Best Christmas Present Ever Ch. 02

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Mom has a plan to help with his girlfriend.
5k words
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Part 2 of the 5 part series

Updated 06/09/2023
Created 05/14/2019
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DomJ69
DomJ69
393 Followers

Thank you Jacky for your support and editing.

*****

Twelve months later, Mary's life hadn't changed much, if at all. She'd been out on a few dates, but hadn't met anyone she liked. Glyn's life had changed quite dramatically. He'd left school and become a trainee mechanic at a local garage, which he enjoyed. What he didn't like was the fact that all his friends had moved away to go to college. All, except Sandy. She had stayed at home to train as a beautician.

Mary was concerned that Glyn was spending so much time with Sandy. Last Christmas she had shown him that he was far too big for a small girl like her, but she was beginning to wonder if she was wrong. Later that night when a movie was ending, she decided to find out if she could help.

"Glyn, Honey, why don't you get us both a beer from the fridge?" She asked with a conspiratorial look on her face.

"Sure, Mom." He replied as he went to get the drinks. As he entered the kitchen, memories of what happened the first time they had a drink together flooded back into his mind. "That was the best hand job ever," he thought. "Could she be wanting to do it again?" His cock twitched and began to grow.

Mary noticed the bulge in his pants as he passed her a beer. Glyn took a seat on the couch and placed a cushion over his lap. "Do you remember the first time we shared a beer?" He asked mischievously.

"Yes I do, but that's not going to happen again." She said, much to his disappointment. "I wanted to ask how you are getting on with Sandy?"

"I get on with her great. You know that."

Mary moved her legs up under her on the chair and sipped her beer. "I know you two like each other, but are you like, boyfriend and girlfriend?"

Glyn swigged his beer. "Not really. We've made-out a few times, but whenever she has felt my, err... You know."

"It's alright, Honey. You can say cock to me. I take it you want to have sex with her?"

"Oh, God, Mom, more than anything in the world." He replied, then guzzled down half of his beer. "Every time she's got me hard, she makes an excuse and ends it."

Mary took a long swig on her beer and composed herself. "This is going to sound strange, okay, so hear me out. I want you to think of yourself as an athlete. All athletes have to train, right? And all athletes need a good coach if they are going to succeed." Glyn nodded and swigged his beer, wondering where this conversation was going. "I've been thinking, what if you were to see a sex coach. You know, someone the same size as Sandy who could train you as to how to have sex with her."

Glyn shifted uncomfortably on the couch. "A sex coach? Do you mean, like, a hooker?"

"I think they're called sex workers nowadays, Hon. But yes, that might be a way to get you trained up so you don't hurt Sandy with that big cock of yours." Mary was startled by what she had just said and looked away as she took another swig on her beer.

Glyn was taken aback by her suggestion and finished the rest of his beer. "I think we're going to need more of these if we are going to continue this conversation." He said, waving his beer bottle, as he rose to leave the room.

In the kitchen Glyn got excited at the thought of fucking a porn star, but then remembered the only hookers he had seen in town were what he considered to be rough. "God knows what I could catch off them?" He thought.

He handed Mary another beer and sat down. "I've been thinking and thanks, Mom, but it's not what I want."

Mary looked at the bulge in his shorts and was slightly puzzled. A nineteen-year-old man turning down sex was not something she expected. "Why not. I'm sure we could find someone nice."

"Mom, could we stop this. It's having an effect on my... On my cock." He said refusing to meet her gaze.

"There's two weeks 'til Christmas and sex lessons was going to be your present. Any ideas what you would like instead?"

"Mom, I'm working now, I don't want you spending your money on me anymore. How about a silly gift that costs a max of ten dollars?"

"That's sweet of you, Hon, but I would like to get you something you want."

Glyn took a swig of his beer and thought. "OK. There is something." He looked his mother straight in the eye. "How about the same as you gave me last year?"

Mary was surprised and she felt her cheeks blush. It was her turn to avoid his gaze and take a sip of her beer. She pictured the soaked panties she gave to him and remembered how she masturbated into them. How she squirted for the first and only time in her life. How she had never come so hard. The memories got her aroused. "If that's what you want. I just thought sex lessons would be good..." She stopped as Glyn raised his hand and interrupted.

"Mom, I... I don't want to fuck some whore. I want to have sex with someone I love. Someone I care about. It just wouldn't be the same."

They were silent for a few moments as Mary thought. "I'm proud of you, Son." She said, feeling her eyes begin to well up. "What you just said just confirmed what a decent young man you are". Now find another movie for us to watch and I'll say nothing more."

Glyn watched the TV, hoping his erection would subside soon. "Me, decent," he thought. "I just asked my mom to masturbate into her panties and give them to me for Christmas. That's not decent. Me jacking off into her used panties, that's not decent. Me wondering if she's as turned on as I am, is not decent. She must be thinking about it. Oh, God I wish my cock would go down."

Mary knew how much her son loved Sandy and she was determined to help. Throughout the following week she searched the net incessantly for information on how a man with a big cock could have sex with a small lady. All she found was porn with guys with big cocks and male prostitutes with big cocks. "Purely for research purposes," she told herself as she watched some of the videos. They brought back memories of her son's big cock and she stopped when she realised how wet she was getting. "Was that because of the video, or Glyn?" She asked herself, not wanting to answer the question.

When she saw an advert for a local gigolo with a big cock, a plan took seed in her mind. She took out her phone and typed in the number. Her heart began to race. Twenty minutes after agreeing a price, she rang Mario's doorbell and waited nervously.

"Hi, I'm Mario and you must be Mary. Please, come on in." Said the tall, dark, handsome man of Italian descent. Mary rushed inside, not wanting any onlookers see her enter. She took a seat in the living room and Mario sat on the sofa next to her.

"So, Mary, what can I do for you today?"

"I, um, err...", her mind went blank as she forgot what she had planned on saying.

"Mary, it's ok, take your time. Would you like a glass of wine to help you relax?"

"No, no, I'm fine thank you." Blurted Mary, all flustered. "I'm here for just research purposes. Here's the fee we agreed upon." She said as she handed him the money.

"And what research would that be?" He asked seductively.

"My, err... My partner has a very big cock and I think he would hurt me if he were to, you know, put it inside me. If yours is as big as you say, then I think you might be able to help."

"I'd be delighted to help such an attractive lady as yourself." He said, placing a hand on her knee. "Wait here a moment." He smiled at her, then left the room.

Mary wondered "What am I doing? What's he doing? Oh, God, I should leave now. Control yourself, Mary, you can do this. Yes, I can, but he is gorgeous."

Mario returned with two glasses of white wine and passed one to Mary. "Here, I think this will help both of us. If you don't want it, just leave it on the table." Mary accepted the wine and took a large sip. "How big is your partner, Mary?"

"He's um, he's just under ten inches and it's thick." Images of her son's cock came to mind and she could feel her face redden.

"That's big," Mario replied. "I can see that might be a problem for such a petite lady as you. Okay, I'll tell you what I would do if I'm with a lady like you. Firstly, I've got to make sure you are completely relaxed. Soft music, candlelight and a massage usually does it. Then the foreplay begins. You will need to be receptive, if you know what I mean?" Mary nodded. "I usually begin with stroking your hair and kissing your lips, before moving down your body."

Mary could feel her heart race as Mario continued. "I will caress your breasts until your nipples are hard and then I will move further down. I will massage your inner thigh, then stroke your pussy. If you are ready, your pussy lips will be visible. If not, I will perform cunnilingus on you until you come for the first time with me."

Mary's heart was pounding against her chest. Listening to all the things this hunk of a man was going to do to her was getting her turned on. She raised a hand to stop him. "Err, Mario, would you mind not referring to me. Could you use 'her' or 'she'?

"Sure, no problem. Whatever you want, Mary." He said. She looked away when he gazed into her eyes and smiled. "Once her pussy lips are nice and red, I'll check if she is sufficiently wet before continuing. If she isn't, I'll apply some lubricant to both my cock and her pussy. When she's ready, I gently ease my cock into her and stop after five inches for her to get used to the size. They usually give me a signal to continue and then I slowly ease my cock in as far as it will go. If I press against her cervix, I stop and draw back a little. Then I'll look down at my cock for a measuring point of how far I can go. Once I know that measurement, we would continue to have passionate sex."

Mary took a sip of her wine to try and hide her embarrassment. "But how do you... How do you stop yourself from going any further?"

"Practice." He said and drank his wine. "This is how I make a living. If I were to hurt any of my clients, they wouldn't come back for more."

"Yes, but..." Mary stopped and composed herself. "But when you are about to come, how do you stop yourself from thrusting it all the way in?" She said the word 'thrusting' as she crossed her legs. The heat from her pussy was distracting her.

"As I said, practice." Mario noticed her facial expression turn to concern. "What's the matter, Mary?"

"I don't think he'll be able to stop himself. I think he would hurt me."

"There's a way you can avoid that, but you'd have to take control. It might not be as enjoyable for you, but with practice, he would learn."

Mary's head jerked towards Mario with her eyes wide open. "Please, tell me more."

"I will, but it would be easier to show you, Mary". Mary looked away from his gaze. She told herself she was here for research, but she couldn't stop the lustful feelings. Mario continued: "First, tell me, when was the last time you had penetrative sex?"

"It was... It was three years ago, before my husband and I divorced," she said, almost feeling ashamed admitting it had been so long.

"That's not long, Mary. I've known many women who have waited far longer than you have. For you to take control, I think it would be good for you if you had some practice before you have sex with your partner."

"What?!" she said in surprise. "You think I should practice with you, now?"

"Showing is far better than telling and you want to get it right for your partner, don't you?" He asked with a knowing smile.

Mary shifted uneasily in her chair. She was amazed she was actually considering allowing this man she had just met to fuck her. "I, I didn't... That's not..."

He rose to his feet, his hardening cock prominent beneath his jeans and in Mary's sight. "Mary, you have already paid for it, so why not enjoy it. I will be gentle and teach you what to do." Mario took her hand and without any resistance, he led her to the bedroom.

Glyn was in the kitchen cooking when Mary got home. As she sat down at the table he noticed she looked both happy and tired, in a kind of sexy way. "What's up, you look happy?"

"Just a good day at work. I can't believe the amount of... Of work I processed today. Pass me a beer would you, Hon."

As he passed her a beer, he smelt an aroma of... of sex. "You look kind of... Funny." 'Fucked' was the word Glyn was about to use.

"Just tired. Do your old mom another favour and run me a bath. I've got some thinking to do."

"Sure, no problem, but only if you never call yourself old again. You're not old. You could get any man you want." Glyn left the room wondering if his mom had recently had sex. The thought of her fucking made his cock twitch and he was relieved he had an excuse to leave the kitchen. A few minutes later he entered the kitchen.

"Glyn", she said quietly. "You can say no and I really won't mind, but would you spend Christmas Eve at home? The present I've got for you, well, if you don't like it, I don't want to spoil your Christmas."

They were both thinking about the previous Christmas and they both sensed the sexual tension in the air.

"Sure, Mom. I'd love to." He said and turned to continue cooking. "Dinner will be ready in half an hour."

"Thank you. I'll go and take that bath now."

Nothing further was said, but the sexual tension was palpable throughout the week. Glyn wondered what his present would be - would it be a repeat of last year, or had his mom got him someone to fuck. His cock was constantly getting erect when in his Mom's presence. Mary had noticed the bulge in his jeans a few times. The first part of her plan was to wear sexier clothes around the house. Instead of changing into comfortable casual clothes, she stayed in her work clothes and undid a couple of buttons on her blouse. Glyn had noticed her skirts were shorter than she usually wore and that she was exposing her cleavage whenever he entered the room.

Christmas Eve arrived and Mary was relieved that Glyn would be out of the house for the day. It would give her some time to relax after she had finished the preparations for the following day. Glyn was meeting up with friends who had returned home from college and had promised to be back at eight o'clock.

As Glyn entered the house that evening, Mary walked from the kitchen with a glass of wine in one hand and a bottle of beer in the other. He was gobsmacked at her outfit and his jaw dropped. She wore an off the shoulder red cocktail dress with black stockings and heels. She looked stunning and was pleased with the effect her outfit had on her son.

"Tonight, I'm Mary, not Mom, okay? She said as she handed him the bottle and headed into the living room. Glyn studied her figure from behind and felt his cock twitch.

"Okay, Mary. I've got to say you are looking beautiful tonight."

"Thank you. I'm glad you noticed." She replied as she sat down and sipped her wine. Glyn took his seat on the sofa. "Glyn, you I know I love you and wouldn't do anything to hurt you."

He nodded and uttered: "Yes, Mom. Sorry. Yes, Mary."

"There are two conditions you have to agree to before we go any further. Firstly, you have got to promise that if tonight goes wrong, you will forgive me and we will get back to normal tomorrow. Do you promise?"

"Of course I do. I promise."

"The next condition is equally important. If I tell you to stop, you stop, no matter what. Do you promise?"

Glyn could only nod. The thought that he was going to fuck his mother had disengaged his brain from his tongue.

"Tell Mary you promise." She said seductively.

"Mary, I promise." He managed to say.

"There's more beer in the fridge, but don't drink too much". She pointed a remote at the TV and said: "We'll talk again after the film. It's Bad Santa, which I think you'll like."

Glyn could barely concentrate on the film. His near permanent erection was getting uncomfortable and he couldn't stop thinking about his mom. Will she be like that porn star who looks just like her? Will she let me come in her pussy? I can't come across her tits. Not unless she asks me to. Will I be able to make her come? These were just some of the thoughts on constant replay in his mind.

Watching Glyn unable to get comfortable on the sofa amused Mary. His erection was clearly visible beneath his jeans and the fact that she had turned him on, meant things were going to the plan. By the time Glyn had got his third bottle, he had given up trying to hide the tented bulge in his jeans. He simply passed Mary another glass of wine and sat back down. She knew she couldn't get drunk tonight, but also knew she had to be a little light headed to go through with her plan. When the film finished, she turned to Glyn.

"One more drink while we talk." She said as she got up and left the room. "This is for him and Sandy." She told herself as she got the drinks. "If that's true, then why am I feeling so fucking horny?" She asked herself. The thought that she could both help her son and enjoy sex resolved the situation in her mind, and she went back to the living room.

"Right then, Glyn." She began. His attention all hers. "If I do or say anything that freaks you out, just stop. If you get up and walk out, I'll understand and tomorrow we'll be back to normal." Mary took a sip of her wine, impressed at how calm she was. "After you said no to a coach, I went to see a man who instructed me in how you could have sex with Sandy. That is what you want, isn't it?"

A croaky "Yes" was his reply.

"This man taught me what to do and told me you will need quite a bit of practice for you not to hurt her. For you to be able to make love to her properly, I'm willing to teach you and let you practice having sex with me. Have another drink and think about what I just said."

Mary sipped her wine. Glyn could barely manage to raise the bottle to his mouth.

"Don't forget to call me Mary tonight." She said watching his eyes shift from her legs, to her crotch, up to her tits and finally meet her gaze.

"Mary, are you okay with this?" He quietly asked.

"Glyn, your happiness means more to me than anything in the world. I would love to have sex with you if that will make you happy." Mary paused, shocked at how simply she had said those words. "And then you'll be able to have sex with Sandy," she said trying to justify her proposal.

Glyn's head was spinning. He wanted to pull her over to the sofa and take her there and then.

"Will you let Mary teach you?"

"Oh, Mary, I've wanted to have sex with you for so long."

Mary was equally surprised and excited by his response. "Do you know what foreplay is? She asked and he nodded. "The point of these lessons is for you to have sex with Sandy, so I don't think it would be appropriate for you to engage in foreplay with me. Once I'm prepared, I'll teach you how. Is that what you want from Mary?"

"God, Mary, yes!"

"I'm going to go upstairs and... And get ready for you. When I call down, I want you to go to your room, take off your clothes and get into bed. Then the lessons will begin."

Mary could see his face was burning up with passion. His pupils were like saucers and she thought she could see his shirt vibrate to his heart beat. She got up, went to the door and turned to face him.

"When the lesson begins, I don't want you to come too quickly." She reached under her dress and pulled her panties down to her ankles. "I came in these earlier. Use them to jerk off." Like an experienced Mistress, she stepped out of her panties and flicked them over to him.

Glyn watched her leave, then quickly undid his zip to free his cock. He groaned with relief as the pain of his cock straining against his jeans left his body. He looked down at the bulbous head, which had turned a dark red, almost purple. "Don't touch it. Not yet." He thought, then removed the rest of his clothes, picked up Mary's panties and sat down on the sofa. The warmth and the aroma from her panties caused him to bring them up to his nose. He spread them across his face, lay back, inhaled her scent and began masturbating. Moments later he knew he was about to come. His back arched off the sofa and the first jet of spunk erupted from his cock and hit the panties. The second and third spurts splashed against his chin. The final spurt hit him on his chest. Breathing heavily, he fell back on the sofa. "Wow", he thought, "If it wasn't for her panties, I would have come over my own face."

DomJ69
DomJ69
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