her, I was thunderstruck she could deep-throat me this easily.

“You are one skilled cocksucker, my dear. I think you like it.” All I got was a muffled “Mmmmh?” while she kept it up. “I’m not gonna last long at this rate. You want me to cum in your mouth?”

“Mmmhmm” without losing rhythm. I took her at her mumble, and quit trying to hold back. I felt the pressure build, and that feeling of an imminent release. “I’m gonna cum babe! It’s all yours!” With that, I pumped out rope after rope, but I never saw them. She took and swallowed every bit, and kept stroking me, milking every last drop. Finally, she sat back up, with the biggest, most self-satisfied smile I’ve ever seen on anyone.

“You like?” she asked me.

“You think? You swallowed all the evidence, but I think I proved it.”

“Maybe.” Her and her code. “I just wanted to make sure you were happy.”

“Happy? Why shouldn’t I be happy? I have a gorgeous naked girl who just sucked my brains out next to me. You didn’t tell me you were a sword swallower.”

“I have a few skills.”

“A few skills…judging by that grin, I think you enjoyed that as much as me.” She curled up next me, still grinning. “You willing to do a bit more of that and go for a second attempt at knocking down your walls in a little bit? I need a few minutes to recover from that!”

“Sure,” she said thru a giggle, then kissed me. “I’m glad I could do something right.”

“Samantha, you did nothing wrong.” I kissed her, and just held her for a few minutes. Then, my hands started to wander a bit, down her back, over her hip, down the outside of her thigh, back up the inside, to her ass, and finally her pussy…and it was drowned. “You really DID like blowing me, judging by how wet you still are. Ready for a second try? Since you like it so much, why don’t you suck me back hard?” She sat up without a word, still smiling, and grabbed my already again semi-rigid cock. This time, she attacked with less urgency, licking and stroking me before engulfing my whole increasing-by-the moment length once again. “God, you are good at that!” She increased her tempo, then varied it. I grabbed her by the back of the head, and pushed her down into a deep-throat to see if I could again. “I think you’d be perfectly happy to swallow another load, but you’re not getting off that easy. Get on your knees.” She complied, again without a word.

​

Once again, I’m looking at a gorgeous ass, bent over. I’m rock hard. I try again. There was just a bit of resistance, but then I finally slid in…with an audible “Oh” from her. I didn’t push more than halfway in right away…I was just glad I got in. But then I thrusted, feeling how tight but also wet she was. Her grip on me was amazing. Even the girls I struggled with the first time previously didn’t grip like she did. I gave her my entire length. She jumped a bit on the thrust, but nothing verbal. “I knew you couldn’t hold out forever,” with a chuckle, and I could actually feel her laugh just a bit. I pulled back almost out, then pushed back in. “You ready to go for this?” She just nodded.

​

I picked up my speed. I spanked her ass, hard this time, but still no words from her. I was determined to fuck her like my life depended on it. The sound of me slapping into her and the warm musky smell of us combined for an amazing sensory mix. I varied the tempo. I reached my hand around her hip and found her clit when I slowed down. At one point, I just filled her with a thrust, held her there, and played with her clit. That got a bit of wiggle reaction from her, but no noise. Time to go for it.

​

I grabbed a hip in each hand, astounded briefly at their perfect fit, and stuffed her hard and deep. Then I accelerated. Faster, harder, deeper…I pounded her. The slapping sound got more intense, and there was a wet slurp accompanying every thrust. Even second time up, her tightness was gonna get me. “I’m not gonna last much longer. You ready?” Again, just a nod. “I’m gonna cum inside you babe!” As I felt the pressure rise again, just before I fired my first shot, I both saw and felt her cum. Her asshole was pulsing open and closed 3 or 4 times, as she clamped down and released on me, milking me with her pussy, almost just like that blowjob earlier. She looked back at me with a puzzled, surprised look on her face.

​

“Well, I know you didn’t fake THAT orgasm,” I said, with a laugh.

​

“Is that what that was?”

​

“Wait…WHAT? Nobody’s ever made you cum before? I mean, it’s not like you’re a tough nut to crack.” She just shook her head. “Well, they were selfish, clueless idiots. You had to know it’s not hard to make yourself cum, you know, flying solo,” I said with a grin.

​

She just shook her head, and said quietly, “I never have.’

​

“Made yourself cum? Wow…” I was feeling pretty good about myself.

​

“Flown solo,” she said, almost sheepishly.

​

I was incredulous. “You’ve never masturbated?” She just shook her head. “Wow…that’s a new one to me.” I pulled her close and kissed her.

​

“Well, that was a new one to me,” she said with a shy smile. I kissed her again, and an idea crossed my mind.

​

“Well, we need to make sure it wasn’t a fluke.”

​

“What do you mean?”

(END PART 1)

Source: reddit.com/r/gonewildstories/comments/dz3d1r/our_first_time