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

"Wow, you look..."

"Yes, I know. Ugly," she interrupts.

Actually, even though she is dressed down, she has on tight workout pants and it gives her an insane cameltoe that makes me instantly crazy and it is difficult to resist the temptation to try and touch her. I wonder if she has staged this incredible display of pussy for my benefit.

"You're always gorgeous, Mrs. Singer. And I love the way your pants look on you."

"Nicholas, are you being bad?" She looks at me sideways. She knows full well what I'm referring to.

"Definitely, Mrs. Singer."

"Well, go on then, be bad," she says offhandedly, looking away. I take this as an invitation, put my hands on her hips and massage her upper thighs. Our eyes meet.

"Yes, those pants are really accentuating your pussy, Mrs. Singer," I say and give a little whistle.

"Nicholas! I should slap you! Ugh, how dare you? You are the cheekiest boy I've ever known! I can't believe you'd say that out loud!"

"Even though you wore that on purpose and arranged yourself in that way, because you knew I would see you? Because you like the attention I give you, because I make you feel young and sexy. Isn't that true?"

"Ugh, Nick. You're infuriating. But right as usual. I wanted you to notice me. Notice...shit, I'll just say it because you did. My pussy. I wanted you to look at me and get aroused by me. And apparently it worked, honey," she smiles and looks down at my pants.

"Yes, it worked," I say, getting in close and massaging her earlobe and neck. "But you don't need to try to impress me, Mrs. Singer, I always find you to be beautiful and irresistible, no matter what you're wearing." She is clearly getting hot as I touch her, panting ever so slightly, closing her eyes and then gazing deep into mine, as my hands explore her.

I decide to take a chance and go one step further than ever before. I very gently move my fingers closer to her breast and with the other hand, continue to massage her earlobe. Although I'm concerned not to do the wrong thing or ruin our friendship, I'm desperate to touch her. I very gently start massaging her breast, and move in to nibble on her ear. I can feel her heart beating fast. She lets me for about half a minute, then speaks.

"Oh, Mmmmmm...Nick...Ahhh...Nick...Oh, honey...please...please...stop, baby, please stop," she says in a low whisper. I stop. Just touching her like that, feeling her closeness and warm response is enough for me. I take my hands off her and back away.

"I'm sorry, Mrs. Singer. I couldn't help it."

"I know, Nick baby. I'm sorry too. It's not your fault. I don't want you to, but you'd better go, OK?

"OK, Mrs. Singer. I..." I turn to leave, but she calls me back.

"Come here quickly, Nick. Let me give you a reward for being so sweet to me." Mrs. Singer takes my hand and gently puts it between her legs. "There," she whispers in my ear.

"Mrs. Sing-"

"Don't speak. Just touch me and give me a little kiss," she cuts me off. Our lips meet and once again I feel an electricity between us, while my fingers massage her pussy lips through her pants. She starts groaning more loudly now, sounding like she might cum. Our lips rest against each other and I can feel her shaking. She groans and deepens our kiss, our tongues meeting for the first time.

After a minute, she stops and sighs. She softly pushes me away, removing my hand. Panting wildly. "OK, Nick, now go. Please. Go, baby," she says, breathless, heat in her eyes. I nod, and leave the room. I go back to hang out with Tommy, in complete shock.

After that amazing encounter, I don't want to stay away too long. Things were heating up between Mrs. Singer and I, but I assumed because she is married and because of our age difference, she is fighting against the temptation of having a fling with me. Of course, I want her to give in to all the heat between us but don't want her to do something that will make her not want to be around me any more.

_______

The next Saturday, I'm over at their house in order to feed Tommy's fish when he is out of town. I go in and Mrs. Singer is lounging on the couch in her robe. She looks beyond amazing, but I don't think she is expecting me and looks surprised. She doesn't get up though, in fact she puts her arms above her head and pulls an even more luxurious position.

"Hello, Mrs. Singer. How are you? Where's Mr. Singer?" She makes an ugly face.

"Ugh. My asshole husband? I don't know and I don't care. But it's nice to see you," she smiles and stretches out on the couch completely.

"You look very relaxed, Mrs. Singer. Would you like a foot massage?"

"You really think that's a good idea, Nick?" She opens her legs a little, puts her hand on her inner thigh and gives herself a little rub. I nearly come in my pants.

"Well, how about a thigh massage instead?" I suggest. she chuckles and gestures with her finger for me to come over.

"Hmmm, how about we start with the feet, Nicholas?" I leap onto the couch and sit by her feet. She raises her legs, allowing me to move closer. She puts her legs across my lap and I start to massage her toes and ankles. I love these times. We have a lovely chat about her job, my school, with a few bits of gossip thrown in. I try to impress her with some of my newly acquired knowledge of modern art, but she's not really listening.

She just sighs and I move up to her calves. "I wonder what people would say if they knew we were here together like this, Mrs. Singer. A schoolboy and a..."

"A what? An old lady?"

"Um, no. I was going to say...a milf" I feel uncertain.

"Nicholas!"

She has that adorable look on her face somewhere between shock and amusement and I take the opportunity to move my hands to her thighs. It doesn't get much better than this. She stretches herself out, lets out a "Mmmmmm" moan and spreads her legs a little more. I can see her underwear and my cock becomes engorged. Her panties are sheer and I can see her pubic hair. I have a hard time controlling myself.

Very quietly, Mrs. Singer asks me, "You know what milf stands for, Nick?" I do, but tell her I don't. "Well, you can look it up, but if I know you at all, I'd say it applies to how you are feeling right now," she says and closes her eyes.

"Mrs Singer, I know what it means."

"Oh." She looks at me and appears a little embarrassed.

"And anyway, I feel like that all the time with you." I move my hand up her leg. I could see a wet patch on her panties and she is completely relaxed now. Her robe has fallen open and her cleavage is accentuated. I'm desperate to fuck her. "Mrs. Singer, I..." She looks at me and as if waking up from a dream, sighs and sits up.

She takes her legs off my knee and adjusts her robe. "Nick, you give the best massages, I was surrendering to you completely. You could have taken complete advantage of me, you bad boy. You make me feel wonderful, thank you," she says, looking away

"Complete advantage, Mrs. Singer?" I want to know if she would have let me fuck her just then.

"Yes, Nick," she says softly and then stands up, adjusting her robe. "Now," she says, letting out a sigh. "You go and feed the fish and I'll see you later, OK, sweetie?"

"Of course, Mrs. Singer." I leave. It feels amazing to have obviously turned her on like that, but of course I'm frustrated as hell. Just like every night, I go on Facebook, find some selfies she has taken and jerk off.

Tommy is back in town the next day, so I'm over again to work on a school project, but I can only think about his gorgeous Mother. It is after dinner time and I find Mrs. Singer, dressed strangely. "Mrs. Singer, what on earth..?"

"Oh, I'm going to a costume party, Nick"

"Hmmm...why an old washer woman?"

"Old, Nick?"

"No, I didn't mean..."

"I know, Nick, I'm only teasing. Plus, I think you like that I'm older, don't you?"

"Mrs. Singer, I...I don't know, maybe. Yes, I suppose so."

"I thought so," she says smiling.

"So, anyway, why a washer woman, and not a...cheerleader or a nurse or a..."

"A hooker...?"

"Um..."

"Well, Nick, you're naming female sexual stereotypes, so..."

"You are dressed like a slut, Mrs. Singer, so why not?"

"Nicholas! How dare you?! This time I really am going to slap you, you...you...Urg!" She walks over to me and goes to playfully slap my face, but I catch her hand and hold it. Our bodies are close, our eyes locked. I look down and can't help but admire her delicious cleavage and the way her breasts look through the thin fabric of her top.

"Mrs. Singer, you do realize I can see your nipples, right? Is this character set in a time before they invented underwear?" She laughs loudly.

"You can only see my nipples if you choose to look, Nick, honey. You don't have to look if you don't like them."

"I love them, Mrs. Singer, you know that. I..."

"Love, Nick?"

"I dream of sucking on your nipples, Mrs. Singer", I whisper in her ear.

"OK, Nick, you're pushing it," she says sternly. But I can tell she's getting excited as well. Her nipples were hard and so is my cock.

"Can I touch you, Mrs. Singer?"

"No, Nick. I don't think that's a good idea. My husband and I are trying to patch things up, and well..."

"Oh, I see." My face falls and I feel like dirt. I fucking hate him and wish he'd leave. I let go of her wrist and back off. "I'll leave you be, Mrs. Singer," I say and walk away.

"Nick, I'm sorry. I can see I've hurt your feelings. I don't want that."

"It's fine, Mrs. Singer, you're right. And anyway, I should get a girl my own age and not..." Now it is Mrs Singer's turn to look disappointed. I had said that on purpose. "Have a good time at the party, Mrs. Singer. Maybe you should put on a bra, though. I don't like the idea of lots of men drooling over you."

"You're right, Nick. The truth is, I only did that for you." I feel better, and we both smile. "Will you be staying over, Nick? Maybe I'll see you later?"

"Yeah, Tommy and I are seeing a movie but we'll be back here later on."

"OK, then. Talk later, sweetie". She gives me a hug and goes to put on a bra.



Later that night, I return with Tommy to their house. It's pretty late, so think I'll go straight to bed in my usual place in the guest room. I open the door and there she is, lying on the bed. In her bra and panties.

"Mrs. Singer, what are y-"

"Heyyy Nicky baby," she interrupts.

"It looks like you found your bra, at least," I say and Mrs Singer laughs uproariously. She'd been drinking again.

"Come sit down with me, baby." For some reason, I'm feeling uneasy, although of course this is something I had dreamed about ever since first setting eyes on this woman. I sit down, but don't touch her. "Where's Mr. Singer?" I ask, wondering what is going on. She makes an angry face and says "Ugh! Fuck him. Seriously, fuck that horrible pencil dick asshole."

"Oh."

"He's off with another woman, so fuck him. I'm gonna fuck another man if I want to. And it's gonna be you. I want you to fuck me. Tonight." She leans towards me and I can smell the alcohol on her breath. Her eyes are half closed and she is clearly out of her mind with booze and anger. Of course, I want to fuck her, but this feels wrong.

"Nick, I know you've wanted to fuck me this whole last year, and now's your chance." She reaches over, grabs the lump in my pants and it feels incredible. "Oh, I knew you were a big boy, Nick baby. Much better than that shrimp dick husband of mine," she says and laughs wildly again. Yeah, her hand on my dick is the most amazing sensation of my life so far and I don't ask her to remove it despite my misgivings.

She continues to stroke my cock while looking into my eyes and licking her lips. I put my hand on her back and make little circles. "Mrs. Singer, do you really think this is a good idea? You've been drinking a lot and you're obviously mad at your husband."

"Ugh, don't be such a jerk, Nick. You gonna fuck me or not?" she says, slurring. I don't like her like this.

"I can't believe I'm saying this, Mrs. Singer, but no. I'm not going to. I'm sorry, I..." She stretches herself out and tries to make herself irresistible. She looks amazing and my heart races. I'm desperate to fuck her, but I don't want it to be like this. I know that if I did, she would regret it and it would probably be the end of our friendship. My mind goes back to the last time she was drunk and how grateful she was that I didn't take advantage of her.

"C'mon Nick baby, I know you want to. Your dick is so hard for me. Touch me, baby. Touch my tits, touch my pussy. Put your finger inside me, come on, kiss me."

I kiss her gently, then, showing unbelievable restraint, say "Come on, Mrs. Singer, let's put you to bed." She gets mad at me then. "OK, fuck you. Fuck you and fuck my fucking husband. Fuck all men. Ugh! You're a fucking asshole, Nicholas, fuck you!" She gets up and storms out of the room.

"Mrs. Singer, I'm sorry, I...", I call out but it's too late. She's gone and I hear her door slam. I feel shitty, uncertain if I'd made the right decision or not. She is obviously conflicted and going through some crazy stuff and I'm probably not helping. Although I'm supposed to stay over, I split and walk home, depressed and conflicted.

_______

I don't go over to their house for weeks after that. I make excuses to Tommy and we always end up hanging out over at my place. One day, however, I'm at the swimming pool near me and she is there. She sees me and waves me over, making a sad face. "Hello, Mrs. Singer. How have you been?" I say, somewhat coldly. She is much more effusive and emotional.

"Nick, I don't know what to say. I'm just...I made a fool of myself and I was rude. I was out of my mind and way out of line. I'm so sorry. I truly am. I've made you hate me, haven't I?"

I feel bad for her. She is so gorgeous, so sweet and she seems sincere in what she is saying. "No, of course not," I say. "I won't ever hate you. I'm just freaked out and didn't know if I would be welcome back."

"I understand, Nick. Now listen. I think what you did and the way you treated me was amazing. I was crazy and even though you have a crush on me, you acted with grace and treated me with respect and care. I think what you did was...very grown up. You showed me what a great guy you are and I really feel like I owe you."

"Thanks, Mrs. Singer. It's just that I really like you, and..."

"I know, Nick. I like you too. How can I make this right between us?" she looks up at me with big searching eyes, and it feels like she means all this and that I matter to her. I shrug and look away. "Come over for dinner, OK? I'll make your favorite and maybe there will be a reward for you, if you want it. How does that sound?"

It sounded great. I love her rewards. I remember her last reward, when she allowed me to touch her pussy after I'd been a "good boy." I tell her I'll be there and I can't help but feel very excited.

I go over that night and as usual Tommy's Dad isn't there. During dinner, Mrs. Singer says she is gonna get an early night and then says that I look tired and perhaps I ought to as well, knowing full well I was going to stay the night. Is this the "reward" I was going to get? By not fucking her when she is drunk, my reward would be to get to fuck her when she's sober?

That sounds unlikely. But I'm still excited and at around 10 o'clock, I make my excuses and say I'm gonna go to bed early. About 20 minutes later, she walks into my room and locks the door behind her. My heart starts racing. She is dressed in a tight low cut blue dress and she looks amazingly hot, with stunning cleavage and insane curves. I'm sitting on the bed and she comes over and sits down next to me, smiling warmly.

"Now, Nick. Again, I want to thank you for being a gentleman the other night, when I...I...made such a fool of myself. And, just thank you for being such a sweet, lovely boy and for making me feel so young and pretty all the time."

"Mrs. Singer, you know I adore you, I..."

"Shut up, Nick, OK? Now, I want to give you a reward. This doesn't mean we're going to be girlfriend and boyfriend, OK? This doesn't mean we're gonna be together, OK? This doesn't mean anything. It just is what it is, do you understand?" I'm getting beyond excited, so I just nod and shut my mouth.

She goes on. "This is just a reward for you, for being a good boy. Something nice for you. But that's it. This will be the only time, got it?"

"Got it, Mrs. Singer," I say, almost salivating with anticipation.

She looks me in the eye, puts her hands on my shoulders and pushes me down on the bed. "Lie down and relax, Nick honey." I lie down on the bed and without saying anything, she starts undoing my shoe laces. She slips off my shoes and socks, then moves towards me on the bed. She starts touching my dick through my pants. This is really happening. Only this time, it is perfect. She looks perfect, smells perfect, feels perfect.

She smiles at me lovingly. I start to speak, but she puts a finger over my lips. "Don't speak, baby," she tells me. She unbuckles my belt, unzips my fly, slips off my pants and pulls off my briefs. My cock is just there, sitting upright, with Mrs. Singer sitting astride one of my legs looking like the mother of all milfs. She starts stroking my cock.

This is it. This is the moment I have fantasized about for months and months, but it feels so much better than I ever could have imagined. My first ever hand job and it's from the woman of my dreams. I groan and open my legs. She continues stroking softly and looks me in the eyes. Very softly she whispers, "You have waited a long time for this and you deserve it. Does that feel good, Nick darling?"

"Yes, Mrs. Sin...Singer." I could barely speak.

"I'm glad you like your reward, Nick baby. I didn't know you'd be so big, baby. I love your cock." I really don't know if I have a big cock or not or if she is just being nice. It looks a lot like those dudes in the porn films I'd seen online. I want to shut my eyes, but I can't take my eyes off her. "Touch my breasts, Nick baby," she whispers to me.

I do as she asks, and everything just gets better. "Mrs. Singer, I'm gonna..." She stops stroking and just squeezes my balls gently..

"Not yet, Nicholas. We're going to make this last a little while, OK?" I nod. For the next 20 minutes, Mrs. Singer plays with my cock as I fondle her breasts, her tummy, her earlobe and her neck. Every time I say I'm about to come, she slows down to prolong the moment. It's heavenly torture.

After a little while, she leans over, gently kisses me on the lips and asks, "You want to come now, Nick, honey?" I nod and she speeds up. I have never felt so good. "OK, Nicholas. You come for Mrs. Singer now," she orders, in a quiet yet firm tone.

"Yes...Mrs...Singer...I..."

"Come for Mrs. Singer, good boy, yes, come...come... that's it, come," she says gently and lovingly, encouraging me with her sweet words as she pumps my cock. I explode like a volcano in a rush of almost inconceivable pleasure. My cum shoots up, splashing on her dress and in her hair. A little goes on her eyelash. She sits there looking at me, gently stroking me until I'm all done, then wipes it off her face, calmly.

"Mrs. Singer, I..." Once again, she puts a finger over my mouth.

"Wait here, honey and don't move." She leaves the room and returns a minute later with some warm, damp towels. She cleans me off with great care and love. "That was wonderful, Nick. Thank you for coming for me. I hope you enjoyed your reward." I nod, unable to speak. "Now, you get some rest, honey. And I'll see you tomorrow."

A tiny little kiss on my mouth and she was gone.

The next morning, I go downstairs and everyone is milling around, including somewhat surprisingly, Tommy's Dad. Mrs. Singer is sitting on the couch in the living room and waves me over. I sit down next to her so that our thighs are touching. Tommy and his Dad are in the next room, so she keeps her voice low. "Now, Nick. I wanted to make sure you were feeling OK about last night," she says in a matter-of-fact tone.