My Friend's Mom - Mrs. Singer

Continued from Part two. Please read parts one and two first then come on back!

Tommy and I are close to graduating High School, then will have the summer off. We've been planning on attending a local college together and it looks like that's happening. In the meantime, we both have summer jobs lined up to keep busy. Although I continue to have mixed feelings about the wisdom of pursuing a relationship with his mom, we seem to be drawn to one another.

I still go over to their house two or three times a week and sometimes Mrs. Singer will flirt with me and we'll fool around a little, other times she'll just be sweet and motherly and I'll just hang out with Tommy. Then, on occasion, she will come on to me hard and we'll hook up. It's never predictable and it's rarely safe and boring. Despite her sometimes expressing affection for me, I don't think she's interested in having a steady relationship and a normal sex life after years of marriage.

On those occasions when she wants sex, I either get a text from her or she'll whisper in my ear when I'm over there. It has become clear that Mrs. Singer is into playing games, which I believe is something she has wanted but has never been able to pursue before. With me as her willing and able apprentice, she can explore all kinds of new, fun avenues and express her new freedom when she feels like it.

About a month after I first slept with her, she proposes that it would be fun for her to try out a prostitute fantasy. She initially suggests that I pick her up on a street corner, but it evolves into the idea of a "happy ending" massage in a motel. She even has the notion that she would put an ad in the paper and work as a masseuse for a whole day, giving much needed relief to all the horny husbands in the area.

She ultimately decides against that, but does book a room and tells me to show up straight after school for my "massage". When I arrive, we pretend we have never met, I pay her $50 and she proceeds to give me a nice back and leg massage. There is a little bit of suggestion of "extra service" when she brushes up against my balls a few times when massaging my thighs. It feels great. She is great at playing the part, with lots of fun banter and easy going questions.

She tells me her name is "Layla," a play on her real name, and that becomes a character she would perform with me from time to time. She tells me to "flip over" and proceeds to massage my chest and legs. "Is there any place on your body that needs special attention?" she asks. Is this how it works in these massage parlors, I wondered? I didn't know how to answer.

"Well, I suppose, yes, I..."

"Well, go ahead and take my hand. Good. Place my hand anywhere on your body that you want me to pay special attention, OK?" I take her hand and move it to my dick. "Fine. Now, if you want a hand job that will be another $30, but I can give you head for another $60. I don't fuck, OK, so don't even ask. Hand or mouth?" Man, she is great at playing this part. I'm a little scared of her but thrilled.

"Hand, please, Layla."

"OK, sugar, go and get your wallet and give me the money, OK?" I grab my wallet and pass her an extra $30. Considering she has probably sucked me off a dozen or so times by now, I don't mind giving her a little money. She's earned it. Laura/Layla then jerks me off. It's hard and fast, not the usual loving and tender service I'm used to from her, but I suppose that is part of the fantasy. She does, however, stick a finger up my asshole to enhance the experience, which she has never done before.

It is intense and I come very quickly. "OK, sugar. You can clean up in the bathroom. Let yourself out." She goes into the other room and I get dressed and leave. This is a pretty cold fantasy. Very real, but it feels dangerous and wild. I love it. Soon after I leave the motel, I receive a text from her telling me to come by the house for dinner.

When I arrive at the house, she jumps up and puts her arms and legs around me as I support her ass. "Baby!" She says, "That was amazing! I loved it! Layla is kind of a cold bitch, right?"

"Totally. But hot. I'd like to meet Layla again sometime," I say with a smile.

"So, you enjoyed it?"

"I sure did, although technically, that hand job wasn't up to your usual standard, Laura."

"No, because Layla has jerked off hundreds of dudes and doesn't care anymore," she says and we both laugh. She kisses me and holds on to me warmly. It's times like these that make me wonder if we have some kind of future together, but she always keeps me guessing.

After dinner, I go to hang out with Tommy as his mom seems to have disappeared. I take a break and go to the bathroom and hear her playing the piano. I'm excited because I recognize that it's a Chopin prelude and I go over to her and tell her.

"Very good, Nick. You're such a clever boy," she says and smiles at me, then moves over on the bench and taps the empty space next to her. "It's very simple, let me show you," she tells me. She slowly demonstrates the opening arpeggio and I copy her. My elbow brushes against her breast and she smiles at me. We play around for a while and then I'm feeling bold.

"Can we get together tonight, Laura?" I ask her softly, as our thighs touch.

"Not tonight, Nick sweetie, I'm sorry. And anyway, I thought you'd be all tapped out after Layla took care of you," she says with a naughty grin. I'm disappointed, but I still give her a hug. Despite her mood swings and manipulations, I still can't help but have feelings for her. I kiss her on the cheek and turn in for sleep in the guest room.

I'm pretty wiped out, so after reading for a few minutes, I drop off to sleep. I'm not sure how much time passes, but after what seems like an hour or so, I'm woken up after sensing a presence in the room. In my sleepy state, I'm only half aware that another person has joined me in bed and I recognize the soft touch and sweet smell of Mrs. Singer. "Hey there," I whisper.

"Hi sweetie," she whispers back.

She cuddles up to me and it becomes clear that she's completely nude. Her skin feels divine and it's a heavenly moment. "Are you OK, Laura?" I ask her, as she seems a little more loving and vulnerable than usual. I kiss her forehead and hold her close.

"I'm OK, thanks for asking. Thank you for always being there for me, Nick. It's been a weird time for me. Really uncertain, really emotional. I know you have taken the brunt of a lot of my craziness and I appreciate you being a friend. And more. You've really helped me."

I was taken aback by this rare show of transparent emotion and my heart swelled for her. "I care for you so much, Laura, you know that. Even if we're not together or whatever, I'll always be around for you and will always adore you," I say, trying to be grown up and supportive.

"Oh, Nick," she says and holds me tight. After a minute, she looks at me and I can see her pretty face in the moonlight through the curtains. "Nick, you can say no, but can we make love?" Of course I'm excited to have sex with her but I'm also rather touched that she would ask me this way. Given her behavior over the last few months, I wonder if this is another game of hers, but she seems genuine.

"I would love that, Laura," I say and I can see her smile sweetly.

"Thank you, Nick baby. I really need you right now."

She moves her leg across me and then lifts her body so she's completely over me, leaving about an inch or two between us. She drapes her nipples across my chest and softly teases my skin. "How does that feel?" she asks me quietly. It feels electric and erotic and I tell her so. She continues to let her nipples fall upon me gently and I just lie back and enjoy it.

She then moves down my body, slides my boxers off, then takes me in her mouth. She is being uncharacteristically loving and there is no edge or angle or motive to her actions. It feels perfect. After a few minutes she asks me if I'd get her ready, meaning would I reciprocate. It's my favorite thing to do, so she doesn't need to ask me twice.

Because she seems to need warmth and love, I'm extra tender with her and treat her like a queen. As I lick her yummy clit, I hold her around the waist. I can feel her body tense up in waves of pleasure as I stimulate her magic spot. For me, this is the loveliest sex we've ever had. "I'm ready for you, my love," she says, although I don't think she's come, and I move up towards her.

I climb on top of her and kiss her softly. Lately, she's been putting rubbers on me, so I ask her if she has one before I go further. "No, babe. It's fine. You can have me like this," she replies. I wonder why, but don't question her. She spreads her legs around me and I penetrate her. "Please be gentle with me, Nick," she says softly and I make love with her softly and slowly. It's wonderful, and I find myself preferring this to the more outlandish ways we've fucked in the past.

I kiss her lovingly as I move in and out of her. I hold her close to me and she strokes my neck and back. "This is nice, Laura," I tell her and I have feelings of love rising in me again.

"Yes it is, thank you. You're a beautiful boy," she says. "You come whenever you like, sweetheart." I'm quite disarmed by her sweetness and I almost don't want to defile her with my sperm. But, after a minute or two, my cock is on fire for her and I feel it rising in me.

"Here it comes, Mrs. Singer," I say, and begin to come.

"Oh yes, sweet boy. You come inside Mrs. Singer now," she says with nice, encouraging words. I hold her tight and let it go. She doesn't express much pleasure, but I can feel her body trembling beneath me and she's holding onto me, wrapping herself around me. "Thank you, Nick. Thank you for loving me," she says with apparent vulnerability.

I wonder if something has happened today and if she's in need of some genuine affection, but I don't ask. I just tell her, "whenever you're in need of someone who loves you, you know you can count on me." I mean it. Even though this has been a little sad, it was a beautiful, moving experience and I wish it was like this with her more often.

Our bodies separate but she stays with me as we cuddle up. It occurs to me then that this is the first time we've had sex with Tommy in the house, but again, I stay quiet. I begin to fall asleep and she stays with me all night.

In the morning, I'm woken up by banging around in the corridor outside and it's unmistakably Tommy. His mom is still in my bed and of course she's still naked. I wake her up softly and put my finger up to my lips. I make a gesture to indicate that her son is outside, when I hear the door to the room opening. Mrs. Singer hides under the covers and I do my best to cover her up.

"Yo! What's up, man?" Tommy says rambunctiously, sticking his head around the door. "You seen my mom?"

"Er...nope," I reply, and I feel her finger stroke the length of my shaft.

"Weird. Her car is here but I can't find her."

"Maybe she went for a run." I start to sweat.

"Yeah. OK, man. If you see her, tell her I'm out tonight. Peace," he says and leaves, unaware that she's lying in my bed, playing around with my cock. My heart is racing, but when she brings her head up from under the covers, she has a giant grin on her face.

"Is he gone?" she mouths to me. I nod, eyes wide. She breathes a sigh of relief, and when we hear the door slam, she laughs out loud. "Holy fuck, Nick! That was close. That was bad," she says as if waking from a dream. "Phew!" she says and laughs again, then collapses on top of me in a state of hysterics. I'm surprised at her reaction, actually. She doesn't seem that freaked out at the idea of her son catching us in bed and seems to be getting off on the thrill. "It seems we have the house to ourselves, lover boy," she whispers to me and reaches down to stroke my cock again. It's playtime.

_______

A week or so before graduation, I'm getting out of school and lined up with various waiting parents, and I see Mrs. Singer. She waves and I go over to her. She tells me that she's taking Tommy out to a game which is why she's out there. She's wearing super tight jeans and I get really hot standing near her. Her ass looks fantastic and then she catches me checking her out.

"You looking at my ass, boy?" she ask me, eyebrows raised.

"Oh, no! Of course not!" I say, half-joking, enjoying the return to those lovely days when we'd have conversations like this.

"Well, it looked to me like you were checking out my ass," she says and puts her hands on her hips. I exhale deeply and shake my head.

"I know there's no way a boy like me could ever get with an incredible woman like you," I tell her. A part of me is still in disbelief that we actually have got together. A lot of heads are turning and looking at her as they pass.

"Well, you can look but you'd better not touch," she says. She told me that once before, back before I'd ever even kissed her.

"You see how many guys are checking you out, Mrs. Singer? I'm not the only one."

"Girls too."

It's true. She is a star, totally hot and luminescent. I begin to have feelings of love tugging at my heart and then ugly jealousy. Yes, we've slept together but I want more. I want a relationship and I feel almost angry that she'll end up with someone else. I was thinking of saying something to her about going on a date but Tommy appeared through the doors and my moment had gone.

"Hey mom," he says, then gives me knucks and a cool nod. "Sup."

"Alright then," Mrs. Singer says and turns to me. "We'll see you soon."

"Say, you wanna come, dude?" Tommy asks me. I look at his Mom and make a questioning face. I can't read her face but she hesitates.

"I could, but..."

"Yeah, come on Nick," she says. So, I go with them to the game. I'm paranoid about being an unwanted guest, but it's great fun. We get hotdogs and soda and there's lots of talk and laughter. I take a selfie of the three of us and then another of just Mrs. Singer and I together. I don't have too many of the two of us, so it's pretty special. At one point, she puts her hand on my knee and I melt with her touch.

"Wanna stay over tonight, baby?" she leans in and whispers in my ear and runs a finger down my leg. I get instant butterflies with the promise of sex and comfort from her. I smile and nod, trying to be cool. Apparently, she's no longer concerned about sleeping with me when Tommy is home. The rest of the game goes by painfully slowly, as does the rest of the evening back at their place.

At about 11PM, Mrs. Singer pops her head round the door to Tommy's room where we're engaged in an epic battle of Dungeons and Dragons and tells us she's going to bed. I stretch and yawn and tell Tommy I'm tired too. "Cool. Later," he says and turns on the TV. I follow his mom down the hall.

She jumps up, wraps her legs around me and kisses me with a giggle and wide smile. "Ready to get a closer look at this ass, naughty boy?" she says and I just nod stupidly. She has lost none of her effect on me and I remain in awe and under her power. I hold her in my arms and carry her into her room. "My pussy needs your tongue, sweetie," she says as I lay her down. I look at her. She's still wearing those tight jeans.

"Thank you for not taking off those jeans yet, Laura," I tell her. They are accentuating her lady parts beautifully and I almost don't want to take them off her. She giggles and lays there in a luxurious pose. "You're a work of art," I tell her and she pulls an even more alluring pose.

"Touch me," she whispers, and I sit on the bed next to her.

"Foot massage, Mrs. Singer?" I say, and she laughs. It's nice to think back on how this all began.

"Yes, as long as you work your way up and don't stop," she tells me. I start on her feet and she giggles sweetly. "Mmmmmm baby. You know, sweetie, that time you gave me the foot massage, I could tell you'd be a good lover and that's when I really wanted to try you."

"But you were still married."

"I'm not sure that mattered much by then. My husband wasn't fucking me anymore and you came along. I'd been tempted before, but when I felt your hands on me, I wanted you to give me everything. You were so adorable," she says and puts a massive grin on my face.

"Were?" I say cheekily and move up to her thighs.

"Mmmmm yeah. You still are. You really do it for me, Nick. You're young, cute and attentive. Men get lazy but you're still keen on pleasing me. And you have a hot cock," she says with a sexy smile.

I move my hands up her body and I reach the magnificent camel toe in her tight jeans. I'm in heaven. She groans and stretches out as I touch her with both my hands, wrapping around her pussy and ass. I get right up in her ass crack and have my thumb in the middle of her camel toe. She is very responsive. I start rubbing her.

"Ooooh...uh...yeah...that feels amazing baby...you should have done this to me that first time you gave me a massage...I might have let you!"

"Would you really?" I ask sincerely, continuing to massage her. She lifts up her ass giving me better access. Her tight pants ride up high on her as my thumb goes to work.

"Maybe...I was always tempted by you...uh..." She pauses, moaning at my touch. "That night that you held me on the couch, remember?"

"I'll never forget any of it."

"I wanted you to take you dick out and fuck me from behind." I stop touching her for a second, taken aback.

"What, really?" I say, in disbelief.

"Don't stop, You might be able to make me come like this. And yeah, if you'd asked, I would have let you fuck me that night, babe."

"Damn. I wish I'd known," I said and carried on stimulating her, now doing my best to get her off. "I think you made me wait like four months longer, or more."

"I'll have to...uh...uh...check my...diary...oooh, yeah...right there...keep going."

Her diary. This I have to read. I don't talk anymore, just keep on rubbing her and she is getting close, though it's a little bit of a struggle.

"Strangle me," she says.

"What?"

"Put your hand on my throat. Now, do it. Don't stop rubbing me."

I do as she asks and her pleasure obviously increases. She's trying to not make any noise, but her body is tensing up and arching as I rub. My left hand is on her throat. I squeeze a little and her moaning goes into overdrive. I get worried that Tommy might hear. "Keep your voice down," I tell her.

"Tighter," she commands and I squeeze a little more. "Tiiii...tighter," she says again and it seems like she's reaching a climax. I squeeze her throat and she's beside herself. I would never normally have done this and it feels like I'm really strangling her, my grip is tight. She's losing it. "I'm coming...holy fuck...Nick...tighter..." she says. I squeeze her throat as hard as I am willing to and she closes her eyes and let's out a high squeak and then says, "fuuuuuuuuuuuckkkk!"

She comes and I loosen my grip on her throat. She stares at me with a dangerous look in her eyes, panting. I go to undo her buttons and very slowly start peeling off her jeans. She lifts up her ass and helps. "You know, when I saw you at school today, Laura, that's exactly what I wanted to do. Did you enjoy it?"

"That was the best orgasm you ever gave me, Nick. That was...hot. No one's ever choked me before. Oh my god, that was intense and hot." I'm not sure what to say so I kiss her belly and peel off her jeans, revealing her panties. They are white with a little flower over her lips. I kiss the flower, feel her wetness and she moans again. As I continue to peel off her layers to slowly reveal her groomed pubic hair, I kiss and lick her.

"I need more, Nick," she says and I want to give her an intense experience.

Her jeans and panties are down by her knees so she's restricted in how much she can spread out. I'm reminded of a little bondage situation and decide to try something a little new with her. "You trust me?" I ask her and she looks at me strangely, but then nods. I pull my shirt over my head, then roll her roughly on her front. Her arms are behind her back and I tie them with my shirt, tight. I hear her moaning but she doesn't resist.