Fun With The New Neighbor free porn video
I was sitting in the backyard by the pool, when I noticed a moving truck pull into the driveway next door. I knew the former owner had recently sold it, so I guessed my new neighbor was moving in. From a distance I noticed an attractive brunette, probably at least a few years older than myself, but no signs of a significant other. A few guys from a local moving company were helping her unload her stuff.
A couple days after she moved in, I went over to introduce myself and welcome her to the neighborhood. After I rang the doorbell, I was treated to an incredible sight. She was dressed in just a tight t-shirt that accented her generous tits, and a pair of tiny shorts that allowed her gorgeous ass to peak out the bottom. She was curvy in all the right places, and I realized she was not just attractive; she was fucking stunning! Shoulder-length brown hair perfectly framed her beautiful brown eyes and slightly pouty lips. With a closer look, she appeared to be at least ten years my senior, but still incredibly sexy. My cock began to swell immediately, and I shifted slightly to make it less obvious. Thankfully, she didn’t appear to notice. There did seem to be a mutual attraction however, as I couldn’t help but notice her eyes taking me in.
“Can I help you?” she asked.
“Hi, I’m Daniel,” I said, “I just wanted to stop by and welcome you to the neighborhood.”
“Hi Daniel,” she said, eyeing me ever so subtly, “My name is Cindy. I just moved to the area from Long Island.”
After a few minutes of conversation, I learned that she was recently divorced and moved upstate to start over with her professional photography career. It was mid-summer and very hot that day. She had faint sheen of sweat on her forehead, and it was clear she was unpacking and getting settled.
“Is there anything I can help you with?” I asked hopefully, while in the back of my mind thinking that I’d love to help her out of those shorts. “It must be tough to do this all by yourself.”
“Thanks Daniel, I may just take you up on your offer,” she said with a slight smile. “Just warning you though, the A/C isn’t working, and I haven’t had a chance to have someone take a look at it yet. I have some beer in the fridge to help keep us cool.”
“Sounds like a plan! Let me go change into an old t-shirt and I’ll be right back.”
As I walked back to my house to change, all I could do is think about my great luck to be invited into the home of such a stunning older woman. Sure, I was only helping her unpack some boxes, maybe move some furniture; but a guy can hope.
I wonder if I have any shot at all? I thought to myself. She did seem to be checking me out.
Within a few minutes, I was knocking at her door. As I stepped inside, the oppressive heat suddenly hit me.
“You weren’t kidding, it is hot in here!”
“Tell me about it. My shirt is clinging to my body it is so soaked in sweat!”
Of course after she brought this to my attention I couldn’t help but notice the damp line running down the back of her t-shirt. You are welcome to take it off any time you want, I thought with a smile. After grabbing a glass of water to keep hydrated, we got to work. Over the next 2-3 hours I helped her move nearly every piece of furniture in the house. By the time everything was where she wanted, I was hot, sweaty, and exhausted.
“Thanks again for your help! How about that beer?” she asked.
“That sounds amazing right now,” I replied. While she went to the kitchen to grab two beers, I stepped into the bathroom to wash my hands and face from sweat and grime.
A moment later I walked back to the living room, and was stunned by what I saw. Cindy was sitting on the couch in nothing but her shorts. Her tits were even better than I imagined! I would guess they were about a 36C, with no noticeable sag. Considering she was probably in her mid-to-late forties, they seemed too good to be true.
She must have seen my eyes nearly pop out of my head as I walked in the room.
“I’m sorry Daniel, but it is so hot in here. I couldn’t stand wearing that shirt a minute longer. I figured it would be ok since you’ve been staring at my tits since the moment you came over!”
“That obvious, huh?” I replied.
“Yes, but I don’t mind. I’m actually flattered a good-looking young man like you finds an older woman like me attractive. It shows I still got it,” she said with a wink.
“That’s an understatement if I ever heard one, you are gorgeous!”
“So what do you plan on doing about it?” she replied with a sultry look.
I didn’t need any further encouragement as my mouth immediately found her left nipple, while I teased the right with my hand. Her skin had a salty flavor from her sweat, which only added to my arousal. As her breathing became deeper, I lightly bit down on her nipple. It was not enough to hurt, but just enough to work her up even more. At the same time I started to gently pinch the other.
“That’s right, bite my nipple! It feels so good!” she panted. “Bite down harder!”
Who am I to deny her request? I clamped down on her tit a little harder than before, and then switched to the other and did the same.
“Oh god, yes!” she moaned. “Your teeth feel so good on my tits!”
While I was working on her right breast, my right hand slowly trailed down her sexy stomach until I reached her navel. I then slowly teased around her belly button with my pinky and she began to squirm. My hand then traveled down to the top of her shorts and blindly felt for the buckle. A moment later, I had opened the button on her shorts and started sliding them down her legs. Underneath was a pair of plain white cotton panties, leaving just enough to the imagination.
“Sorry they’re not sexier, I wasn’t expecting company today,” she said with a smirk.
Rather then respond, I slipped a finger in the waistband; and slowly started to lower them. Now all this time I had been working her tits and hadn’t really looked down; so imagine my surprise when my fingers moved between her legs and found a glorious full bush.
“You have a bush!” I exclaimed after taking my mouth off her nipple.
“Like it?” she asked.
“Like it? I fucking love it! There is nothing I find hotter than a woman with a hairy pussy!”
“I tried shaving it once and hated it. I want to feel like a woman, and a bush is so much sexier.”
With that I couldn’t help but to dive right in. Just for the fun of it, I ran my tongue all around her sexy pubes, making them nice and wet.
“You weren’t kidding when you said you love bush,” Cindy said with a giggle. “Now quit fucking around and lick my pussy!”
“Yes ma’am,” I replied with a grin.
The first thing I noticed was her scent; a combination of sweat and arousal. It was musky and I found it absolutely intoxicating. I started by teasing her outer lips, slowly licking up and down either side. During this her breathing became quicker and she started to squirm. I could tell that I was torturing her and she wanted my tongue in her pussy now. Ever so slowly, I opened up her labia to discover the treasure inside. I was in pure heaven with my face buried in the muff of one of the sexiest women I have ever been with. Her pussy was dripping wet by now, and I couldn’t get enough of her taste and smell.
As I tongue her deeper and deeper, she began to moan. “Yeeesss, right there! Your tongue feels so fucking good in my cunt!” Taking that as a sign of encouragement, I start tongue fucking her faster. I feel her legs clamp around my head, like she’s holding on for dear life. I then slide my tongue up to her clit, and she suddenly tensed. I thought she was going to make my head implode with how tightly she was squeezing.
“Oh my god! Don’t you dare fucking stop! I am almost there!” After another few seconds, she came with a scream. “FUUUUCCKK! I’m coming!”
The way her body convulsed nearly knocked my back out of alignment, but I wasn’t done with her yet. I let her orgasm fade and then starting slowly licking my way down. Her legs were bent back now, giving me a much better angle for what I had in mind to do next. I licked down the length of her pussy lips, but instead of going back up to her clit, I kept traveling south. I took it slow, not knowing what her reaction would be.
“Oh you are a naughty boy, aren’t you?” she said with a devilish smile. “Why don’t I make it easier for you?”
She then turned over onto her knees, with her ass up in the air beckoning to me. I could make out her thick pubes sticking down between her legs, which slowly tapered as they neared her small puckered asshole. I stood there staring at this unbelievably sexy sight for what felt like minutes, until she snapped me out of my reverie.
“Well, quit staring and get in there! I want your tongue in my ass!”
I pulled my shirt over my head (I was still dressed this whole time amazingly enough), and dove in. I pulled her ass cheeks apart and was overwhelmed by an aroma that I could not resist. Between the sweat from our labors earlier, the smell of her pussy juices, and her asshole’s natural scent; I couldn’t wait to stick my tongue into her lovely brown-eye.
“That’s right, get your tongue in there! I want to feel you licking my sweaty, dirty asshole clean! You love it don’t you? You filthy bastard!”
I was slowly discovering how dirty of a girl Cindy was, and I was loving every second of it! As my tongue probed deeper into her asshole, I starting finger fucking Cindy’s pussy. I started with one finger, and then added another, and finally a third. Between the anal stimulation from my tongue, and the fingers in her pussy, I could tell she was close to another orgasm.
“Yes! Keep going! Right there! I’m so close!”
I plunged both my tongue and my fingers in as far as they would go, and that set her over the edge. This one lasted even longer than the first, and I was just glad my head wasn’t trapped between her thighs this time!
“That was fucking incredible!” she said after coming down from her orgasm. “You are very skilled with your tongue. I think its time for me to return the favor.”
She leaned over and started unbuckling my belt while licking her way down my chest. My cock, which had been so far neglected, sprang back into life in no time. Once my belt was taken care of, she pulled my shorts down below my knees and went to work. She started by teasing the tip with her tongue, while one hand traveled down to caress my balls. Her tongue would occasionally dart in and out of my pee slit, and her circles got larger and larger around my mushroom head. She then slowly licked down the underside of my shaft, paying special attention to my super-sensitive frenulum, until she reached the base. She did this a few times; going up and down my cock, until she finally took the head into her mouth. It was fucking amazing and I couldn’t help but moan in pleasure.
“Your cock tastes so good!” she said before swallowing more of my shaft.
Now as I’ve stated before, I’m not huge in the dick department; and this can sometimes work to my benefit. Many girls are able to deep throat me easier than they could a monster cock, and this time was no exception. Cindy had my cock down her throat and her lips were brushing my pubic hair. She started moving her head up and down my shaft, gradually building up speed. I was tempted to start face fucking her since it felt so incredible, but I didn’t want to shoot my load this soon. As if reading my thoughts (which she probably was since this obviously wasn’t her first rodeo), she slowed down and pulled my cock out of her mouth. I was torn between wanting her to continue the amazing blowjob, and my desire to hold off.
Cindy was extremely intuitive however, and quickly started working her tongue down my shaft again. She kept going lower this time and started licking on my balls. She then took them into her mouth and I gasped in pleasure/discomfort.
While working my balls with her mouth, she was generating plenty of saliva, which is good because what she did next caught me by surprise. She took a finger and rubbed it into saliva oozing between my legs, and started to press her finger to my asshole! Now, I have experimented with anal play a few times while masturbating, but never had anyone else touched me there. It’s not something a straight man will typically admit to enjoying, but she obviously was not deterred. Oh my god, it felt amazing.
“Holy shit!” I gasped after having may asshole penetrated, “That feels fucking great!”
“Of course it does, I’m stimulating your prostate,” she said knowingly.
Cindy kept her finger in my ass, moving it slowly in and out, and began working her way up my cock again. She once again took me into her mouth, and I experienced pure bliss. Once she began to make love to my cock with her tongue, she rotated her body so her pussy was right over my face. I buried my face in that lovely cunt again while she continued giving me the best head of my life. This continued on for a few minutes and I could feel myself getting closer and closer. Her moans were growing louder, despite having a mouthful of cock. She edged me up right to the brink before I pulled my dick out of her mouth.
“Too much, huh?” she asked.
I just nodded in agreement, while I allowed myself to calm down a bit. After a minute or two I was ready to fuck her without the fear of coming immediately.
“That blowjob was incredible, but what I really want now is to fuck that beautiful hairy pussy!”
She grinned from ear to ear, and then laid back with her legs spread wide. What a beautiful sight that was! I stood there for a moment, just taking her all in, until she beckoned to me with her finger.
“I can’t wait to feel you inside me. Come fuck me now!”
After the multiple oral ministrations, her pussy was extremely wet and sloppy, and I had no trouble sliding right in. We both gasped as soon as I was buried to the hilt. “Oh god yes, you feel fucking incredible,” I said while slowly beginning to move in and out. I started off nice and slow, wanting to make this last; but soon she urged me to go faster.
“Come on, fuck me with that dick! Harder!” she demanded. “Give me a real fucking!”
I started thrusting faster and harder, and soon I was pounding away at her pussy like there was no tomorrow.
“Yes! Just like that! Fuck my juicy pussy! Give me everything you have!”
With her words fueling me, I began to fuck her even harder. I was driving her body deeper and deeper into the couch, and the whole time she was panting and moaning.
“Keep going just like that! Right there! I’m so fucking close!”
I continued to slam my cock into her, and amazingly I was able to control myself from going past the point of no return. I could tell she was close, so I leaned forward and bit down on her right nipple. That was enough to set her over the edge. She came violently this time, and her juices squirted out all over my cock.
“HOLY SHIT! I felt like I was having a seizure, it was so intense.”
“I could tell; you squirted all over me!” I said with a smile.
She bent over and took my cock in her mouth again, cleaning her juices until it was spotless. I could tell she enjoyed the taste of her own arousal, because she continued licking all around my ball sack and groin. She continued on with this for another minute or two, before pulling away and turning over.
“I want you to fuck my ass Daniel! I need to feel your cock stretching me out. I have lube in the box next to the end table; go get it!”
Now at this point, I was sure that I had died and gone to heaven, because this woman was my ultimate fantasy. Not wasting any time, I shuffled over to the box she indicated and began to dig for the lube. I discovered that that was her sex toy stash, and she had all sorts of goodies in there. There were nipple clamps, anal beads, handcuffs, a rabbit-shaped vibrator, a medium size butt plug, and an 8” long dildo with a harness. Hmmm… I wondered to myself, but the thought was nearly forgotten once I found the bottle of lube at the bottom of the box.
I walked back over to Cindy holding the lube and what was probably a shit-eating grin on my face. She had laid her face down on one end of the couch, with her beautiful ass sticking up in the air beckoning to me. I have her right cheek a soft slap, which elicited a small squeal from Cindy.
“I didn’t smack you hard,” I said while rubbing her ass gently.
“It didn’t hurt, you just caught me by surprise,” she replied.
Moving back to the task at hand, I couldn’t resist another taste of her inviting back door. I slowly started licking all around her rosebud, and gradually started pushing my tongue past her sphincter.
“Yes!” she hissed, “Your tongue feels amazing!”
I stuck a finger into her still moist pussy for some additional lubrication, and then slid it into her tight pucker. By this time she was really getting into it and started pushing back against my finger with each thrust. I then added a second finger to stretch her out a bit more. It was somewhat difficult, so I squeezed some lube onto her asshole and rubbed it in. Now that she was nice and slippery, two fingers easily slid into her tight hole.
“Give me your cock! I need you to fuck my tight asshole now!” she wailed.
Knowing she was ready, I pulled my fingers out of her ass and placed the tip of my cock at her rosebud. I slowly began to apply pressure and her sphincter was welcoming the new intrusion. “Oh God, that’s it! Just go slow until I get used to being stretched.”
I continued easing my dick into her ass; each inch greeted by a moan, until my pubes were brushing against her ass cheeks and my balls were slapping her pussy.
“Your ass is so tight Cindy! It feels fucking incredible!
I held still allowing her to adjust to my cock in her ass, and it was only a matter of seconds before she slowly began to move. I began to slide my cock in and out at a moderate pace, and soon I could tell she was really enjoying herself. As I picked up speed, she started rubbing her clit, and her moans grew louder. Soon I was hammering at her ass the way I did her cunt earlier, and I knew I wasn’t going to last much longer.
“Fuck! Fuck! I’m getting close!”
“Don’t stop! Keeping fucking my ass! I’m almost there!”
God knows how, but I managed to hold off just long enough for her to have a screaming orgasm. By the sounds of it, it was probably the most intense of the afternoon.
“HOLY SHIT! FUCK! Keep going baby, I want your cum in my ass!”
That was what set me over the edge. I reached what was probably the best climax of my life, and pumped her ass full of my seed. This lasted for about thirty seconds or so, and I then practically collapsed from the effort. My cock slowly slid from her now gaping hole, and I flopped back onto the couch exhausted. Thinking this was one of the best afternoons of my life, I figured we would soon get dressed and have those beers we neglected.
To my surprise, Cindy had more in store for me that afternoon. She next did one of the hottest and filthiest things I have ever seen. She stuck her finger into her ass, moving it around a few times, until the cum started leaking out onto the couch. Once there was a nice puddle, she leaned forward and licked it up, not wasting a drop.
“Mmmm, your cum tastes so good Daniel,” she said with a smile.
“You really are one nasty woman, aren’t you?”
“Just wait to see what else I have planned,” she smiled wickedly.
Something about that smile made me a little nervous, but at the same time extremely excited. I sat there and caught my breath for a few more minutes and nursed my now-warm beer. Cindy went to the bathroom, probably to pee and clean herself up a bit. When she came back out, she was still fully nude and sexy as ever.
“Since you did such a wonderful job fucking my ass, I thought it was only fair for me to return the favor.”
“Umm… Excuse me?”
“You heard me,” she said with a smirk. “I know you saw my strap-on when you went to get the lube. I’m going to fuck your ass with it.”
“I don’t know about that, I’ve never done that before,” I replied.
“Don’t worry, I’ll take it easy on you- at first.”
She grabbed the strap-on from her box of goodies, and set it down next to her at the base of the couch. With it out in the open, I was able to get a better look at the dildo. It was flesh-colored, about eight inches in length, and one and a half thick. I couldn’t tell whether I was more nervous or excited over the thought of her fucking my ass with it. To be honest, the idea was turning me on!
Cindy sat down on the floor, and motioned to me to come over. I walked over to her and she turned me around so my ass was in her face. She spread apart my ass cheeks and started to tease the area around my backdoor. She licked from the base of my ball sack to the top of my ass crack, and back down again. It was incredible, but not as incredible as when she first started to tongue my asshole.
“Oh my God, that feels great!” I said. “I had no idea this would feel so good.”
“Just wait, I’m only getting started,” she replied.
With that, she started pushing her tongue deeper and deeper into my ass, loosening my sphincter muscles for what was to come. She tongue fucked my ass for a few minutes with me moaning the whole time, gradually getting louder. Once she thought my ass was slippery enough with her saliva, she pushed her finger into my ass up to the knuckle. Not meeting any resistance, she added a second, which also went in smoothly. I moaned again, and asked for more.
“This isn’t your first time having your ass played with, is it?” she asked me with a devilish grin.
“No, I like to play with my ass sometimes when I masturbate, but this is the first time someone else has ever done it,” I replied. “The fact that it is something I enjoy was not something I wanted to admit I guess.”
“Sounds like you’ve really been missing out. Good thing I came along!”
She fucked my ass with two fingers for a minute or two, and then grabbed the bottle of lube from the floor. She squeezed a generous amount onto her fingers and began to work the lube onto my pucker. The cool sensation from the liquid made me suck in my breath, but it quickly warmed from my body heat. Once I was nice and lubed up, Cindy wrapped the harness from the strap on around her waist and inserted the dildo. The speed with which she was able to accomplish this led me to believe she’d had quite a bit of experience with it.
“Don’t you love my cock?” she asked me.
“I love your cock Cindy, you look sexy as hell.”
“Good, now suck it, bitch”
I slowly took the tip of the dildo into my mouth to get a feel for it, and gradually began taking it in.
“You can do better than that! I want to see you deep throat my cock.”
I’m not going to lie, the thought intimidated me a bit; but I nodded my head and took more of it into my mouth. Once it hit my throat, my gag reflex kicked in, and I nearly spit it out.
“Relax your throat. It will be much easier that way.”
I tried to do as instructed, and after another minute I finally managed to swallow it down to the fake balls at the base.
“That’s a good job for a first try; I’m impressed! Now are you ready to get your ass fucked?”
With my mouth still full of the fake cock, all I could do was nod. She took the dildo out of my mouth and motioned for me to turn around. She the placed the tip of the cock against my pucker and slowly began to apply pressure. I felt my sphincter muscles being stretched more than they were accustomed to, and a slight pain began to build.
“Just relax your ass muscles. Push out like you have to take a shit, and it will help the dildo to go in.”
I pushed out like she said, and finally I felt the mushroom head slip past my asshole and into my rectum.
“Holy fuck! I feel so full back there! I’ve never taken something so big before,” I said. “Just take it slow to start.”
She slid the rest of the dildo into my ass and held there for a minute while I adjusted to its size. Once the initial discomfort started to fade, it began to feel great. I started to push back against the strap on, and she took that as her cue to start moving in and out. She began rather slowly: easing it nearly all the way out, and the all the way in again. It was incredible! With each thrust my prostate was being stimulated, and the intensity continued to grow the longer she fucked me.
“This feels so fucking good!” I shouted. “Faster! Fuck me harder!”
She began to pound my ass the way a man would fuck a pussy, and I was loving every second of it.
“That’s right, take my cock you bitch!” she shouted. "I know you love it. Scream for me!”
“Aaaaghh!” I grunted for her as she pounded my ass again.
“Flip over. I want to look you in the eyes while I fuck your ass.”
As requested, I turned over onto my back and held my legs up in the air. Not the most masculine position, but once she pushed the dildo back into my ass I couldn’t care less. I watched the look of determination on her face as she fucked me and thought it was one of the sexiest things I have ever seen. The sweat began to pour off her brow, down her face, and between her tits, eventually dripping onto my stomach.
The new angle seemed to really get my prostate, and all of a sudden I was getting a strange new sensation, quite different than I had ever experienced before. It was a strong tingling in my rectum that grew stronger as she thrust. I think I was on the verge of my first anal orgasm!
“Holy shit! I’m gonna come!” I yelled. “I’m almost there!”
With that I felt the most intense orgasm of my life, which coursed throughout my entire body. I had no idea you could have an orgasm from anal sex alone, not to mention how mind-blowing it could be! As I shot my load all over my stomach, Cindy caught up with me and had her own orgasm. Once she recovered, she slowly slid the dildo from my ass, and I had a strange empty feeling. My ass felt a bit sore, but in a pleasant way. She then bent down and began to lick all of the jizz from my stomach until I was thoroughly clean.
We collapsed onto the sofa together with her head on my chest. We just stayed there for a while, just enjoying the feeling of each other’s bodies. I was utterly spent, yet completely fulfilled.
“That was the best sex I’ve ever had!” I said to Cindy. “I think I’m in love, where have you been all my life?” I joked.
“I don’t know about love, but I’m glad to have you as my new neighbor,” she replied. “I just got out of a bad marriage and I’m not looking for a relationship, but we can still have fun can’t we?”
“Yes we can….” I thought as I drifted off to sleep.
****
Author's Note: This is my first attempt at writing, so please feel free to comment with any constructive criticism. This is the first of what I hope to be a three to four part series.
A couple days after she moved in, I went over to introduce myself and welcome her to the neighborhood. After I rang the doorbell, I was treated to an incredible sight. She was dressed in just a tight t-shirt that accented her generous tits, and a pair of tiny shorts that allowed her gorgeous ass to peak out the bottom. She was curvy in all the right places, and I realized she was not just attractive; she was fucking stunning! Shoulder-length brown hair perfectly framed her beautiful brown eyes and slightly pouty lips. With a closer look, she appeared to be at least ten years my senior, but still incredibly sexy. My cock began to swell immediately, and I shifted slightly to make it less obvious. Thankfully, she didn’t appear to notice. There did seem to be a mutual attraction however, as I couldn’t help but notice her eyes taking me in.
“Can I help you?” she asked.
“Hi, I’m Daniel,” I said, “I just wanted to stop by and welcome you to the neighborhood.”
“Hi Daniel,” she said, eyeing me ever so subtly, “My name is Cindy. I just moved to the area from Long Island.”
After a few minutes of conversation, I learned that she was recently divorced and moved upstate to start over with her professional photography career. It was mid-summer and very hot that day. She had faint sheen of sweat on her forehead, and it was clear she was unpacking and getting settled.
“Is there anything I can help you with?” I asked hopefully, while in the back of my mind thinking that I’d love to help her out of those shorts. “It must be tough to do this all by yourself.”
“Thanks Daniel, I may just take you up on your offer,” she said with a slight smile. “Just warning you though, the A/C isn’t working, and I haven’t had a chance to have someone take a look at it yet. I have some beer in the fridge to help keep us cool.”
“Sounds like a plan! Let me go change into an old t-shirt and I’ll be right back.”
As I walked back to my house to change, all I could do is think about my great luck to be invited into the home of such a stunning older woman. Sure, I was only helping her unpack some boxes, maybe move some furniture; but a guy can hope.
I wonder if I have any shot at all? I thought to myself. She did seem to be checking me out.
Within a few minutes, I was knocking at her door. As I stepped inside, the oppressive heat suddenly hit me.
“You weren’t kidding, it is hot in here!”
“Tell me about it. My shirt is clinging to my body it is so soaked in sweat!”
Of course after she brought this to my attention I couldn’t help but notice the damp line running down the back of her t-shirt. You are welcome to take it off any time you want, I thought with a smile. After grabbing a glass of water to keep hydrated, we got to work. Over the next 2-3 hours I helped her move nearly every piece of furniture in the house. By the time everything was where she wanted, I was hot, sweaty, and exhausted.
“Thanks again for your help! How about that beer?” she asked.
“That sounds amazing right now,” I replied. While she went to the kitchen to grab two beers, I stepped into the bathroom to wash my hands and face from sweat and grime.
A moment later I walked back to the living room, and was stunned by what I saw. Cindy was sitting on the couch in nothing but her shorts. Her tits were even better than I imagined! I would guess they were about a 36C, with no noticeable sag. Considering she was probably in her mid-to-late forties, they seemed too good to be true.
She must have seen my eyes nearly pop out of my head as I walked in the room.
“I’m sorry Daniel, but it is so hot in here. I couldn’t stand wearing that shirt a minute longer. I figured it would be ok since you’ve been staring at my tits since the moment you came over!”
“That obvious, huh?” I replied.
“Yes, but I don’t mind. I’m actually flattered a good-looking young man like you finds an older woman like me attractive. It shows I still got it,” she said with a wink.
“That’s an understatement if I ever heard one, you are gorgeous!”
“So what do you plan on doing about it?” she replied with a sultry look.
I didn’t need any further encouragement as my mouth immediately found her left nipple, while I teased the right with my hand. Her skin had a salty flavor from her sweat, which only added to my arousal. As her breathing became deeper, I lightly bit down on her nipple. It was not enough to hurt, but just enough to work her up even more. At the same time I started to gently pinch the other.
“That’s right, bite my nipple! It feels so good!” she panted. “Bite down harder!”
Who am I to deny her request? I clamped down on her tit a little harder than before, and then switched to the other and did the same.
“Oh god, yes!” she moaned. “Your teeth feel so good on my tits!”
While I was working on her right breast, my right hand slowly trailed down her sexy stomach until I reached her navel. I then slowly teased around her belly button with my pinky and she began to squirm. My hand then traveled down to the top of her shorts and blindly felt for the buckle. A moment later, I had opened the button on her shorts and started sliding them down her legs. Underneath was a pair of plain white cotton panties, leaving just enough to the imagination.
“Sorry they’re not sexier, I wasn’t expecting company today,” she said with a smirk.
Rather then respond, I slipped a finger in the waistband; and slowly started to lower them. Now all this time I had been working her tits and hadn’t really looked down; so imagine my surprise when my fingers moved between her legs and found a glorious full bush.
“You have a bush!” I exclaimed after taking my mouth off her nipple.
“Like it?” she asked.
“Like it? I fucking love it! There is nothing I find hotter than a woman with a hairy pussy!”
“I tried shaving it once and hated it. I want to feel like a woman, and a bush is so much sexier.”
With that I couldn’t help but to dive right in. Just for the fun of it, I ran my tongue all around her sexy pubes, making them nice and wet.
“You weren’t kidding when you said you love bush,” Cindy said with a giggle. “Now quit fucking around and lick my pussy!”
“Yes ma’am,” I replied with a grin.
The first thing I noticed was her scent; a combination of sweat and arousal. It was musky and I found it absolutely intoxicating. I started by teasing her outer lips, slowly licking up and down either side. During this her breathing became quicker and she started to squirm. I could tell that I was torturing her and she wanted my tongue in her pussy now. Ever so slowly, I opened up her labia to discover the treasure inside. I was in pure heaven with my face buried in the muff of one of the sexiest women I have ever been with. Her pussy was dripping wet by now, and I couldn’t get enough of her taste and smell.
As I tongue her deeper and deeper, she began to moan. “Yeeesss, right there! Your tongue feels so fucking good in my cunt!” Taking that as a sign of encouragement, I start tongue fucking her faster. I feel her legs clamp around my head, like she’s holding on for dear life. I then slide my tongue up to her clit, and she suddenly tensed. I thought she was going to make my head implode with how tightly she was squeezing.
“Oh my god! Don’t you dare fucking stop! I am almost there!” After another few seconds, she came with a scream. “FUUUUCCKK! I’m coming!”
The way her body convulsed nearly knocked my back out of alignment, but I wasn’t done with her yet. I let her orgasm fade and then starting slowly licking my way down. Her legs were bent back now, giving me a much better angle for what I had in mind to do next. I licked down the length of her pussy lips, but instead of going back up to her clit, I kept traveling south. I took it slow, not knowing what her reaction would be.
“Oh you are a naughty boy, aren’t you?” she said with a devilish smile. “Why don’t I make it easier for you?”
She then turned over onto her knees, with her ass up in the air beckoning to me. I could make out her thick pubes sticking down between her legs, which slowly tapered as they neared her small puckered asshole. I stood there staring at this unbelievably sexy sight for what felt like minutes, until she snapped me out of my reverie.
“Well, quit staring and get in there! I want your tongue in my ass!”
I pulled my shirt over my head (I was still dressed this whole time amazingly enough), and dove in. I pulled her ass cheeks apart and was overwhelmed by an aroma that I could not resist. Between the sweat from our labors earlier, the smell of her pussy juices, and her asshole’s natural scent; I couldn’t wait to stick my tongue into her lovely brown-eye.
“That’s right, get your tongue in there! I want to feel you licking my sweaty, dirty asshole clean! You love it don’t you? You filthy bastard!”
I was slowly discovering how dirty of a girl Cindy was, and I was loving every second of it! As my tongue probed deeper into her asshole, I starting finger fucking Cindy’s pussy. I started with one finger, and then added another, and finally a third. Between the anal stimulation from my tongue, and the fingers in her pussy, I could tell she was close to another orgasm.
“Yes! Keep going! Right there! I’m so close!”
I plunged both my tongue and my fingers in as far as they would go, and that set her over the edge. This one lasted even longer than the first, and I was just glad my head wasn’t trapped between her thighs this time!
“That was fucking incredible!” she said after coming down from her orgasm. “You are very skilled with your tongue. I think its time for me to return the favor.”
She leaned over and started unbuckling my belt while licking her way down my chest. My cock, which had been so far neglected, sprang back into life in no time. Once my belt was taken care of, she pulled my shorts down below my knees and went to work. She started by teasing the tip with her tongue, while one hand traveled down to caress my balls. Her tongue would occasionally dart in and out of my pee slit, and her circles got larger and larger around my mushroom head. She then slowly licked down the underside of my shaft, paying special attention to my super-sensitive frenulum, until she reached the base. She did this a few times; going up and down my cock, until she finally took the head into her mouth. It was fucking amazing and I couldn’t help but moan in pleasure.
“Your cock tastes so good!” she said before swallowing more of my shaft.
Now as I’ve stated before, I’m not huge in the dick department; and this can sometimes work to my benefit. Many girls are able to deep throat me easier than they could a monster cock, and this time was no exception. Cindy had my cock down her throat and her lips were brushing my pubic hair. She started moving her head up and down my shaft, gradually building up speed. I was tempted to start face fucking her since it felt so incredible, but I didn’t want to shoot my load this soon. As if reading my thoughts (which she probably was since this obviously wasn’t her first rodeo), she slowed down and pulled my cock out of her mouth. I was torn between wanting her to continue the amazing blowjob, and my desire to hold off.
Cindy was extremely intuitive however, and quickly started working her tongue down my shaft again. She kept going lower this time and started licking on my balls. She then took them into her mouth and I gasped in pleasure/discomfort.
While working my balls with her mouth, she was generating plenty of saliva, which is good because what she did next caught me by surprise. She took a finger and rubbed it into saliva oozing between my legs, and started to press her finger to my asshole! Now, I have experimented with anal play a few times while masturbating, but never had anyone else touched me there. It’s not something a straight man will typically admit to enjoying, but she obviously was not deterred. Oh my god, it felt amazing.
“Holy shit!” I gasped after having may asshole penetrated, “That feels fucking great!”
“Of course it does, I’m stimulating your prostate,” she said knowingly.
Cindy kept her finger in my ass, moving it slowly in and out, and began working her way up my cock again. She once again took me into her mouth, and I experienced pure bliss. Once she began to make love to my cock with her tongue, she rotated her body so her pussy was right over my face. I buried my face in that lovely cunt again while she continued giving me the best head of my life. This continued on for a few minutes and I could feel myself getting closer and closer. Her moans were growing louder, despite having a mouthful of cock. She edged me up right to the brink before I pulled my dick out of her mouth.
“Too much, huh?” she asked.
I just nodded in agreement, while I allowed myself to calm down a bit. After a minute or two I was ready to fuck her without the fear of coming immediately.
“That blowjob was incredible, but what I really want now is to fuck that beautiful hairy pussy!”
She grinned from ear to ear, and then laid back with her legs spread wide. What a beautiful sight that was! I stood there for a moment, just taking her all in, until she beckoned to me with her finger.
“I can’t wait to feel you inside me. Come fuck me now!”
After the multiple oral ministrations, her pussy was extremely wet and sloppy, and I had no trouble sliding right in. We both gasped as soon as I was buried to the hilt. “Oh god yes, you feel fucking incredible,” I said while slowly beginning to move in and out. I started off nice and slow, wanting to make this last; but soon she urged me to go faster.
“Come on, fuck me with that dick! Harder!” she demanded. “Give me a real fucking!”
I started thrusting faster and harder, and soon I was pounding away at her pussy like there was no tomorrow.
“Yes! Just like that! Fuck my juicy pussy! Give me everything you have!”
With her words fueling me, I began to fuck her even harder. I was driving her body deeper and deeper into the couch, and the whole time she was panting and moaning.
“Keep going just like that! Right there! I’m so fucking close!”
I continued to slam my cock into her, and amazingly I was able to control myself from going past the point of no return. I could tell she was close, so I leaned forward and bit down on her right nipple. That was enough to set her over the edge. She came violently this time, and her juices squirted out all over my cock.
“HOLY SHIT! I felt like I was having a seizure, it was so intense.”
“I could tell; you squirted all over me!” I said with a smile.
She bent over and took my cock in her mouth again, cleaning her juices until it was spotless. I could tell she enjoyed the taste of her own arousal, because she continued licking all around my ball sack and groin. She continued on with this for another minute or two, before pulling away and turning over.
“I want you to fuck my ass Daniel! I need to feel your cock stretching me out. I have lube in the box next to the end table; go get it!”
Now at this point, I was sure that I had died and gone to heaven, because this woman was my ultimate fantasy. Not wasting any time, I shuffled over to the box she indicated and began to dig for the lube. I discovered that that was her sex toy stash, and she had all sorts of goodies in there. There were nipple clamps, anal beads, handcuffs, a rabbit-shaped vibrator, a medium size butt plug, and an 8” long dildo with a harness. Hmmm… I wondered to myself, but the thought was nearly forgotten once I found the bottle of lube at the bottom of the box.
I walked back over to Cindy holding the lube and what was probably a shit-eating grin on my face. She had laid her face down on one end of the couch, with her beautiful ass sticking up in the air beckoning to me. I have her right cheek a soft slap, which elicited a small squeal from Cindy.
“I didn’t smack you hard,” I said while rubbing her ass gently.
“It didn’t hurt, you just caught me by surprise,” she replied.
Moving back to the task at hand, I couldn’t resist another taste of her inviting back door. I slowly started licking all around her rosebud, and gradually started pushing my tongue past her sphincter.
“Yes!” she hissed, “Your tongue feels amazing!”
I stuck a finger into her still moist pussy for some additional lubrication, and then slid it into her tight pucker. By this time she was really getting into it and started pushing back against my finger with each thrust. I then added a second finger to stretch her out a bit more. It was somewhat difficult, so I squeezed some lube onto her asshole and rubbed it in. Now that she was nice and slippery, two fingers easily slid into her tight hole.
“Give me your cock! I need you to fuck my tight asshole now!” she wailed.
Knowing she was ready, I pulled my fingers out of her ass and placed the tip of my cock at her rosebud. I slowly began to apply pressure and her sphincter was welcoming the new intrusion. “Oh God, that’s it! Just go slow until I get used to being stretched.”
I continued easing my dick into her ass; each inch greeted by a moan, until my pubes were brushing against her ass cheeks and my balls were slapping her pussy.
“Your ass is so tight Cindy! It feels fucking incredible!
I held still allowing her to adjust to my cock in her ass, and it was only a matter of seconds before she slowly began to move. I began to slide my cock in and out at a moderate pace, and soon I could tell she was really enjoying herself. As I picked up speed, she started rubbing her clit, and her moans grew louder. Soon I was hammering at her ass the way I did her cunt earlier, and I knew I wasn’t going to last much longer.
“Fuck! Fuck! I’m getting close!”
“Don’t stop! Keeping fucking my ass! I’m almost there!”
God knows how, but I managed to hold off just long enough for her to have a screaming orgasm. By the sounds of it, it was probably the most intense of the afternoon.
“HOLY SHIT! FUCK! Keep going baby, I want your cum in my ass!”
That was what set me over the edge. I reached what was probably the best climax of my life, and pumped her ass full of my seed. This lasted for about thirty seconds or so, and I then practically collapsed from the effort. My cock slowly slid from her now gaping hole, and I flopped back onto the couch exhausted. Thinking this was one of the best afternoons of my life, I figured we would soon get dressed and have those beers we neglected.
To my surprise, Cindy had more in store for me that afternoon. She next did one of the hottest and filthiest things I have ever seen. She stuck her finger into her ass, moving it around a few times, until the cum started leaking out onto the couch. Once there was a nice puddle, she leaned forward and licked it up, not wasting a drop.
“Mmmm, your cum tastes so good Daniel,” she said with a smile.
“You really are one nasty woman, aren’t you?”
“Just wait to see what else I have planned,” she smiled wickedly.
Something about that smile made me a little nervous, but at the same time extremely excited. I sat there and caught my breath for a few more minutes and nursed my now-warm beer. Cindy went to the bathroom, probably to pee and clean herself up a bit. When she came back out, she was still fully nude and sexy as ever.
“Since you did such a wonderful job fucking my ass, I thought it was only fair for me to return the favor.”
“Umm… Excuse me?”
“You heard me,” she said with a smirk. “I know you saw my strap-on when you went to get the lube. I’m going to fuck your ass with it.”
“I don’t know about that, I’ve never done that before,” I replied.
“Don’t worry, I’ll take it easy on you- at first.”
She grabbed the strap-on from her box of goodies, and set it down next to her at the base of the couch. With it out in the open, I was able to get a better look at the dildo. It was flesh-colored, about eight inches in length, and one and a half thick. I couldn’t tell whether I was more nervous or excited over the thought of her fucking my ass with it. To be honest, the idea was turning me on!
Cindy sat down on the floor, and motioned to me to come over. I walked over to her and she turned me around so my ass was in her face. She spread apart my ass cheeks and started to tease the area around my backdoor. She licked from the base of my ball sack to the top of my ass crack, and back down again. It was incredible, but not as incredible as when she first started to tongue my asshole.
“Oh my God, that feels great!” I said. “I had no idea this would feel so good.”
“Just wait, I’m only getting started,” she replied.
With that, she started pushing her tongue deeper and deeper into my ass, loosening my sphincter muscles for what was to come. She tongue fucked my ass for a few minutes with me moaning the whole time, gradually getting louder. Once she thought my ass was slippery enough with her saliva, she pushed her finger into my ass up to the knuckle. Not meeting any resistance, she added a second, which also went in smoothly. I moaned again, and asked for more.
“This isn’t your first time having your ass played with, is it?” she asked me with a devilish grin.
“No, I like to play with my ass sometimes when I masturbate, but this is the first time someone else has ever done it,” I replied. “The fact that it is something I enjoy was not something I wanted to admit I guess.”
“Sounds like you’ve really been missing out. Good thing I came along!”
She fucked my ass with two fingers for a minute or two, and then grabbed the bottle of lube from the floor. She squeezed a generous amount onto her fingers and began to work the lube onto my pucker. The cool sensation from the liquid made me suck in my breath, but it quickly warmed from my body heat. Once I was nice and lubed up, Cindy wrapped the harness from the strap on around her waist and inserted the dildo. The speed with which she was able to accomplish this led me to believe she’d had quite a bit of experience with it.
“Don’t you love my cock?” she asked me.
“I love your cock Cindy, you look sexy as hell.”
“Good, now suck it, bitch”
I slowly took the tip of the dildo into my mouth to get a feel for it, and gradually began taking it in.
“You can do better than that! I want to see you deep throat my cock.”
I’m not going to lie, the thought intimidated me a bit; but I nodded my head and took more of it into my mouth. Once it hit my throat, my gag reflex kicked in, and I nearly spit it out.
“Relax your throat. It will be much easier that way.”
I tried to do as instructed, and after another minute I finally managed to swallow it down to the fake balls at the base.
“That’s a good job for a first try; I’m impressed! Now are you ready to get your ass fucked?”
With my mouth still full of the fake cock, all I could do was nod. She took the dildo out of my mouth and motioned for me to turn around. She the placed the tip of the cock against my pucker and slowly began to apply pressure. I felt my sphincter muscles being stretched more than they were accustomed to, and a slight pain began to build.
“Just relax your ass muscles. Push out like you have to take a shit, and it will help the dildo to go in.”
I pushed out like she said, and finally I felt the mushroom head slip past my asshole and into my rectum.
“Holy fuck! I feel so full back there! I’ve never taken something so big before,” I said. “Just take it slow to start.”
She slid the rest of the dildo into my ass and held there for a minute while I adjusted to its size. Once the initial discomfort started to fade, it began to feel great. I started to push back against the strap on, and she took that as her cue to start moving in and out. She began rather slowly: easing it nearly all the way out, and the all the way in again. It was incredible! With each thrust my prostate was being stimulated, and the intensity continued to grow the longer she fucked me.
“This feels so fucking good!” I shouted. “Faster! Fuck me harder!”
She began to pound my ass the way a man would fuck a pussy, and I was loving every second of it.
“That’s right, take my cock you bitch!” she shouted. "I know you love it. Scream for me!”
“Aaaaghh!” I grunted for her as she pounded my ass again.
“Flip over. I want to look you in the eyes while I fuck your ass.”
As requested, I turned over onto my back and held my legs up in the air. Not the most masculine position, but once she pushed the dildo back into my ass I couldn’t care less. I watched the look of determination on her face as she fucked me and thought it was one of the sexiest things I have ever seen. The sweat began to pour off her brow, down her face, and between her tits, eventually dripping onto my stomach.
The new angle seemed to really get my prostate, and all of a sudden I was getting a strange new sensation, quite different than I had ever experienced before. It was a strong tingling in my rectum that grew stronger as she thrust. I think I was on the verge of my first anal orgasm!
“Holy shit! I’m gonna come!” I yelled. “I’m almost there!”
With that I felt the most intense orgasm of my life, which coursed throughout my entire body. I had no idea you could have an orgasm from anal sex alone, not to mention how mind-blowing it could be! As I shot my load all over my stomach, Cindy caught up with me and had her own orgasm. Once she recovered, she slowly slid the dildo from my ass, and I had a strange empty feeling. My ass felt a bit sore, but in a pleasant way. She then bent down and began to lick all of the jizz from my stomach until I was thoroughly clean.
We collapsed onto the sofa together with her head on my chest. We just stayed there for a while, just enjoying the feeling of each other’s bodies. I was utterly spent, yet completely fulfilled.
“That was the best sex I’ve ever had!” I said to Cindy. “I think I’m in love, where have you been all my life?” I joked.
“I don’t know about love, but I’m glad to have you as my new neighbor,” she replied. “I just got out of a bad marriage and I’m not looking for a relationship, but we can still have fun can’t we?”
“Yes we can….” I thought as I drifted off to sleep.
****
Author's Note: This is my first attempt at writing, so please feel free to comment with any constructive criticism. This is the first of what I hope to be a three to four part series.
Annalisa
- 16.10.2022
- 6
- 0
- Category:
- Anal
