My Friend's Mom - Mrs. Singer Pt. 01

Tommy has been my best friend all through high school and we've become practically inseparable over time. We share lots of interests, which mostly include playing video games, and because he has the best system I'd usually find myself spending my evenings after school over at his place.

Sometimes it feels like I'm always there, but his Mom doesn't seem to mind. I don't see much of Tommy's Dad and I'd been wondering if their marriage isn't going so well. Tommy is in his own world of video games and Dungeons & Dragons and seems oblivious to everything else, but I sense something isn't right at home. He also doesn't seem too interested in girls and hasn't noticed that I have a massive thing for his Mom.

I don't know exactly how old Mrs. Singer is, but she's a lot older than me, obviously. Her first name is Laura, though I always call her Mrs. Singer. I just turned 18, so I'm guessing that makes her about 40 years old or maybe a little more. She's an incredibly alluring and beautiful woman and I am absolutely crazy about her. Yes, I want to fuck her and kiss her all over, but I'm just a virgin schoolboy and wouldn't even be sure I'd know what to do with her, if I'm being honest.

Mrs. Singer is a fairly tall woman with long brown hair, pale skin and a slender body, but I think it's her pretty face that makes me adore her so much. She has lovely eyes and a sexy smile, though of course it's her tits and ass that drive me crazy. She dresses well and often wears alluring outfits which draw me in. And then there's the lovely piano playing, her painting and the meals she makes which are so much better than the ones I get at home. I wish I lived at their place.

__________

As I so often do, I come back to the Singer household after school to hang out with Tommy. I'm always on the lookout for his Mom, as well, though. After an hour or so of playing video games, I feel the need to pee, so I walk down the hallway and see Mrs. Singer in her room. She's wearing a business suit and is reading a newspaper on her bed. She sees me. "Hello Nick, how are you?" she says.

"Oh...hey...um..." Unfortunately, my tongue gets tied whenever I talk to her when we're alone. I get nervous. She has a very confident, strong personality and she just makes me crumble.

She smiles at me. "I'm just getting home. I'm so tired," she says, putting her feet up. I'm sure she didn't do it on purpose, but I find this highly erotic. She pulls off her shoes and I feel a tingle in my cock. I start to sweat and feel some panic.

"Mrs...I...er...gotta go...I..."

Again, she just smiles as if she recognizes that she's making me nervous. She has a habit of smiling to herself and I've picked up on this over time. I start to walk away, feeling like an idiot. "Nick?" She calls after me. I poke my head around the door. "Are you staying for dinner?" I just nod, because I know if I try to say anything it will just come out badly. "Great," she goes on. "Give me a little bit. I need to shower."

I close my eyes and picture her in the shower. Did she say that on purpose because she's noticed that I'm always looking at her and paying her attention? I've known her for years now, so I imagine that she's picked up on my schoolboy crush, but maybe I'm just paranoid. I begin to feel sick. I just say "OK," and run off back to Tommy's room.

As usual lately, Tommy's Dad isn't home for dinner, so it's just the three of us. Conversation is lively with Mrs. Singer tolerating our nerdy talk of Sci-fi and D&D. I begin to feel like I may be growing out of all that, but Tommy certainly isn't. Despite being a bit of a dork, I'm also fairly athletic and the fact that I have a decent physique makes me feel good around her. Still, I wonder if she is judging me, thinking I'm a loser, but is just too kind to show it. I ask her where Mr. Singer is and she rolls her eyes.

"Oh, he's working late...again," she replies. All is definitely not well with them and I'm ashamed to say that makes me feel better, I can't help it. I try to steer the conversation to more adult things, like her job, college prospects, books and travel ideas in an attempt to impress her. It seems to work because she looks me in the eye as we speak and ignores her son when he interrupts our talk. She gives me a sweet smile and taps me on the hand.

"OK, boys. I'm gonna clear away and then do my exercises. You two go off and do your homework."

I'm sure she didn't mean this as an overture, but when Tommy runs off to his room, I decide to talk to her. "You look like you're in good shape, Mrs. Singer. Do you...um...exercise...I mean..." Ugh. I had felt confident at first, then it went to hell. She just smiles at me in her usual way that turns me to butter.

"I need to stay trim, Nick," she replies. She makes a little gesture to make herself look thinner and puts her hands on her hips. I'm sure she doesn't mean it to be hot, but it is and I go hard and then start to sweat again. I need to get a hold of myself so I change the subject. I want to impress her, to not just be some jerk kid in her eyes.

"Can I help with the dishes?" I say and start bringing them from the living room into the kitchen, not waiting for her response. Instead of having her tell me no, I just go on and then return to our earlier conversation. "I think you look pretty trim already, Mrs. Singer," I say, my confidence returning.

She stops in her tracks and looks at me. "Really? You think so?" I nod and smile, and she smiles back. I can't believe her reaction. Maybe no one has paid her a compliment in so long, that she is genuinely taken aback, though it isn't much of a compliment really. I want to tell her how beautiful she is but stop myself. I continue to help her, loading the dishwasher and then doing a few by hand. "Thank you so much, Nick. You're very sweet," she tells me. I love it when she gives me attention that way.

I turn bright red. Then, I turn from the sink and nearly bump into her. There is an awkward moment when we nearly collide then try to go around each other, but both move the same way. We both laugh and it feels wonderful and liberating. I'm about half a foot taller than her and she looks up at me with big, brown eyes. It also feels wonderful to dominate her physically that way, because it makes me feel like I could be attractive to her.

My heart quickens and I enter into tongue-tied mode again. She smiles slightly awkwardly and walks around me as I'm frozen to the spot. I begin to wonder if she had thanked me for helping her or for the compliment and want to ask her, but I don't. I don't want to bother her or just turn into an inarticulate fool again, so I finish the dishes and go to hang out with Tommy for the rest of the night.

_________

Mrs. Singer owns an art gallery downtown. From what I can gather, that's her passion and her living. She was an art major and in my limited experience I think she's a pretty good painter. There's even one she has done of herself in the nude that's hanging in her private study. Maybe it wasn't intended for anyone else's eyes, but I'd seen it and found it highly erotic. I have even taken a book out of the library on art history to try to appreciate it further and be able to converse on the subject. I want her to know I'm not just some video game playing dork loser.

After school a few days later, Tommy and I come home. Mrs. Singer is in the living room and she is all dressed up, looking fine. She has a short pink dress on, heels and is made up. Her hair looks ravishing and she is wearing earrings. Tommy runs to his room as usual, which gives me the opportunity to talk to her. I never pass on these opportunities if I can help it.

"Hi Mrs. Singer. You going out?" I ask her.

"Yup!" she replies in a cute way, batting her eyelashes playfully.

"I was going to say!" I blurt out foolishly.

"What were you going to say, Nick?"

"Oh, well, nothing, I..."

"Tell me, please. What?"

I get nervous again. I have dug myself into a hole here. "Well, I...er...figured...um...you were going out because...you...um...look very...er..." I stand there, blushing and fidgeting. I feel like an idiot and I'm sure I sound like one too. She does her customary smile to herself and now I think she knows that I have a crush on her.

"Very what, Nick? You don't normally have difficulty saying what you want to say," she says, although I wonder if she is joking.

"Well, I guess you're making me nervous, Mrs. Singer."

"Why would I make you nervous, Nick? I see you all the time."

"I know, but..."

"OK, well, you're being shy. Now, tell me. I look very...?" she says assertively. She is always so confident and in control. It is one of the things that makes me so crazy about her.

"Mrs. Singer, please." She just looks at me, puts her hands on her hips and makes a face. Fine. I'll tell her. "You look very pretty." There, I said it. Her reaction seems positive and the knot in my stomach loosens up.

"Really, Nick? You think so? That's so sweet. You're a nice boy," she says and squeezes my shoulder. It's hardly a loving gesture but it's something and it sends a shiver down my spine. "OK, well, I've gotta run. There's dinner in the oven for you kids. See you later!" With that, she runs out the door. I'm pleased that she liked my compliment but it bums me out that she called me a kid and that she is obviously going on a date. Is she seeing her husband or someone else?

I don't see her until the next weekend when I'm staying the night over at their house. I walk into the kitchen while she's making tea, and stupidly ask her what she is doing. "Making tea, Nick. You want some? I've only got weird herbal stuff though." I don't want any of her weird herbal tea but I do want to hang out with her so I accept with thanks.

I feel the overwhelming urge to pay her a compliment because she is looking so good. She has tight jeans on and this loose fitting top that reveals her back. I want to touch her skin. I feel that usual tingling in my cock that I so often feel around her. I blurt out some incoherent line about her shoes looking good or something.

"Am I making you nervous again, Nick?" she asks me, seemingly well aware of the fact that she is. Then there's that little smile again.

"I, er...you..." I look at the floor and scratch the back of my head.

"What, Nick? Is there a problem with me? Do you not like me?" she says, with apparent sincerity. I feel overwhelmed and just open my mouth and it all comes out in a tumble.

"Oh, no! What? I do, no. Yes, I...I really do...er..." I'm really in a mess now. She puts her hand up and smiles, probably to put me out of my misery. "Mrs. Singer. I...I think you're awesome," I manage to say, though in a mumble.

"Oh, Nick, you really are so sweet. I like you too. And you don't need to be so nervous around me, OK?" she says while pouring out the tea. She hands me a cup. "I'm glad you like me," she then tells me, glides over to the couch and sits down with a newspaper. Even the way she sits is magnetic.

_______

A few days later, I unexpectedly bump into Mrs. Singer at the dentist. She is sitting in the waiting area and even though I see her immediately, I wait and see if she wants to talk to me, before I say hi. I kind of loiter around the reception desk to see if she notices me and thankfully, she does. "Nick?" I hear her voice. Not only does she notice me and say hello, I'm also picking up on some pretty flirty body language from her, quite different than when we're at her house.

"Hello, Mrs. Singer. How are you?" I say and give her a big smile.

"Oh, you know," she says, putting her hair up in a wonderfully sexy way. "Nobody likes the dentist, Nick," she laughs.

"I suppose not, but, well, you know...um..."

"Being shy again, Nick? Why is it you can't form sentences around me, but I hear you talking non-stop with Tommy?" she asks, raising an eyebrow.

"I...you...um..." Mrs. Singer smiles, leans forward and pushes her tits together. She's giving some intense body language from where I'm standing. She is probably picking up on the fact that I like her, and maybe wants to tease me, or maybe she just enjoys the attention I give her. But, it makes me completely unable to speak. She is so incredible.

"I, what, Nick?" She looks so hot, so gorgeous, it is impossible to try and be cool or smooth with her. I'm just an idiot boy compared to this sophisticated woman.

"You, er..."

Just then, a dental assistant comes out and calls "Laura?" I breathe a sigh of relief and wipe my brow in a gesture of escape. Mrs. Singer giggles at me.

"OK, Nick. You're very funny. I'll see you over at the house soon I hope." She tousles up my hair and walks away. I watch her ass as she walks and get a hard on, which is pretty awkward at the dentist.

Later that night, I see her at their house. She's dressed up and looking good again. "Oh hey, Nick. Long time no see, eh?" She smiles. "You boys out tonight? she asks me. Maybe she's planning on being in and is hoping we'd give her some privacy.

"Oh, I don't know yet. How about you? You look, er..." Oh shit. Here we go again.

"Nick. We've talked about this," she says firmly.

"Yes, I know, I'm sorry. I'm...sorry," I utter pathetically.

"Stop saying you're sorry and just talk to me. Don't be nervous," she says kindly, touching my arm. She is looking me in the eye, then turns away towards a mirror on the wall. Damn, she looks good.

"Well, you look beautiful, Mrs. Singer, so I guess that means you're going out," I say, trying to be confident.

"Nick, did you just check out my ass?" she says, half annoyed, half amused. I'm not sure how she really feels, but I sense she doesn't mind my looking at her so instead of falling apart, I go along with it.

"Yes, absolutely!" I tell her, assertively. It's the truth after all.

"Nicholas! How dare you?!" she says, laughing, though still with a shocked face. She turns back to the mirror and poses. "Well, what do you think?" she asks me. Now it is my turn to be shocked. I just stand there in dumb silence. I'm picking up on strong vibes that she's enjoying this flirty moment with me.

"What do I think of...? I ask her, trying to draw it out.

"You know full well, Nick. Now, you tell me or I'll get angry with you."

"In that case, I definitely won't say!" I'm enjoying this little game too.

"Nicholas!" she exclaims and takes a step closer to me. She holds a finger up and says "You are the most terrible tease! Just tell me, OK?" and pushes her finger into my chest. This is actually getting pretty hot and I start to sweat.

"Fine. You leave me no choice, Mrs. Singer. You have an amazing backside. Now you know." She stands there, maybe unsure how to react. She gives me a quizzical look, then turns away back to the mirror, putting her hair up. Then I see that little smile.

"You can look but you'd better not touch," she mutters and walks out the door.

_______

A week or so later, I'm over again to spend the night, but Tommy is still out so I let myself in. It's around 9pm and I find Mrs. Singer there alone. "Oh, hey Nick. How are you feeling?", she asks me when I approach. I stand there dumbfounded for a second or two because she looks sexier than I'd ever seen her before.

She is wearing a slinky black dress with a sheer lacy fabric and a silky undergarment. It is tasteful but revealing and I feel a tremendous urge to reach out and touch her, but restrain myself. "Oh, go ahead, Nick. Tell me how good I look. Go on, check me out," she says cheekily and I just stand there with my mouth open.

"Mrs. Singer, I..."

"Nick, I'm sorry," she says, laughing. "I had a drink or two and I'm tipsy. It is very naughty of me to imply that a teenage boy would want to check out my ass," she laughs again and sways a little. She is delightfully drunk.

"Mrs. Singer, what's got into you?" But you're right, you do look..."

"Spectacular? Jaw-droppingly sexy?" she interrupts with giggles.

"Yes, all of the above and more," I say calmly, trying to get her to cool out a little. "Are you going out?"

"No, baby, I've just been out. I'm home now. I'm gonna curl up on the couch and watch a movie. Any ideas?" she says, plopping herself down and spreading out, rather sluttishly.

"Um, how about To Die For? Seen it?" I'm messing with her now, and enjoying it.

"No, what's it about," she looks at me quizzically.

"It's about an older woman who..."

She holds a finger in the air. "OK, Nick, I've heard enough, you bad boy. What about you, you going out? Got a date?" she inquires, rather sleepily.

"Um, actually, I'm not feeling too great," I lie. "I might hang out with you. I mean with Tommy, er..."

Mrs. Singer smiles to herself. I catch it and imagine that it means she likes being in my company, that she finds me entertaining, at least. "You can watch the movie with me if you like. It'll be more fun than watching it alone anyway," she answers and my heart leaps.

So, we watch a movie together. With Tommy as well of course, but I make sure I position myself on the couch next to her. As it goes on, I get drowsy and decide to put my head on her shoulder, and her reaction is warm and motherly. She puts her arm around me and I drift off with my head on her bosom, her soft, tender flesh just a thin piece of fabric away. I'm "asleep", right, so what is the harm? I put my arm around her tummy and am in heaven as I touch her. I don't think she minds.

Sleeping over that night, I jerk off thinking about her as usual, but this time my fantasies are fueled by the feeling of actually having my hands on her body. I want more. So, the next morning I wake up and stroll into the kitchen and find her there. She is in her silky pink robe and looks amazing. I make a big yawn to get her attention and she looks up. "Hey Nick, sweetie. Did you sleep well? You were such a sleepy boy last night and such a big baby."

I pretend not to know what she is talking about, but inwardly, my heart is racing. It did not escape my attention that she had called me "sweetie." "What do you mean, Mrs. Singer?" I say, feeling more comfortable around her now.

"Don't you remember, Nick? You were very sleepy and cuddly."

"Mrs. Singer, I'm sorry if I..."

"It's fine, Nick. I liked it. It's nice to be wanted."

"Well, I definitely want you...I mean, I...yeah." She does that subtle smile to herself and I imagine that it's because she thinks I'm cute. At least that's what I hope it is. It must be obvious to her now that I have a crush on her and I feel like she doesn't mind and maybe even likes that I do.

"Want me, Nick? Whatever do you mean?" She is torturing me. I decide to ignore her and go in for a morning hug. She is facing away from me doing some dishes, so I put my arms around her waist from behind, then my head on her shoulder. I know it's pretty forward, but I act all sleepy so maybe I'll get away with it. I feel her breasts against my arm and involuntarily become hard. I don't quite realize at first but she apparently notices, wriggles a little and giggles.

"Oh, Nick, thank you. You really are a softie. Well, not exactly," she says and laughs out loud. Her reference to my erection is apparently delightful to her as she continues smiling but I am mortified. I pull away and catch her as she looks down at the large lump in my briefs before turning back to finish the dishes, her face pulled in an attempt to hold in more laughter. "Now, You sit down and I'll make you some eggs. Bad boy," she says.

Later that day, after Tommy and I were finished with a school project, I want to see if I could find his Mom and pass by her room. She calls me in. "Hey Nick, I'm going out. Do I look OK?" she asks. She is in a petite business-style suit-dress which is smoking hot, and a part of her brassiere is revealed. I just stand there like a moron. "Don't leave me hanging, sweetie. You're always so good at telling me I look good and it boosts my confidence. I have to go out now and play at being businesswoman."