Stood Up

While out to dinner with my mother, I kept getting distracted by a woman sitting at a nearby table working her way through a bottle of wine. She was sitting all alone, hadn't ordered any food, and kept glancing between her phone and the door. The woman was near my mother's age, rather full-figured with a very large bust. Her face was plump and pretty. But at the moment, she looked on the verge of tears. She was dressed nicely in low heels and a very modest, below the knee dress.

After we'd finished eating, my mother grinned at me, slyly motioned to the woman and asked, "She looks sad, doesn't she?"

My face blushed, "Yes, she does."

She then stood up from the table, picked up our check, and reminded me she was going to meet several of her friends at a new wine bar. She then glanced at the woman I'd been admiring all night and whispered, "Why don't you go say hello. See if you can cheer her up."

My face blushed again. When my mom said 'cheer her up' it meant more than just that. The year before, one of her lady friends, Janis, had gotten quite depressed. She'd been divorced and had become very lonely and depressed. During that time, Janis and I began seeing each other. Over the following few months, she taught me how to properly please a woman. That relationship was supposed to be a secret, but my mom and her other lady friends seemed to know about it from the start.

Like the lonely woman across the restaurant, Janis was also rather tall and full-figured with an exaggerated hourglass figure. My mother could also be put in that category and had struggled with her body image for most of her life. I suppose that is part of the reason why she teased me about being attracted to women her size and age.

With my face flushed with embarrassment, I whispered, "I think I may go introduce myself."

My mother kissed my cheek and said, "Good luck, Sweetheart. I'll see you whenever you get home. Even if that isn't until tomorrow!"

After she left, I stood up and summoned all my courage while walking toward the lonely woman's table. When I stood just beside it, I bit my lower lip and whispered, "Excuse ma'am, I just wanted to say you look very pretty tonight."

After wiping a tear from her cheek, she smiled at me weakly, "Excuse me? Were you talking to me?"

I smiled and assured her I was. The sadness in her expression began to fade almost immediately. I tried not to sound too timid when I introduced myself as Chris. She smiled warmly and told me her name was Martha. After standing there awkwardly for a few moments, I summoned my courage again and asked if I can join her.

Her voice was almost free of any unhappiness when she said, "Yes. Please sit down."

Martha and I talked over an appetizer and drinks. After a little casual chit-chat, as my mom called it, Martha shared that she had been stood up. It was her first attempt at internet dating and it was an utter failure until I showed up. I giggled and blushed a little.

After a little prodding, she went on to share that she'd been divorced for almost two years. Her ex-husband, Randall, left her for a younger, prettier girl. I told her I doubted the girl was prettier, younger perhaps, but not prettier.

After flirting with her the best way I knew how, she grinned and asked, "Chris, how old are you?"

My voice sort of cracked when I said, "Twenty."

She spoke in a soft voice, almost like she was talking to herself, "Oh my! That is four years younger than the slut Randall left me for."

After another lull in the conversation, she asked if I wanted something to eat. I told her I was fine with

the appetizer, but she should order if she wants too. After she opened the menu, I told her the desserts were on the back. Martha looked at me like I was crazy. I quickly explained that my mom sometimes liked to start with dessert and then see if she had room for the main course. Biting my lower lip nervously, I needed to say this as nicely as possible, "My mom is a full-figured lady."

Martha liked the idea of having dessert first and seemed to be very pleased I'd been raised by a woman her size. She went on to ask if my father was a small man. I smiled while explaining that I'd never met him. But my mom had shown me pictures and he was about my size.

After turning her attention to the dessert menu, she told me she couldn't decide between the carrot cake or the chocolate cake. Leaning over the table a little, I suggested she order both. She looked at me as if I were crazy again and said, "I couldn't!"

I giggled, "Why not?"

The banter went back and forth until the waiter arrived and Martha ordered a serving of each. When he returned, he set a plate in front of Martha that held a full-quarter of a double-layered, chocolate cake. In front of me, he set the quarter of the double-layered, carrot cake. I let it go untouched while Martha slowly devoured her chocolate cake. She asked if I wanted to try it at one point and I declined.

After wiping her lips on her napkin, she told me she was going to get a box for the carrot cake. I reached across the table and swapped the plates so the carrot cake sat in front of her and encouraged her to at least try it. After the first bite, she told me it was delicious. I told her I knew it would be and encouraged her to have a little more. After eating half of that slice, I told her it wasn't even worth getting a box for and pointed out that there were only a few bites left. When the fork slid out from between her lips after she'd wiped up the last of the frosting from the plate, she looked happier than she had all night.

She waved the waiter over and asked for the check, telling me she had no room for the main course. When he arrived with the check, I tried to grab it, but Martha got to it first. When it was all taken care of and we were ready to leave, I got up first and raced around to the table to hold her chair while she scooted out. Once on her feet, she took hold of my hand and we walked out of the restaurant together. I was with a mature, full-figured woman with huge boobs, wide hips, and the warmest smile I'd ever seen. Walking along beside her, she stood half a head taller and was surely more than twice my weight. I didn't notice, but I bet we attracted a little attention on our way out.

Standing on the curb outside, Martha asked how I'd gotten to the restaurant. I quickly explained that I'd come with my mom, but she left to join her friends. I told her I'd get an Uber. With my hand in my pocket getting my phone, she reached out and laid her large, soft hand on my forearm and said, "You will do no such thing. I'll drive you home."

I answered with a smile, "That's nice of you. I'd like that. Thank you, Martha."

She led me to her car and I held the driver's door open for her before racing to the other side. Once I was buckled-in on the passenger's side of her enormous, full-size car, she pulled out of the parking lot and began asking for direction. I gave her the first few turns, before she casually asked, "Chris, do you have any roommates?"

I giggled while squirming on the huge seat of her car, "Just my mom!"

She glances away from the road to me sitting beside her and said, "Wow, you are young!" After returning her attention to the road and letting a block go by in silence, she sounded like she was afraid to hear my answer when she asked, "Would you like to come to my house for a little while before I take you home?"

I responded in a very soft whisper, "I'd like that very much." After she'd taken the first turn away from the direction of my house, I silently undid the seatbelt and scooted across the huge bench seat close to her.

She wrapped her large, soft arm around my slender shoulder and said, "This evening has turned out better than I hoped it would."

Whispering back, "Is there anything I can do to make it even better?" Before she had a chance to respond, I gently laid my hand on her thigh about halfway between her knee and her hip. My stomach was doing somersaults and I felt dizzy. I'd never been so forward with anyone before.

When it was safe, she looked away from the road, down to my small, pale hand on her enormous thigh. She then lifted her eyes until she was looking into mine. She whispered, "Chris, I don't know about this. You're so young. You're so... You need a girl your age."

I bit my lower lip and answered, "I want to do this. Martha, I want to make you feel good. You're such a nice lady. You deserve some attention."

She whispered, "I don't know. It seems wrong."

Turning my head, I placed several soft kisses over her dress on the side of her enormous breast. Her perfume was musky and I felt the heat of her body radiating through her dress.

With my lips still brushing against her dress, I whispered, "Let me do this, please."

She was struggling to convince herself this would be a socially acceptable encounter. When she pulled up to the next stoplight, I snuggled up even more beside her and placed a kiss on the side of her neck. While waiting for the light to change, I kissed my way to the front of her neck. Nearly wiggling my way into her lap, I then kissed my way up under her chin and until our lips met.

My tongue slipped into her mouth and slithered across the top of her tongue. She began kissing me back while her arms embraced my body. When she next opened her eyes and saw the light had changed, she began to slowly drive while I kissed my way back down her neck. Covering her in kisses as I worked my way toward her ear, I whispered, "Can you lift the steering wheel?"

At the next opportunity, she lifted the steering wheel as far as it would go. I kissed my way down the front of her dress... right down the middle, not veering off to kiss her gigantic breasts, even though I wanted to so badly.

On my knees in the front seat with my head in her lap, I slowly slid her dress up her legs. Scooting down, I began kissing my way up her huge, pantyhose covered, thigh while pulling the dress up as I went. She was running her fingers through my hair and I could smell her excitement.

When I got to her lap, I smushed my face between her thighs and blew my warm breath right between her legs.

She moaned and said, "Chris, you need to stop! I'm trying to drive! We're going to get in an accident!"

Sliding off of her lap, I squirmed up beside her. I kept myself busy kissing her neck and shoulder. The next time she had to stop, I asked her to lean forward a little. As quickly as I could, I reached back and unzipped her dress part way. While sliding her dress off her shoulder and slipping her arm out from the sleeve, she moaned, "I can't believe this is happening!"

She began driving again as I slowly pulled the dress down under her breast. It was huge. The sturdy bra she wore was lacey and sexy. I kissed my way down from her shoulder and over the cup of her bra. Looking up at her face, I whispered, "Are we almost home?"

She answered in a raspy voice, "Almost, just a little farther."

I continued to kiss all around the perimeter of her bra. Her skin was soft, warm, and smelled like musky perfume. Laying my open mouth over the bump her nipple was making, I inhaled and then exhaled through her bra.

When the car turned and finally came to a stop, I looked away from Martha's breast and saw she'd pulled to a stop in the driveway of a nice, two-story suburban home. She turned the car off and sat for a moment breathing heavily. I snuggled against her side, letting my open palm slide over her bra encased breast. While kissing her earlobe, whispered, "Are we going inside?"

She moaned softly, "My neighbors, what will they think if they see you coming inside with me?"

Whispering, "What will they think when they see us leave together in the morning?"

She arched her back and moaned, "Oh my lord!"

After one more kiss on her neck, I slipped out of the car and walked around to her side. Opening the door, I offered my hand to help her out. Martha paused to get her dress back on and zipped up. She then reached out and took my hand. Rising out of the car, we walked hand-in-hand to her door. She fumbled with the keys but eventually got the door opened. After we'd stepped into her home, she closed and locked the door before turning back to face where I stood. The sexual tension could have been cut with a knife.

She was about to say something, but I dropped to my knees and flipped her dress up over my head. Kissing and licking my way up her thick, pantyhose covered legs, my face was soon pressed between her thighs. I opened my mouth wide and exhaled my warm breath through her moist pantyhose.

Martha leaned back against the door and spread her legs wider apart. I scooted in even farther beneath her. I placed kisses and licked along the lips of her nylon-covered pussy. When I finally slid out from under her dress, I remained kneeling on the floor at her feet. Her face was flushed and her chest was heaving. She whimpered softly, "It's been so long."

I licked my lips and asked, "Martha, where is your bedroom?"

She nodded her head toward a flight of stairs and when I rose to my feet, she took my hand and led me to the second floor, down a hall to the master bedroom. I guided her to the bed and had her sit down.

Dropping to my knees once more, I removed her shoes one at a time while she leaned back on her hands and watched. After both shoes had been removed, I held one of her feet in my hands, kissed the bottom of her big toe, and whispered, "Martha, I need you to stand up again."

After setting that foot gently on the floor, she stood up in front of me. While looking into her eyes above me, I slid my hands up the outsides of her thighs, under her dress, until I felt the band of her pantyhose. When I hooked my fingers under that band and began slowly working them down her legs, she maintained eye contact while her chest heaved heavily. She was bare beneath her pantyhose and when I'd gotten them down to her knees, Martha sat back down.

After I'd completely removed her pantyhose, I tossed them aside and picked up her foot once again. I placed kisses on each of her freshly polished toenails. While staring into her eyes, with my lips brushing against the top of her foot, I whispered, "I'm really glad your date stood you up tonight."

She moaned softly, "Chris, why me? I'm old enough to be your mother."

Moving to her other foot, I kissed each of those toenails and licked along the top of her foot which made her moan softly. In between kisses, I whispered, "Why you? Because you looked so pretty in the restaurant. But you were also so sad. And no woman should ever look that sad."

She kept staring into my eyes as I kissed my way across her ankle and up her shin. The skin was soft and freshly shaved. She was prepared for her date, just in case. I worked my way up her shin until I met her knee. Biting my lower lip, I then flipped her dress over my head. Martha laid back on her bed and spread her legs wide. I kissed my way up both thighs, switching between them. The smell of her arousal was strong and unmistakable.

When I kissed along the lines where her thighs met, I backed off a little to admire the beauty before my eyes. Her dark pubic hair was long, but the sides were trimmed so it was shaped into an enormous triangle. Leaning forward, I slid my tongue between her plump lips, inside of her, and slowly licked my way up to her stiff, thimble of a clit. Her thighs squeezed against my head and then released. But they seemed to be quivering against the sides of my head.

From above, I could hear Martha breathing heavily and moaning softly. Licking circles around her clit with the tip of my tongue, she groaned again, "It's been so long."

Gently sucking her thick clit into my mouth, I held it for a short time while tickling it with my tongue. When it slipped out from between my lips, I whispered, "How long has it been?"

She moaned while I began licking circles around her clit again. "I haven't been with anyone since the divorce."

I whispered with my lips brushing against her sex, "How long?"

She arched her back, "More than two years. But even longer since anyone has done what you're doing."

Taking a long lick from the bottom of her pussy to her clit, I whispered, "How long?"

Her clit throbbed on my tongue and her legs began to vibrate. Soon after, she began to writhe about under my lips. Just before her legs clamped down tightly on my head, she groaned, "Decades!"

And then she came. Her thick legs held my head securely in place. Her entire body began to shake and jiggle. Her hands moved to hold my head in place beneath her dress. As her orgasm crested, I pulled back and blew my warm breath onto her peeled-open lips.

After giving her several moments to calm down, I kissed my way out from under her dress. While sitting on my heels, she lifted herself on her elbows. I smiled and said, "You're wearing too many clothes."

Her face was flushed when she moaned the words, "So are you."

Biting my lower lip, I giggled, "If you say so!" I then slipped off my shoes and socks before rising to my feet. I stepped back from Martha and looked into her eyes while undoing the buttons on my shirt. After letting it slide off my narrow, pale shoulders, I reached down and began undoing my pants. Martha's eyes drifted over my skinny, upper body. Her gaze lingered on my collarbones and the impressions of my ribs.

When I lowered the zipper of my pants, I thought I was going to faint! My mother's friend Janis had been the only other person to ever see me naked! Janis had taught me so much about women. Compliments, manners, and respect were paramount. Never rush the sex. Go slow and take your time. The sex is about the woman, not my penis. Janis had also taught me that I shouldn't be ashamed of my petite build, and that is the lesson I struggled with the most. I'd always been short, skinny, and shy. Janis had been the person who helped to teach me they were good qualities, not bad. As I stood there undressing for Martha, I saw she was looking at me the same way Janis did when I undressed for her.

The blush on her face darkened when my zipper had been lowered all the way, "I cannot believe this is happening."

Very slowly I began to lower my pants and underwear together. I watched her staring at my waist when my skinny, little prong of a penis popped out, it was rigid and throbbing. Her eyes opened wide and she chirped, "Oh my!"

After dropping my pants and underwear to my ankles, I stepped out of them and stood there letting her look at my naked body. I struggled to keep from squeezing my eyes shut. But I managed to keep them open but was unable to maintain eye contact.

She sat up from her elbows on the bed and reached out to take my hands. I stood there in front of her naked and erect. She looked from my penis to my eyes and spoke in a soft voice, "Chris, you're beautiful."

Biting my lip while my entire body flushed, I whispered, "Thank you." I giggled a little before saying, "Um, it's your turn."

She hesitated before reaching behind her back to lower the zipper on her dress. I stopped her and told her I wanted to do it. She stood up slowly and turned her back to me. Reaching up, I slowly lowered the zipper until it was down. Sliding it off of her shoulders, I helped it slip over her enormous breasts and wide hips. I kept hold of it while it traveled down her legs and she stepped out of it. I lay it on her dresser before turning to address her bra. I struggled with the five, sturdy hooks and eventually gave up and asked for her help.

With her big, bare bottom still facing me, she made quick work of the bra and let it slide down her arms, leaving her naked. She began to tell me how long it had been since anyone had seen her without clothes. While she was still talking, I dropped to my knees and began kissing the backs of her knees, working my way slowly up the backs of her thighs. Martha stopped talking mid-sentence and stood there as I kissed my way up her body. When I met the bottoms of her butt cheeks, I wrapped my arms around her thighs and kissing my way over them. I covered those big cheeks with kisses before rising back onto my feet and kissing my way up her naked back.