Thirty Five Years Late

There are times it feels like it happened to someone else, but I was once the shyest guy you could have ever found in my school years. I hardly ever talked with girls, from my first crush in 6th grade on through my Senior Year, and through college as well. I went into the workforce a virgin, and for a while, it looked like there was no end in sight to that.

Around the time I turned 30, I realized that putting all my energy into my job and my dick into my hand were not satisfying me any more. I wanted companionship, anywhere from just someone to finally fuck me, to a life partner, so I knew I had to break through my shyness, to get my life on track. Can't even call it getting back on track, since it had never been on track, ever.

Maybe someday I'll tell the story of how I overcame that shyness, and the women who helped me do it, but for this part of my life story, suffice it to say that I did finally lose my virginity, dated several women and then met my wife and got married, and was happy.

For a while.

Then the marriage gradually fell apart, we decided to divorce and I was single again at 52. We'd had no kids, so the split was relatively easy, as divorces go. A lot easier than the last few years of the marriage, at least.

In a lot of ways, I felt like I was back where I was when I turned 30. I was back to having just my job in my life, and took to more traveling assignments. The marriage and its failure had damaged my confidence in a lot of ways, and the prospect of dating again had me feeling scared. Again. I was determined to fight against that feeling, and was beginning to date again, but wasn't clicking with any of the women I met. First date city.

And then one day I was reminded of an incident that had happened in High School back in Maine, when I received a Facebook friend request from a classmate from that school. In my senior year, Kimmy Cartwright had asked me to ask her friend Jane Wallace to Senior Prom, saying that Jane liked me, and wanted to go with me even though we'd never really talked much. I managed to nervously ask Jane, but then doubts crept into my head. Was I just being set up for a big joke at my expense? I couldn't figure out any other reason for it happening. My shyness listened to the doubts, and I cancelled on Jane, and didn't go to Prom.

And that, my friends, was the closest I got to a date before 30. Sad and pathetic, right? I considered it part of a past I'd overcome, and hadn't thought about it in years. I hadn't even told my ex-wife about it.

We all graduated soon after, and went our separate ways.

I had not talked to either Kimmy or Jane since then. Hadn't seen either of them at reunions, before I moved away from the area fifteen years ago, winding up in Seattle, where I met my ex.

And now Kimmy was asking to be a Facebook friend? I thought about rejecting the request because of that incident in high school, but realized that was my old fears talking, and I didn't want to give into that again. What could be the harm in saying "Hi" to someone now? I had quite a few other Facebook friends from the same school.

So, I accepted Kimmy's request, and we got caught up with each other's lives through a series of messages. She was married, with three kids, lived in western New York.. I got a "Sorry" regarding my divorce. Both of us had moved away from our hometown in Maine. And when I mentioned that I'd recently had lunch with a couple of friends from our class when I'd been in our hometown visiting my parents, she mentioned that the only one of our classmates she'd kept in touch with over the years was Jane. Who it turned out was on Facebook, still listed as Jane Wallace. Her profile picture was just what I thought a 52-year-old Jane would look like, and the smile was exactly as I'd remembered it. So I sent her a friend request.

Along with the request, I sent a private message saying, "I don't know if you remember it or not, or have thought about it since, but I feel like I owe you both an apology and explanation for cancelling on you for the prom. I let my shyness convince me that I was getting set up for a joke, and ran away from the risk. I should have had the courage to trust you. I'm sorry I didn't, and sorry if that hurt you."

I think that was already more words than I'd exchanged with her in all of high school. I felt like a very old weight, that I'd gotten so used to that it no longer registered, had been lifted from my shoulders. I didn't care whether I got forgiven, I just needed to do it for myself. Kind of like an alcoholic making amends, doing it to heal himself.

I was surprised when Jane accepted the friend request, and her response to my message only addressed the matter with "I wondered why you did that." The rest of her message was talking about things she'd seen among recent posts on my profile. It turned out we both have an interest in history, and progressive political views. She also had moved away from home, and was now a single mom living outside Chicago.

We struck up an occasional correspondence, sometimes as comments to each other's posts, sometimes privately. The prom didn't come up again. Jane was mom to a 15-year-old daughter, conceived by sperm donor. Given the math, she'd had Amelia at 38. A biological-clock baby, it seemed clear.

We probably averaged a dozen messages to each other per month after the first month, light-hearted stuff, you know how Facebook is.

About six months later, I got notified by my job that I would be travelling to Chicago for about six weeks, maybe more.

"Would you like to get together for dinner while I'm in town?" I sent to her, letting her know where I'd be working, and the hotel I'd be staying at.

"Are you asking me on another date? How do I know you won't cancel on me again?" came her reply, with a little smiley-face to make it clear she was joking.

I responded, "Well, I actually still owe you for cancelling the original date, from high school. No expectations, just two old classmates eating together. Bring your daughter along if that will make you more comfortable. My treat. How about it? Save me from another dinner alone on the road?"

A day later, she responded, "Okay, I'll do it. How's Tuesday the 19th sound? I know a nice Thai place that's about midway between my work and your customer, and it's usually pretty quiet so we can talk. I'll make reservations for 7 PM?" She included her mobile number, in case I needed it. I added her to my phone's contacts.

"Kewl. See you there," and I sent my number.

At 7 PM that night, I entered the Jade Thai restaurant, and spotted Jane immediately, along with her 15-year-old daughter Amelia, whose pictures I'd also seen. "Hello ladies," I said, as Jane spotted me approaching the table. I turned to look at her daughter and said, "You must be Amelia. I'm Jake Kimball." I shook Amelia's hand, but Jane got up and surprised me with both a hug and a peck on the cheek.

Jane looked elegant, in a gray satiny dress that reached her knees, and showed only a little bit of cleavage at the neckline. She was more full-bodied than High School, when she'd been a little thin. I'd long since learned that many of the girls who were curviest in High School tended to only get bigger. The modest weight gain looked very good on her now. I don't know if she had chosen her dress because her daughter was along, but she still looked gorgeous. In my thoughts, I slapped myself across the back of my head for a fool. If only...

"Hiya, boyfriend," she teased. "35 years late for a date? Gotta call the Guinness Book of World Records!" We laughed, and I pushed her chair in as she sat again before seating myself and picking up a menu.

My skin where she'd kissed me still tingled.

I know we ordered food, but I totally can't remember what dishes they were. That's how much of my attention was focused on Jane. Her smile, the mischief in her blue eyes, the little bit of cleavage she showed, everything about her, drew me in. I felt none of my 18-year-old nerves, which thrilled me.

While we were waiting for our food to arrive, Amelia asked, "What was that 35-year-late comment? Did the two of you date in High School?"

I looked at Jane and said, "You didn't tell her?"

She reached to touch my hand, and said, "I wasn't sure you'd want me to share that." More tingles.

"I'm long past the point of being embarrassed by it anymore," I replied. "You see, Amelia, I was terribly shy when I was your age and for many years after that. When I was 18, your mom's friend Kim got me to ask your mom out to Prom, but then I got scared and cancelled. We hadn't dated before that, really hadn't even talked to each other very much, and didn't talk again after Prom and graduation until we reconnected on Facebook a few months ago. So tonight is kind of the completion of my asking your mom out that one time back then. It's not Prom, but it's nice to be here with you both."

"You don't seem shy now," she said.

"I try my best not to be." I joked. "People change, especially when they want to. And I eventually wanted to stop being shy enough to figure out how to overcome it."

Our food arrived, and we started eating, trying to keep the conversation from straying into areas that weren't appropriate for Amelia, but Jane kept slipping little risqué comments in here and there. My head was spinning a little, with how flirtatious she was being with me. By the time the check came, Amelia actually jokingly said to her mom, "Get a room!"

I had my wallet out to get my credit card, and slipped one of my two hotel key cards out, too, and flipped it onto the table, saying, "Already have one, thanks." Amelia's eyes bugged out and she blushed a deep pink, while Jane and I laughed.

When the waiter had run my card and brought back my receipt, Amelia got up to put her coat on. Jane waited until Amelia's back was turned, picked up that key card, looked me straight in the eyes, and paused with the card just over her purse. I nodded, and she slipped the card in. I felt my dick jump in my pants. Was this really happening?

I signed for the meal, slipped the receipt and my credit card back in my wallet, and put it in my back pocket and got up and grabbed my own coat. Just outside the restaurant's doors, Jane gave me another hug and kiss identical to her greeting, before she and Amelia headed to her car. It was around 9.

As soon as I got to my rental car, I texted her "Hilton Midtown Room 302. Tonight? Or tomorrow? The keycard expires Thursday when I check out before heading home for the weekend." I put my phone down and began the drive to my hotel. And picked up some rubbers at the hotel gift shop, before going up to my room.

A reply text came just as I opened my room's door with the second keycard. "Tonight. Expect me around 10:30. XOXO." It was now 9:30.

I washed up, brushed my teeth, dropped the condoms into the nightstand drawer and waited, a little nervously. But only a little.

At 10:25, she unlocked the door herself, and came in, dropping the card by the coffeemaker, and a small overnight bag next to my suitcase. I greeted her with a kiss, then a long hug, stepped back, held her hands and said, "Now I'm really sorry I was so scared back in High School. If you were half as sexy then as you are now, my heart would have been a goner."

She looked sad in response to that. "There's a couple good reasons not to keep having regrets about that, Jake," she began, then paused. "The first is, and it's hard for me to admit this, but Kimmy and I WERE trying to play a joke on you back then. I was supposed to kiss Mike Dunbar right in front of you before the end of the night, and leave with him. It was his idea, but Kimmy and I both thought it would be funny. We made you believe that Mike and I had broken up, which is why I needed a Prom Date, but we really hadn't. I'm so sorry. Your instincts were right. We were such immature bitches back then. You weren't the one who needed to apologize, I was. Can you forgive me?"

I should have been stunned, should have been angry, but wasn't. "That would have been the only time my instincts about a woman were right that whole decade, then. The fact of the matter is I sabotaged myself from fear way worse than you would have hurt me by kissing Dunbar." I realized something in that moment. "If I'd gone to the Prom, even if it ended as you said, maybe I would have gained some confidence and my time in college would have been different. So I do forgive you. And the other reason?"

"Like you just said, if you had gone to Prom, my life would probably be different, too. I don't think I'd have Amelia in my life if Prom had turned out any differently. It's turned out to be kind of a pivotal night for me. I wound up dating Mike for six more years, before I finally broke up with him. None of the guys who followed him worked out, and I finally decided to have Amelia on my own."

"But how would my going to Prom have changed that?" I asked.

"Because one of two things would have happened. If you were even half as charming then as you've been tonight, shy or not, 18-year-old me would have backed out of the joke and Mike would have been pissed, and we wouldn't have stayed together. Or, I'd have gone through with it, felt guilty, and been pissed at him for it, and again we'd have broken up. Only your cancelling kept us together. As it was, what ultimately broke us up was a few years later when he wanted me to trick one of his friends, in just about the same way we were going to trick you. I'd finally grown up, had gotten to feeling guilty about trying to trick you, but he hadn't grown up a bit, and I was just disgusted by it."

"And if you had broken up with him after Prom?" I asked.

"I don't know. I've had years to think about that night and how much my life's path pivoted around it, but none of the other paths I imagined led to Amelia, so I let go of them after she was born." She paused, stepped back into a hug, put her head on my chest, and said, quietly, "Even the ones that featured you in them." She leaned up for a kiss. "You featured in my what-ifs a lot in those years, Jake. And then you wonder if I even thought about you? But I like my life now, and wouldn't undo it for anything."

"We needed to take the paths we took," I agreed. "My ex used to say she wished she had met me when we were younger. At least before she started using my past shyness as a weapon against me during the arguments that eventually broke us apart. I always told her I wasn't ready for her then. The same is true with you. I wasn't nearly ready for a relationship at 18. Too shy. Certainly not charming then."

"I like the changes I see in you since then." She looked up into my eyes. Her blue eyes were sparkling with unshed tears. "And I'd love the chance to know the improved you better, and make up for trying to hurt you then. You say you weren't ready for me then. Think you're ready for me now?"

I leaned down to kiss her, softly at first, then opening my mouth to let my tongue glide along her lips. She opened her own lips, and our tongues met in the middle. I broke the kiss, and whispered, "That answer your question?"

She nodded twice, then moaned and dove for my mouth again, pushing her tongue into my mouth. I pulled her even closer, her soft breasts pressed into my ribs, as my cock filled, nestled between us. Feeling it against her, she slipped her left hand between us to stroke its length, while her right went to the back of my head, running her fingers through my hair.

Behind her, I felt for the zipper to her dress, and started lowering it down, so I could slip my hands under the fabric and touch the skin of her back. She stepped back, and let the dress fall to the floor. Underneath were panties and bra of nearly the same shade of gray as the dress. I could just make out a faint tracing of stretch marks across her flat abdomen, evidence of her motherhood. She was gorgeous, and I lost my breath for a moment. Porn talks about MILFs a lot, but never actually seems to show a woman with stretch marks, just older porn actresses who never seem to actually be moms. "Wow," was all I could say.

She smiled in response, reached for my shirt, and began unbuttoning it, saying "Okay, I've been wanting to do this all night." She untucked the shirt, and pushed it off of my body, then pulled the tshirt underneath off of my head, ran her hands over my pecks, before putting her arms over my shoulders and pressing her body against mine again and resumed kissing me, fiercely.

My hands went to her butt, which I massaged through her panties. She moaned. I skipped my fingers under the waistline, and squeezed bare skin, running my thumbs into the cleft and pulling her cheeks apart. She moaned louder into my mouth. I ran my right index finger along the crease, and under her to her perineum, which I massaged, before pushing further to the beginning of her labia. The position made it impossible to reach further than that.

She broke the kiss and whispered, "You definitely aren't shy any more." She reached her hand down to my belt, and began to undo it, then unbutton my pants and lowered its zipper. They fell to me knees, and she dropped down to hers, running her hand along my erection as she went. "This isn't shy either!" she giggled. She looked up and asked, "May I?"

"Oh, you expect me to say No at this point? I'd be insane." She pulled my boxers down, and my dick bounced out, just a little precum wetting the head. I kicked shoes and pants off, and used my toes to pull my socks off, too.

"Oh, hello, not-so-little-Jake," she said, before licking its head to capture the precum, then licked and sucked at the underside, working her way down to my balls, while pressing her thumb lightly against the frenulum, squeezing the shaft just under the head lightly. I was already moaning. My ex-wife hadn't liked giving head very much, and Jane could have taught a clinic. That was the last time I thought of my wife, putting all my focus on Jane and the pleasure I was feeling.

After licking all over both of my balls, she worked her way back up to the head, and stroked downward with her hand as her mouth sucked my cockhead into her mouth, swirling with her tongue. She began jacking the bottom half of my cock with her fingers, while engulfing the top half with her mouth, lips and tongue driving me crazy. It only took three minutes of this before I had to tell her "Jane, I'm real close." She only sucked harder and stroked faster in response. I exploded into her mouth, shot after shot of cream, and she took it all.

She stood up, running her hands from my dick up my abdomen, across my chest, over my collar bone, to put both hands along my face, and kissed me, and as soon as I opened my mouth to extend my tongue, she squirted the last of my cum into my mouth, and followed it up with her own tongue. I've never been bothered by my own taste, but had never had a woman do that to me, and found it really turned me on, causing my dick to regain its hardness almost immediately.

I reached behind Jane's back, and unfastened her bra, uncovering her B-cup breasts, then pushed my fingers under her panties by her hips and pushed them down her legs. I guided her towards the bed, and laid her down so her butt was right at the edge of the mattress. I grabbed one pillow to kneel on, and looked at her from between her legs, and asked "May I return the favor?"

"You better," she growled, putting her hand on the top of my head and pulling me towards her well-trimmed and very wet pussy. I kissed her there first, short, brief kisses followed by longer harder ones, before I started working all over her with my tongue, licking both the inner and outer lips, thrilling to her taste, encouraged by her moans. I pushed first one, then two fingers into her tunnel, before I even approached her clit, giving her hood a half-dozen soft licks, encouraging her clit to show itself. When it did, I gave it one long lick, and Jane's back arched.