Waitress Jennifer finds a way to cheer a melancholy patron. After bringing a smile to his face with all her holes, she tells him about the man who taught her the joys of kindness.
This is a true story, but it’s not my story. Jennifer is an old friend. That’s her real name by the way. I see no point in changing names “to protect the innocent” when I’m only sharing her first name and she’s anything but innocent.
Now the customer who dined a week ago at the upscale Japanese restaurant where she works, he was innocent. That’s how she described him to me at least. “He looked so innocent. Cute, early middle age, just a touch of grey in his hair, good body, you know he works out and eats well. Good face too, but something boyish in it. Like a part of him never had the chance to grow up. His eyes were very sad.”
Three years as a waitress there and Jennifer had never so much as flirted with a patron, just laughed away the occasional suggestive comment. But that mixture of innocence and sadness (and good looks) sparked her curiosity, so as she brought him the check she said “You look sad.”
That surprised him. He looked up and saw her face for the first time.
The he smiled wide and said “Do I? I’m not sad really. I just have a sad face when I’m not paying attention.”
“Well, if your resting face is sad, maybe you’re missing something and just don’t know it.”
“Oh I know it,” he said and then caught himself, embarrassed.
The customer reached for his sake glass like he was going to take a swig, but of course it was empty so he refilled his water glass and sipped.
“I don’t know why I’m even telling you this. I’ve been happily married since I was nineteen and it’s been wonderful, beautiful. Beautiful wife, beautiful home, three beautiful kids. And, well, in some ways all that happiness and beauty can be really fucking frustrating.”
His lips drew down at the corners, and he got up heavily, made to put on his coat. But Jennifer interrupted him:
“I’ve never been lucky enough to have a relationship like that, not yet anyway. But I know what frustration feels like. Wait there a sec, I’ll get someone to cover for me.’
It was late enough that the dinner crowd had thinned and the evening drinks crowd hadn’t arrived yet. The other waitress, Susan, was happy to look after all the tables, no explanation needed. When Jennifer came back to the table the man had his coat on and she squeezed his hand and grinned at him.
“Today’s your lucky day,” she announced. “Come with me.”
“Anywhere in particular?”
“The back room. I have a present for you. I’ll show it to you and you’ll decide what to do with it.”
That boy followed behind her like a lamb. Jennifer tells me she didn’t know for sure what he was thinking but his trousers already said he was hoping. She led him to the keg room that no one would need for hours and pushed a keg against the door.
At this point I should say that Jennifer has the kind of body any straight man drools over. She works out hard and enjoys sculpting herself. Taut belly, ass rounded with muscle, arms and legs firm. But nowhere ripped. She eats thoughtfully, but she does make sure to eat. Just enough body fat to stay feminine and keep her ass kissable and her pert young chest nice and full.
He must have noticed her ass as he followed her, how it twitches just right as she walks. I’ve certainly noticed. I assume any man with a pulse must.
She took his hand again and put it to her breast. He actually gasped, which warmed Jennifer’s heart. She could hardly believe what she was doing any more than he did, her pulse was pounding, but his shyness gave her confidence.
“I’m going to ask you some questions,” she said. “And with each answer I’ll show you more of your present.”
“I’ve never,” he answered. “Not since the wedding, I’ve never with anyone—”
“Well that answers one question already.” And in a swift motion she pulled off her shirt. She regretted briefly that her bra was a totally functional off-white, not black or lacy or anything.
“Put your hand back on me please. Thank you. Can you squeeze me a little too? Yeah, play with me. Enjoy me. Savour me like you savoured that carafe of sake. Is mine really the first breast besides your wife’s you’ve touched since you were nineteen?”
“Yeah. I went to a strip club and watched once but I couldn’t bring myself to do any more.”
“Aww. It’s okay, I know that feeling too. Here wait a second,” and she reached behind and unhooked her bra. “Go ahead. You can take it off me.”
He did, and she told me his hands were honest-to-God trembling.
“Go on, you can touch me. With both hands. Touch my arms and sides and shoulders. Enjoy me.”
“I don’t know if—”
“Next question. How old are you now?”
She kicked off her shoes, one at a time. “That’s actually two questions because now I know you’ve been married twenty-two years.” She reached under her skirt and pulled her tights down. He couldn’t see under her skirt but now her legs were bare below the knee.
One of his hands was travelling up and down her arm, the other still massaged her breast.
“Why haven’t you had an affair?”
“Too risky. The opportunities never came up. Oh, once or twice I maybe could have, but I didn’t have the heart, I was too shy.”
She loosened and dropped her skirt. Nothing remained but panties.
She took his hand off her breast and led it down, under the flimsy fabric. He felt before he saw her curling hairs, and then lower still, till his fingertips rested against her lower lips and he felt how wet she was. Jennifer let out a sigh.
“For the next hour I’m your present. You can do anything you want to me. Oh, just one more question first. If there’s one thing in the world you’re not getting at home that you’d like to have now, what would it be?”
The man swallowed. He looked at her guiltily for a little while. Then arousal and happiness surged in him and the guilt vanished. A hungry smile shone. “If it’s not too much to ask, then, well…”
He moved his hand around, cupped her ass, still under her panties. His middle finger sought out and found the little shy hole in her rear.
“…can I have you there?”
Jennifer looked at his smile. His hand drew her closer; his finger pressed gently on her back entrance. She could see the urgency in his eyes, and it flattered her that he was still able to keep his self-control. He still was a gentleman, which made generosity a pleasure.
“You don’t do that at home?”
“We tried just once, when we were still dating. She never let me again. I’ve spent the last twenty years wishing I’d gone slower, more gently that time.”
That’s when Jennifer put her bare arms around him and kissed him on the mouth. Her heart was moved. He squeezed her breast, and she clenched her buttocks, squeezing his finger.
She reached down and slipped her panties off.
“Then remember to go gentle with me.”
There was no hurry. She helped him disrobe now, unbuttoning him, undoing his belt. She enjoyed the healthy strength of his body, but most of all she loved how much pleasure her naked skin was giving him. He moved his hands all over her back, arms, sides, breasts; he kissed her mouth and neck and shoulders like he’d been dying of thirst and she a beautiful oasis.
There was a nearby table. She had him lean back on it and then she crouched, hands on his hips, and started to kiss his cock. It was hard as iron now, hard with all his hunger and desire. Her kisses became licks, and then looking in his eyes she took the head of him in her mouth and bobbed up and down.
After she gave him that pleasure for a few sweet minutes she stood up, fished a condom out of her purse.
“I know, I know,” she said as she opened the package, rolled the condom onto his cock. “Trust me, this’ll hurt me more than it hurts you. You’ll thank me tomorrow; it cuts down on next-day stress.”
Now she came to the table itself, next to him, put one knee up on it as she stood with the other, leaned forward a bit to open herself wide up. She took his hand and sucked his fingers lewdly, getting them all wet. “Play with my pussy,” she urged.
Well, he wasn’t going to say no to that. He began stroking her, overjoyed by her shape, her heat and wetness. She gasped as his fingers moved from stroking her outside to he inside. For a while she rode with his touch, then she took his other hand and started wetting those fingers too.
“Put a finger in my ass,” she said. “Be gentle.”
Gentle he was. He teased her little hole, rubbed it, pressed without entering, got it good and wet. As he did so he felt the rubbery ring of muscle respond to him. He didn’t push per se, but just let the corner of his finger sink a bare few millimetres inside, let her asshole squeeze him, nibble him. When she was ready he pushed a little more, half a fingertip.
He wanted her really wet and comfortable so he took his hand from her ass, dribbled more of his own saliva on his fingers, and returned. Several times over he did this, going a little deeper each time, while all the while she pressed her pussy into his other hand.
And then gradually he found that his finger was through. He was in! He could feel it! The tight, tight squeezing ring of her entrance extended another inch or two inside, and then it was more open inside—open, warm, forbidden, and so different from all his prior experience.
“That’s it,” she told him, and she grasped his rock-hard, condom-covered dick and stroked it. “Keep going. Stir around in me. Feel everything. Enjoy me. Yes! I felt what you did there. Do it again. Yeah. Do you like it?”
“Put your fingers deeper in my pussy. All the way up. Yesss. Can you feel that? Can your fingers feel each other through the thin wall between my cunt and ass?”
“I can… oh, God yes, that’s so cool.”
She kissed him deep and gave her tongue to his mouth as he probed her front and back.
Eventually she took his wrists and guided his hands gently out of her. She brought both to her mouth and planted sweet little kisses on his fingertips. “Thank you.” Kiss. “Thank you for touching me there.” Kiss. “Now I want to feel your cock in me.”
She held him by his manhood and guided it to her cunt.
“But I thought that—”
She squeezed his cock.
“Uh-uh-uh. Soon enough, handsome man. First I need you to get me warmer. Come on and pleasure me.”
He pressed forward and filled her up from behind. It was heaven, the heat of her tight womanly body holding him. His hands ran all over her, enjoying the heft of her breasts as she leaned forward, and how good to squeeze her thighs, her calves. Soon he was holding her by the hips and thrusting into her passionately. Hot, oily, and tight her cunt squeezed him.
And as she squeezed she reached behind and slipped her own finger into her ass.
“Now we’re both fucking me,” she said with a wink.
This set him off like a bull. He could see everything: his cock disappearing into her pussy, her finger moving in and out of her asshole; it was glorious. He thrust and thrust in her. Soon she replaced one finger with two, widening her little hole, getting it ready for him. He could feel her fingers as he moved in her. Truly, they really were both fucking her.
“I think now,” she said, taking her fingers out of her ass and putting her hand on his chest. “Now. I’m ready for you.”
He took his cock, so happy and hard, in hand and pulled gently out of her—they both sighed when her pussy released him. He positioned himself right at her smaller entrance, nudging her. He couldn’t believe it was happening. It was so beautiful.
“Remember now, gentle. Slowly slowly. The slowest you’ve ever done.”
So he kept nudging her there, and ever so slowly increased the pressure. Nothing even seemed to move, but she groaned encouragingly, said “Keep like that, I can feel you, I can feel it about to happen…” and he kept up the pressure there, and slowly her hole relaxed, and he sank in almost on his own, the tiniest bit of the tip, and then more, and then the whole head of his cock.
“There,” she said. “Wait a few seconds. Let me get used to you. Ohhh, feel that. You’re inside me there. You’re going to fuck me there as deep as you like. But first wait.”
He waited in bliss while she breathed. He couldn’t believe his eyes. He wanted so much to move back and forth, his body knew how good that squeezing ring would feel once it started to move up him. But he waited. And at long last Jennifer shifted her hips backwards, sinking another inch of him into her.
“Now,” she said, “fuck me slowly.”
Slowly he began to rock back and forth, savouring the experience, breathing heavily, feeling the exciting forbidden gift she was giving him. His cock recapitulated the journey his fingers had made earlier, deeper through that tight tight ring, and then into the depths of her beautiful rear. No words to describe how… different, how wonderful, how her back entrance stroked and kissed him.
“You see how it is?” she said. “My cunt gets tighter the deeper you go in, but my ass is tightest right at the entrance. You can actually get the most pleasure by not going too deep in me, just fucking my ring with the end of your cock. But I want you to go all the way—oh!”
He moved in and out more firmly now, though still slow and gentle compared to his wild thrusts in her pussy. He could feel everything. And at last, going a little deeper each time, he slithered himself up her body until he was all the way in, pressed to the root in her, widening her hole further with the base of his shaft, his balls resting against her pussy. He wrapped his arms around her from behind and squeezed her, impaled her upon him like they were nailed together.
“Oh, yes!” she exclaimed. “Yes, yes, it doesn’t hurt, it’s just so… oh it’s so different, so intense, and calming too. I’m shivering. I can feel you all the way in me, all the way UP me!”
He started longer thrusts now, not too fast but all the way in and almost all the way out, and as he did he rubbed his face against her shoulders, her neck, and she heard the pleasure in his voice as he mumbled “Thank you, thank you, ohhhh God thank you.”
And then she noticed something cool trickling down her shoulder. She looked back in his face.
He had tears in his eyes. Tears of joy.
The ecstasy in her body and delight in her heart at what she’d given him to feel made her decide then and there. “Wait a sec,” she said. “Don’t move.”
That wasn’t an easy command for him to obey, but obey he did.
“Just stay still and touch me a little. That’s it, yes. Play with me there.” She rolled her head back while he played with her clit and lips. “Are you close?”
“Take it out of me. Slowly!”
Even harder for him to follow, but he obeyed. He even hid the disappointment from the face, not wanting to show that to a woman who had been so sweet to him.
“There, you passed the test. You’re a true gentleman. Just this once, I’m going to make an exception,” she said, and she crouched down again. “Just for you.”
And she pulled the condom off.
Then she took him in her mouth again, but not for very long long, just enough to get it nice and slippery wet. Another idea struck her, as long as she was being crazy.
“You have a phone in your trousers? Take it out. Take some pictures to remember me.”
With fumbling hands he took photo after photo. Her sweet eyes looking up as she sucked his cock. Her smiling face, tongue reaching out just touching his glans. Her naked body, her tits and bare legs. She guided him to take a closeup of her pussy, then bent over the table and lifted her other leg so he could photograph both holes all open and fucked and ready.
“Put your cock back in me. You can do it faster this time.”
He lined himself up with her asshole now, so hard, so excited, knowing he was about to feel her skin-to-skin. This time the head slid right in. He took one photo and then was so overwhelmed by the sensation that the camera was forgotten.
“Now do whatever you want to me, however you like, all the way.”
And he did. He pulled her tightly to him, arms wrapped around her again, one hand on her shoulder one on her breast. He moved at a pace that felt right, not so very fast but firm, strong. Bare skin on skin, his cock and her ass touching, stroking, kissing each other.
His breathing sped further, turned to panting, to groaning. She felt each thrust up into her a hot stab, a beautiful love letter, a testament to her beauty and generosity. She could almost feel his orgasm approaching through his excitement, the way his body took over from his mind, the way he took her.
And he whispered “I feel it coming”, and he moved at a crazy pace inside her, and then all at once he planted himself as deep in her as he could and squeezed her so hard and by this and his moans she knew he was pumping his seed up into her body.
Then he panted behind her, dropped his head to her shoulder, breathing, overjoyed.
“Don’t pull out yet,” she said. “Take another picture or two.”
He pulled her cheeks apart so he could capture the way his still-hard cock filled her, widened her. She hadn’t really felt his come shoot into her, but she felt as some of it oozed back out, and she gave herself a little internal squeeze to make more drip down upon his hardness.
A naughty thought came over her.
“Can you record a video?” she asked. “Just point down. Ready? Okay: three, two, one.”
She daintily pulled herself off of his cock. For two seconds the video showed (she made him play it for her afterwards) her open asshole winking, then in one graceful motion she turned and kneeled and pleasured his cock, alternating between sucking the head and licking up the sperm from his shaft.
When he was glistening clean she rose again and gave him a quick happy peck on the lips.
As they dressed, she gave him life advice.
“Save those pictures somewhere very private! Don’t you dare put them online. Keep them for a rainy day when you’re horny and want to remember this. We’re not going to do this again. You don’t really want an affair, I can tell. Just an experience.
“It’s your life, but you’ve shown me a side of you, and let me suggest: don’t let yourself feel trapped in your marriage! It’s not a trap. You choose every day whether to stay or go. If you’re choosing to stay every day, that probably means it’s a good choice. Enjoy it! So many people would kill to have what you have.
“And if that’s still not enough, then maybe leave, or maybe remember you can always leave later when the kids have gone to college. That’s a lot more normal now.”
They were dressed. The man looked different to her. These experiences can leave us changed.
“How did you get to be wise?” he asked.
“Well I’ll tell you a story.”
Once upon a time (she didn’t have to tell me this part), long years ago, she wasn’t the sex goddess he saw now. She had been miserably fat, in the ‘obese’ BMI range, pre-diabetic. She’d come from an overweight family with bad eating habits and had already been hefty in primary school; then in high school she simply ballooned.
Who knows if genetics had some role, but bad habits were the immediate cause. The sugary drinks, the refined food, the sheer volume of caloric intake. Such a common story: she tried to exercise but heavy as she was it was painful and she got discouraged. She tried to diet but it made her miserable and her self-esteem was so shot she couldn’t believe in herself enough to continue. She tried fads, she tried genuinely good advice, but even the truth won’t set you free without the energy to continue. She tried ignoring the problem or embracing to it ironically. She developed a loud personality to cover her unhappiness. She became defensive.
She was trapped, apparently inescapably, in that zone of unhappy mediocrity where people said behind her back “What a pity! She’d have such a pretty face if she only had some discipline.” And she knew it.
And so she passed in loneliness and disappointment her college years, the years someone had once told her would be the best of her life.
And then a guy said Hi to her in the gym. She had just gotten off the treadmill—twenty whole minutes of fruitless uncomfortable power-walking, feeling judged by everybody there—in one of her infrequent doomed lunges at self-improvement. And he just came over and said hi like they’d known each other for years.
He was no bodybuilder, not a hint of steroids about him. Instead he boasted the hard balanced physique of someone who’s been pushing weights around diligently for years. What really struck her was how his shoulders gleamed with sweat under the overhead lights.
Everything about him radiated sex.
Perhaps she was too low on oxygen for her usual defensiveness to kick in. She forgot to push him away or even judge him pre-emptively as a creep. She just said “Hi” back.
“Listen, I’m new in town and looking for a gym buddy. Do you want to work out together? Mondays, Wednesdays, Fridays?”
She looked down at herself and back at him. “You’ve got to be kidding.”
He shook his head. “Come on, it isn’t where we start, it’s where we’re going. Give it a try? It’ll be fun.”
By some miracle of mood, or perhaps it was just the effect of his voice and smile, she said “Okay, what the hell.”
That day he showed her some basic dumbbell exercises, the simple compound movements, none of that crazy shit some PTs invent to keep you going back. And not the barbells a young man might start with: poor Jennifer had neither the strength nor the confidence to start there. She only learned it later but he was picking routines that she could naturally improve in quickly.
Then he took her far away from the treadmill—they’re wonderful, but not when you’re that overweight—and onto a bike. The thing about heavy people is they’re stronger in the legs than you’d think (assuming they’re still walking). Once you take that weight off by sitting them on a bike they can use it. Then the other trick: he gave her only ten minutes on a bike, but with stiff resistance. She’d never tried that before. It made her feel strong. Building her confidence was the most delicate step in those first days.
Then he had her help him. She spotted his bench press. She took photos from the side as he squatted so he could check his form, make sure his back was straight and his hips came down to knee level. He was also showing off, and it was working: she was aroused without knowing it, and arousal helps the drive to work out.
“Okay, here’s what happens next,” he told her an hour later. “Tomorrow morning your arms and legs are probably going to hurt like hell. Don’t worry about that, that a good thing, and after a few more sessions it won’t happen; you’ll even miss it. Give me your number, and we’ll do this again three times a week, and you’re going to see, I promise you, how quickly you get stronger and how much more you’ll be able to lift.”
He was careful not to promise that she’d lose weight. That depends as much on intake as exercise, but even more important he knew you see the strength gains first, and that fat people never see their own weight loss until it’s well in hand.
So the next session he concentrated on strength, and by the third she really was a little stronger, lifting heavier dumbbells, going longer on the bike. He took them to a cafe to celebrate, and that was the first time he so much as mentioned weight.
“You know half my excess calories used to come from coffee house stuff. Milky lattes, croissants, that kind of shit. That stuff’s not for us. Maybe once a year. Try an espresso or Americano with just the littlest bit of skim milk in it, you’ll see, it’s dark and delicious.”
She would have argued with him, but she felt so triumphant from her exercise and was beginning to find it so good to follow his guidance that she gave it a try. And damn, that dark bitter taste was good. It tasted more like coffee without the distraction of all the creamy syrupy stuff.
Thus he changed her eating, much like he grew her strength. Incrementally. Step by sustainable step. One week she cut out the sugary drinks. The next she cut out potato chips. She added new things, experimented. Turned out carrots are fucking good, apples are sweet and juicy, but celery just never worked for her.
For a while he did all her record-keeping. After two months he showed her a graph of how much stronger she’d gotten. That got her so interested he showed her how to log her own workouts, and that led to talking about counting calories. She never did this too diligently, but she did get a sense of how much she wanted to approximately have at each meal, and what everything ‘cost’. She made refinements, substitutions. She began to find intellectual satisfaction in eating healthy: not to mention the great ways it made her body feel.
After four months he shared once concern with her.
“Jennifer, I’m a little worried you’re losing weight too fast.”
“What? Fuck off.”
“No seriously. Have you checked how much you’ve lost?”
She had not. She’d been afraid to touch a scale, and she still looked the same to herself in the mirror (low self-esteem kills your ability to judge). Even now he didn’t ask her weight, but suggested she check how much she’d lost. So she stepped on the scale in the women’s changing room and holy fuck. Holy fuck!
She had lost forty pounds.
God she was thrilled. That had never happened before, ever. She wanted to dance. And yeah, when she looked in the mirror now, she was still fat, but dramatically less so; she wasn’t even technically obese any more.
So she was almost hurt by his concerned response.
“Yeah, see? 40 pounds in four months, that’s… two and a half pounds a week. That’s too much. You should aim for between one and two pounds a week. That way you don’t lose muscle, you don’t risk loose skin. Let’s see, so to lose one less pound a week you’d to eat need 3500 calories more in theory, so 500 more a day… but fuck theory so let’s say 250…”
It almost made her laugh. She used to drink several times that much through a straw every day just between meals without realising it was killing her. That, and the sedentary lifestyle… even if she’d only been gaining half a pound a week, as year followed year… oh what a waste.
And yet she couldn’t even feel proper regret; she was too busy feeling wonderful.
She was resistant to eating more, but he explained about protein and other macronutrients, about her body’s needs, about how “muscle” means firm toned flesh not bulging biceps; and how strong the extra nutrition would make her as she kept losing weight. Earlier she wouldn’t have believed him, but he was her gym buddy and here she was forty pounds lighter, so, what the hell.
It took a lot longer doing it safely, but the results were so much better than she could ever have believed possible.
Even after a year of working out together she had some leftover heft in the belly and thighs that she looked forward to burning away, but already her physique was so good, her arms firm, her posture restored, that she looked positively bursting with life. They knew it was exactly a year because of course they had every workout carefully logged.
That night she took him to her apartment for a celebratory fuck. It was their first time fucking. They made athletic love literally all night long. They were not in love per se, and they weren’t quite friends with benefits either. They were gym buddies!
The next day Jennifer burst out crying. Happy tears, tears of getting back a life of fun and energy and sexual fulfilment she could have lost for no better reason than the sorry state of health education and all the sugary processed shit in stores.
“Why me?” she asked. “Why did you pick me?”
“Honestly? I saw you trying on the treadmill. The exercise you were doing was completely hopeless, but you were trying so hard and so sincerely. It touched something in me. Listen, let me tell you a story.”
And then he told her about an older girl in high school who had taken him under her wing when he was a weedy, shy little bookworm. Taught him to dance, taught him to kiss. Let him put his hand under her shirt. He never got any farther with her but that first experience led him to try so much more, set him on a long road to self-confidence and self-mastery.
“And then,” Jennifer told the man whose seed was still drying on her chin, “I asked him if there was anything I ever could do to thank him. And he said, ‘pass the favour on to others. There’s nothing more fulfilling that random acts of kindness.’ And I remembered him saying that when I saw your sad eyes at the table. Now you go out there and remember too.”
You can imagine how impressed I was with Jennifer when she told me this story.
And why did she tell me? That should be obvious! Six years later, I’m still her gym buddy.