My Best Friend's Mother Ch. 01

"Dylan?" she asked, the relief clear in her eyes, although the confusion didn't move and suspicion started to roam back in and show its face. "Where...this is your room. Why are you in your room?"

"Sorry, Mrs Bailey," I said, and although I had tried to rehearse in my head, the nerves I felt around her wasn't something. "I knew that Mark was going to be coming back late and I didn't want him to disturb you so I thought that bringing you back to my room after you passed out while we were watching the movie, was the best thing to do, or shouldn't I have done that?"

"Oh, Dylan," she said, wrapping me up in a hug. "I didn't mean to sound ungrateful, and I really appreciate how thoughtful you are I was just confused about how I got here."

"Don't worry about it Mrs Bailey, I will always be here, whenever you need me."

She squeezed tighter, and I swore that I hitch in her breathing but it was only for a second so I wasn't completely sure.

"I trust you, Dylan," she said, and it was like music to my ears. "The only thing that is confusing me is that my mouth tastes a little bit salty, do you know anything about that?"

"The only thing I remember you eating was one of those salted cookies that we have downstairs," I replied, fluttering of nervousness in my chest mixing with excitement as I so badly just wanted to shout it that what she was tasting was my baby batter, but I knew that it was too early for something like that. I could tell that I was making progress, but it would be ruined if I let my horniness get in the way too much. "Other than that I'm not sure, Mrs Bailey."

"Well even now it tastes really good!" she said, and my dick was at attention, knowing that she wouldn't question it in the future if something like this happened again. "And again, how many times do I have to tell you to stop calling me Mrs Bailey. Just call me Penelope, I'd love it if you did..." she trailed off, as if nervous, but when I saw where she was looking and realised that the covers weren't covering the most important part of my body anymore, and the massive tent my in boxers was clearly visible for her to see.

I quickly pulled the covers back over my manhood, feeling the blush rising on my cheeks and saw that her face was red as well, although she glances back, as if trying to see more, gave me more courage that this wasn't the worst thing that could have ever happened.

"Sorry!" I exclaimed, still feeling the shame of exposing myself to her accidentally.

"You...don't need to apologise, Dylan," Penelope said. "It's perfectly natural, especially early in the morning. You take care of it and I'll go and make breakfast." Her innocent probing smile, as if making sure that I was okay and wasn't too embarrassed, almost made me cum on the spot. There was something about her pure attitude that made it less embarrassing and made me appreciate her more.

"Don't worry Mrs Ba- Penelope," I corrected myself after seeing her raised eyebrow. "I'll be right down."

"Don't rush now," she said, coming over and giving me a kiss on the forehead, presenting her twin peaks for my viewing pleasure. "And thank you, Dylan. At least I know that I've got one man in the house that I can count on when needed."

She left the room, shutting the door over and I pulled my cock out, and jacked it, thinking of last night and how much I wanted to experience her mouth again, just with her awake next time. Slick precum lubricated my dick as I thought about amazing it would feel to spray my seed inside her fertile pussy, instead of just letting it go to waste down her throat. I didn't want to just fuck her, I wanted to make love to her, to show her how amazing she was and that I truly cared for her. I wanted to cum inside her and let all my sperm enter her womb and fight to fertilise her egg so that she'd become pregnant with my child. I wasn't going to let the relationship, though it was deteriorating, I had with Mark stop me from making his mother my wife and giving her the world.

I felt the orgasm approaching, closing my eyes as I imagined Penelope walking back into the room and seeing me spraying my seed everywhere. That thought pushed me over the edge and I came, feeling relieved, but even more determined after each rope.

I cleaned myself up, before going downstairs and seeing Mark and Penelope arguing.

"...do you care?" I heard Mark shout. "I wasn't the reason that dad left, that was you being too stupid and old to give him what he needed!"

I heard a loud slap echo through the kitchen and rushed over, nearly barrelling Mark and his red cheek over. I watched him run out the door, slamming it shut behind him before I heard the engine of the car start and hastily speed away. I walked into the kitchen, turning off the already forgotten stove.

"Thanks, Dylan," Penelope said, her head still in her hands. "You don't have the stay around for me, you can leave whenever you want."

"No," I said, grabbing her by the hands and pulling her towards me. "We're going out right now, both of us together, and you can't refuse."

"Dylan..."

"Go upstairs and get ready, I'll drive us somewhere, anywhere, and we'll spend the whole day together," I said, seeing that her defences were crumbling. "C'mon, I know you'll enjoy it, Penelope."

Her name coming out of my mouth seemed like the last straw, as she let out a sigh, giving me a teary smile before going upstairs to change. Usually, I would follow her to her room and try and catch a glimpse of as much as possible, but today was different. Today she needed someone that she could trust and I was going to be that person, today and whenever else she needed me to be.

She came down, having changed out of the tank top and shorts she was wearing a T-shirt and jeans. Although it was a very basic outfit, it accentuated her curves in all the right places. As my eyes drifted up from her wide hips and slim waist I saw a blush on her face, embarrassed that I was staring at her so intently.

"Are we still going?" she asked while looking me in the eye. The pink tinge to her cheeks was disappearing, but still present.

"Of course!" I replied and we walked out to the car together, getting in and I drove along.

I stopped at the shopping centre, got out and then went to the other side and opened the door for Penelope.

"Thanks, Dylan," she said as she exited the car. "Where are we going?"

"Although I like what you're wearing, I think that you could expand your wardrobe a bit," I replied. "And don't worry, I'll buy it for you."

My mother and I never struggled for money, which is why she had the luxury to reject Penelope's offer of a room. This was because of the life insurance policy that my father always kept up with. I don't think that he knew he was going to die, but I did know, from all the ramblings of my mother, that he wanted her, and his future children to be taken care of which worked out as I had a lot of money because the way he structured the policy, it allowed me to take half when I turned eighteen. I'm very glad that he did because I knew my mother would have kept the rest for herself if she was able to.

Because of that, I had many millions saved up, and it had only increased because I had invested it straight away. I didn't want to waste it all on a bunch of nothing, so I was only spending some of what I earnt each month on the investments. Now, though, I had a reason to dip into that saved money and it was to cheer up the woman I loved and maybe incline her towards feeling the same way.

"Where are we going first?" I asked, and she pointed toward a cheaper clothing store.

I knew that she didn't actually want anything in that store and just didn't want me to buy her anything expensive, but I wanted to- no needed to spoil her, especially now.

"How about here," I said, having grabbed her by the shoulders and guided her towards a more expensive, luxurious store.

"No, Dylan, you really don't need t-"

"I'm not doing this because I feel obligated to, I am doing this because I want to," I said, as she looked me in the eyes, searching. "No matter what you say, I am going to buy you things from here, and other stores, because I know you're only saying no because you don't think that I should be spending the money on you."

Biting her lip she glanced around, contemplating taking me up on my offer. I knew that she only needed a little push so I grabbed her hand, pulling her into the store and she stopped resisting, letting me pull her along.

"Go and pick out a few things and then try them on. Don't worry about the price, this is my treat for you," I said, squeezing her hand in mine.

"Dylan..." I could still see the hesitation, so I squeezed her hand one more time. "...thank you."

She rushed away, now excited to finally be able to indulge in herself. After a while of looking she came back, a few different outfits in hand and I followed her to the changing rooms. I sat outside, waiting for her to come out and show me the outfit, but instead, she stuck her head through the curtain and beckoned me over.

"Sorry Dylan, but I can't get the back zip done up," she explained. "Can you help me please?"

"Of course, I can help," I said, feeling giddy that she was letting me into the changing room with her.

When I entered she was fully dressed but at that moment it didn't matter because the dress she was wearing was almost better than seeing her naked body. The cream colour blended well with her skin, and the dress hugged her body almost as if it was another skin. Her dress wasn't short, it went to her ankles, but the slits on either side gave me glimpses of her panties, which I saw were plain white.

I snapped from my daze at how beautiful she looked in the dress and zipped the back up for her. Staring over her shoulder into the mirror so I could see the low neckline, created by the dress only having a strap for one shoulder. I wanted so badly to wrap my arms around her waist and start kissing her neck, but she was just getting to the point where she trusted me, and I didn't want to compromise the growing buds of a relationship that I thought I could feel.

"How does it look?" she asked, looking self-consciously back at me as if all she needed was my approval before picking the dress.

"It looks good," I said, trying to keep my words mild but once I saw her face start to drop I decided that I didn't need to be holding back as much. "Actually no, you look really beautiful. You're already the most beautiful woman I have ever seen, and this dress only makes that clearer."

"Oh!" she said, looking up in surprise. "You really believe that?"

"I wouldn't be saying it if I didn't believe it," I replied, her goofy grin giving me more confidence and I lay one hand over the small of her back. She didn't seem to mind or didn't notice at all, so I relaxed and started giving her more compliments.

"I need to change into the next outfit not, mister," she said, lightly guiding me out of the changing room. "But you can come right back in after I've finished to see how it looks."

I sat outside, hearing the occasional rustle within. Before she once again poked her head out, although this time, by the pink tinge to her cheeks, and the darting movements her eyes were making, I knew this was going to be good.

My jaw dropped to the floor as I stepped into the room and saw what she was wearing. She had a black dress on, but this wasn't a normal black dress, no, the reason I reacted strongly to this dress was that there was more skin showing than the dress covering her body. It was like lattice in the way it allowed her creamy skin to show through, and it was also a lot shorter than the last dress There was also a massive diamond-shaped hole in the centre that showed off her belly button and toned abs.

"Spin around for me," I managed to get out, and when she did the dress flew up a tiny bit and I got a full-on glimpse of her perfectly round, curvy ass.

"So, what do you think," she said nervously.

"The other one was good, but this dress is on another level. I don't care what you say, we are getting this dress for you," I said, already salivating at the concept of seeing her looking this sexy when I would take her out to eat at a restaurant, how jealous everyone in the restaurant would be, and how hot she'd look lounging around after we arrived home. "Holy shit!"

"Really?" she said, although I could already tell that she felt elated that I had given her such a compliment. It didn't feel awkward to do, as how can telling the truth about radiant and sexy someone was, after they asked, ever be construed as anything else.

"I've only got a few more outfits left, you can come in every time I change if you want to?"

"Of course, I want to," I said, walking towards the curtain. "I'm really glad to be here with you."

"I'm glad too,"

She tried on the rest of the outfits, which we ended up buying, and although she wasn't as daring with the rest of her choices, it didn't mean that she didn't look extremely sexy and that I wasn't really turned on while checking her out. At times I felt like her boyfriend with how comfortable she was with me touching her and complimenting her. I do not think that it is normal to invite someone into the changing rooms, even after you have changed, as you can always just allow them to see outside the room. But it was like she wanted me to be the first person to see how hot she looked, and not allow any other eyes to break her in before me.

"There is still another thing that we need to get you before we return home," I said, and usually I would be exhausted and have wanted to go home after such a long time shopping, but this wasn't any normal shop. If she agreed with my next request I didn't know if I would be able to contain my excitement.

"What is it?"

"I've heard you mention a few times that you needed new underwear, so why don't we go and get some since we're here already, and I'm paying," I could see the hesitation and decided to give her a way out if she wanted. "You don't have to if you don't want to, just know that the offer still stands, even after we leave."

"...ybe..." I heard mumbling from behind me just as we were about to leave the shopping centre.

"What was that?" I asked

"If you're offering, maybe we can?" she said, although it came out more like a question as if she herself didn't know if she was ready for this or not.

"The offer still stands," I said, trying not to reply too fast as I didn't want it to look like I was just chasing after her body, as I was chasing after her as a person, her body was just a bonus. "Do you want to go now?"

She nodded and followed along as I had seen a store, one that I wasn't sure that she would want to go inside with me, but one that I saw just from looking in the window had a lot of sexy underwear and nightwear.

As I stopped in front of the store, Penelope looked up, her eyes widened and she took a step back as if she was intimidated.

"We can't go in there!" she quietly hissed. "I thought you were talking about normal underwear, not this weird stuff!"

"Penelope," I said, grabbing her hands in mine and pulling her closer to me, causing her to flush. "I know you've probably never bought clothing like this but I really want you to. Not for myself, obviously, but because I have already seen how much more confident and happy you are when the dresses earlier. This will help you in the same way and all I want is to see you as happy as possible, do you understand?"

"But-" I cut her off by putting my finger to her lips.

"I don't only want you to do it for yourself," I said, mentally preparing for what was to come next as I knew I was about to start pushing my luck even further. "I also want to buy you this underwear as I think it is a waste for a woman as beautiful as you to be wearing the underwear that you're wearing right now. Your body should only have the finest clothes on it, and that goes down to your underwear as well."

I prepared myself for her to storm off, not reject what I was saying vehemently, but instead, I saw a contemplative look on her face. She was questioning it, and this time I didn't want to rush anything and waited for her to make up her mind. She walked past me, and I thought that she was going to be walking straight back to the car but the direction she was headed was into the lingerie store.

"What are you waiting for, aren't you coming?" she asked, turning back and waiting for me to rush over to her, which I did.

I didn't bother going around the store with her, as I could tell that she was already pushing herself past her limits and I thought it would be too much right now. She did, however, come over to me once she had picked out a few things, and wordlessly led to one of the changing rooms and I felt my dick start to swell.

She peaked her head out of the dressing room after a few minutes and silently indicated me to enter the room with her. I gulped, standing up and putting my dick in the waistband of my trousers as I obviously didn't want her to notice and then walked up to the curtain, feeling like this was going to be the next big moment in my life.

I moved the curtain a little, stepped into the enclosed area and instantly lay my eyes on the most breathtaking sight I had ever seen. It was black, again like the dress was which contrasted her white, creamy skin perfectly, but this was something different because it was the only two pieces of fabric stopping me from getting to what I wanted to see. Although she had on the bra and panties, there was another piece of the set attached to her things, which was held into place by two straps, one on the front and one on the back, which held the piece together. The mesh material it was made of was on the verge of being see-through, and I could see a lot of her skin, but I wasn't able to see her pussy or nipples.

"I know that this probably wasn't what you were talking about when you mentioned coming into this store to buy some underwear, but I think it looks good, maybe? Hopefully?" she said, and her nerves didn't allow her to stand still.

"You have no idea how sexy you look right now," I had become emboldened by her willingness to show me herself in such a vulnerable state, and also because I was starting to become unbearably horny. My cock was almost pushing itself out of the trap I had put it in within my waistband which meant I needed to keep a constant eye on it. "God, give me a little spin and show me the back."

She spun around and I saw the back of the panties and almost came as I saw just how much of her ass it was exposing. I hadn't ever seen her ass in this much detail before, as I either saw the bottom of it under a dress, or the bottom of it under some shorts. Even the times when I had seen her naked I had only seen her top half, which while attractive, I always prefered ass over tits.

I walked up behind her once again, resting my hand on the small of her back once more and smiling at her in the mirror.

"You have no idea the power you hold," I said, narrowly holding myself back from releasing my barely contained cock from my trousers. "Penelope, you're amazing."

She didn't answer, instead, her embarrassment started to disappear as she gave me a beaming smile and that was too much for me. My dick, which had grown too hard, pushed its way out of my trousers and like a bull in a bullring, it only had one goal. To fuck someone's day up, and it turned out that it wanted to fuck mine up today as the instant it came out of my trousers it hit against Penelope's perfect ass and started spraying shot after shot onto her perfectly new lingerie.

"Dylan?!" Jumping away from the source, although because the room was so small she ended up tripping and falling over right beneath my cock which wasn't done releasing all the pent-up seed that I had stored up while looking at her in all the sexy clothes that she was wearing. The last few spurts landed on her face, and when she went to say something, the last spurt came out and landed directly in her mouth.