The 39.25-Year-Old-Virgin

Author's note:

A re-edited and slightly improved version of the story originally submitted for Valentines 2021.

Made extra long in honor of Omenainen

~~~~

"What? I can't do that! I won't!"

"You don't want to take my virginity?" Lena looked down at herself. "I'm not attractive anymore?"

She looked almost the same as when we broke up four years before. Faint lines now fanned from the corners of her eyes and bracketed her mouth, but she had the same sweet face, thick chestnut hair and expressive dark eyes as when I saw her profile picture online. She might even have lost some weight, though it was hard to be sure the way her huge boobs dominated her frame.

"You're as beautiful as always," I said, "But didn't you say—"

"—that if I still wasn't married when I hit forty, you could take my virginity. Yes. Exactly."

"We'd just watched that movie! I thought you were joking. And your birthday's what... November 14? So that makes you... only 39. And a quarter. As of Sunday, I mean."

Lena shook her head, smiling. "I always liked how good you are with numbers." She picked up her wine from the coffee table. "Besides..." She took a gulp and made a face. "...what's the difference?"

My unease grew. Once we had arrived 17 minutes late for a play and Lena almost hyperventilated with panic. She was fastidious about anniversaries, appointments, and schedules. She also did not drink.

I took the wineglass from her and set it down.

"Lena, you're worrying me. Please tell me what's going on."

We had dated for half a year. Lena was smart, sweet-natured and pretty. She had a large patch of a light brown birthmark on the left side of her neck she was self-conscious about. It didn't bother me, but she wore turtle-necks and high collars and kept it caked with concealer.

She was shorter and rounder than I liked. Small wonder with the amount of food she cooked: the first time she invited me over for dinner she had prepared shish taouk, kofta, fattoush, kibbeh, and a syrup-drenched nammoura that nearly sent me into diabetic shock. All of it was superb, but enough to feed eight and clearly designed to impress.

And that was the problem. It took a while, but eventually I realized everything Lena did was orchestrated to show what a great wife she would be. Her careful choice of clothes, the lavish home-cooked banquets, her spotless, elegantly decorated home, how she theatrically doted over every baby we passed whenever we went out.

"Lena," I said, "In four years, we've exchanged nothing but happy birthday emails. Now out of nowhere you invite me over for one of your wonderful meals and suddenly want to go all the way?"

She shrugged, avoiding my eyes. "Well, why not? It's too late for a husband and kids. I've been saving myself all this time for nothing."

"Not for nothing. You stuck to your principles. What you believe in."

Her mouth tightened. "What my family believes in," she said. "Stay pure... no man will accept a defiled wife. Be a dutiful daughter. Stay at home until marriage."

"But you moved out and came here."

"Yes, when I was 33. I begged Pappy until he relented. He knew how much the job here meant to me. And I'm only two hours away."

"So now you're giving up? Maybe kids are out of the picture, but you're great, Lena. You'll meet someone."

Lena slowly shook her head, shoulders slumping.

"I'm tired of it. Tired of searching through the guys online and meeting the ones my parents find. Even when one seems promising and I do all the right things, it still fizzles out. Like it did with you. Except with everyone else, it usually ends the second I tell them I won't sleep with them. I'm tired of being the dutiful daughter. Doing everything expected of me. Time to live life my own way now. Whatever that is."

I didn't know what to say. It was a Lena I'd never seen. I guess a lot can change in four years.

Lena straightened and wet her lips. "So... will you stay the night?"

"Even if you're not married," I said, taking her hand, "you should do that with someone special."

"You are someone special. My first real boyfriend. The first guy I ever fooled around with. I've missed that. I've... missed you. Anyway, we already did everything else, so why not?"

~~~~

One night after dinner, two months after we started dating, we were sitting on Lena's couch watching some romantic comedy. When the credits rolled, she suddenly slid to her knees on the floor, unzipped me and took me in her mouth.

I was too shocked to protest. Seeing chaste Lena stroking and licking then bobbing with her sweet face and soft eyes looking up was surreal. Until that night, we had only kissed. She had refused even to let me touch her through her clothes.

Even more surprising, Lena was good. Very good. Yet she said she had never done that—or anything sexual—with anyone before.

She brought me to a rocketing orgasm, eagerly continuing her incredible technique even when I groaned I was coming, and swallowed the vast quantities I blasted down her throat.

I collapsed on the couch, trying to quiet my heart and regain my senses, wondering whether my prostate would ever recover.

Lena looked up, innocently. "Was that okay?"

Smoothing her hair, I laughed. "That was the best blowjob in the history of blowjobs, Lena. But what... why..."

She smiled sweetly. "I know it's hard for you that I'm saving myself. I know it's hard to wait. So, I think I should start relieving some of your frustrations."

Lena wore a satisfied little smile the rest of the evening. She shrugged coyly when I asked how she had learned such oral mastery.

But it was just another milestone on her internal "land a husband" Gantt chart. I assured her it wasn't expected or necessary, but she seemed to genuinely enjoy doing it and was so happy afterwards.

We were together every weekend. During the week Lena devoted herself to her job, working ridiculous hours, plus taking night courses to advance her career.

Every Friday she invited me for dinner, cooked a massive meal while refusing to let me help or clean up, then was under the table with my cock in her mouth before we'd even finished the baklava.

One night we were kissing when Lena guided my hand to her breast. Tentatively, I stroked and massaged her through her top, enjoying the weight and surprising firmness of her boobs for the first time. Soon Lena laid back, sighing while I caressed and squeezed, then giggled and stroked my head when I leaned close to nibble her ear and kiss her neck. Lena self-consciously pushed my head away if I went near her birthmark, so I kept to the other side of her neck.

After that, it was like being eighteen again, haltingly progressing through the bases. I sensed each act beyond the blowjobs were not tasks on Lena's schedule, so I let her lead, never pressuring, enjoying each step as her trust grew.

One evening as we made out, Lena stripped off her top and bra to expose her naked breasts. She sat, nervously waiting for a reaction as I gawked in the flickering light from the TV.

Lena's breasts were delightful: huge but perfectly shaped and suited to her curvy body. She had large dark aeroalas and thick nipples yearning for attention.

"Beautiful, Lena," I said. "You're lovely."

"Will you touch me?" Her eyes shone with eagerness.

Never a fan of huge tits, I became a fan of hers. Lena adored leaning back while we kissed, having me caress and massage her breasts, then move down to suckle gently while she held my head to her, sighing happily.

One Friday, she greeted me at her door wearing a skirt. Every other time she wore jeans or scratchy slacks. After the ritual of dinner, watching some show followed by one of her exquisite ball-draining blowjobs, Lena had her top off with me pleasuring her boobs when she guided my hand under her skirt.

"Remember my virginity," she breathed. "No fingers inside. Or anything else. Please?"

Moved by her trust in me, I gently caressed her soft folds. Lena's mouth fell open, her eyes darting with uncertainty at the new sensations, then she closed them as her chest rose and fell. I moved to kiss her neck while massaging one heavy breast with my free hand. Soon she was breathing fast as she cradled me. She stiffened when I moistened two fingers at her entrance then mewled with delight as I lightly swept them up across her clit then down again.

Her hips responded, instinctively lifting and swaying. I took one of her thick nipples into my mouth and increased the tempo between her legs, sensing her reactions to each caress. Lena's excitement rose higher and higher, gasping and sighing as I explored. Long minutes later, she clamped my head to her breast and froze as her orgasm bloomed and swept through her.

I held her until she opened her eyes. She stared in wonder.

"What... how did you... what did you do?"

I hugged her close. "Lena, was that the first time you had an orgasm?"

"Oh, my god. That's what that was?" She mopped her face with her hand and flopped against the back of the couch. "I see why it's so popular. Of course it was the first. You know you're the first man I've been with."

"So, you've never done it to yourself? Ever?"

"Eww, no! That's wrong. That's yucky."

"Oh, Lena. You've been missing out."

Two weeks later, Lena had progressed to letting me stick my head under her skirt and gently lick her to orgasm. She happily went topless and would remove her underwear when we played, but the skirt had to stay on.

The following week we were kissing and caressing with me naked and her wearing only her skirt. Soon we were laying in missionary position, her legs spread wide, humping each other with just her scratchy skirt separating us.

I raised up to fold the damn thing up around her waist. Lena looked between us, wide-eyed at my rampant cock pointing at her soaked and ready virgin pussy.

When she tried to cover herself with her skirt, I caught her hand.

"Do you trust me, Lena?"

She looked from my eyes to my threatening dick, then back. Her eyes searched mine for a moment before she sucked in both her lips and nodded.

Carefully, I lay on her and began sliding my dick back and forth through the slick folds of her pussy. The last time I did that I was eighteen, in my parent's basement rec room with my first girlfriend.

"Oh! Oh, that's nice," Lena breathed, rocking her hips. "That's so nice."

We kept that up, sawing between her pussy lips and across her clit, both of us becoming more and more passionate. I yearned to drive into her, not play such kid games, but I respected her wish. Besides, it was worth it to watch Lena's pleasure and growing excitement.

On one pass, her hips rose slightly too far while I was pushing forward. My dick reversed direction, sliding downward until it lodged just inside her entrance. We froze.

Lena's eyes were lidded, and her mouth hung open, gasping. Her hips bucked involuntarily, pushing me slightly deeper. The slick warmth of her pussy spread around the head of my dick.

I expected her to push me off onto the floor in horror. Instead, she spread her legs further, grabbed my ass and yanked me closer, her hips grinding and rocking.

I pulled back before she could force me into her. Reaching between us, I grasped the shaft of my dick to prevent her, and me, from sliding any deeper.

Lena was panting, lifting her hips, pushing on my ass, drunk with lust. I knew the hunger she felt. I shared it.

Carefully I probed back into her, the head just dipping into the mouth of her virgin passage, stopped by my hand from progressing deeper.

Lena groaned, again trying to force me all the way inside. I withdrew, then repeated the motion again and again, sliding no further than just the mouth of her opening. The slick heat of her against the over-sensitive head of my cock was intoxicating.

Little "oh! oh! oh!" breaths came from Lena, her eyes screwed shut in concentration. I alternated nudging at her entrance with sliding up and along her clit until Lena's breath caught. She shimmied her hips against me, then arched her back and came hard.

Her orgasm set off my own. I pulled out just in time to blast stream after stream of come across her skirt and up her exposed belly to the underside of her tits.

Lena looked dazed when at last she could focus her eyes. She looked at the come streaked up her tummy.

"You didn't do it," she breathed. "I wanted you to do it."

"No, you didn't. You were just caught in the moment. I know what it's like. I've been there lots of times."

"But not now? With me? You didn't want to with me?"

Pulling her close, I said, "More than anything, Lena. But you'd never forgive me. You'd never forgive yourself."

She blinked. "That was so powerful. I really wanted it. Didn't even care. I was thinking it was okay, it wouldn't count, no one would know... every excuse."

"Yup, that's how it goes. I knew you didn't mean it. If you change your mind about 'saving yourself,' it can't be in the heat of the moment like that."

After that, Lena became the most sexually experienced virgin in the world. She was game for everything except going all the way. One night, we entertained ourselves until three in the morning. I was exhausted, but Lena refused to let me stay the night because that would be "sleeping with a man."

Hearing her say that as she mopped come off herself with her skirt was incongruous. I suggested she might be taking terms a little too literally, but she shrugged it off.

Lena was the sweetest person I'd ever known. I never saw her get angry, except at herself, and her heartwarming, sunny outlook on things reminded me of women in 1950s movies.

Yet, dating her was frustrating, but not because of the sex. Fooling around with her kept me satisfied, and even became a strange point of pride that I could accept her wishes without demanding more.

Helping Lena discover sex and her own passion was also rewarding. I felt like a sexual grand master and I loved making her come. When Lena came, she looked like an angel.

The frustration was because our sexual explorations were the only times it seemed we were close and communicating. She dropped her guard to expose her real self—express what she really wanted and thought, but only about sex. At other times, Lena's "perfect wife" act was nearly impenetrable.

She also had never done much of anything. Her parents kept their only daughter sheltered. Lena's life was school and helping her mother run the home. Her friends were basically just study partners. Even through college she concentrated on her studies, following her parent's advice that there would be 'time for boys' later.

We went out during the day on our weekends together. Lena expected us to visit art galleries, museums and see plays, as if we were sweethearts courting in the 1960s. We went to those places, but I also took her hiking, bowling, cycling, and even paintball. It was impossible to tell if she really enjoyed any of it.

Things fell apart one Friday evening while we cuddled on her couch after our usual romp.

"My birthday is in two weeks," Lena said, lazily stroking her fingers over my chest. She was feeling good after two orgasms.

"I know. What would you like to do to celebrate?"

"Whatever you want to do."

"Lena, it's your birthday. There must be something special you'd like." I stroked her cheek. "Tell me. Please? I really want to know."

"You already know what I want."

"I really don't. You never open up. Everything I suggest is the best idea ever. Everywhere we go it's the most wonderful time ever."

She snuggled her head against me. "But it is, as long as I'm with you."

"That's not true, Lena. Remember when we went to see football? You were bored out of your mind."

"I was not. It was great!"

"You were yawning and checking the time when you thought I didn't notice. We were both cold and bored. And all those fans jostling and yelling? I hate football too."

"So why did you take me?"

"As a test. To see if you'd say anything. Suggest doing something else. Or afterwards finally admit you didn't have fun. I hoped we could laugh about it, and maybe you'd break character and open up for once. Be yourself."

"I did have fun! Really. I'd never seen football in a stadium before. It was a great idea."

It was so frustrating. "Lena, please. What do you want for your birthday? For real. Tell me!"

She was quiet for a moment, then said, "You know what I want. We've been together now for six months, so isn't it about time you..."

"Oh, no."

"Yes! If you propose on my birthday, it'll be so wonderful. My parents will be so happy."

That's when I lost it. I told Lena how used I felt, that all I was to her and her family was husband material, how two people need love and friendship to be happy together, and how after six months I still didn't know her.

Lena assured me I would be a wonderful husband and father and she would be a dutiful wife.

"Anyway," she said, "men and women are too different to really be friends. We each have our roles."

"Is that what you believe, Lena, or what your parents believe?"

She looked at me blankly, then frowned as though she had never considered there could be a difference.

~~~~

"After all this time," I said, "there has to be someone more special than me."

Lena pursed her lips, slowly shaking her head.

"Pickings get slim as you get older," she said. "I met most guys online, we'd chat. Things seemed great. Then we'd meet and usually that was it. Either I was too short, too fat, or..." Lena's hand drifted to her neck. "...I grossed them out."

"You're kidding. It's a birthmark. So what?"

"Everyone wants perfection. They also want sex by the second date, if not the first. Blowjobs aren't enough. A couple of guys were really nice, and we went out for a while, but both were kind of clueless. Then my parents set me with one guy from home who... who..."

"Oh, Lena. No!"

She forced a smile. "He tried. Nearly succeeded... right there on the kitchen floor. A knee in the nuts ended that date. And hopefully his chances for children."

We hugged again. Lena squeezed me tighter than before, then pulled away.

"The thing is, pappy insisted I must have done something wrong: led the guy on or dressed immodestly. He couldn't be expected to control himself... that kind of thing. And mamma didn't say much of anything. I guess that's when things started changing. I started thinking a little more for myself."

"I'm really sorry that happened to you, Lena."

"And each year I didn't get married, my family gave up on me a bit more. Guess I gave up on myself, too. Concentrated on work. Finding a guy wasn't as important."

She brightened. "Anyway, why are you still single? When I invited you over, it was a shot in the dark. I never expected you to accept."

"Why wouldn't I?" I patted my stomach. "Never pass up a chance for a free meal."

Lena looked like she was going to throw me out of the house.

"I'm kidding! Kidding!" I said. "I wanted to see you again. Talk. Catch up. I've thought about you often. About when we were together. And if you succeeded in your husband project."

"You had my email. You could've asked."

"I wanted to, but we've only been exchanging polite birthday messages. Didn't seem right to pry. You never asked me anything, either,"

"Yeah," Lena said. "I was afraid you got married."

"What do you mean?"

Lena shrugged. "It's stupid. As long as I didn't know if you were married, I could imagine us getting back together."

"What? Lena, we were done. And we only went out for six months. I'm nothing special."

"You were special to me. I really liked you. And we did things together. Just went out and had fun. Like you wanted to be friends."