An Affair With My Friend's Mom free porn video

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My name is Keith, I was 18 and in my freshman year of college at a small Midwestern University. I was a music major, trumpet my instrument of focus. In addition to many other musical endeavors I was in the jazz band. That winter the jazz band was taking its’ biannual trip to Hawaii to escape the snow for a week and play some gigs in Honolulu. family was allowed to come along on the trip. At the hotel in Hawaii it was 4 to a room. My roommate Jon, a fellow trumpeter, and I shared a bed. Also in the room was Jon’s long time girlfriend Sara (who played sax in the band) sharing a bed with her mom Jackie. I was a little surprised they let us all room together but I guess I was an adult now, not in high school anymore.

Jon’s girlfriend Sara is very athletic, nice body, not the prettiest face. Though as the only way I’d ever known her was as Jon’s girl I’d never really thought about being attracted to her. Jackie, on the other hand, I found I was very attracted to. Yea she was an older woman, but damn did she still have it. She was single at the time. As an aside, Jackie is now remarried to a very rich older man. I don’t know what the guy does but his only son writes all the music for a very famous American pop singer, no bullshit. This guy’s loaded; a testament to Jackie’s hotness. Not saying the guy doesn’t love her and she him….but you know how it goes.

So after our first day in Hawaii, as we got in at around 6am, I was pretty tired. I was also pretty worked up seeing all the barely covered flesh on the Waikiki beach. I decided that before I went to bed I’d go into the bathroom and rub one out. Jon, Sara, and Jackie were down in the bar so I thought I had the place to myself. I turned on that overhead fan thing hotel bathrooms always have to drown out any little noises I might make just in case someone came back while I was busy. I guess I must have forgotten to lock the door ‘cause just as I was getting ready finish Jackie walked in and saw me sitting on the edge of the tub, my rock hard cock in my hand just about to burst. She was wearing a bikini with a towel over her shoulder and even though my hand stopped movie as soon as the door opened that sexy sight was all my dick needed and as she looked at me in surprise I came all over the tile floor.
I looked up at Jackie in horror and tried to cover myself. I could tell she was a little intoxicated, and she just smiled and said “make sure you clean that up big guy.” With that she closed the door and left me to myself. I cleaned up the cum and took a hot shower, not wanting to think about how awkward it was going to be around her for the rest of the week. As I got dressed and walked out into the room she was sitting on her bed reading a book. Jon and Sara were still out. She was now wearing a thin fabric floral print robe that was revealing quite a bit of leg and cleavage. She looked at me over her glasses in an extremely sexy manner. She could tell I was tremendously embarrassed. “Don’t worry about it Keith. I have a son too, I know how you young guys are. I won’t tell anyone.” I didn’t know what to say so I just said “thanks” and went down to the bar to join Jon and Sara.

The next morning I was up quite a bit earlier than Jon and Sara, they had drunk quite a bit the night before. I went out to have some fun in Honolulu but by the time 3pm rolled around I starting to feel really jet lagged. I called Jon and Sara to see what they had gotten up to. “We’re at the zoo” said Jon. “We’re probably gonna head to the aquarium after this and then to the beach for a while before dinner. We’re going to eat at Dukes at 7 if you want to join us” “Sure, I’ll see you guys there.” “Sounds good buddy, seeya.” I hung up the phone and decided to head back to the hotel to catch a little bit of a nap before dinner since I would have the room to myself.

As I entered the room I saw Jackie sitting in her bed under the covers, again reading a book. “What’re you up to?” she asked. “I was just going to take a bit of a nap, feeling a little jet lagged. I don’t want to bother you though.” I was still embarrassed about the previous night. “No, don’t worry. You go ahead, I’ll be quiet” she replied. “Thanks” I said. I went into the bathroom and changed into my boxers and a tank top and quickly got into my bed. “Haha, you don’t have to be embarrassed. I saw a lot more last night” Jackie chuckled. I’m sure my face went completely red. “Yea, sorry about that” I apologized again. “You don’t have to apologize, it’s ok. Hey I kinda liked it. It’s been a while since I’ve seen a handsom young man having an orgasm.” I turned to look at her with a cocked eyebrow. ‘Did she just come on to me?’ I wondered to myself. “Tell ya what” she said with a smile. “Why don’t you come over here and join me in this bed.” She pulled back the covers to reveal a beautiful, and totally naked body. I just stared for a moment. I couldn’t believe how pert her breasts were. Her stomach was flat, her skin taught, and her pussy clean shaven. She would have been hot for a 20 year old, let alone a 40 year old. “C’mon” she said, snapping me out of my trance. “We’ll have some fun.”

“Are you sure? I mean, Sara is my friend, and…..well, really?” I stammered out. “I’m sure, it’s fine. Come on over here, and just go ahead and leave those clothes in that bed.” I slowly pulled off my tank top, still considering this proposition. “That’s it, now the rest” she said, watching me keenly. My dick was already raging hard and pressing against my boxers. I stripped them off and stood up. As I walked over to her bed my hard cock bounced up and down. I could feel it’s weight and the pressure of it straining against its own size. Though I am fairly well endowed at 7 inches long and pretty wide my dick just kept wanting to grow.

I lay down next to her as she threw the covers over me. The bed was warm from her body. She set her book down and took off her glasses. “How old are you?” she asked. “18” I said, I think my voice rose about an octave as I said it. “Have you been with a woman before?” she asked. “No, I’m….I’m a virgin.” She smiled at this. “Well, I’m sorry then.” I looked at her quizzically, my lust growing like a mushroom cloud inside of me. “Why are you sorry?” “Because when you lose your virginity to me you’ll never be satisfied by a woman again.” I looked at her with a look of astonishment on my face. I pulled myself together a bit and said “Well, I guess that’s burden I’m just going to have to live with.” With that she pulled me in for a passionate kiss.

Our warm bodies pressed together as our tongues began exploring each other’s mouths. We wrapped our arms and legs around each other and me granite erection gently rubbed against her leg as we kissed. She grabbed one of my hands and placed it on her breast. It was amazing, I couldn’t believe how well rounded yet supple it was. I began squeezing her breasts one by one, tweaking her nipples occasionally. She began slowly running her fingernails along my side and stomach. With each sweep she moved lower and lower until finally she started circling the base of my penis with her fingers. She pulled away from me for just a moment. She could see in my eyes that I was dying to have her grab my dick. The absence of touch upon it when I was so aroused was like torture. “No touching yourself, you need to touch me first.”

She took my wrist and led my hand down to her bald pussy. She leaned in close again and began whispering into my ear what she wanted me to do. As she directed my fingers she also told me “Suck my nipple. Nibble my ear. Lick my neck, pinch my nipple.” These were the instructions I received in a quiet, airy voice filled with pleasure. Soon she began to take in sharp breaths. “Keep going” she gasped out as she began to reach climax. I kept my fingers moving, sucked on her neck, and pinched her nipple. This was enough, and she began bucking her hips uncontrollably. The breathy noises she had been making turned into moans and screams of pleasure. I kept working on her body until she began to calm down. “Mmmm, pretty damn good for your first time.” “Well, I’m a virgin. But I have fingered a couple girls before.”

She smiled at me and said “In good time baby.” She pushed my shoulder until I was lying on my back, my dick still making a tent out of the bed covers. She got up on her knees and positioned her pussy over my face. “Give ‘er a bit of a lick for me.” I buried my face into her sweet pussy and began lapping up all of the sweet moisture she was producing, which was a lot. It only took about a minute and she quickly shuttered into another orgasm. “Ok” she said as she recovered. She looked down at me from her kneeling position, her crotch still in my face. “Your turn” she said.

She gently grabbed my penis which alone was enough to cause me to gasp in a huge breath. She laughed a bit at my ecstasy. She started by slowly pumping my dick up and down. She got off her knees and began kissing my chest. She circled my nipples with her tongue before taking them into her mouth one by one. She sucked them hard and even bit them, slowly increasing the pressure until she got a reaction out of me over and over. She kissed and licked her way down to my dick. She kissed the head gently and then straddled me.

She positioned herself right over my erection which she grabbed and placed the head of at her entrance. “Ready?” she questioned. “Very” I said with unsuppressed anticipation. She slowly began to lower herself onto me until she was all the way down. “Damn your big, it’s been a while, but you feel huge nonetheless. My god that feels amazing.” “Glad you like it” I said. Not a great line, but my mind was too preoccupied to be trying to come up with good lines. She slowly started to bounce up and down on my dick. It was amazing, she felt so good. “Now start to go back and forth in rhythm with me. You’re a music major, you should have rhythm.” She smiled at me.

I began bucking my hips to match her speed. It didn’t take long before I could start to feel the orgasm building in my balls. “I’m not gonna last long” I said. “It’s ok, I had myself fixed after two k**s. Just cum in me, but I’m gonna ride you hard until you do.” With that she went to town on my dick. She placed her hands on my stomach and bounced up and down at a ferocious speed. My body was sent into pleasure overdrive as my orgasm burst itself through my dick and into Jackie. I could feel my cum dripping down the bottom of my dick and over my balls. Just as I was finishing Jacking screamed with one final orgasm.

She dropped off of me and curled up next to me. We both fell asleep then. Well, at least I did, I’m not sure if she did ‘cause the next thing I knew she was down at my penis with it in her hand. “Time to get up” she said. She put my flaccid dick into her mouth and began sucking. It felt amazing. As my erection quickly rose she started pumping me with one hand, sucking on my head, and massaging my balls with her other. It didn’t take long for me to get hard and then it didn’t take long for me to blow my load right into Jackies mouth. She swallowed it down with a smile; and act so sexy I swear I almost came again just watching her. “Come take a shower with me, we need to get cleaned up before we go meet Sara and Jon for dinner.” I obliged her and we had a nice shower where I fingered her to another orgasm.


Jon, Sara, and I are still friends to this day. That was the only time Jackie and I messed around with each other, and like I said, she’s now remarried. That’s too bad, ‘cause just like she said, I’ve never had that good again.

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How do I explain? What is an affair, and what isn't? All I can do is start from the beginning and let you decide. My wife Rachel and I lived next door to our very best friends and neighbors for several years. In all that time we'd never even discussed, nor approached the possibility of doing anything outside our marriage, let alone with anyone we knew. As friends, we were certainly comfortable discussing and talking about anything and everything of course. Including sex. But that was always...

4 years ago
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BBW STEPMOM

BBW StepmombyFrank2002©It seems I always had this thing for bigger, full figure women. I don't know where is started but I seemed to fantasize about them all the time. My step mom was a bigger woman. My dad divorced and remarried when I was very young. He was away quite a lot with business so it was just me and Sally, that's my stepmom, at home most times. I always thought Sally was quite attractive even when I was young. As I grew older I started to notice her more. She had put on a few more...

4 years ago
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Present from my stepmom

Another hot but fictional story. I was sixteen, it was coming close to the end of the school year and one day I got sent home early from school and my dad was away on business for the week. I walked home wearing my short plaid skirt, white blouse, knee high socks and two inch heels, with no underwear. I arrived home, but before I got inside I heard some voices around back, so I decided to go check it out. As I made my way around, I noticed my stepmom, who was actually only 22, in her smallest...

Group Sex
4 years ago
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Uncontrollable Cock 8211 Part 7 My Sexy Stepmom

After positive actions with my sexy stepmom, my hot sister, and Nisha, I jerked off my cock and had one of the best orgasms. I had cum in my underwear. So I went to sleep naked, leaving the dirty underwear on the floor. In excitement, I didn’t even realize I had left the door open. The next morning, I was still not fully awake when I heard the sound of the door opening. As always, my stepmom had come with a cup of coffee. I was half asleep and lying down on my back, exposing my semi-hard cock....

Incest
2 years ago
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Two Moms Two Sons 11 Joe And Pete Do Something Sexy For Their Moms

POV: PeteJoe and I suddenly bit down on our bottom lips and made eye contact just for a few seconds. Needless to say, my hard-on deflated just a tad. No one said a word for over a minute, but we both surely knew they wanted to see the sight, judging by the looks on their faces.Then both of them came to us, but they went to each other's sons, so I had London press the front of her body onto mine. "We fucked each other for you two, solely to please you," she admitted, wrapping her arms around...

Incest
2 years ago
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Scott and his Stepmom

Scott's had recently turned 18, for his birthday his father and his stepmom decided to get his own laptop so he didn't have to share the family computer no longer. Scott resented his stepmom, he hated the way she made him address as her as Mom or Mommy. Scott's real Mom ran out on him when he was little boy, so now he lives with his father (40), stepmom (52) and two half sisters both younger.Scott was a total nerd, top of all his classed, member of the chess team, and the AV club. He had never...

2 years ago
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Affairs of a HousewifeChapter 3

A few days went by and the guilt of cheating on her husband, now twice, consumed her. She never intended to have thoes affairs. She was looking for some level of recognition, but was not ready for what she did receive and the crushing wave of wanting and lust that consumed her. In the first month of work, she felt like she was so much more than a boring housewife. The looks she received from coworkers, her bosses, and complete strangers on the street always made her feel good about herself....

3 years ago
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Roses video Chapter 10 Maria and Rose swap moms

Both Rose and I kissed each other's moms for about twenty minutes straight. I couldn't help, but to look at Rose and my mom from time to time. It all created the perfect storm of sexuality where the taboo aspect of it still made it quite hot. 'Even as I'm not actually related to Kate, it still feels like incest. Maybe it solely because she is my godmother or that my mom is making out with Rose right now. Who the hell knows? Kate has always been like a second mom to me, and she never had...

4 years ago
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Roses video Chapter 10 Maria and Rose swap moms

POV: Maria Both Rose and I kissed each other's moms for about twenty minutes straight. I couldn't help, but to look at Rose and my mom from time to time. It all created the perfect storm of sexuality where the taboo aspect of it still made it quite hot.'Even as I'm not actually related to Kate, it still feels like incest. Maybe it solely because she is my godmother or that my mom is making out with Rose right now. Who the hell knows? Kate has always been like a second mom to me, and she never...

Incest
2 years ago
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Oh Hello Stepmom

Hello, my Dear Readers. I have been writing incest themed stories, focusing mainly on mom-son relationships, for some time now. I wanted to try something light-hearted, featuring a young & naive stepmom and her stepson, who is expecting nothing sexual from her. This is my humble attempt on the same. Happy Reading! Sidharth was both bothered and excited. He had just landed back in Mumbai, after completing his studies from a university in the UK. He was on his way home, and he was going to meet...

Incest
1 year ago
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Eating at Moms

100% fiction! My name is Mike and I live with my 60 year old mom. I never knew my dad, and my mom had an endless string of men visiting her over the years. Mom was a drinker and a party girl and a slut that always tried to please the men in her life. She's a little woman with dark brown hair that she keeps short. She has nice tits for her size but her perfect bubble butt is her best feature. She wears granny glasses and looks sort of innocent. moms pussy and lower plump belly is now covered...

Incest
3 years ago
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Reese Witherspoon dommed

any of the actresses mentioned below. This story is written down for enjoyment purposes only. Reese witherspoon woke up with a headache. She didn't know where she was. All she could feel that she was blindfolded. Not only that, she was tied to the bed with duct tape, unable to move her hands and legs. She also noticed that she was nude. A duct tape covered her mouth so that she shouldn't shout. All she remembered was going to a producer's home for some script reading of a film they were...

4 years ago
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Uncontrollable Cock 8211 Part 1 My Sexy Stepmom

Hi everyone, my name is Pratyush, and I am from Nepal. I have been a regular reader of ISS (especially after meeting my sexy stepmom) for more than 7-8 years now. When I first came here, I was a virgin, and now, I do not even know how many girls I have slept with. Finally, I realized why not post my stories here in ISS, the same ISS that has taught me so many things. Before starting, I would like to thank every writer here in ISS who has shared their stories and helped people relieve their...

Incest
4 years ago
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The white teenage boy who as 2 pitch black moms

Hi everyone im Brandin. My mom name is Kisha and my other moms name is Latosha. Yes I have 2 black moms.Oh yea they are lesbos by the way. I dont even know my real parents are. any way ill let you read the story now.It was sunday after noon when my mom latosha walked in with the londry wearing a black spandex dress shirt and black spandex pants.she had huge watermelon tits and a big round nice hipo ass real thin abbs thick legs and strong arms when she bent I stared.I dont know why tho she my...

2 years ago
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Tennis Moms

Linda and Stacy were both the same age–thirty-six–and looked great. But they were like night anvisit my msg board it got pics and you can post there to http://piclink.aimoo.com/d day: Linda was a tall, six-foot platinum blond, with small tits, and a runway models body, Stacy was Italian, five-four, with huge breasts and long black hair. Her body was thin, but more curvaceous. They just got finished with a morning of tennis, and now they were in the locker room. They only went there to dry...

3 years ago
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Dinner at moms

We had just got back from holiday a week before and mom had invited us round for dinner, Elaine wasn't feeling too good so i went alone to see mom Tina. I had told mom the night before that Elaine wasn't coming so she wasn't surprised when I turned up with just a bottle of wine for the two of us. When we was on holiday mom promised an all day fucking session and I think today was that day . I let myself in Moms house, she was upstairs getting changed, so I went to have a sneak peak. She had...

3 years ago
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Golfing with Mom

Golfing with Mom I was the youngest of three siblings growing up. My older sisters Kat and Debbie were both older by a few years. My mom Joanne, and dad John were products of the war generation which made my siblings and me 'baby boomers'. I grew up in a suburban neighborhood and had a middle-class neighborhood upbringing. My mom and dad were quite athletic in their youth and still were very active and loved to golf. My sisters were never into sports, but dad and I used to have fun...

4 years ago
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Trapped In Paradise With My Mom

"Honey,are you coming home this Christmas...???”my Mom asked at the other end.I looked reluctantly at the phone in my hand.I had no intentions of going home.There could be no better way to ruin a holiday than to go to my hometown,a remote little hill town far off in the north.People say it's a beautiful place,maybe.But in this season,the end of December,when the whole town will be covered under tons of snow and with its sub-zero temperature;it does not look like a dream holiday to...

4 years ago
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My Fun With Mom

My fun with momChapter 1As Mom and I walked back to the car after dropping dad off at the airport, she put her arm around me and pulled me close. She had been doing this whenever we were together and alone. She giggled as I placed my arm around her shoulders pulling her toward me. I was a little taller than Mom so I kissed the top of her head as we walked. Why I did, I couldn't tell you, except I loved my Mom and at that moment felt a little sorry for her because Dad would be gone for the next...

4 years ago
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Hiking in the Mountains with Mom

Mom had promised me that she and I would celebrate my eighteenth birthday at our cabin by the mountainside. I was eagerly looking forward for the occasion. I had always loved to visit our old little cabin, situated at the foothills. I also knew that perhaps it would be our last holidaying together for this season. With the winters were about to go, but the whether was still very cold. We all were looking forward for the upcoming summers. Within weeks the weather would slowly start getting warm...

4 years ago
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Strip Games With My Mom

This story is imagination story. My family consists of dad, mom, sister and me. We lived in the apartments in Mumbai. My dad works in the private company in Mumbai as supervisor. He was busy with work in developing the company. He was the right hand to boss in that company so he was always busy with the work. He regularly goes to gym to maintain the good physique and was fair and tall. My dad married my mom when he was 25 years and mom was 22 year. Next the mom was the house wife. She is the...

2 years ago
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Strip Games With My Mom

This story is imagination story. My family consists of dad, mom, sister and me. We lived in the apartments in Mumbai. My dad works in the private company in Mumbai as supervisor. He was busy with work in developing the company. He was the right hand to boss in that company so he was always busy with the work. He regularly goes to gym to maintain the good physique and was fair and tall. My dad married my mom when he was 25 years and mom was 22 year. Next the mom was the house wife. She is the...

Incest
4 years ago
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My First Time With My Dearest Mommy With My Mom

My name is Zack.I was born on 11th May 1981 and my zodiac or starsigns are Taurus.My first time with my dearest Mom happened under the very weird circumstances.This wasn’t something planned by me or my Mom and it happened due to my boldness and persistence.Everything started at early September 2002.It was midweek.I had visited my parents to eat when my Dad asked if I would like to accompanied my Mom to a wedding ceremony.I learned that the 2nd cousin of mine was getting married and my Mom...

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