Best Friend and Her Mum

I walked into my bedroom to see Cindy lying spread eagle on my bed with what looked like a miniature oil-rig between her legs. A penis shaped thing was attached to a robotic arm that was somehow motor driven with a pendulum, and it was counterweighted with a…Well the main thing was that this contraption was fucking the hell out of Cindy’s poor little pussy mercilessly.

There was twat juice flying everywhere and Cindy was wincing every time it shoved itself up in her. She was sweating and flushed like she’d been doing it for a while. I think she was about to have an orgasm because she had that tell tale look on her face.

You know the one that chicks get. That look that says, “Um, I’m about to lose control of myself so don’t stare at me. I can’t help it (gasp) I’m gonna act like a wild bitch in heat now! (gasp!) IT FEELS SO FUCKING GOOD (Puff! Pant!) I DON’T CARE WHAT (Wheeze!) I LOOK LIKE! I’M CUMMING! OH MY GOD! I’M CUMMING ALL OVER THE PLACE! (GASP!)! AY-AY-AY-YEEEEEEE-E-E-A-A-AHH! (GASP!) OH MY GOD! I SQUIRTED YOUR DRAPES! I’M SORRY!

I couldn’t (gasp!) help it! Oh god! (gasp!) I made a mess! You didn’t see that did you? (gasp!) Jeezus, that was so unladylike of me. (gasp!) So embarrassing, hee-hee! Don’t look at me. I didn’t mean to knock over the lamp. I don’t normally do this!”

You know that look.

So I decided to sit down and watch from the comfort of my office chair. Cindy saw what I was doing and tried to stop the machine. But I knew she didn’t have the will power and she was going to have to ride it out with me staring at her. She tried to cover her face with a pillow but it was too late. Damn, she’s cute when she’s cumming.

After she was done she turned off the device and just laid there panting, trying to catch her breath. I was so turned on by it that I just pulled out my cock and started jacking off on her tits. I got behind her on my knees straddling her face.

My balls were dangling on her chin and I was tugging and twisting her nipples with my free hand. I was getting ready to cum so I just backed up a few inches and started slapping Cindy’s face with my cock splattering her with pre-cum.

“Hahaha, you liked watching that, did you?” said Cindy.

“Well, (nng) Let me (gasp) put it (mmg) this way…” I said and then I splooged all over her lips and nose.

“I take that as a yes,” she chuckled as I wiped the cum off her face with a hand towel I kept by the side of the bed to wipe cum off girls faces.

“Hey Kurt, have you heard of the Andromeda Club? It’s a place where they do bondage and discipline.”

“I can’t say I have but I saw this coming. I’ve never seen you so excited as when I tied you up at Brian’s house the other day.”

“Yeah I guess I really liked being a slut with your friends. But I keep getting this fantasy of doing that with total strangers. I’d be tied up naked in a public place and guys would just start groping me and then they’d get there dicks out and I’d have to just let them do whatever they want to me,” said Cindy with a far away look in her eyes and both hands on her crotch.

“Wow, I’ve created a monster…A really cute sexy monster though. So when do you want to go?”

“Tonight! I wanna go as a guest sub, that’s a submissive. How about you?”

“Oh you mean I have to participate?”

“Well you don’t have to…” she said looking a little disappointed.

“Well since I’ve never done this before I’ll try being a sub too,” I said.

“Haha! Yessss! Those dominatrix are gonna be fighting over you, Kurt,” said Cindy excitedly.

We showed up at the place around nine and drove into the enclosed parking lot. The person who came out to greet us was a tall muscular German looking chick with huge knockers and a gorgeous face. But the best thing about her was her big thick thighs and meaty ass. I knew all this because she was wearing nothing but a corset, thigh-high fishnet stockings, and 7-inch spiked-heels.

She walked up to the car window and Cindy jumped out to talk to her so her meaty shaved pussy was right in my face. Then she turned around to point to where we should park and gave me a full close up view of her incredible ass. I was thinking to myself, that thing is going to be sitting on my face before the night is through. I was getting excited already!

I parked and Miss Damualla escorted us in. (pronounced Damn-you-all-uh)

“So this is the first time you two have been here, eh? Well, you’re a couple of hotties so you’ll get lots of attention.” she said, “I think I need to put leashes on you until you’re both properly trained in obedience. Do you like pain, Kurt?”

“Um…as long as it doesn’t hurt,” I said.

“That’s okay we’ll just make you a slave boy. And you Cindy?”

“I want to be tied up and have strangers fondle me and stuff like that, hee hee!” said Cindy.

“I don’t think you’ll have any trouble getting that to happen here. I’m going to assign you to a male Dom and he’ll take care of you. Just be sure and tell him what you’re limits are. You’re coming with me, Kurt. I’m having a training session with some new girls that want to become dominatrix, so it should be a lot of fun.”

Miss Damualla introduced Cindy to Voltar and then we left her. Miss Damualla took me into a large room where there were several young women hanging out dressed in leather, and I was instructed to strip. One of the girls caught my eye immediately because she was so fucking pretty and had a hot little body that I couldn’t stop staring at. Her name was Miss Belinda.

She was a tall redhead and it was her first time too. After about 15 minutes of talk and a few demonstrations involving my face being straddled by each of the five girls and the teacher, it became clear that I might not be cut out for the role of slave boy. I was apparently too disobedient and every time someone sat on my face I couldn’t resist the temptation to stick out my tongue, which I guess I wasn’t supposed to do.

Although the students all seemed to enjoy it and couldn’t stop giggling, Miss Damualla was getting a little frustrated with me. It ended up being a game of musical faces (with mine as the only face) and the students taking turns availing themselves of my oral skills. Of course I was hard as a rock the whole time and I could tell a couple of the girls wanted to ride me, but Miss Damualla wouldn’t allow it.

Finally she let me know that I wasn’t working out, and I agreed—It wasn’t my thing. I was having too much fun doing it my way. As I was getting ready to leave, Miss Belinda came over to me and confided she didn’t think this was her thing either but she gave me her number, suggesting we get together sometime in a “vanilla” (non-BDSM) context.

I assured her I would call her and she leaned in to give me a little kiss. Things got a little out of hand and that little kiss turned into a ten minute make-out session in the corner of the room. Since Miss Belinda (who was now just “Belinda”) and I were already half naked, one thing led to another, and I wound up hoisting her up onto a convenient piece of furniture and rousting her roundly.

We weren’t really supposed to be doing that kind of thing in the Andromeda but nobody complained. I think it was kind of a novelty to see two people just having straight sex for a change. I left Belinda gasping for breath after what seemed like a dozen orgasms, but I think she was just really into exhibitionism, so she was putting on a show.

Before taking off I went to see how Cindy was doing. I found her tied up on all fours on top of an ottoman type thing in the middle of the room surrounded by a group of guys with hard-ons. She had a apparatus on her head that held her jaw open and two dudes were taking turns fucking her in the mouth. At the same time two other guys were having a little fuck-fest with Cindy’s asshole. One guy was reaming her out so hard that when he pulled out her asshole just stayed open, dripping with lube.

Then the other guy walked up and flicked her clit a few times with his finger and her sphincter clamped shut like a disturbed anemone. Then he smacked her buns a few times just for fun, and began sliding his big fat cock in and out of her. They went back and forth like that using Cindy’s greased up hole for their pleasure. It was shocking what they were doing to that poor girl. I watched for about 20 minutes and then it was break time.

Cindy was walking funny on the way to the shower and as she was drying off I told her what happened with Miss Damualla. I let her know I was not going to be pursuing BDSM at this time in my life but I thanked her for taking me because I had a great time. I also told her to call me when she was done for the night and I’d come pick her up.

“Kurt I have a favor to ask of you,” she said. “My mom hasn’t had anyone since dad, and she’s not ready for a relationship, but she really needs to get laid. She talks about you a lot, and I know she thinks you’re hot. Would you be into doing my mom? As a favor to me?”

I wanted to jump for joy when Cindy said this to me. But instead I kept my cool.

“Cindy, for you I would do anyone, er, uh -thing, I would do anything.”

“I went home and I got a call about two hours later from Voltar. He said that Cindy would be ready to be picked up in about a half hour. I got there early, and when I walked in, there was Cindy still naked tied to a pillar right there in the entranceway so everyone who walked in could see her and grope her. Her big tits were bound tightly and she had ropes going between her legs which disappeared into her camel toe She looked so vulnerable, everyone who walked by couldn’t resist giving her nipples a little tweak or patting her on the pussy.

She had a ball gag in her mouth so all she could do was stand there and be a play toy. It was disgraceful the way she was being degraded. But I figured if everybody else was doing it I might as well have a little fun with her too.

Finally we left and she was exhausted so I took her home and put her to bed. Then I went home and went to bed. Well, after I fucked her to sleep.

The next day I knew Cindy wasn’t going to be around so I went over pretending I was looking for her as an excuse to pay a visit to her mom.

“Oh Hi Mrs. Segal, is Cindy home?” I asked.

“No Kurt, but you’re welcome to come in. I was just getting ready to go for a swim, would you like to join me?” she said in her sexy accent. God, older women are smooth. God, Latina women are hot. God, I was getting butterflies.

“Well, yeah. That sounds great. I didn’t bring my trunks though,” I said nervously.

“That’s okay,” she said, and I was thinking to myself, ‘what?’

“You left some over here the other day so I saved them for you,” she said.

She walked upstairs to her bedroom and I followed her until the door.

“You can come in my bedroom Kurt,” she said with a little smile.

“Oh okay, I just… uh, well y’know,” I stammered boyishly. I’m usually not nervous around girls, but she was different. Let me describe Cindy’s mom. She looks a lot like Cindy but more filled out. In fact she has even bigger tits than Cindy and that’s pretty darn big. She has darker skin and longish wavy black hair which she always wears down which makes her look sexy all the time.

Her hips are wider and her ass is bigger than Cindy’s but it’s damned perky. Today she was wearing shorts, which I’ve never seen her in before and I could have sworn they were Cindy’s, but they fit her tighter and I couldn’t help noticing that she was showing prominent camel toe. I was a little surprised because I’d never seen her looking this hot before and I almost wondered if this was a set up.

She went into her top drawer and pulled out my trunks and handed them to me.

“You can change into them right here, I want to watch you,” She said with a big smile. Now I knew it was a set-up. Cindy must have told her I agreed and she knew I was coming over specifically for her. And here I’m trying to act all innocent, shiiiit!

“So Cindy told you I was…”

“Yes, of course. Hee hee ha ha!” She said as she raised her t-shirt up over her head. She was wearing a black see-through bra underneath, and my knees went weak when I saw her in it, well, through it.

I must have been staring at her tits because she said, “Are you staring at my tits?”

“Oops,” I said.

‘Come on now, Kurt” she said with a with a smile. “I know you got a big one in there.”

It wasn’t until she said that that I realized I had a full blown hard on. Well, not blown yet but I had a pretty good feeling it would be soon. I was thinking, ‘damn she moves fast!’

“Am I moving too fast for you, Kurt?”

She also seems to know what I’m thinking, like she’s psychic or something.

“That’s okay, Mrs. Segal. I’m just not used to the woman making the first move.”

“Please Kurt, call me Guadalupe. Or just call me Lupe for short.”

Oh, all right Mrs. Segal, I said and as I did she reached back and undid her bra. The back straps fell to the sides and the shoulder straps slid down her arms but the bra remained in place still hugging its contents. She leaned forward and jiggled her giant casabas slightly and the bra started to drop…as did my jaw.

I didn’t know how it was possible, but this woman’s tits were not only bigger than her daughters, but they seemed to defy gravity even more buoyantly as they hung suspended in mid air like a pair of blimps. Dark cone-shaped areolas surrounded extremely large tootsie rolls of about an inch long, I kid you not.

They were the most magnificent breasts I’d ever seen and I realized then why Mrs. Segal was a part of my mom’s La Leche League group 16 years after her last child was born. She was a demonstration model!

She cracked a knowing smile but tried to act nonchalant about her endowment. I stood there agape as she came over and reached for my belt. As she undid my pants her breasts were bumping into me and I looked down at her hair and her muscular shoulders framing her cleavage, which jiggled in the most incredible way.

Her bulbous ass protruded back acting as a counterweight. This was womanhood in all its glory. She epitomized femininity, and the overall effect of her being this close to me—touching me, her energy, her confidence, and her smell—oh my God, it was intoxicating.

She was leading the show, but when my pants dropped to the floor and my erection sprung free, she gasped and I could feel the power shift as she became girlish and giggly. She was twice my age but she had a playfulness about her that made her seem like a teenager. And her skin and physique was as flawless as Cindy’s.

She was a little intimidating at first, but I realized I had something she’d been wanting; ever since she saw me that morning in Cindy’s bedroom. And I got the feeling, by her reaction, that she had never had a cock like mine before.

“Ai, papi…” She cooed in a low, sexy half-whisper, “Me gusta tu verga! Es muy magnifica!”

“By the tone of your voice I’m pretty sure you didn’t just say, ‘Your cock is too big—get out of my house’,” I joked, hinting that I didn’t understand a word she was saying.

“I’m sorry Kurt, When I get a little flustered I start speaking my language. You have a magnificent penis,” she said as she began lightly running her fingers along the shaft and up to the head. It reminded me of Cindy’s first reaction. Then, just the way Cindy did the first time, she started by softly kissing and licking the head. But, unlike Cindy, she knew exactly what to do with it, and within a few seconds she had most of it in her mouth and was doing something amazing with her tongue. Almost immediately I felt like I was going to explode in her mouth, but I tried to hold back.

It was all I could do to keep from cumming, but when she said, “Cum in my mouth, Kurt,” I was helpless to disobey her command. I stood there as she held three quarters of my cock in her mouth sucking intensely like I’ve never felt before, and I just gushed all over her tongue as she gulped it down, and she didn’t stop until I was drained dry.

“Mmmm, papi…” she growled as she looked up at me with an unbelievably sexy grin and her eyes fluttered slightly as they rolled back in her head. For some reason I apologized.

“I’m sorry Mrs. Se— Lupe,” I said, for the first time feeling comfortable calling her by her first name. Or maybe I just didn’t feel comfortable addressing her formally after having cum in her mouth like that.

“Shame on you, Kurt. What a thing to do in a lady’s mouth!” she said with a little pout, but let me know she was kidding by wrinkling her nose mischievously with a tongue-between-the-teeth smile. She stood up and turned around. Then she slowly slid her shorts off her ass, rocking her hips side to side like she was dancing the rumba, before bending all the way over at the hip and stepping out of them.

By the time she turned around to face me I was already on my knees ready to reciprocate what she’d just done. She looked at me, then shook out her hair like a wild woman and growled as she put one leg on my shoulder and leaned in to apply her smooth shaven pussy to my face. It was so hot I almost lost my cool and shoved my tongue right into her snatch with no warning. But I remembered she hadn’t been touched in a while and was probably very sensitive. So I very gently and slowly started kissing her inner thigh.

“Ai, ai, ai you make love like a pro-fess-ee-oh-nal! My daughter been getting it good!”

“I stood up, picking her up with me and laid her down on the bed.”

“Ai, jou so macho, muchacho,” said Lupe grasping me by the shoulders.

I kissed every inch of her below the waist, even spending a few minutes on her toes and feet, until she was practically panting, going crazy with anticipation. I had completely taken charge of the situation, establishing my dominance, because I knew Latin women love that sort of thing. She totally responded to this and submitted to me completely even though she was obviously the more experienced.

This was an incredible feeling because she was a like a goddess to me. I was drunk with power, but tried not to let it go to my head. When I had her at the point where she couldn’t stand it anymore, I grabbed her by the thighs and forcibly spread her legs apart and held them pinned while I lowered my face to her pussy which was quite wet by now.

She gasped loudly and was practically hyperventilating as I placed my tongue flat against her dripping slit and just slowly undulated it from side to side barely moving it for a few seconds. Then I dipped the tip of my tongue into her pussy hole which was clamped tight and held it there for a long time, moving it in and out almost imperceptibly. I felt like I was playing a musical instrument the way she responded to my slightest movement.

“Ai papi! How does such a young man know so well what makes a woman feel pleasure? You are a sexual genius!” she said.

I felt like one of those guys on the posters in the Spanish restaurants, you know, the musclebound conquistador standing on top of the cliff-side holding the incredibly voluptuous babe in the tattered see-through blouse and the skirt slit up the side. It was awesome! And I hadn’t even penetrated her yet!

By the time I had my lips wrapped around her clit she was screaming and pulling on my hair like a wild animal. I don’t even know when exactly she came because the entire time she seemed to be in the throes of orgasmic ecstasy. At one point I could tell she couldn’t take anymore direct contact from my tongue and I came up and looked at her face framed by her tousled hair. God she was hot! As I slowly moved up her body, and positioned my cock so it was barely touching her pussy lips, her face changed. Her eyes widened in an expression of profound desire combined with a tinge of fear in anticipation of what was next.

I decided to tease her a little. I know it seems cruel but I’ve found this actually enhances the sex and prolongs the ecstasy for both me and my partner. I held the tip of my cock right against her opening at the bottom of her slit and squeezed my groin muscle so my cock pushed against her labia seemingly all by itself. Each time it did that she gasped in preparation for my entering her, but I didn’t yet and after a few times she got a little embarrassed and frustrated.

Especially since I was staring right into her eyes and I could see her fearful desire. But I didn’t give in because I was the man and she was going to feel what I wanted her to feel when I wanted her to feel it. She was really loving it that I demanded her to submit to me in every way before I rewarded her.

“You are my master, I am your servant. You may take me anyway, anywhere, anytime you want to,” She cooed in the sexiest voice I had ever heard.

I would like to say that I decided she could have my cock at that point but it wasn’t like that. She had me in a spell and I was her servant. Instead of slowly doling out my length like I had planned to, the minute the tip of my cock was inside her warm wetness she drew me all the way in like quicksand. She held her breath and clutched my arms so tightly I thought she’d draw blood, until I was all the way in. She looked at me and I could see the fire in her eyes.

“Dios mio!” She said as she wrapped her arms and legs around me tightly and began undulating beneath me with her powerful little body. Her vagina was slowly pulsating around my cock, milking it, and I just stayed still and let her do her thing. It was amazing and she kept it going for a good five minutes and then I could tell she was getting fatigued.

I gently kissed her up her neck to her ear and whispered, “Now just relax, I’ll take care of you, baby.”

Lupe relaxed every muscle in her body and I was surprised to see that her pussy remained tight, firmly gripping my cock. I cradled her head in one hand and reached around to grab her by the butt with my other hand. Then I started slowly, persistently sliding my cock all the way in and all the way out, incrementally increasing in intensity over the course of about ten minutes. I slammed my cock deep into her over and over, relentlessly, feeling her pulse quicken, each time I increased the pace. And each time she attained a new level of excitement until she was shouting with every thrust.

I kept slamming her harder and faster until suddenly her vaginal walls opened up momentarily and then clamped down harder than I’ve ever felt a pussy get, almost squeezing me out. But I just countered her strength and overpowered her with one final thrust which, instead of pulling back out, I held there with my pelvis jammed up against her clit and the head of my cock against her cervix.

She exploded in an amazing orgasm that seemed like she was having a seizure. She let out a scream that was so loud it shocked me. I got the idea to start doing quick little thrusts into her pussy and it seemed to keep her in the moment of climax indefinitely. She was still cumming and by the look on her face you’d think I was killing her but when I eased up ever so slightly she grabbed me tightly letting me know she didn’t want me to stop.

So I quickened my pace a little more and settled in for an extended wind sprint. All that time in the gym and on the racing bike was really paying off now because even though I was going at a feverish tempo, I felt fuckin’ good! Shit, I could have done that all day long and I was way past the point of coming. She was holding on for dear life and looking at me like I was the Terminator or something.

She didn’t know what I was gonna pull outta my hat next. I knew one thing for sure though, she hadn’t had it this good in long time, if ever. And after all, I was eighteen, and in top athletic shape, ripped and cut from head to toe, just enough body fat to keep my muscle mass from metabolising—a lean mean fucking machine!

But that wasn’t what made this sex so good. I had never been that inspired by any woman before. She instinctively knew how to take my energy and somehow amplify it, then feed it back to me. She was the perfect sex partner. I just couldn’t imagine it being any better than this.

We had been going at it now for a good half hour and I started worrying about Lupe. She looked like she was in a trance and she hadn’t made a sound for the last five or so minutes. I knew Lupe wasn’t used to this much activity so I started slowing down and gradually brought us back down the earth. Lupe just laid there perfectly still. I softly kissed her on the cheek and then on the lips and she opened her eyes.

She said, “I felt like was riding a white unicorn way up in the clouds, and I could see the whole world down below me and I was weightless floating up and up until I reached space and my body disappeared and I was nothing but a warm glowing light, like brilliant star high above the earth. And I realized how all those stars in the sky got there. They were screwed there by a man like you,” She cracked a smile, put her arms around me and held me tight until we both fell asleep in each others arms.

About two hours later I woke up feeling great. It was an incredible feeling to wake up in Lupe’s bed with her voluptuous naked body draped over me all warm in peaceful slumber. The look on her face was so gorgeous, so sexy, so sophisticated, I just laid there and stared at her feeling contently peaceful.

After a few minutes she yawned and stretched, arching her back, accentuating her hourglass figure. God, those tits! That ass! I was so horny for this woman I could think of only one thing, and you’re gonna think I’m weird, but I just wanted to nuzzle my face between her butt cheeks and then shove my tongue up her ass! What can I say, it’s just my thing.

She got up and sauntered over to her dresser and pulled out a bathing suit. She put it on and I said to myself ‘holy shit, is she gonna wear that out to the pool in the backyard?’ The thing was microscopic! just a thin string in the back and a little triangle in front. And the top would have been obscene on a girl with 21:37 07/07/2010tiny tits; on her it was downright scandalous!

“Lupe!” I said, “You’re gonna get arrested if any of the neighbors see you in that thing.”

“They won’t be able to take their eyes off of me long enough to call the police, Hahaha!”

I loved her confidence. I guess when you got it, you know it, and she was gonna show it.

This little affair developed into something even more interesting when we went out to the pool for a swim, and Cindy came home.

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Posted 18/10/2015 by stuart in category "MILF