Shorty

Matt was living with his grandmother after getting his degree at the age of 23 because she lived close to where he worked and his family lived in another town close to 100 miles away. He is a very quiet young man with very few friends from work, male or female. His grandmother, Pauline would ask on a regular basis if he has a lady friend, the answer is always "no".

Pauline is a 65 year old widow and loved having Matt living with her. Having someone to talk to and care for after a decade of living alone brought her a great deal of satisfaction. Lately, she noticed that Matt seemed to be getting even more quiet, and perhaps even a little more depressed than usual. She was very concerned and decided she would ask about it at dinner on Friday.

Half way through their dinner Friday evening, Pauline brought it up hoping Matt would talk to her about it.

"Matt, I've noticed that you have become even more distant than usual and I'm worried about it."

Matt didn't make a sound or even look up.

She continued "If you feel you can't talk to me about it, you should consider sharing what's bothering you with your girlfriend." He still didn't look up from his plate. "Or do you have a boyfriend? Honestly, I don't know and I'm okay either way."

Matt's head snapped up with a surprised expression "No, I'm not gay if that's what you're asking." Then after a short pause he mumbled under his breath "But I may as well be."

"What do you mean?" she asked.

"Nothing. It's too embarrassing."

"Matt, nothing is too embarrassing when it comes to your happiness. A blind person can see that something is really bothering you and eating you up. Please, please share what it is. Honestly I can't think of anyone else you can share with that cares about you more than me except your mom and dad."

After a long pause, Matt looked up into Pauline's eyes. She could see that he was fighting back tears. "Grandma, I just don't know how to even talk about it. It's a guy thing."

"Okay Matt. Perhaps a perspective from someone outside the GUY CLUB will help." she said. After a pause "Maybe you should talk to your dad since it's a guy thing."

"Okay. Here it is. I probably have the worlds smallest penis. There's no way I could possibly have a girlfriend."

Pauline wasn't expecting that and she didn't want to show any reaction at all so she kept her concerned expression frozen. Matt looked back down to his plate avoiding more eye contact with Pauline.

She thought about it for a minute before responding. "Why would you say you could never have a girlfriend?"

"You're kidding, right? The first time any girlfriend sees what I have, or more accurately what I DON'T have, she would laugh and run away. And I wouldn't blame her."

"Wow! You think a relationship is just about the sex? You think all men that have a small penis are single and never get married, or have kids? And you think intercourse is the only thing couples can do to be intimate? Wow!"

"I don't know. I would hate to go through the rejection that I know I would get."

Pauline thought for a minute, "Would it be okay If I helped? I have some ideas that might make the whole thing a little less dramatic for you. Your grandfather had a tiny willy, too. We came up with some things I think may help you, too"

"Like what?" Matt asked.

"I think you'll just need to trust me. What do you say?"

"Well, I am desperate and have zero ideas myself. So, okay."

"Come on. Let's get started." she said holding out her hand. Matt took her hand as she led him into her bathroom. "Okay, take your clothes off."

Matt looked horrified at her request. "Relax, Matt. Haven't you ever heard - Desperate times call for desperate measures?" He could tell from Pauline's expression that she was serious.

He was a little reluctant as he undressed, but did so because he trusted his grandmother.

When he was completely naked, Pauline thought he had a great body. Trim waist, hint of six-pack abs, well defined chest and arms. Then there was a thick bush where she could see the tip of his circumcised his penis poking out.

Pauline turned on the shower and tested the water until it was warm. "Okay. Step into the shower." She pulled up a chair to sit outside the door as he stood under the shower.

She squirted some shaving cream into her hand and spread it all around his pubic area. Then took a razor and started removing all the hair around his little cock and shaved his balls as well. Matt couldn't help but get an erection since this was the first time since he was a baby that someone else was touching and handling his penis. When she was done, she took the shower head and sprayed the remaining soap off. Pauline noticed Matt's small cock was now hard as a rock at about three inches long, but had a nice thickness.

"There. Without all that pubic hair, you already look bigger."

Matt saw his reflection in the mirror and protested "Oh geeze. Now I look like a XXX!"

"No XXX has a willy that thick, Matty boy. You may be a little shorter than the average, but your girth is probably average for a male adult. Certainly thicker than Grandpa's." she reassured him.

Pauline opened a small case on the counter and took out a penis pump. "This is what we used to make your grandfather a little bigger. Later on it was helpful for keeping him hard enough for intercourse." She squirted tome lube around the sleeve on the end of the tube, then applied some lube to Matt's cock before slipping it over his cock.

"Just relax." She assured him as she gave the tube a few pumps. Matt could see his cock inside the tube getting a little bigger under the suction pressure. After a minute, Pauline released the pressure and then pumped it back up again. "We would do this for about ten minutes at a time. There are also these rings we could slip over the base of his penis that would keep him hard when we made love."

After several minutes of pumping and releasing she put the penis pump back on the counter, then stripped completely naked before stepping into the shower with Matt.

Matt's eyes got big as he saw his naked grandmother in front of him.

"What's the matter, sweetie?"

"Uh. Uh. Nothing. I've never seen a naked woman before. You know... in person. My gosh, you look incredible!"

Pauline had large round breasts with an hourglass figure. She has a little extra weight on her hips and ass, and thin patch of hair covering her pussy.

Pauline smiled and blushed a little that he liked how she looked naked. "Thank you, dear. I just see an old lady looking back in the mirror."

"Not even close! You look fantastic, and so sexy." he said.

"Well, I think it's only fair that you get to have a release after that." she said.

She squirted some body wash into her right hand. Standing on Matt's right side with his arm between her breasts, she reached down taking his cock into her hand and began stroking. Matt placed a hand against the shower wall to steady himself when his knees began to shake.

It wasn't more than a minute when Matt was furiously pumping her hand. Pauline felt his cock become even more rigid just before the pulses of cum rushed out the end of his cock and into the palm of her hand. When she sensed he was done, she took the shower head and sprayed all the soap off.

Pauline took a towel off the hook outside the door and handed it to Matt as he stepped out. She stayed in the shower and squirted a little more soap into her hand and began masturbating herself. "After that I think I could use a little release myself." she said smiling to him.

Matt was frozen watching her rubbing her pussy. Finally he regained his senses and stepped back into the shower. "Grandma, I think it's only fair I should help you like you helped me." He squirted a little soap onto his hand and slipped his hand under hers to take over.

Pauline leaned back against the shower wall and spread her legs a little. "Oh Matt, it's been years since I've been touched down there. Mmmm, That feels so nice, sweetie."

Matt used his four fingers flat against her mound making little circles. Matt pushed a little deeper between her thighs letting his middle finger slip between her lips continuing his circular pressure against her pussy and sliding up and down.

Pauline's legs began to tremble as a crushing orgasm rushed through her whole body. Her hips pushed into his hand fucking his fingers as wave after wave of her orgasm put her into a humping frenzy.

Her pussy became so sensitive she needed to slip her under his. Smiling at Matt, she assured him "When she finishes, she gets so sensitive. Thank you, sweetie. It's been years since I've had one that good."

After spraying herself clean of the soap, she looked over and saw Matt had another erection. She took him by the hand and led him to the bed where she had him lay down.

Kneeling on the bed on Matt's left side, she leaned over him placing a hand next to his right hip with her mouth directly above his cock. She felt her right breast brushing against his stomach. Lowering her head she took his whole cock into her mouth.

Matt placed his left hand on her ass and began rubbing as he felt the warm wetness of her loving mouth engulfing his cock. He moved his hand under her breast feeling it's heft and softness. Pauline moved her head up and down keeping the suction pressure on his cock while swirling her tongue all around it.

"Better slow down, Grandma. He won't last long like that."

Pauline never slowed down or changed her cadence. A few seconds after his warning, he exploded into her sucking mouth unloading pulse after pulse of cum. When she felt his cock begin to soften she let his cock slip out between her lips keeping the cum in her mouth. After swallowing, she smiled looking at Matt "Feel better?"

"You have no idea. I've never had anyone do that for me. Hell, until a few minutes ago I've never seen a naked woman before."

"I love you, Matt, and want to help. I have an idea for tomorrow morning you might like. Would you like to sleep in here tonight since it's Friday and you have tomorrow off?"

* * * * *

Matt woke up to the smell of coffee. He noticed a steaming cup on the nightstand. He looked around for his grandmother and heard the shower running. He hopped out of bed and went to join her in the shower. Pauline was just about done when Matt stepped in.

"Is it okay if I join you, Grandma?"

"Of course you can." she said looking down at his fully erect three inches.

After soaping and rinsing each other off, Pauline led Matt back to the bed. "I wanted to show you that what you have is enough. It's actually a little more than your grandfather and definitely thicker."

"Would it be okay if I licked her first? I really have no idea what I'm doing but I would love to learn."

"Mmmm. I would like that." she said laying on the bed with her heels on the bed rails. She spread her knees offering her pussy for Matt to explore. Matt knelt on the floor between her legs and lowered his face close to her pussy.

"I've seen this on the internet, but don't know what women really like."

"Just explore and have fun, sweetie. I'm sure I will love it."

Matt lowered his face against her mound slipping his tongue between her lips. He heard his grandmother let out soft moans of pleasure as he moved his tongue up to her clitoris and back to her vagina. He felt so proud that he could give a woman such pleasure.

"Mmmm. Oh Matt. That feels so nice." she said as she rotated her hips under his face.

Matt found her swollen clitoris and sucked it between his lips holding it for a moment and then swirled his tongue around it before releasing. Then sliding down finding her vaginal opening plunging his tongue as far inside her as he could reach.

Pauline's moans got louder and hips moved faster as Matt feasted on her pussy. "Oh baby! I'm there! I'm gonna... Ughhh!" She reached down holding his face against her as a climax rushed through her shaking body.

Finally she released Matt's head and slipped a hand between his face and her mound. "Oh my! It's hard to believe that was your first time. You really know what you're doing down there!"

Pauline moved up to her pillow and held out her arm inviting Matt to lay his head on her shoulder. After a few minutes Pauline asked "Are you ready to try something else?"

"Of course, Grandma."

They sat up on the edge of the bed.

Pauline got some lube from the night stand and squirted some on Matt's cock with a little left over for her pussy. She got on her knees on the edge of the bed with her knees spread apart and lowering her shoulders to the mattress.

"I'm guessing you already know where he goes." she said giggling.

Matt got behind his grandmother and guided the end of his cock to her open vagina. Placing his hands on her hips, he slowly penetrated her opening moving all the way in, pressing his hips tight against her ass.

Holding his hips tight against her ass he could feel her warm wet pussy walls engulfing his cock. It was better than he ever imagined it would be. "Oh Grandma, you feel incredible. I never thought it would feel this good."

Pauline was happy that Matt could experience sex. Although she didn't feel him penetrate very deep inside her, she certainly felt him opening her vagina with his girth. She wiggled her ass a little to encourage him to start moving.

Holding her ample hips in each hand he started moving slowly pulling his hips tight against her ass pushing his little cock inside her as far as he could with each push of his hips. He picked up the speed and force of each thrust causing a ripple of waves over her ass.

"Oh Grandma! He's going to finish." Matt said grunting the words.

"Keep him inside her. Don't take him out." she said.

Matt's knees trembled as he erupted inside his grandmother. His body shook as he felt multiple pulses of cum rushing through his cock. Matt slowed to a stop still holding her hips and pressing tight against her ass. Matt could feel Pauline's vagina squeeze his cock. After a few seconds his little cock began to get softer... and shorter until her vagina squeezed him out.

Pauline returned to her pillow holding her arm out for Matt to lay in her arms.

Matt finally broke the silence "I had no idea I would ever be able to do that. I always figured I would never have sex, at least not with a woman. Thank you, Grandma. That was the most incredible experience I've ever had."

"Oh Matt. I'm glad I could help you. If you didn't make her climax a few minutes ago, I'm sure she would have that time. Having you inside her felt wonderful." After another long pause she continued "Tell you what. Until you have a girlfriend, we can have fun from time to time. That is, if you want."

"Are you kidding?" After a pause he continued "If I'm honest I have to tell you, Grandma, a lot of times when I take care of him myself, I'm actually thinking of you."

Pauline smiled "Really? An old lady like me? What do you imagine when you're having fun with your willy?"

"Wow, I guess everything. You have amazing boobs. I think of them a lot. That really gets him hard. Until yesterday I could only imagine what you looked like naked. You're so much more beautiful naked than I ever imagined."

You're sweet. I'm so glad I helped when you took care of him.

* * * * *

During breakfast, Pauline asked "So what are you planning to do today?"

"I don't have anything planned. I think I would like to just hang out with you. Do you have anything on your to do list today?" he replied.

"Actually I didn't have anything planned, but now I'm thinking about getting some new lingerie. Maybe some things you might like?"

Matt thought for a few seconds "I love sexy lingerie."

"Like what?" she asked.

"Wow. You name it, I love just about anything."

"I have a few things, maybe you'd like to see them."

"Especially if you're in them." Matt said playfully.

"Let's go see."

Matt sat on the edge of the bed while Pauline pulled everything out of the bottom drawer of her dresser. She held up each item to her body to show Matt to see his reaction. She decided the on the items to try out first. Matching lace bra and panties, garter and stockings, and a sheer kimono robe.

"Okay, you need to go into the living room while I pick out something to try on for you." she said.

Matt got another cup of coffee and waited in the living room. A few minutes later Pauline came in wearing her lingerie. He could clearly see her panties and bra through the sheer kimono robe. "Oh my gosh. You look so hot!" he said pushing a hand into his crotch.

"Thank you, sweetie. I thought you might like it."

"Like it? That doesn't even begin to describe it. Looking that hot makes me weak."

Pauline asked "Would it be okay if we try something?"

"Anything. Anything at all."

"Good. Take your clothes off." she instructed. She didn't have to say it twice. Matt was completely naked in just a few seconds. Pauline slipped her thumbs into the waist of her sheer lace panties and stepped out of them.

"Put these on." she said holding her panties out for Matt.

Matt wasn't sure where this was going, but trusted his grandmother completely. He looked them over to figure out which side was the front then stepped into them.

"Oooh. I like those on you." Pauline said smiling.

"Really?" Matt said still not sure about the whole thing.

"Oh my, yes." she said looking at the tent Matt made in her panties. She sat on the edge couch in front of Matt rubbing her hands across his cock and ass in her panties.

Pauline dragged her fingernails across the front of the panties causing his little cock to twitch and jump. She hooked the waistband under his balls wrapping her forefinger and thumb around the base of his cock and gently began stroking him.

She scooted up to the edge and moved her mouth to his cock and said "I'll hold still and you move in and out."

She put her lips around the head of his cock and put both hands on Matt's ass cheeks. He began moving in until he was completely inside her mouth. Pauline squeezed his ass cheeks digging her fingernails into his cheeks. She relaxed her grip and Matt began moving his hips in and out.

After a few moments Matt instinctively held Pauline's head with both hands as he fucked her sucking mouth. He felt her tongue swirling all around his head and shaft coaxing his cock to explode inside her mouth.

Matt's knees began to tremble as the pending explosion swelled up from deep in his balls rushing up through is cock for release. "I'm not going to last, Grandma. He's gonna finish, he's.... Ughhhh!"

Pauline held his hips steady when she felt him shaking. She felt the head of his cock expand and his shaft becoming even more rigid moments before the first pulse of hot semen hit the back her mouth. She swallowed his hot seed as quickly as it arrived.

Matt slowed to a stop still twitching in her mouth as her tongue swirled around his softening cock. Pauline released his cock from her mouth and pulled the waistband of her panties from under his balls and tucked his cock into the panties.

"There! I think he's happy." she said lightly patting his cock through the lace.

Matt leaned forward giving Pauline a very long kiss on her lips. Before that passionate kiss, Pauline was content giving Matt a blowjob and letting this session be just for him. After that long sensual kiss from Matt, her pussy came alive wanting more.

She stood up pressing her body against Matt and planted her lips on top of his for another very long and passionate kiss. Since Matt was wearing her panties he knew she wasn't wearing any. He reached down with his right hand slipping his middle finger between her lips feeling her she-cock was wide awake.

Matt sat on the couch instructing Pauline to stand up on the couch straddling him with her feet on either side. She spread her feet further apart lowering her pussy to Matt. She had both hands on the wall to steady herself.
He reached behind her taking a handful of ass flesh in each hand pulling her hips closer to his mouth. He started by swirling his tongue around her clit before sucking her between his lips into his mouth. Pauline gasped as he sucked her between his lips.

Matt sucked her clit, applying pressure, then releasing the suction over and over all while his tongue swirled around her. His right hand squeezing and caressing her ass cheek and left hand moving to her pussy slipping two fingers into her vagina.

Pauline's hips rocked like she was frantically fucking Matt's mouth with her clit as a crushing orgasm rushed through her entire body that resembled a seizure. She pressed her pussy hard into Matt's face, pushing his head into the cushion as her body shook.

A few moments later with her legs still shaking, she lowered herself to her knees to straddle Matt's lap. She held Matt's face with both hands and planted another long passionate kiss tasting herself on his lips.

"Thank you, Matty. That was incredible." she said.

Matt smiled "You've really blown my mind. Thank you. I didn't think that I would ever get to experience sex, you know, real sex. With a real woman. I was beginning to think I would wind up on the receiving end of a gay relationship if I wanted sex. You're amazing!"

"Oh, Matt. You were making it out to be something a whole lot worse than it is. You can, and will have an amazing relationship with a woman. Don't worry about that. And I want you to promise me one thing."

"Okay, Grandma. What?"

Pauline continued "Promise me you will meet women, date women, find that woman, you know, the one. We can explore a physical side to our relationship for now, but it would break my heart if you let that stop you from meeting and dating."

"I get it. I promise I will be open to dating women. I've always avoided it before but I guess I wont put the walls up when I meet someone."

"Good. For the time being, we can continue as we are. Also before, or after a hot date, we can take the edge off so you aren't in a hurry to get physical before you're ready. Besides, getting someone pregnant before you're ready will change the trajectory of the rest of your life."

"Thank you, Grandma. Until I do have a girlfriend, can you be my girlfriend for now?"

"That would be wonderful, sweetie." Pauline assured him. "Can I take you to dinner tonight?"

"No. But as my girlfriend, I will take you." Matt replied with a smile.

* * * * *

After dinner, they cuddled on the couch and watched a movie before bed. Matt said goodnight and was heading to his room. Pauline reminded him that he didn't have to work Sunday and suggested he sleep in her bed.

Matt woke up to the smell of coffee waiting on the nightstand and the sound of the shower running in the bathroom. He took his cup into the bathroom and let Pauline know he will step in and take a shower when she is done.

He joined Pauline in the kitchen just as she finished making breakfast. Most of the discussion was about work and chores. Then Pauline asked "Did you enjoy wearing my panties?"

"I have to admit, I did."

"Enough to try it again?"

"Of course. If that's okay."

"I bet you might enjoy some other things."

"Like what?"

"Well, your grandfather would sometimes wear panties, and sometimes a pair of stockings when we made love. I'll tell you, feeling other legs in stockings against your own is incredible. He used to tell me he always loved the feeling of legs in stockings, but feeling the stockings from the other side was fantastic."

Matt thought about it for a moment "I guess I can try it."

"I'm going to the store a little later to pick up a couple things you might like to try."

"You want me to go with you?" Matt asked.

"Are you okay being seen in the ladies lingerie section of the store?"

"Hmmm. Maybe I'll just wait here and be surprised." he replied. They both chuckled.

Later that afternoon Pauline returned home with a bag and went to her bedroom. She dug through a drawer and took out an open bra bustier, garter belt, and a pair of dark stockings. When she had stripped and put them on, she checked herself out in the mirror, even without the panties she thought it looked good.

Pauline opened her door and called Matt to her room. When Matt came in he froze in the doorway. "Woah! My eyes are having a heart attack! You look incredible. I mean really hot!"

"Thank you, sweetie. I have something for you, too." She reached into her bag and took out a couple pair of panties and stockings. "I think maybe you can try these on." holding out a pair of hold-up stockings.

When Matt was naked, he was hard as a rock. Pauline showed him that when putting them on, there are some silicone rings inside the tops that help them to stay up. Matt slipped them on and stood up.

"Oh my. Those look great on you. You have great legs for stockings." she said admiring how he looked.

"They feel nice. It's like every nerve below my waist is wide awake!"

"Perfect! That's how grandpa felt when he put on stockings."

Pauline got a towel out of the bathroom, then took a bottle of lube out of the nightstand. After spreading the towel on the bed she got on the towel facing up.

"Would you like to have some good ol' fashion sex?"

Matt crawled onto the bed between her legs. Pauline handed him the lube "Put a little on her, and a little on him." she instructed.

When he was done, Pauline pulled her knees back and spread them open wide. Matt didn't need her to tell him what to do next. He positioned himself over her guiding his cock to her vagina slipping all the way in. It wasn't deep, but Pauline certainly felt his girth opening her pussy.

"Mmmm. Yesss. That feels nice." she cooed.

Matt held his upper body up off her as he began slowly moving in and out. He loved the view of Pauline's breasts slowly flowing up and down as he fucked her.

"Oh my gosh. She feels so amazing." Matt said.

Pauline's hooked her heels behind Matt's ass and started pulling his hips into her open legs harder. He took the hint and started pushing his hips into her with a little more force. He loved the view of the ripples in her tits every time he buried his cock into her.

Pauline exclaimed "She is almost there. Fuck me harder, baby. Harder."

Matt picked up the force slamming into her harder. The room was filled with wet slapping sounds and soft grunts.

"I'm not going to last like this." he said.

Panting and grunting, she said "Finish inside her. Cum inside me, baby. I'm there. I'm there! Ughhh!"

Matt felt a ball of fire welling up in his gut then rushing streams of cum into Pauline. Matt kept slamming into her. Pauline pulled her legs back holding them even wider as they both had a climax together.

Matt finally slowed to a stop, still inside her. She could feel his cock twitch and jump inside her every few seconds. Pauline's quivering vagina squeezed him out as he got soft.

He rolled off and laid next to her. Pauline rolled onto her side laying her head on his shoulder, hiking her knee over Matt's thigh.

"Still think you can't have sex with a woman?" she asked.

"Well, you have to admit. It takes a very understanding and loving woman."

Story by - Actual_Mom via Literotica