A (step-)grandmother & grandson develop a safe place in their relationship where they can share and explore their innermost fantasies with each other without fear of being judged.
After completing high school, Mike enrolled in a college about 60 miles from home, but the school was less than a mile from his grandmother’s house. Everyone in the family thought it was a good idea if Mike stayed with his grandmother during the week, and went home on weekends, at least most weekends.
His grandmother was especially fond of this idea. Carol had been living alone for the last eleven years since her husband passed away, and looked forward to having someone to care for. Mike was her only grandson and they were especially close. During the summer for the last few years, Mike would stay with her, sometimes for a couple weeks at a time.
Carol was a fairly typical grandmother. She wasn’t thin, but she wasn’t fat. She was curvy and carried her extra weight well. Her chest was full and round and wore a DD bra. She was 66 years old, but you wouldn’t know it by looking at her. She is a natural blonde and kept her hair that color, fairly short and nicely styled.
Mike was 5’~11″ and 170 pounds with a narrow waist and broad shoulders. When working in the yard during the summers, Carol would watch him work. He would usually be wearing shorts and take his shirt off. Carol would think to herself that Mike was becoming quite a man and will have to beat the girls off with a stick.
Mike would always open the car door for her when they went somewhere together. It didn’t matter if they just went to the store on a quick errand, he always opened and held her door. When they would to go out for dinner, they always dressed up. When he held her door he would get a glimpse of the tops of her stockings when she was getting in or out of the car. Every time he did, he felt a tingle in his pants. He felt that same tingle every time he looked down her blouse at her cleavage when she bent over. He always admired her ample ass and hips swaying when she walked away. Mike thought his grandmother was perhaps the sexiest woman he knows.
Some evenings after they go to bed, Mike would put on a pair of his grandmother’s stockings and panties while he masturbated either thinking of her or looking at his porn magazines There was something about her underwear that would make his climax even more intense.
One Saturday morning when Mike was staying the weekend, Carol got up and headed toward the kitchen. When she rounded the corner, she saw Mike in the kitchen at the sink with his back to her. She was stunned and puzzled at what she saw.
He was naked except for a pair of sheer pantyhose with the legs cut off a little above the knees. Her eyes were immediately drawn to his tight nylon clad ass. She realized that Mike was still unaware of her presence and she stood there just looking at him.
A moment later, Mike put down the cup he was drinking from and turned around. Even though Carol knew she could clearly see through the sheer pantyhose and was about to see his cock, she was still shocked to see the size of Mike’s cock pointing down toward one leg being held tight against his body. It wasn’t the little boy penis she saw years ago. His cock wasn’t completely hard, but Carol could plainly see he was very much aroused.
Mike, on the other hand, experienced a whole new level of shock and horror seeing his grandmother standing in the doorway. Both of Mike’s hands were a blur to cover his crotch as fast as he could, turning slightly to the side while covering himself.
“Holy crap!! … Sorry Grandma. You never get up this early.” he blurted out.
“It’s okay, sweetie. I know what they look like. So the obvious question here is what’s up with the pantyhose?” she asked with a little smirk.
Still covering himself, Mike replied, “I’m heading out for a bike ride. I wear these under my shorts to avoid chaffing.”
“Very smart. Good idea actually. You go ahead and I’ll wait for you to get back and I’ll make us some breakfast.” she said wearing a broad smile.
“That’s okay, grandma, don’t wait. It will be a couple hours.” he replied.
“Okay, sweetie. Have a good ride.”
Carol smiled to herself as Mike tried to get past her without exposing his crotch. It had been a lot of years since she saw a man’s penis and found herself thinking about Mike’s most of the day and just how good he looked.
# # # # #
A few nights after the kitchen incident, Carol got up to get a drink of water. She noticed a light coming from under Mike’s door. She thought he must have fallen asleep doing homework and left the light on. She quietly opened the door so she could reach in and flip the light switch.
What she saw shocked her. Carol stood at the doorway and watched Mike sitting at his desk with his chair turned toward the door wearing a pair of stockings and an open bottom girdle masturbating. He was leaning back with his eyes closed and legs spread wide and stretched bostancı escort bayan out. Carol didn’t move or make a sound, watching for several seconds.
She finally decided to make her presence known and lightly knocked on the door.
“Oh crap!!” Mike sat up and turned away from the door. “I’m really sorry Grandma!”
“Mike, it’s okay. I really didn’t mean to invade your privacy. I just thought you fell asleep with the light on and was only turning it off.”
Mike, still sitting in the chair with his back to the door, said “I’m so sorry.”
“Mike. It’s okay. Really. I know everyone has a thing that flips their switch. It’s okay… Honest.”
Mike didn’t move or make a sound.
Carol walked over beside Mike to sit on the edge of the bed. As she was about to sit down, she noticed two magazines on Mike’s desk. They looked like porn magazines, but not the usual Playboy type. One was called “Shaved”, and the other was titled “Over 50”. Carol said “I’m sorry I interrupted you and we have to get past this.”
Still covering his crotch, Mike turned his head and looked at Carol. She was wearing her nightie. It wasn’t a sexy nightie, but it was sheer enough that Mike could clearly see Carol’s areolas and nipples the size of pencil erasers making a tiny tent on the fabric.
Mike felt his cock beginning to get hard again looking at her tits. Carol saw Mike’s eyes were fixed on her chest and also noticed his hands pressing tighter into his crotch. Then looking at the floor, he said “I’m sorry, Grandma.”
In a reassuring voice, Carol said “No sweetie. You have nothing to be sorry about. I’m sorry I invaded your privacy.” She continued “Look, sweetie. I’m not a prude, I’m not judging you. And I want you to know something.” there was a long pause “This is important, so look at me and listen carefully.” Mike raised his head and looked at his grandmother’s face as she continued “THIS… right here… with me… THIS… is a safe place for you. I’ll never betray your trust, I’m not going to judge you, I won’t laugh at you, or belittle you.”
Mike said “I’m sorry. I just feel so ashamed.”
“Oh sweetie. I don’t want you to feel like that. I’m completely supportive and okay with this.” she replied.
“It just makes me feel like some kind of perv that someone found out. Especially you.”
“I feel bad I interrupted and you didn’t get to finish and would like to help.” Carol said.
Mike looked at Carol and she saw the question mark in his expression.
“You can go ahead and finish what you were doing. I’m guessing you were thinking of naked women when I came in? Or… was it guys?”
“No. I’m not gay if that’s what you’re asking.”
“It’s okay sweetie. I couldn’t be completely sure with what you’re wearing.” She could tell Mike was reluctant. “It’s okay, sweetie. Honest. Most of the men that wear ladies things are completely heterosexual, and there’s probably a lot more that want to but are afraid to. I get it, and I’m perfectly fine with it.”
Carol waited a few seconds, then said “I know I may not be much to look at, but I hope this helps you. Turn your chair toward me.” Mike did as she asked. “Like I said sweetie, THIS… ME… right here, is a safe place for you. Not just this house, but ME. I’m not judging. In fact, I think you look great!”
She stood up and lifted her nightie over her head and was completely naked in front of Mike. Then sat back down on the bed and spread her legs. Mike was now focused on looking at her pussy. She doesn’t shave it, but the hair wasn’t thick and bushy. He could see the lips of her pussy and could also see her clit protruding.
It was like Mike wasn’t sure what he wanted to look at more, going back and forth between her large DD tits, and her pussy.
“Oh Grandma. I’ve always thought you are the most elegant, sexy woman I know. My eyes are having a heart attack! Really, I’ve never seen a naked woman, a real woman. You know, in person before. You look incredible!”
“So this will help?” she asked.
“Well… cards on the table?” he asked.
“Of course, dear.”
“I have to admit,” long pause “nevermind.”
Carol scooted back to the edge and took Mike’s chin between her thumb and finger and pointed his face toward hers. “Mike. Like I said whatever it is. Doesn’t matter. It’s safe with me, no judging.” she replied.
“Okay. Well,” another long pause as Mike reconsidered what he was going to say, then just decided to come out with it “most of the time, I am thinking of you when I… you know… when I do it.”
Carol was touched, and more than little surprised. “Oh my. I would think a young guy like you would be turned on by young women.” there was a long pause “So this will help a lot then, huh?”
“Uh huh.” Mike leaned back in the chair uncovering his cock which was now a raging erection. He stretched his legs out showing his grandmother a full view of his cock sticking out under the edge of his open girdle.
Without saying ümraniye escort anything, he started stroking himself as he looked at her body. Carol sat back against the wall with her legs wide open facing Mike. She began to trace over her lips with her index finger, stopping to swirl her finger around her now swollen and erect clit.
Carol’s left hand cupped her tit while her right fingers rubbed her pussy directly above her mini-cock. Her eyes were glued to Mike’s hard cock being stroked. She was a little surprised at the size. He was long, thick, and straight. Carol thought to herself some young lady is going to be a very lucky girl.
Exposing his masturbation fantasies, and now his hard cock to Carol added a whole new level of pleasure to masturbation. Then he remembered he was still wearing a girdle and stockings which raised his level of excitement even more. He knew he would be blowing his load any minute.
He reached over with his free hand and took the hand towel off the desk and draped it across his girdle, then announced, “He’s not going to last much longer.
Carol was panting, then licked her lips and said “It’s okay sweetie… I’m there, too. I’m there, baby… I’m there!”
Mike felt the explosion welling up in the pit of his stomach and surging through his groin. He pointed his cock up toward his stomach where he placed the hand towel. The first blast of cum shot out the tip of his cock with so much force it hit his chin. Each pulse of cum had slightly less velocity as the previous and the trail of cum finally led from his chin to the towel.
Carol’s hand was a blur on her soaked pussy while she watched Mike cover his chest with cum. Her whole body tensed and began shaking as her climax took over. Mike could see Carol biting her lower lip as convulsions raked her body. Small droplets of fluid flew in every direction.
Mike didn’t want it to end so he kept stroking to milk every last drop from his balls until Carol’s body finally relaxed and her hand quit moving.
They were both panting and looking into each other’s eyes. Neither said a word. Finally, Mike took the towel and wiped off all the cum on his neck and chest. He then sat up and held it out to Carol.
Carol took the towel. She looked down between her legs and saw a big wet spot on the bed and said “Oh no! I’m so sorry.” The bedspread had already been pulled back and the wet spot was on the sheets. As she got up, she turned around and began wiping the sheet with the towel.
Carol was bent over with her ass at eye level right in front of Mike’s face. With Carol bent so far over, he could see her pussy peeking through her thighs. Mike tipped his head a little and looked past her hips to admire her huge tits hanging and swaying under her.
Mike felt his cock getting hard again. He quietly leaned hack in the chair and began stroking his shaft again as he admired the view. Carol straightened up and was turning around toward Mike. He instantly let go of his cock and sat up straight.
“I’m so sorry, Sweetie. Come and sleep in my bed tonight and I will change the sheets tomorrow.” she said.
“That’s okay, Grandma. It’s fine.” Mike replied.
“No. Come on. Let’s go to bed.” Carol held out her hand to Mike. Mike knew there was no point in protesting, he had to comply. His cock was relaxed somewhat as Carol led Mike to her room. “You’ll want to take those off before you go to bed. I’m sure they won’t be very comfortable.” nodding toward the girdle and stockings.
He obediently stripped naked and his cock once again started getting hard and started sticking out again. It didn’t go unnoticed by Carol.
“Okay. You can sleep on that side.” Carol said as she pulled the covers down on her side and slipped between the sheets. Mike did the same.
# # # # #
About 6AM, Carol woke facing away from Mike and was keenly aware that Mike was spooning her. She laid still, replaying the previous evening in her mind, over and over. The vision of Mike in a girdle and stockings stroking himself as he looked at her body is what caused her crushing climax the night before.
Carol became more and more aroused as she replayed it in her mind’s eye. She thought how wonderful it would be to have him inside her. To feel her pussy milking his beautiful cock of every last drop of his hot cum deep inside her.
She wanted to be fucked and she wanted Mike to do it. Carol remembered that guys almost always wake up with an erection and she wanted Mikes. Very slowly she wiggled her hips back pressing her wide hips and ass into Mike and laid still for several minutes not wanting to wake him… yet.
She knew what was about to happen and wasn’t disappointed. Carol could feel Mike’s cock press into the cleft between her ass and thighs. She slowly raised her leg to allow his cock further access. It took only a few seconds when she felt Mike at the entrance to her pussy. She leaned forward a little bit and pressed back slightly and felt him enter her already wet channel.
Even kartal escort though he was still asleep, Mike instinctively pushed his hips forward, pushing his now raging hard cock deeper into her. She needed no additional lubrication, he slipped right in. He suddenly awoke and pulled away. “What’s the matter, sweetie?” Carol asked.
“Oh jeeze. I’m sorry, Grandma.” he replied.
“Don’t be. I thought it was nice. Didn’t you? Would you like to put him back?” she asked.
Mike didn’t say anything, he just rolled back toward her. She raised her leg again offering access to her pussy. Mikes cock found the entrance again and slowly entered her. She felt him penetrate deeper this time. It had been so long since having a cock inside her and it was a tiny bit uncomfortable, but she was horny enough to ignore it.
“That’s it, baby. In and out.” she cooed.
Mike had never felt warm, wet pussy walls wrapped around his cock before. It was pure bliss. He pressed in as far as he could and held himself deep inside her. She could feel Mike flexing his shaft. Carol responded by squeezing his cock with her pussy walls.
She was now well lubricated and felt Mike easily sliding in and out. After several seconds, Carol asked if Mike would like to try something else? Carol kicked the covers down to the foot of the bed and laid on her back raising her legs, pulling her knees back completely offering her wide open gaping pussy to Mike.
Mike knelt in front of her and put the tip of his cock into her pussy. He placed his hands next to her shoulders, holding himself above her so he could see her big tits and slowly slid his entire cock deep into her pussy with his balls tight against her ass.
“I’ve never done this before.” Mike told her.
“That’s okay, sweetheart. It’s perfect.” she said softly. “In and out, sweetie. Does it feel good?”
“Good doesn’t even begin to describe how wonderful you feel.” he replied.
Mike moved slowly, in and out at first. “That’s perfect, sweetie.” Carol whispered. Feeling him deep inside her. Every thrust was exactly what she thought it would be. Glorious.
Mike started picking up speed and fucking her gaping pussy harder. The walls of the room echoed the wet slapping sounds they made as he pounded into her.
Carol saw Mike’s eyes were fixed on her tits. She pressed her tits together for his pleasure. She could feel the weight of her tits and the shock waves ripple through them from the fucking. Carol knew she was about to climax.
“Oh sweetie. I’m there! I’m there baby!” she squealed
“Grandma… I’m going to finish, too!”
“Keep him inside, baby. Fuck her harder! Oh, baby, fuck meee!” With every thrust of his hips, Carol hooked her heels under Mikes ass cheeks and pulled him into her pussy even harder.
Mikes was no longer in control of his own body as he erupted inside her pussy. Her pussy walls were pulsing and milking his shaft to drain every drop from his balls. Her heels were driving into his ass to push his cock harder and deeper inside her.
Mike slowed to a stop with his shaft buried deep inside her. Carol could feel her pussy walls still pulsating around his twitching cock. They were both out of breath and looked into each other’s eyes, grinning at each other.
“I had no idea.” Mike said still grinning.
“It’s a beautiful thing between a man and woman.” Carol whispered back.
Mike rolled off and laid next to Carol, both looking at the ceiling. Mike said “I still can’t believe you were my first. It’s like my wildest fantasy come true.”
Carol broke the long silence “I have an idea. If you would like to…” then she stopped.
“Like to what?” he asked.
“Well, I just thought it sounded a little strange as it was coming out.”
“Grandma, I have completely trusted you because it’s safe. Remember? Well, whatever you are thinking is completely safe with me, too. Okay?”
He had her there, and she knew it. “Okay sweetie. Fair enough. It’s a couple things. First, I’d like us to shop for some other lingerie for you. You really look good in it and I can see us both wearing it together.”
“Really?” he asked.
“Yes. Really, that is, if you want. I can clear out a drawer in here for you to keep your lingerie in. Just in case someone visits so it won’t be in your room. You can keep your magazines in here, too.”
“Oh, crap. Sorry Grandma.” Mike said realizing she took notice of the magazines.
“No, sweetie. It’s fine. In fact, I’d love for us to flip through them together sometime. You can show me the parts that you like the most, and I can tell you what parts flip my switch.”
“That would be wonderful to share that with you.” Mike said.
Carol continued “To be honest, what we did this morning is about the extent of my sexual experience. There are so many things I’ve never done and always wanted to. So right now, we are starting at about the same place and I’m afraid I won’t be a very good teacher.”
“I can’t think of anyone else I would love to learn with.” Mike said.
After a long pause, Carol said “I couldn’t help but notice one of your magazines is called “Shaved”. Does that mean shaved women flip your switch?”
“This is a little embarrassing, but yes.” Mike replied.