Debbie's First free porn video

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I’ve been friends with Debbie for almost fifteen years and have always had the hots for her. She’s a petite, 5’2”, hard bodied, small figured woman. She is in her mid 40’s, but has a body that most teenagers would kill for. Though I don’t consider myself any particular body part kind of guy, I gotta say she has an ass that would cause me to just blatantly stare like some kind of school kid. I consider myself respectful of women, but occasionally I lose large amounts of blood to my brain, and resort to typical Neanderthal. Her ass had had that effect on me.

We were both in relationships and though mine was involved in the lifestyle, hers was not. I occasionally had thoughts about her joining my wife and I for some play time, and even involved her husband in some of these little fantasy scenarios, but they would remain just that… fantasies.

A few years ago, we both found ourselves having relationship issues. We had both separated from our significant others, but neither one really wanted to go into the dating world. I had had a couple brief encounters, but kept them short. She had no real interest in seeing anyone whatsoever though she did try getting together with someone for the companionship and even stepped outside of herself and slept with him, but it was short lived.

We would hang out and listen to each other open up about our problems. Even though our lifestyles were completely different, our situations had a lot of similarities. Suggestions we would have for each other were way off the mark but it was nice to have someone to share with. Even though I had a strong physical attraction to her, I valued her friendship and didn’t want to screw it up making a move on her. We would be physically affectionate towards each other, but it was pretty mild until…

One night, at a party, a friend of hers made a comment to her that she could see some serious sparks between us. I guess she hadn’t really noticed, since I was trying to behave and she was distracted with her relationship issues. The comment (mixed with a few cocktails), must have stirred her curiosity, because at some point our innocent flirting turned into some pretty heavy petting.

Being who she was, some guilt set in afterwards about it. While trying to respect her boundaries, I finally convinced her that above all, our friendship would remain intact, that we were helping fill a void in each other’s lives and it was with someone we cared about and respected. We were safe. No drama, no expectations, just the human contact and physical company that people need to remain sane.

So we would get together as our busy schedules would allow and enjoy each other’s bodies with an intensity and passion that I don’t think either one of us expected. It was awesome. We quickly reached a comfort level with each other that allowed us to open up and explore each other. Did I mention it was awesome? Just checking.

Occasionally, I would try to whisper, or read some fantasies to her involving other people. One of my biggest turn ons is pleasing a woman with one or more other men. I have no desire for the men but seeing a woman as the center of attention, being pleased as her body is worshipped by multiple men is an indescribable, erotic sight.

Her and I had discussed my lifestyle many times, and I would try to ensure her it really wasn’t like those bad 70’s stereotypes. She had confessed about having occasional thoughts of maybe two men pleasing her, and possibly feeling another woman’s body, but they were just thoughts. Not something she could ever see herself doing. Or so she thought.

She was having a holiday party at her house for some family and friends, with some of her sons’ friends also present. One of the guys, Alex, though quite a few years older than her other sons friends and a lot more mature, really caught her eye. He had been flirting with her the better part of the night, and I could tell she was enjoying the attention.

As the night progressed and the drinks flowed I finally enlightened her to the fact that he was coming on to her something fierce. “He’s fuckin hot,” is all she said as she turned and walked away. Those three little words caused me to have an erection I thought was going to rip through my pants. My mind went into overdrive with the erotic images that started going through my head.

Most everyone had left and since Alex had been drinking pretty heavily and didn’t have a designated driver, Debbie insisted that he stay. Though kind of late, the three of us weren’t quite ready for bed yet, so we decided to put a movie in.

The fireplace had made the room extremely warm, so I changed into some shorts. Debbie found a pair for Alex and she changed into some really sexy shorts and a tank top. Damn she looked good. When she saw Alex come out of the bathroom with just the shorts and no shirt on, the look on her face was one of almost pure lust.

He wasn’t overly muscular, but was very defined and in real good shape. And the shorts didn’t do much to hide his package, and it didn’t go unnoticed.

We refilled our drinks, and sat on the couch, Debbie between the two of us. She had a light sheet ta cover up with and spread it over the three of us. Don’t remember what the movie was, but it seemed to have a lot of sexual content.

Debbie and I had our hands on each others thighs, just lightly caressing while watching the movie. I kept trying to steal glances to see if her other hand was on his lap. She brushed against my cock at one point, and when she felt how hard I was, she turned and looked at me with a wondering smile.

I leaned in and gave her a soft kiss, sliding my tongue along her lips, and told her I was going to step outside for a smoke. The questioning look was almost a glare as I got up. When I lifted my part of the sheet, I could see up the leg of her shorts, and noticed she had no panties on. I thought I also caught a glimpse of his hand on her thigh, but wasn’t sure.

I walked out the front door, grabbed a smoke, and quickly walked around the deck to the back of the house, where I had almost a clear shot of the couch. I could see them talking with the light from the fireplace and TV. Then I saw him lean in and kiss her. She seemed to freeze for a second, and then she looked around, I assume to see where I was. Thinking I was out front, she leaned into him and began kissing him back.

I know from past experience that like me, kissing is the one thing that seriously gets her juices flowing. Their making out was getting heavier and more passionate by the second. I moved a little and was able to notice he had a hand in her tank top, pinching her nipples.

I still couldn’t see anything lower due to the sheet but there was movement there as well. Suddenly she stopped and stood up, fixing herself, and began walking towards the front door. I quickly moved back to the front, just as she walked out. She looked a little shaken and flushed so I asked if she was okay.

She told me it had just gotten a bit warm, and needed some air. I told her that I might go upstairs and lay down, for a bit, if that was okay and that she should finish watching the movie with Alex. She said okay and that she would be up as soon as the movie was over. I told her no hurry, and gave her a short, but passionate kiss.

We went back in and I started upstairs as she went to the living room. I made a little noise upstairs like I was getting in to bed and quietly came back down. I was able to move around to the kitchen where I had an unobstructed but hidden view.

She was sitting really close to him again, this time without the sheet, and they were whispering. She was saying that this isn’t something she does and it was the alcohol talking, as her hands were wandering over his arms and chest.

He took her face in his hands and began kissing her again. She would mildly resist but I could tell that what she really wanted to do was just tear his shorts off and straddle his cock, sliding it deep into her and satisfying that craving that had been building.

That thought must have overtaken her, because she appeared to finally give in. She helped him take her tank top off, where he immediately began kissing and sucking on her nipples. She was trying to muffle her moans by biting on his neck but it was a futile attempt. I adjusted my viewing position and noticed they each had their hands in each other’s shorts. It was an incredible site that had me stroking my cock inside my shorts.

They then stopped for a second and Debbie got up, moved the coffee table over and laid the sheet down on the carpet. She then peeled off her shorts, went over to began sliding his shorts down his legs. When his cock came into view, she stopped for a second and just said “Damn!”

Even from my point of view, it was impressive. It wasn’t so big that she feared being hurt but it was definitely going fill her up. It was only a couple inches longer than mine but probably twice as big around.

She got his shorts the rest of the way off and he stepped out of them. She almost couldn’t get her hand all the way around it but began stroking it while licking the little drop of pre-cum that had formed on the head. She was able to get her mouth over it but wasn’t able to go down very far at first. Little by little, she took more of it, as she relaxed her throat.

Now, knowing the feeling of those incredible lips and tongue, while watching her beautiful face on my cock, I could understand the expression on his face. At this point though, she was thinking of one thing. She wanted him inside her, NOW. She laid him down and straddled him while guiding his cock into her extremely wet pussy.

She was so worked up over the whole scenario that her juices were literally running down the inside of her thighs. She rubbed the head along her lips and when it hit her clit it made her shudder. She began slowly sliding herself down on him, while she got used to his size. Even as wet as she was, she had a bit of trouble getting him in.

He pulled her down to kiss him and as he did, a little more slid in. She moaned into his mouth as their tongues intertwined. He held still for a moment while she got used to him. His hips began slowly moving back and forth along with hers as her pussy swallowed more and more of him. Thinking he was all the way in, she gave a final push back, only to discover that she was only about half way there. The slight pain was quickly overcome by an orgasm that sent her entire body into tingly convulsions.

After a minute, she began to slowly rock back and forth on him, feeling herself being completely filled as the waves rushed over her body. She didn’t know how much more she could handle before she went into orgasmic overload, but she was willing to find out. Their hips soon began moving faster, as the passion increased, until you could hear their skin slapping together.

She stopped and told him to roll her over and fuck her. As they did, I realized I had put myself into view. Debbie had her eyes partially closed but I could tell by the pause that she had seen me, with my cock in my hand and a big smile on my face.

At this point, she was too far gone to stop if she wanted to and knowing it was one of my fantasies with her anyway, she kept going, with what appeared to be a new found energy. She started thrusting herself up into his cock as his balls would smack her ass.

I could hear her juices with each thrust and knew she was totally enjoying the fucking her new young stud was delivering to her. I knew if I didn’t stop stroking my cock, I was gonna cum all over the kitchen floor. At that point, I saw him begin to tense up and knew he was getting ready to come.

Debbie sensed this and began thrusting even harder. When she told him to cum inside her, it was all he could take and began filling her pussy with hot squirt after squirt of his thick cum. She could feel it hitting her deep inside and it caused her to start coming again. Her whole body was convulsing as he slowed down. He collapsed on top of her, their bodies slippery with a mixture of sweat and cum. She lifted her head slightly to see if I was still there. I smiled and quietly went upstairs.

About ten minutes later, she came upstairs, holding her shorts and tank top. She looked at me and started for the bathroom when I grabbed her hand and pulled her to me. I kissed her deeply and told her that was incredible. I gently laid her down on the bed and getting on top, easily slid my cock inside her.

With the mixture of his cum and hers, I easily slid all the way in to my balls. Feeling her pussy all slick and wet gripping my cock, caused me to come almost instantly. Adding my cum to her already full pussy caused her to have one more little orgasm. We lay there, gently kissing and caressing for a minute.

She looked at me and as a smile came across her lips, she blew me away by asking "Should I invite him up?"

Stay tuned for part 2…

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Debbie Crosses The Line Again

It had been several weeks since Debbie had her sexual encounter with one of her clients. At firs she was afraid that he was a state inspector and she would lose her license but as time passed she became more confident that he wasn't. Today she had two clients, both female. The morning appointment was at 9:00am and the afternoon wasn't until 5:00. At 8:45 the doorbell rang. Gina was right on time as usual. She has been a client for almost two years now and was never late. Debbie walked her to...

4 years ago
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Debbie Does DaddyChapter 2

The Party Sunday I dressed in a long-sleeve green Henley and brown pants, ready to go to Kara’s father’s party. Debbie took one look at me and said, “No, Daddy, that won’t do. Go change into your blue golf-shirt.” Kara chipped in with, “She’s right, Brett. That green thing is totally wrong.” Sponsor or no, I know when I’m outnumbered, so I retreated back to my room to change. The journey took less than two hours. I drove, with Kara directing. She was guiding us through an up-market suburb...

2 years ago
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Debbie gets ganged

He met Debbie at his house; as per usual, his parents were out working until late that evening. They sat on the love seat in the living room and Jay was hotly kissing her swan-like neck while cupping and rubbing her big, bra-less titties through the tissue-thin fabric of her cut-off top. Her stiff nipples strained against the soft fabric, the round brown aureoles clearly visable through the nearly transparent material. Jay said “how would you like to suck and fuck a couple of guys that I...

2 years ago
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Debbie and the curious Vicar bi

I had spent the night with Debbie and Tony, as usual we had a fantastic night. I stayed the night as I usually did. I woke up at 8am. It was a Sunday morning and Debs and Tony were already up and in the kitchen."Morning Steve, sleep well" asked Debbie."Very well thanks Debs, you always wear me out"...I replied.I was so comfortable now with this fantastic couple, they were so accommodating and nothing was too much trouble, either in the bedroom or as friends.I always had a bi side, ever since I...

1 year ago
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Debbie gives a perfect blow job

I looked at Debbie as she got up from the sofa and went into the kitchen. Everyone from the party had, either left or had gone to bed. It was late now and as I followed Debbie into the kitchen she stopped and turned towards me. We had been waiting for a while to be alone, and now finally we had the opportunity. I moved closer to her and I put my hands around her waist. I leaned forward and we both kissed. Her hand reached down between my legs and she began to feel me getting aroused through my...

Erotic
3 years ago
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Debbie Takes Tissues ShoppingChapter 5

Debbie strode quickly and I stumbled to keep up as she pulled me by the hand. The toy plastic heels I was wearing weren’t made for walking. We walked about two blocks when Debbie pulled me toward the door of a bar. I thought about reminding her that we weren’t old enough to go to a bar but thought better of it. Nothing I said mattered anyway. We entered the bar. It was dimly lit and there wasn’t much in the way of decoration. Just the bar stools and a few tables. All the chairs didn’t even...

3 years ago
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A Night of Firsts

I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.So after a lot of planning over several months, the day had finally come.I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any...

Crossdressing
4 years ago
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A Day of Firsts

A Day of Firsts by Kathy Nelson [email protected] (c):Kathryn Nelson, 1998 It was one of those hectic work periods where I was putting in 70 to 80 hours a week. You know, when there's no time for anything else in your life except the job. But, thank god the rush was over and it looked like things were going to calm down. Friday night had come around and I was going home at a decent hour. I even had the whole weekend off and I was ready to celebrate. Well, more like...

3 years ago
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Debbies daughter caught us fucking

I've been fooling around with my office manager Debbie for a few years. She is now 66 and I am 57. Shes a sweet fuck with  a cute hot pussy. Hasn't always been a hot pussy,she claims I made her that way. I know her and her daughter Katie are close but I didn't realize how close. Debbie has told Katie all our little secrets. I only see Katie once or twice a year and she always says take care of mom. I never read anything into it. One day around 3pm Katie comes to the office to pick up her mom...

4 years ago
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Debbie Grows Up

Debbie Myers was only 20 years old and already she had made it to copywriter for a large ad agency. She graduated from college the year before, and this was her first real job in advertising. A very attractive young lady her blond hair when down stretched all the way to mid back. At 5 foot 6 inches when she had her heels on she looked most men in the eye. Her blue eyes sparkled when she laughed, and that was often. Debbie had been working on a project all day, and late into the night until she...

4 years ago
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Debbie Does Because

There was a time when I thought that I was "one sick puppy." No, that's not right, I am one sick puppy, but there was a time that I thought that I was alone in my particular obsession. Then I got a computer, got turned on to the internet, and found out that there are a lot of other people out there who are just like me. My obsession? Eating my wife's pussy after she has been freshly fucked by someone else! I wasn't always that way. I used to be a clean living, fun-loving guy, and then I...

1 year ago
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Debbie and her Birthday

OK babe got to run (as Mike kisses his wife quickly on the check) or I’ll miss my plane. I’ll call you when I get there ok. See you in about a week babe. Debbie could here his footsteps as Mike walked out of the house she laid there in bed thinking about this morning how dull her like had become mostly the sex Mike just laid there on top of her pumped a few times finished then got off went to go shower (guess he figured that is my birthday present (the prick) at one time she though how hot and...

Fetish
2 years ago
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An Afternoon of Firsts

The bar was crowded for the big football game. Standing room only. I was alone but hoped to find another regular to watch the game with. I ordered a beer and resigned myself to a disappointing spectacle. A good game was much more enhanced when watching with a familiar face or two. Halfway through my beer, I see Jim walk in. Jim was a guy a frequently chatted with and we really hit it off. He was the perfect guy to watch the game with. I flagged him over, shook hands and told him "Looks like...

Seduction
3 years ago
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Debbie

My entire routine had changed as well as my sex life. I had recently moved back from my hiatus out of state so that meant adapting to a different life style as well as a new routine. Not that I cared that things weren’t as comfortable as they used to be, I actually embraced it. I’m the kind of guy that likes change, who welcomes change, so that’s why it was easier for me to adapt to a different culture. Of course the culture was something I was used to – I used to live here, after all. It’s...

Reluctance
2 years ago
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Debbies First Visit

First of all let me just say this, this is a true story of what happened to me a couple years ago whilst at my local Bar.it had been 5 or 6 months since me and my Crazy ex split (thats a whole different story) and despite a few over nighters the first month i was going through a dry spell.Every Friday was always Bar night, me and all the guys would go down to our local bar and stay until it closed, tonight was no different.now due to the pretty low standards of the place, women were pretty...

1 year ago
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Debbie The Cougar Part 2

I was still recovering from the first wave, and knew it was my turn to please her at least the same way she did, if not more (if possible). I slid on the bed to lie next to her and turned her to face me. Stroking her hair away from her face, I leaned closer and kissed her mouth, tasting my own cum on her lips. She sucked my tongue as greedily as she had done my dick and I felt my balls tighten a little as life pounded back into my shaft. I so wanted to fuck this beautiful, sensuous young woman,...

2 years ago
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Debbie succumbs to charm of the shoe salesman

Debbie succumbs to charm of the shoe salesmanWe are Alan and Debbie, happily married for many years. A while ago we were in Devon on a touring holiday and one day drove into Cornwall . We lunched in a small village pub, then went walking and looking at the few shops there. Late in the afternoon we came across a small shoe shop. My wife had been looking for some open sandals for a while. On entering the shop we were met by a gentleman of around mid-50's. My wife would have been 53. Another...

4 years ago
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Debbie wants another child 1

Debbie ,my ex-wife had cheated on me more times than I could count, even after she said she was sorry. After she apologized,I would accept it mainly because we had a child together .and she was my first love The 4 year marriage ended a year ago when she suddenly left me and disappeared with my daughter. I had not heard from her until she wrote me a letter asking me to meet her at a hotel, so I did. I was expecting to see my daughter with her ,but instead it was just her, alone. I...

3 years ago
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Debbie Dan and the DemonChapter 3

"Well Debra," the demon said as Debbie walked (a bit wobbly) down the street after leaving the café. "That went well." "Went well?" Debbie started to rise to the bait. "How can you say that? Okay, okay, I'll stay polite, I believe you are who you say you are, and you obviously control me utterly. But what went well? I just let two perfect strangers violate me, pump their (retch) semen into my mouth and vagina! Besides being unfaithful to Dan, I'll probably get pregnant, or...

4 years ago
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Debbie Does Me

When I hit 18 and started attending college at Sac State (CSUS for those who love acronyms LOL!), I enjoyed the freedom of finally being legal and able to enter strip clubs for the first time. Among the things I love are music and big tits, and in San Francisco I could indulge in both my hobbies. So whenever one of my favorite bands played such legendary places like The Warfield, Slim's or The Fillmore, I would make sure to get into town early and spend a little time, and cash, at the infamous...

2 years ago
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Debbie

There was this girl. The first time I saw her at the store, she smiled at me. I notice these things. Being a lonely guy and super leery of anything wearing a skirt, I notice. The second time, she helped me check out in the self-service lane, and I really noticed her. She was gorgeous. She was friendly. She was not wearing a ring. I made a point to thank her, letting her know I was new to this part of town, and really appreciated her help. She went so far as to say she hoped she saw me there...

3 years ago
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Debbie visits the pool

Towards that end she selected her older thin white bikini to squeeze into; her breasts had grown since the purchase of this garment so now she had a generous amount of titflesh bulging from the top and a portion of pendulous boobs protruding from the bottom of the cups also (double trouble)! Grabbing a towel and suntan lotion and a few other items the nubile teen walked the few blocks to the public pool. Arriving she staked out a spot near the deep end and began applying lotion to her firm...

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