My Best Friend’s Mother Ch. 01

Double Penetration

Mark and I had been best friends ever since I could remember. Our families had always been close, especially since my father died when I was really young. I don’t remember anything about him, but my mother can’t help but sing his praises every time he is brought up in conversations. Because I couldn’t remember anything about him I always felt uncomfortable every time he was brought up, so I chose to spend as much time as possible over at Mark’s place. His father wasn’t in his life anymore, having divorced his mother but leaving them the house so that he could go and travel the world, which meant they had a spare room for me to stay however long I wanted.

While Mark and I were very good friends, almost brothers, our mothers were never as close. They were friendly towards each other, but I could tell that my mother resented how much time I spent over at Mark’s, but I couldn’t stand how much she talked about the father whom I had never met. Just because they weren’t friends didn’t mean that Penelope didn’t try to offer my mother a room. My mother was just always too proud, and too stubborn to accept the goodwill. Or maybe she just wanted and liked the constant reminder that the house brought her of my father, her husband.

Sat in Mark’s room, as I did every day, I peeked out the window and saw the most beautiful woman I had ever seen. Wearing a flowery summer dress, dirty blonde hair cascaded down, framing her sharp jawline. Although wrinkles were starting to appear at the corner of her eyes and mouth, her protruding cheekbones and soft, pink lips removed any doubt over her beauty. Even though she was an older woman in her late thirties or early forties, and I myself had only turned 19 recently, I still would have gone after her if I had been able. There was only one problem, and it definitely wasn’t the cleavage that stuck out the top of her dress, it was the fact that she was Mark’s mother, Penelope.

I had never thought of her in any way but as a second mother before. She had always looked after me, made sure I was fed, and had comforted me back when I used to come over and cry about how much attention my mother was paying to someone who was no longer alive, while not giving me any. Sometimes I considered her my mother because she did more than my biological mother ever did for me when raising me. I hadn’t thought of her that way until I walked into her in the bathroom around four months ago.

I was on my way to have a shower but I was distracted by thoughts of college and what I was going to do in the future considering it didn’t seem like my mother was going to support me in going to any of the universities that I was interested in, and I wasn’t smart enough to get a scholarship. I had tried and knew that I would be able to graduate with an engineering degree, but your words definitely wouldn’t and shouldn’t be enough to get someone into a university. Those thoughts were taking up my every thought and I walked into the bathroom without thinking, not having heard that the shower was on. I had gone to leave but had taken a quick glance at the shower before I was stopped in my tracks.

It was the first time that I had noticed how sexy Penelope was. I felt my dick start to stiffen in my trousers as I looked at her voluptuous body, water and soap sliding down as she rinsed herself. My eyes followed her hands down as she massaged the soap into her skin, pressing her tits up towards her face and letting them drop back down, jiggling and bouncing up and down once they fell to their normal height.

I tried to stay in longer so that I could see her wash other body parts but she had already finished rinsing herself off and had been about to turn the shower off so I hurried out, making sure that she wouldn’t hear or see me. I never would have considered staying and watching if I had walked in on her in the past, but something about that scene was different. It was like I had finally been given a glimpse of her as a woman and it was all I could think about.

As soon as I went back to my room, my heart beating out of my chest, I launched myself at my bed, yanking my trousers off and closing my eyes. I hadn’t needed any extra stimulation that day and even now I just had to imagine the scene that I had witnessed and it was enough for me to cum.

“Dude, foods ready, are you coming,” I heard Mark call from the bottom of the stairs.

“I’ll be down in a second!” I yelled back, sighing as I took one last look down at Penelope, wishing that I could do go down there and do what I want with her.

I got up, pushing my erection up and into the waistband of my trousers before rushing off down the stairs and entering the kitchen. I sat down at the table next to Mark and opposite Penelope.

I was extremely hungry and also wanted to distract myself from the reemerging stiffness in my trousers every time I glanced at Penelope. One of those times I glanced at her and found her already looking back at me. The innocent and warm smile that grew onto her face Escort Haramidere distracted me enough to where I dropped my fork underneath the table without even realising it.

“Oh, sorry!” I exclaimed, hastily pushing my chair out and going under the table. I looked around, seeing that it had dropped almost to the other side of the table and went to pick it up.

“Don’t worry about it Dylan,” I heard Penelope’s voice drift in from above. “And I could have picked it up because you’re going to need a new one anyway.”

“Don’t worry about it Mrs Bailey,” I said, taking a glance up to where I knew she was sitting and stopping in my tracks.

I had known that she was wearing a dress, I wasn’t blind, but what I hadn’t expected at all is that her legs would be slightly spread so that I could see her panties. They were only plain white ones, but something about that made them even more attractive.

“I’ve got to go out mum,” Mark said, as I heard his cutlery hit the plate. “James invited me to a party and it starts in half an hour.”

James was one of Mark’s new friends. While we used to hang out all the time together, Mark started getting bored of that and going out to parties more often. He did try to invite me, but I got bored of it all quickly, and tried to get him to stop going as well but he refused. It bothered me a lot at first, but once I realised my attraction towards Penelope I didn’t mind him abandoning us together in the house all alone. It still sometimes stung knowing that I wasn’t as important in his life anymore, but those feelings just seemed to wash away whenever I looked over at Penelope.

Mark and I both used to be on multiple different sports teams, from basketball to football, to swimming and we were always in contention to be the captains, although I was able to collect a majority of the responsibility and what I think happened is that Mark got a bit jealous which is why he started hanging out with people who don’t have the same interests as him, and ones who will never be able to compete with his athletic achievements. Even that was getting called into question nowadays, as while there was still only an inch difference between us, Mark at six-feet and me at six-feet-one, Mark had started to become bloated with all the drinking he was doing. He also wasn’t coming to practise as much anymore, with him having a whole new friend circle, and with how many nights he would come home drunk and not be able to move in the morning because of the hangover.

Penelope deserved better from her son, and without a man in the house to take care of certain things that Mark used to do, that I was now taking over and also her personal needs, I knew that it was starting to become too much for her. It’s why I couldn’t afford to go out partying with Mark even if I wanted to because if I did then who would look after his mother, Penelope?

“Are you coming this time Dylan?” Mark asked as he did on occasion, knowing that I wouldn’t say ‘yes’.

“I have too much to do, homework and planning for our next football match, so I can’t,” I lied, remembering I was under the table and quickly backing out, fork now in hand, before it started to look weird. “Sorry.”

Without even answering, as if he had prepared for me to answer negatively, he was out of the door and I heard the car outside start to drive away.

“That boy…” she said, shaking her head as she trailed off. “…I guess it’s just me and you for the night!”

She was putting on a brave face, but I knew that this was hurting her. Her son was going out, not even asking her and just expecting her to be fine with it. I had matured past that stage, I had been forced to by the lack of support at home, but Mark was still able to do things without thinking about the consequences it had on others.

“What do you want to do tonight?” I asked, as within the last few weeks this had become sort of a routine.

“You pick the movie, I’ll just go and get changed into something more comfortable,” Penelope said, standing up and looking at the plates on the table.

“Don’t worry about it,” I said, already picking up the plates and taking them towards the sink. “I’ll take care of everything, just change and then come down.”

There was a pause where I expected to hear a reply in answer, or her footsteps going up the stairs before I heard a soft ‘thank you’ just before she rushed off up the stairs at a pace I’d never seen from her before.

I shook it off and finished washing up the dishes then got a blanket, put some popcorn in the microwave and sat down, waiting for her to come back down. This time I get together with her is precious because I know that she will never want to get together with me. Not only because of my age, but also because I am her son’s best friend, and like a son to her. There was no way that she would like me as anything more than a second son, but it didn’t mean that I couldn’t try and change that relationship slowly, even though İkitelli escort I knew there was no hope.

I heard her coming down the stairs and turned to look, seeing her long legs coming into view, unobscured as her shorts rode high. Her ass was almost visible and I felt the blood start to flow in my nether region but it was nothing compared to the white tank top she was wearing. It was a bit small, meaning it rode up a showed a little bit of her stomach and she also wasn’t wearing a bra, which was clearly evident by the twin peaks poking through the material. I had a thought, glancing down at her shorts and wondering whether she was wearing anything beneath that, or had gone full commando.

When I looked back up, she was focused on the screen which was on the intro screen before I had pressed play.

“Scream? What movie is that?” she asked, furrowing her brow.

“It’s a good movie, I think that you might like it,” I replied.

I had experimented with different movies and tried to see which one had the got the best reaction from her and what I had learned was that it was either romance movies or scary movies. Romance movies more on the emotional side as she became more sentimental and more sensitive which is I would use that opportunity to cuddle up with her, but with horror movies, it was a bit more physical. Jumping onto me, clutching onto my arm, pressing her tits against me – which is something that I was really looking forward to with the type of shirt that she was wearing – and she had also jumped directly into my lap one of two times, not moving until the film was over. Those times required an astounding amount of willpower to stop me from getting a boner, and I had to think of absolutely horrible things and wasn’t really able to enjoy the experience. It was still worth it though.

“Okay, if you’re sure…” she said sceptically, sitting down on the couch next to me and plopping something – wine – that was in her hand down on the table in front of us. “I brought two glasses as well. Do you want some?”

“I’ll have a bit,” I replied, hoping she would mirror me as I didn’t want her getting too drunk and becoming unable to react to the film anymore. If she passed out then all the fun would be gone. “Are you ready?”

“Of course!”

As I had expected, everything went how I envisioned it would. She jumped around and then flailed her limbs as she grabbed onto me multiple times throughout the movie.

“You didn’t tell me that it was this scary!” she said, screaming as another jumpscare occurred.

I hadn’t considered scary movies as something that I could use to get closer to her at first, but after the first one played and I was able to see how much she reacted, even to things that weren’t meant to be scary, I couldn’t help myself and eventually started looking for horror movies with a lot of jump-scares and tension in between so that we would have the most amount of contact.

She would also bring wine, as she did today, and start drinking would make her more carefree and remove a lot of her inhibitions. It wasn’t to the point where I could capitalise on it, and move our relationship in a more romantic direction, but it did mean that she sometimes had wardrobe mouth functions and didn’t realise it until I had already been able to enjoy everything that had been on show.

At one point I went to grab a little bit more wine, just to calm the nerves, and saw that the bottle had already been drained of its contents.

I looked over at her as she clung to my arm and saw the flush cheeks and her eyes looked unfocused and hazy, as if she wasn’t watching the movie anymore, and wasn’t even here and instead in someplace else.

I waited for the movie to finish, noticing her movements becoming less and less as time passed until I could see her eyes closed as she had fallen asleep. Looking at the time it was almost midnight, and I knew that Mark was going to be returning home soon and with how loud he was when he was drunk she would definitely wake up if she was down in the living room.

I picked her up princess style, basking in how great it felt to have her in my arms before walking upstairs. As I got to the door outside her room I realised just how close it was to the stairs and to Mark’s room. When he came home he wasn’t going to pay attention to the noise, and it didn’t matter if Penelope was in her room or downstairs. The only solution I could come up with was to take her to my room. which was the further room away, so even if Mark started making a lot of noise the door being closed would drown it all out.

I shoved the door open with my shoulder and gently set her down on the bed. She splayed her limbs, disrupting her tank top and giving me a perfect view of one of her tits. I felt my cock start to ache even more and knew that I was going to have to rub one out or it would be an awkward morning.

I looked back at the door, not wanting to leave this room, and decided just to get Çapa escort bayan it over and done with right here and now. Fishing my engorged member from my trousers, laser-focused on her perfectly perky breast. I started pumping my fist, slowly at first trying to imagine that Penelope was awake and encouraging me to continue masturbating to her partially nude form.

‘Give me all your hot spunk,’ She’d say. ‘Spray it all over me.’

The fantasies were getting out of hand and I wasn’t satisfied by just seeing one of her breasts anymore, I needed more. I walked over to her, feeling unsure of my actions the closer I got to her but once my hand grazed her soft, supple flesh I no longer had any doubts in my mind.

I tugged on her top, yanking the other strap from her shoulder and letting both tits burst free. I reach out, gliding my hands over the first breast I had ever touched and marveled at how soft it felt in my hand. I gave it a squeeze, feeling and watching my fingers fall into her soft flesh.

Still pumping my dick with my other hand, I felt the pressure building and knew that I was going to cum at any second. Panicking, I didn’t know where I was going to cum, as the floor was carpet and I wouldn’t be able to get it out. Before I could even think about anything else I felt the familiar eruption as spurt after spurt of cum shot out of my dick, and to my horror, and also pleasure, it all landed on Penelope’s face, with some even shooting into her mouth.

I stood over there, dick not deflating as I looked at my handy work. Although I never wanted to face the consequences that doing something like this brought, in the moment I didn’t regret doing what I did. Watching as the white cream that was covering her face dripped slowly into her mouth was something that I would cherish for the rest of my life and would always be my go-to fab material if I ever needed any.

I knew that I was going to have to get rid of everything on her face because if she woke up and saw what had happened I’d be arrested and sent to jail. I was going to remove it, but I wasn’t going to get a towel or something to wipe it off. I reached my hand up towards her face, watching as it shook, before scooping up some of my cum and pushing it into her mouth. I took the next scoop, getting even more turned on as she sucked my finger in her sleep, unknowingly slurping all the cum from it. By the time I had finished, there was only one more place with a little bit of cum that I wanted to get rid of the same way; my rock-hard cock.

I climbed up onto the bed carefully, not wanting to risk her waking up if I moved her too much and positioned my cum covered tip right above her lips. I felt like I was about to pass out as the tip of my dick sat between her lips and then the most unexpected thing happened. Like she had been doing with my finger, she started sucking on the head of my cock, like she was sucking on a lollipop. I saw stars as I Instantly came, spewing so many shots down her throat that I lost count. All I knew was the pleasure of being inside her mouth with her lips wrapped around my cock that felt hard as steel. I wanted to move and bask in the pleasure more, but I still had the common sense to not face fuck her like I wanted to, so that she didn’t wake up. I felt slightly ashamed that I had cum so quickly, especially since she wasn’t trying to get me to cum and she also hadn’t used her hand or her tongue, which would no doubt increase the pleasure ten-fold.

As the jets of cum came to a stop I couldn’t tear my eyes away from her throat which kept bobbing up and down as she swallowed all the cum that had just shot out of my balls. I pulled my manhood out of her mouth, seeing one last string of cum attaching us, and wiped it on her bottom lip. I watched in fascination as she sucked on her bottom lip, drawing in the last little bit of cum that I had to offer and also nearly bringing back my hard-on at how sexy her plump lips looked while doing it.

I pulled my trousers up, pulling her top up so her tits were well covered as well and moved the duvet so that she was under it. I slid in as well, not wanting to have to deal with the same noise that I was trying to spare her from and the exhaustion took over and I fell asleep almost instantly.

I woke up in the morning, feeling something heavy on my chest. With half-lidded eyes, I couldn’t see anything which only increased my disorientation. I felt around, grabbing onto something squishy before my eyes flew open as I remember everything that happened last night. On my chest lay, Penelope, as if we were an actual married couple and I basked in the feeling of the girl that I was infatuated with, who I wanted nothing but happiness for, who I loved, lying on top of me with her leg wrapped over both of mine.

I knew that she didn’t do that consciously, but it didn’t change how warm and fuzzy my inside were as I thought about all the possibilities the future held for us. I just had to get past this morning and try even harder to get her attention.

“Wuh…?” I heard a groggy confused voice say into my neck.

A hand reached up to my chest, and as she felt around, no doubt trying to decipher what it was that she was feeling with the alcohol clouding her memory and brushed past the hair I had and she jerked up.

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