My Friend's Mom - Mrs. Singer Pt. 03

Rolling her back on her front again, I see that she's nicely trussed up. She looks at me with a dirty expression on her face, her mouth slightly open. "What are you going to do to me, Mister?" she says in a pathetic voice, playing the part.

"Whatever I want, and there's nothing you can do to stop me."

"Please...please don't hurt me," she says and turns her face away. She's getting off on it. I pull her jeans down and then use them to secure her feet, then leave her panties around her ankles. She can't escape. "Oh god, oh god..." I hear her say. I move alongside her, put my hand around her throat again and then lean down to kiss her pussy. She groans but she's still playing the part.

I tighten my grip on her neck, close to as hard as I was before, and continue to stimulate her clit with my tongue. She tries to close her legs, but I squeeze her throat a little harder and say, "open your legs, lady, or I'll make you black out." She opens her legs again but begs me not to hurt her. I loosen my grip slightly, then proceed with the pussy licking.

With my free hand, I finger her and she starts making noises. They are partly faked sobs but also groans of pleasure. I can feel her body tense up and know by now what that means. As I flick her clit with my tongue, she's being hit by waves of orgasmic sensation. I squeeze her neck and her juices flow as she reaches a climax. I keep going for a little while, then stop when I feel her relax.

I let go of her and she closes her legs and curls up to protect herself. I take off my pants and boxers. "What are you going to do to me?" she pleads.

"I'm going to fuck you, lady," I reply coldly. "Open your legs or you'll be sorry." She does as I say and I get on top of her. I look her in the eye but she turns away. "Look at me," I command and she obeys. "You want me to strangle you again?"

"No, please, anything..." she says, but there's a little hint of a smile on her face and she makes a slight nod before closing her eyes and pretending to cry. I penetrate her and then get both my hands around her neck. I slowly fuck her and play with her throat menacingly with my fingers, occasionally squeezing.

"Look me in the eye, bitch," I tell her and squeeze her throat. She opens her eyes and looks at me. Her arms are completely tucked underneath her, bound tight and I think of a way I might further humiliate her, as I fuck her pussy. I don't want to fuck her ass, in case she's not cool with that, but I know she enjoyed it when I fucked her face before, so I figure that might be intense and she'd probably get off on it.

I pull my cock out of her but don't let go of her neck. "Oh, thank god...is it over?" she says, with wide eyes.

"Not yet, Princess. Sit up."

"Oh, please. What are you going to do with me?" she pleads, helplessly, her arms and legs still secure.

"Whatever I want," I say, and pull her up by the neck, being careful to not actually hurt her. I get her on her knees and then put my dick in her face. "Open wide, Princess," I tell her and she refuses.

"Oh god, no, please."

I squeeze her throat again, hard, and she opens her mouth. "Keep it open, lady, or you'll be sorry," I tell her harshly and she just nods with tears streaming down her face. I get a little worried that she might not be OK, but I figure she'll tell me if she isn't. I put my hard dick in her mouth and start pumping her. She makes some pathetic little sounds and I hold the back of her head. Holding her tight, I ram my big cock all the way down her throat and keep it there.

She gags and makes a muffled cry and I pull out. She gasps for breath and looks at me hopelessly. "Want some more?" I tell her and she begs me to stop. She calls me Mister so I know she's still in character. I pull her hair back hard and she gasps again. "Open up, little princess," I tell her and she obeys.

I fuck her face while holding her head in place. It's a little violent but it feels great and she's making some wild little sounds that are unmistakably of pleasure. I get my dick as far in her mouth as I can then deliver the load. I grab her around the neck, look her in the eye and say, "swallow, princess." She shakes her head but I put my hand over her mouth and she has no choice but to comply. She falls down on the bed, as curled up as she can be with her limbs tied.

I lie down next to her, hold her close and untie her bonds. We both lie there, panting and sweating, looking at each other. I'm uncertain what she's thinking, but eventually she lets out a sly little smile and brings her arms around me. "That was dark, Nicholas. Really dark," she says softly.

"I'm sorry. Did I go too far, I..."

"Babe, no. You...um..." She stops talking and puts her head against my chest. "Hold me," she says softly and I hold her tight, comforting her.

"I would never hurt you, never."

"I know, sweetie." We lie there for a minute or so and she goes on. "I loved it. Not only did you make me come twice, hard, you also...you showed me you could be much more than the sweet young man that you are. You..." She broke off. I move away, then untie her legs. I pull off her jeans then pull up her panties. I take the bed clothes and cover her up.

"Next time, Mrs. Singer, let's agree on a safe word."

She looks at me sweetly, nods and says, "don't leave. Stay with me."

I stay.

_______

A few weeks go by and having graduated, I start my summer job. I'm working at a local hardware and garden store, stocking shelves and doing other menial tasks, and I'm enjoying it. Once in a while, Mrs. Singer shows up and pretends to shop. She'll find me, then stand around, browsing, looking cute.

Today, I'm doing some stocking and my supervisor Jack comes over to me for a chat. Then, I see Mrs. Singer approaching. "Hey guys," she says, flirtatiously. "Can you help me?" She's wearing a summer dress which looks stunning on her, with ample cleavage display. Jack looks her up and down and I start to sweat.

"Certainly, ma'am, how can we help you?" Jack answers her.

"Oh, I need help in the flower department, but there's no one there. I just need help reaching something up high." She stretches out and looks magnificent.

"Oh, sure. No problem," Jack says and starts leading the way.

"Oh, Sir. I'm sure this young man here can help me. I don't want to bother you," Mrs. Singer goes on. I stifle a smile as she looks at me.

"Yes, that's fine. I can help," I say, and we walk off towards the flowers. Jack wanders off, looks back and checks her out again, and we both laugh. "Do you get tired of guys looking at your tits and ass all the time?"

"It depends on who is doing the looking," she says with a sly grin.

"Do you actually need help, Miss?" I ask her when we reach the flowers.

"Yeah," she replies and stretches up to a top shelf, in the meantime pressing her tits in my face. It's amazing and I'm pretty sure a couple of other shoppers notice.

"Let me get that for you, Miss," I say and grab a plant on the top shelf. As I do this, Mrs. Singer grabs my balls. I cough and nearly drop the plant.

Releasing my nuts from her grip, she says, "don't drop that, young man." I hand it to her with a smile. "You're such a nice young man," she says and strokes my cheek. She walks away with a feminine waddle and stands in line to buy the plant. Looking back, I see seven or eight identical plants well within her reach. I can't help but laugh to myself. She's so wonderful. I feel my heart flutter.

Summer goes by and I continue work and continue hanging out at the Singer house. Tommy's mom and I sleep together a few more times that month, but it's much safer than before, more vanilla, more loving. Despite the fact that she seems to enjoy our little role play sessions, I feel bad about being rough with her and only want to treat her nicely. As far as I'm concerned, our affair is going better than ever.

A few days later after work, I figure I'll treat myself to ice cream and stop by the local parlor. I go in and see Mrs. Singer standing in line and she's with a man. A man who looks about her age. He's got a hideous mustache and I instantly hate him. I don't know what to do so I just stand there, a little behind them in line and watch them.

They're laughing and she looks happy. They're not holding hands but at one point, she reaches over, gives him a hug and a kiss on the cheek. Then, they lock arms. I continue to watch them interact with a growing sense of anxiety in my stomach. I feel sick but I don't leave. They order their ice cream and turn to leave. I don't think she has seen me, but I can't know for certain.

As soon as they're gone, I turn to leave without ordering and get in my car. Tears well up in my eyes and despite myself, I start to cry. I feel pathetic. I turn on the car and just drive. I turn on the radio but nothing blocks out this awful feeling. Thoughts race through my mind and I head home and lock myself in my room. I turn my phone off and curl up in bed.

Neither of us ever said we'd be exclusive. She's not my girlfriend, I'm not her boyfriend. She's not cheating on me, she can be with whoever she likes. But that doesn't change the way I feel and I feel lousy. I don't want her to be important, but she is.

_______

Over the next month or so, I avoid her and I avoid Tommy. I get a few texts from both of them, but make excuses about hanging out. I don't answer her. I just want to keep my head down till college and make all this go away. One day, I see her in the aisles at my work and I turn around and slink away. I receive another text from her but don't answer. I decide that college is coming up and I'm going to try and forget about her and move on. There's no future in it, so why torture myself?

As the date of my first day of college approaches, I begin to regret going there in tandem with Tommy. It's not that I don't like him or don't want to be his friend, but I just want to put the whole thing behind me. I begin to think maybe I'll get a girlfriend in college and have a normal relationship. That sounds pretty nice, actually.

Managing to duck Mrs. Singer over the course of the final weeks of summer, I begin college with enthusiasm. The college is only an hour away from home, which seems like the perfect distance away; not too far, not too close. Despite my wanting to impress Mrs. Singer with my knowledge of the arts, I had decided to go for engineering in hopes of securing some kind of career down the road.

During orientation, I bump into Tommy and it's genuinely great to see him. I didn't realize how much I'd missed him, and we make plans to get dinner that week. Settling into my dorm, I try to be open and social and start to make new friends. There's even a couple of girls I like the look of, especially this one pretty redhead called Sophie. Seeing her and talking to her is the second time a lady has given me butterflies in my stomach.

Dinner with Tommy is a blast. Conversation is natural and flowing and we never run out of things to talk about. During the course of the evening, Tommy gets around to the subject of his mother.

"My mom asked after you, Nick," he said.

"Oh yeah?" I tried to stay cool, but I can't help feeling like I'm going to burst. Ugh. The bad feelings return.

"Yeah, she wondered how you are."

"And what did you tell her?"

"I told her I hadn't seen much of you, but that I'd seen you hanging out with a pretty girl. What's her name by the way?"

"Sophie."

"And that I would see you tonight."

"What was her reaction when you told her about Sophie?" I had to ask.

"Oh. Well, now that you mention it, she blushed and didn't say anything. Then she left the room. Weird, huh?"

"Totally. It was probably unrelated. She's always got so much going on."

"Not lately. She's working a lot but she's always home alone."

"Really?" I was genuinely surprised to hear that. "Is she OK?"

"I don't know. She's been pretty quiet recently. She seems kinda depressed."

"Well, she did just get a divorce."

"Yeah, but she was so happy for a while there. Like, insane. I've never seen her so happy. Then, the last month or so, she's been...not so much. I think I caught her crying."

Now I feel like shit. I begin to wonder if I'd completely misjudged the situation or if her change in mood had occurred for reasons that had nothing to do with me. I didn't think I mattered to her, but maybe I do. Could it be that the man I saw her with wasn't a lover or a boyfriend and that I jumped to conclusions? Then, I thought about Sophie and how I'm keen on the possibility of entering into a new relationship with someone my age. This is all fucked up.

"Well, send my regards to her, please." This is all I can think to say. The evening ends and I head back to my dorm. I get a text from Sophie wanting to know if I could hang out. I text back in the affirmative and head over to her shared apartment on the other side of campus.

Walking in the evening air, thoughts race through my head and I begin to get unpleasant sensations in my chest. I'm worried about Mrs. Singer now and want to reach out to her, but I'm excited to see Sophie and hope something might happen between us.

I arrive at her place and there are three girls milling around. They're all so cute. Josie is wearing a bathrobe and slippers and the robe can't hide her big tits and I can't help but look. Wendy is exotic with beautiful long hair and she's wearing a revealing nightgown. Sophie answers the door in tiny little shorts and a tight mini-t-shirt and gives me a hug. She's gorgeous, with outrageous curly red hair.

We're all hanging out and I'm glad to see they've managed to get some beer in. We all have a few drinks and it's a lot of fun. They all seem to like me as well, and it feels great to get attention from some pretty young girls. I almost forget about Mrs. Singer for a while.

Things get pretty loose and flirty, and when Josie and Wendy clear off, I find myself with Sophie sitting on my knee, kissing. It's lovely. There's no game, no motive, no punishment, no stress, just a sweet, pretty girl sharing herself with me. I am grateful to Mrs. Singer for one thing, however, and that's an education. Though I'm not going to try any of our crazy shit on this girl, I definitely feel qualified to please her.

I feel up her titties as we kiss but don't try it on with her beyond that. "Nick, is it OK if we don't go any further tonight?" she asks me sweetly. What was I going to say?

"Of course, whatever you like. I can get going."

"Thank you for being understanding, Nick. That doesn't mean I...we...er..."

"I understand," I say, smiling. I take it to mean that there's sex in my future with her. I was used to waiting and getting blue balls. Mrs. Singer had been the queen of the blue balls. I give Sophie a hug and a gentle kiss and go back to my dorm. College is pretty close to what I'd hoped it would be.

_______

Sophie is now my girlfriend and we actually go on dates together, though we haven't gone much past the kissing stage. Tommy asked a girl out as well and we go on a double date to a cheap burger and milkshake joint. Tommy's love interest's name is Bianca, and she's a gorgeous black girl. I actually feel a little jealous of Tommy with his exotic beau, but mostly because she has better taste in tunes than Sophie. I wonder if he's fucking her.

The subject of his mother comes up again, and I ask after her. Tommy isn't too revealing and I don't try and push it, otherwise it might get weird. He does hint again that she's been lonely and I get a tense feeling in my chest. Then, he brings up the idea of going over for dinner and having another evening like old times. Not quite like old times, I think to myself, but I nod in agreement.

"Why don't we bring Sophie and Bianca? What do you think, ladies? Dinner over at my place with my mom?" Tommy asks. There's some indistinct murmuring, so I guess we'd be playing it by ear. I run through in my mind how it might go, and begin to regret agreeing to this idea. The best case scenario for me is that I make Mrs. Singer jealous of my girlfriend, but there are several worse scenarios that occur to me.

After dinner, I drive Sophie back to her place and she asks me in. As soon as we get inside the door, she takes my hand and leads me to her bedroom. "Ready to fuck me, Nick?" she asks seductively, so I waste no time undressing her and getting her ready for the main event. Her body is incredible; soft, curvy and deliciously young, and I give her lots of attention.

While the sex isn't as explosive, exciting or kinky as it got with Mrs. Singer, I find myself much more able to relax around her. I also find her young pussy to be quite different than Mrs. Singer, like a fresh piece of bubblegum, so I spend a long time pleasuring her. She is extremely responsive, yelling my name out loud over and over. I feel slightly concerned that her roommates might hear, but put that thought away and carry on.

Sophie seems to be most impressed with my pussy eating skills, claiming that I'm the first guy to actually make her come like that. "The two other guys who did that kinda just chewed away and didn't get anywhere," she says with a laugh, after I'd made her climax wildly. She's lying there, sweating and out of breath, spread out on her bed. I could have licked her sweet clit all night long.

Her blow job doesn't measure up to the high standard set by Mrs. Singer, but I always knew she'd be impossible to beat. It's still good of course, and I enjoy seeing my big cock in her pretty little mouth. She just can't get it too far in, that's all. Sophie is a wild little minx when I'm fucking her, however, and her energy is infectious. As I penetrate her, she comments on how big I am, so I guess Mrs. Singer wasn't lying.

I love Sophie's tight pussy. Fucking her feels amazing and again, she's very vocal in her appreciation. We do it in a number of positions, and after I'm finished fucking her, I fuck her again. It's wonderful and I begin to feel that the manipulations of Mrs. Singer are in my rear view mirror.

I stay over and the next morning in the kitchen, Wendy and Josie are lounging around in their underwear while I make coffee. "So, Nick, you were either murdering Sophie last night with a knife or you made her come like eight times," Wendy says and they both laugh hysterically. I feel strangely proud of myself and masculine, and enjoy the attention from these two lovely ladies. I just smile and nod.

"Well, she's alive and well, Wendy," I say in reply.

"I'll have to plug her for details later, Nick," she says smiling.

"Coffee, ladies?" I offer. As much as I like Sophie, I wonder what these two might be like as well. I feel like a new world is opening up for me.

_______

The next weekend, we all decide to drive back home to see our folks, and I'm filled with a sense of dread. Sophie and I head straight over to my place and my parents drill her for information on college and our social life. I feel bad for her and ask my parents to cool out.

"Now, kids, you'll have to stay in separate bedrooms while you're here, OK?" my mother says and I pretend not to care.

Sophie leans over to me and whispers, "I'll have to sneak into your room," and that actually sounds more fun.

That evening, the plan is for us to go over to the Singer household for dinner and I'm dreading it. I'm nervous about seeing her and also scared about her doing or saying something weird or crazy. I remember when she used to get drunk and do bizarre things that she later regretted. I'm also worried that I might still have feelings of love for her.

So, Sophie and I show up and knock on the door. Tommy answers and gives us customary knucks and we go in. Mrs. Singer is in the kitchen cooking and we go in, rather shyly. Mrs. Singer looks over at me and gives me a lovely hug, tits pressing against my chest. It's wonderful as always, but I do my best not to engage with her in that way. She looks stunning and I don't feel so good. I break off and awkwardly introduce Sophie.